Download citation
Download citation
link to html
The title compound, C14H5Cl4NO3, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. Each independent mol­ecule exists as part of an O/C—H...O hydrogen-bonded centrosymmetric dimer. The crystal packing is further stabilized by inter­molecular C—H...Cl and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003273/ci2280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003273/ci2280Isup2.hkl
Contains datablock I

CCDC reference: 636856

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.067
  • Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O1A .. C8B .. 2.90 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact O1B .. C7A .. 2.89 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.12 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3A .. O3B .. 2.97 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C8A .. 2.92 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4,5,6,7-Tetrachloro-2-(2-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione top
Crystal data top
C14H5Cl4NO3F(000) = 1504
Mr = 376.99Dx = 1.774 Mg m3
Monoclinic, P21/cMelting point = 563–565 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.2779 (2) ÅCell parameters from 8247 reflections
b = 14.0350 (2) Åθ = 1.9–30.0°
c = 19.9624 (3) ŵ = 0.85 mm1
β = 124.834 (1)°T = 100 K
V = 2823.53 (8) Å3Block, yellow
Z = 80.50 × 0.43 × 0.39 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
8247 independent reflections
Radiation source: fine-focus sealed tube7498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.9°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1919
Tmin = 0.675, Tmax = 0.734l = 2828
77565 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0308P)2 + 1.7606P]
where P = (Fo2 + 2Fc2)/3
8247 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Å2) top
xyzUiso*/Ueq
Cl1A0.41422 (3)0.80398 (2)0.35681 (2)0.02328 (7)
Cl2A0.60045 (3)0.97858 (2)0.393699 (19)0.02171 (7)
Cl3A0.53026 (3)1.17833 (2)0.425596 (19)0.02114 (6)
Cl4A0.27941 (3)1.20652 (2)0.42656 (2)0.02130 (7)
O1A0.15491 (10)0.77617 (7)0.35023 (6)0.02135 (18)
O2A0.05411 (9)0.90038 (7)0.50611 (5)0.01794 (17)
H2AA0.02790.91090.53510.027*
O3A0.06312 (9)1.06835 (6)0.40837 (5)0.01682 (17)
N1A0.08435 (10)0.91163 (7)0.38057 (6)0.01459 (18)
