#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:31:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180303 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151731.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151731
loop_
_publ_author_name
'Ahmad, Sajjad'
'Thomas, Lynne H.'
'Sutherland, Andrew'
_publ_section_title
;
 Stereoselective synthesis of polyhydroxylated aminocyclohexanes.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2801
_journal_page_last               2808
_journal_paper_doi               10.1039/c0ob00619j
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C8 H12 Cl3 N O4'
_chemical_formula_weight         292.54
_chemical_name_systematic
;
(1S,2S,3S,4S)-1-(2?,2?,2?-trichloromethylcarbonylamino)-2,3,4-
trihydroxycyclohexane
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-08-12T11:31:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.296(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   39.705(2)
_cell_length_b                   5.8312(3)
_cell_length_c                   20.2162(14)
_cell_measurement_reflns_used    7537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.27
_cell_measurement_theta_min      6.05
_cell_volume                     4679.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku R-axis/RAPID'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_unetI/netI     0.1599
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13482
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.3751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear 1.4.0 (Rigaku, 2008)'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.76
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         9273
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1714
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+31.8892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                4852
_reflns_number_total             9273
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c0ob00619j.txt
_cod_data_source_block           sa188a
_cod_database_code               7151731
#BEGIN Tags that were not found in dictionaries:
_symmetry_space_group_name       C2
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.27374(5) 0.0082(4) 0.97397(12) 0.0293(6) Uani d . 1 . . Cl
Cl2 0.28421(5) 0.4328(4) 0.90487(13) 0.0297(6) Uani d . 1 . . Cl
Cl11 0.72097(5) 0.9607(4) 0.52347(13) 0.0320(6) Uani d . 1 . . Cl
Cl9 0.21032(6) 0.6870(4) 0.85186(13) 0.0335(6) Uani d . 1 . . Cl
Cl4 0.27926(5) 0.5903(4) 0.73335(12) 0.0297(6) Uani d . 1 . . Cl
Cl10 0.69122(5) 0.9494(4) 0.65193(12) 0.0293(6) Uani d . 1 . . Cl
Cl8 0.17830(5) 1.0893(5) 0.90672(12) 0.0333(6) Uani d . 1 . . Cl
Cl5 0.28140(5) 0.1820(4) 0.65369(13) 0.0327(6) Uani d . 1 . . Cl
Cl12 0.71696(6) 1.3761(4) 0.60052(14) 0.0342(7) Uani d . 1 . . Cl
Cl3 0.30359(6) 0.0019(4) 0.84472(12) 0.0324(6) Uani d . 1 . . Cl
Cl7 0.21154(6) 1.1156(4) 0.78151(12) 0.0340(6) Uani d . 1 . . Cl
Cl6 0.31208(6) 0.6031(5) 0.60783(13) 0.0356(6) Uani d . 1 . . Cl
