Crystal structure of 4-[4-(eth­oxy­carbon­yl)piperazin-1-yl]benzoic acid

4-[4-(Eth­oxy­carbon­yl)piperazin-1-yl]benzoic acid (EPBA) is the product of a reaction between ethyl 1-piperazine­carboxyl­ate and 4-fluoro­benzoic acid. The conformation of the two independent mol­ecules (A and B) in the asymmetric unit is similar. The piperazine ring adopts a chair conformation in both mol­ecules. The dihedral angles formed by the four approximately planar C atoms of the piperazine ring and the benzene ring is 30.8 (5)° in mol­ecule A and 30.6 (5)% in mol­ecule B.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.077
• wR factor = 0.202
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0108 Ang.

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.645
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.200
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.71 Note
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.64 eA-3
PLAT148_ALERT_3_C s.u. on the      b  - Axis is (Too) Large ......     0.0050 Ang.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1A    --  C1A     ..        6.2 s.u.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          3 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         69 %
PLAT975_ALERT_2_C Check Calcd Residual Density  0.73A From     O2B       0.64 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.79A From     O2A       0.57 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)      0.005 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         16 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          48 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

4-[4-(Ethoxycarbonyl)piperazin-1-yl]benzoic acid

Crystal data

C14H18N2O4	Dx = 1.352 Mg m^−3
Mr = 278.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 999 reflections
a = 18.508 (5) Å	θ = 2.2–25.5°
b = 4.994 (5) Å	µ = 0.10 mm^−1
c = 29.594 (5) Å	T = 173 K
V = 2735 (3) Å^3	Block, colorless
Z = 8	0.29 × 0.21 × 0.15 mm
F(000) = 1184

Data collection

Bruker SMART APEX diffractometer	3100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
