#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226181.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_2226181
loop_
_publ_author_name
'Mitsui, Ryosuke'
'Watanabe, Shoji'
'Nagasawa, Atsushi'
'Okamoto, Akiko'
'Yonezawa, Noriyuki'
_publ_section_title
;
 (4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone
;
_journal_coeditor_code           IS2542
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1304
_journal_paper_doi               10.1107/S1600536810015527
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H11 Br2 Cl O3'
_chemical_formula_moiety         'C18 H11 Br2 Cl O3'
_chemical_formula_sum            'C18 H11 Br2 Cl O3'
_chemical_formula_weight         470.54
_chemical_melting_point_gt       455.0
_chemical_melting_point_lt       455.5
_chemical_name_systematic
;
(4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.6750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1513(2)
_cell_length_b                   10.06343(18)
_cell_length_c                   13.8936(3)
_cell_measurement_reflns_used    28732
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.3
_cell_volume                     1650.80(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29373
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    7.845
_exptl_absorpt_correction_T_max  0.308
_exptl_absorpt_correction_T_min  0.189
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.643
_refine_ls_extinction_coef       0.0162(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0279
_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)+(0.0457P)²+0.9314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                2940
_reflns_number_total             3022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2542.cif
_cod_data_source_block           I
_cod_original_cell_volume        1650.79(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226181
_cod_database_fobs_code          2226181
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.348845(18) 0.93221(2) 0.140206(18) 0.02724(13) Uani d . 1 . .
Br Br2 -0.250748(19) 0.77531(3) 0.077383(18) 0.03487(13) Uani d . 1 . .
Cl Cl1 0.49341(5) 0.85290(6) 0.59621(4) 0.03239(17) Uani d . 1 . .
O O1 0.18770(16) 0.61119(18) 0.17108(14) 0.0377(4) Uani d . 1 . .
O O2 -0.02937(15) 0.63660(18) 0.11024(13) 0.0357(4) Uani d . 1 . .
H H2O 0.0329 0.5982 0.1198 0.043 Uiso d R 1 . .
O O3 0.33774(13) 1.21262(15) 0.17994(12) 0.0256(3) Uani d . 1 . .
C C1 0.09899(18) 0.8215(2) 0.14949(15) 0.0222(4) Uani d . 1 . .
C C2 -0.0097(2) 0.7676(2) 0.11910(17) 0.0264(5) Uani d . 1 . .
C C3 -0.10526(18) 0.8529(3) 0.10204(16) 0.0268(5) Uani d . 1 . .
C C4 -0.09270(18) 0.9868(3) 0.10944(16) 0.0268(5) Uani d . 1 . .
H H4 -0.1579 1.0417 0.1004 0.032 Uiso calc R 1 . .
C C5 0.01632(18) 1.0458(2) 0.13047(16) 0.0232(5) Uani d . 1 . .
C C6 0.02945(19) 1.1856(2) 0.13389(17) 0.0266(5) Uani d . 1 . .
H H6 -0.0361 1.2402 0.1217 0.032 Uiso calc R 1 . .
C C7 0.1339(2) 1.2440(2) 0.15434(17) 0.0259(5) Uani d . 1 . .
H H7 0.1408 1.3377 0.1617 0.031 Uiso calc R 1 . .
C C8 0.23139(18) 1.1645(2) 0.16441(15) 0.0216(4) Uani d . 1 . .
C C9 0.21941(17) 1.0276(2) 0.15487(15) 0.0198(4) Uani d . 1 . .
C C10 0.11426(18) 0.9635(2) 0.14633(15) 0.0203(4) Uani d . 1 . .
C C11 0.18698(19) 0.7270(2) 0.20076(17) 0.0249(5) Uani d . 1 . .
C C12 0.26347(18) 0.7639(2) 0.29783(17) 0.0229(5) Uani d . 1 . .
