#------------------------------------------------------------------------------
#$Date: 2019-09-28 03:36:20 +0300 (Sat, 28 Sep 2019) $
#$Revision: 218890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/42/7234214.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_7234214
loop_
_publ_author_name
'Torubaev, Yury'
'Skabitskiy, Ivan V.'
_publ_section_title
;
 The Energy Frameworks of Aufbau Synthon Modules in 4-Cyanopyridine
 Co-crystals.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01174A
_journal_year                    2019
_chemical_formula_moiety         'C4 F8 I2, 2(C6 H4 N2)'
_chemical_formula_sum            'C16 H8 F8 I2 N4'
_chemical_formula_weight         662.06
_chemical_name_systematic        '4-cyanopyridine 1,4 diiodooctafluorobutane'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2019-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-15 deposited with the CCDC.    2019-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                98.37(5)
_cell_angle_beta                 93.01(4)
_cell_angle_gamma                98.12(6)
_cell_formula_units_Z            1
_cell_length_a                   5.166(5)
_cell_length_b                   5.694(6)
_cell_length_c                   17.261(17)
_cell_measurement_reflns_used    242
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     495.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7197
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.989
_diffrn_reflns_theta_min         2.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0916 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.6526.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_description       prism
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.968
_refine_diff_density_min         -1.567
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.265
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0292
_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)+(0.0017P)²+0.9061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             2558
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c9ce01174a2.cif
_cod_data_source_block           1
_cod_original_cell_volume        495.9(8)
_cod_database_code               7234214
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
I1 I 0.96264(4) 0.40170(4) 0.19387(2) 0.02078(7) Uani 1 1 d .
C2 C 0.3243(6) 0.9474(5) 0.37489(18) 0.0196(6) Uani 1 1 d .
N1 N 0.6795(5) 0.6714(5) 0.30812(16) 0.0235(6) Uani 1 1 d .
C3 C 0.4247(7) 0.9893(6) 0.30480(19) 0.0236(6) Uani 1 1 d .
H3 H 0.375938 1.114266 0.278819 0.028 Uiso 1 1 calc R
C4 C 0.5984(7) 0.8438(6) 0.27351(19) 0.0243(7) Uani 1 1 d .
H4 H 0.663321 0.868895 0.224412 0.029 Uiso 1 1 calc R
C1 C 0.1409(7) 1.0940(6) 0.40865(19) 0.0239(6) Uani 1 1 d .
C6 C 0.4026(6) 0.7651(6) 0.41140(19) 0.0228(6) Uani 1 1 d .
H6 H 0.334444 0.730613 0.459231 0.027 Uiso 1 1 calc R
C5 C 0.5834(7) 0.6346(6) 0.37605(19) 0.0243(7) Uani 1 1 d .
H5 H 0.641647 0.512651 0.401647 0.029 Uiso 1 1 calc R
N2 N -0.0017(6) 1.2142(6) 0.43484(18) 0.0311(7) Uani 1 1 d .
C7 C 1.1457(6) 0.2184(6) 0.09866(18) 0.0228(6) Uani 1 1 d .
C8 C 0.9435(6) 0.0671(6) 0.03591(17) 0.0187(6) Uani 1 1 d .
F3 F 0.7984(4) -0.0937(4) 0.07072(11) 0.0317(5) Uani 1 1 d .
F2 F 1.3003(4) 0.3786(4) 0.06594(13) 0.0381(5) Uani 1 1 d .
F4 F 0.7881(4) 0.2130(4) 0.01036(12) 0.0327(5) Uani 1 1 d .
F1 F 1.3001(4) 0.0738(4) 0.12655(12) 0.0363(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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_3
C3 C2 C1 119.4(3) .
C3 C2 C6 119.2(3) .
C6 C2 C1 121.4(3) .
C4 N1 C5 117.6(3) .
C2 C3 C4 118.0(3) .
N1 C4 C3 123.7(3) .
N2 C1 C2 178.6(4) .
C5 C6 C2 118.0(3) .
N1 C5 C6 123.4(3) .
C8 C7 I1 112.1(2) .
F2 C7 I1 109.5(2) .
F2 C7 C8 109.6(3) .
F2 C7 F1 107.0(3) .
F1 C7 I1 109.6(2) .
F1 C7 C8 108.9(3) .
C7 C8 C8 115.9(3) 2_755
F3 C8 C7 107.5(3) .
F3 C8 C8 108.5(3) 2_755
F3 C8 F4 108.4(3) .
F4 C8 C7 107.9(3) .
F4 C8 C8 108.3(3) 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C7 2.151(3) .
C2 C3 1.380(5) .
C2 C1 1.440(5) .
C2 C6 1.386(5) .
N1 C4 1.325(4) .
N1 C5 1.330(4) .
C3 C4 1.384(5) .
C1 N2 1.141(4) .
C6 C5 1.386(5) .
C7 C8 1.537(4) .
C7 F2 1.334(4) .
C7 F1 1.344(4) .
C8 C8 1.545(6) 2_755
C8 F3 1.332(4) .
C8 F4 1.337(4) .
