# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9-ethyl-3-122-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1562615'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 N4'
_chemical_formula_sum            'C19 H12 N4'
_chemical_formula_weight         296.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   7.0914(2)
_cell_length_b                   12.8955(4)
_cell_length_c                   16.1234(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.0270(10)
_cell_angle_gamma                90
_cell_volume                     1456.18(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      74.45

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.661
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25035
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.412
_diffrn_reflns_theta_max         74.680
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2930
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0325P)²+1.5512P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     227
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.3184(2) 0.76140(13) 0.44615(11) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.1562(3) 0.23465(15) 0.48141(15) 0.0464(5) Uani 1 1 d . U . . .
N3 N 0.2972(3) 0.14550(17) 0.71482(19) 0.0625(7) Uani 1 1 d . . . . .
N4 N 0.4421(3) 0.43345(18) 0.81016(13) 0.0490(5) Uani 1 1 d . . . . .
C1 C 0.2316(3) 0.73236(17) 0.36570(13) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.1938(3) 0.7928(2) 0.29348(14) 0.0410(6) Uani 1 1 d . . . . .
H2 H 0.2261 0.8643 0.2940 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1073(3) 0.7445(3) 0.22107(16) 0.0577(6) Uani 1 1 d . U . . .
H3 H 0.0778 0.7841 0.1710 0.069 Uiso 1 1 calc R U . . .
C4 C 0.0619(4) 0.6395(3) 0.21914(18) 0.0645(6) Uani 1 1 d . U . . .
H4 H 0.0028 0.6088 0.1680 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1017(3) 0.5793(2) 0.29070(19) 0.0540(6) Uani 1 1 d . U . . .
H5 H 0.0731 0.5073 0.2889 0.065 Uiso 1 1 calc R U . . .
C6 C 0.1850(3) 0.62625(18) 0.36589(15) 0.0370(5) Uani 1 1 d . . . . .
C7 C 0.2443(3) 0.59038(16) 0.45074(16) 0.0371(5) Uani 1 1 d . . . . .
C8 C 0.2351(3) 0.49536(17) 0.4882(2) 0.0504(6) Uani 1 1 d . U . . .
H8 H 0.1797 0.4379 0.4564 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3076(4) 0.48348(18) 0.5733(2) 0.0545(6) Uani 1 1 d . U . . .
C10 C 0.3908(4) 0.5702(2) 0.61902(18) 0.0484(7) Uani 1 1 d . . . . .
H10 H 0.4415 0.5616 0.6767 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4010(3) 0.66674(18) 0.58289(14) 0.0369(5) Uani 1 1 d . . . . .
H11 H 0.4574 0.7240 0.6146 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3251(3) 0.67676(15) 0.49795(14) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.2860(5) 0.3756(3) 0.5954(3) 0.0197(6) Uani 0.5 1 d . U P A 1
C14 C 0.3329(5) 0.3370(3) 0.6788(2) 0.0174(7) Uani 0.5 1 d . . P A 1
C13' C 0.3305(7) 0.3945(6) 0.6456(5) 0.0500(14) Uani 0.5 1 d . . P A 2
C14' C 0.2783(7) 0.3035(5) 0.6204(4) 0.0517(14) Uani 0.5 1 d . . P A 2
C15 C 0.2123(3) 0.2857(2) 0.53585(16) 0.0424(5) Uani 1 1 d . U . . .
C16 C 0.3037(3) 0.22503(18) 0.68938(17) 0.0436(6) Uani 1 1 d . . . . .
C17 C 0.3960(3) 0.40348(18) 0.74475(17) 0.0406(5) Uani 1 1 d . . . . .
C18 C 0.3767(3) 0.86737(15) 0.47091(13) 0.0295(4) Uani 1 1 d . . . . .
H18A H 0.4364 0.8999 0.4258 0.035 Uiso 1 1 calc R U . . .
H18B H 0.4733 0.8651 0.5224 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2084(3) 0.93305(16) 0.48732(17) 0.0412(6) Uani 1 1 d . . . . .
H19A H 0.2513 1.0043 0.5002 0.062 Uiso 1 1 calc R U . . .
H19B H 0.1554 0.9042 0.5350 0.062 Uiso 1 1 calc R U . . .
H19C H 0.1099 0.9329 0.4373 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C12 1.371(3) . ?
N1 C1 1.397(3) . ?
N1 C18 1.465(2) . ?
N2 C15 1.119(3) . ?
N3 C16 1.108(3) . ?
N4 C17 1.123(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.443(4) . ?
C7 C8 1.372(3) . ?
C7 C12 1.418(3) . ?
C8 C9 1.396(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(4) . ?
C9 C13 1.451(4) . ?
C9 C13' 1.626(8) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.423(5) . ?
C13 C15 1.543(6) . ?
C14 C17 1.384(4) . ?
