# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_bam126
_database_code_depnum_ccdc_archive 'CCDC 1946969'
loop_
_audit_author_name
_audit_author_address
'John Gorden'
;Auburn University
United States of America
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H38 N4 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         514.65

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   9.0812(5)
_cell_length_b                   9.9887(5)
_cell_length_c                   16.3825(9)
_cell_angle_alpha                103.5190(10)
_cell_angle_beta                 103.2200(10)
_cell_angle_gamma                99.4900(10)
_cell_volume                     1368.65(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7275
_cell_measurement_theta_min      2.1551
_cell_measurement_theta_max      29.6745
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       fragment
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            29332
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             7073
_reflns_number_gt                5267
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1411
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         7073
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.5063P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.34101(13) 0.66604(11) 0.70893(7) 0.0339(3) Uani d . . . 1.0 . .
H H1 0.388264 0.698455 0.678168 0.051 Uiso calc U . R 1.0 . .
H H1W 0.887(2) 0.289(2) 0.5765(12) 0.041 Uiso d U . . 1.0 . .
C C1 0.93468(19) 1.11217(17) 0.30393(11) 0.0344(3) Uani d . . . 1.0 . .
H H1A 0.942309 1.188699 0.280685 0.041 Uiso calc U . R 1.0 . .
C C2 0.85053(18) 1.10680(15) 0.36212(10) 0.0307(3) Uani d . . . 1.0 . .
H H2 0.802659 1.179919 0.379119 0.037 Uiso calc U . R 1.0 . .
H H2W 0.748(2) 0.203(2) 0.5273(12) 0.037 Uiso d U . . 1.0 . .
N N4 0.74673(14) 0.98087(12) 0.45223(7) 0.0245(2) Uani d . . . 1.0 . .
C C3 0.83540(16) 0.98850(14) 0.39737(9) 0.0236(3) Uani d . . . 1.0 . .
C C6 0.63185(16) 0.85007(14) 0.53489(9) 0.0242(3) Uani d . . . 1.0 . .
H H6 0.575483 0.917489 0.549147 0.029 Uiso calc U . R 1.0 . .
C C5 0.73100(15) 0.86455(13) 0.48070(8) 0.0214(3) Uani d . . . 1.0 . .
C C7 0.62149(16) 0.73358(14) 0.56571(8) 0.0220(3) Uani d . . . 1.0 . .
C C9 0.57047(16) 0.57551(14) 0.63241(8) 0.0226(3) Uani d . . . 1.0 . .
N N8 0.53665(14) 0.69534(12) 0.62050(8) 0.0250(2) Uani d . . . 1.0 . .
C C10 0.50930(15) 0.50455(14) 0.69007(8) 0.0220(3) Uani d . . . 1.0 . .
C C11 0.56507(16) 0.39073(14) 0.71131(9) 0.0230(3) Uani d . . . 1.0 . .
H H11 0.638597 0.357428 0.685935 0.028 Uiso calc U . R 1.0 . .
C C12 0.51321(16) 0.32659(14) 0.76927(9) 0.0227(3) Uani d . . . 1.0 . .
C C13 0.40122(16) 0.37994(14) 0.80517(9) 0.0240(3) Uani d . . . 1.0 . .
H H13 0.364866 0.337337 0.843771 0.029 Uiso calc U . R 1.0 . .
C C14 0.34085(16) 0.49268(14) 0.78676(9) 0.0240(3) Uani d . . . 1.0 . .
C C15 0.39694(16) 0.55582(14) 0.72802(9) 0.0243(3) Uani d . . . 1.0 . .
C C16 0.58506(16) 0.20978(15) 0.79721(9) 0.0249(3) Uani d . . . 1.0 . .
C C17 0.59430(18) 0.09827(15) 0.71767(10) 0.0303(3) Uani d . . . 1.0 . .
H H17A 0.491313 0.053026 0.680464 0.045 Uiso calc U . R 1.0 . .
H H17B 0.643696 0.028827 0.736891 0.045 Uiso calc U . R 1.0 . .
H H17C 0.653684 0.143098 0.685835 0.045 Uiso calc U . R 1.0 . .
C C18 0.4912(2) 0.13341(18) 0.84657(12) 0.0388(4) Uani d . . . 1.0 . .
H H18A 0.385141 0.097603 0.811582 0.058 Uiso calc U . R 1.0 . .
H H18B 0.494848 0.198551 0.900749 0.058 Uiso calc U . R 1.0 . .
H H18C 0.53472 0.056282 0.858259 0.058 Uiso calc U . R 1.0 . .
C C19 0.75054(19) 0.27792(18) 0.85711(11) 0.0366(4) Uani d . . . 1.0 . .
H H19A 0.797384 0.206289 0.875114 0.055 Uiso calc U . R 1.0 . .
H H19B 0.746246 0.347144 0.907673 0.055 Uiso calc U . R 1.0 . .
H H19C 0.811379 0.322911 0.825976 0.055 Uiso calc U . R 1.0 . .
C C20 0.22113(17) 0.54906(15) 0.83004(9) 0.0279(3) Uani d . . . 1.0 . .
O O1W 0.78603(14) 0.28539(12) 0.56158(8) 0.0352(3) Uani d . . . 1.0 . .
C C21 0.2867(2) 0.70581(17) 0.88291(11) 0.0397(4) Uani d . . . 1.0 . .
H H21A 0.305031 0.761323 0.844115 0.06 Uiso calc U . R 1.0 . .
H H21B 0.382729 0.715098 0.925593 0.06 Uiso calc U . R 1.0 . .
H H21C 0.213322 0.73856 0.911911 0.06 Uiso calc U . R 1.0 . .
C C22 0.06869(18) 0.53274(17) 0.76012(11) 0.0337(3) Uani d . . . 1.0 . .
H H22A 0.090129 0.579007 0.717528 0.051 Uiso calc U . R 1.0 . .
H H22B -0.002085 0.574958 0.787298 0.051 Uiso calc U . R 1.0 . .
H H22C 0.022929 0.434082 0.731918 0.051 Uiso calc U . R 1.0 . .
C C24 1.01139(19) 1.00352(17) 0.27773(11) 0.0345(3) Uani d . . . 1.0 . .
H H24 1.067492 1.008973 0.237236 0.041 Uiso calc U . R 1.0 . .
C C25 1.00306(18) 0.89135(16) 0.31172(10) 0.0308(3) Uani d . . . 1.0 . .
H H25 1.055746 0.82177 0.295365 0.037 Uiso calc U . R 1.0 . .
C C26 0.91450(16) 0.87970(14) 0.37200(9) 0.0236(3) Uani d . . . 1.0 . .
N N27 0.90728(13) 0.76758(12) 0.40436(8) 0.0241(2) Uani d . . . 1.0 . .
C C28 0.81548(15) 0.75623(13) 0.45748(8) 0.0209(3) Uani d . . . 1.0 . .
C C29 0.80315(16) 0.63686(14) 0.49070(9) 0.0227(3) Uani d . . . 1.0 . .