O1 0.34563(14) 0.0338(13) 0.9940(4) 0.048(2) Uani d . 1 . . O
O9 0.15085(15) 0.8960(12) 0.7353(3) 0.0299(17) Uani d . 1 . . O
O13 0.65615(14) 1.1377(13) 0.4885(3) 0.0315(18) Uani d . 1 . . O
O6 0.34778(15) 0.4530(12) 0.7622(3) 0.0327(17) Uani d . 1 . . O
O10 0.08133(15) 0.5922(11) 0.9143(3) 0.0308(15) Uani d . 1 . . O
H10 0.0718 0.6664 0.9428 0.046 Uiso calc R 1 . . H
O3 0.45368(15) 0.4165(12) 1.0200(3) 0.0329(17) Uani d . 1 . . O
H53 0.4736 0.4411 1.0287 0.049 Uiso calc R 1 . . H
O12 0.01942(14) 0.1680(12) 0.7940(3) 0.0369(18) Uani d . 1 . . O
H12 0.003 0.2519 0.789 0.055 Uiso calc R 1 . . H
O11 0.02890(16) 0.6667(12) 0.7642(3) 0.0383(18) Uani d . 1 . . O
H511 0.0332 0.5862 0.7322 0.057 Uiso calc R 1 . . H
N4 0.64020(18) 1.2753(14) 0.5881(4) 0.030(2) Uani d . 1 . . N
H44 0.6466 1.2987 0.6284 0.036 Uiso calc R 1 . . H
C25 0.6967(2) 1.1153(17) 0.5795(4) 0.022(2) Uani d . 1 . . C
O4 0.49246(13) 0.5952(14) 0.9156(3) 0.0365(17) Uani d . 1 . . O
H54A 0.5004 0.6168 0.879 0.055 Uiso calc R 1 . . H
O2 0.39028(18) 0.7405(12) 0.9286(4) 0.050(2) Uani d . 1 . . O
H52 0.3771 0.8185 0.9497 0.075 Uiso calc R 1 . . H
O7 0.40026(15) 0.0152(12) 0.5811(3) 0.0384(18) Uani d . 1 . . O
H7 0.3886 0.0865 0.5542 0.058 Uiso calc R 1 . . H
N1 0.35720(17) 0.3239(14) 0.9234(4) 0.029(2) Uani d . 1 . . N
H1 0.3483 0.4231 0.8967 0.035 Uiso calc R 1 . . H
C2 0.3371(2) 0.1689(17) 0.9508(5) 0.026(2) Uani d . 1 . . C
C1 0.3003(2) 0.1540(14) 0.9210(4) 0.019(2) Uani d . 1 . . C
C26 0.6615(2) 1.1781(16) 0.5469(5) 0.024(2) Uani d . 1 . . C
C6 0.45630(19) 0.5628(18) 0.9089(5) 0.029(2) Uani d . 1 . . C
H6 0.447 0.6822 0.8797 0.034 Uiso calc R 1 . . H
C18 0.1544(2) 0.8647(17) 0.7949(5) 0.024(2) Uani d . 1 . . C
C9 0.3042(2) 0.4320(17) 0.6775(5) 0.027(2) Uani d . 1 . . C
C10 0.3387(2) 0.3665(17) 0.7112(5) 0.024(2) Uani d . 1 . . C
N3 0.13206(19) 0.7567(14) 0.8333(4) 0.032(2) Uani d . 1 . . N
H43 0.1357 0.7524 0.8753 0.038 Uiso calc R 1 . . H
C17 0.1871(2) 0.9375(16) 0.8322(5) 0.026(2) Uani d . 1 . . C
C5 0.4413(2) 0.5864(17) 0.9750(4) 0.026(2) Uani d . 1 . . C
H5 0.4466 0.7388 0.9928 0.031 Uiso calc R 1 . . H
C3 0.3930(2) 0.3331(17) 0.9362(5) 0.026(2) Uani d . 1 . . C
H3A 0.3994 0.2071 0.966 0.031 Uiso calc R 1 . . H
C13 0.4276(2) -0.1789(16) 0.7354(5) 0.034(3) Uani d . 1 C . C
H13A 0.4375 -0.0875 0.7709 0.041 Uiso calc R 1 . . H
H13B 0.4276 -0.338 0.7493 0.041 Uiso calc R 1 . . H
C20 0.0722(2) 0.6818(17) 0.8501(5) 0.028(2) Uani d . 1 . . C
H20 0.0674 0.8461 0.8536 0.033 Uiso calc R 1 . . H
N2 0.35589(18) 0.2143(17) 0.6774(5) 0.048(3) Uani d . 1 . . N
H42 0.346 0.1506 0.6438 0.058 Uiso calc R 1 . . H
C11 0.3907(2) 0.1469(17) 0.6934(5) 0.030(2) Uani d . 1 . . C
H11 0.3998 0.2505 0.7275 0.036 Uiso calc R 1 . . H
C4 0.40284(19) 0.5597(16) 0.9688(5) 0.028(2) Uani d . 1 . . C
H4A 0.393 0.5691 1.0128 0.034 Uiso calc R 1 . . H
C27 0.6063(2) 1.3437(18) 0.5673(5) 0.033(3) Uani d . 1 . . C
H27 0.601 1.2383 0.5308 0.039 Uiso calc R 1 A 1 H
