# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_benbg1a
_database_code_depnum_ccdc_archive 'CCDC 2218225'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry, Texas A and M University, College Station, USA
United States of America
;
_audit_update_record             
;
2022-11-08 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N3 O S'
_chemical_formula_sum            'C20 H19 N3 O S'
_chemical_formula_weight         349.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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                   13.2629(10)
_cell_length_b                   12.0772(9)
_cell_length_c                   22.1882(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3554.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6974
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      26.261
_cell_measurement_theta_min      2.393
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1056 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.8848. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.458
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.393
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2675
_reflns_number_total             3127
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       ?
_computing_data_reduction        
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+1.9463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45083(3) 0.84436(3) 0.31685(2) 0.02427(13) Uani 1 1 d . . . . .
O1 O 0.37277(8) 0.90588(9) 0.48418(5) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.34973(9) 0.74881(10) 0.42329(6) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.24645(10) 0.60017(10) 0.44317(6) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.203102 0.566310 0.466874 0.026 Uiso 1 1 calc R . . . .
N3 N 0.25956(10) 0.73782(11) 0.51496(6) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.288167 0.800241 0.526193 0.027 Uiso 1 1 calc R . . . .
C1 C 0.28497(11) 0.69764(12) 0.46123(7) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.38664(11) 0.84925(12) 0.43708(7) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.45019(11) 0.89755(12) 0.38907(7) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.51188(11) 0.98828(13) 0.39368(7) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.521399 1.028994 0.429869 0.026 Uiso 1 1 calc R . . . .
C5 C 0.55980(13) 1.01447(14) 0.33849(8) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.605743 1.074157 0.333639 0.033 Uiso 1 1 calc R . . . .
C6 C 0.53282(12) 0.94490(14) 0.29333(8) 0.0286(4) Uani 1 1 d . . . . .
H6 H 0.556759 0.951244 0.253128 0.034 Uiso 1 1 calc R . . . .
C7 C 0.27312(12) 0.54815(13) 0.38628(7) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.303656 0.604571 0.359552 0.026 Uiso 1 1 calc R . . . .
H7B H 0.210809 0.521168 0.366595 0.026 Uiso 1 1 calc R . . . .
C8 C 0.34615(11) 0.45195(13) 0.39278(7) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.35147(12) 0.37244(14) 0.34754(7) 0.0252(4) Uani 1 1 d . . . . .
H9 H 0.306339 0.376542 0.314366 0.030 Uiso 1 1 calc R . . . .
C10 C 0.42137(13) 0.28743(14) 0.35000(8) 0.0293(4) Uani 1 1 d . . . . .
H10 H 0.424267 0.234265 0.318490 0.035 Uiso 1 1 calc R . . . .
C11 C 0.48708(13) 0.27977(14) 0.39834(8) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.536133 0.222516 0.399794 0.034 Uiso 1 1 calc R . . . .
C12 C 0.48047(14) 0.35622(14) 0.44433(8) 0.0313(4) Uani 1 1 d . . . . .
H12 H 0.524020 0.350230 0.478165 0.038 Uiso 1 1 calc R . . . .
C13 C 0.41070(13) 0.44197(14) 0.44165(8) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.407205 0.494210 0.473595 0.033 Uiso 1 1 calc R . . . .
C14 C 0.18831(14) 0.68726(14) 0.55688(8) 0.0311(4) Uani 1 1 d . . . . .
H14A H 0.211680 0.612167 0.568067 0.037 Uiso 1 1 calc R . . . .
H14B H 0.121284 0.680512 0.537595 0.037 Uiso 1 1 calc R . . . .
C15 C 0.18070(12) 0.75888(14) 0.61254(8) 0.0260(4) Uani 1 1 d . . . . .
C16 C 0.23493(13) 0.73403(14) 0.66444(8) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.275893 0.669537 0.665599 0.035 Uiso 1 1 calc R . . . .
C17 C 0.22980(13) 0.80252(15) 0.71453(8) 0.0301(4) Uani 1 1 d . . . . .
H17 H 0.267070 0.784692 0.749783 0.036 Uiso 1 1 calc R . . . .
C18 C 0.17030(13) 0.89710(15) 0.71325(8) 0.0299(4) Uani 1 1 d . . . . .
H18 H 0.166732 0.944017 0.747549 0.036 Uiso 1 1 calc R . . . .
C19 C 0.11620(13) 0.92267(14) 0.66175(8) 0.0304(4) Uani 1 1 d . . . . .
H19 H 0.075596 0.987440 0.660647 0.037 Uiso 1 1 calc R . . . .
C20 C 0.12115(13) 0.85400(14) 0.61181(8) 0.0291(4) Uani 1 1 d . . . . .
H20 H 0.083561 0.871927 0.576694 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.7264(15) . ?
S1 C6 1.7115(17) . ?
O1 C2 1.2624(18) . ?
N1 C1 1.3521(19) . ?
N1 C2 1.343(2) . ?
N2 H2 0.8800 . ?
N2 C1 1.344(2) . ?
N2 C7 1.4536(19) . ?
N3 H3 0.8800 . ?
N3 C1 1.330(2) . ?
N3 C14 1.460(2) . ?
C2 C3 1.478(2) . ?
