# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_5675
_database_code_depnum_ccdc_archive 'CCDC 2052887'
loop_
_audit_author_name
_audit_author_address
'yang wang and yuan pan'
;ocean university of china
China
;
_audit_update_record             
;
2020-12-26 deposited with the CCDC.	2022-05-25 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         ?
_chemical_formula_sum            'C32 H34 Cl N O2'
_chemical_formula_weight         500.05

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'
Cl Cl 0.1484 0.1585 '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                   16.0914(5)
_cell_length_b                   9.8835(3)
_cell_length_c                   18.7907(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.529(4)
_cell_angle_gamma                90
_cell_volume                     2798.68(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26608
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5508
_reflns_number_gt                4881
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0807P)²+0.6346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5508
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
Cl1 Cl 0.37256(3) 0.87542(4) 0.19044(2) 0.03789(13) Uani 1 1 d . . . . .
O2 O 0.56569(8) 0.31037(12) 0.40257(7) 0.0452(3) Uani 1 1 d . . . . .
N1 N 0.55230(9) 0.24615(14) 0.28154(8) 0.0404(3) Uani 1 1 d . . . . .
O1 O 0.70705(8) 0.6788(2) 0.28555(7) 0.0699(5) Uani 1 1 d . . . . .
C12 C 0.38607(8) 0.75783(13) 0.32585(8) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.53837(8) 0.59019(13) 0.35711(7) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.529996 0.580498 0.403365 0.027 Uiso 1 1 calc R U . . .
C2 C 0.48035(8) 0.58551(13) 0.21589(7) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.433698 0.574244 0.170021 0.026 Uiso 1 1 calc R U . . .
C7 C 0.37406(8) 0.62037(13) 0.28774(7) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.334110 0.631130 0.234981 0.027 Uiso 1 1 calc R U . . .
C1 C 0.46307(8) 0.55193(13) 0.28695(7) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.61671(9) 0.63718(13) 0.35871(7) 0.0244(3) Uani 1 1 d . . . . .
C10 C 0.44142(9) 0.39234(13) 0.29059(8) 0.0242(3) Uani 1 1 d . . . . .
C17 C 0.38545(9) 0.87790(14) 0.28655(8) 0.0279(3) Uani 1 1 d . . . . .
C3 C 0.55725(9) 0.63034(13) 0.21282(7) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.33538(9) 0.51427(14) 0.32458(8) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.290503 0.531783 0.343800 0.034 Uiso 1 1 calc R U . . .
C9 C 0.37165(9) 0.39406(14) 0.32678(8) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.355751 0.318300 0.348446 0.035 Uiso 1 1 calc R U . . .
C13 C 0.39712(9) 0.76949(15) 0.40270(8) 0.0300(3) Uani 1 1 d . . . . .
H13 H 0.398042 0.691463 0.430627 0.036 Uiso 1 1 calc R U . . .
C26 C 0.41361(10) 0.32596(14) 0.21336(8) 0.0285(3) Uani 1 1 d . . . . .
C22 C 0.57051(10) 0.66063(16) 0.13757(8) 0.0326(3) Uani 1 1 d . . . . .
C18 C 0.69166(9) 0.67490(16) 0.43287(8) 0.0319(3) Uani 1 1 d . . . . .
C31 C 0.48427(11) 0.24744(15) 0.21018(9) 0.0362(4) Uani 1 1 d . . . . .
C11 C 0.52720(10) 0.31340(14) 0.33440(9) 0.0321(3) Uani 1 1 d . . . . .
C16 C 0.39460(11) 1.00353(16) 0.32154(10) 0.0400(4) Uani 1 1 d . . . . .
H16 H 0.393541 1.081938 0.293875 0.048 Uiso 1 1 calc R U . . .
C4 C 0.63322(9) 0.65079(17) 0.28572(9) 0.0324(3) Uani 1 1 d . . . . .
C27 C 0.33575(12) 0.33408(17) 0.15137(9) 0.0402(4) Uani 1 1 d . . . . .
H27 H 0.288012 0.384604 0.153687 0.048 Uiso 1 1 calc R U . . .
C14 C 0.40678(11) 0.89426(17) 0.43853(9) 0.0405(4) Uani 1 1 d . . . . .
H14 H 0.414221 0.899239 0.489828 0.049 Uiso 1 1 calc R U . . .
C15 C 0.40528(12) 1.01149(17) 0.39759(10) 0.0471(4) Uani 1 1 d . . . . .
H15 H 0.411465 1.095364 0.421318 0.057 Uiso 1 1 calc R U . . .
C25 C 0.48352(12) 0.6456(2) 0.07000(9) 0.0439(4) Uani 1 1 d . . . . .
H25A H 0.462035 0.554627 0.068152 0.066 Uiso 1 1 calc R U . . .
H25B H 0.493772 0.665550 0.023753 0.066 Uiso 1 1 calc R U . . .