C1A0.16866 (12)0.85912 (9)0.36832 (7)0.0155 (2)
C2A0.27257 (12)0.92761 (8)0.38213 (7)0.0144 (2)
C3A0.38086 (12)0.91368 (9)0.37890 (7)0.0163 (2)
C4A0.46194 (12)0.99265 (9)0.39390 (7)0.0164 (2)
C5A0.43084 (12)1.08284 (9)0.40874 (7)0.0162 (2)
C6A0.31912 (12)1.09569 (8)0.41050 (7)0.0153 (2)
C7A0.24306 (12)1.01664 (8)0.39853 (7)0.0141 (2)
C8A0.12074 (11)1.00735 (8)0.39734 (7)0.0141 (2)
C9A0.03457 (12)0.87317 (8)0.36698 (7)0.0153 (2)
C10A0.04917 (12)0.87032 (8)0.43136 (7)0.0154 (2)
C11A0.16753 (12)0.83475 (9)0.41628 (8)0.0176 (2)
H11A0.18020.83350.45800.021*
C12A0.26619 (13)0.80125 (9)0.33926 (8)0.0206 (2)
H12A0.34480.77800.32970.025*
C13A0.24910 (13)0.80197 (9)0.27618 (8)0.0211 (2)
H13A0.31490.77800.22510.025*
C14A0.13278 (12)0.83889 (9)0.29027 (7)0.0183 (2)
H14A0.12080.84060.24830.022*
Cl1B0.75439 (3)0.53921 (2)0.311103 (19)0.02186 (7)
Cl2B0.76340 (3)0.60712 (2)0.46369 (2)0.02081 (6)
Cl3B1.02587 (3)0.68503 (2)0.61642 (2)0.02233 (7)
Cl4B1.28418 (3)0.69176 (2)0.621227 (18)0.01927 (6)
O1B0.96958 (9)0.51731 (7)0.27317 (5)0.02181 (19)
O2B1.38513 (9)0.43930 (6)0.44301 (5)0.01760 (17)
H2BA1.45760.41340.46430.026*
O3B1.35405 (8)0.63371 (6)0.49810 (5)0.01593 (16)
N1B1.17980 (10)0.56633 (7)0.37807 (6)0.01386 (18)
C1B1.04399 (12)0.55114 (8)0.33993 (7)0.0157 (2)
C2B1.01535 (12)0.58388 (8)0.39988 (7)0.0147 (2)
C3B0.89946 (12)0.58099 (9)0.39611 (7)0.0162 (2)
C4B0.90382 (12)0.61234 (8)0.46455 (8)0.0167 (2)
C5B1.02248 (12)0.64677 (8)0.53373 (7)0.0161 (2)
C6B1.13914 (12)0.65041 (8)0.53605 (7)0.0153 (2)
C7B1.13307 (11)0.61837 (8)0.46865 (7)0.0138 (2)
C8B1.23917 (12)0.60960 (8)0.45429 (7)0.0135 (2)
C9B1.24869 (12)0.55246 (8)0.34054 (7)0.0145 (2)
C10B1.35823 (12)0.49157 (9)0.37769 (7)0.0154 (2)
C11B1.43387 (13)0.48653 (10)0.34600 (8)0.0199 (2)
H11B1.50960.44870.37130.024*
C12B1.39616 (14)0.53804 (11)0.27661 (8)0.0232 (3)
H12B1.44810.53520.25640.028*
C13B1.28231 (14)0.59373 (10)0.23679 (8)0.0222 (3)
H13B1.25520.62510.18860.027*
C14B1.20936 (13)0.60200 (9)0.26997 (7)0.0186 (2)
H14C1.13440.64060.24490.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.02519 (15)0.02026 (14)0.03167 (16)0.00359 (11)0.02053 (13)0.00185 (12)
Cl2A0.01787 (13)0.03092 (16)0.02203 (14)0.00315 (11)0.01475 (12)0.00418 (11)
Cl3A0.01715 (13)0.02195 (14)0.02288 (14)0.00399 (11)0.01059 (11)0.00341 (11)