C C13 0.23528(18) 0.8631(2) 0.35778(16) 0.0238(5) Uani d . 1 . .
H H13 0.1678 0.9131 0.3351 0.029 Uiso calc R 1 . .
C C14 0.30470(19) 0.8895(2) 0.45010(17) 0.0261(5) Uani d . 1 . .
H H14 0.2846 0.9559 0.4914 0.031 Uiso calc R 1 . .
C C15 0.40403(18) 0.8174(2) 0.48129(16) 0.0242(5) Uani d . 1 . .
C C16 0.43420(19) 0.7176(2) 0.42328(18) 0.0278(5) Uani d . 1 . .
H H16 0.5024 0.6689 0.4458 0.033 Uiso calc R 1 . .
C C17 0.36288(19) 0.6908(2) 0.33217(18) 0.0268(5) Uani d . 1 . .
H H17 0.3816 0.6217 0.2922 0.032 Uiso calc R 1 . .
C C18 0.3525(2) 1.3542(2) 0.18675(19) 0.0318(5) Uani d . 1 . .
H H18A 0.4326 1.3760 0.1936 0.038 Uiso calc R 1 . .
H H18B 0.3279 1.3873 0.2446 0.038 Uiso calc R 1 . .
H H18C 0.3071 1.3960 0.1267 0.038 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 O2 H2O . . 107.9 ?
C8 O3 C18 . . 117.81(18) ?
C2 C1 C10 . . 119.6(2) ?
C2 C1 C11 . . 114.8(2) ?
C10 C1 C11 . . 124.52(19) ?
O2 C2 C1 . . 123.0(2) ?
O2 C2 C3 . . 117.3(2) ?
C1 C2 C3 . . 119.6(2) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 Br2 . . 120.53(18) ?
C2 C3 Br2 . . 118.32(18) ?
C3 C4 C5 . . 121.0(2) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 121.0(2) ?
C6 C5 C10 . . 119.3(2) ?
C4 C5 C10 . . 119.6(2) ?
C7 C6 C5 . . 121.8(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 119.6(2) ?
C6 C7 H7 . . 120.2 ?
C8 C7 H7 . . 120.2 ?
O3 C8 C9 . . 116.51(19) ?
O3 C8 C7 . . 124.3(2) ?
C9 C8 C7 . . 119.2(2) ?
C8 C9 C10 . . 122.30(19) ?
C8 C9 Br1 . . 116.24(16) ?
C10 C9 Br1 . . 121.15(17) ?
C9 C10 C5 . . 117.0(2) ?
C9 C10 C1 . . 124.8(2) ?
C5 C10 C1 . . 118.17(19) ?
O1 C11 C1 . . 120.4(2) ?
O1 C11 C12 . . 118.9(2) ?
C1 C11 C12 . . 119.97(19) ?
C13 C12 C17 . . 119.2(2) ?
C13 C12 C11 . . 122.0(2) ?
C17 C12 C11 . . 118.7(2) ?
C14 C13 C12 . . 120.6(2) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 118.9(2) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C14 C15 C16 . . 121.7(2) ?
C14 C15 Cl1 . . 119.13(18) ?
C16 C15 Cl1 . . 119.13(18) ?
C17 C16 C15 . . 118.6(2) ?
C17 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C16 C17 C12 . . 120.9(2) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
O3 C18 H18A . . 109.5 ?
O3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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
Br1 C9 . 1.894(2) ?
Br2 C3 . 1.888(2) ?
Cl1 C15 . 1.743(2) ?
O1 C11 . 1.237(3) ?
O2 C2 . 1.340(3) ?
O2 H2O . 0.8326 ?
O3 C8 . 1.349(3) ?
O3 C18 . 1.437(3) ?
C1 C2 . 1.398(3) ?
C1 C10 . 1.443(3) ?
C1 C11 . 1.481(3) ?
C2 C3 . 1.418(3) ?
C3 C4 . 1.357(4) ?
