# 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_5aa
_database_code_depnum_ccdc_archive 'CCDC 1989173'
loop_
_audit_author_name
_audit_author_address
'Gustavo Portalone'
;Sapienza University of Rome
Italy
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37

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                   5.6311(5)
_cell_length_b                   16.1768(13)
_cell_length_c                   18.5883(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.132(7)
_cell_angle_gamma                90
_cell_volume                     1693.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2279
_cell_measurement_theta_min      3.7830
_cell_measurement_theta_max      27.0940

_exptl_crystal_description       tablets
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.91827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            11476
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2959
_reflns_number_gt                1688
_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       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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 0.4773(3) 0.09445(11) 0.44524(10) 0.0539(6) Uani 1 1 d . . . . .
O2 O -0.3433(4) -0.00479(15) 0.19669(12) 0.1003(9) Uani 1 1 d . . . . .
N1 N 0.2600(4) -0.02368(15) 0.43781(12) 0.0474(7) Uani 1 1 d . . . . .
H1 H 0.354(4) -0.0447(16) 0.4741(14) 0.057(9) Uiso 1 1 d . . . . .
N2 N 0.1701(3) 0.08799(13) 0.36475(11) 0.0390(6) Uani 1 1 d . . . . .
C1 C 0.0668(5) -0.06821(17) 0.41224(14) 0.0422(7) Uani 1 1 d . . . . .
C2 C 0.0100(6) -0.14328(19) 0.44398(16) 0.0584(8) Uani 1 1 d . . . . .
H2 H 0.105006 -0.164276 0.480656 0.070(10) Uiso 1 1 calc R . . . .
C3 C -0.1850(6) -0.1864(2) 0.42153(17) 0.0644(9) Uani 1 1 d . . . . .
H3 H -0.221312 -0.237088 0.442371 0.078(10) Uiso 1 1 calc R . . . .
C4 C -0.3275(5) -0.15477(19) 0.36810(17) 0.0594(9) Uani 1 1 d . . . . .
H4 H -0.463095 -0.183288 0.353903 0.062(9) Uiso 1 1 calc R . . . .
C5 C -0.2701(5) -0.08091(17) 0.33545(15) 0.0463(7) Uani 1 1 d . . . . .
H5 H -0.368162 -0.060219 0.299381 0.037(7) Uiso 1 1 calc R . . . .
C6 C -0.0674(4) -0.03649(16) 0.35547(13) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.0109(4) 0.04075(16) 0.32150(13) 0.0368(6) Uani 1 1 d . . . . .
C8 C 0.3141(5) 0.05471(19) 0.41792(14) 0.0417(7) Uani 1 1 d . . . . .
C9 C -0.0371(4) 0.07173(17) 0.25499(13) 0.0421(7) Uani 1 1 d . . . . .
H9 H 0.030366 0.123477 0.247412 0.043(7) Uiso 1 1 calc R . . . .
C10 C -0.1707(5) 0.04183(18) 0.19297(15) 0.0499(8) Uani 1 1 d . . . . .
C11 C -0.1026(4) 0.07616(16) 0.12071(13) 0.0398(7) Uani 1 1 d . . . . .
C12 C -0.2549(5) 0.06228(17) 0.06396(15) 0.0496(8) Uani 1 1 d . . . . .
H12 H -0.394774 0.033046 0.071604 0.077(10) Uiso 1 1 calc R . . . .
C13 C -0.2031(5) 0.09117(18) -0.00424(16) 0.0585(9) Uani 1 1 d . . . . .
H13 H -0.308637 0.081759 -0.041905 0.076(10) Uiso 1 1 calc R . . . .
C14 C 0.0038(5) 0.13367(19) -0.01645(17) 0.0593(9) Uani 1 1 d . . . . .
H14 H 0.038165 0.153680 -0.062155 0.069(10) Uiso 1 1 calc R . . . .
C15 C 0.1587(5) 0.1463(2) 0.03908(16) 0.0620(9) Uani 1 1 d . . . . .
H15 H 0.299947 0.174602 0.030951 0.081(10) Uiso 1 1 calc R . . . .
C16 C 0.1073(5) 0.11749(17) 0.10723(16) 0.0534(8) Uani 1 1 d . . . . .
H16 H 0.215217 0.125998 0.144455 0.064(9) Uiso 1 1 calc R . . . .
C17 C 0.2125(4) 0.17340(17) 0.34548(13) 0.0373(7) Uani 1 1 d . . . . .
C18 C 0.0397(4) 0.23122(17) 0.36072(13) 0.0424(7) Uani 1 1 d . . . . .
H18 H -0.094197 0.215687 0.386588 0.037(7) Uiso 1 1 calc R . . . .
C19 C 0.0642(6) 0.31214(19) 0.33783(15) 0.0551(8) Uani 1 1 d . . . . .
H19 H -0.052537 0.351034 0.348089 0.082(11) Uiso 1 1 calc R . . . .
C20 C 0.2627(6) 0.3343(2) 0.29980(17) 0.0667(10) Uani 1 1 d . . . . .
H20 H 0.278869 0.388400 0.283668 0.074(10) Uiso 1 1 calc R . . . .
C21 C 0.4378(6) 0.2777(2) 0.28520(17) 0.0673(10) Uani 1 1 d . . . . .
H21 H 0.572911 0.294042 0.260241 0.076(9) Uiso 1 1 calc R . . . .
C22 C 0.4138(5) 0.1958(2) 0.30773(15) 0.0532(8) Uani 1 1 d . . . . .
H22 H 0.531004 0.157097 0.297539 0.064(9) Uiso 1 1 calc R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.230(3) . ?
O2 C10 1.232(3) . ?
N1 C8 1.356(3) . ?
N1 C1 1.388(3) . ?
N1 H1 0.92(2) . ?
N2 C8 1.386(3) . ?
N2 C7 1.425(3) . ?
N2 C17 1.447(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.394(3) . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.468(3) . ?
C7 C9 1.361(3) . ?
C9 C10 1.458(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.504(4) . ?
C11 C12 1.376(3) . ?
