#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:31:33 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059450.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_7059450
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      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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-16 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.503(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.678(3)
_cell_length_b                   29.054(10)
_cell_length_c                   7.724(3)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.29
_cell_volume                     1514.2(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      119.96
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8609
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.804
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.354
_exptl_transmission_factor_min   0.272
_refine_diff_density_max         1.832
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0710
_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)+(0.0159P)²+32.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             2651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00678e2.cif
_cod_data_source_block           17gtu196_mct_10_0m
_cod_depositor_comments
;Adding full bibliography for 7059449--7059450.cif.

 Adding full bibliography for 7059449--7059450.cif.
;
_cod_database_code               7059450
_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_max   0.423
_shelx_estimated_absorpt_t_min   0.312
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.49320(16) 0.17316(4) 0.98058(15) 0.0256(3) Uani 1 1 d . . . . .
Br2 Br 0.02628(18) 0.18991(4) 0.24407(16) 0.0279(3) Uani 1 1 d . . . . .
Br3 Br -0.24085(18) 0.21073(4) 0.62289(18) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.1613(11) 0.0832(2) 0.7390(9) 0.0161(16) Uani 1 1 d . . . . .
N1 N 0.3042(15) -0.0794(4) 1.2134(13) 0.027(2) Uani 1 1 d . . . . .
N2 N 0.1785(14) 0.0550(4) 1.1705(13) 0.026(2) Uani 1 1 d . . . . .
C1 C 0.2901(15) -0.0601(4) 1.0816(15) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.1979(14) 0.0360(4) 1.0503(13) 0.012(2) Uani 1 1 d . . . . .
C3 C 0.2246(14) 0.0133(4) 0.9008(14) 0.014(2) Uani 1 1 d . . . . .
C4 C 0.2109(14) 0.0392(4) 0.7397(14) 0.014(2) Uani 1 1 d . . . . .
C5 C 0.2481(14) 0.0185(4) 0.5992(14) 0.016(2) Uani 1 1 d . . . . .
H5 H 0.2401 0.0358 0.4913 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2974(15) -0.0282(4) 0.6180(14) 0.018(2) Uani 1 1 d . . . . .
H6 H 0.3229 -0.0424 0.5215 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3101(15) -0.0544(4) 0.7729(14) 0.019(2) Uani 1 1 d . . . . .
H7 H 0.3447 -0.0860 0.7831 0.022 Uiso 1 1 calc R . . . .
C8 C 0.2718(13) -0.0340(4) 0.9132(13) 0.013(2) Uani 1 1 d . . . . .
C9 C 0.1699(16) 0.1148(3) 0.6010(14) 0.016(2) Uani 1 1 d . . . . .
H9A H 0.0818 0.1044 0.4645 0.019 Uiso 1 1 calc R . . . .
H9B H 0.3069 0.1169 0.6208 0.019 Uiso 1 1 calc R . . . .
C10 C 0.1016(15) 0.1620(4) 0.6375(14) 0.016(2) Uani 1 1 d . . . . .
C11 C 0.2031(13) 0.1735(4) 0.8598(14) 0.018(2) Uani 1 1 d . . . . .
H11A H 0.1611 0.1508 0.9281 0.021 Uiso 1 1 calc R . . . .
H11B H 0.1586 0.2043 0.8777 0.021 Uiso 1 1 calc R . . . .
C12 C 0.1499(15) 0.1995(4) 0.5286(14) 0.020(2) Uani 1 1 d . . . . .
H12A H 0.2954 0.2010 0.5822 0.024 Uiso 1 1 calc R . . . .
H12B H 0.1058 0.2295 0.5543 0.024 Uiso 1 1 calc R . . . .
C13 C -0.1221(16) 0.1574(4) 0.5653(16) 0.023(3) Uani 1 1 d . . . . .
H13A H -0.1451 0.1299 0.6272 0.028 Uiso 1 1 calc R . . . .
