# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yw5
_database_code_depnum_ccdc_archive 'CCDC 1903044'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-07 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N3'
_chemical_formula_weight         337.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   8.0352(17)
_cell_length_b                   12.627(3)
_cell_length_c                   33.738(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3423.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1779
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      30.05

_exptl_crystal_description       brick
_exptl_crystal_colour            lightpurple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.607
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  1.287
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            10427
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         6.100
_diffrn_reflns_theta_max         71.890
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3274
_reflns_number_gt                2908
_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       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        'X-Area Integrate 1.71.0.0 (STOE, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0418P)²+1.0290P] 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         3274
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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 0.70049(12) 0.68108(8) 0.60737(3) 0.0179(2) Uani 1 1 d . . . . .
C2 C 0.64779(13) 0.57811(8) 0.62626(3) 0.0173(2) Uani 1 1 d . . . . .
H2 H 0.724418 0.521288 0.616611 0.021 Uiso 1 1 calc R U . . .
N3 N 0.66300(11) 0.58381(7) 0.66973(3) 0.01789(19) Uani 1 1 d . . . . .
C4 C 0.63468(12) 0.67463(8) 0.68525(3) 0.0169(2) Uani 1 1 d . . . . .
N5 N 0.60678(11) 0.76518(7) 0.66268(3) 0.01790(19) Uani 1 1 d . . . . .
N6 N 0.67597(11) 0.77000(7) 0.62499(3) 0.01854(19) Uani 1 1 d . . . . .
C7 C 0.60038(13) 0.86904(8) 0.68199(3) 0.0198(2) Uani 1 1 d . . . . .
H7A H 0.553457 0.922119 0.663508 0.024 Uiso 1 1 calc R U . . .
H7B H 0.714126 0.891803 0.689375 0.024 Uiso 1 1 calc R U . . .
C8 C 0.49269(13) 0.86163(8) 0.71871(3) 0.0212(2) Uani 1 1 d . . . . .
H8A H 0.493147 0.930449 0.732770 0.025 Uiso 1 1 calc R U . . .
H8B H 0.376600 0.845402 0.710984 0.025 Uiso 1 1 calc R U . . .
C11 C 0.77565(13) 0.68266(8) 0.56732(3) 0.0192(2) Uani 1 1 d . . . . .
C12 C 0.76895(14) 0.59341(9) 0.54297(3) 0.0223(2) Uani 1 1 d . . . . .
H12 H 0.715723 0.530993 0.552275 0.027 Uiso 1 1 calc R U . . .
C13 C 0.83899(15) 0.59453(10) 0.50534(3) 0.0270(3) Uani 1 1 d . . . . .
H13 H 0.833401 0.533161 0.489100 0.032 Uiso 1 1 calc R U . . .
C14 C 0.91672(15) 0.68476(10) 0.49150(3) 0.0302(3) Uani 1 1 d . . . . .
H14 H 0.965577 0.685429 0.465862 0.036 Uiso 1 1 calc R U . . .
C15 C 0.92317(16) 0.77434(10) 0.51518(4) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.975608 0.836705 0.505583 0.036 Uiso 1 1 calc R U . . .
C16 C 0.85359(14) 0.77354(9) 0.55278(3) 0.0241(2) Uani 1 1 d . . . . .
H16 H 0.858982 0.835342 0.568787 0.029 Uiso 1 1 calc R U . . .
C21 C 0.47061(13) 0.54701(8) 0.61490(3) 0.0170(2) Uani 1 1 d . . . . .
C22 C 0.41628(14) 0.44507(8) 0.62362(3) 0.0198(2) Uani 1 1 d . . . . .
H22 H 0.490919 0.395880 0.635363 0.024 Uiso 1 1 calc R U . . .
C23 C 0.25436(15) 0.41457(9) 0.61535(3) 0.0237(2) Uani 1 1 d . . . . .
H23 H 0.218018 0.345138 0.621882 0.028 Uiso 1 1 calc R U . . .
C24 C 0.14518(14) 0.48508(9) 0.59757(3) 0.0241(2) Uani 1 1 d . . . . .
H24 H 0.034095 0.464167 0.591938 0.029 Uiso 1 1 calc R U . . .
C25 C 0.19877(14) 0.58592(9) 0.58807(3) 0.0237(2) Uani 1 1 d . . . . .
H25 H 0.124934 0.634194 0.575527 0.028 Uiso 1 1 calc R U . . .
C26 C 0.36053(13) 0.61671(8) 0.59684(3) 0.0205(2) Uani 1 1 d . . . . .
H26 H 0.396327 0.686332 0.590418 0.025 Uiso 1 1 calc R U . . .
C31 C 0.63030(12) 0.68713(8) 0.72904(3) 0.0180(2) Uani 1 1 d . . . . .
C32 C 0.55689(13) 0.77653(8) 0.74576(3) 0.0191(2) Uani 1 1 d . . . . .
C33 C 0.54434(13) 0.78402(9) 0.78685(3) 0.0231(2) Uani 1 1 d . . . . .
H33 H 0.493168 0.844450 0.798369 0.028 Uiso 1 1 calc R U . . .
C34 C 0.60538(15) 0.70465(9) 0.81110(3) 0.0251(2) Uani 1 1 d . . . . .
H34 H 0.593892 0.709974 0.839056 0.030 Uiso 1 1 calc R U . . .
C35 C 0.68330(14) 0.61739(9) 0.79450(3) 0.0243(2) Uani 1 1 d . . . . .
H35 H 0.728439 0.563791 0.811081 0.029 Uiso 1 1 calc R U . . .
C36 C 0.69530(14) 0.60842(8) 0.75353(3) 0.0206(2) Uani 1 1 d . . . . .
H36 H 0.748073 0.548333 0.742163 0.025 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
C1 N6 1.2857(14) . ?
C1 C11 1.4799(15) . ?
C1 C2 1.5087(14) . ?
C2 N3 1.4735(14) . ?
C2 C21 1.5258(14) . ?
C2 H2 1.0000 . ?
N3 C4 1.2810(14) . ?
C4 N5 1.3918(13) . ?
C4 C31 1.4864(15) . ?
N5 N6 1.3891(13) . ?
N5 C7 1.4652(13) . ?
C7 C8 1.5142(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C32 1.5013(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 C12 1.3957(15) . ?
C11 C16 1.3963(15) . ?
C12 C13 1.3891(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3806(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3858(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3864(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3886(15) . ?
C21 C22 1.3907(15) . ?
C22 C23 1.3852(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.3864(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.3819(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3886(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.3931(15) . ?
C31 C36 1.3940(15) . ?
C32 C33 1.3929(16) . ?
C33 C34 1.3837(17) . ?
C33 H33 0.9500 . ?
C34 C35 1.3856(17) . ?
C34 H34 0.9500 . ?
