2-Chloro-N-(2-nitro­phen­yl)acetamide

The title compound, C₈H₇ClN₂O₃, crystallizes with four mol­ecules in the asymmetric unit. The amide H atom is involved in intra­molecular hydrogen bonding with the O atom of the nitro group as well as the side-chain Cl atom. The C=O group is not involved in hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 303 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.053
• wR factor = 0.123
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N40
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N54
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.12
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C8 H7 Cl N2 O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C8 H7 Cl N2 O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C8 H7 Cl N2 O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              C8 H7 Cl N2 O3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               6977
           Count of symmetry unique reflns         3743
           Completeness (_total/calc)            186.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3234
           Fraction of Friedel pairs measured     0.864
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-Chloro-N-(2-nitrophenyl)acetamide

Crystal data

C8H7ClN2O3	F(000) = 880
Mr = 214.61	Dx = 1.546 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 1486 reflections
a = 16.386 (2) Å	θ = 3.2–20.3°
b = 3.9388 (8) Å	µ = 0.40 mm^−1
c = 28.566 (3) Å	T = 303 K
β = 90.272 (9)°	Long prism, light brown
V = 1843.7 (5) Å^3	0.50 × 0.20 × 0.08 mm
Z = 8

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	3736 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 26.4°, θmin = 4.3°
Rotation method data acquisition using ω scans	h = −20→20
16544 measured reflections	k = −4→3
6977 independent reflections	l = −35→35

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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0523P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.017
6977 reflections	Δρmax = 0.20 e Å^−3
505 parameters	Δρmin = −0.22 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (6)

Special details

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.

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 > σ(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
C2	−0.1760 (2)	−0.1148 (11)	−0.07922 (15)	0.0471 (11)