C14 C16 1.473(4) . ?
C13' C14' 1.277(9) . ?
C13' C17 1.598(8) . ?
C14' C15 1.389(7) . ?
C14' C16 1.494(7) . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C12 N1 C1 108.70(17) . . ?
C12 N1 C18 126.54(17) . . ?
C1 N1 C18 124.58(17) . . ?
C2 C1 N1 128.7(2) . . ?
C2 C1 C6 122.1(2) . . ?
N1 C1 C6 109.1(2) . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 134.7(2) . . ?
C1 C6 C7 106.28(19) . . ?
C8 C7 C12 120.5(2) . . ?
C8 C7 C6 132.6(2) . . ?
C12 C7 C6 106.86(19) . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 C13 108.1(3) . . ?
C10 C9 C13 132.9(3) . . ?
C8 C9 C13' 139.6(3) . . ?
C10 C9 C13' 101.4(3) . . ?
C11 C10 C9 122.5(3) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 117.3(2) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C11 129.97(19) . . ?
N1 C12 C7 109.02(19) . . ?
C11 C12 C7 121.0(2) . . ?
C14 C13 C9 123.3(5) . . ?
C14 C13 C15 109.4(3) . . ?
C9 C13 C15 127.3(4) . . ?
C17 C14 C13 120.6(4) . . ?
C17 C14 C16 123.6(3) . . ?
C13 C14 C16 115.8(3) . . ?
C14' C13' C17 114.2(7) . . ?
C14' C13' C9 115.4(6) . . ?
C17 C13' C9 130.3(5) . . ?
C13' C14' C15 120.0(7) . . ?
C13' C14' C16 113.0(6) . . ?
C15 C14' C16 127.0(5) . . ?
N2 C15 C14' 153.0(4) . . ?
N2 C15 C13 166.9(3) . . ?
N3 C16 C14 164.8(3) . . ?
N3 C16 C14' 153.6(4) . . ?
N4 C17 C14 161.1(3) . . ?
N4 C17 C13' 164.0(4) . . ?
N1 C18 C19 111.80(17) . . ?
N1 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N1 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.050



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9-octyl-3-(122)-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1562621'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N4'
_chemical_formula_sum            'C25 H24 N4'
_chemical_formula_weight         380.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.917(3)
_cell_length_b                   8.777(4)
_cell_length_c                   16.892(7)
_cell_angle_alpha                92.79(2)
_cell_angle_beta                 102.20(2)
_cell_angle_gamma                107.30(2)
_cell_volume                     1087.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2348
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.47

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 The poor quality of reflections could be due to the fact 
 that the crystal does not diffract very well
  Other attempts of crystallization were done, but no single 
  crystals of better quality were obtained. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25848
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         27.715
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5019
_reflns_number_gt                1658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1201P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5019
_refine_ls_number_parameters     263
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.2608
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2955
_refine_ls_wR_factor_gt          0.2271
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.7931(5) 0.4480(4) 0.6258(2) 0.0708(11) Uani 1 1 d . . . . .
N2 N 1.3698(6) 0.6038(5) 0.7238(3) 0.0787(12) Uani 1 1 d . . . . .
N3 N 1.4725(5) 0.8726(4) 0.5650(2) 0.0690(11) Uani 1 1 d . . . . .
N4 N 0.6734(4) 0.8972(4) 0.3015(2) 0.0541(9) Uani 1 1 d . . . . .
C1 C 0.9240(7) 0.5311(6) 0.6203(3) 0.0659(13) Uani 1 1 d . . . . .
C2 C 1.1049(6) 0.6331(5) 0.6153(3) 0.0616(12) Uani 1 1 d . . . . .
C3 C 1.2514(7) 0.6183(5) 0.6749(3) 0.0741(14) Uani 1 1 d . . . . .
C4 C 1.1329(5) 0.7315(5) 0.5579(3) 0.0607(12) Uani 1 1 d . . . . .
C5 C 1.3237(7) 0.8074(5) 0.5629(3) 0.0661(12) Uani 1 1 d . . . . .
C6 C 1.0031(5) 0.7683(5) 0.4920(3) 0.0582(11) Uani 1 1 d . . . . .
C7 C 0.8094(6) 0.7069(5) 0.4822(3) 0.0643(12) Uani 1 1 d . . . . .
H7 H 0.7635 0.6411 0.5192 0.077 Uiso 1 1 calc R U . . .
C8 C 0.6905(6) 0.7421(5) 0.4203(3) 0.0639(12) Uani 1 1 d . . . . .
H8 H 0.5654 0.7025 0.4150 0.077 Uiso 1 1 calc R U . . .
C9 C 0.7643(6) 0.8397(5) 0.3654(3) 0.0576(11) Uani 1 1 d . . . . .
