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The title compound, C24H21N3O6·2CH2Cl2, crystallizes with two independent mol­ecules in the asymmetric unit, each with a different conformation. In the crystal structure, mol­ecules form two-dimensional sheets in the ab plane due to a combination of O—H...O and N—H...O hydrogen bonds. Only edge-to-face stacking inter­actions are observed between fluorenyl aromatic groups of adjacent sheets. Solvent mol­ecules are located within the inter­molecular voids along the b axis and fill the spaces between carbamate linkages or lie between the fluorenyl aromatic groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028273/lh2148sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028273/lh2148Isup2.hkl
Contains datablock I

CCDC reference: 618981

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.061
  • wR factor = 0.112
  • Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor .... 5.45
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C50 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C60 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 C H2 Cl2
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 33.00 From the CIF: _reflns_number_total 15906 Count of symmetry unique reflns 11432 Completeness (_total/calc) 139.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4474 Fraction of Friedel pairs measured 0.391 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Stefanowicz Piotr, resoinsible for idea of compound synthesis, Jaremko \/Lukasz, responsible for manuscript preparation, Jaremko Mariusz, responsible for manuscript preparation, Staszewska Anna, responsible for performing the synthesis, Szewczuk Zbigniew, main author of the idea for project concerning the title compound, Bryndal Iwona,; responsible for structure solution, X-ray measurements and manuscript preparation, Lis Tadeusz, responsile for structure solution and X-ray measurements

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

(2S)-3-(4-Amino-3-nitrophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid dichloromethane disolvate top
Crystal data top
C24H21N3O6·2CH2Cl2F(000) = 1272
Mr = 617.29Dx = 1.415 Mg m3
Monoclinic, P21Melting point: 438 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.362 (3) ÅCell parameters from 12599 reflections
b = 10.489 (3) Åθ = 3.3–30.0°
c = 22.958 (4) ŵ = 0.45 mm1
β = 103.17 (3)°T = 100 K
V = 2898.6 (12) Å3Block, yellow
Z = 40.25 × 0.2 × 0.15 mm
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer
15906 independent reflections
Radiation source: fine-focus sealed tube9639 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 33.0°, θmin = 3.3°
Absorption correction: numerical
(CrysAlisRED; Oxford Diffraction, 2003)
h = 1818
Tmin = 0.913, Tmax = 0.947k = 1612
44865 measured reflectionsl = 3534
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0457P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
15906 reflectionsΔρmax = 0.51 e Å3
715 parametersΔρmin = 0.54 e Å3
7 restraintsAbsolute structure: Flack (1983), with 4474 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (4)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.50747 (15)0.68992 (17)0.06903 (8)0.0200 (4)
