#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/17/2231735.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_2231735
loop_
_publ_author_name
'Huang, Xing'
'Ren, Li-Hong'
'Yin, Rong-Hua'
'Gao, Feng'
_publ_section_title
;
 4-Benzyloxy-2-bromo-1-methoxybenzene
;
_journal_coeditor_code           XU5279
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2330
_journal_paper_doi               10.1107/S1600536811031989
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H13 Br O2'
_chemical_formula_moiety         'C14 H13 Br O2'
_chemical_formula_sum            'C14 H13 Br O2'
_chemical_formula_weight         293.15
_chemical_name_systematic        4-Benzyloxy-2-bromo-1-methoxybenzene
_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                 94.401(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1415(7)
_cell_length_b                   8.2635(7)
_cell_length_c                   25.287(2)
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3116
_cell_measurement_theta_min      2.933
_cell_volume                     1279.5(2)
_computing_cell_refinement       'CrysAlis PRO CCD (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO CCD (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO CCD (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            3982
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    3.199
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.85911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0554
_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)+(0.1035P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                2610
_reflns_number_total             3982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5279.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231735
_cod_database_fobs_code          2231735
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_symmetry_multiplicity
Br Br1 0.52954(11) 0.35775(8) 0.77207(3) 0.0720(3) Uani d . 1 1
O O1 0.1613(7) 0.1331(5) 0.78343(15) 0.0634(11) Uani d . 1 1
O O2 0.6766(7) 0.1821(5) 0.97133(16) 0.0691(13) Uani d . 1 1
C C1 0.2856(9) 0.1387(7) 0.8308(2) 0.0509(14) Uani d . 1 1
C C2 0.4647(9) 0.2388(6) 0.8329(2) 0.0478(14) Uani d . 1 1
C C3 0.6002(10) 0.2562(6) 0.8784(2) 0.0535(16) Uani d . 1 1
H H3 0.7197 0.3254 0.8788 0.064 Uiso calc R 1 1
C C4 0.5592(11) 0.1714(6) 0.9233(2) 0.0547(16) Uani d . 1 1
C C5 0.3786(10) 0.0679(7) 0.9211(2) 0.0605(16) Uani d . 1 1
H H5 0.3478 0.0097 0.9511 0.073 Uiso calc R 1 1
C C6 0.2472(10) 0.0511(6) 0.8754(2) 0.0548(16) Uani d . 1 1
H H6 0.1301 -0.0204 0.8744 0.066 Uiso calc R 1 1
C C7 -0.0252(9) 0.0291(9) 0.7806(2) 0.080(2) Uani d . 1 1
H H7A -0.1048 0.0410 0.7467 0.120 Uiso calc R 1 1
H H7C -0.1177 0.0575 0.8081 0.120 Uiso calc R 1 1
H H7B 0.0217 -0.0812 0.7852 0.120 Uiso calc R 1 1
C C8 0.8485(11) 0.2936(8) 0.9758(3) 0.0695(19) Uani d . 1 1
H H8B 0.7976 0.3985 0.9628 0.083 Uiso calc R 1 1
