# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_xr13
_database_code_depnum_ccdc_archive 'CCDC 1851079'
loop_
_audit_author_name
_audit_author_address
'Eduard '
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2018-06-22 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          373
_chemical_formula_moiety         'C34 H28 Cl N3 O3'
_chemical_formula_sum            'C34 H28 Cl N3 O3'
_chemical_formula_weight         562.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.2201(7)
_cell_length_b                   12.7050(14)
_cell_length_c                   35.317(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2791.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1009
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      19.01
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16780
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.703
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5745
_reflns_number_gt                3690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5745
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4773(6) 0.3349(3) 0.10506(10) 0.0219(9) Uani 1 1 d . . . . .
H1 H 0.332169 0.308175 0.097542 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6183(6) 0.3553(3) 0.06966(10) 0.0227(9) Uani 1 1 d . . . . .
H2 H 0.524075 0.387204 0.049787 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7723(7) 0.4413(3) 0.08357(11) 0.0293(10) Uani 1 1 d . . . . .
H3A H 0.834645 0.480757 0.062034 0.035 Uiso 1 1 calc R U . . .
H3B H 0.890325 0.410837 0.098846 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6277(6) 0.5128(3) 0.10792(11) 0.0250(10) Uani 1 1 d . . . . .
H4 H 0.711867 0.539142 0.130113 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3573(7) 0.4589(3) 0.15451(11) 0.0268(10) Uani 1 1 d . . . . .
C6 C 0.1223(7) 0.3811(3) 0.19954(10) 0.0303(10) Uani 1 1 d . . . . .
H6A H -0.032340 0.391794 0.194095 0.036 Uiso 1 1 calc R U . . .
H6B H 0.174430 0.442210 0.214300 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1522(7) 0.2818(3) 0.22209(10) 0.0245(10) Uani 1 1 d . . . . .
C8 C -0.0168(7) 0.2450(3) 0.24398(10) 0.0306(11) Uani 1 1 d . . . . .
H8 H -0.152813 0.278914 0.242781 0.037 Uiso 1 1 calc R U . . .
C9 C 0.0116(7) 0.1586(3) 0.26773(11) 0.0334(11) Uani 1 1 d . . . . .
H9 H -0.103920 0.134837 0.283103 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2059(8) 0.1079(3) 0.26896(11) 0.0379(11) Uani 1 1 d . . . . .
H10 H 0.224873 0.049047 0.285222 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3744(7) 0.1422(3) 0.24655(11) 0.0341(11) Uani 1 1 d . . . . .
H11 H 0.508464 0.106358 0.247071 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3465(7) 0.2291(3) 0.22337(11) 0.0301(11) Uani 1 1 d . . . . .
H12 H 0.462613 0.252764 0.208114 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5848(7) 0.2597(3) 0.13253(10) 0.0235(10) Uani 1 1 d . . . . .
C14 C 0.5881(7) 0.0716(3) 0.15029(10) 0.0240(10) Uani 1 1 d . . . . .
C15 C 0.7697(7) 0.0683(3) 0.17193(10) 0.0303(10) Uani 1 1 d . . . . .
H15 H 0.858510 0.128825 0.174209 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8244(8) -0.0252(3) 0.19080(11) 0.0370(12) Uani 1 1 d . . . . .
H16 H 0.951333 -0.026448 0.205752 0.044 Uiso 1 1 calc R U . . .
C17 C 0.7038(7) -0.1136(3) 0.18859(11) 0.0354(11) Uani 1 1 d . . . . .
H17 H 0.744815 -0.175423 0.201911 0.042 Uiso 1 1 calc R U . . .
C18 C 0.5156(7) -0.1125(3) 0.16610(10) 0.0272(10) Uani 1 1 d . . . . .
C19 C 0.4566(7) -0.0194(3) 0.14673(11) 0.0248(10) Uani 1 1 d . . . . .
C20 C 0.3796(7) -0.2002(3) 0.16256(11) 0.0364(12) Uani 1 1 d . . . . .
H20 H 0.411756 -0.263796 0.175518 0.044 Uiso 1 1 calc R U . . .
C21 C 0.2013(8) -0.1930(3) 0.14036(11) 0.0376(12) Uani 1 1 d . . . . .
H21 H 0.108065 -0.251701 0.137401 0.045 Uiso 1 1 calc R U . . .
C22 C 0.1575(7) -0.0980(3) 0.12199(12) 0.0377(12) Uani 1 1 d . . . . .
H22 H 0.031870 -0.094311 0.106756 0.045 Uiso 1 1 calc R U . . .
C23 C 0.7117(6) 0.2544(3) 0.05353(10) 0.0223(9) Uani 1 1 d . . . . .
C24 C 0.8981(7) 0.2077(3) 0.06699(11) 0.0295(10) Uani 1 1 d . . . . .
H24 H 0.979215 0.242013 0.086130 0.035 Uiso 1 1 calc R U . . .
C25 C 0.9674(7) 0.1125(3) 0.05313(11) 0.0332(11) Uani 1 1 d . . . . .