C11 C16 1.381(3) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 C22 1.383(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.396(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C8 N1 C1 124.7(2) . . ?
C8 N1 H1 114.5(16) . . ?
C1 N1 H1 120.5(16) . . ?
C8 N2 C7 124.1(2) . . ?
C8 N2 C17 116.8(2) . . ?
C7 N2 C17 118.44(19) . . ?
N1 C1 C2 119.3(3) . . ?
N1 C1 C6 119.4(3) . . ?
C2 C1 C6 121.2(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 116.9(3) . . ?
C1 C6 C7 118.4(2) . . ?
C5 C6 C7 124.7(2) . . ?
C9 C7 N2 116.0(2) . . ?
C9 C7 C6 130.2(2) . . ?
N2 C7 C6 113.8(2) . . ?
O1 C8 N1 123.0(2) . . ?
O1 C8 N2 121.8(3) . . ?
N1 C8 N2 115.2(3) . . ?
C7 C9 C10 134.2(3) . . ?
C7 C9 H9 112.9 . . ?
C10 C9 H9 112.9 . . ?
O2 C10 C9 124.4(3) . . ?
O2 C10 C11 118.6(2) . . ?
C9 C10 C11 116.8(2) . . ?
C12 C11 C16 118.2(3) . . ?
C12 C11 C10 117.7(2) . . ?
C16 C11 C10 124.1(2) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C18 C17 C22 120.4(3) . . ?
C18 C17 N2 118.7(2) . . ?
C22 C17 N2 120.8(2) . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.2(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 118.8(3) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

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
C8 N1 C1 C2 -170.8(3) . . . . ?
C8 N1 C1 C6 8.8(4) . . . . ?
N1 C1 C2 C3 177.3(2) . . . . ?
C6 C1 C2 C3 -2.2(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
N1 C1 C6 C5 -175.4(2) . . . . ?
C2 C1 C6 C5 4.2(4) . . . . ?
N1 C1 C6 C7 4.1(3) . . . . ?
C2 C1 C6 C7 -176.3(2) . . . . ?
C4 C5 C6 C1 -3.1(4) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C8 N2 C7 C9 -152.5(2) . . . . ?
C17 N2 C7 C9 17.7(3) . . . . ?
C8 N2 C7 C6 25.0(3) . . . . ?
C17 N2 C7 C6 -164.8(2) . . . . ?
C1 C6 C7 C9 157.8(3) . . . . ?
C5 C6 C7 C9 -22.8(4) . . . . ?
C1 C6 C7 N2 -19.1(3) . . . . ?
C5 C6 C7 N2 160.3(2) . . . . ?
C1 N1 C8 O1 174.9(2) . . . . ?
C1 N1 C8 N2 -4.3(4) . . . . ?
C7 N2 C8 O1 167.1(2) . . . . ?
C17 N2 C8 O1 -3.2(3) . . . . ?
C7 N2 C8 N1 -13.6(3) . . . . ?
C17 N2 C8 N1 176.0(2) . . . . ?
N2 C7 C9 C10 174.6(3) . . . . ?
C6 C7 C9 C10 -2.4(5) . . . . ?
C7 C9 C10 O2 29.5(5) . . . . ?
C7 C9 C10 C11 -155.5(3) . . . . ?
O2 C10 C11 C12 8.3(4) . . . . ?
C9 C10 C11 C12 -167.0(2) . . . . ?
O2 C10 C11 C16 -168.9(3) . . . . ?
C9 C10 C11 C16 15.8(4) . . . . ?
C16 C11 C12 C13 -2.0(4) . . . . ?
C10 C11 C12 C13 -179.3(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C11 -0.7(5) . . . . ?
C12 C11 C16 C15 2.0(4) . . . . ?
C10 C11 C16 C15 179.2(3) . . . . ?
C8 N2 C17 C18 -113.5(2) . . . . ?
C7 N2 C17 C18 75.6(3) . . . . ?
C8 N2 C17 C22 71.3(3) . . . . ?
C7 N2 C17 C22 -99.6(3) . . . . ?
C22 C17 C18 C19 0.7(4) . . . . ?
N2 C17 C18 C19 -174.5(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C19 C20 C21 C22 1.4(5) . . . . ?
C18 C17 C22 C21 -0.3(4) . . . . ?
N2 C17 C22 C21 174.8(2) . . . . ?
C20 C21 C22 C17 -0.7(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
N1 H1 O1 0.92(2) 1.95(3) 2.865(3) 174(2) 3_656 yes

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_5ba
_database_code_depnum_ccdc_archive 'CCDC 1989174'
loop_
_audit_author_name
_audit_author_address
'Gustavo Portalone'
;Sapienza University of Rome
Italy
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O2'
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.7918(6)
_cell_length_b                   8.1770(2)
_cell_length_c                   24.1081(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.785(3)
_cell_angle_gamma                90
_cell_volume                     3715.15(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9173
_cell_measurement_theta_min      3.3980
_cell_measurement_theta_max      28.2770

_exptl_crystal_description       tablets
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.86940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            28750
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.419
_diffrn_reflns_theta_max         25.192
_diffrn_reflns_theta_full        25.192
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6683
_reflns_number_gt                5177
_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       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0471P)²+0.8297P] 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         6683
_refine_ls_number_parameters     497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06939(6) 0.57325(18) 0.56127(5) 0.0640(4) Uani 1 1 d . . . . .
O2 O -0.09142(7) 0.69168(17) 0.76278(6) 0.0647(4) Uani 1 1 d . . . . .
N1 N -0.04622(8) 0.5408(2) 0.55489(6) 0.0532(4) Uani 1 1 d . . . . .
H1 H -0.0547(10) 0.514(2) 0.5213(9) 0.061(6) Uiso 1 1 d . . . . .
N2 N 0.03793(7) 0.59217(17) 0.64427(5) 0.0412(3) Uani 1 1 d . . . . .
C1 C -0.09758(8) 0.5018(2) 0.58110(7) 0.0459(4) Uani 1 1 d . . . . .