H25C H 0.440244 0.707376 0.075748 0.066 Uiso 1 1 calc R U . . .
C24 C 0.63637(11) 0.5583(2) 0.12579(10) 0.0492(5) Uani 1 1 d . . . . .
H24A H 0.691380 0.562864 0.167957 0.074 Uiso 1 1 calc R U . . .
H24B H 0.646679 0.579418 0.079704 0.074 Uiso 1 1 calc R U . . .
H24C H 0.612201 0.468742 0.122331 0.074 Uiso 1 1 calc R U . . .
C30 C 0.48033(16) 0.18019(18) 0.14435(12) 0.0540(5) Uani 1 1 d . . . . .
H30 H 0.528075 0.129936 0.141827 0.065 Uiso 1 1 calc R U . . .
C28 C 0.33039(15) 0.2647(2) 0.08521(11) 0.0552(5) Uani 1 1 d . . . . .
H28 H 0.278411 0.268167 0.042983 0.066 Uiso 1 1 calc R U . . .
C29 C 0.40189(18) 0.1911(2) 0.08225(12) 0.0617(6) Uani 1 1 d . . . . .
H29 H 0.397520 0.147375 0.037262 0.074 Uiso 1 1 calc R U . . .
C19 C 0.71667(15) 0.8236(2) 0.43078(12) 0.0586(5) Uani 1 1 d . . . . .
H19A H 0.738042 0.837811 0.389653 0.088 Uiso 1 1 calc R U . . .
H19B H 0.762267 0.847241 0.477911 0.088 Uiso 1 1 calc R U . . .
H19C H 0.665404 0.879193 0.423455 0.088 Uiso 1 1 calc R U . . .
C21 C 0.66196(13) 0.6551(2) 0.50087(9) 0.0563(5) Uani 1 1 d . . . . .
H21A H 0.610840 0.710303 0.494748 0.084 Uiso 1 1 calc R U . . .
H21B H 0.709184 0.680687 0.546585 0.084 Uiso 1 1 calc R U . . .
H21C H 0.647171 0.561706 0.504075 0.084 Uiso 1 1 calc R U . . .
C20 C 0.77252(12) 0.5830(2) 0.44520(12) 0.0621(6) Uani 1 1 d . . . . .
H20A H 0.754728 0.489999 0.443778 0.093 Uiso 1 1 calc R U . . .
H20B H 0.816898 0.602422 0.493718 0.093 Uiso 1 1 calc R U . . .
H20C H 0.796445 0.599044 0.405795 0.093 Uiso 1 1 calc R U . . .
C23 C 0.60407(17) 0.8065(2) 0.13827(11) 0.0614(6) Uani 1 1 d . . . . .
H23A H 0.562121 0.868271 0.146254 0.092 Uiso 1 1 calc R U . . .
H23B H 0.610652 0.825969 0.090469 0.092 Uiso 1 1 calc R U . . .
H23C H 0.660367 0.816384 0.178510 0.092 Uiso 1 1 calc R U . . .
C32 C 0.63088(16) 0.1604(3) 0.30125(16) 0.0719(7) Uani 1 1 d . . . . .
H32A H 0.613129 0.067138 0.294353 0.108 Uiso 1 1 calc R U . . .
H32B H 0.667299 0.175495 0.353338 0.108 Uiso 1 1 calc R U . . .
H32C H 0.663949 0.182020 0.269018 0.108 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
Cl1 C17 1.7442(15) . ?
O2 C11 1.2119(19) . ?
N1 C11 1.369(2) . ?
N1 C31 1.403(2) . ?
N1 C32 1.458(2) . ?
O1 C4 1.2208(19) . ?
C12 C17 1.3959(19) . ?
C12 C13 1.396(2) . ?
C12 C7 1.5161(18) . ?
C6 C5 1.3338(19) . ?
C6 C1 1.4930(17) . ?
C6 H6 0.9300 . ?
C2 C3 1.3345(18) . ?
C2 C1 1.4936(17) . ?
C2 H2 0.9300 . ?
C7 C8 1.5061(18) . ?
C7 C1 1.5888(17) . ?
C7 H7 0.9800 . ?
C1 C10 1.6219(17) . ?
C5 C4 1.4917(19) . ?
C5 C18 1.5352(18) . ?
C10 C9 1.5029(18) . ?
C10 C26 1.5104(19) . ?
C10 C11 1.5475(19) . ?
C17 C16 1.388(2) . ?
C3 C4 1.4957(19) . ?
C3 C22 1.5317(18) . ?
C8 C9 1.318(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C26 C27 1.382(2) . ?
C26 C31 1.395(2) . ?
C22 C25 1.532(2) . ?
C22 C24 1.536(2) . ?
C22 C23 1.538(2) . ?
C18 C21 1.526(2) . ?
C18 C19 1.528(2) . ?
C18 C20 1.537(2) . ?
C31 C30 1.386(2) . ?
C16 C15 1.380(3) . ?
C16 H16 0.9300 . ?
