Crystal structure of (E)-4-hy­droxy-N′-(3-meth­oxy­benzyl­idene)benzohydrazide

The mol­ecules of C₁₅H₁₄N₂O₃ are slightly twisted. N—H...O, O—H...N and O—H...O hydrogen bonds play an important role in the crystal packing, resulting in the formation of mol­ecular sheets parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.105
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.376 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.215 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           7 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          4 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

(E)-4-Hydroxy-N'-(3-methoxybenzylidene)benzohydrazide

Crystal data

C15H14N2O3	Dx = 1.351 Mg m^−3
Mr = 270.28	Melting point = 478–479 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.2713 (6) Å	Cell parameters from 5213 reflections
b = 19.0235 (11) Å	θ = 2.9–26.0°
c = 15.6054 (9) Å	µ = 0.10 mm^−1
β = 105.118 (2)°	T = 300 K
V = 2657.1 (3) Å^3	Block, colorless
Z = 8	0.13 × 0.10 × 0.10 mm
F(000) = 1136

Data collection

Bruker SMART diffractometer	3311 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.103
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θmax = 26.0°, θmin = 2.9°
Tmin = 0.988, Tmax = 0.991	h = −11→11
70844 measured reflections	k = −23→23
5213 independent reflections	l = −19→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.602P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
5213 reflections	Δρmax = 0.14 e Å^−3
364 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (6)