C3 C4 1.371(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.356(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.519(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.511(2) . ?
C15 C16 1.390(2) . ?
C15 C20 1.394(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C20 H20 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
C6 S1 C3 91.27(8) . . ?
C2 N1 C1 120.16(13) . . ?
C1 N2 H2 118.5 . . ?
C1 N2 C7 123.01(13) . . ?
C7 N2 H2 118.5 . . ?
C1 N3 H3 117.2 . . ?
C1 N3 C14 125.61(14) . . ?
C14 N3 H3 117.2 . . ?
N2 C1 N1 117.13(14) . . ?
N3 C1 N1 123.51(14) . . ?
N3 C1 N2 119.36(14) . . ?
O1 C2 N1 128.65(14) . . ?
O1 C2 C3 117.76(13) . . ?
N1 C2 C3 113.58(13) . . ?
C2 C3 S1 121.66(11) . . ?
C4 C3 S1 111.32(12) . . ?
C4 C3 C2 126.99(14) . . ?
C3 C4 H4 123.8 . . ?
C3 C4 C5 112.46(15) . . ?
C5 C4 H4 123.8 . . ?
C4 C5 H5 123.8 . . ?
C6 C5 C4 112.48(15) . . ?
C6 C5 H5 123.8 . . ?
S1 C6 H6 123.8 . . ?
C5 C6 S1 112.46(13) . . ?
C5 C6 H6 123.8 . . ?
N2 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
N2 C7 C8 113.78(13) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 119.46(14) . . ?
C13 C8 C7 122.28(14) . . ?
C13 C8 C9 118.23(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.16(16) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.09(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.23(16) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.64(16) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.60(15) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N3 C14 H14A 109.9 . . ?
N3 C14 H14B 109.9 . . ?
N3 C14 C15 108.94(13) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C16 C15 C14 121.25(16) . . ?
C16 C15 C20 118.71(16) . . ?
C20 C15 C14 120.00(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.63(16) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.13(16) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.67(16) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.14(16) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.71(16) . . ?
C19 C20 H20 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.88 2.22 2.9722(17) 143.7 8_655 yes
N3 H3 O1 0.88 1.94 2.6155(17) 132.6 . yes

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
S1 C3 C4 C5 -0.08(17) . . . . ?
O1 C2 C3 S1 -164.60(11) . . . . ?
O1 C2 C3 C4 13.3(2) . . . . ?
N1 C2 C3 S1 14.45(18) . . . . ?
N1 C2 C3 C4 -167.70(14) . . . . ?
N2 C7 C8 C9 158.05(14) . . . . ?
N2 C7 C8 C13 -24.0(2) . . . . ?
N3 C14 C15 C16 -98.16(18) . . . . ?
N3 C14 C15 C20 79.62(19) . . . . ?
C1 N1 C2 O1 3.3(2) . . . . ?
C1 N1 C2 C3 -175.65(13) . . . . ?
C1 N2 C7 C8 103.51(16) . . . . ?
C1 N3 C14 C15 -179.95(15) . . . . ?
C2 N1 C1 N2 176.34(13) . . . . ?
C2 N1 C1 N3 -4.8(2) . . . . ?
C2 C3 C4 C5 -178.12(14) . . . . ?
C3 S1 C6 C5 1.02(14) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 S1 -1.25(19) . . . . ?
C6 S1 C3 C2 177.64(13) . . . . ?
C6 S1 C3 C4 -0.52(12) . . . . ?
C7 N2 C1 N1 1.4(2) . . . . ?
C7 N2 C1 N3 -177.54(14) . . . . ?
C7 C8 C9 C10 175.94(15) . . . . ?
C7 C8 C13 C12 -176.30(15) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C8 C13 C12 1.6(2) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C13 C8 C9 C10 -2.1(2) . . . . ?
C14 N3 C1 N1 178.43(15) . . . . ?
C14 N3 C1 N2 -2.7(2) . . . . ?
C14 C15 C16 C17 177.86(15) . . . . ?
C14 C15 C20 C19 -177.69(15) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C20 C15 C16 C17 0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_benbg3a
_database_code_depnum_ccdc_archive 'CCDC 2218227'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry, Texas A and M University, College Station, USA
United States of America
;
_audit_update_record             
;
2022-11-08 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N3 O'
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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                   15.0645(7)
_cell_length_b                   11.7756(5)
_cell_length_c                   20.4088(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3620.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.473
_cell_measurement_theta_min      2.410
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1207 before and 0.0660 after correction. The Ratio of minimum to maximum transmission is 0.9161. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.216
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3322
_reflns_number_total             4131
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       ?
_computing_data_reduction        
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+1.0770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63420(5) 0.09979(7) 0.47493(4) 0.02052(19) Uani 1 1 d . . . . .
N1 N 0.64231(6) 0.27054(8) 0.41644(5) 0.0188(2) Uani 1 1 d . . . . .
N2 N 0.73174(6) 0.42331(8) 0.44021(5) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.770728 0.456065 0.466163 0.023 Uiso 1 1 calc R . . . .
N3 N 0.72913(6) 0.27451(8) 0.51315(5) 0.0194(2) Uani 1 1 d . . . . .
