2-Amino-5-chloro­benzo­phenone

The asymmetric unit of the title compound (systematic name: 2-benzoyl-4-chloro­aniline), C₁₃H₁₀ClNO, contains four independent mol­ecules with similar dihedral angles between the benzene rings [ranging from 53.7 (2) to 59.8 (2)°]. In the crystal, the mol­ecules are linked by N—H...O hydrogen bonds into a three-dimensional supra­molecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.080
• wR factor = 0.225
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          4 Check

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        40% Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00593 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     27.151 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.557 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.871 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         18 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

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 ..............          8 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        273 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        273 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   7 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

   4 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
   8 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

---

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-Benzoyl-4-chloroaniline

Crystal data

C13H10ClNO	Z = 8
Mr = 231.67	F(000) = 960
Triclinic, P1	Dx = 1.353 Mg m^−3
a = 9.7335 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6473 (7) Å	Cell parameters from 11324 reflections
c = 24.7554 (17) Å	θ = 2.2–28.4°
α = 87.443 (2)°	µ = 0.31 mm^−1
β = 84.272 (2)°	T = 273 K
γ = 62.978 (2)°	Prism, colorless
V = 2274.1 (3) Å^3	0.25 × 0.15 × 0.10 mm

Data collection

Bruker APEX CCD area detector diffractometer	11324 independent reflections
Radiation source: fine-focus sealed tube	4512 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
phi and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.945, Tmax = 0.969	k = −14→14
34850 measured reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.225	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0827P)^2 + 0.4385P] where P = (Fo^2 + 2Fc^2)/3
11324 reflections	(Δ/σ)max = 0.001
577 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.27 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.

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.

All of the H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.88, C —H = 0.95 Å, and with U_ĩso(H) = 1.18–1.21U_eq(C,N).

