# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_22017
_database_code_depnum_ccdc_archive 'CCDC 2170342'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-10-14 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         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34

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'
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                   17.4160(7)
_cell_length_b                   7.3263(4)
_cell_length_c                   11.8242(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.273(2)
_cell_angle_gamma                90
_cell_volume                     1506.25(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9228
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.228
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7128
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'1 deg frames measured for 1 s at detector distance of 40 mm'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            40558
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3474
_reflns_number_gt                2685
_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       'BIS v6.2.14 (Bruker_AXS, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2019)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
C. B. HÃ1/4bschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX4 v2021.6-RC4 (Bruker AXS, 2021)'

_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)+(0.0524P)²+0.5674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.53587(5) 0.32430(15) 0.87910(8) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.49339(6) 0.2984(2) 0.69778(9) 0.0576(4) Uani 1 1 d . . . . .
C1 C 0.65282(7) 0.29955(19) 0.62484(11) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.609099 0.264875 0.570587 0.030 Uiso 1 1 calc R U . . .
C2 C 0.69758(8) 0.46058(19) 0.58375(11) 0.0255(3) Uani 1 1 d . . . . .
C3 C 0.68825(9) 0.5425(2) 0.47816(12) 0.0329(3) Uani 1 1 d . . . . .
H3 H 0.648782 0.503050 0.424948 0.039 Uiso 1 1 calc R U . . .
C4 C 0.73751(10) 0.6832(2) 0.45138(14) 0.0416(4) Uani 1 1 d . . . . .
H4 H 0.731906 0.739515 0.378989 0.050 Uiso 1 1 calc R U . . .
C5 C 0.79459(10) 0.7423(2) 0.52887(15) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.827391 0.839720 0.509568 0.049 Uiso 1 1 calc R U . . .
C6 C 0.80445(9) 0.6604(2) 0.63494(13) 0.0331(3) Uani 1 1 d . . . . .
H6 H 0.843664 0.701088 0.688178 0.040 Uiso 1 1 calc R U . . .
C7 C 0.75608(7) 0.51859(19) 0.66148(11) 0.0250(3) Uani 1 1 d . . . . .
C8 C 0.76131(7) 0.40385(19) 0.76780(11) 0.0244(3) Uani 1 1 d . . . . .
H8 H 0.801392 0.450341 0.824535 0.029 Uiso 1 1 calc R U . . .
C9 C 0.68274(7) 0.3976(2) 0.81503(11) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.674023 0.429795 0.891065 0.030 Uiso 1 1 calc R U . . .
C10 C 0.62657(7) 0.34335(19) 0.74156(11) 0.0249(3) Uani 1 1 d . . . . .
C11 C 0.71314(8) 0.1430(2) 0.64234(12) 0.0273(3) Uani 1 1 d . . . . .
H11A H 0.687493 0.031570 0.668817 0.033 Uiso 1 1 calc R U . . .
H11B H 0.735669 0.114717 0.569374 0.033 Uiso 1 1 calc R U . . .
C12 C 0.77781(7) 0.20083(19) 0.73071(11) 0.0238(3) Uani 1 1 d . . . . .
H12 H 0.773100 0.121871 0.798953 0.029 Uiso 1 1 calc R U . . .
C13 C 0.85858(7) 0.17640(18) 0.69203(11) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.88113(8) 0.2384(2) 0.58710(11) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.844639 0.296164 0.536130 0.033 Uiso 1 1 calc R U . . .
C15 C 0.95635(8) 0.2163(2) 0.55685(12) 0.0321(3) Uani 1 1 d . . . . .
H15 H 0.971167 0.259827 0.485627 0.039 Uiso 1 1 calc R U . . .
C16 C 1.00994(8) 0.1310(2) 0.62999(13) 0.0342(3) Uani 1 1 d . . . . .
H16 H 1.061452 0.116643 0.609073 0.041 Uiso 1 1 calc R U . . .
C17 C 0.98855(8) 0.0671(2) 0.73293(13) 0.0317(3) Uani 1 1 d . . . . .
H17 H 1.025173 0.007886 0.783034 0.038 Uiso 1 1 calc R U . . .
C18 C 0.91337(8) 0.08918(19) 0.76342(12) 0.0268(3) Uani 1 1 d . . . . .
H18 H 0.898963 0.043900 0.834451 0.032 Uiso 1 1 calc R U . . .
C19 C 0.54531(8) 0.3199(2) 0.76770(12) 0.0291(3) Uani 1 1 d . . . . .
C20 C 0.45865(8) 0.3002(3) 0.91353(13) 0.0427(4) Uani 1 1 d . . . . .
H20A H 0.459417 0.288378 0.996149 0.064 Uiso 1 1 calc R U . . .
H20B H 0.436487 0.189606 0.878308 0.064 Uiso 1 1 calc R U . . .
H20C H 0.427435 0.406110 0.889609 0.064 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 C19 1.3371(17) . ?
O1 C20 1.4381(16) . ?
O2 C19 1.2004(17) . ?
C1 C2 1.510(2) . ?
C1 C10 1.5129(18) . ?
C1 C11 1.5610(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.3865(19) . ?
C2 C7 1.3988(19) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.5107(19) . ?
C8 C9 1.5079(18) . ?
C8 C12 1.5816(19) . ?
C8 H8 1.0000 . ?
C9 C10 1.3314(18) . ?
C9 H9 0.9500 . ?
C10 C19 1.4757(18) . ?
C11 C12 1.5510(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5145(18) . ?
C12 H12 1.0000 . ?
C13 C18 1.3926(18) . ?
C13 C14 1.3984(19) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C20 116.45(11) . . ?
C2 C1 C10 108.44(11) . . ?
C2 C1 C11 105.12(11) . . ?
C10 C1 C11 105.72(11) . . ?
C2 C1 H1 112.4 . . ?
C10 C1 H1 112.4 . . ?
C11 C1 H1 112.4 . . ?
C3 C2 C7 120.24(14) . . ?
C3 C2 C1 126.30(13) . . ?
C7 C2 C1 113.34(12) . . ?
C2 C3 C4 118.97(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.75(15) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.61(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.84(15) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 120.58(13) . . ?
C6 C7 C8 126.69(13) . . ?
C2 C7 C8 112.63(12) . . ?
C9 C8 C7 108.19(11) . . ?
C9 C8 C12 104.91(11) . . ?
C7 C8 C12 107.21(10) . . ?
