# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_scx20_089
_database_code_depnum_ccdc_archive 'CCDC 2077955'
loop_
_audit_author_name
_audit_author_address
'Qi Jiang'
;Boehringer Ingelheim Pharmaceuticals Inc
United States of America
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        AS-CND
_chemical_formula_moiety         'C19 H27 O8, C19 H23 N2 O'
_chemical_formula_sum            'C38 H50 N2 O9'
_chemical_formula_weight         678.80
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   30.0476(16)
_cell_length_b                   6.6972(3)
_cell_length_c                   21.9220(12)
_cell_angle_alpha                90
_cell_angle_beta                 127.752(7)
_cell_angle_gamma                90
_cell_volume                     3488.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9768
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.753
_cell_measurement_theta_min      2.549
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4879
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       'solvent exporation in iPrOH/Heptane'
_exptl_crystal_recrystallization_method 'solvnet diffusion'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            62257
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.753
_diffrn_reflns_theta_max         66.753
_diffrn_reflns_theta_min         2.549
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5497
_reflns_number_total             6129
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.077
_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)+(0.0616P)²+9.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1600
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), N2(H2A), C29(H29),
 C30(H30), C32(H32), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C18(H18A,
 H18B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C37(H37)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 0.37806(16) 0.3082(5) 0.0958(2) 0.0251(8) Uani 1 1 d . . . . .
O2 O 0.39118(16) 0.4890(5) 0.1413(2) 0.0272(8) Uani 1 1 d . . . . .
O3 O 0.38654(16) 0.7045(5) 0.0548(2) 0.0264(8) Uani 1 1 d . . . . .
O4 O 0.46753(15) 0.5356(5) 0.1068(2) 0.0268(8) Uani 1 1 d . . . . .
O5 O 0.55421(15) 0.4053(6) 0.1708(2) 0.0269(9) Uani 1 1 d . . . . .
O6 O 0.57386(15) 0.5992(6) 0.1055(2) 0.0272(9) Uani 1 1 d . . . . .
O7 O 0.73445(16) 0.6833(7) 0.3833(2) 0.0361(10) Uani 1 1 d . . . . .
O8 O 0.74267(18) 0.9742(7) 0.3403(2) 0.0430(11) Uani 1 1 d . . . . .
C1 C 0.2497(3) 0.3035(12) -0.1863(4) 0.0481(18) Uani 1 1 d . . . . .
H1A H 0.247041 0.268791 -0.231859 0.072 Uiso 1 1 calc R U . . .
H1B H 0.231745 0.433199 -0.194381 0.072 Uiso 1 1 calc R U . . .
H1C H 0.230640 0.201170 -0.177900 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3112(3) 0.3147(9) -0.1161(3) 0.0337(13) Uani 1 1 d . . . . .
H2 H 0.328706 0.431454 -0.122658 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3424(3) 0.1264(9) -0.1097(3) 0.0372(15) Uani 1 1 d . . . . .
H3A H 0.324643 0.008909 -0.105039 0.045 Uiso 1 1 calc R U . . .
H3B H 0.338865 0.110588 -0.157367 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4041(3) 0.1331(9) -0.0408(3) 0.0324(13) Uani 1 1 d . . . . .
H4A H 0.422492 0.244088 -0.047636 0.039 Uiso 1 1 calc R U . . .
H4B H 0.422342 0.007068 -0.038492 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4132(2) 0.1618(8) 0.0356(3) 0.0271(12) Uani 1 1 d . . . . .
H5 H 0.397975 0.040147 0.043444 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3792(2) 0.3425(8) 0.0314(3) 0.0233(11) Uani 1 1 d . . . . .
C7 C 0.3177(2) 0.3451(8) -0.0413(3) 0.0260(12) Uani 1 1 d . . . . .
H7 H 0.299094 0.228076 -0.037092 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2854(2) 0.5317(9) -0.0468(3) 0.0304(13) Uani 1 1 d . . . . .
H8A H 0.293259 0.642088 -0.069044 0.037 Uiso 1 1 calc R U . . .
H8B H 0.244590 0.502899 -0.083196 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2992(2) 0.6027(9) 0.0288(3) 0.0317(13) Uani 1 1 d . . . . .
H9A H 0.287764 0.498079 0.048620 0.038 Uiso 1 1 calc R U . . .
H9B H 0.276669 0.723650 0.018779 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3611(2) 0.6507(8) 0.0907(3) 0.0283(13) Uani 1 1 d . . . . .
C11 C 0.3721(3) 0.8188(9) 0.1437(3) 0.0342(14) Uani 1 1 d . . . . .
H11A H 0.354401 0.788866 0.168149 0.051 Uiso 1 1 calc R U . . .
H11B H 0.356290 0.942763 0.113928 0.051 Uiso 1 1 calc R U . . .
H11C H 0.412763 0.834500 0.183446 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4097(2) 0.5415(8) 0.0428(3) 0.0238(12) Uani 1 1 d . . . . .
H12 H 0.406552 0.567842 -0.004628 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4972(2) 0.3789(8) 0.1028(3) 0.0234(11) Uani 1 1 d . . . . .
H13 H 0.494414 0.388856 0.055002 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4756(2) 0.1813(8) 0.1072(3) 0.0275(12) Uani 1 1 d . . . . .
H14 H 0.477024 0.183461 0.153938 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5120(3) 0.0061(9) 0.1159(4) 0.0413(15) Uani 1 1 d . . . . .
H15A H 0.494996 -0.119876 0.114929 0.062 Uiso 1 1 calc R U . . .
H15B H 0.549874 0.018067 0.164997 0.062 Uiso 1 1 calc R U . . .
H15C H 0.514381 0.008122 0.073241 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5876(2) 0.5278(8) 0.1645(3) 0.0246(12) Uani 1 1 d . . . . .
C17 C 0.6434(2) 0.5539(8) 0.2429(3) 0.0275(12) Uani 1 1 d . . . . .
H17A H 0.667832 0.438424 0.253609 0.033 Uiso 1 1 calc R U . . .
H17B H 0.637392 0.555449 0.282493 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6732(2) 0.7454(8) 0.2489(3) 0.0274(12) Uani 1 1 d . . . . .
H18A H 0.645152 0.854788 0.223958 0.033 Uiso 1 1 calc R U . . .
H18B H 0.688321 0.727867 0.219927 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7210(2) 0.8073(9) 0.3312(3) 0.0294(13) Uani 1 1 d . . . . .
O9 O 0.83165(17) 0.1804(6) 0.4597(2) 0.0326(9) Uani 1 1 d . . . . .
H9 H 0.807247 0.111091 0.421323 0.049 Uiso 1 1 calc R U . . .
N1 N 0.9396(2) 0.3250(10) 0.3552(3) 0.0448(14) Uani 1 1 d . . . . .
N2 N 0.82819(18) 0.5970(7) 0.5184(2) 0.0216(9) Uani 1 1 d . . . . .
H2A H 0.791174 0.631203 0.468343 0.026 Uiso 1 1 calc R U . . .
C20 C 0.9029(3) 0.6352(11) 0.2881(4) 0.0456(18) Uani 1 1 d . . . . .
H20 H 0.925638 0.622263 0.271778 0.055 Uiso 1 1 calc R U . . .
C21 C 0.8694(4) 0.7945(11) 0.2661(4) 0.054(2) Uani 1 1 d . . . . .
H21 H 0.868787 0.893576 0.234612 0.065 Uiso 1 1 calc R U . . .