C10 C 0.9536(6) 0.9039(5) 0.3755(3) 0.0560(11) Uani 1 1 d . . . . .
C11 C 1.0753(6) 0.8704(5) 0.4371(3) 0.0571(11) Uani 1 1 d . . . . .
H11 H 1.2003 0.9131 0.4426 0.068 Uiso 1 1 calc R U . . .
C12 C 0.9793(6) 1.0077(5) 0.3103(3) 0.0601(12) Uani 1 1 d . . . . .
C13 C 1.1352(6) 1.1085(5) 0.2903(3) 0.0651(12) Uani 1 1 d . . . . .
H13 H 1.2521 1.1183 0.3196 0.078 Uiso 1 1 calc R U . . .
C14 C 1.1048(6) 1.1907(5) 0.2256(3) 0.0718(13) Uani 1 1 d . . . . .
H14 H 1.2042 1.2583 0.2102 0.086 Uiso 1 1 calc R U . . .
C15 C 0.9323(7) 1.1778(5) 0.1820(3) 0.0792(14) Uani 1 1 d . . . . .
H15 H 0.9190 1.2355 0.1377 0.095 Uiso 1 1 calc R U . . .
C16 C 0.7791(6) 1.0822(5) 0.2022(3) 0.0687(13) Uani 1 1 d . . . . .
H16 H 0.6632 1.0766 0.1732 0.082 Uiso 1 1 calc R U . . .
C17 C 0.8040(6) 0.9939(5) 0.2676(3) 0.0618(12) Uani 1 1 d . . . . .
C18 C 0.4798(5) 0.8524(5) 0.2699(3) 0.0715(13) Uani 1 1 d D . . . .
H18A H 0.4494 0.9436 0.2480 0.086 Uiso 1 1 calc R U . . .
H18B H 0.4198 0.8255 0.3142 0.086 Uiso 1 1 calc R U . . .
C19 C 0.4096(6) 0.7127(6) 0.2047(3) 0.0907(16) Uani 1 1 d D . . . .
H19A H 0.4520 0.6260 0.2252 0.109 Uiso 1 1 calc R U . . .
H19B H 0.4620 0.7441 0.1586 0.109 Uiso 1 1 calc R U . . .
C20 C 0.2043(7) 0.6493(8) 0.1745(4) 0.127(2) Uani 1 1 d D . . . .
H20A H 0.1723 0.5407 0.1479 0.153 Uiso 1 1 calc R U . . .
H20B H 0.1521 0.6423 0.2217 0.153 Uiso 1 1 calc R U . . .
C21 C 0.1229(7) 0.7339(8) 0.1220(4) 0.127(2) Uani 1 1 d D . . . .
H21A H 0.1817 0.7511 0.0769 0.153 Uiso 1 1 calc R U . . .
H21B H 0.1400 0.8384 0.1501 0.153 Uiso 1 1 calc R U . . .
C22 C -0.0899(7) 0.6446(8) 0.0871(4) 0.122(2) Uani 1 1 d D . . . .
H22A H -0.1116 0.5427 0.0553 0.146 Uiso 1 1 calc R U . . .
H22B H -0.1531 0.6260 0.1308 0.146 Uiso 1 1 calc R U . . .
C23 C -0.1491(7) 0.7628(7) 0.0339(4) 0.109(2) Uani 1 1 d D . . . .
H23A H -0.1104 0.8672 0.0659 0.131 Uiso 1 1 calc R U . . .
H23B H -0.0886 0.7737 -0.0108 0.131 Uiso 1 1 calc R U . . .
C24 C -0.3415(8) 0.7149(8) 0.0012(4) 0.116(2) Uani 1 1 d . . . . .
H24A H -0.3793 0.6127 -0.0327 0.140 Uiso 1 1 calc R U . . .
H24B H -0.4020 0.6992 0.0459 0.140 Uiso 1 1 calc R U . . .
C26 C -0.3963(10) 0.8228(8) -0.0436(4) 0.135(2) Uani 1 1 d . . . . .
H26A H -0.5266 0.7865 -0.0615 0.203 Uiso 1 1 calc R U . . .
H26B H -0.3440 0.8332 -0.0902 0.203 Uiso 1 1 calc R U . . .
H26C H -0.3569 0.9251 -0.0109 0.203 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.101(5) . ?
N2 C3 1.153(6) . ?
N3 C5 1.138(5) . ?
N4 C9 1.371(5) . ?
N4 C17 1.376(5) . ?
N4 C18 1.437(5) . ?
C1 C2 1.468(6) . ?
C2 C4 1.341(6) . ?
C2 C3 1.409(7) . ?
C4 C5 1.440(6) . ?
C4 C6 1.466(6) . ?
C6 C11 1.410(6) . ?
C6 C7 1.435(6) . ?
C7 C8 1.364(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(5) . ?
C10 C11 1.369(6) . ?