C24 0.1093(2) 0.3887(17) 0.7927(5) 0.034(3) Uani d . 1 . . C
H24A 0.1269 0.3738 0.7606 0.041 Uiso calc R 1 . . H
H24B 0.1167 0.3151 0.8335 0.041 Uiso calc R 1 . . H
C19 0.10158(19) 0.6458(16) 0.8054(5) 0.024(2) Uani d . 1 . . C
H19 0.0962 0.7181 0.7627 0.028 Uiso calc R 1 . . H
C15 0.4117(2) 0.1678(17) 0.6329(5) 0.030(2) Uani d . 1 . . C
H15 0.4115 0.3265 0.6169 0.036 Uiso calc R 1 . . H
C8 0.4106(2) 0.3013(17) 0.8713(5) 0.032(3) Uani d . 1 . . C
H8A 0.4019 0.4125 0.8396 0.039 Uiso calc R 1 . . H
H8B 0.4056 0.1495 0.8542 0.039 Uiso calc R 1 . . H
C22 0.0483(2) 0.3035(16) 0.8138(5) 0.029(2) Uani d . 1 . . C
H22 0.0564 0.2436 0.8566 0.035 Uiso calc R 1 . . H
C14 0.4478(2) 0.0905(18) 0.6481(5) 0.033(2) Uani d . 1 C . C
H14 0.4609 0.0984 0.6076 0.04 Uiso calc R 1 . . H
C21 0.0408(2) 0.5564(18) 0.8236(5) 0.031(3) Uani d . 1 . . C
H21 0.0232 0.5696 0.8567 0.038 Uiso calc R 1 . . H
C23 0.0764(2) 0.2746(16) 0.7661(5) 0.033(3) Uani d . 1 . . C
H23A 0.0699 0.3432 0.7239 0.04 Uiso calc R 1 . . H
H23B 0.0804 0.1125 0.7588 0.04 Uiso calc R 1 . . H
C30 0.54435(19) 1.6011(18) 0.5850(4) 0.026(2) Uani d P 0.5 B 1 C
H30A 0.5531 1.7025 0.6201 0.032 Uiso calc PR 0.5 B 1 H
O14 0.51177(13) 1.6866(12) 0.5635(3) 0.0318(17) Uani d P. 1 . . O
H514 0.4971 1.5971 0.575 0.048 Uiso calc R 1 . . H
C31 0.5667(4) 1.638(3) 0.5214(10) 0.020(4) Uiso d P 0.5 B 1 C
H31 0.566 1.7976 0.5064 0.025 Uiso calc PR 0.5 B 1 H
O15 0.5551(3) 1.483(2) 0.4696(6) 0.022(3) Uiso d P 0.5 B 1 O
H15A 0.5355 1.5123 0.4595 0.033 Uiso calc PR 0.5 B 1 H
C32 0.6027(4) 1.561(3) 0.5379(10) 0.021(4) Uiso d P 0.5 B 1 C
H32 0.6159 1.5659 0.4975 0.025 Uiso calc PR 0.5 B 1 H
O16 0.6159(3) 1.729(3) 0.5838(7) 0.032(3) Uiso d P 0.5 B 1 O
H516 0.6349 1.7663 0.573 0.048 Uiso calc PR 0.5 B 1 H
C29 0.5456(4) 1.374(3) 0.6090(9) 0.013(4) Uiso d P 0.5 B 1 C
H29A 0.5332 1.2757 0.5783 0.015 Uiso calc PR 0.5 B 1 H
H29B 0.5343 1.368 0.651 0.015 Uiso calc PR 0.5 B 1 H
C30A 0.54435(19) 1.6011(18) 0.5850(4) 0.026(2) Uani d P 0.5 B 2 C
H30B 0.5474 1.6389 0.632 0.032 Uiso calc PR 0.5 B 2 H
C31A 0.5713(5) 1.704(4) 0.5504(11) 0.034(5) Uiso d P 0.5 B 2 C
H31A 0.5705 1.87 0.5579 0.04 Uiso calc PR 0.5 B 2 H
O15A 0.5653(3) 1.662(2) 0.4798(7) 0.033(3) Uiso d P 0.5 B 2 O
H15B 0.5761 1.7543 0.4582 0.049 Uiso calc PR 0.5 B 2 H
C32A 0.6068(5) 1.620(4) 0.5681(10) 0.024(4) Uiso d P 0.5 B 2 C
H32A 0.6237 1.6824 0.5385 0.029 Uiso calc PR 0.5 B 2 H
O16A 0.6113(3) 1.705(2) 0.6358(7) 0.034(3) Uiso d P 0.5 B 2 O
H16A 0.624 1.6189 0.6565 0.051 Uiso calc PR 0.5 B 2 H
C29A 0.5449(5) 1.327(4) 0.5783(12) 0.038(6) Uiso d P 0.5 B 2 C
H29C 0.5456 1.2772 0.5326 0.045 Uiso calc PR 0.5 B 2 H
H29D 0.5261 1.2551 0.6 0.045 Uiso calc PR 0.5 B 2 H
O50 0.4774(3) -0.287(2) 0.6836(6) 0.019(3) Uiso d P 0.5 C 3 O
H50 0.4879 -0.2929 0.6491 0.029 Uiso calc PR 0.5 C 3 H
O50A 0.4870(3) -0.169(3) 0.6856(7) 0.034(4) Uiso d P 0.5 C 4 O
H50A 0.4964 -0.1627 0.6501 0.051 Uiso calc PR 0.5 C 4 H
C12 0.3913(2) -0.0990(19) 0.7206(6) 0.041(3) Uani d . 1 . . C