O2A0.35497 (15)0.61680 (18)0.00490 (8)0.0224 (4)
H2OA0.35090.69200.00800.027*
O3A0.45934 (17)0.04129 (18)0.26065 (8)0.0235 (4)
O4A0.45313 (17)0.15834 (18)0.28255 (8)0.0246 (4)
O5A0.65010 (14)0.34547 (17)0.04272 (7)0.0149 (4)
O6A0.73120 (14)0.34610 (17)0.14191 (8)0.0160 (4)
N1A0.56961 (16)0.4457 (2)0.10964 (9)0.0130 (4)
H1A0.58040.47960.14560.016*
N2A0.44883 (18)0.0732 (2)0.24476 (9)0.0164 (5)
N3A0.4600 (2)0.1133 (2)0.15041 (10)0.0223 (5)
H3A10.47320.14210.18740.027*
H3A20.46230.16560.12070.027*
C1A0.4458 (2)0.6038 (2)0.04807 (11)0.0155 (5)
C2A0.4642 (2)0.4643 (2)0.06677 (11)0.0130 (5)
H2A0.46710.41410.03010.016*
C3A0.3670 (2)0.4117 (2)0.09152 (12)0.0162 (5)
H3110.35990.46150.12710.019*
H3120.29670.42000.06080.019*
C4A0.3876 (2)0.2729 (2)0.10849 (11)0.0137 (5)
C5A0.4063 (2)0.2338 (2)0.16716 (11)0.0139 (5)
H5A0.40340.29420.19760.017*
C6A0.4298 (2)0.1043 (2)0.18268 (11)0.0150 (5)
C7A0.4362 (2)0.0104 (2)0.13930 (11)0.0150 (5)
C8A0.4154 (2)0.0540 (2)0.07891 (11)0.0167 (5)
H8A0.41800.00530.04800.020*
C9A0.3916 (2)0.1801 (3)0.06428 (11)0.0161 (5)
H9A0.37760.20530.02350.019*
C10A0.6498 (2)0.3772 (2)0.09447 (11)0.0124 (5)
C11A0.8200 (2)0.2692 (3)0.12739 (11)0.0178 (5)
H1A10.85940.31880.10190.021*
H1A20.78840.19190.10520.021*
C12A0.9003 (2)0.2318 (3)0.18500 (11)0.0152 (5)
H12A0.93260.30970.20750.018*
C13A0.9924 (2)0.1501 (3)0.17000 (11)0.0166 (5)
C14A1.0661 (2)0.1811 (3)0.13510 (12)0.0208 (6)
H14A1.06340.26240.11660.025*
C15A1.1447 (2)0.0902 (3)0.12764 (12)0.0241 (6)
H15A1.19520.10880.10320.029*
C16A1.1489 (2)0.0278 (3)0.15605 (13)0.0234 (6)
H16A1.20400.08790.15160.028*
C17A1.0741 (2)0.0594 (3)0.19077 (12)0.0212 (6)
H17A1.07660.14060.20940.025*
C18A0.9954 (2)0.0310 (3)0.19758 (11)0.0155 (5)
C19A0.9085 (2)0.0271 (3)0.23189 (11)0.0170 (5)
C20A0.8795 (2)0.0685 (3)0.26794 (12)0.0208 (6)
H20A0.91770.14780.27270.025*
C21A0.7940 (2)0.0459 (3)0.29679 (13)0.0275 (7)
H21A0.77360.11010.32150.033*
C22A0.7381 (2)0.0704 (3)0.28969 (13)0.0284 (7)
H22A0.67980.08460.30960.034*
C23A0.7663 (2)0.1663 (3)0.25377 (12)0.0233 (6)
H23A0.72750.24520.24870.028*
C24A0.8528 (2)0.1438 (3)0.22551 (11)0.0162 (5)
O1B0.51099 (16)1.18527 (18)0.43616 (8)0.0220 (4)
O2B0.64840 (16)1.10912 (18)0.50908 (8)0.0223 (4)
H2OB0.65161.18470.52150.027*
O3B0.54907 (17)0.46849 (18)0.24280 (8)0.0241 (4)
O4B0.56097 (18)0.67111 (19)0.22676 (8)0.0275 (5)
O5B0.33648 (14)0.85061 (17)0.45331 (8)0.0169 (4)
O6B0.26709 (14)0.89983 (18)0.35571 (8)0.0181 (4)
N1B0.44199 (18)0.9478 (2)0.39692 (9)0.0163 (4)
H1B0.44280.97750.36120.020*
N2B0.56075 (18)0.5810 (2)0.26140 (9)0.0169 (5)
N3B0.5576 (2)0.3807 (2)0.35106 (10)0.0224 (5)
H3B10.56050.32320.37930.027*
H3B20.54150.35760.31320.027*
C1B0.5640 (2)1.0970 (2)0.46229 (10)0.0151 (5)
C2B0.5423 (2)0.9572 (3)0.44401 (11)0.0145 (5)
H2B0.53100.90810.47950.017*
C3B0.6424 (2)0.9004 (3)0.42367 (11)0.0169 (5)
H3210.65760.95230.39040.020*
H3220.70880.90440.45720.020*
C4B0.6226 (2)0.7635 (2)0.40322 (11)0.0162 (5)
C5B0.5982 (2)0.7321 (2)0.34366 (11)0.0148 (5)
H5B0.59480.79760.31470.018*
C6B0.5781 (2)0.6051 (2)0.32447 (11)0.0145 (5)
