Towards extracting the charge density from normal-resolution data

The limiting factor for charge-density studies is crystal quality. Although area detection and low temperatures enable redundant data collection, only compounds that form well diffracting single crystals without disorder are amenable to these studies. If thermal motion and electron density ρ(r) were de-convoluted, multipole parameters could also be refined with lower-resolution data, such as those commonly collected for macromolecules. Using the invariom database for first refining conventional parameters (x, y, z and atomic displacement parameters), de-convolution can be achieved. In a subsequent least-squares refinement of multipole parameters only, information on the charge density becomes accessible also for data not fulfilling charge-density requirements. A critical aspect of this procedure is the missing information on the correlation between refined and non-refined parameters. This correlation is investigated in detail by comparing a full multipole refinement on high-resolution and a blocked refinement on `normal-resolution' data sets of ciprofloxacin hexahydrate. Topological properties and dipole moments are shown to be in excellent agreement for the two refinements. A `normal-resolution' data set of ciprofloxacin hydrochloride 1.4-hydrate is also evaluated in this manner.

Computing details

Data collection: APEX2 (Bruker, 2008) for CIPRO. Cell refinement: SAINT (Bruker, 1995-2008) for CIPRO. Data reduction: SAINT (Bruker, 1995-2008) for CIPRO. Program(s) used to solve structure: known coordinates for CIPRO. For both compounds, program(s) used to refine structure: Koritsanszky et al., (2003). Molecular graphics: ORTEP (Burnett & Johnson, 1996) XDGRAPH, Koritsanszky et al., (2003) for CIPRO; Koritsanszky et al., (2003) for cipro_hcl. Software used to prepare material for publication: XDCIF and enCIFer for CIPRO; Koritsanszky et al., (2003) for cipro_hcl.

(CIPRO) 1-cyclopropyl-6-fiuoro-4-oxo-7-(1-piperazinyl)- 1,4-dihydroquinoline-3-carboxylic acid) hexahydrate

Crystal data

C17H18FN3O3·6(H2O)	Z = 2.0
Mr = 439.44	F(000) = 468
Triclinic, P1	Dx = 1.424 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5070 (1) Å	Cell parameters from 9849 reflections
b = 9.9649 (1) Å	θ = 2.6–55.5°
c = 11.0233 (1) Å	µ = 0.12 mm^−1
α = 94.182 (1)°	T = 100 K
β = 100.118 (1)°	Plate, colourless
γ = 91.432 (1)°	0.17 × 0.08 × 0.07 mm
V = 1024.57 (2) Å^3

Data collection

Bruker APEX2 diffractometer	26308 independent reflections
Radiation source: Mo microsource	26308 reflections with F > 3(σ)F
Graphite monochromator	Rint = 0.025
ω scans	θmax = 55.6°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996-2008)	h = −22→21
Tmin = 0.967, Tmax = 0.999	k = −23→23
140939 measured reflections	l = 0→25

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	Primary atom site location: other
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters not refined
wR(F^2) = 0.023	w1 = 1/[s^2(Fo)]
S = 2.43	(Δ/σ)max < 0.001
21377 reflections	Δρmax = 0.27 e Å^−3
549 parameters	Δρmin = −0.36 e Å^−3

