#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150992.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_7150992
loop_
_publ_author_name
'Aciro, Caroline'
'Claridge, Timothy D. W.'
'Davies, Stephen G.'
'Roberts, Paul M.'
'Russell, Angela J.'
'Thomson, James E.'
_publ_section_title
;
 Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes:
 development of a metal-free dihydroxylation protocol
;
_journal_issue                   20
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3751
_journal_page_last               3761
_journal_paper_doi               10.1039/b808811j
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C17.50 H18 Cl6.67 N0.67 O4.67'
_chemical_formula_sum            'C17.5 H18 Cl6.67 N0.67 O4.67'
_chemical_formula_weight         548.69
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-01-31
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 106.7096(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   24.5125(2)
_cell_length_b                   9.82110(10)
_cell_length_c                   30.9595(4)
_cell_measurement_reflns_used    8099
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     7138.47(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14748
_diffrn_reflns_theta_full        26.917
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         5.138
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       plate
_exptl_crystal_F_000             3340
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.00
_refine_diff_density_min         -1.53
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0918
_refine_ls_shift/su_max          0.003363
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method= Quasi-Unit weights
W = 1.0 or 1./2F
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1107
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0951
_reflns_limit_h_max              30
_reflns_limit_h_min              -31
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                5826
_reflns_number_total             7984
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            b808811j.txt
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C17.50 H18 Cl6.67 N0.67 O4.67'
_cod_database_code               7150992
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
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.4895(2) -0.1750(7) 0.94748(18) 0.0424 1.0000 Uani . . . . . .
Cl2 Cl 0.44306(7) -0.2354(2) 0.97711(6) 0.0671 1.0000 Uani . . . . . .
C3 C 0.5528(2) -0.1793(5) 0.97640(17) 0.0322 1.0000 Uani . . . . . .
O4 O 0.58655(15) -0.1100(4) 0.96126(11) 0.0367 1.0000 Uani . . . . . .
O5 O 0.56513(15) -0.2514(4) 1.01023(12) 0.0356 1.0000 Uani . . . . . .
Cl6 Cl 0.46949(6) -0.00493(17) 0.93059(5) 0.0517 1.0000 Uani . . . . . .
Cl7 Cl 0.48342(7) -0.27780(18) 0.89910(5) 0.0557 1.0000 Uani . . . . . .
C8 C 0.3356(3) -0.1472(6) 0.80758(19) 0.0464 1.0000 Uani . . . . . .
C9 C 0.3215(2) -0.1719(6) 0.85302(19) 0.0386 1.0000 Uani . . . . . .
O10 O 0.31925(15) -0.0541(3) 0.87296(11) 0.0318 1.0000 Uani . . . . . .
C11 C 0.2967(2) -0.0576(5) 0.91227(16) 0.0303 1.0000 Uani . . . . . .
C12 C 0.3217(2) 0.0684(5) 0.93942(15) 0.0276 1.0000 Uani . . . . . .
C13 C 0.2980(2) 0.1966(5) 0.91252(16) 0.0287 1.0000 Uani . . . . . .
N14 N 0.32552(17) 0.3229(4) 0.93801(13) 0.0279 1.0000 Uani . . . . . .
C15 C 0.2939(2) 0.3782(5) 0.97004(17) 0.0303 1.0000 Uani . . . . . .
C16 C 0.3262(2) 0.4868(5) 1.00141(17) 0.0299 1.0000 Uani . . . . . .
C17 C 0.3106(2) 0.6235(5) 0.99356(18) 0.0335 1.0000 Uani . . . . . .
C18 C 0.3390(2) 0.7235(5) 1.02294(19) 0.0393 1.0000 Uani . . . . . .
C19 C 0.3833(2) 0.6882(6) 1.0596(2) 0.0416 1.0000 Uani . . . . . .
C20 C 0.3987(2) 0.5525(6) 1.06859(19) 0.0416 1.0000 Uani . . . . . .
