# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_bm1320_structure_1_of_1
_audit_block_doi                 10.5517/cc4jzsd
_database_code_depnum_ccdc_archive 'CCDC 135494'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S0108270199005752 1999
_audit_update_record             
;
1999-10-06 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
#data_carphcn

_chemical_name_systematic        
;
N-(4-cyanophenyl)-carbazole 
;
_chemical_name_common            N-(4-cyanophenyl)-carbazole
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_chemical_compound_source        ?


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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x, y+1/2, -z+1/2'
'x, 1/2-y, 1/2+z'


_cell_length_a                   8.2739(12)
_cell_length_b                   20.681(4)
_cell_length_c                   8.5913(11)
_cell_angle_alpha                90.0
_cell_angle_beta                 104.937(12)
_cell_angle_gamma                90.00
_cell_volume                     1420.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.04
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.72
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_standards_number         3
_diffrn_standards_interval_time  90
_diffrn_standards_decay_%        none
_diffrn_reflns_number            3457
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3251
_reflns_number_gt                2043
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD-4 Software'
_computing_data_reduction        'Xtal3.4 (Hall et al., 1995)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w = 1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.9105P] where P = (Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2043
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.077
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.115
_refine_ls_wR_factor_gt          0.095
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.01
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.48460(15) 0.62320(6) 0.49386(15) 0.0570(3) Uani 1 d . . .
C1 C 0.65506(19) 0.63916(7) 0.53279(19) 0.0581(4) Uani 1 d . . .
C13 C 0.40610(18) 0.58513(7) 0.59030(17) 0.0538(4) Uani 1 d . . .
C12 C 0.40949(19) 0.64661(7) 0.33962(18) 0.0555(4) Uani 1 d . . .
C7 C 0.5320(2) 0.67804(7) 0.2803(2) 0.0601(4) Uani 1 d . . .
C18 C 0.30309(18) 0.53398(7) 0.52291(18) 0.0583(4) Uani 1 d . . .
H6 H 0.2835 0.5252 0.4134 0.070 Uiso 1 calc R . .
C17 C 0.22996(19) 0.49624(7) 0.6173(2) 0.0617(4) Uani 1 d . . .
H7 H 0.1592 0.4626 0.5713 0.074 Uiso 1 calc R . .
C2 C 0.6874(2) 0.67261(7) 0.4017(2) 0.0618(4) Uani 1 d . . .
C14 C 0.4339(2) 0.59822(8) 0.75307(19) 0.0624(4) Uani 1 d . . .
H9 H 0.5002 0.6332 0.7981 0.075 Uiso 1 calc R . .
C16 C 0.2615(2) 0.50828(8) 0.7804(2) 0.0638(4) Uani 1 d . . .
C15 C 0.3635(2) 0.55944(8) 0.84852(19) 0.0669(4) Uani 1 d . . .
H11 H 0.3845 0.5676 0.9584 0.080 Uiso 1 calc R . .
C11 C 0.2439(2) 0.64491(7) 0.25273(19) 0.0636(4) Uani 1 d . . .
H12 H 0.1635 0.6242 0.2930 0.076 Uiso 1 calc R . .
C6 C 0.7805(2) 0.62374(8) 0.6678(2) 0.0686(4) Uani 1 d . . .
H13 H 0.7575 0.6012 0.7534 0.082 Uiso 1 calc R . .
C8 C 0.4855(3) 0.70758(8) 0.1297(2) 0.0738(5) Uani 1 d . . .
H14 H 0.5649 0.7283 0.0880 0.089 Uiso 1 calc R . .
C10 C 0.2020(2) 0.67477(8) 0.1049(2) 0.0744(5) Uani 1 d . . .
H15 H 0.0912 0.6742 0.0443 0.089 Uiso 1 calc R . .
C4 C 0.9761(2) 0.67613(10) 0.5438(3) 0.0888(6) Uani 1 d . . .
H16 H 1.0856 0.6883 0.5493 0.107 Uiso 1 calc R . .
C3 C 0.8518(2) 0.69134(8) 0.4097(3) 0.0790(5) Uani 1 d . . .
H17 H 0.8763 0.7139 0.3249 0.095 Uiso 1 calc R . .
C9 C 0.3217(3) 0.70580(8) 0.0440(2) 0.0805(5) Uani 1 d . . .
H18 H 0.2898 0.7256 -0.0565 0.097 Uiso 1 calc R . .
C19 C 0.1899(3) 0.46672(11) 0.8786(2) 0.0900(6) Uani 1 d . . .
C5 C 0.9414(2) 0.64287(9) 0.6715(3) 0.0808(5) Uani 1 d . . .
H20 H 1.0281 0.6333 0.7614 0.097 Uiso 1 calc R . .
N2 N 0.1334(3) 0.43284(12) 0.9542(2) 0.1395(9) Uani 1 d . . .


_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 1.3971(19) . ?
N1 C1 1.4024(19) . ?
N1 C13 1.4162(17) . ?
C1 C6 1.380(2) . ?
C1 C2 1.405(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.388(2) . ?
C12 C11 1.381(2) . ?
C12 C7 1.406(2) . ?
C7 C8 1.392(2) . ?
C7 C2 1.436(2) . ?
C18 C17 1.373(2) . ?
C17 C16 1.381(2) . ?
C2 C3 1.398(2) . ?
