#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:42:31 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/08/7230847.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_7230847
loop_
_publ_author_name
'Ateş, Özge Dilara'
'Zorlu, Yunus'
'Kanmazalp, Sibel Demir'
'Chumakov, Yurii'
'Gürek, Ayşe Gül'
'Ayhan, Mehmet Menaf'
_publ_section_title
;
 Halogen bonding driven crystal engineering of iodophthalonitrile
 derivatives
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              3858
_journal_paper_doi               10.1039/C8CE00594J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C8 H2 I2 N2'
_chemical_formula_sum            'C8 H2 I2 N2'
_chemical_formula_weight         379.92
_chemical_name_common            Phthalonitrile
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-11-30 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.091(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.305(7)
_cell_length_b                   4.1552(14)
_cell_length_c                   21.526(7)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      22.1294
_cell_measurement_theta_min      1.9258
_cell_volume                     1898.1(11)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8570
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    6.572
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.078
_refine_diff_density_max         2.201
_refine_diff_density_min         -3.710
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0682
_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)+(0.0873P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                2214
_reflns_number_total             3260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00594j2.cif
_cod_data_source_block           I_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7230844--7230847.cif.'
_cod_database_code               7230847
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.3730(6) 0.665(4) 0.2077(7) 0.026(4) Uani d . . 1
C C2 0.4187(5) 0.604(3) 0.2592(6) 0.020(2) Uani d U . 1
C C3 0.4019(5) 0.459(3) 0.3129(6) 0.018(2) Uani d U . 1
C C4 0.4468(5) 0.408(3) 0.3623(6) 0.021(2) Uani d U . 1
C C5 0.5102(5) 0.501(4) 0.3571(6) 0.025(2) Uani d U . 1
H H5 0.5413 0.4647 0.3907 0.03 Uiso calc U R 1
C C6 0.5263(6) 0.642(3) 0.3029(6) 0.024(2) Uani d U . 1
H H6 0.5688 0.7048 0.2996 0.029 Uiso calc U R 1
C C7 0.4815(6) 0.696(3) 0.2528(6) 0.022(2) Uani d U . 1
C C8 0.4985(6) 0.862(4) 0.1980(7) 0.030(4) Uani d . . 1
C C9 0.3198(6) 0.991(3) 0.5798(5) 0.020(3) Uani d . . 1
C C10 0.2516(5) 1.013(3) 0.5825(6) 0.019(2) Uani d U . 1
C C11 0.2122(6) 0.881(3) 0.5348(6) 0.018(2) Uani d U . 1
C C12 0.1458(5) 0.923(3) 0.5389(6) 0.019(2) Uani d U . 1
C C13 0.1233(6) 1.069(3) 0.5912(6) 0.021(2) Uani d U . 1
H H13 0.0792 1.0848 0.5944 0.025 Uiso calc U R 1
C C14 0.1641(6) 1.189(3) 0.6372(6) 0.022(2) Uani d U . 1
H H14 0.1482 1.2919 0.6719 0.026 Uiso calc U R 1
