#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224528.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_2224528
loop_
_publ_author_name
'Ru, Zong-Ling'
'Wang, Guo-Xi'
_publ_section_title
;
 Methyl 1-bromo-2-naphthoate
;
_journal_coeditor_code           XU2693
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3264
_journal_paper_doi               10.1107/S1600536809050466
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 Br O2'
_chemical_formula_moiety         'C12 H9 Br O2'
_chemical_formula_sum            'C12 H9 Br O2'
_chemical_formula_weight         265.10
_chemical_name_systematic
;
Methyl 1-bromo-2-naphthoate
;
_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                 93.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3614(19)
_cell_length_b                   9.3014(19)
_cell_length_c                   12.069(2)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.09
_cell_volume                     1048.8(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       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  0.0859
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10520
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0519
_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)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                1751
_reflns_number_total             2400
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2693.cif
_cod_data_source_block           I
_cod_original_cell_volume        1048.7(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224528
_cod_database_fobs_code          2224528
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 0.29147(5) 0.80840(4) 0.47073(3) 0.0664(2) Uani d . 1 . .
C C2 0.4234(4) 0.6858(3) 0.4033(3) 0.0450(8) Uani d . 1 . .
C C1 0.5663(4) 0.6855(3) 0.4501(3) 0.0485(9) Uani d . 1 . .
C C4 0.4815(4) 0.5034(4) 0.2735(3) 0.0553(9) Uani d . 1 . .
H H4 0.4533 0.4410 0.2159 0.066 Uiso calc R 1 . .
C C3 0.3790(4) 0.5986(3) 0.3159(3) 0.0471(8) Uani d . 1 . .
C C5 0.6197(5) 0.5021(4) 0.3156(3) 0.0608(10) Uani d . 1 . .
H H5 0.6849 0.4405 0.2852 0.073 Uiso calc R 1 . .
C C6 0.6655(4) 0.5916(4) 0.4039(3) 0.0512(9) Uani d . 1 . .
C C10 0.6150(5) 0.7727(4) 0.5411(3) 0.0596(10) Uani d . 1 . .
H H10 0.5517 0.8347 0.5733 0.072 Uiso calc R 1 . .
C C9 0.7542(5) 0.7662(5) 0.5817(4) 0.0715(12) Uani d . 1 . .
H H9 0.7842 0.8239 0.6417 0.086 Uiso calc R 1 . .
C C8 0.8523(5) 0.6753(5) 0.5355(5) 0.0774(14) Uani d . 1 . .
H H8 0.9468 0.6730 0.5642 0.093 Uiso calc R 1 . .
C C12 0.0587(5) 0.4584(5) 0.1631(4) 0.0812(13) Uani d . 1 . .
H H12A 0.0394 0.3588 0.1475 0.122 Uiso calc R 1 . .
H H12B 0.0531 0.5120 0.0950 0.122 Uiso calc R 1 . .
H H12C -0.0107 0.4948 0.2112 0.122 Uiso calc R 1 . .
C C7 0.8094(5) 0.5901(5) 0.4484(4) 0.0699(12) Uani d . 1 . .
H H7 0.8754 0.5298 0.4174 0.084 Uiso calc R 1 . .
C C11 0.2313(4) 0.5993(4) 0.2617(3) 0.0552(9) Uani d . 1 . .
O O1 0.1996(3) 0.4727(3) 0.2164(2) 0.0678(7) Uani d . 1 . .
O O2 0.1531(4) 0.7005(3) 0.2538(3) 0.0835(10) Uani d . 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'
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
C3 C2 C1 . . 122.4(3) ?
C3 C2 Br1 . . 120.7(3) ?
C1 C2 Br1 . . 116.9(2) ?
C6 C1 C10 . . 118.1(4) ?
C6 C1 C2 . . 118.1(3) ?
C10 C1 C2 . . 123.8(3) ?
C5 C4 C3 . . 121.1(3) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C2 C3 C4 . . 117.8(3) ?
C2 C3 C11 . . 124.1(3) ?
C4 C3 C11 . . 118.1(3) ?
C4 C5 C6 . . 121.2(4) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.4(4) ?
C5 C6 C7 . . 121.4(4) ?
C1 C6 C7 . . 119.3(4) ?
C9 C10 C1 . . 120.4(4) ?
C9 C10 H10 . . 119.8 ?
C1 C10 H10 . . 119.8 ?
C10 C9 C8 . . 121.5(4) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C7 C8 C9 . . 119.7(4) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
O1 C12 H12A . . 109.5 ?
O1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C8 C7 C6 . . 121.0(4) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
O2 C11 O1 . . 123.2(4) ?
O2 C11 C3 . . 125.9(3) ?
O1 C11 C3 . . 110.8(3) ?
C11 O1 C12 . . 116.3(3) ?
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 C2 . 1.901(3) ?
C2 C3 . 1.374(5) ?
C2 C1 . 1.418(5) ?
C1 C6 . 1.415(5) ?
C1 C10 . 1.417(5) ?
C4 C5 . 1.360(5) ?
C4 C3 . 1.425(5) ?
C4 H4 . 0.9300 ?
C3 C11 . 1.491(5) ?
C5 C6 . 1.398(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.418(5) ?
C10 C9 . 1.364(6) ?
C10 H10 . 0.9300 ?
C9 C8 . 1.390(7) ?
C9 H9 . 0.9300 ?
C8 C7 . 1.357(6) ?
C8 H8 . 0.9300 ?
C12 O1 . 1.436(5) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C7 H7 . 0.9300 ?
C11 O2 . 1.193(4) ?
C11 O1 . 1.324(4) ?
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
C3 C2 C1 C6 . . . . 0.2(5) ?
Br1 C2 C1 C6 . . . . 177.9(2) ?
C3 C2 C1 C10 . . . . -179.1(3) ?
Br1 C2 C1 C10 . . . . -1.5(4) ?
C1 C2 C3 C4 . . . . 1.2(5) ?
Br1 C2 C3 C4 . . . . -176.4(2) ?
C1 C2 C3 C11 . . . . -177.7(3) ?
Br1 C2 C3 C11 . . . . 4.7(4) ?
C5 C4 C3 C2 . . . . -2.1(5) ?
C5 C4 C3 C11 . . . . 176.9(4) ?
C3 C4 C5 C6 . . . . 1.6(6) ?
C4 C5 C6 C1 . . . . -0.1(5) ?
C4 C5 C6 C7 . . . . 179.7(4) ?
C10 C1 C6 C5 . . . . 178.6(3) ?
C2 C1 C6 C5 . . . . -0.8(5) ?
C10 C1 C6 C7 . . . . -1.2(5) ?
C2 C1 C6 C7 . . . . 179.4(3) ?
C6 C1 C10 C9 . . . . 0.5(5) ?
C2 C1 C10 C9 . . . . 179.9(4) ?
C1 C10 C9 C8 . . . . 0.3(6) ?
C10 C9 C8 C7 . . . . -0.4(7) ?
C9 C8 C7 C6 . . . . -0.3(7) ?
C5 C6 C7 C8 . . . . -178.7(4) ?
C1 C6 C7 C8 . . . . 1.1(6) ?
C2 C3 C11 O2 . . . . 30.4(6) ?
C4 C3 C11 O2 . . . . -148.5(4) ?
C2 C3 C11 O1 . . . . -153.4(3) ?
C4 C3 C11 O1 . . . . 27.7(4) ?
O2 C11 O1 C12 . . . . -4.8(6) ?
C3 C11 O1 C12 . . . . 178.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9120559
