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

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

data_js1259_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1982444'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2020-02-06 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O4 [+ solvent]'
_chemical_formula_sum            'C23 H21 N3 O4 [+ solvent]'
_chemical_formula_weight         403.43

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

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.260(5)
_cell_length_b                   7.7137(14)
_cell_length_c                   20.218(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.209(3)
_cell_angle_gamma                90
_cell_volume                     4307.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5334
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28555
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         33.111
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7823
_reflns_number_gt                4323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.139 0.250 131 29 ' '
2 0.000 0.139 0.750 132 29 ' '
3 0.500 0.356 0.250 131 29 ' '
4 0.500 -0.357 0.750 132 29 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
'The unit cell contains one acetone molecule which has been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.5000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7823
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.30000(3) 0.94028(13) 0.51586(6) 0.0563(3) Uani 1 1 d . . . . .
O2 O 0.43346(3) 0.45296(14) 0.48490(6) 0.0575(3) Uani 1 1 d . . . . .
O3 O 0.29738(4) 0.35305(14) 0.38977(6) 0.0717(3) Uani 1 1 d . . . . .
O4 O 0.26449(4) 0.61204(14) 0.36493(5) 0.0596(3) Uani 1 1 d . . . . .
N1 N 0.33574(4) 1.01761(17) 0.42915(7) 0.0554(3) Uani 1 1 d . . . . .
H1N1 H 0.3259(7) 1.129(2) 0.4234(9) 0.076(5) Uiso 1 1 d . . . . .
N2 N 0.47525(4) 0.69545(17) 0.52829(7) 0.0543(3) Uani 1 1 d . . . . .
H1N2 H 0.5049(7) 0.657(2) 0.5218(8) 0.073(5) Uiso 1 1 d . . . . .
N3 N 0.37329(4) 0.57076(14) 0.57536(6) 0.0442(3) Uani 1 1 d . . . . .
C1 C 0.32520(4) 0.90701(16) 0.47544(7) 0.0433(3) Uani 1 1 d . . . . .
C2 C 0.35836(5) 0.9326(2) 0.38355(8) 0.0532(4) Uani 1 1 d . . . . .
C3 C 0.37002(6) 1.0025(3) 0.32602(9) 0.0757(5) Uani 1 1 d . . . . .
H3 H 0.365192 1.119339 0.315408 0.091 Uiso 1 1 calc R U . . .
C4 C 0.38893(7) 0.8923(4) 0.28550(10) 0.0907(7) Uani 1 1 d . . . . .
H4 H 0.397280 0.935452 0.246568 0.109 Uiso 1 1 calc R U . . .
C5 C 0.39592(6) 0.7201(4) 0.30059(9) 0.0806(6) Uani 1 1 d . . . . .
H5 H 0.408127 0.648314 0.271225 0.097 Uiso 1 1 calc R U . . .
C6 C 0.38493(5) 0.6496(2) 0.35999(8) 0.0598(4) Uani 1 1 d . . . . .
H6 H 0.390043 0.532755 0.370526 0.072 Uiso 1 1 calc R U . . .
C7 C 0.36632(4) 0.75981(18) 0.40195(7) 0.0451(3) Uani 1 1 d . . . . .
C8 C 0.34952(4) 0.73113(15) 0.46766(6) 0.0377(3) Uani 1 1 d . . . . .
C9 C 0.39254(4) 0.69387(17) 0.53283(6) 0.0406(3) Uani 1 1 d . . . . .
C10 C 0.43531(4) 0.59606(19) 0.51096(7) 0.0458(3) Uani 1 1 d . . . . .
C11 C 0.46659(4) 0.8489(2) 0.56024(7) 0.0506(3) Uani 1 1 d . . . . .
C12 C 0.49868(5) 0.9811(2) 0.58269(9) 0.0680(4) Uani 1 1 d . . . . .
H12 H 0.530801 0.973976 0.578664 0.082 Uiso 1 1 calc R U . . .
C13 C 0.48179(6) 1.1242(3) 0.61132(9) 0.0734(5) Uani 1 1 d . . . . .
H13 H 0.502755 1.215657 0.626271 0.088 Uiso 1 1 calc R U . . .
C14 C 0.43448(6) 1.1341(2) 0.61819(9) 0.0658(4) Uani 1 1 d . . . . .
H14 H 0.423817 1.231972 0.637618 0.079 Uiso 1 1 calc R U . . .