C9 C8 H8 112.0 . . ?
C7 C8 H8 112.0 . . ?
C12 C8 H8 112.0 . . ?
C10 C9 C8 114.58(12) . . ?
C10 C9 H9 122.7 . . ?
C8 C9 H9 122.7 . . ?
C9 C10 C19 125.15(12) . . ?
C9 C10 C1 114.17(12) . . ?
C19 C10 C1 120.65(11) . . ?
C12 C11 C1 110.25(11) . . ?
C12 C11 H11A 109.6 . . ?
C1 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C1 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 114.56(11) . . ?
C13 C12 C8 112.43(11) . . ?
C11 C12 C8 107.88(10) . . ?
C13 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
C8 C12 H12 107.2 . . ?
C18 C13 C14 118.00(12) . . ?
C18 C13 C12 119.16(12) . . ?
C14 C13 C12 122.84(12) . . ?
C15 C14 C13 120.53(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.30(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.97(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.83(13) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.35(13) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
O2 C19 O1 123.47(13) . . ?
O2 C19 C10 124.39(13) . . ?
O1 C19 C10 112.14(11) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C1 C2 C3 -132.49(14) . . . . ?
C11 C1 C2 C3 114.81(15) . . . . ?
C10 C1 C2 C7 51.48(15) . . . . ?
C11 C1 C2 C7 -61.23(14) . . . . ?
C7 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C3 C4 -176.16(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C2 -1.0(2) . . . . ?
C5 C6 C7 C8 175.10(13) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
C1 C2 C7 C6 177.48(12) . . . . ?
C3 C2 C7 C8 -175.42(12) . . . . ?
C1 C2 C7 C8 0.88(16) . . . . ?
C6 C7 C8 C9 130.70(14) . . . . ?
C2 C7 C8 C9 -52.95(15) . . . . ?
C6 C7 C8 C12 -116.64(14) . . . . ?
C2 C7 C8 C12 59.71(14) . . . . ?
C7 C8 C9 C10 53.51(16) . . . . ?
C12 C8 C9 C10 -60.68(15) . . . . ?
C8 C9 C10 C19 177.88(13) . . . . ?
C8 C9 C10 C1 -0.29(18) . . . . ?
C2 C1 C10 C9 -52.52(16) . . . . ?
C11 C1 C10 C9 59.79(15) . . . . ?
C2 C1 C10 C19 129.22(13) . . . . ?
C11 C1 C10 C19 -118.47(14) . . . . ?
C2 C1 C11 C12 59.82(14) . . . . ?
C10 C1 C11 C12 -54.80(14) . . . . ?
C1 C11 C12 C13 -128.62(12) . . . . ?
C1 C11 C12 C8 -2.59(15) . . . . ?
C9 C8 C12 C13 -173.99(10) . . . . ?
C7 C8 C12 C13 71.13(13) . . . . ?
C9 C8 C12 C11 58.74(13) . . . . ?
C7 C8 C12 C11 -56.14(13) . . . . ?
C11 C12 C13 C18 -131.53(13) . . . . ?
C8 C12 C13 C18 104.83(14) . . . . ?
C11 C12 C13 C14 48.69(18) . . . . ?
C8 C12 C13 C14 -74.94(16) . . . . ?
C18 C13 C14 C15 -1.3(2) . . . . ?
C12 C13 C14 C15 178.51(13) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C13 -0.4(2) . . . . ?
C14 C13 C18 C17 1.2(2) . . . . ?
C12 C13 C18 C17 -178.56(13) . . . . ?
C20 O1 C19 O2 0.4(2) . . . . ?
C20 O1 C19 C10 -179.20(14) . . . . ?
C9 C10 C19 O2 168.02(18) . . . . ?
C1 C10 C19 O2 -13.9(2) . . . . ?
C9 C10 C19 O1 -12.3(2) . . . . ?
C1 C10 C19 O1 165.71(13) . . . . ?

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
C20 H20A O2 0.98 2.51 3.457(2) 163.7 4_566 yes

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_22018
_database_code_depnum_ccdc_archive 'CCDC 2170343'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-10-14 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         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6874(7)
_cell_length_b                   14.9785(12)
_cell_length_c                   11.1842(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.606(2)
_cell_angle_gamma                90
_cell_volume                     1487.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'1 deg frames measured 3 and 1 s at detector distance of 40 mm'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            57415
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3047
_reflns_number_gt                2445
_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       'BIS v6.2.14 (Bruker_AXS, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2019)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
C. B. HÃ1/4bschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX4 v2021.6-RC4 (Bruker AXS, 2021)'
_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)+(0.0592P)²+0.7699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.84118(13) 0.66332(8) 0.88008(12) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.80089(14) 0.56716(9) 1.01563(12) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.48143(19) 0.61391(11) 0.91559(15) 0.0213(4) Uani 1 1 d . . . . .
H1 H 0.528033 0.571576 0.990160 0.026 Uiso 1 1 calc R U . . .
C2 C 0.40473(18) 0.69133(12) 0.95051(16) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.3909(2) 0.70545(15) 1.06759(18) 0.0344(5) Uani 1 1 d . . . . .
H3 H 0.429808 0.663163 1.136359 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3190(2) 0.78265(17) 1.0833(2) 0.0447(6) Uani 1 1 d . . . . .
H4 H 0.310558 0.793309 1.163815 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2600(2) 0.84366(15) 0.9829(2) 0.0414(6) Uani 1 1 d . . . . .
H5 H 0.211172 0.895800 0.994829 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2717(2) 0.82929(13) 0.8649(2) 0.0336(5) Uani 1 1 d . . . . .
H6 H 0.229383 0.870556 0.795114 0.040 Uiso 1 1 calc R U . . .
C7 C 0.34617(18) 0.75380(11) 0.85021(17) 0.0235(4) Uani 1 1 d . . . . .
C8 C 0.37263(18) 0.72838(11) 0.73020(16) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.335170 0.775155 0.660760 0.027 Uiso 1 1 calc R U . . .
C9 C 0.53955(18) 0.71176(11) 0.77387(15) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.598983 0.740905 0.735604 0.024 Uiso 1 1 calc R U . . .
C10 C 0.59642(18) 0.65281(10) 0.87054(15) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.36276(19) 0.56715(11) 0.79318(16) 0.0231(4) Uani 1 1 d . . . . .