H2A	−0.2134	0.0530	−0.0668	0.056*
H2B	−0.2085	−0.2968	−0.0926	0.056*
C3	−0.1267 (3)	−0.2573 (11)	−0.03913 (16)	0.0458 (11)
C6	0.0127 (3)	−0.2795 (11)	−0.00422 (14)	0.0399 (10)
C7	0.0958 (3)	−0.2253 (11)	−0.01232 (15)	0.0472 (11)
C8	0.1546 (3)	−0.3264 (14)	0.02093 (18)	0.0617 (14)
H8	0.2098	−0.2957	0.0147	0.074*
C9	0.1312 (4)	−0.4702 (14)	0.06262 (18)	0.0710 (16)
H9	0.1698	−0.5312	0.0851	0.085*
C10	0.0500 (4)	−0.5212 (13)	0.07028 (18)	0.0651 (14)
H10	0.0336	−0.6221	0.0981	0.078*
C11	−0.0090 (3)	−0.4274 (12)	0.03783 (16)	0.0548 (12)
H11	−0.0638	−0.4644	0.0444	0.066*
N5	−0.0453 (2)	−0.1808 (9)	−0.03731 (12)	0.0445 (9)
H5N	−0.0275	−0.0546	−0.0596	0.053*
N12	0.1272 (3)	−0.0735 (12)	−0.05490 (15)	0.0650 (12)
O4	−0.16229 (19)	−0.4311 (9)	−0.01034 (12)	0.0675 (11)
O13	0.0808 (2)	0.0920 (10)	−0.08022 (12)	0.0714 (10)
O14	0.1980 (3)	−0.1119 (16)	−0.06464 (18)	0.142 (2)
Cl1	−0.11904 (7)	0.0767 (3)	−0.12488 (4)	0.0633 (4)
C16	−0.1774 (3)	−0.8202 (12)	−0.32420 (17)	0.0580 (13)
H16B	−0.2121	−0.6419	−0.3367	0.070*
H16A	−0.2128	−0.9906	−0.3105	0.070*
C17	−0.1251 (3)	−0.6713 (12)	−0.28590 (17)	0.0488 (12)
C20	0.0166 (3)	−0.6453 (11)	−0.25457 (15)	0.0453 (11)
C21	0.0990 (3)	−0.7066 (11)	−0.26399 (15)	0.0454 (11)
C22	0.1595 (3)	−0.6110 (14)	−0.23221 (18)	0.0659 (15)
H22A	0.2142	−0.6515	−0.2388	0.079*
C23	0.1378 (4)	−0.4580 (14)	−0.19148 (19)	0.0708 (15)
H23A	0.1781	−0.3938	−0.1702	0.085*
C24	0.0584 (3)	−0.3976 (13)	−0.18148 (17)	0.0624 (13)
H24A	0.0444	−0.2979	−0.1531	0.075*
C25	−0.0019 (3)	−0.4832 (12)	−0.21313 (16)	0.0549 (12)
H25A	−0.0560	−0.4309	−0.2065	0.066*
N19	−0.0438 (2)	−0.7391 (9)	−0.28697 (13)	0.0471 (9)
H19N	−0.0273	−0.8547	−0.3106	0.057*
N26	0.1271 (3)	−0.8741 (12)	−0.30618 (16)	0.0670 (12)
O18	−0.15902 (19)	−0.4963 (9)	−0.25598 (13)	0.0653 (10)
O27	0.1994 (2)	−0.8659 (15)	−0.31548 (16)	0.1231 (18)
O28	0.0787 (2)	−1.0152 (10)	−0.33197 (12)	0.0778 (12)
Cl15	−0.12368 (7)	−1.0087 (4)	−0.37133 (4)	0.0701 (4)
C30	−0.3051 (3)	0.1255 (12)	0.04524 (16)	0.0532 (12)
H30B	−0.2683	−0.0439	0.0580	0.064*
H30A	−0.2719	0.3047	0.0320	0.064*
C31	−0.3539 (3)	0.2754 (11)	0.08543 (16)	0.0495 (12)
C34	−0.4937 (2)	0.3170 (10)	0.11742 (14)	0.0389 (10)
C35	−0.5769 (3)	0.2581 (11)	0.10991 (15)	0.0448 (11)
C36	−0.6358 (3)	0.3514 (13)	0.14336 (17)	0.0602 (13)
H36A	−0.6908	0.3058	0.1381	0.072*
C37	−0.6114 (4)	0.5095 (14)	0.18365 (18)	0.0691 (16)
H37A	−0.6500	0.5742	0.2057	0.083*
