# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1990760'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          574
_chemical_formula_moiety         'C30 H28 N2'
_chemical_formula_sum            'C30 H28 N2'
_chemical_formula_weight         416.54

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.609(12)
_cell_length_b                   7.722(7)
_cell_length_c                   12.775(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.76(3)
_cell_angle_gamma                90
_cell_volume                     1145.1(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            10668
_diffrn_reflns_av_unetI/netI     0.1629
_diffrn_reflns_av_R_equivalents  0.1722
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         25.672
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2162
_reflns_number_gt                725
_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (H?bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.1306P)²] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     183
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.2727
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.2974
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.998
_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
C1 C 0.6137(5) 0.3269(7) 0.2747(4) 0.0972(18) Uani 1 1 d D . . . .
H1A H 0.604532 0.219673 0.235937 0.117 Uiso 1 1 calc R U . A 1
H1B H 0.662559 0.302456 0.335101 0.117 Uiso 1 1 calc R U . A 1
C2 C 0.6747(8) 0.4540(14) 0.2067(10) 0.116(3) Uani 0.678(13) 1 d D U P B 1
H2A H 0.731768 0.394488 0.165242 0.139 Uiso 0.678(13) 1 calc R U P B 1
H2B H 0.714049 0.539286 0.249970 0.139 Uiso 0.678(13) 1 calc R U P B 1
C3 C 0.5892(8) 0.5425(16) 0.1359(8) 0.120(3) Uani 0.678(13) 1 d D U P B 1
H3A H 0.563038 0.458787 0.084187 0.144 Uiso 0.678(13) 1 calc R U P B 1
H3B H 0.629439 0.633133 0.098587 0.144 Uiso 0.678(13) 1 calc R U P B 1
C2B C 0.627(3) 0.428(2) 0.1745(11) 0.115(4) Uani 0.322(13) 1 d D U P B 2
H2C H 0.703344 0.405965 0.147770 0.138 Uiso 0.322(13) 1 calc R U P B 2
H2D H 0.571923 0.383658 0.123608 0.138 Uiso 0.322(13) 1 calc R U P B 2
C3B C 0.6111(9) 0.622(2) 0.181(2) 0.119(4) Uani 0.322(13) 1 d D U P B 2
H3C H 0.646576 0.670678 0.243323 0.143 Uiso 0.322(13) 1 calc R U P B 2
H3D H 0.639521 0.680714 0.119269 0.143 Uiso 0.322(13) 1 calc R U P B 2
C4 C 0.4830(7) 0.6230(8) 0.1853(5) 0.123(2) Uani 1 1 d D . . . .
H4A H 0.502206 0.737769 0.211079 0.147 Uiso 1 1 calc R U . B 1
H4B H 0.422821 0.635170 0.132468 0.147 Uiso 1 1 calc R U . B 1
C5 C 0.2427(6) 0.6446(7) 0.3294(5) 0.102(2) Uani 1 1 d . . . . .
H5 H 0.237120 0.732539 0.279853 0.122 Uiso 1 1 calc R U . . .
C6 C 0.1588(7) 0.6211(11) 0.4038(6) 0.135(3) Uani 1 1 d . . . . .
H6 H 0.095395 0.694701 0.403313 0.161 Uiso 1 1 calc R U . . .
C7 C 0.1653(5) 0.4944(9) 0.4777(6) 0.115(2) Uani 1 1 d . . . . .
H7 H 0.107037 0.486580 0.526802 0.138 Uiso 1 1 calc R U . . .
C8 C 0.2548(5) 0.3773(7) 0.4828(4) 0.0873(17) Uani 1 1 d . . . . .
H8 H 0.258071 0.289878 0.532781 0.105 Uiso 1 1 calc R U . . .
N9 N 0.4417(3) 0.3050(5) 0.3940(3) 0.0675(12) Uani 1 1 d . . . . .
C10 C 0.5002(4) 0.3806(7) 0.3120(4) 0.0761(15) Uani 1 1 d . . . . .
C11 C 0.4397(6) 0.5168(7) 0.2727(4) 0.0823(16) Uani 1 1 d . . . . .
C12 C 0.3370(5) 0.5302(6) 0.3318(5) 0.0789(16) Uani 1 1 d . . . . .
C13 C 0.3407(4) 0.3987(6) 0.4073(4) 0.0702(14) Uani 1 1 d . . . . .
C14 C 0.4715(4) 0.1508(6) 0.4480(4) 0.0600(13) Uani 1 1 d . . . . .
C15 C 0.5726(8) 0.1405(10) 0.5036(7) 0.067(3) Uani 0.556(8) 1 d D U P C 1
H15 H 0.621495 0.235796 0.507090 0.080 Uiso 0.556(8) 1 calc R U P C 1
C16 C 0.6020(9) -0.0080(10) 0.5537(7) 0.071(3) Uani 0.556(8) 1 d D U P C 1
H16 H 0.671999 -0.014867 0.589689 0.085 Uiso 0.556(8) 1 calc R U P C 1
C15B C 0.4885(10) -0.0022(13) 0.3954(9) 0.069(3) Uani 0.444(8) 1 d D U P C 2
H15B H 0.481471 -0.005018 0.322798 0.083 Uiso 0.444(8) 1 calc R U P C 2
C16B C 0.5156(10) -0.1493(12) 0.4486(9) 0.065(3) Uani 0.444(8) 1 d D U P C 2
H16B H 0.525427 -0.251778 0.411577 0.078 Uiso 0.444(8) 1 calc R U P C 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 C10 1.467(6) . ?
C1 C2 1.495(7) . ?
C1 C2B 1.510(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.499(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2B C3B 1.506(14) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4 1.489(9) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4 C11 1.478(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.382(8) . ?
C5 C12 1.407(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(7) . ?
C7 H7 0.9300 . ?
C8 C13 1.406(6) . ?
C8 H8 0.9300 . ?
N9 C10 1.384(6) . ?
N9 C13 1.390(6) . ?
