#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230849.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230849
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Garudachari, B.'
'Isloor, Arun M.'
'Satyanarayan, M. N.'
_publ_section_title
;
 2-(4-Bromophenyl)-2-oxoethyl 4-chlorobenzoate
;
_journal_coeditor_code           RZ2606
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1723
_journal_paper_doi               10.1107/S1600536811022963
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H10 Br Cl O3'
_chemical_formula_moiety         'C15 H10 Br Cl O3'
_chemical_formula_sum            'C15 H10 Br Cl O3'
_chemical_formula_weight         353.59
_chemical_name_systematic
;
2-(4-Bromophenyl)-2-oxoethyl 4-chlorobenzoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   17.1061(11)
_cell_length_b                   5.3062(4)
_cell_length_c                   24.0376(16)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.30
_cell_volume                     2138.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18463
_diffrn_reflns_theta_full        27.31
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_T_max  0.6573
_exptl_absorpt_correction_T_min  0.3640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.538
_refine_ls_abs_structure_details 'Flack (1983), 3590 Friedel pairs'
_refine_ls_abs_structure_Flack   0.065(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8890
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0741P)²+0.4681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                5931
_reflns_number_total             8890
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2606.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230849
_cod_database_fobs_code          2230849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.67824(3) 1.30681(17) 0.56131(3) 0.0834(2) Uani d . 1 1 . .
Cl Cl1A -0.15600(8) 0.7707(5) 0.61298(7) 0.0905(6) Uani d . 1 1 . .
O O1A 0.3290(2) 0.9241(10) 0.63191(17) 0.0841(16) Uani d . 1 1 . .
O O2A 0.1988(2) 1.1811(8) 0.58442(16) 0.0632(10) Uani d . 1 1 . .
O O3A 0.1936(2) 0.8415(10) 0.52826(15) 0.0736(12) Uani d . 1 1 . .
C C1A 0.4376(3) 1.3623(11) 0.56106(19) 0.0501(12) Uani d . 1 1 . .
H H1AA 0.3959 1.4676 0.5447 0.060 Uiso calc R 1 1 . .
C C2A 0.5157(3) 1.4119(11) 0.55351(19) 0.0526(13) Uani d . 1 1 . .
H H2AA 0.5265 1.5531 0.5334 0.063 Uiso calc R 1 1 . .
C C3A 0.5759(3) 1.2477(12) 0.57638(18) 0.0502(13) Uani d . 1 1 . .
C C4A 0.5622(3) 1.0413(15) 0.60918(18) 0.0556(12) Uani d . 1 1 . .
H H4AA 0.6038 0.9348 0.6252 0.067 Uiso calc R 1 1 . .
C C5A 0.4865(3) 0.9992(11) 0.61718(18) 0.0503(12) Uani d . 1 1 . .
H H5AA 0.4771 0.8628 0.6392 0.060 Uiso calc R 1 1 . .
C C6A 0.4229(3) 1.1541(10) 0.59333(17) 0.0462(12) Uani d . 1 1 . .
C C7A 0.3413(3) 1.0949(12) 0.60142(19) 0.0533(15) Uani d . 1 1 . .
C C8A 0.2734(3) 1.2495(13) 0.5706(2) 0.0622(15) Uani d . 1 1 . .
H H8AA 0.2839 1.4259 0.5798 0.075 Uiso calc R 1 1 . .
H H8AB 0.2698 1.2297 0.5300 0.075 Uiso calc R 1 1 . .
C C9A 0.1655(3) 0.9666(12) 0.5602(2) 0.0533(15) Uani d . 1 1 . .
C C10A 0.0870(3) 0.9183(11) 0.57661(18) 0.0471(12) Uani d . 1 1 . .
C C11A 0.0551(3) 1.0787(13) 0.61134(18) 0.0536(13) Uani d . 1 1 . .
H H11A 0.0844 1.2180 0.6271 0.064 Uiso calc R 1 1 . .
C C12A -0.0192(3) 1.0367(17) 0.6231(2) 0.0652(14) Uani d . 1 1 . .
H H12A -0.0405 1.1465 0.6464 0.078 Uiso calc R 1 1 . .