/w–scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −22→21
Tmin = 0.972, Tmax = 0.985	k = −5→5
12918 measured reflections	l = −35→25
4042 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.077	w = 1/[σ^2(Fo^2) + (0.1131P)^2 + 0.9875P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.202	(Δ/σ)max = 0.002
S = 1.08	Δρmax = 0.65 e Å^−3
4042 reflections	Δρmin = −0.47 e Å^−3
363 parameters	Absolute structure: Flack x determined using 850 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.2 (10)

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
O1A	0.6918 (3)	0.2291 (13)	0.3795 (3)	0.044 (2)
H1A	0.6528	0.2795	0.3678	0.065*
O2A	0.6971 (2)	0.6589 (12)	0.3981 (2)	0.0289 (13)
O3A	1.1546 (2)	−0.0268 (10)	0.61300 (19)	0.0282 (13)
O4A	1.1990 (3)	−0.2288 (9)	0.5501 (2)	0.0209 (14)
N1A	0.9933 (3)	0.2577 (10)	0.4888 (3)	0.0173 (18)
N2A	1.1101 (3)	0.0764 (13)	0.5433 (2)	0.0260 (15)
C1A	0.7243 (4)	0.4362 (14)	0.3986 (3)	0.0196 (16)
C2A	0.7949 (4)	0.3828 (13)	0.4214 (3)	0.0197 (16)
C3A	0.8164 (3)	0.5513 (14)	0.4560 (3)	0.0217 (16)
H3AA	0.7865	0.6969	0.4647	0.026*
C4A	0.8816 (3)	0.5082 (14)	0.4781 (3)	0.0219 (16)
H4AA	0.8957	0.6237	0.5021	0.026*
C5A	0.9277 (4)	0.2923 (16)	0.4653 (3)	0.0215 (19)
C6A	0.9066 (3)	0.1323 (14)	0.4308 (3)	0.0204 (16)
H6AA	0.9369	−0.0110	0.4216	0.024*
C7A	0.8404 (4)	0.1743 (18)	0.4086 (3)	0.0212 (16)
H7AA	0.8266	0.0591	0.3845	0.025*
C8A	0.9880 (4)	0.2484 (15)	0.5397 (3)	0.022 (2)
H8AA	0.9564	0.3955	0.5503	0.026*
H8AB	0.9658	0.0767	0.5490	0.026*
C9A	1.0603 (4)	0.2747 (17)	0.5609 (3)	0.027 (2)
H9AA	1.0797	0.4562	0.5551	0.033*
H9AB	1.0558	0.2519	0.5940	0.033*
C10A	1.1159 (4)	0.0718 (17)	0.4939 (3)	0.0285 (19)
H10A	1.1459	−0.0828	0.4846	0.034*
H10B	1.1402	0.2372	0.4834	0.034*
C11A	1.0420 (3)	0.0510 (15)	0.4721 (3)	0.0225 (17)
H11A	1.0470	0.0688	0.4389	0.027*
H11B	1.0211	−0.1275	0.4785	0.027*
C12A	1.1547 (3)	−0.0536 (14)	0.5723 (2)	0.0183 (16)
C13A	1.2448 (4)	−0.3858 (16)	0.5793 (3)	0.0301 (19)
H13A	1.2154	−0.4868	0.6014	0.036*
H13B	1.2788	−0.2686	0.5959	0.036*
C14A	1.2859 (4)	−0.5770 (15)	0.5485 (3)	0.0271 (18)
H14A	1.3186	−0.6875	0.5667	0.041*
H14B	1.3141	−0.4739	0.5265	0.041*
