#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226459.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_2226459
loop_
_publ_author_name
'Haridharan, N.'
'Ramkumar, V.'
'Dhamodharan, R.'
_publ_section_title
;
 2-Oxo-4-trifluoromethyl-2H-chromen-7-yl
 2-bromo-2-methylpropanoate
;
_journal_coeditor_code           HB5450
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1606
_journal_paper_doi               10.1107/S1600536810020234
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H10 Br F3 O4'
_chemical_formula_moiety         'C14 H10 Br F3 O4'
_chemical_formula_sum            'C14 H10 Br F3 O4'
_chemical_formula_weight         379.13
_chemical_name_systematic
;
2-Oxo-4-trifluoromethyl-2H-chromen-7-yl 2-bromo-2-methylpropanoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.982(2)
_cell_angle_beta                 91.797(2)
_cell_angle_gamma                104.387(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1842(4)
_cell_length_b                   11.0297(6)
_cell_length_c                   11.0619(7)
_cell_measurement_reflns_used    3404
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.43
_cell_volume                     717.61(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9951
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.80
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    2.913
_exptl_absorpt_correction_T_max  0.5415
_exptl_absorpt_correction_T_min  0.3887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.853
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0395
_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)+(0.0464P)²+0.4480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                2390
_reflns_number_total             3796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5450.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               2226459
_cod_database_fobs_code          2226459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.06908(6) -0.04175(3) 0.29516(4) 0.06662(16) Uani d . 1 . .
C C1 0.2614(5) 0.5339(3) -0.2219(3) 0.0450(7) Uani d . 1 . .
C C2 0.4147(5) 0.4806(3) -0.2966(3) 0.0450(7) Uani d . 1 . .
H H2 0.4574 0.5118 -0.3675 0.054 Uiso calc R 1 . .
C C3 0.4972(4) 0.3873(3) -0.2666(2) 0.0363(6) Uani d . 1 . .
C C4 0.4377(4) 0.3379(2) -0.1559(2) 0.0322(5) Uani d . 1 . .
C C5 0.5183(4) 0.2437(3) -0.1127(2) 0.0375(6) Uani d . 1 . .
H H5 0.6232 0.2098 -0.1557 0.045 Uiso calc R 1 . .
C C6 0.4449(5) 0.2007(3) -0.0080(3) 0.0408(6) Uani d . 1 . .
H H6 0.4995 0.1385 0.0202 0.049 Uiso calc R 1 . .
C C7 0.2881(4) 0.2518(3) 0.0548(2) 0.0359(6) Uani d . 1 . .
C C8 0.2074(4) 0.3459(3) 0.0179(2) 0.0386(6) Uani d . 1 . .
H H8 0.1041 0.3801 0.0622 0.046 Uiso calc R 1 . .
C C9 0.2849(4) 0.3880(2) -0.0872(2) 0.0333(6) Uani d . 1 . .
C C10 0.6453(5) 0.3300(3) -0.3523(3) 0.0464(7) Uani d . 1 . .
C C11 0.0108(4) 0.1442(3) 0.1690(3) 0.0361(6) Uani d . 1 . .
C C12 -0.0307(4) 0.1167(3) 0.2974(3) 0.0389(6) Uani d . 1 . .
C C13 0.1076(6) 0.2198(3) 0.4010(3) 0.0541(8) Uani d . 1 . .
H H13A 0.2639 0.2317 0.3887 0.081 Uiso calc R 1 . .
H H13B 0.0784 0.1940 0.4787 0.081 Uiso calc R 1 . .
H H13C 0.0672 0.2983 0.4005 0.081 Uiso calc R 1 . .
C C14 -0.2790(5) 0.0855(3) 0.3145(3) 0.0516(8) Uani d . 1 . .
H H14A -0.3331 0.1596 0.3129 0.077 Uiso calc R 1 . .
H H14B -0.3045 0.0591 0.3923 0.077 Uiso calc R 1 . .
H H14C -0.3569 0.0179 0.2493 0.077 Uiso calc R 1 . .
F F1 0.6893(4) 0.3893(2) -0.44723(18) 0.0775(6) Uani d . 1 . .
F F2 0.8423(3) 0.3353(2) -0.29621(18) 0.0652(5) Uani d . 1 . .
F F3 0.5518(3) 0.20819(19) -0.39741(17) 0.0645(5) Uani d . 1 . .
O O1 0.2025(3) 0.48421(18) -0.11926(17) 0.0429(5) Uani d . 1 . .
O O2 0.1777(4) 0.6161(2) -0.2441(2) 0.0648(6) Uani d . 1 . .
O O3 0.2269(3) 0.2130(2) 0.16562(17) 0.0452(5) Uani d . 1 . .
O O4 -0.1216(3) 0.1118(2) 0.08271(19) 0.0498(5) 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'
F F 0.0171 0.0103 '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 . . 117.5(3) ?
O2 C1 C2 . . 125.6(3) ?
O1 C1 C2 . . 116.9(2) ?
C3 C2 C1 . . 121.9(3) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
C2 C3 C4 . . 120.6(3) ?
C2 C3 C10 . . 119.4(3) ?
C4 C3 C10 . . 119.9(2) ?
