N-(3-Chloro-4-methyl­phenyl)-N′-hydroxy-2-oxo-2-phenyl­acet­amidine

The title compound, C₁₅H₁₃ClN₂O₂, contains two independent molecules in the asymmetric unit. In both mol­ecules, the oxime moiety has an E configuration. Intermolecular O—H...N [O...N = 2.776 (2) and 2.771 (2) Å] and intramolecular N—H...O [N...O = 2.532 (3) and 2.534 (3) Å] hydrogen bonds are highly effective in the crystal structure. The O—H...N intermolecular hydrogen bonds link the independent mol­ecules into dimers, which are, in turn, interlinked through N—H...Cl interactions to form layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.100
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.753
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.420
           From the CIF: _refine_ls_abs_structure_Flack_su    0.060
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.42
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4'    -   C5'      =       5.82 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         N1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C4
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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           28.24
           From the CIF: _reflns_number_total               7041
           Count of symmetry unique reflns         3637
           Completeness (_total/calc)            193.59%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3404
           Fraction of Friedel pairs measured     0.936
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(3-chloro-4-methylphenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine

Crystal data

C15H13ClN2O2	F(000) = 1200
Mr = 288.73	Dx = 1.342 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 13878 reflections
a = 25.6412 (14) Å	θ = 2.3–26.9°
b = 4.9773 (3) Å	µ = 0.27 mm^−1
c = 22.3894 (16) Å	T = 293 K
V = 2857.4 (3) Å^3	Rod shaped, pale yellow
Z = 8	0.40 × 0.30 × 0.15 mm

Data collection

Stoe IPDS-2 diffractometer	3175 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.091
Plane graphite monochromator	θmax = 28.2°, θmin = 1.6°
Detector resolution: 6.67 pixels mm^-1	h = −34→33
φ scans	k = −6→5
32785 measured reflections	l = −29→29