H11A H 0.412674 0.521204 0.760709 0.028 Uiso 1 1 calc R U . . .
H11B H 0.285987 0.537266 0.816758 0.028 Uiso 1 1 calc R U . . .
C12 C 0.28588(18) 0.63754(12) 0.68489(16) 0.0224(4) Uani 1 1 d . . . . .
H12 H 0.182359 0.647147 0.681803 0.027 Uiso 1 1 calc R U . . .
C13 C 0.26641(19) 0.60813(12) 0.54948(16) 0.0237(4) Uani 1 1 d . . . . .
C14 C 0.1257(2) 0.58293(12) 0.46079(17) 0.0274(4) Uani 1 1 d . . . . .
H14 H 0.043588 0.583569 0.486750 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1005(2) 0.55670(14) 0.33490(18) 0.0343(4) Uani 1 1 d . . . . .
H15 H 0.002351 0.539457 0.276108 0.041 Uiso 1 1 calc R U . . .
C16 C 0.2180(2) 0.55567(13) 0.29513(17) 0.0330(4) Uani 1 1 d . . . . .
H16 H 0.201708 0.538090 0.208892 0.040 Uiso 1 1 calc R U . . .
C17 C 0.3576(3) 0.58019(19) 0.3812(2) 0.0505(6) Uani 1 1 d . . . . .
H17 H 0.439079 0.579716 0.354415 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3831(2) 0.60592(19) 0.5076(2) 0.0493(7) Uani 1 1 d . . . . .
H18 H 0.481851 0.622244 0.566128 0.059 Uiso 1 1 calc R U . . .
C19 C 0.75443(18) 0.62241(11) 0.93031(15) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.9988(2) 0.63955(14) 0.93551(19) 0.0342(4) Uani 1 1 d . . . . .
H20A H 1.052133 0.674305 0.893050 0.051 Uiso 1 1 calc R U . . .
H20B H 1.009466 0.575738 0.921862 0.051 Uiso 1 1 calc R U . . .
H20C H 1.041678 0.652481 1.029249 0.051 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 C19 1.332(2) . ?
O1 C20 1.443(2) . ?
O2 C19 1.206(2) . ?
C1 C2 1.510(2) . ?
C1 C10 1.511(2) . ?
C1 C11 1.558(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.385(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.513(2) . ?
C8 C9 1.511(2) . ?
C8 C12 1.573(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.332(2) . ?
C9 H9 0.9500 . ?
C10 C19 1.476(2) . ?
C11 C12 1.553(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.515(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.379(2) . ?
C13 C18 1.387(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.359(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C20 116.27(14) . . ?
C2 C1 C10 107.15(13) . . ?
C2 C1 C11 107.82(14) . . ?
C10 C1 C11 105.28(13) . . ?
C2 C1 H1 112.1 . . ?
C10 C1 H1 112.1 . . ?
C11 C1 H1 112.1 . . ?
C3 C2 C7 119.72(18) . . ?
C3 C2 C1 127.27(17) . . ?
C7 C2 C1 113.00(14) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.68(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.43(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.04(17) . . ?
C6 C7 C8 126.27(17) . . ?
C2 C7 C8 112.69(15) . . ?
C9 C8 C7 107.12(13) . . ?
C9 C8 C12 109.04(13) . . ?
C7 C8 C12 104.20(13) . . ?
C9 C8 H8 112.0 . . ?
C7 C8 H8 112.0 . . ?
C12 C8 H8 112.0 . . ?
C10 C9 C8 114.37(14) . . ?
C10 C9 H9 122.8 . . ?
C8 C9 H9 122.8 . . ?
C9 C10 C19 126.07(15) . . ?
C9 C10 C1 113.93(15) . . ?
C19 C10 C1 119.96(14) . . ?
C12 C11 C1 109.57(13) . . ?
C12 C11 H11A 109.8 . . ?
C1 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C1 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 114.28(14) . . ?
C13 C12 C8 114.23(14) . . ?
C11 C12 C8 107.98(13) . . ?
C13 C12 H12 106.6 . . ?
C11 C12 H12 106.6 . . ?
C8 C12 H12 106.6 . . ?
C14 C13 C18 117.06(16) . . ?
C14 C13 C12 119.37(15) . . ?
C18 C13 C12 123.57(16) . . ?
C13 C14 C15 121.99(17) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C16 C15 C14 119.91(17) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 118.97(17) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 121.13(19) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 120.93(19) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O2 C19 O1 123.41(15) . . ?
O2 C19 C10 124.12(15) . . ?
O1 C19 C10 112.47(14) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C1 C2 C3 -125.46(18) . . . . ?
C11 C1 C2 C3 121.65(18) . . . . ?
C10 C1 C2 C7 53.33(18) . . . . ?
C11 C1 C2 C7 -59.55(18) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 178.34(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C5 C6 C7 C2 2.0(3) . . . . ?
C5 C6 C7 C8 -178.60(17) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C1 C2 C7 C6 179.95(16) . . . . ?
C3 C2 C7 C8 179.38(15) . . . . ?
C1 C2 C7 C8 0.5(2) . . . . ?
C6 C7 C8 C9 126.87(18) . . . . ?
C2 C7 C8 C9 -53.70(18) . . . . ?
C6 C7 C8 C12 -117.66(18) . . . . ?
C2 C7 C8 C12 61.77(17) . . . . ?
C7 C8 C9 C10 53.91(19) . . . . ?
C12 C8 C9 C10 -58.29(18) . . . . ?
C8 C9 C10 C19 178.59(14) . . . . ?
C8 C9 C10 C1 0.6(2) . . . . ?
C2 C1 C10 C9 -54.68(18) . . . . ?
C11 C1 C10 C9 59.92(18) . . . . ?
C2 C1 C10 C19 127.23(15) . . . . ?
C11 C1 C10 C19 -118.16(15) . . . . ?
C2 C1 C11 C12 51.86(17) . . . . ?
C10 C1 C11 C12 -62.28(16) . . . . ?
C1 C11 C12 C13 136.64(14) . . . . ?
C1 C11 C12 C8 8.34(17) . . . . ?
C9 C8 C12 C13 -78.63(17) . . . . ?
C7 C8 C12 C13 167.26(14) . . . . ?
C9 C8 C12 C11 49.69(17) . . . . ?
C7 C8 C12 C11 -64.42(16) . . . . ?
C11 C12 C13 C14 104.64(18) . . . . ?