C27 C28 1.395(2) . ?
C27 H27 0.9300 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C30 C29 1.390(3) . ?
C30 H30 0.9300 . ?
C28 C29 1.379(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C31 111.06(12) . . ?
C11 N1 C32 123.26(17) . . ?
C31 N1 C32 124.38(16) . . ?
C17 C12 C13 116.85(13) . . ?
C17 C12 C7 122.40(12) . . ?
C13 C12 C7 120.74(12) . . ?
C5 C6 C1 125.17(12) . . ?
C5 C6 H6 117.4 . . ?
C1 C6 H6 117.4 . . ?
C3 C2 C1 125.34(12) . . ?
C3 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
C8 C7 C12 114.31(11) . . ?
C8 C7 C1 103.12(10) . . ?
C12 C7 C1 114.83(10) . . ?
C8 C7 H7 108.1 . . ?
C12 C7 H7 108.1 . . ?
C1 C7 H7 108.1 . . ?
C6 C1 C2 112.66(10) . . ?
C6 C1 C7 109.82(10) . . ?
C2 C1 C7 111.40(10) . . ?
C6 C1 C10 109.20(10) . . ?
C2 C1 C10 111.34(10) . . ?
C7 C1 C10 101.89(9) . . ?
C6 C5 C4 118.84(12) . . ?
C6 C5 C18 122.71(12) . . ?
C4 C5 C18 118.44(12) . . ?
C9 C10 C26 115.03(12) . . ?
C9 C10 C11 115.69(12) . . ?
C26 C10 C11 101.58(11) . . ?
C9 C10 C1 102.34(10) . . ?
C26 C10 C1 112.18(10) . . ?
C11 C10 C1 110.37(10) . . ?
C16 C17 C12 121.99(14) . . ?
C16 C17 Cl1 117.21(12) . . ?
C12 C17 Cl1 120.80(11) . . ?
C2 C3 C4 118.54(12) . . ?
C2 C3 C22 122.43(12) . . ?
C4 C3 C22 119.03(12) . . ?
C9 C8 C7 113.10(12) . . ?
C9 C8 H8 123.5 . . ?
C7 C8 H8 123.5 . . ?
C8 C9 C10 112.88(12) . . ?
C8 C9 H9 123.6 . . ?
C10 C9 H9 123.6 . . ?
C14 C13 C12 121.82(14) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C27 C26 C31 120.52(14) . . ?
C27 C26 C10 131.32(14) . . ?
C31 C26 C10 108.14(13) . . ?
C3 C22 C25 111.32(12) . . ?
C3 C22 C24 109.33(13) . . ?
C25 C22 C24 107.03(13) . . ?
C3 C22 C23 109.72(12) . . ?
C25 C22 C23 108.28(15) . . ?
C24 C22 C23 111.13(15) . . ?
C21 C18 C19 107.93(16) . . ?
C21 C18 C5 110.61(12) . . ?
C19 C18 C5 109.90(13) . . ?
C21 C18 C20 107.16(15) . . ?
C19 C18 C20 110.85(16) . . ?
C5 C18 C20 110.33(13) . . ?
C30 C31 C26 121.47(17) . . ?
C30 C31 N1 128.68(16) . . ?
C26 C31 N1 109.81(13) . . ?
O2 C11 N1 125.71(15) . . ?
O2 C11 C10 127.20(14) . . ?
N1 C11 C10 107.09(13) . . ?
C15 C16 C17 119.68(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O1 C4 C5 120.67(14) . . ?
O1 C4 C3 120.78(13) . . ?
C5 C4 C3 118.55(12) . . ?
C26 C27 C28 118.49(18) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C15 C14 C13 119.75(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.90(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C31 C30 C29 117.11(18) . . ?
C31 C30 H30 121.4 . . ?
C29 C30 H30 121.4 . . ?
C29 C28 C27 120.22(19) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 122.13(17) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C17 C12 C7 C8 -153.24(13) . . . . ?
C13 C12 C7 C8 25.84(17) . . . . ?
C17 C12 C7 C1 87.85(15) . . . . ?
C13 C12 C7 C1 -93.08(14) . . . . ?
C5 C6 C1 C2 -6.17(18) . . . . ?
C5 C6 C1 C7 -130.97(13) . . . . ?
C5 C6 C1 C10 118.09(14) . . . . ?
C3 C2 C1 C6 7.30(18) . . . . ?
C3 C2 C1 C7 131.23(13) . . . . ?
C3 C2 C1 C10 -115.77(14) . . . . ?
C8 C7 C1 C6 -91.98(12) . . . . ?
C12 C7 C1 C6 33.02(14) . . . . ?
C8 C7 C1 C2 142.48(11) . . . . ?
C12 C7 C1 C2 -92.51(13) . . . . ?
C8 C7 C1 C10 23.68(12) . . . . ?
C12 C7 C1 C10 148.68(11) . . . . ?
C1 C6 C5 C4 -1.5(2) . . . . ?