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

	x	y	z	Uiso*/Ueq
Cl1	−0.22973 (12)	0.40371 (11)	0.57327 (5)	0.0702 (4)
Cl4	0.32333 (13)	0.90689 (11)	0.92390 (5)	0.0699 (4)
Cl3	0.82354 (14)	0.92281 (11)	0.92846 (5)	0.0726 (4)
Cl2	0.25035 (13)	0.42264 (11)	0.57452 (5)	0.0742 (4)
O2	0.8276 (3)	0.0336 (3)	0.70037 (10)	0.0603 (8)
O1	0.3672 (3)	0.0469 (3)	0.69319 (11)	0.0660 (8)
O3	0.6319 (3)	0.5398 (3)	0.79903 (11)	0.0618 (8)
O4	0.0801 (3)	0.5417 (3)	0.80924 (11)	0.0638 (8)
N3	0.6669 (4)	0.2790 (3)	0.74839 (12)	0.0612 (9)
H3A	0.6444	0.3403	0.7735	0.073*
H3B	0.7476	0.1989	0.7494	0.073*
N2	0.5589 (4)	0.7840 (3)	0.75068 (12)	0.0608 (9)
H2A	0.5241	0.8453	0.7253	0.073*
H2B	0.5574	0.7041	0.7489	0.073*
C1	0.7822 (4)	−0.0228 (4)	0.61666 (14)	0.0399 (9)
C2	0.6802 (4)	0.7143 (4)	0.83548 (15)	0.0419 (9)
N4	0.1714 (4)	0.2712 (4)	0.75153 (13)	0.0708 (11)
H4A	0.1431	0.3318	0.7773	0.085*
H4B	0.2566	0.1947	0.7521	0.085*
C3	0.2427 (4)	0.4567 (4)	0.87849 (15)	0.0435 (9)
C4	0.1757 (4)	0.6974 (4)	0.83300 (15)	0.0446 (9)
C5	0.7346 (4)	0.4793 (4)	0.88307 (14)	0.0417 (9)
C6	0.5002 (4)	0.2495 (4)	0.62529 (15)	0.0448 (9)
H6	0.5168	0.1854	0.5981	0.054*
C7	0.7443 (4)	0.7518 (4)	0.87631 (15)	0.0446 (9)
H7	0.7884	0.6877	0.9038	0.054*
C8	0.6051 (4)	0.2112 (4)	0.66532 (14)	0.0414 (9)
C9	0.6786 (4)	0.5782 (4)	0.83669 (15)	0.0441 (9)
N1	0.0435 (4)	0.7667 (4)	0.75073 (13)	0.0697 (10)
H1A	0.0088	0.8263	0.7248	0.084*
H1B	0.0344	0.6900	0.7514	0.084*
C10	0.2946 (4)	−0.0435 (4)	0.62334 (15)	0.0460 (10)
C11	0.5753 (5)	0.3087 (4)	0.70726 (15)	0.0470 (10)
C12	0.0196 (4)	0.2353 (4)	0.62564 (15)	0.0466 (10)
H12	0.0446	0.1728	0.5970	0.056*
C13	0.2405 (4)	0.7356 (4)	0.87332 (15)	0.0447 (9)
H13	0.2788	0.6742	0.9021	0.054*
C14	0.7410 (4)	0.0742 (4)	0.66330 (15)	0.0422 (9)
C15	0.1613 (4)	0.5656 (4)	0.83826 (15)	0.0467 (10)
C16	0.6155 (4)	0.8130 (4)	0.79311 (15)	0.0467 (10)
C17	0.1186 (4)	0.1997 (4)	0.66732 (15)	0.0456 (10)
C18	−0.1129 (4)	0.3602 (4)	0.62636 (15)	0.0463 (10)
C19	0.1906 (5)	−0.0987 (4)	0.61899 (15)	0.0518 (10)
H19	0.0956	−0.0609	0.6397	0.062*
C20	0.1119 (4)	0.7934 (4)	0.79014 (16)	0.0513 (10)
C21	0.7963 (4)	0.0193 (4)	0.56358 (15)	0.0505 (10)
H21	0.7745	0.1126	0.5561	0.061*
C22	0.0815 (5)	0.2965 (4)	0.70985 (15)	0.0499 (10)
C52	0.2646 (5)	0.0684 (4)	0.66352 (15)	0.0463 (10)