C10 C12 1.472(6) . ?
C11 H11 0.9300 . ?
C12 C17 1.389(6) . ?
C12 C13 1.406(5) . ?
C13 C14 1.356(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(6) . ?
C16 H16 0.9300 . ?
C18 C19 1.494(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.515(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.364(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.597(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.519(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.429(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C26 1.354(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C9 N4 C17 106.5(3) . . ?
C9 N4 C18 127.1(4) . . ?
C17 N4 C18 126.0(4) . . ?
N1 C1 C2 175.7(5) . . ?
C4 C2 C3 121.2(4) . . ?
C4 C2 C1 123.6(4) . . ?
C3 C2 C1 115.1(4) . . ?
N2 C3 C2 178.9(5) . . ?
C2 C4 C5 112.2(4) . . ?
C2 C4 C6 130.5(4) . . ?
C5 C4 C6 117.2(4) . . ?
N3 C5 C4 177.0(5) . . ?
C11 C6 C7 119.7(4) . . ?
C11 C6 C4 117.3(4) . . ?
C7 C6 C4 123.0(4) . . ?
C8 C7 C6 122.2(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 117.3(4) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
N4 C9 C8 127.7(4) . . ?
N4 C9 C10 111.0(4) . . ?
C8 C9 C10 121.1(4) . . ?
C11 C10 C9 122.5(4) . . ?
C11 C10 C12 131.9(4) . . ?
C9 C10 C12 105.6(4) . . ?
C10 C11 C6 117.1(4) . . ?
C10 C11 H11 121.4 . . ?
C6 C11 H11 121.4 . . ?
C17 C12 C13 122.5(4) . . ?
C17 C12 C10 104.7(4) . . ?
C13 C12 C10 132.8(4) . . ?
C14 C13 C12 116.0(4) . . ?
C14 C13 H13 122.0 . . ?
C12 C13 H13 122.0 . . ?
C13 C14 C15 122.5(5) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 121.9(5) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 117.5(4) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
N4 C17 C12 112.2(4) . . ?
N4 C17 C16 128.1(4) . . ?
C12 C17 C16 119.6(4) . . ?
N4 C18 C19 112.6(4) . . ?
N4 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N4 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 115.2(5) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 117.6(5) . . ?
C21 C20 H20A 107.9 . . ?
C19 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
C19 C20 H20B 107.9 . . ?
H20A C20 H20B 107.2 . . ?
C20 C21 C22 112.7(5) . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 102.7(5) . . ?
C23 C22 H22A 111.2 . . ?
C21 C22 H22A 111.2 . . ?
C23 C22 H22B 111.2 . . ?
C21 C22 H22B 111.2 . . ?
H22A C22 H22B 109.1 . . ?
C24 C23 C22 113.1(5) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C26 C24 C23 113.4(6) . . ?
C26 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C26 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C3 C2 C4 C5 3.4(6) . . . . ?
C1 C2 C4 C5 -175.1(4) . . . . ?
C3 C2 C4 C6 -178.4(4) . . . . ?
C1 C2 C4 C6 3.0(7) . . . . ?
C2 C4 C6 C11 -175.9(4) . . . . ?
C5 C4 C6 C11 2.2(5) . . . . ?
C2 C4 C6 C7 4.9(7) . . . . ?
C5 C4 C6 C7 -177.0(4) . . . . ?
C11 C6 C7 C8 1.0(6) . . . . ?
C4 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
C17 N4 C9 C8 177.2(4) . . . . ?
C18 N4 C9 C8 -9.2(7) . . . . ?
C17 N4 C9 C10 2.6(4) . . . . ?
C18 N4 C9 C10 176.3(4) . . . . ?
C7 C8 C9 N4 -176.4(4) . . . . ?
C7 C8 C9 C10 -2.3(6) . . . . ?
N4 C9 C10 C11 177.4(4) . . . . ?
C8 C9 C10 C11 2.4(6) . . . . ?
N4 C9 C10 C12 -1.2(4) . . . . ?
C8 C9 C10 C12 -176.2(4) . . . . ?
C9 C10 C11 C6 -0.6(6) . . . . ?
C12 C10 C11 C6 177.6(4) . . . . ?
C7 C6 C11 C10 -1.0(6) . . . . ?
C4 C6 C11 C10 179.7(3) . . . . ?
C11 C10 C12 C17 -179.0(4) . . . . ?
C9 C10 C12 C17 -0.6(4) . . . . ?
C11 C10 C12 C13 -1.2(8) . . . . ?
C9 C10 C12 C13 177.2(4) . . . . ?
C17 C12 C13 C14 -0.8(6) . . . . ?
C10 C12 C13 C14 -178.3(4) . . . . ?
C12 C13 C14 C15 0.3(7) . . . . ?
C13 C14 C15 C16 1.0(7) . . . . ?
