#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/36/4513635.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_4513635
loop_
_publ_author_name
'Pang, Xue'
'Wang, Hui'
'Wang, Weizhou'
'Jin, Wei Jun'
_publ_section_title
;
 Phosphorescent π-Hole···π Bonding Cocrystals of
 Pyrene with Halo-perfluorobenzenes (F, Cl, Br, I)
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4938
_journal_paper_doi               10.1021/acs.cgd.5b00844
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C22 H10 Br2 F4'
_chemical_formula_weight         510.12
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.290(8)
_cell_angle_beta                 90.150(9)
_cell_angle_gamma                102.722(9)
_cell_formula_units_Z            1
_cell_length_a                   7.046(4)
_cell_length_b                   8.334(4)
_cell_length_c                   8.623(5)
_cell_measurement_reflns_used    768
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.98
_cell_volume                     439.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1535
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    4.652
_exptl_absorpt_correction_T_max  0.7072
_exptl_absorpt_correction_T_min  0.4718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0422
_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)+(0.0324P)²+1.0630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                1364
_reflns_number_total             1535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00844_si_001.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4513628--4513635.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513635
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.50399(8) 0.69154(8) 0.74183(7) 0.0311(2) Uani 1 1 d .
C1 C 0.4979(7) 0.5830(7) 0.8904(6) 0.0226(11) Uani 1 1 d .
C2 C 0.5690(7) 0.6872(7) 1.0647(7) 0.0249(11) Uani 1 1 d .
C3 C 0.5711(7) 0.6060(7) 1.1724(6) 0.0238(11) Uani 1 1 d .
C4 C 0.9894(7) 0.2967(7) 1.1512(7) 0.0248(11) Uani 1 1 d .
H4 H 0.9994 0.2477 1.2307 0.030 Uiso 1 1 calc R
C5 C 0.9126(7) 0.1811(7) 0.9848(7) 0.0241(11) Uani 1 1 d .
H5 H 0.8682 0.0526 0.9502 0.029 Uiso 1 1 calc R
C7 C 0.8192(8) 0.1282(7) 0.6846(7) 0.0296(12) Uani 1 1 d .
H7 H 0.7784 -0.0012 0.6465 0.035 Uiso 1 1 calc R
C8 C 0.8019(8) 0.1974(8) 0.5681(7) 0.0338(13) Uani 1 1 d .
H8 H 0.7477 0.1156 0.4511 0.041 Uiso 1 1 calc R
C9 C 0.8629(8) 0.3850(7) 0.6203(7) 0.0269(12) Uani 1 1 d .
H9 H 0.8491 0.4304 0.5385 0.032 Uiso 1 1 calc R
C10 C 0.9439(7) 0.5083(7) 0.7899(7) 0.0221(11) Uani 1 1 d .
C11 C 0.9600(6) 0.4394(6) 0.9127(6) 0.0181(10) Uani 1 1 d .
C12 C 0.8965(7) 0.2469(6) 0.8595(6) 0.0206(10) Uani 1 1 d .
F1 F 0.6392(5) 0.8700(4) 1.1303(4) 0.0320(7) Uani 1 1 d .
F2 F 0.6424(5) 0.7123(4) 1.3392(4) 0.0324(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0311(3) 0.0354(3) 0.0294(3) 0.0176(2) 0.0012(2) 0.0071(2)
C1 0.014(2) 0.027(3) 0.020(3) 0.004(2) 0.003(2) 0.008(2)
C2 0.020(3) 0.019(3) 0.028(3) 0.005(2) 0.003(2) 0.002(2)
C3 0.022(3) 0.023(3) 0.015(2) -0.001(2) -0.001(2) 0.004(2)
C4 0.023(3) 0.025(3) 0.030(3) 0.015(2) 0.005(2) 0.008(2)
C5 0.025(3) 0.014(2) 0.035(3) 0.012(2) 0.002(2) 0.005(2)
C7 0.034(3) 0.018(3) 0.022(3) -0.001(2) -0.002(2) -0.001(2)
C8 0.034(3) 0.033(3) 0.017(3) -0.001(2) -0.007(2) 0.003(3)
C9 0.028(3) 0.031(3) 0.019(3) 0.010(2) 0.001(2) 0.006(2)
C10 0.020(3) 0.022(3) 0.024(3) 0.009(2) 0.004(2) 0.008(2)
C11 0.013(2) 0.018(2) 0.019(2) 0.005(2) 0.0047(19) 0.0038(19)
C12 0.020(2) 0.016(2) 0.021(3) 0.004(2) 0.002(2) 0.005(2)
F1 0.0405(18) 0.0155(15) 0.0274(16) 0.0011(13) 0.0012(14) 0.0014(13)
F2 0.0374(18) 0.0280(17) 0.0161(15) -0.0010(13) -0.0033(13) 0.0019(14)
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 118.0(5) . 2_667
C2 C1 Br1 121.2(4) . .
C3 C1 Br1 120.7(4) 2_667 .
F1 C2 C3 119.0(5) . .
F1 C2 C1 119.9(5) . .
C3 C2 C1 121.1(5) . .
F2 C3 C2 118.8(5) . .
F2 C3 C1 120.3(5) . 2_667
C2 C3 C1 120.9(5) . 2_667
C5 C4 C10 121.3(5) . 2_767
C5 C4 H4 119.4 . .
C10 C4 H4 119.4 2_767 .
C4 C5 C12 121.7(4) . .
C4 C5 H5 119.2 . .
C12 C5 H5 119.2 . .
C8 C7 C12 120.9(5) . .
C8 C7 H7 119.6 . .
C12 C7 H7 119.6 . .
C7 C8 C9 120.5(5) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C10 121.3(5) . .
C8 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C9 C10 C11 119.0(5) . .
C9 C10 C4 123.0(5) . 2_767
C11 C10 C4 118.0(4) . 2_767
C11 C11 C12 119.4(5) 2_767 .
C11 C11 C10 120.8(5) 2_767 .
C12 C11 C10 119.8(4) . .
C7 C12 C11 118.6(5) . .
C7 C12 C5 122.5(5) . .
C11 C12 C5 118.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.863(5) .
C1 C2 1.383(7) .
C1 C3 1.384(7) 2_667
C2 F1 1.337(6) .
C2 C3 1.371(7) .
C3 F2 1.334(6) .
C3 C1 1.384(7) 2_667
C4 C5 1.350(7) .
C4 C10 1.433(7) 2_767
C4 H4 0.9500 .
C5 C12 1.426(7) .
C5 H5 0.9500 .
C7 C8 1.378(8) .
C7 C12 1.409(7) .
C7 H7 0.9500 .
C8 C9 1.383(8) .
C8 H8 0.9500 .
C9 C10 1.388(7) .
C9 H9 0.9500 .
C10 C11 1.424(7) .
C10 C4 1.433(7) 2_767
C11 C11 1.416(9) 2_767
C11 C12 1.420(7) .
