Crystal structures of two polymorphic forms of DOTAM-mono-acid dihydrate

The structural chemistry of 2-[4,7,10-tris­(carbamoylmeth­yl)-1,4,7,10-tetra­aza­cyclo­dodecan-1-yl]acetic acid dihydrate, C₁₆H₃₁N₇O₅·2H₂O, is described. The macrocyclic compound, also known by the abbreviation DOTAM-mono-acid, crystallized at room temperature and was isolated concomitantly as two polymorphic forms. The structures of both polymorphs were determined at 90 K. The first polymorph crystallized as a zwitterionic dihydrate [systematic name: 4,7,10-tris­(carbamoylmeth­yl)-1-(carboxyl­atometh­yl)-1,4,7,10-tetra­aza­cyclo­dodecan-1-ium dihydrate] in the space group P2₁/n, with Z′ = 1. The second polymorph crystallized as a zwitterionic dihydrate in the space group P2₁ at 90 K, with Z′ = 2. The two independent mol­ecules are related by a local center. In each polymorph, the zwitterion is formed between the negatively-charged carboxyl­ate group and the ring N atom that bears the acetate pendant arm. Extensive inter- and intra­molecular hydrogen bonding exists in both polymorphic structures. In polymorph 1, an inter­molecular hydrogen-bonding network propagating parallel to the a direction creates an infinite chain. A second hydrogen-bonding network is observed through a water molecule of hydration in the b direction. Polymorph 2 also has two inter­molecular hydrogen-bonding networks. One propagates parallel to the a direction, while the other propagates in the [10] direction. Increasing the temperature of polymorph 2 yields the same structure at T = 180 K, but the pseudocenter becomes exact at 299 K. The higher-temperature structure has Z′ = 1 in the space group P2₁/c.

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXS97 (Sheldrick, 2008).

4,7,10-Tris(carbamoylmethyl)-1-(carboxylatomethyl)-1,4,7,10-tetraazacyclododecan-1-ium dihydrate (Jurek3_90K)

Crystal data

C16H31N7O5·2H2O	F(000) = 944
Mr = 437.51	Dx = 1.349 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7361 (4) Å	Cell parameters from 4008 reflections
b = 13.7118 (5) Å	θ = 2.4–29.9°
c = 16.1437 (7) Å	µ = 0.11 mm^−1
β = 92.249 (3)°	T = 90 K
V = 2153.52 (15) Å^3	Needle, colourless
Z = 4	0.27 × 0.11 × 0.09 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	6554 independent reflections
Radiation source: fine-focus sealed tube	4645 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 30.6°, θmin = 2.0°
Absorption correction: multi-scan SADABS; Bruker, 2009)	h = −13→11
Tmin = 0.897, Tmax = 0.971	k = −19→19
22980 measured reflections	l = −22→23

Refinement

Refinement on F^2	21 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.2788P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6554 reflections	Δρmax = 0.42 e Å^−3
304 parameters	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.75214 (10)	0.65184 (7)	0.71673 (6)	0.0138 (2)
O2	0.88865 (10)	0.61026 (7)	0.82679 (6)	0.0126 (2)
O3	1.08858 (11)	0.70545 (7)	0.49900 (6)	0.0186 (2)
O4	0.45079 (10)	0.59949 (7)	0.45185 (6)	0.0133 (2)
O5	0.17985 (10)	0.79903 (7)	0.78710 (6)	0.0151 (2)
N1	0.73037 (11)	0.83643 (8)	0.77334 (7)	0.0093 (2)
H1N	0.6974 (16)	0.8096 (12)	0.7259 (10)	0.011*
N2	0.85964 (11)	0.85879 (8)	0.60661 (7)	0.0099 (2)
N3	0.56783 (11)	0.81519 (8)	0.55270 (7)	0.0093 (2)
N4	0.45217 (12)	0.81194 (8)	0.72286 (7)	0.0103 (2)
N5	0.89823 (13)	0.66196 (9)	0.56566 (8)	0.0161 (3)
H51N	0.8958 (17)	0.6043 (10)	0.5433 (10)	0.019*
H52N	0.8436 (16)	0.6764 (12)	0.6054 (10)	0.019*
N6	0.55038 (12)	0.61413 (8)	0.58026 (7)	0.0113 (2)
H61N	0.5223 (16)	0.5558 (10)	0.5928 (10)	0.014*
H62N	0.5992 (15)	0.6497 (11)	0.6164 (9)	0.014*
N7	0.17517 (14)	0.63597 (9)	0.77020 (8)	0.0176 (3)
H71N	0.0897 (14)	0.6329 (13)	0.7887 (11)	0.021*
H72N	0.2176 (17)	0.5851 (11)	0.7490 (11)	0.021*
C1	0.86468 (14)	0.88577 (10)	0.75678 (8)	0.0113 (3)
H1A	0.9397	0.8371	0.7608	0.014*
H1B	0.8837	0.9361	0.7997	0.014*
C2	0.86319 (14)	0.93289 (10)	0.67211 (8)	0.0113 (3)