C8 C12 C13 C14 -130.30(17) . . . . ?
C11 C12 C13 C18 -76.2(2) . . . . ?
C8 C12 C13 C18 48.8(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 C15 179.00(17) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C12 C13 C18 C17 -178.6(2) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C20 O1 C19 O2 -1.3(2) . . . . ?
C20 O1 C19 C10 178.27(14) . . . . ?
C9 C10 C19 O2 -178.06(17) . . . . ?
C1 C10 C19 O2 -0.2(2) . . . . ?
C9 C10 C19 O1 2.4(2) . . . . ?
C1 C10 C19 O1 -179.81(14) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_22062
_database_code_depnum_ccdc_archive 'CCDC 2170630'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-10-14 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         ' 2(C21 H26 N O), 2 Cl, H2 O'
_chemical_formula_sum            'C42 H54 Cl2 N2 O3'
_chemical_formula_weight         705.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   16.0511(5)
_cell_length_b                   7.7600(3)
_cell_length_c                   17.0992(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.5120(10)
_cell_angle_gamma                90
_cell_volume                     1888.96(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'1 deg frames measured 3 and 2 s, detector distance of 40 mm'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            75469
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8672
_reflns_number_gt                7487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_max     0.997
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'BIS v6.2.14 (Bruker_AXS, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2019)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
C. B. Hübschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX4 v2021.6-RC4 (Bruker AXS, 2021)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8672
_refine_ls_number_parameters     461
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Cl1 Cl 0.37684(4) 0.76130(10) 0.44627(4) 0.03078(17) Uani 1 1 d . . . . .
Cl2 Cl 0.11392(4) 0.74676(10) 0.56430(4) 0.03481(18) Uani 1 1 d . . . . .
O1W O 0.22807(16) 0.9586(3) 0.48824(14) 0.0470(6) Uani 1 1 d . . . . .
H1W H 0.272004 0.879541 0.481721 0.16(3) Uiso 1 1 d R . . . .
H2W H 0.193904 0.897541 0.509819 0.24(4) Uiso 1 1 d R . . . .
O1A O 0.62544(12) 0.3378(3) 0.97043(12) 0.0319(5) Uani 1 1 d . . . . .
N1A N 0.09176(18) 0.3705(4) 0.50419(15) 0.0290(5) Uani 1 1 d . . . . .
H1AA H 0.091(2) 0.475(5) 0.521(2) 0.035 Uiso 1 1 d . U . . .
H1AB H 0.035(2) 0.327(4) 0.4878(19) 0.035 Uiso 1 1 d . U . . .
C1A C 0.22652(17) 0.3341(4) 0.83324(16) 0.0228(6) Uani 1 1 d . . . . .
H1A H 0.214014 0.365965 0.883510 0.027 Uiso 1 1 calc R U . . .
C2A C 0.16698(17) 0.4565(4) 0.75540(16) 0.0241(5) Uani 1 1 d . . . . .
H2AA H 0.142643 0.552684 0.777049 0.029 Uiso 1 1 calc R U . . .
H2AB H 0.207117 0.505906 0.731175 0.029 Uiso 1 1 calc R U . . .
C3A C 0.08422(16) 0.3590(4) 0.68214(15) 0.0228(5) Uani 1 1 d . . . . .
H3A H 0.041603 0.440178 0.635301 0.027 Uiso 1 1 calc R U . . .
C4A C 0.03135(15) 0.2617(4) 0.72178(14) 0.0234(5) Uani 1 1 d . . . . .
C5A C -0.06351(16) 0.2753(4) 0.69699(15) 0.0244(5) Uani 1 1 d . . . . .
H5A H -0.101309 0.356537 0.653448 0.029 Uiso 1 1 calc R U . . .
C6A C -0.10317(19) 0.1684(4) 0.73664(17) 0.0288(6) Uani 1 1 d . . . . .
H6A H -0.168245 0.176877 0.720117 0.035 Uiso 1 1 calc R U . . .
C7A C -0.04752(18) 0.0497(4) 0.80021(17) 0.0298(6) Uani 1 1 d . . . . .
H7A H -0.074906 -0.023990 0.826388 0.036 Uiso 1 1 calc R U . . .
C8A C 0.04801(18) 0.0383(4) 0.82570(17) 0.0301(6) Uani 1 1 d . . . . .
H8A H 0.086124 -0.041521 0.869939 0.036 Uiso 1 1 calc R U . . .
C9A C 0.08737(17) 0.1440(4) 0.78620(16) 0.0245(6) Uani 1 1 d . . . . .
C10A C 0.18885(17) 0.1467(4) 0.80465(16) 0.0238(6) Uani 1 1 d . . . . .
H10A H 0.226760 0.062062 0.851906 0.029 Uiso 1 1 calc R U . . .
C11A C 0.19373(17) 0.1059(4) 0.71929(16) 0.0262(6) Uani 1 1 d . . . . .
H11C H 0.180349 -0.017850 0.704942 0.031 Uiso 1 1 calc R U . . .
H11D H 0.257732 0.130234 0.727279 0.031 Uiso 1 1 calc R U . . .
C12A C 0.12116(16) 0.2168(4) 0.64244(15) 0.0245(6) Uani 1 1 d . . . . .
H12A H 0.066855 0.140431 0.605725 0.029 Uiso 1 1 calc R U . . .
C13A C 0.16321(17) 0.2785(5) 0.58418(17) 0.0310(7) Uani 1 1 d . . . . .
H13C H 0.216307 0.357199 0.618272 0.037 Uiso 1 1 calc R U . . .
H13D H 0.187984 0.178454 0.565520 0.037 Uiso 1 1 calc R U . . .
C14A C 0.1132(3) 0.3717(5) 0.4286(2) 0.0490(9) Uani 1 1 d . . . . .
H14D H 0.061941 0.428503 0.378080 0.073 Uiso 1 1 calc R U . . .
H14E H 0.119789 0.252945 0.412764 0.073 Uiso 1 1 calc R U . . .
H14F H 0.171907 0.434431 0.445005 0.073 Uiso 1 1 calc R U . . .
C15A C 0.33272(17) 0.3384(4) 0.86750(15) 0.0223(5) Uani 1 1 d . . . . .
C16A C 0.38926(16) 0.2633(5) 0.94913(14) 0.0256(5) Uani 1 1 d . . . . .
H16A H 0.360192 0.212725 0.980949 0.031 Uiso 1 1 calc R U . . .