Cl4A0.02335 (15)0.01432 (13)0.02956 (15)0.00174 (11)0.01708 (13)0.00272 (11)
O1A0.0249 (5)0.0147 (4)0.0292 (5)0.0006 (3)0.0183 (4)0.0007 (3)
O2A0.0180 (4)0.0223 (4)0.0163 (4)0.0005 (3)0.0113 (3)0.0013 (3)
O3A0.0179 (4)0.0166 (4)0.0192 (4)0.0010 (3)0.0124 (3)0.0006 (3)
N1A0.0161 (5)0.0136 (4)0.0175 (4)0.0009 (4)0.0116 (4)0.0004 (4)
C1A0.0170 (5)0.0157 (5)0.0155 (5)0.0017 (4)0.0102 (4)0.0022 (4)
C2A0.0153 (5)0.0147 (5)0.0134 (5)0.0011 (4)0.0083 (4)0.0014 (4)
C3A0.0177 (5)0.0176 (5)0.0149 (5)0.0030 (4)0.0101 (4)0.0015 (4)
C4A0.0137 (5)0.0231 (6)0.0142 (5)0.0021 (4)0.0091 (4)0.0033 (4)
C5A0.0147 (5)0.0192 (5)0.0141 (5)0.0018 (4)0.0079 (4)0.0023 (4)
C6A0.0165 (5)0.0151 (5)0.0144 (5)0.0005 (4)0.0089 (4)0.0007 (4)
C7A0.0149 (5)0.0155 (5)0.0129 (5)0.0007 (4)0.0086 (4)0.0006 (4)
C8A0.0151 (5)0.0147 (5)0.0129 (5)0.0001 (4)0.0082 (4)0.0009 (4)
C9A0.0154 (5)0.0128 (5)0.0196 (5)0.0006 (4)0.0112 (4)0.0016 (4)
C10A0.0168 (5)0.0118 (5)0.0184 (5)0.0016 (4)0.0106 (4)0.0011 (4)
C11A0.0189 (6)0.0148 (5)0.0239 (6)0.0018 (4)0.0151 (5)0.0028 (4)
C12A0.0158 (5)0.0165 (6)0.0293 (6)0.0004 (4)0.0128 (5)0.0010 (5)
C13A0.0178 (6)0.0188 (6)0.0214 (6)0.0012 (5)0.0081 (5)0.0013 (5)
C14A0.0193 (6)0.0176 (5)0.0176 (5)0.0003 (4)0.0103 (5)0.0009 (4)
Cl1B0.01391 (13)0.02459 (15)0.02302 (14)0.00280 (11)0.00815 (11)0.00255 (11)
Cl2B0.01889 (13)0.01837 (13)0.03211 (16)0.00161 (11)0.01866 (13)0.00234 (11)
Cl3B0.02644 (15)0.02432 (15)0.02538 (15)0.00025 (12)0.02019 (13)0.00373 (11)
Cl4B0.01899 (13)0.02241 (14)0.01783 (13)0.00403 (11)0.01134 (11)0.00657 (10)
O1B0.0186 (4)0.0292 (5)0.0153 (4)0.0040 (4)0.0083 (4)0.0041 (3)
O2B0.0173 (4)0.0192 (4)0.0177 (4)0.0035 (3)0.0108 (3)0.0035 (3)
O3B0.0148 (4)0.0159 (4)0.0175 (4)0.0011 (3)0.0095 (3)0.0022 (3)
N1B0.0135 (4)0.0157 (4)0.0131 (4)0.0001 (4)0.0080 (4)0.0011 (3)
C1B0.0161 (5)0.0148 (5)0.0165 (5)0.0000 (4)0.0096 (4)0.0008 (4)
C2B0.0149 (5)0.0134 (5)0.0163 (5)0.0005 (4)0.0092 (4)0.0007 (4)
C3B0.0141 (5)0.0143 (5)0.0187 (5)0.0001 (4)0.0085 (4)0.0011 (4)
C4B0.0170 (5)0.0136 (5)0.0242 (6)0.0023 (4)0.0145 (5)0.0029 (4)
C5B0.0204 (6)0.0133 (5)0.0205 (5)0.0021 (4)0.0151 (5)0.0007 (4)
C6B0.0164 (5)0.0132 (5)0.0165 (5)0.0001 (4)0.0096 (4)0.0006 (4)
C7B0.0145 (5)0.0120 (5)0.0160 (5)0.0012 (4)0.0093 (4)0.0009 (4)