H2A	0.7816	0.9756	0.6652	0.014*
H2B	0.9463	0.9738	0.6674	0.014*
C3	0.79448 (14)	0.89506 (10)	0.52925 (8)	0.0119 (3)
H3A	0.8158	0.8497	0.4838	0.014*
H3B	0.8347	0.9593	0.5161	0.014*
C4	0.63922 (14)	0.90579 (9)	0.53241 (8)	0.0109 (3)
H4A	0.6182	0.9558	0.5743	0.013*
H4B	0.6030	0.9295	0.4779	0.013*
C5	0.42287 (14)	0.83518 (9)	0.56961 (8)	0.0106 (3)
H5A	0.3698	0.7739	0.5632	0.013*
H5B	0.3856	0.8820	0.5278	0.013*
C6	0.40176 (14)	0.87653 (9)	0.65596 (8)	0.0107 (3)
H6A	0.4499	0.9400	0.6612	0.013*
H6B	0.3025	0.8886	0.6623	0.013*
C7	0.48326 (14)	0.86240 (10)	0.80098 (8)	0.0116 (3)
H7A	0.4792	0.8155	0.8475	0.014*
H7B	0.4136	0.9137	0.8093	0.014*
C8	0.62529 (13)	0.90828 (9)	0.80071 (8)	0.0111 (3)
H8A	0.6233	0.9651	0.7629	0.013*
H8B	0.6513	0.9318	0.8571	0.013*
C9	0.75523 (14)	0.75491 (9)	0.83400 (8)	0.0111 (2)
H9A	0.6693	0.7398	0.8622	0.013*
H9B	0.8256	0.7748	0.8766	0.013*
C10	0.80444 (14)	0.66421 (9)	0.78819 (8)	0.0097 (2)
C11	0.99691 (14)	0.82153 (10)	0.59215 (8)	0.0129 (3)
H11A	1.0479	0.8148	0.6461	0.015*
H11B	1.0465	0.8697	0.5588	0.015*
C12	0.99703 (14)	0.72369 (10)	0.54774 (8)	0.0122 (3)
C13	0.57327 (14)	0.74683 (9)	0.48297 (8)	0.0116 (3)
H13A	0.6696	0.7408	0.4661	0.014*
H13B	0.5182	0.7733	0.4353	0.014*
C14	0.51948 (13)	0.64721 (9)	0.50425 (8)	0.0099 (2)
C15	0.37930 (14)	0.72027 (9)	0.73099 (8)	0.0121 (3)
H15A	0.4367	0.6770	0.7672	0.015*
H15B	0.3723	0.6894	0.6756	0.015*
C16	0.23549 (14)	0.72280 (10)	0.76522 (8)	0.0108 (3)
O6	0.79085 (11)	0.47683 (8)	0.48577 (7)	0.0179 (2)
H61	0.8343 (18)	0.4214 (11)	0.4903 (12)	0.027*
H62	0.7143 (16)	0.4654 (14)	0.5088 (11)	0.027*
O7	0.32448 (11)	0.49460 (7)	0.67654 (7)	0.0172 (2)
H71	0.2860 (18)	0.5025 (13)	0.6265 (10)	0.026*
H72	0.3229 (19)	0.4329 (11)	0.6868 (11)	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0158 (5)	0.0129 (5)	0.0126 (4)	−0.0007 (4)	−0.0011 (4)	−0.0017 (3)
O2	0.0119 (5)	0.0100 (5)	0.0160 (5)	0.0016 (4)	−0.0010 (4)	0.0012 (3)
O3	0.0205 (6)	0.0176 (5)	0.0184 (5)	0.0031 (4)	0.0096 (4)	−0.0005 (4)
O4	0.0167 (5)	0.0096 (4)	0.0132 (4)	−0.0004 (4)	−0.0033 (4)	−0.0016 (3)
O5	0.0129 (5)	0.0104 (5)	0.0223 (5)	0.0009 (4)	0.0046 (4)	−0.0028 (4)
N1	0.0080 (5)	0.0096 (5)	0.0102 (5)	−0.0001 (4)	0.0001 (4)	−0.0013 (4)
N2	0.0084 (5)	0.0101 (5)	0.0112 (5)	0.0009 (4)	0.0000 (4)	−0.0018 (4)
N3	0.0091 (5)	0.0068 (5)	0.0121 (5)	−0.0014 (4)	0.0015 (4)	−0.0008 (4)
N4	0.0111 (6)	0.0088 (5)	0.0111 (5)	−0.0014 (4)	0.0011 (4)	0.0002 (4)
N5	0.0176 (7)	0.0140 (6)	0.0170 (6)	−0.0004 (5)	0.0061 (5)	−0.0059 (4)
N6	0.0141 (6)	0.0073 (5)	0.0124 (5)	−0.0005 (4)	−0.0014 (4)	0.0000 (4)
N7	0.0142 (6)	0.0099 (6)	0.0294 (7)	−0.0006 (5)	0.0098 (5)	−0.0026 (5)
C1	0.0085 (6)	0.0135 (6)	0.0118 (6)	−0.0018 (5)	0.0002 (5)	−0.0021 (5)
C2	0.0115 (7)	0.0094 (6)	0.0131 (6)	−0.0022 (5)	0.0016 (5)	−0.0028 (4)
C3	0.0138 (7)	0.0111 (6)	0.0109 (6)	−0.0024 (5)	0.0009 (5)	0.0007 (4)
C4	0.0122 (7)	0.0077 (6)	0.0128 (6)	−0.0007 (5)	0.0000 (5)	0.0007 (4)
C5	0.0093 (6)	0.0095 (6)	0.0128 (6)	0.0005 (5)	−0.0008 (5)	−0.0002 (4)
C6	0.0102 (6)	0.0085 (6)	0.0135 (6)	0.0006 (5)	0.0009 (5)	−0.0004 (4)
C7	0.0103 (6)	0.0121 (6)	0.0125 (6)	0.0014 (5)	0.0014 (5)	−0.0011 (5)
C8	0.0098 (6)	0.0097 (6)	0.0140 (6)	0.0020 (5)	0.0020 (5)	−0.0031 (4)
C9	0.0128 (7)	0.0103 (6)	0.0102 (5)	0.0022 (5)	0.0005 (5)	0.0001 (4)
C10	0.0089 (6)	0.0087 (6)	0.0119 (6)	−0.0025 (5)	0.0028 (5)	0.0003 (4)
C11	0.0096 (7)	0.0144 (7)	0.0148 (6)	−0.0001 (5)	0.0017 (5)	−0.0026 (5)
C12	0.0124 (7)	0.0136 (6)	0.0107 (6)	0.0030 (5)	0.0001 (5)	0.0004 (5)
C13	0.0144 (7)	0.0102 (6)	0.0103 (6)	−0.0020 (5)	0.0020 (5)	−0.0010 (4)
C14	0.0090 (6)	0.0089 (6)	0.0119 (6)	0.0024 (5)	0.0018 (5)	−0.0011 (4)
C15	0.0112 (7)	0.0088 (6)	0.0166 (6)	0.0009 (5)	0.0038 (5)	0.0007 (5)
C16	0.0113 (7)	0.0112 (6)	0.0099 (6)	−0.0002 (5)	0.0000 (5)	−0.0002 (4)
O6	0.0170 (6)	0.0142 (5)	0.0227 (5)	0.0018 (4)	0.0042 (4)	−0.0004 (4)
O7	0.0191 (6)	0.0095 (5)	0.0231 (5)	−0.0008 (4)	0.0032 (4)	0.0001 (4)

