#------------------------------------------------------------------------------
#$Date: 2020-07-03 04:16:45 +0300 (Fri, 03 Jul 2020) $
#$Revision: 253683 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558478.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_1558478
loop_
_publ_author_name
'Vik, Erik C.'
'Li, Ping'
'Maier, Josef M.'
'Madukwe, Daniel O.'
'Rassolov, Vitaly A.'
'Pellechia, Perry J.'
'Masson, Eric'
'Shimizu, Ken D.'
_publ_section_title
;
 Large Transition State Stabilization from a Weak Hydrogen Bond
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02806A
_journal_year                    2020
_chemical_formula_moiety         'C15 H12 Cl N O3'
_chemical_formula_sum            'C15 H12 Cl N O3'
_chemical_formula_weight         289.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.3570(9)
_cell_length_b                   6.8190(3)
_cell_length_c                   20.0691(8)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.34
_cell_volume                     2648.72(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            61497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        30.053
_diffrn_reflns_theta_max         30.053
_diffrn_reflns_theta_min         2.240
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9558.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²+2.2210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5865
_reflns_number_total             7769
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02806a2.cif
_cod_data_source_block           ecv1_169
_cod_database_code               1558478
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.843
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C3A(H3AA), C6A(H6A), C7A(H7A), C2B(H2B), C3B(H3BA), C6B(H6B),
 C7B(H7B)
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB)
2.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C13A(H13A), C15A(H15A), C8B(H8B), C9B(H9B),
 C12B(H12B), C13B(H13B), C15B(H15B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl -0.15625(2) 0.39535(7) -0.03546(2) 0.02570(10) Uani 1 1 d . . . . .
O1A O 0.03967(6) 0.60561(17) 0.28361(6) 0.0215(2) Uani 1 1 d . . . . .
O2A O 0.09291(6) 0.12408(15) 0.15938(6) 0.0178(2) Uani 1 1 d . . . . .
O3A O 0.10465(5) 0.73673(17) 0.17648(6) 0.0170(2) Uani 1 1 d . . . . .
H3A H 0.1073(12) 0.860(4) 0.1677(12) 0.042(6) Uiso 1 1 d . . . . .
N1A N 0.06056(6) 0.38804(17) 0.20807(6) 0.0117(2) Uani 1 1 d . . . . .
C1A C 0.22137(8) 0.1929(3) 0.40673(9) 0.0270(4) Uani 1 1 d . . . . .
H1AA H 0.200195 0.097685 0.428332 0.032 Uiso 1 1 calc R . . . .
H1AB H 0.271237 0.207965 0.438884 0.032 Uiso 1 1 calc R . . . .
C2A C 0.18267(8) 0.3903(3) 0.38725(8) 0.0212(3) Uani 1 1 d . . . . .
H2A H 0.184913 0.472008 0.429581 0.025 Uiso 1 1 calc R . . . .
C3A C 0.10926(7) 0.3123(2) 0.33392(8) 0.0158(3) Uani 1 1 d . . . . .
H3AA H 0.083604 0.261495 0.362040 0.019 Uiso 1 1 calc R . . . .
C4A C 0.06609(7) 0.4562(2) 0.27592(8) 0.0142(3) Uani 1 1 d . . . . .
C5A C 0.09236(7) 0.2095(2) 0.21260(8) 0.0133(3) Uani 1 1 d . . . . .
C6A C 0.12571(7) 0.1459(2) 0.29190(8) 0.0155(3) Uani 1 1 d . . . . .
H6A H 0.106867 0.017409 0.299171 0.019 Uiso 1 1 calc R . . . .
C7A C 0.20684(8) 0.1443(3) 0.32641(9) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.228930 0.022413 0.318617 0.026 Uiso 1 1 calc R . . . .
C8A C 0.22829(8) 0.3343(3) 0.30355(9) 0.0230(3) Uani 1 1 d . . . . .
H8A H 0.248523 0.347756 0.269766 0.028 Uiso 1 1 calc R . . . .