C8B0.0169 (5)0.0108 (5)0.0145 (5)0.0014 (4)0.0099 (4)0.0008 (4)
C9B0.0155 (5)0.0155 (5)0.0149 (5)0.0017 (4)0.0101 (4)0.0024 (4)
C10B0.0166 (5)0.0162 (5)0.0143 (5)0.0021 (4)0.0094 (4)0.0026 (4)
C11B0.0175 (5)0.0260 (6)0.0180 (5)0.0000 (5)0.0112 (5)0.0031 (5)
C12B0.0234 (6)0.0330 (7)0.0190 (6)0.0049 (5)0.0156 (5)0.0043 (5)
C13B0.0277 (6)0.0256 (6)0.0167 (5)0.0045 (5)0.0147 (5)0.0003 (5)
C14B0.0216 (6)0.0176 (5)0.0164 (5)0.0008 (5)0.0108 (5)0.0002 (4)
Geometric parameters (Å, º) top
Cl1A—C3A1.7144 (13)Cl1B—C3B1.7155 (12)
Cl2A—C4A1.7144 (12)Cl2B—C4B1.7158 (12)
Cl3A—C5A1.7117 (13)Cl3B—C5B1.7136 (12)
Cl4A—C6A1.7141 (12)Cl4B—C6B1.7146 (12)
O1A—C1A1.2019 (15)O1B—C1B1.2022 (15)
O2A—C10A1.3606 (15)O2B—C10B1.3623 (14)
O2A—H2AA0.82O2B—H2BA0.82
O3A—C8A1.2084 (15)O3B—C8B1.2081 (14)
N1A—C8A1.3948 (15)N1B—C8B1.3957 (14)
N1A—C1A1.4014 (15)N1B—C1B1.3983 (15)
N1A—C9A1.4297 (15)N1B—C9B1.4279 (15)
C1A—C2A1.4920 (17)C1B—C2B1.4992 (17)
C2A—C3A1.3813 (16)C2B—C3B1.3819 (16)
C2A—C7A1.3911 (16)C2B—C7B1.3934 (16)
C3A—C4A1.4030 (18)C3B—C4B1.4071 (17)
C4A—C5A1.4017 (18)C4B—C5B1.4017 (17)
C5A—C6A1.4038 (17)C5B—C6B1.4074 (17)
C6A—C7A1.3802 (17)C6B—C7B1.3796 (16)
C7A—C8A1.4940 (16)C7B—C8B1.4903 (16)
C9A—C14A1.3860 (17)C9B—C14B1.3871 (16)
C9A—C10A1.3959 (16)C9B—C10B1.3963 (17)
C10A—C11A1.3971 (17)C10B—C11B1.3924 (17)
C11A—C12A1.3873 (18)C11B—C12B1.3867 (18)
C11A—H11A0.93C11B—H11B0.93
C12A—C13A1.3898 (19)C12B—C13B1.388 (2)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.3888 (18)C13B—C14B1.3900 (18)
C13A—H13A0.93C13B—H13B0.93
C14A—H14A0.93C14B—H14C0.93
C10A—O2A—H2AA109.5C10B—O2B—H2BA109.5
C8A—N1A—C1A112.40 (10)C8B—N1B—C1B112.20 (10)
C8A—N1A—C9A124.17 (10)C8B—N1B—C9B122.30 (10)
C1A—N1A—C9A122.98 (10)C1B—N1B—C9B124.96 (10)
O1A—C1A—N1A124.81 (11)O1B—C1B—N1B125.36 (11)
O1A—C1A—C2A129.65 (11)O1B—C1B—C2B129.03 (11)
N1A—C1A—C2A105.54 (10)N1B—C1B—C2B105.61 (10)
C3A—C2A—C7A121.68 (11)C3B—C2B—C7B121.35 (11)
C3A—C2A—C1A130.13 (11)C3B—C2B—C1B130.63 (11)
C7A—C2A—C1A108.18 (10)C7B—C2B—C1B107.98 (10)
C2A—C3A—C4A117.56 (11)C2B—C3B—C4B118.10 (11)
C2A—C3A—Cl1A121.12 (10)C2B—C3B—Cl1B121.26 (9)
C4A—C3A—Cl1A121.31 (9)C4B—C3B—Cl1B120.63 (9)
C5A—C4A—C3A120.85 (11)C5B—C4B—C3B120.41 (11)
C5A—C4A—Cl2A119.65 (10)C5B—C4B—Cl2B119.84 (9)
C3A—C4A—Cl2A119.50 (10)C3B—C4B—Cl2B119.75 (10)
C4A—C5A—C6A120.61 (11)C4B—C5B—C6B120.70 (11)