C35 C36 1.3903(16) . ?
C35 H35 0.9500 . ?
C36 H36 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
N6 C1 C11 118.23(9) . . ?
N6 C1 C2 120.94(9) . . ?
C11 C1 C2 120.79(9) . . ?
N3 C2 C1 110.81(8) . . ?
N3 C2 C21 109.88(8) . . ?
C1 C2 C21 112.18(8) . . ?
N3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C21 C2 H2 107.9 . . ?
C4 N3 C2 115.83(8) . . ?
N3 C4 N5 122.72(9) . . ?
N3 C4 C31 120.36(9) . . ?
N5 C4 C31 116.92(9) . . ?
N6 N5 C4 118.18(8) . . ?
N6 N5 C7 112.44(8) . . ?
C4 N5 C7 119.85(9) . . ?
C1 N6 N5 116.52(8) . . ?
N5 C7 C8 109.18(8) . . ?
N5 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N5 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C32 C8 C7 110.20(9) . . ?
C32 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C32 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C12 C11 C16 118.30(10) . . ?
C12 C11 C1 120.71(9) . . ?
C16 C11 C1 120.99(10) . . ?
C13 C12 C11 120.95(10) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.05(11) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.71(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.43(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.56(11) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C26 C21 C22 118.66(10) . . ?
C26 C21 C2 122.78(9) . . ?
C22 C21 C2 118.56(9) . . ?
C23 C22 C21 120.63(10) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.19(10) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.66(10) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.01(10) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.82(10) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C32 C31 C36 119.76(10) . . ?
C32 C31 C4 119.91(9) . . ?
C36 C31 C4 120.31(9) . . ?
C33 C32 C31 119.25(10) . . ?
C33 C32 C8 122.10(10) . . ?
C31 C32 C8 118.64(10) . . ?
C34 C33 C32 120.91(10) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C35 119.80(10) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C36 119.87(10) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 120.35(10) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?

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
N6 C1 C2 N3 -32.93(13) . . . . ?
C11 C1 C2 N3 149.55(9) . . . . ?
N6 C1 C2 C21 90.28(12) . . . . ?
C11 C1 C2 C21 -87.24(11) . . . . ?
C1 C2 N3 C4 33.24(12) . . . . ?
C21 C2 N3 C4 -91.30(10) . . . . ?
C2 N3 C4 N5 -5.93(14) . . . . ?
C2 N3 C4 C31 174.04(8) . . . . ?
N3 C4 N5 N6 -26.93(14) . . . . ?
C31 C4 N5 N6 153.11(9) . . . . ?
N3 C4 N5 C7 -170.72(10) . . . . ?
C31 C4 N5 C7 9.32(13) . . . . ?
C11 C1 N6 N5 -179.37(9) . . . . ?
C2 C1 N6 N5 3.05(14) . . . . ?
C4 N5 N6 C1 27.46(13) . . . . ?
C7 N5 N6 C1 173.79(9) . . . . ?
N6 N5 C7 C8 168.37(8) . . . . ?
C4 N5 C7 C8 -45.92(12) . . . . ?
N5 C7 C8 C32 55.98(11) . . . . ?
N6 C1 C11 C12 -164.50(10) . . . . ?
C2 C1 C11 C12 13.09(15) . . . . ?
N6 C1 C11 C16 14.90(15) . . . . ?
C2 C1 C11 C16 -167.52(10) . . . . ?
C16 C11 C12 C13 0.46(16) . . . . ?
C1 C11 C12 C13 179.87(10) . . . . ?
C11 C12 C13 C14 0.02(17) . . . . ?
C12 C13 C14 C15 -0.58(18) . . . . ?
C13 C14 C15 C16 0.65(18) . . . . ?
C14 C15 C16 C11 -0.17(18) . . . . ?
C12 C11 C16 C15 -0.38(16) . . . . ?
C1 C11 C16 C15 -179.79(10) . . . . ?
N3 C2 C21 C26 110.32(11) . . . . ?
C1 C2 C21 C26 -13.42(14) . . . . ?
N3 C2 C21 C22 -68.56(11) . . . . ?
C1 C2 C21 C22 167.70(9) . . . . ?
C26 C21 C22 C23 -1.58(15) . . . . ?
C2 C21 C22 C23 177.35(9) . . . . ?
C21 C22 C23 C24 1.16(16) . . . . ?
C22 C23 C24 C25 0.11(16) . . . . ?
C23 C24 C25 C26 -0.92(16) . . . . ?
C22 C21 C26 C25 0.77(16) . . . . ?
C2 C21 C26 C25 -178.11(10) . . . . ?
C24 C25 C26 C21 0.48(16) . . . . ?
N3 C4 C31 C32 -162.72(10) . . . . ?
N5 C4 C31 C32 17.25(14) . . . . ?
N3 C4 C31 C36 15.53(15) . . . . ?
N5 C4 C31 C36 -164.50(9) . . . . ?
C36 C31 C32 C33 -2.28(15) . . . . ?
C4 C31 C32 C33 175.98(9) . . . . ?
C36 C31 C32 C8 178.12(10) . . . . ?
C4 C31 C32 C8 -3.62(14) . . . . ?
C7 C8 C32 C33 147.16(10) . . . . ?
C7 C8 C32 C31 -33.25(13) . . . . ?
C31 C32 C33 C34 0.75(16) . . . . ?
C8 C32 C33 C34 -179.65(10) . . . . ?
C32 C33 C34 C35 1.37(17) . . . . ?
C33 C34 C35 C36 -1.96(17) . . . . ?
C34 C35 C36 C31 0.43(16) . . . . ?
C32 C31 C36 C35 1.70(15) . . . . ?
C4 C31 C36 C35 -176.55(10) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_yw7
_database_code_depnum_ccdc_archive 'CCDC 1903046'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-07 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30.50 H26 Cl N3 O'
_chemical_formula_weight         485.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.6209(8)
_cell_length_b                   10.4364(8)
_cell_length_c                   14.6138(12)
_cell_angle_alpha                87.2358(13)
_cell_angle_beta                 82.3312(13)
_cell_angle_gamma                64.4367(12)
_cell_volume                     1311.79(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4817
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.44

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             510
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9102
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28832
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.406
_diffrn_reflns_theta_max         29.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7431
_reflns_number_gt                4772
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0955P)²+0.6103P] 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         7431
_refine_ls_number_parameters     334
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2137
_refine_ls_wR_factor_gt          0.1863
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.052
_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 0.46025(18) 0.56881(17) 0.72066(10) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.5471(2) 0.4761(2) 0.63918(13) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.495558 0.421468 0.615497 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5976(2) 0.43544(19) 0.73278(13) 0.0235(4) Uani 1 1 d . . . . .
N4 N 0.53809(17) 0.34053(16) 0.78392(11) 0.0244(3) Uani 1 1 d . . . . .