H H29 0.857057 0.567246 0.476696 0.027 Uiso calc U . R 1.0 . .
C C30 0.70846(15) 0.62896(13) 0.54418(8) 0.0212(3) Uani d . . . 1.0 . .
N N31 0.67212(13) 0.53086(12) 0.58780(7) 0.0230(2) Uani d . . . 1.0 . .
H H31 0.706885 0.455667 0.587087 0.028 Uiso calc U . R 1.0 . .
C C23 0.1820(2) 0.46741(18) 0.89382(11) 0.0360(4) Uani d . . . 1.0 . .
H H23A 0.140621 0.369021 0.862968 0.054 Uiso calc U . R 1.0 . .
H H23B 0.106267 0.504333 0.919042 0.054 Uiso calc U . R 1.0 . .
H H23C 0.274522 0.477816 0.939337 0.054 Uiso calc U . R 1.0 . .
O O1S 0.8159(2) 0.93674(15) 0.89744(10) 0.0624(4) Uani d . . . 1.0 . .
C C2S 0.7876(4) 0.7114(2) 0.91845(17) 0.0725(7) Uani d . . . 1.0 . .
H H2SA 0.702968 0.630057 0.906513 0.087 Uiso calc U . R 1.0 A 1
H H2SB 0.882888 0.679742 0.917929 0.087 Uiso calc U . R 1.0 A 1
C C3S 0.8043(3) 0.8172(2) 1.00370(14) 0.0601(6) Uani d . . . 1.0 . .
H H3SA 0.725864 0.786053 1.030918 0.072 Uiso calc U . R 1.0 . .
H H3SB 0.90642 0.832464 1.043706 0.072 Uiso calc U . R 1.0 . .
C C4S 0.7824(3) 0.9488(3) 0.97859(16) 0.0676(6) Uani d . . . 1.0 . .
H H4SC 0.676254 0.958185 0.973379 0.081 Uiso calc U . R 1.0 . .
H H4SD 0.851892 1.03143 1.022563 0.081 Uiso calc U . R 1.0 . .
C C1SA 0.7518(10) 0.7981(5) 0.8515(3) 0.0555(16) Uani d . P . 0.642(17) B 1
H H1SA 0.797746 0.770101 0.804065 0.067 Uiso calc U P R 0.642(17) B 1
H H1SB 0.640534 0.783289 0.827224 0.067 Uiso calc U P R 0.642(17) B 1
C C1SB 0.838(2) 0.7940(9) 0.8649(7) 0.064(3) Uani d . P . 0.358(17) B 2
H H1SC 0.778154 0.752397 0.804304 0.077 Uiso calc U P R 0.358(17) B 2
H H1SD 0.947228 0.797585 0.86858 0.077 Uiso calc U P R 0.358(17) B 2


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 . 1.3566(16) ?
O1 H1 . 0.82 ?
C1 C2 . 1.356(2) ?
C1 C24 . 1.420(2) ?
C1 H1A . 0.93 ?
C2 C3 . 1.4320(18) ?
C2 H2 . 0.93 ?
N4 C3 . 1.3434(18) ?
N4 C5 . 1.3480(16) ?
C3 C26 . 1.4327(19) ?
C6 C7 . 1.3704(18) ?
C6 C5 . 1.4152(19) ?
C6 H6 . 0.93 ?
C5 C28 . 1.4555(17) ?
C7 N8 . 1.3873(17) ?
C7 C30 . 1.4378(18) ?
C9 N8 . 1.3298(17) ?
C9 N31 . 1.3701(17) ?
C9 C10 . 1.4583(18) ?
C10 C11 . 1.4015(18) ?
C10 C15 . 1.4155(18) ?
C11 C12 . 1.3868(18) ?
C11 H11 . 0.93 ?
C12 C13 . 1.4036(18) ?
C12 C16 . 1.5364(18) ?
C13 C14 . 1.3952(18) ?
C13 H13 . 0.93 ?
C14 C15 . 1.4091(19) ?
C14 C20 . 1.5393(18) ?
C16 C17 . 1.532(2) ?
C16 C18 . 1.534(2) ?
C16 C19 . 1.536(2) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 C23 . 1.535(2) ?
C20 C22 . 1.539(2) ?
C20 C21 . 1.542(2) ?
O1W H1W . 0.89(2) ?
O1W H2W . 0.84(2) ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C24 C25 . 1.362(2) ?
C24 H24 . 0.93 ?
C25 C26 . 1.4219(19) ?
C25 H25 . 0.93 ?
C26 N27 . 1.3449(16) ?
N27 C28 . 1.3461(17) ?
C28 C29 . 1.4205(17) ?
C29 C30 . 1.3667(18) ?
C29 H29 . 0.93 ?
C30 N31 . 1.3815(16) ?
N31 H31 . 0.86 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
O1S C1SA . 1.367(5) ?
O1S C4S . 1.413(3) ?
O1S C1SB . 1.466(8) ?
C2S C1SB . 1.436(10) ?
C2S C3S . 1.500(3) ?
C2S C1SA . 1.560(6) ?
C2S H2SA . 0.97 ?
C2S H2SB . 0.97 ?
C3S C4S . 1.496(3) ?
C3S H3SA . 0.97 ?
C3S H3SB . 0.97 ?
C4S H4SC . 0.97 ?
C4S H4SD . 0.97 ?
C1SA H1SA . 0.97 ?
C1SA H1SB . 0.97 ?
C1SB H1SC . 0.97 ?
C1SB H1SD . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 O1 H1 . . 109.5 ?
C2 C1 C24 . . 121.44(13) ?
C2 C1 H1A . . 119.3 ?
C24 C1 H1A . . 119.3 ?
C1 C2 C3 . . 119.97(14) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C3 N4 C5 . . 117.43(11) ?
N4 C3 C2 . . 119.74(12) ?
N4 C3 C26 . . 121.57(12) ?
C2 C3 C26 . . 118.69(13) ?
C7 C6 C5 . . 117.91(12) ?
C7 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
N4 C5 C6 . . 118.72(12) ?
N4 C5 C28 . . 121.05(12) ?
C6 C5 C28 . . 120.22(11) ?
C6 C7 N8 . . 129.68(12) ?
C6 C7 C30 . . 121.43(12) ?
N8 C7 C30 . . 108.88(11) ?
N8 C9 N31 . . 112.78(11) ?
N8 C9 C10 . . 122.56(12) ?
N31 C9 C10 . . 124.61(12) ?
C9 N8 C7 . . 105.82(11) ?
C11 C10 C15 . . 119.74(12) ?
C11 C10 C9 . . 120.97(12) ?
C15 C10 C9 . . 119.23(12) ?
C12 C11 C10 . . 121.57(12) ?
C12 C11 H11 . . 119.2 ?
C10 C11 H11 . . 119.2 ?
C11 C12 C13 . . 117.01(12) ?
C11 C12 C16 . . 120.72(12) ?
C13 C12 C16 . . 122.13(12) ?
C14 C13 C12 . . 124.31(12) ?
C14 C13 H13 . . 117.8 ?
