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#$Date: 2021-03-03 22:05:59 +0200 (Wed, 03 Mar 2021) $
#$Revision: 262403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518518.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_4518518
loop_
_publ_author_name
'Gómez, Paula'
'Georgakopoulos, Stamatis'
'Más-Montoya, Miriam'
'Cerdá, Jesús'
'Pérez, José'
'Ortí, Enrique'
'Aragó, Juan'
'Curiel, David'
_publ_section_title
;
 Improving the Robustness of Organic Semiconductors through Hydrogen
 Bonding.
;
_journal_issue                   7
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              8620
_journal_page_last               8630
_journal_paper_doi               10.1021/acsami.0c18928
_journal_volume                  13
_journal_year                    2021
_chemical_formula_sum            'C26 H16 N2'
_chemical_formula_weight         356.41
_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   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 97.995(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3982(3)
_cell_length_b                   7.4255(3)
_cell_length_c                   18.0900(8)
_cell_measurement_reflns_used    8954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.33
_cell_measurement_theta_min      4.38
_cell_volume                     851.10(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_collection       'APEX3 2017.3 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω-scans and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22457
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.419
_diffrn_reflns_theta_min         4.937
_diffrn_source                   'high brilliance microfocus sealed tube '
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       lath
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0493
_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)+(0.0665P)²+0.4741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1469
_reflns_number_total             1732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am0c18928_si_001.cif
_cod_data_source_block           pgp42_0msp_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518518
_shelx_shelxl_version_number     2018/1
_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   0.917
_shelx_estimated_absorpt_t_max   0.981
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
C1 C 0.8298(3) 0.6407(2) 0.60748(10) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.958095 0.679416 0.591731 0.024 Uiso 1 1 calc R U . . .
C2 C 0.8067(3) 0.6545(2) 0.68072(10) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.916585 0.704425 0.715398 0.024 Uiso 1 1 calc R U . . .
C2A C 0.6167(3) 0.5939(2) 0.70529(10) 0.0188(4) Uani 1 1 d . . . . .
C2B C 0.5433(3) 0.5909(2) 0.77695(10) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.6301(3) 0.6447(2) 0.84899(10) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.766272 0.698050 0.857773 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5136(3) 0.6184(3) 0.90705(11) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.571036 0.653837 0.956147 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3108(3) 0.5400(3) 0.89459(11) 0.0247(4) Uani 1 1 d . . . . .
H5 H 0.234183 0.524057 0.935496 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2212(3) 0.4859(2) 0.82411(11) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.084831 0.432903 0.815761 0.028 Uiso 1 1 calc R U . . .
C6A C 0.3397(3) 0.5125(2) 0.76560(10) 0.0203(4) Uani 1 1 d . . . . .
N7 N 0.2902(2) 0.4710(2) 0.69083(9) 0.0204(4) Uani 1 1 d . . . . .
H0 H 0.180(4) 0.415(3) 0.6708(13) 0.033(6) Uiso 1 1 d . . . . .
C7A C 0.4557(3) 0.5208(2) 0.65381(10) 0.0188(4) Uani 1 1 d . . . . .
C7B C 0.4702(3) 0.5083(2) 0.57595(10) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.3103(3) 0.4427(2) 0.52223(10) 0.0193(4) Uani 1 1 d . . . . .
H8 H 0.181035 0.404899 0.537503 0.023 Uiso 1 1 calc R U . . .
C8A C 0.3341(3) 0.4310(2) 0.44689(10) 0.0191(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 0.0181 0.0091 '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 0.0311 0.0180 '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
C2 C1 C8A 121.86(16) . 3_666 ?
C2 C1 H1 119.1 . . ?
C8A C1 H1 119.1 3_666 . ?
C1 C2 C2A 119.63(16) . . ?
C1 C2 H2 120.2 . . ?
C2A C2 H2 120.2 . . ?
C7A C2A C2 119.78(16) . . ?
C7A C2A C2B 106.92(15) . . ?
C2 C2A C2B 133.30(16) . . ?
C3 C2B C6A 119.33(17) . . ?
C3 C2B C2A 134.10(17) . . ?
C6A C2B C2A 106.56(16) . . ?
C4 C3 C2B 118.65(17) . . ?
C4 C3 H3 120.7 . . ?
C2B C3 H3 120.7 . . ?
C3 C4 C5 121.17(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.39(18) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C6A 117.25(18) . . ?
C5 C6 H6 121.4 . . ?
C6A C6 H6 121.4 . . ?
N7 C6A C6 129.41(17) . . ?
N7 C6A C2B 108.38(16) . . ?
C6 C6A C2B 122.21(17) . . ?
C7A N7 C6A 109.17(15) . . ?
C7A N7 H0 124.7(16) . . ?
C6A N7 H0 126.0(16) . . ?
N7 C7A C2A 108.96(15) . . ?
N7 C7A C7B 128.39(16) . . ?
C2A C7A C7B 122.63(16) . . ?
C8 C7B C7A 124.55(16) . . ?
C8 C7B C8A 119.35(17) . 3_666 ?
C7A C7B C8A 116.10(16) . 3_666 ?
C8A C8 C7B 122.16(16) . . ?
C8A C8 H8 118.9 . . ?
C7B C8 H8 118.9 . . ?
C8 C8A C1 121.56(16) . 3_666 ?
C8 C8A C7B 118.49(16) . 3_666 ?
C1 C8A C7B 119.96(16) 3_666 3_666 ?
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
C1 C2 1.357(3) . ?
C1 C8A 1.437(2) 3_666 ?
C1 H1 0.9500 . ?
C2 C2A 1.424(2) . ?
C2 H2 0.9500 . ?
C2A C7A 1.399(2) . ?
C2A C2B 1.439(3) . ?
C2B C3 1.402(3) . ?
C2B C6A 1.415(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C6A 1.399(3) . ?
C6 H6 0.9500 . ?
C6A N7 1.381(2) . ?
N7 C7A 1.380(2) . ?
N7 H0 0.85(3) . ?
C7A C7B 1.427(3) . ?
C7B C8 1.397(2) . ?
C7B C8A 1.444(2) 3_666 ?
C8 C8A 1.395(3) . ?
C8 H8 0.9500 . ?
