#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024918.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_4024918
loop_
_publ_author_name
'Gon-Ann Lee'
'Wen-Chieh Wang'
'Shih-Fen Jiang'
'Chih-Yi Chang'
'Ru-Ting Tsai'
_publ_section_title
;
The Crossed [2+2] Cycloaddition of 1-Phenylcyclopropene and
1-Bromo-2-phenylcyclopropene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7994
_journal_page_last               7997
_journal_paper_doi               10.1021/jo901636k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H12 Br2'
_chemical_formula_sum            'C18 H12 Br2'
_chemical_formula_weight         388.10
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.90300(10)
_cell_length_b                   11.5700(2)
_cell_length_c                   32.8950(7)
_cell_measurement_reflns_used    20273
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      1.958
_cell_volume                     3007.84(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15409
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    5.376
_exptl_absorpt_correction_T_max  0.6549
_exptl_absorpt_correction_T_min  0.5152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0368
_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)+(0.0407P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                2012
_reflns_number_total             2649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901636k_si_004.cif
_cod_data_source_block           7
_cod_database_code               4024918
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.63051(5) 0.95950(4) 0.056877(14) 0.03124(16) Uani 1 1 d . . .
Br2 Br 0.77490(5) 0.74812(4) -0.004290(13) 0.02802(15) Uani 1 1 d . . .
C1 C 0.6235(5) 0.8023(3) 0.07277(13) 0.0205(10) Uani 1 1 d . . .
C2 C 0.6805(5) 0.7154(4) 0.04714(12) 0.0218(10) Uani 1 1 d . . .
C3 C 0.6720(5) 0.6006(4) 0.05966(12) 0.0215(9) Uani 1 1 d . . .
H3 H 0.7107 0.5403 0.0419 0.026 Uiso 1 1 d R . .
C4 C 0.6086(5) 0.5725(3) 0.09768(12) 0.0197(10) Uani 1 1 d . . .
C5 C 0.5463(4) 0.6604(4) 0.12364(12) 0.0190(9) Uani 1 1 d . . .
C6 C 0.5551(5) 0.7744(4) 0.11027(12) 0.0211(10) Uani 1 1 d . . .
H6 H 0.5133 0.8355 0.1273 0.025 Uiso 1 1 d R . .
C7 C 0.4690(5) 0.6355(3) 0.16397(12) 0.0196(9) Uani 1 1 d . . .
C8 C 0.5189(5) 0.6961(4) 0.19837(14) 0.0296(11) Uani 1 1 d . . .
H8 H 0.6014 0.7566 0.1960 0.036 Uiso 1 1 d R . .
C9 C 0.4467(6) 0.6727(4) 0.23570(14) 0.0350(12) Uani 1 1 d . . .
H9 H 0.4841 0.7150 0.2592 0.042 Uiso 1 1 d R . .
C10 C 0.3261(6) 0.5866(4) 0.23977(14) 0.0345(12) Uani 1 1 d . . .
H10 H 0.2763 0.5704 0.2658 0.041 Uiso 1 1 d R . .
C11 C 0.2750(5) 0.5260(4) 0.20568(13) 0.0277(11) Uani 1 1 d . . .
H11 H 0.1932 0.4651 0.2082 0.033 Uiso 1 1 d R . .
C12 C 0.3442(5) 0.5503(3) 0.16810(13) 0.0248(10) Uani 1 1 d . . .
H12 H 0.3048 0.5098 0.1445 0.030 Uiso 1 1 d R . .
C13 C 0.6066(5) 0.4473(3) 0.10981(12) 0.0190(9) Uani 1 1 d . . .
C14 C 0.6825(5) 0.4100(4) 0.14560(13) 0.0254(10) Uani 1 1 d . . .
H14 H 0.7423 0.4640 0.1625 0.031 Uiso 1 1 d R . .
C15 C 0.6775(5) 0.2953(4) 0.15682(13) 0.0254(10) Uani 1 1 d . . .
H15 H 0.7304 0.2711 0.1816 0.030 Uiso 1 1 d R . .
C16 C 0.5959(5) 0.2160(4) 0.13221(13) 0.0260(11) Uani 1 1 d . . .
H16 H 0.5907 0.1362 0.1401 0.031 Uiso 1 1 d R . .
C17 C 0.5209(5) 0.2504(3) 0.09643(13) 0.0238(10) Uani 1 1 d . . .
H17 H 0.4634 0.1959 0.0793 0.029 Uiso 1 1 d R . .
C18 C 0.5287(5) 0.3659(3) 0.08522(12) 0.0206(10) Uani 1 1 d . . .
H18 H 0.4800 0.3909 0.0599 0.025 Uiso 1 1 d R . .
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0(4) . . ?
C6 C1 Br1 118.8(3) . . ?
C2 C1 Br1 121.3(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 Br2 121.9(3) . . ?
C3 C2 Br2 118.4(3) . . ?
C4 C3 C2 120.5(4) . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 C13 118.0(4) . . ?
C5 C4 C13 121.9(4) . . ?
C6 C5 C4 118.2(4) . . ?
C6 C5 C7 119.1(4) . . ?
C4 C5 C7 122.7(4) . . ?
C1 C6 C5 121.4(4) . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 C5 120.7(4) . . ?
C12 C7 C5 120.8(4) . . ?
C9 C8 C7 120.5(4) . . ?
C8 C9 C10 120.8(4) . . ?
C11 C10 C9 119.2(4) . . ?
C12 C11 C10 120.5(4) . . ?
C11 C12 C7 120.6(4) . . ?
C18 C13 C14 118.4(4) . . ?
C18 C13 C4 120.3(4) . . ?
C14 C13 C4 121.3(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C16 119.7(4) . . ?
C17 C16 C15 120.6(4) . . ?
C16 C17 C18 119.1(4) . . ?
C13 C18 C17 121.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.893(4) . ?
Br2 C2 1.887(4) . ?
C1 C6 1.385(6) . ?
C1 C2 1.387(6) . ?
C2 C3 1.393(6) . ?
C3 C4 1.386(5) . ?
C4 C5 1.416(5) . ?
C4 C13 1.502(5) . ?
C5 C6 1.392(5) . ?
C5 C7 1.489(6) . ?
C7 C8 1.389(6) . ?
C7 C12 1.401(5) . ?
C8 C9 1.381(6) . ?
C9 C10 1.385(6) . ?
C10 C11 1.383(6) . ?
C11 C12 1.381(6) . ?
C13 C18 1.386(5) . ?
C13 C14 1.390(6) . ?
C14 C15 1.378(6) . ?
C15 C16 1.383(6) . ?
C16 C17 1.377(6) . ?
C17 C18 1.387(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26668260