7041 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)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0463P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 0.75	Δρmax = 0.16 e Å^−3
7041 reflections	Δρmin = −0.15 e Å^−3
367 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0088 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 3418 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.42 (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
Cl1	−0.20397 (3)	0.3646 (3)	0.08262 (5)	0.1223 (4)
O1	0.02413 (7)	0.4379 (4)	0.18187 (9)	0.0815 (6)
O2	0.06502 (6)	0.4247 (5)	−0.01021 (8)	0.0888 (7)
H2	0.0905	0.4623	−0.0306	0.133*
N1	−0.00806 (7)	0.3135 (6)	0.06172 (11)	0.0809 (8)
H1	−0.0130	0.3751	0.0263	0.097*
N2	0.08091 (7)	0.3792 (5)	0.04948 (9)	0.0671 (6)
C1	−0.05266 (9)	0.2123 (6)	0.09121 (13)	0.0644 (7)
C2	−0.10019 (9)	0.3230 (7)	0.07668 (15)	0.0749 (8)
H2A	−0.1023	0.4607	0.0487	0.090*
C3	−0.14466 (10)	0.2278 (7)	0.10404 (15)	0.0753 (9)
C4	−0.14337 (11)	0.0349 (7)	0.14752 (17)	0.0866 (9)
C5	−0.09529 (13)	−0.0774 (7)	0.15976 (18)	0.0978 (11)
H5	−0.0932	−0.2124	0.1884	0.117*
C6	−0.05008 (10)	0.0032 (7)	0.13112 (16)	0.0805 (8)
H6	−0.0186	−0.0826	0.1388	0.097*
C7	0.04148 (8)	0.3253 (6)	0.08261 (12)	0.0604 (7)
C8	0.05319 (9)	0.3201 (6)	0.14830 (12)	0.0604 (7)
C9	0.10153 (9)	0.1852 (5)	0.16941 (12)	0.0547 (7)
C10	0.12172 (11)	0.2645 (6)	0.22378 (15)	0.0766 (9)
H10	0.1051	0.3978	0.2458	0.092*
C11	0.16667 (12)	0.1454 (7)	0.24542 (15)	0.0863 (10)
H11	0.1804	0.1997	0.2819	0.104*
C12	0.19052 (11)	−0.0483 (7)	0.21392 (15)	0.0822 (9)
H12	0.2208	−0.1265	0.2287	0.099*
C13	0.17088 (10)	−0.1313 (6)	0.16079 (15)	0.0800 (9)
H13	0.1875	−0.2678	0.1397	0.096*
C14	0.12639 (9)	−0.0142 (6)	0.13776 (13)	0.0664 (7)
H14	0.1133	−0.0698	0.1010	0.080*
C15	−0.19151 (15)	−0.0510 (10)	0.1825 (2)	0.1364 (17)
H15A	−0.2198	−0.0836	0.1554	0.205*
H15B	−0.2011	0.0890	0.2099	0.205*
H15C	−0.1840	−0.2123	0.2044	0.205*
Cl1'	0.04507 (3)	0.2216 (2)	0.45069 (5)	0.1152 (4)
O1'	0.27102 (6)	0.0067 (4)	0.34046 (9)	0.0776 (6)
O2'	0.31347 (6)	−0.0313 (5)	0.53234 (9)	0.0898 (7)
H2'	0.3386	−0.0813	0.5521	0.135*
N1'	0.24103 (7)	0.1175 (5)	0.46284 (10)	0.0690 (6)
H1'	0.2347	0.0401	0.4964	0.083*
N2'	0.32912 (7)	0.0157 (5)	0.47350 (9)	0.0682 (6)
C1'	0.19930 (9)	0.2558 (6)	0.43612 (13)	0.0617 (7)
C2'	0.14888 (9)	0.1805 (6)	0.45255 (16)	0.0689 (8)