C22 C 0.8349(3) 0.8170(10) 0.2889(4) 0.0426(16) Uani 1 1 d . . . . .
H22 H 0.810893 0.929764 0.272318 0.051 Uiso 1 1 calc R U . . .
C23 C 0.8361(3) 0.6763(9) 0.3350(3) 0.0304(13) Uani 1 1 d . . . . .
H23 H 0.813122 0.693837 0.350760 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8708(2) 0.5049(9) 0.3598(3) 0.0252(12) Uani 1 1 d . . . . .
C25 C 0.9050(2) 0.4850(10) 0.3357(3) 0.0357(15) Uani 1 1 d . . . . .
C26 C 0.9397(3) 0.1874(11) 0.3980(4) 0.0447(17) Uani 1 1 d . . . . .
H26 H 0.963600 0.075306 0.412212 0.054 Uiso 1 1 calc R U . . .
C27 C 0.9071(3) 0.1929(10) 0.4244(3) 0.0378(14) Uani 1 1 d . . . . .
H27 H 0.909279 0.086695 0.454915 0.045 Uiso 1 1 calc R U . . .
C28 C 0.8726(2) 0.3504(8) 0.4061(3) 0.0250(12) Uani 1 1 d . . . . .
C29 C 0.8372(2) 0.3654(8) 0.4344(3) 0.0242(12) Uani 1 1 d . . . . .
H29 H 0.798963 0.416445 0.391450 0.029 Uiso 1 1 calc R U . . .
C30 C 0.8665(2) 0.5184(8) 0.5018(3) 0.0216(11) Uani 1 1 d . . . . .
H30 H 0.877796 0.634854 0.485471 0.026 Uiso 1 1 calc R U . . .
C31 C 0.9204(2) 0.4382(8) 0.5770(3) 0.0261(12) Uani 1 1 d . . . . .
H31A H 0.953882 0.486742 0.582728 0.031 Uiso 1 1 calc R U . . .
H31B H 0.920498 0.290413 0.576122 0.031 Uiso 1 1 calc R U . . .
C32 C 0.9221(2) 0.5122(9) 0.6451(3) 0.0274(12) Uani 1 1 d . . . . .
H32 H 0.959130 0.476642 0.695006 0.033 Uiso 1 1 calc R U . . .
C33 C 0.8745(2) 0.4093(9) 0.6396(3) 0.0329(14) Uani 1 1 d . . . . .
H33A H 0.872931 0.460442 0.680584 0.039 Uiso 1 1 calc R U . . .
H33B H 0.881694 0.263765 0.647315 0.039 Uiso 1 1 calc R U . . .
C34 C 0.8181(2) 0.4488(9) 0.5601(3) 0.0275(12) Uani 1 1 d . . . . .
H34A H 0.803009 0.322921 0.530306 0.033 Uiso 1 1 calc R U . . .
H34B H 0.790401 0.502516 0.566316 0.033 Uiso 1 1 calc R U . . .
C35 C 0.8530(2) 0.7838(8) 0.5660(3) 0.0249(12) Uani 1 1 d . . . . .
H35A H 0.828803 0.832266 0.579414 0.030 Uiso 1 1 calc R U . . .
H35B H 0.854737 0.889246 0.535904 0.030 Uiso 1 1 calc R U . . .
C36 C 0.9131(2) 0.7396(8) 0.6409(3) 0.0240(12) Uani 1 1 d . . . . .
H36 H 0.914290 0.779676 0.685837 0.029 Uiso 1 1 calc R U . . .
C37 C 0.9566(2) 0.8599(9) 0.6438(3) 0.0281(12) Uani 1 1 d . . . . .
H37 H 0.959751 0.839770 0.603691 0.034 Uiso 1 1 calc R U . . .
C38 C 0.9905(3) 0.9903(9) 0.6974(3) 0.0306(13) Uani 1 1 d . . . . .
H38A H 0.988(3) 1.016(12) 0.736(4) 0.06(2) Uiso 1 1 d . . . . .
H38B H 1.014(3) 1.056(12) 0.694(4) 0.06(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.460(5) . ?
O1 C6 1.452(6) . ?
O2 C10 1.412(7) . ?
O3 C10 1.441(6) . ?
O3 C12 1.404(6) . ?
O4 C12 1.415(6) . ?
O4 C13 1.415(6) . ?
O5 C13 1.435(6) . ?
O5 C16 1.366(6) . ?
O6 C16 1.191(6) . ?
O7 C19 1.262(7) . ?
O8 C19 1.246(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.519(9) . ?
C2 H2 1.0000 . ?
C2 C3 1.524(9) . ?
C2 C7 1.542(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.535(7) . ?
C5 H5 1.0000 . ?
C5 C6 1.550(7) . ?
C5 C14 1.548(8) . ?
C6 C7 1.533(8) . ?
C6 C12 1.549(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.541(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(8) . ?
C10 C11 1.501(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C13 H13 1.0000 . ?
C13 C14 1.503(8) . ?
C14 H14 1.0000 . ?
C14 C15 1.534(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.506(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.522(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.522(8) . ?
O9 H9 0.8400 . ?
O9 C29 1.409(6) . ?
N1 C25 1.366(9) . ?
N1 C26 1.312(10) . ?
N2 H2A 1.0000 . ?
N2 C30 1.500(6) . ?
N2 C34 1.500(7) . ?
N2 C35 1.502(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.338(11) . ?
C20 C25 1.422(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.406(10) . ?
C22 H22 0.9500 . ?
C22 C23 1.366(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.417(8) . ?
C24 C25 1.419(7) . ?
C24 C28 1.427(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.412(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.356(8) . ?
C28 C29 1.526(7) . ?
C29 H29 1.0000 . ?
C29 C30 1.554(7) . ?
C30 H30 1.0000 . ?
C30 C31 1.536(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.542(7) . ?
C32 H32 1.0000 . ?
C32 C33 1.525(8) . ?
C32 C36 1.540(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.537(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.554(7) . ?
C36 H36 1.0000 . ?
C36 C37 1.504(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.310(8) . ?
C38 H38A 0.91(8) . ?
C38 H38B 0.88(8) . ?

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
C6 O1 O2 112.0(3) . . ?
C10 O2 O1 109.0(3) . . ?
C12 O3 C10 113.5(4) . . ?
C12 O4 C13 113.4(4) . . ?
C16 O5 C13 116.8(4) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 110.5(5) . . ?
C1 C2 C7 111.5(5) . . ?
C3 C2 H2 108.3 . . ?
C3 C2 C7 109.9(5) . . ?
C7 C2 H2 108.3 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.1(5) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.4(5) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5 107.0 . . ?
C4 C5 C6 111.3(5) . . ?
C4 C5 C14 114.3(5) . . ?
C6 C5 H5 107.0 . . ?
C14 C5 H5 107.0 . . ?
C14 C5 C6 109.9(4) . . ?
O1 C6 C5 103.1(4) . . ?
O1 C6 C7 106.4(4) . . ?
O1 C6 C12 110.1(4) . . ?
C7 C6 C5 113.6(4) . . ?
C7 C6 C12 112.1(4) . . ?
C12 C6 C5 111.0(4) . . ?
C2 C7 H7 106.3 . . ?
C6 C7 C2 113.1(4) . . ?
C6 C7 H7 106.3 . . ?
C6 C7 C8 113.0(4) . . ?
C8 C7 C2 111.1(5) . . ?