C1 C6 C5 C18 179.97(12) . . . . ?
C6 C1 C10 C9 91.93(12) . . . . ?
C2 C1 C10 C9 -143.04(11) . . . . ?
C7 C1 C10 C9 -24.19(12) . . . . ?
C6 C1 C10 C26 -144.24(11) . . . . ?
C2 C1 C10 C26 -19.21(15) . . . . ?
C7 C1 C10 C26 99.65(12) . . . . ?
C6 C1 C10 C11 -31.75(14) . . . . ?
C2 C1 C10 C11 93.28(13) . . . . ?
C7 C1 C10 C11 -147.87(11) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
C7 C12 C17 C16 178.59(13) . . . . ?
C13 C12 C17 Cl1 179.73(10) . . . . ?
C7 C12 C17 Cl1 -1.16(18) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C22 179.01(12) . . . . ?
C12 C7 C8 C9 -140.81(13) . . . . ?
C1 C7 C8 C9 -15.47(15) . . . . ?
C7 C8 C9 C10 -1.10(18) . . . . ?
C26 C10 C9 C8 -105.15(15) . . . . ?
C11 C10 C9 C8 136.80(14) . . . . ?
C1 C10 C9 C8 16.76(16) . . . . ?
C17 C12 C13 C14 0.2(2) . . . . ?
C7 C12 C13 C14 -178.92(13) . . . . ?
C9 C10 C26 C27 42.8(2) . . . . ?
C11 C10 C26 C27 168.57(15) . . . . ?
C1 C10 C26 C27 -73.58(18) . . . . ?
C9 C10 C26 C31 -138.34(13) . . . . ?
C11 C10 C26 C31 -12.61(14) . . . . ?
C1 C10 C26 C31 105.24(13) . . . . ?
C2 C3 C22 C25 5.4(2) . . . . ?
C4 C3 C22 C25 -175.02(14) . . . . ?
C2 C3 C22 C24 -112.69(16) . . . . ?
C4 C3 C22 C24 66.93(17) . . . . ?
C2 C3 C22 C23 125.20(17) . . . . ?
C4 C3 C22 C23 -55.18(19) . . . . ?
C6 C5 C18 C21 -1.8(2) . . . . ?
C4 C5 C18 C21 179.67(15) . . . . ?
C6 C5 C18 C19 -120.85(17) . . . . ?
C4 C5 C18 C19 60.60(19) . . . . ?
C6 C5 C18 C20 116.61(17) . . . . ?
C4 C5 C18 C20 -61.94(19) . . . . ?
C27 C26 C31 C30 2.8(2) . . . . ?
C10 C26 C31 C30 -176.17(14) . . . . ?
C27 C26 C31 N1 -174.99(13) . . . . ?
C10 C26 C31 N1 6.04(16) . . . . ?
C11 N1 C31 C30 -173.17(16) . . . . ?
C32 N1 C31 C30 -5.9(3) . . . . ?
C11 N1 C31 C26 4.43(17) . . . . ?
C32 N1 C31 C26 171.73(17) . . . . ?
C31 N1 C11 O2 167.28(15) . . . . ?
C32 N1 C11 O2 -0.2(3) . . . . ?
C31 N1 C11 C10 -12.63(16) . . . . ?
C32 N1 C11 C10 179.90(17) . . . . ?
C9 C10 C11 O2 -39.5(2) . . . . ?
C26 C10 C11 O2 -164.76(15) . . . . ?
C1 C10 C11 O2 76.09(18) . . . . ?
C9 C10 C11 N1 140.43(13) . . . . ?
C26 C10 C11 N1 15.14(14) . . . . ?
C1 C10 C11 N1 -104.01(13) . . . . ?
C12 C17 C16 C15 0.4(2) . . . . ?
Cl1 C17 C16 C15 -179.80(13) . . . . ?
C6 C5 C4 O1 -171.72(17) . . . . ?
C18 C5 C4 O1 6.9(2) . . . . ?
C6 C5 C4 C3 8.7(2) . . . . ?
C18 C5 C4 C3 -172.71(13) . . . . ?
C2 C3 C4 O1 172.76(17) . . . . ?
C22 C3 C4 O1 -6.9(2) . . . . ?
C2 C3 C4 C5 -7.7(2) . . . . ?
C22 C3 C4 C5 172.71(13) . . . . ?
C31 C26 C27 C28 -1.5(2) . . . . ?
C10 C26 C27 C28 177.17(15) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C26 C31 C30 C29 -1.8(2) . . . . ?
N1 C31 C30 C29 175.50(16) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C27 C28 C29 C30 1.5(3) . . . . ?