C15 C 0.40249(5) 0.9988(2) 0.59625(7) 0.0545(3) Uani 1 1 d . . . . .
H15 H 0.370681 1.005165 0.601743 0.065 Uiso 1 1 calc R U . . .
C16 C 0.41813(4) 0.85483(18) 0.56627(7) 0.0451(3) Uani 1 1 d . . . . .
C17 C 0.34628(5) 0.6390(2) 0.62486(8) 0.0582(4) Uani 1 1 d . . . . .
H17A H 0.328102 0.741929 0.607501 0.070 Uiso 1 1 calc R U . . .
H17B H 0.368114 0.667453 0.667296 0.070 Uiso 1 1 calc R U . . .
C18 C 0.31302(7) 0.4946(3) 0.63417(10) 0.0806(5) Uani 1 1 d . . . . .
H18A H 0.282022 0.540691 0.639104 0.097 Uiso 1 1 calc R U . . .
H18B H 0.326814 0.428587 0.674473 0.097 Uiso 1 1 calc R U . . .
C19 C 0.30649(5) 0.3796(2) 0.57209(8) 0.0564(4) Uani 1 1 d . . . . .
H19A H 0.272984 0.379448 0.547825 0.068 Uiso 1 1 calc R U . . .
H19B H 0.316174 0.261431 0.584692 0.068 Uiso 1 1 calc R U . . .
C20 C 0.33921(4) 0.45870(17) 0.52871(7) 0.0443(3) Uani 1 1 d . . . . .
H20 H 0.356640 0.367943 0.509700 0.053 Uiso 1 1 calc R U . . .
C21 C 0.31316(4) 0.58207(16) 0.47274(7) 0.0404(3) Uani 1 1 d . . . . .
H21 H 0.286259 0.634405 0.489300 0.048 Uiso 1 1 calc R U . . .
C22 C 0.29183(4) 0.49999(18) 0.40610(7) 0.0471(3) Uani 1 1 d . . . . .
C23 C 0.24203(9) 0.5498(3) 0.29875(9) 0.0937(7) Uani 1 1 d . . . . .
H23A H 0.266434 0.506369 0.276502 0.140 Uiso 1 1 calc R U . . .
H23B H 0.224881 0.643019 0.272683 0.140 Uiso 1 1 calc R U . . .
H23C H 0.219760 0.458442 0.302858 0.140 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2194(16) . ?
O2 C10 1.2194(17) . ?
O3 C22 1.2001(17) . ?
O4 C22 1.3285(16) . ?
O4 C23 1.437(2) . ?
N1 C1 1.3455(18) . ?
N1 C2 1.392(2) . ?
N1 H1N1 0.900(18) . ?
N2 C10 1.3482(18) . ?
N2 C11 1.3950(19) . ?
N2 H1N2 0.923(18) . ?
N3 C9 1.4613(16) . ?
N3 C20 1.4765(18) . ?
N3 C17 1.4780(18) . ?
C1 C8 1.5439(17) . ?
C2 C3 1.383(2) . ?
C2 C7 1.390(2) . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5186(18) . ?
C8 C21 1.5600(16) . ?
C8 C9 1.6183(17) . ?
C9 C16 1.5216(19) . ?
C9 C10 1.5657(16) . ?
C11 C12 1.376(2) . ?
C11 C16 1.4010(17) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9300 . ?
C17 C18 1.495(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.516(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.5296(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.5414(17) . ?
C20 H20 0.9800 . ?
C21 C22 1.4953(19) . ?
C21 H21 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C22 O4 C23 116.74(13) . . ?
C1 N1 C2 111.25(12) . . ?
C1 N1 H1N1 125.8(11) . . ?
C2 N1 H1N1 122.3(11) . . ?
C10 N2 C11 112.56(10) . . ?
C10 N2 H1N2 121.1(11) . . ?
C11 N2 H1N2 126.2(11) . . ?
C9 N3 C20 106.15(10) . . ?
C9 N3 C17 118.48(11) . . ?
C20 N3 C17 106.30(10) . . ?
O1 C1 N1 125.40(13) . . ?
O1 C1 C8 126.08(12) . . ?
N1 C1 C8 108.51(11) . . ?
C3 C2 C7 123.02(17) . . ?
C3 C2 N1 126.72(16) . . ?
C7 C2 N1 110.21(12) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.81(18) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 121.12(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 117.76(17) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 119.17(14) . . ?
C6 C7 C8 132.65(13) . . ?
C2 C7 C8 108.13(12) . . ?