C9A C 0.21392(8) 0.4796(3) 0.33896(9) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.221798 0.615202 0.334786 0.027 Uiso 1 1 calc R . . . .
C10A C 0.02064(7) 0.4864(2) 0.14046(7) 0.0126(3) Uani 1 1 d . . . . .
C11A C 0.04347(7) 0.6662(2) 0.12643(8) 0.0136(3) Uani 1 1 d . . . . .
C12A C 0.00264(8) 0.7636(2) 0.06117(8) 0.0170(3) Uani 1 1 d . . . . .
H12A H 0.017033 0.887323 0.050867 0.020 Uiso 1 1 calc R . . . .
C13A C -0.05861(8) 0.6816(2) 0.01135(8) 0.0182(3) Uani 1 1 d . . . . .
H13A H -0.085984 0.748096 -0.033118 0.022 Uiso 1 1 calc R . . . .
C14A C -0.07962(7) 0.5020(2) 0.02687(8) 0.0169(3) Uani 1 1 d . . . . .
C15A C -0.04076(7) 0.4028(2) 0.09121(8) 0.0150(3) Uani 1 1 d . . . . .
H15A H -0.055730 0.280012 0.101524 0.018 Uiso 1 1 calc R . . . .
Cl1B Cl 0.77046(2) 0.60461(7) 0.38056(2) 0.03096(11) Uani 1 1 d . . . . .
O1B O 0.46656(6) 0.40827(18) 0.22035(6) 0.0237(3) Uani 1 1 d . . . . .
O2B O 0.56202(6) 0.84935(16) 0.12018(6) 0.0204(2) Uani 1 1 d . . . . .
O3B O 0.54561(6) 0.23881(17) 0.12759(6) 0.0194(2) Uani 1 1 d . . . . .
H3B H 0.5544(12) 0.115(4) 0.1205(13) 0.044(7) Uiso 1 1 d . . . . .
N1B N 0.52635(6) 0.60110(18) 0.17306(6) 0.0135(2) Uani 1 1 d . . . . .
C1B C 0.32658(8) 0.7723(3) 0.02126(9) 0.0266(4) Uani 1 1 d . . . . .
H1BA H 0.311740 0.879097 0.044768 0.032 Uiso 1 1 calc R . . . .
H1BB H 0.289991 0.743716 -0.028277 0.032 Uiso 1 1 calc R . . . .
C2B C 0.35102(8) 0.5889(3) 0.06975(9) 0.0231(3) Uani 1 1 d . . . . .
H2B H 0.314747 0.515262 0.078594 0.028 Uiso 1 1 calc R . . . .
C3B C 0.41003(7) 0.6830(2) 0.13912(8) 0.0175(3) Uani 1 1 d . . . . .
H3BA H 0.390940 0.748123 0.171211 0.021 Uiso 1 1 calc R . . . .
C4B C 0.46762(7) 0.5450(2) 0.18265(8) 0.0159(3) Uani 1 1 d . . . . .
C5B C 0.51649(8) 0.7704(2) 0.13212(8) 0.0157(3) Uani 1 1 d . . . . .
C6B C 0.44230(8) 0.8339(2) 0.10602(8) 0.0180(3) Uani 1 1 d . . . . .
H6B H 0.438971 0.969767 0.122989 0.022 Uiso 1 1 calc R . . . .
C7B C 0.39771(8) 0.8112(3) 0.02091(9) 0.0230(3) Uani 1 1 d . . . . .
H7B H 0.400005 0.921941 -0.010640 0.028 Uiso 1 1 calc R . . . .
C8B C 0.41322(8) 0.6087(3) 0.00067(9) 0.0254(4) Uani 1 1 d . . . . .
H8B H 0.437942 0.580494 -0.027966 0.031 Uiso 1 1 calc R . . . .
C9B C 0.38637(8) 0.4781(3) 0.02978(9) 0.0254(4) Uani 1 1 d . . . . .
H9B H 0.388793 0.339568 0.026275 0.030 Uiso 1 1 calc R . . . .
C10B C 0.59131(7) 0.5036(2) 0.20910(8) 0.0140(3) Uani 1 1 d . . . . .