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

	x	y	z	Uiso*/Ueq
F(1)	−0.33041 (2)	0.128501 (16)	0.583331 (13)	0.014
O(1)	0.40556 (2)	0.624874 (18)	0.788839 (18)	0.013
O(2)	0.20853 (2)	0.706873 (18)	0.846774 (18)	0.014
O(3)	−0.01115 (2)	0.50713 (2)	0.80849 (2)	0.016
O(41)	0.51182 (2)	0.36471 (2)	0.80791 (3)	0.026
O(51)	0.67356 (2)	0.70055 (2)	0.93738 (2)	0.022
O(61)	−0.12183 (3)	0.06556 (2)	−0.12583 (2)	0.023
O(71)	−0.05229 (2)	0.79597 (2)	0.91017 (2)	0.023
O(81)	−0.21502 (2)	0.44175 (2)	0.940160 (18)	0.02
O(91)	−0.350385 (19)	0.086219 (17)	0.003843 (15)	0.014
N(1)	0.173705 (16)	0.368938 (15)	0.515141 (18)	0.009
N(2)	−0.224784 (16)	0.041636 (17)	0.374680 (17)	0.009
N(3)	−0.373673 (18)	−0.120529 (16)	0.16149 (2)	0.01
C(1)	0.23903 (2)	0.331137 (19)	0.408529 (19)	0.01
C(2)	0.39767 (2)	0.31248 (2)	0.42943 (2)	0.015
C(3)	0.29518 (2)	0.19174 (2)	0.39580 (2)	0.014
C(4)	0.042358 (18)	0.311660 (16)	0.527949 (16)	0.008
C(5)	0.23805 (2)	0.466670 (18)	0.599536 (18)	0.009
C(6)	0.18357 (2)	0.516919 (18)	0.700278 (18)	0.009
C(7)	0.27224 (2)	0.624085 (18)	0.785512 (18)	0.01
C(8)	0.04731 (2)	0.465583 (18)	0.720270 (18)	0.01
C(9)	−0.019977 (19)	0.357695 (18)	0.629511 (18)	0.009
C(10)	−0.14968 (2)	0.294736 (19)	0.644502 (19)	0.011
C(11)	−0.21172 (2)	0.192560 (19)	0.561187 (19)	0.01
C(12)	−0.154884 (19)	0.147620 (18)	0.455192 (18)	0.009
C(13)	−0.147237 (19)	−0.013351 (18)	0.279650 (18)	0.01
C(14)	−0.22180 (2)	−0.142848 (18)	0.214810 (19)	0.011
C(15)	−0.44930 (2)	−0.065780 (19)	0.260541 (18)	0.011
C(16)	−0.375520 (19)	0.064366 (18)	0.321621 (18)	0.01
C(17)	−0.026449 (18)	0.209634 (17)	0.440695 (18)	0.009
H(312)	−0.423665	−0.210191	0.125194	0.021
H(322)	−0.379127	−0.056162	0.092919	0.019
H(11)	0.18946	0.377106	0.324337	0.019
H(21)	0.453071	0.326278	0.525467	0.025
H(22)	0.453526	0.347794	0.358382	0.027
H(31)	0.281114	0.142335	0.302329	0.025
H(32)	0.285136	0.127921	0.470686	0.024
H(51)	0.340119	0.506949	0.584611	0.023
H(101)	−0.200137	0.324322	0.722497	0.022
H(131)	−0.04084	−0.03961	0.326597	0.023
H(132)	−0.137794	0.058737	0.210353	0.018
H(141)	−0.168923	−0.181592	0.139094	0.023
H(142)	−0.222171	−0.22205	0.279162	0.022
H(151)	−0.444035	−0.144201	0.326186	0.021
H(152)	−0.561212	−0.050565	0.219506	0.027
H(161)	−0.378851	0.140817	0.254241	0.021
H(162)	−0.434578	0.098612	0.394673	0.024
H(171)	0.019181	0.181411	0.35964	0.019
H(411)	0.605704	0.379675	0.857162	0.037
H(412)	0.473843	0.453226	0.805564	0.032
H(511)	0.700726	0.609699	0.950508	0.034
H(512)	0.578841	0.686763	0.889438	0.034
H(611)	−0.090236	−0.024967	−0.119118	0.03
H(612)	−0.056548	0.118209	−0.06257	0.03
H(711)	0.005844	0.730424	0.87646	0.031
H(712)	−0.144418	0.753243	0.908953	0.035
H(811)	−0.177398	0.405722	1.017357	0.031
H(812)	−0.135598	0.460565	0.8999	0.03
H(911)	−0.280529	0.071047	−0.048582	0.027
H(912)	−0.316432	0.165416	0.057121	0.024

