#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/07/7230747.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_7230747
loop_
_publ_author_name
'Yu, Chin-Yang'
'Lai, Yu-Chun'
_publ_section_title
;
 Synthesis, aggregation induced emission and through space conjugation of
 triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              19341
_journal_paper_doi               10.1039/C8RA03025A
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C16 H11 Br'
_chemical_formula_sum            'C16 H11 Br'
_chemical_formula_weight         283.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.738(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8830(16)
_cell_length_b                   11.6713(13)
_cell_length_c                   7.3807(8)
_cell_measurement_reflns_used    5737
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.199
_cell_measurement_theta_min      2.938
_cell_volume                     1194.5(2)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14005
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_T_max  0.8756
_exptl_absorpt_correction_T_min  0.5787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.443
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+2.8961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                1723
_reflns_number_total             2147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra03025a2.cif
_cod_data_source_block           d19302
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7230747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.1542(3) 0.6053(3) 0.3098(6) 0.0346(9) Uani 1 1 d .
C2 C 0.1551(3) 0.5032(3) 0.4055(5) 0.0334(9) Uani 1 1 d .
C3 C 0.2314(3) 0.4900(3) 0.5356(5) 0.0366(9) Uani 1 1 d .
H3 H 0.2276 0.4321 0.6255 0.044 Uiso 1 1 calc R
C4 C 0.3120(3) 0.5596(3) 0.5354(5) 0.0351(9) Uani 1 1 d .
H4 H 0.3631 0.5488 0.6241 0.042 Uiso 1 1 calc R
C5 C 0.3186(3) 0.6453(3) 0.4061(5) 0.0319(8) Uani 1 1 d .
C6 C 0.2348(3) 0.6763(3) 0.3075(5) 0.0338(9) Uani 1 1 d .
H6 H 0.2324 0.7452 0.2391 0.041 Uiso 1 1 calc R
C7 C 0.4157(3) 0.6763(3) 0.3391(5) 0.0360(9) Uani 1 1 d .
H7 H 0.4477 0.7441 0.3800 0.043 Uiso 1 1 calc R
C8 C 0.4563(3) 0.6065(3) 0.2206(5) 0.0338(9) Uani 1 1 d .
H8 H 0.5185 0.6224 0.1785 0.041 Uiso 1 1 calc R
C9 C 0.4012(3) 0.5025(3) 0.1558(5) 0.0323(8) Uani 1 1 d .
C10 C 0.3257(3) 0.5161(3) 0.0252(5) 0.0342(9) Uani 1 1 d .
H10 H 0.3291 0.5742 -0.0643 0.041 Uiso 1 1 calc R
C11 C 0.2457(3) 0.4446(3) 0.0263(5) 0.0351(9) Uani 1 1 d .
H11 H 0.1947 0.4539 -0.0630 0.042 Uiso 1 1 calc R
C12 C 0.2398(3) 0.3593(3) 0.1576(5) 0.0337(9) Uani 1 1 d .
C13 C 0.3238(3) 0.3301(3) 0.2562(6) 0.0371(9) Uani 1 1 d .
H13 H 0.3265 0.2612 0.3249 0.045 Uiso 1 1 calc R
C14 C 0.4040(3) 0.4016(3) 0.2549(6) 0.0369(9) Uani 1 1 d .
H14 H 0.4613 0.3809 0.3226 0.044 Uiso 1 1 calc R
C15 C 0.1425(3) 0.3294(3) 0.2244(6) 0.0386(9) Uani 1 1 d .
H15 H 0.1106 0.2613 0.1843 0.046 Uiso 1 1 calc R
C16 C 0.1013(3) 0.3996(3) 0.3407(6) 0.0367(9) Uani 1 1 d .
H16 H 0.0388 0.3837 0.3813 0.044 Uiso 1 1 calc R
Br1 Br 0.05053(3) 0.63595(4) 0.13880(7) 0.0543(2) Uani 1 1 d .
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
C2 C1 C6 122.0(4)
C2 C1 Br1 119.2(3)
C6 C1 Br1 117.5(3)
C1 C2 C3 115.5(4)
C1 C2 C16 122.9(4)
C3 C2 C16 118.8(3)
C4 C3 C2 121.3(4)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.2(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 117.8(4)
C4 C5 C7 119.3(4)
C6 C5 C7 120.5(4)
C5 C6 C1 119.5(4)
C5 C6 H6 120.3
C1 C6 H6 120.3
C8 C7 C5 118.7(3)
C8 C7 H7 120.6
C5 C7 H7 120.6
C7 C8 C9 118.5(3)
C7 C8 H8 120.8
C9 C8 H8 120.8
C14 C9 C10 117.4(4)
C14 C9 C8 121.2(4)
C10 C9 C8 118.8(3)
C11 C10 C9 120.1(4)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.4(4)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 117.7(4)
C13 C12 C15 121.2(4)
C11 C12 C15 118.5(4)
C12 C13 C14 120.1(4)
C12 C13 H13 119.9
C14 C13 H13 119.9
C9 C14 C13 120.7(4)
C9 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C12 119.3(3)
C16 C15 H15 120.4
C12 C15 H15 120.4
C15 C16 C2 118.8(3)
C15 C16 H16 120.6
C2 C16 H16 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(6)
C1 C6 1.392(5)
C1 Br1 1.903(4)
C2 C3 1.404(6)
C2 C16 1.488(5)
C3 C4 1.383(5)
C3 H3 0.9500
C4 C5 1.389(6)
C4 H4 0.9500
C5 C6 1.391(5)
C5 C7 1.502(5)
C6 H6 0.9500
C7 C8 1.339(6)
C7 H7 0.9500
C8 C9 1.500(5)
C8 H8 0.9500
C9 C14 1.386(6)
C9 C10 1.399(5)
C10 C11 1.388(5)
C10 H10 0.9500
C11 C12 1.395(6)
C11 H11 0.9500
C12 C13 1.387(6)
C12 C15 1.501(5)
C13 C14 1.392(6)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.335(6)
C15 H15 0.9500
C16 H16 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204731