C14 C15 1.379(2) . ?
C16 C15 1.386(2) . ?
C16 C19 1.435(2) . ?
C11 C10 1.374(2) . ?
C6 C5 1.382(2) . ?
C8 C9 1.366(3) . ?
C10 C9 1.390(2) . ?
C4 C3 1.368(3) . ?
C4 C5 1.386(3) . ?
C19 N2 1.134(2) . ?

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 108.59(12) . . ?
C12 N1 C13 126.05(13) . . ?
C1 N1 C13 125.17(13) . . ?
C6 C1 N1 129.66(14) . . ?
C6 C1 C2 122.02(15) . . ?
N1 C1 C2 108.22(14) . . ?
C14 C13 C18 119.66(13) . . ?
C14 C13 N1 120.03(13) . . ?
C18 C13 N1 120.31(13) . . ?
C11 C12 N1 129.83(13) . . ?
C11 C12 C7 121.55(14) . . ?
N1 C12 C7 108.54(14) . . ?
C8 C7 C12 119.14(16) . . ?
C8 C7 C2 133.68(15) . . ?
C12 C7 C2 107.15(14) . . ?
C17 C18 C13 120.25(14) . . ?
C18 C17 C16 119.99(15) . . ?
C3 C2 C1 118.75(17) . . ?
C3 C2 C7 133.73(16) . . ?
C1 C2 C7 107.49(13) . . ?
C15 C14 C13 120.09(15) . . ?
C17 C16 C15 120.11(14) . . ?
C17 C16 C19 119.34(16) . . ?
C15 C16 C19 120.54(16) . . ?
C14 C15 C16 119.85(15) . . ?
C10 C11 C12 117.86(15) . . ?
C1 C6 C5 117.68(17) . . ?
C9 C8 C7 119.19(16) . . ?
C11 C10 C9 121.36(18) . . ?
C3 C4 C5 121.11(17) . . ?
C4 C3 C2 119.20(18) . . ?
C8 C9 C10 120.89(17) . . ?
N2 C19 C16 178.6(2) . . ?
C6 C5 C4 121.24(19) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.12
_refine_diff_density_rms         0.022



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1581448'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            DCNPhCz
_chemical_name_systematic        5-(9H-carbazol-9-yl)isophthalonitrile
_chemical_formula_moiety         'C20 H11 N3'
_chemical_formula_sum            'C20 H11 N3'
_chemical_formula_weight         293.32
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.718(4)
_cell_length_b                   4.7260(10)
_cell_length_c                   19.164(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.969(7)
_cell_angle_gamma                90
_cell_volume                     1505.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    180
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      0.988
_cell_measurement_theta_min      0.981
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0942
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11931
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         1.225
_diffrn_ambient_temperature      287.12
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1643
_reflns_number_total             3712
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1982
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.030
_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)+(0.0469P)²+0.6544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1710
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C004(H004), C007(H007), C008(H008)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N00C N 0.57972(17) 0.7646(7) 0.30216(15) 0.0870(9) Uani 1 1 d . . . . .
N00D N 0.38114(17) -0.0662(7) 0.52040(15) 0.0862(9) Uani 1 1 d . . . . .
N001 N 0.23052(12) 0.7400(5) 0.31114(11) 0.0530(6) Uani 1 1 d . . . . .
C00A C 0.12124(16) 1.0298(6) 0.30339(15) 0.0538(7) Uani 1 1 d . . . . .
C00B C 0.14871(16) 1.0080(6) 0.23490(15) 0.0560(8) Uani 1 1 d . . . . .
C00E C 0.16277(17) 0.8446(7) 0.41994(16) 0.0628(8) Uani 1 1 d . . . . .
H00E H 0.1973 0.7351 0.4501 0.075 Uiso 1 1 calc R . . . .
C00F C 0.52183(19) 0.6958(7) 0.32384(15) 0.0625(8) Uani 1 1 d . . . . .
C00G C 0.37830(18) 0.1010(7) 0.47752(16) 0.0628(8) Uani 1 1 d . . . . .
C00H C 0.25423(17) 0.7539(7) 0.18368(15) 0.0654(9) Uani 1 1 d . . . . .
H00H H 0.2979 0.6308 0.1881 0.079 Uiso 1 1 calc R . . . .
C00I C 0.12141(19) 1.1198(7) 0.16953(18) 0.0741(9) Uani 1 1 d . . . . .
H00I H 0.0772 1.2403 0.1644 0.089 Uiso 1 1 calc R . . . .
C00J C 0.09992(19) 0.9941(8) 0.44417(18) 0.0726(10) Uani 1 1 d . . . . .
H00J H 0.0918 0.9838 0.4914 0.087 Uiso 1 1 calc R . . . .
C00K C 0.05932(18) 1.1779(7) 0.32968(19) 0.0731(9) Uani 1 1 d . . . . .
H00K H 0.0250 1.2899 0.3001 0.088 Uiso 1 1 calc R . . . .
C00L C 0.2260(2) 0.8683(8) 0.12004(16) 0.0780(10) Uani 1 1 d . . . . .
H00L H 0.2514 0.8228 0.0806 0.094 Uiso 1 1 calc R . . . .
C00M C 0.0491(2) 1.1583(8) 0.3993(2) 0.0801(10) Uani 1 1 d . . . . .