H25 H 1.095386 0.081588 0.062722 0.040 Uiso 1 1 calc R U . . .
C26 C 0.8516(7) 0.0619(3) 0.02538(11) 0.0316(11) Uani 1 1 d . . . . .
H26 H 0.898829 -0.004063 0.015862 0.038 Uiso 1 1 calc R U . . .
C27 C 0.6670(7) 0.1074(3) 0.01147(11) 0.0320(11) Uani 1 1 d . . . . .
H27 H 0.586783 0.072801 -0.007736 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5981(6) 0.2033(3) 0.02537(10) 0.0275(10) Uani 1 1 d . . . . .
H28 H 0.471135 0.234474 0.015467 0.033 Uiso 1 1 calc R U . . .
C29 C 0.5381(6) 0.6053(3) 0.08631(10) 0.0237(10) Uani 1 1 d . . . . .
C30 C 0.3416(7) 0.6014(3) 0.06800(10) 0.0294(10) Uani 1 1 d . . . . .
H30 H 0.256259 0.539588 0.069859 0.035 Uiso 1 1 calc R U . . .
C31 C 0.2669(7) 0.6859(3) 0.04699(11) 0.0330(11) Uani 1 1 d . . . . .
H31 H 0.132164 0.682204 0.034397 0.040 Uiso 1 1 calc R U . . .
C32 C 0.3903(7) 0.7750(3) 0.04466(11) 0.0310(11) Uani 1 1 d . . . . .
C33 C 0.5845(7) 0.7820(3) 0.06256(12) 0.0369(11) Uani 1 1 d . . . . .
H33 H 0.668209 0.844346 0.060837 0.044 Uiso 1 1 calc R U . . .
C34 C 0.6572(7) 0.6963(3) 0.08333(11) 0.0327(11) Uani 1 1 d . . . . .
H34 H 0.792350 0.700597 0.095775 0.039 Uiso 1 1 calc R U . . .
CL1 Cl 0.29441(19) 0.88205(9) 0.01902(3) 0.0470(4) Uani 1 1 d . . . . .
N1 N 0.4613(5) 0.4403(2) 0.12123(9) 0.0238(8) Uani 1 1 d . . . . .
N2 N 0.5125(6) 0.1595(3) 0.13047(9) 0.0251(9) Uani 1 1 d . . . . .
N3 N 0.2781(6) -0.0133(3) 0.12435(8) 0.0290(8) Uani 1 1 d . . . . .
O1 O 0.2408(4) 0.3733(2) 0.16443(6) 0.0260(6) Uani 1 1 d . . . . .
O2 O 0.3648(5) 0.5411(2) 0.17156(8) 0.0361(8) Uani 1 1 d . . . . .
O3 O 0.7290(5) 0.2895(2) 0.15323(7) 0.0311(7) Uani 1 1 d . . . . .
H2N H 0.392(7) 0.144(3) 0.1150(11) 0.048(14) 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
C1 N1 1.459(4) . ?
C1 C13 1.517(5) . ?
C1 C2 1.549(5) . ?
C1 H1 1.0000 . ?
C2 C23 1.518(5) . ?
C2 C3 1.534(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.540(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.464(5) . ?
C4 C29 1.508(5) . ?
C4 H4 1.0000 . ?
C5 O2 1.206(4) . ?
C5 O1 1.353(4) . ?
C5 N1 1.362(5) . ?
C6 O1 1.446(4) . ?
C6 C7 1.503(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.383(5) . ?
C7 C8 1.386(5) . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O3 1.218(4) . ?
C13 N2 1.352(5) . ?
C14 C15 1.365(5) . ?
C14 N2 1.399(5) . ?
C14 C19 1.422(5) . ?
C15 C16 1.404(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.353(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(5) . ?
C17 H17 0.9500 . ?
C18 C20 1.405(6) . ?
C18 C19 1.414(5) . ?
C19 N3 1.365(5) . ?
C20 C21 1.362(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(5) . ?
C21 H21 0.9500 . ?
C22 N3 1.314(5) . ?
C22 H22 0.9500 . ?
C23 C28 1.382(5) . ?
C23 C24 1.387(5) . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.378(5) . ?
C29 C30 1.384(5) . ?
C30 C31 1.386(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.370(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.366(6) . ?
C32 CL1 1.739(4) . ?
C33 C34 1.388(5) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
N2 H2N 0.95(4) . ?

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
N1 C1 C13 111.0(3) . . ?
N1 C1 C2 101.6(3) . . ?
C13 C1 C2 111.8(3) . . ?
N1 C1 H1 110.7 . . ?
C13 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
C23 C2 C3 118.8(3) . . ?
C23 C2 C1 112.2(3) . . ?
C3 C2 C1 102.4(3) . . ?
C23 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
C2 C3 C4 103.5(3) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C29 113.0(3) . . ?
N1 C4 C3 102.8(3) . . ?
C29 C4 C3 113.1(3) . . ?
N1 C4 H4 109.2 . . ?