C23	0.8413 (4)	0.3404 (4)	0.87202 (16)	0.0501 (10)
H23	0.8788	0.3124	0.8363	0.060*
C24	0.8145 (4)	−0.1618 (4)	0.62641 (16)	0.0493 (10)
H24	0.8060	−0.1917	0.6619	0.059*
C25	0.3751 (4)	0.3784 (4)	0.62560 (16)	0.0479 (10)
C26	0.2493 (4)	0.8601 (4)	0.87180 (15)	0.0478 (10)
C27	0.4016 (4)	0.4008 (4)	0.88200 (15)	0.0491 (10)
H27	0.4591	0.4368	0.8603	0.059*
C28	0.8590 (4)	−0.2570 (4)	0.58436 (17)	0.0547 (11)
H28	0.8799	−0.3502	0.5916	0.066*
C29	0.6782 (4)	0.5194 (4)	0.93601 (16)	0.0510 (10)
H29	0.6060	0.6120	0.9441	0.061*
C30	0.7437 (4)	0.8804 (4)	0.87671 (16)	0.0502 (10)
C31	0.1272 (5)	0.9185 (4)	0.78939 (17)	0.0614 (12)
H31	0.0911	0.9811	0.7607	0.074*
C32	0.8920 (5)	0.2442 (4)	0.91293 (18)	0.0583 (11)
H32	0.9638	0.1515	0.9049	0.070*
C33	0.1927 (5)	0.9517 (4)	0.82900 (18)	0.0597 (12)
H33	0.1995	1.0362	0.8273	0.072*
C34	0.3474 (5)	0.4746 (4)	0.66614 (18)	0.0625 (12)
H34	0.2624	0.5631	0.6660	0.075*
C35	0.6778 (5)	0.9772 (4)	0.83648 (17)	0.0602 (12)
H35	0.6749	1.0657	0.8374	0.072*
C36	0.1628 (5)	0.3999 (4)	0.91087 (17)	0.0648 (12)
H36	0.0571	0.4343	0.9084	0.078*
C37	−0.1510 (5)	0.4535 (4)	0.66879 (18)	0.0589 (11)
H37	−0.2413	0.5382	0.6694	0.071*
C38	−0.0569 (5)	0.4218 (4)	0.70959 (17)	0.0598 (12)
H38	−0.0851	0.4851	0.7381	0.072*
C39	0.8723 (5)	−0.2140 (4)	0.53205 (19)	0.0630 (12)
H39	0.9014	−0.2776	0.5035	0.076*
C40	0.4736 (5)	0.2923 (4)	0.91764 (18)	0.0650 (12)
H40	0.5798	0.2551	0.9198	0.078*
C41	0.6172 (5)	0.9438 (4)	0.79555 (17)	0.0589 (11)
H41	0.5755	1.0095	0.7683	0.071*
C42	0.8373 (5)	0.2840 (5)	0.96577 (19)	0.0630 (12)
H42	0.8726	0.2191	0.9938	0.076*
C43	0.2284 (5)	−0.2083 (4)	0.58428 (18)	0.0632 (12)
H43	0.1597	−0.2459	0.5818	0.076*
C44	0.4348 (5)	−0.1013 (4)	0.59149 (18)	0.0649 (12)
H44	0.5056	−0.0659	0.5939	0.078*
C45	0.7294 (5)	0.4214 (4)	0.97693 (16)	0.0623 (12)
H45	0.6906	0.4484	1.0127	0.075*
C46	0.8425 (5)	−0.0766 (4)	0.52181 (16)	0.0657 (12)
H46	0.8536	−0.0480	0.4863	0.079*
C47	0.4442 (5)	0.4398 (4)	0.70622 (16)	0.0581 (11)
H47	0.4230	0.5047	0.7336	0.070*
C48	0.3678 (5)	−0.2631 (4)	0.5530 (2)	0.0725 (14)
H48	0.3928	−0.3369	0.5291	0.087*
C49	0.3894 (6)	0.2389 (4)	0.94993 (19)	0.0742 (14)
H49	0.4380	0.1656	0.9739	0.089*
C50	0.2337 (6)	0.2945 (5)	0.94652 (19)	0.0765 (14)
H50	0.1758	0.2600	0.9688	0.092*