Geometric parameters (Å, º)

O1—C10	1.2542 (16)	C3—C4	1.5216 (19)
O2—C10	1.2520 (16)	C3—H3A	0.9900
O3—C12	1.2374 (16)	C3—H3B	0.9900
O4—C14	1.2436 (16)	C4—H4A	0.9900
O5—C16	1.2352 (16)	C4—H4B	0.9900
N1—C8	1.4994 (16)	C5—C6	1.5262 (18)
N1—C9	1.4995 (17)	C5—H5A	0.9900
N1—C1	1.5054 (17)	C5—H5B	0.9900
N1—H1N	0.897 (17)	C6—H6A	0.9900
N2—C11	1.4581 (17)	C6—H6B	0.9900
N2—C3	1.4654 (16)	C7—C8	1.5194 (19)
N2—C2	1.4659 (16)	C7—H7A	0.9900
N3—C4	1.4669 (16)	C7—H7B	0.9900
N3—C13	1.4674 (16)	C8—H8A	0.9900
N3—C5	1.4737 (17)	C8—H8B	0.9900
N4—C15	1.4518 (17)	C9—C10	1.5333 (18)
N4—C7	1.4597 (17)	C9—H9A	0.9900
N4—C6	1.4664 (17)	C9—H9B	0.9900
N5—C12	1.3218 (18)	C11—C12	1.5212 (19)
N5—H51N	0.868 (13)	C11—H11A	0.9900
N5—H52N	0.873 (13)	C11—H11B	0.9900
N6—C14	1.3315 (17)	C13—C14	1.5074 (18)
N6—H61N	0.872 (12)	C13—H13A	0.9900
N6—H62N	0.885 (13)	C13—H13B	0.9900
N7—C16	1.3313 (18)	C15—C16	1.5257 (18)
N7—H71N	0.896 (13)	C15—H15A	0.9900
N7—H72N	0.886 (13)	C15—H15B	0.9900
C1—C2	1.5115 (18)	O6—H61	0.871 (14)
C1—H1A	0.9900	O6—H62	0.860 (14)
C1—H1B	0.9900	O7—H71	0.883 (14)
C2—H2A	0.9900	O7—H72	0.862 (14)
C2—H2B	0.9900
C8—N1—C9	113.07 (10)	N4—C6—H6A	108.9
C8—N1—C1	111.38 (10)	C5—C6—H6A	108.9
C9—N1—C1	109.38 (10)	N4—C6—H6B	108.9
C8—N1—H1N	107.2 (10)	C5—C6—H6B	108.9
C9—N1—H1N	107.1 (10)	H6A—C6—H6B	107.7
C1—N1—H1N	108.5 (10)	N4—C7—C8	110.59 (10)
C11—N2—C3	110.57 (10)	N4—C7—H7A	109.5
C11—N2—C2	111.26 (10)	C8—C7—H7A	109.5
C3—N2—C2	112.12 (10)	N4—C7—H7B	109.5
C4—N3—C13	109.76 (10)	C8—C7—H7B	109.5
C4—N3—C5	110.45 (10)	H7A—C7—H7B	108.1
C13—N3—C5	108.94 (10)	N1—C8—C7	111.13 (10)
C15—N4—C7	114.70 (10)	N1—C8—H8A	109.4
C15—N4—C6	116.03 (11)	C7—C8—H8A	109.4
C7—N4—C6	113.71 (10)	N1—C8—H8B	109.4
C12—N5—H51N	120.0 (11)	C7—C8—H8B	109.4
C12—N5—H52N	119.1 (11)	H8A—C8—H8B	108.0
H51N—N5—H52N	120.3 (16)	N1—C9—C10	109.58 (10)
C14—N6—H61N	117.7 (11)	N1—C9—H9A	109.8
C14—N6—H62N	121.1 (11)	C10—C9—H9A	109.8
H61N—N6—H62N	121.2 (16)	N1—C9—H9B	109.8
C16—N7—H71N	118.7 (11)	C10—C9—H9B	109.8
C16—N7—H72N	117.9 (11)	H9A—C9—H9B	108.2
H71N—N7—H72N	123.0 (16)	O2—C10—O1	127.75 (12)
N1—C1—C2	112.03 (11)	O2—C10—C9	116.75 (11)
N1—C1—H1A	109.2	O1—C10—C9	115.47 (11)
C2—C1—H1A	109.2	N2—C11—C12	113.71 (11)
N1—C1—H1B	109.2	N2—C11—H11A	108.8
C2—C1—H1B	109.2	C12—C11—H11A	108.8
H1A—C1—H1B	107.9	N2—C11—H11B	108.8
N2—C2—C1	110.80 (11)	C12—C11—H11B	108.8
N2—C2—H2A	109.5	H11A—C11—H11B	107.7
C1—C2—H2A	109.5	O3—C12—N5	123.94 (13)
N2—C2—H2B	109.5	O3—C12—C11	119.46 (12)
C1—C2—H2B	109.5	N5—C12—C11	116.59 (12)
H2A—C2—H2B	108.1	N3—C13—C14	112.37 (10)
N2—C3—C4	113.69 (10)	N3—C13—H13A	109.1
N2—C3—H3A	108.8	C14—C13—H13A	109.1
C4—C3—H3A	108.8	N3—C13—H13B	109.1
N2—C3—H3B	108.8	C14—C13—H13B	109.1
C4—C3—H3B	108.8	H13A—C13—H13B	107.9
H3A—C3—H3B	107.7	O4—C14—N6	122.93 (12)
N3—C4—C3	113.93 (11)	O4—C14—C13	120.27 (12)
N3—C4—H4A	108.8	N6—C14—C13	116.80 (12)
C3—C4—H4A	108.8	N4—C15—C16	118.15 (11)
N3—C4—H4B	108.8	N4—C15—H15A	107.8
C3—C4—H4B	108.8	C16—C15—H15A	107.8
H4A—C4—H4B	107.7	N4—C15—H15B	107.8
N3—C5—C6	113.74 (11)	C16—C15—H15B	107.8
N3—C5—H5A	108.8	H15A—C15—H15B	107.1
C6—C5—H5A	108.8	O5—C16—N7	122.69 (13)
N3—C5—H5B	108.8	O5—C16—C15	122.80 (12)
C6—C5—H5B	108.8	N7—C16—C15	114.51 (12)
H5A—C5—H5B	107.7	H61—O6—H62	103.3 (17)
N4—C6—C5	113.28 (11)	H71—O7—H72	106.6 (17)
C8—N1—C1—C2	−81.10 (13)	C1—N1—C8—C7	168.84 (10)
C9—N1—C1—C2	153.18 (11)	N4—C7—C8—N1	−49.07 (14)
C11—N2—C2—C1	−82.74 (13)	C8—N1—C9—C10	153.17 (11)
C3—N2—C2—C1	152.85 (11)	C1—N1—C9—C10	−82.08 (13)
N1—C1—C2—N2	−68.85 (14)	N1—C9—C10—O2	146.35 (11)
C11—N2—C3—C4	162.15 (11)	N1—C9—C10—O1	−35.40 (16)
C2—N2—C3—C4	−73.06 (14)	C3—N2—C11—C12	−74.07 (14)
C13—N3—C4—C3	−70.27 (14)	C2—N2—C11—C12	160.65 (11)
C5—N3—C4—C3	169.59 (10)	N2—C11—C12—O3	146.20 (13)
N2—C3—C4—N3	−57.67 (14)	N2—C11—C12—N5	−35.08 (17)
C4—N3—C5—C6	−78.61 (13)	C4—N3—C13—C14	171.90 (11)
C13—N3—C5—C6	160.77 (11)	C5—N3—C13—C14	−67.05 (14)
C15—N4—C6—C5	−66.53 (14)	N3—C13—C14—O4	142.24 (12)
C7—N4—C6—C5	157.22 (11)	N3—C13—C14—N6	−38.36 (16)
N3—C5—C6—N4	−59.22 (15)	C7—N4—C15—C16	63.41 (16)
C15—N4—C7—C8	140.88 (11)	C6—N4—C15—C16	−72.42 (15)
C6—N4—C7—C8	−82.26 (13)	N4—C15—C16—O5	−0.95 (19)
C9—N1—C8—C7	−67.51 (14)	N4—C15—C16—N7	179.54 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.897 (17)	2.234 (16)	2.7022 (15)	112.1 (13)
N5—H51N···O6	0.87 (1)	2.21 (1)	3.0156 (16)	154 (2)
N5—H52N···O1	0.87 (1)	2.06 (1)	2.8744 (15)	154 (2)
N6—H61N···O4^i	0.87 (1)	2.27 (1)	2.9746 (15)	138 (1)
N6—H61N···O7	0.87 (1)	2.54 (1)	3.1950 (16)	133 (1)
N6—H62N···O1	0.89 (1)	2.16 (1)	2.9394 (15)	147 (1)
N7—H71N···O2^ii	0.90 (1)	2.10 (1)	2.9901 (16)	174 (2)
N7—H72N···O7	0.89 (1)	2.02 (1)	2.8861 (16)	165 (2)
O6—H61···O3^iii	0.87 (1)	1.90 (1)	2.7683 (15)	174 (2)
O6—H62···O4^i	0.86 (1)	1.96 (2)	2.7982 (15)	163 (2)
O7—H71···O6^i	0.88 (1)	1.96 (1)	2.8372 (16)	177 (2)
O7—H72···O5^iv	0.86 (1)	1.88 (1)	2.7458 (14)	178 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1/2, y−1/2, −z+3/2.

4,7,10-Tris(carbamoylmethyl)-1-(carboxylatomethyl)-1,4,7,10-tetraazacyclododecan-1-ium dihydrate (Jurek2_90K)

Crystal data

C16H31N7O5·2H2O	F(000) = 944
Mr = 437.51	Dx = 1.334 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.8070 (6) Å	Cell parameters from 9945 reflections
b = 14.9505 (8) Å	θ = 3.7–36.6°
c = 16.6376 (10) Å	µ = 0.11 mm^−1
β = 95.903 (4)°	T = 90 K
V = 2179.0 (2) Å^3	Prism, colourless
Z = 4	0.44 × 0.33 × 0.30 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	19751 independent reflections
Radiation source: fine-focus sealed tube	18244 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 36.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.892, Tmax = 0.928	k = −24→24
54344 measured reflections	l = −27→27