H12A 0.3807 -0.2015 0.6886 0.049 Uiso calc R 1 . . H
H12B 0.3785 -0.1055 0.7609 0.049 Uiso calc R 1 . . H
C7 0.4489(2) 0.3296(18) 0.8783(5) 0.034(3) Uani d . 1 . . C
H7A 0.4582 0.2092 0.9062 0.04 Uiso calc R 1 . . H
H7B 0.459 0.319 0.8352 0.04 Uiso calc R 1 . . H
O8 0.46264(16) 0.2410(12) 0.6971(3) 0.0395(19) Uani d . 1 . . O
H8 0.4728 0.1649 0.7252 0.059 Uiso calc R 1 . . H
C51 0.5810(2) 1.281(2) 0.6184(8) 0.075(5) Uani d . 1 B . C
H51A 0.5896 1.3326 0.6611 0.09 Uiso calc R 1 D 1 H
H51B 0.5795 1.115 0.6202 0.09 Uiso calc R 1 D 1 H
C16 0.4481(2) -0.153(2) 0.6736(6) 0.040(3) Uani d . 1 . . C
H16 0.4351 -0.2377 0.64 0.048 Uiso calc R 1 C 3 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0264(11) 0.0294(15) 0.0323(15) -0.0034(11) 0.0063(10) 0.0034(11)
Cl2 0.0224(11) 0.0277(14) 0.0388(15) 0.0052(11) -0.0011(10) 0.0049(12)
Cl11 0.0248(11) 0.0360(16) 0.0352(15) 0.0089(12) 0.0025(10) -0.0031(13)
Cl9 0.0261(12) 0.0261(14) 0.0481(17) 0.0004(12) -0.0041(11) 0.0052(13)
Cl4 0.0242(11) 0.0362(15) 0.0288(14) 0.0062(11) 0.0031(10) -0.0054(12)
Cl10 0.0267(11) 0.0320(15) 0.0292(14) 0.0037(11) 0.0025(10) 0.0086(12)
Cl8 0.0261(11) 0.0405(16) 0.0333(14) -0.0053(12) 0.0002(10) -0.0140(12)
Cl5 0.0219(11) 0.0296(15) 0.0466(17) -0.0018(11) -0.0018(11) -0.0075(13)
Cl12 0.0303(13) 0.0260(15) 0.0462(18) -0.0084(12) -0.0015(12) -0.0041(13)
Cl3 0.0356(13) 0.0334(16) 0.0286(14) -0.0075(12) 0.0076(11) -0.0102(11)
Cl7 0.0353(13) 0.0355(16) 0.0312(14) -0.0066(12) -0.0020(11) 0.0061(12)
Cl6 0.0372(13) 0.0377(16) 0.0321(14) 0.0035(13) 0.0037(11) 0.0069(13)
O1 0.024(3) 0.062(6) 0.060(5) 0.006(4) 0.002(3) 0.040(5)
O9 0.029(3) 0.040(5) 0.020(4) 0.006(3) -0.004(3) -0.009(3)
O13 0.024(3) 0.050(5) 0.020(4) 0.005(3) 0.002(3) -0.009(4)
O6 0.030(3) 0.039(4) 0.029(4) 0.002(3) -0.005(3) -0.003(4)
O10 0.034(4) 0.029(4) 0.029(4) 0.006(3) -0.003(3) -0.006(3)
O3 0.029(3) 0.038(4) 0.031(4) -0.004(3) -0.013(3) 0.007(3)
O12 0.025(3) 0.047(5) 0.038(4) -0.010(3) -0.005(3) 0.010(4)
O11 0.031(4) 0.057(5) 0.026(4) -0.004(4) -0.010(3) 0.007(4)
N4 0.019(4) 0.042(5) 0.030(5) 0.011(4) 0.003(4) -0.014(4)
C25 0.025(4) 0.030(6) 0.012(5) 0.001(4) -0.002(4) -0.002(4)
O4 0.015(3) 0.066(5) 0.028(4) -0.007(3) 0.001(3) 0.008(4)
O2 0.039(5) 0.025(4) 0.086(7) 0.004(3) -0.005(4) 0.015(4)
O7 0.031(4) 0.047(5) 0.037(4) 0.012(3) -0.007(3) -0.017(4)
N1 0.015(4) 0.031(5) 0.040(5) 0.000(4) -0.009(4) 0.016(4)
C2 0.027(5) 0.026(6) 0.023(5) 0.008(5) 0.005(4) -0.002(4)
C1 0.023(4) 0.012(5) 0.021(5) -0.010(4) 0.003(4) -0.001(4)
C26 0.027(5) 0.021(5) 0.025(6) -0.011(4) 0.003(4) 0.000(4)
C6 0.017(4) 0.040(7) 0.029(6) -0.005(5) -0.004(4) 0.013(5)
C18 0.021(5) 0.022(5) 0.029(6) 0.006(4) -0.010(4) -0.007(5)
C9 0.031(5) 0.029(6) 0.019(5) -0.001(5) -0.005(4) 0.002(5)
C10 0.017(4) 0.024(5) 0.029(6) 0.000(4) -0.005(4) -0.002(5)
N3 0.031(5) 0.034(5) 0.030(5) -0.005(4) -0.016(4) -0.005(4)
C17 0.025(5) 0.017(5) 0.037(6) -0.002(4) 0.001(4) 0.003(5)
C5 0.031(5) 0.029(6) 0.018(5) -0.001(5) 0.000(4) 0.007(4)