N5 N 0.38634(17) 0.42682(16) 0.83044(11) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.3244(2) 0.54175(19) 0.76399(12) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.285344 0.507211 0.714872 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4027(2) 0.4820(2) 0.91727(13) 0.0284(4) Uani 1 1 d . . . . .
H7A H 0.462614 0.539169 0.904193 0.034 Uiso 1 1 calc R U . . .
H7B H 0.458778 0.402361 0.957600 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2412(2) 0.5736(2) 0.96484(14) 0.0338(5) Uani 1 1 d . . . . .
H8A H 0.184528 0.514368 0.981517 0.041 Uiso 1 1 calc R U . . .
H8B H 0.249279 0.614943 1.022368 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1938(2) 0.6751(2) 0.80688(14) 0.0269(4) Uani 1 1 d . . . . .
C12 C 0.1527(2) 0.6914(2) 0.90191(14) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.0286(3) 0.8170(3) 0.93654(17) 0.0416(5) Uani 1 1 d . . . . .
H13 H -0.000465 0.829924 1.001348 0.050 Uiso 1 1 calc R U . . .
C14 C -0.0521(3) 0.9224(3) 0.8779(2) 0.0487(6) Uani 1 1 d . . . . .
H14 H -0.135869 1.007430 0.902525 0.058 Uiso 1 1 calc R U . . .
C15 C -0.0117(3) 0.9049(2) 0.78349(19) 0.0462(6) Uani 1 1 d . . . . .
H15 H -0.068258 0.977343 0.743136 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1112(2) 0.7817(2) 0.74795(16) 0.0357(5) Uani 1 1 d . . . . .
H16 H 0.139440 0.769717 0.683048 0.043 Uiso 1 1 calc R U . . .
C21 C 0.6298(3) 0.5329(3) 0.56749(13) 0.0346(5) Uani 1 1 d . . . . .
C22 C 0.5683(4) 0.6758(3) 0.54869(19) 0.0670(9) Uani 1 1 d . . . . .
H22 H 0.473607 0.739324 0.582394 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6456(6) 0.7267(4) 0.4801(2) 0.0982(15) Uani 1 1 d . . . . .
H23 H 0.602859 0.825241 0.466679 0.118 Uiso 1 1 calc R U . . .
C24 C 0.7841(5) 0.6354(5) 0.4312(2) 0.0861(13) Uani 1 1 d . . . . .
H24 H 0.838464 0.671440 0.386097 0.103 Uiso 1 1 calc R U . . .
C25 C 0.8413(4) 0.4955(5) 0.44770(19) 0.0666(9) Uani 1 1 d . . . . .
H25 H 0.934485 0.432187 0.412578 0.080 Uiso 1 1 calc R U . . .
C26 C 0.7653(3) 0.4424(3) 0.51585(17) 0.0504(6) Uani 1 1 d . . . . .
H26 H 0.806957 0.343157 0.526915 0.060 Uiso 1 1 calc R U . . .
C31 C 0.7385(2) 0.4383(2) 0.76251(13) 0.0253(4) Uani 1 1 d . . . . .
C32 C 0.7440(3) 0.5653(2) 0.78046(17) 0.0372(5) Uani 1 1 d . . . . .
H32 H 0.656576 0.653044 0.774012 0.045 Uiso 1 1 calc R U . . .
C33 C 0.8771(3) 0.5640(3) 0.80782(18) 0.0457(6) Uani 1 1 d . . . . .
H33 H 0.880188 0.651231 0.820268 0.055 Uiso 1 1 calc R U . . .
C34 C 1.0050(3) 0.4379(3) 0.81715(16) 0.0417(6) Uani 1 1 d . . . . .
H34 H 1.095758 0.438094 0.835822 0.050 Uiso 1 1 calc R U . . .
C35 C 1.0007(2) 0.3112(3) 0.79928(16) 0.0389(5) Uani 1 1 d . . . . .
H35 H 1.088612 0.223917 0.805666 0.047 Uiso 1 1 calc R U . . .
C36 C 0.8678(2) 0.3112(2) 0.77193(15) 0.0334(5) Uani 1 1 d . . . . .
H36 H 0.865304 0.223745 0.759598 0.040 Uiso 1 1 calc R U . . .
C40 C 0.5729(2) 0.2088(2) 0.74822(14) 0.0281(4) Uani 1 1 d . . . . .
O40 O 0.67875(17) 0.15750(16) 0.68555(11) 0.0386(4) Uani 1 1 d . . . . .
C41 C 0.4857(2) 0.1269(2) 0.79207(16) 0.0326(5) Uani 1 1 d . . . . .
C42 C 0.4720(3) 0.0300(3) 0.7356(2) 0.0487(6) Uani 1 1 d . . . . .
H42 H 0.511625 0.021756 0.671976 0.058 Uiso 1 1 calc R U . . .
C43 C 0.4001(3) -0.0545(3) 0.7728(2) 0.0602(8) Uani 1 1 d . . . . .
H43 H 0.389510 -0.119683 0.734171 0.072 Uiso 1 1 calc R U . . .
C44 C 0.3442(3) -0.0445(3) 0.8649(2) 0.0572(8) Uani 1 1 d . . . . .
H44 H 0.294711 -0.102248 0.889742 0.069 Uiso 1 1 calc R U . . .
C45 C 0.3596(3) 0.0486(3) 0.9208(2) 0.0504(6) Uani 1 1 d . . . . .
H45 H 0.322739 0.053956 0.984777 0.061 Uiso 1 1 calc R U . . .
C46 C 0.4294(3) 0.1356(2) 0.88433(17) 0.0392(5) Uani 1 1 d . . . . .
H46 H 0.438070 0.201280 0.923384 0.047 Uiso 1 1 calc R U . . .
C51 C 0.076(3) 1.093(3) 0.4596(17) 0.54(4) Uani 0.5 1 d D . P A -1
H51A H 0.149345 1.057322 0.402444 0.652 Uiso 0.5 1 calc R U P A -1
H51B H 0.020041 1.197528 0.459712 0.652 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.1667(10) 1.0190(6) 0.5685(5) 0.266(3) Uani 0.5 1 d D . P A -1
Cl2 Cl -0.0574(9) 1.0004(10) 0.4862(5) 0.334(8) Uani 0.5 1 d D . P A -1


_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 C3 1.472(2) . ?
N1 C2 1.483(2) . ?
N1 C6 1.507(2) . ?
C2 C21 1.485(3) . ?
C2 C3 1.493(3) . ?
C2 H2 1.0000 . ?
C3 N4 1.473(2) . ?
C3 C31 1.490(2) . ?
N4 C40 1.379(2) . ?
N4 N5 1.437(2) . ?
N5 C6 1.470(2) . ?
N5 C7 1.473(2) . ?