C C13A -0.0615(3) 0.8289(14) 0.5998(2) 0.0604(15) Uani d . 1 1 . .
C C14A -0.0303(3) 0.6605(12) 0.56479(19) 0.0569(14) Uani d . 1 1 . .
H H14A -0.0592 0.5200 0.5493 0.068 Uiso calc R 1 1 . .
C C15A 0.0445(3) 0.7093(13) 0.55400(19) 0.0548(14) Uani d . 1 1 . .
H H15A 0.0665 0.5996 0.5312 0.066 Uiso calc R 1 1 . .
Br Br1B 0.06535(3) 0.5564(2) 0.73157(2) 0.0802(2) Uani d . 1 1 . .
Cl Cl1B 0.92955(6) -0.0329(3) 0.77621(5) 0.0628(4) Uani d . 1 1 . .
O O1B 0.4359(2) 0.0185(11) 0.78999(16) 0.0786(11) Uani d . 1 1 . .
O O2B 0.54903(19) 0.2829(8) 0.75497(14) 0.0627(10) Uani d . 1 1 . .
O O3B 0.5851(2) 0.5857(10) 0.70158(16) 0.0768(12) Uani d . 1 1 . .
C C1B 0.2738(3) 0.1656(11) 0.7806(2) 0.0593(14) Uani d . 1 1 . .
H H1BA 0.2901 0.0219 0.8020 0.071 Uiso calc R 1 1 . .
C C2B 0.1972(3) 0.2425(14) 0.7741(2) 0.0666(17) Uani d . 1 1 . .
H H2BA 0.1620 0.1554 0.7920 0.080 Uiso calc R 1 1 . .
C C3B 0.1714(3) 0.4476(12) 0.74136(18) 0.0525(14) Uani d . 1 1 . .
C C4B 0.2241(3) 0.5826(13) 0.71591(19) 0.0553(14) Uani d . 1 1 . .
H H4BA 0.2066 0.7235 0.6939 0.066 Uiso calc R 1 1 . .
C C5B 0.3026(3) 0.5066(13) 0.72344(19) 0.0552(14) Uani d . 1 1 . .
H H5BA 0.3382 0.5967 0.7065 0.066 Uiso calc R 1 1 . .
C C6B 0.3285(3) 0.2963(12) 0.75623(17) 0.0495(12) Uani d . 1 1 . .
C C7B 0.4133(3) 0.2139(12) 0.76452(19) 0.0579(14) Uani d . 1 1 . .
C C8B 0.4699(3) 0.3840(13) 0.74273(18) 0.0605(16) Uani d . 1 1 . .
H H8BA 0.4527 0.4044 0.7020 0.073 Uiso calc R 1 1 . .
H H8BB 0.4697 0.5487 0.7602 0.073 Uiso calc R 1 1 . .
C C9B 0.6007(3) 0.4055(12) 0.7307(2) 0.0558(14) Uani d . 1 1 . .
C C10B 0.6816(3) 0.2864(12) 0.74456(18) 0.0488(11) Uani d . 1 1 . .
C C11B 0.7416(3) 0.3983(13) 0.7210(2) 0.0677(16) Uani d . 1 1 . .
H H11B 0.7300 0.5398 0.6980 0.081 Uiso calc R 1 1 . .
C C12B 0.8182(3) 0.2997(15) 0.7317(2) 0.0657(15) Uani d . 1 1 . .
H H12B 0.8586 0.3755 0.7168 0.079 Uiso calc R 1 1 . .
C C13B 0.8332(3) 0.0859(12) 0.76505(18) 0.0497(12) Uani d . 1 1 . .
C C14B 0.7754(3) -0.0248(12) 0.78855(18) 0.0545(15) Uani d . 1 1 . .
H H14B 0.7873 -0.1653 0.8118 0.065 Uiso calc R 1 1 . .
C C15B 0.6984(3) 0.0746(13) 0.77740(18) 0.0525(13) Uani d . 1 1 . .
H H15B 0.6584 -0.0031 0.7923 0.063 Uiso calc R 1 1 . .
Br Br1C 0.32100(3) -0.72787(16) 0.94037(3) 0.0849(3) Uani d . 1 1 . .
