# 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_18072
_database_code_depnum_ccdc_archive 'CCDC 1896570'
loop_
_audit_author_name
_audit_author_address
'Jeffery Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-02-11 deposited with the CCDC.	2019-06-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_18072               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.934 Why?  
RESPONSE: The datum crystal exhibited extremely weak diffraction past 1 
angstrom resolution.  Attempts to collect on a more strongly diffracting 
crystal were unsuccessful.  However, enough data was collected to build 
a reliable model.
;
_vrf_PLAT911_18072               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        109 Report
RESPONSE: The datum crystal exhibited extremely weak diffraction past 1 
angstrom resolution.  Attempts to collect on a more strongly diffracting 
crystal were unsuccessful.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O2'
_chemical_formula_sum            'C21 H19 N3 O2'
_chemical_formula_weight         345.39

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.6371(4)
_cell_length_b                   14.5261(8)
_cell_length_c                   16.1757(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1794.49(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2686
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      50.28
_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6075
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12623
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.090
_diffrn_reflns_theta_max         68.318
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.860
_reflns_number_total             2809
_reflns_number_gt                1792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.590
_reflns_Friedel_fraction_max     0.750
_reflns_Friedel_fraction_full    0.759

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

_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 

For the data crystal, mean I/σ(I) was less than 2 for reflections beyond 
1Å resolution.  Reflections between 1 and 0.83Å resolution were used 
for least-squares refinement to improve the data-to-variable ratio at the 
expense of agreement factors.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2809
_refine_ls_number_parameters     314
_refine_ls_number_restraints     269
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.932
_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
O1 O 0.915(4) 0.7133(18) 0.4317(16) 0.050(4) Uani 0.70(9) 1 d D U P A 1
O2 O 1.059(2) 0.595(2) 0.385(2) 0.057(5) Uani 0.70(9) 1 d D U P A 1
N1 N 0.924(2) 0.6314(18) 0.412(2) 0.045(4) Uani 0.70(9) 1 d D U P A 1
O1B O 0.950(6) 0.694(4) 0.428(4) 0.053(7) Uani 0.30(9) 1 d D U P A 2
O2B O 1.061(5) 0.575(4) 0.366(4) 0.060(7) Uani 0.30(9) 1 d D U P A 2
N1B N 0.941(4) 0.614(4) 0.403(5) 0.051(6) Uani 0.30(9) 1 d D U P A 2
N2 N 0.3097(5) 0.4234(3) 0.4461(3) 0.0379(11) Uani 1 1 d . . . . .
H2A H 0.242(6) 0.438(4) 0.495(3) 0.057 Uiso 1 1 d . U . . .
N3 N 0.0680(5) 0.3895(3) 0.5625(3) 0.0411(11) Uani 1 1 d . . . . .
C1 C 0.7679(5) 0.5733(4) 0.4175(3) 0.0410(13) Uani 1 1 d D . . . .
C2 C 0.6261(6) 0.6117(3) 0.4581(3) 0.0439(14) Uani 1 1 d . . . . .
H2 H 0.633014 0.671802 0.480984 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4757(6) 0.5610(3) 0.4647(3) 0.0406(13) Uani 1 1 d . . . . .
H3 H 0.376492 0.586858 0.491445 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4654(5) 0.4717(3) 0.4325(3) 0.0387(13) Uani 1 1 d . . . . .
