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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228052.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_2228052
loop_
_publ_author_name
'Kato, Yuichi'
'Nagasawa, Atsushi'
'Kataoka, Kotaro'
'Okamoto, Akiko'
'Yonezawa, Noriyuki'
_publ_section_title
;
 (4-Bromophenyl)(3,6-dimethoxy-2-naphthyl)methanone
;
_journal_coeditor_code           VM2049
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2795
_journal_paper_doi               10.1107/S160053681004016X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H15 Br O3'
_chemical_formula_moiety         'C19 H15 Br O3'
_chemical_formula_sum            'C19 H15 Br O3'
_chemical_formula_weight         371.22
_chemical_melting_point_gt       416.9
_chemical_melting_point_lt       419.5
_chemical_name_systematic
;
(4-Bromophenyl)(3,6-dimethoxy-2-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                 105.9710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.88917(14)
_cell_length_b                   21.0182(4)
_cell_length_c                   10.06272(18)
_cell_measurement_reflns_used    26572
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      4.2
_cell_volume                     1604.16(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29541
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.21
_diffrn_standards_number         29541
_exptl_absorpt_coefficient_mu    3.598
_exptl_absorpt_correction_T_max  0.5331
_exptl_absorpt_correction_T_min  0.1609
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.431
_refine_diff_density_min         -1.025
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.6344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2767
_reflns_number_total             2934
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2049.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228052
_cod_database_fobs_code          2228052
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.24719(3) 0.056869(10) 0.494126(19) 0.03961(11) Uani d . 1 . .
O O1 -0.46425(17) 0.28009(7) -0.69867(14) 0.0406(3) Uani d . 1 . .
O O2 0.20106(17) 0.19970(6) -0.05734(13) 0.0342(3) Uani d . 1 . .
O O3 0.24997(19) 0.03129(7) -0.18371(14) 0.0405(3) Uani d . 1 . .
C C1 -0.3611(2) 0.24042(10) -0.6033(2) 0.0324(4) Uani d . 1 . .
C C2 -0.3738(3) 0.17558(10) -0.6441(2) 0.0384(4) Uani d . 1 . .
H H2 -0.4485 0.1636 -0.7292 0.046 Uiso calc R 1 . .
C C3 -0.2762(3) 0.13090(10) -0.5582(2) 0.0375(4) Uani d . 1 . .
H H3 -0.2853 0.0885 -0.5854 0.045 Uiso calc R 1 . .
C C4 -0.1608(2) 0.14784(9) -0.4282(2) 0.0302(4) Uani d . 1 . .
C C5 -0.0537(2) 0.10319(9) -0.33881(19) 0.0303(4) Uani d . 1 . .
H H5 -0.0616 0.0605 -0.3643 0.036 Uiso calc R 1 . .
C C6 0.0620(2) 0.12056(9) -0.21526(18) 0.0284(4) Uani d . 1 . .
C C7 0.0759(2) 0.18618(9) -0.17702(18) 0.0279(4) Uani d . 1 . .
C C8 -0.0283(2) 0.23056(9) -0.26096(19) 0.0284(4) Uani d . 1 . .
H H8 -0.0198 0.2730 -0.2340 0.034 Uiso calc R 1 . .
C C9 -0.1488(2) 0.21296(9) -0.38808(19) 0.0278(4) Uani d . 1 . .
C C10 -0.2524(2) 0.25890(10) -0.47798(19) 0.0303(4) Uani d . 1 . .
H H10 -0.2466 0.3015 -0.4520 0.036 Uiso calc R 1 . .
C C11 0.1740(2) 0.06982(9) -0.1299(2) 0.0308(4) Uani d . 1 . .
C C12 0.1884(2) 0.06594(8) 0.02077(19) 0.0291(4) Uani d . 1 . .
C C13 0.0583(2) 0.09052(9) 0.0753(2) 0.0349(4) Uani d . 1 . .
H H13 -0.0401 0.1100 0.0169 0.042 Uiso calc R 1 . .
C C14 0.0731(3) 0.08652(9) 0.2154(2) 0.0363(4) Uani d . 1 . .
H H14 -0.0155 0.1024 0.2509 0.044 Uiso calc R 1 . .
C C15 0.2217(3) 0.05857(8) 0.3014(2) 0.0312(4) Uani d . 1 . .
C C16 0.3515(3) 0.03239(10) 0.2499(2) 0.0370(4) Uani d . 1 . .
H H16 0.4493 0.0127 0.3087 0.044 Uiso calc R 1 . .
C C17 0.3339(3) 0.03590(10) 0.1099(2) 0.0358(4) Uani d . 1 . .
H H17 0.4200 0.0180 0.0743 0.043 Uiso calc R 1 . .
C C18 -0.4465(3) 0.34656(10) -0.6723(2) 0.0454(5) Uani d . 1 . .
H H18A -0.5287 0.3692 -0.7451 0.055 Uiso calc R 1 . .
H H18B -0.3286 0.3596 -0.6683 0.055 Uiso calc R 1 . .
H H18C -0.4704 0.3558 -0.5857 0.055 Uiso calc R 1 . .
C C19 0.2347(2) 0.26549(10) -0.0224(2) 0.0348(4) Uani d . 1 . .
H H19A 0.3294 0.2689 0.0609 0.042 Uiso calc R 1 . .
H H19B 0.1305 0.2847 -0.0086 0.042 Uiso calc R 1 . .
H H19C 0.2667 0.2869 -0.0962 0.042 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'
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
C1 O1 C18 . . 117.51(15) ?
C7 O2 C19 . . 117.30(14) ?
O1 C1 C10 . . 125.22(19) ?