C3 0.017(5) 0.033(6) 0.028(6) -0.009(4) -0.013(4) 0.003(5)
C13 0.051(6) 0.021(6) 0.030(6) 0.014(5) -0.002(5) 0.000(4)
C20 0.019(4) 0.030(6) 0.034(6) 0.004(4) 0.001(4) -0.002(5)
N2 0.019(4) 0.077(7) 0.048(6) 0.018(5) -0.009(4) -0.035(6)
C11 0.016(4) 0.033(6) 0.040(6) 0.006(4) 0.000(4) -0.010(5)
C4 0.012(4) 0.032(6) 0.041(6) 0.006(4) 0.008(4) 0.011(5)
C27 0.035(6) 0.036(6) 0.026(6) 0.008(5) -0.019(5) -0.013(5)
C24 0.026(5) 0.035(7) 0.042(7) 0.001(5) 0.008(5) -0.021(5)
C19 0.014(4) 0.029(6) 0.028(5) -0.014(4) -0.005(4) -0.009(4)
C15 0.033(5) 0.031(6) 0.027(6) -0.004(5) -0.011(4) -0.002(5)
C8 0.039(6) 0.029(6) 0.028(6) -0.009(5) -0.009(5) 0.004(5)
C22 0.023(5) 0.037(6) 0.027(6) -0.016(4) -0.002(4) -0.004(5)
C14 0.024(5) 0.040(7) 0.036(6) -0.008(5) -0.004(4) -0.007(5)
C21 0.020(5) 0.045(7) 0.029(6) 0.001(5) -0.004(4) 0.013(5)
C23 0.037(6) 0.030(6) 0.031(6) -0.009(5) -0.008(5) -0.010(5)
C30 0.013(4) 0.046(7) 0.020(5) 0.013(5) 0.003(4) -0.013(5)
O14 0.013(3) 0.046(5) 0.036(4) 0.005(3) 0.002(3) -0.004(4)
C30A 0.013(4) 0.046(7) 0.020(5) 0.013(5) 0.003(4) -0.013(5)
C12 0.035(6) 0.047(8) 0.040(7) -0.004(6) 0.012(5) -0.005(6)
C7 0.016(5) 0.059(7) 0.027(6) 0.006(5) 0.005(4) -0.004(5)
O8 0.027(4) 0.059(5) 0.032(4) -0.013(3) -0.006(3) -0.006(4)
C51 0.012(5) 0.071(10) 0.141(14) -0.011(6) -0.006(7) 0.053(9)
C16 0.028(5) 0.056(8) 0.038(7) 0.020(5) 0.004(5) 0.003(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 N4 C27 122.3(8) . . ?
C26 C25 Cl11 110.1(6) . . ?
C26 C25 Cl12 107.1(7) . . ?
Cl11 C25 Cl12 110.2(5) . . ?
C26 C25 Cl10 110.3(6) . . ?
Cl11 C25 Cl10 109.5(5) . . ?
Cl12 C25 Cl10 109.6(5) . . ?
C2 N1 C3 123.1(8) . . ?
O1 C2 N1 125.3(8) . . ?
O1 C2 C1 118.7(8) . . ?
N1 C2 C1 115.9(8) . . ?
C2 C1 Cl1 111.2(6) . . ?
C2 C1 Cl2 110.3(6) . . ?
Cl1 C1 Cl2 109.9(5) . . ?
C2 C1 Cl3 105.9(6) . . ?
Cl1 C1 Cl3 110.2(4) . . ?
Cl2 C1 Cl3 109.3(5) . . ?
O13 C26 N4 126.1(9) . . ?
O13 C26 C25 119.7(8) . . ?
N4 C26 C25 114.2(8) . . ?
O4 C6 C5 108.8(7) . . ?
O4 C6 C7 109.7(8) . . ?
C5 C6 C7 111.8(8) . . ?
O9 C18 N3 125.0(8) . . ?
O9 C18 C17 121.1(9) . . ?
N3 C18 C17 113.9(8) . . ?
C10 C9 Cl6 108.5(6) . . ?
C10 C9 Cl5 110.7(7) . . ?
Cl6 C9 Cl5 110.3(5) . . ?
C10 C9 Cl4 110.2(6) . . ?
Cl6 C9 Cl4 109.0(5) . . ?
Cl5 C9 Cl4 108.1(5) . . ?
O6 C10 N2 125.7(8) . . ?
O6 C10 C9 121.0(9) . . ?
N2 C10 C9 113.3(8) . . ?
C18 N3 C19 122.1(8) . . ?
C18 C17 Cl7 110.2(7) . . ?
C18 C17 Cl9 108.1(6) . . ?
Cl7 C17 Cl9 109.0(5) . . ?
C18 C17 Cl8 111.6(6) . . ?
Cl7 C17 Cl8 108.6(5) . . ?
Cl9 C17 Cl8 109.3(5) . . ?
O3 C5 C6 111.7(8) . . ?
O3 C5 C4 108.1(7) . . ?
C6 C5 C4 109.7(7) . . ?
N1 C3 C8 108.3(8) . . ?
N1 C3 C4 110.7(8) . . ?
C8 C3 C4 111.2(8) . . ?
C16 C13 C12 109.2(8) . . ?
O10 C20 C19 107.9(7) . . ?
O10 C20 C21 109.2(7) . . ?
C19 C20 C21 111.0(7) . . ?
C10 N2 C11 124.1(8) . . ?
N2 C11 C15 109.7(8) . . ?
N2 C11 C12 109.7(8) . . ?
C15 C11 C12 111.3(8) . . ?
O2 C4 C3 108.2(7) . . ?
O2 C4 C5 107.9(7) . . ?
C3 C4 C5 111.6(8) . . ?
C32 C27 N4 116.9(11) . . ?