H2'A	0.1435	0.0427	0.4799	0.083*
C3'	0.10738 (10)	0.3142 (8)	0.42744 (17)	0.0783 (10)
C4'	0.11279 (12)	0.5175 (7)	0.38652 (17)	0.0834 (10)
C5'	0.16413 (11)	0.5932 (6)	0.37281 (16)	0.0817 (9)
H5'	0.1697	0.7333	0.3461	0.098*
C6'	0.20632 (10)	0.4664 (6)	0.39774 (14)	0.0708 (8)
H6'	0.2399	0.5238	0.3885	0.085*
C7'	0.29039 (8)	0.0934 (6)	0.44109 (11)	0.0595 (7)
C8'	0.30250 (8)	0.1000 (6)	0.37548 (12)	0.0577 (6)
C9'	0.35389 (9)	0.2035 (5)	0.35574 (13)	0.0569 (7)
C10'	0.37528 (11)	0.1050 (7)	0.30424 (14)	0.0825 (9)
H10'	0.3574	−0.0239	0.2823	0.099*
C11'	0.42325 (14)	0.1952 (8)	0.28455 (17)	0.0966 (11)
H11'	0.4379	0.1228	0.2501	0.116*
C12'	0.44882 (11)	0.3878 (8)	0.31511 (17)	0.0918 (10)
H12'	0.4809	0.4494	0.3013	0.110*
C13'	0.42803 (11)	0.4930 (7)	0.36600 (16)	0.0843 (9)
H13'	0.4457	0.6273	0.3866	0.101*
C14'	0.38063 (10)	0.4003 (6)	0.38705 (13)	0.0696 (7)
H14'	0.3667	0.4698	0.4222	0.084*
C15'	0.06702 (15)	0.6585 (9)	0.3567 (2)	0.1249 (16)
H15D	0.0457	0.5283	0.3366	0.187*
H15E	0.0799	0.7867	0.3282	0.187*
H15F	0.0466	0.7496	0.3864	0.187*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0428 (4)	0.2051 (11)	0.1189 (8)	−0.0002 (5)	−0.0020 (4)	0.0014 (8)
O1	0.0586 (10)	0.1173 (16)	0.0687 (12)	0.0230 (10)	0.0087 (10)	−0.0126 (12)
O2	0.0459 (8)	0.167 (2)	0.0535 (11)	−0.0069 (11)	0.0000 (8)	0.0241 (13)
N1	0.0386 (10)	0.140 (2)	0.0638 (15)	−0.0061 (12)	−0.0016 (10)	0.0255 (15)
N2	0.0435 (10)	0.1076 (18)	0.0502 (13)	−0.0002 (10)	0.0011 (10)	0.0064 (12)
C1	0.0427 (14)	0.092 (2)	0.0590 (18)	−0.0071 (12)	0.0043 (12)	−0.0001 (17)
C2	0.0446 (14)	0.115 (2)	0.0652 (19)	−0.0099 (14)	−0.0024 (13)	0.0099 (17)
C3	0.0446 (15)	0.119 (3)	0.062 (2)	−0.0145 (14)	0.0052 (13)	−0.0104 (18)
C4	0.0646 (17)	0.110 (2)	0.085 (2)	−0.0304 (17)	0.0074 (16)	−0.003 (2)
C5	0.092 (2)	0.094 (2)	0.107 (3)	−0.0260 (19)	0.005 (2)	0.029 (2)
C6	0.0620 (15)	0.084 (2)	0.095 (2)	−0.0054 (15)	−0.0017 (16)	0.0142 (19)
C7	0.0376 (11)	0.0844 (18)	0.0591 (16)	0.0043 (11)	0.0009 (11)	0.0046 (15)
C8	0.0458 (12)	0.0802 (18)	0.0552 (16)	0.0002 (12)	0.0059 (12)	0.0032 (15)
C9	0.0471 (13)	0.0682 (18)	0.0487 (16)	0.0010 (11)	0.0016 (11)	0.0009 (13)
C10	0.0750 (18)	0.097 (2)	0.0576 (17)	0.0225 (15)	−0.0068 (15)	−0.0152 (17)
C11	0.082 (2)	0.109 (2)	0.068 (2)	0.0175 (18)	−0.0279 (16)	−0.015 (2)