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.1292P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.47 e Å^−3
19751 reflections	Δρmin = −0.22 e Å^−3
608 parameters	Absolute structure: Refined as an inversion twin
96 restraints	Absolute structure parameter: 0.5 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.58754 (9)	0.49100 (6)	0.37387 (5)	0.01231 (14)
O2A	0.69538 (10)	0.35482 (7)	0.36765 (6)	0.01694 (16)
O3A	0.81747 (10)	0.60008 (7)	0.12696 (5)	0.01430 (15)
O4A	0.34203 (12)	0.85434 (7)	0.35313 (5)	0.01980 (18)
O5A	0.21503 (10)	0.51130 (7)	0.59212 (5)	0.01647 (16)
N1A	0.80918 (10)	0.54434 (7)	0.48743 (5)	0.00982 (15)
N2A	0.84069 (11)	0.66219 (7)	0.33772 (5)	0.01149 (15)
N3A	0.57947 (11)	0.73200 (7)	0.41763 (6)	0.01237 (16)
N4A	0.57205 (10)	0.62859 (7)	0.57086 (6)	0.01091 (15)
N5A	0.65987 (11)	0.56396 (8)	0.22163 (6)	0.01345 (17)
N6A	0.26469 (12)	0.75745 (8)	0.25260 (6)	0.01596 (18)
N7A	0.36030 (11)	0.51552 (8)	0.48792 (6)	0.01404 (17)
C1A	0.94804 (12)	0.56003 (9)	0.44324 (7)	0.01316 (19)
H11A	0.9484	0.5164	0.3985	0.016*
H12A	1.0412	0.5500	0.4808	0.016*
C2A	0.95135 (12)	0.65394 (9)	0.40928 (6)	0.01347 (19)
H21A	0.9266	0.6975	0.4508	0.016*
H22A	1.0550	0.6675	0.3946	0.016*
C3A	0.78260 (14)	0.75388 (8)	0.32370 (7)	0.01495 (19)
H31A	0.7143	0.7547	0.2726	0.018*
H32A	0.8700	0.7937	0.3166	0.018*
C4A	0.69564 (14)	0.79207 (8)	0.39068 (7)	0.01518 (19)
H41A	0.7697	0.8069	0.4376	0.018*
H42A	0.6456	0.8484	0.3712	0.018*
C5A	0.51990 (13)	0.76605 (8)	0.49151 (7)	0.01390 (19)
H51A	0.4099	0.7516	0.4899	0.017*
H52A	0.5309	0.8319	0.4938	0.017*
C6A	0.60531 (12)	0.72487 (8)	0.56666 (6)	0.01231 (18)
H6A1	0.7164	0.7338	0.5654	0.015*
H6A2	0.5745	0.7551	0.6154	0.015*
C7A	0.69450 (12)	0.57837 (8)	0.61651 (6)	0.01204 (17)
H7A1	0.6589	0.5166	0.6251	0.014*
H7A2	0.7182	0.6065	0.6702	0.014*
C8A	0.83940 (12)	0.57465 (8)	0.57386 (6)	0.01134 (17)
H81A	0.8867	0.6348	0.5752	0.014*
H82A	0.9128	0.5331	0.6034	0.014*
C9A	0.76592 (13)	0.44760 (8)	0.48187 (6)	0.01278 (18)
H91A	0.7023	0.4323	0.5256	0.015*
H92A	0.8590	0.4101	0.4885	0.015*
C10A	0.67678 (12)	0.42863 (8)	0.39966 (6)	0.01149 (17)
C11A	0.90551 (12)	0.63008 (9)	0.26570 (7)	0.01397 (19)
H11C	0.9772	0.5806	0.2815	0.017*
H11D	0.9651	0.6791	0.2442	0.017*
C12A	0.78799 (12)	0.59713 (8)	0.19860 (6)	0.01049 (17)
C13A	0.46107 (13)	0.70715 (8)	0.35451 (7)	0.01365 (18)
H13A	0.3987	0.6594	0.3760	0.016*
H13B	0.5111	0.6810	0.3093	0.016*
C14A	0.35271 (13)	0.78096 (8)	0.31996 (6)	0.01257 (18)
C15A	0.42625 (13)	0.61245 (9)	0.60394 (7)	0.01433 (19)
H15A	0.3680	0.6692	0.6019	0.017*
H15B	0.4478	0.5954	0.6615	0.017*
C16A	0.32642 (12)	0.54065 (8)	0.56097 (6)	0.01175 (17)
H1N	0.732 (2)	0.5723 (13)	0.4629 (11)	0.014*
H51N	0.5839 (18)	0.5444 (13)	0.1865 (10)	0.014*
H52N	0.648 (2)	0.5526 (13)	0.2725 (9)	0.014*
H61N	0.1965 (19)	0.7940 (12)	0.2302 (11)	0.014*
H62N	0.283 (2)	0.7111 (11)	0.2245 (10)	0.014*
H71N	0.300 (2)	0.4760 (12)	0.4620 (11)	0.014*
H72N	0.4421 (18)	0.5384 (13)	0.4691 (11)	0.014*
O1B	0.40048 (9)	0.50904 (6)	0.11485 (5)	0.01242 (14)
O2B	0.30847 (10)	0.64890 (7)	0.12055 (6)	0.01742 (17)
O3B	0.17071 (10)	0.40471 (7)	0.36523 (5)	0.01655 (17)
O4B	0.59382 (13)	0.14222 (7)	0.13144 (7)	0.0254 (2)
O5B	0.76517 (10)	0.49399 (7)	−0.10486 (5)	0.01651 (16)
N1B	0.17151 (10)	0.46403 (7)	0.00192 (5)	0.01104 (15)
N2B	0.13082 (11)	0.34790 (7)	0.15296 (6)	0.01283 (16)
N3B	0.39299 (11)	0.28116 (8)	0.07169 (6)	0.01431 (17)
N4B	0.40031 (11)	0.38440 (7)	−0.08500 (6)	0.01380 (17)
N5B	0.32276 (11)	0.43972 (8)	0.26787 (6)	0.01374 (17)
N6B	0.71536 (13)	0.23068 (8)	0.22815 (7)	0.01752 (19)
N7B	0.62496 (11)	0.48761 (8)	0.00158 (6)	0.01353 (17)
C1B	0.03397 (12)	0.45459 (9)	0.04841 (7)	0.01432 (19)
H11B	−0.0592	0.4691	0.0123	0.017*
H12B	0.0421	0.4982	0.0934	0.017*
C2B	0.01869 (13)	0.36156 (9)	0.08219 (7)	0.0150 (2)
H21B	−0.0857	0.3532	0.0980	0.018*
H22B	0.0353	0.3167	0.0402	0.018*
C3B	0.18465 (15)	0.25517 (9)	0.16200 (7)	0.0171 (2)
H31B	0.0956	0.2158	0.1666	0.020*
H32B	0.2525	0.2502	0.2131	0.020*
C4B	0.27039 (15)	0.22122 (9)	0.09305 (8)	0.0173 (2)
H41B	0.3153	0.1621	0.1083	0.021*
H42B	0.1965	0.2125	0.0447	0.021*
C5B	0.45587 (14)	0.24890 (9)	−0.00189 (7)	0.0166 (2)
H51B	0.4489	0.1828	−0.0042	0.020*
H52B	0.5650	0.2656	0.0004	0.020*
C6B	0.37047 (13)	0.28827 (9)	−0.07771 (7)	0.01462 (19)
H6B1	0.4020	0.2569	−0.1257	0.018*
H6B2	0.2596	0.2786	−0.0764	0.018*
C7B	0.27345 (14)	0.43155 (8)	−0.13068 (7)	0.01434 (19)
H7B1	0.2470	0.4007	−0.1829	0.017*
H7B2	0.3059	0.4932	−0.1423	0.017*
C8B	0.13300 (13)	0.43537 (8)	−0.08460 (6)	0.01313 (18)
H81B	0.0584	0.4779	−0.1119	0.016*
H82B	0.0845	0.3756	−0.0857	0.016*
C9B	0.22696 (14)	0.55861 (8)	0.00672 (7)	0.01411 (19)
H91B	0.1390	0.6001	0.0002	0.017*
H92B	0.2921	0.5704	−0.0372	0.017*
C10B	0.31846 (12)	0.57383 (8)	0.08866 (6)	0.01211 (18)
C11B	0.07201 (13)	0.37829 (10)	0.22720 (7)	0.0165 (2)
H11E	0.0126	0.3291	0.2487	0.020*
H11F	0.0013	0.4289	0.2141	0.020*
C12B	0.19538 (12)	0.40801 (8)	0.29284 (6)	0.01203 (18)
C13B	0.51162 (14)	0.29628 (9)	0.13796 (7)	0.01515 (19)
H13C	0.4626	0.3191	0.1848	0.018*
H13D	0.5802	0.3439	0.1215	0.018*
C14B	0.60936 (14)	0.21520 (9)	0.16576 (7)	0.01523 (19)
C15B	0.54429 (14)	0.40095 (10)	−0.11916 (8)	0.0195 (2)
H15C	0.5205	0.4235	−0.1750	0.023*
H15D	0.5981	0.3432	−0.1226	0.023*
C16B	0.65234 (12)	0.46660 (8)	−0.07318 (6)	0.01168 (17)