N9 C14 1.417(5) . ?
C10 C11 1.358(6) . ?
C11 C12 1.423(8) . ?
C12 C13 1.401(6) . ?
C14 C16B 1.327(11) 3_656 ?
C14 C15 1.366(9) . ?
C14 C15B 1.374(11) . ?
C14 C16 1.394(9) 3_656 ?
C15 C16 1.355(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C15B C16B 1.359(9) . ?
C15B H15B 0.9300 . ?
C16B H16B 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
C10 C1 C2 115.9(6) . . ?
C10 C1 C2B 103.3(13) . . ?
C10 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
C10 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 109.6(8) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 117.9(9) . . ?
C2 C3 H3A 107.8 . . ?
C4 C3 H3A 107.8 . . ?
C2 C3 H3B 107.8 . . ?
C4 C3 H3B 107.8 . . ?
H3A C3 H3B 107.2 . . ?
C3B C2B C1 117.1(16) . . ?
C3B C2B H2C 108.0 . . ?
C1 C2B H2C 108.0 . . ?
C3B C2B H2D 108.0 . . ?
C1 C2B H2D 108.0 . . ?
H2C C2B H2D 107.3 . . ?
C4 C3B C2B 97.5(17) . . ?
C4 C3B H3C 112.3 . . ?
C2B C3B H3C 112.3 . . ?
C4 C3B H3D 112.3 . . ?
C2B C3B H3D 112.3 . . ?
H3C C3B H3D 109.9 . . ?
C11 C4 C3B 112.1(10) . . ?
C11 C4 C3 111.8(7) . . ?
C11 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C11 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C12 117.2(6) . . ?
C6 C5 H5 121.4 . . ?
C12 C5 H5 121.4 . . ?
C7 C6 C5 122.6(7) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 122.6(7) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C13 115.6(5) . . ?
C7 C8 H8 122.2 . . ?
C13 C8 H8 122.2 . . ?
C10 N9 C13 107.2(4) . . ?
C10 N9 C14 127.1(4) . . ?
C13 N9 C14 125.4(4) . . ?
C11 C10 N9 110.5(5) . . ?
C11 C10 C1 124.2(6) . . ?
N9 C10 C1 125.3(5) . . ?
C10 C11 C12 107.0(5) . . ?
C10 C11 C4 122.0(6) . . ?
C12 C11 C4 131.0(6) . . ?
C13 C12 C5 119.2(6) . . ?
C13 C12 C11 107.1(5) . . ?
C5 C12 C11 133.7(6) . . ?
N9 C13 C12 108.1(5) . . ?
N9 C13 C8 129.1(5) . . ?
C12 C13 C8 122.8(5) . . ?
C16B C14 C15B 117.7(6) 3_656 . ?
C15 C14 C16 118.9(5) . 3_656 ?
C16B C14 N9 121.0(6) 3_656 . ?
C15 C14 N9 120.3(5) . . ?
C15B C14 N9 121.3(6) . . ?
C16 C14 N9 120.8(5) 3_656 . ?
C16 C15 C14 120.3(7) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C14 120.8(7) . 3_656 ?
C15 C16 H16 119.6 . . ?
C14 C16 H16 119.6 3_656 . ?
C16B C15B C14 120.5(9) . . ?
C16B C15B H15B 119.8 . . ?
C14 C15B H15B 119.8 . . ?
C14 C16B C15B 121.8(10) 3_656 . ?
C14 C16B H16B 119.1 3_656 . ?
C15B C16B H16B 119.1 . . ?

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
C10 C1 C2 C3 -37.8(14) . . . . ?
C1 C2 C3 C4 51.3(18) . . . . ?
C10 C1 C2B C3B 54(2) . . . . ?
C1 C2B C3B C4 -77(3) . . . . ?
C2B C3B C4 C11 55.8(17) . . . . ?
C2 C3 C4 C11 -37.3(14) . . . . ?
C12 C5 C6 C7 0.5(10) . . . . ?
C5 C6 C7 C8 -1.5(11) . . . . ?
C6 C7 C8 C13 1.1(8) . . . . ?
C13 N9 C10 C11 -0.6(5) . . . . ?
C14 N9 C10 C11 173.4(4) . . . . ?
C13 N9 C10 C1 177.2(4) . . . . ?
C14 N9 C10 C1 -8.8(8) . . . . ?
C2 C1 C10 C11 13.9(9) . . . . ?
C2B C1 C10 C11 -12.1(10) . . . . ?
C2 C1 C10 N9 -163.6(7) . . . . ?
C2B C1 C10 N9 170.4(9) . . . . ?
N9 C10 C11 C12 -0.1(6) . . . . ?
C1 C10 C11 C12 -177.9(5) . . . . ?
N9 C10 C11 C4 179.1(4) . . . . ?
C1 C10 C11 C4 1.2(8) . . . . ?
C3B C4 C11 C10 -26.8(12) . . . . ?
C3 C4 C11 C10 9.7(9) . . . . ?
C3B C4 C11 C12 152.2(12) . . . . ?
C3 C4 C11 C12 -171.4(7) . . . . ?
C6 C5 C12 C13 0.7(8) . . . . ?
C6 C5 C12 C11 -177.3(6) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C4 C11 C12 C13 -178.4(5) . . . . ?
C10 C11 C12 C5 178.8(5) . . . . ?
C4 C11 C12 C5 -0.2(10) . . . . ?
C10 N9 C13 C12 1.0(5) . . . . ?
C14 N9 C13 C12 -173.1(4) . . . . ?
C10 N9 C13 C8 -177.3(5) . . . . ?
C14 N9 C13 C8 8.6(8) . . . . ?
C5 C12 C13 N9 -179.5(4) . . . . ?
C11 C12 C13 N9 -1.0(5) . . . . ?
C5 C12 C13 C8 -1.1(7) . . . . ?
C11 C12 C13 C8 177.4(4) . . . . ?
C7 C8 C13 N9 178.3(4) . . . . ?