H3 H 0.707675 0.207616 0.524031 0.023 Uiso 1 1 calc R . . . .
C1 C 0.70092(7) 0.32035(9) 0.45711(6) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.61287(7) 0.16443(10) 0.42845(6) 0.0176(2) Uani 1 1 d . . . . .
C3 C 0.54736(8) 0.12229(10) 0.37868(6) 0.0183(2) Uani 1 1 d . . . . .
C4 C 0.48923(8) 0.03487(10) 0.39503(6) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.491516 0.001877 0.437474 0.025 Uiso 1 1 calc R . . . .
C5 C 0.42789(8) -0.00431(10) 0.34952(6) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.387450 -0.062780 0.361247 0.030 Uiso 1 1 calc R . . . .
C6 C 0.42557(9) 0.04161(11) 0.28716(6) 0.0277(3) Uani 1 1 d . . . . .
H6 H 0.384185 0.013798 0.255914 0.033 Uiso 1 1 calc R . . . .
C7 C 0.48349(9) 0.12804(12) 0.27022(6) 0.0292(3) Uani 1 1 d . . . . .
H7 H 0.482260 0.159077 0.227260 0.035 Uiso 1 1 calc R . . . .
C8 C 0.54329(8) 0.16922(11) 0.31608(6) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.581822 0.229970 0.304711 0.030 Uiso 1 1 calc R . . . .
C9 C 0.70422(8) 0.48387(10) 0.38127(6) 0.0196(2) Uani 1 1 d . . . . .
H9A H 0.681894 0.428327 0.348793 0.023 Uiso 1 1 calc R . . . .
H9B H 0.756492 0.522281 0.361955 0.023 Uiso 1 1 calc R . . . .
C10 C 0.63298(8) 0.57095(10) 0.39432(5) 0.0181(2) Uani 1 1 d . . . . .
C11 C 0.55151(8) 0.53804(11) 0.42056(6) 0.0261(3) Uani 1 1 d . . . . .
H11 H 0.540665 0.460172 0.429736 0.031 Uiso 1 1 calc R . . . .
C12 C 0.48636(9) 0.61767(12) 0.43335(7) 0.0298(3) Uani 1 1 d . . . . .
H12 H 0.431091 0.594252 0.451224 0.036 Uiso 1 1 calc R . . . .
C13 C 0.50133(9) 0.73151(11) 0.42021(6) 0.0269(3) Uani 1 1 d . . . . .
H13 H 0.456925 0.786366 0.429737 0.032 Uiso 1 1 calc R . . . .
C14 C 0.58138(9) 0.76470(11) 0.39313(7) 0.0268(3) Uani 1 1 d . . . . .
H14 H 0.591737 0.842460 0.383359 0.032 Uiso 1 1 calc R . . . .
C15 C 0.64653(8) 0.68464(10) 0.38022(6) 0.0221(3) Uani 1 1 d . . . . .
H15 H 0.701236 0.708103 0.361444 0.027 Uiso 1 1 calc R . . . .
C16 C 0.79283(9) 0.32678(11) 0.55779(6) 0.0243(3) Uani 1 1 d . . . . .
H16A H 0.771206 0.402527 0.571506 0.029 Uiso 1 1 calc R . . . .
H16B H 0.850635 0.336666 0.535421 0.029 Uiso 1 1 calc R . . . .
C17 C 0.80401(8) 0.25161(11) 0.61687(6) 0.0222(3) Uani 1 1 d . . . . .
C18 C 0.86749(9) 0.16709(12) 0.61710(7) 0.0309(3) Uani 1 1 d . . . . .
H18 H 0.904863 0.157245 0.580043 0.037 Uiso 1 1 calc R . . . .
C19 C 0.87716(10) 0.09635(13) 0.67104(7) 0.0372(3) Uani 1 1 d . . . . .
H19 H 0.921374 0.038823 0.670894 0.045 Uiso 1 1 calc R . . . .
C20 C 0.82275(10) 0.10943(12) 0.72482(7) 0.0344(3) Uani 1 1 d . . . . .
H20 H 0.829297 0.061044 0.761753 0.041 Uiso 1 1 calc R . . . .
C21 C 0.75894(10) 0.19293(13) 0.72469(7) 0.0338(3) Uani 1 1 d . . . . .
H21 H 0.721279 0.201944 0.761660 0.041 Uiso 1 1 calc R . . . .
C22 C 0.74912(9) 0.26393(12) 0.67114(7) 0.0285(3) Uani 1 1 d . . . . .
H22 H 0.704747 0.321247 0.671488 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2580(14) . ?
N1 C1 1.3462(15) . ?
N1 C2 1.3483(15) . ?
N2 H2 0.8800 . ?
N2 C1 1.3433(15) . ?
N2 C9 1.4586(15) . ?
N3 H3 0.8800 . ?
N3 C1 1.3341(15) . ?
N3 C16 1.4594(15) . ?
C2 C3 1.5005(16) . ?
C3 C4 1.3921(17) . ?
C3 C8 1.3935(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3890(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3833(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3845(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3866(18) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5081(16) . ?
C10 C11 1.3940(17) . ?
C10 C15 1.3844(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3823(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3855(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3830(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3861(18) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5053(17) . ?
C17 C18 1.3802(18) . ?
