# 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_vn075
_database_code_depnum_ccdc_archive 'CCDC 1841783'
_audit_update_record             
;
2018-05-07 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H34 N4'
_chemical_formula_weight         546.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.658(3)
_cell_length_b                   13.839(3)
_cell_length_c                   8.1732(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.54(3)
_cell_angle_gamma                90
_cell_volume                     1518.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5662
_cell_measurement_theta_min      1.517
_cell_measurement_theta_max      25.242

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5662
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3754
_reflns_number_gt                2154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'STOE X-Area'
_computing_cell_refinement       'STOE X-Area'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3754
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.95355(10) 0.38772(11) 0.14091(18) 0.0420(4) Uani 1 1 d . . . . .
H1A H 0.9715 0.4366 0.0885 0.050 Uiso 1 1 calc R U . . .
N2 N 0.87307(10) 0.56997(11) 0.02575(18) 0.0420(4) Uani 1 1 d . . . . .
C1 C 1.00728(13) 0.30399(13) 0.1738(2) 0.0435(4) Uani 1 1 d . . . . .
C2 C 0.95039(14) 0.24169(14) 0.2587(2) 0.0502(5) Uani 1 1 d . . . . .
H2A H 0.9680 0.1794 0.2952 0.060 Uiso 1 1 calc R U . . .
C3 C 0.86578(14) 0.28898(15) 0.2772(2) 0.0507(5) Uani 1 1 d . . . . .
H3A H 0.8158 0.2646 0.3289 0.061 Uiso 1 1 calc R U . . .
C4 C 0.86698(12) 0.38263(14) 0.2035(2) 0.0436(4) Uani 1 1 d . . . . .
C5 C 0.79568(12) 0.45581(14) 0.1958(2) 0.0431(4) Uani 1 1 d . . . . .
C6 C 0.79835(12) 0.54292(13) 0.1092(2) 0.0421(4) Uani 1 1 d . . . . .
C7 C 0.72192(13) 0.61750(15) 0.0922(3) 0.0516(5) Uani 1 1 d . . . . .
H7A H 0.6643 0.6166 0.1378 0.062 Uiso 1 1 calc R U . . .
C8 C 0.75061(14) 0.68779(15) -0.0020(3) 0.0540(5) Uani 1 1 d . . . . .
H8A H 0.7163 0.7446 -0.0352 0.065 Uiso 1 1 calc R U . . .
C9 C 0.84545(13) 0.65802(13) -0.0419(2) 0.0439(4) Uani 1 1 d . . . . .
C10 C 0.90087(13) 0.71567(14) -0.1313(2) 0.0482(5) Uani 1 1 d . . . . .
H10A H 0.8727 0.7749 -0.1670 0.058 Uiso 1 1 calc R U . . .
C11 C 0.71141(13) 0.43598(14) 0.2865(2) 0.0451(4) Uani 1 1 d . . . . .
C12 C 0.72688(14) 0.44740(15) 0.4608(2) 0.0518(5) Uani 1 1 d . . . . .
C13 C 0.65117(17) 0.42163(16) 0.5445(3) 0.0604(6) Uani 1 1 d . . . . .
H13A H 0.6621 0.4277 0.6598 0.072 Uiso 1 1 calc R U . . .
C14 C 0.56016(16) 0.38727(16) 0.4633(3) 0.0597(5) Uani 1 1 d . . . . .
C15 C 0.54507(14) 0.37988(15) 0.2911(3) 0.0576(5) Uani 1 1 d . . . . .
H15A H 0.4833 0.3594 0.2342 0.069 Uiso 1 1 calc R U . . .
C16 C 0.61922(13) 0.40206(14) 0.2003(2) 0.0499(5) Uani 1 1 d . . . . .
C17 C 0.82366(17) 0.4885(2) 0.5566(3) 0.0751(7) Uani 1 1 d . . . . .
H17A H 0.8679 0.5025 0.4809 0.113 Uiso 1 1 calc R U . . .
H17B H 0.8101 0.5468 0.6120 0.113 Uiso 1 1 calc R U . . .
H17C H 0.8542 0.4422 0.6376 0.113 Uiso 1 1 calc R U . . .
C18 C 0.47873(19) 0.35889(19) 0.5578(4) 0.0840(8) Uani 1 1 d . . . . .
H18A H 0.4214 0.3369 0.4807 0.126 Uiso 1 1 calc R U . . .
H18B H 0.5024 0.3080 0.6347 0.126 Uiso 1 1 calc R U . . .
H18C H 0.4609 0.4138 0.6177 0.126 Uiso 1 1 calc R U . . .
C19 C 0.60111(16) 0.38884(19) 0.0142(3) 0.0706(7) Uani 1 1 d . . . . .
H19A H 0.6596 0.4074 -0.0277 0.106 Uiso 1 1 calc R U . . .
H19B H 0.5862 0.3223 -0.0123 0.106 Uiso 1 1 calc R U . . .
H19C H 0.5460 0.4284 -0.0360 0.106 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.372(2) . ?
N1 C4 1.373(2) . ?
N2 C9 1.363(2) . ?
N2 C6 1.379(2) . ?
C1 C10 1.388(2) 3_765 ?
C1 C2 1.423(3) . ?
C2 C3 1.360(3) . ?
C3 C4 1.430(3) . ?
C4 C5 1.398(2) . ?
C5 C6 1.402(3) . ?
C5 C11 1.504(2) . ?
C6 C7 1.456(2) . ?
C7 C8 1.343(3) . ?
C8 C9 1.452(3) . ?
C9 C10 1.395(3) . ?
C10 C1 1.388(2) 3_765 ?
C11 C16 1.406(3) . ?
C11 C12 1.410(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.518(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.389(3) . ?
C14 C18 1.517(3) . ?
C15 C16 1.395(3) . ?
C16 C19 1.507(3) . ?

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 C4 110.48(15) . . ?
C9 N2 C6 105.59(14) . . ?
N1 C1 C10 126.31(17) . 3_765 ?
N1 C1 C2 106.67(15) . . ?
C10 C1 C2 127.01(17) 3_765 . ?
C3 C2 C1 108.28(17) . . ?
C2 C3 C4 108.27(16) . . ?
N1 C4 C5 125.87(17) . . ?
N1 C4 C3 106.28(15) . . ?
C5 C4 C3 127.85(17) . . ?
C4 C5 C6 124.29(16) . . ?
C4 C5 C11 115.79(16) . . ?
C6 C5 C11 119.92(16) . . ?
N2 C6 C5 124.97(15) . . ?
N2 C6 C7 110.04(16) . . ?
C5 C6 C7 124.98(17) . . ?
C8 C7 C6 106.80(17) . . ?
C7 C8 C9 106.81(17) . . ?
N2 C9 C10 126.00(16) . . ?
N2 C9 C8 110.75(16) . . ?
C10 C9 C8 123.19(17) . . ?
C1 C10 C9 128.36(17) 3_765 . ?
C16 C11 C12 119.92(17) . . ?
C16 C11 C5 120.63(17) . . ?
C12 C11 C5 119.39(16) . . ?
C13 C12 C11 118.83(18) . . ?
C13 C12 C17 119.91(19) . . ?
C11 C12 C17 121.25(18) . . ?
C14 C13 C12 122.5(2) . . ?
C13 C14 C15 117.77(18) . . ?
C13 C14 C18 121.6(2) . . ?
C15 C14 C18 120.7(2) . . ?
C14 C15 C16 122.39(19) . . ?
C15 C16 C11 118.51(18) . . ?
C15 C16 C19 120.62(18) . . ?
C11 C16 C19 120.87(17) . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043