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F(1)	0.01252 (5)	0.01698 (5)	0.01436 (6)	−0.00611 (5)	0.00629 (4)	−0.00327 (4)
O(1)	0.00972 (6)	0.01264 (5)	0.01667 (6)	−0.00204 (4)	0.00113 (5)	−0.00242 (6)
O(2)	0.01401 (6)	0.01155 (5)	0.01601 (6)	−0.00166 (4)	0.00420 (5)	−0.00513 (5)
O(3)	0.01487 (6)	0.01760 (6)	0.01470 (6)	−0.00507 (6)	0.00789 (6)	−0.00741 (7)
O(41)	0.01902 (8)	0.01191 (6)	0.04679 (14)	−0.00189 (5)	0.00295 (8)	−0.00021 (7)
O(51)	0.01710 (7)	0.02009 (7)	0.02593 (9)	−0.00240 (6)	−0.00147 (7)	−0.00556 (6)
O(61)	0.02381 (9)	0.02390 (8)	0.02310 (8)	0.00263 (6)	0.00823 (8)	0.00056 (7)
O(71)	0.01881 (7)	0.01755 (7)	0.03079 (10)	0.00098 (5)	0.00636 (7)	−0.00562 (7)
O(81)	0.01637 (7)	0.02718 (9)	0.01901 (7)	0.00322 (6)	0.00682 (6)	0.00782 (7)
O(91)	0.01435 (6)	0.01497 (5)	0.01285 (6)	−0.00331 (4)	0.00091 (5)	−0.00017 (5)
N(1)	0.00806 (5)	0.00936 (5)	0.00897 (6)	−0.00108 (3)	0.00262 (4)	−0.00120 (4)
N(2)	0.00761 (5)	0.00985 (5)	0.00982 (5)	−0.00052 (3)	0.00145 (4)	−0.00206 (5)
N(3)	0.00997 (5)	0.01061 (6)	0.01002 (6)	−0.00049 (4)	0.00056 (4)	−0.00141 (4)
C(1)	0.01004 (6)	0.01140 (6)	0.00957 (6)	0.00030 (5)	0.00335 (5)	−0.00010 (5)
C(2)	0.00990 (6)	0.01749 (7)	0.01758 (8)	−0.00102 (5)	0.00538 (6)	−0.00268 (6)
C(3)	0.01351 (7)	0.01213 (6)	0.01594 (8)	0.00119 (5)	0.00482 (6)	−0.00205 (5)
C(4)	0.00753 (5)	0.00880 (5)	0.00829 (5)	−0.00062 (4)	0.00180 (4)	−0.00084 (5)
C(5)	0.00881 (5)	0.00938 (5)	0.01001 (6)	−0.00143 (4)	0.00249 (5)	−0.00123 (5)
C(6)	0.00901 (5)	0.00879 (5)	0.00955 (6)	−0.00101 (4)	0.00206 (5)	−0.00133 (5)
C(7)	0.00998 (6)	0.00859 (5)	0.01041 (6)	−0.00108 (4)	0.00159 (5)	−0.00117 (5)
C(8)	0.00917 (6)	0.00997 (5)	0.00937 (6)	−0.00097 (4)	0.00269 (5)	−0.00196 (5)
C(9)	0.00817 (5)	0.00951 (5)	0.00891 (6)	−0.00083 (4)	0.00232 (5)	−0.00152 (5)
C(10)	0.00956 (6)	0.01184 (6)	0.01023 (6)	−0.00221 (5)	0.00371 (5)	−0.00278 (5)
C(11)	0.00914 (5)	0.01114 (5)	0.01009 (6)	−0.00233 (5)	0.00342 (5)	−0.00194 (5)
C(12)	0.00797 (5)	0.00942 (5)	0.00897 (6)	−0.00112 (4)	0.00193 (5)	−0.00151 (5)
C(13)	0.00848 (5)	0.01069 (5)	0.01095 (6)	−0.00014 (4)	0.00199 (5)	−0.00195 (5)
C(14)	0.01044 (6)	0.00978 (5)	0.01234 (6)	0.00097 (4)	0.00089 (5)	−0.00202 (5)
C(15)	0.00882 (5)	0.01268 (6)	0.01101 (6)	−0.00182 (4)	0.00160 (5)	−0.00106 (5)
C(16)	0.00861 (5)	0.01049 (5)	0.01159 (6)	0.00055 (4)	0.00142 (5)	−0.00144 (5)
C(17)	0.00832 (5)	0.01016 (5)	0.00898 (6)	−0.00128 (4)	0.00224 (5)	−0.00175 (5)
H(312)	0.012466	0.020259	0.027236	−0.00604	−0.000618	−0.003937
H(322)	0.012466	0.023691	0.021345	−0.001161	0.001165	0.003503
H(11)	0.012152	0.025599	0.020031	0.000597	0.004321	0.003973
H(21)	0.01773	0.03068	0.025338	0.001917	−0.000026	−0.004297
H(22)	0.01773	0.033094	0.033704	−0.001579	0.017884	0.001341
H(31)	0.016399	0.03468	0.023617	0.001166	0.006277	−0.009335
H(32)	0.016399	0.028997	0.028636	0.002022	0.006399	0.007124
H(51)	0.011179	0.028485	0.031433	−0.007308	0.009433	−0.002995
H(101)	0.0125	0.032667	0.02242	−0.003904	0.014024	−0.006658
H(131)	0.012092	0.027603	0.027389	0.005131	−0.001685	−0.002188
H(132)	0.012092	0.022171	0.021223	0.000176	0.007578	0.004083
H(141)	0.013258	0.032191	0.024668	0.001434	0.007339	−0.007819
H(142)	0.013258	0.023491	0.028278	−0.002792	0.000465	0.0069
H(151)	0.013103	0.023397	0.02626	−0.001473	0.005756	0.004726
H(152)	0.013103	0.033697	0.032172	0.001761	−0.001411	−0.003681
H(161)	0.012387	0.025126	0.025378	−0.001755	0.001542	0.007094
H(162)	0.012387	0.033722	0.025594	−0.00107	0.010119	−0.00579
H(171)	0.010932	0.028052	0.019966	−0.001507	0.010896	−0.00472
H(411)	0.039458	0.030199	0.034449	−0.001431	−0.006333	−0.003113
H(412)	0.039458	0.019753	0.033311	0.002783	0.001594	−0.001265
H(511)	0.032998	0.023394	0.040557	0.000231	−0.001556	−0.002216
H(512)	0.032998	0.02987	0.034753	−0.004092	−0.003575	−0.003751
H(611)	0.034603	0.028388	0.027518	0.002275	0.006794	−0.003028
H(612)	0.034603	0.032895	0.021302	−0.004922	0.002692	−0.005226
H(711)	0.033627	0.026326	0.032324	0.003758	0.010079	−0.008854
H(712)	0.033627	0.033533	0.037353	−0.003786	0.009987	−0.009533
H(811)	0.029997	0.04238	0.021156	−0.004962	0.009232	−0.000791
H(812)	0.029997	0.036604	0.026509	−0.004545	0.013682	−0.002478
H(911)	0.021381	0.035769	0.024674	0.001992	0.010449	−0.001112
H(912)	0.021381	0.023467	0.02502	−0.003013	0.000988	−0.005993

