##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1057743'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2015-03-13
_journal_date_accepted     2015-04-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      5
_journal_page_first     o326
_journal_page_last     o327
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015006738
_journal_coeditor_code     TK5362
_publ_contact_author_name     'B. S. Palakshamurthy'
_publ_contact_author_address
;
Department of Physics, Yuvaraja's College (Constituent College),
University of Mysore, Mysore, Karnataka 570 005, India,
;
_publ_contact_author_email     'palaksha.bspm@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Devarajegowda, H. C.' .
;
Department of Physics, Yuvaraja's College (Constituent College),
University of Mysore, Mysore, Karnataka 570 005,
India
;
    'Suchetan, P. A.' .
;
Department of Studies and Research in Chemistry, U.C.S., Tumkur University,
Tumkur, Karnataka 572 103,
India
;
    'Srinivasa, H. T.' .
;
Raman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore,
 Karnataka 560080, India
;
    'Sreenivasa, S.' .
;
Department of Studies and Research in Chemistry, Tumkur University, Tumkur,
Karnataka 572 103, India
;
    'Palakshamurthy, B. S.' .
;
Department of Physics, Yuvaraja's College (Constituent College),
University of Mysore, Mysore, Karnataka 570 005,
India
;
_publ_section_synopsis     .
_chemical_name_systematic
;
4-Bromophenyl-2-oxo-2H-chromene-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H9 Br O4'
_chemical_formula_sum     'C16 H9 Br O4'
_chemical_formula_iupac     'C16 H9 Br O4'
_chemical_formula_weight     345.14
_chemical_melting_point     523
_symmetry_space_group_name_hall     '-P 2ybc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     16.0782(10)
_cell_length_b     7.2618(4)
_cell_length_c     12.7396(8)
_cell_angle_alpha     90
_cell_angle_beta     113.311(4)
_cell_angle_gamma     90
_cell_volume     1366.01(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2395
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     296(2)
_cell_special_details     Prism
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.240
_exptl_crystal_size_mid     0.180
_exptl_crystal_size_min     0.160
_exptl_crystal_density_diffrn     1.678
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     3.022
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_shelx_estimated_absorpt_T_min     0.531
_shelx_estimated_absorpt_T_max     0.643
_exptl_absorpt_correction_T_min     0.526
_exptl_absorpt_correction_T_max     0.617
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     Graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     2.01
_diffrn_reflns_number     20483
_diffrn_reflns_av_R_equivalents     0.0374
_diffrn_reflns_theta_min     2.759
_diffrn_reflns_theta_max     24.995
_diffrn_reflns_theta_full     24.995
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details     ?
_reflns_number_total     2395
_reflns_number_gt     1831
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0510
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0739
_refine_ls_wR_factor_ref     0.0789
_refine_ls_goodness_of_fit_ref     1.011
_refine_ls_restrained_S_all     1.011
_refine_ls_number_reflns     2395
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0319P)²+0.8274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.446
_refine_diff_density_min     -0.535
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.0062(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.94359(2) 0.14526(6) 0.64830(3) 0.0907(2) Uani d 1 . .
    O O1 0.31144(12) 0.1686(2) -0.06316(14) 0.0517(5) Uani d 1 . .
    O O2 0.44603(13) 0.1964(3) -0.06745(15) 0.0612(5) Uani d 1 . .
    O O3 0.58965(12) 0.2657(3) 0.15291(14) 0.0556(5) Uani d 1 . .
    O O4 0.56890(11) 0.0734(2) 0.27929(13) 0.0428(4) Uani d 1 . .
    C C1 0.25543(17) 0.1424(3) -0.0061(2) 0.0460(6) Uani d 1 . .
    C C2 0.1631(2) 0.1504(4) -0.0694(3) 0.0613(8) Uani d 1 . .
    H H2 0.1403 0.1720 -0.1477 0.074 Uiso calc 1 . .
    C C3 0.1059(2) 0.1257(4) -0.0142(3) 0.0709(9) Uani d 1 . .
    H H3 0.0436 0.1322 -0.0558 0.085 Uiso calc 1 . .