C7B0.5779 (2)0.5043 (2)0.36579 (11)0.0164 (5)
C8B0.6038 (2)0.5391 (3)0.42715 (12)0.0192 (6)
H8B0.60620.47500.45670.023*
C9B0.6255 (2)0.6641 (3)0.44491 (11)0.0182 (5)
H9B0.64290.68360.48640.022*
C10B0.3482 (2)0.8955 (2)0.40585 (10)0.0140 (5)
C11B0.1626 (2)0.8393 (3)0.35876 (13)0.0204 (6)
H1B10.10140.87800.32850.025*
H1B20.14750.85430.39870.025*
C12B0.1662 (2)0.6956 (3)0.34746 (12)0.0185 (5)
H12B0.22490.65420.37900.022*
C13B0.0529 (2)0.6372 (3)0.34641 (12)0.0209 (6)
C14B0.0051 (2)0.6335 (3)0.39183 (14)0.0294 (7)
H14B0.02540.67030.42980.035*
C15B0.1092 (3)0.5745 (3)0.38028 (16)0.0349 (8)
H15B0.14940.56960.41090.042*
C16B0.1542 (3)0.5229 (3)0.32400 (16)0.0342 (8)
H16B0.22480.48240.31690.041*
C17B0.0981 (2)0.5294 (3)0.27807 (15)0.0272 (7)
H17B0.13080.49700.23940.033*
C18B0.0073 (2)0.5848 (3)0.29007 (13)0.0209 (6)
C19B0.0874 (2)0.5996 (3)0.25230 (12)0.0215 (6)
C20B0.0826 (2)0.5625 (3)0.19331 (14)0.0287 (7)
H20B0.01880.52030.17060.034*
C21B0.1724 (3)0.5881 (3)0.16831 (14)0.0313 (7)
H21B0.17000.56300.12830.038*
C22B0.2658 (2)0.6502 (3)0.20127 (14)0.0283 (7)
H22B0.32610.66770.18320.034*
C23B0.2728 (2)0.6872 (3)0.26036 (12)0.0224 (6)
H23B0.33740.72830.28290.027*
C24B0.1823 (2)0.6623 (2)0.28553 (12)0.0181 (5)
Cl10.26953 (8)0.89283 (8)0.08922 (4)0.0445 (2)
Cl20.19003 (7)0.63040 (8)0.08664 (4)0.0424 (2)
C300.2405 (3)0.7484 (3)0.12973 (14)0.0405 (9)
H3010.30900.71690.14040.049*
H3020.18430.76400.16730.049*
Cl30.7247 (2)0.8811 (3)0.59695 (16)0.0396 (6)0.764 (6)
Cl40.8450 (2)0.7309 (3)0.70065 (11)0.0796 (9)0.764 (6)
C400.7272 (5)0.7495 (6)0.6435 (2)0.058 (2)0.764 (6)
H4010.66200.75490.66170.070*0.764 (6)
H4020.71820.67180.61840.070*0.764 (6)
Cl310.7556 (8)0.8714 (13)0.5978 (6)0.0396 (6)0.236 (6)
Cl410.8038 (7)0.7773 (9)0.7161 (4)0.0796 (9)0.236 (6)
C4010.751 (3)0.7373 (18)0.6417 (4)0.058 (2)0.236 (6)
H4110.67330.70720.63600.070*0.236 (6)
H4120.79560.66780.62980.070*0.236 (6)
Cl50.14199 (8)0.79174 (14)0.02583 (4)0.0656 (4)
Cl60.04682 (11)0.96014 (12)0.01272 (6)0.0818 (4)
C500.0034 (3)0.8244 (4)0.02774 (15)0.0412 (9)
H5010.04360.75060.01110.049*
H5020.00180.83570.06980.049*
Cl70.15154 (9)0.74663 (16)0.56067 (6)0.0796 (4)
Cl80.06225 (12)0.61957 (15)0.55271 (6)0.0851 (4)
C600.0379 (3)0.7227 (5)0.59415 (19)0.0604 (12)
H6010.06550.68700.63470.073*
H6020.00290.80600.59840.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0245 (10)0.0156 (9)0.0178 (9)0.0003 (8)0.0003 (8)0.0001 (8)
O2A0.0232 (10)0.0140 (9)0.0248 (10)0.0017 (8)0.0057 (8)0.0101 (8)
O3A0.0381 (12)0.0138 (9)0.0189 (9)0.0023 (9)0.0071 (9)0.0073 (8)
O4A0.0414 (12)0.0207 (10)0.0114 (9)0.0010 (9)0.0049 (8)0.0032 (8)
O5A0.0177 (9)0.0131 (9)0.0131 (8)0.0035 (7)0.0016 (7)0.0032 (7)
O6A0.0165 (9)0.0167 (9)0.0137 (8)0.0075 (7)0.0010 (7)0.0005 (7)
N1A0.0159 (10)0.0122 (10)0.0091 (9)0.0009 (8)0.0011 (8)0.0011 (8)
N2A0.0210 (11)0.0146 (11)0.0138 (10)0.0008 (9)0.0041 (9)0.0038 (9)
N3A0.0371 (14)0.0112 (11)0.0199 (11)0.0046 (10)0.0092 (10)0.0016 (9)
C1A0.0232 (13)0.0110 (12)0.0141 (12)0.0031 (10)0.0081 (10)0.0046 (10)
C2A0.0157 (12)0.0122 (12)0.0101 (11)0.0020 (10)0.0006 (9)0.0011 (10)
C3A0.0163 (12)0.0135 (12)0.0195 (12)0.0021 (10)0.0057 (10)0.0025 (10)