C38	−0.5308 (3)	0.5728 (12)	0.19159 (16)	0.0602 (13)
H38A	−0.5144	0.6746	0.2195	0.072*
C39	−0.4724 (3)	0.4851 (11)	0.15798 (16)	0.0517 (12)
H39A	−0.4180	0.5418	0.1632	0.062*
N33	−0.4358 (2)	0.2178 (9)	0.08439 (12)	0.0471 (9)
H33N	−0.4540	0.1072	0.0606	0.057*
N40	−0.6087 (3)	0.0906 (11)	0.06849 (15)	0.0627 (11)
O32	−0.3177 (2)	0.4375 (10)	0.11464 (13)	0.0769 (11)
O41	−0.6807 (3)	0.0996 (16)	0.05997 (17)	0.134 (2)
O42	−0.5624 (2)	−0.0522 (10)	0.04097 (13)	0.0767 (11)
Cl29	−0.36111 (7)	−0.0630 (4)	−0.00039 (4)	0.0673 (4)
C44	−0.3032 (3)	−0.9299 (12)	−0.20122 (14)	0.0483 (11)
H44B	−0.2670	−1.1013	−0.1883	0.058*
H44A	−0.2693	−0.7483	−0.2133	0.058*
C45	−0.3556 (3)	−0.7862 (11)	−0.16123 (16)	0.0447 (11)
C48	−0.4969 (3)	−0.7688 (11)	−0.13101 (14)	0.0427 (11)
C49	−0.5793 (3)	−0.8370 (12)	−0.14141 (16)	0.0503 (11)
C50	−0.6394 (3)	−0.7471 (14)	−0.10838 (19)	0.0671 (15)
H50A	−0.6938	−0.7987	−0.1144	0.081*
C51	−0.6186 (4)	−0.5850 (13)	−0.0677 (2)	0.0717 (17)
H51A	−0.6588	−0.5188	−0.0467	0.086*
C52	−0.5375 (4)	−0.5212 (13)	−0.05815 (18)	0.0691 (15)
H52A	−0.5230	−0.4180	−0.0300	0.083*
C53	−0.4779 (3)	−0.6072 (12)	−0.08943 (16)	0.0551 (12)
H53A	−0.4238	−0.5560	−0.0826	0.066*
N47	−0.4355 (2)	−0.8616 (9)	−0.16313 (12)	0.0477 (9)
H47N	−0.4512	−0.9808	−0.1867	0.057*
N54	−0.6059 (3)	−1.0097 (12)	−0.18281 (16)	0.0654 (12)
O46	−0.32114 (19)	−0.6107 (9)	−0.13307 (13)	0.0683 (10)
O55	−0.6785 (2)	−1.0229 (15)	−0.19165 (17)	0.1267 (19)
O56	−0.5577 (2)	−1.1441 (11)	−0.20930 (13)	0.0808 (12)
Cl43	−0.35812 (7)	−1.1129 (3)	−0.24879 (4)	0.0645 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.029 (2)	0.050 (3)	0.062 (3)	0.000 (2)	−0.009 (2)	0.001 (2)
C3	0.038 (3)	0.042 (3)	0.057 (3)	−0.004 (2)	−0.001 (2)	−0.008 (2)
C6	0.035 (2)	0.051 (3)	0.034 (2)	0.002 (2)	−0.0017 (19)	−0.005 (2)
C7	0.041 (3)	0.061 (3)	0.040 (3)	−0.005 (2)	0.003 (2)	−0.007 (2)
C8	0.026 (2)	0.095 (4)	0.064 (3)	0.005 (3)	−0.015 (2)	−0.014 (3)
C9	0.075 (4)	0.092 (4)	0.045 (3)	0.009 (3)	−0.025 (3)	−0.011 (3)
C10	0.067 (4)	0.075 (4)	0.053 (3)	0.003 (3)	−0.004 (3)	0.011 (3)
C11	0.044 (3)	0.078 (3)	0.043 (3)	−0.001 (3)	0.006 (2)	0.005 (3)
N5	0.035 (2)	0.056 (2)	0.042 (2)	−0.0070 (17)	0.0021 (17)	0.0047 (18)
N12	0.037 (3)	0.099 (3)	0.059 (3)	−0.015 (2)	−0.001 (2)	−0.004 (3)
O4	0.044 (2)	0.088 (3)	0.071 (2)	−0.0130 (18)	0.0015 (19)	0.030 (2)
O13	0.055 (2)	0.108 (3)	0.051 (2)	−0.018 (2)	−0.0006 (19)	0.016 (2)