C31 C30 C29 C28 -0.3(3) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_exp_5688
_database_code_depnum_ccdc_archive 'CCDC 2052888'
loop_
_audit_author_name
_audit_author_address
'yang wang and yuan pan'
;ocean university of china
China
;
_audit_update_record             
;
2020-12-26 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-13
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H34 Cl N O2'
_chemical_formula_sum            'C32 H34 Cl N O2'
_chemical_formula_weight         500.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   10.1923(3)
_cell_length_b                   9.7537(3)
_cell_length_c                   13.7328(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.786(2)
_cell_angle_gamma                90
_cell_volume                     1364.55(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12974
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      29.7770
_cell_measurement_theta_min      2.6850
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33145
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.891
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  75.00   0.50    2.59    --   -1.70  37.00-120.00  192
  2  ω    -21.00  23.00   0.50    2.59    --   -1.70  37.00-150.00   88
  3  ω    -25.00  86.00   0.50    2.59    --   -1.70  57.00 -60.00  222
  4  ω    -25.00  79.00   0.50    2.59    --   -1.70  57.00  60.00  208
  5  ω    -24.00  31.00   0.50    2.59    --   -1.70 -82.00-150.00  110
  6  ω    -25.00  77.00   0.50    2.59    --   -1.70  57.00   0.00  204
  7  ω    -25.00  87.00   0.50    2.59    --   -1.70  19.00-180.00  224
  8  ω    -64.00 -39.00   0.50    2.59    --    1.90 -37.00 -90.00   50
  9  ω     -4.00  21.00   0.50    2.59    --    1.90 -37.00 -90.00   50
 10  ω      4.00  34.00   0.50    2.59    --    1.90 -82.00 150.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0437945000
_diffrn_orient_matrix_UB_12      -0.0314813000
_diffrn_orient_matrix_UB_13      -0.0323374000
_diffrn_orient_matrix_UB_21      0.0067060000
_diffrn_orient_matrix_UB_22      0.0630899000
_diffrn_orient_matrix_UB_23      -0.0250238000
_diffrn_orient_matrix_UB_31      0.0537233000
_diffrn_orient_matrix_UB_32      0.0178052000
_diffrn_orient_matrix_UB_33      0.0315852000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5122
_reflns_number_total             5337
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.176
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2435 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.3824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.20525(8) 0.97108(8) 0.56254(7) 0.0452(2) Uani 1 1 d . . . . .
O1 O 0.6583(2) 1.0268(2) 0.58270(19) 0.0428(5) Uani 1 1 d . . . . .
O2 O 0.3521(3) 0.5077(2) 0.35305(15) 0.0406(6) Uani 1 1 d . . . . .
N1 N 0.7820(3) 0.8938(3) 0.4824(2) 0.0397(6) Uani 1 1 d . . . . .
C1 C 0.6990(3) 0.9160(3) 0.5569(2) 0.0329(6) Uani 1 1 d . . . . .
C2 C 0.6618(3) 0.7734(3) 0.5994(2) 0.0256(5) Uani 1 1 d . . . . .
C3 C 0.5087(2) 0.7484(3) 0.57690(19) 0.0229(5) Uani 1 1 d . . . . .
C4 C 0.4462(3) 0.8287(3) 0.6652(2) 0.0278(6) Uani 1 1 d . . . . .
H4 H 0.441358 0.928305 0.648161 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5519(3) 0.8091(3) 0.7442(2) 0.0347(6) Uani 1 1 d . . . . .
H5 H 0.536735 0.819324 0.811755 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4668(2) 0.8041(3) 0.4797(2) 0.0234(5) Uani 1 1 d . . . . .
H6 H 0.476202 0.899946 0.469635 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4172(2) 0.7300(3) 0.40566(18) 0.0229(5) Uani 1 1 d . . . . .
C8 C 0.3932(3) 0.5798(3) 0.42014(18) 0.0249(5) Uani 1 1 d . . . . .
C9 C 0.4207(2) 0.5202(3) 0.51902(19) 0.0218(5) Uani 1 1 d . . . . .
C10 C 0.4788(2) 0.5993(3) 0.58741(18) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.503083 0.557004 0.647643 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7531(3) 0.6793(3) 0.54636(19) 0.0267(6) Uani 1 1 d . . . . .
C12 C 0.8184(3) 0.7552(3) 0.4765(2) 0.0338(6) Uani 1 1 d . . . . .
C13 C 0.9110(3) 0.6981(4) 0.4172(2) 0.0432(8) Uani 1 1 d . . . . .
H13 H 0.953533 0.751388 0.369595 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9392(3) 0.5608(4) 0.4299(2) 0.0463(8) Uani 1 1 d . . . . .
H14 H 1.002840 0.518910 0.390510 0.056 Uiso 1 1 calc R U . . .
C15 C 0.8769(3) 0.4830(4) 0.4985(3) 0.0436(8) Uani 1 1 d . . . . .
H15 H 0.898287 0.388694 0.505862 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7823(3) 0.5418(3) 0.5575(2) 0.0337(6) Uani 1 1 d . . . . .
H16 H 0.739002 0.488037 0.604409 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6667(3) 0.7766(3) 0.7097(2) 0.0311(6) Uani 1 1 d . . . . .
