#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/28/7202802.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_7202802
loop_
_publ_author_name
'Dobrzycki, Lukasz'
'Woźniak, Krzysztof'
_publ_section_title
;
 Structural consequences of benzidine dihydrochloride substitution in
 the solid state
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1029
_journal_paper_doi               10.1039/b702072d
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C12 H4 F8 N2'
_chemical_formula_weight         328.17
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   10.7907(4)
_cell_length_b                   8.9839(4)
_cell_length_c                   23.1750(8)
_cell_measurement_temperature    104(2)
_cell_volume                     2246.64(15)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
;
_computing_molecular_graphics    Diamond
_computing_publication_material  SHELXTL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      104(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31614
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        2
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0273
_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)+(0.0534P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                2059
_reflns_number_total             2814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b702072d.txt
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7202802
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
F2 F 0.81995(6) 0.24325(7) 0.20346(3) 0.02217(18) Uani 1 1 d . . .
F3 F 0.83150(6) 0.24482(8) 0.31932(3) 0.02108(18) Uani 1 1 d . . .
F5 F 0.46565(6) -0.04349(8) 0.32636(3) 0.02052(17) Uani 1 1 d . . .
F6 F 0.45903(6) -0.05019(7) 0.21205(3) 0.02108(17) Uani 1 1 d . . .
F8 F 0.46991(6) 0.21842(7) 0.51582(3) 0.02080(17) Uani 1 1 d . . .
F9 F 0.45829(6) 0.22066(7) 0.40001(3) 0.02125(17) Uani 1 1 d . . .
F11 F 0.85077(6) -0.01320(8) 0.39236(3) 0.02030(17) Uani 1 1 d . . .
F12 F 0.86192(6) -0.00986(8) 0.50766(3) 0.01949(17) Uani 1 1 d . . .
N1 N 0.63724(10) 0.08845(12) 0.14434(4) 0.0196(2) Uani 1 1 d . . .
N2 N 0.67401(10) 0.11491(12) 0.57396(4) 0.0187(2) Uani 1 1 d . . .
C1 C 0.63880(10) 0.09766(12) 0.20435(5) 0.0157(2) Uani 1 1 d . . .
C2 C 0.73162(11) 0.17143(12) 0.23417(4) 0.0161(2) Uani 1 1 d . . .
C3 C 0.73682(10) 0.17283(12) 0.29356(5) 0.0155(2) Uani 1 1 d . . .
C4 C 0.64802(10) 0.10292(12) 0.32745(4) 0.0147(2) Uani 1 1 d . . .
C5 C 0.55522(10) 0.03044(12) 0.29739(5) 0.0152(2) Uani 1 1 d . . .
C6 C 0.55032(10) 0.02658(12) 0.23810(4) 0.0156(2) Uani 1 1 d . . .
C7 C 0.66736(10) 0.10742(12) 0.51443(4) 0.0145(2) Uani 1 1 d . . .
C8 C 0.56530(10) 0.16256(12) 0.48465(5) 0.0155(2) Uani 1 1 d . . .
C9 C 0.55921(10) 0.16178(12) 0.42537(5) 0.0152(2) Uani 1 1 d . . .
C10 C 0.65400(10) 0.10382(12) 0.39150(4) 0.0143(2) Uani 1 1 d . . .
C11 C 0.75547(10) 0.04770(13) 0.42153(4) 0.0149(2) Uani 1 1 d . . .
C12 C 0.76223(10) 0.04903(12) 0.48098(4) 0.0150(2) Uani 1 1 d . . .
H1A H 0.6696(14) 0.1683(18) 0.1253(6) 0.042(4) Uiso 1 1 d . . .
H1B H 0.5679(13) 0.0577(15) 0.1313(5) 0.026(4) Uiso 1 1 d . . .
H2A H 0.6037(15) 0.1075(17) 0.5906(6) 0.046(5) Uiso 1 1 d . . .
H2B H 0.7309(14) 0.0609(16) 0.5895(5) 0.027(4) Uiso 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'
N N 0.0061 0.0033 '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'
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
C1 N1 H1A 115.5(9) . . ?
C1 N1 H1B 112.6(9) . . ?
H1A N1 H1B 114.8(13) . . ?
C7 N2 H2A 113.6(10) . . ?
C7 N2 H2B 115.2(9) . . ?
H2A N2 H2B 113.7(13) . . ?
C2 C1 C6 115.83(10) . . ?
C2 C1 N1 122.34(10) . . ?
C6 C1 N1 121.75(10) . . ?
F2 C2 C3 119.50(10) . . ?
F2 C2 C1 118.35(9) . . ?
C3 C2 C1 122.15(10) . . ?
F3 C3 C2 118.52(10) . . ?
F3 C3 C4 119.30(9) . . ?
C2 C3 C4 122.19(10) . . ?
C5 C4 C3 115.33(9) . . ?
C5 C4 C10 122.49(9) . . ?
C3 C4 C10 122.17(10) . . ?
F5 C5 C6 117.15(10) . . ?
F5 C5 C4 119.95(9) . . ?
C6 C5 C4 122.88(10) . . ?
F6 C6 C5 119.29(10) . . ?
F6 C6 C1 119.07(9) . . ?
C5 C6 C1 121.62(10) . . ?
N2 C7 C12 122.51(10) . . ?
N2 C7 C8 121.24(10) . . ?
C12 C7 C8 116.22(9) . . ?
F8 C8 C9 119.90(10) . . ?
F8 C8 C7 117.98(9) . . ?