H14C	1.2516	−0.6926	0.5326	0.041*
O1B	0.5524 (3)	0.7761 (13)	0.3627 (3)	0.045 (2)
H1B	0.5911	0.7222	0.3744	0.067*
O2B	0.5460 (2)	0.3407 (11)	0.34180 (19)	0.0242 (12)
O3B	0.0883 (3)	1.0119 (11)	0.12725 (19)	0.0296 (13)
O4B	0.0441 (3)	1.2149 (11)	0.1901 (2)	0.0222 (14)
N1B	0.2507 (3)	0.7383 (12)	0.2493 (3)	0.0208 (19)
N2B	0.1310 (3)	0.9039 (12)	0.1970 (2)	0.0219 (14)
C1B	0.5191 (3)	0.5682 (13)	0.3412 (3)	0.0182 (16)
C2B	0.4492 (4)	0.6208 (14)	0.3179 (3)	0.0194 (16)
C3B	0.4035 (4)	0.8309 (17)	0.3305 (3)	0.0202 (16)
H3BA	0.4176	0.9480	0.3543	0.024*
C4B	0.3379 (4)	0.8706 (15)	0.3089 (3)	0.0205 (16)
H4BA	0.3066	1.0094	0.3188	0.025*
C5B	0.3175 (3)	0.7085 (16)	0.2727 (3)	0.0179 (17)
C6B	0.3630 (4)	0.4965 (14)	0.2608 (3)	0.0237 (16)
H6BA	0.3492	0.3795	0.2369	0.028*
C7B	0.4273 (4)	0.4547 (15)	0.2829 (3)	0.0222 (17)
H7BA	0.4573	0.3093	0.2741	0.027*
C8B	0.2016 (3)	0.9471 (15)	0.2664 (3)	0.0237 (17)
H8BA	0.2210	1.1259	0.2586	0.028*
H8BB	0.1986	0.9348	0.2998	0.028*
C9B	0.1267 (4)	0.9150 (17)	0.2462 (3)	0.0260 (18)
H9BA	0.1043	0.7484	0.2578	0.031*
H9BB	0.0959	1.0677	0.2554	0.031*
C10B	0.1800 (4)	0.7025 (18)	0.1806 (3)	0.0238 (19)
H10C	0.1830	0.7130	0.1472	0.029*
H10D	0.1617	0.5226	0.1888	0.029*
C11B	0.2552 (4)	0.7435 (14)	0.2011 (3)	0.022 (2)
H11C	0.2881	0.6001	0.1905	0.026*
H11D	0.2751	0.9176	0.1910	0.026*
C12B	0.0880 (4)	1.0370 (15)	0.1678 (3)	0.0241 (18)
C13B	−0.0015 (4)	1.3737 (16)	0.1605 (3)	0.0266 (18)
H13C	−0.0346	1.2564	0.1433	0.032*
H13D	0.0285	1.4762	0.1389	0.032*
C14B	−0.0436 (4)	1.5605 (15)	0.1900 (3)	0.0276 (18)
H14E	−0.0708	1.6860	0.1711	0.041*
H14F	−0.0103	1.6605	0.2095	0.041*
H14G	−0.0772	1.4574	0.2088	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.047 (4)	0.052 (5)	0.033 (5)	0.000 (3)	0.003 (3)	0.007 (3)
O2A	0.025 (3)	0.024 (3)	0.038 (4)	0.001 (2)	−0.001 (2)	0.006 (3)
O3A	0.025 (3)	0.037 (3)	0.022 (3)	0.003 (2)	−0.005 (2)	−0.003 (3)
O4A	0.020 (3)	0.026 (3)	0.017 (4)	0.002 (2)	0.001 (2)	0.001 (2)
N1A	0.014 (3)	0.010 (4)	0.027 (5)	0.005 (2)	−0.001 (3)	0.000 (2)
N2A	0.025 (3)	0.035 (4)	0.018 (4)	0.004 (3)	−0.001 (3)	−0.003 (3)
C1A	0.024 (4)	0.007 (4)	0.028 (5)	−0.002 (3)	0.002 (3)	0.003 (3)