C9 C4 C5 . . 117.5(2) ?
C9 C4 C3 . . 116.5(2) ?
C5 C4 C3 . . 126.0(2) ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 118.8(2) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C8 C7 C6 . . 122.4(2) ?
C8 C7 O3 . . 119.5(2) ?
C6 C7 O3 . . 117.8(2) ?
C7 C8 C9 . . 117.7(2) ?
C7 C8 H8 . . 121.2 ?
C9 C8 H8 . . 121.2 ?
O1 C9 C8 . . 115.6(2) ?
O1 C9 C4 . . 121.9(2) ?
C8 C9 C4 . . 122.5(2) ?
F3 C10 F1 . . 107.5(2) ?
F3 C10 F2 . . 106.4(3) ?
F1 C10 F2 . . 106.6(2) ?
F3 C10 C3 . . 111.5(2) ?
F1 C10 C3 . . 112.1(3) ?
F2 C10 C3 . . 112.4(2) ?
O4 C11 O3 . . 123.6(2) ?
O4 C11 C12 . . 126.0(2) ?
O3 C11 C12 . . 110.4(2) ?
C14 C12 C11 . . 110.2(2) ?
C14 C12 C13 . . 112.9(3) ?
C11 C12 C13 . . 114.2(2) ?
C14 C12 Br1 . . 107.64(19) ?
C11 C12 Br1 . . 102.84(17) ?
C13 C12 Br1 . . 108.4(2) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 O1 C9 . . 122.1(2) ?
C11 O3 C7 . . 117.3(2) ?
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 C12 . 1.990(3) ?
C1 O2 . 1.205(3) ?
C1 O1 . 1.366(3) ?
C1 C2 . 1.444(4) ?
C2 C3 . 1.340(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.447(4) ?
C3 C10 . 1.507(4) ?
C4 C9 . 1.391(4) ?
C4 C5 . 1.404(4) ?
C5 C6 . 1.375(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.373(4) ?
C7 O3 . 1.400(3) ?
C8 C9 . 1.382(4) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.378(3) ?
C10 F3 . 1.324(4) ?
C10 F1 . 1.332(3) ?
C10 F2 . 1.333(4) ?
C11 O4 . 1.181(3) ?
C11 O3 . 1.368(3) ?
C11 C12 . 1.520(4) ?
C12 C14 . 1.513(4) ?
C12 C13 . 1.529(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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
C5 H5 F2 . 0.93 2.47 3.019(3) 118
C6 H6 O4 1_655 0.93 2.52 3.261(4) 136
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 . . . . -178.7(3) ?
O1 C1 C2 C3 . . . . -0.5(4) ?
C1 C2 C3 C4 . . . . -1.1(4) ?
C1 C2 C3 C10 . . . . 176.3(3) ?
C2 C3 C4 C9 . . . . 2.8(4) ?
C10 C3 C4 C9 . . . . -174.5(2) ?
C2 C3 C4 C5 . . . . -177.8(3) ?
C10 C3 C4 C5 . . . . 4.8(4) ?
C9 C4 C5 C6 . . . . 1.5(4) ?
C3 C4 C5 C6 . . . . -177.9(3) ?
C4 C5 C6 C7 . . . . 0.2(4) ?
C5 C6 C7 C8 . . . . -1.6(4) ?
C5 C6 C7 O3 . . . . -175.8(2) ?
C6 C7 C8 C9 . . . . 1.2(4) ?
O3 C7 C8 C9 . . . . 175.3(2) ?
C7 C8 C9 O1 . . . . -178.8(2) ?
C7 C8 C9 C4 . . . . 0.6(4) ?
C5 C4 C9 O1 . . . . 177.5(2) ?
C3 C4 C9 O1 . . . . -3.1(4) ?
C5 C4 C9 C8 . . . . -1.9(4) ?
C3 C4 C9 C8 . . . . 177.5(2) ?
C2 C3 C10 F3 . . . . -115.9(3) ?
C4 C3 C10 F3 . . . . 61.5(3) ?
C2 C3 C10 F1 . . . . 4.7(4) ?
C4 C3 C10 F1 . . . . -177.9(2) ?
C2 C3 C10 F2 . . . . 124.8(3) ?
C4 C3 C10 F2 . . . . -57.8(3) ?
O4 C11 C12 C14 . . . . -20.7(4) ?
O3 C11 C12 C14 . . . . 159.3(2) ?
O4 C11 C12 C13 . . . . -149.0(3) ?
O3 C11 C12 C13 . . . . 31.0(3) ?
O4 C11 C12 Br1 . . . . 93.8(3) ?
O3 C11 C12 Br1 . . . . -86.2(2) ?
O2 C1 O1 C9 . . . . 178.6(3) ?
C2 C1 O1 C9 . . . . 0.3(4) ?
C8 C9 O1 C1 . . . . -178.9(2) ?
C4 C9 O1 C1 . . . . 1.6(4) ?
O4 C11 O3 C7 . . . . 3.3(4) ?
C12 C11 O3 C7 . . . . -176.7(2) ?
C8 C7 O3 C11 . . . . 71.5(3) ?
C6 C7 O3 C11 . . . . -114.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745197