H11N	0.242 (2)	0.4295 (13)	0.0248 (11)	0.014*
H53N	0.3971 (18)	0.4546 (14)	0.3023 (10)	0.014*
H54N	0.329 (2)	0.4431 (13)	0.2161 (9)	0.014*
H63N	0.7750 (19)	0.1869 (11)	0.2433 (11)	0.014*
H64N	0.705 (2)	0.2732 (11)	0.2582 (10)	0.014*
H73N	0.683 (2)	0.5241 (12)	0.0296 (11)	0.014*
H74N	0.5426 (18)	0.4696 (13)	0.0206 (11)	0.014*
O6A	0.12209 (11)	0.94241 (8)	0.24370 (6)	0.01890 (18)
H61A	0.194 (2)	0.9312 (15)	0.2816 (11)	0.028*
H62A	0.165 (2)	0.9610 (16)	0.2027 (11)	0.028*
O6B	0.90130 (13)	0.07386 (9)	0.26895 (6)	0.0250 (2)
H61B	0.975 (2)	0.0366 (15)	0.2543 (14)	0.037*
H62B	0.853 (3)	0.0504 (18)	0.3095 (12)	0.037*
O7B	−0.02579 (11)	0.23159 (7)	−0.08592 (6)	0.01882 (17)
H71B	−0.117 (2)	0.2095 (16)	−0.0929 (13)	0.028*
H72B	0.037 (2)	0.1904 (14)	−0.0983 (13)	0.028*
O7A	1.01919 (12)	0.77567 (7)	0.57597 (6)	0.02094 (19)
H71A	1.109 (2)	0.7927 (17)	0.5929 (14)	0.031*
H72A	0.966 (2)	0.8147 (14)	0.5979 (13)	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0106 (3)	0.0136 (4)	0.0124 (3)	−0.0004 (3)	−0.0005 (2)	0.0010 (3)
O2A	0.0175 (4)	0.0151 (4)	0.0176 (4)	0.0005 (3)	−0.0011 (3)	−0.0062 (3)
O3A	0.0147 (3)	0.0187 (4)	0.0098 (3)	−0.0016 (3)	0.0028 (3)	−0.0028 (3)
O4A	0.0294 (5)	0.0146 (4)	0.0140 (3)	0.0085 (3)	−0.0044 (3)	−0.0045 (3)
O5A	0.0114 (3)	0.0210 (4)	0.0176 (4)	−0.0021 (3)	0.0044 (3)	0.0011 (3)
N1A	0.0091 (3)	0.0101 (4)	0.0098 (3)	0.0004 (3)	−0.0010 (3)	−0.0007 (3)
N2A	0.0122 (3)	0.0138 (4)	0.0083 (3)	−0.0014 (3)	0.0004 (3)	−0.0018 (3)
N3A	0.0139 (4)	0.0119 (4)	0.0110 (3)	0.0002 (3)	−0.0003 (3)	−0.0010 (3)
N4A	0.0093 (3)	0.0105 (4)	0.0129 (3)	0.0000 (3)	0.0010 (3)	−0.0007 (3)
N5A	0.0116 (4)	0.0185 (5)	0.0102 (3)	−0.0027 (3)	0.0006 (3)	−0.0007 (3)
N6A	0.0171 (4)	0.0152 (5)	0.0147 (4)	0.0022 (3)	−0.0027 (3)	−0.0030 (3)
N7A	0.0111 (4)	0.0175 (5)	0.0137 (4)	−0.0019 (3)	0.0022 (3)	−0.0026 (3)
C1A	0.0089 (4)	0.0183 (5)	0.0124 (4)	0.0013 (3)	0.0014 (3)	−0.0009 (4)
C2A	0.0119 (4)	0.0176 (5)	0.0106 (4)	−0.0046 (4)	−0.0002 (3)	−0.0015 (4)
C3A	0.0206 (5)	0.0118 (5)	0.0127 (4)	−0.0027 (4)	0.0026 (4)	0.0009 (4)
C4A	0.0188 (5)	0.0117 (5)	0.0151 (4)	−0.0013 (4)	0.0023 (4)	−0.0009 (4)
C5A	0.0159 (4)	0.0136 (5)	0.0121 (4)	0.0040 (4)	0.0007 (3)	−0.0008 (4)
C6A	0.0130 (4)	0.0109 (5)	0.0126 (4)	0.0000 (3)	−0.0003 (3)	−0.0014 (4)
C7A	0.0133 (4)	0.0125 (5)	0.0104 (4)	0.0010 (3)	0.0014 (3)	0.0004 (3)
C8A	0.0108 (4)	0.0139 (5)	0.0089 (3)	0.0009 (3)	−0.0009 (3)	−0.0015 (3)
C9A	0.0167 (4)	0.0099 (5)	0.0111 (4)	0.0000 (3)	−0.0016 (3)	0.0000 (3)
C10A	0.0100 (4)	0.0133 (5)	0.0110 (4)	−0.0021 (3)	0.0005 (3)	−0.0008 (3)
C11A	0.0098 (4)	0.0213 (6)	0.0109 (4)	−0.0027 (4)	0.0013 (3)	−0.0035 (4)
C12A	0.0101 (4)	0.0115 (5)	0.0098 (4)	0.0008 (3)	0.0008 (3)	−0.0014 (3)
C13A	0.0156 (4)	0.0106 (5)	0.0141 (4)	0.0028 (3)	−0.0020 (3)	−0.0026 (4)
C14A	0.0140 (4)	0.0132 (5)	0.0104 (4)	0.0025 (3)	0.0008 (3)	−0.0009 (3)
C15A	0.0122 (4)	0.0171 (5)	0.0142 (4)	−0.0009 (4)	0.0035 (3)	−0.0031 (4)
C16A	0.0090 (4)	0.0137 (5)	0.0125 (4)	0.0012 (3)	0.0009 (3)	0.0013 (4)
O1B	0.0112 (3)	0.0137 (4)	0.0122 (3)	0.0001 (3)	0.0003 (2)	−0.0009 (3)
O2B	0.0161 (4)	0.0158 (4)	0.0195 (4)	0.0015 (3)	−0.0017 (3)	−0.0085 (3)
O3B	0.0167 (4)	0.0224 (5)	0.0109 (3)	−0.0046 (3)	0.0034 (3)	−0.0033 (3)
O4B	0.0330 (5)	0.0169 (5)	0.0242 (4)	0.0103 (4)	−0.0072 (4)	−0.0076 (4)
O5B	0.0118 (3)	0.0225 (5)	0.0158 (3)	−0.0038 (3)	0.0040 (3)	−0.0017 (3)
N1B	0.0096 (3)	0.0124 (4)	0.0106 (3)	0.0008 (3)	−0.0014 (3)	−0.0025 (3)
N2B	0.0124 (4)	0.0157 (4)	0.0102 (3)	−0.0011 (3)	0.0004 (3)	−0.0028 (3)
N3B	0.0140 (4)	0.0154 (4)	0.0133 (4)	0.0020 (3)	0.0000 (3)	−0.0035 (3)
N4B	0.0109 (3)	0.0158 (4)	0.0151 (4)	−0.0034 (3)	0.0034 (3)	−0.0040 (3)
N5B	0.0113 (4)	0.0191 (5)	0.0108 (3)	−0.0028 (3)	0.0007 (3)	−0.0012 (3)
N6B	0.0187 (4)	0.0159 (5)	0.0169 (4)	0.0039 (4)	−0.0034 (3)	−0.0008 (4)
N7B	0.0110 (4)	0.0176 (5)	0.0121 (3)	−0.0019 (3)	0.0015 (3)	−0.0035 (3)
C1B	0.0098 (4)	0.0196 (5)	0.0134 (4)	0.0026 (4)	0.0006 (3)	−0.0023 (4)
C2B	0.0116 (4)	0.0201 (6)	0.0131 (4)	−0.0037 (4)	−0.0001 (3)	−0.0031 (4)
C3B	0.0213 (5)	0.0145 (5)	0.0156 (4)	−0.0023 (4)	0.0032 (4)	0.0005 (4)
C4B	0.0206 (5)	0.0131 (5)	0.0181 (5)	−0.0007 (4)	0.0016 (4)	−0.0039 (4)
C5B	0.0159 (4)	0.0186 (6)	0.0149 (4)	0.0056 (4)	0.0000 (4)	−0.0045 (4)
C6B	0.0140 (4)	0.0155 (5)	0.0140 (4)	0.0002 (4)	−0.0004 (3)	−0.0040 (4)
C7B	0.0179 (5)	0.0138 (5)	0.0114 (4)	−0.0021 (4)	0.0021 (3)	−0.0020 (4)
C8B	0.0137 (4)	0.0149 (5)	0.0102 (4)	0.0000 (4)	−0.0017 (3)	−0.0024 (4)
C9B	0.0179 (4)	0.0108 (5)	0.0129 (4)	0.0001 (4)	−0.0022 (3)	−0.0023 (4)
C10B	0.0108 (4)	0.0134 (5)	0.0121 (4)	−0.0011 (3)	0.0009 (3)	−0.0027 (3)
C11B	0.0104 (4)	0.0261 (6)	0.0131 (4)	−0.0033 (4)	0.0020 (3)	−0.0065 (4)
C12B	0.0108 (4)	0.0142 (5)	0.0112 (4)	−0.0007 (3)	0.0014 (3)	−0.0028 (4)
C13B	0.0167 (4)	0.0133 (5)	0.0147 (4)	0.0037 (4)	−0.0021 (3)	−0.0032 (4)
C14B	0.0165 (5)	0.0155 (5)	0.0137 (4)	0.0041 (4)	0.0011 (3)	−0.0009 (4)
C15B	0.0150 (5)	0.0274 (7)	0.0170 (5)	−0.0080 (4)	0.0061 (4)	−0.0101 (5)
C16B	0.0089 (4)	0.0144 (5)	0.0116 (4)	0.0002 (3)	0.0004 (3)	−0.0008 (4)
O6A	0.0176 (4)	0.0258 (5)	0.0132 (3)	0.0070 (3)	0.0013 (3)	0.0019 (3)
O6B	0.0273 (5)	0.0303 (6)	0.0177 (4)	0.0145 (4)	0.0041 (4)	0.0071 (4)
O7B	0.0157 (4)	0.0173 (4)	0.0236 (4)	−0.0043 (3)	0.0027 (3)	−0.0065 (3)
O7A	0.0192 (4)	0.0197 (5)	0.0242 (4)	−0.0046 (3)	0.0035 (3)	−0.0080 (4)