C2A	0.017 (4)	0.014 (4)	0.028 (5)	0.004 (3)	0.001 (3)	0.004 (3)
C3A	0.018 (3)	0.019 (4)	0.029 (4)	0.000 (3)	0.004 (3)	−0.001 (3)
C4A	0.018 (3)	0.017 (4)	0.030 (4)	0.000 (3)	0.000 (3)	−0.001 (3)
C5A	0.019 (3)	0.018 (4)	0.027 (5)	−0.004 (3)	0.005 (3)	0.006 (4)
C6A	0.016 (3)	0.013 (4)	0.032 (5)	0.005 (3)	0.003 (3)	0.003 (3)
C7A	0.024 (4)	0.026 (4)	0.014 (4)	0.005 (4)	0.003 (3)	0.003 (4)
C8A	0.020 (4)	0.033 (6)	0.012 (5)	0.008 (3)	0.003 (3)	−0.005 (3)
C9A	0.021 (4)	0.034 (5)	0.027 (5)	0.003 (3)	0.001 (3)	−0.009 (4)
C10A	0.022 (4)	0.040 (5)	0.024 (5)	0.005 (3)	0.001 (3)	0.003 (4)
C11A	0.022 (4)	0.025 (4)	0.020 (4)	0.002 (3)	−0.005 (3)	−0.001 (3)
C12A	0.014 (3)	0.024 (4)	0.017 (5)	−0.006 (3)	0.000 (3)	−0.001 (3)
C13A	0.027 (4)	0.029 (5)	0.035 (5)	0.007 (3)	−0.006 (4)	−0.003 (4)
C14A	0.025 (4)	0.016 (4)	0.041 (5)	0.001 (3)	−0.004 (3)	0.000 (3)
O1B	0.032 (3)	0.037 (4)	0.065 (6)	−0.004 (3)	−0.007 (3)	−0.006 (3)
O2B	0.020 (2)	0.020 (3)	0.032 (3)	0.001 (2)	0.002 (2)	−0.001 (3)
O3B	0.029 (3)	0.038 (3)	0.022 (3)	0.007 (2)	−0.003 (2)	−0.005 (3)
O4B	0.020 (3)	0.026 (3)	0.021 (4)	0.008 (2)	−0.003 (2)	0.003 (2)
N1B	0.014 (3)	0.034 (5)	0.015 (4)	0.004 (2)	−0.001 (3)	−0.004 (2)
N2B	0.013 (3)	0.026 (3)	0.026 (4)	0.007 (2)	0.000 (3)	−0.001 (3)
C1B	0.013 (3)	0.018 (4)	0.024 (4)	−0.002 (3)	0.001 (3)	0.000 (3)
C2B	0.023 (4)	0.015 (4)	0.021 (4)	−0.002 (3)	0.004 (3)	0.005 (3)
C3B	0.020 (3)	0.017 (4)	0.024 (4)	−0.004 (3)	−0.004 (3)	−0.002 (3)
C4B	0.021 (3)	0.020 (4)	0.020 (4)	0.002 (3)	0.003 (3)	−0.001 (3)
C5B	0.012 (3)	0.028 (4)	0.014 (4)	0.001 (3)	0.001 (3)	0.000 (3)
C6B	0.025 (4)	0.020 (4)	0.026 (4)	−0.001 (3)	0.000 (3)	−0.007 (3)
C7B	0.019 (3)	0.018 (4)	0.030 (5)	0.005 (3)	0.002 (3)	−0.001 (3)
C8B	0.019 (3)	0.030 (5)	0.022 (4)	0.007 (3)	0.003 (3)	−0.004 (3)
C9B	0.018 (4)	0.035 (5)	0.025 (5)	0.005 (3)	0.000 (3)	−0.001 (3)
C10B	0.023 (4)	0.031 (4)	0.017 (5)	0.003 (3)	−0.001 (3)	−0.002 (4)
C11B	0.019 (4)	0.017 (5)	0.029 (6)	0.001 (3)	0.001 (3)	0.000 (3)
C12B	0.015 (3)	0.023 (4)	0.035 (6)	0.000 (3)	−0.003 (3)	0.000 (3)
C13B	0.030 (4)	0.030 (5)	0.020 (4)	0.006 (3)	−0.006 (3)	0.001 (3)
C14B	0.026 (4)	0.025 (4)	0.032 (5)	0.001 (3)	0.003 (3)	0.008 (3)