C7 C8 C1 100.92(10) . . ?
C7 C8 C21 119.81(10) . . ?
C1 C8 C21 109.10(9) . . ?
C7 C8 C9 114.72(8) . . ?
C1 C8 C9 110.32(10) . . ?
C21 C8 C9 101.97(9) . . ?
N3 C9 C16 118.02(11) . . ?
N3 C9 C10 104.99(10) . . ?
C16 C9 C10 101.30(9) . . ?
N3 C9 C8 106.59(9) . . ?
C16 C9 C8 114.93(10) . . ?
C10 C9 C8 110.34(10) . . ?
O2 C10 N2 125.74(11) . . ?
O2 C10 C9 126.37(11) . . ?
N2 C10 C9 107.85(12) . . ?
C12 C11 N2 127.84(12) . . ?
C12 C11 C16 122.38(14) . . ?
N2 C11 C16 109.77(12) . . ?
C11 C12 C13 117.99(14) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 121.19(16) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.41(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.76(14) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 118.26(13) . . ?
C15 C16 C9 133.21(11) . . ?
C11 C16 C9 108.44(11) . . ?
N3 C17 C18 104.37(14) . . ?
N3 C17 H17A 110.9 . . ?
C18 C17 H17A 110.9 . . ?
N3 C17 H17B 110.9 . . ?
C18 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 C19 107.56(13) . . ?
C17 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
C17 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 C20 104.99(13) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N3 C20 C19 105.01(11) . . ?
N3 C20 C21 104.67(10) . . ?
C19 C20 C21 114.48(10) . . ?
N3 C20 H20 110.8 . . ?
C19 C20 H20 110.8 . . ?
C21 C20 H20 110.8 . . ?
C22 C21 C20 116.04(11) . . ?
C22 C21 C8 113.48(10) . . ?
C20 C21 C8 106.52(9) . . ?
C22 C21 H21 106.8 . . ?
C20 C21 H21 106.8 . . ?
C8 C21 H21 106.8 . . ?
O3 C22 O4 122.32(14) . . ?
O3 C22 C21 126.62(12) . . ?
O4 C22 C21 111.05(11) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_js1266_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1982445'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2020-02-06 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O4, H2 O'
_chemical_formula_sum            'C23 H23 N3 O5'
_chemical_formula_weight         421.44

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0958(6)
_cell_length_b                   15.2107(11)
_cell_length_c                   14.0883(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.6250(10)
_cell_angle_gamma                90
_cell_volume                     1947.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5877
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23822
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         30.659
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5989
_reflns_number_gt                4705
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²+0.3778P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5989
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.89483(10) 0.35175(6) 0.35988(6) 0.01909(19) Uani 1 1 d . . . . .
O2 O 0.47628(10) 0.11378(6) 0.40680(6) 0.01668(18) Uani 1 1 d . . . . .
O3 O 1.04517(9) 0.17005(6) 0.36162(6) 0.01769(19) Uani 1 1 d . . . . .
O4 O 1.00021(10) 0.10357(6) 0.50022(6) 0.01960(19) Uani 1 1 d . . . . .
N1 N 0.85450(12) 0.29309(7) 0.21094(8) 0.0173(2) Uani 1 1 d . . . . .
H1N1 H 0.910(2) 0.3328(14) 0.1810(15) 0.047(6) Uiso 1 1 d . . . . .
N2 N 0.34280(11) 0.22677(7) 0.33864(7) 0.0153(2) Uani 1 1 d . . . . .
H2N2 H 0.259(2) 0.2021(13) 0.3412(14) 0.037(5) Uiso 1 1 d . . . . .
N3 N 0.62518(11) 0.27205(7) 0.47840(7) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.83940(13) 0.29673(8) 0.30656(9) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.78561(13) 0.21882(8) 0.17026(8) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.78746(14) 0.19061(9) 0.07705(9) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.838491 0.222811 0.031063 0.024 Uiso 1 1 calc R U . . .
C4 C 0.71215(15) 0.11347(9) 0.05260(9) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.710278 0.093209 -0.011232 0.025 Uiso 1 1 calc R U . . .
C5 C 0.63985(14) 0.06591(9) 0.12043(9) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.588566 0.013634 0.102548 0.023 Uiso 1 1 calc R U . . .
C6 C 0.64192(13) 0.09436(8) 0.21498(8) 0.0157(2) Uani 1 1 d . . . . .
H6 H 0.594555 0.060826 0.261572 0.019 Uiso 1 1 calc R U . . .