C17 C22 1.3899(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3881(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3838(19) . ?
C22 H22 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
C1 N1 C2 120.49(10) . . ?
C1 N2 H2 118.2 . . ?
C1 N2 C9 123.70(10) . . ?
C9 N2 H2 118.2 . . ?
C1 N3 H3 117.5 . . ?
C1 N3 C16 125.03(10) . . ?
C16 N3 H3 117.5 . . ?
N2 C1 N1 117.49(10) . . ?
N3 C1 N1 124.14(10) . . ?
N3 C1 N2 118.37(10) . . ?
O1 C2 N1 127.86(11) . . ?
O1 C2 C3 118.57(10) . . ?
N1 C2 C3 113.56(10) . . ?
C4 C3 C2 119.74(10) . . ?
C4 C3 C8 119.03(11) . . ?
C8 C3 C2 121.23(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.26(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.15(12) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.08(12) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.87(12) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.59(12) . . ?
C7 C8 H8 119.7 . . ?
N2 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
N2 C9 C10 112.90(9) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C11 C10 C9 120.35(11) . . ?
C15 C10 C9 121.06(11) . . ?
C15 C10 C11 118.59(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.60(12) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.29(12) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.51(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.07(12) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.92(12) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N3 C16 H16A 109.9 . . ?
N3 C16 H16B 109.9 . . ?
N3 C16 C17 109.00(10) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C18 C17 C16 120.29(12) . . ?
C18 C17 C22 118.99(12) . . ?
C22 C17 C16 120.70(12) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.54(13) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.13(14) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.60(13) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.55(13) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.18(13) . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.88 2.22 2.9832(13) 144.3 8_765 yes
N3 H3 O1 0.88 1.96 2.6243(12) 131.2 . yes

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
O1 C2 C3 C4 22.45(16) . . . . ?
O1 C2 C3 C8 -157.68(11) . . . . ?
N1 C2 C3 C4 -157.90(10) . . . . ?
N1 C2 C3 C8 21.97(16) . . . . ?
N2 C9 C10 C11 -59.86(15) . . . . ?
N2 C9 C10 C15 120.58(12) . . . . ?
N3 C16 C17 C18 89.26(14) . . . . ?
N3 C16 C17 C22 -88.88(14) . . . . ?
C1 N1 C2 O1 -0.90(18) . . . . ?
C1 N1 C2 C3 179.50(10) . . . . ?
C1 N2 C9 C10 97.99(13) . . . . ?
C1 N3 C16 C17 177.23(11) . . . . ?
C2 N1 C1 N2 175.98(10) . . . . ?
C2 N1 C1 N3 -4.89(17) . . . . ?
C2 C3 C4 C5 179.56(11) . . . . ?
C2 C3 C8 C7 178.83(11) . . . . ?
C3 C4 C5 C6 1.46(18) . . . . ?
C4 C3 C8 C7 -1.29(18) . . . . ?
C4 C5 C6 C7 -1.01(19) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C3 1.8(2) . . . . ?
C8 C3 C4 C5 -0.32(17) . . . . ?
C9 N2 C1 N1 0.96(16) . . . . ?
C9 N2 C1 N3 -178.22(10) . . . . ?
C9 C10 C11 C12 179.22(12) . . . . ?
C9 C10 C15 C14 -179.09(11) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C10 C15 C14 1.35(18) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C10 -0.26(19) . . . . ?
C15 C10 C11 C12 -1.21(19) . . . . ?
C16 N3 C1 N1 179.75(11) . . . . ?
C16 N3 C1 N2 -1.13(17) . . . . ?
C16 C17 C18 C19 -178.99(13) . . . . ?
C16 C17 C22 C21 178.79(12) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C18 C17 C22 C21 0.62(19) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C20 C21 C22 C17 -0.1(2) . . . . ?
C22 C17 C18 C19 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bnbg2
_database_code_depnum_ccdc_archive 'CCDC 2218226'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry, Texas A and M University, College Station, USA
United States of America
;
_audit_update_record             
;
2022-11-08 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3435(5)
_cell_length_b                   12.5993(7)
_cell_length_c                   15.2448(9)
_cell_angle_alpha                84.540(2)
_cell_angle_beta                 72.858(2)
_cell_angle_gamma                81.087(2)
_cell_volume                     1691.88(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.468
_cell_measurement_theta_min      2.329
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1091 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.9384. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34170
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.098
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4911
_reflns_number_total             5950
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.6757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C2B(H2BB,H2BC), C9B(H9BA,H9BB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), N1B(H1B),
 N2B(H2BA), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C11B(H11B),
 C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C18B(H18B), C19B(H19B),
 C20B(H20B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29398(12) 0.25431(8) 0.56119(7) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.29009(12) 0.34335(8) 0.33403(7) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.28923(14) 0.16692(10) 0.25259(8) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.278431 0.237672 0.247696 0.029 Uiso 1 1 calc R . . . .
N2 N 0.37044(14) 0.01144(10) 0.32574(9) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.378904 -0.021947 0.275949 0.030 Uiso 1 1 calc R . . . .
N3 N 0.34216(13) 0.16951(9) 0.39554(8) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.33394(16) 0.11859(11) 0.32376(10) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.25700(19) 0.11121(13) 0.18241(10) 0.0274(4) Uani 1 1 d . . . . .