O1 C1 C2 . . 113.82(17) ?
C10 C1 C2 . . 120.96(17) ?
C3 C2 C1 . . 119.73(18) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 121.30(19) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 122.78(18) ?
C5 C4 C9 . . 118.58(16) ?
C3 C4 C9 . . 118.61(17) ?
C6 C5 C4 . . 122.20(17) ?
C6 C5 H5 . . 118.9 ?
C4 C5 H5 . . 118.9 ?
C5 C6 C7 . . 118.89(16) ?
C5 C6 C11 . . 118.06(17) ?
C7 C6 C11 . . 122.98(16) ?
O2 C7 C8 . . 124.72(16) ?
O2 C7 C6 . . 115.05(15) ?
C8 C7 C6 . . 120.19(16) ?
C7 C8 C9 . . 121.22(17) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C8 C9 C10 . . 121.58(18) ?
C8 C9 C4 . . 118.88(16) ?
C10 C9 C4 . . 119.50(17) ?
C1 C10 C9 . . 119.90(19) ?
C1 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
O3 C11 C12 . . 120.38(17) ?
O3 C11 C6 . . 120.23(18) ?
C12 C11 C6 . . 119.37(16) ?
C13 C12 C17 . . 118.65(18) ?
C13 C12 C11 . . 121.55(16) ?
C17 C12 C11 . . 119.78(17) ?
C14 C13 C12 . . 121.02(17) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C15 C14 C13 . . 118.84(18) ?
C15 C14 H14 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
C14 C15 C16 . . 121.49(18) ?
C14 C15 Br1 . . 118.80(15) ?
C16 C15 Br1 . . 119.71(14) ?
C17 C16 C15 . . 119.00(17) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C16 C17 C12 . . 120.94(18) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 C15 . 1.8942(19) ?
O1 C1 . 1.359(2) ?
O1 C18 . 1.422(3) ?
O2 C7 . 1.361(2) ?
O2 C19 . 1.433(2) ?
O3 C11 . 1.219(2) ?
C1 C10 . 1.372(3) ?
C1 C2 . 1.419(3) ?
C2 C3 . 1.362(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.419(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.409(3) ?
C4 C9 . 1.423(3) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.428(3) ?
C6 C11 . 1.496(3) ?
C7 C8 . 1.370(3) ?
C8 C9 . 1.417(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.418(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.491(3) ?
C12 C13 . 1.390(3) ?
C12 C17 . 1.398(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.383(3) ?
C16 C17 . 1.379(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
C19 H19A O1 1_656 0.96 2.53 3.477(2) 170
C5 H5 Br 3 0.93 2.98 3.8441(18) 155
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
C18 O1 C1 C10 . . . . 6.0(3) ?
C18 O1 C1 C2 . . . . -173.88(17) ?
O1 C1 C2 C3 . . . . 179.56(18) ?
C10 C1 C2 C3 . . . . -0.3(3) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . -177.87(19) ?
C2 C3 C4 C9 . . . . 0.2(3) ?
C3 C4 C5 C6 . . . . 177.68(18) ?
C9 C4 C5 C6 . . . . -0.3(3) ?
C4 C5 C6 C7 . . . . -0.9(3) ?
C4 C5 C6 C11 . . . . -178.08(17) ?
C19 O2 C7 C8 . . . . -4.8(2) ?
C19 O2 C7 C6 . . . . 172.93(15) ?
C5 C6 C7 O2 . . . . -176.14(16) ?
C11 C6 C7 O2 . . . . 0.9(2) ?
C5 C6 C7 C8 . . . . 1.7(3) ?
C11 C6 C7 C8 . . . . 178.79(16) ?
O2 C7 C8 C9 . . . . 176.31(16) ?
C6 C7 C8 C9 . . . . -1.4(3) ?
C7 C8 C9 C10 . . . . -177.62(16) ?
C7 C8 C9 C4 . . . . 0.1(3) ?
C5 C4 C9 C8 . . . . 0.8(3) ?
C3 C4 C9 C8 . . . . -177.36(17) ?
C5 C4 C9 C10 . . . . 178.52(16) ?
C3 C4 C9 C10 . . . . 0.4(3) ?
O1 C1 C10 C9 . . . . -178.98(17) ?
C2 C1 C10 C9 . . . . 0.9(3) ?
C8 C9 C10 C1 . . . . 176.76(17) ?
C4 C9 C10 C1 . . . . -0.9(2) ?
C5 C6 C11 O3 . . . . 46.0(3) ?
C7 C6 C11 O3 . . . . -131.1(2) ?
C5 C6 C11 C12 . . . . -132.63(18) ?
C7 C6 C11 C12 . . . . 50.3(2) ?
O3 C11 C12 C13 . . . . -154.64(19) ?
C6 C11 C12 C13 . . . . 24.0(3) ?
O3 C11 C12 C17 . . . . 24.1(3) ?
C6 C11 C12 C17 . . . . -157.30(19) ?
C17 C12 C13 C14 . . . . 1.1(3) ?
C11 C12 C13 C14 . . . . 179.87(18) ?
C12 C13 C14 C15 . . . . 1.2(3) ?
C13 C14 C15 C16 . . . . -2.7(3) ?
C13 C14 C15 Br1 . . . . 176.93(15) ?
C14 C15 C16 C17 . . . . 1.8(3) ?
Br1 C15 C16 C17 . . . . -177.86(15) ?
C15 C16 C17 C12 . . . . 0.7(3) ?
C13 C12 C17 C16 . . . . -2.1(3) ?
C11 C12 C17 C16 . . . . 179.15(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231330
2 PubChem 91130960
