#------------------------------------------------------------------------------
#$Date: 2019-02-03 22:56:14 +0200 (Sun, 03 Feb 2019) $
#$Revision: 213457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108362
loop_
_publ_author_name
'Kader, Thomas'
'Stöger, Berthold'
'Fröhlich, Johannes'
'Kautny, Paul'
_publ_section_title
;
 The phase transitions of 4-aminopyridine-based indolocarbazoles:
 twinning, local- and pseudo-symmetry
;
_journal_coeditor_code           WF5145SUP1
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              97
_journal_page_last               106
_journal_paper_doi               10.1107/S2052520618017341
_journal_volume                  75
_journal_year                    2019
_chemical_formula_sum            'C17 H10 N2'
_chemical_formula_weight         242.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.53(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.064(8)
_cell_length_b                   16.58(3)
_cell_length_c                   17.57(3)
_cell_measurement_reflns_used    1692
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.29
_cell_measurement_theta_min      2.62
_cell_volume                     1183(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_min         1.159
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       rod
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0550
_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)+(0.0477P)²+0.2046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1908
_reflns_number_total             2763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wf5145sup1.cif
_cod_data_source_block           2NICz-LT
_cod_depositor_comments
'Adding full bibliography for 2108362--2108368.cif.'
_cod_original_cell_volume        1184(4)
_cod_database_code               2108362
_cod_database_fobs_code          2108362
_publcif_datablock.id            {e19d9317-f09c-4335-b8a7-eec07f5790ce}
_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_min   0.957
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N2 N 0.7416(10) 0.23658(13) 0.36549(10) 0.0341(6) Uani 1 1 d . .
N8 N 0.7519(8) 0.24803(12) 0.59699(8) 0.0237(4) Uani 1 1 d . .
C1 C 0.8947(9) 0.29941(15) 0.40130(14) 0.0319(8) Uani 1 1 d . .
H1 H 0.9959 0.3397 0.3715 0.038 Uiso 1 1 calc R U
C3 C 0.5911(9) 0.17722(16) 0.40626(13) 0.0307(7) Uani 1 1 d . .
H3 H 0.4854 0.1342 0.3795 0.037 Uiso 1 1 calc R U
C4 C 0.2985(8) 0.06311(14) 0.56817(13) 0.0298(7) Uani 1 1 d . .
H4 H 0.2298 0.0309 0.5260 0.036 Uiso 1 1 calc R U
C3A C 0.5877(8) 0.17767(14) 0.48767(13) 0.0242(7) Uani 1 1 d . .
C3B C 0.4733(7) 0.13457(13) 0.55673(13) 0.0237(6) Uani 1 1 d . .
C3C C 0.7506(11) 0.24419(15) 0.51806(10) 0.0236(5) Uani 1 1 d . .
C5 C 0.2249(9) 0.03923(15) 0.64303(13) 0.0327(7) Uani 1 1 d . .
H5 H 0.1071 -0.0095 0.6505 0.039 Uiso 1 1 calc R U
C6 C 0.3222(9) 0.08608(15) 0.70710(14) 0.0316(7) Uani 1 1 d . .
H6 H 0.2668 0.0686 0.7566 0.038 Uiso 1 1 calc R U
C7 C 0.4977(8) 0.15734(14) 0.69850(13) 0.0247(7) Uani 1 1 d . .
H7 H 0.5631 0.1891 0.7412 0.030 Uiso 1 1 calc R U
C7A C 0.5749(9) 0.18059(14) 0.62376(12) 0.0240(7) Uani 1 1 d . .
C9 C 1.0095(8) 0.35011(14) 0.69022(13) 0.0271(7) Uani 1 1 d . .
H9 H 0.9442 0.3238 0.7354 0.032 Uiso 1 1 calc R U
C8A C 0.9302(8) 0.31883(13) 0.61753(12) 0.0215(6) Uani 1 1 d . .
C10 C 1.1893(8) 0.42186(15) 0.69233(13) 0.0278(7) Uani 1 1 d . .