C8 C7 H7 106.3 . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.5(5) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C8 C9 C10 114.1(4) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
O2 C10 O3 108.8(4) . . ?
O2 C10 C9 112.6(4) . . ?
O2 C10 C11 103.7(4) . . ?
O3 C10 C9 109.5(4) . . ?
O3 C10 C11 107.2(4) . . ?
C11 C10 C9 114.8(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 106.6(4) . . ?
O3 C12 C6 112.7(4) . . ?
O3 C12 H12 108.3 . . ?
O4 C12 C6 112.5(4) . . ?
O4 C12 H12 108.3 . . ?
C6 C12 H12 108.3 . . ?
O4 C13 O5 103.9(4) . . ?
O4 C13 H13 111.3 . . ?
O4 C13 C14 109.6(4) . . ?
O5 C13 H13 111.3 . . ?
O5 C13 C14 109.2(4) . . ?
C14 C13 H13 111.3 . . ?
C5 C14 H14 107.7 . . ?
C13 C14 C5 108.2(4) . . ?
C13 C14 H14 107.7 . . ?
C13 C14 C15 112.3(4) . . ?
C15 C14 C5 113.0(5) . . ?
C15 C14 H14 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C17 109.2(4) . . ?
O6 C16 O5 124.3(5) . . ?
O6 C16 C17 126.5(5) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.5(5) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.3(5) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
O7 C19 C18 116.1(5) . . ?
O8 C19 O7 126.8(5) . . ?
O8 C19 C18 117.1(5) . . ?
C29 O9 H9 109.5 . . ?
C26 N1 C25 116.4(5) . . ?
C30 N2 H2A 108.5 . . ?
C30 N2 C35 109.5(4) . . ?
C34 N2 H2A 108.5 . . ?
C34 N2 C30 112.8(4) . . ?
C34 N2 C35 109.1(4) . . ?
C35 N2 H2A 108.5 . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C25 120.9(6) . . ?
C25 C20 H20 119.6 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(6) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(6) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.5(5) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 117.6(5) . . ?
C23 C24 C28 123.9(5) . . ?
C25 C24 C28 118.5(5) . . ?
N1 C25 C20 117.9(5) . . ?
N1 C25 C24 122.8(6) . . ?
C24 C25 C20 119.3(6) . . ?
N1 C26 H26 117.4 . . ?
N1 C26 C27 125.1(6) . . ?
C27 C26 H26 117.4 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.7(6) . . ?
C28 C27 H27 120.2 . . ?
C24 C28 C29 120.6(5) . . ?
C27 C28 C24 117.6(5) . . ?
C27 C28 C29 121.8(5) . . ?
O9 C29 C28 112.5(5) . . ?
O9 C29 H29 109.0 . . ?
O9 C29 C30 109.9(4) . . ?
C28 C29 H29 109.0 . . ?
C28 C29 C30 107.5(4) . . ?
C30 C29 H29 109.0 . . ?
N2 C30 C29 113.0(4) . . ?
N2 C30 H30 107.0 . . ?
N2 C30 C31 108.9(4) . . ?
C29 C30 H30 107.0 . . ?
C31 C30 C29 113.7(4) . . ?
C31 C30 H30 107.0 . . ?
C30 C31 H31A 110.0 . . ?
C30 C31 H31B 110.0 . . ?
C30 C31 C32 108.4(4) . . ?
H31A C31 H31B 108.4 . . ?
C32 C31 H31A 110.0 . . ?
C32 C31 H31B 110.0 . . ?
C31 C32 H32 109.8 . . ?
C33 C32 C31 107.7(5) . . ?
C33 C32 H32 109.8 . . ?
C33 C32 C36 108.6(5) . . ?
C36 C32 C31 111.1(4) . . ?
C36 C32 H32 109.8 . . ?
C32 C33 H33A 109.7 . . ?
C32 C33 H33B 109.7 . . ?
C32 C33 C34 110.0(4) . . ?
H33A C33 H33B 108.2 . . ?
C34 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
N2 C34 C33 108.1(4) . . ?
N2 C34 H34A 110.1 . . ?
N2 C34 H34B 110.1 . . ?
C33 C34 H34A 110.1 . . ?
C33 C34 H34B 110.1 . . ?
H34A C34 H34B 108.4 . . ?
N2 C35 H35A 109.7 . . ?
N2 C35 H35B 109.7 . . ?
N2 C35 C36 109.7(4) . . ?
H35A C35 H35B 108.2 . . ?
C36 C35 H35A 109.7 . . ?
C36 C35 H35B 109.7 . . ?
C32 C36 C35 107.5(4) . . ?
C32 C36 H36 107.9 . . ?
C35 C36 H36 107.9 . . ?
C37 C36 C32 114.2(5) . . ?
C37 C36 C35 111.2(4) . . ?
C37 C36 H36 107.9 . . ?
C36 C37 H37 117.5 . . ?
C38 C37 C36 125.0(5) . . ?
C38 C37 H37 117.5 . . ?
C37 C38 H38A 120(5) . . ?
C37 C38 H38B 119(5) . . ?
H38A C38 H38B 121(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 O2 C10 O3 -73.2(5) . . . . ?
O1 O2 C10 C9 48.3(5) . . . . ?
O1 O2 C10 C11 172.9(4) . . . . ?
O1 C6 C7 C2 -162.1(4) . . . . ?
O1 C6 C7 C8 70.5(5) . . . . ?
O1 C6 C12 O3 -54.6(6) . . . . ?
O1 C6 C12 O4 65.9(5) . . . . ?
O2 O1 C6 C5 134.2(4) . . . . ?
O2 O1 C6 C7 -106.0(4) . . . . ?
O2 O1 C6 C12 15.7(5) . . . . ?
O4 C13 C14 C5 63.6(5) . . . . ?
O4 C13 C14 C15 -171.1(5) . . . . ?
O5 C13 C14 C5 176.8(4) . . . . ?
O5 C13 C14 C15 -57.9(6) . . . . ?
O5 C16 C17 C18 -156.4(4) . . . . ?
O6 C16 C17 C18 24.4(8) . . . . ?
C1 C2 C3 C4 179.3(5) . . . . ?
C1 C2 C7 C6 176.0(5) . . . . ?
C1 C2 C7 C8 -55.7(7) . . . . ?
C2 C3 C4 C5 57.7(6) . . . . ?
C2 C7 C8 C9 -166.9(5) . . . . ?
C3 C2 C7 C6 53.1(6) . . . . ?
C3 C2 C7 C8 -178.6(4) . . . . ?
C3 C4 C5 C6 -51.6(6) . . . . ?
C3 C4 C5 C14 -176.8(5) . . . . ?
C4 C5 C6 O1 162.4(4) . . . . ?
C4 C5 C6 C7 47.6(6) . . . . ?
C4 C5 C6 C12 -79.7(5) . . . . ?
C4 C5 C14 C13 70.2(6) . . . . ?
C4 C5 C14 C15 -54.7(6) . . . . ?
C5 C6 C7 C2 -49.4(6) . . . . ?
C5 C6 C7 C8 -176.7(4) . . . . ?
C5 C6 C12 O3 -168.2(4) . . . . ?
C5 C6 C12 O4 -47.7(5) . . . . ?
C6 O1 O2 C10 44.8(5) . . . . ?
C6 C5 C14 C13 -55.8(5) . . . . ?
C6 C5 C14 C15 179.3(4) . . . . ?
C6 C7 C8 C9 -38.5(6) . . . . ?