C7 C8 C13 C12 0.2(7) . . . . ?
C10 N9 C14 C16B 125.4(8) . . . 3_656 ?
C13 N9 C14 C16B -61.7(8) . . . 3_656 ?
C10 N9 C14 C15 62.9(8) . . . . ?
C13 N9 C14 C15 -124.1(7) . . . . ?
C10 N9 C14 C15B -54.4(9) . . . . ?
C13 N9 C14 C15B 118.6(8) . . . . ?
C10 N9 C14 C16 -117.8(7) . . . 3_656 ?
C13 N9 C14 C16 55.2(8) . . . 3_656 ?
C16 C14 C15 C16 1.8(14) 3_656 . . . ?
N9 C14 C15 C16 -178.9(6) . . . . ?
C14 C15 C16 C14 -1.9(14) . . . 3_656 ?
C16B C14 C15B C16B 1.1(16) 3_656 . . . ?
N9 C14 C15B C16B -179.1(8) . . . . ?
C14 C15B C16B C14 -1.1(17) . . . 3_656 ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# 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_208RMB19
_database_code_depnum_ccdc_archive 'CCDC 1998402'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          574
_chemical_formula_moiety         'C30 H28 N2'
_chemical_formula_sum            'C30 H28 N2'
_chemical_formula_weight         416.54

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4789(10)
_cell_length_b                   7.7861(6)
_cell_length_c                   12.4833(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.539(3)
_cell_angle_gamma                90
_cell_volume                     1115.30(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5718
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            13999
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         30.088
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3260
_reflns_number_gt                1696
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hï?1/2bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.1325P)²+0.2084P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     281
_refine_ls_number_restraints     789
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0828
_refine_ls_wR_factor_ref         0.2513
_refine_ls_wR_factor_gt          0.2076
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.998
_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
C1 C 0.6253(7) 0.3099(10) 0.2712(8) 0.0621(14) Uani 0.537(3) 1 d D U P A 1
H1A H 0.615137 0.206725 0.225487 0.075 Uiso 0.537(3) 1 calc R U P A 1
H1B H 0.674006 0.278073 0.334752 0.075 Uiso 0.537(3) 1 calc R U P A 1
C2 C 0.6843(5) 0.4504(8) 0.2092(5) 0.0766(13) Uani 0.537(3) 1 d D U P A 1
H2A H 0.750404 0.400845 0.170389 0.092 Uiso 0.537(3) 1 calc R U P A 1
H2B H 0.715975 0.537208 0.260114 0.092 Uiso 0.537(3) 1 calc R U P A 1
C3 C 0.6008(5) 0.5384(8) 0.1289(4) 0.0673(11) Uani 0.537(3) 1 d D U P A 1
H3A H 0.644194 0.628224 0.090425 0.081 Uiso 0.537(3) 1 calc R U P A 1
H3B H 0.573799 0.452474 0.075270 0.081 Uiso 0.537(3) 1 calc R U P A 1
C4 C 0.5026(6) 0.6143(8) 0.1752(5) 0.0659(13) Uani 0.537(3) 1 d D U P A 1
H4A H 0.440761 0.628591 0.119016 0.079 Uiso 0.537(3) 1 calc R U P A 1
H4B H 0.524207 0.730079 0.201765 0.079 Uiso 0.537(3) 1 calc R U P A 1
C5 C 0.2616(5) 0.6605(8) 0.3171(5) 0.0568(13) Uani 0.537(3) 1 d D U P A 1
H5 H 0.258916 0.746544 0.263106 0.068 Uiso 0.537(3) 1 calc R U P A 1
C6 C 0.1770(6) 0.6486(8) 0.3942(6) 0.0750(16) Uani 0.537(3) 1 d D U P A 1
H6 H 0.119303 0.735898 0.396179 0.090 Uiso 0.537(3) 1 calc R U P A 1
C7 C 0.1719(6) 0.5163(9) 0.4688(6) 0.0636(14) Uani 0.537(3) 1 d D U P A 1
H7 H 0.107195 0.507971 0.514442 0.076 Uiso 0.537(3) 1 calc R U P A 1
C8 C 0.2630(7) 0.3938(10) 0.4767(7) 0.0523(14) Uani 0.537(3) 1 d D U P A 1
H8 H 0.264781 0.306873 0.530108 0.063 Uiso 0.537(3) 1 calc R U P A 1
N9 N 0.4495(10) 0.3067(17) 0.3896(12) 0.0459(13) Uani 0.537(3) 1 d D U P A 1
C10 C 0.5116(6) 0.3719(10) 0.3049(7) 0.0483(12) Uani 0.537(3) 1 d D U P A 1
C11 C 0.4553(5) 0.5141(9) 0.2643(5) 0.0507(11) Uani 0.537(3) 1 d D U P A 1
C12 C 0.3526(5) 0.5366(8) 0.3234(5) 0.0460(11) Uani 0.537(3) 1 d D U P A 1
C13 C 0.3503(6) 0.4088(11) 0.4011(7) 0.0449(12) Uani 0.537(3) 1 d D U P A 1
C1B C 0.6044(7) 0.3447(11) 0.2751(9) 0.0610(15) Uani 0.463(3) 1 d D U P A 2
H1C H 0.604980 0.220667 0.257568 0.073 Uiso 0.463(3) 1 calc R U P A 2
H1D H 0.665186 0.365827 0.331265 0.073 Uiso 0.463(3) 1 calc R U P A 2
C2B C 0.6316(7) 0.4470(9) 0.1765(6) 0.0774(15) Uani 0.463(3) 1 d D U P A 2
H2C H 0.598723 0.387025 0.112659 0.093 Uiso 0.463(3) 1 calc R U P A 2
H2D H 0.717223 0.452454 0.169329 0.093 Uiso 0.463(3) 1 calc R U P A 2
C3B C 0.5832(6) 0.6293(9) 0.1792(7) 0.0888(16) Uani 0.463(3) 1 d D U P A 2
