#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227174.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_2227174
loop_
_publ_author_name
'Gowda, Ramakrishna'
'Basanagouda, Mahantesha'
'Kulkarni, Manohar V.'
'Gowda, K.V. Arjuna'
_publ_section_title
;
 4-Bromomethyl-6-methoxy-2H-chromen-2-one
;
_journal_coeditor_code           BH2314
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2906
_journal_paper_doi               10.1107/S1600536810042005
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H9 Br O3'
_chemical_formula_moiety         'C11 H9 Br O3'
_chemical_formula_sum            'C11 H9 Br O3'
_chemical_formula_weight         269.09
_chemical_name_systematic
;
4-Bromomethyl-6-methoxy-2H-chromen-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.927(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3573(3)
_cell_length_b                   9.2859(6)
_cell_length_c                   25.2677(17)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.33
_cell_volume                     1021.79(12)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9950
_diffrn_reflns_theta_full        26.58
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.005
_exptl_absorpt_correction_T_max  0.5014
_exptl_absorpt_correction_T_min  0.4343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0467P)²+1.2030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                1501
_reflns_number_total             2128
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2314.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227174
_cod_database_fobs_code          2227174
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.3658(8) 0.2636(4) 0.73840(14) 0.0406(9) Uani d . 1 . .
C C2 0.4641(8) 0.1339(4) 0.71330(13) 0.0375(8) Uani d . 1 . .
H H2 0.3944 0.0462 0.7260 0.045 Uiso calc R 1 . .
C C3 0.6518(7) 0.1332(4) 0.67239(13) 0.0321(7) Uani d . 1 . .
C C4 0.7577(7) 0.2706(4) 0.65171(12) 0.0318(7) Uani d . 1 . .
C C5 0.9489(7) 0.2851(4) 0.60828(13) 0.0348(8) Uani d . 1 . .
H H5 1.0139 0.2035 0.5905 0.042 Uiso calc R 1 . .
C C6 1.0401(7) 0.4188(4) 0.59198(13) 0.0378(9) Uani d . 1 . .
C C7 0.9456(8) 0.5407(4) 0.61872(14) 0.0429(9) Uani d . 1 . .
H H7 1.0121 0.6311 0.6081 0.051 Uiso calc R 1 . .
C C8 0.7556(8) 0.5293(4) 0.66048(14) 0.0401(9) Uani d . 1 . .
H H8 0.6889 0.6113 0.6778 0.048 Uiso calc R 1 . .
C C9 0.6642(7) 0.3941(4) 0.67652(13) 0.0345(8) Uani d . 1 . .
C C10 0.7530(9) -0.0074(4) 0.65024(14) 0.0421(9) Uani d . 1 . .
H H10A 0.7086 -0.0837 0.6751 0.050 Uiso calc R 1 . .
H H10B 0.9733 -0.0052 0.6460 0.050 Uiso calc R 1 . .
C C11 1.2815(9) 0.3270(5) 0.51587(15) 0.0535(11) Uani d . 1 . .
H H11A 1.4005 0.2554 0.5347 0.080 Uiso calc R 1 . .
H H11B 1.3939 0.3612 0.4863 0.080 Uiso calc R 1 . .
H H11C 1.0908 0.2856 0.5033 0.080 Uiso calc R 1 . .
O O1 0.4744(5) 0.3905(3) 0.71899(9) 0.0397(6) Uani d . 1 . .
O O2 0.1939(7) 0.2719(3) 0.77495(11) 0.0569(7) Uani d . 1 . .
O O3 1.2213(6) 0.4438(3) 0.55030(10) 0.0500(7) Uani d . 1 . .
Br Br1 0.54925(10) -0.04981(5) 0.582134(17) 0.0612(2) 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
O2 C1 O1 . . 116.7(3) ?
O2 C1 C2 . . 126.3(4) ?
O1 C1 C2 . . 117.0(3) ?
C3 C2 C1 . . 123.0(3) ?
C3 C2 H2 . . 118.5 ?
C1 C2 H2 . . 118.5 ?