H2A H 0.345100 0.057470 0.156276 0.033 Uiso 1 1 calc R . . . .
H2B H 0.243343 0.163956 0.132120 0.033 Uiso 1 1 calc R . . . .
C3 C 0.11724(17) 0.05463(12) 0.21835(10) 0.0223(3) Uani 1 1 d . . . . .
C4 C 0.11671(18) -0.04666(12) 0.18955(10) 0.0244(3) Uani 1 1 d . . . . .
H4 H 0.205380 -0.081551 0.148707 0.029 Uiso 1 1 calc R . . . .
C5 C -0.01207(19) -0.09718(13) 0.21990(11) 0.0304(4) Uani 1 1 d . . . . .
H5 H -0.011124 -0.166338 0.199591 0.036 Uiso 1 1 calc R . . . .
C6 C -0.14171(19) -0.04771(14) 0.27944(12) 0.0339(4) Uani 1 1 d . . . . .
H6 H -0.229959 -0.082401 0.299969 0.041 Uiso 1 1 calc R . . . .
C7 C -0.14200(19) 0.05271(14) 0.30891(11) 0.0319(4) Uani 1 1 d . . . . .
H7 H -0.230758 0.087133 0.350018 0.038 Uiso 1 1 calc R . . . .
C8 C -0.01353(18) 0.10338(12) 0.27880(10) 0.0268(3) Uani 1 1 d . . . . .
H8 H -0.014773 0.172280 0.299702 0.032 Uiso 1 1 calc R . . . .
C9 C 0.39693(17) -0.05301(12) 0.40518(11) 0.0273(4) Uani 1 1 d . . . . .
H9A H 0.395411 -0.004556 0.452994 0.033 Uiso 1 1 calc R . . . .
H9B H 0.498519 -0.095486 0.386927 0.033 Uiso 1 1 calc R . . . .
C10 C 0.28030(16) -0.12865(11) 0.44522(10) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.13522(17) -0.10672(12) 0.43566(10) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.107857 -0.043218 0.402131 0.029 Uiso 1 1 calc R . . . .
C12 C 0.02999(18) -0.17665(13) 0.47460(11) 0.0279(4) Uani 1 1 d . . . . .
H12 H -0.068788 -0.161000 0.467347 0.033 Uiso 1 1 calc R . . . .
C13 C 0.06797(18) -0.26897(13) 0.52390(11) 0.0287(4) Uani 1 1 d . . . . .
H13 H -0.004111 -0.317006 0.550408 0.034 Uiso 1 1 calc R . . . .
C14 C 0.21171(18) -0.29084(13) 0.53433(11) 0.0300(4) Uani 1 1 d . . . . .
H14 H 0.238333 -0.353975 0.568521 0.036 Uiso 1 1 calc R . . . .
C15 C 0.31711(18) -0.22134(12) 0.49529(11) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.415690 -0.237231 0.502823 0.034 Uiso 1 1 calc R . . . .
C16 C 0.31360(16) 0.27650(11) 0.39641(10) 0.0197(3) Uani 1 1 d . . . . .
C17 C 0.31235(16) 0.32073(12) 0.48299(10) 0.0218(3) Uani 1 1 d . . . . .
C18 C 0.30123(18) 0.31438(13) 0.62887(11) 0.0310(4) Uani 1 1 d . . . . .
H18 H 0.291213 0.288700 0.690748 0.037 Uiso 1 1 calc R . . . .
C19 C 0.3243(2) 0.41416(14) 0.59654(12) 0.0398(5) Uani 1 1 d . . . . .
H19 H 0.334607 0.470886 0.630136 0.048 Uiso 1 1 calc R . . . .
C20 C 0.3306(2) 0.41926(13) 0.50172(12) 0.0350(4) Uani 1 1 d . . . . .
H20 H 0.344786 0.480235 0.459912 0.042 Uiso 1 1 calc R . . . .
O1B O 0.70130(13) 0.90451(8) 0.07972(8) 0.0314(3) Uani 1 1 d . . . . .
O2B O 0.44029(12) 0.84254(8) 0.19703(8) 0.0296(3) Uani 1 1 d . . . . .
N1B N 0.44995(14) 0.51269(9) 0.25402(9) 0.0236(3) Uani 1 1 d . . . . .
H1B H 0.368930 0.482937 0.284101 0.028 Uiso 1 1 calc R . . . .
N2B N 0.29424(14) 0.67411(10) 0.26448(9) 0.0255(3) Uani 1 1 d . . . . .
H2BA H 0.285664 0.744821 0.260009 0.031 Uiso 1 1 calc R . . . .
N3B N 0.55853(14) 0.66458(9) 0.19342(8) 0.0210(3) Uani 1 1 d . . . . .
C1B C 0.43367(17) 0.61967(11) 0.23760(10) 0.0209(3) Uani 1 1 d . . . . .
C2B C 0.59239(18) 0.44271(12) 0.22546(11) 0.0262(3) Uani 1 1 d . . . . .
H2BB H 0.618001 0.407367 0.280733 0.031 Uiso 1 1 calc R . . . .
