#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:14:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238761 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/79/7237935.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_7237935
loop_
_publ_author_name
'Tu, Jin'
'Fan, Yunhao'
'Wang, Jiaqiang'
'Li, Xiaoyu'
'Liu, Fan'
'Han, Mengmeng'
'Wang, Can'
'Li, Qianqian'
'Li, Zhen'
_publ_section_title
;
 Halogen-substituted triphenylamine derivatives with intense
 mechanoluminescence properties
;
_journal_issue                   39
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              12256
_journal_paper_doi               10.1039/C9TC03515J
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-12-07 deposited with the CCDC.	2019-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.999(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0916(17)
_cell_length_b                   11.4255(16)
_cell_length_c                   10.9413(16)
_cell_measurement_reflns_used    57
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      7.5
_cell_volume                     1478.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  bruker
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9559
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0378P)²+0.3419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2273
_reflns_number_total             3056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9tc03515j4.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7237935
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.78412(11) 0.14310(11) 0.00306(13) 0.0450(3) Uani 1 1 d .
C2 C 0.86034(13) 0.07894(13) -0.04716(14) 0.0538(4) Uani 1 1 d .
H2 H 0.9297 0.1114 -0.0528 0.065 Uiso 1 1 calc R
C3 C 0.83359(14) -0.03354(14) -0.08914(15) 0.0609(4) Uani 1 1 d .
H3 H 0.8854 -0.0768 -0.1225 0.073 Uiso 1 1 calc R
C4 C 0.73142(14) -0.08212(13) -0.08221(15) 0.0597(4) Uani 1 1 d .
H4 H 0.7136 -0.1576 -0.1115 0.072 Uiso 1 1 calc R
C5 C 0.65588(13) -0.01884(13) -0.03193(16) 0.0592(4) Uani 1 1 d .
H5 H 0.5866 -0.0517 -0.0268 0.071 Uiso 1 1 calc R
C6 C 0.68156(12) 0.09370(12) 0.01141(15) 0.0541(4) Uani 1 1 d .
H6 H 0.6300 0.1360 0.0461 0.065 Uiso 1 1 calc R
C7 C 0.74047(11) 0.35295(11) -0.00186(13) 0.0454(3) Uani 1 1 d .
C8 C 0.67122(12) 0.34612(12) -0.12000(14) 0.0531(4) Uani 1 1 d .
H8 H 0.6722 0.2793 -0.1683 0.064 Uiso 1 1 calc R
C9 C 0.60134(13) 0.43789(13) -0.16566(15) 0.0576(4) Uani 1 1 d .
H9 H 0.5545 0.4315 -0.2444 0.069 Uiso 1 1 calc R
C10 C 0.59884(12) 0.53921(12) -0.09773(15) 0.0528(4) Uani 1 1 d .
C11 C 0.66814(12) 0.54636(12) 0.02052(16) 0.0557(4) Uani 1 1 d .
H11 H 0.6674 0.6139 0.0678 0.067 Uiso 1 1 calc R
C12 C 0.73764(12) 0.45500(12) 0.06842(15) 0.0535(4) Uani 1 1 d .
H12 H 0.7831 0.4609 0.1480 0.064 Uiso 1 1 calc R
C13 C 0.52300(14) 0.63464(15) -0.1496(2) 0.0711(5) Uani 1 1 d .
H13 H 0.4761 0.6219 -0.2273 0.085 Uiso 1 1 calc R
C14 C 0.91775(11) 0.27947(12) 0.12798(13) 0.0460(3) Uani 1 1 d .
C15 C 0.98844(13) 0.36592(14) 0.10096(16) 0.0616(4) Uani 1 1 d .
H15 H 0.9647 0.4134 0.0314 0.074 Uiso 1 1 calc R
C16 C 1.09360(14) 0.38293(17) 0.1756(2) 0.0753(5) Uani 1 1 d .
H16 H 1.1402 0.4418 0.1560 0.090 Uiso 1 1 calc R
C17 C 1.13005(15) 0.31445(18) 0.27765(18) 0.0754(6) Uani 1 1 d .
H17 H 1.2014 0.3260 0.3277 0.090 Uiso 1 1 calc R
C18 C 1.06066(16) 0.22810(19) 0.30614(15) 0.0747(5) Uani 1 1 d .