C2 C -0.16318(10) 0.4457(3) 0.54657(8) 0.0648(5) Uani 1 1 d . . . . .
H2 H -0.173784 0.444588 0.506234 0.078 Uiso 1 1 calc R U . . .
C3 C -0.21201(11) 0.3923(3) 0.57192(10) 0.0759(6) Uani 1 1 d . . . . .
H3 H -0.256319 0.356665 0.548888 0.091 Uiso 1 1 calc R U . . .
C4 C -0.19551(10) 0.3912(3) 0.63191(9) 0.0672(6) Uani 1 1 d . . . . .
H4 H -0.227984 0.349586 0.649144 0.081 Uiso 1 1 calc R U . . .
C5 C -0.13187(9) 0.4509(2) 0.66618(8) 0.0517(4) Uani 1 1 d . . . . .
H5 H -0.121766 0.450152 0.706468 0.062 Uiso 1 1 calc R U . . .
C6 C -0.08154(8) 0.51315(19) 0.64134(7) 0.0408(4) Uani 1 1 d . . . . .
C7 C -0.01254(8) 0.57962(19) 0.67542(6) 0.0385(4) Uani 1 1 d . . . . .
C8 C 0.02251(9) 0.5680(2) 0.58499(7) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.00889(9) 0.6227(2) 0.73234(7) 0.0474(4) Uani 1 1 d . . . . .
H9 H 0.057130 0.645185 0.747290 0.057 Uiso 1 1 calc R U . . .
C10 C -0.03047(10) 0.6402(2) 0.77470(7) 0.0478(4) Uani 1 1 d . . . . .
C11 C 0.01075(10) 0.6003(2) 0.83617(7) 0.0505(4) Uani 1 1 d . . . . .
C12 C -0.01134(12) 0.6605(2) 0.88177(8) 0.0633(5) Uani 1 1 d . . . . .
H12 H -0.052239 0.723818 0.873706 0.076 Uiso 1 1 calc R U . . .
C13 C 0.02690(16) 0.6272(3) 0.93885(9) 0.0847(7) Uani 1 1 d . . . . .
H13 H 0.011870 0.670384 0.968779 0.102 Uiso 1 1 calc R U . . .
C14 C 0.08670(17) 0.5315(3) 0.95228(10) 0.0907(8) Uani 1 1 d . . . . .
C15 C 0.10720(14) 0.4657(3) 0.90723(10) 0.0855(7) Uani 1 1 d . . . . .
H15 H 0.146532 0.397138 0.915557 0.103 Uiso 1 1 calc R U . . .
C16 C 0.06990(12) 0.5004(3) 0.84961(8) 0.0655(5) Uani 1 1 d . . . . .
H16 H 0.084839 0.456041 0.819813 0.079 Uiso 1 1 calc R U . . .
C17 C 0.10919(8) 0.65013(19) 0.67339(6) 0.0385(4) Uani 1 1 d . . . . .
C18 C 0.12533(9) 0.8102(2) 0.66496(7) 0.0488(4) Uani 1 1 d . . . . .
H18 H 0.091108 0.878442 0.640989 0.059 Uiso 1 1 calc R U . . .
C19 C 0.19275(10) 0.8685(2) 0.69240(8) 0.0580(5) Uani 1 1 d . . . . .
H19 H 0.204037 0.976390 0.686752 0.070 Uiso 1 1 calc R U . . .
C20 C 0.24329(10) 0.7679(2) 0.72804(8) 0.0570(5) Uani 1 1 d . . . . .
H20 H 0.288713 0.807426 0.746301 0.068 Uiso 1 1 calc R U . . .
C21 C 0.22648(9) 0.6085(2) 0.73662(8) 0.0546(5) Uani 1 1 d . . . . .
H21 H 0.260539 0.540798 0.761031 0.065 Uiso 1 1 calc R U . . .
C22 C 0.15921(9) 0.5484(2) 0.70913(7) 0.0466(4) Uani 1 1 d . . . . .
H22 H 0.147937 0.440512 0.714745 0.056 Uiso 1 1 calc R U . . .
C23 C 0.1314(2) 0.5015(5) 1.01507(12) 0.1520(15) Uani 1 1 d . . . . .
H23A H 0.156163 0.600016 1.030989 0.228 Uiso 1 1 calc R U . . .
H23B H 0.165015 0.416075 1.016233 0.228 Uiso 1 1 calc R U . . .
H23C H 0.101062 0.469631 1.037601 0.228 Uiso 1 1 calc R U . . .
O1A O 0.42969(7) 0.4557(2) 0.52717(5) 0.0763(4) Uani 1 1 d . . . . .
O2A O 0.58248(7) 0.39209(16) 0.80802(5) 0.0607(3) Uani 1 1 d . . . . .
N1A N 0.54340(8) 0.5097(2) 0.58000(7) 0.0572(4) Uani 1 1 d . . . . .
H1A H 0.5536(11) 0.520(3) 0.5448(10) 0.081(7) Uiso 1 1 d . . . . .
N2A N 0.45613(7) 0.47750(18) 0.62555(6) 0.0474(3) Uani 1 1 d . . . . .
C1A C 0.59291(9) 0.5608(2) 0.63136(7) 0.0488(4) Uani 1 1 d . . . . .
C2A C 0.65816(10) 0.6196(3) 0.62970(9) 0.0624(5) Uani 1 1 d . . . . .
H2A H 0.669785 0.616937 0.595137 0.075 Uiso 1 1 calc R U . . .
C3A C 0.70552(10) 0.6821(3) 0.67971(9) 0.0654(5) Uani 1 1 d . . . . .
H3A H 0.749628 0.719664 0.679094 0.078 Uiso 1 1 calc R U . . .
C4A C 0.68759(10) 0.6888(2) 0.73063(9) 0.0579(5) Uani 1 1 d . . . . .
H4A H 0.718899 0.734835 0.763888 0.069 Uiso 1 1 calc R U . . .
C5A C 0.62362(9) 0.6278(2) 0.73233(7) 0.0499(4) Uani 1 1 d . . . . .