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.43409 (17)	0.27645 (8)	0.84360 (9)	0.0583 (4)
O2A	0.50983 (17)	0.14048 (8)	0.48887 (9)	0.0572 (4)
H2A	0.4658	0.1573	0.4409	0.086*
O3A	0.25586 (17)	0.54386 (7)	1.08045 (9)	0.0536 (4)
N1A	0.26003 (19)	0.33795 (8)	0.74482 (10)	0.0447 (4)
H1A	0.2151	0.3461	0.6911	0.054*
N2A	0.24503 (19)	0.38366 (9)	0.81022 (10)	0.0445 (4)
C1A	0.3853 (2)	0.24216 (9)	0.69253 (12)	0.0352 (4)
C2A	0.5205 (2)	0.20673 (10)	0.70688 (13)	0.0436 (5)
H2A1	0.5851	0.2058	0.7636	0.052*
C3A	0.5603 (2)	0.17300 (11)	0.63865 (13)	0.0471 (5)
H3A	0.6518	0.1501	0.6492	0.057*
C4A	0.4647 (2)	0.17309 (9)	0.55460 (12)	0.0386 (5)
C5A	0.3262 (2)	0.20502 (10)	0.53997 (12)	0.0416 (5)
H5A	0.2594	0.2033	0.4840	0.050*
C6A	0.2875 (2)	0.23933 (10)	0.60853 (12)	0.0398 (5)
H6A	0.1945	0.2609	0.5983	0.048*
C7A	0.3611 (2)	0.28530 (10)	0.76666 (12)	0.0392 (5)
C8A	0.1550 (2)	0.43474 (10)	0.78455 (13)	0.0440 (5)
H8AA	0.1032	0.4378	0.7250	0.053*
C9A	0.1313 (2)	0.48859 (10)	0.84627 (13)	0.0421 (5)
C10A	0.2082 (2)	0.48732 (10)	0.93602 (13)	0.0432 (5)
H10A	0.2769	0.4518	0.9579	0.052*
C11A	0.1817 (2)	0.53895 (10)	0.99222 (13)	0.0439 (5)
C12A	0.0746 (3)	0.58989 (11)	0.96013 (16)	0.0560 (6)
H12A	0.0518	0.6228	0.9987	0.067*
C13A	0.0025 (3)	0.59198 (12)	0.87190 (17)	0.0625 (6)
H13A	−0.0670	0.6272	0.8505	0.075*
C14A	0.0317 (2)	0.54234 (11)	0.81427 (15)	0.0550 (6)
H14A	−0.0155	0.5450	0.7540	0.066*
C15A	0.3876 (3)	0.50331 (13)	1.10988 (15)	0.0653 (7)
H15A	0.3614	0.4549	1.1149	0.098*
H15B	0.4440	0.5202	1.1667	0.098*
H15C	0.4467	0.5073	1.0680	0.098*
O1B	0.09195 (17)	0.78644 (7)	0.80813 (9)	0.0548 (4)
O2B	0.02120 (15)	0.63829 (7)	0.43779 (9)	0.0514 (4)
H2B	0.0628	0.6534	0.4012	0.077*
O3B	0.33565 (17)	1.02397 (7)	1.12977 (9)	0.0571 (4)
N1B	0.19818 (18)	0.87025 (9)	0.74304 (10)	0.0455 (4)
H1B	0.2149	0.8885	0.6952	0.055*
N2B	0.22473 (18)	0.91065 (9)	0.81927 (10)	0.0427 (4)
C1B	0.1108 (2)	0.76347 (10)	0.66236 (11)	0.0356 (4)
C2B	0.0026 (2)	0.71118 (10)	0.64794 (12)	0.0419 (5)
H2B1	−0.0523	0.7042	0.6893	0.050*