C17A C 0.48664(16) 0.2597(5) 0.98571(15) 0.0264(5) Uani 1 1 d . . . . .
H17A H 0.523190 0.207459 1.041546 0.032 Uiso 1 1 calc R U . . .
C18A C 0.52963(16) 0.3326(4) 0.94017(16) 0.0247(6) Uani 1 1 d . . . . .
C19A C 0.47593(18) 0.4093(4) 0.85901(17) 0.0294(6) Uani 1 1 d . . . . .
H19A H 0.505437 0.460251 0.827662 0.035 Uiso 1 1 calc R U . . .
C20A C 0.37874(18) 0.4114(4) 0.82369(16) 0.0270(6) Uani 1 1 d . . . . .
H20A H 0.342544 0.464199 0.767948 0.032 Uiso 1 1 calc R U . . .
C21A C 0.68140(17) 0.2545(5) 1.05228(17) 0.0362(6) Uani 1 1 d . . . . .
H21D H 0.748014 0.270718 1.068709 0.054 Uiso 1 1 calc R U . . .
H21E H 0.666786 0.131116 1.046612 0.054 Uiso 1 1 calc R U . . .
H21F H 0.667970 0.304313 1.097921 0.054 Uiso 1 1 calc R U . . .
O1B O 1.11817(12) 0.6566(3) 0.97345(12) 0.0326(5) Uani 1 1 d . . . . .
N1B N 0.58097(16) 0.6507(3) 0.49382(14) 0.0248(5) Uani 1 1 d . . . . .
H1BA H 0.588(2) 0.538(5) 0.5061(18) 0.030 Uiso 1 1 d . U . . .
H1BB H 0.528(2) 0.690(4) 0.4843(18) 0.030 Uiso 1 1 d . U . . .
C1B C 0.71767(17) 0.6627(4) 0.82261(16) 0.0233(6) Uani 1 1 d . . . . .
H1B H 0.702335 0.624132 0.870287 0.028 Uiso 1 1 calc R U . . .
C2B C 0.66042(17) 0.5479(4) 0.74103(16) 0.0253(6) Uani 1 1 d . . . . .
H2BA H 0.701466 0.508446 0.715661 0.030 Uiso 1 1 calc R U . . .
H2BB H 0.637243 0.444904 0.759194 0.030 Uiso 1 1 calc R U . . .
C3B C 0.57631(16) 0.6489(3) 0.67062(15) 0.0210(5) Uani 1 1 d . . . . .
H3B H 0.533956 0.570893 0.621839 0.025 Uiso 1 1 calc R U . . .
C4B C 0.52348(16) 0.7370(4) 0.71219(14) 0.0210(5) Uani 1 1 d . . . . .
C5B C 0.42772(16) 0.7264(4) 0.68532(16) 0.0248(6) Uani 1 1 d . . . . .
H5B H 0.389145 0.652028 0.638301 0.030 Uiso 1 1 calc R U . . .
C6B C 0.38872(18) 0.8261(4) 0.72816(17) 0.0283(6) Uani 1 1 d . . . . .
H6B H 0.323448 0.817879 0.710825 0.034 Uiso 1 1 calc R U . . .
C7B C 0.44412(19) 0.9361(4) 0.79532(17) 0.0305(6) Uani 1 1 d . . . . .
H7B H 0.416806 1.003062 0.824051 0.037 Uiso 1 1 calc R U . . .
C8B C 0.54013(19) 0.9501(4) 0.82153(16) 0.0289(6) Uani 1 1 d . . . . .
H8B H 0.578126 1.026825 0.867554 0.035 Uiso 1 1 calc R U . . .
C9B C 0.57937(17) 0.8507(4) 0.77961(15) 0.0230(5) Uani 1 1 d . . . . .
C10B C 0.68074(17) 0.8500(4) 0.79791(17) 0.0244(6) Uani 1 1 d . . . . .
H10B H 0.718594 0.930617 0.847319 0.029 Uiso 1 1 calc R U . . .
C11B C 0.68701(17) 0.9016(4) 0.71418(15) 0.0242(6) Uani 1 1 d . . . . .
H11A H 0.750887 0.877488 0.721767 0.029 Uiso 1 1 calc R U . . .
H11B H 0.674723 1.026513 0.703216 0.029 Uiso 1 1 calc R U . . .
C12B C 0.61339(16) 0.7974(3) 0.63455(15) 0.0222(6) Uani 1 1 d . . . . .
H12B H 0.559182 0.876404 0.601099 0.027 Uiso 1 1 calc R U . . .
C13B C 0.65249(16) 0.7466(5) 0.57230(16) 0.0284(6) Uani 1 1 d . . . . .
H13A H 0.672117 0.851424 0.552163 0.034 Uiso 1 1 calc R U . . .
H13B H 0.708631 0.673091 0.604073 0.034 Uiso 1 1 calc R U . . .
C14B C 0.5860(2) 0.6808(4) 0.40984(18) 0.0364(7) Uani 1 1 d . . . . .
H14A H 0.536007 0.615845 0.362067 0.055 Uiso 1 1 calc R U . . .
H14B H 0.647214 0.642448 0.416730 0.055 Uiso 1 1 calc R U . . .
H14C H 0.578171 0.804026 0.395638 0.055 Uiso 1 1 calc R U . . .
C15B C 0.82439(17) 0.6564(4) 0.86051(15) 0.0231(5) Uani 1 1 d . . . . .
C16B C 0.87272(17) 0.5902(4) 0.81782(16) 0.0262(6) Uani 1 1 d . . . . .
H16B H 0.838374 0.542941 0.760399 0.031 Uiso 1 1 calc R U . . .
C17B C 0.97036(18) 0.5914(4) 0.85715(17) 0.0289(6) Uani 1 1 d . . . . .
H17B H 1.001668 0.544124 0.826612 0.035 Uiso 1 1 calc R U . . .
C18B C 1.02227(18) 0.6609(4) 0.94037(17) 0.0261(6) Uani 1 1 d . . . . .
C19B C 0.97576(17) 0.7297(4) 0.98456(16) 0.0273(6) Uani 1 1 d . . . . .
H19B H 1.010182 0.778470 1.041617 0.033 Uiso 1 1 calc R U . . .
C20B C 0.87837(16) 0.7260(4) 0.94410(15) 0.0252(6) Uani 1 1 d . . . . .