Geometric parameters (Å, º)

F(1)—C(11)	1.3505 (3)	C(2)—H(21)	1.0937
O(1)—C(7)	1.2614 (3)	C(2)—H(22)	1.0937
O(2)—C(7)	1.2613 (3)	C(3)—H(31)	1.0937
O(3)—C(8)	1.2524 (3)	C(3)—H(32)	1.0937
O(41)—H(411)	0.9618	C(4)—C(9)	1.4095 (2)
O(41)—H(412)	0.9618	C(4)—C(17)	1.4106 (2)
O(51)—H(511)	0.9618	C(5)—C(6)	1.3734 (3)
O(51)—H(512)	0.9618	C(5)—H(51)	1.0844
O(61)—H(611)	0.9618	C(6)—C(7)	1.5047 (3)
O(61)—H(612)	0.9618	C(6)—C(8)	1.4395 (3)
O(71)—H(711)	0.9618	C(8)—C(9)	1.4662 (3)
O(71)—H(712)	0.9618	C(9)—C(10)	1.4105 (3)
O(81)—H(811)	0.9618	C(10)—C(11)	1.3680 (3)
O(81)—H(812)	0.9618	C(10)—H(101)	1.0822
O(91)—H(911)	0.9618	C(11)—C(12)	1.4196 (3)
O(91)—H(912)	0.9618	C(12)—C(17)	1.3941 (2)
N(1)—C(1)	1.4534 (2)	C(13)—C(14)	1.5233 (3)
N(1)—C(4)	1.3939 (2)	C(13)—H(131)	1.0993
N(1)—C(5)	1.3514 (2)	C(13)—H(132)	1.0993
N(2)—C(12)	1.4020 (2)	C(14)—H(141)	1.0993
N(2)—C(13)	1.4659 (2)	C(14)—H(142)	1.0993
N(3)—H(312)	1.0218	C(15)—C(16)	1.5128 (3)
N(3)—H(322)	1.0218	C(15)—H(151)	1.0993
C(1)—C(2)	1.5035 (3)	C(15)—H(152)	1.0993
C(1)—C(3)	1.5063 (3)	C(16)—H(161)	1.0993
C(1)—H(11)	1.1011	C(16)—H(162)	1.0993
C(2)—C(3)	1.5113 (3)	C(17)—H(171)	1.0822
C(1)—N(1)—C(4)	121.137 (15)	O(1)—C(7)—C(6)	116.921 (18)
C(1)—N(1)—C(5)	119.119 (14)	O(2)—C(7)—C(6)	118.117 (19)
C(4)—N(1)—C(5)	119.643 (15)	O(3)—C(8)—C(6)	123.74 (2)
C(12)—N(2)—C(13)	116.136 (14)	O(3)—C(8)—C(9)	121.253 (19)
N(1)—C(1)—C(2)	118.111 (18)	C(6)—C(8)—C(9)	115.007 (17)
N(1)—C(1)—C(3)	118.626 (17)	C(4)—C(9)—C(8)	122.153 (16)
C(2)—C(1)—C(3)	60.279 (14)	C(4)—C(9)—C(10)	118.158 (17)
C(1)—C(2)—C(3)	59.955 (13)	C(8)—C(9)—C(10)	119.673 (17)
C(1)—C(3)—C(2)	59.766 (13)	C(9)—C(10)—C(11)	119.911 (18)
N(1)—C(4)—C(9)	118.724 (15)	F(1)—C(11)—C(10)	118.158 (17)
N(1)—C(4)—C(17)	120.432 (15)	F(1)—C(11)—C(12)	118.483 (17)
C(9)—C(4)—C(17)	120.844 (16)	C(10)—C(11)—C(12)	123.323 (17)
N(1)—C(5)—C(6)	124.877 (17)	N(2)—C(12)—C(11)	119.714 (16)
C(5)—C(6)—C(7)	117.210 (16)	N(2)—C(12)—C(17)	123.554 (17)
C(5)—C(6)—C(8)	119.561 (18)	C(11)—C(12)—C(17)	116.670 (17)
C(7)—C(6)—C(8)	123.228 (17)	N(2)—C(13)—C(14)	110.507 (14)
O(1)—C(7)—O(2)	124.96 (2)	C(4)—C(17)—C(12)	120.996 (17)