H H8A 0.9648 0.2583 0.9546 0.083 Uiso calc R 1 1
C C9 0.9321(11) 0.3061(7) 1.0329(2) 0.0573(16) Uani d . 1 1
C C10 1.1363(11) 0.2430(7) 1.0508(3) 0.0678(19) Uani d . 1 1
H H10 1.2196 0.1869 1.0276 0.081 Uiso calc R 1 1
C C11 1.2111(11) 0.2643(8) 1.1021(3) 0.072(2) Uani d . 1 1
H H11 1.3478 0.2234 1.1135 0.087 Uiso calc R 1 1
C C12 1.0936(13) 0.3434(8) 1.1375(3) 0.0714(19) Uani d . 1 1
H H12 1.1467 0.3536 1.1728 0.086 Uiso calc R 1 1
C C13 0.8960(13) 0.4075(7) 1.1202(3) 0.075(2) Uani d . 1 1
H H13 0.8154 0.4652 1.1435 0.091 Uiso calc R 1 1
C C14 0.8152(12) 0.3870(7) 1.0678(3) 0.0700(19) Uani d . 1 1
H H14 0.6792 0.4292 1.0566 0.084 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'
Br Br -0.2901 2.4595 '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
O1 C1 C2 116.4(5)
O1 C1 C6 125.4(5)
O1 C7 H7A 109.5
O1 C7 H7C 109.5
O1 C7 H7B 109.5
O2 C4 C3 125.7(6)
O2 C4 C5 116.0(5)
O2 C8 H8B 109.9
O2 C8 H8A 109.9
O2 C8 C9 108.9(5)
C1 O1 C7 117.0(4)
C1 C2 Br1 119.9(4)
C1 C2 C3 121.8(5)
C1 C6 H6 119.6
C2 C1 C6 118.1(5)
C2 C3 H3 120.0
C3 C2 Br1 118.3(4)
C3 C4 C5 118.3(6)
C4 O2 C8 117.2(5)
C4 C3 C2 120.1(6)
C4 C3 H3 120.0
C4 C5 H5 119.6
C5 C6 C1 120.9(5)
C5 C6 H6 119.6
C6 C5 C4 120.8(5)
C6 C5 H5 119.6
H7A C7 H7C 109.5
H7A C7 H7B 109.5
H7C C7 H7B 109.5
H8B C8 H8A 108.3
C9 C8 H8B 109.9
C9 C8 H8A 109.9
C9 C10 H10 120.3
C9 C14 C13 120.9(7)
C9 C14 H14 119.6
C10 C9 C8 121.1(6)
C10 C11 H11 118.8
C10 C11 C12 122.4(6)
C11 C10 C9 119.3(6)
C11 C10 H10 120.3
C11 C12 H12 120.7
C11 C12 C13 118.6(7)
C12 C11 H11 118.8
C12 C13 H13 119.9
C12 C13 C14 120.2(7)
C13 C12 H12 120.7
C13 C14 H14 119.6
C14 C9 C8 120.2(6)
C14 C9 C10 118.6(6)
C14 C13 H13 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.893(5)
O1 C1 1.370(6)
O1 C7 1.430(7)
O2 C4 1.367(7)
O2 C8 1.399(7)
C1 C2 1.374(7)
C1 C6 1.377(8)
C2 C3 1.375(8)
C3 H3 0.9300
C3 C4 1.374(8)
C4 C5 1.398(8)
C5 H5 0.9300
C5 C6 1.364(8)
C6 H6 0.9300
C7 H7A 0.9600
C7 H7C 0.9600
C7 H7B 0.9600
C8 H8B 0.9700
C8 H8A 0.9700
C8 C9 1.499(8)
C9 C10 1.401(9)
C9 C14 1.356(9)
C10 H10 0.9300
C10 C11 1.354(9)
C11 H11 0.9300
C11 C12 1.360(9)
C12 H12 0.9300
C12 C13 1.365(9)
C13 H13 0.9300
C13 C14 1.387(9)
C14 H14 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
C5 H5 O2 3_657 0.93 2.54 3.453(7) 169
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
Br1 C2 C3 C4 -179.7(4)
O1 C1 C2 Br1 -0.7(7)
O1 C1 C2 C3 179.1(5)
O1 C1 C6 C5 -178.6(5)
O2 C4 C5 C6 178.5(6)
O2 C8 C9 C10 109.0(7)
O2 C8 C9 C14 -74.4(7)
C1 C2 C3 C4 0.5(9)
C2 C1 C6 C5 2.4(9)
C2 C3 C4 O2 -177.7(5)
C2 C3 C4 C5 0.3(9)
C3 C4 C5 C6 0.3(9)
C4 O2 C8 C9 170.9(5)
C4 C5 C6 C1 -1.7(9)
C6 C1 C2 Br1 178.4(4)
C6 C1 C2 C3 -1.8(8)
C7 O1 C1 C2 179.8(5)
C7 O1 C1 C6 0.9(8)
C8 O2 C4 C3 2.6(9)
C8 O2 C4 C5 -175.4(5)
C8 C9 C10 C11 176.5(6)
C8 C9 C14 C13 -176.3(6)
C9 C10 C11 C12 1.0(11)
C10 C9 C14 C13 0.2(9)
C10 C11 C12 C13 -2.0(11)
C11 C12 C13 C14 2.1(10)
C12 C13 C14 C9 -1.3(10)
C14 C9 C10 C11 -0.1(9)