C3B	−0.0245 (2)	0.66956 (11)	0.57357 (13)	0.0443 (5)
H3B	−0.0972	0.6347	0.5650	0.053*
C4B	0.0561 (2)	0.67953 (10)	0.51149 (12)	0.0364 (4)
C5B	0.1669 (2)	0.72987 (10)	0.52587 (12)	0.0395 (5)
H5B	0.2234	0.7357	0.4851	0.047*
C6B	0.1938 (2)	0.77149 (10)	0.60057 (12)	0.0391 (5)
H6B	0.2685	0.8054	0.6098	0.047*
C7B	0.1325 (2)	0.80650 (10)	0.74351 (12)	0.0398 (5)
C8B	0.2720 (2)	0.97284 (11)	0.81420 (13)	0.0444 (5)
H8BA	0.2831	0.9889	0.7600	0.053*
C9B	0.3094 (2)	1.01972 (10)	0.89046 (13)	0.0406 (5)
C10B	0.2934 (2)	0.99840 (10)	0.97275 (13)	0.0413 (5)
H10B	0.2493	0.9553	0.9784	0.050*
C11B	0.3427 (2)	1.04106 (10)	1.04576 (13)	0.0432 (5)
C12B	0.4064 (2)	1.10571 (10)	1.03710 (15)	0.0487 (5)
H12B	0.4415	1.1342	1.0866	0.058*
C13B	0.4175 (2)	1.12758 (11)	0.95555 (16)	0.0524 (6)
H13B	0.4581	1.1715	0.9496	0.063*
C14B	0.3690 (2)	1.08499 (11)	0.88184 (14)	0.0486 (5)
H14B	0.3764	1.1003	0.8266	0.058*
C15B	0.2675 (3)	0.95877 (13)	1.14034 (16)	0.0703 (7)
H15D	0.1643	0.9597	1.1077	0.105*
H15E	0.2746	0.9511	1.2021	0.105*
H15F	0.3177	0.9214	1.1184	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0767 (11)	0.0669 (10)	0.0272 (8)	0.0185 (8)	0.0063 (7)	−0.0019 (7)
O2A	0.0749 (10)	0.0647 (10)	0.0332 (8)	0.0202 (8)	0.0163 (7)	−0.0020 (7)
O3A	0.0674 (10)	0.0563 (9)	0.0421 (9)	0.0040 (8)	0.0233 (8)	−0.0093 (7)
N1A	0.0599 (11)	0.0465 (10)	0.0263 (8)	0.0091 (9)	0.0087 (8)	−0.0062 (7)
N2A	0.0578 (11)	0.0449 (10)	0.0343 (9)	0.0003 (9)	0.0180 (8)	−0.0083 (8)
C1A	0.0442 (11)	0.0326 (10)	0.0285 (10)	−0.0021 (9)	0.0088 (8)	0.0007 (8)
C2A	0.0470 (12)	0.0498 (12)	0.0290 (11)	0.0036 (10)	0.0010 (9)	−0.0024 (9)
C3A	0.0455 (12)	0.0531 (13)	0.0401 (12)	0.0110 (10)	0.0064 (10)	−0.0024 (10)
C4A	0.0535 (13)	0.0344 (11)	0.0291 (10)	0.0023 (9)	0.0130 (9)	0.0003 (8)
C5A	0.0523 (13)	0.0412 (11)	0.0269 (10)	0.0025 (10)	0.0026 (9)	−0.0007 (9)
C6A	0.0418 (11)	0.0401 (11)	0.0350 (11)	0.0064 (9)	0.0055 (9)	0.0015 (9)
C7A	0.0483 (12)	0.0409 (11)	0.0298 (11)	−0.0014 (10)	0.0125 (9)	0.0010 (9)
C8A	0.0493 (12)	0.0455 (12)	0.0389 (11)	−0.0026 (10)	0.0144 (10)	−0.0063 (10)