C51	0.4694 (5)	−0.2091 (5)	0.5569 (2)	0.0806 (15)
H51	0.5634	−0.2464	0.5356	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0616 (7)	0.0552 (7)	0.0837 (8)	−0.0151 (6)	−0.0241 (6)	0.0102 (6)
Cl4	0.0772 (8)	0.0564 (7)	0.0854 (9)	−0.0362 (6)	−0.0124 (6)	−0.0117 (6)
Cl3	0.0900 (9)	0.0613 (7)	0.0841 (9)	−0.0463 (7)	−0.0240 (7)	−0.0006 (6)
Cl2	0.0572 (7)	0.0612 (7)	0.0912 (9)	−0.0117 (6)	−0.0290 (6)	0.0080 (6)
O2	0.0649 (19)	0.0551 (17)	0.0468 (17)	−0.0116 (15)	−0.0217 (15)	0.0016 (13)
O1	0.072 (2)	0.0572 (18)	0.070 (2)	−0.0249 (16)	−0.0351 (17)	0.0057 (15)
O3	0.087 (2)	0.0549 (17)	0.0497 (17)	−0.0348 (16)	−0.0201 (16)	−0.0029 (13)
O4	0.075 (2)	0.0559 (18)	0.0651 (19)	−0.0282 (16)	−0.0307 (16)	−0.0019 (14)
N3	0.081 (3)	0.053 (2)	0.048 (2)	−0.0266 (19)	−0.009 (2)	−0.0068 (17)
N2	0.075 (2)	0.058 (2)	0.044 (2)	−0.0249 (19)	−0.0133 (18)	0.0072 (17)
C1	0.036 (2)	0.036 (2)	0.043 (2)	−0.0107 (17)	−0.0071 (17)	0.0017 (17)
C2	0.040 (2)	0.043 (2)	0.042 (2)	−0.0187 (19)	−0.0002 (18)	−0.0018 (18)
N4	0.100 (3)	0.063 (2)	0.055 (2)	−0.038 (2)	−0.019 (2)	−0.0048 (18)
C3	0.044 (2)	0.035 (2)	0.052 (2)	−0.0168 (19)	−0.010 (2)	−0.0053 (18)
C4	0.041 (2)	0.041 (2)	0.041 (2)	−0.0099 (19)	−0.0013 (18)	−0.0035 (18)
C5	0.044 (2)	0.041 (2)	0.042 (2)	−0.0208 (19)	−0.0040 (19)	−0.0014 (18)
C6	0.044 (2)	0.036 (2)	0.051 (2)	−0.0144 (19)	−0.0028 (19)	−0.0020 (18)
C7	0.046 (2)	0.036 (2)	0.049 (2)	−0.0172 (19)	−0.0029 (19)	0.0027 (17)
C8	0.045 (2)	0.039 (2)	0.042 (2)	−0.0213 (19)	−0.0009 (19)	0.0024 (18)
C9	0.043 (2)	0.045 (2)	0.041 (2)	−0.0176 (19)	−0.0026 (18)	−0.0065 (19)
N1	0.084 (3)	0.064 (2)	0.051 (2)	−0.020 (2)	−0.028 (2)	0.0092 (18)
C10	0.045 (3)	0.037 (2)	0.054 (3)	−0.015 (2)	−0.018 (2)	0.0035 (18)
C11	0.056 (3)	0.045 (2)	0.044 (2)	−0.027 (2)	−0.003 (2)	−0.0013 (19)
C12	0.052 (3)	0.040 (2)	0.048 (2)	−0.021 (2)	−0.005 (2)	0.0022 (18)
C13	0.049 (2)	0.039 (2)	0.043 (2)	−0.0172 (19)	−0.0048 (19)	0.0006 (17)
C14	0.043 (2)	0.038 (2)	0.045 (2)	−0.0177 (19)	−0.007 (2)	0.0018 (18)
C15	0.048 (2)	0.043 (2)	0.045 (2)	−0.015 (2)	−0.008 (2)	−0.0077 (18)
C16	0.044 (2)	0.046 (2)	0.043 (2)	−0.014 (2)	−0.0020 (19)	0.0022 (19)
C17	0.057 (3)	0.043 (2)	0.040 (2)	−0.026 (2)	−0.003 (2)	0.0036 (18)
C18	0.043 (2)	0.041 (2)	0.054 (3)	−0.019 (2)	−0.0020 (19)	0.0025 (19)