H00M H 0.0073 1.2568 0.4168 0.096 Uiso 1 1 calc R . . . .
C00N C 0.1610(2) 1.0486(8) 0.11309(17) 0.0838(11) Uani 1 1 d . . . . .
H00N H 0.1436 1.1234 0.0692 0.101 Uiso 1 1 calc R . . . .
C002 C 0.21500(15) 0.8293(6) 0.24104(14) 0.0517(7) Uani 1 1 d . . . . .
C003 C 0.30377(15) 0.6229(6) 0.34098(14) 0.0495(7) Uani 1 1 d . . . . .
C004 C 0.37583(16) 0.7176(6) 0.31952(14) 0.0520(7) Uani 1 1 d . . . . .
H004 H 0.3757 0.8569 0.2853 0.062 Uiso 1 1 calc R . . . .
C005 C 0.17237(15) 0.8641(6) 0.34934(14) 0.0507(7) Uani 1 1 d . . . . .
C006 C 0.44785(16) 0.6048(6) 0.34909(14) 0.0508(7) Uani 1 1 d . . . . .
C007 C 0.30443(16) 0.4157(6) 0.39206(14) 0.0526(7) Uani 1 1 d . . . . .
H007 H 0.2563 0.3461 0.4056 0.063 Uiso 1 1 calc R . . . .
C008 C 0.44978(17) 0.4033(6) 0.40145(14) 0.0551(7) Uani 1 1 d . . . . .
H008 H 0.4984 0.3305 0.4218 0.066 Uiso 1 1 calc R . . . .
C009 C 0.37749(17) 0.3124(6) 0.42295(14) 0.0539(7) Uani 1 1 d . . . . .


_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
N00C C00F 1.140(3) . ?
N00D C00G 1.137(4) . ?
N001 C002 1.407(3) . ?
N001 C003 1.410(3) . ?
N001 C005 1.405(3) . ?
C00A C00B 1.439(4) . ?
C00A C00K 1.387(4) . ?
C00A C005 1.401(4) . ?
C00B C00I 1.392(4) . ?
C00B C002 1.389(4) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.386(4) . ?
C00E C005 1.382(4) . ?
C00F C006 1.440(4) . ?
C00G C009 1.445(4) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.372(4) . ?
C00H C002 1.384(4) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.367(4) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.383(5) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.366(4) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.377(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C003 C004 1.387(3) . ?
C003 C007 1.384(4) . ?
C004 H004 0.9300 . ?
C004 C006 1.383(4) . ?
C006 C008 1.381(4) . ?
C007 H007 0.9300 . ?
C007 C009 1.389(4) . ?
C008 H008 0.9300 . ?
C008 C009 1.385(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
C002 N001 C003 124.9(2) . . ?
C005 N001 C002 107.7(2) . . ?
C005 N001 C003 124.9(2) . . ?
C00K C00A C00B 133.5(3) . . ?
C00K C00A C005 118.9(3) . . ?
C005 C00A C00B 107.6(2) . . ?
C00I C00B C00A 133.5(3) . . ?
C002 C00B C00A 107.1(2) . . ?
C002 C00B C00I 119.4(3) . . ?
C00J C00E H00E 121.2 . . ?
C005 C00E H00E 121.2 . . ?
C005 C00E C00J 117.6(3) . . ?
N00C C00F C006 178.1(3) . . ?
N00D C00G C009 178.1(3) . . ?
C00L C00H H00H 121.4 . . ?
C00L C00H C002 117.2(3) . . ?
C002 C00H H00H 121.4 . . ?
C00B C00I H00I 120.7 . . ?
C00N C00I C00B 118.6(3) . . ?
C00N C00I H00I 120.7 . . ?
C00E C00J H00J 119.5 . . ?
C00M C00J C00E 121.1(3) . . ?
C00M C00J H00J 119.5 . . ?
C00A C00K H00K 120.2 . . ?
C00M C00K C00A 119.7(3) . . ?
C00M C00K H00K 120.2 . . ?
C00H C00L H00L 119.2 . . ?
C00H C00L C00N 121.7(3) . . ?
C00N C00L H00L 119.2 . . ?
C00J C00M H00M 119.5 . . ?
C00K C00M C00J 120.9(3) . . ?
C00K C00M H00M 119.5 . . ?
C00I C00N C00L 121.2(3) . . ?
C00I C00N H00N 119.4 . . ?
C00L C00N H00N 119.4 . . ?
C00B C002 N001 109.3(2) . . ?
C00H C002 N001 128.7(3) . . ?
C00H C002 C00B 122.0(3) . . ?
C004 C003 N001 119.9(2) . . ?
C007 C003 N001 120.5(2) . . ?
C007 C003 C004 119.7(2) . . ?
C003 C004 H004 120.0 . . ?
C006 C004 C003 120.0(3) . . ?
C006 C004 H004 120.0 . . ?
C00A C005 N001 108.4(2) . . ?
C00E C005 N001 129.8(3) . . ?
C00E C005 C00A 121.8(3) . . ?
C004 C006 C00F 119.3(3) . . ?
C008 C006 C00F 119.6(3) . . ?
C008 C006 C004 121.1(3) . . ?
C003 C007 H007 120.3 . . ?
C003 C007 C009 119.5(3) . . ?
C009 C007 H007 120.3 . . ?
C006 C008 H008 120.8 . . ?