H3C H 0.624546 0.693340 0.237202 0.107 Uiso 0.463(3) 1 calc R U P A 2
H3D H 0.600866 0.686498 0.110647 0.107 Uiso 0.463(3) 1 calc R U P A 2
C4B C 0.4623(6) 0.6414(10) 0.1951(6) 0.0706(15) Uani 0.463(3) 1 d D U P A 2
H4C H 0.420034 0.612552 0.127350 0.085 Uiso 0.463(3) 1 calc R U P A 2
H4D H 0.442826 0.761466 0.213697 0.085 Uiso 0.463(3) 1 calc R U P A 2
C5B C 0.2220(6) 0.6400(9) 0.3415(6) 0.0520(14) Uani 0.463(3) 1 d D U P A 2
H5B H 0.214923 0.734042 0.293258 0.062 Uiso 0.463(3) 1 calc R U P A 2
C6B C 0.1361(5) 0.6036(8) 0.4153(6) 0.0572(14) Uani 0.463(3) 1 d D U P A 2
H6B H 0.065684 0.667799 0.412306 0.069 Uiso 0.463(3) 1 calc R U P A 2
C7B C 0.1500(7) 0.4758(10) 0.4934(7) 0.0634(16) Uani 0.463(3) 1 d D U P A 2
H7B H 0.094271 0.465373 0.547936 0.076 Uiso 0.463(3) 1 calc R U P A 2
C8B C 0.2455(8) 0.3625(13) 0.4922(8) 0.0523(15) Uani 0.463(3) 1 d D U P A 2
H8B H 0.253056 0.269753 0.541374 0.063 Uiso 0.463(3) 1 calc R U P A 2
N9B N 0.4329(11) 0.3068(19) 0.3968(13) 0.0439(14) Uani 0.463(3) 1 d D U P A 2
C10B C 0.4903(7) 0.3919(12) 0.3157(9) 0.0502(13) Uani 0.463(3) 1 d D U P A 2
C11B C 0.4225(6) 0.5266(9) 0.2806(6) 0.0513(13) Uani 0.463(3) 1 d D U P A 2
C12B C 0.3206(6) 0.5294(10) 0.3420(7) 0.0482(13) Uani 0.463(3) 1 d D U P A 2
C13B C 0.3285(7) 0.3937(12) 0.4150(8) 0.0448(13) Uani 0.463(3) 1 d D U P A 2
C14 C 0.47126(17) 0.1513(2) 0.44727(15) 0.0421(5) Uani 1 1 d . U . . .
C15 C 0.5761(3) 0.1379(5) 0.5006(3) 0.0468(10) Uani 0.537(3) 1 d D U P A 1
H15 H 0.628440 0.232436 0.502174 0.056 Uiso 0.537(3) 1 calc R U P A 1
C16 C 0.6063(3) -0.0129(5) 0.5523(3) 0.0490(10) Uani 0.537(3) 1 d D U P A 1
H16 H 0.680227 -0.022671 0.587857 0.059 Uiso 0.537(3) 1 calc R U P A 1
C15B C 0.4936(3) 0.0008(5) 0.3898(3) 0.0390(9) Uani 0.463(3) 1 d D U P A 2
H15B H 0.490677 0.001992 0.313671 0.047 Uiso 0.463(3) 1 calc R U P A 2
C16B C 0.5200(4) -0.1495(5) 0.4444(3) 0.0403(10) Uani 0.463(3) 1 d D U P A 2
H16B H 0.532193 -0.252518 0.405476 0.048 Uiso 0.463(3) 1 calc R U 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 C10 1.464(5) . ?
C1 C2 1.510(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.530(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.411(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.475(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.390(7) . ?
C5 C12 1.422(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(5) . ?
C7 H7 0.9500 . ?
C8 C13 1.399(6) . ?
C8 H8 0.9500 . ?
N9 C10 1.388(5) . ?
N9 C13 1.400(5) . ?
N9 C14 1.426(6) . ?
C10 C11 1.371(5) . ?
C11 C12 1.418(6) . ?
C12 C13 1.390(5) . ?
C1B C10B 1.464(6) . ?
C1B C2B 1.506(7) . ?
C1B H1C 0.9900 . ?
C1B H1D 0.9900 . ?
C2B C3B 1.525(8) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B C4B 1.410(7) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B C11B 1.475(6) . ?
C4B H4C 0.9900 . ?
C4B H4D 0.9900 . ?
C5B C6B 1.397(8) . ?
C5B C12B 1.421(6) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.399(7) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.408(6) . ?
C7B H7B 0.9500 . ?
C8B C13B 1.395(6) . ?
C8B H8B 0.9500 . ?
N9B C10B 1.390(5) . ?
N9B C13B 1.401(5) . ?
N9B C14 1.428(6) . ?
C10B C11B 1.371(6) . ?
C11B C12B 1.415(7) . ?
C12B C13B 1.397(5) . ?
C14 C16B 1.353(4) 3_656 ?
C14 C15 1.364(4) . ?
C14 C16 1.398(4) 3_656 ?
C14 C15B 1.401(4) . ?
C15 C16 1.379(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C15B C16B 1.385(5) . ?
C15B H15B 0.9500 . ?
C16B H16B 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
C10 C1 C2 108.9(4) . . ?
C10 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C10 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 112.3(5) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 114.3(4) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C11 113.7(4) . . ?
C3 C4 H4A 108.8 . . ?
C11 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C11 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C12 116.2(4) . . ?
C6 C5 H5 121.9 . . ?
C12 C5 H5 121.9 . . ?
C5 C6 C7 123.8(4) . . ?
C5 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C6 C7 C8 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C13 C8 C7 115.9(4) . . ?
C13 C8 H8 122.0 . . ?
C7 C8 H8 122.0 . . ?
C10 N9 C13 107.8(3) . . ?
C10 N9 C14 127.5(4) . . ?
C13 N9 C14 124.2(4) . . ?