C19	0.052 (3)	0.048 (2)	0.055 (3)	−0.021 (2)	−0.016 (2)	0.009 (2)
C20	0.045 (2)	0.047 (2)	0.046 (3)	−0.007 (2)	−0.002 (2)	0.001 (2)
C21	0.058 (3)	0.038 (2)	0.047 (3)	−0.014 (2)	−0.007 (2)	0.0028 (19)
C22	0.069 (3)	0.052 (3)	0.040 (2)	−0.038 (2)	−0.001 (2)	0.003 (2)
C52	0.056 (3)	0.040 (2)	0.045 (2)	−0.022 (2)	−0.013 (2)	0.0093 (18)
C23	0.053 (3)	0.043 (2)	0.053 (3)	−0.021 (2)	0.002 (2)	−0.008 (2)
C24	0.046 (2)	0.041 (2)	0.056 (3)	−0.015 (2)	−0.006 (2)	0.004 (2)
C25	0.043 (2)	0.037 (2)	0.057 (3)	−0.012 (2)	−0.0074 (19)	0.0043 (19)
C26	0.047 (2)	0.040 (2)	0.054 (3)	−0.0183 (19)	0.003 (2)	−0.0048 (19)
C27	0.048 (3)	0.046 (2)	0.055 (3)	−0.022 (2)	−0.008 (2)	−0.005 (2)
C28	0.053 (3)	0.041 (2)	0.071 (3)	−0.022 (2)	−0.002 (2)	−0.004 (2)
C29	0.059 (3)	0.040 (2)	0.052 (3)	−0.021 (2)	−0.004 (2)	−0.003 (2)
C30	0.057 (3)	0.039 (2)	0.054 (3)	−0.020 (2)	−0.005 (2)	−0.0039 (19)
C31	0.068 (3)	0.049 (3)	0.054 (3)	−0.016 (2)	−0.007 (2)	0.013 (2)
C32	0.053 (3)	0.039 (2)	0.077 (3)	−0.016 (2)	−0.002 (2)	0.002 (2)
C33	0.062 (3)	0.040 (2)	0.069 (3)	−0.019 (2)	0.011 (2)	0.001 (2)
C34	0.056 (3)	0.040 (2)	0.073 (3)	−0.007 (2)	0.003 (2)	−0.003 (2)
C35	0.073 (3)	0.041 (2)	0.064 (3)	−0.025 (2)	0.001 (2)	0.003 (2)
C36	0.059 (3)	0.069 (3)	0.083 (3)	−0.041 (3)	−0.023 (3)	0.019 (3)
C37	0.057 (3)	0.044 (2)	0.070 (3)	−0.021 (2)	0.012 (2)	−0.005 (2)
C38	0.073 (3)	0.052 (3)	0.057 (3)	−0.032 (3)	0.005 (3)	−0.012 (2)
C39	0.067 (3)	0.055 (3)	0.065 (3)	−0.025 (2)	−0.001 (2)	−0.021 (2)
C40	0.061 (3)	0.045 (3)	0.084 (3)	−0.016 (2)	−0.027 (3)	−0.003 (2)
C41	0.069 (3)	0.046 (3)	0.054 (3)	−0.020 (2)	−0.008 (2)	0.015 (2)
C42	0.064 (3)	0.058 (3)	0.069 (3)	−0.027 (3)	−0.018 (3)	0.021 (2)
C43	0.064 (3)	0.047 (3)	0.084 (3)	−0.026 (2)	−0.032 (3)	0.005 (2)
C44	0.039 (3)	0.062 (3)	0.091 (3)	−0.019 (2)	−0.007 (2)	−0.012 (3)
C45	0.083 (3)	0.060 (3)	0.046 (3)	−0.034 (3)	−0.004 (2)	0.004 (2)
C46	0.080 (3)	0.059 (3)	0.047 (3)	−0.023 (3)	0.000 (2)	−0.005 (2)
C47	0.072 (3)	0.043 (2)	0.051 (3)	−0.019 (2)	0.004 (2)	−0.012 (2)
C48	0.062 (3)	0.044 (3)	0.097 (4)	−0.007 (2)	−0.019 (3)	−0.018 (2)
C49	0.098 (4)	0.047 (3)	0.084 (4)	−0.034 (3)	−0.044 (3)	0.021 (2)
C50	0.080 (4)	0.084 (4)	0.087 (4)	−0.054 (3)	−0.030 (3)	0.033 (3)
C51	0.049 (3)	0.074 (3)	0.107 (4)	−0.016 (3)	−0.002 (3)	−0.028 (3)