Geometric parameters (Å, º)

O1A—C10A	1.2657 (14)	O5B—C16B	1.2413 (13)
O2A—C10A	1.2434 (15)	N1B—C9B	1.4954 (16)
O3A—C12A	1.2464 (13)	N1B—C8B	1.5068 (14)
O4A—C14A	1.2360 (15)	N1B—C1B	1.5095 (15)
O5A—C16A	1.2362 (14)	N1B—H11N	0.865 (17)
N1A—C9A	1.4960 (16)	N2B—C11B	1.4601 (15)
N1A—C8A	1.5050 (14)	N2B—C3B	1.4679 (17)
N1A—C1A	1.5087 (14)	N2B—C2B	1.4711 (15)
N1A—H1N	0.865 (16)	N3B—C13B	1.4565 (15)
N2A—C11A	1.4605 (14)	N3B—C4B	1.4744 (17)
N2A—C2A	1.4641 (14)	N3B—C5B	1.4757 (16)
N2A—C3A	1.4734 (16)	N4B—C15B	1.4630 (15)
N3A—C13A	1.4501 (15)	N4B—C7B	1.4656 (16)
N3A—C4A	1.4658 (16)	N4B—C6B	1.4683 (17)
N3A—C5A	1.4759 (15)	N5B—C12B	1.3234 (15)
N4A—C7A	1.4613 (15)	N5B—H53N	0.854 (14)
N4A—C15A	1.4680 (14)	N5B—H54N	0.870 (14)
N4A—C6A	1.4720 (16)	N6B—C14B	1.3428 (16)
N5A—C12A	1.3248 (14)	N6B—H63N	0.861 (14)
N5A—H51N	0.891 (14)	N6B—H64N	0.819 (14)
N5A—H52N	0.880 (14)	N7B—C16B	1.3287 (14)
N6A—C14A	1.3422 (15)	N7B—H73N	0.851 (14)
N6A—H61N	0.867 (14)	N7B—H74N	0.864 (14)
N6A—H62N	0.862 (14)	C1B—C2B	1.5113 (19)
N7A—C16A	1.3349 (15)	C1B—H11B	0.9900
N7A—H71N	0.875 (14)	C1B—H12B	0.9900
N7A—H72N	0.884 (14)	C2B—H21B	0.9900
C1A—C2A	1.5148 (18)	C2B—H22B	0.9900
C1A—H11A	0.9900	C3B—C4B	1.5238 (18)
C1A—H12A	0.9900	C3B—H31B	0.9900
C2A—H21A	0.9900	C3B—H32B	0.9900
C2A—H22A	0.9900	C4B—H41B	0.9900
C3A—C4A	1.5264 (17)	C4B—H42B	0.9900
C3A—H31A	0.9900	C5B—C6B	1.5193 (17)
C3A—H32A	0.9900	C5B—H51B	0.9900
C4A—H41A	0.9900	C5B—H52B	0.9900
C4A—H42A	0.9900	C6B—H6B1	0.9900
C5A—C6A	1.5213 (16)	C6B—H6B2	0.9900
C5A—H51A	0.9900	C7B—C8B	1.5219 (16)
C5A—H52A	0.9900	C7B—H7B1	0.9900
C6A—H6A1	0.9900	C7B—H7B2	0.9900
C6A—H6A2	0.9900	C8B—H81B	0.9900
C7A—C8A	1.5237 (15)	C8B—H82B	0.9900
C7A—H7A1	0.9900	C9B—C10B	1.5277 (15)
C7A—H7A2	0.9900	C9B—H91B	0.9900
C8A—H81A	0.9900	C9B—H92B	0.9900
C8A—H82A	0.9900	C11B—C12B	1.5254 (15)
C9A—C10A	1.5319 (15)	C11B—H11E	0.9900
C9A—H91A	0.9900	C11B—H11F	0.9900
C9A—H92A	0.9900	C13B—C14B	1.5305 (17)
C11A—C12A	1.5241 (15)	C13B—H13C	0.9900
C11A—H11C	0.9900	C13B—H13D	0.9900
C11A—H11D	0.9900	C15B—C16B	1.5180 (17)
C13A—C14A	1.5317 (16)	C15B—H15C	0.9900
C13A—H13A	0.9900	C15B—H15D	0.9900
C13A—H13B	0.9900	O6A—H61A	0.861 (16)
C15A—C16A	1.5189 (17)	O6A—H62A	0.862 (16)
C15A—H15A	0.9900	O6B—H61B	0.909 (16)
C15A—H15B	0.9900	O6B—H62B	0.904 (17)
O1B—C10B	1.2590 (15)	O7B—H71B	0.861 (16)
O2B—C10B	1.2484 (15)	O7B—H72B	0.868 (16)
O3B—C12B	1.2466 (13)	O7A—H71A	0.849 (17)
O4B—C14B	1.2325 (17)	O7A—H72A	0.853 (17)
C9A—N1A—C8A	111.66 (9)	C8B—N1B—C1B	110.45 (8)
C9A—N1A—C1A	109.52 (9)	C9B—N1B—H11N	109.0 (13)
C8A—N1A—C1A	110.26 (8)	C8B—N1B—H11N	109.3 (13)
C9A—N1A—H1N	104.7 (14)	C1B—N1B—H11N	107.2 (12)
C8A—N1A—H1N	111.0 (13)	C11B—N2B—C3B	110.26 (10)
C1A—N1A—H1N	109.6 (12)	C11B—N2B—C2B	111.50 (9)
C11A—N2A—C2A	110.84 (9)	C3B—N2B—C2B	113.34 (10)
C11A—N2A—C3A	109.54 (9)	C13B—N3B—C4B	113.45 (10)
C2A—N2A—C3A	113.48 (9)	C13B—N3B—C5B	112.18 (9)
C13A—N3A—C4A	114.08 (9)	C4B—N3B—C5B	110.36 (10)
C13A—N3A—C5A	113.63 (9)	C15B—N4B—C7B	111.23 (10)
C4A—N3A—C5A	111.26 (10)	C15B—N4B—C6B	111.55 (10)
C7A—N4A—C15A	110.36 (9)	C7B—N4B—C6B	112.35 (9)
C7A—N4A—C6A	112.79 (9)	C12B—N5B—H53N	119.9 (12)
C15A—N4A—C6A	111.38 (9)	C12B—N5B—H54N	118.0 (13)
C12A—N5A—H51N	122.5 (12)	H53N—N5B—H54N	122.1 (17)
C12A—N5A—H52N	122.8 (12)	C14B—N6B—H63N	116.7 (13)
H51N—N5A—H52N	114.2 (17)	C14B—N6B—H64N	119.7 (13)
C14A—N6A—H61N	120.5 (13)	H63N—N6B—H64N	120.8 (18)
C14A—N6A—H62N	122.5 (12)	C16B—N7B—H73N	120.5 (13)
H61N—N6A—H62N	115.9 (18)	C16B—N7B—H74N	120.6 (13)
C16A—N7A—H71N	117.4 (12)	H73N—N7B—H74N	118.4 (18)
C16A—N7A—H72N	118.7 (12)	N1B—C1B—C2B	112.54 (10)
H71N—N7A—H72N	123.9 (17)	N1B—C1B—H11B	109.1