H5A H 0.612254 0.633025 0.766978 0.060 Uiso 1 1 calc R U . . .
C6A C 0.57505(9) 0.5578(2) 0.68307(7) 0.0435(4) Uani 1 1 d . . . . .
C7A C 0.50509(9) 0.49623(19) 0.68216(7) 0.0428(4) Uani 1 1 d . . . . .
C8A C 0.47453(10) 0.4803(2) 0.57463(7) 0.0541(5) Uani 1 1 d . . . . .
C9A C 0.48175(9) 0.4665(2) 0.72857(7) 0.0491(4) Uani 1 1 d . . . . .
H9A H 0.432767 0.457556 0.719863 0.059 Uiso 1 1 calc R U . . .
C10A C 0.52180(9) 0.4462(2) 0.79045(7) 0.0454(4) Uani 1 1 d . . . . .
C11A C 0.48248(9) 0.4844(2) 0.83269(7) 0.0430(4) Uani 1 1 d . . . . .
C12A C 0.42613(9) 0.5942(2) 0.81998(7) 0.0533(4) Uani 1 1 d . . . . .
H12A H 0.412392 0.647965 0.784275 0.064 Uiso 1 1 calc R U . . .
C13A C 0.39047(10) 0.6239(3) 0.86008(8) 0.0628(5) Uani 1 1 d . . . . .
H13A H 0.353834 0.700133 0.851362 0.075 Uiso 1 1 calc R U . . .
C14A C 0.40809(11) 0.5427(3) 0.91294(8) 0.0633(5) Uani 1 1 d . . . . .
C15A C 0.46514(11) 0.4365(2) 0.92598(8) 0.0605(5) Uani 1 1 d . . . . .
H15A H 0.478572 0.382522 0.961646 0.073 Uiso 1 1 calc R U . . .
C16A C 0.50255(10) 0.4090(2) 0.88696(7) 0.0500(4) Uani 1 1 d . . . . .
H16A H 0.541548 0.339297 0.897110 0.060 Uiso 1 1 calc R U . . .
C17A C 0.38298(9) 0.4334(2) 0.61841(6) 0.0458(4) Uani 1 1 d . . . . .
C18A C 0.33437(10) 0.5543(2) 0.61821(7) 0.0544(5) Uani 1 1 d . . . . .
H18A H 0.348128 0.663518 0.622486 0.065 Uiso 1 1 calc R U . . .
C19A C 0.26480(10) 0.5107(3) 0.61155(8) 0.0657(5) Uani 1 1 d . . . . .
H19A H 0.231365 0.591091 0.610992 0.079 Uiso 1 1 calc R U . . .
C20A C 0.24499(11) 0.3496(3) 0.60579(9) 0.0743(6) Uani 1 1 d . . . . .
H20A H 0.198106 0.321082 0.601186 0.089 Uiso 1 1 calc R U . . .
C21A C 0.29398(12) 0.2303(3) 0.60677(9) 0.0739(6) Uani 1 1 d . . . . .
H21A H 0.280417 0.120978 0.603477 0.089 Uiso 1 1 calc R U . . .
C22A C 0.36342(10) 0.2721(2) 0.61265(8) 0.0594(5) Uani 1 1 d . . . . .
H22A H 0.396581 0.191461 0.612696 0.071 Uiso 1 1 calc R U . . .
C23A C 0.36549(14) 0.5681(4) 0.95485(11) 0.1056(9) Uani 1 1 d . . . . .
H23D H 0.379093 0.487889 0.985315 0.158 Uiso 1 1 calc R U . . .
H23E H 0.315848 0.556979 0.934313 0.158 Uiso 1 1 calc R U . . .
H23F H 0.374532 0.675630 0.971488 0.158 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 C8 1.2304(19) . ?
O2 C10 1.226(2) . ?
N1 C8 1.350(2) . ?
N1 C1 1.388(2) . ?
N1 H1 0.81(2) . ?
N2 C8 1.381(2) . ?
N2 C7 1.4250(19) . ?
N2 C17 1.4498(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(2) . ?
C7 C9 1.353(2) . ?
C9 C10 1.468(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.493(2) . ?
C11 C16 1.382(3) . ?
C11 C12 1.391(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 C23 1.522(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.376(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1A C8A 1.232(2) . ?
O2A C10A 1.227(2) . ?
N1A C8A 1.351(2) . ?
N1A C1A 1.388(2) . ?
N1A H1A 0.93(2) . ?
N2A C8A 1.383(2) . ?
N2A C7A 1.420(2) . ?
N2A C17A 1.451(2) . ?
C1A C2A 1.390(2) . ?
C1A C6A 1.396(2) . ?
C2A C3A 1.379(3) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.379(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.373(2) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.402(2) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.467(2) . ?
C7A C9A 1.357(2) . ?
C9A C10A 1.469(2) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.491(2) . ?
C11A C16A 1.390(2) . ?
C11A C12A 1.391(2) . ?
C12A C13A 1.382(3) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.384(3) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.383(3) . ?
C14A C23A 1.515(3) . ?
C15A C16A 1.382(2) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A C22A 1.370(3) . ?
C17A C18A 1.379(2) . ?
C18A C19A 1.383(3) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.369(3) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.371(3) . ?
C20A H20A 0.9300 . ?
C21A C22A 1.381(3) . ?
C21A H21A 0.9300 . ?
C22A H22A 0.9300 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 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
C8 N1 C1 123.42(14) . . ?
C8 N1 H1 116.8(14) . . ?
C1 N1 H1 116.0(14) . . ?
C8 N2 C7 124.48(13) . . ?
C8 N2 C17 114.99(12) . . ?
C7 N2 C17 120.21(12) . . ?
N1 C1 C2 118.92(16) . . ?
N1 C1 C6 119.63(15) . . ?
C2 C1 C6 121.39(16) . . ?
C3 C2 C1 119.87(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.86(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.63(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.90(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.08(16) . . ?
C1 C6 C7 119.07(14) . . ?
C5 C6 C7 123.75(15) . . ?
C9 C7 N2 117.56(14) . . ?
