#------------------------------------------------------------------------------
#$Date: 2019-11-26 01:35:18 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/22/4132297.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_4132297
loop_
_publ_author_name
'Hashim, Mohamed I.'
'Le, Ha T. M.'
'Chen, Teng-Hao'
'Chen, Yu-Sheng'
'Daugulis, Olafs'
'Hsu, Chia-Wei'
'Jacobson, Allan J.'
'Kaveevivitchai, Watchareeya'
'Liang, Xiao'
'Makarenko, Tatyana'
'Miljanić, Ognjen Š'
'Popovs, Ilja'
'Tran, Hung Vu'
'Wang, Xiqu'
'Wu, Chia-Hua'
'Wu, Judy I.'
_publ_section_title
;
 Dissecting Porosity in Molecular Crystals: Influence of Geometry,
 Hydrogen Bonding, and [π···π] Stacking on the
 Solid-State Packing of Fluorinated Aromatics.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6014
_journal_page_last               6026
_journal_paper_doi               10.1021/jacs.8b02869
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C12 H6 F4 N4'
_chemical_formula_weight         282.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.711(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3834(3)
_cell_length_b                   5.7482(3)
_cell_length_c                   16.8992(8)
_cell_measurement_reflns_used    3114
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      5.28
_cell_volume                     518.21(5)
_computing_cell_refinement       'SAINT v7.60A (Bruker-Nonius, 2013)'
_computing_data_collection       'APEX2 v2013.4-1 (Bruker-Nonius, 2013)'
_computing_data_reduction        'SAINT v7.60A (Bruker-Nonius, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker DUO APEX II CCD'
_diffrn_measurement_method       'narrow frame'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_number            884
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         5.282
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SAINT v7.60A'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0294
_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)+(0.0309P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                876
_reflns_number_total             884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b02869_si_002.cif
_cod_data_source_block           2cif_K1434
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4132297
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.18871(15) 0.13223(14) 0.49852(5) 0.0196(3) Uani 1 1 d . .
F2 F 0.48904(15) 0.15504(14) 0.39068(5) 0.0190(3) Uani 1 1 d . .
N1 N -0.1265(2) 0.3549(2) 0.69316(7) 0.0167(3) Uani 1 1 d . .
H1N H -0.235(4) 0.268(4) 0.7171(11) 0.031(5) Uiso 1 1 d . .
N2 N -0.0562(2) 0.5680(2) 0.72237(7) 0.0176(3) Uani 1 1 d . .
C1 C -0.0020(3) 0.2914(3) 0.63320(8) 0.0164(3) Uani 1 1 d . .
H1 H -0.0213 0.1492 0.6044 0.020 Uiso 1 1 calc R U
C2 C 0.1605(2) 0.4715(2) 0.62082(8) 0.0139(3) Uani 1 1 d . .
C3 C 0.1170(3) 0.6389(3) 0.67873(8) 0.0161(3) Uani 1 1 d . .
H3 H 0.2012 0.7842 0.6856 0.019 Uiso 1 1 calc R U
C4 C 0.3321(2) 0.4862(2) 0.56050(8) 0.0135(3) Uani 1 1 d . .
C5 C 0.3427(3) 0.3178(2) 0.50160(8) 0.0143(3) Uani 1 1 d . .
C6 C 0.5014(3) 0.3307(2) 0.44415(8) 0.0141(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C1 N1 N2 112.23(12) . .
C3 N2 N1 104.94(11) . .
N1 C1 C2 107.46(13) . .
C1 C2 C3 103.69(12) . .
C1 C2 C4 127.97(13) . .
C3 C2 C4 128.33(13) . .
N2 C3 C2 111.68(13) . .
C6 C4 C5 113.33(13) 3_666 .
C6 C4 C2 123.58(13) 3_666 .
C5 C4 C2 123.09(13) . .
F1 C5 C6 116.84(12) . .
F1 C5 C4 119.52(12) . .
C6 C5 C4 123.63(13) . .
F2 C6 C5 116.83(12) . .
F2 C6 C4 120.14(12) . 3_666
C5 C6 C4 123.03(13) . 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.3477(16) .
F2 C6 1.3506(16) .
N1 C1 1.3385(18) .
N1 N2 1.3554(18) .
N2 C3 1.3278(19) .
C1 C2 1.390(2) .
C2 C3 1.414(2) .
C2 C4 1.4668(18) .
C4 C6 1.392(2) 3_666
C4 C5 1.395(2) .
C5 C6 1.379(2) .
C6 C4 1.392(2) 3_666
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_4
C1 N1 N2 C3 0.25(16) . .
N2 N1 C1 C2 -0.31(16) . .
N1 C1 C2 C3 0.23(15) . .
N1 C1 C2 C4 -178.44(13) . .
N1 N2 C3 C2 -0.09(16) . .
C1 C2 C3 N2 -0.09(16) . .
C4 C2 C3 N2 178.58(13) . .
C1 C2 C4 C6 -176.17(14) . 3_666
C3 C2 C4 C6 5.5(2) . 3_666
C1 C2 C4 C5 4.3(2) . .
C3 C2 C4 C5 -174.04(13) . .
C6 C4 C5 F1 -179.10(12) 3_666 .
C2 C4 C5 F1 0.5(2) . .
C6 C4 C5 C6 -0.2(2) 3_666 .
C2 C4 C5 C6 179.39(13) . .
F1 C5 C6 F2 -0.56(19) . .
C4 C5 C6 F2 -179.52(12) . .
F1 C5 C6 C4 179.15(12) . 3_666
C4 C5 C6 C4 0.2(2) . 3_666