C9 C8 C7 122.12(10) . . ?
F9 C9 C8 118.22(9) . . ?
F9 C9 C10 119.73(9) . . ?
C8 C9 C10 122.05(10) . . ?
C9 C10 C11 115.59(9) . . ?
C9 C10 C4 122.28(9) . . ?
C11 C10 C4 122.12(9) . . ?
F11 C11 C12 117.68(9) . . ?
F11 C11 C10 119.78(9) . . ?
C12 C11 C10 122.53(10) . . ?
F12 C12 C11 119.77(9) . . ?
F12 C12 C7 118.74(9) . . ?
C11 C12 C7 121.48(10) . . ?
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
F2 C2 1.3533(12) . ?
F3 C3 1.3485(12) . ?
F5 C5 1.3512(12) . ?
F6 C6 1.3456(12) . ?
F8 C8 1.3540(12) . ?
F9 C9 1.3458(12) . ?
F11 C11 1.3468(12) . ?
F12 C12 1.3488(12) . ?
N1 C1 1.3932(14) . ?
N1 H1A 0.912(16) . ?
N1 H1B 0.854(14) . ?
N2 C7 1.3832(14) . ?
N2 H2A 0.853(16) . ?
N2 H2B 0.862(15) . ?
C1 C2 1.3856(15) . ?
C1 C6 1.3897(15) . ?
C2 C3 1.3776(15) . ?
C3 C4 1.3889(15) . ?
C4 C5 1.3828(15) . ?
C4 C10 1.4859(14) . ?
C5 C6 1.3755(15) . ?
C7 C12 1.3870(15) . ?
C7 C8 1.3909(15) . ?
C8 C9 1.3753(15) . ?
C9 C10 1.3905(15) . ?
C10 C11 1.3920(15) . ?
C11 C12 1.3797(14) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.912(16) 2.283(16) 3.1497(15) 158.7(13) 7_565
N1 H1B F11 0.854(14) 2.489(14) 3.3337(13) 170.6(12) 6_556
N2 H2A F5 0.853(16) 2.144(15) 2.8319(11) 137.4(13) 5_656
N2 H2B N1 0.862(15) 2.332(15) 3.1854(15) 170.5(12) 2_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 -179.68(9) . . . . ?
N1 C1 C2 F2 3.50(16) . . . . ?
C6 C1 C2 C3 0.74(16) . . . . ?
N1 C1 C2 C3 -176.09(11) . . . . ?
F2 C2 C3 F3 -0.83(15) . . . . ?
C1 C2 C3 F3 178.75(10) . . . . ?
F2 C2 C3 C4 179.12(10) . . . . ?
C1 C2 C3 C4 -1.31(17) . . . . ?
F3 C3 C4 C5 -179.26(9) . . . . ?
C2 C3 C4 C5 0.79(16) . . . . ?
F3 C3 C4 C10 -0.37(15) . . . . ?
C2 C3 C4 C10 179.69(10) . . . . ?
C3 C4 C5 F5 178.73(9) . . . . ?
C10 C4 C5 F5 -0.17(16) . . . . ?
C3 C4 C5 C6 0.21(16) . . . . ?
C10 C4 C5 C6 -178.69(10) . . . . ?
F5 C5 C6 F6 -0.57(15) . . . . ?
C4 C5 C6 F6 177.99(10) . . . . ?
F5 C5 C6 C1 -179.29(9) . . . . ?
C4 C5 C6 C1 -0.74(18) . . . . ?
C2 C1 C6 F6 -178.48(9) . . . . ?
N1 C1 C6 F6 -1.63(16) . . . . ?
C2 C1 C6 C5 0.25(16) . . . . ?
N1 C1 C6 C5 177.10(10) . . . . ?
N2 C7 C8 F8 -2.70(15) . . . . ?
C12 C7 C8 F8 179.01(9) . . . . ?
N2 C7 C8 C9 177.24(10) . . . . ?
C12 C7 C8 C9 -1.06(16) . . . . ?
F8 C8 C9 F9 1.54(15) . . . . ?
C7 C8 C9 F9 -178.40(10) . . . . ?
F8 C8 C9 C10 -179.11(9) . . . . ?
C7 C8 C9 C10 0.95(17) . . . . ?
F9 C9 C10 C11 178.94(10) . . . . ?
C8 C9 C10 C11 -0.40(16) . . . . ?
F9 C9 C10 C4 -0.55(16) . . . . ?
C8 C9 C10 C4 -179.89(10) . . . . ?
C5 C4 C10 C9 -59.78(15) . . . . ?
C3 C4 C10 C9 121.40(12) . . . . ?
C5 C4 C10 C11 120.77(12) . . . . ?
C3 C4 C10 C11 -58.05(15) . . . . ?
C9 C10 C11 F11 178.79(9) . . . . ?
C4 C10 C11 F11 -1.72(16) . . . . ?
C9 C10 C11 C12 0.03(16) . . . . ?
C4 C10 C11 C12 179.52(10) . . . . ?
F11 C11 C12 F12 -0.17(16) . . . . ?
C10 C11 C12 F12 178.61(10) . . . . ?
F11 C11 C12 C7 -178.98(10) . . . . ?
C10 C11 C12 C7 -0.20(18) . . . . ?
N2 C7 C12 F12 3.59(16) . . . . ?
C8 C7 C12 F12 -178.14(10) . . . . ?
N2 C7 C12 C11 -177.59(11) . . . . ?
C8 C7 C12 C11 0.69(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63751