C6 C11 1.508(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.519(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C12 1.509(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 C12 1.390(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.398(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.376(4) . ?
C21 C26 1.380(3) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.342(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.388(3) . ?
C31 C36 1.389(3) . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C40 O40 1.221(2) . ?
C40 C41 1.505(3) . ?
C41 C46 1.376(3) . ?
C41 C42 1.396(3) . ?
C42 C43 1.390(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.372(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.366(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.394(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 Cl1 1.89(2) . ?
C51 Cl2 1.90(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?

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
C3 N1 C2 60.71(12) . . ?
C3 N1 C6 104.67(13) . . ?
C2 N1 C6 112.76(15) . . ?
N1 C2 C21 116.78(17) . . ?
N1 C2 C3 59.26(12) . . ?
C21 C2 C3 122.22(17) . . ?
N1 C2 H2 115.6 . . ?
C21 C2 H2 115.6 . . ?
C3 C2 H2 115.6 . . ?
N1 C3 N4 105.90(14) . . ?
N1 C3 C31 120.37(15) . . ?
N4 C3 C31 116.66(15) . . ?
N1 C3 C2 60.03(12) . . ?
N4 C3 C2 114.88(15) . . ?
C31 C3 C2 124.67(16) . . ?
C40 N4 N5 121.03(15) . . ?
C40 N4 C3 120.34(15) . . ?
N5 N4 C3 108.04(13) . . ?
N4 N5 C6 101.89(13) . . ?
N4 N5 C7 109.06(14) . . ?
C6 N5 C7 111.02(15) . . ?
N5 C6 N1 105.97(13) . . ?
N5 C6 C11 113.53(15) . . ?
N1 C6 C11 111.50(15) . . ?
N5 C6 H6 108.6 . . ?
N1 C6 H6 108.6 . . ?
C11 C6 H6 108.6 . . ?
N5 C7 C8 108.12(15) . . ?
N5 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N5 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C12 C8 C7 110.26(16) . . ?
C12 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C12 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C12 C11 C16 120.27(19) . . ?
C12 C11 C6 121.86(17) . . ?
C16 C11 C6 117.85(18) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 C8 119.68(18) . . ?
C13 C12 C8 121.71(19) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C2 120.3(2) . . ?
C26 C21 C2 120.5(2) . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C32 C31 C36 119.13(18) . . ?
C32 C31 C3 121.46(18) . . ?
C36 C31 C3 119.41(17) . . ?
C33 C32 C31 119.9(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.7(2) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.0(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C31 C36 C35 120.4(2) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
O40 C40 N4 119.74(18) . . ?
O40 C40 C41 121.32(18) . . ?
N4 C40 C41 118.81(17) . . ?
C46 C41 C42 119.1(2) . . ?
C46 C41 C40 124.00(19) . . ?
C42 C41 C40 116.7(2) . . ?
C43 C42 C41 119.8(3) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C44 C43 C42 120.4(3) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C45 C44 C43 120.0(2) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.2(3) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C41 C46 C45 120.4(2) . . ?
C41 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
Cl1 C51 Cl2 90.3(13) . . ?
Cl1 C51 H51A 113.6 . . ?
Cl2 C51 H51A 113.6 . . ?
Cl1 C51 H51B 113.6 . . ?
Cl2 C51 H51B 113.6 . . ?
H51A C51 H51B 110.9 . . ?

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
C3 N1 C2 C21 -113.25(19) . . . . ?
C6 N1 C2 C21 152.18(16) . . . . ?
C6 N1 C2 C3 -94.57(15) . . . . ?
C2 N1 C3 N4 -109.92(16) . . . . ?
C6 N1 C3 N4 -1.76(18) . . . . ?
C2 N1 C3 C31 115.03(19) . . . . ?
C6 N1 C3 C31 -136.81(16) . . . . ?
C6 N1 C3 C2 108.16(15) . . . . ?
C21 C2 C3 N1 104.2(2) . . . . ?
N1 C2 C3 N4 94.65(16) . . . . ?
C21 C2 C3 N4 -161.18(18) . . . . ?
N1 C2 C3 C31 -108.1(2) . . . . ?
C21 C2 C3 C31 -3.9(3) . . . . ?
N1 C3 N4 C40 123.82(17) . . . . ?
C31 C3 N4 C40 -99.2(2) . . . . ?
C2 C3 N4 C40 60.0(2) . . . . ?
N1 C3 N4 N5 -21.14(18) . . . . ?
C31 C3 N4 N5 115.85(17) . . . . ?
C2 C3 N4 N5 -85.01(18) . . . . ?
C40 N4 N5 C6 -109.51(17) . . . . ?
C3 N4 N5 C6 35.16(17) . . . . ?
C40 N4 N5 C7 133.07(17) . . . . ?
C3 N4 N5 C7 -82.26(17) . . . . ?
N4 N5 C6 N1 -35.72(17) . . . . ?
C7 N5 C6 N1 80.28(17) . . . . ?
N4 N5 C6 C11 -158.43(14) . . . . ?
C7 N5 C6 C11 -42.44(19) . . . . ?
C3 N1 C6 N5 23.34(18) . . . . ?
C2 N1 C6 N5 87.33(17) . . . . ?
C3 N1 C6 C11 147.34(15) . . . . ?
C2 N1 C6 C11 -148.67(15) . . . . ?
N4 N5 C7 C8 179.59(15) . . . . ?
C6 N5 C7 C8 68.12(19) . . . . ?
N5 C7 C8 C12 -57.2(2) . . . . ?
N5 C6 C11 C12 8.1(2) . . . . ?
N1 C6 C11 C12 -111.48(19) . . . . ?
N5 C6 C11 C16 -170.09(17) . . . . ?
N1 C6 C11 C16 70.3(2) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C6 C11 C12 C13 -178.89(18) . . . . ?
C16 C11 C12 C8 178.72(19) . . . . ?
C6 C11 C12 C8 0.5(3) . . . . ?
C7 C8 C12 C11 24.0(3) . . . . ?
C7 C8 C12 C13 -156.6(2) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C8 C12 C13 C14 -179.1(2) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C6 C11 C16 C15 178.6(2) . . . . ?
N1 C2 C21 C22 -34.3(3) . . . . ?
C3 C2 C21 C22 -103.2(3) . . . . ?
N1 C2 C21 C26 148.8(2) . . . . ?
C3 C2 C21 C26 79.8(3) . . . . ?
C26 C21 C22 C23 -1.7(5) . . . . ?
C2 C21 C22 C23 -178.7(3) . . . . ?
C21 C22 C23 C24 -0.5(6) . . . . ?
C22 C23 C24 C25 2.6(6) . . . . ?
C23 C24 C25 C26 -2.3(5) . . . . ?
C22 C21 C26 C25 2.0(4) . . . . ?