Geometric parameters (Å, º)

Cl1—C18	1.732 (4)	C18—C37	1.381 (5)
Cl4—C26	1.732 (4)	C19—C43	1.368 (5)
Cl3—C30	1.737 (4)	C19—H19	0.9300
Cl2—C25	1.740 (4)	C20—C31	1.405 (5)
O2—C14	1.236 (4)	C21—C46	1.378 (5)
O1—C52	1.230 (4)	C21—H21	0.9300
O3—C9	1.237 (4)	C22—C38	1.401 (5)
O4—C15	1.232 (4)	C23—C32	1.366 (5)
N3—C11	1.352 (5)	C23—H23	0.9300
N3—H3A	0.8600	C24—C28	1.380 (5)
N3—H3B	0.8600	C24—H24	0.9300
N2—C16	1.342 (5)	C25—C34	1.384 (5)
N2—H2A	0.8600	C26—C33	1.383 (5)
N2—H2B	0.8600	C27—C40	1.379 (5)
C1—C24	1.381 (5)	C27—H27	0.9300
C1—C21	1.383 (5)	C28—C39	1.368 (5)
C1—C14	1.483 (5)	C28—H28	0.9300
C2—C7	1.399 (5)	C29—C45	1.378 (5)
C2—C16	1.426 (5)	C29—H29	0.9300
C2—C9	1.455 (5)	C30—C35	1.379 (5)
N4—C22	1.358 (5)	C31—C33	1.361 (6)
N4—H4A	0.8600	C31—H31	0.9300
N4—H4B	0.8600	C32—C42	1.371 (5)
C3—C36	1.368 (5)	C32—H32	0.9300
C3—C27	1.393 (5)	C33—H33	0.9300
C3—C15	1.478 (5)	C34—C47	1.359 (6)
C4—C13	1.398 (5)	C34—H34	0.9300
C4—C20	1.419 (5)	C35—C41	1.358 (5)
C4—C15	1.471 (5)	C35—H35	0.9300
C5—C29	1.377 (5)	C36—C50	1.358 (5)
C5—C23	1.387 (5)	C36—H36	0.9300
C5—C9	1.490 (5)	C37—C38	1.359 (6)
C6—C25	1.359 (5)	C37—H37	0.9300
C6—C8	1.406 (5)	C38—H38	0.9300
C6—H6	0.9300	C39—C46	1.372 (5)
C7—C30	1.367 (5)	C39—H39	0.9300
C7—H7	0.9300	C40—C49	1.373 (6)
C8—C11	1.415 (5)	C40—H40	0.9300
C8—C14	1.456 (5)	C41—H41	0.9300
N1—C20	1.343 (5)	C42—C45	1.379 (5)
N1—H1A	0.8600	C42—H42	0.9300
N1—H1B	0.8600	C43—C48	1.377 (6)
C10—C44	1.389 (5)	C43—H43	0.9300
C10—C19	1.397 (5)	C44—C51	1.358 (6)
C10—C52	1.491 (5)	C44—H44	0.9300
C11—C47	1.401 (5)	C45—H45	0.9300
C12—C18	1.368 (5)	C46—H46	0.9300
C12—C17	1.403 (5)	C47—H47	0.9300
C12—H12	0.9300	C48—C51	1.363 (6)
C13—C26	1.366 (5)	C48—H48	0.9300
C13—H13	0.9300	C49—C50	1.363 (6)
C16—C41	1.404 (5)	C49—H49	0.9300
C17—C22	1.408 (5)	C50—H50	0.9300
C17—C52	1.471 (5)	C51—H51	0.9300
C11—N3—H3A	120.0	C28—C24—C1	121.1 (4)
C11—N3—H3B	120.0	C28—C24—H24	119.4
H3A—N3—H3B	120.0	C1—C24—H24	119.4
C16—N2—H2A	120.0	C6—C25—C34	120.2 (4)
C16—N2—H2B	120.0	C6—C25—Cl2	119.7 (3)
H2A—N2—H2B	120.0	C34—C25—Cl2	120.0 (3)
C24—C1—C21	118.5 (3)	C13—C26—C33	119.1 (4)
C24—C1—C14	119.1 (3)	C13—C26—Cl4	120.8 (3)
C21—C1—C14	122.3 (3)	C33—C26—Cl4	120.0 (3)
C7—C2—C16	118.4 (3)	C40—C27—C3	120.0 (4)
C7—C2—C9	120.6 (3)	C40—C27—H27	120.0
C16—C2—C9	121.0 (3)	C3—C27—H27	120.0
C22—N4—H4A	120.0	C39—C28—C24	119.8 (4)
C22—N4—H4B	120.0	C39—C28—H28	120.1
H4A—N4—H4B	120.0	C24—C28—H28	120.1
C36—C3—C27	118.0 (4)	C5—C29—C45	119.5 (4)
C36—C3—C15	119.4 (3)	C5—C29—H29	120.3
C27—C3—C15	122.4 (4)	C45—C29—H29	120.3
C13—C4—C20	118.9 (4)	C7—C30—C35	120.0 (4)
C13—C4—C15	119.8 (3)	C7—C30—Cl3	120.0 (3)
C20—C4—C15	121.0 (4)	C35—C30—Cl3	120.0 (3)
C29—C5—C23	119.2 (3)	C33—C31—C20	122.5 (4)
C29—C5—C9	122.2 (3)	C33—C31—H31	118.7
C23—C5—C9	118.5 (3)	C20—C31—H31	118.7
