# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1547241'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_date             2017-04-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H32 N2'
_chemical_formula_sum            'C36 H32 N2'
_chemical_formula_weight         492.63
_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 0.0181 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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   38.7879(10)
_cell_length_b                   8.0972(2)
_cell_length_c                   8.3462(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2621.32(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4745
_cell_measurement_temperature    120
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.9074.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0940
0.00 0.00 -1.00 0.0830
2.00 -1.00 0.00 0.0300
-2.00 1.00 0.00 0.0220
-1.00 0.00 0.00 0.0130
1.00 0.00 0.00 0.0090

_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19651
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.614
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_min         4.560
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'shutterless ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'ImuS microsource'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1692
_reflns_number_total             2285
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.034
_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)+(0.0440P)²+0.9330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          
;
 Methyl group C(4)H₃ is disordered between positions A and B, 
 bonded to C(3) and C(2), respectively, with the occupancies of 82% 
 and 18%. Methyl group C(6)H₃ was refined as a rigid body 
 rotating around the C---C bond, with a common refined U for three 
 H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Uiso(H6A)=Uiso(H6B)=Uiso(H6C)=FVAR(1)
 Uiso(H4AA)=Uiso(H4AB)=Uiso(H4AC)=FVAR(2)
 Fixed Sof: H2(0.82) H3(0.18) C4A(0.82) H4AA(0.82) H4AB(0.82) H4AC(0.82)
 C4B(0.18) H4BA(0.18) H4BB(0.18) H4BC(0.18)
3.a Riding coordinates:
 C4B(H4BA,H4BB,H4BC)
3.b Rotating group:
 C6(H6A,H6B,H6C), C4A(H4AA,H4AB,H4AC)
3.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N N 0.34162(4) 0.87174(17) 0.70554(17) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.46819(5) 0.5678(2) 0.5499(2) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.49473(5) 0.6661(2) 0.4891(2) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.4910 0.7818 0.4813 0.029 Uiso 0.82 1 calc R . P A 1
C3 C 0.52613(5) 0.6030(2) 0.4395(2) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.5435 0.6742 0.3989 0.028 Uiso 0.18 1 calc R . P B 2
C5 C 0.33433(5) 1.0368(2) 0.7675(2) 0.0247(4) Uani 1 1 d . . . . .
H5A H 0.3495 1.0588 0.8603 0.030 Uiso 1 1 calc R . . . .
H5B H 0.3102 1.0407 0.8057 0.030 Uiso 1 1 calc R . . . .
C6 C 0.33965(6) 1.1708(2) 0.6426(2) 0.0344(5) Uani 1 1 d . . . . .
H6A H 0.3238 1.1530 0.5530 0.045(4) Uiso 1 1 d GR . . . .
H6B H 0.3635 1.1667 0.6035 0.045(4) Uiso 1 1 d GR . . . .
H6C H 0.3352 1.2790 0.6909 0.045(4) Uiso 1 1 d GR . . . .
C7 C 0.37472(4) 0.8112(2) 0.6823(2) 0.0196(4) Uani 1 1 d . . . . .
C8 C 0.40593(5) 0.8711(2) 0.7399(2) 0.0238(4) Uani 1 1 d . . . . .
H8 H 0.4069 0.9662 0.8063 0.029 Uiso 1 1 calc R . . . .
C9 C 0.43553(5) 0.7870(2) 0.6969(2) 0.0259(4) Uani 1 1 d . . . . .
H9 H 0.4571 0.8260 0.7356 0.031 Uiso 1 1 calc R . . . .
C10 C 0.43511(5) 0.6457(2) 0.5980(2) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.40360(4) 0.5871(2) 0.5424(2) 0.0210(4) Uani 1 1 d . . . . .
H11 H 0.4028 0.4917 0.4763 0.025 Uiso 1 1 calc R . . . .
C12 C 0.37324(4) 0.6689(2) 0.5840(2) 0.0185(4) Uani 1 1 d . . . . .
C13 C 0.33721(4) 0.6447(2) 0.54438(19) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.31969(5) 0.5316(2) 0.4480(2) 0.0207(4) Uani 1 1 d . . . . .