C006 C008 C009 118.3(3) . . ?
C009 C008 H008 120.8 . . ?
C007 C009 C00G 119.5(3) . . ?
C008 C009 C00G 119.1(3) . . ?
C008 C009 C007 121.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ???/????'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1814229'
loop_
_audit_author_name
_audit_author_address
'yuan jie' njupt
_audit_update_record             
;
2018-01-02 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            mPhCzN
_chemical_name_systematic        3-(9H-carbazol-9-yl)benzonitrile
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.231(3)
_cell_length_b                   16.032(4)
_cell_length_c                   8.461(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.900(6)
_cell_angle_gamma                90
_cell_volume                     1384.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.926
_cell_measurement_theta_min      0.912
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.701
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          5
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17904
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.274
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             6206
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         6206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.042
_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)+(0.0599P)²+0.4384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1576
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00H(H00H), C00D(H00D), C00G(H00G), C00K(H00K), C00J(H00J),
 C00I(H00I), C00E(H00E), C00F(H00F), C00C(H00C), C005(H005), C009(H009)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.75683(9) 0.32496(6) 0.26390(11) 0.02513(19) Uani 1 1 d . . . . .
N002 N 0.85615(11) -0.02347(7) 0.08426(15) 0.0362(2) Uani 1 1 d . . . . .
C00L C 0.40755(13) 0.33718(9) 0.48192(17) 0.0392(3) Uani 1 1 d . . . . .
H00L H 0.3270 0.3427 0.5306 0.047 Uiso 1 1 calc R . . . .
C00H C 0.45153(12) 0.40186(8) 0.39201(17) 0.0348(3) Uani 1 1 d . . . . .
H00H H 0.4019 0.4517 0.3783 0.042 Uiso 1 1 calc R . . . .
C00D C 1.08436(12) 0.22598(8) 0.26358(15) 0.0326(3) Uani 1 1 d . . . . .
H00D H 1.1737 0.2408 0.2855 0.039 Uiso 1 1 calc R . . . .
C00G C 0.48025(13) 0.26338(9) 0.50232(15) 0.0352(3) Uani 1 1 d . . . . .
H00G H 0.4483 0.2200 0.5657 0.042 Uiso 1 1 calc R . . . .
C00B C 0.56991(11) 0.39280(7) 0.32162(14) 0.0263(2) Uani 1 1 d . . . . .
C00K C 0.70226(14) 0.55399(8) 0.04414(17) 0.0385(3) Uani 1 1 d . . . . .
H00K H 0.6860 0.6067 -0.0046 0.046 Uiso 1 1 calc R . . . .
C00J C 0.61627(13) 0.52346(7) 0.14910(16) 0.0343(3) Uani 1 1 d . . . . .
H00J H 0.5412 0.5547 0.1729 0.041 Uiso 1 1 calc R . . . .
C00I C 0.81261(14) 0.50849(8) 0.00875(15) 0.0363(3) Uani 1 1 d . . . . .
H00I H 0.8694 0.5305 -0.0652 0.044 Uiso 1 1 calc R . . . .
C00E C 0.98694(12) 0.28437(8) 0.28477(15) 0.0304(2) Uani 1 1 d . . . . .
H00E H 1.0097 0.3387 0.3219 0.036 Uiso 1 1 calc R . . . .
C00A C 0.88488(11) 0.04260(7) 0.12650(14) 0.0273(2) Uani 1 1 d . . . . .
C00F C 0.84160(13) 0.43189(8) 0.07871(14) 0.0312(2) Uani 1 1 d . . . . .
H00F H 0.9173 0.4013 0.0548 0.037 Uiso 1 1 calc R . . . .
C00C C 0.59768(12) 0.25215(8) 0.43223(14) 0.0288(2) Uani 1 1 d . . . . .
H00C H 0.6458 0.2016 0.4446 0.035 Uiso 1 1 calc R . . . .
C003 C 0.75533(11) 0.40174(7) 0.18541(13) 0.0246(2) Uani 1 1 d . . . . .
C004 C 0.64217(11) 0.31800(7) 0.34304(13) 0.0242(2) Uani 1 1 d . . . . .
C005 C 0.82118(11) 0.18318(7) 0.20149(12) 0.0236(2) Uani 1 1 d . . . . .
H005 H 0.7318 0.1681 0.1817 0.028 Uiso 1 1 calc R . . . .
C006 C 0.64164(11) 0.44571(7) 0.21967(13) 0.0262(2) Uani 1 1 d . . . . .
C007 C 0.85541(11) 0.26332(7) 0.25153(13) 0.0249(2) Uani 1 1 d . . . . .
C008 C 0.92066(11) 0.12523(7) 0.18083(12) 0.0243(2) Uani 1 1 d . . . . .
C009 C 1.05250(11) 0.14599(8) 0.21060(14) 0.0291(2) Uani 1 1 d . . . . .
H009 H 1.1192 0.1062 0.1950 0.035 Uiso 1 1 calc R . . . .


_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
N001 C003 1.3982(14) . ?
N001 C004 1.3941(15) . ?
N001 C007 1.4209(14) . ?
N002 C00A 1.1496(16) . ?
C00L H00L 0.9500 . ?
C00L C00H 1.379(2) . ?
C00L C00G 1.402(2) . ?
C00H H00H 0.9500 . ?
C00H C00B 1.3930(17) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.3879(17) . ?
