# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_w
_database_code_depnum_ccdc_archive 'CCDC 1473570'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;
_audit_creation_date             2016-03-26
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_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 0.0030 0.0020 '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 0.0060 0.0030 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8410(14)
_cell_length_b                   7.3130(15)
_cell_length_c                   35.529(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1777.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    293
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1329
_reflns_number_total             2018
_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         0.198
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.032
_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)+(0.0746P)²+0.1863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1553
_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:
 C6(H6), C4(H4), C8(H8), C5(H5), C12(H12), C10(H10), C9(H9), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.0370(3) 0.3803(3) 0.59102(5) 0.0744(6) Uani 1 1 d . . . . .
C2 C 0.4063(2) 0.4020(3) 0.57689(5) 0.0431(4) Uani 1 1 d . . . . .
C3 C 0.4539(2) 0.4527(3) 0.53742(5) 0.0447(5) Uani 1 1 d . . . . .
C7 C 0.5157(2) 0.3119(3) 0.64264(5) 0.0445(5) Uani 1 1 d . . . . .
C6 C 0.5409(3) 0.3605(3) 0.60296(5) 0.0485(5) Uani 1 1 d . . . . .
H6 H 0.6697 0.3629 0.5946 0.058 Uiso 1 1 calc R . . . .
C1 C 0.2013(3) 0.3912(3) 0.58563(5) 0.0495(5) Uani 1 1 d . . . . .
C4 C 0.3206(3) 0.4262(3) 0.50838(5) 0.0515(5) Uani 1 1 d . . . . .
H4 H 0.1984 0.3773 0.5138 0.062 Uiso 1 1 calc R . . . .
C8 C 0.3673(3) 0.3787(3) 0.66567(5) 0.0532(5) Uani 1 1 d . . . . .
H8 H 0.2744 0.4583 0.6558 0.064 Uiso 1 1 calc R . . . .
C5 C 0.3654(3) 0.4707(3) 0.47179(5) 0.0523(5) Uani 1 1 d . . . . .
H5 H 0.2741 0.4495 0.4529 0.063 Uiso 1 1 calc R . . . .
C12 C 0.6544(3) 0.1973(3) 0.65875(6) 0.0584(6) Uani 1 1 d . . . . .
H12 H 0.7582 0.1555 0.6442 0.070 Uiso 1 1 calc R . . . .
C10 C 0.4924(3) 0.2102(3) 0.71813(6) 0.0648(6) Uani 1 1 d . . . . .
H10 H 0.4836 0.1754 0.7433 0.078 Uiso 1 1 calc R . . . .
C9 C 0.3573(3) 0.3274(3) 0.70304(6) 0.0628(6) Uani 1 1 d . . . . .
H9 H 0.2576 0.3730 0.7181 0.075 Uiso 1 1 calc R . . . .
C11 C 0.6408(3) 0.1443(3) 0.69594(6) 0.0671(6) Uani 1 1 d . . . . .
H11 H 0.7324 0.0639 0.7060 0.081 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
N1 C1 1.143(2) . ?
C2 C3 1.487(2) . ?
C2 C6 1.341(3) . ?
C2 C1 1.439(2) . ?
C3 C4 1.390(2) . ?
C3 C5 1.396(3) 5_666 ?
C7 C6 1.464(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.389(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C5 C3 1.396(3) 5_666 ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.370(3) . ?
C10 C11 1.373(3) . ?
C9 H9 0.9300 . ?
C11 H11 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
C6 C2 C3 123.89(16) . . ?
C6 C2 C1 120.53(17) . . ?
C1 C2 C3 115.53(15) . . ?
C4 C3 C2 121.44(16) . . ?
C4 C3 C5 117.56(16) . 5_666 ?
C5 C3 C2 121.00(16) 5_666 . ?
C8 C7 C6 124.52(17) . . ?
C12 C7 C6 117.55(16) . . ?
C12 C7 C8 117.87(17) . . ?
C2 C6 C7 129.72(17) . . ?
C2 C6 H6 115.1 . . ?
C7 C6 H6 115.1 . . ?
N1 C1 C2 177.1(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.51(17) . . ?
C5 C4 H4 119.2 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.36(19) . . ?
C9 C8 H8 119.8 . . ?
C3 C5 H5 119.5 5_666 . ?
C4 C5 C3 120.93(17) . 5_666 ?