H17 H 0.742986 0.757613 0.748925 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8324(5) 1.0031(5) 0.4226(4) 0.0640(12) Uani 1 1 d . . . . .
H18A H 0.928094 1.007433 0.431038 0.096 Uiso 1 1 calc R U . . .
H18B H 0.794047 1.090591 0.442198 0.096 Uiso 1 1 calc R U . . .
H18C H 0.808989 0.985113 0.353972 0.096 Uiso 1 1 calc R U . . .
C19 C 0.3102(3) 0.7797(3) 0.6883(2) 0.0283(6) Uani 1 1 d . . . . .
C20 C 0.1970(3) 0.8315(3) 0.6427(2) 0.0288(6) Uani 1 1 d . . . . .
C21 C 0.0725(3) 0.7787(3) 0.6588(2) 0.0351(6) Uani 1 1 d . . . . .
H21 H -0.002620 0.816399 0.626049 0.042 Uiso 1 1 calc R U . . .
C22 C 0.0598(3) 0.6710(4) 0.7229(2) 0.0404(7) Uani 1 1 d . . . . .
H22 H -0.024186 0.632304 0.733054 0.048 Uiso 1 1 calc R U . . .
C23 C 0.1692(4) 0.6195(4) 0.7723(2) 0.0419(7) Uani 1 1 d . . . . .
H23 H 0.160147 0.547117 0.817973 0.050 Uiso 1 1 calc R U . . .
C24 C 0.2924(3) 0.6738(3) 0.7551(2) 0.0364(7) Uani 1 1 d . . . . .
H24 H 0.366797 0.637756 0.789818 0.044 Uiso 1 1 calc R U . . .
C25 C 0.3797(3) 0.3715(3) 0.53871(19) 0.0259(5) Uani 1 1 d . . . . .
C26 C 0.4081(4) 0.3303(3) 0.6450(2) 0.0399(7) Uani 1 1 d . . . . .
H26A H 0.502921 0.333628 0.658945 0.060 Uiso 1 1 calc R U . . .
H26B H 0.375940 0.237033 0.655766 0.060 Uiso 1 1 calc R U . . .
H26C H 0.363552 0.393983 0.688181 0.060 Uiso 1 1 calc R U . . .
C27 C 0.2310(3) 0.3575(3) 0.5191(3) 0.0404(7) Uani 1 1 d . . . . .
H27A H 0.184766 0.425332 0.557956 0.061 Uiso 1 1 calc R U . . .
H27B H 0.202797 0.265113 0.537116 0.061 Uiso 1 1 calc R U . . .
H27C H 0.210747 0.373121 0.449775 0.061 Uiso 1 1 calc R U . . .
C28 C 0.4539(4) 0.2706(3) 0.4742(3) 0.0420(8) Uani 1 1 d . . . . .
H28A H 0.430578 0.288154 0.405534 0.063 Uiso 1 1 calc R U . . .
H28B H 0.429753 0.176425 0.490852 0.063 Uiso 1 1 calc R U . . .
H28C H 0.548670 0.282952 0.485025 0.063 Uiso 1 1 calc R U . . .
C29 C 0.3813(3) 0.7940(3) 0.3060(2) 0.0305(6) Uani 1 1 d . . . . .
C30 C 0.4069(4) 0.9492(3) 0.3057(2) 0.0425(8) Uani 1 1 d . . . . .
H30A H 0.352271 0.993529 0.354056 0.064 Uiso 1 1 calc R U . . .
H30B H 0.385034 0.986373 0.240956 0.064 Uiso 1 1 calc R U . . .
H30C H 0.499684 0.966605 0.322027 0.064 Uiso 1 1 calc R U . . .
C31 C 0.2347(4) 0.7714(4) 0.2822(3) 0.0531(10) Uani 1 1 d . . . . .
H31A H 0.216934 0.672870 0.276955 0.080 Uiso 1 1 calc R U . . .
H31B H 0.210907 0.816240 0.220326 0.080 Uiso 1 1 calc R U . . .
H31C H 0.182756 0.810556 0.334251 0.080 Uiso 1 1 calc R U . . .
C32 C 0.4648(5) 0.7298(4) 0.2268(2) 0.0531(10) Uani 1 1 d . . . . .
H32A H 0.558052 0.744386 0.243133 0.080 Uiso 1 1 calc R U . . .
H32B H 0.442812 0.772721 0.163872 0.080 Uiso 1 1 calc R U . . .
H32C H 0.446896 0.631172 0.222818 0.080 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
Cl1 C20 1.754(3) . ?
O1 C1 1.214(4) . ?
O2 C8 1.223(3) . ?
N1 C1 1.366(4) . ?
N1 C12 1.404(4) . ?
N1 C18 1.450(4) . ?
C1 C2 1.560(4) . ?
C2 C3 1.600(3) . ?
C2 C11 1.509(4) . ?
C2 C17 1.515(4) . ?