C4A—C5A—Cl3A119.93 (9)C4B—C5B—Cl3B119.78 (9)
C6A—C5A—Cl3A119.46 (10)C6B—C5B—Cl3B119.52 (9)
C7A—C6A—C5A117.81 (11)C7B—C6B—C5B117.98 (11)
C7A—C6A—Cl4A121.68 (9)C7B—C6B—Cl4B121.63 (9)
C5A—C6A—Cl4A120.50 (9)C5B—C6B—Cl4B120.39 (9)
C6A—C7A—C2A121.42 (11)C6B—C7B—C2B121.46 (11)
C6A—C7A—C8A130.35 (11)C6B—C7B—C8B130.41 (11)
C2A—C7A—C8A108.21 (10)C2B—C7B—C8B108.10 (10)
O3A—C8A—N1A125.83 (11)O3B—C8B—N1B125.29 (11)
O3A—C8A—C7A128.55 (11)O3B—C8B—C7B128.69 (11)
N1A—C8A—C7A105.62 (10)N1B—C8B—C7B106.02 (10)
C14A—C9A—C10A121.27 (11)C14B—C9B—C10B121.14 (11)
C14A—C9A—N1A119.37 (11)C14B—C9B—N1B119.84 (11)
C10A—C9A—N1A119.36 (11)C10B—C9B—N1B118.97 (10)
O2A—C10A—C9A118.14 (11)O2B—C10B—C11B123.20 (11)
O2A—C10A—C11A123.38 (11)O2B—C10B—C9B118.12 (10)
C9A—C10A—C11A118.47 (11)C11B—C10B—C9B118.67 (11)
C12A—C11A—C10A120.15 (12)C12B—C11B—C10B119.90 (12)
C12A—C11A—H11A119.9C12B—C11B—H11B120.0
C10A—C11A—H11A119.9C10B—C11B—H11B120.0
C11A—C12A—C13A120.89 (12)C11B—C12B—C13B121.20 (12)
C11A—C12A—H12A119.6C11B—C12B—H12B119.4
C13A—C12A—H12A119.6C13B—C12B—H12B119.4
C14A—C13A—C12A119.30 (12)C12B—C13B—C14B119.09 (12)
C14A—C13A—H13A120.4C12B—C13B—H13B120.5
C12A—C13A—H13A120.4C14B—C13B—H13B120.5
C9A—C14A—C13A119.88 (12)C9B—C14B—C13B119.79 (12)
C9A—C14A—H14A120.1C9B—C14B—H14C120.1
C13A—C14A—H14A120.1C13B—C14B—H14C120.1
C8A—N1A—C1A—O1A177.24 (11)C8B—N1B—C1B—O1B178.01 (12)
C9A—N1A—C1A—O1A4.64 (19)C9B—N1B—C1B—O1B6.33 (19)
C8A—N1A—C1A—C2A2.54 (13)C8B—N1B—C1B—C2B2.95 (13)
C9A—N1A—C1A—C2A175.14 (10)C9B—N1B—C1B—C2B174.62 (10)
O1A—C1A—C2A—C3A1.0 (2)O1B—C1B—C2B—C3B2.6 (2)
N1A—C1A—C2A—C3A179.24 (12)N1B—C1B—C2B—C3B176.36 (12)
O1A—C1A—C2A—C7A177.57 (12)O1B—C1B—C2B—C7B179.64 (13)
N1A—C1A—C2A—C7A2.19 (12)N1B—C1B—C2B—C7B1.36 (13)
C7A—C2A—C3A—C4A0.83 (17)C7B—C2B—C3B—C4B1.15 (18)
C1A—C2A—C3A—C4A179.23 (11)C1B—C2B—C3B—C4B176.32 (12)
C7A—C2A—C3A—Cl1A178.82 (9)C7B—C2B—C3B—Cl1B179.58 (9)
C1A—C2A—C3A—Cl1A0.42 (18)C1B—C2B—C3B—Cl1B2.96 (19)
C2A—C3A—C4A—C5A2.18 (17)C2B—C3B—C4B—C5B0.97 (18)
Cl1A—C3A—C4A—C5A177.47 (9)Cl1B—C3B—C4B—C5B179.75 (9)
C2A—C3A—C4A—Cl2A178.05 (9)C2B—C3B—C4B—Cl2B178.29 (9)
Cl1A—C3A—C4A—Cl2A2.30 (14)Cl1B—C3B—C4B—Cl2B0.99 (15)
C3A—C4A—C5A—C6A1.27 (17)C3B—C4B—C5B—C6B0.12 (18)
Cl2A—C4A—C5A—C6A178.96 (9)Cl2B—C4B—C5B—C6B179.14 (9)
C3A—C4A—C5A—Cl3A179.18 (9)C3B—C4B—C5B—Cl3B179.79 (9)