C7 C2 C3 C4 -57.2(6) . . . . ?
C7 C6 C12 O3 63.6(5) . . . . ?
C7 C6 C12 O4 -175.9(4) . . . . ?
C7 C8 C9 C10 57.6(7) . . . . ?
C8 C9 C10 O2 -95.2(5) . . . . ?
C8 C9 C10 O3 26.0(6) . . . . ?
C8 C9 C10 C11 146.6(5) . . . . ?
C10 O3 C12 O4 -95.1(5) . . . . ?
C10 O3 C12 C6 28.8(6) . . . . ?
C12 O3 C10 O2 32.6(6) . . . . ?
C12 O3 C10 C9 -90.8(5) . . . . ?
C12 O3 C10 C11 144.1(5) . . . . ?
C12 O4 C13 O5 178.1(4) . . . . ?
C12 O4 C13 C14 -65.3(5) . . . . ?
C12 C6 C7 C2 77.4(6) . . . . ?
C12 C6 C7 C8 -49.9(6) . . . . ?
C13 O4 C12 O3 -179.3(4) . . . . ?
C13 O4 C12 C6 56.7(5) . . . . ?
C13 O5 C16 O6 -6.5(7) . . . . ?
C13 O5 C16 C17 174.3(4) . . . . ?
C14 C5 C6 O1 -69.9(5) . . . . ?
C14 C5 C6 C7 175.3(4) . . . . ?
C14 C5 C6 C12 48.0(5) . . . . ?
C16 O5 C13 O4 -88.9(5) . . . . ?
C16 O5 C13 C14 154.3(4) . . . . ?
C16 C17 C18 C19 164.2(4) . . . . ?
C17 C18 C19 O7 7.7(7) . . . . ?
C17 C18 C19 O8 -172.0(5) . . . . ?
O9 C29 C30 N2 -75.7(5) . . . . ?
O9 C29 C30 C31 49.0(6) . . . . ?
N1 C26 C27 C28 -0.5(10) . . . . ?
N2 C30 C31 C32 -13.5(6) . . . . ?
N2 C35 C36 C32 -8.3(5) . . . . ?
N2 C35 C36 C37 117.3(5) . . . . ?
C20 C21 C22 C23 0.9(10) . . . . ?
C21 C20 C25 N1 179.1(6) . . . . ?
C21 C20 C25 C24 0.1(9) . . . . ?
C21 C22 C23 C24 -0.9(9) . . . . ?
C22 C23 C24 C25 0.6(8) . . . . ?
C22 C23 C24 C28 -178.1(5) . . . . ?
C23 C24 C25 N1 -179.2(5) . . . . ?
C23 C24 C25 C20 -0.2(8) . . . . ?
C23 C24 C28 C27 178.8(5) . . . . ?
C23 C24 C28 C29 -2.0(8) . . . . ?
C24 C28 C29 O9 163.2(4) . . . . ?
C24 C28 C29 C30 -75.8(6) . . . . ?
C25 N1 C26 C27 0.2(9) . . . . ?
C25 C20 C21 C22 -0.5(10) . . . . ?
C25 C24 C28 C27 0.1(7) . . . . ?
C25 C24 C28 C29 179.3(5) . . . . ?
C26 N1 C25 C20 -178.8(5) . . . . ?
C26 N1 C25 C24 0.2(8) . . . . ?
C26 C27 C28 C24 0.3(8) . . . . ?
C26 C27 C28 C29 -178.9(5) . . . . ?
C27 C28 C29 O9 -17.6(7) . . . . ?
C27 C28 C29 C30 103.4(6) . . . . ?
C28 C24 C25 N1 -0.3(8) . . . . ?
C28 C24 C25 C20 178.6(5) . . . . ?
C28 C29 C30 N2 161.6(4) . . . . ?
C28 C29 C30 C31 -73.7(5) . . . . ?
C29 C30 C31 C32 -140.4(4) . . . . ?
C30 N2 C34 C33 64.1(5) . . . . ?
C30 N2 C35 C36 -56.4(5) . . . . ?
C30 C31 C32 C33 67.7(6) . . . . ?
C30 C31 C32 C36 -51.1(6) . . . . ?
C31 C32 C33 C34 -55.6(6) . . . . ?
C31 C32 C36 C35 63.4(5) . . . . ?
C31 C32 C36 C37 -60.4(6) . . . . ?
C32 C33 C34 N2 -7.0(6) . . . . ?
C32 C36 C37 C38 -118.7(6) . . . . ?
C33 C32 C36 C35 -54.8(5) . . . . ?
C33 C32 C36 C37 -178.6(4) . . . . ?
C34 N2 C30 C29 75.3(5) . . . . ?
C34 N2 C30 C31 -52.0(5) . . . . ?
C34 N2 C35 C36 67.4(5) . . . . ?
C35 N2 C30 C29 -163.1(4) . . . . ?
C35 N2 C30 C31 69.7(5) . . . . ?
C35 N2 C34 C33 -57.8(6) . . . . ?
C35 C36 C37 C38 119.5(6) . . . . ?
C36 C32 C33 C34 64.8(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_scx21_011
_database_code_depnum_ccdc_archive 'CCDC 2077969'
loop_
_audit_author_name
_audit_author_address
'QI JIANG'
;Boehringer Ingelheim Pharmaceuticals Inc
United States of America
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_scx21_011           
;
PROBLEM: Short Inter D-H..H-D       H5B      ..H7A      .       1.70 Ang.
RESPONSE: H2O molecules may disorded in the crystal lattice. No SQUEEZE use because the dihydrate structure is indicated
;
_vrf_PLAT035_scx21_011           
;
PROBLEM: _chemical_absolute_configuration Info  Not Given     Please Do !
RESPONSE: The absolute configuration is correct
;
_vrf_PLAT420_scx21_011           
;
PROBLEM: D-H Bond Without Acceptor  O7       --H7A      .     Please Check
RESPONSE: The H2O molecules in the crystal lattice may be disordered
;
# Added during the CSD deposition process: Thursday 15 April 2021 10:43 PM
# end Validation Reply Form

_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'QN HCl 2H2O'
_chemical_formula_moiety         'Cl, C20 H25 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H29 Cl N2 O4'
_chemical_formula_weight         396.90
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.7848(3)
_cell_length_b                   10.6171(5)
_cell_length_c                   15.4805(8)
_cell_angle_alpha                98.689(2)
_cell_angle_beta                 97.586(2)
_cell_angle_gamma                108.323(2)
_cell_volume                     1027.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.245
_cell_measurement_theta_min      2.942
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4263
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation in aqueous solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28580
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.245
_diffrn_reflns_theta_max         67.245
_diffrn_reflns_theta_min         2.942
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                6911
_reflns_number_total             6948
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.098
_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)+(0.1935P)²+0.2661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A), O7(H7A,H7B), O8(H8A)
2.b Ternary CH refined with riding coordinates:
 N4(H4A), N2(H2A), C31(H31), C11(H11), C18(H18), C12(H12), C34(H34), C38(H38),
 C32(H32), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C33(H33A,H33B), C16(H16A,H16B), C35(H35A,H35B), C37(H37A,
 H37B), C13(H13A,H13B), C17(H17A,H17B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C24(H24), C28(H28), C4(H4B), C8(H8), C29(H29), C27(H27), C7(H7),
 C23(H23), C3(H3), C39(H39), C19(H19)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.15060(19) 0.74680(12) 0.47247(9) 0.0234(4) Uani 1 1 d . . . . .
