#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:31:33 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059449.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_7059449
loop_
_publ_author_name
'Canımkurbey, Betül'
'Taşkan, Mustafa Can'
'Demir, Sevde'
'Duygulu, Ercan'
'Atilla, Devrim'
'Yuksel, Fatma'
_publ_section_title
;
 Synthesis and investigation of the electrical properties of novel
 liquid-crystal phthalocyanines bearing triple branched alkylthia chains
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7424
_journal_page_last               7435
_journal_paper_doi               10.1039/D0NJ00678E
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C13 H11 Br3 N2 O'
_chemical_formula_sum            'C13 H11 Br3 N2 O'
_chemical_formula_weight         450.97
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2018-10-11 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                93.785(7)
_cell_angle_beta                 94.273(6)
_cell_angle_gamma                104.845(6)
_cell_formula_units_Z            2
_cell_length_a                   6.4706(6)
_cell_length_b                   7.4628(7)
_cell_length_c                   16.4827(16)
_cell_measurement_reflns_used    4110
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.0539
_cell_measurement_theta_min      2.8348
_cell_volume                     764.23(13)
_computing_cell_refinement       'APEX2 v2014.9-0 (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  'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11028
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.24
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    7.911
_exptl_absorpt_correction_T_max  0.60
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.686
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+1.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2150
_reflns_number_total             2687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00678e2.cif
_cod_data_source_block           I
_cod_depositor_comments
;Adding full bibliography for 7059449--7059450.cif.

 Adding full bibliography for 7059449--7059450.cif.
;
_cod_database_code               7059449
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7244(7) 0.9514(7) 0.8237(3) 0.0460(11) Uani d . . . 1 . .
H H1A 0.7116 1.0243 0.7779 0.055 Uiso calc U . R 1 . .
H H1B 0.8164 0.872 0.8099 0.055 Uiso calc U . R 1 . .
C C2 0.5033(9) 0.7138(8) 0.9081(3) 0.0530(13) Uani d . . . 1 . .
H H2A 0.3607 0.6316 0.9091 0.064 Uiso calc U . R 1 . .
H H2B 0.5338 0.797 0.9578 0.064 Uiso calc U . R 1 . .
C C3 0.5029(7) 0.8291(6) 0.8353(3) 0.0403(10) Uani d . . . 1 . .
C C4 0.3447(8) 0.9443(7) 0.8535(3) 0.0502(12) Uani d . . . 1 . .
H H4A 0.3974 1.0222 0.9041 0.06 Uiso calc U . R 1 . .
H H4B 0.2078 0.8604 0.8617 0.06 Uiso calc U . R 1 . .
C C5 0.4341(7) 0.7078(7) 0.7558(3) 0.0435(11) Uani d . . . 1 . .
H H5A 0.4387 0.7846 0.7104 0.052 Uiso calc U . R 1 . .
H H5B 0.5303 0.6289 0.7479 0.052 Uiso calc U . R 1 . .
C C6 0.1231(8) 0.4815(6) 0.6927(3) 0.0412(10) Uani d . . . 1 . .
C C7 -0.0890(8) 0.3782(7) 0.6972(3) 0.0457(11) Uani d . . . 1 . .
H H7 -0.1545 0.3895 0.7449 0.055 Uiso calc U . R 1 . .
C C8 -0.2009(8) 0.2610(7) 0.6323(3) 0.0464(12) Uani d . . . 1 . .
H H8 -0.3413 0.1928 0.6363 0.056 Uiso calc U . R 1 . .
C C9 -0.1058(8) 0.2433(6) 0.5607(3) 0.0417(11) Uani d . . . 1 . .
C C10 0.1063(7) 0.3448(6) 0.5562(3) 0.0385(10) Uani d . . . 1 . .
C C11 0.2199(7) 0.4639(6) 0.6213(3) 0.0421(11) Uani d . . . 1 . .
H H11 0.3604 0.5319 0.6174 0.051 Uiso calc U . R 1 . .
C C12 0.2059(8) 0.3271(7) 0.4815(3) 0.0479(12) Uani d . . . 1 . .
C C13 -0.2211(8) 0.1259(7) 0.4908(3) 0.0500(12) Uani d . . . 1 . .
N N1 0.2814(8) 0.3122(7) 0.4223(3) 0.0685(14) Uani d . . . 1 . .
N N2 -0.3107(8) 0.0353(8) 0.4343(3) 0.0725(14) Uani d . . . 1 . .
O O1 0.2178(5) 0.5948(5) 0.75954(19) 0.0498(8) Uani d . . . 1 . .
Br Br1 0.29963(11) 1.10053(10) 0.76888(4) 0.0730(2) Uani d . . . 1 . .
Br Br2 0.86213(9) 1.12043(8) 0.91905(3) 0.0629(2) Uani d . . . 1 . .
Br Br3 0.70892(13) 0.56520(10) 0.90828(4) 0.0783(2) Uani d . . . 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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 Br2 . . 114.3(3) ?