H18 H 1.0852 0.1813 0.3760 0.090 Uiso 1 1 calc R
C19 C 0.95382(14) 0.20996(15) 0.23128(15) 0.0608(4) Uani 1 1 d .
H19 H 0.9072 0.1512 0.2510 0.073 Uiso 1 1 calc R
N1 N 0.81062(10) 0.25959(10) 0.04765(12) 0.0534(3) Uani 1 1 d .
O1 O 0.51541(11) 0.72782(10) -0.10160(15) 0.0867(4) 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'
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
C2 C1 C6 119.50(13)
C2 C1 N1 120.65(13)
C6 C1 N1 119.84(13)
C1 C2 C3 119.87(14)
C4 C3 C2 120.67(15)
C5 C4 C3 119.56(14)
C4 C5 C6 120.56(15)
C1 C6 C5 119.82(14)
C8 C7 N1 121.13(12)
C8 C7 C12 118.61(13)
N1 C7 C12 120.25(13)
C9 C8 C7 120.13(13)
C8 C9 C10 121.69(14)
C9 C10 C11 118.32(13)
C9 C10 C13 119.95(15)
C11 C10 C13 121.72(14)
C12 C11 C10 120.86(13)
C11 C12 C7 120.38(14)
O1 C13 C10 126.26(18)
C19 C14 C15 119.02(14)
C19 C14 N1 120.47(13)
C15 C14 N1 120.47(13)
C16 C15 C14 120.83(16)
C17 C16 C15 120.54(18)
C16 C17 C18 119.42(16)
C17 C18 C19 120.60(17)
C14 C19 C18 119.58(16)
C7 N1 C14 121.16(11)
C7 N1 C1 120.14(11)
C14 N1 C1 117.99(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(2)
C1 C6 1.3827(19)
C1 N1 1.4308(17)
C2 C3 1.380(2)
C3 C4 1.371(2)
C4 C5 1.367(2)
C5 C6 1.383(2)
C7 C8 1.3885(19)
C7 N1 1.3999(17)
C7 C12 1.4011(19)
C8 C9 1.3739(19)
C9 C10 1.379(2)
C10 C11 1.390(2)
C10 C13 1.461(2)
C11 C12 1.374(2)
C13 O1 1.199(2)
C14 C19 1.376(2)
C14 C15 1.378(2)
C14 N1 1.4243(17)
C15 C16 1.374(2)
C16 C17 1.360(3)
C17 C18 1.372(3)
C18 C19 1.394(2)
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
C6 C1 C2 C3 0.3(2)
N1 C1 C2 C3 179.67(13)
C1 C2 C3 C4 0.4(2)
C2 C3 C4 C5 -0.7(2)
C3 C4 C5 C6 0.3(2)
C2 C1 C6 C5 -0.8(2)
N1 C1 C6 C5 179.88(13)
C4 C5 C6 C1 0.5(2)
N1 C7 C8 C9 178.65(14)
C12 C7 C8 C9 -0.3(2)
C7 C8 C9 C10 1.1(2)
C8 C9 C10 C11 -1.0(2)
C8 C9 C10 C13 -179.82(15)
C9 C10 C11 C12 0.2(2)
C13 C10 C11 C12 179.02(15)
C10 C11 C12 C7 0.5(2)
C8 C7 C12 C11 -0.4(2)
N1 C7 C12 C11 -179.42(13)
C9 C10 C13 O1 -177.71(18)
C11 C10 C13 O1 3.5(3)
C19 C14 C15 C16 0.1(2)
N1 C14 C15 C16 -177.67(15)
C14 C15 C16 C17 0.1(3)
C15 C16 C17 C18 -0.2(3)
C16 C17 C18 C19 0.2(3)
C15 C14 C19 C18 -0.1(2)
N1 C14 C19 C18 177.66(14)
C17 C18 C19 C14 -0.1(3)
C8 C7 N1 C14 146.52(14)
C12 C7 N1 C14 -34.5(2)
C8 C7 N1 C1 -23.6(2)
C12 C7 N1 C1 155.37(14)
C19 C14 N1 C7 139.20(15)
C15 C14 N1 C7 -43.1(2)
C19 C14 N1 C1 -50.5(2)
C15 C14 N1 C1 127.25(15)
C2 C1 N1 C7 122.22(15)
C6 C1 N1 C7 -58.42(19)
C2 C1 N1 C14 -48.22(19)
C6 C1 N1 C14 131.14(15)