C14 C15 C16 C17 -1.8(7) . . . . ?
C9 N4 C17 C12 -3.1(5) . . . . ?
C18 N4 C17 C12 -176.8(4) . . . . ?
C9 N4 C17 C16 -178.5(4) . . . . ?
C18 N4 C17 C16 7.8(7) . . . . ?
C13 C12 C17 N4 -175.8(4) . . . . ?
C10 C12 C17 N4 2.3(5) . . . . ?
C13 C12 C17 C16 0.1(6) . . . . ?
C10 C12 C17 C16 178.1(4) . . . . ?
C15 C16 C17 N4 176.4(4) . . . . ?
C15 C16 C17 C12 1.2(6) . . . . ?
C9 N4 C18 C19 -89.4(5) . . . . ?
C17 N4 C18 C19 83.1(5) . . . . ?
N4 C18 C19 C20 174.4(4) . . . . ?
C18 C19 C20 C21 77.3(8) . . . . ?
C19 C20 C21 C22 173.6(5) . . . . ?
C20 C21 C22 C23 178.1(6) . . . . ?
C21 C22 C23 C24 -174.5(6) . . . . ?
C22 C23 C24 C26 177.5(6) . . . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.047



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9-butyl-3-(122)-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1562616'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N4'
_chemical_formula_sum            'C21 H16 N4'
_chemical_formula_weight         324.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   8.7842(7)
_cell_length_b                   24.486(2)
_cell_length_c                   8.1096(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.652(3)
_cell_angle_gamma                90
_cell_volume                     1632.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2651
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.51

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22892
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.1497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3749
_reflns_number_gt                2127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0681P)²+0.0951P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.4690(2) 0.62851(7) 0.2971(2) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.3492(2) 0.46311(8) 0.9454(3) 0.0281(5) Uani 1 1 d . . . . .
N3 N 0.0530(2) 0.35718(9) 0.7639(3) 0.0287(5) Uani 1 1 d . . . . .
N4 N -0.0956(2) 0.41418(8) 0.2217(3) 0.0286(5) Uani 1 1 d . . . . .
C1 C 0.5821(2) 0.65165(9) 0.4489(3) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.6898(2) 0.69442(9) 0.4637(3) 0.0205(5) Uani 1 1 d . . . . .
H2 H 0.6928 0.7134 0.3627 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7924(3) 0.70831(9) 0.6308(3) 0.0224(6) Uani 1 1 d . . . . .
H3 H 0.8667 0.7376 0.6444 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7902(3) 0.68066(10) 0.7804(3) 0.0227(6) Uani 1 1 d . . . . .
H4 H 0.8635 0.6910 0.8934 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6818(3) 0.63818(9) 0.7651(3) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.6793 0.6195 0.8667 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5765(2) 0.62348(9) 0.5978(3) 0.0186(5) Uani 1 1 d . . . . .
C7 C 0.4519(2) 0.58220(9) 0.5331(3) 0.0164(5) Uani 1 1 d . . . . .
C8 C 0.3931(3) 0.54228(9) 0.6142(3) 0.0185(5) Uani 1 1 d . . . . .
H8 H 0.4349 0.5388 0.7389 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2710(2) 0.50682(9) 0.5119(3) 0.0189(5) Uani 1 1 d . . . . .
C10 C 0.2126(3) 0.51252(9) 0.3258(3) 0.0216(5) Uani 1 1 d . . . . .
H10 H 0.1315 0.4880 0.2565 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2686(3) 0.55197(9) 0.2423(3) 0.0206(5) Uani 1 1 d . . . . .
H11 H 0.2268 0.5555 0.1176 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3901(2) 0.58703(9) 0.3478(3) 0.0178(5) Uani 1 1 d . . . . .
C13 C 0.2141(3) 0.46531(9) 0.6042(3) 0.0206(5) Uani 1 1 d . . . . .
C14 C 0.0971(3) 0.42586(9) 0.5426(3) 0.0205(5) Uani 1 1 d . . . . .
C15 C 0.2913(3) 0.46442(9) 0.7955(3) 0.0204(5) Uani 1 1 d . . . . .
C16 C 0.0712(3) 0.38772(10) 0.6648(3) 0.0212(5) Uani 1 1 d . . . . .
C17 C -0.0062(3) 0.41971(9) 0.3620(3) 0.0214(5) Uani 1 1 d . . . . .
C18 C 0.4352(3) 0.64585(9) 0.1152(3) 0.0215(5) Uani 1 1 d . . . . .
H18A H 0.4045 0.6134 0.0375 0.026 Uiso 1 1 calc R U . . .
H18B H 0.5360 0.6612 0.1054 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3010(3) 0.68801(9) 0.0508(3) 0.0220(5) Uani 1 1 d . . . . .
H19A H 0.2066 0.6755 0.0804 0.026 Uiso 1 1 calc R U . . .