C2 C3 C4 . . 118.7(3) ?
C2 C3 C10 . . 119.3(3) ?
C4 C3 C10 . . 122.0(3) ?
C9 C4 C5 . . 117.9(3) ?
C9 C4 C3 . . 117.6(3) ?
C5 C4 C3 . . 124.5(3) ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
O3 C6 C5 . . 124.7(3) ?
O3 C6 C7 . . 115.4(3) ?
C5 C6 C7 . . 119.9(3) ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 119.0(3) ?
C7 C8 H8 . . 120.5 ?
C9 C8 H8 . . 120.5 ?
C4 C9 C8 . . 122.1(3) ?
C4 C9 O1 . . 122.0(3) ?
C8 C9 O1 . . 115.9(3) ?
C3 C10 Br1 . . 112.1(2) ?
C3 C10 H10A . . 109.2 ?
Br1 C10 H10A . . 109.2 ?
C3 C10 H10B . . 109.2 ?
Br1 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
O3 C11 H11A . . 109.5 ?
O3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C1 O1 C9 . . 121.6(3) ?
C6 O3 C11 . . 118.0(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
C1 O2 . 1.211(4) ?
C1 O1 . 1.367(4) ?
C1 C2 . 1.434(5) ?
C2 C3 . 1.340(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.459(5) ?
C3 C10 . 1.493(5) ?
C4 C9 . 1.375(5) ?
C4 C5 . 1.406(5) ?
C5 C6 . 1.371(5) ?
C5 H5 . 0.9300 ?
C6 O3 . 1.357(4) ?
C6 C7 . 1.388(5) ?
C7 C8 . 1.367(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.382(5) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.377(4) ?
C10 Br1 . 1.950(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O3 . 1.420(5) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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
C2 H2 O1 2_546 0.93 2.60 3.451(4) 152
C2 H2 O2 2_546 0.93 2.58 3.446(5) 155
C10 H10A O2 2_546 0.97 2.57 3.437(5) 148
C8 H8 O2 2_556 0.93 2.56 3.433(5) 156
C10 H10A O1 2_646 0.97 2.98 3.601(4) 122
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
O2 C1 C2 C3 . . . . 179.0(3) ?
O1 C1 C2 C3 . . . . -0.5(5) ?
C1 C2 C3 C4 . . . . -1.0(5) ?
C1 C2 C3 C10 . . . . 177.4(3) ?
C2 C3 C4 C9 . . . . 1.6(4) ?
C10 C3 C4 C9 . . . . -176.7(3) ?
C2 C3 C4 C5 . . . . -178.5(3) ?
C10 C3 C4 C5 . . . . 3.2(5) ?
C9 C4 C5 C6 . . . . 0.7(5) ?
C3 C4 C5 C6 . . . . -179.2(3) ?
C4 C5 C6 O3 . . . . -179.3(3) ?
C4 C5 C6 C7 . . . . 0.5(5) ?
O3 C6 C7 C8 . . . . 178.2(3) ?
C5 C6 C7 C8 . . . . -1.6(5) ?
C6 C7 C8 C9 . . . . 1.4(5) ?
C5 C4 C9 C8 . . . . -0.9(5) ?
C3 C4 C9 C8 . . . . 179.0(3) ?
C5 C4 C9 O1 . . . . 179.3(3) ?
C3 C4 C9 O1 . . . . -0.8(4) ?
C7 C8 C9 C4 . . . . -0.2(5) ?
C7 C8 C9 O1 . . . . 179.6(3) ?
C2 C3 C10 Br1 . . . . 106.3(3) ?
C4 C3 C10 Br1 . . . . -75.4(3) ?
O2 C1 O1 C9 . . . . -178.1(3) ?
C2 C1 O1 C9 . . . . 1.4(5) ?
C4 C9 O1 C1 . . . . -0.8(5) ?
C8 C9 O1 C1 . . . . 179.4(3) ?
C5 C6 O3 C11 . . . . 10.6(5) ?
C7 C6 O3 C11 . . . . -169.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13989553