Cl Cl1C 1.15846(7) -0.2313(4) 0.89129(6) 0.0805(5) Uani d . 1 1 . .
O O1C 0.6700(2) -0.3571(9) 0.86746(17) 0.0800(14) Uani d . 1 1 . .
O O2C 0.7989(2) -0.6225(9) 0.91351(17) 0.0693(12) Uani d . 1 1 . .
O O3C 0.8057(2) -0.2890(10) 0.97126(16) 0.0758(12) Uani d . 1 1 . .
C C1C 0.5592(3) -0.7933(11) 0.93756(19) 0.0515(13) Uani d . 1 1 . .
H H1CA 0.5997 -0.9063 0.9520 0.062 Uiso calc R 1 1 . .
C C2C 0.4832(3) -0.8341(12) 0.9467(2) 0.0552(14) Uani d . 1 1 . .
H H2CA 0.4729 -0.9727 0.9678 0.066 Uiso calc R 1 1 . .
C C3C 0.4234(3) -0.6727(13) 0.92500(19) 0.0533(13) Uani d . 1 1 . .
C C4C 0.4372(3) -0.4662(16) 0.89371(19) 0.0611(14) Uani d . 1 1 . .
H H4CA 0.3958 -0.3569 0.8788 0.073 Uiso calc R 1 1 . .
C C5C 0.5134(3) -0.4232(13) 0.88469(18) 0.0549(13) Uani d . 1 1 . .
H H5CA 0.5231 -0.2843 0.8635 0.066 Uiso calc R 1 1 . .
C C6C 0.5757(3) -0.5854(10) 0.90700(18) 0.0450(12) Uani d . 1 1 . .
C C7C 0.6575(3) -0.5282(11) 0.8977(2) 0.0519(14) Uani d . 1 1 . .
C C8C 0.7228(3) -0.6899(14) 0.9273(2) 0.0642(15) Uani d . 1 1 . .
H H8CA 0.7264 -0.6749 0.9679 0.077 Uiso calc R 1 1 . .
H H8CB 0.7108 -0.8643 0.9168 0.077 Uiso calc R 1 1 . .
C C9C 0.8341(3) -0.4191(13) 0.93900(19) 0.0511(13) Uani d . 1 1 . .
C C10C 0.9124(3) -0.3701(10) 0.92392(18) 0.0482(13) Uani d . 1 1 . .
C C11C 0.9457(3) -0.5376(11) 0.89043(19) 0.0517(13) Uani d . 1 1 . .
H H11C 0.9170 -0.6783 0.8748 0.062 Uiso calc R 1 1 . .
C C12C 1.0218(3) -0.4933(14) 0.8805(2) 0.0573(14) Uani d . 1 1 . .
H H12C 1.0445 -0.6050 0.8585 0.069 Uiso calc R 1 1 . .
C C13C 1.0634(3) -0.2850(12) 0.9034(2) 0.0514(13) Uani d . 1 1 . .
C C14C 1.0313(3) -0.1212(12) 0.9361(2) 0.0566(13) Uani d . 1 1 . .
H H14C 1.0605 0.0188 0.9516 0.068 Uiso calc R 1 1 . .
C C15C 0.9556(3) -0.1613(13) 0.9465(2) 0.0542(13) Uani d . 1 1 . .
H H15C 0.9339 -0.0477 0.9687 0.065 Uiso calc R 1 1 . .
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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9A O2A C8A . . 115.7(5) ?
C6A C1A C2A . . 119.9(5) ?
C6A C1A H1AA . . 120.1 ?
C2A C1A H1AA . . 120.1 ?
C3A C2A C1A . . 118.9(5) ?
C3A C2A H2AA . . 120.6 ?
C1A C2A H2AA . . 120.6 ?
C2A C3A C4A . . 121.8(4) ?
C2A C3A Br1A . . 117.9(4) ?
C4A C3A Br1A . . 120.4(4) ?
C5A C4A C3A . . 118.6(5) ?
C5A C4A H4AA . . 120.7 ?
C3A C4A H4AA . . 120.7 ?
C4A C5A C6A . . 122.0(5) ?
C4A C5A H5AA . . 119.0 ?