O14	0.044 (3)	0.257 (6)	0.124 (4)	0.001 (3)	0.029 (3)	0.055 (4)
Cl1	0.0532 (9)	0.0855 (9)	0.0514 (8)	0.0080 (8)	0.0012 (7)	0.0124 (7)
C16	0.042 (3)	0.068 (3)	0.064 (3)	0.000 (2)	−0.001 (2)	0.012 (3)
C17	0.036 (3)	0.058 (3)	0.053 (3)	−0.001 (2)	−0.005 (2)	0.016 (3)
C20	0.037 (3)	0.058 (3)	0.041 (3)	−0.003 (2)	−0.003 (2)	0.006 (2)
C21	0.036 (3)	0.063 (3)	0.037 (2)	−0.003 (2)	0.000 (2)	0.001 (2)
C22	0.038 (3)	0.097 (4)	0.062 (3)	0.006 (3)	−0.005 (3)	−0.002 (3)
C23	0.063 (4)	0.095 (4)	0.054 (4)	−0.007 (3)	−0.019 (3)	−0.007 (3)
C24	0.060 (4)	0.080 (3)	0.047 (3)	0.004 (3)	−0.011 (3)	−0.005 (3)
C25	0.047 (3)	0.073 (3)	0.045 (3)	0.005 (2)	0.006 (2)	0.001 (3)
N19	0.033 (2)	0.067 (2)	0.042 (2)	0.0001 (19)	−0.0013 (17)	−0.0047 (19)
N26	0.038 (3)	0.102 (3)	0.061 (3)	0.010 (2)	0.011 (2)	−0.001 (3)
O18	0.041 (2)	0.091 (3)	0.064 (2)	0.0113 (18)	0.0043 (18)	−0.0099 (19)
O27	0.043 (2)	0.225 (5)	0.102 (3)	0.000 (3)	0.014 (2)	−0.062 (4)
O28	0.058 (2)	0.123 (3)	0.053 (2)	0.006 (2)	−0.001 (2)	−0.027 (2)
Cl15	0.0527 (9)	0.1052 (11)	0.0524 (9)	−0.0122 (7)	−0.0075 (7)	−0.0045 (7)
C30	0.039 (3)	0.058 (3)	0.062 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C31	0.043 (3)	0.058 (3)	0.048 (3)	−0.005 (2)	0.003 (2)	0.010 (2)
C34	0.035 (2)	0.048 (3)	0.034 (2)	0.002 (2)	−0.0010 (19)	0.004 (2)
C35	0.045 (3)	0.051 (3)	0.038 (2)	0.000 (2)	−0.002 (2)	−0.001 (2)
C36	0.036 (3)	0.089 (4)	0.056 (3)	−0.001 (3)	0.005 (2)	0.014 (3)
C37	0.070 (4)	0.095 (4)	0.041 (3)	0.019 (3)	0.008 (3)	−0.001 (3)
C38	0.063 (4)	0.079 (3)	0.039 (3)	0.006 (3)	0.000 (3)	−0.002 (3)
C39	0.050 (3)	0.064 (3)	0.041 (3)	0.002 (2)	−0.008 (2)	−0.007 (2)
N33	0.035 (2)	0.064 (2)	0.042 (2)	−0.0037 (19)	−0.0008 (17)	−0.0071 (19)
N40	0.040 (3)	0.089 (3)	0.060 (3)	−0.009 (2)	−0.003 (2)	−0.003 (3)
O32	0.047 (2)	0.111 (3)	0.072 (3)	−0.015 (2)	−0.0061 (19)	−0.031 (2)
O41	0.040 (3)	0.248 (6)	0.115 (4)	0.000 (3)	−0.020 (2)	−0.077 (4)
O42	0.053 (2)	0.119 (3)	0.058 (2)	−0.008 (2)	0.0041 (19)	−0.020 (2)
Cl29	0.0539 (8)	0.0954 (11)	0.0526 (8)	0.0071 (7)	0.0052 (6)	−0.0109 (7)
C44	0.034 (2)	0.062 (3)	0.048 (3)	−0.003 (2)	−0.003 (2)	0.002 (2)
C45	0.030 (2)	0.052 (3)	0.052 (3)	−0.007 (2)	−0.006 (2)	0.005 (2)
C48	0.046 (3)	0.047 (3)	0.036 (2)	0.007 (2)	0.007 (2)	0.007 (2)
C49	0.038 (3)	0.070 (3)	0.043 (3)	0.000 (2)	0.008 (2)	0.010 (2)
C50	0.049 (3)	0.085 (4)	0.067 (4)	0.003 (3)	0.019 (3)	0.018 (3)