C2 C21 C26 C25 179.0(2) . . . . ?
C24 C25 C26 C21 0.0(4) . . . . ?
N1 C3 C31 C32 0.7(3) . . . . ?
N4 C3 C31 C32 -129.8(2) . . . . ?
C2 C3 C31 C32 73.3(3) . . . . ?
N1 C3 C31 C36 -178.86(17) . . . . ?
N4 C3 C31 C36 50.6(2) . . . . ?
C2 C3 C31 C36 -106.2(2) . . . . ?
C36 C31 C32 C33 -0.3(3) . . . . ?
C3 C31 C32 C33 -179.9(2) . . . . ?
C31 C32 C33 C34 0.3(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C32 C31 C36 C35 0.2(3) . . . . ?
C3 C31 C36 C35 179.80(19) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
N5 N4 C40 O40 156.48(17) . . . . ?
C3 N4 C40 O40 16.1(3) . . . . ?
N5 N4 C40 C41 -27.6(2) . . . . ?
C3 N4 C40 C41 -168.02(16) . . . . ?
O40 C40 C41 C46 144.7(2) . . . . ?
N4 C40 C41 C46 -31.2(3) . . . . ?
O40 C40 C41 C42 -30.8(3) . . . . ?
N4 C40 C41 C42 153.3(2) . . . . ?
C46 C41 C42 C43 0.9(4) . . . . ?
C40 C41 C42 C43 176.6(2) . . . . ?
C41 C42 C43 C44 -0.8(4) . . . . ?
C42 C43 C44 C45 -0.3(4) . . . . ?
C43 C44 C45 C46 1.3(4) . . . . ?
C42 C41 C46 C45 0.0(3) . . . . ?
C40 C41 C46 C45 -175.4(2) . . . . ?
C44 C45 C46 C41 -1.1(4) . . . . ?

_refine_diff_density_max         0.814
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_yw6
_database_code_depnum_ccdc_archive 'CCDC 1903045'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-07 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br N3 O'
_chemical_formula_weight         354.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.9776(14)
_cell_length_b                   8.2312(5)
_cell_length_c                   15.9421(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.9609(12)
_cell_angle_gamma                90
_cell_volume                     2873.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4513
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.60

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.866
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18168
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         29.641
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4052
_reflns_number_gt                2908
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0355P)²+2.1838P] 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         4052
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.24503(2) 0.21891(3) 0.73664(2) 0.04076(10) Uani 1 1 d . . . . .
C1 C 0.44225(10) 0.6171(2) 0.57531(13) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.44722(10) 0.6328(3) 0.48351(13) 0.0268(5) Uani 1 1 d . . . . .
O2 O 0.41406(8) 0.5583(2) 0.43028(10) 0.0375(4) Uani 1 1 d . . . . .
N3 N 0.49269(8) 0.7343(2) 0.45914(12) 0.0268(4) Uani 1 1 d . . . . .
N5 N 0.52694(8) 0.7751(2) 0.60036(11) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.53114(10) 0.7990(2) 0.51680(13) 0.0241(4) Uani 1 1 d . . . . .
N6 N 0.48209(8) 0.6847(2) 0.62960(11) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.57648(11) 0.8221(3) 0.66396(14) 0.0359(6) Uani 1 1 d . . . . .
H7A H 0.609532 0.740169 0.665543 0.043 Uiso 1 1 calc R U . . .
H7B H 0.560684 0.825659 0.720241 0.043 Uiso 1 1 calc R U . . .
C8 C 0.60146(12) 0.9858(3) 0.64333(15) 0.0377(6) Uani 1 1 d . . . . .
H8A H 0.638622 1.008414 0.681150 0.045 Uiso 1 1 calc R U . . .
H8B H 0.570862 1.070626 0.652828 0.045 Uiso 1 1 calc R U . . .
C11 C 0.39399(10) 0.5205(3) 0.61208(14) 0.0253(5) Uani 1 1 d . . . . .
C12 C 0.40161(10) 0.4783(3) 0.69748(14) 0.0281(5) Uani 1 1 d . . . . .
H12 H 0.437795 0.510077 0.730280 0.034 Uiso 1 1 calc R U . . .
C13 C 0.35743(10) 0.3913(3) 0.73493(14) 0.0295(5) Uani 1 1 d . . . . .
H13 H 0.362938 0.364035 0.793002 0.035 Uiso 1 1 calc R U . . .
C14 C 0.30519(10) 0.3445(3) 0.68659(14) 0.0279(5) Uani 1 1 d . . . . .
C15 C 0.29601(10) 0.3836(3) 0.60239(15) 0.0319(5) Uani 1 1 d . . . . .
H15 H 0.259700 0.350653 0.570206 0.038 Uiso 1 1 calc R U . . .
C16 C 0.34034(11) 0.4715(3) 0.56504(15) 0.0298(5) Uani 1 1 d . . . . .
H16 H 0.334228 0.498731 0.507009 0.036 Uiso 1 1 calc R U . . .
C31 C 0.58109(10) 0.9044(3) 0.49250(13) 0.0255(5) Uani 1 1 d . . . . .
C32 C 0.61687(11) 0.9922(3) 0.55307(14) 0.0296(5) Uani 1 1 d . . . . .
C33 C 0.66389(11) 1.0897(3) 0.52841(15) 0.0341(5) Uani 1 1 d . . . . .
H33 H 0.688361 1.149675 0.569553 0.041 Uiso 1 1 calc R U . . .
C34 C 0.67535(11) 1.1001(3) 0.44472(16) 0.0361(6) Uani 1 1 d . . . . .
H34 H 0.707995 1.165438 0.428553 0.043 Uiso 1 1 calc R U . . .
C35 C 0.63899(12) 1.0147(3) 0.38440(15) 0.0358(6) Uani 1 1 d . . . . .
H35 H 0.646484 1.023002 0.326754 0.043 Uiso 1 1 calc R U . . .
C36 C 0.59203(11) 0.9179(3) 0.40756(14) 0.0308(5) Uani 1 1 d . . . . .
H36 H 0.567105 0.860429 0.365879 0.037 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
Br1 C14 1.907(2) . ?
C1 N6 1.302(3) . ?
C1 C2 1.483(3) . ?
C1 C11 1.486(3) . ?
C2 O2 1.233(3) . ?
C2 N3 1.384(3) . ?
N3 C4 1.307(3) . ?
N5 N6 1.350(2) . ?
N5 C4 1.358(3) . ?
N5 C7 1.474(3) . ?
C4 C31 1.477(3) . ?
C7 C8 1.502(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C32 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 C16 1.401(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C31 C32 1.393(3) . ?
C31 C36 1.400(3) . ?
C32 C33 1.392(3) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 H36 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
N6 C1 C2 121.10(19) . . ?
N6 C1 C11 115.37(19) . . ?