C9A	0.0450 (12)	0.0403 (11)	0.0441 (12)	−0.0050 (10)	0.0169 (10)	−0.0082 (9)
C10A	0.0502 (12)	0.0407 (11)	0.0442 (12)	0.0009 (9)	0.0222 (10)	−0.0020 (9)
C11A	0.0515 (13)	0.0434 (12)	0.0419 (12)	−0.0077 (10)	0.0212 (10)	−0.0078 (10)
C12A	0.0589 (14)	0.0465 (13)	0.0655 (16)	0.0012 (11)	0.0215 (12)	−0.0200 (11)
C13A	0.0578 (15)	0.0512 (14)	0.0730 (17)	0.0118 (11)	0.0072 (13)	−0.0147 (13)
C14A	0.0520 (14)	0.0534 (14)	0.0555 (14)	0.0007 (11)	0.0071 (11)	−0.0116 (11)
C15A	0.0728 (16)	0.0820 (17)	0.0445 (14)	0.0122 (14)	0.0212 (12)	−0.0030 (12)
O1B	0.0828 (11)	0.0569 (9)	0.0305 (8)	−0.0083 (8)	0.0249 (8)	−0.0005 (7)
O2B	0.0628 (9)	0.0577 (9)	0.0376 (8)	−0.0053 (7)	0.0203 (7)	−0.0119 (7)
O3B	0.0770 (11)	0.0564 (10)	0.0427 (9)	−0.0050 (8)	0.0243 (8)	−0.0114 (7)
N1B	0.0596 (11)	0.0526 (11)	0.0263 (9)	−0.0061 (9)	0.0149 (8)	−0.0037 (8)
N2B	0.0491 (10)	0.0508 (11)	0.0275 (9)	0.0003 (8)	0.0090 (7)	−0.0048 (8)
C1B	0.0400 (11)	0.0418 (11)	0.0240 (10)	0.0045 (9)	0.0067 (8)	0.0021 (8)
C2B	0.0465 (12)	0.0522 (12)	0.0321 (11)	−0.0004 (10)	0.0194 (9)	0.0011 (9)
C3B	0.0473 (12)	0.0485 (12)	0.0400 (12)	−0.0057 (10)	0.0165 (10)	−0.0053 (10)
C4B	0.0421 (11)	0.0407 (11)	0.0263 (10)	0.0067 (9)	0.0089 (9)	−0.0011 (8)
C5B	0.0414 (11)	0.0504 (12)	0.0304 (10)	0.0037 (10)	0.0161 (9)	0.0037 (9)
C6B	0.0408 (11)	0.0469 (12)	0.0299 (10)	−0.0016 (9)	0.0099 (9)	0.0014 (9)
C7B	0.0440 (12)	0.0480 (12)	0.0269 (11)	0.0021 (10)	0.0081 (9)	0.0022 (9)
C8B	0.0486 (12)	0.0520 (13)	0.0348 (11)	0.0006 (10)	0.0148 (10)	0.0014 (9)
C9B	0.0396 (11)	0.0419 (12)	0.0405 (12)	0.0040 (9)	0.0106 (9)	−0.0017 (9)
C10B	0.0433 (11)	0.0399 (11)	0.0431 (12)	−0.0001 (9)	0.0159 (9)	−0.0046 (9)
C11B	0.0457 (12)	0.0409 (12)	0.0445 (12)	0.0064 (10)	0.0144 (10)	−0.0078 (10)
C12B	0.0503 (13)	0.0395 (12)	0.0540 (14)	0.0053 (10)	0.0098 (11)	−0.0118 (10)
C13B	0.0524 (13)	0.0350 (12)	0.0694 (16)	0.0015 (10)	0.0150 (12)	0.0001 (11)
C14B	0.0548 (13)	0.0449 (13)	0.0485 (13)	0.0077 (10)	0.0177 (11)	0.0087 (10)
C15B	0.099 (2)	0.0647 (16)	0.0586 (16)	−0.0104 (15)	0.0407 (14)	−0.0043 (13)