C51	0.082 (5)	0.067 (3)	0.066 (4)	0.017 (3)	0.037 (3)	0.003 (3)
C52	0.074 (4)	0.077 (4)	0.056 (3)	−0.002 (3)	0.017 (3)	−0.005 (3)
C53	0.050 (3)	0.066 (3)	0.049 (3)	−0.006 (3)	0.004 (2)	−0.003 (3)
N47	0.038 (2)	0.067 (2)	0.038 (2)	−0.0027 (19)	−0.0016 (17)	−0.0074 (19)
N54	0.046 (3)	0.093 (3)	0.057 (3)	−0.011 (2)	−0.011 (2)	0.006 (2)
O46	0.040 (2)	0.092 (3)	0.074 (2)	−0.0184 (19)	−0.0054 (18)	−0.022 (2)
O55	0.039 (3)	0.229 (6)	0.112 (4)	−0.008 (3)	−0.021 (2)	−0.041 (3)
O56	0.051 (2)	0.133 (3)	0.058 (2)	−0.017 (2)	−0.0034 (19)	−0.028 (2)
Cl43	0.0519 (8)	0.0901 (10)	0.0515 (8)	0.0048 (8)	0.0007 (6)	−0.0108 (8)

Geometric parameters (Å, º)

C2—C3	1.506 (6)	C30—C31	1.521 (6)
C2—Cl1	1.775 (4)	C30—Cl29	1.755 (4)
C2—H2A	0.9700	C30—H30B	0.9700
C2—H2B	0.9700	C30—H30A	0.9700
C3—O4	1.220 (5)	C31—O32	1.204 (5)
C3—N5	1.368 (5)	C31—N33	1.361 (6)
C6—C11	1.383 (6)	C34—C39	1.378 (6)
C6—N5	1.392 (5)	C34—N33	1.397 (5)
C6—C7	1.400 (6)	C34—C35	1.399 (6)
C7—C8	1.407 (6)	C35—C36	1.410 (6)
C7—N12	1.452 (6)	C35—N40	1.449 (6)
C8—C9	1.375 (7)	C36—C37	1.366 (7)
C8—H8	0.9300	C36—H36A	0.9300
C9—C10	1.365 (7)	C37—C38	1.363 (7)
C9—H9	0.9300	C37—H37A	0.9300
C10—C11	1.385 (7)	C38—C39	1.402 (6)
C10—H10	0.9300	C38—H38A	0.9300
C11—H11	0.9300	C39—H39A	0.9300
N5—H5N	0.8600	N33—H33N	0.8600
N12—O14	1.203 (5)	N40—O41	1.205 (5)
N12—O13	1.233 (5)	N40—O42	1.230 (5)
C16—C17	1.505 (6)	C44—C45	1.541 (6)
C16—Cl15	1.775 (5)	C44—Cl43	1.779 (4)
C16—H16B	0.9700	C44—H44B	0.9700
C16—H16A	0.9700	C44—H44A	0.9700
C17—O18	1.232 (5)	C45—O46	1.200 (5)
C17—N19	1.360 (6)	C45—N47	1.343 (5)
C20—C25	1.380 (6)	C48—C53	1.382 (6)
C20—C21	1.399 (6)	C48—C49	1.407 (6)
C20—N19	1.402 (5)	C48—N47	1.413 (5)
C21—C22	1.393 (6)	C49—C50	1.411 (6)
C21—N26	1.451 (6)	C49—N54	1.431 (6)
C22—C23	1.359 (7)	C50—C51	1.368 (7)
C22—H22A	0.9300	C50—H50A	0.9300
C23—C24	1.356 (7)	C51—C52	1.378 (7)
C23—H23A	0.9300	C51—H51A	0.9300
C24—C25	1.378 (7)	C52—C53	1.369 (6)
C24—H24A	0.9300	C52—H52A	0.9300
C25—H25A	0.9300	C53—H53A	0.9300
N19—H19N	0.8600	N47—H47N	0.8600
N26—O28	1.214 (5)	N54—O55	1.216 (5)
N26—O27	1.216 (5)	N54—O56	1.217 (5)
C3—C2—Cl1	115.8 (3)	C31—C30—Cl29	116.8 (3)
C3—C2—H2A	108.3	C31—C30—H30B	108.1
Cl1—C2—H2A	108.3	Cl29—C30—H30B	108.1
C3—C2—H2B	108.3	C31—C30—H30A	108.1
Cl1—C2—H2B	108.3	Cl29—C30—H30A	108.1
H2A—C2—H2B	107.4	H30B—C30—H30A	107.3
O4—C3—N5	124.5 (4)	O32—C31—N33	125.9 (5)
O4—C3—C2	117.7 (4)	O32—C31—C30	118.0 (4)
N5—C3—C2	117.7 (4)	N33—C31—C30	116.1 (4)