C12	0.0643 (16)	0.105 (3)	0.077 (2)	0.0247 (16)	−0.0164 (14)	−0.0047 (19)
C13	0.0730 (17)	0.089 (2)	0.078 (2)	0.0275 (15)	−0.0046 (15)	−0.0105 (18)
C14	0.0588 (13)	0.0801 (18)	0.0603 (16)	0.0044 (14)	−0.0043 (13)	−0.0132 (15)
C15	0.096 (2)	0.188 (4)	0.125 (3)	−0.066 (3)	0.030 (2)	0.018 (3)
Cl1'	0.0425 (3)	0.1770 (10)	0.1260 (8)	0.0026 (4)	0.0056 (4)	−0.0624 (8)
O1'	0.0542 (10)	0.1179 (16)	0.0609 (11)	−0.0087 (10)	−0.0092 (9)	−0.0115 (12)
O2'	0.0514 (9)	0.166 (2)	0.0519 (11)	0.0075 (12)	0.0031 (8)	0.0135 (13)
N1'	0.0416 (11)	0.1079 (17)	0.0574 (14)	0.0069 (10)	0.0039 (10)	0.0074 (13)
N2'	0.0444 (10)	0.112 (2)	0.0486 (13)	0.0020 (11)	−0.0006 (9)	0.0062 (13)
C1'	0.0419 (13)	0.0799 (19)	0.0632 (19)	0.0024 (12)	−0.0012 (13)	−0.0136 (17)
C2'	0.0480 (14)	0.087 (2)	0.072 (2)	0.0005 (12)	0.0023 (14)	−0.0113 (17)
C3'	0.0447 (15)	0.102 (3)	0.088 (2)	0.0125 (14)	−0.0038 (15)	−0.040 (2)
C4'	0.0712 (18)	0.093 (2)	0.086 (2)	0.0331 (17)	−0.0223 (16)	−0.036 (2)
C5'	0.0739 (19)	0.079 (2)	0.092 (2)	0.0154 (15)	−0.0063 (16)	−0.0150 (18)
C6'	0.0521 (14)	0.0758 (19)	0.084 (2)	0.0070 (13)	−0.0023 (14)	−0.0088 (19)
C7'	0.0390 (11)	0.0871 (19)	0.0524 (16)	−0.0031 (11)	−0.0035 (11)	−0.0022 (15)
C8'	0.0412 (12)	0.0752 (18)	0.0567 (16)	0.0024 (11)	−0.0048 (11)	−0.0006 (14)
C9'	0.0454 (13)	0.0698 (18)	0.0556 (17)	0.0009 (11)	−0.0012 (12)	0.0011 (14)
C10'	0.0682 (18)	0.115 (3)	0.0647 (19)	−0.0108 (17)	0.0145 (15)	−0.0148 (19)
C11'	0.081 (2)	0.121 (3)	0.087 (3)	−0.005 (2)	0.033 (2)	−0.008 (2)
C12'	0.0589 (16)	0.121 (3)	0.096 (3)	−0.0160 (19)	0.0134 (17)	0.018 (2)
C13'	0.0604 (16)	0.100 (2)	0.092 (2)	−0.0200 (15)	−0.0033 (16)	0.005 (2)
C14'	0.0569 (14)	0.0792 (19)	0.0729 (18)	−0.0025 (13)	0.0058 (13)	−0.0093 (16)
C15'	0.090 (2)	0.147 (3)	0.138 (4)	0.063 (2)	−0.040 (2)	−0.044 (3)

Geometric parameters (Å, º)

Cl1—C3	1.734 (3)	Cl1'—C3'	1.742 (3)
O1—C8	1.210 (3)	O1'—C8'	1.217 (3)
O2—N2	1.416 (3)	O2'—N2'	1.397 (3)
O2—H2	0.82	O2'—H2'	0.82
N1—C7	1.355 (3)	N1'—C7'	1.361 (3)
N1—C1	1.413 (3)	N1'—C1'	1.406 (3)
N1—H1	0.86	N1'—H1'	0.86
N2—C7	1.282 (3)	N2'—C7'	1.289 (3)
C1—C6	1.373 (4)	C1'—C6'	1.367 (4)
C1—C2	1.377 (4)	C1'—C2'	1.395 (4)
C2—C3	1.378 (4)	C2'—C3'	1.375 (4)
C2—H2A	0.93	C2'—H2'A	0.9300
C3—C4	1.368 (5)	C3'—C4'	1.372 (5)