C11B C 0.59965(7) 0.3172(2) 0.18537(8) 0.0159(3) Uani 1 1 d . . . . .
C12B C 0.66289(8) 0.2226(2) 0.22195(9) 0.0198(3) Uani 1 1 d . . . . .
H12B H 0.669696 0.096580 0.205943 0.024 Uiso 1 1 calc R . . . .
C13B C 0.71599(8) 0.3100(3) 0.28140(9) 0.0220(3) Uani 1 1 d . . . . .
H13B H 0.758990 0.244699 0.306076 0.026 Uiso 1 1 calc R . . . .
C14B C 0.70559(7) 0.4942(2) 0.30446(8) 0.0200(3) Uani 1 1 d . . . . .
C15B C 0.64385(7) 0.5927(2) 0.26862(8) 0.0170(3) Uani 1 1 d . . . . .
H15B H 0.637471 0.719376 0.284466 0.020 Uiso 1 1 calc R . . . .
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 0.0000 0.0000 '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 0.0060 '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
C11A O3A H3A 108.6(15) . . ?
C4A N1A C10A 122.73(12) . . ?
C5A N1A C4A 113.19(12) . . ?
C5A N1A C10A 123.86(12) . . ?
H1AA C1A H1AB 110.3 . . ?
C2A C1A H1AA 112.9 . . ?
C2A C1A H1AB 112.9 . . ?
C2A C1A C7A 94.20(12) . . ?
C7A C1A H1AA 112.9 . . ?
C7A C1A H1AB 112.9 . . ?
C1A C2A H2A 116.3 . . ?
C1A C2A C3A 98.67(13) . . ?
C3A C2A H2A 116.3 . . ?
C9A C2A C1A 100.31(13) . . ?
C9A C2A H2A 116.3 . . ?
C9A C2A C3A 106.41(12) . . ?
C2A C3A H3AA 111.1 . . ?
C4A C3A C2A 114.52(13) . . ?
C4A C3A H3AA 111.1 . . ?
C4A C3A C6A 105.32(11) . . ?
C6A C3A C2A 103.28(12) . . ?
C6A C3A H3AA 111.1 . . ?
O1A C4A N1A 123.72(13) . . ?
O1A C4A C3A 128.27(13) . . ?
N1A C4A C3A 108.01(12) . . ?
O2A C5A N1A 123.39(13) . . ?
O2A C5A C6A 127.71(13) . . ?
N1A C5A C6A 108.88(12) . . ?
C3A C6A H6A 111.5 . . ?
C3A C6A C7A 103.18(12) . . ?
C5A C6A C3A 104.53(12) . . ?
C5A C6A H6A 111.5 . . ?
C5A C6A C7A 114.10(12) . . ?
C7A C6A H6A 111.5 . . ?
C1A C7A C6A 98.99(12) . . ?
C1A C7A H7A 116.2 . . ?
C6A C7A H7A 116.2 . . ?
C8A C7A C1A 100.37(14) . . ?
C8A C7A C6A 106.27(12) . . ?
C8A C7A H7A 116.2 . . ?
C7A C8A H8A 126.0 . . ?
C9A C8A C7A 108.01(14) . . ?
C9A C8A H8A 126.0 . . ?
C2A C9A H9A 126.1 . . ?
C8A C9A C2A 107.82(15) . . ?
C8A C9A H9A 126.1 . . ?
C11A C10A N1A 119.11(12) . . ?
C15A C10A N1A 119.25(13) . . ?
C15A C10A C11A 121.62(13) . . ?
O3A C11A C10A 118.22(13) . . ?
O3A C11A C12A 123.39(14) . . ?
C10A C11A C12A 118.38(13) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.65(14) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A C12A 119.46(14) . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A Cl1A 120.17(11) . . ?
C15A C14A Cl1A 118.53(12) . . ?
C15A C14A C13A 121.30(14) . . ?
C10A C15A H15A 120.7 . . ?
C14A C15A C10A 118.58(14) . . ?
C14A C15A H15A 120.7 . . ?