C25—C6—C8	121.3 (4)	C23—C32—C42	120.1 (4)
C25—C6—H6	119.4	C23—C32—H32	119.9
C8—C6—H6	119.4	C42—C32—H32	119.9
C30—C7—C2	121.6 (4)	C31—C33—C26	120.2 (4)
C30—C7—H7	119.2	C31—C33—H33	119.9
C2—C7—H7	119.2	C26—C33—H33	119.9
C6—C8—C11	118.5 (3)	C47—C34—C25	120.1 (4)
C6—C8—C14	120.4 (3)	C47—C34—H34	120.0
C11—C8—C14	121.1 (3)	C25—C34—H34	120.0
O3—C9—C2	121.3 (3)	C41—C35—C30	120.1 (4)
O3—C9—C5	117.5 (3)	C41—C35—H35	119.9
C2—C9—C5	121.3 (3)	C30—C35—H35	119.9
C20—N1—H1A	120.0	C50—C36—C3	121.8 (4)
C20—N1—H1B	120.0	C50—C36—H36	119.1
H1A—N1—H1B	120.0	C3—C36—H36	119.1
C44—C10—C19	118.6 (4)	C38—C37—C18	120.2 (4)
C44—C10—C52	119.1 (4)	C38—C37—H37	119.9
C19—C10—C52	122.2 (4)	C18—C37—H37	119.9
N3—C11—C47	119.2 (4)	C37—C38—C22	121.8 (4)
N3—C11—C8	122.5 (3)	C37—C38—H38	119.1
C47—C11—C8	118.3 (4)	C22—C38—H38	119.1
C18—C12—C17	121.2 (4)	C28—C39—C46	119.7 (4)
C18—C12—H12	119.4	C28—C39—H39	120.1
C17—C12—H12	119.4	C46—C39—H39	120.1
C26—C13—C4	122.2 (4)	C49—C40—C27	120.3 (4)
C26—C13—H13	118.9	C49—C40—H40	119.8
C4—C13—H13	118.9	C27—C40—H40	119.8
O2—C14—C8	121.4 (3)	C35—C41—C16	122.1 (4)
O2—C14—C1	117.0 (3)	C35—C41—H41	119.0
C8—C14—C1	121.6 (3)	C16—C41—H41	119.0
O4—C15—C4	121.2 (4)	C32—C42—C45	119.2 (4)
O4—C15—C3	117.1 (3)	C32—C42—H42	120.4
C4—C15—C3	121.7 (3)	C45—C42—H42	120.4
N2—C16—C41	119.4 (4)	C19—C43—C48	120.2 (4)
N2—C16—C2	122.9 (4)	C19—C43—H43	119.9
C41—C16—C2	117.7 (4)	C48—C43—H43	119.9
C12—C17—C22	118.9 (4)	C51—C44—C10	120.5 (4)
C12—C17—C52	119.6 (3)	C51—C44—H44	119.8
C22—C17—C52	121.3 (4)	C10—C44—H44	119.8
C12—C18—C37	119.8 (4)	C29—C45—C42	121.1 (4)
C12—C18—Cl1	120.1 (3)	C29—C45—H45	119.5
C37—C18—Cl1	120.0 (3)	C42—C45—H45	119.5
C43—C19—C10	120.0 (4)	C39—C46—C21	120.7 (4)
C43—C19—H19	120.0	C39—C46—H46	119.6
C10—C19—H19	120.0	C21—C46—H46	119.6
N1—C20—C31	120.3 (4)	C34—C47—C11	121.7 (4)
N1—C20—C4	122.7 (4)	C34—C47—H47	119.2
C31—C20—C4	117.0 (4)	C11—C47—H47	119.2
C46—C21—C1	120.1 (4)	C51—C48—C43	120.0 (4)
C46—C21—H21	120.0	C51—C48—H48	120.0
C1—C21—H21	120.0	C43—C48—H48	120.0
N4—C22—C38	119.1 (4)	C50—C49—C40	119.4 (4)
N4—C22—C17	122.8 (4)	C50—C49—H49	120.3
C38—C22—C17	118.0 (4)	C40—C49—H49	120.3
O1—C52—C17	121.2 (4)	C36—C50—C49	120.4 (4)
O1—C52—C10	117.4 (3)	C36—C50—H50	119.8
C17—C52—C10	121.4 (3)	C49—C50—H50	119.8
C32—C23—C5	120.9 (4)	C44—C51—C48	120.8 (4)
C32—C23—H23	119.6	C44—C51—H51	119.6
C5—C23—H23	119.6	C48—C51—H51	119.6
C16—C2—C7—C30	1.0 (5)	C44—C10—C52—O1	−47.5 (5)
C9—C2—C7—C30	−178.4 (3)	C19—C10—C52—O1	128.3 (4)
C25—C6—C8—C11	1.8 (5)	C44—C10—C52—C17	132.0 (4)
C25—C6—C8—C14	−178.1 (3)	C19—C10—C52—C17	−52.2 (5)
C7—C2—C9—O3	−175.1 (3)	C29—C5—C23—C32	−0.8 (6)
C16—C2—C9—O3	5.5 (6)	C9—C5—C23—C32	−177.6 (4)
C7—C2—C9—C5	4.3 (5)	C21—C1—C24—C28	−0.4 (5)
C16—C2—C9—C5	−175.1 (3)	C14—C1—C24—C28	−177.5 (3)
C29—C5—C9—O3	−126.8 (4)	C8—C6—C25—C34	−0.8 (6)