C00D C009 1.3898(17) . ?
C00G H00G 0.9500 . ?
C00G C00C 1.3873(18) . ?
C00B C004 1.4139(15) . ?
C00B C006 1.4451(17) . ?
C00K H00K 0.9500 . ?
C00K C00J 1.381(2) . ?
C00K C00I 1.394(2) . ?
C00J H00J 0.9500 . ?
C00J C006 1.3988(16) . ?
C00I H00I 0.9500 . ?
C00I C00F 1.3865(18) . ?
C00E H00E 0.9500 . ?
C00E C007 1.3973(16) . ?
C00A C008 1.4413(16) . ?
C00F H00F 0.9500 . ?
C00F C003 1.3914(17) . ?
C00C H00C 0.9500 . ?
C00C C004 1.3921(16) . ?
C003 C006 1.4069(16) . ?
C005 H005 0.9500 . ?
C005 C007 1.3902(15) . ?
C005 C008 1.3977(15) . ?
C008 C009 1.3954(17) . ?
C009 H009 0.9500 . ?

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
C003 N001 C007 124.21(10) . . ?
C004 N001 C003 108.43(9) . . ?
C004 N001 C007 127.18(9) . . ?
C00H C00L H00L 119.6 . . ?
C00H C00L C00G 120.80(12) . . ?
C00G C00L H00L 119.6 . . ?
C00L C00H H00H 120.6 . . ?
C00L C00H C00B 118.89(12) . . ?
C00B C00H H00H 120.6 . . ?
C00E C00D H00D 119.7 . . ?
C00E C00D C009 120.61(11) . . ?
C009 C00D H00D 119.7 . . ?
C00L C00G H00G 119.2 . . ?
C00C C00G C00L 121.64(12) . . ?
C00C C00G H00G 119.2 . . ?
C00H C00B C004 119.72(11) . . ?
C00H C00B C006 133.28(11) . . ?
C004 C00B C006 106.98(10) . . ?
C00J C00K H00K 119.6 . . ?
C00J C00K C00I 120.88(12) . . ?
C00I C00K H00K 119.6 . . ?
C00K C00J H00J 120.6 . . ?
C00K C00J C006 118.84(12) . . ?
C006 C00J H00J 120.6 . . ?
C00K C00I H00I 119.2 . . ?
C00F C00I C00K 121.65(12) . . ?
C00F C00I H00I 119.2 . . ?
C00D C00E H00E 120.0 . . ?
C00D C00E C007 120.08(11) . . ?
C007 C00E H00E 120.0 . . ?
N002 C00A C008 179.51(13) . . ?
C00I C00F H00F 121.4 . . ?
C00I C00F C003 117.26(12) . . ?
C003 C00F H00F 121.4 . . ?
C00G C00C H00C 121.4 . . ?
C00G C00C C004 117.25(11) . . ?
C004 C00C H00C 121.4 . . ?
N001 C003 C006 109.01(10) . . ?
C00F C003 N001 128.84(11) . . ?
C00F C003 C006 121.96(11) . . ?
N001 C004 C00B 108.68(10) . . ?
C00C C004 N001 129.63(10) . . ?
C00C C004 C00B 121.69(11) . . ?
C007 C005 H005 120.6 . . ?
C007 C005 C008 118.81(10) . . ?
C008 C005 H005 120.6 . . ?
C00J C006 C00B 133.70(11) . . ?
C00J C006 C003 119.38(11) . . ?
C003 C006 C00B 106.82(10) . . ?
C00E C007 N001 119.73(10) . . ?
C005 C007 N001 119.99(10) . . ?
C005 C007 C00E 120.25(10) . . ?
C005 C008 C00A 118.65(10) . . ?
C009 C008 C00A 119.89(10) . . ?
C009 C008 C005 121.46(10) . . ?
C00D C009 C008 118.75(10) . . ?
C00D C009 H009 120.6 . . ?
C008 C009 H009 120.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PE/DCM'
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1588870'
loop_
_audit_author_name
_audit_author_address
'yuan jie' njupt
_audit_update_record             
;
2017-12-04 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            MCNPhCz
_chemical_name_systematic        3-(9H-carbazol-9-yl)benzonitrile
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   41.374(7)
_cell_length_b                   3.9588(7)
_cell_length_c                   17.309(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.876(4)
_cell_angle_gamma                90
_cell_volume                     2630.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.922
_cell_measurement_theta_min      0.907
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.536
_diffrn_reflns_theta_min         1.061
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4662
_reflns_number_total             5905
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+1.1538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00K(H00K), C00I(H00I), C00A(H00A), C00G(H00G), C00H(H00H),
 C00C(H00C), C00J(H00J), C00E(H00E), C00F(H00F), C00D(H00D), C006(H006)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.37822(2) 0.5554(2) 0.33831(5) 0.01360(14) Uani 1 1 d . . . . .
N002 N 0.29089(2) 0.6849(3) -0.01949(6) 0.0270(2) Uani 1 1 d . . . . .
C00L C 0.47895(2) 0.5400(3) 0.33873(6) 0.01864(18) Uani 1 1 d . . . . .
H00L H 0.5023 0.5436 0.3412 0.022 Uiso 1 1 calc R . . . .
C00K C 0.37460(3) 0.9283(3) 0.53370(6) 0.01839(18) Uani 1 1 d . . . . .