H2BC H 0.673012 0.486866 0.192913 0.031 Uiso 1 1 calc R . . . .
C3B C 0.58891(17) 0.35727(12) 0.16323(10) 0.0234(3) Uani 1 1 d . . . . .
C4B C 0.65949(18) 0.25395(12) 0.17408(12) 0.0309(4) Uani 1 1 d . . . . .
H4B H 0.709266 0.237385 0.220733 0.037 Uiso 1 1 calc R . . . .
C5B C 0.6583(2) 0.17434(14) 0.11758(14) 0.0404(4) Uani 1 1 d . . . . .
H5B H 0.707008 0.103643 0.125723 0.048 Uiso 1 1 calc R . . . .
C6B C 0.5866(2) 0.19763(15) 0.04956(13) 0.0414(5) Uani 1 1 d . . . . .
H6B H 0.586577 0.143260 0.010462 0.050 Uiso 1 1 calc R . . . .
C7B C 0.5146(2) 0.30047(15) 0.03845(12) 0.0382(4) Uani 1 1 d . . . . .
H7B H 0.464425 0.316627 -0.008027 0.046 Uiso 1 1 calc R . . . .
C8B C 0.51582(19) 0.37986(13) 0.09506(11) 0.0301(4) Uani 1 1 d . . . . .
H8B H 0.466232 0.450337 0.087189 0.036 Uiso 1 1 calc R . . . .
C9B C 0.15635(17) 0.62506(13) 0.30043(11) 0.0267(3) Uani 1 1 d . . . . .
H9BA H 0.070715 0.682232 0.322312 0.032 Uiso 1 1 calc R . . . .
H9BB H 0.164852 0.576209 0.354027 0.032 Uiso 1 1 calc R . . . .
C10B C 0.12176(16) 0.56207(12) 0.23096(10) 0.0230(3) Uani 1 1 d . . . . .
C11B C 0.17332(18) 0.58549(14) 0.13708(11) 0.0319(4) Uani 1 1 d . . . . .
H11B H 0.230352 0.643612 0.114809 0.038 Uiso 1 1 calc R . . . .
C12B C 0.1421(2) 0.52452(18) 0.07556(13) 0.0455(5) Uani 1 1 d . . . . .
H12B H 0.179288 0.540150 0.011328 0.055 Uiso 1 1 calc R . . . .
C13B C 0.0570(2) 0.44119(17) 0.10745(17) 0.0518(6) Uani 1 1 d . . . . .
H13B H 0.035365 0.399502 0.065337 0.062 Uiso 1 1 calc R . . . .
C14B C 0.0036(2) 0.41878(14) 0.20060(17) 0.0478(5) Uani 1 1 d . . . . .
H14B H -0.055729 0.361863 0.222743 0.057 Uiso 1 1 calc R . . . .
C15B C 0.03582(19) 0.47849(13) 0.26195(13) 0.0348(4) Uani 1 1 d . . . . .
H15B H -0.001265 0.462173 0.326085 0.042 Uiso 1 1 calc R . . . .
C16B C 0.55096(17) 0.77108(11) 0.17331(10) 0.0212(3) Uani 1 1 d . . . . .
C17B C 0.69638(17) 0.80039(11) 0.11448(10) 0.0222(3) Uani 1 1 d . . . . .
C18B C 0.8455(2) 0.90824(14) 0.02483(11) 0.0353(4) Uani 1 1 d . . . . .
H18B H 0.881573 0.970864 -0.008786 0.042 Uiso 1 1 calc R . . . .
C19B C 0.9292(2) 0.81181(15) 0.02473(12) 0.0378(4) Uani 1 1 d . . . . .
H19B H 1.032569 0.793987 -0.008075 0.045 Uiso 1 1 calc R . . . .
C20B C 0.83280(18) 0.74142(13) 0.08344(12) 0.0298(4) Uani 1 1 d . . . . .
H20B H 0.859268 0.667351 0.097962 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.3730(18) . ?
O1 C18 1.3593(18) . ?
O2 C16 1.2550(17) . ?
N1 H1 0.8800 . ?
N1 C1 1.3361(19) . ?
N1 C2 1.4581(19) . ?
N2 H2 0.8800 . ?
N2 C1 1.3399(18) . ?
N2 C9 1.454(2) . ?
N3 C1 1.3466(18) . ?
N3 C16 1.3335(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.519(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.477(2) . ?
C17 C20 1.347(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.332(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.425(2) . ?
C20 H20 0.9500 . ?
O1B C17B 1.3697(17) . ?
O1B C18B 1.366(2) . ?
O2B C16B 1.2505(18) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.3407(18) . ?
N1B C2B 1.4512(19) . ?
N2B H2BA 0.8800 . ?
N2B C1B 1.3407(19) . ?
N2B C9B 1.4520(19) . ?
N3B C1B 1.3430(19) . ?
N3B C16B 1.3434(18) . ?
C2B H2BB 0.9900 . ?
C2B H2BC 0.9900 . ?
C2B C3B 1.511(2) . ?
C3B C4B 1.384(2) . ?
C3B C8B 1.389(2) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.379(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.384(3) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.385(2) . ?
C8B H8B 0.9500 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.516(2) . ?
C10B C11B 1.387(2) . ?