C6A C5A H5AA . . 119.0 ?
C5A C6A C1A . . 118.8(4) ?
C5A C6A C7A . . 120.0(5) ?
C1A C6A C7A . . 121.2(5) ?
O1A C7A C6A . . 121.4(5) ?
O1A C7A C8A . . 120.0(4) ?
C6A C7A C8A . . 118.6(5) ?
O2A C8A C7A . . 112.8(5) ?
O2A C8A H8AA . . 109.0 ?
C7A C8A H8AA . . 109.0 ?
O2A C8A H8AB . . 109.0 ?
C7A C8A H8AB . . 109.0 ?
H8AA C8A H8AB . . 107.8 ?
O3A C9A O2A . . 124.0(5) ?
O3A C9A C10A . . 125.1(5) ?
O2A C9A C10A . . 110.8(5) ?
C15A C10A C11A . . 119.6(4) ?
C15A C10A C9A . . 117.7(5) ?
C11A C10A C9A . . 122.6(5) ?
C12A C11A C10A . . 121.2(6) ?
C12A C11A H11A . . 119.4 ?
C10A C11A H11A . . 119.4 ?
C11A C12A C13A . . 118.7(6) ?
C11A C12A H12A . . 120.7 ?
C13A C12A H12A . . 120.7 ?
C12A C13A C14A . . 121.4(4) ?
C12A C13A Cl1A . . 120.1(5) ?
C14A C13A Cl1A . . 118.4(5) ?
C15A C14A C13A . . 118.1(5) ?
C15A C14A H14A . . 120.9 ?
C13A C14A H14A . . 120.9 ?
C10A C15A C14A . . 120.9(5) ?
C10A C15A H15A . . 119.6 ?
C14A C15A H15A . . 119.6 ?
C9B O2B C8B . . 114.3(5) ?
C2B C1B C6B . . 121.4(5) ?
C2B C1B H1BA . . 119.3 ?
C6B C1B H1BA . . 119.3 ?
C1B C2B C3B . . 120.2(5) ?
C1B C2B H2BA . . 119.9 ?
C3B C2B H2BA . . 119.9 ?
C2B C3B C4B . . 120.2(5) ?
C2B C3B Br1B . . 120.8(4) ?
C4B C3B Br1B . . 119.0(4) ?
C5B C4B C3B . . 119.5(6) ?
C5B C4B H4BA . . 120.2 ?
C3B C4B H4BA . . 120.2 ?
C4B C5B C6B . . 120.2(5) ?
C4B C5B H5BA . . 119.9 ?
C6B C5B H5BA . . 119.9 ?
C1B C6B C5B . . 118.4(4) ?
C1B C6B C7B . . 121.2(5) ?
C5B C6B C7B . . 120.4(5) ?
O1B C7B C6B . . 121.1(6) ?
O1B C7B C8B . . 121.6(5) ?
C6B C7B C8B . . 117.2(5) ?
O2B C8B C7B . . 110.8(5) ?
O2B C8B H8BA . . 109.5 ?
C7B C8B H8BA . . 109.5 ?
O2B C8B H8BB . . 109.5 ?
C7B C8B H8BB . . 109.5 ?
H8BA C8B H8BB . . 108.1 ?
O3B C9B O2B . . 124.5(5) ?
O3B C9B C10B . . 124.2(5) ?
O2B C9B C10B . . 111.2(5) ?
C15B C10B C11B . . 119.6(5) ?
C15B C10B C9B . . 123.6(5) ?
C11B C10B C9B . . 116.8(5) ?
C12B C11B C10B . . 120.5(6) ?
C12B C11B H11B . . 119.8 ?
C10B C11B H11B . . 119.8 ?
C13B C12B C11B . . 118.4(5) ?
C13B C12B H12B . . 120.8 ?
C11B C12B H12B . . 120.8 ?
C14B C13B C12B . . 121.8(5) ?
C14B C13B Cl1B . . 121.6(4) ?
C12B C13B Cl1B . . 116.6(4) ?
C13B C14B C15B . . 119.5(5) ?
C13B C14B H14B . . 120.3 ?
C15B C14B H14B . . 120.3 ?
C10B C15B C14B . . 120.2(5) ?