H14 H 0.3318 0.4443 0.3968 0.025 Uiso 1 1 calc R . . . .
C15 C 0.28446(5) 0.5488(2) 0.4281(2) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.2723 0.4732 0.3620 0.030 Uiso 1 1 calc R . . . .
C16 C 0.26666(5) 0.6764(2) 0.5044(2) 0.0270(5) Uani 1 1 d . . . . .
H16 H 0.2424 0.6852 0.4895 0.032 Uiso 1 1 calc R . . . .
C17 C 0.28321(5) 0.7901(2) 0.6007(2) 0.0236(4) Uani 1 1 d . . . . .
H17 H 0.2708 0.8762 0.6523 0.028 Uiso 1 1 calc R . . . .
C18 C 0.31877(4) 0.7741(2) 0.6198(2) 0.0183(4) Uani 1 1 d . . . . .
C4A C 0.55171(6) 0.7266(3) 0.3684(3) 0.0270(6) Uani 0.82 1 d . . P C 1
H4AA H 0.5685 0.7588 0.4506 0.042(4) Uiso 0.82 1 d GR . P C 1
H4AB H 0.5638 0.6756 0.2781 0.042(4) Uiso 0.82 1 d GR . P C 1
H4AC H 0.5393 0.8247 0.3311 0.042(4) Uiso 0.82 1 d GR . P C 1
C4B C 0.4968(3) 0.8584(12) 0.4607(12) 0.024(2) Uiso 0.18 1 d . . P D 2
H4BA H 0.4743 0.8994 0.4258 0.036 Uiso 0.18 1 d R . P D 2
H4BB H 0.5141 0.8819 0.3778 0.036 Uiso 0.18 1 d R . P D 2
H4BC H 0.5035 0.9134 0.5606 0.036 Uiso 0.18 1 d R . P D 2


_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
N C5 1.460(2) . ?
N C7 1.388(2) . ?
N C18 1.387(2) . ?
C1 C2 1.397(3) . ?
C1 C3 1.404(3) 5_666 ?
C1 C10 1.485(2) . ?
C2 C3 1.384(3) . ?
C2 C4B 1.578(9) . ?
C3 C1 1.404(3) 5_666 ?
C3 C4A 1.529(3) . ?
C5 C6 1.519(3) . ?
C7 C8 1.390(2) . ?
C7 C12 1.415(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.410(3) . ?
C10 C11 1.391(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.450(2) . ?
C13 C14 1.395(2) . ?
C13 C18 1.416(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.396(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.394(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
C7 N C5 123.49(15) . . ?
C18 N C5 125.51(15) . . ?
C18 N C7 108.51(14) . . ?
C2 C1 C3 117.94(17) . 5_666 ?
C2 C1 C10 119.56(17) . . ?
C3 C1 C10 122.49(17) 5_666 . ?
C1 C2 C4B 130.9(4) . . ?
C3 C2 C1 123.20(17) . . ?
C3 C2 C4B 105.9(4) . . ?
C1 C3 C4A 124.58(18) 5_666 . ?
C2 C3 C1 118.86(17) . 5_666 ?
C2 C3 C4A 116.48(17) . . ?
N C5 C6 112.61(15) . . ?
N C7 C8 129.34(16) . . ?
N C7 C12 109.34(15) . . ?
C8 C7 C12 121.32(16) . . ?
C9 C8 C7 117.50(17) . . ?
C8 C9 C10 122.79(17) . . ?
C9 C10 C1 119.51(16) . . ?
C11 C10 C1 121.58(16) . . ?
C11 C10 C9 118.85(16) . . ?
C10 C11 C12 119.76(16) . . ?
C7 C12 C13 106.33(14) . . ?
C11 C12 C7 119.77(16) . . ?
C11 C12 C13 133.87(16) . . ?
C14 C13 C12 133.60(16) . . ?
C14 C13 C18 119.71(16) . . ?
C18 C13 C12 106.61(15) . . ?
C15 C14 C13 118.95(16) . . ?