H00K H 0.3593 0.9797 0.5616 0.022 Uiso 1 1 calc R . . . .
C00I C 0.40996(3) 1.0128(3) 0.57185(6) 0.01879(18) Uani 1 1 d . . . . .
H00I H 0.4182 1.1226 0.6244 0.023 Uiso 1 1 calc R . . . .
C00A C 0.33761(2) 0.5750(2) 0.19403(5) 0.01380(16) Uani 1 1 d . . . . .
H00A H 0.3545 0.6891 0.1788 0.017 Uiso 1 1 calc R . . . .
C00G C 0.43298(3) 0.9368(2) 0.53310(6) 0.01695(17) Uani 1 1 d . . . . .
H00G H 0.4570 0.9912 0.5590 0.020 Uiso 1 1 calc R . . . .
C00B C 0.29700(2) 0.6024(3) 0.04854(6) 0.01920(18) Uani 1 1 d . . . . .
C00H C 0.45253(2) 0.4003(3) 0.26913(6) 0.01727(17) Uani 1 1 d . . . . .
H00H H 0.4584 0.3069 0.2255 0.021 Uiso 1 1 calc R . . . .
C00C C 0.36118(2) 0.7716(2) 0.45630(6) 0.01599(17) Uani 1 1 d . . . . .
H00C H 0.3372 0.7156 0.4311 0.019 Uiso 1 1 calc R . . . .
C00J C 0.28714(2) 0.2471(3) 0.23742(7) 0.01867(18) Uani 1 1 d . . . . .
H00J H 0.2700 0.1369 0.2528 0.022 Uiso 1 1 calc R . . . .
C00E C 0.31976(2) 0.3161(2) 0.29824(6) 0.01606(17) Uani 1 1 d . . . . .
H00E H 0.3247 0.2518 0.3544 0.019 Uiso 1 1 calc R . . . .
C00F C 0.27923(2) 0.3365(3) 0.15489(6) 0.01868(18) Uani 1 1 d . . . . .
H00F H 0.2570 0.2877 0.1137 0.022 Uiso 1 1 calc R . . . .
C00D C 0.47119(2) 0.6731(3) 0.40407(6) 0.01682(17) Uani 1 1 d . . . . .
H00D H 0.4891 0.7643 0.4516 0.020 Uiso 1 1 calc R . . . .
C003 C 0.43665(2) 0.6710(2) 0.39879(5) 0.01286(15) Uani 1 1 d . . . . .
C004 C 0.41024(2) 0.5349(2) 0.32760(5) 0.01267(15) Uani 1 1 d . . . . .
C005 C 0.42018(2) 0.7783(2) 0.45509(5) 0.01324(15) Uani 1 1 d . . . . .
C006 C 0.41792(2) 0.3951(2) 0.26243(6) 0.01493(16) Uani 1 1 d . . . . .
H006 H 0.4002 0.2997 0.2152 0.018 Uiso 1 1 calc R . . . .
C007 C 0.30476(2) 0.5003(2) 0.13370(6) 0.01560(17) Uani 1 1 d . . . . .
C008 C 0.34522(2) 0.4801(2) 0.27672(5) 0.01281(15) Uani 1 1 d . . . . .
C009 C 0.38442(2) 0.6998(2) 0.41695(5) 0.01286(15) Uani 1 1 d . . . . .


_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
N001 C004 1.4070(11) . ?
N001 C008 1.4159(11) . ?
N001 C009 1.4089(12) . ?
N002 C00B 1.1556(14) . ?
C00L H00L 0.9500 . ?
C00L C00H 1.4040(14) . ?
C00L C00D 1.3895(14) . ?
C00K H00K 0.9500 . ?
C00K C00I 1.4028(15) . ?
C00K C00C 1.3904(13) . ?
C00I H00I 0.9500 . ?
C00I C00G 1.3872(14) . ?
C00A H00A 0.9500 . ?
C00A C007 1.4027(12) . ?
C00A C008 1.3974(12) . ?
C00G H00G 0.9500 . ?
C00G C005 1.4016(13) . ?
C00B C007 1.4445(14) . ?
C00H H00H 0.9500 . ?
C00H C006 1.3930(13) . ?
C00C H00C 0.9500 . ?
C00C C009 1.3991(12) . ?
C00J H00J 0.9500 . ?
C00J C00E 1.3947(14) . ?
C00J C00F 1.3872(15) . ?
C00E H00E 0.9500 . ?
C00E C008 1.4007(12) . ?
C00F H00F 0.9500 . ?
C00F C007 1.4000(14) . ?
C00D H00D 0.9500 . ?
C00D C003 1.3977(12) . ?
C003 C004 1.4138(12) . ?
C003 C005 1.4454(12) . ?
C004 C006 1.3953(12) . ?
C005 C009 1.4118(13) . ?
C006 H006 0.9500 . ?

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
C004 N001 C008 125.45(8) . . ?
C004 N001 C009 108.00(7) . . ?
C009 N001 C008 126.17(7) . . ?
C00H C00L H00L 119.8 . . ?
C00D C00L H00L 119.8 . . ?
C00D C00L C00H 120.37(9) . . ?
C00I C00K H00K 118.9 . . ?
C00C C00K H00K 118.9 . . ?
C00C C00K C00I 122.15(9) . . ?
C00K C00I H00I 119.9 . . ?