Geometric parameters (Å, º)

O1A—C1A	1.324 (10)	O1B—C1B	1.365 (9)
O1A—H1A	0.8400	O1B—H1B	0.8400
O2A—C1A	1.221 (9)	O2B—C1B	1.241 (9)
O3A—C12A	1.212 (8)	O3B—C12B	1.207 (9)
O4A—C12A	1.367 (8)	O4B—C12B	1.372 (9)
O4A—C13A	1.441 (9)	O4B—C13B	1.451 (9)
N1A—C5A	1.409 (10)	N1B—C5B	1.425 (10)
N1A—C11A	1.457 (9)	N1B—C11B	1.430 (11)
N1A—C8A	1.510 (10)	N1B—C8B	1.473 (9)
N2A—C12A	1.357 (9)	N2B—C12B	1.351 (9)
N2A—C9A	1.450 (10)	N2B—C10B	1.439 (9)
N2A—C10A	1.464 (10)	N2B—C9B	1.460 (10)
C1A—C2A	1.494 (10)	C1B—C2B	1.490 (10)
C2A—C3A	1.384 (10)	C2B—C7B	1.387 (11)
C2A—C7A	1.392 (11)	C2B—C3B	1.399 (11)
C3A—C4A	1.390 (9)	C3B—C4B	1.388 (10)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.427 (10)	C4B—C5B	1.394 (11)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.352 (12)	C5B—C6B	1.399 (10)
C6A—C7A	1.406 (10)	C6B—C7B	1.376 (10)
C6A—H6AA	0.9500	C6B—H6BA	0.9500
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C9A	1.485 (11)	C8B—C9B	1.519 (9)
C8A—H8AA	0.9900	C8B—H8BA	0.9900
C8A—H8AB	0.9900	C8B—H8BB	0.9900
C9A—H9AA	0.9900	C9B—H9BA	0.9900
C9A—H9AB	0.9900	C9B—H9BB	0.9900
C10A—C11A	1.517 (9)	C10B—C11B	1.532 (11)
C10A—H10A	0.9900	C10B—H10C	0.9900
C10A—H10B	0.9900	C10B—H10D	0.9900
C11A—H11A	0.9900	C11B—H11C	0.9900
C11A—H11B	0.9900	C11B—H11D	0.9900
C13A—C14A	1.523 (11)	C13B—C14B	1.496 (11)
C13A—H13A	0.9900	C13B—H13C	0.9900
C13A—H13B	0.9900	C13B—H13D	0.9900
C14A—H14A	0.9800	C14B—H14E	0.9800
C14A—H14B	0.9800	C14B—H14F	0.9800
C14A—H14C	0.9800	C14B—H14G	0.9800
C1A—O1A—H1A	109.5	C1B—O1B—H1B	109.5
C12A—O4A—C13A	114.4 (7)	C12B—O4B—C13B	114.2 (7)
C5A—N1A—C11A	116.8 (7)	C5B—N1B—C11B	115.9 (6)
C5A—N1A—C8A	116.1 (6)	C5B—N1B—C8B	116.2 (7)
C11A—N1A—C8A	110.9 (6)	C11B—N1B—C8B	111.5 (6)
C12A—N2A—C9A	119.0 (7)	C12B—N2B—C10B	119.9 (7)
C12A—N2A—C10A	125.4 (6)	C12B—N2B—C9B	126.0 (6)
C9A—N2A—C10A	114.7 (7)	C10B—N2B—C9B	113.5 (6)
O2A—C1A—O1A	121.2 (7)	O2B—C1B—O1B	120.6 (6)
O2A—C1A—C2A	122.0 (7)	O2B—C1B—C2B	121.1 (6)
O1A—C1A—C2A	116.8 (6)	O1B—C1B—C2B	118.3 (6)
C3A—C2A—C7A	118.9 (6)	C7B—C2B—C3B	118.2 (6)
C3A—C2A—C1A	118.4 (6)	C7B—C2B—C1B	119.7 (6)
C7A—C2A—C1A	122.7 (7)	C3B—C2B—C1B	122.2 (7)
C2A—C3A—C4A	120.3 (6)	C4B—C3B—C2B	120.8 (7)
