#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228464.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_2228464
loop_
_publ_author_name
'Gowda, Ramakrishna'
'Gowda, K.V. Arjuna'
'Basanagouda, Mahantesha'
'Kulkarni, Manohar V.'
_publ_section_title
;
 4-Bromomethyl-7,8-dimethylcoumarin
;
_journal_coeditor_code           LH5165
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3352
_journal_paper_doi               10.1107/S1600536810049135
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H11 Br O2'
_chemical_formula_moiety         'C12 H11 Br O2'
_chemical_formula_sum            'C12 H11 Br O2'
_chemical_formula_weight         267.12
_chemical_name_common
;
4-bromomethyl-6,7-dimethyl-2H-chromen-2-one
;
_chemical_name_systematic
;
4-Bromomethyl-7,8-dimethylcoumarin
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 118.908(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.5025(14)
_cell_length_b                   9.8785(7)
_cell_length_c                   13.1639(10)
_cell_measurement_reflns_used    5018
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.4
_cell_volume                     2106.3(3)
_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 PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      292(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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14710
_diffrn_reflns_theta_full        31.85
_diffrn_reflns_theta_max         31.85
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.878
_exptl_absorpt_correction_T_max  0.571
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.780
_refine_diff_density_min         -0.727
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0406
_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)+(0.0574P)²+1.9612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2516
_reflns_number_total             3610
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5165.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228464
_cod_database_fobs_code          2228464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.36207(15) 0.1296(2) 0.0849(2) 0.0332(5) Uani d . 1 . .
C C2 0.39174(15) 0.1512(2) 0.2032(2) 0.0363(5) Uani d . 1 . .
C C3 0.40658(16) 0.2836(3) 0.24674(19) 0.0398(5) Uani d . 1 . .
H H3 0.4263 0.2974 0.3257 0.048 Uiso calc R 1 . .
C C4 0.39291(16) 0.3930(3) 0.17644(19) 0.0366(5) Uani d . 1 . .
H H4 0.4033 0.4797 0.2079 0.044 Uiso calc R 1 . .
C C5 0.36354(14) 0.3756(2) 0.05795(17) 0.0289(4) Uani d . 1 . .
C C6 0.34902(13) 0.2433(2) 0.01547(17) 0.0292(4) Uani d . 1 . .
C C7 0.34654(14) 0.4850(2) -0.02371(18) 0.0303(4) Uani d . 1 . .
C C8 0.31617(15) 0.4562(2) -0.13705(19) 0.0354(5) Uani d . 1 . .
H H8 0.3025 0.5272 -0.1896 0.043 Uiso calc R 1 . .
C C9 0.30411(16) 0.3200(2) -0.1796(2) 0.0371(5) Uani d . 1 . .
C C10 0.34498(19) -0.0090(2) 0.0328(3) 0.0460(6) Uani d . 1 . .
H H10A 0.3014 -0.0043 -0.0461 0.069 Uiso calc R 1 . .
H H10B 0.3287 -0.0674 0.0764 0.069 Uiso calc R 1 . .
H H10C 0.3939 -0.0443 0.0346 0.069 Uiso calc R 1 . .
C C11 0.4099(2) 0.0349(3) 0.2855(3) 0.0530(7) Uani d . 1 . .
H H11A 0.3594 -0.0110 0.2678 0.079 Uiso calc R 1 . .
H H11B 0.4350 0.0684 0.3637 0.079 Uiso calc R 1 . .
H H11C 0.4469 -0.0271 0.2778 0.079 Uiso calc R 1 . .
C C12 0.36044(16) 0.6286(2) 0.0163(2) 0.0383(5) Uani d . 1 . .
H H12A 0.3423 0.6421 0.0734 0.046 Uiso calc R 1 . .
H H12B 0.3287 0.6883 -0.0489 0.046 Uiso calc R 1 . .
O O1 0.32072(11) 0.21805(17) -0.10098(13) 0.0360(4) Uani d . 1 . .
O O2 0.28162(15) 0.2864(2) -0.27881(15) 0.0554(5) Uani d . 1 . .