C4A0.0125 (12)0.0135 (12)0.0160 (12)0.0017 (10)0.0052 (10)0.0001 (10)
C5A0.0164 (12)0.0104 (11)0.0154 (12)0.0005 (10)0.0044 (10)0.0015 (10)
C6A0.0183 (13)0.0142 (12)0.0127 (11)0.0008 (10)0.0041 (10)0.0025 (10)
C7A0.0187 (13)0.0117 (12)0.0168 (12)0.0004 (10)0.0086 (10)0.0006 (10)
C8A0.0214 (13)0.0166 (13)0.0129 (12)0.0004 (11)0.0058 (10)0.0025 (10)
C9A0.0190 (13)0.0192 (13)0.0106 (11)0.0013 (11)0.0045 (10)0.0016 (10)
C10A0.0148 (12)0.0065 (11)0.0158 (12)0.0014 (9)0.0032 (10)0.0025 (9)
C11A0.0180 (13)0.0177 (13)0.0185 (12)0.0093 (10)0.0059 (10)0.0035 (11)
C12A0.0142 (12)0.0155 (12)0.0160 (12)0.0016 (10)0.0034 (10)0.0024 (10)
C13A0.0145 (12)0.0194 (13)0.0151 (12)0.0021 (10)0.0014 (10)0.0015 (10)
C14A0.0157 (13)0.0234 (14)0.0218 (14)0.0010 (11)0.0011 (11)0.0035 (12)
C15A0.0160 (13)0.0367 (17)0.0208 (14)0.0009 (12)0.0067 (11)0.0025 (13)
C16A0.0194 (14)0.0253 (15)0.0257 (14)0.0087 (12)0.0055 (12)0.0003 (12)
C17A0.0228 (14)0.0177 (13)0.0217 (13)0.0049 (11)0.0019 (11)0.0020 (11)
C18A0.0154 (12)0.0153 (12)0.0150 (12)0.0020 (10)0.0018 (10)0.0017 (10)
C19A0.0121 (12)0.0207 (13)0.0163 (12)0.0012 (11)0.0006 (10)0.0024 (11)
C20A0.0182 (13)0.0202 (14)0.0215 (13)0.0005 (11)0.0008 (11)0.0066 (11)
C21A0.0221 (15)0.0330 (16)0.0277 (15)0.0043 (13)0.0064 (12)0.0139 (14)
C22A0.0209 (14)0.0424 (19)0.0246 (15)0.0024 (13)0.0106 (12)0.0084 (14)
C23A0.0199 (14)0.0279 (16)0.0218 (14)0.0049 (12)0.0039 (11)0.0044 (12)
C24A0.0154 (12)0.0223 (14)0.0101 (11)0.0003 (10)0.0013 (9)0.0010 (10)
O1B0.0298 (11)0.0157 (9)0.0182 (9)0.0009 (8)0.0010 (8)0.0017 (8)
O2B0.0270 (10)0.0158 (10)0.0190 (9)0.0019 (8)0.0049 (8)0.0046 (8)
O3B0.0400 (12)0.0157 (9)0.0169 (9)0.0047 (9)0.0069 (9)0.0040 (8)
O4B0.0492 (13)0.0189 (10)0.0138 (9)0.0041 (10)0.0058 (9)0.0049 (8)
O5B0.0198 (9)0.0151 (9)0.0155 (9)0.0005 (8)0.0034 (7)0.0019 (7)
O6B0.0175 (9)0.0174 (9)0.0168 (9)0.0038 (8)0.0016 (7)0.0022 (8)
N1B0.0199 (11)0.0188 (11)0.0094 (9)0.0042 (9)0.0017 (8)0.0014 (9)
N2B0.0199 (11)0.0153 (11)0.0141 (10)0.0007 (9)0.0013 (9)0.0010 (9)
N3B0.0382 (14)0.0110 (11)0.0177 (11)0.0029 (10)0.0056 (10)0.0026 (9)
C1B0.0201 (13)0.0164 (13)0.0090 (11)0.0032 (10)0.0038 (10)0.0015 (10)
C2B0.0157 (12)0.0162 (12)0.0101 (11)0.0007 (10)0.0002 (10)0.0009 (10)
C3B0.0194 (13)0.0167 (13)0.0160 (12)0.0030 (11)0.0067 (10)0.0050 (11)
C4B0.0166 (12)0.0157 (13)0.0168 (12)0.0018 (10)0.0045 (10)0.0005 (10)
C5B0.0153 (12)0.0141 (12)0.0149 (12)0.0008 (10)0.0036 (10)0.0020 (10)
C6B0.0168 (12)0.0154 (12)0.0109 (11)0.0001 (10)0.0023 (10)0.0021 (10)
C7B0.0185 (13)0.0168 (13)0.0147 (12)0.0008 (10)0.0051 (10)0.0030 (10)
C8B0.0249 (14)0.0197 (13)0.0139 (12)0.0017 (11)0.0062 (11)0.0036 (11)
C9B0.0221 (13)0.0197 (14)0.0128 (12)0.0015 (11)0.0040 (10)0.0013 (10)
C10B0.0201 (13)0.0094 (11)0.0112 (11)0.0038 (10)0.0006 (10)0.0007 (10)
C11B0.0175 (13)0.0215 (14)0.0216 (13)0.0007 (11)0.0031 (11)0.0029 (11)
C12B0.0148 (12)0.0197 (13)0.0197 (13)0.0025 (10)0.0011 (10)0.0017 (11)
C13B0.0169 (13)0.0179 (13)0.0259 (14)0.0013 (11)0.0011 (11)0.0009 (12)
C14B0.0271 (15)0.0317 (17)0.0316 (16)0.0043 (13)0.0112 (13)0.0061 (14)
C15B0.0243 (16)0.0348 (18)0.050 (2)0.0052 (14)0.0184 (15)0.0080 (16)