C12 C13 H13 . . 117.8 ?
C13 C14 C15 . . 117.11(12) ?
C13 C14 C20 . . 121.94(12) ?
C15 C14 C20 . . 120.93(12) ?
O1 C15 C14 . . 118.61(12) ?
O1 C15 C10 . . 121.12(12) ?
C14 C15 C10 . . 120.27(12) ?
C17 C16 C18 . . 107.66(12) ?
C17 C16 C19 . . 108.64(12) ?
C18 C16 C19 . . 108.89(13) ?
C17 C16 C12 . . 110.99(11) ?
C18 C16 C12 . . 112.26(11) ?
C19 C16 C12 . . 108.33(12) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C23 C20 C22 . . 107.45(13) ?
C23 C20 C14 . . 111.61(12) ?
C22 C20 C14 . . 110.20(12) ?
C23 C20 C21 . . 107.23(13) ?
C22 C20 C21 . . 110.11(13) ?
C14 C20 C21 . . 110.16(12) ?
H1W O1W H2W . . 103.6(18) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C25 C24 C1 . . 120.19(14) ?
C25 C24 H24 . . 119.9 ?
C1 C24 H24 . . 119.9 ?
C24 C25 C26 . . 120.56(14) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
N27 C26 C25 . . 119.51(12) ?
N27 C26 C3 . . 121.37(12) ?
C25 C26 C3 . . 119.11(12) ?
C26 N27 C28 . . 117.78(11) ?
N27 C28 C29 . . 118.73(11) ?
N27 C28 C5 . . 120.60(11) ?
C29 C28 C5 . . 120.66(12) ?
C30 C29 C28 . . 116.97(12) ?
C30 C29 H29 . . 121.5 ?
C28 C29 H29 . . 121.5 ?
C29 C30 N31 . . 132.04(12) ?
C29 C30 C7 . . 122.77(12) ?
N31 C30 C7 . . 105.18(11) ?
C9 N31 C30 . . 107.33(11) ?
C9 N31 H31 . . 126.3 ?
C30 N31 H31 . . 126.3 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C1SA O1S C4S . . 104.2(3) ?
C4S O1S C1SB . . 108.6(4) ?
C1SB C2S C3S . . 104.9(4) ?
C3S C2S C1SA . . 102.4(3) ?
C3S C2S H2SA . . 111.3 ?
C1SA C2S H2SA . . 111.3 ?
C3S C2S H2SB . . 111.3 ?
C1SA C2S H2SB . . 111.3 ?
H2SA C2S H2SB . . 109.2 ?
C4S C3S C2S . . 103.83(18) ?
C4S C3S H3SA . . 111.0 ?
C2S C3S H3SA . . 111.0 ?
C4S C3S H3SB . . 111.0 ?
C2S C3S H3SB . . 111.0 ?
H3SA C3S H3SB . . 109.0 ?
O1S C4S C3S . . 107.13(17) ?
O1S C4S H4SC . . 110.3 ?
C3S C4S H4SC . . 110.3 ?
O1S C4S H4SD . . 110.3 ?
C3S C4S H4SD . . 110.3 ?
H4SC C4S H4SD . . 108.5 ?
O1S C1SA C2S . . 105.8(3) ?
O1S C1SA H1SA . . 110.6 ?
C2S C1SA H1SA . . 110.6 ?
O1S C1SA H1SB . . 110.6 ?
C2S C1SA H1SB . . 110.6 ?
H1SA C1SA H1SB . . 108.7 ?
C2S C1SB O1S . . 107.3(6) ?
C2S C1SB H1SC . . 110.3 ?
O1S C1SB H1SC . . 110.3 ?
C2S C1SB H1SD . . 110.3 ?
O1S C1SB H1SD . . 110.3 ?
H1SC C1SB H1SD . . 108.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C24 C1 C2 C3 . . . . -1.1(2) ?
C5 N4 C3 C2 . . . . 177.27(12) ?
C5 N4 C3 C26 . . . . -1.93(19) ?
C1 C2 C3 N4 . . . . -177.29(14) ?
C1 C2 C3 C26 . . . . 1.9(2) ?
C3 N4 C5 C6 . . . . -176.74(12) ?
C3 N4 C5 C28 . . . . 4.08(19) ?
C7 C6 C5 N4 . . . . -177.76(12) ?
C7 C6 C5 C28 . . . . 1.4(2) ?
C5 C6 C7 N8 . . . . 178.66(13) ?
C5 C6 C7 C30 . . . . 0.1(2) ?
N31 C9 N8 C7 . . . . -0.63(16) ?
C10 C9 N8 C7 . . . . 176.98(12) ?
C6 C7 N8 C9 . . . . -178.17(14) ?
C30 C7 N8 C9 . . . . 0.49(15) ?
N8 C9 C10 C11 . . . . -170.37(13) ?
N31 C9 C10 C11 . . . . 6.9(2) ?
N8 C9 C10 C15 . . . . 6.8(2) ?
N31 C9 C10 C15 . . . . -175.87(13) ?
C15 C10 C11 C12 . . . . -0.2(2) ?
C9 C10 C11 C12 . . . . 176.93(13) ?
C10 C11 C12 C13 . . . . 0.6(2) ?
C10 C11 C12 C16 . . . . -175.16(12) ?
C11 C12 C13 C14 . . . . -0.5(2) ?
C16 C12 C13 C14 . . . . 175.14(13) ?
C12 C13 C14 C15 . . . . 0.1(2) ?
C12 C13 C14 C20 . . . . -178.39(13) ?
C13 C14 C15 O1 . . . . -179.78(13) ?
C20 C14 C15 O1 . . . . -1.2(2) ?
C13 C14 C15 C10 . . . . 0.2(2) ?
C20 C14 C15 C10 . . . . 178.75(13) ?
C11 C10 C15 O1 . . . . 179.83(13) ?
C9 C10 C15 O1 . . . . 2.6(2) ?
C11 C10 C15 C14 . . . . -0.2(2) ?
C9 C10 C15 C14 . . . . -177.38(13) ?
C11 C12 C16 C17 . . . . -48.24(17) ?
C13 C12 C16 C17 . . . . 136.27(14) ?
C11 C12 C16 C18 . . . . -168.78(13) ?
C13 C12 C16 C18 . . . . 15.72(19) ?
C11 C12 C16 C19 . . . . 70.95(16) ?
C13 C12 C16 C19 . . . . -104.54(15) ?
C13 C14 C20 C23 . . . . 0.6(2) ?
C15 C14 C20 C23 . . . . -177.90(13) ?
C13 C14 C20 C22 . . . . -118.73(15) ?
C15 C14 C20 C22 . . . . 62.80(17) ?
C13 C14 C20 C21 . . . . 119.57(15) ?
C15 C14 C20 C21 . . . . -58.90(18) ?
C2 C1 C24 C25 . . . . -0.7(3) ?
C1 C24 C25 C26 . . . . 1.6(2) ?
C24 C25 C26 N27 . . . . 179.64(14) ?