C11B O3B H3B 110.5(15) . . ?
C4B N1B C10B 122.53(12) . . ?
C5B N1B C4B 112.96(12) . . ?
C5B N1B C10B 124.16(12) . . ?
H1BA C1B H1BB 110.3 . . ?
C2B C1B H1BA 112.9 . . ?
C2B C1B H1BB 112.9 . . ?
C2B C1B C7B 94.09(12) . . ?
C7B C1B H1BA 112.9 . . ?
C7B C1B H1BB 112.9 . . ?
C1B C2B H2B 116.1 . . ?
C1B C2B C3B 99.20(14) . . ?
C3B C2B H2B 116.1 . . ?
C9B C2B C1B 100.53(14) . . ?
C9B C2B H2B 116.1 . . ?
C9B C2B C3B 106.33(12) . . ?
C2B C3B H3BA 111.1 . . ?
C4B C3B C2B 114.44(13) . . ?
C4B C3B H3BA 111.1 . . ?
C4B C3B C6B 105.32(11) . . ?
C6B C3B C2B 103.26(12) . . ?
C6B C3B H3BA 111.1 . . ?
O1B C4B N1B 123.54(14) . . ?
O1B C4B C3B 128.39(13) . . ?
N1B C4B C3B 108.06(12) . . ?
O2B C5B N1B 123.50(13) . . ?
O2B C5B C6B 127.81(14) . . ?
N1B C5B C6B 108.69(12) . . ?
C3B C6B H6B 111.3 . . ?
C3B C6B C7B 103.13(12) . . ?
C5B C6B C3B 104.79(12) . . ?
C5B C6B H6B 111.3 . . ?
C5B C6B C7B 114.47(12) . . ?
C7B C6B H6B 111.3 . . ?
C1B C7B C6B 99.03(12) . . ?
C1B C7B H7B 116.4 . . ?
C6B C7B H7B 116.4 . . ?
C8B C7B C1B 99.88(14) . . ?
C8B C7B C6B 106.28(12) . . ?
C8B C7B H7B 116.4 . . ?
C7B C8B H8B 125.9 . . ?
C9B C8B C7B 108.11(15) . . ?
C9B C8B H8B 125.9 . . ?
C2B C9B H9B 126.1 . . ?
C8B C9B C2B 107.71(16) . . ?
C8B C9B H9B 126.1 . . ?
C11B C10B N1B 119.21(13) . . ?
C15B C10B N1B 119.43(13) . . ?
C15B C10B C11B 121.32(13) . . ?
O3B C11B C10B 117.83(13) . . ?
O3B C11B C12B 123.66(14) . . ?
C12B C11B C10B 118.51(14) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B C11B 120.84(15) . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B H13B 120.4 . . ?
C12B C13B C14B 119.20(14) . . ?
C14B C13B H13B 120.4 . . ?
C13B C14B Cl1B 120.24(12) . . ?
C15B C14B Cl1B 118.51(13) . . ?
C15B C14B C13B 121.25(14) . . ?
C10B C15B H15B 120.6 . . ?
C14B C15B C10B 118.86(14) . . ?
C14B C15B H15B 120.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C14A 1.7439(15) . ?
O1A C4A 1.2057(18) . ?
O2A C5A 1.2209(18) . ?
O3A H3A 0.86(3) . ?
O3A C11A 1.3555(17) . ?
N1A C4A 1.3958(18) . ?
N1A C5A 1.3784(18) . ?
N1A C10A 1.4283(17) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.541(2) . ?
C1A C7A 1.543(2) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.571(2) . ?
C2A C9A 1.517(2) . ?
C3A H3AA 1.0000 . ?
C3A C4A 1.504(2) . ?
C3A C6A 1.540(2) . ?
C5A C6A 1.507(2) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.571(2) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.509(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.328(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.392(2) . ?
C10A C15A 1.3876(19) . ?
C11A C12A 1.397(2) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.385(2) . ?
C14A C15A 1.381(2) . ?
C15A H15A 0.9500 . ?
Cl1B C14B 1.7407(16) . ?
O1B C4B 1.2071(19) . ?