H10 H 1.2497 0.4450 0.7402 0.033 Uiso 1 1 calc R U
C11 C 1.2834(9) 0.46097(15) 0.62460(12) 0.0306(7) Uani 1 1 d . .
H11 H 1.3996 0.5106 0.6283 0.037 Uiso 1 1 calc R U
C12 C 1.2102(8) 0.42857(13) 0.55180(13) 0.0287(6) Uani 1 1 d . .
H12 H 1.2812 0.4549 0.5071 0.034 Uiso 1 1 calc R U
C12A C 1.0309(8) 0.35686(13) 0.54717(13) 0.0239(6) Uani 1 1 d . .
C12B C 0.9084(8) 0.30683(14) 0.48208(13) 0.0237(7) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N2 C3 120.9(2)
C3C N8 C7A 107.9(2)
C3C N8 C8A 106.3(2)
C7A N8 C8A 145.85(18)
N2 C1 C12B 122.2(3)
N2 C1 H1 118.9
C12B C1 H1 118.9
N2 C3 C3A 122.4(3)
N2 C3 H3 118.8
C3A C3 H3 118.8
C3B C4 C5 119.5(2)
C3B C4 H4 120.3
C5 C4 H4 120.3
C3C C3A C3 111.8(3)
C3C C3A C3B 102.9(2)
C3 C3A C3B 145.2(3)
C4 C3B C7A 117.5(2)
C4 C3B C3A 133.8(2)
C7A C3B C3A 108.6(2)
C12B C3C C3A 130.1(2)
C12B C3C N8 115.7(3)
C3A C3C N8 114.2(3)
C4 C5 C6 121.7(3)
C4 C5 H5 119.2
C6 C5 H5 119.2
C7 C6 C5 120.9(3)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C7A 117.4(2)
C6 C7 H7 121.3
C7A C7 H7 121.3
C7 C7A N8 130.7(2)
C7 C7A C3B 123.0(3)
N8 C7A C3B 106.3(2)
C10 C9 C8A 116.4(2)
C10 C9 H9 121.8
C8A C9 H9 121.8
C9 C8A N8 129.6(2)
C9 C8A C12A 123.2(3)
N8 C8A C12A 107.2(2)
C9 C10 C11 121.4(2)
C9 C10 H10 119.3
C11 C10 H10 119.3
C12 C11 C10 122.1(3)
C12 C11 H11 118.9
C10 C11 H11 118.9
C12A C12 C11 118.3(2)
C12A C12 H12 120.9
C11 C12 H12 120.9
C12 C12A C8A 118.5(2)
C12 C12A C12B 133.1(2)
C8A C12A C12B 108.4(2)
C3C C12B C1 112.6(3)
C3C C12B C12A 102.5(2)
C1 C12B C12A 144.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C1 1.359(4)
N2 C3 1.371(4)
N8 C3C 1.388(3)
N8 C7A 1.417(4)
N8 C8A 1.421(4)
C1 C12B 1.424(4)
C1 H1 0.9500
C3 C3A 1.431(4)
C3 H3 0.9500
C4 C3B 1.399(4)
C4 C5 1.413(4)
C4 H4 0.9500
C3A C3C 1.386(4)
C3A C3B 1.493(4)
C3B C7A 1.454(4)
C3C C12B 1.382(4)
C5 C6 1.415(4)
C5 H5 0.9500
C6 C7 1.390(4)
C6 H6 0.9500
C7 C7A 1.412(4)
C7 H7 0.9500
C9 C10 1.396(4)
C9 C8A 1.408(4)
C9 H9 0.9500
C8A C12A 1.456(4)
C10 C11 1.417(4)
C10 H10 0.9500
C11 C12 1.412(4)
C11 H11 0.9500
C12 C12A 1.396(4)
C12 H12 0.9500
C12A C12B 1.488(4)
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
C7 H7 N2 0.95 2.59 3.540(6) 174.5 4_566
C9 H9 N2 0.95 2.65 3.594(6) 174.7 4_566