C24 C25 C26 C3 . . . . -0.7(2) ?
N4 C3 C26 N27 . . . . -2.2(2) ?
C2 C3 C26 N27 . . . . 178.59(13) ?
N4 C3 C26 C25 . . . . 178.16(13) ?
C2 C3 C26 C25 . . . . -1.0(2) ?
C25 C26 N27 C28 . . . . -176.42(13) ?
C3 C26 N27 C28 . . . . 3.94(19) ?
C26 N27 C28 C29 . . . . 178.49(12) ?
C26 N27 C28 C5 . . . . -1.76(19) ?
N4 C5 C28 N27 . . . . -2.35(19) ?
C6 C5 C28 N27 . . . . 178.48(12) ?
N4 C5 C28 C29 . . . . 177.39(12) ?
C6 C5 C28 C29 . . . . -1.77(19) ?
N27 C28 C29 C30 . . . . -179.80(12) ?
C5 C28 C29 C30 . . . . 0.44(19) ?
C28 C29 C30 N31 . . . . -179.01(13) ?
C28 C29 C30 C7 . . . . 1.2(2) ?
C6 C7 C30 C29 . . . . -1.5(2) ?
N8 C7 C30 C29 . . . . 179.69(13) ?
C6 C7 C30 N31 . . . . 178.61(13) ?
N8 C7 C30 N31 . . . . -0.18(14) ?
N8 C9 N31 C30 . . . . 0.53(16) ?
C10 C9 N31 C30 . . . . -177.03(12) ?
C29 C30 N31 C9 . . . . 179.96(14) ?
C7 C30 N31 C9 . . . . -0.19(14) ?
C1SB C2S C3S C4S . . . . 28.9(9) ?
C1SA C2S C3S C4S . . . . -1.6(4) ?
C1SA O1S C4S C3S . . . . 40.0(5) ?
C1SB O1S C4S C3S . . . . 7.3(9) ?
C2S C3S C4S O1S . . . . -22.3(3) ?
C4S O1S C1SA C2S . . . . -40.3(6) ?
C3S C2S C1SA O1S . . . . 25.8(6) ?
C3S C2S C1SB O1S . . . . -25.1(13) ?
C4S O1S C1SB C2S . . . . 11.4(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N8 . 0.82 1.81 2.5583(15) 150.2 ?
O1W H1W N27 2_766 0.89(2) 2.02(2) 2.8742(16) 162.0(18) ?
C2 H2 O1 2_676 0.93 2.64 3.3375(17) 131.9 ?
O1W H2W N4 1_545 0.84(2) 2.27(2) 3.0644(16) 156.8(17) ?
N31 H31 O1W . 0.86 1.95 2.7953(15) 168.4 ?



####################################################################### 
# 
# 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_bam115b_JN
_database_code_depnum_ccdc_archive 'CCDC 2015766'
loop_
_audit_author_name
_audit_author_address
'John Gorden'
;Auburn University
United States of America
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         C25H26N4O7S2U
_chemical_formula_sum            'C25 H26 N4 O7 S2 U'
_chemical_formula_iupac          ?
_chemical_formula_weight         796.65

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.585(5)
_cell_length_b                   20.419(11)
_cell_length_c                   16.091(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.633(8)
_cell_angle_gamma                90
_cell_volume                     2763.(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.3733
_cell_measurement_theta_max      26.4161
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       fragment
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536

_exptl_absorpt_coefficient_mu    6.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.58

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker SMART APEX I'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            33110
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         26.57
_diffrn_reflns_theta_full        26.57
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
The structure was solved and refined using the Bruker SHELXTL Software Package,
using the space group P 1 21/n 1, with Z = 4 for the formula unit,
C25H26N4O7S2U.
The final anisotropic full--matrix least--squares refinement on F2 with 357
variables
converged at R1 = 4.50%, for the observed data and wR2 = 12.81% for all data.
The goodness--of--fit was 1.069. The largest peak in the final difference
electron density
synthesis was 3.750 e--/Å3 and the largest hole was --1.150 e--/Å3 with an
RMS
deviation of 0.194 e--/Å3. On the basis of the final model, the calculated
density was
1.915 g/cm3 and F(000), 1536 e--. Atoms C9 C8 C18 and C19 were restrained with
DELU
to prevent non--positive definites. Additionally C19 was restrained to
approximate isotropic
behavior with ISOR.
;

_reflns_number_total             5707
_reflns_number_gt                4613
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1281
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         5707
_refine_ls_number_parameters     357
_refine_ls_number_restraints     11
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+9.7154P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         3.750
_refine_diff_density_min         -1.150
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U U1 0.59643(3) 0.20955(2) 0.63405(2) 0.02897(11) Uani d . . . 1 . .
S S1S 0.3327(3) 0.54814(11) 0.85411(14) 0.0489(5) Uani d . . . 1 . .
S S1 0.4087(2) 0.25460(8) 0.42215(12) 0.0342(4) Uani d . . . 1 . .
N N1 0.5311(7) 0.4237(3) 0.7257(4) 0.0321(13) Uani d . . . 1 . .
H H1 0.499019 0.448527 0.762079 0.038 Uiso calc U . R 1 . .
O O1 0.6239(6) 0.2271(2) 0.7719(3) 0.0359(11) Uani d . . . 1 . .
C C1 0.5278(9) 0.2571(3) 0.8144(4) 0.0322(15) Uani d . . . 1 . .
N N2 0.7220(7) 0.5690(3) 0.5277(4) 0.0331(13) Uani d . . . 1 . .
O O2 0.8035(7) 0.2151(2) 0.6421(3) 0.0393(12) Uani d . . . 1 . .
C C2 0.4843(10) 0.2262(4) 0.8842(5) 0.0378(16) Uani d . . . 1 . .
H H2 0.516141 0.183258 0.897549 0.045 Uiso calc U . R 1 . .
N N3 0.8000(7) 0.4521(3) 0.4478(4) 0.0299(12) Uani d . . . 1 . .
O O3 0.3872(8) 0.2066(2) 0.6237(4) 0.0425(13) Uani d . . . 1 . .
C C3 0.3955(10) 0.2585(4) 0.9327(5) 0.0426(18) Uani d . . . 1 . .
H H3 0.37241 0.238212 0.980465 0.051 Uiso calc U . R 1 . .
O O4 0.6245(8) 0.0989(3) 0.6907(4) 0.0525(16) Uani d . . . 1 . .
N N4 0.5838(7) 0.3327(3) 0.6622(4) 0.0322(13) Uani d . . . 1 . .
C C4 0.3396(10) 0.3210(4) 0.9117(5) 0.0425(18) Uani d . . . 1 . .
H H4 0.27626 0.341834 0.94427 0.051 Uiso calc U . R 1 . .
C C5 0.3776(9) 0.3528(4) 0.8424(5) 0.0354(16) Uani d . . . 1 . .
H H5 0.339717 0.394818 0.828348 0.043 Uiso calc U . R 1 . .
O O5 0.5879(7) 0.1063(2) 0.5534(3) 0.0464(14) Uani d . . . 1 . .