H13B H -0.1903 0.1523 0.4211 0.028 Uiso 1 1 calc R . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C9 120.3(8) . . ?
N1 C1 C8 178.5(12) . . ?
N2 C2 C3 178.8(11) . . ?
C4 C3 C2 119.0(10) . . ?
C8 C3 C2 121.8(9) . . ?
C8 C3 C4 119.1(9) . . ?
O1 C4 C3 114.6(9) . . ?
O1 C4 C5 125.4(9) . . ?
C5 C4 C3 120.0(10) . . ?
C4 C5 C6 119.2(9) . . ?
C7 C6 C5 121.9(9) . . ?
C6 C7 C8 119.3(10) . . ?
C3 C8 C1 118.7(9) . . ?
C7 C8 C1 120.7(10) . . ?
C7 C8 C3 120.5(9) . . ?
O1 C9 C10 107.1(8) . . ?
C9 C10 C11 111.2(8) . . ?
C12 C10 C9 109.9(9) . . ?
C12 C10 C11 109.3(8) . . ?
C12 C10 C13 112.6(9) . . ?
C13 C10 C9 106.0(8) . . ?
C13 C10 C11 107.8(8) . . ?
C10 C11 Br1 112.5(7) . . ?
C10 C12 Br2 113.7(7) . . ?
C10 C13 Br3 114.3(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.962(9) . ?
Br2 C12 1.954(10) . ?
Br3 C13 1.954(11) . ?
O1 C4 1.334(13) . ?
O1 C9 1.431(12) . ?
N1 C1 1.121(14) . ?
N2 C2 1.149(13) . ?
C1 C8 1.454(14) . ?
C2 C3 1.428(14) . ?
C3 C4 1.415(14) . ?
C3 C8 1.411(15) . ?
C4 C5 1.385(14) . ?
C5 C6 1.397(15) . ?
C6 C7 1.381(15) . ?
C7 C8 1.384(14) . ?
C9 C10 1.540(15) . ?
C10 C11 1.546(13) . ?
C10 C12 1.527(14) . ?
C10 C13 1.538(15) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C5 C6 -179.6(9) . . . . ?
O1 C9 C10 C11 46.3(11) . . . . ?
O1 C9 C10 C12 167.5(8) . . . . ?
O1 C9 C10 C13 -70.5(9) . . . . ?
C2 C3 C4 O1 -3.9(13) . . . . ?
C2 C3 C4 C5 176.1(9) . . . . ?
C2 C3 C8 C1 1.1(14) . . . . ?
C2 C3 C8 C7 -175.5(9) . . . . ?
C3 C4 C5 C6 0.5(14) . . . . ?
C4 O1 C9 C10 179.3(8) . . . . ?
C4 C3 C8 C1 178.5(9) . . . . ?
C4 C3 C8 C7 1.9(14) . . . . ?
C4 C5 C6 C7 0.1(15) . . . . ?
C5 C6 C7 C8 0.4(16) . . . . ?
C6 C7 C8 C1 -178.0(9) . . . . ?
C6 C7 C8 C3 -1.4(15) . . . . ?
C8 C3 C4 O1 178.6(8) . . . . ?
C8 C3 C4 C5 -1.5(14) . . . . ?
C9 O1 C4 C3 171.1(8) . . . . ?
C9 O1 C4 C5 -8.9(14) . . . . ?
C9 C10 C11 Br1 57.4(10) . . . . ?
C9 C10 C12 Br2 58.9(10) . . . . ?
C9 C10 C13 Br3 173.3(6) . . . . ?
C11 C10 C12 Br2 -178.8(7) . . . . ?
C11 C10 C13 Br3 54.2(10) . . . . ?
C12 C10 C11 Br1 -64.2(10) . . . . ?
C12 C10 C13 Br3 -66.4(10) . . . . ?
C13 C10 C11 Br1 173.1(7) . . . . ?
C13 C10 C12 Br2 -59.1(11) . . . . ?