C5 C 0.6109(6) 0.4339(4) 0.3931(3) 0.0439(14) Uani 1 1 d . . . . .
H5 H 0.605379 0.373143 0.371404 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7633(6) 0.4847(4) 0.3854(3) 0.0427(14) Uani 1 1 d . . . . .
H6 H 0.862985 0.459441 0.358626 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2278(6) 0.3574(3) 0.3973(3) 0.0390(13) Uani 1 1 d . . . . .
C8 C 0.0832(5) 0.3096(3) 0.4307(3) 0.0373(12) Uani 1 1 d . . . . .
C9 C -0.0022(6) 0.2438(3) 0.3812(4) 0.0456(14) Uani 1 1 d . . . . .
H9 H -0.099100 0.210936 0.403368 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0506(6) 0.2259(4) 0.3025(4) 0.0490(15) Uani 1 1 d . . . . .
H10 H -0.007286 0.180417 0.270375 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1892(7) 0.2749(4) 0.2699(4) 0.0485(15) Uani 1 1 d . . . . .
H11 H 0.224106 0.263559 0.214466 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2785(6) 0.3398(4) 0.3158(4) 0.0452(14) Uani 1 1 d . . . . .
H12 H 0.373900 0.372370 0.292046 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0094(6) 0.3286(4) 0.5121(3) 0.0425(14) Uani 1 1 d . . . . .
H13 H -0.089057 0.293330 0.529086 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0278(6) 0.4033(4) 0.6404(3) 0.0484(15) Uani 1 1 d D . . . .
H14 H -0.129202 0.359812 0.642223 0.058 Uiso 1 1 calc R U . B 1
C15 C -0.0963(6) 0.5011(4) 0.6430(3) 0.0460(13) Uani 0.57(4) 1 d D U P C 1
C16 C 0.003(2) 0.5798(8) 0.625(2) 0.048(3) Uani 0.57(4) 1 d D U P C 1
H16 H 0.119857 0.574326 0.605408 0.058 Uiso 0.57(4) 1 calc R U P C 1
C17 C -0.074(3) 0.6669(8) 0.6356(13) 0.050(3) Uani 0.57(4) 1 d D U P C 1
H17 H -0.005314 0.720536 0.626372 0.060 Uiso 0.57(4) 1 calc R U P C 1
C18 C -0.243(3) 0.6761(10) 0.6590(13) 0.048(3) Uani 0.57(4) 1 d D U P C 1
H18 H -0.293779 0.735665 0.664167 0.057 Uiso 0.57(4) 1 calc R U P C 1
C19 C -0.3433(19) 0.5985(13) 0.6755(14) 0.052(3) Uani 0.57(4) 1 d D U P C 1
H19 H -0.463156 0.604537 0.690167 0.063 Uiso 0.57(4) 1 calc R U P C 1
C20 C -0.2674(13) 0.5119(11) 0.6705(16) 0.051(3) Uani 0.57(4) 1 d D U P C 1
H20 H -0.333405 0.459293 0.686041 0.061 Uiso 0.57(4) 1 calc R U P C 1
C15B C -0.0963(6) 0.5011(4) 0.6430(3) 0.0460(13) Uani 0.43(4) 1 d D U P C 2
C16B C 0.028(3) 0.5694(10) 0.625(3) 0.049(3) Uani 0.43(4) 1 d D U P C 2
H16B H 0.146483 0.553425 0.613841 0.058 Uiso 0.43(4) 1 calc R U P C 2
C17B C -0.026(3) 0.6619(10) 0.6236(18) 0.050(3) Uani 0.43(4) 1 d D U P C 2
H17B H 0.056434 0.708545 0.609878 0.060 Uiso 0.43(4) 1 calc R U P C 2
C18B C -0.193(4) 0.6860(12) 0.6416(17) 0.050(3) Uani 0.43(4) 1 d D U P C 2
H18B H -0.226765 0.748996 0.641146 0.060 Uiso 0.43(4) 1 calc R U P C 2
C19B C -0.316(3) 0.6189(16) 0.6606(18) 0.050(3) Uani 0.43(4) 1 d D U P C 2
H19B H -0.431785 0.635830 0.676015 0.060 Uiso 0.43(4) 1 calc R U P C 2
C20B C -0.2685(16) 0.5269(13) 0.6569(19) 0.049(3) Uani 0.43(4) 1 d D U P C 2
H20B H -0.355369 0.480791 0.664074 0.059 Uiso 0.43(4) 1 calc R U P C 2
C21 C 0.0932(7) 0.3828(4) 0.7122(3) 0.0578(16) Uani 1 1 d . . . . .
H21A H 0.127367 0.317795 0.710653 0.087 Uiso 1 1 calc R U . . .
H21B H 0.032531 0.395810 0.764272 0.087 Uiso 1 1 calc R U . . .
H21C H 0.197926 0.421492 0.708074 0.087 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Nineteen 
frame series were integrated and filtered for statistical outliers using 
SAINT (Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the 
combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.1060
-1.00 0.00 0.00 0.0850
0.00 -1.00 1.00 0.0370
0.00 1.00 -1.00 0.0030
0.00 1.00 1.00 0.0420
0.00 -1.00 -1.00 0.0010