C4 C5 H5 119.5 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.20(19) . . ?
C11 C12 H12 119.4 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.86(19) . . ?
C10 C9 H9 119.6 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -179.10(18) . . . . ?
C3 C2 C6 C7 178.77(19) . . . . ?
C3 C4 C5 C3 -1.1(3) . . . 5_666 ?
C7 C8 C9 C10 0.0(3) . . . . ?
C7 C12 C11 C10 -2.4(4) . . . . ?
C6 C2 C3 C4 154.7(2) . . . . ?
C6 C2 C3 C5 -25.4(3) . . . 5_666 ?
C6 C7 C8 C9 -178.8(2) . . . . ?
C6 C7 C12 C11 -179.7(2) . . . . ?
C1 C2 C3 C4 -22.5(3) . . . . ?
C1 C2 C3 C5 157.37(19) . . . 5_666 ?
C1 C2 C6 C7 -4.2(3) . . . . ?
C8 C7 C6 C2 -32.2(3) . . . . ?
C8 C7 C12 C11 2.9(3) . . . . ?
C5 C3 C4 C5 1.1(3) 5_666 . . . ?
C12 C7 C6 C2 150.7(2) . . . . ?
C12 C7 C8 C9 -1.7(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C11 C10 C9 C8 0.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_w1
_database_code_depnum_ccdc_archive 'CCDC 1473571'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;
_audit_creation_date             2016-03-26
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H8 N)'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   26.818(6)
_cell_length_b                   6.8919(8)
_cell_length_c                   9.7465(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.459(17)
_cell_angle_gamma                90
_cell_volume                     1771.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3046
_cell_measurement_temperature    293
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.807
_diffrn_reflns_theta_max         24.807
_diffrn_reflns_theta_min         3.055
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1627
_reflns_number_total             3034
_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         0.476
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.055
_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)+(0.1323P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2549
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.759(5) 0.241(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C35A-C36 \\sim C36-C35
 with sigma of 0.02
 C27-C36 \\sim C36-C27A
 with sigma of 0.02
 C33A-C36 \\sim C36-C33
 with sigma of 0.02
 N34A-C36 \\sim C36-N34
 with sigma of 0.02
 N34A-C27A \\sim N34-C27
 with sigma of 0.02
4. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(C35A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C30A) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
6. Others
 Sof(N34A)=Sof(C33A)=Sof(C27A)=Sof(C35A)=Sof(H35A)=Sof(C28A)=Sof(C29A)=
 Sof(H29A)=Sof(C30A)=Sof(H30A)=1-FVAR(1)
 Sof(C27)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C33)=Sof(N34)=
 Sof(C35)=Sof(H35)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C29(H29), C30(H30), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
  C35A(H35A), C29A(H29A), C30A(H30A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.4249(2) 0.1058(8) 0.1652(5) 0.0587(14) Uani 1 1 d . U . . .
C2 C 0.46371(19) 0.0483(8) 0.0799(5) 0.0551(14) Uani 1 1 d . U . . .
C3 C 0.4877(2) 0.1870(7) 0.0124(6) 0.0657(16) Uani 1 1 d . . . . .
H3 H 0.4794 0.3170 0.0205 0.079 Uiso 1 1 calc R . . . .
C4 C 0.5226(2) 0.1397(8) -0.0641(6) 0.0642(16) Uani 1 1 d . . . . .
H4 H 0.5379 0.2375 -0.1077 0.077 Uiso 1 1 calc R . . . .
C7 C 0.4179(3) 0.3106(9) 0.1761(7) 0.085(2) Uani 1 1 d . . . . .
N8 N 0.4116(3) 0.4811(8) 0.1823(8) 0.122(3) Uani 1 1 d . . . . .
C9 C 0.39812(19) -0.0125(7) 0.2267(5) 0.0482(13) Uani 1 1 d . . . . .
H9 H 0.4057 -0.1417 0.2118 0.058 Uiso 1 1 calc R . . . .
C10 C 0.35958(18) 0.0061(6) 0.3124(5) 0.0421(12) Uani 1 1 d . . . . .
C11 C 0.3359(2) -0.1585(8) 0.3484(6) 0.0641(15) Uani 1 1 d . . . . .
H11 H 0.3456 -0.2785 0.3184 0.077 Uiso 1 1 calc R . . . .
C12 C 0.2987(2) -0.1512(10) 0.4264(6) 0.083(2) Uani 1 1 d . . . . .