C11—C6—N5	122.1 (4)	C39—C34—N33	122.2 (4)
C11—C6—C7	117.5 (4)	C39—C34—C35	116.8 (4)
N5—C6—C7	120.4 (4)	N33—C34—C35	121.0 (4)
C6—C7—C8	120.6 (4)	C34—C35—C36	121.5 (4)
C6—C7—N12	123.4 (4)	C34—C35—N40	123.1 (4)
C8—C7—N12	115.9 (4)	C36—C35—N40	115.4 (4)
C9—C8—C7	120.5 (5)	C37—C36—C35	119.4 (5)
C9—C8—H8	119.7	C37—C36—H36A	120.3
C7—C8—H8	119.7	C35—C36—H36A	120.3
C10—C9—C8	118.4 (5)	C38—C37—C36	120.2 (5)
C10—C9—H9	120.8	C38—C37—H37A	119.9
C8—C9—H9	120.8	C36—C37—H37A	119.9
C9—C10—C11	122.0 (5)	C37—C38—C39	120.3 (5)
C9—C10—H10	119.0	C37—C38—H38A	119.8
C11—C10—H10	119.0	C39—C38—H38A	119.8
C6—C11—C10	120.9 (5)	C34—C39—C38	121.6 (5)
C6—C11—H11	119.6	C34—C39—H39A	119.2
C10—C11—H11	119.6	C38—C39—H39A	119.2
C3—N5—C6	128.8 (4)	C31—N33—C34	127.7 (4)
C3—N5—H5N	115.6	C31—N33—H33N	116.2
C6—N5—H5N	115.6	C34—N33—H33N	116.2
O14—N12—O13	121.5 (5)	O41—N40—O42	119.4 (5)
O14—N12—C7	119.2 (5)	O41—N40—C35	119.9 (4)
O13—N12—C7	119.3 (4)	O42—N40—C35	120.7 (4)
C17—C16—Cl15	115.6 (3)	C45—C44—Cl43	115.7 (3)
C17—C16—H16B	108.4	C45—C44—H44B	108.4
Cl15—C16—H16B	108.4	Cl43—C44—H44B	108.4
C17—C16—H16A	108.4	C45—C44—H44A	108.4
Cl15—C16—H16A	108.4	Cl43—C44—H44A	108.4
H16B—C16—H16A	107.5	H44B—C44—H44A	107.4
O18—C17—N19	124.8 (5)	O46—C45—N47	127.6 (4)
O18—C17—C16	117.7 (4)	O46—C45—C44	116.5 (4)
N19—C17—C16	117.5 (4)	N47—C45—C44	115.9 (4)
C25—C20—C21	117.5 (4)	C53—C48—C49	118.8 (4)
C25—C20—N19	122.0 (4)	C53—C48—N47	121.3 (4)
C21—C20—N19	120.5 (4)	C49—C48—N47	120.0 (4)
C22—C21—C20	120.8 (4)	C48—C49—C50	118.8 (5)
C22—C21—N26	115.9 (4)	C48—C49—N54	123.6 (4)
C20—C21—N26	123.3 (4)	C50—C49—N54	117.5 (5)
C23—C22—C21	119.3 (5)	C51—C50—C49	121.0 (5)
C23—C22—H22A	120.3	C51—C50—H50A	119.5
C21—C22—H22A	120.3	C49—C50—H50A	119.5
C24—C23—C22	120.9 (5)	C50—C51—C52	119.2 (5)
C24—C23—H23A	119.6	C50—C51—H51A	120.4
C22—C23—H23A	119.6	C52—C51—H51A	120.4
C23—C24—C25	120.3 (5)	C53—C52—C51	121.1 (5)
C23—C24—H24A	119.8	C53—C52—H52A	119.5
C25—C24—H24A	119.8	C51—C52—H52A	119.5
C24—C25—C20	121.1 (5)	C52—C53—C48	121.1 (5)
C24—C25—H25A	119.5	C52—C53—H53A	119.4
C20—C25—H25A	119.5	C48—C53—H53A	119.4
C17—N19—C20	128.5 (4)	C45—N47—C48	127.9 (4)
C17—N19—H19N	115.7	C45—N47—H47N	116.1
C20—N19—H19N	115.7	C48—N47—H47N	116.1
O28—N26—O27	120.9 (5)	O55—N54—O56	119.3 (5)
O28—N26—C21	120.2 (4)	O55—N54—C49	119.1 (5)
O27—N26—C21	118.9 (5)	O56—N54—C49	121.6 (4)
Cl1—C2—C3—O4	−170.2 (3)	Cl29—C30—C31—O32	−172.3 (4)