C10B C15B H15B . . 119.9 ?
C14B C15B H15B . . 119.9 ?
C9C O2C C8C . . 116.2(4) ?
C2C C1C C6C . . 120.6(5) ?
C2C C1C H1CA . . 119.7 ?
C6C C1C H1CA . . 119.7 ?
C3C C2C C1C . . 120.2(5) ?
C3C C2C H2CA . . 119.9 ?
C1C C2C H2CA . . 119.9 ?
C2C C3C C4C . . 121.0(4) ?
C2C C3C Br1C . . 119.1(4) ?
C4C C3C Br1C . . 119.9(4) ?
C3C C4C C5C . . 119.1(6) ?
C3C C4C H4CA . . 120.4 ?
C5C C4C H4CA . . 120.4 ?
C4C C5C C6C . . 120.8(6) ?
C4C C5C H5CA . . 119.6 ?
C6C C5C H5CA . . 119.6 ?
C1C C6C C5C . . 118.4(4) ?
C1C C6C C7C . . 122.6(5) ?
C5C C6C C7C . . 119.0(5) ?
O1C C7C C8C . . 121.3(5) ?
O1C C7C C6C . . 121.8(5) ?
C8C C7C C6C . . 116.9(4) ?
O2C C8C C7C . . 112.0(5) ?
O2C C8C H8CA . . 109.2 ?
C7C C8C H8CA . . 109.2 ?
O2C C8C H8CB . . 109.2 ?
C7C C8C H8CB . . 109.2 ?
H8CA C8C H8CB . . 107.9 ?
O3C C9C O2C . . 123.9(5) ?
O3C C9C C10C . . 123.8(6) ?
O2C C9C C10C . . 112.3(5) ?
C15C C10C C11C . . 119.3(4) ?
C15C C10C C9C . . 119.0(5) ?
C11C C10C C9C . . 121.6(5) ?
C12C C11C C10C . . 119.7(5) ?
C12C C11C H11C . . 120.2 ?
C10C C11C H11C . . 120.2 ?
C13C C12C C11C . . 119.8(5) ?
C13C C12C H12C . . 120.1 ?
C11C C12C H12C . . 120.1 ?
C14C C13C C12C . . 120.8(5) ?
C14C C13C Cl1C . . 119.5(5) ?
C12C C13C Cl1C . . 119.7(4) ?
C13C C14C C15C . . 120.4(5) ?
C13C C14C H14C . . 119.8 ?
C15C C14C H14C . . 119.8 ?
C10C C15C C14C . . 120.0(5) ?
C10C C15C H15C . . 120.0 ?
C14C C15C H15C . . 120.0 ?
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
Br1A C3A . 1.884(4) ?
Cl1A C13A . 1.735(5) ?
O1A C7A . 1.210(7) ?
O2A C9A . 1.351(7) ?
O2A C8A . 1.428(6) ?
O3A C9A . 1.187(6) ?
C1A C6A . 1.401(7) ?
C1A C2A . 1.409(6) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.376(7) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.396(9) ?
C4A C5A . 1.366(6) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.392(7) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.481(6) ?
C7A C8A . 1.493(7) ?
C8A H8AA . 0.9700 ?
C8A H8AB . 0.9700 ?
C9A C10A . 1.495(6) ?
C10A C15A . 1.377(8) ?
C10A C11A . 1.379(7) ?
C11A C12A . 1.375(6) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.375(10) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.405(8) ?
C14A C15A . 1.379(7) ?
C14A H14A . 0.9300 ?
C15A H15A . 0.9300 ?
Br1B C3B . 1.873(5) ?
Cl1B C13B . 1.735(5) ?
O1B C7B . 1.227(8) ?
O2B C9B . 1.324(7) ?
O2B C8B . 1.431(5) ?
O3B C9B . 1.183(7) ?
C1B C2B . 1.351(7) ?
C1B C6B . 1.387(7) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.364(9) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.385(7) ?
C4B C5B . 1.379(6) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.387(8) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.488(7) ?
C7B C8B . 1.493(9) ?
C8B H8BA . 0.9700 ?
C8B H8BB . 0.9700 ?
C9B C10B . 1.497(7) ?