(cipro_hcl) 1-cyclopropyl-6-fiuoro-4-oxo-7-(1-piperazinyl)- 1,4-dihydroquinoline-3-carboxylic acid) 1.4hydrate hydrochloride

Crystal data

C17H19FN3O3·1.4(H2O)·Cl	Z = 4
Mr = 393.02	F(000) = 824.0
Monoclinic, P21/c	Dx = 1.491 Mg m^−3
Hall symbol: -P 2ybc	Synchrotron radiation, λ = 0.7660 Å
a = 12.872 (1) Å	µ = 0.26 mm^−1
b = 19.576 (1) Å	T = 100 K
c = 6.948 (1) Å	Thin plate, colourless
β = 90.55 (5)°	0.62 × 0.31 × 0.01 mm
V = 1750.7 (3) Å^3

Data collection

MAR 345 diffractometer	5732 reflections with F > 3(σ)F
Radiation source: Synchrotron	Rint = 0.0
φ scans	θmax = 36.7°
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996-2008)	h = −19→20
Tmin = 0.792, Tmax = 0.998	k = −29→28
68821 measured reflections	l = −8→9
6338 independent reflections

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	Primary atom site location: other
R[F^2 > 2σ(F^2)] = 0.038	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.050	(Δ/σ)max = 0.003
S = 2.77	Δρmax = 1.01 e Å^−3
5732 reflections	Δρmin = −0.82 e Å^−3
291 parameters