C9 C7 C6 127.91(14) . . ?
N2 C7 C6 114.47(13) . . ?
O1 C8 N1 122.32(15) . . ?
O1 C8 N2 121.09(15) . . ?
N1 C8 N2 116.59(14) . . ?
C7 C9 C10 131.45(16) . . ?
C7 C9 H9 114.3 . . ?
C10 C9 H9 114.3 . . ?
O2 C10 C9 124.31(16) . . ?
O2 C10 C11 120.51(15) . . ?
C9 C10 C11 115.07(16) . . ?
C16 C11 C12 118.17(18) . . ?
C16 C11 C10 121.92(15) . . ?
C12 C11 C10 119.89(18) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 C23 121.6(3) . . ?
C15 C14 C23 119.9(3) . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C22 C17 C18 120.80(15) . . ?
C22 C17 N2 120.87(14) . . ?
C18 C17 N2 118.32(14) . . ?
C17 C18 C19 119.43(16) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.31(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.84(17) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.38(17) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.22(16) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8A N1A C1A 123.77(15) . . ?
C8A N1A H1A 114.8(13) . . ?
C1A N1A H1A 119.6(13) . . ?
C8A N2A C7A 124.32(14) . . ?
C8A N2A C17A 115.01(13) . . ?
C7A N2A C17A 120.27(13) . . ?
N1A C1A C2A 119.17(16) . . ?
N1A C1A C6A 119.27(15) . . ?
C2A C1A C6A 121.52(17) . . ?
C3A C2A C1A 119.48(18) . . ?
C3A C2A H2A 120.3 . . ?
C1A C2A H2A 120.3 . . ?
C4A C3A C2A 120.13(18) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C5A C4A C3A 120.15(18) . . ?
C5A C4A H4A 119.9 . . ?
C3A C4A H4A 119.9 . . ?
C4A C5A C6A 121.54(17) . . ?
C4A C5A H5A 119.2 . . ?
C6A C5A H5A 119.2 . . ?
C1A C6A C5A 117.01(16) . . ?
C1A C6A C7A 119.21(15) . . ?
C5A C6A C7A 123.55(15) . . ?
C9A C7A N2A 117.97(15) . . ?
C9A C7A C6A 127.36(15) . . ?
N2A C7A C6A 114.53(13) . . ?
O1A C8A N1A 122.54(16) . . ?
O1A C8A N2A 120.76(16) . . ?
N1A C8A N2A 116.70(15) . . ?
C7A C9A C10A 130.06(16) . . ?
C7A C9A H9A 115.0 . . ?
C10A C9A H9A 115.0 . . ?
O2A C10A C9A 123.95(15) . . ?
O2A C10A C11A 119.97(15) . . ?
C9A C10A C11A 115.94(15) . . ?
C16A C11A C12A 118.23(16) . . ?
C16A C11A C10A 119.42(15) . . ?
C12A C11A C10A 122.35(15) . . ?
C13A C12A C11A 120.39(17) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C14A 121.40(18) . . ?
C12A C13A H13A 119.3 . . ?
C14A C13A H13A 119.3 . . ?
C15A C14A C13A 118.00(17) . . ?
C15A C14A C23A 121.1(2) . . ?
C13A C14A C23A 120.9(2) . . ?
C16A C15A C14A 121.17(17) . . ?
C16A C15A H15A 119.4 . . ?
C14A C15A H15A 119.4 . . ?
C15A C16A C11A 120.68(17) . . ?
C15A C16A H16A 119.7 . . ?
C11A C16A H16A 119.7 . . ?
C22A C17A C18A 121.01(17) . . ?
C22A C17A N2A 119.50(16) . . ?
C18A C17A N2A 119.49(16) . . ?
C17A C18A C19A 118.95(19) . . ?
C17A C18A H18A 120.5 . . ?
C19A C18A H18A 120.5 . . ?
C20A C19A C18A 120.3(2) . . ?
C20A C19A H19A 119.9 . . ?
C18A C19A H19A 119.9 . . ?
C19A C20A C21A 120.2(2) . . ?
C19A C20A H20A 119.9 . . ?
C21A C20A H20A 119.9 . . ?
C20A C21A C22A 120.2(2) . . ?
C20A C21A H21A 119.9 . . ?
C22A C21A H21A 119.9 . . ?
C17A C22A C21A 119.35(19) . . ?
C17A C22A H22A 120.3 . . ?
C21A C22A H22A 120.3 . . ?
C14A C23A H23D 109.5 . . ?
C14A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C14A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 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
C8 N1 C1 C2 -167.79(18) . . . . ?
C8 N1 C1 C6 9.6(3) . . . . ?
N1 C1 C2 C3 173.9(2) . . . . ?
C6 C1 C2 C3 -3.4(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 3.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
N1 C1 C6 C5 -171.38(16) . . . . ?
C2 C1 C6 C5 5.9(3) . . . . ?
N1 C1 C6 C7 5.2(2) . . . . ?
C2 C1 C6 C7 -177.49(16) . . . . ?
C4 C5 C6 C1 -3.9(3) . . . . ?
C4 C5 C6 C7 179.67(17) . . . . ?
C8 N2 C7 C9 -173.51(16) . . . . ?
C17 N2 C7 C9 -0.3(2) . . . . ?
C8 N2 C7 C6 9.1(2) . . . . ?
C17 N2 C7 C6 -177.65(13) . . . . ?
C1 C6 C7 C9 169.41(17) . . . . ?
C5 C6 C7 C9 -14.2(3) . . . . ?
C1 C6 C7 N2 -13.6(2) . . . . ?
C5 C6 C7 N2 162.77(15) . . . . ?
C1 N1 C8 O1 166.60(18) . . . . ?
C1 N1 C8 N2 -14.2(3) . . . . ?
C7 N2 C8 O1 -176.54(16) . . . . ?
C17 N2 C8 O1 9.9(2) . . . . ?
C7 N2 C8 N1 4.3(2) . . . . ?
C17 N2 C8 N1 -169.26(15) . . . . ?
N2 C7 C9 C10 172.92(17) . . . . ?