H19B H 0.2658 0.6905 -0.0791 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3499(2) 0.74463(9) 0.1284(3) 0.0214(5) Uani 1 1 d . . . . .
H20A H 0.4502 0.7561 0.1085 0.026 Uiso 1 1 calc R U . . .
H20B H 0.3744 0.7432 0.2572 0.026 Uiso 1 1 calc R U . . .
C21 C 0.2170(3) 0.78682(10) 0.0473(3) 0.0284(6) Uani 1 1 d . . . . .
H21A H 0.1914 0.7881 -0.0805 0.043 Uiso 1 1 calc R U . . .
H21B H 0.2548 0.8228 0.0982 0.043 Uiso 1 1 calc R U . . .
H21C H 0.1192 0.7767 0.0719 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C12 1.372(3) . ?
N1 C1 1.400(3) . ?
N1 C18 1.461(3) . ?
N2 C15 1.141(3) . ?
N3 C16 1.149(3) . ?
N4 C17 1.140(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(3) . ?
C7 C8 1.377(3) . ?
C7 C12 1.411(3) . ?
C8 C9 1.401(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(3) . ?
C9 C13 1.452(3) . ?
C10 C11 1.367(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.370(3) . ?
C13 C15 1.458(3) . ?
C14 C17 1.433(3) . ?
C14 C16 1.437(3) . ?
C18 C19 1.515(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.520(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C12 N1 C1 108.23(18) . . ?
C12 N1 C18 124.99(19) . . ?
C1 N1 C18 126.76(19) . . ?
C2 C1 N1 129.2(2) . . ?
C2 C1 C6 121.7(2) . . ?
N1 C1 C6 109.13(19) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 133.8(2) . . ?
C1 C6 C7 106.41(19) . . ?
C8 C7 C12 120.0(2) . . ?
C8 C7 C6 133.4(2) . . ?
C12 C7 C6 106.60(19) . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 C13 117.3(2) . . ?
C10 C9 C13 123.8(2) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 117.4(2) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C11 128.8(2) . . ?
N1 C12 C7 109.62(19) . . ?
C11 C12 C7 121.5(2) . . ?
C14 C13 C9 131.0(2) . . ?
C14 C13 C15 112.7(2) . . ?
C9 C13 C15 116.3(2) . . ?
C13 C14 C17 124.7(2) . . ?
C13 C14 C16 119.2(2) . . ?
C17 C14 C16 116.1(2) . . ?
N2 C15 C13 178.6(3) . . ?
N3 C16 C14 179.0(2) . . ?
N4 C17 C14 176.0(3) . . ?
N1 C18 C19 113.72(18) . . ?
N1 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
N1 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 114.02(18) . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 112.22(19) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.066



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9-dodecyl-3-(122)-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1562623'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H32 N4'
_chemical_formula_sum            'C29 H32 N4'
_chemical_formula_weight         436.58

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7023(13)
_cell_length_b                   8.9110(15)
_cell_length_c                   20.022(4)
_cell_angle_alpha                77.669(9)
_cell_angle_beta                 84.775(8)
_cell_angle_gamma                73.953(7)
_cell_volume                     1289.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3647
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      20.28

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27439
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         26.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5387
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0608P)²+0.2913P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5387
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.7425(4) 1.1303(3) 0.39469(14) 0.0960(9) Uani 1 1 d . . . . .
N2 N 1.2909(4) 1.0284(4) 0.31635(16) 0.1159(10) Uani 1 1 d . . . . .
N3 N 1.4515(3) 0.6600(3) 0.44369(14) 0.0972(9) Uani 1 1 d . . . . .
N4 N 0.7488(3) 0.4872(3) 0.66799(11) 0.0668(6) Uani 1 1 d . . . . .
C1 C 0.8810(4) 1.0408(4) 0.39964(15) 0.0729(8) Uani 1 1 d . . . . .
C2 C 1.0594(3) 0.9361(3) 0.40473(14) 0.0654(7) Uani 1 1 d . . . . .
C3 C 1.1879(4) 0.9882(4) 0.35532(16) 0.0790(9) Uani 1 1 d . . . . .
C4 C 1.1094(3) 0.8005(3) 0.45252(14) 0.0611(7) Uani 1 1 d . . . . .
C5 C 1.3015(4) 0.7212(4) 0.44824(14) 0.0708(8) Uani 1 1 d . . . . .
C6 C 1.0061(3) 0.7248(3) 0.50692(13) 0.0586(7) Uani 1 1 d . . . . .
C7 C 0.8167(3) 0.7818(3) 0.51540(14) 0.0689(8) Uani 1 1 d . . . . .
H7 H 0.7554 0.8699 0.4844 0.083 Uiso 1 1 calc R U . . .