C10B C15B . 1.370(8) ?
C10B C11B . 1.401(7) ?
C11B C12B . 1.386(8) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.384(9) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.365(6) ?
C14B C15B . 1.395(6) ?
C14B H14B . 0.9300 ?
C15B H15B . 0.9300 ?
Br1C C3C . 1.884(4) ?
Cl1C C13C . 1.732(5) ?
O1C C7C . 1.208(6) ?
O2C C9C . 1.325(8) ?
O2C C8C . 1.451(5) ?
O3C C9C . 1.210(6) ?
C1C C2C . 1.378(6) ?
C1C C6C . 1.386(7) ?
C1C H1CA . 0.9300 ?
C2C C3C . 1.356(8) ?
C2C H2CA . 0.9300 ?
C3C C4C . 1.376(10) ?
C4C C5C . 1.382(6) ?
C4C H4CA . 0.9300 ?
C5C C6C . 1.392(7) ?
C5C H5CA . 0.9300 ?
C6C C7C . 1.491(6) ?
C7C C8C . 1.474(8) ?
C8C H8CA . 0.9700 ?
C8C H8CB . 0.9700 ?
C9C C10C . 1.477(6) ?
C10C C15C . 1.382(8) ?
C10C C11C . 1.395(7) ?
C11C C12C . 1.390(6) ?
C11C H11C . 0.9300 ?
C12C C13C . 1.368(9) ?
C12C H12C . 0.9300 ?
C13C C14C . 1.358(7) ?
C14C C15C . 1.383(7) ?
C14C H14C . 0.9300 ?
C15C H15C . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5A H5AA O3B . 0.93 2.59 3.227(7) 126 yes
C5B H5BA O1A . 0.93 2.48 3.217(7) 136 yes
C15B H15B O1C . 0.93 2.59 3.254(7) 129 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A C3A . . . . 2.5(7) ?
C1A C2A C3A C4A . . . . -3.3(8) ?
C1A C2A C3A Br1A . . . . 175.9(4) ?
C2A C3A C4A C5A . . . . 1.8(8) ?
Br1A C3A C4A C5A . . . . -177.3(4) ?
C3A C4A C5A C6A . . . . 0.5(8) ?
C4A C5A C6A C1A . . . . -1.3(8) ?
C4A C5A C6A C7A . . . . 177.7(5) ?
C2A C1A C6A C5A . . . . -0.2(7) ?
C2A C1A C6A C7A . . . . -179.2(5) ?
C5A C6A C7A O1A . . . . 5.4(8) ?
C1A C6A C7A O1A . . . . -175.7(5) ?
C5A C6A C7A C8A . . . . -174.0(5) ?
C1A C6A C7A C8A . . . . 4.9(7) ?
C9A O2A C8A C7A . . . . -76.3(6) ?
O1A C7A C8A O2A . . . . 3.6(8) ?
C6A C7A C8A O2A . . . . -177.0(5) ?
C8A O2A C9A O3A . . . . -1.7(7) ?
C8A O2A C9A C10A . . . . -178.6(4) ?
O3A C9A C10A C15A . . . . 1.5(8) ?
O2A C9A C10A C15A . . . . 178.3(5) ?
O3A C9A C10A C11A . . . . -176.0(5) ?
O2A C9A C10A C11A . . . . 0.8(7) ?
C15A C10A C11A C12A . . . . -1.2(8) ?
C9A C10A C11A C12A . . . . 176.3(5) ?
C10A C11A C12A C13A . . . . 0.5(9) ?
C11A C12A C13A C14A . . . . 0.2(9) ?
C11A C12A C13A Cl1A . . . . -179.3(5) ?
C12A C13A C14A C15A . . . . -0.2(8) ?
Cl1A C13A C14A C15A . . . . 179.3(4) ?
C11A C10A C15A C14A . . . . 1.2(8) ?
C9A C10A C15A C14A . . . . -176.4(5) ?
C13A C14A C15A C10A . . . . -0.5(8) ?
C6B C1B C2B C3B . . . . 2.3(9) ?
C1B C2B C3B C4B . . . . -1.9(9) ?
C1B C2B C3B Br1B . . . . 179.8(5) ?
