#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239703.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_2239703
loop_
_publ_author_name
'Xue, Yue-yuan'
'Qin, Yong-qi'
_publ_section_title
;
 2',7'-Dibromospiro[cyclopropane-1,9'-fluorene]
;
_journal_coeditor_code           CV5463
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o821
_journal_paper_doi               10.1107/S1600536814014585
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C15 H10 Br2'
_chemical_formula_moiety         'C15 H10 Br2'
_chemical_formula_sum            'C15 H10 Br2'
_chemical_formula_weight         350.05
_chemical_name_systematic
;
2',7'-Dibromospiro[cyclopropane-1,9'-fluorene]
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_Hall           '-C 2c 2'
_space_group_name_H-M_alt        'C m c m'
_symmetry_space_group_name_Hall  '-C 2c 2'
_symmetry_space_group_name_H-M   'C m c m'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9485(17)
_cell_length_b                   11.0619(11)
_cell_length_c                   6.8127(10)
_cell_measurement_reflns_used    933
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.20
_cell_volume                     1277.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1550
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3276
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.199
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.319
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.684
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                471
_reflns_number_total             640
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5463sup1.cif
_cod_data_source_block           I
_cod_database_code               2239703
_cod_database_fobs_code          2239703
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'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, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -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_occupancy
Br Br1 0.31110(3) 0.12115(5) 0.7500 0.0746(4) Uani d 1
C C1 0.0691(3) 0.1592(4) 0.7500 0.0396(11) Uani d 1
C C2 0.1489(3) 0.1851(4) 0.7500 0.0470(12) Uani d 1
H H2 0.1666 0.2647 0.7500 0.056 Uiso d 1
C C3 0.2011(3) 0.0894(5) 0.7500 0.0478(12) Uani d 1
C C4 0.1763(3) -0.0277(4) 0.7500 0.0506(12) Uani d 1
H H4 0.2130 -0.0901 0.7500 0.061 Uiso d 1
C C5 0.0965(3) -0.0541(4) 0.7500 0.0450(12) Uani d 1
H H5 0.0792 -0.1339 0.7500 0.054 Uiso d 1
C C6 0.0429(2) 0.0393(4) 0.7500 0.0380(10) Uani d 1
C C13 0.0000 0.2412(5) 0.7500 0.0424(16) Uani d 1
C C14 0.0000 0.3609(3) 0.6418(11) 0.0725(18) Uani d 1
H H14 0.0485 0.3846 0.5754 0.087 Uiso 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'
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
C2 C1 C6 . . 120.5(4)
C2 C1 C13 . . 130.3(4)
C6 C1 C13 . . 109.3(4)
C3 C2 C1 . . 117.9(4)
C3 C2 H2 . . 121.3
C1 C2 H2 . . 120.8
C4 C3 C2 . . 122.1(5)
C4 C3 Br1 . . 118.7(4)
C2 C3 Br1 . . 119.2(4)
C3 C4 C5 . . 120.2(4)
C3 C4 H4 . . 120.0
C5 C4 H4 . . 119.8
C6 C5 C4 . . 119.1(4)
C6 C5 H5 . . 120.4
C4 C5 H5 . . 120.5
C5 C6 C1 . . 120.2(4)
C5 C6 C6 . 11 131.3(3)
C1 C6 C6 . 11 108.5(3)
C1 C13 C1 11 . 104.5(5)
C1 C13 C14 11 . 122.36(19)
C1 C13 C14 . . 122.36(19)
C1 C13 C14 11 10_557 122.36(19)
C1 C13 C14 . 10_557 122.36(19)
C14 C13 C14 . 10_557 58.2(6)
C14 C14 C13 10_557 . 60.9(3)
C14 C14 H14 10_557 . 117.6
C13 C14 H14 . . 117.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C3 . 1.897(5)
C1 C2 . 1.383(6)
C1 C6 . 1.398(6)
C1 C13 . 1.481(6)
C2 C3 . 1.380(7)
C2 H2 . 0.9300
C3 C4 . 1.361(7)
C4 C5 . 1.384(6)
C4 H4 . 0.9299
C5 C6 . 1.375(6)
C5 H5 . 0.9299
C6 C6 11 1.454(8)
C13 C1 11 1.481(6)
C13 C14 . 1.516(7)
C13 C14 10_557 1.516(7)
C14 C14 10_557 1.475(14)
C14 H14 . 0.9741
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_4
_geom_torsion
C6 C1 C2 C3 . . 0.0
C13 C1 C2 C3 . . 180.0
C1 C2 C3 C4 . . 0.0
C1 C2 C3 Br1 . . 180.0
C2 C3 C4 C5 . . 0.0
Br1 C3 C4 C5 . . 180.0
C3 C4 C5 C6 . . 0.0
C4 C5 C6 C1 . . 0.0
C4 C5 C6 C6 . 11 180.0
C2 C1 C6 C5 . . 0.0
C13 C1 C6 C5 . . 180.0
C2 C1 C6 C6 . 11 180.0
C13 C1 C6 C6 . 11 0.0
C2 C1 C13 C1 . 11 180.0
C6 C1 C13 C1 . 11 0.0
C2 C1 C13 C14 . . 35.1(4)
C6 C1 C13 C14 . . -144.9(4)
C2 C1 C13 C14 . 10_557 -35.1(4)
C6 C1 C13 C14 . 10_557 144.9(4)
C1 C13 C14 C14 11 10_557 110.6(3)
C1 C13 C14 C14 . 10_557 -110.6(3)