C11 C10 N9 109.3(4) . . ?
C11 C10 C1 125.1(4) . . ?
N9 C10 C1 125.3(4) . . ?
C10 C11 C12 107.3(3) . . ?
C10 C11 C4 121.8(4) . . ?
C12 C11 C4 130.9(4) . . ?
C13 C12 C11 107.8(3) . . ?
C13 C12 C5 119.8(4) . . ?
C11 C12 C5 132.4(4) . . ?
C12 C13 C8 123.9(4) . . ?
C12 C13 N9 107.7(4) . . ?
C8 C13 N9 128.4(4) . . ?
C10B C1B C2B 111.0(5) . . ?
C10B C1B H1C 109.4 . . ?
C2B C1B H1C 109.4 . . ?
C10B C1B H1D 109.4 . . ?
C2B C1B H1D 109.4 . . ?
H1C C1B H1D 108.0 . . ?
C1B C2B C3B 113.0(6) . . ?
C1B C2B H2C 109.0 . . ?
C3B C2B H2C 109.0 . . ?
C1B C2B H2D 109.0 . . ?
C3B C2B H2D 109.0 . . ?
H2C C2B H2D 107.8 . . ?
C4B C3B C2B 115.2(6) . . ?
C4B C3B H3C 108.5 . . ?
C2B C3B H3C 108.5 . . ?
C4B C3B H3D 108.5 . . ?
C2B C3B H3D 108.5 . . ?
H3C C3B H3D 107.5 . . ?
C3B C4B C11B 112.8(5) . . ?
C3B C4B H4C 109.0 . . ?
C11B C4B H4C 109.0 . . ?
C3B C4B H4D 109.0 . . ?
C11B C4B H4D 109.0 . . ?
H4C C4B H4D 107.8 . . ?
C6B C5B C12B 116.7(5) . . ?
C6B C5B H5B 121.6 . . ?
C12B C5B H5B 121.6 . . ?
C5B C6B C7B 122.3(4) . . ?
C5B C6B H6B 118.8 . . ?
C7B C6B H6B 118.8 . . ?
C6B C7B C8B 120.8(5) . . ?
C6B C7B H7B 119.6 . . ?
C8B C7B H7B 119.6 . . ?
C13B C8B C7B 116.4(5) . . ?
C13B C8B H8B 121.8 . . ?
C7B C8B H8B 121.8 . . ?
C10B N9B C13B 108.2(4) . . ?
C10B N9B C14 125.4(4) . . ?
C13B N9B C14 126.3(4) . . ?
C11B C10B N9B 108.8(4) . . ?
C11B C10B C1B 125.9(4) . . ?
N9B C10B C1B 125.3(4) . . ?
C10B C11B C12B 108.0(4) . . ?
C10B C11B C4B 120.7(5) . . ?
C12B C11B C4B 131.3(4) . . ?
C13B C12B C11B 107.5(4) . . ?
C13B C12B C5B 120.0(5) . . ?
C11B C12B C5B 132.5(5) . . ?
C8B C13B C12B 123.3(4) . . ?
C8B C13B N9B 129.2(4) . . ?
C12B C13B N9B 107.5(4) . . ?
C15 C14 C16 119.5(2) . 3_656 ?
C16B C14 C15B 119.6(2) 3_656 . ?
C15 C14 N9 116.9(8) . . ?
C16 C14 N9 123.6(8) 3_656 . ?
C16B C14 N9B 117.6(8) 3_656 . ?
C15B C14 N9B 122.8(9) . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C14 120.4(3) . 3_656 ?
C15 C16 H16 119.8 . . ?
C14 C16 H16 119.8 3_656 . ?
C16B C15B C14 119.7(3) . . ?
C16B C15B H15B 120.1 . . ?
C14 C15B H15B 120.1 . . ?
C14 C16B C15B 120.7(3) 3_656 . ?
C14 C16B H16B 119.7 3_656 . ?
C15B C16B H16B 119.7 . . ?

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
C10 C1 C2 C3 -44.1(10) . . . . ?
C1 C2 C3 C4 58.8(8) . . . . ?
C2 C3 C4 C11 -37.6(8) . . . . ?
C12 C5 C6 C7 -5.8(11) . . . . ?
C5 C6 C7 C8 7.0(12) . . . . ?
C6 C7 C8 C13 -4.5(13) . . . . ?
C13 N9 C10 C11 1.2(16) . . . . ?
C14 N9 C10 C11 173.5(16) . . . . ?
C13 N9 C10 C1 175.3(12) . . . . ?
C14 N9 C10 C1 -12(3) . . . . ?
C2 C1 C10 C11 15.4(14) . . . . ?
C2 C1 C10 N9 -157.8(13) . . . . ?
N9 C10 C11 C12 -1.7(13) . . . . ?
C1 C10 C11 C12 -175.8(10) . . . . ?
N9 C10 C11 C4 178.3(11) . . . . ?
C1 C10 C11 C4 4.1(14) . . . . ?
C3 C4 C11 C10 7.3(11) . . . . ?
C3 C4 C11 C12 -172.8(8) . . . . ?
C10 C11 C12 C13 1.5(10) . . . . ?
C4 C11 C12 C13 -178.4(9) . . . . ?
C10 C11 C12 C5 -179.9(9) . . . . ?
C4 C11 C12 C5 0.1(15) . . . . ?
C6 C5 C12 C13 2.6(11) . . . . ?
C6 C5 C12 C11 -175.8(9) . . . . ?
C11 C12 C13 C8 178.0(10) . . . . ?
C5 C12 C13 C8 -0.8(14) . . . . ?
C11 C12 C13 N9 -0.8(12) . . . . ?
C5 C12 C13 N9 -179.6(11) . . . . ?
C7 C8 C13 C12 1.7(15) . . . . ?
C7 C8 C13 N9 -179.8(13) . . . . ?
C10 N9 C13 C12 -0.2(16) . . . . ?