C14 C15 C16 120.55(17) . . ?
C17 C16 C15 121.94(17) . . ?
C16 C17 C18 117.65(17) . . ?
N C18 C13 109.17(15) . . ?
N C18 C17 129.63(16) . . ?
C17 C18 C13 121.19(16) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol, toluene'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1547242'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_date             2017-04-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H26 N4'
_chemical_formula_sum            'C36 H26 N4'
_chemical_formula_weight         514.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H26 N4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3712(5)
_cell_length_b                   12.2475(7)
_cell_length_c                   12.7385(7)
_cell_angle_alpha                92.853(5)
_cell_angle_beta                 102.427(5)
_cell_angle_gamma                111.744(6)
_cell_volume                     1312.61(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.9150
_cell_measurement_theta_min      1.8260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.2495
_exptl_crystal_size_mid          0.1749
_exptl_crystal_size_min          0.0572
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15132
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.809
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -88.00   -1.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469  -57.0000  150.0000 174

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   21.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   21.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469   57.0000  -60.0000 174

#__ type_ start__ end____ width___ exp.time_
  5 omega  -94.00  -35.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -178.0000 -120.0000 118

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   89.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -       20.1719   77.0000 -180.0000 194

#__ type_ start__ end____ width___ exp.time_
  7 omega  -49.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -       20.1719  -77.0000   60.0000 196

#__ type_ start__ end____ width___ exp.time_
  8 omega  -88.00  -45.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469  -57.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega  -38.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469   57.0000 -180.0000 174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0465518000
_diffrn_orient_matrix_UB_12      0.0178476000
_diffrn_orient_matrix_UB_13      0.0544429000
_diffrn_orient_matrix_UB_21      -0.0689927000
_diffrn_orient_matrix_UB_22      -0.0279133000
_diffrn_orient_matrix_UB_23      0.0187842000
_diffrn_orient_matrix_UB_31      0.0127612000
_diffrn_orient_matrix_UB_32      -0.0535791000
_diffrn_orient_matrix_UB_33      -0.0013200000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3317
_reflns_number_total             4626
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.035
_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)+(0.0590P)²+0.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1449
_refine_special_details          
; The highest residual electron density is between C(22) and its inversion 
equivalent, close to the carbazole plane 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(1)
 Uiso(H36A)=Uiso(H36B)=Uiso(H36C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C35(H35A,H35B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C28(H28), C29(H29), C32(H32)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.0995(2) 0.96130(17) 0.42085(15) 0.0279(5) Uani 1 1 d . . . . .
N2 N 0.6291(3) 1.2332(2) 0.26545(19) 0.0422(6) Uani 1 1 d . . . . .
C1 C 1.0342(3) 0.8414(2) 0.42892(18) 0.0271(6) Uani 1 1 d . . . . .
C2 C 1.0957(3) 0.7748(2) 0.4960(2) 0.0333(6) Uani 1 1 d . . . . .
H2 H 1.1960 0.8094 0.5438 0.040 Uiso 1 1 calc R . . . .
C3 C 1.0043(3) 0.6570(2) 0.4897(2) 0.0375(7) Uani 1 1 d . . . . .
H3 H 1.0434 0.6113 0.5343 0.045 Uiso 1 1 calc R . . . .
C4 C 0.8537(3) 0.6030(2) 0.4182(2) 0.0373(6) Uani 1 1 d . . . . .
H4 H 0.7949 0.5224 0.4158 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7918(3) 0.6683(2) 0.35116(19) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.6917 0.6325 0.3035 0.037 Uiso 1 1 calc R . . . .
C6 C 0.8819(3) 0.7888(2) 0.35625(18) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.8565(3) 0.8826(2) 0.29967(18) 0.0250(5) Uani 1 1 d . . . . .
C8 C 0.7341(3) 0.8865(2) 0.21808(18) 0.0280(6) Uani 1 1 d . . . . .
H8 H 0.6435 0.8180 0.1895 0.034 Uiso 1 1 calc R . . . .