Geometric parameters (Å, º)

O1A—C7A	1.226 (2)	O1B—C7B	1.225 (2)
O2A—C4A	1.355 (2)	O2B—C4B	1.360 (2)
O2A—H2A	0.8194	O2B—H2B	0.8198
O3A—C11A	1.372 (2)	O3B—C11B	1.369 (2)
O3A—C15A	1.416 (3)	O3B—C15B	1.421 (3)
N1A—C7A	1.353 (2)	N1B—C7B	1.358 (2)
N1A—N2A	1.375 (2)	N1B—N2B	1.383 (2)
N1A—H1A	0.8478	N1B—H1B	0.8736
N2A—C8A	1.275 (2)	N2B—C8B	1.271 (2)
C1A—C6A	1.387 (2)	C1B—C2B	1.388 (3)
C1A—C2A	1.389 (3)	C1B—C6B	1.390 (2)
C1A—C7A	1.483 (3)	C1B—C7B	1.477 (3)
C2A—C3A	1.373 (3)	C2B—C3B	1.373 (3)
C2A—H2A1	0.9300	C2B—H2B1	0.9300
C3A—C4A	1.378 (3)	C3B—C4B	1.382 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.385 (3)	C4B—C5B	1.379 (3)
C5A—C6A	1.378 (3)	C5B—C6B	1.377 (2)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C8A—C9A	1.461 (3)	C8B—C9B	1.455 (3)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C14A	1.381 (3)	C9B—C14B	1.380 (3)
C9A—C10A	1.396 (3)	C9B—C10B	1.391 (3)
C10A—C11A	1.381 (3)	C10B—C11B	1.376 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.384 (3)	C11B—C12B	1.386 (3)
C12A—C13A	1.365 (3)	C12B—C13B	1.368 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.379 (3)	C13B—C14B	1.383 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C4A—O2A—H2A	109.6	C4B—O2B—H2B	109.5
C11A—O3A—C15A	116.91 (15)	C11B—O3B—C15B	116.88 (16)
C7A—N1A—N2A	118.59 (16)	C7B—N1B—N2B	118.10 (16)
C7A—N1A—H1A	120.9	C7B—N1B—H1B	122.7
N2A—N1A—H1A	120.0	N2B—N1B—H1B	118.9
C8A—N2A—N1A	115.67 (16)	C8B—N2B—N1B	116.77 (16)
C6A—C1A—C2A	118.28 (17)	C2B—C1B—C6B	118.26 (17)
C6A—C1A—C7A	124.35 (17)	C2B—C1B—C7B	117.84 (16)
C2A—C1A—C7A	117.18 (16)	C6B—C1B—C7B	123.90 (18)
C3A—C2A—C1A	121.01 (18)	C3B—C2B—C1B	121.04 (17)
C3A—C2A—H2A1	119.5	C3B—C2B—H2B1	119.5
C1A—C2A—H2A1	119.5	C1B—C2B—H2B1	119.5
C2A—C3A—C4A	120.08 (19)	C2B—C3B—C4B	119.98 (19)
C2A—C3A—H3A	120.0	C2B—C3B—H3B	120.0
C4A—C3A—H3A	120.0	C4B—C3B—H3B	120.0
O2A—C4A—C3A	118.10 (18)	O2B—C4B—C5B	122.75 (16)
O2A—C4A—C5A	122.16 (17)	O2B—C4B—C3B	117.43 (17)
C3A—C4A—C5A	119.73 (17)	C5B—C4B—C3B	119.81 (17)
C6A—C5A—C4A	119.84 (17)	C6B—C5B—C4B	120.00 (17)
C6A—C5A—H5A	120.1	C6B—C5B—H5B	120.0
C4A—C5A—H5A	120.1	C4B—C5B—H5B	120.0
C5A—C6A—C1A	120.91 (18)	C5B—C6B—C1B	120.86 (18)
C5A—C6A—H6A	119.5	C5B—C6B—H6B	119.6
C1A—C6A—H6A	119.5	C1B—C6B—H6B	119.6
O1A—C7A—N1A	121.15 (17)	O1B—C7B—N1B	121.12 (17)
O1A—C7A—C1A	122.06 (18)	O1B—C7B—C1B	122.05 (18)
N1A—C7A—C1A	116.69 (16)	N1B—C7B—C1B	116.82 (16)
N2A—C8A—C9A	121.71 (19)	N2B—C8B—C9B	122.14 (18)
N2A—C8A—H8AA	119.1	N2B—C8B—H8BA	118.9
C9A—C8A—H8AA	119.1	C9B—C8B—H8BA	118.9
C14A—C9A—C10A	119.58 (18)	C14B—C9B—C10B	119.63 (18)
C14A—C9A—C8A	118.82 (19)	C14B—C9B—C8B	119.20 (19)
C10A—C9A—C8A	121.59 (19)	C10B—C9B—C8B	121.09 (18)
C11A—C10A—C9A	119.74 (19)	C11B—C10B—C9B	119.99 (19)
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.0
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.0
O3A—C11A—C10A	124.05 (19)	O3B—C11B—C10B	124.36 (18)
O3A—C11A—C12A	116.09 (18)	O3B—C11B—C12B	115.60 (18)
