#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202537.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_7202537
loop_
_publ_author_name
'McKeown, Neil B.'
'Badriya, Samer'
'Helliwell, Madeleine'
'Shkunov, Maxim'
_publ_section_title
;
 The synthesis of robust, polymeric hole-transport materials from
 oligoarylamine substituted styrenes
;
_journal_issue                   20
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2088
_journal_paper_doi               10.1039/b614235d
_journal_volume                  17
_journal_year                    2007
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.33
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             19101-03-07
_audit_creation_method           'by teXsan v1.7'
_audit_update_record
;
?
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.19(4)
_cell_length_b                   7.739(10)
_cell_length_c                   23.46(3)
_cell_measurement_reflns_used    38287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      1.74
_cell_volume                     2939(9)
_computing_cell_refinement       'DENZO (Otwinowski, Z. 1988)'
_computing_data_collection       'MSC RAXIS11 Control'
_computing_data_reduction        'DENZO (Otwinowski, Z. 1988)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.584
_diffrn_measured_fraction_theta_max 0.584
_diffrn_measurement_device       'Rigaku RAXIS'
_diffrn_measurement_method       '120 x 2 degree phi scans'
_diffrn_radiation_detector       'image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38287
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0161(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0372
_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)+(0.0593P)²+0.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                1497
_reflns_number_total             1980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614235d.txt
_cod_data_source_block           s926
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               7202537
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45748(8) 0.02891(15) 0.63705(5) 0.0588(4) Uani 1 d . . .
C1 C 0.53342(10) -0.0518(2) 0.63069(7) 0.0586(4) Uani 1 d . . .
C2 C 0.59972(12) -0.0066(2) 0.59660(7) 0.0707(5) Uani 1 d . . .
H2 H 0.5977 0.0902 0.5732 0.085 Uiso 1 calc R . .
C3 C 0.66836(13) -0.1095(3) 0.59861(9) 0.0846(6) Uani 1 d . . .
H3 H 0.7138 -0.0821 0.5760 0.101 Uiso 1 calc R . .
C4 C 0.67169(14) -0.2534(3) 0.63344(10) 0.0917(7) Uani 1 d . . .
H4 H 0.7188 -0.3222 0.6333 0.110 Uiso 1 calc R . .
C5 C 0.60713(15) -0.2963(2) 0.66796(8) 0.0826(6) Uani 1 d . . .
H5 H 0.6103 -0.3924 0.6916 0.099 Uiso 1 calc R . .
C6 C 0.53656(11) -0.1945(2) 0.66728(7) 0.0621(5) Uani 1 d . . .
C7 C 0.45975(11) -0.19927(19) 0.69760(7) 0.0597(5) Uani 1 d . . .
C8 C 0.42744(14) -0.3071(2) 0.73915(8) 0.0742(5) Uani 1 d . . .
H8 H 0.4588 -0.3977 0.7536 0.089 Uiso 1 calc R . .
C9 C 0.34943(15) -0.2793(2) 0.75858(8) 0.0814(6) Uani 1 d . . .
H9 H 0.3277 -0.3507 0.7867 0.098 Uiso 1 calc R . .
C10 C 0.30213(12) -0.1461(2) 0.73703(8) 0.0767(5) Uani 1 d . . .
H10 H 0.2485 -0.1310 0.7503 0.092 Uiso 1 calc R . .
C11 C 0.33244(11) -0.0352(2) 0.69637(7) 0.0655(5) Uani 1 d . . .
H11 H 0.3004 0.0545 0.6821 0.079 Uiso 1 calc R . .
C12 C 0.41210(10) -0.06182(19) 0.67756(6) 0.0556(4) Uani 1 d . . .
C13 C 0.43177(10) 0.18146(18) 0.60834(7) 0.0555(4) Uani 1 d . . .
C14 C 0.40449(11) 0.32233(19) 0.63888(7) 0.0644(5) Uani 1 d . . .
H14 H 0.4027 0.3180 0.6785 0.077 Uiso 1 calc R . .
C15 C 0.37988(11) 0.4695(2) 0.61071(7) 0.0665(5) Uani 1 d . . .
H15 H 0.3604 0.5631 0.6316 0.080 Uiso 1 calc R . .
C16 C 0.38348(10) 0.48119(19) 0.55191(7) 0.0599(5) Uani 1 d . . .
C17 C 0.41251(11) 0.3398(2) 0.52252(7) 0.0680(5) Uani 1 d . . .
H17 H 0.4169 0.3454 0.4830 0.082 Uiso 1 calc R . .
C18 C 0.43515(10) 0.1906(2) 0.54999(7) 0.0637(5) Uani 1 d . . .
H18 H 0.4528 0.0956 0.5290 0.076 Uiso 1 calc R . .
C19 C 0.35663(12) 0.6356(2) 0.52072(8) 0.0791(6) Uani 1 d . . .