C21 C 0.3695(2) 0.4526(6) 1.03948(17) 0.0342 1.0000 Uani . . . . . .
C22 C 0.3341(2) 0.4349(5) 0.90700(17) 0.0339 1.0000 Uani . . . . . .
C23 C 0.3671(2) 0.3889(5) 0.87520(17) 0.0336 1.0000 Uani . . . . . .
C24 C 0.4247(2) 0.3604(6) 0.89024(18) 0.0406 1.0000 Uani . . . . . .
C25 C 0.4536(3) 0.3183(7) 0.8600(2) 0.0509 1.0000 Uani . . . . . .
C26 C 0.4258(3) 0.3055(7) 0.8147(2) 0.0494 1.0000 Uani . . . . . .
C27 C 0.3677(3) 0.3327(7) 0.79940(19) 0.0493 1.0000 Uani . . . . . .
C28 C 0.3391(3) 0.3737(7) 0.82972(18) 0.0450 1.0000 Uani . . . . . .
C29 C 0.2330(2) 0.2016(6) 0.89811(18) 0.0355 1.0000 Uani . . . . . .
C30 C 0.2097(2) 0.0742(6) 0.86965(19) 0.0416 1.0000 Uani . . . . . .
C31 C 0.2322(2) -0.0559(6) 0.89589(19) 0.0389 1.0000 Uani . . . . . .
O32 O 0.30636(14) 0.0630(4) 0.98055(11) 0.0319 1.0000 Uani . . . . . .
O33 O 0.31261(19) -0.2815(4) 0.86531(14) 0.0470 1.0000 Uani . . . . . .
Cl34 Cl 0.39094(8) -0.0357(2) 0.81312(5) 0.0603 1.0000 Uani . . . . . .
Cl35 Cl 0.35317(18) -0.3024(2) 0.78750(10) 0.1395 1.0000 Uani . . . . . .
Cl36 Cl 0.27317(9) -0.0764(5) 0.77140(6) 0.1389 1.0000 Uani . . . . . .
H111 H 0.3110 -0.1390 0.9303 0.0375 1.0000 Uiso R . . . . .
H121 H 0.3631 0.0680 0.9460 0.0339 1.0000 Uiso R . . . . .
H131 H 0.3111 0.1930 0.8855 0.0335 1.0000 Uiso R . . . . .
H151 H 0.2884 0.3016 0.9879 0.0365 1.0000 Uiso R . . . . .
H152 H 0.2574 0.4127 0.9525 0.0368 1.0000 Uiso R . . . . .
H171 H 0.2802 0.6475 0.9685 0.0409 1.0000 Uiso R . . . . .
H181 H 0.3271 0.8137 1.0174 0.0498 1.0000 Uiso R . . . . .
H191 H 0.4037 0.7565 1.0785 0.0505 1.0000 Uiso R . . . . .
H201 H 0.4281 0.5287 1.0934 0.0491 1.0000 Uiso R . . . . .
H211 H 0.3792 0.3611 1.0456 0.0418 1.0000 Uiso R . . . . .
H221 H 0.3548 0.5081 0.9254 0.0409 1.0000 Uiso R . . . . .
H222 H 0.2972 0.4670 0.8898 0.0408 1.0000 Uiso R . . . . .
H241 H 0.4433 0.3683 0.9209 0.0481 1.0000 Uiso R . . . . .
H251 H 0.4926 0.2993 0.8708 0.0630 1.0000 Uiso R . . . . .
H261 H 0.4461 0.2789 0.7949 0.0627 1.0000 Uiso R . . . . .
H271 H 0.3477 0.3235 0.7689 0.0581 1.0000 Uiso R . . . . .
H281 H 0.3002 0.3900 0.8194 0.0531 1.0000 Uiso R . . . . .
H291 H 0.2192 0.2026 0.9245 0.0411 1.0000 Uiso R . . . . .
H292 H 0.2202 0.2834 0.8807 0.0408 1.0000 Uiso R . . . . .