C4—C5	1.381 (5)	C4'—C5'	1.403 (5)
C4—C15	1.523 (4)	C4'—C15'	1.522 (4)
C5—C6	1.384 (4)	C5'—C6'	1.371 (4)
C5—H5	0.93	C5'—H5'	0.93
C6—H6	0.93	C6'—H6'	0.93
C7—C8	1.501 (4)	C7'—C8'	1.502 (4)
C8—C9	1.487 (3)	C8'—C9'	1.482 (3)
C9—C14	1.376 (4)	C9'—C10'	1.368 (4)
C9—C10	1.380 (4)	C9'—C14'	1.386 (4)
C10—C11	1.384 (4)	C10'—C11'	1.382 (4)
C10—H10	0.93	C10'—H10'	0.93
C11—C12	1.342 (4)	C11'—C12'	1.348 (5)
C11—H11	0.93	C11'—H11'	0.93
C12—C13	1.356 (4)	C12'—C13'	1.363 (5)
C12—H12	0.93	C12'—H12'	0.93
C13—C14	1.381 (4)	C13'—C14'	1.383 (4)
C13—H13	0.93	C13'—H13'	0.93
C14—H14	0.93	C14'—H14'	0.93
C15—H15A	0.96	C15'—H15D	0.96
C15—H15B	0.96	C15'—H15E	0.96
C15—H15C	0.96	C15'—H15F	0.96
N2—O2—H2	109.5	N2'—O2'—H2'	109.5
C7—N1—C1	127.8 (2)	C7'—N1'—C1'	126.8 (2)
C7—N1—H1	116.1	C7'—N1'—H1'	116.6
C1—N1—H1	116.1	C1'—N1'—H1'	116.6
C7—N2—O2	110.65 (18)	C7'—N2'—O2'	111.09 (18)
C6—C1—C2	120.0 (3)	C6'—C1'—C2'	119.6 (3)
C6—C1—N1	122.4 (2)	C6'—C1'—N1'	122.9 (2)
C2—C1—N1	117.6 (3)	C2'—C1'—N1'	117.5 (3)
C1—C2—C3	119.3 (3)	C3'—C2'—C1'	118.6 (3)
C1—C2—H2A	120.3	C3'—C2'—H2'A	120.7
C3—C2—H2A	120.3	C1'—C2'—H2'A	120.7
C4—C3—C2	122.5 (3)	C4'—C3'—C2'	123.5 (3)
C4—C3—Cl1	119.6 (2)	C4'—C3'—Cl1'	119.2 (2)
C2—C3—Cl1	117.9 (3)	C2'—C3'—Cl1'	117.4 (3)
C3—C4—C5	116.5 (3)	C3'—C4'—C5'	116.0 (3)
C3—C4—C15	122.9 (3)	C3'—C4'—C15'	123.7 (4)
C5—C4—C15	120.5 (4)	C5'—C4'—C15'	120.2 (4)
C4—C5—C6	122.6 (3)	C6'—C5'—C4'	121.8 (3)
C4—C5—H5	118.7	C6'—C5'—H5'	119.1
C6—C5—H5	118.7	C4'—C5'—H5'	119.1
C1—C6—C5	118.7 (3)	C1'—C6'—C5'	120.3 (3)
C1—C6—H6	120.6	C1'—C6'—H6'	119.8
C5—C6—H6	120.6	C5'—C6'—H6'	119.8
N2—C7—N1	123.3 (2)	N2'—C7'—N1'	122.8 (2)
N2—C7—C8	114.4 (2)	N2'—C7'—C8'	113.44 (19)
N1—C7—C8	121.7 (2)	N1'—C7'—C8'	122.7 (2)
O1—C8—C9	122.3 (3)	O1'—C8'—C9'	122.0 (2)
O1—C8—C7	118.5 (2)	O1'—C8'—C7'	119.0 (2)
C9—C8—C7	119.1 (2)	C9'—C8'—C7'	118.9 (2)
C14—C9—C10	119.1 (2)	C10'—C9'—C14'	118.8 (2)
C14—C9—C8	123.2 (2)	C10'—C9'—C8'	118.9 (3)
C10—C9—C8	117.6 (2)	C14'—C9'—C8'	122.3 (2)
C9—C10—C11	119.9 (3)	C9'—C10'—C11'	120.6 (3)
C9—C10—H10	120.0	C9'—C10'—H10'	119.7
C11—C10—H10	120.0	C11'—C10'—H10'	119.7
C12—C11—C10	120.2 (3)	C12'—C11'—C10'	120.1 (3)
C12—C11—H11	119.9	C12'—C11'—H11'	119.9
C10—C11—H11	119.9	C10'—C11'—H11'	119.9
C11—C12—C13	120.7 (3)	C11'—C12'—C13'	120.5 (3)
C11—C12—H12	119.7	C11'—C12'—H12'	119.8
