#------------------------------------------------------------------------------
#$Date: 2019-05-08 01:10:40 +0300 (Wed, 08 May 2019) $
#$Revision: 214975 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/33/7123399.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_7123399
loop_
_publ_author_name
'Nieland, Esther'
'Topornicki, Thomas'
'Kunde, Tom'
'Schmidt, Bernd M.'
_publ_section_title
;
 [2+2] Halogen-bonded boxes employing azobenzenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03061A
_journal_year                    2019
_chemical_formula_moiety         'C12 H4 F4 I2 N2 '
_chemical_formula_sum            'C12 H4 F4 I2 N2'
_chemical_formula_weight         505.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-12 deposited with the CCDC.    2019-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.213(2)
_cell_length_b                   4.470(2)
_cell_length_c                   13.278(3)
_cell_measurement_reflns_used    5813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      3.08
_cell_volume                     664.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7433
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    4.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.530
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.5608
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0136
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0160P)²+0.5087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0329
_refine_ls_wR_factor_ref         0.0335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1390
_reflns_number_total             1469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03061a2.cif
_cod_data_source_block           mo_h18_038_0m_a
_cod_original_cell_volume        664.1(4)
_cod_original_formula_sum        'C12 H4 F4 I2 N2 '
_cod_database_code               7123399
_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.
;
_shelx_estimated_absorpt_t_min   0.334
_shelx_estimated_absorpt_t_max   0.783
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.08223(2) 0.10029(3) 0.65951(2) 0.01328(5) Uani 1 1 d . .
F1 F 0.26586(11) 0.7491(3) 0.36639(9) 0.0259(3) Uani 1 1 d . .
C1 C 0.38459(16) 0.7401(4) 0.51902(13) 0.0115(3) Uani 1 1 d . .
N1 N 0.46078(15) 0.9396(4) 0.47109(13) 0.0151(3) Uani 1 1 d . .
F2 F 0.49581(11) 0.6872(3) 0.67582(9) 0.0230(3) Uani 1 1 d . .
C2 C 0.28282(18) 0.6450(4) 0.46095(14) 0.0144(4) Uani 1 1 d . .
C3 C 0.19725(17) 0.4549(4) 0.49624(14) 0.0136(4) Uani 1 1 d . .
H3 H 0.1296 0.3950 0.4544 0.016 Uiso 1 1 calc R U
C6 C 0.39797(17) 0.6210(4) 0.61690(14) 0.0124(4) Uani 1 1 d . .
C5 C 0.31542(17) 0.4330(4) 0.65621(14) 0.0127(4) Uani 1 1 d . .
H5 H 0.3271 0.3583 0.7231 0.015 Uiso 1 1 calc R U
C4 C 0.21428(16) 0.3551(4) 0.59526(14) 0.0106(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
I I -0.4742 1.8119 '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'
C C 0.0033 0.0016 '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'
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_1
C2 C1 C6 115.44(17) .
C2 C1 N1 115.95(16) .
C6 C1 N1 128.60(17) .
N1 N1 C1 114.6(2) 3_676
F1 C2 C3 118.00(17) .
F1 C2 C1 118.14(17) .
C3 C2 C1 123.84(17) .
C2 C3 C4 117.40(17) .
C2 C3 H3 121.3 .
C4 C3 H3 121.3 .
F2 C6 C5 117.31(17) .
F2 C6 C1 119.49(17) .
C5 C6 C1 123.19(17) .
C6 C5 C4 118.27(17) .
C6 C5 H5 120.9 .
C4 C5 H5 120.9 .
C3 C4 C5 121.77(17) .
C3 C4 I1 120.14(14) .
C5 C4 I1 118.01(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C4 2.0924(19) .
F1 C2 1.341(2) .
C1 C2 1.402(3) .
C1 C6 1.404(3) .
C1 N1 1.414(2) .
N1 N1 1.253(3) 3_676
F2 C6 1.339(2) .
C2 C3 1.385(3) .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C6 C5 1.377(3) .
C5 C4 1.395(3) .
C5 H5 0.9500 .
