#------------------------------------------------------------------------------
#$Date: 2019-09-20 12:26:41 +0300 (Fri, 20 Sep 2019) $
#$Revision: 218591 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/40/7234009.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_7234009
loop_
_publ_author_name
'N. Venkatramaiah'
'Deisy M. G. C. Rocha'
'P. Srikanth'
'Filipe A. Almeida Paz'
'Joao P. C. Tome'
_publ_section_title
;
 Synthesis and photophysical characterization of dimethylamine-derived
 Zn(ii)phthalocyanines: exploring their potential as selective
 chemosensors for trinitrophenol
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1056
_journal_page_last               1067
_journal_paper_doi               10.1039/C4TC02253J
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C10 H8 F N3'
_chemical_formula_sum            'C10 H8 F N3'
_chemical_formula_weight         189.19
_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
_cell_angle_alpha                108.015(10)
_cell_angle_beta                 103.788(10)
_cell_angle_gamma                92.762(10)
_cell_formula_units_Z            2
_cell_length_a                   6.4282(18)
_cell_length_b                   8.584(2)
_cell_length_c                   8.968(3)
_cell_measurement_reflns_used    3458
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.48
_cell_volume                     453.0(2)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 2012.4 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13052
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         3.554
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS V2012/1 (Bruker AXS Inc.)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       Block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.2544
_exptl_transmission_factor_min   0.2161
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0553
_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)+(0.0341P)²+0.3185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                891
_reflns_number_total             1636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

data item '_space_group_crystal_system' value 'Triclinic' was changed
to 'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7234009
_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   0.980
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2014/6
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1710(3) 0.8931(2) 0.5089(2) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.6007(4) 0.9347(3) 0.7078(3) 0.0334(7) Uani 1 1 d . . . . .
N2 N 0.8364(5) 0.3605(3) 0.2499(3) 0.0441(8) Uani 1 1 d . . . . .
N3 N 0.2327(5) 0.3343(3) -0.0305(3) 0.0436(7) Uani 1 1 d . . . . .
C1 C 0.4628(5) 1.0363(4) 0.7956(4) 0.0407(9) Uani 1 1 d . . . . .
H1A H 0.3998 1.1086 0.7361 0.061 Uiso 1 1 calc R U . . .
H1B H 0.5494 1.1037 0.9046 0.061 Uiso 1 1 calc R U . . .
H1C H 0.3467 0.9644 0.8048 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8288(5) 0.9559(4) 0.7940(4) 0.0410(9) Uani 1 1 d . . . . .
H2A H 0.8562 0.8674 0.8409 0.061 Uiso 1 1 calc R U . . .
H2B H 0.8663 1.0632 0.8811 0.061 Uiso 1 1 calc R U . . .
H2C H 0.9171 0.9513 0.7178 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5239(5) 0.8115(3) 0.5625(3) 0.0275(7) Uani 1 1 d . . . . .
C4 C 0.3131(5) 0.7883(4) 0.4609(4) 0.0289(7) Uani 1 1 d . . . . .
C5 C 0.2374(5) 0.6692(3) 0.3127(3) 0.0302(8) Uani 1 1 d . . . . .
H5 H 0.0931 0.6618 0.2503 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3737(5) 0.5580(3) 0.2528(3) 0.0279(8) Uani 1 1 d . . . . .
C7 C 0.5834(5) 0.5731(3) 0.3494(3) 0.0268(7) Uani 1 1 d . . . . .
C8 C 0.6588(5) 0.6965(3) 0.5008(3) 0.0293(8) Uani 1 1 d . . . . .
H8 H 0.8028 0.7035 0.5634 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2963(5) 0.4335(4) 0.0959(4) 0.0326(8) Uani 1 1 d . . . . .
C10 C 0.7259(5) 0.4561(4) 0.2934(4) 0.0310(8) 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'
N N 0.0061 0.0033 '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'
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
C3 N1 C2 119.3(3) . .
C3 N1 C1 123.8(3) . .
C2 N1 C1 116.4(2) . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C4 124.6(3) . .
N1 C3 C8 120.7(3) . .
C4 C3 C8 114.7(3) . .
C5 C4 F1 115.7(3) . .
C5 C4 C3 125.0(3) . .
F1 C4 C3 119.3(3) . .
C4 C5 C6 119.5(3) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C7 C6 C5 118.1(3) . .
C7 C6 C9 122.0(3) . .
C5 C6 C9 119.9(3) . .
C6 C7 C8 121.7(3) . .
C6 C7 C10 119.4(3) . .
C8 C7 C10 119.0(3) . .
C7 C8 C3 121.1(3) . .
C7 C8 H8 119.5 . .
C3 C8 H8 119.5 . .
N3 C9 C6 179.4(4) . .
N2 C10 C7 178.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C4 1.362(3) .
N1 C3 1.360(4) .
N1 C2 1.458(4) .
N1 C1 1.466(4) .
N2 C10 1.149(4) .
N3 C9 1.152(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.407(4) .
C3 C8 1.416(4) .
C4 C5 1.361(4) .
C5 C6 1.398(4) .
C5 H5 0.9500 .
C6 C7 1.394(4) .
C6 C9 1.433(4) .
C7 C8 1.395(4) .
C7 C10 1.448(4) .
C8 H8 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 N3 0.95 2.52 3.440(4) 163.0 2_565
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
C2 N1 C3 C4 -173.7(3) . . . .
C1 N1 C3 C4 14.6(4) . . . .
C2 N1 C3 C8 4.9(4) . . . .
C1 N1 C3 C8 -166.8(3) . . . .
N1 C3 C4 C5 177.4(3) . . . .
C8 C3 C4 C5 -1.3(4) . . . .
N1 C3 C4 F1 -1.0(4) . . . .
C8 C3 C4 F1 -179.6(2) . . . .
F1 C4 C5 C6 179.0(2) . . . .
C3 C4 C5 C6 0.6(4) . . . .
C4 C5 C6 C7 0.5(4) . . . .
C4 C5 C6 C9 -179.2(3) . . . .
C5 C6 C7 C8 -0.9(4) . . . .
C9 C6 C7 C8 178.8(3) . . . .
C5 C6 C7 C10 177.8(3) . . . .
C9 C6 C7 C10 -2.5(4) . . . .
C6 C7 C8 C3 0.1(4) . . . .
C10 C7 C8 C3 -178.5(2) . . . .
N1 C3 C8 C7 -177.8(3) . . . .
C4 C3 C8 C7 0.9(4) . . . .