N1A—C1A—C2A	111.94 (9)	C2B—C1B—H11B	109.1
N1A—C1A—H11A	109.2	N1B—C1B—H12B	109.1
C2A—C1A—H11A	109.2	C2B—C1B—H12B	109.1
N1A—C1A—H12A	109.2	H11B—C1B—H12B	107.8
C2A—C1A—H12A	109.2	N2B—C2B—C1B	110.32 (9)
H11A—C1A—H12A	107.9	N2B—C2B—H21B	109.6
N2A—C2A—C1A	110.16 (9)	C1B—C2B—H21B	109.6
N2A—C2A—H21A	109.6	N2B—C2B—H22B	109.6
C1A—C2A—H21A	109.6	C1B—C2B—H22B	109.6
N2A—C2A—H22A	109.6	H21B—C2B—H22B	108.1
C1A—C2A—H22A	109.6	N2B—C3B—C4B	114.66 (10)
H21A—C2A—H22A	108.1	N2B—C3B—H31B	108.6
N2A—C3A—C4A	115.12 (9)	C4B—C3B—H31B	108.6
N2A—C3A—H31A	108.5	N2B—C3B—H32B	108.6
C4A—C3A—H31A	108.5	C4B—C3B—H32B	108.6
N2A—C3A—H32A	108.5	H31B—C3B—H32B	107.6
C4A—C3A—H32A	108.5	N3B—C4B—C3B	114.26 (10)
H31A—C3A—H32A	107.5	N3B—C4B—H41B	108.7
N3A—C4A—C3A	114.37 (10)	C3B—C4B—H41B	108.7
N3A—C4A—H41A	108.7	N3B—C4B—H42B	108.7
C3A—C4A—H41A	108.7	C3B—C4B—H42B	108.7
N3A—C4A—H42A	108.7	H41B—C4B—H42B	107.6
C3A—C4A—H42A	108.7	N3B—C5B—C6B	111.48 (10)
H41A—C4A—H42A	107.6	N3B—C5B—H51B	109.3
N3A—C5A—C6A	110.90 (9)	C6B—C5B—H51B	109.3
N3A—C5A—H51A	109.5	N3B—C5B—H52B	109.3
C6A—C5A—H51A	109.5	C6B—C5B—H52B	109.3
N3A—C5A—H52A	109.5	H51B—C5B—H52B	108.0
C6A—C5A—H52A	109.5	N4B—C6B—C5B	111.74 (10)
H51A—C5A—H52A	108.0	N4B—C6B—H6B1	109.3
N4A—C6A—C5A	110.54 (9)	C5B—C6B—H6B1	109.3
N4A—C6A—H6A1	109.5	N4B—C6B—H6B2	109.3
C5A—C6A—H6A1	109.5	C5B—C6B—H6B2	109.3
N4A—C6A—H6A2	109.5	H6B1—C6B—H6B2	107.9
C5A—C6A—H6A2	109.5	N4B—C7B—C8B	111.87 (9)
H6A1—C6A—H6A2	108.1	N4B—C7B—H7B1	109.2
N4A—C7A—C8A	112.67 (9)	C8B—C7B—H7B1	109.2
N4A—C7A—H7A1	109.1	N4B—C7B—H7B2	109.2
C8A—C7A—H7A1	109.1	C8B—C7B—H7B2	109.2
N4A—C7A—H7A2	109.1	H7B1—C7B—H7B2	107.9
C8A—C7A—H7A2	109.1	N1B—C8B—C7B	112.16 (9)
H7A1—C7A—H7A2	107.8	N1B—C8B—H81B	109.2
N1A—C8A—C7A	112.44 (8)	C7B—C8B—H81B	109.2
N1A—C8A—H81A	109.1	N1B—C8B—H82B	109.2
C7A—C8A—H81A	109.1	C7B—C8B—H82B	109.2
N1A—C8A—H82A	109.1	H81B—C8B—H82B	107.9
C7A—C8A—H82A	109.1	N1B—C9B—C10B	109.14 (9)
H81A—C8A—H82A	107.8	N1B—C9B—H91B	109.9
N1A—C9A—C10A	109.76 (9)	C10B—C9B—H91B	109.9
N1A—C9A—H91A	109.7	N1B—C9B—H92B	109.9
C10A—C9A—H91A	109.7	C10B—C9B—H92B	109.9
N1A—C9A—H92A	109.7	H91B—C9B—H92B	108.3
C10A—C9A—H92A	109.7	O2B—C10B—O1B	127.42 (10)
H91A—C9A—H92A	108.2	O2B—C10B—C9B	117.35 (11)
O2A—C10A—O1A	127.82 (10)	O1B—C10B—C9B	115.18 (10)
O2A—C10A—C9A	117.95 (10)	N2B—C11B—C12B	114.07 (9)
O1A—C10A—C9A	114.18 (10)	N2B—C11B—H11E	108.7
N2A—C11A—C12A	114.45 (9)	C12B—C11B—H11E	108.7
N2A—C11A—H11C	108.6	N2B—C11B—H11F	108.7
C12A—C11A—H11C	108.6	C12B—C11B—H11F	108.7
N2A—C11A—H11D	108.6	H11E—C11B—H11F	107.6
C12A—C11A—H11D	108.6	O3B—C12B—N5B	123.71 (10)
H11C—C11A—H11D	107.6	O3B—C12B—C11B	119.87 (10)
O3A—C12A—N5A	123.86 (10)	N5B—C12B—C11B	116.36 (9)
O3A—C12A—C11A	119.77 (10)	N3B—C13B—C14B	116.31 (10)
N5A—C12A—C11A	116.33 (9)	N3B—C13B—H13C	108.2
N3A—C13A—C14A	117.46 (10)	C14B—C13B—H13C	108.2
N3A—C13A—H13A	107.9	N3B—C13B—H13D	108.2
C14A—C13A—H13A	107.9	C14B—C13B—H13D	108.2
N3A—C13A—H13B	107.9	H13C—C13B—H13D	107.4
C14A—C13A—H13B	107.9	O4B—C14B—N6B	123.09 (12)
H13A—C13A—H13B	107.2	O4B—C14B—C13B	121.93 (11)
O4A—C14A—N6A	122.77 (11)	N6B—C14B—C13B	114.95 (11)
O4A—C14A—C13A	123.02 (10)	N4B—C15B—C16B	115.91 (10)
N6A—C14A—C13A	114.13 (10)	N4B—C15B—H15C	108.3
N4A—C15A—C16A	115.21 (9)	C16B—C15B—H15C	108.3
N4A—C15A—H15A	108.5	N4B—C15B—H15D	108.3
C16A—C15A—H15A	108.5	C16B—C15B—H15D	108.3
N4A—C15A—H15B	108.5	H15C—C15B—H15D	107.4
C16A—C15A—H15B	108.5	O5B—C16B—N7B	123.35 (11)
H15A—C15A—H15B	107.5	O5B—C16B—C15B	119.14 (10)
O5A—C16A—N7A	122.89 (11)	N7B—C16B—C15B	117.38 (10)
O5A—C16A—C15A	119.97 (10)	H61A—O6A—H62A	107 (2)
N7A—C16A—C15A	117.05 (10)	H61B—O6B—H62B	111 (2)