C3 C1 H1A . . 108.7 ?
Br2 C1 H1A . . 108.7 ?
C3 C1 H1B . . 108.7 ?
Br2 C1 H1B . . 108.7 ?
H1A C1 H1B . . 107.6 ?
C3 C2 Br3 . . 114.5(3) ?
C3 C2 H2A . . 108.6 ?
Br3 C2 H2A . . 108.6 ?
C3 C2 H2B . . 108.6 ?
Br3 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
C5 C3 C1 . . 104.5(4) ?
C5 C3 C2 . . 111.8(4) ?
C1 C3 C2 . . 113.0(4) ?
C5 C3 C4 . . 111.7(4) ?
C1 C3 C4 . . 111.9(4) ?
C2 C3 C4 . . 104.1(4) ?
C3 C4 Br1 . . 114.2(3) ?
C3 C4 H4A . . 108.7 ?
Br1 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
Br1 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
O1 C5 C3 . . 108.2(4) ?
O1 C5 H5A . . 110.1 ?
C3 C5 H5A . . 110.1 ?
O1 C5 H5B . . 110.1 ?
C3 C5 H5B . . 110.1 ?
H5A C5 H5B . . 108.4 ?
O1 C6 C11 . . 124.6(4) ?
O1 C6 C7 . . 116.1(4) ?
C11 C6 C7 . . 119.3(4) ?
C8 C7 C6 . . 120.8(4) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 120.2(4) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C8 C9 C10 . . 119.1(4) ?
C8 C9 C13 . . 121.5(4) ?
C10 C9 C13 . . 119.4(4) ?
C11 C10 C9 . . 121.0(4) ?
C11 C10 C12 . . 119.7(4) ?
C9 C10 C12 . . 119.2(4) ?
C10 C11 C6 . . 119.5(4) ?
C10 C11 H11 . . 120.2 ?
C6 C11 H11 . . 120.2 ?
N1 C12 C10 . . 179.1(6) ?
N2 C13 C9 . . 178.6(6) ?
C6 O1 C5 . . 117.4(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 . 1.523(6) ?
C1 Br2 . 1.952(5) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.523(6) ?
C2 Br3 . 1.938(5) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C5 . 1.511(6) ?
C3 C4 . 1.529(6) ?
C4 Br1 . 1.928(5) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 O1 . 1.445(6) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 O1 . 1.347(6) ?
C6 C11 . 1.388(6) ?
C6 C7 . 1.402(7) ?
C7 C8 . 1.367(7) ?
C7 H7 . 0.93 ?
C8 C9 . 1.386(7) ?
C8 H8 . 0.93 ?
C9 C10 . 1.397(6) ?
C9 C13 . 1.434(7) ?
C10 C11 . 1.379(7) ?
C10 C12 . 1.446(7) ?
C11 H11 . 0.93 ?
C12 N1 . 1.135(6) ?
C13 N2 . 1.138(7) ?
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
_geom_hbond_publ_flag
C11 H11 N1 2_666 0.93 2.47 3.385(7) 168.5 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br2 C1 C3 C5 . . . . -178.0(3) ?
Br2 C1 C3 C2 . . . . -56.2(5) ?
Br2 C1 C3 C4 . . . . 61.0(5) ?
Br3 C2 C3 C5 . . . . 64.2(5) ?
Br3 C2 C3 C1 . . . . -53.4(5) ?
Br3 C2 C3 C4 . . . . -175.1(4) ?
C5 C3 C4 Br1 . . . . -56.9(5) ?
C1 C3 C4 Br1 . . . . 59.9(5) ?
C2 C3 C4 Br1 . . . . -177.7(3) ?
C1 C3 C5 O1 . . . . -176.3(4) ?
C2 C3 C5 O1 . . . . 61.1(5) ?
C4 C3 C5 O1 . . . . -55.1(5) ?
O1 C6 C7 C8 . . . . 179.1(5) ?
C11 C6 C7 C8 . . . . 0.0(7) ?
C6 C7 C8 C9 . . . . -0.3(8) ?
C7 C8 C9 C10 . . . . 0.9(7) ?
C7 C8 C9 C13 . . . . -178.1(5) ?
C8 C9 C10 C11 . . . . -1.1(7) ?
C13 C9 C10 C11 . . . . 177.9(5) ?
C8 C9 C10 C12 . . . . -179.9(5) ?
C13 C9 C10 C12 . . . . -0.9(7) ?
C9 C10 C11 C6 . . . . 0.8(7) ?
C12 C10 C11 C6 . . . . 179.5(4) ?
O1 C6 C11 C10 . . . . -179.3(4) ?
C7 C6 C11 C10 . . . . -0.2(7) ?
C11 C6 O1 C5 . . . . 1.1(7) ?
C7 C6 O1 C5 . . . . -178.0(4) ?
C3 C5 O1 C6 . . . . 177.3(4) ?