Cl1—C2—C3—N5	10.3 (5)	Cl29—C30—C31—N33	6.5 (6)
C11—C6—C7—C8	1.5 (6)	C39—C34—C35—C36	−3.0 (6)
N5—C6—C7—C8	−179.7 (4)	N33—C34—C35—C36	178.8 (4)
C11—C6—C7—N12	179.8 (4)	C39—C34—C35—N40	178.7 (4)
N5—C6—C7—N12	−1.3 (7)	N33—C34—C35—N40	0.6 (6)
C6—C7—C8—C9	−2.1 (7)	C34—C35—C36—C37	1.4 (7)
N12—C7—C8—C9	179.4 (5)	N40—C35—C36—C37	179.7 (4)
C7—C8—C9—C10	1.9 (8)	C35—C36—C37—C38	−0.7 (8)
C8—C9—C10—C11	−1.2 (8)	C36—C37—C38—C39	1.8 (8)
N5—C6—C11—C10	−179.6 (4)	N33—C34—C39—C38	−177.7 (4)
C7—C6—C11—C10	−0.7 (7)	C35—C34—C39—C38	4.1 (6)
C9—C10—C11—C6	0.6 (8)	C37—C38—C39—C34	−3.6 (7)
O4—C3—N5—C6	0.4 (7)	O32—C31—N33—C34	−3.5 (7)
C2—C3—N5—C6	179.9 (4)	C30—C31—N33—C34	177.9 (4)
C11—C6—N5—C3	−12.3 (7)	C39—C34—N33—C31	−2.3 (7)
C7—C6—N5—C3	168.9 (4)	C35—C34—N33—C31	175.7 (4)
C6—C7—N12—O14	−161.4 (5)	C34—C35—N40—O41	−167.0 (5)
C8—C7—N12—O14	17.0 (7)	C36—C35—N40—O41	14.7 (7)
C6—C7—N12—O13	18.7 (7)	C34—C35—N40—O42	10.7 (7)
C8—C7—N12—O13	−162.9 (4)	C36—C35—N40—O42	−167.6 (4)
Cl15—C16—C17—O18	169.9 (3)	Cl43—C44—C45—O46	−167.4 (4)
Cl15—C16—C17—N19	−9.9 (5)	Cl43—C44—C45—N47	10.0 (5)
C25—C20—C21—C22	0.9 (7)	C53—C48—C49—C50	−1.8 (6)
N19—C20—C21—C22	179.3 (4)	N47—C48—C49—C50	178.9 (4)
C25—C20—C21—N26	−179.9 (4)	C53—C48—C49—N54	−178.5 (4)
N19—C20—C21—N26	−1.5 (7)	N47—C48—C49—N54	2.3 (7)
C20—C21—C22—C23	0.4 (8)	C48—C49—C50—C51	2.4 (7)
N26—C21—C22—C23	−178.9 (5)	N54—C49—C50—C51	179.2 (4)
C21—C22—C23—C24	0.0 (8)	C49—C50—C51—C52	−2.5 (8)
C22—C23—C24—C25	−1.6 (9)	C50—C51—C52—C53	2.2 (8)
C23—C24—C25—C20	3.0 (8)	C51—C52—C53—C48	−1.7 (8)
C21—C20—C25—C24	−2.5 (7)	C49—C48—C53—C52	1.5 (7)
N19—C20—C25—C24	179.1 (4)	N47—C48—C53—C52	−179.2 (4)
O18—C17—N19—C20	3.5 (7)	O46—C45—N47—C48	−4.0 (7)
C16—C17—N19—C20	−176.7 (4)	C44—C45—N47—C48	178.9 (4)
C25—C20—N19—C17	5.3 (7)	C53—C48—N47—C45	−6.6 (7)
C21—C20—N19—C17	−173.1 (4)	C49—C48—N47—C45	172.6 (4)
C22—C21—N26—O28	167.9 (5)	C48—C49—N54—O55	−171.5 (5)
C20—C21—N26—O28	−11.4 (7)	C50—C49—N54—O55	11.9 (7)
C22—C21—N26—O27	−13.3 (7)	C48—C49—N54—O56	8.7 (7)
C20—C21—N26—O27	167.5 (5)	C50—C49—N54—O56	−168.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O13	0.86	1.96	2.637 (5)	135
N5—H5N···Cl1	0.86	2.44	2.952 (4)	119
N19—H19N···O28	0.86	1.95	2.625 (5)	135
N19—H19N···Cl15	0.86	2.42	2.936 (4)	119
N33—H33N···O42	0.86	1.96	2.636 (5)	134
N33—H33N···Cl29	0.86	2.41	2.935 (4)	120
N47—H47N···O56	0.86	1.97	2.638 (5)	134
N47—H47N···Cl43	0.86	2.40	2.934 (4)	121