C14 N9 C13 C12 -172.8(15) . . . . ?
C10 N9 C13 C8 -179.0(12) . . . . ?
C14 N9 C13 C8 8(2) . . . . ?
C10B C1B C2B C3B 34.2(12) . . . . ?
C1B C2B C3B C4B -55.4(11) . . . . ?
C2B C3B C4B C11B 44.7(11) . . . . ?
C12B C5B C6B C7B 6.1(10) . . . . ?
C5B C6B C7B C8B -8.4(12) . . . . ?
C6B C7B C8B C13B 4.8(14) . . . . ?
C13B N9B C10B C11B -1.9(18) . . . . ?
C14 N9B C10B C11B 174.5(17) . . . . ?
C13B N9B C10B C1B 178.1(13) . . . . ?
C14 N9B C10B C1B -6(3) . . . . ?
C2B C1B C10B C11B -8.8(17) . . . . ?
C2B C1B C10B N9B 171.3(15) . . . . ?
N9B C10B C11B C12B 1.1(15) . . . . ?
C1B C10B C11B C12B -178.9(12) . . . . ?
N9B C10B C11B C4B 179.3(12) . . . . ?
C1B C10B C11B C4B -0.6(17) . . . . ?
C3B C4B C11B C10B -17.5(13) . . . . ?
C3B C4B C11B C12B 160.3(10) . . . . ?
C10B C11B C12B C13B 0.1(12) . . . . ?
C4B C11B C12B C13B -177.9(10) . . . . ?
C10B C11B C12B C5B 179.2(10) . . . . ?
C4B C11B C12B C5B 1.2(18) . . . . ?
C6B C5B C12B C13B -0.8(12) . . . . ?
C6B C5B C12B C11B -179.8(10) . . . . ?
C7B C8B C13B C12B 0.5(17) . . . . ?
C7B C8B C13B N9B 178.0(15) . . . . ?
C11B C12B C13B C8B 176.8(11) . . . . ?
C5B C12B C13B C8B -2.5(16) . . . . ?
C11B C12B C13B N9B -1.2(14) . . . . ?
C5B C12B C13B N9B 179.5(12) . . . . ?
C10B N9B C13B C8B -176.0(14) . . . . ?
C14 N9B C13B C8B 8(3) . . . . ?
C10B N9B C13B C12B 1.9(18) . . . . ?
C14 N9B C13B C12B -174.4(18) . . . . ?
C10 N9 C14 C15 61(2) . . . . ?
C13 N9 C14 C15 -127.5(14) . . . . ?
C10 N9 C14 C16 -115.9(15) . . . 3_656 ?
C13 N9 C14 C16 55(2) . . . 3_656 ?
C10B N9B C14 C16B 127.6(16) . . . 3_656 ?
C13B N9B C14 C16B -57(2) . . . 3_656 ?
C10B N9B C14 C15B -56(2) . . . . ?
C13B N9B C14 C15B 119.7(16) . . . . ?
C16 C14 C15 C16 1.6(5) 3_656 . . . ?
N9 C14 C15 C16 -175.8(7) . . . . ?
C14 C15 C16 C14 -1.6(6) . . . 3_656 ?
C16B C14 C15B C16B 2.4(6) 3_656 . . . ?
N9B C14 C15B C16B -174.0(7) . . . . ?
C14 C15B C16B C14 -2.5(6) . . . 3_656 ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.077



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# 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_117RMB19
_database_code_depnum_ccdc_archive 'CCDC 1990761'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2020-03-16 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          568
_chemical_formula_moiety         'C30 H24 N2'
_chemical_formula_sum            'C30 H24 N2'
_chemical_formula_weight         412.51

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5168(10)
_cell_length_b                   7.6482(6)
_cell_length_c                   12.8491(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.876(3)
_cell_angle_gamma                90
_cell_volume                     1131.65(16)
_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4948
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      29.45

_exptl_crystal_description       platy-prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.127
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            19288
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2307
_reflns_number_gt                1122
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (H?bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0854P)²+0.2598P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2307
_refine_ls_number_parameters     200
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.611(3) 0.339(3) 0.266(2) 0.083(2) Uani 0.5 1 d D U P A 1
H1 H 0.659100 0.250243 0.292277 0.099 Uiso 0.5 1 calc R U P A 1
C2 C 0.6394(9) 0.4390(16) 0.1807(9) 0.095(2) Uani 0.5 1 d D U P A 1
H2 H 0.694990 0.399488 0.134521 0.114 Uiso 0.5 1 calc R U P A 1
C3 C 0.5849(13) 0.5980(12) 0.1635(9) 0.103(2) Uani 0.5 1 d D U P A 1
H3 H 0.624244 0.686342 0.129007 0.124 Uiso 0.5 1 calc R U P A 1
C4 C 0.4726(13) 0.628(3) 0.1969(16) 0.092(3) Uani 0.5 1 d D U P A 1
H4 H 0.424742 0.714234 0.168594 0.110 Uiso 0.5 1 calc R U P A 1
C1B C 0.614(3) 0.326(3) 0.280(2) 0.082(2) Uani 0.5 1 d . U P A 2
H1A H 0.605694 0.212258 0.246957 0.099 Uiso 0.5 1 calc R U P A 2
H1B H 0.662758 0.310228 0.341559 0.099 Uiso 0.5 1 calc R U P A 2
C2B C 0.6752(10) 0.4441(17) 0.2071(9) 0.098(2) Uani 0.5 1 d . U P A 2
H2A H 0.721098 0.526685 0.247677 0.117 Uiso 0.5 1 calc R U P A 2
H2B H 0.728489 0.375047 0.166298 0.117 Uiso 0.5 1 calc R U P A 2
C3B C 0.5990(12) 0.5426(14) 0.1356(9) 0.101(2) Uani 0.5 1 d . U P A 2
H3A H 0.644142 0.636018 0.105007 0.121 Uiso 0.5 1 calc R U P A 2
H3B H 0.574931 0.465115 0.079542 0.121 Uiso 0.5 1 calc R U P A 2
C4B C 0.4970(13) 0.618(3) 0.1797(16) 0.091(3) Uani 0.5 1 d . U P A 2
H4A H 0.438846 0.628109 0.124596 0.109 Uiso 0.5 1 calc R U P A 2
H4B H 0.516262 0.735621 0.202086 0.109 Uiso 0.5 1 calc R U P A 2
C5 C 0.2419(3) 0.6520(4) 0.3292(3) 0.0853(11) Uani 1 1 d D . . . .