C2A—C3A—H3AA	119.9	C4B—C3B—H3BA	119.6
C4A—C3A—H3AA	119.9	C2B—C3B—H3BA	119.6
C3A—C4A—C5A	120.7 (7)	C3B—C4B—C5B	120.6 (7)
C3A—C4A—H4AA	119.7	C3B—C4B—H4BA	119.7
C5A—C4A—H4AA	119.7	C5B—C4B—H4BA	119.7
C6A—C5A—N1A	123.3 (7)	C4B—C5B—C6B	118.1 (7)
C6A—C5A—C4A	118.3 (7)	C4B—C5B—N1B	123.2 (7)
N1A—C5A—C4A	118.4 (7)	C6B—C5B—N1B	118.5 (7)
C5A—C6A—C7A	121.1 (7)	C7B—C6B—C5B	121.0 (7)
C5A—C6A—H6AA	119.4	C7B—C6B—H6BA	119.5
C7A—C6A—H6AA	119.4	C5B—C6B—H6BA	119.5
C2A—C7A—C6A	120.7 (7)	C6B—C7B—C2B	121.2 (7)
C2A—C7A—H7AA	119.6	C6B—C7B—H7BA	119.4
C6A—C7A—H7AA	119.6	C2B—C7B—H7BA	119.4
C9A—C8A—N1A	111.2 (7)	N1B—C8B—C9B	110.7 (6)
C9A—C8A—H8AA	109.4	N1B—C8B—H8BA	109.5
N1A—C8A—H8AA	109.4	C9B—C8B—H8BA	109.5
C9A—C8A—H8AB	109.4	N1B—C8B—H8BB	109.5
N1A—C8A—H8AB	109.4	C9B—C8B—H8BB	109.5
H8AA—C8A—H8AB	108.0	H8BA—C8B—H8BB	108.1
N2A—C9A—C8A	111.1 (7)	N2B—C9B—C8B	110.2 (6)
N2A—C9A—H9AA	109.4	N2B—C9B—H9BA	109.6
C8A—C9A—H9AA	109.4	C8B—C9B—H9BA	109.6
N2A—C9A—H9AB	109.4	N2B—C9B—H9BB	109.6
C8A—C9A—H9AB	109.4	C8B—C9B—H9BB	109.6
H9AA—C9A—H9AB	108.0	H9BA—C9B—H9BB	108.1
N2A—C10A—C11A	111.1 (6)	N2B—C10B—C11B	110.2 (6)
N2A—C10A—H10A	109.4	N2B—C10B—H10C	109.6
C11A—C10A—H10A	109.4	C11B—C10B—H10C	109.6
N2A—C10A—H10B	109.4	N2B—C10B—H10D	109.6
C11A—C10A—H10B	109.4	C11B—C10B—H10D	109.6
H10A—C10A—H10B	108.0	H10C—C10B—H10D	108.1
N1A—C11A—C10A	111.4 (6)	N1B—C11B—C10B	109.8 (7)
N1A—C11A—H11A	109.4	N1B—C11B—H11C	109.7
C10A—C11A—H11A	109.4	C10B—C11B—H11C	109.7
N1A—C11A—H11B	109.4	N1B—C11B—H11D	109.7
C10A—C11A—H11B	109.4	C10B—C11B—H11D	109.7
H11A—C11A—H11B	108.0	H11C—C11B—H11D	108.2
O3A—C12A—N2A	125.1 (7)	O3B—C12B—N2B	125.6 (7)
O3A—C12A—O4A	123.3 (7)	O3B—C12B—O4B	123.2 (7)
N2A—C12A—O4A	111.5 (6)	N2B—C12B—O4B	111.1 (7)
O4A—C13A—C14A	106.1 (7)	O4B—C13B—C14B	107.0 (6)
O4A—C13A—H13A	110.5	O4B—C13B—H13C	110.3
C14A—C13A—H13A	110.5	C14B—C13B—H13C	110.3
O4A—C13A—H13B	110.5	O4B—C13B—H13D	110.3
C14A—C13A—H13B	110.5	C14B—C13B—H13D	110.3
H13A—C13A—H13B	108.7	H13C—C13B—H13D	108.6
C13A—C14A—H14A	109.5	C13B—C14B—H14E	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14E—C14B—H14F	109.5
C13A—C14A—H14C	109.5	C13B—C14B—H14G	109.5