C10A—C11A—C12A	119.9 (2)	C10B—C11B—C12B	120.03 (19)
C13A—C12A—C11A	120.1 (2)	C13B—C12B—C11B	119.9 (2)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.1
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.1
C12A—C13A—C14A	120.7 (2)	C12B—C13B—C14B	120.5 (2)
C12A—C13A—H13A	119.7	C12B—C13B—H13B	119.7
C14A—C13A—H13A	119.7	C14B—C13B—H13B	119.7
C13A—C14A—C9A	119.9 (2)	C9B—C14B—C13B	119.9 (2)
C13A—C14A—H14A	120.1	C9B—C14B—H14B	120.1
C9A—C14A—H14A	120.1	C13B—C14B—H14B	120.1
O3A—C15A—H15A	109.5	O3B—C15B—H15D	109.5
O3A—C15A—H15B	109.5	O3B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O3A—C15A—H15C	109.5	O3B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C7A—N1A—N2A—C8A	175.70 (18)	C7B—N1B—N2B—C8B	−172.99 (18)
C6A—C1A—C2A—C3A	3.6 (3)	C6B—C1B—C2B—C3B	−1.6 (3)
C7A—C1A—C2A—C3A	−171.59 (18)	C7B—C1B—C2B—C3B	179.43 (18)
C1A—C2A—C3A—C4A	−0.9 (3)	C1B—C2B—C3B—C4B	−0.2 (3)
C2A—C3A—C4A—O2A	178.58 (18)	C2B—C3B—C4B—O2B	−177.96 (17)
C2A—C3A—C4A—C5A	−2.4 (3)	C2B—C3B—C4B—C5B	2.0 (3)
O2A—C4A—C5A—C6A	−178.03 (18)	O2B—C4B—C5B—C6B	177.99 (17)
C3A—C4A—C5A—C6A	3.0 (3)	C3B—C4B—C5B—C6B	−2.0 (3)
C4A—C5A—C6A—C1A	−0.3 (3)	C4B—C5B—C6B—C1B	0.1 (3)
C2A—C1A—C6A—C5A	−3.0 (3)	C2B—C1B—C6B—C5B	1.6 (3)
C7A—C1A—C6A—C5A	171.83 (17)	C7B—C1B—C6B—C5B	−179.48 (17)
N2A—N1A—C7A—O1A	2.8 (3)	N2B—N1B—C7B—O1B	3.0 (3)
N2A—N1A—C7A—C1A	−173.49 (16)	N2B—N1B—C7B—C1B	−177.75 (16)
C6A—C1A—C7A—O1A	165.80 (19)	C2B—C1B—C7B—O1B	20.7 (3)
C2A—C1A—C7A—O1A	−19.4 (3)	C6B—C1B—C7B—O1B	−158.18 (19)
C6A—C1A—C7A—N1A	−17.9 (3)	C2B—C1B—C7B—N1B	−158.50 (17)
C2A—C1A—C7A—N1A	156.92 (17)	C6B—C1B—C7B—N1B	22.6 (3)
N1A—N2A—C8A—C9A	−178.14 (16)	N1B—N2B—C8B—C9B	−177.69 (16)
N2A—C8A—C9A—C14A	−179.67 (19)	N2B—C8B—C9B—C14B	176.00 (19)
N2A—C8A—C9A—C10A	1.2 (3)	N2B—C8B—C9B—C10B	−0.6 (3)
C14A—C9A—C10A—C11A	1.3 (3)	C14B—C9B—C10B—C11B	−2.8 (3)
C8A—C9A—C10A—C11A	−179.55 (17)	C8B—C9B—C10B—C11B	173.83 (17)
C15A—O3A—C11A—C10A	14.2 (3)	C15B—O3B—C11B—C10B	−2.4 (3)
C15A—O3A—C11A—C12A	−165.74 (19)	C15B—O3B—C11B—C12B	178.49 (19)
C9A—C10A—C11A—O3A	−177.20 (18)	C9B—C10B—C11B—O3B	−178.14 (17)
C9A—C10A—C11A—C12A	2.8 (3)	C9B—C10B—C11B—C12B	0.9 (3)
O3A—C11A—C12A—C13A	175.5 (2)	O3B—C11B—C12B—C13B	−179.62 (18)
C10A—C11A—C12A—C13A	−4.4 (3)	C10B—C11B—C12B—C13B	1.2 (3)
C11A—C12A—C13A—C14A	2.0 (4)	C11B—C12B—C13B—C14B	−1.5 (3)
C12A—C13A—C14A—C9A	2.1 (3)	C10B—C9B—C14B—C13B	2.5 (3)
C10A—C9A—C14A—C13A	−3.7 (3)	C8B—C9B—C14B—C13B	−174.18 (18)
C8A—C9A—C14A—C13A	177.1 (2)	C12B—C13B—C14B—C9B	−0.3 (3)

Hydrogen-bond geometry (Å, º)

Cg₄ is the centroid of the C9B–C14B ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2B^i	0.85	2.58	3.354 (2)	153
N1B—H1B···O3A^ii	0.87	2.32	3.178 (3)	170
O2A—H2A···O1A^iii	0.82	1.94	2.702 (2)	155
O2A—H2A···N2A^iii	0.82	2.60	3.231 (2)	135
O2B—H2B···O1B^ii	0.82	1.92	2.696 (2)	157
O2B—H2B···N2B^ii	0.82	2.52	3.110 (2)	129
C13B—H13B···O1A^iv	0.93	2.57	3.352 (3)	143
C3B—H3B···Cg^v	0.93	2.70	3.604 (2)	165

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