C23—C5—C9—O3	49.9 (5)	C8—C6—C25—Cl2	178.8 (3)
C29—C5—C9—C2	53.8 (5)	C4—C13—C26—C33	−0.1 (6)
C23—C5—C9—C2	−129.5 (4)	C4—C13—C26—Cl4	177.4 (3)
C6—C8—C11—N3	177.7 (3)	C36—C3—C27—C40	−0.5 (6)
C14—C8—C11—N3	−2.3 (6)	C15—C3—C27—C40	−175.4 (3)
C6—C8—C11—C47	−1.2 (5)	C1—C24—C28—C39	0.3 (6)
C14—C8—C11—C47	178.7 (3)	C23—C5—C29—C45	0.4 (6)
C20—C4—C13—C26	−2.4 (6)	C9—C5—C29—C45	177.1 (4)
C15—C4—C13—C26	−176.6 (3)	C2—C7—C30—C35	0.5 (6)
C6—C8—C14—O2	−173.9 (3)	C2—C7—C30—Cl3	179.6 (3)
C11—C8—C14—O2	6.2 (5)	N1—C20—C31—C33	178.6 (4)
C6—C8—C14—C1	6.3 (5)	C4—C20—C31—C33	−3.2 (6)
C11—C8—C14—C1	−173.6 (3)	C5—C23—C32—C42	0.2 (6)
C24—C1—C14—O2	49.8 (5)	C20—C31—C33—C26	0.8 (6)
C21—C1—C14—O2	−127.2 (4)	C13—C26—C33—C31	0.9 (6)
C24—C1—C14—C8	−130.4 (4)	Cl4—C26—C33—C31	−176.6 (3)
C21—C1—C14—C8	52.6 (5)	C6—C25—C34—C47	−0.8 (6)
C13—C4—C15—O4	166.5 (3)	Cl2—C25—C34—C47	179.6 (3)
C20—C4—C15—O4	−7.7 (6)	C7—C30—C35—C41	−1.8 (6)
C13—C4—C15—C3	−13.3 (5)	Cl3—C30—C35—C41	179.1 (3)
C20—C4—C15—C3	172.5 (3)	C27—C3—C36—C50	1.6 (6)
C36—C3—C15—O4	−47.7 (5)	C15—C3—C36—C50	176.6 (4)
C27—C3—C15—O4	127.2 (4)	C12—C18—C37—C38	0.3 (6)
C36—C3—C15—C4	132.2 (4)	Cl1—C18—C37—C38	−177.8 (3)
C27—C3—C15—C4	−53.0 (5)	C18—C37—C38—C22	1.1 (6)
C7—C2—C16—N2	176.4 (3)	N4—C22—C38—C37	179.4 (4)
C9—C2—C16—N2	−4.2 (6)	C17—C22—C38—C37	−2.6 (6)
C7—C2—C16—C41	−1.3 (5)	C24—C28—C39—C46	0.5 (6)
C9—C2—C16—C41	178.1 (3)	C3—C27—C40—C49	−0.2 (6)
C18—C12—C17—C22	−1.5 (5)	C30—C35—C41—C16	1.6 (6)
C18—C12—C17—C52	−176.4 (3)	N2—C16—C41—C35	−177.7 (4)
C17—C12—C18—C37	−0.1 (6)	C2—C16—C41—C35	0.0 (6)
C17—C12—C18—Cl1	178.0 (3)	C23—C32—C42—C45	0.8 (6)
C44—C10—C19—C43	0.6 (6)	C10—C19—C43—C48	−1.0 (6)
C52—C10—C19—C43	−175.2 (3)	C19—C10—C44—C51	0.1 (6)
C13—C4—C20—N1	−178.0 (3)	C52—C10—C44—C51	176.1 (4)
C15—C4—C20—N1	−3.8 (6)	C5—C29—C45—C42	0.6 (6)
C13—C4—C20—C31	3.9 (5)	C32—C42—C45—C29	−1.2 (7)
C15—C4—C20—C31	178.1 (3)	C28—C39—C46—C21	−1.3 (7)
C24—C1—C21—C46	−0.4 (6)	C1—C21—C46—C39	1.2 (6)
C14—C1—C21—C46	176.7 (4)	C25—C34—C47—C11	1.4 (6)
C12—C17—C22—N4	−179.4 (3)	N3—C11—C47—C34	−179.3 (4)
C52—C17—C22—N4	−4.5 (6)	C8—C11—C47—C34	−0.4 (6)
C12—C17—C22—C38	2.7 (5)	C19—C43—C48—C51	0.7 (7)
C52—C17—C22—C38	177.5 (3)	C27—C40—C49—C50	−0.2 (7)
C12—C17—C52—O1	165.7 (3)	C3—C36—C50—C49	−1.9 (7)
C22—C17—C52—O1	−9.1 (6)	C40—C49—C50—C36	1.2 (7)
C12—C17—C52—C10	−13.9 (5)	C10—C44—C51—C48	−0.4 (7)
C22—C17—C52—C10	171.3 (3)	C43—C48—C51—C44	0.0 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.86	2.21	2.971 (5)	147
N1—H1B···O4	0.86	2.01	2.642 (5)	130
N2—H2A···O1^ii	0.86	2.16	2.962 (4)	154
N2—H2B···O3	0.86	1.99	2.629 (4)	130
N3—H3A···O3	0.86	2.19	2.960 (4)	149
N3—H3B···O2	0.86	1.98	2.623 (4)	130
N4—H4A···O4	0.86	2.19	2.986 (5)	153
N4—H4B···O1	0.86	2.03	2.654 (5)	129

Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z.