H14A—C14A—H14C	109.5	H14E—C14B—H14G	109.5
H14B—C14A—H14C	109.5	H14F—C14B—H14G	109.5
O2A—C1A—C2A—C3A	24.7 (11)	O2B—C1B—C2B—C7B	−24.7 (11)
O1A—C1A—C2A—C3A	−154.3 (7)	O1B—C1B—C2B—C7B	156.3 (7)
O2A—C1A—C2A—C7A	−154.0 (8)	O2B—C1B—C2B—C3B	153.9 (7)
O1A—C1A—C2A—C7A	27.0 (11)	O1B—C1B—C2B—C3B	−25.1 (11)
C7A—C2A—C3A—C4A	−1.4 (11)	C7B—C2B—C3B—C4B	0.4 (11)
C1A—C2A—C3A—C4A	179.8 (6)	C1B—C2B—C3B—C4B	−178.3 (7)
C2A—C3A—C4A—C5A	0.7 (11)	C2B—C3B—C4B—C5B	−2.8 (12)
C11A—N1A—C5A—C6A	4.9 (11)	C3B—C4B—C5B—C6B	3.7 (11)
C8A—N1A—C5A—C6A	−129.0 (8)	C3B—C4B—C5B—N1B	179.7 (7)
C11A—N1A—C5A—C4A	−174.5 (7)	C11B—N1B—C5B—C4B	131.7 (8)
C8A—N1A—C5A—C4A	51.5 (9)	C8B—N1B—C5B—C4B	−2.2 (11)
C3A—C4A—C5A—C6A	0.4 (11)	C11B—N1B—C5B—C6B	−52.3 (9)
C3A—C4A—C5A—N1A	179.9 (7)	C8B—N1B—C5B—C6B	173.8 (7)
N1A—C5A—C6A—C7A	179.7 (7)	C4B—C5B—C6B—C7B	−2.3 (11)
C4A—C5A—C6A—C7A	−0.9 (12)	N1B—C5B—C6B—C7B	−178.6 (7)
C3A—C2A—C7A—C6A	1.0 (12)	C5B—C6B—C7B—C2B	0.1 (12)
C1A—C2A—C7A—C6A	179.7 (7)	C3B—C2B—C7B—C6B	0.9 (11)
C5A—C6A—C7A—C2A	0.1 (12)	C1B—C2B—C7B—C6B	179.6 (7)
C5A—N1A—C8A—C9A	−166.9 (6)	C5B—N1B—C8B—C9B	−166.6 (7)
C11A—N1A—C8A—C9A	56.5 (8)	C11B—N1B—C8B—C9B	57.6 (8)
C12A—N2A—C9A—C8A	−137.3 (8)	C12B—N2B—C9B—C8B	−134.8 (7)
C10A—N2A—C9A—C8A	53.3 (9)	C10B—N2B—C9B—C8B	54.0 (8)
N1A—C8A—C9A—N2A	−54.1 (9)	N1B—C8B—C9B—N2B	−53.1 (9)
C12A—N2A—C10A—C11A	139.4 (7)	C12B—N2B—C10B—C11B	132.7 (7)
C9A—N2A—C10A—C11A	−52.0 (9)	C9B—N2B—C10B—C11B	−55.6 (9)
C5A—N1A—C11A—C10A	168.5 (6)	C5B—N1B—C11B—C10B	165.3 (6)
C8A—N1A—C11A—C10A	−55.3 (8)	C8B—N1B—C11B—C10B	−58.8 (8)
N2A—C10A—C11A—N1A	52.7 (9)	N2B—C10B—C11B—N1B	57.2 (9)
C9A—N2A—C12A—O3A	3.5 (11)	C10B—N2B—C12B—O3B	−3.5 (11)
C10A—N2A—C12A—O3A	171.6 (7)	C9B—N2B—C12B—O3B	−174.1 (7)
C9A—N2A—C12A—O4A	−178.7 (6)	C10B—N2B—C12B—O4B	178.4 (6)
C10A—N2A—C12A—O4A	−10.5 (10)	C9B—N2B—C12B—O4B	7.7 (10)
C13A—O4A—C12A—O3A	1.5 (9)	C13B—O4B—C12B—O3B	−0.8 (10)
C13A—O4A—C12A—N2A	−176.4 (6)	C13B—O4B—C12B—N2B	177.4 (6)
C12A—O4A—C13A—C14A	176.7 (6)	C12B—O4B—C13B—C14B	−178.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B	0.84	2.14	2.973 (8)	170
C8A—H8AB···O3B^i	0.99	2.56	3.225 (11)	124
O1B—H1B···O2A	0.84	2.11	2.934 (8)	168

Symmetry code: (i) −x+1, −y+1, z+1/2.