H301 H 0.1680 0.0733 0.8615 0.0468 1.0000 Uiso R . . . . .
H302 H 0.2214 0.0760 0.8425 0.0469 1.0000 Uiso R . . . . .
H311 H 0.2184 -0.0610 0.9222 0.0473 1.0000 Uiso R . . . . .
H312 H 0.2191 -0.1344 0.8769 0.0468 1.0000 Uiso R . . . . .
H141 H 0.3600 0.2982 0.9548 0.0420 1.0000 Uiso R . . . . .
H321 H 0.3361 0.0713 1.0007 0.0492 1.0000 Uiso R . . . . .
C37 C 0.1213(3) 0.5411(7) 0.8291(2) 0.0515 1.0000 Uani . . . . . .
C38 C 0.1243(2) 0.5097(6) 0.87831(18) 0.0388 1.0000 Uani . . . . . .
O39 O 0.16847(17) 0.5049(5) 0.90708(14) 0.0505 1.0000 Uani . . . . . .
O40 O 0.07369(16) 0.4890(5) 0.88269(12) 0.0476 1.0000 Uani . . . . . .
Cl41 Cl 0.18793(8) 0.5926(2) 0.82451(7) 0.0693 1.0000 Uani . . . . . .
Cl42 Cl 0.10547(13) 0.3838(3) 0.80009(7) 0.1066 1.0000 Uani . . . . . .
Cl43 Cl 0.07252(11) 0.6695(4) 0.80775(9) 0.1316 1.0000 Uani . . . . . .
Cl1 Cl 0.05028(14) 0.0371(3) 0.78752(14) 0.1419 1.0000 Uani . . . . . .
H402 H 0.0759 0.4605 0.9079 0.0701 1.0000 Uiso R . . . . .
C4 C 0.0000 0.116(2) 0.7500 0.2928 0.5000 Uani S T . . . .
H42 H 0.0191 0.1744 0.7332 0.3820 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl2 . C1 . C3 . 112.3(4) yes
Cl2 . C1 . Cl6 . 107.8(3) yes
C3 . C1 . Cl6 . 109.9(4) yes
Cl2 . C1 . Cl7 . 109.8(3) yes
C3 . C1 . Cl7 . 107.3(4) yes
Cl6 . C1 . Cl7 . 109.7(3) yes
C1 . C3 . O4 . 115.1(4) yes
C1 . C3 . O5 . 117.9(5) yes
O4 . C3 . O5 . 126.9(5) yes
C9 . C8 . Cl34 . 112.5(4) yes
C9 . C8 . Cl35 . 109.1(4) yes
Cl34 . C8 . Cl35 . 108.9(4) yes
C9 . C8 . Cl36 . 105.0(4) yes
Cl34 . C8 . Cl36 . 109.2(4) yes
Cl35 . C8 . Cl36 . 112.2(4) yes
C8 . C9 . O10 . 109.6(5) yes
C8 . C9 . O33 . 122.7(5) yes
O10 . C9 . O33 . 127.6(5) yes
C9 . O10 . C11 . 116.3(4) yes
O10 . C11 . C12 . 104.4(4) yes
O10 . C11 . C31 . 109.1(4) yes
C12 . C11 . C31 . 113.1(4) yes
O10 . C11 . H111 . 109.3 no
C12 . C11 . H111 . 109.1 no
C31 . C11 . H111 . 111.6 no
C11 . C12 . C13 . 109.8(4) yes
C11 . C12 . O32 . 107.1(4) yes
C13 . C12 . O32 . 111.1(4) yes
C11 . C12 . H121 . 110.0 no
C13 . C12 . H121 . 109.1 no
O32 . C12 . H121 . 109.7 no
C12 . C13 . N14 . 110.3(4) yes
C12 . C13 . C29 . 112.8(4) yes
N14 . C13 . C29 . 113.3(4) yes
C12 . C13 . H131 . 105.5 no
N14 . C13 . H131 . 105.4 no
C29 . C13 . H131 . 108.9 no
C13 . N14 . C15 . 113.3(4) yes
C13 . N14 . C22 . 112.7(4) yes