C2 C1 C11 123.50(19) . . ?
O2 C2 N3 120.3(2) . . ?
O2 C2 C1 123.1(2) . . ?
N3 C2 C1 116.50(19) . . ?
C4 N3 C2 119.17(18) . . ?
N6 N5 C4 122.17(18) . . ?
N6 N5 C7 115.16(17) . . ?
C4 N5 C7 121.89(19) . . ?
N3 C4 N5 122.4(2) . . ?
N3 C4 C31 120.34(19) . . ?
N5 C4 C31 117.23(19) . . ?
C1 N6 N5 118.38(18) . . ?
N5 C7 C8 110.31(19) . . ?
N5 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N5 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C32 110.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C32 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C32 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C16 C11 C12 118.2(2) . . ?
C16 C11 C1 122.6(2) . . ?
C12 C11 C1 119.1(2) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 Br1 119.05(17) . . ?
C13 C14 Br1 119.38(17) . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C32 C31 C36 119.7(2) . . ?
C32 C31 C4 120.70(19) . . ?
C36 C31 C4 119.6(2) . . ?
C33 C32 C31 119.4(2) . . ?
C33 C32 C8 121.6(2) . . ?
C31 C32 C8 118.9(2) . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.7(2) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 120.4(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 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
N6 C1 C2 O2 172.9(2) . . . . ?
C11 C1 C2 O2 -4.9(3) . . . . ?
N6 C1 C2 N3 -5.7(3) . . . . ?
C11 C1 C2 N3 176.56(18) . . . . ?
O2 C2 N3 C4 -173.1(2) . . . . ?
C1 C2 N3 C4 5.5(3) . . . . ?
C2 N3 C4 N5 -2.4(3) . . . . ?
C2 N3 C4 C31 178.41(18) . . . . ?
N6 N5 C4 N3 -1.1(3) . . . . ?
C7 N5 C4 N3 168.3(2) . . . . ?
N6 N5 C4 C31 178.15(18) . . . . ?
C7 N5 C4 C31 -12.5(3) . . . . ?
C2 C1 N6 N5 2.5(3) . . . . ?
C11 C1 N6 N5 -179.57(18) . . . . ?
C4 N5 N6 C1 0.9(3) . . . . ?
C7 N5 N6 C1 -169.1(2) . . . . ?
N6 N5 C7 C8 -147.3(2) . . . . ?
C4 N5 C7 C8 42.7(3) . . . . ?
N5 C7 C8 C32 -50.4(3) . . . . ?
N6 C1 C11 C16 164.9(2) . . . . ?
C2 C1 C11 C16 -17.2(3) . . . . ?
N6 C1 C11 C12 -14.1(3) . . . . ?
C2 C1 C11 C12 163.8(2) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C1 C11 C12 C13 178.7(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C12 C13 C14 Br1 178.14(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
Br1 C14 C15 C16 -178.39(17) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C1 C11 C16 C15 -178.9(2) . . . . ?
N3 C4 C31 C32 170.8(2) . . . . ?
N5 C4 C31 C32 -8.4(3) . . . . ?
N3 C4 C31 C36 -8.3(3) . . . . ?
N5 C4 C31 C36 172.5(2) . . . . ?
C36 C31 C32 C33 -1.3(3) . . . . ?
C4 C31 C32 C33 179.6(2) . . . . ?
C36 C31 C32 C8 175.5(2) . . . . ?
C4 C31 C32 C8 -3.6(3) . . . . ?
C7 C8 C32 C33 -149.6(2) . . . . ?
C7 C8 C32 C31 33.6(3) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C8 C32 C33 C34 -176.7(2) . . . . ?
C32 C33 C34 C35 1.1(4) . . . . ?
C33 C34 C35 C36 -0.9(4) . . . . ?
C34 C35 C36 C31 -0.5(4) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
C4 C31 C36 C35 -179.3(2) . . . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_yw9
_database_code_depnum_ccdc_archive 'CCDC 1903047'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-07 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 N3 O2'
_chemical_formula_weight         433.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.4665(10)
_cell_length_b                   10.3663(11)
_cell_length_c                   12.9597(14)
_cell_angle_alpha                101.761(3)
_cell_angle_beta                 90.841(3)
_cell_angle_gamma                113.945(3)
_cell_volume                     1131.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1350
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.99

_exptl_crystal_description       irregular
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8700
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13778
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.615
_diffrn_reflns_theta_max         24.417
_diffrn_reflns_theta_full        24.417
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3719
_reflns_number_gt                2122
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0622P)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         3719
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.3059(4) 0.1188(4) 0.6502(3) 0.0393(9) Uani 1 1 d . . . . .
H1A H 0.243559 0.176192 0.653187 0.047 Uiso 1 1 calc R U . . .
H1B H 0.255133 0.030369 0.592688 0.047 Uiso 1 1 calc R U . . .
C2 C 0.4677(3) 0.2070(3) 0.6258(2) 0.0333(8) Uani 1 1 d . . . . .
H2A H 0.528487 0.147791 0.616028 0.040 Uiso 1 1 calc R U . . .
H2B H 0.462958 0.240277 0.560026 0.040 Uiso 1 1 calc R U . . .
N3 N 0.5410(3) 0.3325(3) 0.71674(19) 0.0263(6) Uani 1 1 d . . . . .
C4 C 0.5723(3) 0.2879(3) 0.8115(2) 0.0249(7) Uani 1 1 d . . . . .
H4 H 0.591310 0.369404 0.874313 0.030 Uiso 1 1 calc R U . . .
N5 N 0.7211(3) 0.2680(3) 0.79979(18) 0.0263(6) Uani 1 1 d . . . . .
C6 C 0.8613(3) 0.4065(3) 0.8406(2) 0.0272(8) Uani 1 1 d . . . . .
H6 H 0.841447 0.487855 0.883760 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7989(3) 0.3600(3) 0.7262(2) 0.0253(7) Uani 1 1 d . . . . .
N9 N 0.6945(3) 0.4215(3) 0.69696(19) 0.0275(6) Uani 1 1 d . . . . .
O10 O 0.8864(2) 0.6455(2) 0.72808(17) 0.0374(6) Uani 1 1 d . . . . .
C10 C 0.7460(4) 0.5699(3) 0.7115(2) 0.0303(8) Uani 1 1 d . . . . .
C11 C 0.6328(4) 0.6332(3) 0.7001(2) 0.0329(8) Uani 1 1 d . . . . .
C12 C 0.6809(5) 0.7790(4) 0.7488(3) 0.0562(11) Uani 1 1 d . . . . .
H12 H 0.779346 0.831037 0.789781 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5860(6) 0.8484(5) 0.7377(4) 0.0731(13) Uani 1 1 d . . . . .
H13 H 0.619654 0.948007 0.771200 0.088 Uiso 1 1 calc R U . . .