C10B C15B 1.386(2) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.387(2) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.380(3) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.377(3) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.379(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.470(2) . ?
C17B C20B 1.349(2) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.339(3) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.421(2) . ?
C20B H20B 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
C18 O1 C17 106.55(12) . . ?
C1 N1 H1 117.5 . . ?
C1 N1 C2 124.90(13) . . ?
C2 N1 H1 117.5 . . ?
C1 N2 H2 118.0 . . ?
C1 N2 C9 123.96(13) . . ?
C9 N2 H2 118.0 . . ?
C16 N3 C1 120.22(12) . . ?
N1 C1 N2 118.32(13) . . ?
N1 C1 N3 124.73(13) . . ?
N2 C1 N3 116.93(13) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
N1 C2 C3 113.47(12) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C4 C3 C2 120.34(14) . . ?
C8 C3 C2 121.12(13) . . ?
C8 C3 C4 118.53(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.56(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.45(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.42(15) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.29(16) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.6 . . ?
C7 C8 C3 120.75(15) . . ?
C7 C8 H8 119.6 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N2 C9 C10 112.53(12) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 121.93(13) . . ?
C15 C10 C9 119.40(13) . . ?
C15 C10 C11 118.65(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.57(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.34(15) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.40(15) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.38(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.66(14) . . ?
C14 C15 H15 119.7 . . ?
O2 C16 N3 129.02(13) . . ?
O2 C16 C17 116.62(12) . . ?
N3 C16 C17 114.36(12) . . ?
O1 C17 C16 119.00(12) . . ?
C20 C17 O1 109.57(13) . . ?
C20 C17 C16 131.40(14) . . ?
O1 C18 H18 124.7 . . ?
C19 C18 O1 110.69(14) . . ?
C19 C18 H18 124.7 . . ?
C18 C19 H19 126.7 . . ?
C18 C19 C20 106.63(15) . . ?
C20 C19 H19 126.7 . . ?
C17 C20 C19 106.55(15) . . ?
C17 C20 H20 126.7 . . ?
C19 C20 H20 126.7 . . ?
C18B O1B C17B 105.90(13) . . ?
C1B N1B H1B 117.8 . . ?
C1B N1B C2B 124.31(13) . . ?
C2B N1B H1B 117.8 . . ?
C1B N2B H2BA 117.6 . . ?
C1B N2B C9B 124.86(12) . . ?
C9B N2B H2BA 117.6 . . ?
C1B N3B C16B 120.87(13) . . ?
N1B C1B N2B 118.07(13) . . ?
N1B C1B N3B 117.39(13) . . ?
N2B C1B N3B 124.52(13) . . ?
N1B C2B H2BB 109.0 . . ?
N1B C2B H2BC 109.0 . . ?
N1B C2B C3B 113.02(12) . . ?
H2BB C2B H2BC 107.8 . . ?
C3B C2B H2BB 109.0 . . ?
C3B C2B H2BC 109.0 . . ?
C4B C3B C2B 119.66(14) . . ?
C4B C3B C8B 118.87(14) . . ?
C8B C3B C2B 121.47(14) . . ?
C3B C4B H4B 119.7 . . ?
C3B C4B C5B 120.69(16) . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B C4B 120.09(17) . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B H6B 120.1 . . ?
C5B C6B C7B 119.79(16) . . ?
C7B C6B H6B 120.1 . . ?
C6B C7B H7B 120.0 . . ?
C6B C7B C8B 120.02(17) . . ?
C8B C7B H7B 120.0 . . ?
C3B C8B H8B 119.7 . . ?
C7B C8B C3B 120.54(16) . . ?
C7B C8B H8B 119.7 . . ?
N2B C9B H9BA 108.8 . . ?
N2B C9B H9BB 108.8 . . ?
N2B C9B C10B 113.76(12) . . ?
H9BA C9B H9BB 107.7 . . ?
C10B C9B H9BA 108.8 . . ?
C10B C9B H9BB 108.8 . . ?
C11B C10B C9B 122.07(14) . . ?
C15B C10B C9B 119.13(14) . . ?
C15B C10B C11B 118.80(15) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B C10B 120.36(17) . . ?
C12B C11B H11B 119.8 . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B C11B 120.14(18) . . ?
C13B C12B H12B 119.9 . . ?
C12B C13B H13B 120.2 . . ?
C14B C13B C12B 119.66(17) . . ?
C14B C13B H13B 120.2 . . ?
C13B C14B H14B 119.8 . . ?
C13B C14B C15B 120.36(18) . . ?
C15B C14B H14B 119.8 . . ?
C10B C15B H15B 119.7 . . ?
C14B C15B C10B 120.65(18) . . ?
C14B C15B H15B 119.7 . . ?
O2B C16B N3B 128.75(14) . . ?
O2B C16B C17B 119.76(13) . . ?
N3B C16B C17B 111.49(12) . . ?
O1B C17B C16B 118.03(13) . . ?
C20B C17B O1B 110.23(14) . . ?
C20B C17B C16B 131.70(14) . . ?
O1B C18B H18B 124.5 . . ?
C19B C18B O1B 110.94(15) . . ?
C19B C18B H18B 124.5 . . ?
C18B C19B H19B 126.8 . . ?