C15 . N14 . C22 . 110.1(4) yes
C13 . N14 . H141 . 106.7 no
C15 . N14 . H141 . 107.0 no
C22 . N14 . H141 . 106.6 no
N14 . C15 . C16 . 113.6(4) yes
N14 . C15 . H151 . 106.0 no
C16 . C15 . H151 . 108.5 no
N14 . C15 . H152 . 108.7 no
C16 . C15 . H152 . 110.2 no
H151 . C15 . H152 . 109.7 no
C15 . C16 . C17 . 120.1(5) yes
C15 . C16 . C21 . 120.7(5) yes
C17 . C16 . C21 . 119.1(5) yes
C16 . C17 . C18 . 120.4(5) yes
C16 . C17 . H171 . 119.9 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 119.6(5) yes
C17 . C18 . H181 . 118.7 no
C19 . C18 . H181 . 121.7 no
C18 . C19 . C20 . 120.9(5) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 119.7 no
C19 . C20 . C21 . 119.2(5) yes
C19 . C20 . H201 . 121.0 no
C21 . C20 . H201 . 119.8 no
C20 . C21 . C16 . 120.6(5) yes
C20 . C21 . H211 . 119.7 no
C16 . C21 . H211 . 119.7 no
N14 . C22 . C23 . 113.2(4) yes
N14 . C22 . H221 . 108.2 no
C23 . C22 . H221 . 108.5 no
N14 . C22 . H222 . 107.9 no
C23 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 109.5 no
C22 . C23 . C24 . 121.8(5) yes
C22 . C23 . C28 . 119.5(5) yes
C24 . C23 . C28 . 118.7(5) yes
C23 . C24 . C25 . 120.2(5) yes
C23 . C24 . H241 . 118.8 no
C25 . C24 . H241 . 121.0 no
C24 . C25 . C26 . 120.8(6) yes
C24 . C25 . H251 . 119.2 no
C26 . C25 . H251 . 120.0 no
C25 . C26 . C27 . 119.3(5) yes
C25 . C26 . H261 . 119.5 no
C27 . C26 . H261 . 121.2 no
C26 . C27 . C28 . 119.5(5) yes
C26 . C27 . H271 . 121.0 no
C28 . C27 . H271 . 119.5 no
C23 . C28 . C27 . 121.4(5) yes
C23 . C28 . H281 . 119.5 no
C27 . C28 . H281 . 119.1 no
C13 . C29 . C30 . 108.9(4) yes
C13 . C29 . H291 . 110.0 no
C30 . C29 . H291 . 109.1 no
C13 . C29 . H292 . 109.4 no
C30 . C29 . H292 . 110.4 no
H291 . C29 . H292 . 109.0 no
C29 . C30 . C31 . 110.9(4) yes
C29 . C30 . H301 . 110.0 no
C31 . C30 . H301 . 108.5 no
C29 . C30 . H302 . 109.3 no
C31 . C30 . H302 . 109.1 no
H301 . C30 . H302 . 109.0 no
C30 . C31 . C11 . 111.6(4) yes
C30 . C31 . H311 . 109.4 no
C11 . C31 . H311 . 107.4 no
C30 . C31 . H312 . 109.8 no
C11 . C31 . H312 . 109.1 no
H311 . C31 . H312 . 109.6 no
C12 . O32 . H321 . 105.7 no
C38 . C37 . Cl41 . 111.0(4) yes
C38 . C37 . Cl42 . 105.6(4) yes
Cl41 . C37 . Cl42 . 106.4(4) yes
C38 . C37 . Cl43 . 110.8(4) yes
Cl41 . C37 . Cl43 . 108.4(4) yes
Cl42 . C37 . Cl43 . 114.5(4) yes