H5 H 0.236740 0.740665 0.279788 0.102 Uiso 1 1 calc R U . . .
C6 C 0.1568(4) 0.6302(5) 0.4015(3) 0.1034(13) Uani 1 1 d D . . . .
H6 H 0.092055 0.702899 0.399087 0.124 Uiso 1 1 calc R U . . .
C7 C 0.1643(3) 0.5042(5) 0.4774(3) 0.0939(12) Uani 1 1 d D . . . .
H7 H 0.107023 0.497697 0.527461 0.113 Uiso 1 1 calc R U . . .
C8 C 0.2560(3) 0.3860(4) 0.4807(3) 0.0723(9) Uani 1 1 d D . . . .
H8 H 0.260020 0.297757 0.530479 0.087 Uiso 1 1 calc R U . . .
N9 N 0.44231(19) 0.3095(2) 0.39363(18) 0.0563(7) Uani 1 1 d . . . . .
C10 C 0.5030(3) 0.3829(3) 0.3115(2) 0.0592(8) Uani 1 1 d . . . . .
C11 C 0.4400(3) 0.5227(3) 0.2727(2) 0.0680(9) Uani 1 1 d . . . . .
C12 C 0.3371(3) 0.5373(3) 0.3316(2) 0.0631(9) Uani 1 1 d . . . . .
C13 C 0.3410(2) 0.4053(3) 0.4069(2) 0.0556(8) Uani 1 1 d . . . . .
C14 C 0.4720(2) 0.1525(3) 0.4480(2) 0.0489(7) Uani 1 1 d . . . . .
C15 C 0.5769(4) 0.1378(5) 0.4986(4) 0.0559(15) Uani 0.612(5) 1 d . . P B 1
H15 H 0.628726 0.230968 0.498391 0.067 Uiso 0.612(5) 1 calc R U P B 1
C16 C 0.6059(4) -0.0146(5) 0.5498(4) 0.0572(15) Uani 0.612(5) 1 d . . P B 1
H16 H 0.677923 -0.024932 0.582916 0.069 Uiso 0.612(5) 1 calc R U P B 1
C15B C 0.4795(7) 0.1514(8) 0.5533(6) 0.055(2) Uani 0.388(5) 1 d . . P B 2
H15B H 0.465732 0.254043 0.589924 0.066 Uiso 0.388(5) 1 calc R U P B 2
C16B C 0.5072(7) 0.0007(8) 0.6070(6) 0.059(3) Uani 0.388(5) 1 d . . P B 2
H16B H 0.511980 0.001479 0.679284 0.071 Uiso 0.388(5) 1 calc R U P B 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 1.384(10) . ?
C1 C10 1.42(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(9) . ?
C3 H3 0.9300 . ?
C4 C11 1.32(2) . ?
C4 H4 0.9300 . ?
C1B C10 1.42(3) . ?
C1B C2B 1.486(16) . ?
C1B H1A 0.9700 . ?
C1B H1B 0.9700 . ?
C2B C3B 1.469(15) . ?
C2B H2A 0.9700 . ?
C2B H2B 0.9700 . ?
C3B C4B 1.433(12) . ?
C3B H3A 0.9700 . ?
C3B H3B 0.9700 . ?
C4B C11 1.553(18) . ?
C4B H4A 0.9700 . ?
C4B H4B 0.9700 . ?
C5 C6 1.371(5) . ?
C5 C12 1.404(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(4) . ?
C8 H8 0.9300 . ?
N9 C13 1.390(3) . ?
N9 C10 1.393(3) . ?
N9 C14 1.428(3) . ?
C10 C11 1.381(4) . ?
C11 C12 1.420(4) . ?
C12 C13 1.398(4) . ?
C14 C15B 1.355(7) . ?
C14 C15 1.368(5) . ?
C14 C16 1.385(5) 3_656 ?
C14 C16B 1.390(7) 3_656 ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C15B C16B 1.378(9) . ?
C15B H15B 0.9300 . ?
C16B H16B 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
C2 C1 C10 114.1(14) . . ?
C2 C1 H1 122.9 . . ?
C10 C1 H1 122.9 . . ?
C1 C2 C3 120.2(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.2(10) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C11 C4 C3 113.8(12) . . ?
C11 C4 H4 123.1 . . ?
C3 C4 H4 123.1 . . ?
C10 C1B C2B 115.5(12) . . ?
C10 C1B H1A 108.4 . . ?
C2B C1B H1A 108.4 . . ?
C10 C1B H1B 108.4 . . ?
C2B C1B H1B 108.4 . . ?
H1A C1B H1B 107.5 . . ?
C3B C2B C1B 115.0(13) . . ?
C3B C2B H2A 108.5 . . ?
C1B C2B H2A 108.5 . . ?
C3B C2B H2B 108.5 . . ?
C1B C2B H2B 108.5 . . ?
H2A C2B H2B 107.5 . . ?
C4B C3B C2B 116.4(10) . . ?
C4B C3B H3A 108.2 . . ?
C2B C3B H3A 108.2 . . ?
C4B C3B H3B 108.2 . . ?
C2B C3B H3B 108.2 . . ?
H3A C3B H3B 107.3 . . ?
C3B C4B C11 118.3(12) . . ?
C3B C4B H4A 107.7 . . ?
C11 C4B H4A 107.7 . . ?
C3B C4B H4B 107.7 . . ?
C11 C4B H4B 107.7 . . ?