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl(1)	−0.20203	0.49929	0.19796	0.032
F(1)	0.0777	0.81003	0.38906	0.02
O(1)	0.6807	0.72031	0.01987	0.023
O(2)	0.62565	0.8264	0.06165	0.02
O(3)	0.44655	0.84788	0.18513	0.018
O(41)	0.75002	0.59834	−0.14838	0.037
O(51)	0.0292	0.54383	0.0613	0.042	0.4
N(1)	0.39877	0.64086	0.18849	0.015
N(2)	0.04445	0.67324	0.40873	0.019
N(3)	−0.14999	0.61086	0.49431	0.021
C(1)	0.38386	0.56732	0.18335	0.017
C(2)	0.47071	0.52244	0.25247	0.023
C(3)	0.37456	0.53041	0.37157	0.022
C(4)	0.31748	0.68382	0.24018	0.015
C(5)	0.4891	0.66762	0.13337	0.015
C(6)	0.50894	0.73666	0.12987	0.015
C(7)	0.61202	0.75964	0.06666	0.017
C(8)	0.43061	0.78426	0.18355	0.014
C(9)	0.33163	0.75519	0.23636	0.014
C(10)	0.24807	0.798	0.28507	0.016
C(11)	0.15603	0.76926	0.33525	0.016
C(12)	0.13942	0.6979	0.34218	0.016
C(13)	0.04171	0.60274	0.47504	0.025
C(14)	−0.05248	0.59329	0.60037	0.023
C(15)	−0.14482	0.67969	0.40258	0.02
C(16)	−0.04673	0.68772	0.28761	0.019
C(17)	0.22165	0.65581	0.2925	0.016
H(2)	0.56333	0.84694	0.10996	0.03
H(312)	−0.20812	0.60574	0.59238	0.037
H(322)	−0.16776	0.57573	0.39038	0.036
H(11)	0.33568	0.5497	0.06134	0.032
H(21)	0.54087	0.54605	0.31255	0.037
H(22)	0.48818	0.47617	0.17079	0.039
H(31)	0.31791	0.48878	0.37291	0.036
H(32)	0.38407	0.56241	0.49952	0.034
H(51)	0.5488	0.63212	0.08839	0.035
H(101)	0.25622	0.853	0.2881	0.031
H(131)	0.11132	0.5937	0.56435	0.033
H(132)	0.04171	0.56844	0.34981	0.034
H(141)	−0.06096	0.53993	0.64687	0.036
H(142)	−0.04965	0.62954	0.7211	0.035
H(151)	−0.14794	0.71715	0.52019	0.037
H(152)	−0.21538	0.68742	0.31489	0.039
H(161)	−0.04802	0.65045	0.16931	0.035
H(162)	−0.04515	0.74086	0.23666	0.035
H(171)	0.2119	0.60097	0.28493	0.031
H(411)	0.73203	0.64084	−0.08785	0.04
H(412)	0.77047	0.56964	−0.04229	0.043
H(511)	0.08318	0.52522	−0.01781	0.036	0.4
H(512)	−0.02948	0.53117	−0.01765	0.037	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl(1)	0.0448	0.0255	0.0262	−0.0079	−0.0126	0.0026
F(1)	0.0159	0.0227	0.0206	0.0033	0.0023	0.0009
O(1)	0.0154	0.0226	0.0321	−0.0008	0.0079	−0.0026
O(2)	0.0169	0.0222	0.0209	−0.0047	0.0023	−0.0001
O(3)	0.0165	0.0152	0.0229	−0.0016	0.0017	0.0008