H19 H 0.3707 0.6399 0.4823 0.095 Uiso 1 calc R . .
C20 C 0.31609(14) 0.7654(3) 0.54010(10) 0.1011(7) Uani 1 d . . .
H20A H 0.3003 0.7683 0.5782 0.121 Uiso 1 calc R . .
H20B H 0.3025 0.8565 0.5160 0.121 Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.30(16) . . ?
C1 N1 C13 125.63(14) . . ?
C12 N1 C13 126.04(17) . . ?
C2 C1 N1 129.48(19) . . ?
C2 C1 C6 121.74(17) . . ?
N1 C1 C6 108.76(15) . . ?
C3 C2 C1 117.6(2) . . ?
C2 C3 C4 121.4(2) . . ?
C5 C4 C3 121.2(2) . . ?
C4 C5 C6 119.1(2) . . ?
C5 C6 C1 119.00(18) . . ?
C5 C6 C7 133.9(2) . . ?
C1 C6 C7 107.06(15) . . ?
C8 C7 C12 119.2(2) . . ?
C8 C7 C6 133.80(17) . . ?
C12 C7 C6 107.02(18) . . ?
C9 C8 C7 119.39(18) . . ?
C8 C9 C10 120.72(19) . . ?
C11 C10 C9 121.5(2) . . ?
C10 C11 C12 117.60(17) . . ?
C11 C12 N1 129.59(16) . . ?
C11 C12 C7 121.53(17) . . ?
N1 C12 C7 108.85(19) . . ?
C18 C13 C14 119.40(15) . . ?
C18 C13 N1 120.28(14) . . ?
C14 C13 N1 120.32(16) . . ?
C15 C14 C13 119.88(17) . . ?
C14 C15 C16 121.41(16) . . ?
C17 C16 C15 117.49(15) . . ?
C17 C16 C19 119.93(18) . . ?
C15 C16 C19 122.57(17) . . ?
C18 C17 C16 121.66(17) . . ?
C17 C18 C13 120.12(15) . . ?
C20 C19 C16 127.8(2) . . ?
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
N1 C1 1.387(3) . ?
N1 C12 1.391(2) . ?
N1 C13 1.421(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.400(2) . ?
C2 C3 1.368(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.363(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.433(4) . ?
C7 C8 1.386(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.360(4) . ?
C9 C10 1.380(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.378(4) . ?
C13 C18 1.372(3) . ?
C13 C14 1.377(2) . ?
C14 C15 1.375(2) . ?
C15 C16 1.384(3) . ?
C16 C17 1.376(2) . ?
C16 C19 1.467(3) . ?
C17 C18 1.372(2) . ?
C19 C20 1.283(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -178.16(15) . . . . ?
C13 N1 C1 C2 0.0(3) . . . . ?
C12 N1 C1 C6 -0.04(16) . . . . ?
C13 N1 C1 C6 178.10(13) . . . . ?
N1 C1 C2 C3 179.70(15) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C5 C6 C7 -178.87(17) . . . . ?
C2 C1 C6 C5 -2.1(2) . . . . ?
N1 C1 C6 C5 179.61(14) . . . . ?
C2 C1 C6 C7 177.57(14) . . . . ?
N1 C1 C6 C7 -0.72(16) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C1 C6 C7 C8 -179.26(16) . . . . ?
C5 C6 C7 C12 -179.19(17) . . . . ?
C1 C6 C7 C12 1.20(16) . . . . ?
C12 C7 C8 C9 1.5(2) . . . . ?
C6 C7 C8 C9 -178.02(17) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 N1 179.57(15) . . . . ?
C10 C11 C12 C7 1.9(2) . . . . ?
C1 N1 C12 C11 -177.07(15) . . . . ?
C13 N1 C12 C11 4.8(2) . . . . ?
C1 N1 C12 C7 0.81(16) . . . . ?
C13 N1 C12 C7 -177.32(13) . . . . ?
C8 C7 C12 C11 -2.8(2) . . . . ?
C6 C7 C12 C11 176.85(14) . . . . ?
C8 C7 C12 N1 179.14(13) . . . . ?
C6 C7 C12 N1 -1.24(16) . . . . ?
C1 N1 C13 C18 53.9(2) . . . . ?
C12 N1 C13 C18 -128.24(17) . . . . ?
C1 N1 C13 C14 -125.03(17) . . . . ?
C12 N1 C13 C14 52.8(2) . . . . ?
C18 C13 C14 C15 0.9(2) . . . . ?
N1 C13 C14 C15 179.89(15) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C19 179.17(16) . . . . ?
C15 C16 C17 C18 1.6(2) . . . . ?
C19 C16 C17 C18 -177.43(16) . . . . ?
C16 C17 C18 C13 -2.2(3) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
N1 C13 C18 C17 -178.15(15) . . . . ?
C17 C16 C19 C20 167.6(2) . . . . ?
C15 C16 C19 C20 -11.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16097608
2 PubChem 23071473