O2B C5B 1.2205(18) . ?
O3B H3B 0.89(3) . ?
O3B C11B 1.3532(18) . ?
N1B C4B 1.4003(18) . ?
N1B C5B 1.3806(19) . ?
N1B C10B 1.4287(18) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.534(2) . ?
C1B C7B 1.545(2) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.567(2) . ?
C2B C9B 1.515(2) . ?
C3B H3BA 1.0000 . ?
C3B C4B 1.501(2) . ?
C3B C6B 1.537(2) . ?
C5B C6B 1.507(2) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.573(2) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.515(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.322(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.395(2) . ?
C10B C15B 1.386(2) . ?
C11B C12B 1.393(2) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.386(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.388(2) . ?
C14B C15B 1.380(2) . ?
C15B H15B 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3A H3A O2A 0.86(3) 1.83(3) 2.6617(16) 163(2) 1_565 yes
O3B H3B O2B 0.89(3) 1.82(3) 2.6911(16) 166(2) 1_545 yes
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
Cl1A C14A C15A C10A 179.26(11) . . . . ?
O2A C5A C6A C3A 178.78(14) . . . . ?
O2A C5A C6A C7A 66.8(2) . . . . ?
O3A C11A C12A C13A 178.42(13) . . . . ?
N1A C5A C6A C3A -0.06(15) . . . . ?
N1A C5A C6A C7A -112.02(14) . . . . ?
N1A C10A C11A O3A 2.87(19) . . . . ?
N1A C10A C11A C12A -177.87(12) . . . . ?
N1A C10A C15A C14A 178.46(12) . . . . ?
C1A C2A C3A C4A -151.66(13) . . . . ?
C1A C2A C3A C6A -37.71(14) . . . . ?
C1A C2A C9A C8A 32.41(16) . . . . ?
C1A C7A C8A C9A -32.97(16) . . . . ?
C2A C1A C7A C6A -59.31(14) . . . . ?
C2A C1A C7A C8A 49.18(13) . . . . ?
C2A C3A C4A O1A -70.0(2) . . . . ?
C2A C3A C4A N1A 110.12(14) . . . . ?
C2A C3A C6A C5A -118.84(12) . . . . ?
C2A C3A C6A C7A 0.76(14) . . . . ?
C3A C2A C9A C8A -69.91(16) . . . . ?
C3A C6A C7A C1A 36.39(15) . . . . ?
C3A C6A C7A C8A -67.26(15) . . . . ?
C4A N1A C5A O2A 179.39(13) . . . . ?
C4A N1A C5A C6A -1.71(16) . . . . ?
C4A N1A C10A C11A 69.99(17) . . . . ?
C4A N1A C10A C15A -108.46(16) . . . . ?
C4A C3A C6A C5A 1.61(14) . . . . ?
C4A C3A C6A C7A 121.21(12) . . . . ?
C5A N1A C4A O1A -177.09(13) . . . . ?
C5A N1A C4A C3A 2.78(16) . . . . ?
C5A N1A C10A C11A -115.78(15) . . . . ?
C5A N1A C10A C15A 65.77(18) . . . . ?
C5A C6A C7A C1A 149.17(13) . . . . ?
C5A C6A C7A C8A 45.51(17) . . . . ?
C6A C3A C4A O1A 177.25(14) . . . . ?
C6A C3A C4A N1A -2.63(15) . . . . ?
C6A C7A C8A C9A 69.67(16) . . . . ?
C7A C1A C2A C3A 59.69(13) . . . . ?
C7A C1A C2A C9A -48.86(14) . . . . ?
C7A C8A C9A C2A 0.38(17) . . . . ?
C9A C2A C3A C4A -48.14(17) . . . . ?
C9A C2A C3A C6A 65.80(15) . . . . ?
C10A N1A C4A O1A -2.3(2) . . . . ?
C10A N1A C4A C3A 177.57(12) . . . . ?
C10A N1A C5A O2A 4.7(2) . . . . ?
C10A N1A C5A C6A -176.43(12) . . . . ?