C16B0.0208 (15)0.0250 (16)0.061 (2)0.0028 (13)0.0171 (15)0.0164 (16)
C17B0.0194 (14)0.0197 (14)0.0412 (18)0.0016 (12)0.0045 (13)0.0132 (13)
C18B0.0166 (13)0.0140 (12)0.0315 (15)0.0047 (10)0.0040 (12)0.0028 (11)
C19B0.0191 (13)0.0175 (14)0.0271 (14)0.0023 (11)0.0034 (11)0.0033 (12)
C20B0.0225 (15)0.0269 (16)0.0349 (16)0.0003 (12)0.0025 (13)0.0150 (13)
C21B0.0391 (18)0.0296 (17)0.0267 (15)0.0017 (14)0.0104 (14)0.0091 (14)
C22B0.0254 (15)0.0290 (16)0.0338 (16)0.0024 (13)0.0136 (13)0.0037 (14)
C23B0.0251 (14)0.0171 (13)0.0246 (14)0.0024 (11)0.0046 (12)0.0016 (11)
C24B0.0147 (12)0.0119 (12)0.0254 (14)0.0037 (10)0.0000 (11)0.0023 (11)
Cl10.0563 (6)0.0270 (4)0.0416 (5)0.0115 (4)0.0066 (4)0.0028 (4)
Cl20.0348 (4)0.0358 (5)0.0546 (5)0.0038 (4)0.0058 (4)0.0124 (4)
C300.050 (2)0.0354 (19)0.0275 (16)0.0110 (17)0.0089 (15)0.0072 (15)
Cl30.0529 (16)0.0283 (7)0.0317 (4)0.0087 (12)0.0030 (12)0.0107 (5)
Cl40.0613 (14)0.0783 (15)0.0718 (12)0.0055 (11)0.0419 (11)0.0307 (11)
C400.020 (4)0.082 (3)0.063 (3)0.011 (3)0.010 (2)0.051 (3)
Cl310.0529 (16)0.0283 (7)0.0317 (4)0.0087 (12)0.0030 (12)0.0107 (5)
Cl410.0613 (14)0.0783 (15)0.0718 (12)0.0055 (11)0.0419 (11)0.0307 (11)
C4010.020 (4)0.082 (3)0.063 (3)0.011 (3)0.010 (2)0.051 (3)
Cl50.0454 (6)0.1205 (11)0.0332 (5)0.0132 (6)0.0137 (4)0.0145 (6)
Cl60.0818 (8)0.0540 (7)0.0818 (8)0.0010 (6)0.0397 (7)0.0023 (6)
C500.0341 (19)0.058 (2)0.0319 (17)0.0064 (17)0.0080 (15)0.0009 (17)
Cl70.0478 (6)0.1219 (12)0.0706 (7)0.0041 (7)0.0167 (6)0.0336 (8)
Cl80.0946 (9)0.0996 (10)0.0655 (7)0.0368 (8)0.0273 (7)0.0215 (8)
C600.041 (2)0.085 (3)0.054 (2)0.001 (2)0.0086 (19)0.013 (2)
Geometric parameters (Å, º) top
O1A—C1A1.208 (3)N1B—H1B0.8800
O2A—C1A1.325 (3)N2B—C6B1.437 (3)
O2A—H2OA0.8400N3B—C7B1.349 (3)
O3A—N2A1.253 (3)N3B—H3B10.8800
O4A—N2A1.238 (3)N3B—H3B20.8800
O5A—C10A1.235 (3)C1B—C2B1.532 (4)
O6A—C10A1.344 (3)C2B—C3B1.539 (4)
O6A—C11A1.461 (3)C2B—H2B1.0000
N1A—C10A1.333 (3)C3B—C4B1.513 (4)
N1A—C2A1.456 (3)C3B—H3210.9900
N1A—H1A0.8800C3B—H3220.9900
N2A—C6A1.428 (3)C4B—C5B1.372 (4)
N3A—C7A1.342 (3)C4B—C9B1.410 (4)
N3A—H3A10.8800C5B—C6B1.408 (4)
N3A—H3A20.8800C5B—H5B0.9500
C1A—C2A1.527 (3)C6B—C7B1.421 (4)
C2A—C3A1.544 (4)C7B—C8B1.419 (4)
C2A—H2A1.0000C8B—C9B1.381 (4)
C3A—C4A1.513 (4)C8B—H8B0.9500
C3A—H3110.9900C9B—H9B0.9500
C3A—H3120.9900C11B—C12B1.532 (4)
C4A—C5A1.376 (3)C11B—H1B10.9900
C4A—C9A1.415 (3)C11B—H1B20.9900
C5A—C6A1.417 (4)C12B—C24B1.521 (4)
C5A—H5A0.9500C12B—C13B1.524 (4)
C6A—C7A1.415 (4)C12B—H12B1.0000
C7A—C8A1.427 (4)C13B—C14B1.394 (4)
C8A—C9A1.380 (4)C13B—C18B1.400 (4)
C8A—H8A0.9500C14B—C15B1.398 (4)
C9A—H9A0.9500C14B—H14B0.9500
C11A—C12A1.513 (3)C15B—C16B1.395 (5)
C11A—H1A10.9900C15B—H15B0.9500
C11A—H1A20.9900C16B—C17B1.389 (5)
C12A—C24A1.520 (4)C16B—H16B0.9500
C12A—C13A1.526 (4)C17B—C18B1.396 (4)
C12A—H12A1.0000C17B—H17B0.9500
C13A—C14A1.382 (4)C18B—C19B1.465 (4)
C13A—C18A1.398 (4)C19B—C20B1.397 (4)
C14A—C15A1.399 (4)C19B—C24B1.408 (4)
C14A—H14A0.9500C20B—C21B1.387 (5)
C15A—C16A1.395 (4)C20B—H20B0.9500
C15A—H15A0.9500C21B—C22B1.390 (4)
C16A—C17A1.391 (4)C21B—H21B0.9500
C16A—H16A0.9500C22B—C23B1.395 (4)
C17A—C18A1.393 (4)C22B—H22B0.9500