C9B—N1B—C8B	111.11 (9)	H71B—O7B—H72B	108 (2)
C9B—N1B—C1B	109.62 (9)	H71A—O7A—H72A	101 (2)
C9A—N1A—C1A—C2A	150.72 (9)	C9B—N1B—C1B—C2B	−151.25 (9)
C8A—N1A—C1A—C2A	−86.03 (11)	C8B—N1B—C1B—C2B	86.00 (11)
C11A—N2A—C2A—C1A	−83.65 (11)	C11B—N2B—C2B—C1B	86.96 (12)
C3A—N2A—C2A—C1A	152.60 (9)	C3B—N2B—C2B—C1B	−147.92 (10)
N1A—C1A—C2A—N2A	−75.06 (11)	N1B—C1B—C2B—N2B	75.42 (11)
C11A—N2A—C3A—C4A	173.49 (10)	C11B—N2B—C3B—C4B	−171.14 (10)
C2A—N2A—C3A—C4A	−62.05 (13)	C2B—N2B—C3B—C4B	63.07 (13)
C13A—N3A—C4A—C3A	−60.03 (13)	C13B—N3B—C4B—C3B	60.43 (14)
C5A—N3A—C4A—C3A	169.81 (10)	C5B—N3B—C4B—C3B	−172.70 (10)
N2A—C3A—C4A—N3A	−48.02 (14)	N2B—C3B—C4B—N3B	49.94 (15)
C13A—N3A—C5A—C6A	135.10 (10)	C13B—N3B—C5B—C6B	−142.70 (11)
C4A—N3A—C5A—C6A	−94.50 (12)	C4B—N3B—C5B—C6B	89.73 (13)
C7A—N4A—C6A—C5A	153.91 (9)	C15B—N4B—C6B—C5B	81.83 (12)
C15A—N4A—C6A—C5A	−81.37 (11)	C7B—N4B—C6B—C5B	−152.49 (10)
N3A—C5A—C6A—N4A	−67.60 (12)	N3B—C5B—C6B—N4B	69.60 (13)
C15A—N4A—C7A—C8A	166.52 (9)	C15B—N4B—C7B—C8B	−165.19 (10)
C6A—N4A—C7A—C8A	−68.20 (12)	C6B—N4B—C7B—C8B	68.96 (12)
C9A—N1A—C8A—C7A	−69.78 (12)	C9B—N1B—C8B—C7B	66.01 (12)
C1A—N1A—C8A—C7A	168.22 (9)	C1B—N1B—C8B—C7B	−172.11 (10)
N4A—C7A—C8A—N1A	−50.93 (13)	N4B—C7B—C8B—N1B	47.21 (14)
C8A—N1A—C9A—C10A	157.49 (9)	C8B—N1B—C9B—C10B	−159.06 (9)
C1A—N1A—C9A—C10A	−80.09 (10)	C1B—N1B—C9B—C10B	78.59 (11)
N1A—C9A—C10A—O2A	145.13 (10)	N1B—C9B—C10B—O2B	−144.75 (10)
N1A—C9A—C10A—O1A	−37.13 (13)	N1B—C9B—C10B—O1B	37.76 (13)
C2A—N2A—C11A—C12A	154.25 (10)	C3B—N2B—C11B—C12B	80.71 (13)
C3A—N2A—C11A—C12A	−79.77 (12)	C2B—N2B—C11B—C12B	−152.46 (11)
N2A—C11A—C12A—O3A	153.13 (11)	N2B—C11B—C12B—O3B	−154.40 (12)
N2A—C11A—C12A—N5A	−28.87 (16)	N2B—C11B—C12B—N5B	28.22 (17)
C4A—N3A—C13A—C14A	−66.98 (13)	C4B—N3B—C13B—C14B	66.53 (13)
C5A—N3A—C13A—C14A	61.99 (14)	C5B—N3B—C13B—C14B	−59.37 (14)
N3A—C13A—C14A—O4A	−14.61 (17)	N3B—C13B—C14B—O4B	3.51 (18)
N3A—C13A—C14A—N6A	168.56 (10)	N3B—C13B—C14B—N6B	−178.51 (11)
C7A—N4A—C15A—C16A	−96.35 (11)	C7B—N4B—C15B—C16B	103.60 (13)
C6A—N4A—C15A—C16A	137.57 (10)	C6B—N4B—C15B—C16B	−130.10 (12)
N4A—C15A—C16A—O5A	167.48 (10)	N4B—C15B—C16B—O5B	−169.19 (12)
N4A—C15A—C16A—N7A	−15.95 (15)	N4B—C15B—C16B—N7B	14.68 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N···O1A	0.87 (2)	2.21 (2)	2.6940 (12)	115 (2)
N5A—H51N···O1B	0.89 (1)	1.98 (1)	2.8660 (13)	174 (2)
N5A—H52N···O1A	0.88 (1)	2.04 (2)	2.8884 (13)	162 (2)
N6A—H61N···O6A	0.87 (1)	2.33 (2)	3.0343 (16)	138 (2)
N6A—H62N···O2B	0.86 (1)	2.00 (2)	2.7899 (14)	153 (2)
N7A—H71N···O3B	0.88 (1)	2.16 (2)	2.9997 (14)	161 (2)
N7A—H72N···O1A	0.88 (1)	2.25 (2)	2.9191 (13)	132 (2)
N1B—H11N···N3B	0.87 (2)	2.66 (2)	3.4873 (15)	160 (2)
N5B—H53N···O1A	0.85 (1)	2.03 (1)	2.8792 (13)	174 (2)
N5B—H54N···O1B	0.87 (1)	2.11 (2)	2.8954 (13)	151 (2)
N6B—H63N···O6B	0.86 (1)	2.04 (2)	2.9001 (16)	173 (2)
N6B—H64N···O2A	0.82 (1)	2.20 (2)	2.9910 (15)	162 (2)
N7B—H73N···O3A	0.85 (1)	2.22 (1)	3.0538 (13)	166 (2)
N7B—H74N···O1B	0.86 (1)	2.19 (2)	2.8860 (13)	138 (2)
O6A—H61A···O4A	0.86 (2)	2.03 (2)	2.8417 (13)	157 (2)
O6A—H62A···O5B^i	0.86 (2)	1.86 (2)	2.7181 (13)	172 (2)
O6B—H61B···O6A^ii	0.91 (2)	1.93 (2)	2.8263 (13)	167 (2)
O6B—H62B···O5A^iii	0.90 (2)	1.89 (2)	2.7848 (14)	169 (2)
O7B—H71B···O2B^iv	0.86 (2)	1.93 (2)	2.7863 (13)	172 (2)
O7B—H72B···O3A^v	0.87 (2)	1.95 (2)	2.8205 (14)	178 (2)
O7A—H71A···O2A^vi	0.85 (2)	2.01 (2)	2.8486 (14)	170 (2)
O7A—H72A···O3B^vii	0.85 (2)	1.95 (2)	2.7951 (15)	173 (2)

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x+1, y−1, z; (iii) −x+1, y−1/2, −z+1; (iv) −x, y−1/2, −z; (v) −x+1, y−1/2, −z; (vi) −x+2, y+1/2, −z+1; (vii) −x+1, y+1/2, −z+1.