C13—C12—H12	119.7	C13'—C12'—H12'	119.7
C12—C13—C14	120.4 (3)	C12'—C13'—C14'	120.0 (3)
C12—C13—H13	119.8	C12'—C13'—H13'	120.0
C14—C13—H13	119.8	C14'—C13'—H13'	120.0
C9—C14—C13	119.7 (3)	C13'—C14'—C9'	119.9 (3)
C9—C14—H14	120.2	C13'—C14'—H14'	120.1
C13—C14—H14	120.2	C9'—C14'—H14'	120.1
C4—C15—H15A	109.5	C4'—C15'—H15D	109.5
C4—C15—H15B	109.5	C4'—C15'—H15E	109.5
H15A—C15—H15B	109.5	H15D—C15'—H15E	109.5
C4—C15—H15C	109.5	C4'—C15'—H15F	109.5
H15A—C15—H15C	109.5	H15D—C15'—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15'—H15F	109.5
C7—N1—C1—C6	−32.2 (5)	C7'—N1'—C1'—C6'	−26.1 (4)
C7—N1—C1—C2	150.7 (3)	C7'—N1'—C1'—C2'	157.3 (3)
C6—C1—C2—C3	2.1 (5)	C6'—C1'—C2'—C3'	2.7 (4)
N1—C1—C2—C3	179.4 (3)	N1'—C1'—C2'—C3'	179.5 (3)
C1—C2—C3—C4	3.2 (5)	C1'—C2'—C3'—C4'	0.5 (5)
C1—C2—C3—Cl1	−177.8 (3)	C1'—C2'—C3'—Cl1'	−178.1 (2)
C2—C3—C4—C5	−5.0 (5)	C2'—C3'—C4'—C5'	−2.6 (5)
Cl1—C3—C4—C5	176.1 (3)	Cl1'—C3'—C4'—C5'	176.0 (2)
C2—C3—C4—C15	173.5 (4)	C2'—C3'—C4'—C15'	177.4 (3)
Cl1—C3—C4—C15	−5.5 (5)	Cl1'—C3'—C4'—C15'	−4.0 (4)
C3—C4—C5—C6	1.6 (5)	C3'—C4'—C5'—C6'	1.6 (5)
C15—C4—C5—C6	−176.9 (4)	C15'—C4'—C5'—C6'	−178.4 (3)
C2—C1—C6—C5	−5.3 (5)	C2'—C1'—C6'—C5'	−3.7 (4)
N1—C1—C6—C5	177.6 (3)	N1'—C1'—C6'—C5'	179.8 (3)
C4—C5—C6—C1	3.4 (6)	C4'—C5'—C6'—C1'	1.5 (5)
O2—N2—C7—N1	0.3 (4)	O2'—N2'—C7'—N1'	−1.4 (4)
O2—N2—C7—C8	−170.2 (2)	O2'—N2'—C7'—C8'	−169.8 (2)
C1—N1—C7—N2	168.1 (3)	C1'—N1'—C7'—N2'	164.3 (3)
C1—N1—C7—C8	−22.0 (5)	C1'—N1'—C7'—C8'	−28.4 (4)
N2—C7—C8—O1	133.0 (3)	N2'—C7'—C8'—O1'	134.9 (3)
N1—C7—C8—O1	−37.6 (4)	N1'—C7'—C8'—O1'	−33.5 (4)
N2—C7—C8—C9	−43.3 (4)	N2'—C7'—C8'—C9'	−41.2 (4)
N1—C7—C8—C9	146.0 (3)	N1'—C7'—C8'—C9'	150.5 (2)
O1—C8—C9—C14	159.4 (3)	O1'—C8'—C9'—C10'	−25.5 (4)
C7—C8—C9—C14	−24.4 (4)	C7'—C8'—C9'—C10'	150.4 (3)
O1—C8—C9—C10	−20.0 (4)	O1'—C8'—C9'—C14'	153.2 (3)
C7—C8—C9—C10	156.2 (3)	C7'—C8'—C9'—C14'	−30.8 (4)
C14—C9—C10—C11	0.6 (5)	C14'—C9'—C10'—C11'	1.6 (5)
C8—C9—C10—C11	−180.0 (3)	C8'—C9'—C10'—C11'	−179.6 (3)
C9—C10—C11—C12	−0.5 (5)	C9'—C10'—C11'—C12'	−2.0 (6)
C10—C11—C12—C13	−0.4 (6)	C10'—C11'—C12'—C13'	0.8 (6)
C11—C12—C13—C14	1.1 (5)	C11'—C12'—C13'—C14'	0.7 (5)
C10—C9—C14—C13	0.0 (4)	C12'—C13'—C14'—C9'	−1.1 (5)
C8—C9—C14—C13	−179.3 (3)	C10'—C9'—C14'—C13'	0.0 (4)
C12—C13—C14—C9	−0.9 (5)	C8'—C9'—C14'—C13'	−178.8 (3)