    C C4 0.1389(2) 0.0915(4) 0.1017(3) 0.0673(9) Uani d 1 . .
    H H4 0.0990 0.0734 0.1372 0.081 Uiso calc 1 . .
    C C5 0.23074(18) 0.0840(4) 0.1648(3) 0.0547(7) Uani d 1 . .
    H H5 0.2530 0.0613 0.2429 0.066 Uiso calc 1 . .
    C C6 0.29078(17) 0.1108(3) 0.1108(2) 0.0413(6) Uani d 1 . .
    C C7 0.38706(16) 0.1145(3) 0.1709(2) 0.0394(6) Uani d 1 . .
    H H7 0.4122 0.0939 0.2493 0.047 Uiso calc 1 . .
    C C8 0.44200(16) 0.1472(3) 0.11609(19) 0.0364(6) Uani d 1 . .
    C C9 0.40485(18) 0.1736(3) -0.0079(2) 0.0440(6) Uani d 1 . .
    C C10 0.54071(17) 0.1702(3) 0.18007(19) 0.0385(6) Uani d 1 . .
    C C11 0.65769(16) 0.0988(3) 0.36007(19) 0.0370(5) Uani d 1 . .
    C C12 0.66608(17) 0.1487(3) 0.4677(2) 0.0433(6) Uani d 1 . .
    H H12 0.6149 0.1711 0.4827 0.052 Uiso calc 1 . .
    C C13 0.75178(19) 0.1654(4) 0.5536(2) 0.0517(7) Uani d 1 . .
    H H13 0.7590 0.2000 0.6270 0.062 Uiso calc 1 . .
    C C14 0.82608(18) 0.1301(4) 0.5288(2) 0.0499(7) Uani d 1 . .
    C C15 0.81735(18) 0.0805(4) 0.4214(2) 0.0538(7) Uani d 1 . .
    H H15 0.8686 0.0581 0.4065 0.065 Uiso calc 1 . .
    C C16 0.73210(17) 0.0637(4) 0.3352(2) 0.0452(6) Uani d 1 . .
    H H16 0.7251 0.0293 0.2619 0.054 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C14 . 1.903(3) ?
    O1 C1 . 1.376(3) ?
    O1 C9 . 1.384(3) ?
    O2 C9 . 1.200(3) ?
    O3 C10 . 1.198(3) ?
    O4 C10 . 1.358(3) ?
    O4 C11 . 1.403(3) ?
    C1 C2 . 1.382(4) ?
    C1 C6 . 1.387(4) ?
    C2 C3 . 1.373(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.380(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.374(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.402(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.430(3) ?
    C7 C8 . 1.346(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.463(3) ?
    C8 C10 . 1.479(3) ?
    C11 C12 . 1.372(3) ?
    C11 C16 . 1.377(3) ?
    C12 C13 . 1.385(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.375(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.368(4) ?
    C15 C16 . 1.381(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C1 O1 C9 . . 122.67(19) ?
    C10 O4 C11 . . 118.88(18) ?
    O1 C1 C2 . . 117.5(2) ?
    O1 C1 C6 . . 121.0(2) ?
    C2 C1 C6 . . 121.5(3) ?
    C3 C2 C1 . . 118.6(3) ?
    C3 C2 H2 . . 120.7 ?
    C1 C2 H2 . . 120.7 ?
    C2 C3 C4 . . 121.3(3) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 120.2(3) ?
    C5 C4 H4 . . 119.9 ?
    C3 C4 H4 . . 119.9 ?
    C4 C5 C6 . . 119.8(3) ?
    C4 C5 H5 . . 120.1 ?
    C6 C5 H5 . . 120.1 ?
    C1 C6 C5 . . 118.7(2) ?
    C1 C6 C7 . . 117.9(2) ?
    C5 C6 C7 . . 123.3(2) ?
    C8 C7 C6 . . 121.3(2) ?
    C8 C7 H7 . . 119.4 ?
    C6 C7 H7 . . 119.4 ?
    C7 C8 C9 . . 120.8(2) ?
    C7 C8 C10 . . 121.0(2) ?