C00G C00I C00K 120.26(9) . . ?
C00G C00I H00I 119.9 . . ?
C007 C00A H00A 120.3 . . ?
C008 C00A H00A 120.3 . . ?
C008 C00A C007 119.47(8) . . ?
C00I C00G H00G 120.6 . . ?
C00I C00G C005 118.81(9) . . ?
C005 C00G H00G 120.6 . . ?
N002 C00B C007 179.76(13) . . ?
C00L C00H H00H 119.2 . . ?
C006 C00H C00L 121.66(9) . . ?
C006 C00H H00H 119.2 . . ?
C00K C00C H00C 121.3 . . ?
C00K C00C C009 117.36(9) . . ?
C009 C00C H00C 121.3 . . ?
C00E C00J H00J 119.4 . . ?
C00F C00J H00J 119.4 . . ?
C00F C00J C00E 121.21(9) . . ?
C00J C00E H00E 119.9 . . ?
C00J C00E C008 120.13(9) . . ?
C008 C00E H00E 119.9 . . ?
C00J C00F H00F 120.8 . . ?
C00J C00F C007 118.44(9) . . ?
C007 C00F H00F 120.8 . . ?
C00L C00D H00D 120.5 . . ?
C00L C00D C003 119.04(9) . . ?
C003 C00D H00D 120.5 . . ?
C00D C003 C004 119.90(8) . . ?
C00D C003 C005 132.96(8) . . ?
C004 C003 C005 107.12(8) . . ?
N001 C004 C003 108.85(8) . . ?
C006 C004 N001 129.69(8) . . ?
C006 C004 C003 121.40(8) . . ?
C00G C005 C003 132.63(8) . . ?
C00G C005 C009 120.21(8) . . ?
C009 C005 C003 107.16(8) . . ?
C00H C006 C004 117.61(8) . . ?
C00H C006 H006 121.2 . . ?
C004 C006 H006 121.2 . . ?
C00A C007 C00B 119.09(9) . . ?
C00F C007 C00A 121.26(9) . . ?
C00F C007 C00B 119.64(9) . . ?
C00A C008 N001 120.05(8) . . ?
C00A C008 C00E 119.48(8) . . ?
C00E C008 N001 120.46(8) . . ?
N001 C009 C005 108.85(7) . . ?
C00C C009 N001 129.94(8) . . ?
C00C C009 C005 121.20(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/PE'
####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1581453'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            scnphcz
_chemical_name_systematic        2-(9H-carbazol-9-yl)benzonitrile
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   14.753(3)
_cell_length_b                   24.611(4)
_cell_length_c                   8.0508(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2923.1(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    180
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0.989
_cell_measurement_theta_min      0.983
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ????
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19120
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.616
_diffrn_reflns_theta_min         3.220
_diffrn_ambient_temperature      294.54
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.754
_reflns_number_gt                4515
_reflns_number_total             6549
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         6549
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.065
_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)+(0.0628P)²+0.5399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C004(H004), C005(H005), C007(H007)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.30068(10) 0.36361(6) 0.5127(2) 0.0440(3) Uani 1 1 d . . . . .
N008 N 0.10226(16) 0.41246(12) 0.7186(3) 0.0838(8) Uani 1 1 d . . . . .
C00A C 0.44494(14) 0.42982(12) 0.9046(3) 0.0645(6) Uani 1 1 d . . . . .
H00A H 0.4780 0.4430 0.9943 0.077 Uiso 1 1 calc R . . . .
C00B C 0.44886(13) 0.37554(12) 0.8656(3) 0.0621(6) Uani 1 1 d . . . . .
H00B H 0.4849 0.3522 0.9280 0.075 Uiso 1 1 calc R . . . .
C00C C 0.22893(17) 0.41084(10) 0.0967(3) 0.0624(6) Uani 1 1 d . . . . .
H00C H 0.2494 0.4098 -0.0125 0.075 Uiso 1 1 calc R . . . .
C00D C 0.11622(16) 0.43718(10) 0.2939(3) 0.0594(5) Uani 1 1 d . . . . .
H00D H 0.0617 0.4544 0.3181 0.071 Uiso 1 1 calc R . . . .
C00E C 0.13144(14) 0.41186(10) 0.5873(3) 0.0577(5) Uani 1 1 d . . . . .
C00F C 0.14822(18) 0.43601(10) 0.1331(3) 0.0657(6) Uani 1 1 d . . . . .
H00F H 0.1149 0.4524 0.0486 0.079 Uiso 1 1 calc R . . . .
C00G C 0.39835(11) 0.35548(8) 0.7314(2) 0.0480(4) Uani 1 1 d . . . . .
C00H C 0.38974(12) 0.30335(8) 0.6516(3) 0.0535(5) Uani 1 1 d . . . . .
C00I C 0.30742(17) 0.26715(9) 0.4108(4) 0.0672(6) Uani 1 1 d . . . . .
H00I H 0.2670 0.2717 0.3233 0.081 Uiso 1 1 calc R . . . .
C00J C 0.42929(16) 0.25234(10) 0.6787(4) 0.0773(8) Uani 1 1 d . . . . .
H00J H 0.4692 0.2469 0.7665 0.093 Uiso 1 1 calc R . . . .
C00K C 0.3486(2) 0.21725(10) 0.4442(5) 0.0860(9) Uani 1 1 d . . . . .