Cl2 Cl 0.6507(2) 0.25762(13) 0.53565(10) 0.0262(4) Uani 1 1 d . . . . .
O4 O 0.0231(6) 0.5570(4) 0.2850(3) 0.0184(8) Uani 1 1 d . . . . .
H4 H 0.030742 0.612539 0.331238 0.028 Uiso 1 1 calc R U . . .
O2 O -0.6923(6) 0.4607(4) -0.2843(3) 0.0207(9) Uani 1 1 d . . . . .
H2 H -0.752039 0.416744 -0.336012 0.031 Uiso 1 1 calc R U . . .
O3 O 0.9407(7) 0.8835(4) 0.1763(3) 0.0225(9) Uani 1 1 d . . . . .
O1 O -0.0424(7) 0.1277(4) -0.1754(3) 0.0225(9) Uani 1 1 d . . . . .
O6 O 0.1234(8) 0.2836(5) 0.5628(3) 0.0270(10) Uani 1 1 d G . . . .
H6A H 0.131127 0.206266 0.566777 0.041 Uiso 1 1 d G U . . .
O5 O 0.6871(8) 0.7255(5) 0.4116(3) 0.0263(10) Uani 1 1 d . . . . .
O7 O 0.5505(8) 0.9453(5) 0.4187(4) 0.0347(12) Uani 1 1 d G . . . .
H7A H 0.617974 0.943051 0.468511 0.052 Uiso 1 1 d G U . . .
H7B H 0.421739 0.903413 0.419670 0.052 Uiso 1 1 d G U . . .
N4 N 0.4096(7) 0.4700(5) 0.3388(3) 0.0170(10) Uani 1 1 d . . . . .
H4A H 0.506978 0.561512 0.372011 0.020 Uiso 1 1 calc R U . . .
N3 N 0.1198(8) 0.6738(5) -0.0137(3) 0.0221(11) Uani 1 1 d . . . . .
O8 O 0.2371(10) 1.0556(5) 0.5781(4) 0.0420(13) Uani 1 1 d G . . . .
H8A H 0.217667 0.978227 0.546770 0.063 Uiso 1 1 d G U . . .
N2 N -0.2578(8) 0.5389(5) -0.3416(3) 0.0194(10) Uani 1 1 d . . . . .
H2A H -0.274626 0.445782 -0.373283 0.023 Uiso 1 1 calc R U . . .
N1 N -0.5386(8) 0.3410(5) 0.0142(3) 0.0220(10) Uani 1 1 d . . . . .
C25 C 0.3187(10) 0.7207(5) 0.0380(4) 0.0185(11) Uani 1 1 d . . . . .
C5 C -0.4166(9) 0.2948(5) -0.0372(4) 0.0193(12) Uani 1 1 d . . . . .
C36 C 0.2503(9) 0.4124(6) 0.3957(4) 0.0185(12) Uani 1 1 d . . . . .
H36A H 0.181187 0.478556 0.414655 0.022 Uiso 1 1 calc R U . . .
H36B H 0.323267 0.394254 0.449719 0.022 Uiso 1 1 calc R U . . .
C30 C 0.1859(9) 0.6297(5) 0.1620(4) 0.0157(11) Uani 1 1 d . . . . .
C9 C -0.6496(9) 0.4336(5) -0.1095(4) 0.0188(11) Uani 1 1 d . . . . .
H9 H -0.732567 0.483216 -0.131653 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4902(10) 0.7869(6) -0.0014(4) 0.0230(12) Uani 1 1 d . . . . .
H24 H 0.463648 0.797046 -0.061350 0.028 Uiso 1 1 calc R U . . .
C10 C -0.5281(9) 0.3880(5) -0.1615(4) 0.0176(11) Uani 1 1 d . . . . .
C28 C -0.0360(10) 0.6103(6) 0.0228(4) 0.0215(12) Uani 1 1 d . . . . .
H28 H -0.175077 0.578949 -0.011716 0.026 Uiso 1 1 calc R U . . .
C4 C -0.2908(9) 0.2246(6) 0.0014(4) 0.0211(12) Uani 1 1 d . . . . .
H4B H -0.294445 0.211879 0.060663 0.025 Uiso 1 1 calc R U . . .
C8 C -0.6518(10) 0.4072(6) -0.0229(4) 0.0226(12) Uani 1 1 d . . . . .
H8 H -0.740028 0.438823 0.010915 0.027 Uiso 1 1 calc R U . . .
C29 C -0.0112(9) 0.5854(5) 0.1098(4) 0.0191(12) Uani 1 1 d . . . . .
H29 H -0.131130 0.538089 0.132053 0.023 Uiso 1 1 calc R U . . .
C26 C 0.3613(9) 0.7032(5) 0.1268(4) 0.0164(11) Uani 1 1 d . . . . .
C33 C 0.1600(9) 0.3435(5) 0.1979(4) 0.0184(11) Uani 1 1 d . . . . .
H33A H 0.203656 0.316723 0.141414 0.022 Uiso 1 1 calc R U . . .
H33B H 0.015750 0.347309 0.183559 0.022 Uiso 1 1 calc R U . . .
C31 C 0.2181(9) 0.5972(5) 0.2542(3) 0.0157(11) Uani 1 1 d . . . . .
H31 H 0.319932 0.679518 0.296605 0.019 Uiso 1 1 calc R U . . .
C16 C -0.3950(10) 0.5952(6) -0.3984(4) 0.0242(13) Uani 1 1 d . . . . .
H16A H -0.543260 0.532541 -0.412075 0.029 Uiso 1 1 calc R U . . .
H16B H -0.345567 0.604148 -0.455281 0.029 Uiso 1 1 calc R U . . .
C11 C -0.5200(9) 0.4193(5) -0.2543(4) 0.0167(11) Uani 1 1 d . . . . .
H11 H -0.527539 0.336038 -0.296526 0.020 Uiso 1 1 calc R U . . .
C35 C 0.0838(9) 0.2804(6) 0.3409(4) 0.0202(12) Uani 1 1 d . . . . .
H35A H 0.063135 0.208373 0.376065 0.024 Uiso 1 1 calc R U . . .
H35B H -0.053085 0.294376 0.325407 0.024 Uiso 1 1 calc R U . . .
C6 C -0.4072(9) 0.3129(5) -0.1265(4) 0.0174(11) Uani 1 1 d . . . . .
C18 C -0.0045(9) 0.7753(6) -0.2872(4) 0.0205(12) Uani 1 1 d . . . . .
H18 H 0.027356 0.833010 -0.332540 0.025 Uiso 1 1 calc R U . . .
C2 C -0.1635(10) 0.1883(5) -0.1352(4) 0.0200(12) Uani 1 1 d . . . . .
C12 C -0.3082(9) 0.5313(5) -0.2494(3) 0.0170(11) Uani 1 1 d . . . . .
H12 H -0.195479 0.506359 -0.215080 0.020 Uiso 1 1 calc R U . . .
C34 C 0.1595(9) 0.2382(5) 0.2561(4) 0.0190(11) Uani 1 1 d . . . . .
H34 H 0.061091 0.146775 0.223270 0.023 Uiso 1 1 calc R U . . .
C38 C 0.3847(9) 0.2329(5) 0.2819(4) 0.0190(12) Uani 1 1 d . . . . .
H38 H 0.381784 0.175263 0.327533 0.023 Uiso 1 1 calc R U . . .