C9 C 0.7473(3) 0.9932(2) 0.17921(19) 0.0286(6) Uani 1 1 d . . . . .
C10 C 0.8850(3) 1.0964(2) 0.2238(2) 0.0316(6) Uani 1 1 d . . . . .
H10 H 0.8928 1.1676 0.1980 0.038 Uiso 1 1 calc R . . . .
C11 C 1.0083(3) 1.0947(2) 0.3045(2) 0.0313(6) Uani 1 1 d . . . . .
H11 H 1.0986 1.1634 0.3330 0.038 Uiso 1 1 calc R . . . .
C12 C 0.9936(3) 0.9873(2) 0.34207(18) 0.0259(6) Uani 1 1 d . . . . .
C13 C 0.6205(3) 0.9968(2) 0.08905(19) 0.0299(6) Uani 1 1 d . . . . .
C14 C 0.5611(3) 0.9141(2) -0.0041(2) 0.0309(6) Uani 1 1 d . . . . .
H14 H 0.6002 0.8549 -0.0083 0.037 Uiso 1 1 calc R . . . .
C15 C 0.5559(3) 1.0833(2) 0.09211(19) 0.0306(6) Uani 1 1 d . . . . .
C16 C 0.6003(3) 1.1673(2) 0.1891(2) 0.0329(6) Uani 1 1 d . . . . .
C17 C 1.2613(3) 1.0428(2) 0.47306(19) 0.0312(6) Uani 1 1 d . . . . .
H17A H 1.2975 1.0171 0.5409 0.037 Uiso 1 1 calc R . . . .
H17B H 1.2627 1.1214 0.4899 0.037 Uiso 1 1 calc R . . . .
C18 C 1.3745(3) 1.0495(2) 0.4021(2) 0.0361(6) Uani 1 1 d . . . . .
H18A H 1.3429 1.0796 0.3368 0.043(4) Uiso 1 1 calc GR . . . .
H18B H 1.3718 0.9716 0.3839 0.043(4) Uiso 1 1 calc GR . . . .
H18C H 1.4803 1.1015 0.4407 0.043(4) Uiso 1 1 calc GR . . . .
N3 N 1.0284(2) 0.69097(19) 1.02024(16) 0.0348(5) Uani 1 1 d . . . . .
N4 N 0.6220(3) 0.2567(2) 0.64277(18) 0.0450(6) Uani 1 1 d . . . . .
C19 C 1.1446(3) 0.6520(2) 1.0053(2) 0.0333(6) Uani 1 1 d . . . . .
C20 C 1.2855(3) 0.6644(2) 1.0780(2) 0.0367(6) Uani 1 1 d . . . . .
H20 H 1.3154 0.7048 1.1480 0.044 Uiso 1 1 calc R . . . .
C21 C 1.3788(3) 0.6144(2) 1.0420(2) 0.0421(7) Uani 1 1 d . . . . .
H21 H 1.4725 0.6210 1.0902 0.051 Uiso 1 1 calc R . . . .
C22 C 1.3418(3) 0.5548(2) 0.9384(2) 0.0420(7) Uani 1 1 d . . . . .
H22 H 1.4094 0.5233 0.9174 0.050 Uiso 1 1 calc R . . . .
C23 C 1.1976(3) 0.5430(2) 0.8648(2) 0.0371(6) Uani 1 1 d . . . . .
H23 H 1.1690 0.5029 0.7947 0.045 Uiso 1 1 calc R . . . .
C24 C 1.0996(3) 0.5918(2) 0.89828(19) 0.0299(6) Uani 1 1 d . . . . .
C25 C 0.9503(3) 0.5970(2) 0.84766(19) 0.0288(6) Uani 1 1 d . . . . .
C26 C 0.8475(3) 0.5554(2) 0.74367(19) 0.0291(6) Uani 1 1 d . . . . .
H26 H 0.8724 0.5143 0.6918 0.035 Uiso 1 1 calc R . . . .
C27 C 0.7085(3) 0.5754(2) 0.71797(19) 0.0308(6) Uani 1 1 d . . . . .