H20B H 0.847092 0.772994 0.974742 0.030 Uiso 1 1 calc R U . . .
C21B C 1.17210(18) 0.7350(5) 1.05772(17) 0.0361(7) Uani 1 1 d . . . . .
H21A H 1.239061 0.727370 1.073918 0.054 Uiso 1 1 calc R U . . .
H21B H 1.160155 0.675158 1.102011 0.054 Uiso 1 1 calc R U . . .
H21C H 1.154055 0.856397 1.055000 0.054 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
O1W H1W 0.9791 . ?
O1W H2W 0.9211 . ?
O1A C18A 1.378(3) . ?
O1A C21A 1.422(3) . ?
N1A C14A 1.483(3) . ?
N1A C13A 1.499(4) . ?
N1A H1AA 0.87(4) . ?
N1A H1AB 0.89(3) . ?
C1A C15A 1.526(3) . ?
C1A C2A 1.553(4) . ?
C1A C10A 1.564(4) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.539(4) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.510(3) . ?
C3A C12A 1.550(3) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.383(3) . ?
C4A C9A 1.393(4) . ?
C5A C6A 1.397(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.390(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.390(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.386(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.509(3) . ?
C10A C11A 1.530(3) . ?
C10A H10A 1.0000 . ?
C11A C12A 1.553(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.516(3) . ?
C12A H12A 1.0000 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A C20A 1.392(3) . ?
C15A C16A 1.393(3) . ?
C16A C17A 1.390(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.378(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.385(4) . ?
C19A C20A 1.389(3) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
O1B C18B 1.373(3) . ?
O1B C21B 1.430(3) . ?
N1B C14B 1.494(3) . ?
N1B C13B 1.500(3) . ?
N1B H1BA 0.90(4) . ?
N1B H1BB 0.85(3) . ?
C1B C15B 1.527(3) . ?
C1B C2B 1.549(4) . ?
C1B C10B 1.553(4) . ?
C1B H1B 1.0000 . ?
C2B C3B 1.544(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.500(3) . ?
C3B C12B 1.550(3) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.389(3) . ?
C4B C9B 1.399(4) . ?
C5B C6B 1.397(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.377(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.396(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.386(4) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.508(3) . ?
C10B C11B 1.534(4) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.555(3) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C12B C13B 1.516(3) . ?
C12B H12B 1.0000 . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B H14A 0.9800 . ?
C14B H14B 0.9800 . ?
C14B H14C 0.9800 . ?
C15B C16B 1.386(3) . ?
C15B C20B 1.393(3) . ?
C16B C17B 1.391(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.384(4) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.391(4) . ?
C19B C20B 1.387(3) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C21B H21A 0.9800 . ?
C21B H21B 0.9800 . ?
C21B H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1W O1W H2W 108.5 . . ?
C18A O1A C21A 116.4(2) . . ?
C14A N1A C13A 114.3(2) . . ?
C14A N1A H1AA 109(2) . . ?
C13A N1A H1AA 106(2) . . ?
C14A N1A H1AB 110.3(19) . . ?
C13A N1A H1AB 110(2) . . ?
H1AA N1A H1AB 107(3) . . ?
C15A C1A C2A 116.8(2) . . ?
C15A C1A C10A 110.0(2) . . ?
C2A C1A C10A 107.8(2) . . ?
C15A C1A H1A 107.3 . . ?
C2A C1A H1A 107.3 . . ?
C10A C1A H1A 107.3 . . ?
C3A C2A C1A 110.8(2) . . ?
C3A C2A H2AA 109.5 . . ?
C1A C2A H2AA 109.5 . . ?
C3A C2A H2AB 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 108.1 . . ?
C4A C3A C2A 109.46(19) . . ?
C4A C3A C12A 104.4(2) . . ?
C2A C3A C12A 110.2(2) . . ?
C4A C3A H3A 110.9 . . ?
C2A C3A H3A 110.9 . . ?
C12A C3A H3A 110.9 . . ?
C5A C4A C9A 120.6(3) . . ?
C5A C4A C3A 126.3(3) . . ?
C9A C4A C3A 113.0(2) . . ?
C4A C5A C6A 119.3(3) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
C7A C6A C5A 120.1(2) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 120.3(3) . . ?
C6A C7A H7A 119.8 . . ?
C8A C7A H7A 119.8 . . ?
C9A C8A C7A 119.6(3) . . ?
C9A C8A H8A 120.2 . . ?
C7A C8A H8A 120.2 . . ?
C8A C9A C4A 120.0(2) . . ?
C8A C9A C10A 126.7(2) . . ?
C4A C9A C10A 113.3(2) . . ?
C9A C10A C11A 108.9(2) . . ?
C9A C10A C1A 107.6(2) . . ?
C11A C10A C1A 107.9(2) . . ?
C9A C10A H10A 110.8 . . ?
C11A C10A H10A 110.8 . . ?
C1A C10A H10A 110.8 . . ?
C10A C11A C12A 110.1(2) . . ?
C10A C11A H11C 109.6 . . ?
C12A C11A H11C 109.6 . . ?
C10A C11A H11D 109.6 . . ?
C12A C11A H11D 109.6 . . ?
H11C C11A H11D 108.2 . . ?
C13A C12A C3A 116.1(2) . . ?
C13A C12A C11A 110.1(2) . . ?
C3A C12A C11A 108.25(19) . . ?
C13A C12A H12A 107.3 . . ?
C3A C12A H12A 107.3 . . ?
C11A C12A H12A 107.3 . . ?
N1A C13A C12A 111.4(2) . . ?
N1A C13A H13C 109.3 . . ?
C12A C13A H13C 109.3 . . ?
N1A C13A H13D 109.3 . . ?
C12A C13A H13D 109.3 . . ?
H13C C13A H13D 108.0 . . ?
N1A C14A H14D 109.5 . . ?
N1A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N1A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C20A C15A C16A 116.6(2) . . ?
C20A C15A C1A 125.4(2) . . ?
C16A C15A C1A 118.1(2) . . ?
C17A C16A C15A 122.4(2) . . ?
C17A C16A H16A 118.8 . . ?
C15A C16A H16A 118.8 . . ?
C18A C17A C16A 119.3(2) . . ?
C18A C17A H17A 120.3 . . ?
C16A C17A H17A 120.3 . . ?
C17A C18A O1A 124.3(2) . . ?
C17A C18A C19A 120.0(2) . . ?