C27 C 0.5728(10) 0.7567(5) 0.1760(4) 0.0183(11) Uani 1 1 d . . . . .
H27 H 0.602478 0.746523 0.235747 0.022 Uiso 1 1 calc R U . . .
C22 C 0.7348(10) 0.8235(5) 0.1361(4) 0.0188(11) Uani 1 1 d . . . . .
C7 C -0.2794(9) 0.2575(5) -0.1747(4) 0.0183(11) Uani 1 1 d . . . . .
H7 H -0.273633 0.268124 -0.234229 0.022 Uiso 1 1 calc R U . . .
C37 C 0.5372(9) 0.3784(6) 0.3251(4) 0.0210(12) Uani 1 1 d . . . . .
H37A H 0.619039 0.378320 0.382997 0.025 Uiso 1 1 calc R U . . .
H37B H 0.637952 0.411177 0.285951 0.025 Uiso 1 1 calc R U . . .
C23 C 0.6924(9) 0.8359(6) 0.0459(4) 0.0203(12) Uani 1 1 d . . . . .
H23 H 0.805646 0.878631 0.018464 0.024 Uiso 1 1 calc R U . . .
C32 C 0.3140(8) 0.4835(5) 0.2478(4) 0.0169(11) Uani 1 1 d . . . . .
H32 H 0.431799 0.509324 0.214194 0.020 Uiso 1 1 calc R U . . .
C3 C -0.1655(9) 0.1755(6) -0.0461(4) 0.0219(12) Uani 1 1 d . . . . .
H3 H -0.078607 0.132149 -0.018691 0.026 Uiso 1 1 calc R U . . .
C14 C -0.2174(10) 0.7759(6) -0.2623(4) 0.0198(12) Uani 1 1 d . . . . .
H14 H -0.202080 0.868879 -0.230849 0.024 Uiso 1 1 calc R U . . .
C39 C 0.4625(11) 0.1736(6) 0.2048(4) 0.0274(14) Uani 1 1 d . . . . .
H39 H 0.458001 0.211547 0.153141 0.033 Uiso 1 1 calc R U . . .
C13 C -0.2913(9) 0.6742(6) -0.2028(4) 0.0181(11) Uani 1 1 d . . . . .
H13A H -0.430915 0.673164 -0.189979 0.022 Uiso 1 1 calc R U . . .
H13B H -0.189583 0.702086 -0.145576 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1762(10) 0.8313(7) -0.2089(4) 0.0266(13) Uani 1 1 d . . . . .
H19 H 0.166232 0.789157 -0.158962 0.032 Uiso 1 1 calc R U . . .
C17 C -0.0309(10) 0.6277(6) -0.3309(4) 0.0216(12) Uani 1 1 d . . . . .
H17A H 0.010979 0.625816 -0.389872 0.026 Uiso 1 1 calc R U . . .
H17B H 0.061637 0.593429 -0.293113 0.026 Uiso 1 1 calc R U . . .
C1 C -0.0357(11) 0.1364(6) -0.2663(4) 0.0250(13) Uani 1 1 d . . . . .
H1A H -0.176828 0.088582 -0.302915 0.038 Uiso 1 1 calc R U . . .
H1B H 0.064278 0.094874 -0.287062 0.038 Uiso 1 1 calc R U . . .
H1C H 0.010202 0.231849 -0.271270 0.038 Uiso 1 1 calc R U . . .
C15 C -0.3830(10) 0.7342(6) -0.3483(4) 0.0235(13) Uani 1 1 d . . . . .
H15A H -0.343522 0.802204 -0.385961 0.028 Uiso 1 1 calc R U . . .
H15B H -0.522767 0.729695 -0.334000 0.028 Uiso 1 1 calc R U . . .
C21 C 0.9943(10) 0.8786(6) 0.2676(4) 0.0257(13) Uani 1 1 d . . . . .
H21A H 0.950122 0.783956 0.274285 0.039 Uiso 1 1 calc R U . . .
H21B H 0.922110 0.927585 0.303298 0.039 Uiso 1 1 calc R U . . .
H21C H 1.147666 0.920888 0.288081 0.039 Uiso 1 1 calc R U . . .
C40 C 0.5360(13) 0.0734(7) 0.2035(5) 0.0334(16) Uani 1 1 d . . . . .
C20 C 0.3481(12) 0.9356(8) -0.2055(5) 0.0383(17) Uani 1 1 d . . . . .
H20A H 0.472(14) 0.974(9) -0.144(6) 0.03(2) Uiso 1 1 d . . . . .
H40A H 0.513(14) 0.028(9) 0.245(6) 0.03(2) Uiso 1 1 d . . . . .
H20B H 0.336(18) 0.983(11) -0.253(7) 0.06(3) Uiso 1 1 d . . . . .
H5A H 0.819(15) 0.735(8) 0.428(6) 0.03(2) Uiso 1 1 d . . . . .
H40B H 0.608(14) 0.039(9) 0.152(6) 0.03(2) Uiso 1 1 d . . . . .
H6B H -0.008(12) 0.262(6) 0.545(4) 0.005(14) Uiso 1 1 d . . . . .
H8B H 0.360(12) 1.097(7) 0.568(4) 0.007(14) Uiso 1 1 d . . . . .
H5B H 0.656(15) 0.798(10) 0.425(6) 0.04(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8400 . ?
O4 C31 1.426(7) . ?
O2 H2 0.8400 . ?
O2 C11 1.420(7) . ?
O3 C22 1.355(8) . ?
O3 C21 1.425(7) . ?
O1 C2 1.350(8) . ?
O1 C1 1.430(7) . ?
O6 H6A 0.8499 . ?
O6 H6B 0.84(7) . ?
O5 H5A 0.87(10) . ?
O5 H5B 0.87(10) . ?
O7 H7A 0.8502 . ?
O7 H7B 0.8495 . ?
N4 H4A 1.0000 . ?
N4 C36 1.522(7) . ?
N4 C37 1.502(8) . ?
N4 C32 1.518(6) . ?
N3 C25 1.371(8) . ?
N3 C28 1.309(9) . ?
O8 H8A 0.8503 . ?
O8 H8B 0.86(8) . ?
N2 H2A 1.0000 . ?
N2 C16 1.513(8) . ?
N2 C12 1.518(7) . ?
N2 C17 1.503(8) . ?
N1 C5 1.367(8) . ?
N1 C8 1.326(8) . ?
C25 C24 1.422(9) . ?
C25 C26 1.420(8) . ?
C5 C4 1.429(8) . ?
C5 C6 1.430(8) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C35 1.534(8) . ?
C30 C29 1.366(8) . ?
C30 C26 1.427(8) . ?
C30 C31 1.522(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(9) . ?
C9 C8 1.411(9) . ?
C24 H24 0.9500 . ?
C24 C23 1.364(9) . ?
C10 C11 1.526(7) . ?
C10 C6 1.424(8) . ?
C28 H28 0.9500 . ?
C28 C29 1.410(8) . ?
C4 H4B 0.9500 . ?
C4 C3 1.364(9) . ?
C8 H8 0.9500 . ?
C29 H29 0.9500 . ?
C26 C27 1.425(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.537(7) . ?
C33 C32 1.537(7) . ?
C31 H31 1.0000 . ?
C31 C32 1.537(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.533(9) . ?
C11 H11 1.0000 . ?
C11 C12 1.534(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C34 1.527(8) . ?
C6 C7 1.419(8) . ?