C37 . C38 . O39 . 121.6(5) yes
C37 . C38 . O40 . 111.1(5) yes
O39 . C38 . O40 . 127.3(5) yes
C38 . O40 . H402 . 110.6 no
H42 5_556 C4 . Cl1 . 106.2 no
H42 5_556 C4 . Cl1 5_556 106.2 no
Cl1 . C4 . Cl1 5_556 123.2(15) yes
H42 5_556 C4 . H42 . 108.0 no
Cl1 . C4 . H42 . 106.2 no
Cl1 5_556 C4 . H42 . 106.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . Cl2 . 1.757(6) yes
C1 . C3 . 1.553(7) yes
C1 . Cl6 . 1.777(6) yes
C1 . Cl7 . 1.777(6) yes
C3 . O4 . 1.261(6) yes
C3 . O5 . 1.228(6) yes
C8 . C9 . 1.560(8) yes
C8 . Cl34 . 1.714(6) yes
C8 . Cl35 . 1.746(7) yes
C8 . Cl36 . 1.759(7) yes
C9 . O10 . 1.320(6) yes
C9 . O33 . 1.184(6) yes
O10 . C11 . 1.475(5) yes
C11 . C12 . 1.522(7) yes
C11 . C31 . 1.516(7) yes
C11 . H111 . 0.980 no
C12 . C13 . 1.529(7) yes
C12 . O32 . 1.429(5) yes
C12 . H121 . 0.977 no
C13 . N14 . 1.520(6) yes
C13 . C29 . 1.526(7) yes
C13 . H131 . 0.979 no
N14 . C15 . 1.524(6) yes
N14 . C22 . 1.514(6) yes
N14 . H141 . 0.890 no
C15 . C16 . 1.506(7) yes
C15 . H151 . 0.966 no
C15 . H152 . 0.965 no
C16 . C17 . 1.398(7) yes
C16 . C21 . 1.382(7) yes
C17 . C18 . 1.383(7) yes
C17 . H171 . 0.937 no
C18 . C19 . 1.369(8) yes
C18 . H181 . 0.933 no
C19 . C20 . 1.391(8) yes
C19 . H191 . 0.935 no
C20 . C21 . 1.385(8) yes
C20 . H201 . 0.919 no
C21 . H211 . 0.935 no
C22 . C23 . 1.512(7) yes
C22 . H221 . 0.965 no
C22 . H222 . 0.962 no
C23 . C24 . 1.381(8) yes
C23 . C28 . 1.386(7) yes
C24 . C25 . 1.390(8) yes
C24 . H241 . 0.930 no
C25 . C26 . 1.378(9) yes
C25 . H251 . 0.936 no
C26 . C27 . 1.391(9) yes
C26 . H261 . 0.933 no
C27 . C28 . 1.383(8) yes
C27 . H271 . 0.935 no
C28 . H281 . 0.929 no
C29 . C30 . 1.542(7) yes
C29 . H291 . 0.970 no
C29 . H292 . 0.967 no
C30 . C31 . 1.529(8) yes
C30 . H301 . 0.980 no
C30 . H302 . 0.963 no
C31 . H311 . 0.967 no
C31 . H312 . 0.967 no
O32 . H321 . 0.816 no
C37 . C38 . 1.535(8) yes
C37 . Cl41 . 1.755(6) yes
C37 . Cl42 . 1.773(7) yes
C37 . Cl43 . 1.733(7) yes
C38 . O39 . 1.189(6) yes
C38 . O40 . 1.302(7) yes
O40 . H402 . 0.818 no
Cl1 . C4 . 1.625(11) yes
C4 . H42 5_556 0.980 no
C4 . H42 . 0.980 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N14 . H141 . O5 2_657 178 0.89 1.90 2.788(2) yes
O32 . H321 . O4 2_657 167 0.82 1.96 2.762(2) yes
O40 . H402 . O4 3_455 174 0.82 1.74 2.554(2) yes