C32 C27 C51 116.6(11) . . ?
N4 C27 C51 111.3(9) . . ?
C32 C27 C32A 26.4(9) . . ?
N4 C27 C32A 105.0(10) . . ?
C51 C27 C32A 104.2(11) . . ?
C23 C24 C19 107.8(7) . . ?
N3 C19 C20 110.5(7) . . ?
N3 C19 C24 108.9(7) . . ?
C20 C19 C24 113.0(8) . . ?
O7 C15 C11 111.7(8) . . ?
O7 C15 C14 104.1(8) . . ?
C11 C15 C14 110.4(8) . . ?
C3 C8 C7 112.6(8) . . ?
O12 C22 C23 111.0(7) . . ?
O12 C22 C21 114.2(8) . . ?
C23 C22 C21 110.1(8) . . ?
O8 C14 C16 109.8(8) . . ?
O8 C14 C15 109.0(8) . . ?
C16 C14 C15 110.2(8) . . ?
O11 C21 C22 112.9(9) . . ?
O11 C21 C20 109.2(8) . . ?
C22 C21 C20 110.4(7) . . ?
C22 C23 C24 111.1(8) . . ?
C29 C30 O14 116.8(9) . . ?
C29 C30 C31 112.8(11) . . ?
O14 C30 C31 102.8(9) . . ?
O15 C31 C32 104.8(15) . . ?
O15 C31 C30 109.1(13) . . ?
C32 C31 C30 108.6(15) . . ?
C27 C32 O16 107.9(14) . . ?
C27 C32 C31 116.1(15) . . ?
O16 C32 C31 105.6(15) . . ?
C30 C29 C51 113.9(12) . . ?
O15A C31A C32A 107.7(17) . . ?
O16A C32A C31A 101.6(16) . . ?
O16A C32A C27 110.5(14) . . ?
C31A C32A C27 107.9(16) . . ?
C11 C12 C13 111.0(8) . . ?
C6 C7 C8 108.4(8) . . ?
C27 C51 C29 117.4(11) . . ?
C27 C51 C29A 102.1(12) . . ?
C29 C51 C29A 24.3(10) . . ?
O50 C16 C14 124.7(10) . . ?
O50 C16 C13 106.4(9) . . ?
C14 C16 C13 112.1(9) . . ?
O50 C16 O50A 30.3(7) . . ?
C14 C16 O50A 96.2(10) . . ?
C13 C16 O50A 114.4(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.742(9) ?
Cl2 C1 . 1.774(9) ?
Cl11 C25 . 1.753(9) ?
Cl9 C17 . 1.768(9) ?
Cl4 C9 . 1.777(10) ?
Cl10 C25 . 1.772(9) ?
Cl8 C17 . 1.788(10) ?
Cl5 C9 . 1.776(10) ?
Cl12 C25 . 1.767(10) ?
Cl3 C1 . 1.786(9) ?
Cl7 C17 . 1.765(9) ?
Cl6 C9 . 1.760(10) ?
O1 C2 . 1.217(11) ?
O9 C18 . 1.224(11) ?
O13 C26 . 1.219(10) ?
O6 C10 . 1.194(10) ?
O10 C20 . 1.438(10) ?
O3 C5 . 1.425(10) ?
O12 C22 . 1.443(10) ?
O11 C21 . 1.432(10) ?
N4 C26 . 1.328(12) ?
N4 C27 . 1.457(11) ?
C25 C26 . 1.575(11) ?
O4 C6 . 1.451(9) ?
O2 C4 . 1.416(10) ?
O7 C15 . 1.439(10) ?
N1 C2 . 1.335(12) ?
N1 C3 . 1.439(10) ?
C2 C1 . 1.571(11) ?
C6 C5 . 1.482(12) ?
C6 C7 . 1.520(13) ?
C18 N3 . 1.347(12) ?
C18 C17 . 1.546(11) ?
C9 C10 . 1.566(12) ?
C10 N2 . 1.319(12) ?
N3 C19 . 1.473(10) ?
C5 C4 . 1.536(11) ?
C3 C8 . 1.512(13) ?
C3 C4 . 1.524(13) ?
C13 C16 . 1.512(14) ?
C13 C12 . 1.540(12) ?
C20 C19 . 1.506(12) ?
C20 C21 . 1.531(12) ?
N2 C11 . 1.465(10) ?
C11 C15 . 1.502(13) ?
C11 C12 . 1.536(14) ?
C27 C32 . 1.41(2) ?
C27 C51 . 1.503(15) ?
C27 C32A . 1.61(2) ?
C24 C23 . 1.550(12) ?
C24 C19 . 1.552(12) ?
C15 C14 . 1.528(12) ?
C8 C7 . 1.532(11) ?
C22 C23 . 1.501(13) ?
C22 C21 . 1.518(13) ?
C14 O8 . 1.439(10) ?
C14 C16 . 1.509(14) ?
C30 C29 . 1.410(19) ?
C30 O14 . 1.444(9) ?
C30 C31 . 1.59(2) ?