C14 C 0.4426(6) 0.7740(5) 0.6784(4) 0.0699(13) Uani 1 1 d . . . . .
H14 H 0.377671 0.822311 0.671494 0.084 Uiso 1 1 calc R U . . .
C15 C 0.3945(5) 0.6317(5) 0.6298(3) 0.0577(11) Uani 1 1 d . . . . .
H15 H 0.296167 0.580962 0.588446 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4882(4) 0.5597(4) 0.6402(3) 0.0449(10) Uani 1 1 d . . . . .
H16 H 0.453450 0.460082 0.606325 0.054 Uiso 1 1 calc R U . . .
C21 C 0.3094(3) 0.0760(3) 0.7542(2) 0.0293(8) Uani 1 1 d . . . . .
C22 C 0.1849(4) -0.0407(3) 0.7767(3) 0.0359(9) Uani 1 1 d . . . . .
H22 H 0.096987 -0.095088 0.725367 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1873(4) -0.0784(3) 0.8728(3) 0.0369(9) Uani 1 1 d . . . . .
H23 H 0.101840 -0.158506 0.887322 0.044 Uiso 1 1 calc R U . . .
C24 C 0.3155(4) 0.0014(3) 0.9479(3) 0.0370(9) Uani 1 1 d . . . . .
H24 H 0.317648 -0.023592 1.014258 0.044 Uiso 1 1 calc R U . . .
C25 C 0.4398(4) 0.1170(3) 0.9261(2) 0.0306(8) Uani 1 1 d . . . . .
H25 H 0.527450 0.171185 0.977659 0.037 Uiso 1 1 calc R U . . .
C26 C 0.4380(3) 0.1550(3) 0.8289(2) 0.0266(8) Uani 1 1 d . . . . .
C31 C 0.8732(3) 0.3032(3) 0.6412(2) 0.0274(8) Uani 1 1 d . . . . .
O32 O 0.9015(3) 0.3706(2) 0.55917(18) 0.0503(7) Uani 1 1 d . . . . .
C33 C 0.9794(4) 0.3084(4) 0.4928(3) 0.0509(11) Uani 1 1 d . . . . .
H33 H 1.014798 0.335112 0.428804 0.061 Uiso 1 1 calc R U . . .
C34 C 0.9985(4) 0.2064(4) 0.5297(3) 0.0453(10) Uani 1 1 d . . . . .
H34 H 1.048387 0.147384 0.498146 0.054 Uiso 1 1 calc R U . . .
C35 C 0.9292(4) 0.2024(4) 0.6265(3) 0.0498(11) Uani 1 1 d . . . . .
H35 H 0.923860 0.139747 0.671993 0.060 Uiso 1 1 calc R U . . .
C41 C 1.0067(3) 0.3968(3) 0.8754(2) 0.0276(8) Uani 1 1 d . . . . .
C42 C 1.0043(4) 0.2836(4) 0.9173(2) 0.0354(8) Uani 1 1 d . . . . .
H42 H 0.907492 0.208331 0.923552 0.043 Uiso 1 1 calc R U . . .
C43 C 1.1418(4) 0.2786(4) 0.9503(3) 0.0414(9) Uani 1 1 d . . . . .
H43 H 1.138958 0.201095 0.979983 0.050 Uiso 1 1 calc R U . . .
C44 C 1.2820(4) 0.3861(4) 0.9400(3) 0.0437(10) Uani 1 1 d . . . . .
H44 H 1.376366 0.384022 0.963667 0.052 Uiso 1 1 calc R U . . .
C45 C 1.2857(4) 0.4970(4) 0.8951(3) 0.0434(9) Uani 1 1 d . . . . .
H45 H 1.382712 0.569224 0.885565 0.052 Uiso 1 1 calc R U . . .
C46 C 1.1487(4) 0.5036(4) 0.8639(3) 0.0365(9) Uani 1 1 d . . . . .
H46 H 1.152129 0.581587 0.834645 0.044 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
C1 C21 1.505(4) . ?
C1 C2 1.509(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N3 1.477(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 N9 1.431(3) . ?
N3 C4 1.463(4) . ?
C4 C26 1.509(4) . ?
C4 N5 1.510(3) . ?
C4 H4 1.0000 . ?
N5 C8 1.478(4) . ?
N5 C6 1.492(4) . ?
C6 C41 1.490(4) . ?
C6 C8 1.494(4) . ?
C6 H6 1.0000 . ?
C8 N9 1.458(4) . ?
C8 C31 1.465(4) . ?
N9 C10 1.382(4) . ?
O10 C10 1.227(3) . ?
C10 C11 1.486(4) . ?
C11 C12 1.390(5) . ?
C11 C16 1.392(4) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.360(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.387(4) . ?
C21 C22 1.391(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(4) . ?
C25 H25 0.9500 . ?
C31 C35 1.335(4) . ?
C31 O32 1.360(3) . ?
O32 C33 1.370(4) . ?
C33 C34 1.319(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.424(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C41 C42 1.382(4) . ?
C41 C46 1.386(4) . ?
C42 C43 1.388(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.374(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.379(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.385(4) . ?
C45 H45 0.9500 . ?
C46 H46 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
C21 C1 C2 111.3(3) . . ?
C21 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C21 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N3 C2 C1 107.1(3) . . ?
N3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
N3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
N9 N3 C4 101.8(2) . . ?
N9 N3 C2 109.4(2) . . ?
C4 N3 C2 111.5(2) . . ?
N3 C4 C26 112.7(2) . . ?
N3 C4 N5 106.5(2) . . ?
C26 C4 N5 113.3(2) . . ?
N3 C4 H4 108.1 . . ?
C26 C4 H4 108.1 . . ?
N5 C4 H4 108.1 . . ?
C8 N5 C6 60.41(18) . . ?
C8 N5 C4 103.3(2) . . ?
C6 N5 C4 112.0(2) . . ?
C41 C6 N5 117.7(2) . . ?
C41 C6 C8 120.8(3) . . ?
N5 C6 C8 59.33(17) . . ?
C41 C6 H6 115.7 . . ?
N5 C6 H6 115.7 . . ?
C8 C6 H6 115.7 . . ?
N9 C8 C31 117.5(2) . . ?
N9 C8 N5 106.7(2) . . ?
C31 C8 N5 118.5(2) . . ?
N9 C8 C6 115.2(2) . . ?
C31 C8 C6 123.7(3) . . ?
N5 C8 C6 60.26(18) . . ?
C10 N9 N3 121.5(2) . . ?
C10 N9 C8 120.4(2) . . ?
N3 N9 C8 108.1(2) . . ?
O10 C10 N9 118.4(3) . . ?
O10 C10 C11 121.6(3) . . ?
N9 C10 C11 119.9(3) . . ?
C12 C11 C16 118.7(3) . . ?