C6 C7 C9 C10 -10.1(3) . . . . ?
C7 C9 C10 O2 -35.7(3) . . . . ?
C7 C9 C10 C11 148.01(18) . . . . ?
O2 C10 C11 C16 161.01(18) . . . . ?
C9 C10 C11 C16 -22.6(2) . . . . ?
O2 C10 C11 C12 -17.2(3) . . . . ?
C9 C10 C11 C12 159.24(16) . . . . ?
C16 C11 C12 C13 2.9(3) . . . . ?
C10 C11 C12 C13 -178.79(18) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C23 176.7(3) . . . . ?
C13 C14 C15 C16 2.5(4) . . . . ?
C23 C14 C15 C16 -175.7(3) . . . . ?
C12 C11 C16 C15 -1.9(3) . . . . ?
C10 C11 C16 C15 179.89(19) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
C8 N2 C17 C22 -107.51(17) . . . . ?
C7 N2 C17 C22 78.67(19) . . . . ?
C8 N2 C17 C18 73.29(18) . . . . ?
C7 N2 C17 C18 -100.53(17) . . . . ?
C22 C17 C18 C19 0.5(2) . . . . ?
N2 C17 C18 C19 179.74(14) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C18 C17 C22 C21 -0.2(2) . . . . ?
N2 C17 C22 C21 -179.39(14) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C8A N1A C1A C2A -166.93(18) . . . . ?
C8A N1A C1A C6A 10.7(3) . . . . ?
N1A C1A C2A C3A 175.14(18) . . . . ?
C6A C1A C2A C3A -2.4(3) . . . . ?
C1A C2A C3A C4A -1.3(3) . . . . ?
C2A C3A C4A C5A 2.5(3) . . . . ?
C3A C4A C5A C6A -0.1(3) . . . . ?
N1A C1A C6A C5A -172.92(15) . . . . ?
C2A C1A C6A C5A 4.6(2) . . . . ?
N1A C1A C6A C7A 1.7(2) . . . . ?
C2A C1A C6A C7A 179.26(16) . . . . ?
C4A C5A C6A C1A -3.4(2) . . . . ?
C4A C5A C6A C7A -177.77(16) . . . . ?
C8A N2A C7A C9A -170.23(16) . . . . ?
C17A N2A C7A C9A 2.1(2) . . . . ?
C8A N2A C7A C6A 13.9(2) . . . . ?
C17A N2A C7A C6A -173.83(14) . . . . ?
C1A C6A C7A C9A 171.70(17) . . . . ?
C5A C6A C7A C9A -14.0(3) . . . . ?
C1A C6A C7A N2A -12.8(2) . . . . ?
C5A C6A C7A N2A 161.45(15) . . . . ?
C1A N1A C8A O1A 170.35(19) . . . . ?
C1A N1A C8A N2A -10.1(3) . . . . ?
C7A N2A C8A O1A 176.64(18) . . . . ?
C17A N2A C8A O1A 4.0(3) . . . . ?
C7A N2A C8A N1A -2.9(3) . . . . ?
C17A N2A C8A N1A -175.55(16) . . . . ?
N2A C7A C9A C10A 167.43(17) . . . . ?
C6A C7A C9A C10A -17.2(3) . . . . ?
C7A C9A C10A O2A -29.2(3) . . . . ?
C7A C9A C10A C11A 155.11(17) . . . . ?
O2A C10A C11A C16A -22.3(2) . . . . ?
C9A C10A C11A C16A 153.54(16) . . . . ?
O2A C10A C11A C12A 157.35(17) . . . . ?
C9A C10A C11A C12A -26.8(2) . . . . ?
C16A C11A C12A C13A -1.4(3) . . . . ?
C10A C11A C12A C13A 178.95(16) . . . . ?
C11A C12A C13A C14A -1.9(3) . . . . ?
C12A C13A C14A C15A 3.3(3) . . . . ?
C12A C13A C14A C23A -175.9(2) . . . . ?
C13A C14A C15A C16A -1.5(3) . . . . ?
C23A C14A C15A C16A 177.8(2) . . . . ?
C14A C15A C16A C11A -1.8(3) . . . . ?
C12A C11A C16A C15A 3.2(3) . . . . ?
C10A C11A C16A C15A -177.13(16) . . . . ?
C8A N2A C17A C22A 79.8(2) . . . . ?
C7A N2A C17A C22A -93.19(19) . . . . ?
C8A N2A C17A C18A -100.93(18) . . . . ?
C7A N2A C17A C18A 86.06(19) . . . . ?
C22A C17A C18A C19A -0.6(3) . . . . ?
N2A C17A C18A C19A -179.80(15) . . . . ?
C17A C18A C19A C20A 0.6(3) . . . . ?
C18A C19A C20A C21A 0.2(3) . . . . ?
C19A C20A C21A C22A -1.0(3) . . . . ?
C18A C17A C22A C21A -0.2(3) . . . . ?
N2A C17A C22A C21A 179.00(16) . . . . ?
C20A C21A C22A C17A 1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.81(2) 2.05(2) 2.8527(19) 174.4(19) 3_566 yes
C22 H22 O2 0.93 2.46 3.365(2) 164.1 2_546 yes
N1A H1A O1A 0.93(2) 1.87(2) 2.8072(19) 177.7(19) 3_666 yes
C18A H18A O2A 0.93 2.60 3.422(2) 147.1 2_656 yes

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_9h
_database_code_depnum_ccdc_archive 'CCDC 1989175'
loop_
_audit_author_name
_audit_author_address
'Gustavo Portalone'
;Sapienza University of Rome
Italy
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O2 S'
_chemical_formula_sum            'C24 H18 N2 O2 S'
_chemical_formula_weight         398.46

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'

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

_cell_length_a                   6.5760(4)
_cell_length_b                   16.9049(10)
_cell_length_c                   17.5937(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1955.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      3.6830
_cell_measurement_theta_max      22.3290
_exptl_crystal_description       tablets
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.86838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            10762
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.307
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3540
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0646P)²+0.2597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.6242(2) -0.07653(8) -0.96614(7) 0.0522(4) Uani 1 1 d . . . . .