C28 C 0.6746(3) 0.6403(2) 0.7969(2) 0.0363(6) Uani 1 1 d . . . . .
H28 H 0.5826 0.6552 0.7792 0.044 Uiso 1 1 calc R . . . .
C29 C 0.7745(3) 0.6824(2) 0.8998(2) 0.0359(6) Uani 1 1 d . . . . .
H29 H 0.7504 0.7248 0.9511 0.043 Uiso 1 1 calc R . . . .
C30 C 0.9111(3) 0.6601(2) 0.92477(19) 0.0316(6) Uani 1 1 d . . . . .
C31 C 0.6007(3) 0.5363(2) 0.6083(2) 0.0305(6) Uani 1 1 d . . . . .
C32 C 0.5423(3) 0.6120(2) 0.55424(19) 0.0303(6) Uani 1 1 d . . . . .
H32 H 0.5687 0.6879 0.5894 0.036 Uiso 1 1 calc R . . . .
C33 C 0.5546(3) 0.4214(2) 0.55094(19) 0.0300(6) Uani 1 1 d . . . . .
C34 C 0.5967(3) 0.3316(2) 0.6035(2) 0.0325(6) Uani 1 1 d . . . . .
C35 C 1.0354(3) 0.7641(3) 1.1166(2) 0.0452(7) Uani 1 1 d . . . . .
H35A H 1.0942 0.7450 1.1805 0.054 Uiso 1 1 calc R . . . .
H35B H 0.9287 0.7464 1.1243 0.054 Uiso 1 1 calc R . . . .
C36 C 1.1150(4) 0.8957(3) 1.1096(3) 0.0739(11) Uani 1 1 d . . . . .
H36A H 1.1171 0.9416 1.1736 0.097(7) Uiso 1 1 calc GR . . . .
H36B H 1.0565 0.9148 1.0467 0.097(7) Uiso 1 1 calc GR . . . .
H36C H 1.2216 0.9137 1.1039 0.097(7) Uiso 1 1 calc GR . . . .


_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 1.385(3) . ?
N1 C12 1.389(3) . ?
N1 C17 1.455(3) . ?
N2 C16 1.148(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.414(3) . ?
C2 C3 1.366(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.381(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.451(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.414(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.411(3) . ?
C9 C13 1.480(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.391(3) . ?
C13 C14 1.387(3) . ?
C13 C15 1.404(3) . ?
C14 C15 1.400(3) 2_675 ?
C15 C14 1.400(3) 2_675 ?
C15 C16 1.447(4) . ?
C17 C18 1.518(3) . ?
N3 C19 1.383(3) . ?
N3 C30 1.379(3) . ?
N3 C35 1.458(3) . ?
N4 C34 1.143(3) . ?
C19 C20 1.391(3) . ?
C19 C24 1.415(3) . ?
C20 C21 1.375(4) . ?
C21 C22 1.383(4) . ?
C22 C23 1.422(4) . ?
C23 C24 1.390(3) . ?
C24 C25 1.435(3) . ?
C25 C26 1.401(3) . ?
C25 C30 1.409(3) . ?
C26 C27 1.387(3) . ?
C27 C28 1.410(3) . ?
C27 C31 1.473(3) . ?
C28 C29 1.381(3) . ?
C29 C30 1.381(4) . ?
C31 C32 1.383(3) . ?
C31 C33 1.419(3) . ?
C32 C33 1.391(3) 2_666 ?
C33 C32 1.391(3) 2_666 ?
C33 C34 1.446(3) . ?
C35 C36 1.522(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.72(19) . . ?
C1 N1 C17 125.70(18) . . ?
C12 N1 C17 124.9(2) . . ?
N1 C1 C2 129.6(2) . . ?
N1 C1 C6 109.26(19) . . ?
C2 C1 C6 121.1(2) . . ?
C3 C2 C1 117.9(2) . . ?
C2 C3 C4 122.1(2) . . ?
C5 C4 C3 120.5(2) . . ?
C4 C5 C6 118.8(2) . . ?
C1 C6 C7 106.4(2) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 133.9(2) . . ?