C18B C19B C20B 106.38(15) . . ?
C20B C19B H19B 126.8 . . ?
C17B C20B C19B 106.54(15) . . ?
C17B C20B H20B 126.7 . . ?
C19B C20B H20B 126.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88 1.99 2.6495(15) 130.2 . yes
N2 H2 O2B 0.88 2.09 2.9006(16) 152.6 1_545 yes
N1B H1B O2 0.88 2.01 2.7729(16) 144.7 . yes
N2B H2BA O2B 0.88 2.01 2.6604(16) 130.0 . yes

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
O1 C17 C20 C19 0.41(19) . . . . ?
O1 C18 C19 C20 0.7(2) . . . . ?
O2 C16 C17 O1 161.56(12) . . . . ?
O2 C16 C17 C20 -20.5(2) . . . . ?
N1 C2 C3 C4 -139.46(14) . . . . ?
N1 C2 C3 C8 42.0(2) . . . . ?
N2 C9 C10 C11 -26.6(2) . . . . ?
N2 C9 C10 C15 155.30(14) . . . . ?
N3 C16 C17 O1 -19.35(19) . . . . ?
N3 C16 C17 C20 158.63(17) . . . . ?
C1 N1 C2 C3 68.19(19) . . . . ?
C1 N2 C9 C10 114.66(15) . . . . ?
C1 N3 C16 O2 -6.7(2) . . . . ?
C1 N3 C16 C17 174.39(12) . . . . ?
C2 N1 C1 N2 8.8(2) . . . . ?
C2 N1 C1 N3 -169.68(14) . . . . ?
C2 C3 C4 C5 -177.97(14) . . . . ?
C2 C3 C8 C7 177.90(14) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C3 0.3(2) . . . . ?
C8 C3 C4 C5 0.6(2) . . . . ?
C9 N2 C1 N1 -169.60(13) . . . . ?
C9 N2 C1 N3 9.0(2) . . . . ?
C9 C10 C11 C12 -178.79(14) . . . . ?
C9 C10 C15 C14 178.64(15) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C10 C15 C14 0.4(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C15 C10 C11 C12 -0.6(2) . . . . ?
C16 N3 C1 N1 -4.3(2) . . . . ?
C16 N3 C1 N2 177.19(13) . . . . ?
C16 C17 C20 C19 -177.71(15) . . . . ?
C17 O1 C18 C19 -0.50(18) . . . . ?
C18 O1 C17 C16 178.42(13) . . . . ?
C18 O1 C17 C20 0.03(17) . . . . ?
C18 C19 C20 C17 -0.7(2) . . . . ?
O1B C17B C20B C19B -0.76(18) . . . . ?
O1B C18B C19B C20B -0.07(19) . . . . ?
O2B C16B C17B O1B -6.6(2) . . . . ?
O2B C16B C17B C20B 176.10(15) . . . . ?
N1B C2B C3B C4B -139.81(14) . . . . ?
N1B C2B C3B C8B 40.0(2) . . . . ?
N2B C9B C10B C11B -26.2(2) . . . . ?
N2B C9B C10B C15B 153.91(14) . . . . ?
N3B C16B C17B O1B 172.68(12) . . . . ?
N3B C16B C17B C20B -4.6(2) . . . . ?
C1B N1B C2B C3B -121.06(15) . . . . ?
C1B N2B C9B C10B -65.54(19) . . . . ?
C1B N3B C16B O2B 6.8(2) . . . . ?
C1B N3B C16B C17B -172.38(12) . . . . ?
C2B N1B C1B N2B 177.22(13) . . . . ?
C2B N1B C1B N3B -1.4(2) . . . . ?
C2B C3B C4B C5B -179.73(15) . . . . ?
C2B C3B C8B C7B 179.67(15) . . . . ?
C3B C4B C5B C6B 0.1(3) . . . . ?
C4B C3B C8B C7B -0.5(2) . . . . ?
C4B C5B C6B C7B -0.6(3) . . . . ?
C5B C6B C7B C8B 0.5(3) . . . . ?
C6B C7B C8B C3B 0.0(2) . . . . ?
C8B C3B C4B C5B 0.4(2) . . . . ?
C9B N2B C1B N1B -7.7(2) . . . . ?
C9B N2B C1B N3B 170.85(14) . . . . ?
C9B C10B C11B C12B 178.60(15) . . . . ?
C9B C10B C15B C14B -179.29(15) . . . . ?
C10B C11B C12B C13B 1.2(3) . . . . ?
C11B C10B C15B C14B 0.8(2) . . . . ?
C11B C12B C13B C14B -0.1(3) . . . . ?
C12B C13B C14B C15B -0.6(3) . . . . ?
C13B C14B C15B C10B 0.2(3) . . . . ?
C15B C10B C11B C12B -1.5(2) . . . . ?
C16B N3B C1B N1B 179.02(12) . . . . ?
C16B N3B C1B N2B 0.5(2) . . . . ?
C16B C17B C20B C19B 176.69(15) . . . . ?
C17B O1B C18B C19B -0.38(18) . . . . ?
C18B O1B C17B C16B -177.13(13) . . . . ?
C18B O1B C17B C20B 0.71(16) . . . . ?
C18B C19B C20B C17B 0.51(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