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 N1 1.235(8) . ?
O2 N1 1.231(10) . ?
N1 C1 1.465(8) . ?
O1B N1B 1.236(12) . ?
O2B N1B 1.231(13) . ?
N1B C1 1.468(12) . ?
N2 C7 1.391(6) . ?
N2 C4 1.399(6) . ?
N2 H2A 0.97(5) . ?
N3 C13 1.283(6) . ?
N3 C14 1.471(6) . ?
C1 C2 1.385(7) . ?
C1 C6 1.387(7) . ?
C2 C3 1.368(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(6) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.398(7) . ?
C7 C8 1.412(6) . ?
C8 C9 1.407(7) . ?
C8 C13 1.459(7) . ?
C9 C10 1.361(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15B 1.513(6) . ?
C14 C15 1.513(6) . ?
C14 C21 1.514(7) . ?
C14 H14 1.0000 . ?
C15 C20 1.389(9) . ?
C15 C16 1.403(9) . ?
C16 C17 1.405(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.356(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(12) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C15B C20B 1.386(10) . ?
C15B C16B 1.405(10) . ?
C16B C17B 1.406(11) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.358(12) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.386(13) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.386(11) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
O2 N1 O1 123.5(9) . . ?
O2 N1 C1 116.9(14) . . ?
O1 N1 C1 119.5(12) . . ?
O2B N1B O1B 123(2) . . ?
O2B N1B C1 124(3) . . ?
O1B N1B C1 112(3) . . ?
C7 N2 C4 129.7(4) . . ?
C7 N2 H2A 112(3) . . ?
C4 N2 H2A 118(3) . . ?
C13 N3 C14 117.6(4) . . ?
C2 C1 C6 122.1(4) . . ?
C2 C1 N1 115.8(13) . . ?
C6 C1 N1 122.1(13) . . ?
C2 C1 N1B 128(2) . . ?
C6 C1 N1B 110(2) . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 N2 123.5(5) . . ?
C5 C4 C3 119.4(4) . . ?
N2 C4 C3 117.0(4) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N2 C7 C12 122.5(4) . . ?
N2 C7 C8 118.2(5) . . ?
C12 C7 C8 119.2(5) . . ?
C9 C8 C7 118.6(5) . . ?
C9 C8 C13 117.6(4) . . ?
C7 C8 C13 123.7(5) . . ?
C10 C9 C8 121.6(5) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 121.7(6) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C7 119.7(5) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
N3 C13 C8 124.6(5) . . ?
N3 C13 H13 117.7 . . ?
C8 C13 H13 117.7 . . ?
N3 C14 C15B 108.9(4) . . ?
N3 C14 C15 108.9(4) . . ?
N3 C14 C21 109.0(4) . . ?
C15B C14 C21 112.0(5) . . ?
C15 C14 C21 112.0(5) . . ?
N3 C14 H14 108.9 . . ?
C15 C14 H14 108.9 . . ?
C21 C14 H14 108.9 . . ?
C20 C15 C16 118.8(8) . . ?
C20 C15 C14 116.2(8) . . ?
C16 C15 C14 124.9(8) . . ?
C15 C16 C17 118.9(9) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 121.5(10) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.9(9) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.8(9) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 121.0(9) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C20B C15B C16B 119.0(10) . . ?
C20B C15B C14 125.9(9) . . ?