O1A C18A C19A 115.7(2) . . ?
C18A C19A C20A 119.7(2) . . ?
C18A C19A H19A 120.2 . . ?
C20A C19A H19A 120.2 . . ?
C19A C20A C15A 122.0(2) . . ?
C19A C20A H20A 119.0 . . ?
C15A C20A H20A 119.0 . . ?
O1A C21A H21D 109.5 . . ?
O1A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
O1A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C18B O1B C21B 116.5(2) . . ?
C14B N1B C13B 115.0(2) . . ?
C14B N1B H1BA 108.8(18) . . ?
C13B N1B H1BA 108.4(19) . . ?
C14B N1B H1BB 104.8(19) . . ?
C13B N1B H1BB 106(2) . . ?
H1BA N1B H1BB 114(3) . . ?
C15B C1B C2B 116.5(2) . . ?
C15B C1B C10B 111.0(2) . . ?
C2B C1B C10B 107.5(2) . . ?
C15B C1B H1B 107.2 . . ?
C2B C1B H1B 107.2 . . ?
C10B C1B H1B 107.2 . . ?
C3B C2B C1B 110.6(2) . . ?
C3B C2B H2BA 109.5 . . ?
C1B C2B H2BA 109.5 . . ?
C3B C2B H2BB 109.5 . . ?
C1B C2B H2BB 109.5 . . ?
H2BA C2B H2BB 108.1 . . ?
C4B C3B C2B 110.1(2) . . ?
C4B C3B C12B 104.7(2) . . ?
C2B C3B C12B 109.24(19) . . ?
C4B C3B H3B 110.9 . . ?
C2B C3B H3B 110.9 . . ?
C12B C3B H3B 110.9 . . ?
C5B C4B C9B 120.0(2) . . ?
C5B C4B C3B 126.7(2) . . ?
C9B C4B C3B 113.0(2) . . ?
C4B C5B C6B 119.3(2) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
C7B C6B C5B 120.5(2) . . ?
C7B C6B H6B 119.7 . . ?
C5B C6B H6B 119.7 . . ?
C6B C7B C8B 120.5(2) . . ?
C6B C7B H7B 119.7 . . ?
C8B C7B H7B 119.7 . . ?
C9B C8B C7B 119.2(3) . . ?
C9B C8B H8B 120.4 . . ?
C7B C8B H8B 120.4 . . ?
C8B C9B C4B 120.4(2) . . ?
C8B C9B C10B 126.8(2) . . ?
C4B C9B C10B 112.8(2) . . ?
C9B C10B C11B 109.6(2) . . ?
C9B C10B C1B 107.4(2) . . ?
C11B C10B C1B 108.5(2) . . ?
C9B C10B H10B 110.4 . . ?
C11B C10B H10B 110.4 . . ?
C1B C10B H10B 110.4 . . ?
C10B C11B C12B 109.3(2) . . ?
C10B C11B H11A 109.8 . . ?
C12B C11B H11A 109.8 . . ?
C10B C11B H11B 109.8 . . ?
C12B C11B H11B 109.8 . . ?
H11A C11B H11B 108.3 . . ?
C13B C12B C3B 116.4(2) . . ?
C13B C12B C11B 110.88(19) . . ?
C3B C12B C11B 108.32(19) . . ?
C13B C12B H12B 106.9 . . ?
C3B C12B H12B 106.9 . . ?
C11B C12B H12B 106.9 . . ?
N1B C13B C12B 111.30(19) . . ?
N1B C13B H13A 109.4 . . ?
C12B C13B H13A 109.4 . . ?
N1B C13B H13B 109.4 . . ?
C12B C13B H13B 109.4 . . ?
H13A C13B H13B 108.0 . . ?
N1B C14B H14A 109.5 . . ?
N1B C14B H14B 109.5 . . ?
H14A C14B H14B 109.5 . . ?
N1B C14B H14C 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?
C16B C15B C20B 116.7(2) . . ?
C16B C15B C1B 125.4(2) . . ?
C20B C15B C1B 117.8(2) . . ?
C15B C16B C17B 121.5(2) . . ?
C15B C16B H16B 119.3 . . ?
C17B C16B H16B 119.3 . . ?
C18B C17B C16B 120.6(2) . . ?
C18B C17B H17B 119.7 . . ?
C16B C17B H17B 119.7 . . ?
O1B C18B C17B 116.2(2) . . ?
O1B C18B C19B 124.5(2) . . ?
C17B C18B C19B 119.3(2) . . ?
C20B C19B C18B 119.0(2) . . ?
C20B C19B H19B 120.5 . . ?
C18B C19B H19B 120.5 . . ?
C19B C20B C15B 122.9(2) . . ?
C19B C20B H20B 118.6 . . ?
C15B C20B H20B 118.6 . . ?
O1B C21B H21A 109.5 . . ?
O1B C21B H21B 109.5 . . ?
H21A C21B H21B 109.5 . . ?
O1B C21B H21C 109.5 . . ?
H21A C21B H21C 109.5 . . ?
H21B C21B H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15A C1A C2A C3A 131.7(2) . . . . ?
C10A C1A C2A C3A 7.2(3) . . . . ?
C1A C2A C3A C4A 50.8(3) . . . . ?
C1A C2A C3A C12A -63.5(3) . . . . ?
C2A C3A C4A C5A 124.3(3) . . . . ?
C12A C3A C4A C5A -117.7(3) . . . . ?
C2A C3A C4A C9A -58.7(3) . . . . ?
C12A C3A C4A C9A 59.3(3) . . . . ?
C9A C4A C5A C6A -0.6(4) . . . . ?
C3A C4A C5A C6A 176.1(3) . . . . ?
C4A C5A C6A C7A -0.1(4) . . . . ?
C5A C6A C7A C8A 1.0(4) . . . . ?
C6A C7A C8A C9A -1.1(4) . . . . ?
C7A C8A C9A C4A 0.5(4) . . . . ?
C7A C8A C9A C10A -178.9(3) . . . . ?
C5A C4A C9A C8A 0.4(4) . . . . ?
C3A C4A C9A C8A -176.7(3) . . . . ?
C5A C4A C9A C10A 179.9(3) . . . . ?
C3A C4A C9A C10A 2.7(3) . . . . ?
C8A C9A C10A C11A 120.5(3) . . . . ?
C4A C9A C10A C11A -59.0(3) . . . . ?