C3 C4 1.593(4) . ?
C3 C6 1.492(4) . ?
C3 C10 1.494(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.518(4) . ?
C4 C19 1.509(4) . ?
C5 H5 0.9500 . ?
C5 C17 1.315(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.334(4) . ?
C7 C8 1.499(3) . ?
C7 C29 1.538(4) . ?
C8 C9 1.496(3) . ?
C9 C10 1.339(4) . ?
C9 C25 1.535(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(4) . ?
C11 C16 1.381(4) . ?
C12 C13 1.383(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.390(4) . ?
C19 C24 1.398(4) . ?
C20 C21 1.394(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.532(4) . ?
C25 C27 1.537(4) . ?
C25 C28 1.539(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.536(4) . ?
C29 C31 1.535(4) . ?
C29 C32 1.536(5) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C1 N1 C12 111.5(3) . . ?
C1 N1 C18 123.1(3) . . ?
C12 N1 C18 125.2(3) . . ?
O1 C1 N1 125.8(3) . . ?
O1 C1 C2 126.6(3) . . ?
N1 C1 C2 107.5(2) . . ?
C1 C2 C3 108.1(2) . . ?
C11 C2 C1 101.6(2) . . ?
C11 C2 C3 115.2(2) . . ?
C11 C2 C17 119.6(2) . . ?
C17 C2 C1 110.7(2) . . ?
C17 C2 C3 101.4(2) . . ?
C4 C3 C2 100.93(19) . . ?
C6 C3 C2 111.6(2) . . ?
C6 C3 C4 113.1(2) . . ?
C6 C3 C10 112.8(2) . . ?
C10 C3 C2 109.3(2) . . ?
C10 C3 C4 108.5(2) . . ?
C3 C4 H4 108.5 . . ?
C5 C4 C3 101.0(2) . . ?
C5 C4 H4 108.5 . . ?
C19 C4 C3 113.3(2) . . ?
C19 C4 H4 108.5 . . ?
C19 C4 C5 116.5(2) . . ?
C4 C5 H5 123.5 . . ?
C17 C5 C4 113.1(2) . . ?
C17 C5 H5 123.5 . . ?
C3 C6 H6 117.4 . . ?
C7 C6 C3 125.1(2) . . ?
C7 C6 H6 117.4 . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 C29 122.1(2) . . ?
C8 C7 C29 118.7(2) . . ?
O2 C8 C7 121.0(2) . . ?
O2 C8 C9 120.7(2) . . ?
C9 C8 C7 118.3(2) . . ?
C8 C9 C25 118.9(2) . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 C25 122.5(2) . . ?
C3 C10 H10 117.3 . . ?
C9 C10 C3 125.5(2) . . ?
C9 C10 H10 117.3 . . ?
C12 C11 C2 108.8(3) . . ?
C16 C11 C2 132.1(3) . . ?
C16 C11 C12 119.0(3) . . ?
C11 C12 N1 109.8(3) . . ?
C13 C12 N1 127.4(3) . . ?
C13 C12 C11 122.7(3) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 118.9(3) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C2 C17 H17 124.3 . . ?
C5 C17 C2 111.3(2) . . ?
C5 C17 H17 124.3 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C4 123.0(3) . . ?
C20 C19 C24 116.2(3) . . ?
C24 C19 C4 120.7(3) . . ?
C19 C20 Cl1 120.6(2) . . ?
C19 C20 C21 122.7(3) . . ?
C21 C20 Cl1 116.6(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 H24 119.0 . . ?
C23 C24 C19 122.0(3) . . ?
C23 C24 H24 119.0 . . ?
C9 C25 C27 109.0(2) . . ?
C9 C25 C28 111.2(2) . . ?
C26 C25 C9 111.8(2) . . ?
C26 C25 C27 107.4(3) . . ?
C26 C25 C28 107.4(2) . . ?
C27 C25 C28 110.0(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C7 111.5(2) . . ?
C30 C29 C32 107.6(3) . . ?
C31 C29 C7 109.5(2) . . ?
C31 C29 C30 107.8(3) . . ?
C31 C29 C32 110.4(3) . . ?
C32 C29 C7 110.0(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
Cl1 C20 C21 C22 -178.5(2) . . . . ?
O1 C1 C2 C3 64.1(3) . . . . ?
O1 C1 C2 C11 -174.2(3) . . . . ?
O1 C1 C2 C17 -46.1(4) . . . . ?
O2 C8 C9 C10 172.9(3) . . . . ?
O2 C8 C9 C25 -7.9(4) . . . . ?
N1 C1 C2 C3 -113.5(3) . . . . ?
N1 C1 C2 C11 8.2(3) . . . . ?
N1 C1 C2 C17 136.3(2) . . . . ?
N1 C12 C13 C14 174.3(3) . . . . ?
C1 N1 C12 C11 3.0(3) . . . . ?
C1 N1 C12 C13 -172.7(3) . . . . ?