C17A—H17A0.9500C23B—C24B1.396 (4)
C18A—C19A1.470 (4)C23B—H23B0.9500
C19A—C24A1.396 (4)Cl1—C301.771 (3)
C19A—C20A1.398 (4)Cl2—C301.783 (4)
C20A—C21A1.390 (4)C30—H3010.9900
C20A—H20A0.9500C30—H3020.9900
C21A—C22A1.393 (4)Cl3—C401.741 (3)
C21A—H21A0.9500Cl4—C401.735 (4)
C22A—C23A1.395 (4)C40—H4010.9900
C22A—H22A0.9500C40—H4020.9900
C23A—C24A1.391 (4)Cl31—C4011.739 (5)
C23A—H23A0.9500Cl41—C4011.737 (5)
O1B—C1B1.212 (3)C401—H4110.9900
O2B—C1B1.322 (3)C401—H4120.9900
O2B—H2OB0.8400Cl5—C501.758 (4)
O3B—N2B1.252 (3)Cl6—C501.736 (4)
O4B—N2B1.236 (3)C50—H5010.9900
O5B—C10B1.226 (3)C50—H5020.9900
O6B—C10B1.344 (3)Cl7—C601.766 (4)
O6B—C11B1.455 (3)Cl8—C601.753 (5)
N1B—C10B1.340 (3)C60—H6010.9900
N1B—C2B1.451 (3)C60—H6020.9900
C1A—O2A—H2OA109.5N1B—C2B—C3B110.9 (2)
C10A—O6A—C11A114.33 (18)C1B—C2B—C3B110.5 (2)
C10A—N1A—C2A120.0 (2)N1B—C2B—H2B108.6
C10A—N1A—H1A120.0C1B—C2B—H2B108.6
C2A—N1A—H1A120.0C3B—C2B—H2B108.6
O4A—N2A—O3A120.2 (2)C4B—C3B—C2B112.1 (2)
O4A—N2A—C6A120.4 (2)C4B—C3B—H321109.2
O3A—N2A—C6A119.5 (2)C2B—C3B—H321109.2
C7A—N3A—H3A1120.0C4B—C3B—H322109.2
C7A—N3A—H3A2120.0C2B—C3B—H322109.2
H3A1—N3A—H3A2120.0H321—C3B—H322107.9
O1A—C1A—O2A124.8 (2)C5B—C4B—C9B117.7 (2)
O1A—C1A—C2A124.3 (2)C5B—C4B—C3B121.4 (2)
O2A—C1A—C2A110.8 (2)C9B—C4B—C3B120.9 (2)
N1A—C2A—C1A111.8 (2)C4B—C5B—C6B121.5 (2)
N1A—C2A—C3A110.78 (19)C4B—C5B—H5B119.3
C1A—C2A—C3A111.6 (2)C6B—C5B—H5B119.3
N1A—C2A—H2A107.5C5B—C6B—C7B121.5 (2)
C1A—C2A—H2A107.5C5B—C6B—N2B117.2 (2)
C3A—C2A—H2A107.5C7B—C6B—N2B121.3 (2)
C4A—C3A—C2A109.8 (2)N3B—C7B—C8B118.9 (2)
C4A—C3A—H311109.7N3B—C7B—C6B125.2 (2)
C2A—C3A—H311109.7C8B—C7B—C6B115.9 (2)
C4A—C3A—H312109.7C9B—C8B—C7B121.5 (2)
C2A—C3A—H312109.7C9B—C8B—H8B119.3
H311—C3A—H312108.2C7B—C8B—H8B119.3
C5A—C4A—C9A118.1 (2)C8B—C9B—C4B121.9 (2)
C5A—C4A—C3A121.3 (2)C8B—C9B—H9B119.1
C9A—C4A—C3A120.6 (2)C4B—C9B—H9B119.0
C4A—C5A—C6A120.7 (2)O5B—C10B—N1B125.1 (2)
C4A—C5A—H5A119.6O5B—C10B—O6B123.9 (2)
C6A—C5A—H5A119.6N1B—C10B—O6B111.0 (2)
C7A—C6A—C5A122.1 (2)O6B—C11B—C12B111.2 (2)
C7A—C6A—N2A121.4 (2)O6B—C11B—H1B1109.4
C5A—C6A—N2A116.6 (2)C12B—C11B—H1B1109.4
N3A—C7A—C6A125.7 (2)O6B—C11B—H1B2109.4
N3A—C7A—C8A118.6 (2)C12B—C11B—H1B2109.4
C6A—C7A—C8A115.7 (2)H1B1—C11B—H1B2108.0
C9A—C8A—C7A121.7 (2)C24B—C12B—C13B102.0 (2)
C9A—C8A—H8A119.2C24B—C12B—C11B113.5 (2)
C7A—C8A—H8A119.2C13B—C12B—C11B109.7 (2)
C8A—C9A—C4A121.7 (2)C24B—C12B—H12B110.4
C8A—C9A—H9A119.2C13B—C12B—H12B110.4
C4A—C9A—H9A119.2C11B—C12B—H12B110.4
O5A—C10A—N1A124.2 (2)C14B—C13B—C18B120.8 (3)
O5A—C10A—O6A123.3 (2)C14B—C13B—C12B128.8 (3)
N1A—C10A—O6A112.5 (2)C18B—C13B—C12B110.3 (2)
O6A—C11A—C12A108.7 (2)C13B—C14B—C15B118.6 (3)
O6A—C11A—H1A1109.9C13B—C14B—H14B120.7
C12A—C11A—H1A1109.9C15B—C14B—H14B120.7
O6A—C11A—H1A2109.9C16B—C15B—C14B120.2 (3)
C12A—C11A—H1A2109.9C16B—C15B—H15B119.9
H1A1—C11A—H1A2108.3C14B—C15B—H15B119.9
C11A—C12A—C24A115.2 (2)C17B—C16B—C15B121.4 (3)
C11A—C12A—C13A108.8 (2)C17B—C16B—H16B119.3
C24A—C12A—C13A102.1 (2)C15B—C16B—H16B119.3
C11A—C12A—H12A110.2C16B—C17B—C18B118.4 (3)
C24A—C12A—H12A110.2C16B—C17B—H17B120.8
C13A—C12A—H12A110.2C18B—C17B—H17B120.8
C14A—C13A—C18A121.3 (2)C17B—C18B—C13B120.4 (3)