C2B C3B C4B C5B . . . . 0.7(8) ?
Br1B C3B C4B C5B . . . . 179.1(4) ?
C3B C4B C5B C6B . . . . 0.1(8) ?
C2B C1B C6B C5B . . . . -1.5(8) ?
C2B C1B C6B C7B . . . . 178.7(5) ?
C4B C5B C6B C1B . . . . 0.3(8) ?
C4B C5B C6B C7B . . . . -179.9(5) ?
C1B C6B C7B O1B . . . . 4.9(8) ?
C5B C6B C7B O1B . . . . -174.8(5) ?
C1B C6B C7B C8B . . . . -172.6(5) ?
C5B C6B C7B C8B . . . . 7.7(7) ?
C9B O2B C8B C7B . . . . 171.7(4) ?
O1B C7B C8B O2B . . . . 1.1(7) ?
C6B C7B C8B O2B . . . . 178.6(4) ?
C8B O2B C9B O3B . . . . 0.8(8) ?
C8B O2B C9B C10B . . . . -179.0(4) ?
O3B C9B C10B C15B . . . . -178.7(6) ?
O2B C9B C10B C15B . . . . 1.2(7) ?
O3B C9B C10B C11B . . . . -0.2(8) ?
O2B C9B C10B C11B . . . . 179.6(5) ?
C15B C10B C11B C12B . . . . -1.5(9) ?
C9B C10B C11B C12B . . . . -180.0(5) ?
C10B C11B C12B C13B . . . . 1.4(9) ?
C11B C12B C13B C14B . . . . -1.7(9) ?
C11B C12B C13B Cl1B . . . . 179.0(5) ?
C12B C13B C14B C15B . . . . 2.0(8) ?
Cl1B C13B C14B C15B . . . . -178.7(4) ?
C11B C10B C15B C14B . . . . 1.8(8) ?
C9B C10B C15B C14B . . . . -179.8(5) ?
C13B C14B C15B C10B . . . . -2.0(8) ?
C6C C1C C2C C3C . . . . 1.0(8) ?
C1C C2C C3C C4C . . . . -0.1(8) ?
C1C C2C C3C Br1C . . . . -178.0(4) ?
C2C C3C C4C C5C . . . . -0.3(8) ?
Br1C C3C C4C C5C . . . . 177.5(4) ?
C3C C4C C5C C6C . . . . -0.2(8) ?
C2C C1C C6C C5C . . . . -1.6(7) ?
C2C C1C C6C C7C . . . . 177.8(5) ?
C4C C5C C6C C1C . . . . 1.2(7) ?
C4C C5C C6C C7C . . . . -178.3(5) ?
C1C C6C C7C O1C . . . . 174.4(5) ?
C5C C6C C7C O1C . . . . -6.2(7) ?
C1C C6C C7C C8C . . . . -5.8(7) ?
C5C C6C C7C C8C . . . . 173.6(5) ?
C9C O2C C8C C7C . . . . 77.1(6) ?
O1C C7C C8C O2C . . . . -2.3(8) ?
C6C C7C C8C O2C . . . . 178.0(4) ?
C8C O2C C9C O3C . . . . -1.4(8) ?
C8C O2C C9C C10C . . . . 178.1(4) ?
O3C C9C C10C C15C . . . . -1.6(8) ?
O2C C9C C10C C15C . . . . 178.9(5) ?
O3C C9C C10C C11C . . . . 174.3(5) ?
O2C C9C C10C C11C . . . . -5.2(7) ?
C15C C10C C11C C12C . . . . 0.4(7) ?
C9C C10C C11C C12C . . . . -175.5(5) ?
C10C C11C C12C C13C . . . . -0.5(8) ?
C11C C12C C13C C14C . . . . 0.5(8) ?
C11C C12C C13C Cl1C . . . . 179.6(4) ?
C12C C13C C14C C15C . . . . -0.6(8) ?
Cl1C C13C C14C C15C . . . . -179.7(4) ?
C11C C10C C15C C14C . . . . -0.4(7) ?
C9C C10C C15C C14C . . . . 175.6(5) ?
C13C C14C C15C C10C . . . . 0.5(8) ?