H12 H 0.2832 -0.2652 0.4477 0.099 Uiso 1 1 calc R . . . .
C13 C 0.2842(2) 0.0198(10) 0.4728(6) 0.0736(19) Uani 1 1 d . . . . .
H13 H 0.2585 0.0241 0.5252 0.088 Uiso 1 1 calc R . . . .
C14 C 0.3074(2) 0.1879(10) 0.4426(6) 0.0768(19) Uani 1 1 d . . . . .
H14 H 0.2981 0.3063 0.4763 0.092 Uiso 1 1 calc R . . . .
C15 C 0.3446(2) 0.1800(8) 0.3619(6) 0.0649(16) Uani 1 1 d . . . . .
H15 H 0.3599 0.2944 0.3405 0.078 Uiso 1 1 calc R . . . .
C27 C 0.92494(19) 0.6012(7) 0.7592(5) 0.0335(15) Uani 0.788(10) 1 d D . P A 1
C28 C 0.9632(3) 0.5475(17) 0.8821(6) 0.0352(17) Uani 0.788(10) 1 d . U P A 1
C29 C 0.9782(3) 0.3566(15) 0.9096(11) 0.0443(19) Uani 0.788(10) 1 d . . P A 1
H29 H 0.9638 0.2583 0.8498 0.053 Uiso 0.788(10) 1 calc R . P A 1
C30 C 1.0140(3) 0.3119(10) 1.0246(11) 0.0445(17) Uani 0.788(10) 1 d . . P A 1
H30 H 1.0234 0.1829 1.0408 0.053 Uiso 0.788(10) 1 calc R . P A 1
C33 C 0.9162(2) 0.8049(9) 0.7361(7) 0.058(2) Uani 0.788(10) 1 d D . P A 1
N34 N 0.9104(11) 0.9644(19) 0.723(2) 0.113(5) Uani 0.788(10) 1 d D . P A 1
C35 C 0.8986(3) 0.4698(15) 0.6716(8) 0.043(2) Uani 0.788(10) 1 d D . P A 1
H35 H 0.9069 0.3414 0.6944 0.052 Uiso 0.788(10) 1 calc R . P A 1
C36 C 0.85898(19) 0.4936(6) 0.5462(5) 0.0460(12) Uani 1 1 d D . . . .
C37 C 0.8370(2) 0.3247(8) 0.4881(5) 0.0668(16) Uani 1 1 d . . . . .
H37 H 0.8475 0.2063 0.5292 0.080 Uiso 1 1 calc R . . . .
C38 C 0.7998(2) 0.3282(9) 0.3707(6) 0.0753(18) Uani 1 1 d . . . . .
H38 H 0.7852 0.2129 0.3335 0.090 Uiso 1 1 calc R . . . .
C39 C 0.7844(2) 0.4995(11) 0.3091(6) 0.0727(18) Uani 1 1 d . . . . .
H39 H 0.7593 0.5013 0.2296 0.087 Uiso 1 1 calc R . . . .
C40 C 0.8054(2) 0.6686(10) 0.3626(6) 0.080(2) Uani 1 1 d . . . . .
H40 H 0.7946 0.7852 0.3192 0.096 Uiso 1 1 calc R . . . .
C41 C 0.8429(2) 0.6695(8) 0.4815(5) 0.0659(16) Uani 1 1 d . . . . .
H41 H 0.8572 0.7859 0.5176 0.079 Uiso 1 1 calc R . . . .
N34A N 0.912(4) 0.032(3) 0.731(9) 0.111(19) Uani 0.212(10) 1 d D . P A 2
C33A C 0.9158(8) 0.193(3) 0.744(2) 0.048(7) Uani 0.212(10) 1 d D . P A 2
C27A C 0.9246(6) 0.397(2) 0.7605(15) 0.027(5) Uani 0.212(10) 1 d D . P A 2
C35A C 0.8975(13) 0.525(5) 0.672(3) 0.034(10) Uani 0.212(10) 1 d D U P A 2
H35A H 0.9043 0.6551 0.6948 0.041 Uiso 0.212(10) 1 calc R . P A 2
C28A C 0.9631(9) 0.451(7) 0.886(2) 0.027(6) Uani 0.212(10) 1 d . U P A 2
C29A C 0.9800(11) 0.644(5) 0.905(3) 0.037(7) Uani 0.212(10) 1 d . U P A 2
H29A H 0.9689 0.7409 0.8401 0.045 Uiso 0.212(10) 1 calc R . P A 2
C30A C 1.0155(18) 0.681(5) 1.031(5) 0.043(9) Uani 0.212(10) 1 d . U P A 2
H30A H 1.0236 0.8099 1.0540 0.052 Uiso 0.212(10) 1 calc R . P A 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
C1 C2 1.499(7) . ?
