#------------------------------------------------------------------------------
#$Date: 2016-10-07 05:02:09 +0300 (Fri, 07 Oct 2016) $
#$Revision: 187004 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/18/2241872.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_2241872
loop_
_publ_author_name
'Caruso, Alessio'
'Blair, Benjamin'
'Tanski, Joseph M.'
_publ_section_title
;
 Crystal structures of 6-chloroindan-1-one and 6-bromoindan-1-one exhibit
 different intermolecular packing interactions
;
_journal_coeditor_code           SJ5508
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1536
_journal_page_last               1540
_journal_paper_doi               10.1107/S2056989016015371
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C9 H7 Br O'
_chemical_formula_moiety         'C9 H7 Br O'
_chemical_formula_sum            'C9 H7 Br O'
_chemical_formula_weight         211.06
_chemical_name_common            6-Bromoindanone
_chemical_name_systematic        6-Bromoindan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.964(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.489(2)
_cell_length_b                   17.101(6)
_cell_length_c                   7.224(3)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.5492
_cell_measurement_theta_min      2.3820
_cell_volume                     781.2(5)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009)
and Mercury (Macrae et al.,  2008)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0455
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4453
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    5.192
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Bruker 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.150
_refine_diff_density_min         -1.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                3600
_reflns_number_total             4453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5508sup1.cif
_cod_data_source_block           II
_cod_database_code               2241872
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'
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
Br Br1 0.34409(5) 0.45945(2) 0.19485(4) 0.02009(16) Uani d 1
O O1 0.4929(3) 0.12531(11) 0.2717(4) 0.0233(5) Uani d 1
C C1 0.3083(4) 0.14135(17) 0.2062(4) 0.0159(5) Uani d 1
C C2 0.1260(4) 0.08352(17) 0.1453(4) 0.0179(5) Uani d 1
H H2A 0.1117 0.0502 0.2537 0.021 Uiso calc 1
H H2B 0.1515 0.0494 0.0419 0.021 Uiso calc 1
C C3 -0.0764(5) 0.13304(17) 0.0755(4) 0.0192(6) Uani d 1
H H3A -0.1424 0.1212 -0.0589 0.023 Uiso calc 1
H H3B -0.1806 0.1229 0.1539 0.023 Uiso calc 1
C C4 -0.0002(4) 0.21670(16) 0.0973(4) 0.0154(5) Uani d 1
C C5 -0.1162(5) 0.28574(17) 0.0538(4) 0.0194(5) Uani d 1
H H5A -0.2646 0.2838 0.0039 0.023 Uiso calc 1
C C6 -0.0119(4) 0.35734(17) 0.0842(4) 0.0178(5) Uani d 1
H H6A -0.0895 0.4045 0.0544 0.021 Uiso calc 1
C C7 0.2070(4) 0.36019(16) 0.1585(4) 0.0158(5) Uani d 1
C C8 0.3257(4) 0.29262(17) 0.2034(4) 0.0155(5) Uani d 1
H H8A 0.474 0.2947 0.2538 0.019 Uiso calc 1
C C9 0.2184(4) 0.22114(15) 0.1714(4) 0.0143(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'
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
O1 C1 C9 126.1(3)
O1 C1 C2 126.6(3)
C9 C1 C2 107.3(2)
C1 C2 C3 106.6(2)
C1 C2 H2A 110.4
C3 C2 H2A 110.4
C1 C2 H2B 110.4
C3 C2 H2B 110.4
H2A C2 H2B 108.6
C4 C3 C2 104.5(2)
C4 C3 H3A 110.9
C2 C3 H3A 110.9
C4 C3 H3B 110.9
C2 C3 H3B 110.9
H3A C3 H3B 108.9
C5 C4 C9 119.2(2)
C5 C4 C3 129.0(2)
C9 C4 C3 111.8(2)
C6 C5 C4 119.3(3)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C5 C6 C7 120.4(3)
C5 C6 H6A 119.8
C7 C6 H6A 119.8
C8 C7 C6 121.5(3)
C8 C7 Br1 119.5(2)
C6 C7 Br1 119.0(2)
C7 C8 C9 117.3(2)
C7 C8 H8A 121.3
C9 C8 H8A 121.3
C8 C9 C4 122.3(2)
C8 C9 C1 127.8(2)
C4 C9 C1 109.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.907(3)
O1 C1 1.216(3)
C1 C9 1.483(4)
C1 C2 1.529(4)
C2 C3 1.549(4)
C2 H2A 0.99
C2 H2B 0.99
C3 C4 1.510(4)
C3 H3A 0.99
C3 H3B 0.99
C4 C5 1.398(4)
C4 C9 1.401(4)
C5 C6 1.392(4)
C5 H5A 0.95
C6 C7 1.402(4)
C6 H6A 0.95
C7 C8 1.386(4)
C8 C9 1.400(4)
C8 H8A 0.95
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
C3 H3B O1 1_455 0.99 2.45 3.408(4) 161.6 y
C5 H5A O1 4_465 0.95 2.55 3.253(4) 130.6 y
C2 H2B Br1 4_565 0.99 3.05 3.898(3) 145.0 y
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
O1 C1 C2 C3 179.0(3)
C9 C1 C2 C3 -0.8(3)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 179.3(3)
C2 C3 C4 C9 -0.4(3)
C9 C4 C5 C6 0.3(4)
C3 C4 C5 C6 -179.4(3)
C4 C5 C6 C7 -0.3(4)
C5 C6 C7 C8 0.1(4)
C5 C6 C7 Br1 179.2(2)
C6 C7 C8 C9 0.0(4)
Br1 C7 C8 C9 -179.01(19)
C7 C8 C9 C4 -0.1(4)
C7 C8 C9 C1 179.6(3)
C5 C4 C9 C8 -0.1(4)
C3 C4 C9 C8 179.6(2)
C5 C4 C9 C1 -179.8(2)
C3 C4 C9 C1 -0.1(3)
O1 C1 C9 C8 1.1(5)
C2 C1 C9 C8 -179.2(3)
O1 C1 C9 C4 -179.2(3)
C2 C1 C9 C4 0.6(3)

_cod_database_fobs_code 2241872