C4 C5 . 1.418(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.415(3) ?
C5 C10 . 1.424(3) ?
C6 C7 . 1.366(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.408(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.388(3) ?
C9 C10 . 1.411(3) ?
C11 C12 . 1.492(3) ?
C12 C13 . 1.394(3) ?
C12 C17 . 1.398(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.390(3) ?
C16 C17 . 1.381(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
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
O2 H2O O1 0.83 1.85 2.585(3) 146
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
C10 C1 C2 O2 . . . . 172.9(2) ?
C11 C1 C2 O2 . . . . -18.3(3) ?
C10 C1 C2 C3 . . . . -10.9(3) ?
C11 C1 C2 C3 . . . . 157.8(2) ?
O2 C2 C3 C4 . . . . -180.0(2) ?
C1 C2 C3 C4 . . . . 3.7(3) ?
O2 C2 C3 Br2 . . . . 4.2(3) ?
C1 C2 C3 Br2 . . . . -172.17(16) ?
C2 C3 C4 C5 . . . . 2.6(3) ?
Br2 C3 C4 C5 . . . . 178.36(16) ?
C3 C4 C5 C6 . . . . 177.2(2) ?
C3 C4 C5 C10 . . . . -1.5(3) ?
C4 C5 C6 C7 . . . . 179.8(2) ?
C10 C5 C6 C7 . . . . -1.6(3) ?
C5 C6 C7 C8 . . . . 5.3(3) ?
C18 O3 C8 C9 . . . . 177.92(19) ?
C18 O3 C8 C7 . . . . 0.1(3) ?
C6 C7 C8 O3 . . . . 176.8(2) ?
C6 C7 C8 C9 . . . . -1.0(3) ?
O3 C8 C9 C10 . . . . 174.84(18) ?
C7 C8 C9 C10 . . . . -7.2(3) ?
O3 C8 C9 Br1 . . . . -11.4(2) ?
C7 C8 C9 Br1 . . . . 166.54(16) ?
C8 C9 C10 C5 . . . . 10.7(3) ?
Br1 C9 C10 C5 . . . . -162.76(15) ?
C8 C9 C10 C1 . . . . -171.3(2) ?
Br1 C9 C10 C1 . . . . 15.2(3) ?
C6 C5 C10 C9 . . . . -6.2(3) ?
C4 C5 C10 C9 . . . . 172.45(18) ?
C6 C5 C10 C1 . . . . 175.64(19) ?
C4 C5 C10 C1 . . . . -5.7(3) ?
C2 C1 C10 C9 . . . . -166.1(2) ?
C11 C1 C10 C9 . . . . 26.3(3) ?
C2 C1 C10 C5 . . . . 11.9(3) ?
C11 C1 C10 C5 . . . . -155.7(2) ?
C2 C1 C11 O1 . . . . 40.3(3) ?
C10 C1 C11 O1 . . . . -151.6(2) ?
C2 C1 C11 C12 . . . . -129.7(2) ?
C10 C1 C11 C12 . . . . 38.5(3) ?
O1 C11 C12 C13 . . . . -149.6(2) ?
C1 C11 C12 C13 . . . . 20.5(3) ?
O1 C11 C12 C17 . . . . 26.3(3) ?
C1 C11 C12 C17 . . . . -163.6(2) ?
C17 C12 C13 C14 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 176.0(2) ?
C12 C13 C14 C15 . . . . 1.3(3) ?
C13 C14 C15 C16 . . . . -1.5(3) ?
C13 C14 C15 Cl1 . . . . 178.49(17) ?
C14 C15 C16 C17 . . . . 0.2(3) ?
Cl1 C15 C16 C17 . . . . -179.73(18) ?
C15 C16 C17 C12 . . . . 1.2(3) ?
C13 C12 C17 C16 . . . . -1.4(3) ?
C11 C12 C17 C16 . . . . -177.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744989