C1 C7 1.431(8) . ?
C1 C9 1.302(7) . ?
C2 C3 1.384(7) . ?
C2 C4 1.363(7) 3_655 ?
C3 H3 0.9300 . ?
C3 C4 1.339(8) . ?
C4 C2 1.363(7) 3_655 ?
C4 H4 0.9300 . ?
C7 N8 1.190(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.447(7) . ?
C10 C11 1.376(6) . ?
C10 C15 1.380(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.345(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(7) . ?
C15 H15 0.9300 . ?
C27 C28 1.475(8) . ?
C27 C33 1.434(8) . ?
C27 C35 1.353(9) . ?
C28 C29 1.388(9) . ?
C28 C30 1.393(10) 3_767 ?
C29 H29 0.9300 . ?
C29 C30 1.372(11) . ?
C30 C28 1.393(10) 3_767 ?
C30 H30 0.9300 . ?
C33 N34 1.114(14) . ?
C35 H35 0.9300 . ?
C35 C36 1.475(8) . ?
C36 C37 1.379(6) . ?
C36 C41 1.398(6) . ?
C36 C35A 1.471(18) . ?
C37 H37 0.9300 . ?
C37 C38 1.375(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.354(8) . ?
C39 H39 0.9300 . ?
C39 C40 1.357(8) . ?
C40 H40 0.9300 . ?
C40 C41 1.390(7) . ?
C41 H41 0.9300 . ?
N34A C33A 1.12(3) . ?
C33A C27A 1.43(3) . ?
C27A C35A 1.35(3) . ?
C27A C28A 1.49(3) . ?
C35A H35A 0.9300 . ?
C28A C29A 1.41(3) . ?
C28A C30A 1.28(4) 3_767 ?
C29A H29A 0.9300 . ?
C29A C30A 1.44(4) . ?
C30A C28A 1.28(4) 3_767 ?
C30A H30A 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
C7 C1 C2 114.5(5) . . ?
C9 C1 C2 125.9(5) . . ?
C9 C1 C7 119.6(5) . . ?
C3 C2 C1 120.7(5) . . ?
C4 C2 C1 122.8(5) 3_655 . ?
C4 C2 C3 116.5(5) 3_655 . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(5) . . ?
C4 C3 H3 119.0 . . ?
C2 C4 H4 119.2 3_655 . ?
C3 C4 C2 121.6(5) . 3_655 ?
C3 C4 H4 119.2 . . ?
N8 C7 C1 178.6(9) . . ?
C1 C9 H9 111.9 . . ?
C1 C9 C10 136.2(5) . . ?
C10 C9 H9 111.9 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 C15 116.7(5) . . ?
C15 C10 C9 124.3(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.1(5) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(6) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C33 C27 C28 116.3(6) . . ?
C35 C27 C28 123.4(7) . . ?
C35 C27 C33 120.3(6) . . ?
C29 C28 C27 122.0(10) . . ?
C29 C28 C30 117.1(5) . 3_767 ?
C30 C28 C27 120.9(10) 3_767 . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(6) . . ?
C30 C29 H29 119.8 . . ?
C28 C30 H30 118.8 3_767 . ?
C29 C30 C28 122.5(5) . 3_767 ?
C29 C30 H30 118.8 . . ?
N34 C33 C27 177.4(8) . . ?
C27 C35 H35 114.2 . . ?
C27 C35 C36 131.6(8) . . ?
C36 C35 H35 114.2 . . ?
C37 C36 C35 115.9(6) . . ?
C37 C36 C41 118.2(5) . . ?
C37 C36 C35A 130.7(15) . . ?
C41 C36 C35 125.9(6) . . ?
C41 C36 C35A 111.1(14) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 C36 121.2(5) . . ?
C38 C37 H37 119.4 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.1(5) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.8 . . ?
C38 C39 C40 120.4(5) . . ?
C40 C39 H39 119.8 . . ?