C7 C 0.71383(12) 0.17202(8) 0.24002(8) 0.0137(2) Uani 1 1 d . . . . .
C8 C 0.73665(12) 0.22014(8) 0.33382(8) 0.0129(2) Uani 1 1 d . . . . .
C9 C 0.59252(12) 0.25892(8) 0.37630(8) 0.0126(2) Uani 1 1 d . . . . .
C10 C 0.46704(12) 0.18914(8) 0.37442(8) 0.0132(2) Uani 1 1 d . . . . .
C11 C 0.36758(13) 0.31413(8) 0.30993(8) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.26473(14) 0.37238(9) 0.27092(9) 0.0201(3) Uani 1 1 d . . . . .
H12 H 0.164352 0.356249 0.260716 0.024 Uiso 1 1 calc R U . . .
C13 C 0.31498(15) 0.45576(9) 0.24728(10) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.247490 0.497522 0.220384 0.028 Uiso 1 1 calc R U . . .
C14 C 0.46228(15) 0.47899(9) 0.26235(10) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.494080 0.536111 0.245321 0.026 Uiso 1 1 calc R U . . .
C15 C 0.56377(14) 0.41901(8) 0.30231(9) 0.0184(2) Uani 1 1 d . . . . .
H15 H 0.664254 0.434935 0.312454 0.022 Uiso 1 1 calc R U . . .
C16 C 0.51566(13) 0.33591(8) 0.32694(8) 0.0144(2) Uani 1 1 d . . . . .
C17 C 0.65441(14) 0.36128(8) 0.51702(9) 0.0182(2) Uani 1 1 d . . . . .
H17A H 0.562338 0.390455 0.534781 0.022 Uiso 1 1 calc R U . . .
H17B H 0.704447 0.398589 0.470805 0.022 Uiso 1 1 calc R U . . .
C18 C 0.75487(15) 0.34207(9) 0.60441(9) 0.0220(3) Uani 1 1 d . . . . .
H18A H 0.697893 0.320923 0.658104 0.026 Uiso 1 1 calc R U . . .
H18B H 0.811876 0.394808 0.624660 0.026 Uiso 1 1 calc R U . . .
C19 C 0.85556(14) 0.26991(9) 0.56823(9) 0.0196(3) Uani 1 1 d . . . . .
H19A H 0.904365 0.236969 0.621467 0.024 Uiso 1 1 calc R U . . .
H19B H 0.931362 0.294500 0.527549 0.024 Uiso 1 1 calc R U . . .
C20 C 0.74603(13) 0.21160(8) 0.51072(8) 0.0149(2) Uani 1 1 d . . . . .
H20 H 0.705689 0.166175 0.553762 0.018 Uiso 1 1 calc R U . . .
C21 C 0.79785(12) 0.16576(8) 0.41918(8) 0.0135(2) Uani 1 1 d . . . . .
H21 H 0.748119 0.107156 0.415369 0.016 Uiso 1 1 calc R U . . .
C22 C 0.96103(13) 0.14862(8) 0.42196(8) 0.0147(2) Uani 1 1 d . . . . .
C23 C 1.15529(14) 0.08443(9) 0.51530(10) 0.0214(3) Uani 1 1 d . . . . .
H23A H 1.186361 0.043913 0.465984 0.032 Uiso 1 1 calc R U . . .
H23B H 1.172706 0.057297 0.577906 0.032 Uiso 1 1 calc R U . . .
H23C H 1.211881 0.139099 0.512245 0.032 Uiso 1 1 calc R U . . .
O5 O 0.48485(12) 0.07096(7) 0.60167(7) 0.0239(2) Uani 1 1 d . . . . .
H1O5 H 0.507(2) 0.0126(16) 0.6061(16) 0.055(6) Uiso 1 1 d . . . . .
H2O5 H 0.495(3) 0.0890(16) 0.5401(18) 0.061(7) Uiso 1 1 d . . . . .


_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 C1 1.2182(15) . ?
O2 C10 1.2352(15) . ?
O3 C22 1.2142(15) . ?
O4 C22 1.3327(15) . ?
O4 C23 1.4465(15) . ?
N1 C1 1.3615(16) . ?
N1 C2 1.4015(16) . ?
N1 H1N1 0.91(2) . ?
N2 C10 1.3441(15) . ?
N2 C11 1.4102(16) . ?
N2 H2N2 0.85(2) . ?
N3 C9 1.4690(15) . ?