C31 O15 . 1.45(2) ?
C31 C32 . 1.53(2) ?
C32 O16 . 1.44(2) ?
C29 C51 . 1.514(18) ?
C31A O15A . 1.46(2) ?
C31A C32A . 1.53(3) ?
C32A O16A . 1.46(2) ?
C29A C51 . 1.65(2) ?
O50 C16 . 1.413(13) ?
O50A C16 . 1.560(16) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 O1 7.4(16) . . . . ?
C3 N1 C2 C1 -168.6(8) . . . . ?
O1 C2 C1 Cl1 20.1(11) . . . . ?
N1 C2 C1 Cl1 -163.6(7) . . . . ?
O1 C2 C1 Cl2 142.3(8) . . . . ?
N1 C2 C1 Cl2 -41.4(10) . . . . ?
O1 C2 C1 Cl3 -99.5(9) . . . . ?
N1 C2 C1 Cl3 76.7(9) . . . . ?
C27 N4 C26 O13 0.9(16) . . . . ?
C27 N4 C26 C25 -179.6(9) . . . . ?
Cl11 C25 C26 O13 -7.0(11) . . . . ?
Cl12 C25 C26 O13 112.8(9) . . . . ?
Cl10 C25 C26 O13 -128.0(8) . . . . ?
Cl11 C25 C26 N4 173.5(7) . . . . ?
Cl12 C25 C26 N4 -66.8(9) . . . . ?
Cl10 C25 C26 N4 52.5(10) . . . . ?
Cl6 C9 C10 O6 106.6(10) . . . . ?
Cl5 C9 C10 O6 -132.2(9) . . . . ?
Cl4 C9 C10 O6 -12.7(12) . . . . ?
Cl6 C9 C10 N2 -72.5(10) . . . . ?
Cl5 C9 C10 N2 48.6(11) . . . . ?
Cl4 C9 C10 N2 168.2(8) . . . . ?
O9 C18 N3 C19 5.4(15) . . . . ?
C17 C18 N3 C19 -171.3(8) . . . . ?
O9 C18 C17 Cl7 12.4(12) . . . . ?
N3 C18 C17 Cl7 -170.7(7) . . . . ?
O9 C18 C17 Cl9 -106.7(9) . . . . ?
N3 C18 C17 Cl9 70.2(9) . . . . ?
O9 C18 C17 Cl8 133.1(8) . . . . ?
N3 C18 C17 Cl8 -50.0(10) . . . . ?
O4 C6 C5 O3 -61.8(11) . . . . ?
C7 C6 C5 O3 59.6(9) . . . . ?
O4 C6 C5 C4 178.2(8) . . . . ?
C7 C6 C5 C4 -60.4(10) . . . . ?
C2 N1 C3 C8 120.2(10) . . . . ?
C2 N1 C3 C4 -117.8(10) . . . . ?
O6 C10 N2 C11 -7.6(18) . . . . ?
C9 C10 N2 C11 171.5(9) . . . . ?
C10 N2 C11 C15 -128.0(11) . . . . ?
C10 N2 C11 C12 109.3(12) . . . . ?
N1 C3 C4 O2 -54.1(10) . . . . ?
C8 C3 C4 O2 66.2(9) . . . . ?
N1 C3 C4 C5 -172.8(8) . . . . ?
C8 C3 C4 C5 -52.5(10) . . . . ?
O3 C5 C4 O2 175.1(8) . . . . ?
C6 C5 C4 O2 -62.8(11) . . . . ?
O3 C5 C4 C3 -66.0(10) . . . . ?
C6 C5 C4 C3 56.2(11) . . . . ?
C26 N4 C27 C32 -84.8(14) . . . . ?
C26 N4 C27 C51 137.3(11) . . . . ?
C26 N4 C27 C32A -110.2(12) . . . . ?
C18 N3 C19 C20 -141.7(9) . . . . ?
C18 N3 C19 C24 93.7(11) . . . . ?
O10 C20 C19 N3 -57.2(10) . . . . ?
C21 C20 C19 N3 -176.9(8) . . . . ?
O10 C20 C19 C24 65.1(10) . . . . ?
C21 C20 C19 C24 -54.6(10) . . . . ?
C23 C24 C19 N3 177.7(8) . . . . ?
C23 C24 C19 C20 54.6(11) . . . . ?
N2 C11 C15 O7 -62.8(10) . . . . ?
C12 C11 C15 O7 58.7(10) . . . . ?
N2 C11 C15 C14 -177.9(8) . . . . ?
C12 C11 C15 C14 -56.3(10) . . . . ?
N1 C3 C8 C7 174.9(8) . . . . ?
C4 C3 C8 C7 53.2(11) . . . . ?
O7 C15 C14 O8 176.6(7) . . . . ?
C11 C15 C14 O8 -63.6(11) . . . . ?
O7 C15 C14 C16 -62.5(10) . . . . ?
C11 C15 C14 C16 57.3(11) . . . . ?
O12 C22 C21 O11 -61.9(10) . . . . ?