C8 C7 C6 133.9(2) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 C6 106.6(2) . . ?
C7 C8 C9 119.8(2) . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 C13 120.1(2) . . ?
C10 C9 C13 120.5(2) . . ?
C11 C10 C9 121.8(2) . . ?
C10 C11 C12 118.0(2) . . ?
N1 C12 C7 109.0(2) . . ?
N1 C12 C11 129.6(2) . . ?
C11 C12 C7 121.5(2) . . ?
C14 C13 C9 120.7(2) . . ?
C14 C13 C15 116.8(2) . . ?
C15 C13 C9 122.6(2) . . ?
C13 C14 C15 122.2(2) . 2_675 ?
C13 C15 C16 120.9(2) . . ?
C14 C15 C13 121.0(2) 2_675 . ?
C14 C15 C16 117.9(2) 2_675 . ?
N2 C16 C15 177.2(3) . . ?
N1 C17 C18 112.26(19) . . ?
C19 N3 C35 126.0(2) . . ?
C30 N3 C19 109.0(2) . . ?
C30 N3 C35 124.7(2) . . ?
N3 C19 C20 129.4(2) . . ?
N3 C19 C24 109.0(2) . . ?
C20 C19 C24 121.6(2) . . ?
C21 C20 C19 117.3(2) . . ?
C20 C21 C22 124.0(3) . . ?
C21 C22 C23 118.2(3) . . ?
C24 C23 C22 119.5(2) . . ?
C19 C24 C25 106.1(2) . . ?
C23 C24 C19 119.5(2) . . ?
C23 C24 C25 134.5(2) . . ?
C26 C25 C24 133.5(2) . . ?
C26 C25 C30 119.1(2) . . ?
C30 C25 C24 107.4(2) . . ?
C27 C26 C25 120.1(2) . . ?
C26 C27 C28 119.1(2) . . ?
C26 C27 C31 121.3(2) . . ?
C28 C27 C31 119.5(2) . . ?
C29 C28 C27 121.7(2) . . ?
C30 C29 C28 118.5(2) . . ?
N3 C30 C25 108.5(2) . . ?
N3 C30 C29 130.0(2) . . ?
C29 C30 C25 121.5(2) . . ?
C32 C31 C27 121.2(2) . . ?
C32 C31 C33 116.3(2) . . ?
C33 C31 C27 122.5(2) . . ?
C31 C32 C33 122.2(2) . 2_666 ?
C31 C33 C34 120.7(2) . . ?
C32 C33 C31 121.5(2) 2_666 . ?
C32 C33 C34 117.6(2) 2_666 . ?
N4 C34 C33 176.4(3) . . ?
N3 C35 C36 111.3(2) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0286 0.0000 0.0000 -1.0000 -0.0544 -0.0188 0.0013
0 0 1 0.0286 -0.0000 -0.0000 1.0000 0.0544 0.0188 -0.0013
0 1 0 0.0881 0.0000 1.0000 -0.0000 0.0178 -0.0279 -0.0536
-1 0 0 0.0803 -1.0000 0.0000 -0.0000 -0.0466 0.0690 -0.0128
-1 1 1 0.0731 -1.0000 1.0000 1.0000 0.0257 0.0599 -0.0677
1 -1 -1 0.0731 1.0000 -1.0000 -1.0000 -0.0257 -0.0599 0.0677
-2 0 1 0.0771 -2.0000 -0.0000 1.0000 -0.0387 0.1568 -0.0268
-5 -2 2 0.0789 -5.0000 -2.0000 2.0000 -0.1596 0.4384 0.0407
2 5 -1 0.1010 2.0000 5.0000 -1.0000 0.1279 -0.2963 -0.2411
1 -1 1 0.0730 1.0000 -1.0000 1.0000 0.0831 -0.0223 0.0650
-1 1 -1 0.0697 -1.0000 1.0000 -1.0000 -0.0831 0.0223 -0.0650

_olex2_submission_special_instructions 'No special instructions were received'

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol, chloroform, deuterochloroform'
_exptl_crystal_preparation       ', Luminescent'