C8A C9A C10A C1A -122.8(3) . . . . ?
C4A C9A C10A C1A 57.7(3) . . . . ?
C15A C1A C10A C9A 170.58(19) . . . . ?
C2A C1A C10A C9A -61.0(3) . . . . ?
C15A C1A C10A C11A -72.1(2) . . . . ?
C2A C1A C10A C11A 56.3(2) . . . . ?
C9A C10A C11A C12A 47.9(3) . . . . ?
C1A C10A C11A C12A -68.6(3) . . . . ?
C4A C3A C12A C13A 169.9(2) . . . . ?
C2A C3A C12A C13A -72.7(3) . . . . ?
C4A C3A C12A C11A -65.8(2) . . . . ?
C2A C3A C12A C11A 51.7(3) . . . . ?
C10A C11A C12A C13A 140.2(2) . . . . ?
C10A C11A C12A C3A 12.4(3) . . . . ?
C14A N1A C13A C12A -156.4(3) . . . . ?
C3A C12A C13A N1A -62.5(3) . . . . ?
C11A C12A C13A N1A 174.1(2) . . . . ?
C2A C1A C15A C20A -15.3(4) . . . . ?
C10A C1A C15A C20A 108.0(3) . . . . ?
C2A C1A C15A C16A 164.9(3) . . . . ?
C10A C1A C15A C16A -71.8(3) . . . . ?
C20A C15A C16A C17A -0.3(5) . . . . ?
C1A C15A C16A C17A 179.6(3) . . . . ?
C15A C16A C17A C18A 0.0(5) . . . . ?
C16A C17A C18A O1A 179.4(3) . . . . ?
C16A C17A C18A C19A 0.3(5) . . . . ?
C21A O1A C18A C17A 3.0(4) . . . . ?
C21A O1A C18A C19A -178.0(3) . . . . ?
C17A C18A C19A C20A -0.4(4) . . . . ?
O1A C18A C19A C20A -179.5(3) . . . . ?
C18A C19A C20A C15A 0.1(5) . . . . ?
C16A C15A C20A C19A 0.2(4) . . . . ?
C1A C15A C20A C19A -179.6(3) . . . . ?
C15B C1B C2B C3B -135.3(2) . . . . ?
C10B C1B C2B C3B -10.1(3) . . . . ?
C1B C2B C3B C4B -48.7(3) . . . . ?
C1B C2B C3B C12B 65.8(3) . . . . ?
C2B C3B C4B C5B -127.4(3) . . . . ?
C12B C3B C4B C5B 115.2(3) . . . . ?
C2B C3B C4B C9B 58.3(3) . . . . ?
C12B C3B C4B C9B -59.0(3) . . . . ?
C9B C4B C5B C6B -2.0(4) . . . . ?
C3B C4B C5B C6B -175.9(3) . . . . ?
C4B C5B C6B C7B 1.1(4) . . . . ?
C5B C6B C7B C8B 0.2(4) . . . . ?
C6B C7B C8B C9B -0.5(4) . . . . ?
C7B C8B C9B C4B -0.4(4) . . . . ?
C7B C8B C9B C10B 179.1(3) . . . . ?
C5B C4B C9B C8B 1.7(4) . . . . ?
C3B C4B C9B C8B 176.3(2) . . . . ?
C5B C4B C9B C10B -177.9(2) . . . . ?
C3B C4B C9B C10B -3.3(3) . . . . ?
C8B C9B C10B C11B -120.1(3) . . . . ?
C4B C9B C10B C11B 59.5(3) . . . . ?
C8B C9B C10B C1B 122.3(3) . . . . ?
C4B C9B C10B C1B -58.2(3) . . . . ?
C15B C1B C10B C9B -168.26(19) . . . . ?
C2B C1B C10B C9B 63.3(3) . . . . ?
C15B C1B C10B C11B 73.4(2) . . . . ?
C2B C1B C10B C11B -55.1(3) . . . . ?
C9B C10B C11B C12B -47.5(3) . . . . ?
C1B C10B C11B C12B 69.5(2) . . . . ?
C4B C3B C12B C13B -167.7(2) . . . . ?
C2B C3B C12B C13B 74.4(3) . . . . ?
C4B C3B C12B C11B 66.6(2) . . . . ?
C2B C3B C12B C11B -51.3(3) . . . . ?
C10B C11B C12B C13B -142.1(2) . . . . ?
C10B C11B C12B C3B -13.2(3) . . . . ?
C14B N1B C13B C12B 146.5(3) . . . . ?
C3B C12B C13B N1B 57.3(3) . . . . ?
C11B C12B C13B N1B -178.3(2) . . . . ?
C2B C1B C15B C16B 15.6(4) . . . . ?
C10B C1B C15B C16B -107.8(3) . . . . ?
C2B C1B C15B C20B -165.9(3) . . . . ?
C10B C1B C15B C20B 70.7(3) . . . . ?
C20B C15B C16B C17B 0.8(4) . . . . ?
C1B C15B C16B C17B 179.3(3) . . . . ?
C15B C16B C17B C18B -0.6(4) . . . . ?
C21B O1B C18B C17B 177.3(3) . . . . ?
C21B O1B C18B C19B -2.6(4) . . . . ?
C16B C17B C18B O1B -179.8(3) . . . . ?
C16B C17B C18B C19B 0.1(4) . . . . ?
O1B C18B C19B C20B -179.8(3) . . . . ?
C17B C18B C19B C20B 0.3(4) . . . . ?
C18B C19B C20B C15B -0.1(5) . . . . ?
C16B C15B C20B C19B -0.4(4) . . . . ?
C1B C15B C20B C19B -179.1(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
O1W H1W Cl1 0.98 2.23 3.185(2) 164.0 . yes
O1W H2W Cl2 0.92 2.23 3.155(2) 178.8 . yes
N1A H1AA Cl2 0.87(4) 2.21(4) 3.061(3) 169(3) . yes
N1A H1AB Cl2 0.89(3) 2.21(3) 3.102(3) 173(3) 2_546 yes
C13A H13D O1W 0.99 2.42 3.394(4) 167.6 1_545 yes
N1B H1BA Cl1 0.90(4) 2.27(4) 3.162(3) 172(3) 2_646 yes
N1B H1BB Cl1 0.85(3) 2.27(3) 3.110(2) 171(3) . yes
C14B H14B O1W 0.98 2.38 3.180(4) 138.0 2_646 yes

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050