Br Br1 0.478174(17) 0.67133(3) 0.08473(2) 0.04795(12) 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
C6 C1 C2 . . 117.3(2) ?
C6 C1 C10 . . 120.4(2) ?
C2 C1 C10 . . 122.3(2) ?
C1 C2 C3 . . 119.6(2) ?
C1 C2 C11 . . 121.2(2) ?
C3 C2 C11 . . 119.2(2) ?
C4 C3 C2 . . 121.7(2) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C3 C4 C5 . . 120.4(2) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 117.4(2) ?
C4 C5 C7 . . 124.5(2) ?
C6 C5 C7 . . 118.09(18) ?
O1 C6 C1 . . 115.77(19) ?
O1 C6 C5 . . 120.65(19) ?
C1 C6 C5 . . 123.6(2) ?
C8 C7 C5 . . 119.4(2) ?
C8 C7 C12 . . 120.0(2) ?
C5 C7 C12 . . 120.64(19) ?
C7 C8 C9 . . 122.3(2) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
O2 C9 O1 . . 116.7(2) ?
O2 C9 C8 . . 125.9(2) ?
O1 C9 C8 . . 117.38(19) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 C12 Br1 . . 109.33(17) ?
C7 C12 H12A . . 109.8 ?
Br1 C12 H12A . . 109.8 ?
C7 C12 H12B . . 109.8 ?
Br1 C12 H12B . . 109.8 ?
H12A C12 H12B . . 108.3 ?
C9 O1 C6 . . 122.16(18) ?
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 C6 . 1.393(3) ?
C1 C2 . 1.394(3) ?
C1 C10 . 1.495(3) ?
C2 C3 . 1.401(4) ?
C2 C11 . 1.502(3) ?
C3 C4 . 1.364(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.396(3) ?
C5 C7 . 1.447(3) ?
C6 O1 . 1.382(2) ?
C7 C8 . 1.346(3) ?
C7 C12 . 1.492(3) ?
C8 C9 . 1.433(3) ?
C8 H8 . 0.9300 ?
C9 O2 . 1.210(3) ?
C9 O1 . 1.368(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 Br1 . 1.959(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
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
_geom_hbond_publ_flag
C12 H12B O2 4_554 0.97 2.40 3.342(3) 163 yes
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
C6 C1 C2 C3 . . . . 0.3(4) ?
C10 C1 C2 C3 . . . . 180.0(2) ?
C6 C1 C2 C11 . . . . -178.3(2) ?
C10 C1 C2 C11 . . . . 1.3(4) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C11 C2 C3 C4 . . . . 178.6(3) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . 0.0(4) ?
C3 C4 C5 C7 . . . . 179.5(2) ?
C2 C1 C6 O1 . . . . 179.1(2) ?
C10 C1 C6 O1 . . . . -0.5(3) ?
C2 C1 C6 C5 . . . . -0.4(4) ?
C10 C1 C6 C5 . . . . 180.0(2) ?
C4 C5 C6 O1 . . . . -179.3(2) ?
C7 C5 C6 O1 . . . . 1.2(3) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C7 C5 C6 C1 . . . . -179.3(2) ?
C4 C5 C7 C8 . . . . -178.3(2) ?
C6 C5 C7 C8 . . . . 1.2(3) ?
C4 C5 C7 C12 . . . . 0.3(4) ?
C6 C5 C7 C12 . . . . 179.7(2) ?
C5 C7 C8 C9 . . . . -3.5(4) ?
C12 C7 C8 C9 . . . . 178.0(2) ?
C7 C8 C9 O2 . . . . -175.6(3) ?
C7 C8 C9 O1 . . . . 3.3(4) ?
C8 C7 C12 Br1 . . . . -101.7(2) ?
C5 C7 C12 Br1 . . . . 79.8(2) ?
O2 C9 O1 C6 . . . . 178.2(2) ?
C8 C9 O1 C6 . . . . -0.8(4) ?
C1 C6 O1 C9 . . . . 179.1(2) ?
C5 C6 O1 C9 . . . . -1.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656376