H4A C4B H4B 107.1 . . ?
C6 C5 C12 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C12 C5 H5 120.8 . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C13 C8 C7 117.0(3) . . ?
C13 C8 H8 121.5 . . ?
C7 C8 H8 121.5 . . ?
C13 N9 C10 108.2(2) . . ?
C13 N9 C14 125.4(2) . . ?
C10 N9 C14 126.2(2) . . ?
C11 C10 N9 108.6(3) . . ?
C11 C10 C1B 127.4(6) . . ?
N9 C10 C1B 123.9(6) . . ?
C11 C10 C1 119.7(5) . . ?
N9 C10 C1 131.7(5) . . ?
C4 C11 C10 125.7(6) . . ?
C4 C11 C12 126.4(6) . . ?
C10 C11 C12 107.9(3) . . ?
C10 C11 C4B 114.5(6) . . ?
C12 C11 C4B 137.6(6) . . ?
C13 C12 C5 118.9(3) . . ?
C13 C12 C11 107.0(3) . . ?
C5 C12 C11 134.0(3) . . ?
C8 C13 N9 129.2(2) . . ?
C8 C13 C12 122.5(3) . . ?
N9 C13 C12 108.3(3) . . ?
C15 C14 C16 119.7(3) . 3_656 ?
C15B C14 C16B 119.6(4) . 3_656 ?
C15 C14 C16B 90.8(4) . 3_656 ?
C16 C14 C16B 59.0(4) 3_656 3_656 ?
C15B C14 N9 120.3(3) . . ?
C15 C14 N9 120.3(3) . . ?
C16 C14 N9 120.0(3) 3_656 . ?
C16B C14 N9 120.1(4) 3_656 . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C14 120.1(4) . 3_656 ?
C15 C16 H16 119.9 . . ?
C14 C16 H16 119.9 3_656 . ?
C14 C15B C16B 121.0(6) . . ?
C14 C15B H15B 119.5 . . ?
C16B C15B H15B 119.5 . . ?
C15B C16B H16B 120.3 . . ?
C14 C16B H16B 120.3 3_656 . ?

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
C10 C1 C2 C3 19(3) . . . . ?
C1 C2 C3 C4 -29(2) . . . . ?
C2 C3 C4 C11 22(2) . . . . ?
C10 C1B C2B C3B -32(3) . . . . ?
C1B C2B C3B C4B 43(2) . . . . ?
C2B C3B C4B C11 -31(2) . . . . ?
C12 C5 C6 C7 2.2(5) . . . . ?
C5 C6 C7 C8 -3.7(6) . . . . ?
C6 C7 C8 C13 2.3(5) . . . . ?
C13 N9 C10 C11 -0.6(3) . . . . ?
C14 N9 C10 C11 173.4(2) . . . . ?
C13 N9 C10 C1B 176.0(17) . . . . ?
C14 N9 C10 C1B -10.0(18) . . . . ?
C13 N9 C10 C1 179.1(19) . . . . ?
C14 N9 C10 C1 -6.9(19) . . . . ?
C2B C1B C10 C11 9(3) . . . . ?
C2B C1B C10 N9 -167.1(12) . . . . ?
C2 C1 C10 C11 -4(3) . . . . ?
C2 C1 C10 N9 176.5(10) . . . . ?
C3 C4 C11 C10 -6(2) . . . . ?
C3 C4 C11 C12 171.0(8) . . . . ?
N9 C10 C11 C4 177.3(12) . . . . ?
C1 C10 C11 C4 -2(2) . . . . ?
N9 C10 C11 C12 -0.2(3) . . . . ?
C1B C10 C11 C12 -176.6(18) . . . . ?
C1 C10 C11 C12 -179.9(16) . . . . ?
N9 C10 C11 C4B -179.7(9) . . . . ?
C1B C10 C11 C4B 4(2) . . . . ?
C3B C4B C11 C10 7.2(18) . . . . ?
C3B C4B C11 C12 -172.1(7) . . . . ?
C6 C5 C12 C13 0.3(4) . . . . ?
C6 C5 C12 C11 -178.2(3) . . . . ?
C4 C11 C12 C13 -176.6(12) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C4B C11 C12 C13 -179.8(12) . . . . ?
C4 C11 C12 C5 2.0(13) . . . . ?
C10 C11 C12 C5 179.5(3) . . . . ?
C4B C11 C12 C5 -1.1(13) . . . . ?
C7 C8 C13 N9 178.4(3) . . . . ?
C7 C8 C13 C12 0.2(4) . . . . ?
C10 N9 C13 C8 -177.3(3) . . . . ?
C14 N9 C13 C8 8.7(4) . . . . ?
C10 N9 C13 C12 1.1(3) . . . . ?
C14 N9 C13 C12 -172.9(2) . . . . ?
C5 C12 C13 C8 -1.5(4) . . . . ?
C11 C12 C13 C8 177.3(3) . . . . ?
C5 C12 C13 N9 179.9(2) . . . . ?
C11 C12 C13 N9 -1.2(3) . . . . ?
C13 N9 C14 C15B -58.3(5) . . . . ?
C10 N9 C14 C15B 128.7(5) . . . . ?
C13 N9 C14 C15 -127.6(4) . . . . ?
C10 N9 C14 C15 59.4(4) . . . . ?
C13 N9 C14 C16 51.9(4) . . . 3_656 ?
C10 N9 C14 C16 -121.0(4) . . . 3_656 ?
C13 N9 C14 C16B 121.4(5) . . . 3_656 ?
C10 N9 C14 C16B -51.6(5) . . . 3_656 ?
C16 C14 C15 C16 1.3(7) 3_656 . . . ?
N9 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C14 -1.3(7) . . . 3_656 ?
C16B C14 C15B C16B -0.1(11) 3_656 . . . ?
N9 C14 C15B C16B 179.5(5) . . . . ?
C14 C15B C16B C14 0.1(11) . . . 3_656 ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_preparation       Luminescent