O(41)	0.0546	0.0328	0.0227	0.0159	0.0062	0.0039
O(51)	0.0481	0.0398	0.0382	−0.0042	0.0163	−0.0121
N(1)	0.0134	0.0161	0.0147	−0.0015	−0.0013	−0.0011
N(2)	0.0132	0.0209	0.0232	−0.0005	−0.0006	0.0059
N(3)	0.0154	0.0243	0.022	−0.0037	0.0013	−0.0007
C(1)	0.0176	0.0158	0.0178	−0.0008	0	−0.0016
C(2)	0.0227	0.02	0.0253	0.0038	0.0018	0.0025
C(3)	0.0244	0.018	0.0221	−0.0004	0.0024	0.002
C(4)	0.0131	0.0166	0.0143	−0.0012	−0.0013	0.0007
C(5)	0.0141	0.0173	0.0145	−0.0007	0	−0.0007
C(6)	0.0123	0.0173	0.0146	−0.0011	0.0005	0.0003
C(7)	0.0134	0.0214	0.0166	−0.0017	0.002	−0.0011
C(8)	0.0138	0.0154	0.0134	−0.001	−0.0008	0.0007
C(9)	0.0126	0.0167	0.0131	0	−0.0005	0.0007
C(10)	0.0146	0.0174	0.0156	0.0003	−0.0003	0.0013
C(11)	0.014	0.0188	0.0157	0.001	0.0006	0.0014
C(12)	0.0125	0.019	0.0175	−0.0003	−0.0006	0.0033
C(13)	0.0161	0.023	0.0354	0	0.0015	0.0109
C(14)	0.0184	0.025	0.0271	−0.0053	−0.0012	0.0073
C(15)	0.013	0.0244	0.0232	0.0004	0.0008	−0.0003
C(16)	0.0125	0.0243	0.0205	0.0004	−0.0003	0.0033
C(17)	0.0129	0.0177	0.0186	−0.0012	−0.0003	0.0017
H(2)	0.0261	0.0316	0.0334	0.001	0.0072	−0.0002
H(312)	0.0268	0.0448	0.0389	−0.0081	0.0019	0.0018
H(322)	0.0342	0.0383	0.0359	−0.0094	−0.0059	−0.0028
H(11)	0.0382	0.0307	0.0266	0.0009	−0.0046	−0.0035
H(21)	0.0338	0.0389	0.038	−0.0009	−0.0028	0.0024
H(22)	0.0522	0.0274	0.038	0.0087	0.0041	−0.0039
H(31)	0.0365	0.0266	0.0441	−0.0029	−0.0024	0.0036
H(32)	0.0381	0.0338	0.0295	0.0044	−0.0049	−0.005
H(51)	0.0324	0.0313	0.0403	0.0089	0.008	−0.0024
H(101)	0.0317	0.0206	0.0407	−0.0006	0.0033	−0.0011
H(131)	0.0275	0.0374	0.0333	−0.0031	−0.0089	0.0063
H(132)	0.0416	0.0319	0.0289	−0.0066	−0.0025	−0.0041
H(141)	0.0343	0.0303	0.0443	−0.0065	−0.003	0.0086
H(142)	0.031	0.0402	0.0337	−0.0046	−0.0028	−0.0066
H(151)	0.0362	0.0366	0.0377	−0.0046	0.0008	−0.0034
H(152)	0.0258	0.0467	0.0438	−0.0036	−0.011	0.0091
H(161)	0.0345	0.0372	0.034	−0.0028	−0.0061	−0.0066
H(162)	0.0319	0.0287	0.0436	−0.0014	−0.0038	0.0086
H(171)	0.0345	0.0208	0.0389	−0.0018	−0.0004	−0.0013
H(411)	0.0418	0.0379	0.039	0.0102	0.0096	−0.0036
H(412)	0.0445	0.0438	0.0404	0.0132	0.0074	0.0051
H(511)	0.0406	0.0339	0.0324	−0.0008	−0.0018	−0.0039
H(512)	0.0391	0.0375	0.0344	−0.0083	−0.0131	−0.0017