C16B C15B C14 115.0(9) . . ?
C15B C16B C17B 118.7(11) . . ?
C15B C16B H16B 120.7 . . ?
C17B C16B H16B 120.7 . . ?
C18B C17B C16B 121.3(12) . . ?
C18B C17B H17B 119.4 . . ?
C16B C17B H17B 119.4 . . ?
C17B C18B C19B 120.2(11) . . ?
C17B C18B H18B 119.9 . . ?
C19B C18B H18B 119.9 . . ?
C18B C19B C20B 119.4(11) . . ?
C18B C19B H19B 120.3 . . ?
C20B C19B H19B 120.3 . . ?
C15B C20B C19B 121.1(11) . . ?
C15B C20B H20B 119.4 . . ?
C19B C20B H20B 119.4 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O2 N1 C1 C2 171.1(18) . . . . ?
O1 N1 C1 C2 -10(3) . . . . ?
O2 N1 C1 C6 -8(3) . . . . ?
O1 N1 C1 C6 170.9(18) . . . . ?
O2B N1B C1 C2 180(5) . . . . ?
O1B N1B C1 C2 -4(8) . . . . ?
O2B N1B C1 C6 2(8) . . . . ?
O1B N1B C1 C6 178(5) . . . . ?
C6 C1 C2 C3 -1.7(7) . . . . ?
N1 C1 C2 C3 179.3(14) . . . . ?
N1B C1 C2 C3 -180(4) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C7 N2 C4 C5 -34.9(8) . . . . ?
C7 N2 C4 C3 148.6(5) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C2 C3 C4 N2 176.6(4) . . . . ?
N2 C4 C5 C6 -176.9(4) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C2 C1 C6 C5 1.1(7) . . . . ?
N1 C1 C6 C5 -179.9(15) . . . . ?
N1B C1 C6 C5 179(3) . . . . ?
C4 N2 C7 C12 -11.5(7) . . . . ?
C4 N2 C7 C8 171.3(4) . . . . ?
N2 C7 C8 C9 179.0(4) . . . . ?
C12 C7 C8 C9 1.7(6) . . . . ?
N2 C7 C8 C13 3.1(7) . . . . ?
C12 C7 C8 C13 -174.2(4) . . . . ?
C7 C8 C9 C10 -0.5(7) . . . . ?
C13 C8 C9 C10 175.7(4) . . . . ?
C8 C9 C10 C11 -1.2(7) . . . . ?
C9 C10 C11 C12 1.6(8) . . . . ?
C10 C11 C12 C7 -0.3(7) . . . . ?
N2 C7 C12 C11 -178.5(4) . . . . ?
C8 C7 C12 C11 -1.4(7) . . . . ?
C14 N3 C13 C8 176.7(4) . . . . ?
C9 C8 C13 N3 -176.8(4) . . . . ?
C7 C8 C13 N3 -0.8(7) . . . . ?
C13 N3 C14 C15B -118.0(5) . . . . ?
C13 N3 C14 C15 -118.0(5) . . . . ?
C13 N3 C14 C21 119.5(5) . . . . ?
N3 C14 C15 C20 136.4(12) . . . . ?
C21 C14 C15 C20 -102.9(13) . . . . ?
N3 C14 C15 C16 -47.6(19) . . . . ?
C21 C14 C15 C16 73.1(19) . . . . ?
C20 C15 C16 C17 1(3) . . . . ?
C14 C15 C16 C17 -175.3(16) . . . . ?
C15 C16 C17 C18 -3(4) . . . . ?
C16 C17 C18 C19 2(3) . . . . ?
C17 C18 C19 C20 2(2) . . . . ?
C18 C19 C20 C15 -5(3) . . . . ?
C16 C15 C20 C19 4(3) . . . . ?
C14 C15 C20 C19 179.9(14) . . . . ?
N3 C14 C15B C20B 126.7(17) . . . . ?
C21 C14 C15B C20B -112.6(17) . . . . ?
N3 C14 C15B C16B -50(2) . . . . ?
C21 C14 C15B C16B 71(2) . . . . ?
C20B C15B C16B C17B 2(5) . . . . ?
C14 C15B C16B C17B 178(3) . . . . ?
C15B C16B C17B C18B 2(5) . . . . ?
C16B C17B C18B C19B -1(4) . . . . ?
C17B C18B C19B C20B -3(3) . . . . ?
C16B C15B C20B C19B -6(4) . . . . ?
C14 C15B C20B C19B 178.0(16) . . . . ?
C18B C19B C20B C15B 7(4) . . . . ?

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 H2A N3 0.97(5) 1.86(5) 2.681(6) 141(4) . yes

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.058