C14A—C13A—C12A128.6 (2)C17B—C18B—C19B130.8 (3)
C18A—C13A—C12A110.1 (2)C13B—C18B—C19B108.7 (2)
C13A—C14A—C15A118.6 (3)C20B—C19B—C24B120.1 (3)
C13A—C14A—H14A120.7C20B—C19B—C18B131.2 (3)
C15A—C14A—H14A120.7C24B—C19B—C18B108.7 (2)
C16A—C15A—C14A120.0 (3)C21B—C20B—C19B119.0 (3)
C16A—C15A—H15A120.0C21B—C20B—H20B120.5
C14A—C15A—H15A120.0C19B—C20B—H20B120.5
C17A—C16A—C15A121.3 (3)C20B—C21B—C22B120.6 (3)
C17A—C16A—H16A119.3C20B—C21B—H21B119.7
C15A—C16A—H16A119.3C22B—C21B—H21B119.7
C16A—C17A—C18A118.3 (3)C21B—C22B—C23B121.3 (3)
C16A—C17A—H17A120.8C21B—C22B—H22B119.4
C18A—C17A—H17A120.8C23B—C22B—H22B119.4
C17A—C18A—C13A120.3 (2)C22B—C23B—C24B118.2 (3)
C17A—C18A—C19A131.0 (3)C22B—C23B—H23B120.9
C13A—C18A—C19A108.7 (2)C24B—C23B—H23B120.9
C24A—C19A—C20A120.3 (2)C23B—C24B—C19B120.7 (3)
C24A—C19A—C18A108.8 (2)C23B—C24B—C12B129.2 (2)
C20A—C19A—C18A130.9 (3)C19B—C24B—C12B110.1 (2)
C21A—C20A—C19A119.0 (3)Cl1—C30—Cl2110.92 (19)
C21A—C20A—H20A120.5Cl1—C30—H301109.5
C19A—C20A—H20A120.5Cl2—C30—H301109.5
C20A—C21A—C22A120.3 (3)Cl1—C30—H302109.5
C20A—C21A—H21A119.9Cl2—C30—H302109.5
C22A—C21A—H21A119.9H301—C30—H302108.0
C21A—C22A—C23A121.1 (3)Cl4—C40—Cl3116.6 (4)
C21A—C22A—H22A119.4Cl4—C40—H401108.1
C23A—C22A—H22A119.4Cl3—C40—H401108.1
C24A—C23A—C22A118.4 (3)Cl4—C40—H402108.1
C24A—C23A—H23A120.8Cl3—C40—H402108.1
C22A—C23A—H23A120.8H401—C40—H402107.3
C23A—C24A—C19A120.9 (3)Cl41—C401—Cl31108.6 (9)
C23A—C24A—C12A128.8 (2)Cl41—C401—H411110.0
C19A—C24A—C12A110.3 (2)Cl31—C401—H411110.0
C1B—O2B—H2OB109.5Cl41—C401—H412110.0
C10B—O6B—C11B116.2 (2)Cl31—C401—H412110.0
C10B—N1B—C2B122.4 (2)H411—C401—H412108.3
C10B—N1B—H1B118.8Cl6—C50—Cl5112.2 (2)
C2B—N1B—H1B118.8Cl6—C50—H501109.2
O4B—N2B—O3B121.2 (2)Cl5—C50—H501109.2
O4B—N2B—C6B119.5 (2)Cl6—C50—H502109.2
O3B—N2B—C6B119.3 (2)Cl5—C50—H502109.2
C7B—N3B—H3B1120.0H501—C50—H502107.9
C7B—N3B—H3B2120.0Cl8—C60—Cl7112.7 (2)
H3B1—N3B—H3B2120.0Cl8—C60—H601109.1
O1B—C1B—O2B124.5 (2)Cl7—C60—H601109.1
O1B—C1B—C2B123.7 (2)Cl8—C60—H602109.1
O2B—C1B—C2B111.8 (2)Cl7—C60—H602109.1
N1B—C2B—C1B109.7 (2)H601—C60—H602107.8
C10A—N1A—C2A—C1A114.1 (2)C10B—N1B—C2B—C1B110.1 (3)
C10A—N1A—C2A—C3A120.7 (2)C10B—N1B—C2B—C3B127.5 (2)
O1A—C1A—C2A—N1A4.5 (4)O1B—C1B—C2B—N1B7.3 (3)
O2A—C1A—C2A—N1A174.0 (2)O2B—C1B—C2B—N1B173.8 (2)
O1A—C1A—C2A—C3A120.2 (3)O1B—C1B—C2B—C3B115.3 (3)
O2A—C1A—C2A—C3A61.3 (3)O2B—C1B—C2B—C3B63.6 (3)
N1A—C2A—C3A—C4A55.7 (3)N1B—C2B—C3B—C4B56.2 (3)
C1A—C2A—C3A—C4A179.0 (2)C1B—C2B—C3B—C4B178.1 (2)
C2A—C3A—C4A—C5A113.4 (3)C2B—C3B—C4B—C5B103.9 (3)
C2A—C3A—C4A—C9A64.6 (3)C2B—C3B—C4B—C9B74.3 (3)
C9A—C4A—C5A—C6A0.6 (4)C9B—C4B—C5B—C6B0.8 (4)
C3A—C4A—C5A—C6A177.5 (2)C3B—C4B—C5B—C6B179.1 (2)
C4A—C5A—C6A—C7A0.6 (4)C4B—C5B—C6B—C7B2.5 (4)
C4A—C5A—C6A—N2A179.5 (2)C4B—C5B—C6B—N2B175.9 (2)
O4A—N2A—C6A—C7A173.2 (2)O4B—N2B—C6B—C5B2.0 (4)
O3A—N2A—C6A—C7A7.9 (4)O3B—N2B—C6B—C5B175.9 (2)
O4A—N2A—C6A—C5A5.7 (4)O4B—N2B—C6B—C7B179.7 (2)
O3A—N2A—C6A—C5A173.1 (2)O3B—N2B—C6B—C7B2.5 (4)
C5A—C6A—C7A—N3A178.7 (3)C5B—C6B—C7B—N3B178.8 (3)
N2A—C6A—C7A—N3A0.1 (4)N2B—C6B—C7B—N3B2.9 (4)
C5A—C6A—C7A—C8A1.2 (4)C5B—C6B—C7B—C8B2.6 (4)
N2A—C6A—C7A—C8A180.0 (2)N2B—C6B—C7B—C8B175.7 (2)
N3A—C7A—C8A—C9A179.3 (2)N3B—C7B—C8B—C9B179.9 (3)