C C6 0.4733(8) 0.3214(3) 0.7933(4) 0.0320(15) Uani d . . . 1 . .
O O6 0.5544(6) 0.2470(2) 0.4943(3) 0.0323(10) Uani d . . . 1 . .
C C7 0.5292(8) 0.3576(3) 0.7256(4) 0.0308(15) Uani d . . . 1 . .
C C8 0.5942(8) 0.4451(3) 0.6568(4) 0.0302(14) Uani d U . . 1 . .
C C9 0.6264(9) 0.5051(3) 0.6310(4) 0.0323(15) Uani d U . . 1 . .
H H9 0.606075 0.542451 0.660102 0.039 Uiso calc U . R 1 . .
C C10 0.6933(9) 0.5090(3) 0.5567(4) 0.0298(14) Uani d . . . 1 . .
C C19 0.6262(8) 0.3842(3) 0.6184(4) 0.0244(12) Uani d U . . 1 . .
C C18 0.6965(9) 0.3881(3) 0.5477(4) 0.0306(14) Uani d U . . 1 . .
H H18 0.721172 0.35 0.521472 0.037 Uiso calc U . R 1 . .
C C17 0.7305(8) 0.4501(3) 0.5156(4) 0.0273(13) Uani d . . . 1 . .
C C16 0.8314(8) 0.5120(3) 0.4207(4) 0.0316(15) Uani d . . . 1 . .
C C15 0.9089(8) 0.5176(4) 0.3495(5) 0.0358(16) Uani d . . . 1 . .
H H15 0.937113 0.480087 0.323218 0.043 Uiso calc U . R 1 . .
C C14 0.9409(9) 0.5778(4) 0.3206(5) 0.0380(17) Uani d . . . 1 . .
H H14 0.994106 0.581217 0.2758 0.046 Uiso calc U . R 1 . .
C C11 0.7914(8) 0.5706(3) 0.4593(4) 0.0304(14) Uani d . . . 1 . .
C C12 0.8239(9) 0.6320(4) 0.4252(5) 0.0380(17) Uani d . . . 1 . .
H H12 0.796293 0.670489 0.449645 0.046 Uiso calc U . R 1 . .
C C20 0.6123(10) 0.0723(4) 0.6191(6) 0.044(2) Uani d . . . 1 . .
C C1S 0.3325(13) 0.6130(5) 0.7820(6) 0.061(2) Uani d . . . 1 . .
H H01A 0.299964 0.596975 0.725075 0.091 Uiso calc U . R 1 . .
H H01B 0.437608 0.631115 0.78929 0.091 Uiso calc U . R 1 . .
H H01C 0.259886 0.646354 0.792365 0.091 Uiso calc U . R 1 . .
O O1S 0.4765(9) 0.5086(3) 0.8480(4) 0.0647(19) Uani d . . . 1 . .
C C21 0.6212(12) -0.0006(4) 0.6148(7) 0.058(2) Uani d . . . 1 . .
H H00A 0.519399 -0.017718 0.587959 0.087 Uiso calc U . R 1 . .
H H00B 0.650782 -0.018055 0.671213 0.087 Uiso calc U . R 1 . .
H H00D 0.699351 -0.012849 0.582611 0.087 Uiso calc U . R 1 . .
C C22 0.4758(13) 0.3130(5) 0.3565(6) 0.058(3) Uani d . . . 1 . .
H H01D 0.57342 0.298178 0.342469 0.087 Uiso calc U . R 1 . .
H H01E 0.493539 0.354096 0.385975 0.087 Uiso calc U . R 1 . .
H H01F 0.397043 0.318595 0.305455 0.087 Uiso calc U . R 1 . .
C C23 0.4134(11) 0.1826(4) 0.3606(6) 0.054(2) Uani d . . . 1 . .
H H00E 0.332681 0.185238 0.309898 0.081 Uiso calc U . R 1 . .
H H00F 0.394245 0.145012 0.393013 0.081 Uiso calc U . R 1 . .
H H00G 0.515821 0.178621 0.34579 0.081 Uiso calc U . R 1 . .
C C2S 0.3900(15) 0.5933(6) 0.9491(6) 0.077(4) Uani d . . . 1 . .
H H01G 0.482536 0.618993 0.946374 0.115 Uiso calc U . R 1 . .
H H01H 0.414024 0.563704 0.996341 0.115 Uiso calc U . R 1 . .
H H01I 0.304722 0.621776 0.956315 0.115 Uiso calc U . R 1 . .
C C13 0.8940(9) 0.6351(4) 0.3581(5) 0.0406(18) Uani d . . . 1 . .
H H13 0.912169 0.675804 0.335757 0.049 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
U1 O2 . 1.760(6) ?
U1 O3 . 1.772(6) ?
U1 O1 . 2.213(5) ?
U1 O6 . 2.333(5) ?
U1 O4 . 2.430(5) ?
U1 O5 . 2.468(5) ?
U1 N4 . 2.562(6) ?
U1 C20 . 2.819(8) ?
S1S O1S . 1.495(7) ?
S1S C1S . 1.761(10) ?
S1S C2S . 1.769(10) ?
S1 O6 . 1.534(5) ?
S1 C22 . 1.765(9) ?
S1 C23 . 1.778(8) ?
N1 C7 . 1.350(9) ?
N1 C8 . 1.399(9) ?
N1 H1 . 0.86 ?
O1 C1 . 1.323(9) ?
C1 C2 . 1.403(10) ?
C1 C6 . 1.411(10) ?
N2 C10 . 1.351(8) ?
N2 C11 . 1.353(9) ?
C2 C3 . 1.366(11) ?
C2 H2 . 0.93 ?
N3 C16 . 1.345(9) ?
N3 C17 . 1.346(9) ?
C3 C4 . 1.380(12) ?
C3 H3 . 0.93 ?
O4 C20 . 1.259(10) ?
N4 C7 . 1.308(9) ?
N4 C19 . 1.356(9) ?
C4 C5 . 1.385(11) ?
C4 H4 . 0.93 ?
C5 C6 . 1.404(10) ?
C5 H5 . 0.93 ?
O5 C20 . 1.248(10) ?
C6 C7 . 1.476(10) ?
C8 C9 . 1.340(10) ?
C8 C19 . 1.438(9) ?
C9 C10 . 1.429(10) ?
C9 H9 . 0.93 ?
C10 C17 . 1.439(9) ?
C19 C18 . 1.393(9) ?
C18 C17 . 1.419(9) ?
C18 H18 . 0.93 ?
C16 C11 . 1.422(10) ?
C16 C15 . 1.441(10) ?
C15 C14 . 1.362(10) ?
C15 H15 . 0.93 ?
C14 C13 . 1.412(11) ?
C14 H14 . 0.93 ?
C11 C12 . 1.420(9) ?
C12 C13 . 1.340(11) ?
C12 H12 . 0.93 ?
C20 C21 . 1.491(11) ?
C1S H01A . 0.96 ?
C1S H01B . 0.96 ?