O1 O -0.2960(6) -0.0131(3) -1.0202(2) 0.0759(12) Uani 1 1 d . . . . .
O2 O -0.7047(7) -0.2039(3) -1.0560(2) 0.0819(14) Uani 1 1 d . . . . .
N1 N -0.9783(7) -0.0853(3) -0.8835(2) 0.0564(11) Uani 1 1 d . . . . .
N2 N -0.9708(7) -0.1483(3) -0.9976(2) 0.0602(12) Uani 1 1 d . . . . .
H2A H -1.101541 -0.147734 -0.996063 0.072 Uiso 1 1 calc R U . . .
C1 C -0.7056(9) -0.0042(3) -0.8270(3) 0.0550(14) Uani 1 1 d . . . . .
C2 C -0.6400(11) 0.0364(4) -0.7619(3) 0.0753(18) Uani 1 1 d . . . . .
H2 H -0.512687 0.060346 -0.761126 0.090 Uiso 1 1 calc R U . . .
C3 C -0.7641(13) 0.0407(4) -0.6992(3) 0.090(2) Uani 1 1 d . . . . .
H3 H -0.719461 0.067899 -0.656405 0.108 Uiso 1 1 calc R U . . .
C4 C -0.9517(13) 0.0060(4) -0.6985(3) 0.083(2) Uani 1 1 d . . . . .
H4 H -1.033562 0.009604 -0.655480 0.100 Uiso 1 1 calc R U . . .
C5 C -1.0182(10) -0.0338(4) -0.7609(3) 0.0688(16) Uani 1 1 d . . . . .
H5 H -1.146190 -0.057246 -0.760561 0.083 Uiso 1 1 calc R U . . .
C6 C -0.8951(9) -0.0398(3) -0.8256(3) 0.0534(13) Uani 1 1 d . . . . .
C7 C -0.8733(8) -0.1051(3) -0.9419(2) 0.0474(12) Uani 1 1 d . . . . .
C8 C -0.5708(8) -0.0074(3) -0.8951(3) 0.0502(13) Uani 1 1 d . . . . .
C9 C -0.4003(9) 0.0381(3) -0.9040(3) 0.0604(14) Uani 1 1 d . . . . .
H9 H -0.368992 0.074128 -0.865759 0.072 Uiso 1 1 calc R U . . .
C10 C -0.8868(10) -0.1918(3) -1.0546(3) 0.0537(13) Uani 1 1 d . . . . .
C11 C -1.0233(9) -0.2199(3) -1.1161(3) 0.0500(13) Uani 1 1 d . . . . .
C12 C -1.2160(10) -0.1912(4) -1.1269(3) 0.0658(16) Uani 1 1 d . . . . .
H12 H -1.268845 -0.154143 -1.093208 0.079 Uiso 1 1 calc R U . . .
C13 C -1.3325(11) -0.2168(4) -1.1875(3) 0.086(2) Uani 1 1 d . . . . .
H13 H -1.462120 -0.196275 -1.195176 0.103 Uiso 1 1 calc R U . . .
C14 C -1.2555(11) -0.2726(4) -1.2362(4) 0.083(2) Uani 1 1 d . . . . .
H14 H -1.333819 -0.290299 -1.276776 0.099 Uiso 1 1 calc R U . . .
C15 C -1.0650(11) -0.3021(4) -1.2255(3) 0.0717(18) Uani 1 1 d . . . . .
H15 H -1.013837 -0.339733 -1.258993 0.086 Uiso 1 1 calc R U . . .
C16 C -0.9470(10) -0.2768(3) -1.1652(3) 0.0608(15) Uani 1 1 d . . . . .
H16 H -0.817706 -0.297672 -1.157661 0.073 Uiso 1 1 calc R U . . .
C17 C -0.2657(8) 0.0339(3) -0.9689(3) 0.0610(14) Uani 1 1 d . . . . .
C18 C -0.0837(9) 0.0881(3) -0.9756(3) 0.0658(15) Uani 1 1 d . . . . .
C19 C -0.0187(9) 0.1345(4) -0.9171(4) 0.0755(18) Uani 1 1 d . . . . .
H19 H -0.090849 0.136148 -0.871633 0.091 Uiso 1 1 calc R U . . .
C20 C 0.1654(10) 0.1813(4) -0.9266(4) 0.0775(19) Uani 1 1 d . . . . .
C21 C 0.2583(12) 0.1756(5) -0.9948(5) 0.092(2) Uani 1 1 d . . . . .
H21 H 0.376598 0.205121 -1.000957 0.111 Uiso 1 1 calc R U . . .
C22 C 0.2010(14) 0.1336(5) -1.0529(5) 0.111(3) Uani 1 1 d . . . . .
H22 H 0.272719 0.134106 -1.098466 0.134 Uiso 1 1 calc R U . . .
C23 C 0.0240(10) 0.0869(4) -1.0434(4) 0.085(2) Uani 1 1 d . . . . .
H23 H -0.020702 0.055078 -1.083106 0.103 Uiso 1 1 calc R U . . .
C24 C 0.2371(13) 0.2284(5) -0.8630(5) 0.129(3) Uani 1 1 d . . . . .
H24A H 0.218474 0.283549 -0.874150 0.194 Uiso 1 1 calc R U . . .
H24B H 0.378773 0.218012 -0.854545 0.194 Uiso 1 1 calc R U . . .
H24C H 0.161252 0.214885 -0.818209 0.194 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
S1 C8 1.746(5) . ?
S1 C7 1.760(5) . ?
O1 C17 1.219(6) . ?
O2 C10 1.216(7) . ?
N1 C7 1.283(6) . ?
N1 C6 1.389(6) . ?
N2 C10 1.359(6) . ?
N2 C7 1.380(6) . ?
N2 H2A 0.8600 . ?
C1 C6 1.384(8) . ?
C1 C2 1.404(7) . ?
C1 C8 1.492(7) . ?
C2 C3 1.373(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(7) . ?
C5 H5 0.9300 . ?
C8 C9 1.368(7) . ?
C9 C17 1.447(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.484(7) . ?
C11 C12 1.370(8) . ?
C11 C16 1.387(7) . ?
C12 C13 1.382(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.512(8) . ?
C18 C19 1.363(8) . ?
C18 C23 1.386(8) . ?
C19 C20 1.456(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.349(9) . ?
C20 C24 1.453(10) . ?
C21 C22 1.301(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.416(10) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C8 S1 C7 101.4(2) . . ?
C7 N1 C6 121.4(5) . . ?
C10 N2 C7 128.3(5) . . ?
C10 N2 H2A 115.8 . . ?
C7 N2 H2A 115.8 . . ?
C6 C1 C2 118.3(5) . . ?
C6 C1 C8 122.3(4) . . ?
C2 C1 C8 119.4(6) . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.5(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 N1 125.6(5) . . ?
C1 C6 C5 120.3(5) . . ?
N1 C6 C5 114.1(5) . . ?
N1 C7 N2 117.2(5) . . ?
N1 C7 S1 128.6(4) . . ?
N2 C7 S1 114.0(4) . . ?
C9 C8 C1 123.9(5) . . ?
C9 C8 S1 117.4(4) . . ?
C1 C8 S1 118.7(4) . . ?
C8 C9 C17 124.3(5) . . ?
C8 C9 H9 117.9 . . ?
C17 C9 H9 117.9 . . ?
O2 C10 N2 120.5(5) . . ?
O2 C10 C11 121.8(5) . . ?
N2 C10 C11 117.7(5) . . ?
C12 C11 C16 119.6(5) . . ?
C12 C11 C10 123.2(5) . . ?
C16 C11 C10 117.2(5) . . ?
C11 C12 C13 120.6(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.4(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.6(6) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.3(6) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
O1 C17 C9 121.1(5) . . ?
O1 C17 C18 117.8(5) . . ?
C9 C17 C18 121.1(5) . . ?
C19 C18 C23 119.9(6) . . ?
C19 C18 C17 122.5(6) . . ?
C23 C18 C17 117.6(6) . . ?
C18 C19 C20 119.1(6) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 116.1(7) . . ?
C21 C20 C24 125.3(7) . . ?
C19 C20 C24 118.6(7) . . ?
C22 C21 C20 127.3(8) . . ?
C22 C21 H21 116.4 . . ?
C20 C21 H21 116.4 . . ?
C21 C22 C23 116.7(8) . . ?
C21 C22 H22 121.6 . . ?
C23 C22 H22 121.6 . . ?
C18 C23 C22 120.9(7) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C6 C1 C2 C3 -0.7(9) . . . . ?
C8 C1 C2 C3 179.0(5) . . . . ?
C1 C2 C3 C4 0.2(11) . . . . ?
C2 C3 C4 C5 0.0(11) . . . . ?
C3 C4 C5 C6 0.4(10) . . . . ?
C2 C1 C6 N1 -176.6(5) . . . . ?
C8 C1 C6 N1 3.7(8) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
C8 C1 C6 C5 -178.7(5) . . . . ?
C7 N1 C6 C1 7.2(8) . . . . ?
C7 N1 C6 C5 -170.6(5) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C4 C5 C6 N1 177.0(5) . . . . ?
C6 N1 C7 N2 -178.1(5) . . . . ?
C6 N1 C7 S1 -4.7(7) . . . . ?
C10 N2 C7 N1 -162.8(5) . . . . ?
C10 N2 C7 S1 22.9(7) . . . . ?
C8 S1 C7 N1 -5.8(5) . . . . ?
C8 S1 C7 N2 167.7(4) . . . . ?
C6 C1 C8 C9 167.9(5) . . . . ?
C2 C1 C8 C9 -11.8(7) . . . . ?
C6 C1 C8 S1 -15.5(6) . . . . ?
C2 C1 C8 S1 164.8(4) . . . . ?
C7 S1 C8 C9 -168.5(4) . . . . ?
C7 S1 C8 C1 14.7(4) . . . . ?
C1 C8 C9 C17 178.2(5) . . . . ?
S1 C8 C9 C17 1.6(7) . . . . ?
C7 N2 C10 O2 8.8(9) . . . . ?
C7 N2 C10 C11 -168.1(4) . . . . ?
O2 C10 C11 C12 -162.8(6) . . . . ?
N2 C10 C11 C12 14.1(8) . . . . ?
O2 C10 C11 C16 15.8(8) . . . . ?
N2 C10 C11 C16 -167.3(4) . . . . ?
C16 C11 C12 C13 -1.8(8) . . . . ?
C10 C11 C12 C13 176.8(5) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C15 -0.6(10) . . . . ?
C13 C14 C15 C16 0.4(10) . . . . ?
C14 C15 C16 C11 -0.9(9) . . . . ?
C12 C11 C16 C15 1.6(8) . . . . ?
C10 C11 C16 C15 -177.1(5) . . . . ?
C8 C9 C17 O1 -1.5(8) . . . . ?
C8 C9 C17 C18 178.0(5) . . . . ?
O1 C17 C18 C19 -170.1(5) . . . . ?
C9 C17 C18 C19 10.3(8) . . . . ?
O1 C17 C18 C23 6.9(8) . . . . ?
C9 C17 C18 C23 -172.6(5) . . . . ?
C23 C18 C19 C20 -0.8(9) . . . . ?
C17 C18 C19 C20 176.2(5) . . . . ?
C18 C19 C20 C21 0.7(8) . . . . ?
C18 C19 C20 C24 -178.0(7) . . . . ?
C19 C20 C21 C22 0.5(11) . . . . ?
C24 C20 C21 C22 179.1(8) . . . . ?
C20 C21 C22 C23 -1.6(12) . . . . ?
C19 C18 C23 C22 -0.2(9) . . . . ?
C17 C18 C23 C22 -177.4(6) . . . . ?
C21 C22 C23 C18 1.4(11) . . . . ?

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 O1 0.86 2.64 3.155(6) 119.2 1_455 yes

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041