C6A—C7A—C8A—C9A0.6 (4)C6B—C7B—C8B—C9B1.2 (4)
C7A—C8A—C9A—C4A0.6 (4)C7B—C8B—C9B—C4B0.4 (4)
C5A—C4A—C9A—C8A1.2 (4)C5B—C4B—C9B—C8B0.6 (4)
C3A—C4A—C9A—C8A177.0 (2)C3B—C4B—C9B—C8B177.6 (2)
C2A—N1A—C10A—O5A13.3 (4)C2B—N1B—C10B—O5B0.1 (4)
C2A—N1A—C10A—O6A166.6 (2)C2B—N1B—C10B—O6B179.1 (2)
C11A—O6A—C10A—O5A0.9 (3)C11B—O6B—C10B—O5B4.1 (4)
C11A—O6A—C10A—N1A179.1 (2)C11B—O6B—C10B—N1B176.7 (2)
C10A—O6A—C11A—C12A175.2 (2)C10B—O6B—C11B—C12B83.6 (3)
O6A—C11A—C12A—C24A65.5 (3)O6B—C11B—C12B—C24B62.4 (3)
O6A—C11A—C12A—C13A179.3 (2)O6B—C11B—C12B—C13B175.8 (2)
C11A—C12A—C13A—C14A59.0 (3)C24B—C12B—C13B—C14B177.8 (3)
C24A—C12A—C13A—C14A178.9 (3)C11B—C12B—C13B—C14B61.5 (4)
C11A—C12A—C13A—C18A121.3 (2)C24B—C12B—C13B—C18B3.4 (3)
C24A—C12A—C13A—C18A0.9 (3)C11B—C12B—C13B—C18B117.3 (3)
C18A—C13A—C14A—C15A0.1 (4)C18B—C13B—C14B—C15B1.0 (5)
C12A—C13A—C14A—C15A179.8 (2)C12B—C13B—C14B—C15B179.7 (3)
C13A—C14A—C15A—C16A1.2 (4)C13B—C14B—C15B—C16B1.2 (5)
C14A—C15A—C16A—C17A1.8 (4)C14B—C15B—C16B—C17B0.6 (5)
C15A—C16A—C17A—C18A1.2 (4)C15B—C16B—C17B—C18B2.5 (5)
C16A—C17A—C18A—C13A0.0 (4)C16B—C17B—C18B—C13B2.7 (4)
C16A—C17A—C18A—C19A178.5 (3)C16B—C17B—C18B—C19B176.7 (3)
C14A—C13A—C18A—C17A0.6 (4)C14B—C13B—C18B—C17B1.0 (4)
C12A—C13A—C18A—C17A179.2 (2)C12B—C13B—C18B—C17B177.9 (2)
C14A—C13A—C18A—C19A179.3 (2)C14B—C13B—C18B—C19B178.6 (3)
C12A—C13A—C18A—C19A0.4 (3)C12B—C13B—C18B—C19B2.5 (3)
C17A—C18A—C19A—C24A178.4 (3)C17B—C18B—C19B—C20B0.3 (5)
C13A—C18A—C19A—C24A0.2 (3)C13B—C18B—C19B—C20B179.2 (3)
C17A—C18A—C19A—C20A0.2 (5)C17B—C18B—C19B—C24B179.9 (3)
C13A—C18A—C19A—C20A178.4 (3)C13B—C18B—C19B—C24B0.4 (3)
C24A—C19A—C20A—C21A0.5 (4)C24B—C19B—C20B—C21B0.1 (4)
C18A—C19A—C20A—C21A178.6 (3)C18B—C19B—C20B—C21B179.5 (3)
C19A—C20A—C21A—C22A0.1 (4)C19B—C20B—C21B—C22B0.2 (5)
C20A—C21A—C22A—C23A0.0 (5)C20B—C21B—C22B—C23B0.7 (5)
C21A—C22A—C23A—C24A0.7 (4)C21B—C22B—C23B—C24B1.1 (4)
C22A—C23A—C24A—C19A1.3 (4)C22B—C23B—C24B—C19B1.0 (4)
C22A—C23A—C24A—C12A179.3 (3)C22B—C23B—C24B—C12B177.9 (3)
C20A—C19A—C24A—C23A1.3 (4)C20B—C19B—C24B—C23B0.5 (4)
C18A—C19A—C24A—C23A179.7 (2)C18B—C19B—C24B—C23B179.2 (2)
C20A—C19A—C24A—C12A179.3 (2)C20B—C19B—C24B—C12B178.5 (3)
C18A—C19A—C24A—C12A0.8 (3)C18B—C19B—C24B—C12B1.8 (3)
C11A—C12A—C24A—C23A62.7 (4)C13B—C12B—C24B—C23B178.0 (3)
C13A—C12A—C24A—C23A179.6 (3)C11B—C12B—C24B—C23B64.1 (4)
C11A—C12A—C24A—C19A116.7 (2)C13B—C12B—C24B—C19B3.1 (3)
C13A—C12A—C24A—C19A1.0 (3)C11B—C12B—C24B—C19B114.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O5Ai0.841.802.631 (3)173
N1A—H1A···O3B0.882.353.134 (3)148
N3A—H3A1···O3A0.882.032.643 (3)126
N3A—H3A1···O4Bii0.882.322.958 (3)129
N3A—H3A2···O1Aii0.882.082.932 (3)163
O2B—H2OB···O5Biii0.841.832.669 (3)178
N1B—H1B···O3Aiv0.882.373.186 (3)154
N3B—H3B2···O3B0.882.012.630 (3)126
N3B—H3B2···O4A0.882.392.942 (3)121
N3B—H3B1···O1Bii0.882.132.977 (3)161
C5B—H5B···O3Aiv0.952.503.277 (3)139
C8B—H8B···O5Bv0.952.413.326 (3)162
C30—H301···O1Avi0.992.493.170 (4)125
C40—H401···O4Aiii0.992.353.239 (7)149
Symmetry codes: (i) x+1, y+1/2, z; (ii) x, y1, z; (iii) x+1, y+1/2, z+1; (iv) x, y+1, z; (v) x+1, y1/2, z+1; (vi) x1, y, z.
 

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