C8 C 0.7206(3) 0.7117(4) 0.56781(15) 0.0712(8) Uani 1 1 d . . . . .
H8 H 0.5961 0.7514 0.5727 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8135(3) 0.5800(3) 0.61345(14) 0.0610(7) Uani 1 1 d . . . . .
C10 C 1.0015(3) 0.5173(3) 0.60593(13) 0.0579(7) Uani 1 1 d . . . . .
C11 C 1.0964(3) 0.5899(3) 0.55313(13) 0.0602(7) Uani 1 1 d . . . . .
H11 H 1.2208 0.5493 0.5481 0.072 Uiso 1 1 calc R U . . .
C12 C 1.0523(3) 0.3769(3) 0.65956(13) 0.0605(7) Uani 1 1 d . . . . .
C13 C 1.2122(4) 0.2611(3) 0.67688(16) 0.0731(8) Uani 1 1 d . . . . .
H13 H 1.3197 0.2674 0.6527 0.088 Uiso 1 1 calc R U . . .
C14 C 1.2083(4) 0.1371(4) 0.73044(17) 0.0895(10) Uani 1 1 d . . . . .
H14 H 1.3146 0.0585 0.7424 0.107 Uiso 1 1 calc R U . . .
C15 C 1.0490(5) 0.1265(4) 0.76710(17) 0.0910(10) Uani 1 1 d . . . . .
H15 H 1.0508 0.0409 0.8032 0.109 Uiso 1 1 calc R U . . .
C16 C 0.8885(4) 0.2397(4) 0.75128(16) 0.0794(9) Uani 1 1 d . . . . .
H16 H 0.7822 0.2330 0.7763 0.095 Uiso 1 1 calc R U . . .
C17 C 0.8913(4) 0.3636(3) 0.69685(14) 0.0644(7) Uani 1 1 d . . . . .
C18 C 0.5597(3) 0.5131(4) 0.69303(15) 0.0756(8) Uani 1 1 d . . . . .
H18A H 0.5363 0.4108 0.7125 0.091 Uiso 1 1 calc R U . . .
H18B H 0.4812 0.5629 0.6547 0.091 Uiso 1 1 calc R U . . .
C19 C 0.5140(4) 0.6165(4) 0.74642(16) 0.0866(9) Uani 1 1 d . . . . .
H19A H 0.5303 0.7210 0.7262 0.104 Uiso 1 1 calc R U . . .
H19B H 0.5970 0.5700 0.7835 0.104 Uiso 1 1 calc R U . . .
C20 C 0.3202(4) 0.6348(4) 0.77521(17) 0.1013(11) Uani 1 1 d . . . . .
H20A H 0.2869 0.7246 0.7982 0.122 Uiso 1 1 calc R U . . .
H20B H 0.2400 0.6591 0.7375 0.122 Uiso 1 1 calc R U . . .
C21 C 0.2914(4) 0.4912(4) 0.82416(16) 0.0909(10) Uani 1 1 d . . . . .
H21A H 0.3738 0.4655 0.8613 0.109 Uiso 1 1 calc R U . . .
H21B H 0.3222 0.4021 0.8008 0.109 Uiso 1 1 calc R U . . .
C22 C 0.1007(4) 0.5097(4) 0.85415(17) 0.0977(10) Uani 1 1 d . . . . .
H22A H 0.0683 0.6014 0.8760 0.117 Uiso 1 1 calc R U . . .
H22B H 0.0189 0.5315 0.8171 0.117 Uiso 1 1 calc R U . . .
C23 C 0.0727(4) 0.3680(4) 0.90530(17) 0.0971(10) Uani 1 1 d . . . . .
H23A H 0.1069 0.2761 0.8836 0.117 Uiso 1 1 calc R U . . .
H23B H 0.1535 0.3472 0.9426 0.117 Uiso 1 1 calc R U . . .
C24 C -0.1154(4) 0.3840(4) 0.93454(17) 0.1022(11) Uani 1 1 d . . . . .
H24A H -0.1478 0.4745 0.9571 0.123 Uiso 1 1 calc R U . . .
H24B H -0.1961 0.4086 0.8969 0.123 Uiso 1 1 calc R U . . .
C25 C -0.1495(4) 0.2440(4) 0.98403(18) 0.1039(11) Uani 1 1 d . . . . .
H25A H -0.0677 0.2180 1.0214 0.125 Uiso 1 1 calc R U . . .
H25B H -0.1200 0.1538 0.9613 0.125 Uiso 1 1 calc R U . . .
C26 C -0.3377(5) 0.2643(4) 1.01344(19) 0.1086(11) Uani 1 1 d . . . . .
H26A H -0.3649 0.3527 1.0372 0.130 Uiso 1 1 calc R U . . .
H26B H -0.4190 0.2948 0.9757 0.130 Uiso 1 1 calc R U . . .