C18 H18 1.0000 . ?
C18 C14 1.545(9) . ?
C18 C19 1.503(8) . ?
C18 C17 1.555(8) . ?
C2 C7 1.380(8) . ?
C2 C3 1.408(8) . ?
C12 H12 1.0000 . ?
C12 C13 1.541(8) . ?
C34 H34 1.0000 . ?
C34 C38 1.548(8) . ?
C38 H38 1.0000 . ?
C38 C37 1.551(8) . ?
C38 C39 1.499(9) . ?
C27 H27 0.9500 . ?
C27 C22 1.383(9) . ?
C22 C23 1.422(8) . ?
C7 H7 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C23 H23 0.9500 . ?
C32 H32 1.0000 . ?
C3 H3 0.9500 . ?
C14 H14 1.0000 . ?
C14 C13 1.532(8) . ?
C14 C15 1.531(8) . ?
C39 H39 0.9500 . ?
C39 C40 1.308(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C20 1.320(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C40 H40A 0.86(9) . ?
C40 H40B 1.07(9) . ?
C20 H20A 1.11(9) . ?
C20 H20B 0.96(11) . ?

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
C31 O4 H4 109.5 . . ?
C11 O2 H2 109.5 . . ?
C22 O3 C21 117.2(5) . . ?
C2 O1 C1 116.7(4) . . ?
H6A O6 H6B 100.2 . . ?
H5A O5 H5B 115(8) . . ?
H7A O7 H7B 104.5 . . ?
C36 N4 H4A 108.5 . . ?
C37 N4 H4A 108.5 . . ?
C37 N4 C36 108.1(4) . . ?
C37 N4 C32 107.9(4) . . ?
C32 N4 H4A 108.5 . . ?
C32 N4 C36 115.1(4) . . ?
C28 N3 C25 116.8(5) . . ?
H8A O8 H8B 97.5 . . ?
C16 N2 H2A 108.6 . . ?
C16 N2 C12 114.4(5) . . ?
C12 N2 H2A 108.6 . . ?
C17 N2 H2A 108.6 . . ?
C17 N2 C16 108.4(4) . . ?
C17 N2 C12 108.2(4) . . ?
C8 N1 C5 116.1(5) . . ?
N3 C25 C24 117.5(5) . . ?
N3 C25 C26 123.5(5) . . ?
C26 C25 C24 119.0(5) . . ?
N1 C5 C4 117.5(5) . . ?
N1 C5 C6 124.1(5) . . ?
C4 C5 C6 118.4(5) . . ?
N4 C36 H36A 109.9 . . ?
N4 C36 H36B 109.9 . . ?
N4 C36 C35 108.9(4) . . ?
H36A C36 H36B 108.3 . . ?
C35 C36 H36A 109.9 . . ?
C35 C36 H36B 109.9 . . ?
C29 C30 C26 118.4(5) . . ?
C29 C30 C31 120.7(5) . . ?
C26 C30 C31 120.9(5) . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(5) . . ?
C8 C9 H9 119.9 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.7(6) . . ?
C23 C24 H24 119.7 . . ?
C9 C10 C11 120.5(5) . . ?
C9 C10 C6 118.5(5) . . ?
C6 C10 C11 121.0(5) . . ?
N3 C28 H28 117.8 . . ?
N3 C28 C29 124.4(6) . . ?
C29 C28 H28 117.8 . . ?
C5 C4 H4B 119.7 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4B 119.7 . . ?
N1 C8 C9 124.2(6) . . ?
N1 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C30 C29 C28 119.8(6) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C25 C26 C30 117.1(5) . . ?
C25 C26 C27 119.7(5) . . ?
C27 C26 C30 123.2(5) . . ?
H33A C33 H33B 108.2 . . ?
C34 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
C32 C33 H33A 109.7 . . ?
C32 C33 H33B 109.7 . . ?
C32 C33 C34 109.7(4) . . ?
O4 C31 C30 111.0(4) . . ?
O4 C31 H31 109.1 . . ?
O4 C31 C32 111.0(4) . . ?
C30 C31 H31 109.1 . . ?
C30 C31 C32 107.6(4) . . ?
C32 C31 H31 109.1 . . ?
N2 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
N2 C16 C15 109.4(4) . . ?
H16A C16 H16B 108.2 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
O2 C11 C10 110.7(5) . . ?
O2 C11 H11 109.1 . . ?
O2 C11 C12 110.8(4) . . ?
C10 C11 H11 109.1 . . ?
C10 C11 C12 108.0(4) . . ?
C12 C11 H11 109.1 . . ?
C36 C35 H35A 109.9 . . ?
C36 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C34 C35 C36 108.8(4) . . ?
C34 C35 H35A 109.9 . . ?
C34 C35 H35B 109.9 . . ?
C10 C6 C5 116.9(5) . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 C10 123.7(5) . . ?
C14 C18 H18 108.1 . . ?
C14 C18 C17 108.2(5) . . ?
C19 C18 H18 108.1 . . ?
C19 C18 C14 112.8(5) . . ?
C19 C18 C17 111.3(5) . . ?
C17 C18 H18 108.1 . . ?
O1 C2 C7 125.3(5) . . ?
O1 C2 C3 114.2(5) . . ?
C7 C2 C3 120.5(5) . . ?
N2 C12 C11 111.1(4) . . ?
N2 C12 H12 107.4 . . ?
N2 C12 C13 108.0(4) . . ?
C11 C12 H12 107.4 . . ?
C11 C12 C13 115.3(5) . . ?
C13 C12 H12 107.4 . . ?
C33 C34 H34 109.7 . . ?
C33 C34 C38 110.8(5) . . ?
C35 C34 C33 108.0(5) . . ?
C35 C34 H34 109.7 . . ?
C35 C34 C38 108.9(5) . . ?
C38 C34 H34 109.7 . . ?
C34 C38 H38 108.1 . . ?
C34 C38 C37 108.5(4) . . ?
C37 C38 H38 108.1 . . ?
C39 C38 C34 113.3(5) . . ?
C39 C38 H38 108.1 . . ?
C39 C38 C37 110.6(5) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 C26 119.5(5) . . ?
C22 C27 H27 120.2 . . ?
O3 C22 C27 125.4(5) . . ?
O3 C22 C23 114.0(5) . . ?
C27 C22 C23 120.5(5) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 C6 120.1(5) . . ?
C2 C7 H7 119.9 . . ?
N4 C37 C38 108.9(4) . . ?
N4 C37 H37A 109.9 . . ?
N4 C37 H37B 109.9 . . ?
C38 C37 H37A 109.9 . . ?
C38 C37 H37B 109.9 . . ?
H37A C37 H37B 108.3 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N4 C32 C33 108.4(4) . . ?
N4 C32 C31 112.0(4) . . ?
N4 C32 H32 107.1 . . ?
C33 C32 C31 114.8(5) . . ?
C33 C32 H32 107.1 . . ?
C31 C32 H32 107.1 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C18 C14 H14 109.7 . . ?
C13 C14 C18 111.0(5) . . ?
C13 C14 H14 109.7 . . ?
C15 C14 C18 108.2(5) . . ?
C15 C14 H14 109.7 . . ?
C15 C14 C13 108.5(5) . . ?
C38 C39 H39 117.6 . . ?
C40 C39 C38 124.8(6) . . ?
C40 C39 H39 117.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 C12 110.1(5) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C18 C19 H19 118.1 . . ?