C23 C22 C21 O11 63.5(10) . . . . ?
O12 C22 C21 C20 175.5(7) . . . . ?
C23 C22 C21 C20 -59.1(10) . . . . ?
O10 C20 C21 O11 171.7(7) . . . . ?
C19 C20 C21 O11 -69.3(10) . . . . ?
O10 C20 C21 C22 -63.5(10) . . . . ?
C19 C20 C21 C22 55.6(11) . . . . ?
O12 C22 C23 C24 -171.1(8) . . . . ?
C21 C22 C23 C24 61.5(11) . . . . ?
C19 C24 C23 C22 -57.7(11) . . . . ?
C31A C30 C31 O15 178(3) . . . . ?
C29 C30 C31 O15 57.0(15) . . . . ?
O14 C30 C31 O15 -67.3(14) . . . . ?
C29A C30 C31 O15 41.4(15) . . . . ?
C31A C30 C31 C32 64(3) . . . . ?
C29 C30 C31 C32 -56.7(17) . . . . ?
O14 C30 C31 C32 179.0(13) . . . . ?
C29A C30 C31 C32 -72.3(16) . . . . ?
N4 C27 C32 O16 -57.2(17) . . . . ?
C51 C27 C32 O16 78.5(15) . . . . ?
C32A C27 C32 O16 11.0(19) . . . . ?
N4 C27 C32 C31 -175.2(14) . . . . ?
C51 C27 C32 C31 -40(2) . . . . ?
C32A C27 C32 C31 -107(3) . . . . ?
O15 C31 C32 C27 -67(2) . . . . ?
C30 C31 C32 C27 50(2) . . . . ?
O15 C31 C32 O16 173.9(14) . . . . ?
C30 C31 C32 O16 -69.3(17) . . . . ?
C29 C30 C31A O15A 88.4(17) . . . . ?
O14 C30 C31A O15A -56.8(18) . . . . ?
C31 C30 C31A O15A 16.2(19) . . . . ?
C29A C30 C31A O15A 63.7(18) . . . . ?
C29 C30 C31A C32A -31(3) . . . . ?
O14 C30 C31A C32A -176.7(15) . . . . ?
C31 C30 C31A C32A -104(3) . . . . ?
C29A C30 C31A C32A -56(2) . . . . ?
C30 C31A C32A O16A -68(2) . . . . ?
O15A C31A C32A O16A 171.1(15) . . . . ?
C30 C31A C32A C27 48(2) . . . . ?
O15A C31A C32A C27 -73.0(18) . . . . ?
C32 C27 C32A O16A 172(3) . . . . ?
N4 C27 C32A O16A -66.7(15) . . . . ?
C51 C27 C32A O16A 50.6(16) . . . . ?
C32 C27 C32A C31A 63(2) . . . . ?
N4 C27 C32A C31A -176.2(13) . . . . ?
C51 C27 C32A C31A -58.9(17) . . . . ?
C31A C30 C29 C51 25(2) . . . . ?
O14 C30 C29 C51 169.2(11) . . . . ?
C31 C30 C29 C51 52.9(17) . . . . ?
C29A C30 C29 C51 92(3) . . . . ?
C31A C30 C29A C51 67.5(16) . . . . ?
C29 C30 C29A C51 -57(2) . . . . ?
O14 C30 C29A C51 -169.5(10) . . . . ?
C31 C30 C29A C51 87.2(13) . . . . ?
N2 C11 C12 C13 177.6(8) . . . . ?
C15 C11 C12 C13 56.0(11) . . . . ?
C16 C13 C12 C11 -55.0(12) . . . . ?
O4 C6 C7 C8 -179.4(8) . . . . ?
C5 C6 C7 C8 59.7(10) . . . . ?
C3 C8 C7 C6 -55.5(11) . . . . ?
C32 C27 C51 C29 33.2(18) . . . . ?
N4 C27 C51 C29 171.4(11) . . . . ?
C32A C27 C51 C29 58.4(16) . . . . ?
C32 C27 C51 C29A 54.0(16) . . . . ?
N4 C27 C51 C29A -167.8(11) . . . . ?
C32A C27 C51 C29A 79.2(14) . . . . ?
C30 C29 C51 C27 -41.3(19) . . . . ?
C30 C29 C51 C29A -96(3) . . . . ?
C30 C29A C51 C27 -80.0(14) . . . . ?
C30 C29A C51 C29 52(2) . . . . ?
O8 C14 C16 O50 -68.8(14) . . . . ?
C15 C14 C16 O50 171.0(11) . . . . ?
O8 C14 C16 C13 61.4(11) . . . . ?
C15 C14 C16 C13 -58.8(11) . . . . ?
O8 C14 C16 O50A -57.8(10) . . . . ?
C15 C14 C16 O50A -178.0(9) . . . . ?
C12 C13 C16 O50 -163.3(9) . . . . ?
C12 C13 C16 C14 57.4(12) . . . . ?
C12 C13 C16 O50A 165.5(10) . . . . ?