Geometric parameters (Å, º)

F(1)—C(11)	1.3418	C(4)—C(9)	1.4094
O(1)—C(7)	1.2188	C(4)—C(17)	1.4010
O(2)—C(7)	1.3193	C(5)—C(6)	1.3759
O(3)—C(8)	1.2625	C(6)—C(7)	1.4720
N(1)—C(1)	1.4532	C(6)—C(8)	1.4252
N(1)—C(4)	1.3922	C(8)—C(9)	1.4458
N(1)—C(5)	1.3346	C(9)—C(10)	1.4074
N(2)—C(12)	1.3970	C(10)—C(11)	1.3600
N(2)—C(13)	1.4559	C(11)—C(12)	1.4144
N(2)—C(16)	1.4652	C(12)—C(17)	1.3878
C(1)—C(2)	1.4972	C(13)—C(14)	1.5108
C(1)—C(3)	1.5003	C(15)—C(16)	1.5088
C(2)—C(3)	1.5034
C(7)—O(2)—H(2)	107.1	O(1)—C(7)—O(2)	121.46
C(1)—N(1)—C(4)	120.38	O(1)—C(7)—C(6)	122.99
C(1)—N(1)—C(5)	119.81	O(2)—C(7)—C(6)	115.54
C(4)—N(1)—C(5)	119.71	O(3)—C(8)—C(6)	122.16
C(12)—N(2)—C(13)	117.16	O(3)—C(8)—C(9)	121.98
C(12)—N(2)—C(16)	116.19	C(6)—C(8)—C(9)	115.86
C(13)—N(2)—C(16)	110.09	C(4)—C(9)—C(8)	120.62
N(1)—C(1)—C(2)	118.4	C(4)—C(9)—C(10)	119.13
N(1)—C(1)—C(3)	117.87	C(8)—C(9)—C(10)	120.25
C(2)—C(1)—C(3)	60.21	C(9)—C(10)—C(11)	118.99
C(1)—C(2)—C(3)	60	F(1)—C(11)—C(10)	118.94
C(1)—C(3)—C(2)	59.8	F(1)—C(11)—C(12)	117.64
N(1)—C(4)—C(9)	119.77	C(10)—C(11)—C(12)	123.35
N(1)—C(4)—C(17)	119.73	N(2)—C(12)—C(11)	119.06
C(9)—C(4)—C(17)	120.48	N(2)—C(12)—C(17)	123.29
N(1)—C(5)—C(6)	123.58	C(11)—C(12)—C(17)	117.54
C(5)—C(6)—C(7)	118.27	N(2)—C(13)—C(14)	108.7
C(5)—C(6)—C(8)	120.4	N(2)—C(16)—C(15)	110.19
C(7)—C(6)—C(8)	121.33	C(4)—C(17)—C(12)	120.49