C20 C19 C18 123.8(6) . . ?
C20 C19 H19 118.1 . . ?
N2 C17 C18 109.4(5) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
C14 C15 C16 109.0(5) . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C39 C40 H40A 116(6) . . ?
C39 C40 H40B 125(5) . . ?
H40A C40 H40B 119(7) . . ?
C19 C20 H20A 119(4) . . ?
C19 C20 H20B 113(7) . . ?
H20A C20 H20B 126(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C31 C32 N4 -74.5(5) . . . . ?
O4 C31 C32 C33 49.5(6) . . . . ?
O2 C11 C12 N2 -75.8(6) . . . . ?
O2 C11 C12 C13 47.5(6) . . . . ?
O3 C22 C23 C24 -176.4(5) . . . . ?
O1 C2 C7 C6 177.7(5) . . . . ?
O1 C2 C3 C4 -176.0(5) . . . . ?
N4 C36 C35 C34 11.3(6) . . . . ?
N3 C25 C24 C23 -179.9(5) . . . . ?
N3 C25 C26 C30 1.5(8) . . . . ?
N3 C25 C26 C27 -179.3(5) . . . . ?
N3 C28 C29 C30 0.5(9) . . . . ?
N2 C16 C15 C14 6.3(7) . . . . ?
N2 C12 C13 C14 -3.4(6) . . . . ?
N1 C5 C4 C3 179.9(5) . . . . ?
N1 C5 C6 C10 2.3(8) . . . . ?
N1 C5 C6 C7 -178.3(5) . . . . ?
C25 N3 C28 C29 -1.3(8) . . . . ?
C25 C24 C23 C22 -1.0(8) . . . . ?
C25 C26 C27 C22 -0.9(8) . . . . ?
C5 N1 C8 C9 -1.2(8) . . . . ?
C5 C4 C3 C2 -2.5(8) . . . . ?
C5 C6 C7 C2 -0.7(8) . . . . ?
C36 N4 C37 C38 57.0(6) . . . . ?
C36 N4 C32 C33 -56.7(6) . . . . ?
C36 N4 C32 C31 70.8(6) . . . . ?
C36 C35 C34 C33 -67.2(6) . . . . ?
C36 C35 C34 C38 53.2(6) . . . . ?
C30 C26 C27 C22 178.3(5) . . . . ?
C30 C31 C32 N4 163.9(4) . . . . ?
C30 C31 C32 C33 -72.1(6) . . . . ?
C9 C10 C11 O2 -17.2(7) . . . . ?
C9 C10 C11 C12 104.3(6) . . . . ?
C9 C10 C6 C5 -2.2(7) . . . . ?
C9 C10 C6 C7 178.5(5) . . . . ?
C24 C25 C26 C30 -176.7(5) . . . . ?
C24 C25 C26 C27 2.5(8) . . . . ?
C10 C9 C8 N1 1.2(9) . . . . ?
C10 C11 C12 N2 162.8(5) . . . . ?
C10 C11 C12 C13 -73.8(6) . . . . ?
C10 C6 C7 C2 178.6(5) . . . . ?
C28 N3 C25 C24 178.5(5) . . . . ?
C28 N3 C25 C26 0.3(8) . . . . ?
C4 C5 C6 C10 -177.6(5) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C8 N1 C5 C4 179.2(5) . . . . ?
C8 N1 C5 C6 -0.6(8) . . . . ?
C8 C9 C10 C11 -178.4(5) . . . . ?
C8 C9 C10 C6 0.6(8) . . . . ?
C29 C30 C26 C25 -2.3(7) . . . . ?
C29 C30 C26 C27 178.5(5) . . . . ?
C29 C30 C31 O4 -17.7(7) . . . . ?
C29 C30 C31 C32 103.9(6) . . . . ?
C26 C25 C24 C23 -1.6(8) . . . . ?
C26 C30 C29 C28 1.4(8) . . . . ?
C26 C30 C31 O4 164.4(4) . . . . ?
C26 C30 C31 C32 -74.0(6) . . . . ?
C26 C27 C22 O3 177.3(5) . . . . ?
C26 C27 C22 C23 -1.7(8) . . . . ?
C33 C34 C38 C37 53.7(6) . . . . ?
C33 C34 C38 C39 -69.5(6) . . . . ?
C31 C30 C29 C28 -176.5(5) . . . . ?
C31 C30 C26 C25 175.6(5) . . . . ?
C31 C30 C26 C27 -3.5(8) . . . . ?
C16 N2 C12 C11 71.3(6) . . . . ?
C16 N2 C12 C13 -56.1(6) . . . . ?
C16 N2 C17 C18 58.6(6) . . . . ?
C11 C10 C6 C5 176.8(5) . . . . ?
C11 C10 C6 C7 -2.6(8) . . . . ?
C11 C12 C13 C14 -128.3(5) . . . . ?
C35 C34 C38 C37 -64.9(6) . . . . ?
C35 C34 C38 C39 171.8(5) . . . . ?
C6 C5 C4 C3 -0.2(8) . . . . ?
C6 C10 C11 O2 163.9(4) . . . . ?
C6 C10 C11 C12 -74.6(6) . . . . ?
C18 C14 C13 C12 -56.7(6) . . . . ?
C18 C14 C15 C16 57.0(6) . . . . ?
C12 N2 C16 C15 54.9(6) . . . . ?
C12 N2 C17 C18 -66.0(6) . . . . ?
C34 C33 C32 N4 -1.2(6) . . . . ?
C34 C33 C32 C31 -127.2(5) . . . . ?
C34 C38 C37 N4 7.9(6) . . . . ?
C34 C38 C39 C40 -127.0(7) . . . . ?
C27 C22 C23 C24 2.7(8) . . . . ?
C7 C2 C3 C4 3.6(8) . . . . ?
C37 N4 C36 C35 -69.4(6) . . . . ?
C37 N4 C32 C33 64.0(5) . . . . ?
C37 N4 C32 C31 -168.4(4) . . . . ?
C37 C38 C39 C40 111.0(8) . . . . ?
C32 N4 C36 C35 51.2(6) . . . . ?
C32 N4 C37 C38 -68.0(5) . . . . ?
C32 C33 C34 C35 61.4(6) . . . . ?
C32 C33 C34 C38 -57.8(6) . . . . ?
C3 C2 C7 C6 -2.0(8) . . . . ?
C14 C18 C19 C20 -122.1(7) . . . . ?
C14 C18 C17 N2 5.1(6) . . . . ?
C39 C38 C37 N4 132.8(5) . . . . ?
C13 C14 C15 C16 -63.5(6) . . . . ?
C19 C18 C14 C13 -68.2(6) . . . . ?
C19 C18 C14 C15 172.9(5) . . . . ?
C19 C18 C17 N2 129.5(5) . . . . ?
C17 N2 C16 C15 -65.9(6) . . . . ?
C17 N2 C12 C11 -167.8(4) . . . . ?
C17 N2 C12 C13 64.8(6) . . . . ?
C17 C18 C14 C13 55.3(6) . . . . ?
C17 C18 C14 C15 -63.6(6) . . . . ?
C17 C18 C19 C20 116.1(8) . . . . ?
C1 O1 C2 C7 -0.2(8) . . . . ?
C1 O1 C2 C3 179.5(5) . . . . ?
C15 C14 C13 C12 62.1(6) . . . . ?
C21 O3 C22 C27 -0.8(8) . . . . ?
C21 O3 C22 C23 178.3(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