C10A C11A C12A C13A -0.8(2) . . . . ?
C11A C10A C15A C14A 0.1(2) . . . . ?
C11A C12A C13A C14A 0.5(2) . . . . ?
C12A C13A C14A Cl1A -179.51(11) . . . . ?
C12A C13A C14A C15A 0.1(2) . . . . ?
C13A C14A C15A C10A -0.4(2) . . . . ?
C15A C10A C11A O3A -178.72(13) . . . . ?
C15A C10A C11A C12A 0.5(2) . . . . ?
Cl1B C14B C15B C10B -178.39(11) . . . . ?
O2B C5B C6B C3B -178.69(15) . . . . ?
O2B C5B C6B C7B 69.1(2) . . . . ?
O3B C11B C12B C13B -179.22(14) . . . . ?
N1B C5B C6B C3B 1.78(16) . . . . ?
N1B C5B C6B C7B -110.45(15) . . . . ?
N1B C10B C11B O3B 1.47(19) . . . . ?
N1B C10B C11B C12B -178.84(13) . . . . ?
N1B C10B C15B C14B 177.90(13) . . . . ?
C1B C2B C3B C4B -151.44(13) . . . . ?
C1B C2B C3B C6B -37.53(14) . . . . ?
C1B C2B C9B C8B 32.44(16) . . . . ?
C1B C7B C8B C9B -33.34(16) . . . . ?
C2B C1B C7B C6B -59.01(14) . . . . ?
C2B C1B C7B C8B 49.40(14) . . . . ?
C2B C3B C4B O1B -70.6(2) . . . . ?
C2B C3B C4B N1B 109.73(14) . . . . ?
C2B C3B C6B C5B -119.62(13) . . . . ?
C2B C3B C6B C7B 0.47(15) . . . . ?
C3B C2B C9B C8B -70.51(16) . . . . ?
C3B C6B C7B C1B 36.40(15) . . . . ?
C3B C6B C7B C8B -66.74(15) . . . . ?
C4B N1B C5B O2B 176.53(14) . . . . ?
C4B N1B C5B C6B -3.91(17) . . . . ?
C4B N1B C10B C11B 73.15(18) . . . . ?
C4B N1B C10B C15B -104.42(17) . . . . ?
C4B C3B C6B C5B 0.73(15) . . . . ?
C4B C3B C6B C7B 120.82(13) . . . . ?
C5B N1B C4B O1B -175.36(14) . . . . ?
C5B N1B C4B C3B 4.38(17) . . . . ?
C5B N1B C10B C11B -114.03(16) . . . . ?
C5B N1B C10B C15B 68.40(19) . . . . ?
C5B C6B C7B C1B 149.62(14) . . . . ?
C5B C6B C7B C8B 46.47(18) . . . . ?
C6B C3B C4B O1B 176.76(16) . . . . ?
C6B C3B C4B N1B -2.96(16) . . . . ?
C6B C7B C8B C9B 69.18(16) . . . . ?
C7B C1B C2B C3B 59.44(14) . . . . ?
C7B C1B C2B C9B -49.21(14) . . . . ?
C7B C8B C9B C2B 0.76(17) . . . . ?
C9B C2B C3B C4B -47.53(17) . . . . ?
C9B C2B C3B C6B 66.38(16) . . . . ?
C10B N1B C4B O1B -1.8(2) . . . . ?
C10B N1B C4B C3B 177.93(13) . . . . ?
C10B N1B C5B O2B 3.1(2) . . . . ?
C10B N1B C5B C6B -177.34(13) . . . . ?
C10B C11B C12B C13B 1.1(2) . . . . ?
C11B C10B C15B C14B 0.4(2) . . . . ?
C11B C12B C13B C14B 0.0(2) . . . . ?
C12B C13B C14B Cl1B 178.16(12) . . . . ?
C12B C13B C14B C15B -1.0(2) . . . . ?
C13B C14B C15B C10B 0.8(2) . . . . ?
C15B C10B C11B O3B 178.99(13) . . . . ?
C15B C10B C11B C12B -1.3(2) . . . . ?