C C15 0.2294(6) 1.162(3) 0.6343(6) 0.0214(19) Uani d U . 1
C C16 0.2733(7) 1.290(4) 0.6812(7) 0.028(2) Uani d U . 1
I I1 0.30805(4) 0.3214(2) 0.31817(4) 0.0236(3) Uani d . . 1
I I2 0.42670(4) 0.2033(2) 0.44677(4) 0.0272(3) Uani d . . 1
I I3 0.24948(4) 0.6735(2) 0.45913(4) 0.0252(3) Uani d . . 1
I I4 0.08091(4) 0.7374(2) 0.46909(5) 0.0288(3) Uani d . . 1
N N1 0.5128(5) 0.986(3) 0.1548(6) 0.040(4) Uani d . . 1
N N2 0.3362(6) 0.724(3) 0.1681(6) 0.034(3) Uani d . . 1
N N3 0.3724(5) 0.998(3) 0.5801(6) 0.037(3) Uani d . . 1
N N4 0.3083(6) 1.393(4) 0.7187(6) 0.047(3) Uani d U . 1
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'
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
N2 C1 C2 177.2(16)
C3 C2 C7 121.3(12)
C3 C2 C1 121.3(11)
C7 C2 C1 117.4(12)
C2 C3 C4 119.9(11)
C2 C3 I1 119.0(9)
C4 C3 I1 121.1(9)
C3 C4 C5 119.8(12)
C3 C4 I2 123.4(8)
C5 C4 I2 116.8(9)
C6 C5 C4 119.6(12)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C7 121.3(11)
C5 C6 H6 119.3
C7 C6 H6 119.3
C6 C7 C2 118.1(12)
C6 C7 C8 120.5(11)
C2 C7 C8 121.3(13)
N1 C8 C7 178.4(16)
N3 C9 C10 174.3(17)
C11 C10 C15 123.0(11)
C11 C10 C9 119.0(11)
C15 C10 C9 117.9(12)
C10 C11 C12 116.3(11)
C10 C11 I3 120.1(8)
C12 C11 I3 123.4(10)
C13 C12 C11 120.8(12)
C13 C12 I4 119.0(9)
C11 C12 I4 120.1(9)
C14 C13 C12 120.2(11)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 121.0(12)
C13 C14 H14 119.5
C15 C14 H14 119.5
C10 C15 C14 118.5(12)
C10 C15 C16 119.1(11)
C14 C15 C16 122.4(12)
N4 C16 C15 180.(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.133(19)
C1 C2 1.43(2)
C2 C3 1.379(17)
C2 C7 1.412(16)
C3 C4 1.381(17)
C3 I1 2.092(11)
C4 C5 1.417(15)
C4 I2 2.087(13)
C5 C6 1.376(18)
C5 H5 0.95
C6 C7 1.393(19)
C6 H6 0.95
C7 C8 1.440(19)
C8 N1 1.128(17)
C9 N3 1.121(15)
C9 C10 1.462(15)
C10 C11 1.381(18)
C10 C15 1.393(17)
C11 C12 1.434(16)
C11 I3 2.064(12)
C12 C13 1.401(17)
C12 I4 2.097(13)
C13 C14 1.350(18)
C13 H13 0.95
C14 C15 1.404(17)
C14 H14 0.95
C15 C16 1.42(2)
C16 N4 1.132(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 N3 3_666 0.95 2.69 3.431(18) 134.9
C13 H13 N1 4_586 0.95 2.68 3.376(16) 130.3
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
C7 C2 C3 C4 2.(2)
C1 C2 C3 C4 -178.9(13)
C7 C2 C3 I1 -178.8(10)
C1 C2 C3 I1 0.7(18)
C2 C3 C4 C5 -1.(2)
I1 C3 C4 C5 179.2(10)
C2 C3 C4 I2 178.1(10)
I1 C3 C4 I2 -1.5(17)
C3 C4 C5 C6 0.(2)
I2 C4 C5 C6 -178.8(10)
C4 C5 C6 C7 0.(2)
C5 C6 C7 C2 1.(2)
C5 C6 C7 C8 176.4(13)
C3 C2 C7 C6 -1.(2)
C1 C2 C7 C6 179.2(13)
C3 C2 C7 C8 -177.0(13)
C1 C2 C7 C8 3.(2)
C15 C10 C11 C12 3.9(19)
C9 C10 C11 C12 -177.5(12)
C15 C10 C11 I3 178.9(10)
C9 C10 C11 I3 -2.6(17)
C10 C11 C12 C13 -4.5(19)
I3 C11 C12 C13 -179.3(9)
C10 C11 C12 I4 179.5(9)
I3 C11 C12 I4 4.8(15)
C11 C12 C13 C14 3.(2)
I4 C12 C13 C14 179.4(10)
C12 C13 C14 C15 -2.(2)
C11 C10 C15 C14 -2.(2)
C9 C10 C15 C14 179.3(13)
C11 C10 C15 C16 179.7(13)
C9 C10 C15 C16 1.1(19)
C13 C14 C15 C10 1.(2)
C13 C14 C15 C16 178.9(13)