C1 C2 C3 C4 -83.5(2) . . . . ?
C1 C2 C3 C6 36.9(3) . . . . ?
C1 C2 C3 C10 162.3(2) . . . . ?
C1 C2 C11 C12 -6.5(3) . . . . ?
C1 C2 C11 C16 171.3(3) . . . . ?
C1 C2 C17 C5 91.3(3) . . . . ?
C2 C3 C4 C5 -31.5(3) . . . . ?
C2 C3 C4 C19 -156.9(2) . . . . ?
C2 C3 C6 C7 118.4(3) . . . . ?
C2 C3 C10 C9 -124.8(3) . . . . ?
C2 C11 C12 N1 2.8(3) . . . . ?
C2 C11 C12 C13 178.7(3) . . . . ?
C2 C11 C16 C15 -177.5(3) . . . . ?
C3 C2 C11 C12 110.0(3) . . . . ?
C3 C2 C11 C16 -72.1(4) . . . . ?
C3 C2 C17 C5 -23.2(3) . . . . ?
C3 C4 C5 C17 19.8(3) . . . . ?
C3 C4 C19 C20 -87.5(3) . . . . ?
C3 C4 C19 C24 89.8(3) . . . . ?
C3 C6 C7 C8 3.6(4) . . . . ?
C3 C6 C7 C29 -177.5(3) . . . . ?
C4 C3 C6 C7 -128.6(3) . . . . ?
C4 C3 C10 C9 126.0(3) . . . . ?
C4 C5 C17 C2 2.2(4) . . . . ?
C4 C19 C20 Cl1 -6.3(4) . . . . ?
C4 C19 C20 C21 174.9(3) . . . . ?
C4 C19 C24 C23 -175.0(3) . . . . ?
C5 C4 C19 C20 156.0(3) . . . . ?
C5 C4 C19 C24 -26.8(4) . . . . ?
C6 C3 C4 C5 -150.8(2) . . . . ?
C6 C3 C4 C19 83.8(3) . . . . ?
C6 C3 C10 C9 -0.1(4) . . . . ?
C6 C7 C8 O2 -177.5(3) . . . . ?
C6 C7 C8 C9 2.6(4) . . . . ?
C6 C7 C29 C30 -1.4(4) . . . . ?
C6 C7 C29 C31 -120.6(3) . . . . ?
C6 C7 C29 C32 118.0(3) . . . . ?
C7 C8 C9 C10 -7.2(3) . . . . ?
C7 C8 C9 C25 172.0(2) . . . . ?
C8 C7 C29 C30 177.6(3) . . . . ?
C8 C7 C29 C31 58.4(4) . . . . ?
C8 C7 C29 C32 -63.1(3) . . . . ?
C8 C9 C10 C3 5.9(4) . . . . ?
C8 C9 C25 C26 -176.7(3) . . . . ?
C8 C9 C25 C27 -58.1(3) . . . . ?
C8 C9 C25 C28 63.3(3) . . . . ?
C10 C3 C4 C5 83.2(2) . . . . ?
C10 C3 C4 C19 -42.1(3) . . . . ?
C10 C3 C6 C7 -5.0(4) . . . . ?
C10 C9 C25 C26 2.5(4) . . . . ?
C10 C9 C25 C27 121.0(3) . . . . ?
C10 C9 C25 C28 -117.6(3) . . . . ?
C11 C2 C3 C4 163.6(2) . . . . ?
C11 C2 C3 C6 -76.0(3) . . . . ?
C11 C2 C3 C10 49.4(3) . . . . ?
C11 C2 C17 C5 -151.1(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 N1 C1 O1 175.2(3) . . . . ?
C12 N1 C1 C2 -7.2(3) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C11 -0.5(5) . . . . ?
C16 C11 C12 N1 -175.4(3) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C17 C2 C3 C4 33.0(3) . . . . ?
C17 C2 C3 C6 153.3(2) . . . . ?
C17 C2 C3 C10 -81.2(2) . . . . ?
C17 C2 C11 C12 -128.7(3) . . . . ?
C17 C2 C11 C16 49.2(4) . . . . ?
C18 N1 C1 O1 -0.5(5) . . . . ?
C18 N1 C1 C2 177.1(3) . . . . ?
C18 N1 C12 C11 178.6(3) . . . . ?
C18 N1 C12 C13 3.0(5) . . . . ?
C19 C4 C5 C17 143.0(3) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C19 C24 C23 2.4(4) . . . . ?
C20 C21 C22 C23 1.9(5) . . . . ?
C21 C22 C23 C24 -1.9(5) . . . . ?
C22 C23 C24 C19 -0.3(5) . . . . ?
C24 C19 C20 Cl1 176.3(2) . . . . ?
C24 C19 C20 C21 -2.4(4) . . . . ?
C25 C9 C10 C3 -173.3(2) . . . . ?
C29 C7 C8 O2 3.6(4) . . . . ?
C29 C7 C8 C9 -176.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.621