C39 C40 H40 119.6 . . ?
C39 C40 C41 120.8(6) . . ?
C41 C40 H40 119.6 . . ?
C36 C41 H41 120.4 . . ?
C40 C41 C36 119.3(5) . . ?
C40 C41 H41 120.4 . . ?
N34A C33A C27A 175(6) . . ?
C33A C27A C28A 114(2) . . ?
C35A C27A C33A 120.8(17) . . ?
C35A C27A C28A 125(2) . . ?
C36 C35A H35A 114.7 . . ?
C27A C35A C36 131(3) . . ?
C27A C35A H35A 114.7 . . ?
C29A C28A C27A 120(4) . . ?
C30A C28A C27A 120(4) 3_767 . ?
C30A C28A C29A 119(2) 3_767 . ?
C28A C29A H29A 122.3 . . ?
C28A C29A C30A 115(2) . . ?
C30A C29A H29A 122.3 . . ?
C28A C30A C29A 124(3) 3_767 . ?
C28A C30A H30A 117.8 3_767 . ?
C29A C30A H30A 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 179.8(5) . . . . ?
C1 C9 C10 C11 173.7(6) . . . . ?
C1 C9 C10 C15 -6.4(9) . . . . ?
C2 C1 C9 C10 179.9(5) . . . . ?
C2 C3 C4 C2 0.1(9) . . . 3_655 ?
C4 C2 C3 C4 -0.1(9) 3_655 . . . ?
C7 C1 C2 C3 -3.5(7) . . . . ?
C7 C1 C2 C4 176.4(5) . . . 3_655 ?
C7 C1 C9 C10 -0.5(10) . . . . ?
C9 C1 C2 C3 176.1(5) . . . . ?
C9 C1 C2 C4 -4.0(8) . . . 3_655 ?
C9 C10 C11 C12 -178.7(5) . . . . ?
C9 C10 C15 C14 179.7(5) . . . . ?
C10 C11 C12 C13 -0.8(10) . . . . ?
C11 C10 C15 C14 -0.4(8) . . . . ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C12 C13 C14 C15 1.6(10) . . . . ?
C13 C14 C15 C10 -1.0(9) . . . . ?
C15 C10 C11 C12 1.4(8) . . . . ?
C27 C28 C29 C30 179.7(7) . . . . ?
C27 C35 C36 C37 -174.6(9) . . . . ?
C27 C35 C36 C41 6.6(15) . . . . ?
C28 C27 C35 C36 179.1(8) . . . . ?
C28 C29 C30 C28 0.0(12) . . . 3_767 ?
C30 C28 C29 C30 0.0(11) 3_767 . . . ?
C33 C27 C28 C29 -174.6(6) . . . . ?
C33 C27 C28 C30 5.0(9) . . . 3_767 ?
C33 C27 C35 C36 -0.3(14) . . . . ?
C35 C27 C28 C29 5.9(10) . . . . ?
C35 C27 C28 C30 -174.5(8) . . . 3_767 ?
C35 C36 C37 C38 -179.7(7) . . . . ?
C35 C36 C41 C40 179.3(7) . . . . ?
C36 C37 C38 C39 0.6(10) . . . . ?
C37 C36 C41 C40 0.5(8) . . . . ?
C37 C36 C35A C27A 5(5) . . . . ?
C37 C38 C39 C40 -0.1(10) . . . . ?
C38 C39 C40 C41 -0.2(10) . . . . ?
C39 C40 C41 C36 0.0(9) . . . . ?
C41 C36 C37 C38 -0.8(9) . . . . ?
C41 C36 C35A C27A -176(3) . . . . ?
C33A C27A C35A C36 -4(5) . . . . ?
C33A C27A C28A C29A 172(2) . . . . ?
C33A C27A C28A C30A -1(3) . . . 3_767 ?
C27A C28A C29A C30A 178(2) . . . . ?
C35A C36 C37 C38 178(2) . . . . ?
C35A C36 C41 C40 -178.2(19) . . . . ?
C35A C27A C28A C29A -12(4) . . . . ?
C35A C27A C28A C30A 175(3) . . . 3_767 ?
C28A C27A C35A C36 180(3) . . . . ?
C28A C29A C30A C28A 9(4) . . . 3_767 ?
C30A C28A C29A C30A -9(4) 3_767 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.759(5)
2 0.241(5)