N3 C17 1.4818(16) . ?
N3 C20 1.4884(15) . ?
C1 C8 1.5528(16) . ?
C2 C3 1.3824(17) . ?
C2 C7 1.3992(16) . ?
C3 C4 1.3940(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3880(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4000(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3879(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.5167(16) . ?
C8 C21 1.5423(16) . ?
C8 C9 1.5800(16) . ?
C9 C16 1.5162(16) . ?
C9 C10 1.5580(16) . ?
C11 C12 1.3838(17) . ?
C11 C16 1.3971(16) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3925(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3979(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3869(17) . ?
C15 H15 0.9500 . ?
C17 C18 1.5275(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5318(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5367(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5580(16) . ?
C20 H20 1.0000 . ?
C21 C22 1.5056(16) . ?
C21 H21 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 H1O5 0.91(2) . ?
O5 H2O5 0.92(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
C22 O4 C23 116.56(10) . . ?
C1 N1 C2 111.95(10) . . ?
C1 N1 H1N1 121.2(13) . . ?
C2 N1 H1N1 126.7(13) . . ?
C10 N2 C11 111.48(10) . . ?
C10 N2 H2N2 122.3(13) . . ?
C11 N2 H2N2 125.7(13) . . ?
C9 N3 C17 120.59(10) . . ?
C9 N3 C20 109.21(9) . . ?
C17 N3 C20 109.63(9) . . ?
O1 C1 N1 125.48(11) . . ?
O1 C1 C8 126.85(11) . . ?
N1 C1 C8 107.66(10) . . ?
C3 C2 C7 122.39(12) . . ?
C3 C2 N1 127.87(11) . . ?
C7 C2 N1 109.71(10) . . ?
C2 C3 C4 117.95(12) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 120.77(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.52(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.38(11) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 118.96(11) . . ?
C6 C7 C8 132.56(10) . . ?
C2 C7 C8 108.47(10) . . ?
C7 C8 C21 116.78(10) . . ?
C7 C8 C1 101.92(9) . . ?
C21 C8 C1 113.29(9) . . ?
C7 C8 C9 115.30(9) . . ?
C21 C8 C9 100.43(9) . . ?
C1 C8 C9 109.44(9) . . ?
N3 C9 C16 114.35(9) . . ?
N3 C9 C10 102.97(9) . . ?
C16 C9 C10 101.32(9) . . ?
N3 C9 C8 106.71(9) . . ?
C16 C9 C8 119.19(9) . . ?
C10 C9 C8 111.04(9) . . ?
O2 C10 N2 125.14(11) . . ?
O2 C10 C9 126.06(10) . . ?
N2 C10 C9 108.60(10) . . ?
C12 C11 C16 123.04(12) . . ?
C12 C11 N2 127.10(11) . . ?
C16 C11 N2 109.86(10) . . ?
C11 C12 C13 117.03(12) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C14 C13 C12 121.21(12) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.59(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.05(12) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 119.07(11) . . ?
C15 C16 C9 132.41(11) . . ?
C11 C16 C9 108.44(10) . . ?
N3 C17 C18 102.20(10) . . ?
N3 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
N3 C17 H17B 111.3 . . ?
C18 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C17 C18 C19 102.33(10) . . ?
C17 C18 H18A 111.3 . . ?
C19 C18 H18A 111.3 . . ?
C17 C18 H18B 111.3 . . ?
C19 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
C18 C19 C20 101.89(10) . . ?
C18 C19 H19A 111.4 . . ?
C20 C19 H19A 111.4 . . ?
C18 C19 H19B 111.4 . . ?
C20 C19 H19B 111.4 . . ?
H19A C19 H19B 109.3 . . ?
N3 C20 C19 104.87(10) . . ?
N3 C20 C21 105.69(9) . . ?
C19 C20 C21 118.77(10) . . ?
N3 C20 H20 109.0 . . ?
C19 C20 H20 109.0 . . ?
C21 C20 H20 109.0 . . ?
C22 C21 C8 115.68(10) . . ?
C22 C21 C20 113.03(9) . . ?
C8 C21 C20 107.06(9) . . ?
C22 C21 H21 106.9 . . ?
C8 C21 H21 106.9 . . ?
C20 C21 H21 106.9 . . ?
O3 C22 O4 124.33(11) . . ?
O3 C22 C21 125.98(11) . . ?
O4 C22 C21 109.67(10) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H1O5 O5 H2O5 109(2) . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.058