    C9 C8 C10 . . 118.1(2) ?
    O2 C9 O1 . . 116.2(2) ?
    O2 C9 C8 . . 127.5(2) ?
    O1 C9 C8 . . 116.3(2) ?
    O3 C10 O4 . . 123.6(2) ?
    O3 C10 C8 . . 126.2(2) ?
    O4 C10 C8 . . 110.2(2) ?
    C12 C11 C16 . . 121.9(2) ?
    C12 C11 O4 . . 115.9(2) ?
    C16 C11 O4 . . 122.1(2) ?
    C11 C12 C13 . . 119.1(2) ?
    C11 C12 H12 . . 120.4 ?
    C13 C12 H12 . . 120.4 ?
    C14 C13 C12 . . 119.0(2) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C15 C14 C13 . . 121.6(2) ?
    C15 C14 Br1 . . 119.5(2) ?
    C13 C14 Br1 . . 118.9(2) ?
    C14 C15 C16 . . 119.7(2) ?
    C14 C15 H15 . . 120.2 ?
    C16 C15 H15 . . 120.2 ?
    C11 C16 C15 . . 118.7(2) ?
    C11 C16 H16 . . 120.7 ?
    C15 C16 H16 . . 120.7 ?
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
    C9 O1 C1 C2 . . . . 176.4(2) ?
    C9 O1 C1 C6 . . . . -3.1(4) ?
    O1 C1 C2 C3 . . . . -179.7(2) ?
    C6 C1 C2 C3 . . . . -0.2(4) ?
    C1 C2 C3 C4 . . . . -0.7(4) ?
    C2 C3 C4 C5 . . . . 0.9(5) ?
    C3 C4 C5 C6 . . . . -0.2(4) ?
    O1 C1 C6 C5 . . . . -179.7(2) ?
    C2 C1 C6 C5 . . . . 0.9(4) ?
    O1 C1 C6 C7 . . . . 2.8(3) ?
    C2 C1 C6 C7 . . . . -176.7(2) ?
    C4 C5 C6 C1 . . . . -0.7(4) ?
    C4 C5 C6 C7 . . . . 176.7(3) ?
    C1 C6 C7 C8 . . . . -0.1(3) ?
    C5 C6 C7 C8 . . . . -177.6(2) ?
    C6 C7 C8 C9 . . . . -2.2(3) ?
    C6 C7 C8 C10 . . . . 173.5(2) ?
    C1 O1 C9 O2 . . . . 179.7(2) ?
    C1 O1 C9 C8 . . . . 0.7(3) ?
    C7 C8 C9 O2 . . . . -176.9(3) ?
    C10 C8 C9 O2 . . . . 7.3(4) ?
    C7 C8 C9 O1 . . . . 2.0(3) ?
    C10 C8 C9 O1 . . . . -173.9(2) ?
    C11 O4 C10 O3 . . . . 6.3(3) ?
    C11 O4 C10 C8 . . . . -170.71(19) ?
    C7 C8 C10 O3 . . . . -148.3(3) ?
    C9 C8 C10 O3 . . . . 27.6(4) ?
    C7 C8 C10 O4 . . . . 28.7(3) ?
    C9 C8 C10 O4 . . . . -155.5(2) ?
    C10 O4 C11 C12 . . . . 124.6(2) ?
    C10 O4 C11 C16 . . . . -59.7(3) ?
    C16 C11 C12 C13 . . . . 0.4(4) ?
    O4 C11 C12 C13 . . . . 176.2(2) ?
    C11 C12 C13 C14 . . . . -0.5(4) ?
    C12 C13 C14 C15 . . . . 0.5(4) ?
    C12 C13 C14 Br1 . . . . -177.94(19) ?
    C13 C14 C15 C16 . . . . -0.5(4) ?
    Br1 C14 C15 C16 . . . . 178.0(2) ?
    C12 C11 C16 C15 . . . . -0.3(4) ?
    O4 C11 C16 C15 . . . . -175.9(2) ?
    C14 C15 C16 C11 . . . . 0.4(4) ?
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
    C12 H12 O3 4_566 0.93 2.40 3.124(3) 134