C12 C11 C10 116.4(3) . . ?
C16 C11 C10 124.8(3) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.2(4) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C26 C21 C22 119.6(3) . . ?
C26 C21 C1 119.5(3) . . ?
C22 C21 C1 120.9(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.4(3) . . ?
C21 C26 C4 121.9(3) . . ?
C25 C26 C4 118.5(3) . . ?
C35 C31 O32 109.7(3) . . ?
C35 C31 C8 134.7(3) . . ?
O32 C31 C8 115.5(3) . . ?
C31 O32 C33 106.2(3) . . ?
C34 C33 O32 110.8(3) . . ?
C34 C33 H33 124.6 . . ?
O32 C33 H33 124.6 . . ?
C33 C34 C35 106.2(3) . . ?
C33 C34 H34 126.9 . . ?
C35 C34 H34 126.9 . . ?
C31 C35 C34 107.1(3) . . ?
C31 C35 H35 126.4 . . ?
C34 C35 H35 126.4 . . ?
C42 C41 C46 119.0(3) . . ?
C42 C41 C6 122.1(3) . . ?
C46 C41 C6 118.9(3) . . ?
C41 C42 C43 120.7(3) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 119.9(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C46 120.4(3) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 120.1(3) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?

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
C21 C1 C2 N3 -55.8(3) . . . . ?
C1 C2 N3 N9 -179.0(2) . . . . ?
C1 C2 N3 C4 69.0(3) . . . . ?
N9 N3 C4 C26 -160.7(2) . . . . ?
C2 N3 C4 C26 -44.1(3) . . . . ?
N9 N3 C4 N5 -35.9(3) . . . . ?
C2 N3 C4 N5 80.7(3) . . . . ?
N3 C4 N5 C8 23.6(3) . . . . ?
C26 C4 N5 C8 148.0(2) . . . . ?
N3 C4 N5 C6 86.7(3) . . . . ?
C26 C4 N5 C6 -148.9(2) . . . . ?
C8 N5 C6 C41 -111.2(3) . . . . ?
C4 N5 C6 C41 155.6(2) . . . . ?
C4 N5 C6 C8 -93.2(2) . . . . ?
C6 N5 C8 N9 -109.9(3) . . . . ?
C4 N5 C8 N9 -2.0(3) . . . . ?
C6 N5 C8 C31 114.7(3) . . . . ?
C4 N5 C8 C31 -137.4(3) . . . . ?
C4 N5 C8 C6 107.9(2) . . . . ?
C41 C6 C8 N9 -158.4(3) . . . . ?
N5 C6 C8 N9 95.6(3) . . . . ?
C41 C6 C8 C31 -0.2(4) . . . . ?
N5 C6 C8 C31 -106.2(3) . . . . ?
C41 C6 C8 N5 106.0(3) . . . . ?
C4 N3 N9 C10 -110.4(3) . . . . ?
C2 N3 N9 C10 131.4(3) . . . . ?
C4 N3 N9 C8 35.0(3) . . . . ?
C2 N3 N9 C8 -83.1(3) . . . . ?
C31 C8 N9 C10 -99.1(3) . . . . ?
N5 C8 N9 C10 125.0(3) . . . . ?
C6 C8 N9 C10 60.5(3) . . . . ?
C31 C8 N9 N3 115.0(3) . . . . ?
N5 C8 N9 N3 -20.9(3) . . . . ?
C6 C8 N9 N3 -85.4(3) . . . . ?
N3 N9 C10 O10 156.2(3) . . . . ?
C8 N9 C10 O10 14.8(4) . . . . ?
N3 N9 C10 C11 -27.6(4) . . . . ?
C8 N9 C10 C11 -168.9(3) . . . . ?
O10 C10 C11 C12 -24.7(5) . . . . ?
N9 C10 C11 C12 159.2(3) . . . . ?
O10 C10 C11 C16 151.5(3) . . . . ?
N9 C10 C11 C16 -24.6(5) . . . . ?
C16 C11 C12 C13 0.2(6) . . . . ?
C10 C11 C12 C13 176.7(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C13 C14 C15 -0.4(7) . . . . ?
C13 C14 C15 C16 0.6(7) . . . . ?
C12 C11 C16 C15 -0.1(5) . . . . ?
C10 C11 C16 C15 -176.2(3) . . . . ?
C14 C15 C16 C11 -0.4(6) . . . . ?
C2 C1 C21 C26 21.6(4) . . . . ?
C2 C1 C21 C22 -159.0(3) . . . . ?
C26 C21 C22 C23 0.3(5) . . . . ?
C1 C21 C22 C23 -179.0(3) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C22 C21 C26 C25 -0.6(5) . . . . ?
C1 C21 C26 C25 178.8(3) . . . . ?
C22 C21 C26 C4 -176.3(3) . . . . ?
C1 C21 C26 C4 3.1(4) . . . . ?
C24 C25 C26 C21 0.4(5) . . . . ?
C24 C25 C26 C4 176.2(3) . . . . ?
N3 C4 C26 C21 7.7(4) . . . . ?
N5 C4 C26 C21 -113.2(3) . . . . ?
N3 C4 C26 C25 -168.0(3) . . . . ?
N5 C4 C26 C25 71.0(4) . . . . ?
N9 C8 C31 C35 -153.5(4) . . . . ?
N5 C8 C31 C35 -22.9(5) . . . . ?
C6 C8 C31 C35 48.7(5) . . . . ?
N9 C8 C31 O32 30.7(4) . . . . ?
N5 C8 C31 O32 161.3(3) . . . . ?
C6 C8 C31 O32 -127.1(3) . . . . ?
C35 C31 O32 C33 -0.6(4) . . . . ?
C8 C31 O32 C33 176.2(3) . . . . ?
C31 O32 C33 C34 0.5(4) . . . . ?
O32 C33 C34 C35 -0.2(4) . . . . ?
O32 C31 C35 C34 0.5(4) . . . . ?
C8 C31 C35 C34 -175.5(3) . . . . ?
C33 C34 C35 C31 -0.2(4) . . . . ?
N5 C6 C41 C42 -30.4(4) . . . . ?
C8 C6 C41 C42 -99.5(4) . . . . ?
N5 C6 C41 C46 148.6(3) . . . . ?
C8 C6 C41 C46 79.6(4) . . . . ?
C46 C41 C42 C43 1.8(5) . . . . ?
C6 C41 C42 C43 -179.1(3) . . . . ?
C41 C42 C43 C44 -0.9(5) . . . . ?
C42 C43 C44 C45 -1.2(5) . . . . ?
C43 C44 C45 C46 2.4(5) . . . . ?
C44 C45 C46 C41 -1.5(5) . . . . ?
C42 C41 C46 C45 -0.6(5) . . . . ?
C6 C41 C46 C45 -179.7(3) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056