C1S H01C . 0.96 ?
C21 H00A . 0.96 ?
C21 H00B . 0.96 ?
C21 H00D . 0.96 ?
C22 H01D . 0.96 ?
C22 H01E . 0.96 ?
C22 H01F . 0.96 ?
C23 H00E . 0.96 ?
C23 H00F . 0.96 ?
C23 H00G . 0.96 ?
C2S H01G . 0.96 ?
C2S H01H . 0.96 ?
C2S H01I . 0.96 ?
C13 H13 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 U1 O3 . . 178.0(2) ?
O2 U1 O1 . . 90.8(2) ?
O3 U1 O1 . . 90.0(2) ?
O2 U1 O6 . . 90.4(2) ?
O3 U1 O6 . . 87.9(2) ?
O1 U1 O6 . . 151.37(17) ?
O2 U1 O4 . . 90.6(2) ?
O3 U1 O4 . . 91.5(2) ?
O1 U1 O4 . . 77.99(19) ?
O6 U1 O4 . . 130.60(18) ?
O2 U1 O5 . . 90.9(2) ?
O3 U1 O5 . . 90.0(2) ?
O1 U1 O5 . . 130.64(17) ?
O6 U1 O5 . . 77.93(17) ?
O4 U1 O5 . . 52.67(19) ?
O2 U1 N4 . . 90.1(2) ?
O3 U1 N4 . . 88.4(2) ?
O1 U1 N4 . . 70.34(19) ?
O6 U1 N4 . . 81.05(18) ?
O4 U1 N4 . . 148.3(2) ?
O5 U1 N4 . . 158.96(19) ?
O2 U1 C20 . . 90.3(2) ?
O3 U1 C20 . . 91.3(2) ?
O1 U1 C20 . . 104.4(2) ?
O6 U1 C20 . . 104.2(2) ?
O4 U1 C20 . . 26.4(2) ?
O5 U1 C20 . . 26.2(2) ?
N4 U1 C20 . . 174.8(2) ?
O1S S1S C1S . . 104.7(5) ?
O1S S1S C2S . . 104.4(5) ?
C1S S1S C2S . . 98.1(5) ?
O6 S1 C22 . . 101.9(4) ?
O6 S1 C23 . . 103.4(3) ?
C22 S1 C23 . . 100.3(5) ?
C7 N1 C8 . . 108.5(6) ?
C7 N1 H1 . . 125.8 ?
C8 N1 H1 . . 125.8 ?
C1 O1 U1 . . 129.9(5) ?
O1 C1 C2 . . 120.0(7) ?
O1 C1 C6 . . 121.2(6) ?
C2 C1 C6 . . 118.8(7) ?
C10 N2 C11 . . 116.4(6) ?
C3 C2 C1 . . 120.6(7) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C16 N3 C17 . . 116.1(6) ?
C2 C3 C4 . . 121.0(7) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C20 O4 U1 . . 94.3(5) ?
C7 N4 C19 . . 106.3(6) ?
C7 N4 U1 . . 123.6(5) ?
C19 N4 U1 . . 130.1(4) ?
C3 C4 C5 . . 120.1(7) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.9(7) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C20 O5 U1 . . 92.8(5) ?
C5 C6 C1 . . 119.5(6) ?
C5 C6 C7 . . 120.1(6) ?
C1 C6 C7 . . 120.1(6) ?
S1 O6 U1 . . 135.0(3) ?
N4 C7 N1 . . 112.6(6) ?
N4 C7 C6 . . 127.1(6) ?
N1 C7 C6 . . 120.4(6) ?
C9 C8 N1 . . 131.8(6) ?
C9 C8 C19 . . 126.0(7) ?
N1 C8 C19 . . 102.1(6) ?
C8 C9 C10 . . 116.9(6) ?
C8 C9 H9 . . 121.5 ?
C10 C9 H9 . . 121.5 ?
N2 C10 C9 . . 118.2(6) ?
N2 C10 C17 . . 121.7(6) ?
C9 C10 C17 . . 120.1(6) ?
N4 C19 C18 . . 132.4(6) ?
N4 C19 C8 . . 110.6(6) ?
C18 C19 C8 . . 116.9(6) ?
C19 C18 C17 . . 120.2(6) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
N3 C17 C18 . . 118.6(6) ?
N3 C17 C10 . . 121.6(6) ?
C18 C17 C10 . . 119.8(6) ?
N3 C16 C11 . . 122.8(6) ?
N3 C16 C15 . . 119.0(6) ?
C11 C16 C15 . . 118.2(6) ?
C14 C15 C16 . . 120.0(7) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C15 C14 C13 . . 120.5(7) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
N2 C11 C12 . . 119.3(6) ?
N2 C11 C16 . . 121.3(6) ?
C12 C11 C16 . . 119.4(7) ?
C13 C12 C11 . . 120.6(7) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
O5 C20 O4 . . 120.2(7) ?
O5 C20 C21 . . 121.2(8) ?
O4 C20 C21 . . 118.5(8) ?
O5 C20 U1 . . 61.0(4) ?
O4 C20 U1 . . 59.2(4) ?
C21 C20 U1 . . 177.8(7) ?
S1S C1S H01A . . 109.5 ?
S1S C1S H01B . . 109.5 ?
H01A C1S H01B . . 109.5 ?
S1S C1S H01C . . 109.5 ?
H01A C1S H01C . . 109.5 ?
H01B C1S H01C . . 109.5 ?
C20 C21 H00A . . 109.5 ?
C20 C21 H00B . . 109.5 ?
H00A C21 H00B . . 109.5 ?
C20 C21 H00D . . 109.5 ?
H00A C21 H00D . . 109.5 ?
H00B C21 H00D . . 109.5 ?
S1 C22 H01D . . 109.5 ?
S1 C22 H01E . . 109.5 ?
H01D C22 H01E . . 109.5 ?
S1 C22 H01F . . 109.5 ?
H01D C22 H01F . . 109.5 ?
H01E C22 H01F . . 109.5 ?
S1 C23 H00E . . 109.5 ?
S1 C23 H00F . . 109.5 ?
H00E C23 H00F . . 109.5 ?
S1 C23 H00G . . 109.5 ?
H00E C23 H00G . . 109.5 ?
H00F C23 H00G . . 109.5 ?
S1S C2S H01G . . 109.5 ?
S1S C2S H01H . . 109.5 ?
H01G C2S H01H . . 109.5 ?
S1S C2S H01I . . 109.5 ?
H01G C2S H01I . . 109.5 ?
H01H C2S H01I . . 109.5 ?
C12 C13 C14 . . 121.2(7) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
U1 O1 C1 C2 . . . . 128.9(6) ?
U1 O1 C1 C6 . . . . -54.1(9) ?
O1 C1 C2 C3 . . . . 174.7(7) ?
C6 C1 C2 C3 . . . . -2.3(12) ?
C1 C2 C3 C4 . . . . 3.4(13) ?
C2 C3 C4 C5 . . . . -2.2(13) ?
C3 C4 C5 C6 . . . . -0.1(12) ?