H00K H 0.3353 0.1876 0.3768 0.103 Uiso 1 1 calc R . . . .
C00L C 0.4079(2) 0.21062(10) 0.5730(6) 0.0918(11) Uani 1 1 d . . . . .
H00L H 0.4344 0.1768 0.5895 0.110 Uiso 1 1 calc R . . . .
C002 C 0.24900(11) 0.38765(7) 0.3844(2) 0.0409(3) Uani 1 1 d . . . . .
C003 C 0.34343(10) 0.39201(7) 0.6415(2) 0.0407(3) Uani 1 1 d . . . . .
C004 C 0.33981(12) 0.44699(8) 0.6788(2) 0.0452(4) Uani 1 1 d . . . . .
H004 H 0.3038 0.4707 0.6176 0.054 Uiso 1 1 calc R . . . .
C005 C 0.28018(14) 0.38705(9) 0.2213(2) 0.0534(5) Uani 1 1 d . . . . .
H005 H 0.3353 0.3707 0.1960 0.064 Uiso 1 1 calc R . . . .
C006 C 0.16627(12) 0.41230(7) 0.4207(2) 0.0455(4) Uani 1 1 d . . . . .
C007 C 0.39198(14) 0.46531(10) 0.8112(3) 0.0562(5) Uani 1 1 d . . . . .
H007 H 0.3915 0.5021 0.8379 0.067 Uiso 1 1 calc R . . . .
C009 C 0.33053(12) 0.30956(7) 0.5165(3) 0.0497(4) Uani 1 1 d . . . . .


_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
N001 C002 1.414(2) . ?
N001 C003 1.401(2) . ?
N001 C009 1.401(2) . ?
N008 C00E 1.142(3) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.373(4) . ?
C00A C007 1.392(4) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.402(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.374(4) . ?
C00C C005 1.386(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.379(4) . ?
C00D C006 1.401(3) . ?
C00E C006 1.436(3) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.440(3) . ?
C00G C003 1.410(2) . ?
C00H C00J 1.401(3) . ?
C00H C009 1.404(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.396(4) . ?
C00I C009 1.389(3) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.370(5) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.366(5) . ?
C00L H00L 0.9300 . ?
C002 C005 1.391(2) . ?
C002 C006 1.394(3) . ?
C003 C004 1.387(3) . ?
C004 H004 0.9300 . ?
C004 C007 1.390(3) . ?
C005 H005 0.9300 . ?
C007 H007 0.9300 . ?

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
C003 N001 C002 125.11(14) . . ?
C003 N001 C009 108.44(15) . . ?
C009 N001 C002 125.61(16) . . ?
C00B C00A H00A 119.7 . . ?
C00B C00A C007 120.70(19) . . ?
C007 C00A H00A 119.7 . . ?
C00A C00B H00B 120.1 . . ?
C00A C00B C00G 119.73(19) . . ?
C00G C00B H00B 120.1 . . ?
C00F C00C H00C 119.7 . . ?
C00F C00C C005 120.6(2) . . ?
C005 C00C H00C 119.7 . . ?
C00F C00D H00D 120.2 . . ?
C00F C00D C006 119.7(2) . . ?
C006 C00D H00D 120.2 . . ?
N008 C00E C006 178.3(3) . . ?
C00C C00F C00D 120.4(2) . . ?
C00C C00F H00F 119.8 . . ?
C00D C00F H00F 119.8 . . ?
C00B C00G C00H 134.74(19) . . ?
C00B C00G C003 118.4(2) . . ?
C003 C00G C00H 106.78(16) . . ?
C00J C00H C00G 133.8(2) . . ?
C00J C00H C009 118.5(2) . . ?
C009 C00H C00G 107.66(16) . . ?
C00K C00I H00I 122.1 . . ?
C009 C00I H00I 122.1 . . ?
C009 C00I C00K 115.9(3) . . ?
C00H C00J H00J 120.7 . . ?
C00L C00J C00H 118.6(3) . . ?
C00L C00J H00J 120.7 . . ?
C00I C00K H00K 119.0 . . ?
C00L C00K C00I 122.0(3) . . ?
C00L C00K H00K 119.0 . . ?
C00J C00L H00L 119.0 . . ?
C00K C00L C00J 122.0(2) . . ?
C00K C00L H00L 119.0 . . ?
C005 C002 N001 120.46(17) . . ?
C005 C002 C006 119.49(17) . . ?
C006 C002 N001 120.05(16) . . ?
N001 C003 C00G 108.69(16) . . ?
C004 C003 N001 129.02(15) . . ?
C004 C003 C00G 122.23(16) . . ?
C003 C004 H004 121.3 . . ?
C003 C004 C007 117.45(18) . . ?
C007 C004 H004 121.3 . . ?
C00C C005 C002 119.9(2) . . ?
C00C C005 H005 120.1 . . ?
C002 C005 H005 120.1 . . ?
C00D C006 C00E 119.68(19) . . ?
C002 C006 C00D 119.92(19) . . ?
C002 C006 C00E 120.39(17) . . ?
C00A C007 H007 119.3 . . ?
C004 C007 C00A 121.4(2) . . ?
C004 C007 H007 119.3 . . ?
N001 C009 C00H 108.39(17) . . ?
C00I C009 N001 128.5(2) . . ?
C00I C009 C00H 123.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????/???'