C27 C -0.3809(5) 0.1262(4) 1.06137(18) 0.1149(12) Uani 1 1 d . . . . .
H27A H -0.3020 0.0967 1.0998 0.138 Uiso 1 1 calc R U . . .
H27B H -0.3524 0.0369 1.0381 0.138 Uiso 1 1 calc R U . . .
C28 C -0.5712(6) 0.1501(5) 1.0887(2) 0.1441(16) Uani 1 1 d . . . . .
H28A H -0.5958 0.2338 1.1150 0.173 Uiso 1 1 calc R U . . .
H28B H -0.6500 0.1889 1.0501 0.173 Uiso 1 1 calc R U . . .
C29 C -0.6211(7) 0.0148(6) 1.1310(2) 0.170(2) Uani 1 1 d . . . . .
H29A H -0.7477 0.0443 1.1430 0.255 Uiso 1 1 calc R U . . .
H29B H -0.5527 -0.0195 1.1718 0.255 Uiso 1 1 calc R U . . .
H29C H -0.5960 -0.0704 1.1062 0.255 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.139(3) . ?
N2 C3 1.137(3) . ?
N3 C5 1.138(3) . ?
N4 C9 1.366(3) . ?
N4 C17 1.388(3) . ?
N4 C18 1.469(3) . ?
C1 C2 1.430(4) . ?
C2 C4 1.357(4) . ?
C2 C3 1.433(4) . ?
C4 C6 1.449(4) . ?
C4 C5 1.456(4) . ?
C6 C11 1.402(3) . ?
C6 C7 1.413(3) . ?
C7 C8 1.369(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(3) . ?
C10 C11 1.378(3) . ?
C10 C12 1.450(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 C17 1.409(3) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C18 C19 1.513(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.529(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.493(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.515(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.499(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.493(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.488(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.492(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.486(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.491(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.442(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
C9 N4 C17 109.1(2) . . ?
C9 N4 C18 126.1(2) . . ?
C17 N4 C18 124.9(2) . . ?
N1 C1 C2 176.7(3) . . ?
C4 C2 C1 124.6(2) . . ?
C4 C2 C3 121.1(3) . . ?
C1 C2 C3 114.2(3) . . ?
N2 C3 C2 179.4(4) . . ?
C2 C4 C6 131.2(2) . . ?
C2 C4 C5 113.1(2) . . ?
C6 C4 C5 115.7(3) . . ?
N3 C5 C4 178.8(3) . . ?
C11 C6 C7 118.4(2) . . ?
C11 C6 C4 119.1(2) . . ?
C7 C6 C4 122.5(3) . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N4 C9 C8 129.5(2) . . ?
N4 C9 C10 109.2(2) . . ?
C8 C9 C10 121.3(2) . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 C12 133.5(2) . . ?
C9 C10 C12 106.8(2) . . ?
C10 C11 C6 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 119.5(3) . . ?
C13 C12 C10 134.5(2) . . ?
C17 C12 C10 105.9(2) . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 117.4(3) . . ?
C15 C16 H16 121.3 . . ?
C17 C16 H16 121.3 . . ?
C16 C17 N4 129.2(2) . . ?
C16 C17 C12 121.7(3) . . ?
N4 C17 C12 109.1(2) . . ?
N4 C18 C19 112.8(2) . . ?
N4 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N4 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 112.4(3) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 114.2(3) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 114.6(3) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 114.8(3) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.5 . . ?
C24 C23 C22 115.3(3) . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C22 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C25 C24 C23 116.8(3) . . ?
C25 C24 H24A 108.1 . . ?
C23 C24 H24A 108.1 . . ?
C25 C24 H24B 108.1 . . ?
C23 C24 H24B 108.1 . . ?
H24A C24 H24B 107.3 . . ?
C24 C25 C26 115.7(3) . . ?
C24 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
C24 C25 H25B 108.4 . . ?
C26 C25 H25B 108.4 . . ?
H25A C25 H25B 107.4 . . ?
C27 C26 C25 118.0(3) . . ?
C27 C26 H26A 107.8 . . ?
C25 C26 H26A 107.8 . . ?
C27 C26 H26B 107.8 . . ?
C25 C26 H26B 107.8 . . ?
H26A C26 H26B 107.2 . . ?
C26 C27 C28 116.4(3) . . ?
C26 C27 H27A 108.2 . . ?
C28 C27 H27A 108.2 . . ?
C26 C27 H27B 108.2 . . ?
C28 C27 H27B 108.2 . . ?
H27A C27 H27B 107.3 . . ?
C29 C28 C27 117.7(4) . . ?
C29 C28 H28A 107.9 . . ?
C27 C28 H28A 107.9 . . ?
C29 C28 H28B 107.9 . . ?
C27 C28 H28B 107.9 . . ?
H28A C28 H28B 107.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029