C4 C5 C6 C1 . . . . 1.1(11) ?
C4 C5 C6 C7 . . . . -173.0(7) ?
O1 C1 C6 C5 . . . . -176.9(7) ?
C2 C1 C6 C5 . . . . 0.1(11) ?
O1 C1 C6 C7 . . . . -2.9(10) ?
C2 C1 C6 C7 . . . . 174.1(7) ?
C22 S1 O6 U1 . . . . 159.1(5) ?
C23 S1 O6 U1 . . . . -97.1(5) ?
C19 N4 C7 N1 . . . . 0.8(8) ?
U1 N4 C7 N1 . . . . -178.5(4) ?
C19 N4 C7 C6 . . . . -177.7(7) ?
U1 N4 C7 C6 . . . . 3.0(10) ?
C8 N1 C7 N4 . . . . -0.7(8) ?
C8 N1 C7 C6 . . . . 178.0(6) ?
C5 C6 C7 N4 . . . . -161.8(7) ?
C1 C6 C7 N4 . . . . 24.2(11) ?
C5 C6 C7 N1 . . . . 19.7(10) ?
C1 C6 C7 N1 . . . . -154.3(7) ?
C7 N1 C8 C9 . . . . -177.2(8) ?
C7 N1 C8 C19 . . . . 0.3(7) ?
N1 C8 C9 C10 . . . . 179.3(7) ?
C19 C8 C9 C10 . . . . 2.4(11) ?
C11 N2 C10 C9 . . . . 177.4(6) ?
C11 N2 C10 C17 . . . . -1.7(10) ?
C8 C9 C10 N2 . . . . 177.8(7) ?
C8 C9 C10 C17 . . . . -3.1(10) ?
C7 N4 C19 C18 . . . . 177.1(7) ?
U1 N4 C19 C18 . . . . -3.7(11) ?
C7 N4 C19 C8 . . . . -0.6(8) ?
U1 N4 C19 C8 . . . . 178.6(4) ?
C9 C8 C19 N4 . . . . 177.9(7) ?
N1 C8 C19 N4 . . . . 0.2(7) ?
C9 C8 C19 C18 . . . . -0.3(10) ?
N1 C8 C19 C18 . . . . -177.9(6) ?
N4 C19 C18 C17 . . . . -178.9(7) ?
C8 C19 C18 C17 . . . . -1.2(10) ?
C16 N3 C17 C18 . . . . -179.2(6) ?
C16 N3 C17 C10 . . . . -0.4(9) ?
C19 C18 C17 N3 . . . . 179.3(6) ?
C19 C18 C17 C10 . . . . 0.5(10) ?
N2 C10 C17 N3 . . . . 2.0(10) ?
C9 C10 C17 N3 . . . . -177.1(6) ?
N2 C10 C17 C18 . . . . -179.2(7) ?
C9 C10 C17 C18 . . . . 1.7(10) ?
C17 N3 C16 C11 . . . . -1.4(10) ?
C17 N3 C16 C15 . . . . 178.7(6) ?
N3 C16 C15 C14 . . . . 179.5(7) ?
C11 C16 C15 C14 . . . . -0.4(10) ?
C16 C15 C14 C13 . . . . -2.1(11) ?
C10 N2 C11 C12 . . . . 179.6(6) ?
C10 N2 C11 C16 . . . . -0.1(10) ?
N3 C16 C11 N2 . . . . 1.7(11) ?
C15 C16 C11 N2 . . . . -178.3(6) ?
N3 C16 C11 C12 . . . . -178.0(6) ?
C15 C16 C11 C12 . . . . 2.0(10) ?
N2 C11 C12 C13 . . . . 179.3(7) ?
C16 C11 C12 C13 . . . . -1.1(11) ?
U1 O5 C20 O4 . . . . 2.2(9) ?
U1 O5 C20 C21 . . . . 179.8(8) ?
U1 O4 C20 O5 . . . . -2.2(9) ?
U1 O4 C20 C21 . . . . -179.9(7) ?
C11 C12 C13 C14 . . . . -1.5(11) ?
C15 C14 C13 C12 . . . . 3.1(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1S . 0.86 1.89 2.732(8) 167.2 ?
C18 H18 O6 . 0.93 2.53 3.179(8) 126.9 ?
C1S H01C O3 2_556 0.96 2.37 3.265(11) 155.0 ?
C22 H01F O1 4_565 0.96 2.48 3.161(11) 127.9 ?
C23 H00E O1 4_565 0.96 2.52 3.191(10) 127.0 ?
C2S H01I O3 2_556 0.96 2.55 3.356(12) 141.3 ?



# start Validation Reply Form
_vrf_PLAT971_bam115b_JN          
;
PROBLEM: Check Calcd Resid. Dens.  0.88A   From O2              3.61 eA-3  
RESPONSE: This is the result of unresolved twinning. Data was
collected using an older detector with poorer resolution.Attempts
to resolve the twinning did not result in convergence. 
;
_vrf_PLAT973_bam115b_JN          
;
PROBLEM: Check Calcd Positive Resid. Density on        U1       1.84 eA-3  
RESPONSE: Structure contains a heavy atom and has some
unresolved twinning.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_Hiti070117_0m
_database_code_depnum_ccdc_archive 'CCDC 2067348'
loop_
_audit_author_name
_audit_author_address
'John Gorden'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_audit_creation_date             2017-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H12 N4 O'
_chemical_formula_sum            'C19 H12 N4 O'
_chemical_formula_weight         312.33
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.6597(6)
_cell_length_b                   30.064(3)
_cell_length_c                   7.2617(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.293(2)
_cell_angle_gamma                90
_cell_volume                     1380.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    180(2)
_diffrn_ambient_temperature      180(2)
_cell_measurement_theta_max      27.467
_cell_measurement_theta_min      2.710
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0671 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.8880. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5027
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             648.2625
_exptl_crystal_preparation       'Single crystal cut to size'
_exptl_crystal_recrystallization_method 
'Grown from a solution of ligand in DMSO layered with a UO2 solution (EtOH)'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13927
_diffrn_reflns_theta_full        27.4803
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.71
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -8
_reflns_limit_k_max              38
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -4
_reflns_number_gt                2482
_reflns_number_total             3173
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.4138
_refine_diff_density_min         -0.3338
_refine_diff_density_rms         0.0882
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             7.5161
_refine_ls_goodness_of_fit_ref   1.0665
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.0665
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+1.0683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1332
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C15(H15), C12(H12), C2(H2), C5(H5), C3(H3), C4(H4),
 C14(H14), C13(H13), N1(H1a)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     direct
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.126
;
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_refinement_flags_posn
N2 N -0.4687(3) -0.10978(6) 0.0395(2) 0.0212(4) Uani 1.000000 .
C10 C -0.2987(3) -0.08296(6) 0.0990(3) 0.0183(4) Uani 1.000000 .
N3 N -0.0604(3) -0.14021(5) 0.0500(2) 0.0202(4) Uani 1.000000 .