Cl2A—C4A—C5A—Cl3A0.59 (14)Cl2B—C4B—C5B—Cl3B0.95 (14)
C4A—C5A—C6A—C7A1.04 (17)C4B—C5B—C6B—C7B0.57 (17)
Cl3A—C5A—C6A—C7A178.52 (9)Cl3B—C5B—C6B—C7B179.52 (9)
C4A—C5A—C6A—Cl4A178.64 (9)C4B—C5B—C6B—Cl4B179.49 (9)
Cl3A—C5A—C6A—Cl4A1.81 (14)Cl3B—C5B—C6B—Cl4B0.60 (14)
C5A—C6A—C7A—C2A2.41 (17)C5B—C6B—C7B—C2B0.41 (17)
Cl4A—C6A—C7A—C2A177.26 (9)Cl4B—C6B—C7B—C2B179.31 (9)
C5A—C6A—C7A—C8A179.69 (11)C5B—C6B—C7B—C8B177.20 (11)
Cl4A—C6A—C7A—C8A0.64 (18)Cl4B—C6B—C7B—C8B1.70 (18)
C3A—C2A—C7A—C6A1.50 (18)C3B—C2B—C7B—C6B0.46 (18)
C1A—C2A—C7A—C6A177.21 (10)C1B—C2B—C7B—C6B177.51 (11)
C3A—C2A—C7A—C8A179.82 (10)C3B—C2B—C7B—C8B178.55 (11)
C1A—C2A—C7A—C8A1.11 (12)C1B—C2B—C7B—C8B0.57 (13)
C1A—N1A—C8A—O3A178.16 (11)C1B—N1B—C8B—O3B176.94 (11)
C9A—N1A—C8A—O3A5.66 (18)C9B—N1B—C8B—O3B5.01 (18)
C1A—N1A—C8A—C7A1.89 (12)C1B—N1B—C8B—C7B3.30 (13)
C9A—N1A—C8A—C7A174.38 (10)C9B—N1B—C8B—C7B175.23 (10)
C6A—C7A—C8A—O3A1.5 (2)C6B—C7B—C8B—O3B4.2 (2)
C2A—C7A—C8A—O3A179.65 (12)C2B—C7B—C8B—O3B177.95 (12)
C6A—C7A—C8A—N1A178.51 (12)C6B—C7B—C8B—N1B175.55 (12)
C2A—C7A—C8A—N1A0.40 (12)C2B—C7B—C8B—N1B2.31 (12)
C8A—N1A—C9A—C14A112.96 (13)C8B—N1B—C9B—C14B112.89 (13)
C1A—N1A—C9A—C14A58.76 (16)C1B—N1B—C9B—C14B57.98 (16)
C8A—N1A—C9A—C10A67.43 (15)C8B—N1B—C9B—C10B64.67 (15)
C1A—N1A—C9A—C10A120.84 (12)C1B—N1B—C9B—C10B124.45 (13)
C14A—C9A—C10A—O2A176.47 (11)C14B—C9B—C10B—O2B174.83 (11)
N1A—C9A—C10A—O2A3.13 (16)N1B—C9B—C10B—O2B7.64 (16)
C14A—C9A—C10A—C11A2.04 (18)C14B—C9B—C10B—C11B4.65 (18)
N1A—C9A—C10A—C11A178.36 (11)N1B—C9B—C10B—C11B172.89 (11)
O2A—C10A—C11A—C12A176.98 (11)O2B—C10B—C11B—C12B176.49 (12)
C9A—C10A—C11A—C12A1.45 (18)C9B—C10B—C11B—C12B2.96 (18)
C10A—C11A—C12A—C13A0.32 (19)C10B—C11B—C12B—C13B1.2 (2)
C11A—C12A—C13A—C14A1.54 (19)C11B—C12B—C13B—C14B3.7 (2)
C10A—C9A—C14A—C13A0.84 (19)C10B—C9B—C14B—C13B2.16 (19)
N1A—C9A—C14A—C13A179.56 (11)N1B—C9B—C14B—C13B175.35 (11)
C12A—C13A—C14A—C9A0.96 (19)C12B—C13B—C14B—C9B2.01 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2AA···O3Ai0.822.012.8259 (16)172
O2B—H2BA···O3Bii0.822.092.8959 (16)168
C11A—H11A···O3Ai0.932.593.2588 (16)129
C11B—H11B···O3Bii0.932.443.1711 (16)136
C12B—H12B···Cl2Aiii0.932.823.5240 (16)134
Symmetry codes: (i) x, y+2, z+1; (ii) x+3, y+1, z+1; (iii) x+2, y1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds