# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_donw082
_database_code_depnum_ccdc_archive 'CCDC 2071160'
loop_
_audit_author_name
_audit_author_address
'Glenn Yap'
;University of Delaware
United States of America
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-05-27 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         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30

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                   13.1732(9)
_cell_length_b                   6.5528(5)
_cell_length_c                   15.2376(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.3850(10)
_cell_angle_gamma                90
_cell_volume                     1268.19(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7588
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.244
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7237
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'APEX3 (Bruker, 2007)'
_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 AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            14948
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.603
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3149
_reflns_number_gt                2813
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0659P)²+0.3130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.44759(6) 0.48226(12) 0.37317(5) 0.02476(19) Uani 1 1 d . . . . .
N1 N 0.55164(7) 0.26055(13) 0.47616(6) 0.02053(19) Uani 1 1 d . . . . .
C1 C 0.50772(7) 0.33384(15) 0.39216(6) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.55021(7) 0.20959(15) 0.32604(6) 0.0186(2) Uani 1 1 d . . . . .
C3 C 0.65525(8) 0.31129(15) 0.31871(7) 0.0197(2) Uani 1 1 d . . . . .
C4 C 0.74089(8) 0.17169(15) 0.37781(7) 0.0206(2) Uani 1 1 d . . . . .
C5 C 0.74022(8) 0.17709(14) 0.47920(7) 0.0198(2) Uani 1 1 d . . . . .
C6 C 0.62743(8) 0.09703(15) 0.47577(6) 0.0201(2) Uani 1 1 d . . . . .
C7 C 0.58976(8) 0.00954(15) 0.37779(7) 0.0202(2) Uani 1 1 d . . . . .
C8 C 0.69136(8) -0.04000(16) 0.35142(7) 0.0229(2) Uani 1 1 d . . . . .
C9 C 0.76996(8) 0.36727(15) 0.53451(7) 0.0207(2) Uani 1 1 d . . . . .
C10 C 0.83210(8) 0.51734(15) 0.52040(7) 0.0203(2) Uani 1 1 d . . . . .
C11 C 0.95270(8) 0.81079(15) 0.57637(7) 0.0205(2) Uani 1 1 d . . . . .
C12 C 0.98641(8) 0.97578(15) 0.63447(7) 0.0224(2) Uani 1 1 d . . . . .
C13 C 0.93459(8) 1.02662(16) 0.69967(7) 0.0243(2) Uani 1 1 d . . . . .
C14 C 0.84773(8) 0.91132(16) 0.70598(7) 0.0244(2) Uani 1 1 d . . . . .
C15 C 0.81327(8) 0.74725(15) 0.64781(7) 0.0217(2) Uani 1 1 d . . . . .
C16 C 0.86572(7) 0.69307(14) 0.58215(6) 0.0184(2) Uani 1 1 d . . . . .
H1 H 0.5520(12) 0.341(2) 0.5273(11) 0.041(4) Uiso 1 1 d . . . . .
H2 H 0.4982(11) 0.1941(19) 0.2669(9) 0.023(3) Uiso 1 1 d . . . . .
H3 H 0.6606(11) 0.460(2) 0.3387(9) 0.026(3) Uiso 1 1 d . . . . .
H4 H 0.6592(11) 0.308(2) 0.2538(9) 0.025(3) Uiso 1 1 d . . . . .
H5 H 0.8125(12) 0.196(2) 0.3679(9) 0.028(3) Uiso 1 1 d . . . . .
H6 H 0.7884(10) 0.069(2) 0.5099(9) 0.022(3) Uiso 1 1 d . . . . .
H7 H 0.6277(11) -0.001(2) 0.5262(9) 0.024(3) Uiso 1 1 d . . . . .
H8 H 0.5353(10) -0.099(2) 0.3694(9) 0.024(3) Uiso 1 1 d . . . . .
H9 H 0.6780(11) -0.070(2) 0.2849(10) 0.031(4) Uiso 1 1 d . . . . .
H10 H 0.7334(11) -0.153(2) 0.3880(9) 0.026(3) Uiso 1 1 d . . . . .
H11 H 0.7450(12) 0.374(2) 0.5915(10) 0.033(4) Uiso 1 1 d . . . . .
H12 H 0.8607(12) 0.512(2) 0.4659(10) 0.031(4) Uiso 1 1 d . . . . .
H13 H 0.9892(11) 0.774(2) 0.5288(9) 0.025(3) Uiso 1 1 d . . . . .
H14 H 1.0468(12) 1.056(2) 0.6299(10) 0.035(4) Uiso 1 1 d . . . . .
H15 H 0.9558(12) 1.144(2) 0.7398(10) 0.035(4) Uiso 1 1 d . . . . .
H16 H 0.8109(11) 0.948(2) 0.7514(10) 0.032(4) Uiso 1 1 d . . . . .
H17 H 0.7506(11) 0.667(2) 0.6518(9) 0.028(3) 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 1.2391(12) . ?
N1 C1 1.3456(13) . ?
N1 C6 1.4656(13) . ?
N1 H1 0.939(16) . ?
C1 C2 1.5134(13) . ?
C2 C7 1.5471(13) . ?
C2 C3 1.5664(13) . ?
C2 H2 0.982(14) . ?
C3 C4 1.5432(14) . ?
C3 H3 1.016(14) . ?
C3 H4 1.003(13) . ?
C4 C8 1.5402(14) . ?
C4 C5 1.5478(14) . ?
C4 H5 1.006(15) . ?
C5 C9 1.4972(13) . ?
C5 C6 1.5634(14) . ?
C5 H6 0.983(13) . ?
C6 C7 1.5527(13) . ?
C6 H7 1.001(14) . ?
C7 C8 1.5309(15) . ?
C7 H8 0.995(13) . ?
C8 H9 1.001(14) . ?
C8 H10 1.000(14) . ?
C9 C10 1.3329(14) . ?
C9 H11 1.007(15) . ?
C10 C16 1.4786(13) . ?
C10 H12 1.000(15) . ?
C11 C12 1.3933(14) . ?
C11 C16 1.4033(14) . ?
C11 H13 1.001(14) . ?
C12 C13 1.3871(16) . ?
C12 H14 0.973(16) . ?
C13 C14 1.3956(15) . ?
C13 H15 0.975(15) . ?
C14 C15 1.3907(14) . ?
C14 H16 0.977(15) . ?
C15 C16 1.4040(14) . ?
C15 H17 0.994(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 112.24(8) . . ?
C1 N1 H1 119.7(10) . . ?
C6 N1 H1 124.0(10) . . ?
O1 C1 N1 126.10(9) . . ?
O1 C1 C2 126.38(9) . . ?
N1 C1 C2 107.43(8) . . ?
C1 C2 C7 104.51(8) . . ?
C1 C2 C3 107.96(8) . . ?
C7 C2 C3 102.26(7) . . ?
C1 C2 H2 112.1(8) . . ?
C7 C2 H2 116.0(8) . . ?
C3 C2 H2 113.1(8) . . ?
C4 C3 C2 103.24(8) . . ?
C4 C3 H3 114.3(8) . . ?
C2 C3 H3 112.2(8) . . ?
C4 C3 H4 110.0(8) . . ?
C2 C3 H4 109.8(8) . . ?
H3 C3 H4 107.3(11) . . ?
C8 C4 C3 100.84(8) . . ?
C8 C4 C5 99.61(8) . . ?
C3 C4 C5 111.84(8) . . ?
C8 C4 H5 116.7(8) . . ?
C3 C4 H5 112.9(8) . . ?
C5 C4 H5 113.6(8) . . ?
C9 C5 C4 120.73(8) . . ?
C9 C5 C6 113.74(8) . . ?
C4 C5 C6 102.47(7) . . ?
C9 C5 H6 107.1(8) . . ?
C4 C5 H6 106.5(8) . . ?
C6 C5 H6 105.2(8) . . ?
N1 C6 C7 103.27(8) . . ?
N1 C6 C5 113.38(8) . . ?
C7 C6 C5 102.39(8) . . ?
N1 C6 H7 109.4(8) . . ?
C7 C6 H7 115.8(8) . . ?
C5 C6 H7 112.3(8) . . ?
C8 C7 C2 104.22(8) . . ?
C8 C7 C6 104.60(8) . . ?
C2 C7 C6 98.96(7) . . ?
C8 C7 H8 117.7(8) . . ?
C2 C7 H8 114.0(7) . . ?
C6 C7 H8 115.1(8) . . ?
C7 C8 C4 94.58(8) . . ?
C7 C8 H9 112.1(8) . . ?
C4 C8 H9 112.9(8) . . ?
C7 C8 H10 113.8(8) . . ?
C4 C8 H10 112.8(8) . . ?
H9 C8 H10 110.1(11) . . ?
C10 C9 C5 127.12(9) . . ?
C10 C9 H11 117.6(9) . . ?
C5 C9 H11 115.0(9) . . ?
C9 C10 C16 124.40(9) . . ?
C9 C10 H12 119.4(8) . . ?
C16 C10 H12 116.2(8) . . ?
C12 C11 C16 120.97(9) . . ?
C12 C11 H13 121.0(8) . . ?
C16 C11 H13 118.0(8) . . ?
C13 C12 C11 120.47(10) . . ?
C13 C12 H14 119.3(9) . . ?
C11 C12 H14 120.2(9) . . ?
C12 C13 C14 119.18(10) . . ?
C12 C13 H15 121.6(9) . . ?
C14 C13 H15 119.2(9) . . ?
C15 C14 C13 120.64(10) . . ?
C15 C14 H16 120.3(9) . . ?
C13 C14 H16 119.0(9) . . ?
C14 C15 C16 120.70(9) . . ?
C14 C15 H17 120.4(8) . . ?
C16 C15 H17 118.9(8) . . ?
C11 C16 C15 118.04(9) . . ?
C11 C16 C10 119.99(9) . . ?
C15 C16 C10 121.97(9) . . ?

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 N1 C1 O1 -174.00(9) . . . . ?
C6 N1 C1 C2 2.78(11) . . . . ?
O1 C1 C2 C7 -162.52(9) . . . . ?
N1 C1 C2 C7 20.71(10) . . . . ?
O1 C1 C2 C3 89.14(11) . . . . ?
N1 C1 C2 C3 -87.62(9) . . . . ?
C1 C2 C3 C4 102.60(9) . . . . ?
C7 C2 C3 C4 -7.28(9) . . . . ?
C2 C3 C4 C8 40.35(9) . . . . ?
C2 C3 C4 C5 -64.72(10) . . . . ?
C8 C4 C5 C9 -172.73(9) . . . . ?
C3 C4 C5 C9 -66.87(11) . . . . ?
C8 C4 C5 C6 -45.06(9) . . . . ?
C3 C4 C5 C6 60.80(9) . . . . ?
C1 N1 C6 C7 -24.95(10) . . . . ?
C1 N1 C6 C5 85.06(10) . . . . ?
C9 C5 C6 N1 34.33(11) . . . . ?
C4 C5 C6 N1 -97.65(9) . . . . ?
C9 C5 C6 C7 144.89(8) . . . . ?
C4 C5 C6 C7 12.90(9) . . . . ?
C1 C2 C7 C8 -141.14(8) . . . . ?
C3 C2 C7 C8 -28.67(9) . . . . ?
C1 C2 C7 C6 -33.49(9) . . . . ?
C3 C2 C7 C6 78.98(8) . . . . ?
N1 C6 C7 C8 142.00(8) . . . . ?
C5 C6 C7 C8 24.01(9) . . . . ?
N1 C6 C7 C2 34.66(9) . . . . ?
C5 C6 C7 C2 -83.33(8) . . . . ?
C2 C7 C8 C4 52.55(9) . . . . ?
C6 C7 C8 C4 -50.86(9) . . . . ?
C3 C4 C8 C7 -56.37(9) . . . . ?
C5 C4 C8 C7 58.26(8) . . . . ?
C4 C5 C9 C10 -25.46(15) . . . . ?
C6 C5 C9 C10 -147.86(10) . . . . ?
C5 C9 C10 C16 -174.54(9) . . . . ?
C16 C11 C12 C13 0.23(15) . . . . ?
C11 C12 C13 C14 -0.45(15) . . . . ?
C12 C13 C14 C15 0.03(16) . . . . ?
C13 C14 C15 C16 0.60(16) . . . . ?
C12 C11 C16 C15 0.40(14) . . . . ?
C12 C11 C16 C10 -179.35(9) . . . . ?
C14 C15 C16 C11 -0.81(15) . . . . ?
C14 C15 C16 C10 178.93(9) . . . . ?
C9 C10 C16 C11 162.05(10) . . . . ?
C9 C10 C16 C15 -17.68(15) . . . . ?

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 0.939(16) 1.908(17) 2.8459(11) 176.7(14) 3_666 yes

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_donw089
_database_code_depnum_ccdc_archive 'CCDC 2071162'
loop_
_audit_author_name
_audit_author_address
'Glenn Yap'
;University of Delaware
United States of America
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-05-27 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         'C20 H15 N O3'
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33

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                   15.3278(15)
_cell_length_b                   5.7994(6)
_cell_length_c                   17.8481(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.6770(10)
_cell_angle_gamma                90
_cell_volume                     1541.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.55

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            35133
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.002
_diffrn_reflns_theta_max         30.733
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4790
_reflns_number_gt                4093
_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 2014/5 (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)+(0.0983P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4790
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.58187(5) 0.69471(15) 0.55933(5) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.51237(5) 0.22370(12) 0.31443(4) 0.02345(16) Uani 1 1 d . . . . .
O3 O 0.34383(6) 0.38476(17) 0.23121(6) 0.0479(3) Uani 1 1 d . . . . .
N1 N 0.60566(5) 0.35634(15) 0.49833(5) 0.02471(18) Uani 1 1 d . . . . .
C1 C 0.63141(6) 0.54974(18) 0.54005(5) 0.02386(19) Uani 1 1 d . . . . .
C2 C 0.73059(6) 0.55725(17) 0.55631(5) 0.02260(19) Uani 1 1 d . . . . .
C3 C 0.78858(7) 0.72051(19) 0.59862(6) 0.0275(2) Uani 1 1 d . . . . .
C4 C 0.87987(7) 0.6918(2) 0.60395(6) 0.0324(2) Uani 1 1 d . . . . .
C5 C 0.91066(7) 0.5038(2) 0.56882(7) 0.0342(2) Uani 1 1 d . . . . .
C6 C 0.85228(7) 0.3393(2) 0.52705(6) 0.0297(2) Uani 1 1 d . . . . .
C7 C 0.76055(6) 0.37008(17) 0.52054(5) 0.02282(19) Uani 1 1 d . . . . .
C8 C 0.68001(6) 0.22835(17) 0.47973(5) 0.02205(18) Uani 1 1 d . . . . .
C9 C 0.66619(6) 0.21281(16) 0.39037(5) 0.02113(18) Uani 1 1 d . . . . .
C10 C 0.43824(6) 0.08402(18) 0.29270(5) 0.0245(2) Uani 1 1 d . . . . .
C11 C 0.45777(7) -0.13351(18) 0.32042(6) 0.0280(2) Uani 1 1 d . . . . .
C12 C 0.54900(7) -0.12853(18) 0.36245(6) 0.0291(2) Uani 1 1 d . . . . .
C13 C 0.57922(6) 0.09030(16) 0.35704(5) 0.02178(19) Uani 1 1 d . . . . .
C14 C 0.35444(7) 0.1840(2) 0.25079(7) 0.0325(2) Uani 1 1 d . . . . .
C15 C 0.79206(7) 0.23300(18) 0.32195(6) 0.0259(2) Uani 1 1 d . . . . .
C16 C 0.87016(7) 0.1467(2) 0.30481(6) 0.0316(2) Uani 1 1 d . . . . .
C17 C 0.90336(7) -0.0675(2) 0.33266(6) 0.0319(2) Uani 1 1 d . . . . .
C18 C 0.85764(7) -0.19553(19) 0.37681(7) 0.0303(2) Uani 1 1 d . . . . .
C19 C 0.77987(7) -0.10998(17) 0.39414(6) 0.0270(2) Uani 1 1 d . . . . .
C20 C 0.74681(6) 0.10663(16) 0.36758(5) 0.02146(18) Uani 1 1 d . . . . .
H1 H 0.5458(12) 0.316(3) 0.4790(10) 0.045(4) Uiso 1 1 d . . . . .
H2 H 0.7663(11) 0.842(3) 0.6232(10) 0.043(4) Uiso 1 1 d . . . . .
H3 H 0.9207(12) 0.801(3) 0.6305(10) 0.051(5) Uiso 1 1 d . . . . .
H4 H 0.9761(12) 0.485(3) 0.5737(10) 0.055(5) Uiso 1 1 d . . . . .
H5 H 0.8758(10) 0.206(3) 0.5018(9) 0.036(4) Uiso 1 1 d . . . . .
H6 H 0.6825(9) 0.068(2) 0.5009(8) 0.025(3) Uiso 1 1 d . . . . .
H7 H 0.6592(9) 0.373(2) 0.3695(7) 0.024(3) Uiso 1 1 d . . . . .
H8 H 0.4178(10) -0.263(3) 0.3114(9) 0.034(4) Uiso 1 1 d . . . . .
H9 H 0.5827(10) -0.258(3) 0.3910(9) 0.038(4) Uiso 1 1 d . . . . .
H10 H 0.3018(12) 0.069(3) 0.2391(10) 0.048(4) Uiso 1 1 d . . . . .
H11 H 0.7714(9) 0.382(2) 0.3019(8) 0.027(3) Uiso 1 1 d . . . . .
H12 H 0.8976(10) 0.235(3) 0.2703(9) 0.039(4) Uiso 1 1 d . . . . .
H13 H 0.9579(11) -0.128(3) 0.3196(9) 0.042(4) Uiso 1 1 d . . . . .
H14 H 0.8783(10) -0.347(3) 0.3961(9) 0.040(4) Uiso 1 1 d . . . . .
H15 H 0.7488(10) -0.202(3) 0.4272(9) 0.040(4) 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 1.2351(12) . ?
O2 C13 1.3632(11) . ?
O2 C10 1.3746(12) . ?
O3 C14 1.2154(15) . ?
N1 C1 1.3525(12) . ?
N1 C8 1.4625(12) . ?
N1 H1 0.929(17) . ?
C1 C2 1.4793(13) . ?
C2 C7 1.3912(13) . ?
C2 C3 1.3926(14) . ?
C3 C4 1.3900(15) . ?
C3 H2 0.934(17) . ?
C4 C5 1.3945(18) . ?
C4 H3 0.935(18) . ?
C5 C6 1.3968(16) . ?
C5 H4 0.993(18) . ?
C6 C7 1.3946(13) . ?
C6 H5 1.002(15) . ?
C7 C8 1.5181(13) . ?
C8 C9 1.5611(13) . ?
C8 H6 1.003(13) . ?
C9 C13 1.5035(13) . ?
C9 C20 1.5197(12) . ?
C9 H7 1.000(13) . ?
C10 C11 1.3623(15) . ?
C10 C14 1.4461(14) . ?
C11 C12 1.4222(15) . ?
C11 H8 0.956(15) . ?
C12 C13 1.3622(14) . ?
C12 H9 0.983(16) . ?
C14 H10 1.028(17) . ?
C15 C20 1.3959(13) . ?
C15 C16 1.3965(14) . ?
C15 H11 0.958(14) . ?
C16 C17 1.3891(17) . ?
C16 H12 0.970(16) . ?
C17 C18 1.3874(16) . ?
C17 H13 0.985(16) . ?
C18 C19 1.3917(14) . ?
C18 H14 0.971(16) . ?
C19 C20 1.3950(13) . ?
C19 H15 0.997(16) . ?

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
C13 O2 C10 106.57(8) . . ?
C1 N1 C8 113.83(8) . . ?
C1 N1 H1 123.0(10) . . ?
C8 N1 H1 122.9(10) . . ?
O1 C1 N1 126.81(9) . . ?
O1 C1 C2 126.60(9) . . ?
N1 C1 C2 106.57(8) . . ?
C7 C2 C3 122.81(9) . . ?
C7 C2 C1 108.81(8) . . ?
C3 C2 C1 128.38(9) . . ?
C4 C3 C2 117.32(10) . . ?
C4 C3 H2 122.1(10) . . ?
C2 C3 H2 120.6(10) . . ?
C3 C4 C5 120.33(10) . . ?
C3 C4 H3 119.7(11) . . ?
C5 C4 H3 119.9(11) . . ?
C4 C5 C6 122.13(10) . . ?
C4 C5 H4 119.4(10) . . ?
C6 C5 H4 118.4(10) . . ?
C7 C6 C5 117.59(10) . . ?
C7 C6 H5 121.6(9) . . ?
C5 C6 H5 120.8(9) . . ?
C2 C7 C6 119.81(9) . . ?
C2 C7 C8 108.87(8) . . ?
C6 C7 C8 131.32(9) . . ?
N1 C8 C7 101.85(7) . . ?
N1 C8 C9 109.66(7) . . ?
C7 C8 C9 114.83(8) . . ?
N1 C8 H6 110.4(7) . . ?
C7 C8 H6 111.6(8) . . ?
C9 C8 H6 108.4(8) . . ?
C13 C9 C20 113.80(8) . . ?
C13 C9 C8 108.96(7) . . ?
C20 C9 C8 111.99(7) . . ?
C13 C9 H7 106.6(7) . . ?
C20 C9 H7 107.5(7) . . ?
C8 C9 H7 107.6(7) . . ?
C11 C10 O2 110.32(9) . . ?
C11 C10 C14 130.64(10) . . ?
O2 C10 C14 118.92(9) . . ?
C10 C11 C12 106.08(9) . . ?
C10 C11 H8 125.9(9) . . ?
C12 C11 H8 128.0(9) . . ?
C13 C12 C11 106.85(9) . . ?
C13 C12 H9 127.1(9) . . ?
C11 C12 H9 126.0(9) . . ?
C12 C13 O2 110.18(9) . . ?
C12 C13 C9 134.17(9) . . ?
O2 C13 C9 115.57(8) . . ?
O3 C14 C10 125.09(11) . . ?
O3 C14 H10 121.1(10) . . ?
C10 C14 H10 113.8(10) . . ?
C20 C15 C16 120.63(10) . . ?
C20 C15 H11 121.7(8) . . ?
C16 C15 H11 117.7(8) . . ?
C17 C16 C15 120.17(10) . . ?
C17 C16 H12 121.4(9) . . ?
C15 C16 H12 118.3(9) . . ?
C18 C17 C16 119.37(9) . . ?
C18 C17 H13 121.0(9) . . ?
C16 C17 H13 119.6(9) . . ?
C17 C18 C19 120.63(10) . . ?
C17 C18 H14 121.4(9) . . ?
C19 C18 H14 118.0(9) . . ?
C18 C19 C20 120.46(9) . . ?
C18 C19 H15 119.6(9) . . ?
C20 C19 H15 119.9(9) . . ?
C19 C20 C15 118.71(9) . . ?
C19 C20 C9 121.80(8) . . ?
C15 C20 C9 119.41(8) . . ?

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 O1 175.45(10) . . . . ?
C8 N1 C1 C2 -3.02(11) . . . . ?
O1 C1 C2 C7 -176.10(10) . . . . ?
N1 C1 C2 C7 2.38(11) . . . . ?
O1 C1 C2 C3 2.88(17) . . . . ?
N1 C1 C2 C3 -178.65(10) . . . . ?
C7 C2 C3 C4 0.44(15) . . . . ?
C1 C2 C3 C4 -178.40(10) . . . . ?
C2 C3 C4 C5 -0.94(16) . . . . ?
C3 C4 C5 C6 0.37(18) . . . . ?
C4 C5 C6 C7 0.73(17) . . . . ?
C3 C2 C7 C6 0.65(15) . . . . ?
C1 C2 C7 C6 179.70(9) . . . . ?
C3 C2 C7 C8 -179.95(9) . . . . ?
C1 C2 C7 C8 -0.91(11) . . . . ?
C5 C6 C7 C2 -1.21(15) . . . . ?
C5 C6 C7 C8 179.55(10) . . . . ?
C1 N1 C8 C7 2.41(10) . . . . ?
C1 N1 C8 C9 -119.63(9) . . . . ?
C2 C7 C8 N1 -0.77(10) . . . . ?
C6 C7 C8 N1 178.53(11) . . . . ?
C2 C7 C8 C9 117.64(9) . . . . ?
C6 C7 C8 C9 -63.06(14) . . . . ?
N1 C8 C9 C13 -60.00(10) . . . . ?
C7 C8 C9 C13 -173.92(7) . . . . ?
N1 C8 C9 C20 173.20(8) . . . . ?
C7 C8 C9 C20 59.28(10) . . . . ?
C13 O2 C10 C11 -0.43(10) . . . . ?
C13 O2 C10 C14 175.86(8) . . . . ?
O2 C10 C11 C12 0.60(11) . . . . ?
C14 C10 C11 C12 -175.12(11) . . . . ?
C10 C11 C12 C13 -0.54(12) . . . . ?
C11 C12 C13 O2 0.29(11) . . . . ?
C11 C12 C13 C9 176.72(10) . . . . ?
C10 O2 C13 C12 0.07(10) . . . . ?
C10 O2 C13 C9 -177.09(7) . . . . ?
C20 C9 C13 C12 60.01(14) . . . . ?
C8 C9 C13 C12 -65.73(13) . . . . ?
C20 C9 C13 O2 -123.70(8) . . . . ?
C8 C9 C13 O2 110.55(8) . . . . ?
C11 C10 C14 O3 176.99(12) . . . . ?
O2 C10 C14 O3 1.57(17) . . . . ?
C20 C15 C16 C17 0.47(16) . . . . ?
C15 C16 C17 C18 0.75(16) . . . . ?
C16 C17 C18 C19 -0.87(17) . . . . ?
C17 C18 C19 C20 -0.24(17) . . . . ?
C18 C19 C20 C15 1.44(16) . . . . ?
C18 C19 C20 C9 -175.34(9) . . . . ?
C16 C15 C20 C19 -1.56(15) . . . . ?
C16 C15 C20 C9 175.30(9) . . . . ?
C13 C9 C20 C19 -68.35(12) . . . . ?
C8 C9 C20 C19 55.78(12) . . . . ?
C13 C9 C20 C15 114.89(10) . . . . ?
C8 C9 C20 C15 -120.98(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.929(17) 1.916(17) 2.8301(12) 167.5(15) 3_666 yes

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_donw087
_database_code_depnum_ccdc_archive 'CCDC 2071161'
loop_
_audit_author_name
_audit_author_address
'Glenn Yap'
;University of Delaware
United States of America
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-05-27 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         'C21 H18 N2 O2, 0.5(C H Cl3)'
_chemical_formula_sum            'C21.50 H18.50 Cl1.50 N2 O2'
_chemical_formula_weight         390.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.9474(5)
_cell_length_b                   13.1954(5)
_cell_length_c                   13.9109(6)
_cell_angle_alpha                65.0970(10)
_cell_angle_beta                 73.267(2)
_cell_angle_gamma                76.047(2)
_cell_volume                     1886.70(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9633
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      75.28

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.599
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            47661
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.584
_diffrn_reflns_theta_max         75.630
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             7482
_reflns_number_gt                6885
_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 2014/5 (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)+(0.0702P)²+0.9683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7482
_refine_ls_number_parameters     645
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.228
_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
O1A O 0.23002(12) 0.19096(11) 0.32932(10) 0.0364(3) Uani 1 1 d . . . . .
O2A O 0.13654(12) 0.08562(12) 0.80100(12) 0.0408(3) Uani 1 1 d . . . . .
N1A N 0.29338(14) 0.06647(12) 0.48502(12) 0.0310(3) Uani 1 1 d . . . . .
N2A N 0.31397(16) 0.12473(13) 0.80322(13) 0.0389(4) Uani 1 1 d . . . . .
C1A C 0.23278(15) 0.09861(15) 0.40635(13) 0.0293(3) Uani 1 1 d . . . . .
C2A C 0.17343(15) 0.00140(14) 0.43044(13) 0.0282(3) Uani 1 1 d . . . . .
C3A C 0.10104(16) -0.00953(16) 0.37422(14) 0.0317(4) Uani 1 1 d . . . . .
C4A C 0.05883(16) -0.11181(16) 0.41313(15) 0.0344(4) Uani 1 1 d . . . . .
C5A C 0.08764(16) -0.19953(16) 0.50633(16) 0.0344(4) Uani 1 1 d . . . . .
C6A C 0.15947(16) -0.18761(15) 0.56279(15) 0.0323(4) Uani 1 1 d . . . . .
C7A C 0.20283(15) -0.08556(14) 0.52352(13) 0.0285(3) Uani 1 1 d . . . . .
C8A C 0.28332(16) -0.04843(14) 0.56499(13) 0.0291(3) Uani 1 1 d . . . . .
C9A C 0.23346(16) -0.04710(15) 0.67983(14) 0.0299(4) Uani 1 1 d . . . . .
C10A C 0.25641(17) 0.07421(14) 0.77212(14) 0.0324(4) Uani 1 1 d . . . . .
C11A C 0.30912(16) 0.00741(14) 0.71012(13) 0.0299(4) Uani 1 1 d . . . . .
C12A C 0.43097(17) -0.00556(17) 0.68173(15) 0.0364(4) Uani 1 1 d . . . . .
C13A C 0.49450(18) 0.04663(18) 0.71310(17) 0.0409(4) Uani 1 1 d . . . . .
C14A C 0.4325(2) 0.11035(17) 0.77299(17) 0.0420(4) Uani 1 1 d . . . . .
C15A C 0.0794(2) 0.1507(2) 0.8671(2) 0.0509(5) Uani 1 1 d . . . . .
C16A C 0.10635(18) -0.1807(2) 0.83824(15) 0.0391(4) Uani 1 1 d . . . . .
C17A C 0.0879(2) -0.2874(2) 0.91606(17) 0.0491(6) Uani 1 1 d . . . . .
C18A C 0.1754(2) -0.37792(19) 0.92082(17) 0.0506(6) Uani 1 1 d . . . . .
C19A C 0.2835(2) -0.36221(18) 0.85012(17) 0.0473(5) Uani 1 1 d . . . . .
C20A C 0.30316(19) -0.25508(16) 0.77384(15) 0.0383(4) Uani 1 1 d . . . . .
C21A C 0.21428(16) -0.16384(15) 0.76562(13) 0.0312(4) Uani 1 1 d . . . . .
H1A H 0.338(2) 0.112(2) 0.489(2) 0.056(7) Uiso 1 1 d . . . . .
H2A H 0.084(2) 0.0494(19) 0.3101(18) 0.037(5) Uiso 1 1 d . . . . .
H3A H 0.011(2) -0.123(2) 0.3721(19) 0.045(6) Uiso 1 1 d . . . . .
H4A H 0.058(2) -0.2695(19) 0.5316(18) 0.038(6) Uiso 1 1 d . . . . .
H5A H 0.1776(19) -0.2482(18) 0.6279(17) 0.033(5) Uiso 1 1 d . . . . .
H6A H 0.3618(18) -0.0971(16) 0.5615(15) 0.023(4) Uiso 1 1 d . . . . .
H7A H 0.158(2) -0.0022(18) 0.6786(16) 0.031(5) Uiso 1 1 d . . . . .
H8A H 0.473(2) -0.053(2) 0.640(2) 0.046(6) Uiso 1 1 d . . . . .
H9A H 0.581(2) 0.039(2) 0.693(2) 0.054(7) Uiso 1 1 d . . . . .
H10A H 0.472(2) 0.148(2) 0.797(2) 0.049(6) Uiso 1 1 d . . . . .
H11A H 0.102(3) 0.227(3) 0.833(2) 0.061(8) Uiso 1 1 d . . . . .
H12A H 0.100(2) 0.110(2) 0.942(2) 0.060(8) Uiso 1 1 d . . . . .
H13A H -0.006(3) 0.154(3) 0.876(2) 0.069(8) Uiso 1 1 d . . . . .
H14A H 0.047(2) -0.120(2) 0.833(2) 0.052(7) Uiso 1 1 d . . . . .
H15A H 0.012(3) -0.296(2) 0.968(2) 0.065(8) Uiso 1 1 d . . . . .
H16A H 0.164(2) -0.449(2) 0.972(2) 0.049(6) Uiso 1 1 d . . . . .
H17A H 0.350(3) -0.427(3) 0.853(2) 0.069(8) Uiso 1 1 d . . . . .
H18A H 0.382(2) -0.246(2) 0.727(2) 0.046(6) Uiso 1 1 d . . . . .
O1B O 0.43453(12) 0.21663(11) 0.46772(11) 0.0390(3) Uani 1 1 d . . . . .
O2B O 0.00833(10) 0.62468(11) 0.38413(10) 0.0324(3) Uani 1 1 d . . . . .
N1B N 0.34325(13) 0.36409(12) 0.33981(12) 0.0288(3) Uani 1 1 d . . . . .
N2B N -0.08163(13) 0.54095(13) 0.31623(12) 0.0327(3) Uani 1 1 d . . . . .
C1B C 0.42120(15) 0.31620(15) 0.40579(14) 0.0300(4) Uani 1 1 d . . . . .
C2B C 0.48938(14) 0.40503(15) 0.38587(14) 0.0290(3) Uani 1 1 d . . . . .
C3B C 0.58044(16) 0.39647(16) 0.43379(15) 0.0337(4) Uani 1 1 d . . . . .
C4B C 0.63790(16) 0.49011(17) 0.39468(17) 0.0366(4) Uani 1 1 d . . . . .
C5B C 0.60607(16) 0.58703(17) 0.30924(17) 0.0378(4) Uani 1 1 d . . . . .
C6B C 0.51411(16) 0.59514(16) 0.26250(15) 0.0334(4) Uani 1 1 d . . . . .
C7B C 0.45458(14) 0.50189(15) 0.30287(14) 0.0284(3) Uani 1 1 d . . . . .
C8B C 0.35361(14) 0.48256(14) 0.26945(13) 0.0272(3) Uani 1 1 d . . . . .
C9B C 0.23772(14) 0.56173(14) 0.28733(13) 0.0261(3) Uani 1 1 d . . . . .
C10B C 0.01629(14) 0.56270(14) 0.32486(13) 0.0273(3) Uani 1 1 d . . . . .
C11B C 0.13149(14) 0.52682(14) 0.27577(13) 0.0269(3) Uani 1 1 d . . . . .
C12B C 0.13819(16) 0.46385(15) 0.21574(14) 0.0312(4) Uani 1 1 d . . . . .
C13B C 0.03551(17) 0.43940(16) 0.20544(15) 0.0345(4) Uani 1 1 d . . . . .
C14B C -0.07100(17) 0.47988(16) 0.25599(15) 0.0351(4) Uani 1 1 d . . . . .
C15B C -0.10838(16) 0.65986(18) 0.43491(16) 0.0355(4) Uani 1 1 d . . . . .
C16B C 0.25328(17) 0.76427(15) 0.24836(15) 0.0333(4) Uani 1 1 d . . . . .
C17B C 0.26566(19) 0.87473(16) 0.17744(17) 0.0395(4) Uani 1 1 d . . . . .
C18B C 0.27458(18) 0.90585(16) 0.06770(16) 0.0393(4) Uani 1 1 d . . . . .
C19B C 0.27236(19) 0.82595(17) 0.02865(16) 0.0408(4) Uani 1 1 d . . . . .
C20B C 0.26037(17) 0.71541(16) 0.09929(14) 0.0333(4) Uani 1 1 d . . . . .
C21B C 0.25036(14) 0.68335(14) 0.20987(13) 0.0264(3) Uani 1 1 d . . . . .
H1B H 0.301(2) 0.323(2) 0.333(2) 0.052(7) Uiso 1 1 d . . . . .
H2B H 0.602(2) 0.328(2) 0.4921(19) 0.039(6) Uiso 1 1 d . . . . .
H3B H 0.702(2) 0.486(2) 0.4249(19) 0.043(6) Uiso 1 1 d . . . . .
H4B H 0.649(2) 0.651(2) 0.2809(19) 0.045(6) Uiso 1 1 d . . . . .
H5B H 0.4944(18) 0.6609(18) 0.2032(17) 0.030(5) Uiso 1 1 d . . . . .
H6B H 0.3778(18) 0.4909(17) 0.1897(17) 0.031(5) Uiso 1 1 d . . . . .
H7B H 0.2244(18) 0.5569(17) 0.3643(17) 0.031(5) Uiso 1 1 d . . . . .
H8B H 0.214(2) 0.4379(18) 0.1779(17) 0.034(5) Uiso 1 1 d . . . . .
H9B H 0.040(2) 0.393(2) 0.1620(19) 0.043(6) Uiso 1 1 d . . . . .
H10B H -0.147(2) 0.4670(19) 0.2522(18) 0.039(6) Uiso 1 1 d . . . . .
H11B H -0.146(2) 0.594(2) 0.4839(19) 0.042(6) Uiso 1 1 d . . . . .
H12B H -0.149(2) 0.708(2) 0.380(2) 0.052(7) Uiso 1 1 d . . . . .
H13B H -0.098(2) 0.699(2) 0.476(2) 0.052(7) Uiso 1 1 d . . . . .
H14B H 0.247(2) 0.7404(19) 0.3248(19) 0.040(6) Uiso 1 1 d . . . . .
H15B H 0.266(2) 0.930(2) 0.207(2) 0.048(6) Uiso 1 1 d . . . . .
H16B H 0.284(2) 0.983(2) 0.0192(19) 0.041(6) Uiso 1 1 d . . . . .
H17B H 0.277(2) 0.847(2) -0.048(2) 0.051(7) Uiso 1 1 d . . . . .
H18B H 0.2611(19) 0.6601(19) 0.0699(18) 0.036(5) Uiso 1 1 d . . . . .
Cl1 Cl 0.42458(8) 0.13625(6) 0.03657(9) 0.0620(2) Uani 0.8858(18) 1 d D . P A 1
Cl2 Cl 0.42940(7) 0.34607(8) 0.05549(8) 0.0602(3) Uani 0.8858(18) 1 d D . P A 1
Cl3 Cl 0.23530(7) 0.31978(10) -0.00674(9) 0.0744(3) Uani 0.8858(18) 1 d D . P A
1
C1S C 0.3403(2) 0.2470(2) 0.07540(18) 0.0454(7) Uani 0.8858(18) 1 d D . P A 1
H1S H 0.299209 0.216235 0.153316 0.054 Uiso 0.8858(18) 1 calc R U P A 1
Cl1' Cl 0.2153(6) 0.2733(5) 0.0492(7) 0.0620(2) Uani 0.1142(18) 1 d D . P A 2
Cl2' Cl 0.4062(5) 0.1274(6) 0.0888(7) 0.0602(3) Uani 0.1142(18) 1 d D . P A 2
Cl3' Cl 0.4471(6) 0.3002(8) 0.0956(7) 0.0744(3) Uani 0.1142(18) 1 d D . P A 2
C1S' C 0.3305(13) 0.2458(15) 0.104(2) 0.0454(7) Uani 0.1142(18) 1 d D . P A 2
H1S' H 0.294704 0.219032 0.183696 0.054 Uiso 0.1142(18) 1 calc R U P A 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.239(2) . ?
O2A C10A 1.360(2) . ?
O2A C15A 1.439(2) . ?
N1A C1A 1.349(2) . ?
N1A C8A 1.463(2) . ?
N1A H1A 0.91(3) . ?
N2A C10A 1.319(2) . ?
N2A C14A 1.346(3) . ?
C1A C2A 1.483(2) . ?
C2A C3A 1.387(2) . ?
C2A C7A 1.390(2) . ?
C3A C4A 1.387(3) . ?
C3A H2A 0.94(2) . ?
C4A C5A 1.393(3) . ?
C4A H3A 0.99(2) . ?
C5A C6A 1.391(3) . ?
C5A H4A 0.96(2) . ?
C6A C7A 1.391(2) . ?
C6A H5A 0.96(2) . ?
C7A C8A 1.511(2) . ?
C8A C9A 1.542(2) . ?
C8A H6A 1.00(2) . ?
C9A C11A 1.517(2) . ?
C9A C21A 1.521(2) . ?
C9A H7A 0.96(2) . ?
C10A C11A 1.406(2) . ?
C11A C12A 1.382(3) . ?
C12A C13A 1.392(3) . ?
C12A H8A 0.99(3) . ?
C13A C14A 1.373(3) . ?
C13A H9A 0.98(3) . ?
C14A H10A 0.97(3) . ?
C15A H11A 0.98(3) . ?
C15A H12A 1.02(3) . ?
C15A H13A 0.99(3) . ?
C16A C17A 1.389(3) . ?
C16A C21A 1.390(3) . ?
C16A H14A 0.93(3) . ?
C17A C18A 1.377(4) . ?
C17A H15A 0.97(3) . ?
C18A C19A 1.381(4) . ?
C18A H16A 0.93(3) . ?
C19A C20A 1.390(3) . ?
C19A H17A 1.01(3) . ?
C20A C21A 1.388(3) . ?
C20A H18A 0.98(3) . ?
O1B C1B 1.232(2) . ?
O2B C10B 1.358(2) . ?
O2B C15B 1.434(2) . ?
N1B C1B 1.352(2) . ?
N1B C8B 1.467(2) . ?
N1B H1B 0.88(3) . ?
N2B C10B 1.318(2) . ?
N2B C14B 1.351(2) . ?
C1B C2B 1.474(2) . ?
C2B C7B 1.385(2) . ?
C2B C3B 1.391(2) . ?
C3B C4B 1.386(3) . ?
C3B H2B 0.97(2) . ?
C4B C5B 1.392(3) . ?
C4B H3B 0.96(2) . ?
C5B C6B 1.392(3) . ?
C5B H4B 0.98(2) . ?
C6B C7B 1.395(2) . ?
C6B H5B 0.95(2) . ?
C7B C8B 1.519(2) . ?
C8B C9B 1.547(2) . ?
C8B H6B 1.03(2) . ?
C9B C11B 1.520(2) . ?
C9B C21B 1.525(2) . ?
C9B H7B 1.01(2) . ?
C10B C11B 1.415(2) . ?
C11B C12B 1.381(2) . ?
C12B C13B 1.400(2) . ?
C12B H8B 0.97(2) . ?
C13B C14B 1.368(3) . ?
C13B H9B 1.01(2) . ?
C14B H10B 0.98(2) . ?
C15B H11B 0.97(2) . ?
C15B H12B 0.94(3) . ?
C15B H13B 0.97(3) . ?
C16B C17B 1.389(3) . ?
C16B C21B 1.392(2) . ?
C16B H14B 0.96(2) . ?
C17B C18B 1.382(3) . ?
C17B H15B 0.98(3) . ?
C18B C19B 1.383(3) . ?
C18B H16B 0.97(2) . ?
C19B C20B 1.388(3) . ?
C19B H17B 0.98(3) . ?
C20B C21B 1.389(2) . ?
C20B H18B 0.97(2) . ?
Cl1 C1S 1.756(3) . ?
Cl2 C1S 1.764(3) . ?
Cl3 C1S 1.767(3) . ?
C1S H1S 1.0000 . ?
Cl1' C1S' 1.657(12) . ?
Cl2' C1S' 1.672(14) . ?
Cl3' C1S' 1.667(13) . ?
C1S' H1S' 1.0000 . ?

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
C10A O2A C15A 117.39(17) . . ?
C1A N1A C8A 114.48(14) . . ?
C1A N1A H1A 123.5(17) . . ?
C8A N1A H1A 122.0(17) . . ?
C10A N2A C14A 116.84(17) . . ?
O1A C1A N1A 125.82(16) . . ?
O1A C1A C2A 127.96(16) . . ?
N1A C1A C2A 106.21(14) . . ?
C3A C2A C7A 122.14(16) . . ?
C3A C2A C1A 129.41(16) . . ?
C7A C2A C1A 108.45(15) . . ?
C2A C3A C4A 117.77(17) . . ?
C2A C3A H2A 120.9(14) . . ?
C4A C3A H2A 121.3(14) . . ?
C3A C4A C5A 120.61(17) . . ?
C3A C4A H3A 119.2(14) . . ?
C5A C4A H3A 120.1(14) . . ?
C6A C5A C4A 121.28(17) . . ?
C6A C5A H4A 119.5(14) . . ?
C4A C5A H4A 119.2(13) . . ?
C7A C6A C5A 118.29(17) . . ?
C7A C6A H5A 121.1(13) . . ?
C5A C6A H5A 120.6(13) . . ?
C2A C7A C6A 119.90(16) . . ?
C2A C7A C8A 109.56(14) . . ?
C6A C7A C8A 130.53(16) . . ?
N1A C8A C7A 101.30(13) . . ?
N1A C8A C9A 110.27(14) . . ?
C7A C8A C9A 114.56(14) . . ?
N1A C8A H6A 110.6(11) . . ?
C7A C8A H6A 109.1(11) . . ?
C9A C8A H6A 110.6(11) . . ?
C11A C9A C21A 110.73(14) . . ?
C11A C9A C8A 112.06(14) . . ?
C21A C9A C8A 112.53(14) . . ?
C11A C9A H7A 107.7(13) . . ?
C21A C9A H7A 107.0(12) . . ?
C8A C9A H7A 106.5(12) . . ?
N2A C10A O2A 119.17(17) . . ?
N2A C10A C11A 125.14(18) . . ?
O2A C10A C11A 115.69(16) . . ?
C12A C11A C10A 115.89(17) . . ?
C12A C11A C9A 123.78(16) . . ?
C10A C11A C9A 120.32(16) . . ?
C11A C12A C13A 120.48(18) . . ?
C11A C12A H8A 119.6(14) . . ?
C13A C12A H8A 119.9(14) . . ?
C14A C13A C12A 117.97(19) . . ?
C14A C13A H9A 120.1(15) . . ?
C12A C13A H9A 121.9(15) . . ?
N2A C14A C13A 123.68(19) . . ?
N2A C14A H10A 114.6(15) . . ?
C13A C14A H10A 121.7(15) . . ?
O2A C15A H11A 111.4(17) . . ?
O2A C15A H12A 109.7(16) . . ?
H11A C15A H12A 111(2) . . ?
O2A C15A H13A 106.0(18) . . ?
H11A C15A H13A 111(2) . . ?
H12A C15A H13A 108(2) . . ?
C17A C16A C21A 120.3(2) . . ?
C17A C16A H14A 120.8(16) . . ?
C21A C16A H14A 118.8(16) . . ?
C18A C17A C16A 120.4(2) . . ?
C18A C17A H15A 120.9(17) . . ?
C16A C17A H15A 118.6(17) . . ?
C17A C18A C19A 119.9(2) . . ?
C17A C18A H16A 120.9(16) . . ?
C19A C18A H16A 119.2(16) . . ?
C18A C19A C20A 119.8(2) . . ?
C18A C19A H17A 121.6(17) . . ?
C20A C19A H17A 118.6(17) . . ?
C21A C20A C19A 120.9(2) . . ?
C21A C20A H18A 121.1(14) . . ?
C19A C20A H18A 118.0(14) . . ?
C20A C21A C16A 118.65(18) . . ?
C20A C21A C9A 121.32(16) . . ?
C16A C21A C9A 120.03(18) . . ?
C10B O2B C15B 116.32(14) . . ?
C1B N1B C8B 113.91(14) . . ?
C1B N1B H1B 120.8(17) . . ?
C8B N1B H1B 124.3(17) . . ?
C10B N2B C14B 117.47(16) . . ?
O1B C1B N1B 126.27(16) . . ?
O1B C1B C2B 127.05(16) . . ?
N1B C1B C2B 106.64(15) . . ?
C7B C2B C3B 122.95(16) . . ?
C7B C2B C1B 108.76(15) . . ?
C3B C2B C1B 128.14(17) . . ?
C4B C3B C2B 117.28(18) . . ?
C4B C3B H2B 121.4(13) . . ?
C2B C3B H2B 121.3(13) . . ?
C3B C4B C5B 120.42(17) . . ?
C3B C4B H3B 119.4(14) . . ?
C5B C4B H3B 120.1(14) . . ?
C6B C5B C4B 121.84(17) . . ?
C6B C5B H4B 118.7(14) . . ?
C4B C5B H4B 119.4(14) . . ?
C5B C6B C7B 117.95(18) . . ?
C5B C6B H5B 121.2(12) . . ?
C7B C6B H5B 120.8(12) . . ?
C2B C7B C6B 119.52(16) . . ?
C2B C7B C8B 109.35(14) . . ?
C6B C7B C8B 131.11(16) . . ?
N1B C8B C7B 101.19(13) . . ?
N1B C8B C9B 112.27(13) . . ?
C7B C8B C9B 113.50(14) . . ?
N1B C8B H6B 109.7(11) . . ?
C7B C8B H6B 110.0(11) . . ?
C9B C8B H6B 109.8(12) . . ?
C11B C9B C21B 109.62(13) . . ?
C11B C9B C8B 113.15(14) . . ?
C21B C9B C8B 110.76(13) . . ?
C11B C9B H7B 108.6(12) . . ?
C21B C9B H7B 108.7(12) . . ?
C8B C9B H7B 105.8(12) . . ?
N2B C10B O2B 118.80(15) . . ?
N2B C10B C11B 124.84(16) . . ?
O2B C10B C11B 116.36(14) . . ?
C12B C11B C10B 115.71(15) . . ?
C12B C11B C9B 124.21(15) . . ?
C10B C11B C9B 120.04(15) . . ?
C11B C12B C13B 120.59(17) . . ?
C11B C12B H8B 120.7(13) . . ?
C13B C12B H8B 118.7(13) . . ?
C14B C13B C12B 118.20(17) . . ?
C14B C13B H9B 120.6(13) . . ?
C12B C13B H9B 121.2(14) . . ?
N2B C14B C13B 123.19(17) . . ?
N2B C14B H10B 113.6(13) . . ?
C13B C14B H10B 123.2(13) . . ?
O2B C15B H11B 109.4(14) . . ?
O2B C15B H12B 108.0(16) . . ?
H11B C15B H12B 113(2) . . ?
O2B C15B H13B 105.9(16) . . ?
H11B C15B H13B 109(2) . . ?
H12B C15B H13B 111(2) . . ?
C17B C16B C21B 120.52(17) . . ?
C17B C16B H14B 122.0(13) . . ?
C21B C16B H14B 117.4(13) . . ?
C18B C17B C16B 120.34(18) . . ?
C18B C17B H15B 120.7(14) . . ?
C16B C17B H15B 119.0(14) . . ?
C17B C18B C19B 119.56(17) . . ?
C17B C18B H16B 119.5(14) . . ?
C19B C18B H16B 121.0(14) . . ?
C18B C19B C20B 120.22(18) . . ?
C18B C19B H17B 120.6(15) . . ?
C20B C19B H17B 119.2(15) . . ?
C19B C20B C21B 120.73(17) . . ?
C19B C20B H18B 118.9(13) . . ?
C21B C20B H18B 120.4(13) . . ?
C20B C21B C16B 118.63(16) . . ?
C20B C21B C9B 120.66(15) . . ?
C16B C21B C9B 120.70(15) . . ?
Cl1 C1S Cl2 111.19(14) . . ?
Cl1 C1S Cl3 109.28(13) . . ?
Cl2 C1S Cl3 106.86(16) . . ?
Cl1 C1S H1S 109.8 . . ?
Cl2 C1S H1S 109.8 . . ?
Cl3 C1S H1S 109.8 . . ?
Cl1' C1S' Cl3' 142.4(15) . . ?
Cl1' C1S' Cl2' 104.4(8) . . ?
Cl3' C1S' Cl2' 96.3(8) . . ?
Cl1' C1S' H1S' 102.7 . . ?
Cl3' C1S' H1S' 102.7 . . ?
Cl2' C1S' H1S' 102.7 . . ?

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
C8A N1A C1A O1A -178.63(16) . . . . ?
C8A N1A C1A C2A 0.5(2) . . . . ?
O1A C1A C2A C3A -0.5(3) . . . . ?
N1A C1A C2A C3A -179.59(17) . . . . ?
O1A C1A C2A C7A 178.70(17) . . . . ?
N1A C1A C2A C7A -0.39(19) . . . . ?
C7A C2A C3A C4A -0.7(3) . . . . ?
C1A C2A C3A C4A 178.38(17) . . . . ?
C2A C3A C4A C5A 0.7(3) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C4A C5A C6A C7A -0.4(3) . . . . ?
C3A C2A C7A C6A 0.2(3) . . . . ?
C1A C2A C7A C6A -179.11(15) . . . . ?
C3A C2A C7A C8A 179.44(16) . . . . ?
C1A C2A C7A C8A 0.16(19) . . . . ?
C5A C6A C7A C2A 0.4(3) . . . . ?
C5A C6A C7A C8A -178.72(17) . . . . ?
C1A N1A C8A C7A -0.37(19) . . . . ?
C1A N1A C8A C9A -122.08(16) . . . . ?
C2A C7A C8A N1A 0.10(18) . . . . ?
C6A C7A C8A N1A 179.27(18) . . . . ?
C2A C7A C8A C9A 118.77(16) . . . . ?
C6A C7A C8A C9A -62.1(2) . . . . ?
N1A C8A C9A C11A -57.82(19) . . . . ?
C7A C8A C9A C11A -171.30(14) . . . . ?
N1A C8A C9A C21A 176.61(14) . . . . ?
C7A C8A C9A C21A 63.13(19) . . . . ?
C14A N2A C10A O2A 179.69(16) . . . . ?
C14A N2A C10A C11A -0.2(3) . . . . ?
C15A O2A C10A N2A -1.6(3) . . . . ?
C15A O2A C10A C11A 178.28(17) . . . . ?
N2A C10A C11A C12A 0.7(3) . . . . ?
O2A C10A C11A C12A -179.23(16) . . . . ?
N2A C10A C11A C9A 179.62(16) . . . . ?
O2A C10A C11A C9A -0.3(2) . . . . ?
C21A C9A C11A C12A 88.7(2) . . . . ?
C8A C9A C11A C12A -37.9(2) . . . . ?
C21A C9A C11A C10A -90.21(19) . . . . ?
C8A C9A C11A C10A 143.25(16) . . . . ?
C10A C11A C12A C13A -0.7(3) . . . . ?
C9A C11A C12A C13A -179.60(17) . . . . ?
C11A C12A C13A C14A 0.3(3) . . . . ?
C10A N2A C14A C13A -0.3(3) . . . . ?
C12A C13A C14A N2A 0.2(3) . . . . ?
C21A C16A C17A C18A -1.3(3) . . . . ?
C16A C17A C18A C19A 2.1(3) . . . . ?
C17A C18A C19A C20A -0.5(3) . . . . ?
C18A C19A C20A C21A -1.8(3) . . . . ?
C19A C20A C21A C16A 2.6(3) . . . . ?
C19A C20A C21A C9A -177.80(18) . . . . ?
C17A C16A C21A C20A -1.1(3) . . . . ?
C17A C16A C21A C9A 179.33(17) . . . . ?
C11A C9A C21A C20A -75.2(2) . . . . ?
C8A C9A C21A C20A 51.1(2) . . . . ?
C11A C9A C21A C16A 104.44(19) . . . . ?
C8A C9A C21A C16A -129.28(17) . . . . ?
C8B N1B C1B O1B -175.75(17) . . . . ?
C8B N1B C1B C2B 2.15(19) . . . . ?
O1B C1B C2B C7B 174.04(17) . . . . ?
N1B C1B C2B C7B -3.84(19) . . . . ?
O1B C1B C2B C3B -1.6(3) . . . . ?
N1B C1B C2B C3B -179.46(17) . . . . ?
C7B C2B C3B C4B -0.4(3) . . . . ?
C1B C2B C3B C4B 174.65(17) . . . . ?
C2B C3B C4B C5B -1.4(3) . . . . ?
C3B C4B C5B C6B 2.1(3) . . . . ?
C4B C5B C6B C7B -0.9(3) . . . . ?
C3B C2B C7B C6B 1.6(3) . . . . ?
C1B C2B C7B C6B -174.31(15) . . . . ?
C3B C2B C7B C8B 179.91(16) . . . . ?
C1B C2B C7B C8B 4.02(19) . . . . ?
C5B C6B C7B C2B -0.9(3) . . . . ?
C5B C6B C7B C8B -178.83(17) . . . . ?
C1B N1B C8B C7B 0.19(18) . . . . ?
C1B N1B C8B C9B -121.16(16) . . . . ?
C2B C7B C8B N1B -2.63(17) . . . . ?
C6B C7B C8B N1B 175.44(17) . . . . ?
C2B C7B C8B C9B 117.85(15) . . . . ?
C6B C7B C8B C9B -64.1(2) . . . . ?
N1B C8B C9B C11B -54.28(18) . . . . ?
C7B C8B C9B C11B -168.28(13) . . . . ?
N1B C8B C9B C21B -177.81(13) . . . . ?
C7B C8B C9B C21B 68.18(18) . . . . ?
C14B N2B C10B O2B 179.46(15) . . . . ?
C14B N2B C10B C11B 0.0(3) . . . . ?
C15B O2B C10B N2B 1.2(2) . . . . ?
C15B O2B C10B C11B -179.28(15) . . . . ?
N2B C10B C11B C12B -0.5(2) . . . . ?
O2B C10B C11B C12B 180.00(15) . . . . ?
N2B C10B C11B C9B 177.19(15) . . . . ?
O2B C10B C11B C9B -2.3(2) . . . . ?
C21B C9B C11B C12B 99.53(19) . . . . ?
C8B C9B C11B C12B -24.6(2) . . . . ?
C21B C9B C11B C10B -77.97(18) . . . . ?
C8B C9B C11B C10B 157.87(14) . . . . ?
C10B C11B C12B C13B 0.4(2) . . . . ?
C9B C11B C12B C13B -177.21(16) . . . . ?
C11B C12B C13B C14B 0.2(3) . . . . ?
C10B N2B C14B C13B 0.7(3) . . . . ?
C12B C13B C14B N2B -0.8(3) . . . . ?
C21B C16B C17B C18B 0.4(3) . . . . ?
C16B C17B C18B C19B -0.7(3) . . . . ?
C17B C18B C19B C20B 0.5(3) . . . . ?
C18B C19B C20B C21B 0.0(3) . . . . ?
C19B C20B C21B C16B -0.4(3) . . . . ?
C19B C20B C21B C9B -179.73(17) . . . . ?
C17B C16B C21B C20B 0.2(3) . . . . ?
C17B C16B C21B C9B 179.53(16) . . . . ?
C11B C9B C21B C20B -56.4(2) . . . . ?
C8B C9B C21B C20B 69.10(19) . . . . ?
C11B C9B C21B C16B 124.20(17) . . . . ?
C8B C9B C21B C16B -110.25(18) . . . . ?

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
N1A H1A O1B 0.91(3) 1.89(3) 2.794(2) 169(2) . yes
N1B H1B O1A 0.88(3) 2.13(3) 2.9925(19) 166(2) . yes

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.055