C17 C -0.0898(3) -0.09840(6) 0.1035(3) 0.0183(4) Uani 1.000000 .
C16 C -0.2314(3) -0.16655(6) -0.0096(3) 0.0202(4) Uani 1.000000 .
C6 C 0.1733(3) 0.08482(6) 0.3842(3) 0.0181(4) Uani 1.000000 .
C8 C -0.1524(3) -0.01251(6) 0.2144(3) 0.0187(4) Uani 1.000000 .
C11 C -0.4373(3) -0.15127(7) -0.0140(3) 0.0205(4) Uani 1.000000 .
C18 C 0.0868(3) -0.06940(6) 0.1630(3) 0.0190(4) Uani 1.000000 .
H18 H 0.2206(3) -0.07887(6) 0.1654(3) 0.0228(5) Uiso 1.000000 R
C19 C 0.0544(3) -0.02705(6) 0.2168(3) 0.0179(4) Uani 1.000000 .
C9 C -0.3263(3) -0.03912(6) 0.1575(3) 0.0199(4) Uani 1.000000 .
H9 H -0.4582(3) -0.02887(6) 0.1571(3) 0.0238(5) Uiso 1.000000 R
C15 C -0.2101(3) -0.21066(7) -0.0730(3) 0.0248(5) Uani 1.000000 .
H15 H -0.0778(3) -0.22097(7) -0.0714(3) 0.0298(5) Uiso 1.000000 R
C1 C 0.3918(3) 0.09194(6) 0.4238(3) 0.0188(4) Uani 1.000000 .
C12 C -0.6124(3) -0.18115(7) -0.0771(3) 0.0264(5) Uani 1.000000 .
H12 H -0.7459(3) -0.17208(7) -0.0771(3) 0.0317(6) Uiso 1.000000 R
C2 C 0.4797(3) 0.13293(7) 0.4971(3) 0.0236(4) Uani 1.000000 .
H2 H 0.6244(3) 0.13754(7) 0.5259(3) 0.0283(5) Uiso 1.000000 R
C5 C 0.0486(3) 0.11968(7) 0.4146(3) 0.0236(4) Uani 1.000000 .
H5 H -0.0961(3) 0.11545(7) 0.3872(3) 0.0283(5) Uiso 1.000000 R
C7 C 0.0834(3) 0.04164(6) 0.3138(3) 0.0174(4) Uani 1.000000 .
C3 C 0.3531(3) 0.16650(7) 0.5267(3) 0.0264(5) Uani 1.000000 .
H3 H 0.4127(3) 0.19372(7) 0.5756(3) 0.0317(6) Uiso 1.000000 R
C4 C 0.1360(4) 0.16001(7) 0.4840(3) 0.0282(5) Uani 1.000000 .
H4 H 0.0507(4) 0.18297(7) 0.5026(3) 0.0339(6) Uiso 1.000000 R
C14 C -0.3809(3) -0.23770(7) -0.1358(3) 0.0282(5) Uani 1.000000 .
H14 H -0.3652(3) -0.26627(7) -0.1785(3) 0.0338(6) Uiso 1.000000 R
C13 C -0.5840(3) -0.22275(7) -0.1369(3) 0.0290(5) Uani 1.000000 .
H13 H -0.6993(3) -0.24183(7) -0.1794(3) 0.0348(6) Uiso 1.000000 R
O1 O 0.5211(2) 0.05982(5) 0.3953(2) 0.0258(3) Uani 1.000000 .
H1 H 0.4528(8) 0.0370(3) 0.358(4) 0.0387(5) Uiso 1.000000 GR
N1 N -0.1249(2) 0.03098(5) 0.2782(2) 0.0203(4) Uani 1.000000 .
H1a H -0.2216(2) 0.04829(5) 0.2929(2) 0.0243(4) Uiso 1.000000 R
N4 N 0.1956(2) 0.00816(5) 0.2797(2) 0.0190(4) Uani 1.000000 .


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
N2 C10 1.346(2) . ?
N2 C11 1.343(3) . ?
C10 C17 1.457(3) . ?
C10 C9 1.415(3) . ?
N3 C17 1.348(2) . ?
N3 C16 1.342(2) . ?
C17 C18 1.418(3) . ?
C16 C11 1.437(3) . ?
C16 C15 1.426(3) . ?
C6 C1 1.408(3) . ?
C6 C5 1.397(3) . ?
C6 C7 1.453(3) . ?
C8 C19 1.440(3) . ?
C8 C9 1.361(3) . ?
C8 N1 1.380(2) . ?
C11 C12 1.429(3) . ?
C18 C19 1.368(3) . ?
C19 N4 1.394(2) . ?
C15 C14 1.356(3) . ?
C1 C2 1.396(3) . ?
C1 O1 1.352(2) . ?
C12 C13 1.356(3) . ?
C2 C3 1.375(3) . ?
C5 C4 1.371(3) . ?
C7 N1 1.367(2) . ?
C7 N4 1.322(2) . ?
C3 C4 1.394(3) . ?
C14 C13 1.423(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N2 C10 117.24(17) . . ?
C17 C10 N2 121.17(17) . . ?
C9 C10 N2 118.62(17) . . ?
C9 C10 C17 120.21(17) . . ?
C16 N3 C17 117.24(17) . . ?
N3 C17 C10 120.95(17) . . ?
C18 C17 C10 120.38(17) . . ?
C18 C17 N3 118.67(17) . . ?
C11 C16 N3 121.73(18) . . ?
C15 C16 N3 119.49(18) . . ?
C15 C16 C11 118.77(18) . . ?
C5 C6 C1 118.74(18) . . ?
C7 C6 C1 119.51(17) . . ?
C7 C6 C5 121.75(17) . . ?
C9 C8 C19 123.03(18) . . ?
N1 C8 C19 104.96(16) . . ?
N1 C8 C9 132.01(18) . . ?
C16 C11 N2 121.66(18) . . ?
C12 C11 N2 119.44(18) . . ?
C12 C11 C16 118.90(18) . . ?
C19 C18 C17 117.97(17) . . ?
C18 C19 C8 120.99(17) . . ?
N4 C19 C8 108.50(16) . . ?
N4 C19 C18 130.52(17) . . ?
C8 C9 C10 117.41(17) . . ?
C14 C15 C16 120.5(2) . . ?
C2 C1 C6 119.67(18) . . ?
O1 C1 C6 121.80(17) . . ?
O1 C1 C2 118.53(17) . . ?
C13 C12 C11 120.1(2) . . ?
C3 C2 C1 120.22(19) . . ?
C4 C5 C6 121.15(19) . . ?
N1 C7 C6 123.86(17) . . ?
N4 C7 C6 123.47(17) . . ?
N4 C7 N1 112.66(17) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 119.75(19) . . ?
C13 C14 C15 120.6(2) . . ?
C14 C13 C12 121.1(2) . . ?
C7 N1 C8 107.78(16) . . ?
C7 N4 C19 106.10(16) . . ?


_olex2_exptl_crystal_mounting_method 
'Mounted on a thin glass fiber using Paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'