C29 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
O2 C5 O1 126.0(4) . . ?
O2 C5 N1 124.3(4) . . ?
O1 C5 N1 109.8(3) . . ?
O1 C6 C7 109.5(3) . . ?
O1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
O1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C12 C7 C8 118.8(4) . . ?
C12 C7 C6 122.2(4) . . ?
C8 C7 C6 119.0(4) . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 121.0(4) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O3 C13 N2 124.8(4) . . ?
O3 C13 C1 120.9(4) . . ?
N2 C13 C1 114.3(3) . . ?
C15 C14 N2 125.7(4) . . ?
C15 C14 C19 120.0(4) . . ?
N2 C14 C19 114.3(4) . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 122.8(4) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 C17 C18 118.8(4) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C20 C18 C19 117.6(4) . . ?
C20 C18 C17 122.7(4) . . ?
C19 C18 C17 119.7(4) . . ?
N3 C19 C18 122.6(4) . . ?
N3 C19 C14 118.2(4) . . ?
C18 C19 C14 119.2(4) . . ?
C21 C20 C18 119.3(4) . . ?
C21 C20 H20 120.4 . . ?
C18 C20 H20 120.4 . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N3 C22 C21 124.5(4) . . ?
N3 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
C28 C23 C24 118.2(4) . . ?
C28 C23 C2 118.1(3) . . ?
C24 C23 C2 123.6(4) . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 120.0(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 119.7(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.1(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.8(4) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C34 C29 C30 118.0(4) . . ?
C34 C29 C4 119.6(4) . . ?
C30 C29 C4 122.4(4) . . ?
C29 C30 C31 121.2(4) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 119.0(4) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C33 C32 C31 121.4(4) . . ?
C33 C32 CL1 119.6(4) . . ?
C31 C32 CL1 119.0(3) . . ?
C32 C33 C34 118.8(4) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C29 C34 C33 121.6(4) . . ?
C29 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C5 N1 C1 122.0(3) . . ?
C5 N1 C4 120.2(3) . . ?
C1 N1 C4 113.8(3) . . ?
C13 N2 C14 127.8(4) . . ?
C13 N2 H2N 119(3) . . ?
C14 N2 H2N 113(3) . . ?
C22 N3 C19 117.0(4) . . ?
C5 O1 C6 116.1(3) . . ?

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
N1 C1 C2 C23 164.0(3) . . . . ?
C13 C1 C2 C23 45.6(4) . . . . ?
N1 C1 C2 C3 35.5(4) . . . . ?
C13 C1 C2 C3 -82.9(4) . . . . ?
C23 C2 C3 C4 -163.8(3) . . . . ?
C1 C2 C3 C4 -39.5(4) . . . . ?
C2 C3 C4 N1 27.7(4) . . . . ?
C2 C3 C4 C29 -94.5(4) . . . . ?
O1 C6 C7 C12 38.0(5) . . . . ?
O1 C6 C7 C8 -145.6(3) . . . . ?
C12 C7 C8 C9 2.1(6) . . . . ?
C6 C7 C8 C9 -174.4(3) . . . . ?
C7 C8 C9 C10 -1.5(6) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C8 C7 C12 C11 -1.2(6) . . . . ?
C6 C7 C12 C11 175.2(4) . . . . ?
C10 C11 C12 C7 -0.4(6) . . . . ?
N1 C1 C13 O3 -35.4(5) . . . . ?
C2 C1 C13 O3 77.3(4) . . . . ?
N1 C1 C13 N2 147.2(3) . . . . ?
C2 C1 C13 N2 -100.2(4) . . . . ?
N2 C14 C15 C16 179.0(4) . . . . ?
C19 C14 C15 C16 -0.5(6) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C20 -179.2(4) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C20 C18 C19 N3 -1.8(6) . . . . ?
C17 C18 C19 N3 179.5(4) . . . . ?
C20 C18 C19 C14 178.7(4) . . . . ?
C17 C18 C19 C14 -0.1(6) . . . . ?
C15 C14 C19 N3 -179.0(3) . . . . ?
N2 C14 C19 N3 1.5(5) . . . . ?
C15 C14 C19 C18 0.6(6) . . . . ?
N2 C14 C19 C18 -179.0(3) . . . . ?
C19 C18 C20 C21 1.3(6) . . . . ?
C17 C18 C20 C21 -180.0(4) . . . . ?
C18 C20 C21 C22 -0.6(6) . . . . ?
C20 C21 C22 N3 0.4(7) . . . . ?
C3 C2 C23 C28 -148.3(3) . . . . ?
C1 C2 C23 C28 92.4(4) . . . . ?
C3 C2 C23 C24 35.6(5) . . . . ?
C1 C2 C23 C24 -83.7(5) . . . . ?
C28 C23 C24 C25 -0.7(6) . . . . ?
C2 C23 C24 C25 175.4(4) . . . . ?
C23 C24 C25 C26 0.1(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C26 C27 C28 -0.1(6) . . . . ?
C26 C27 C28 C23 -0.5(6) . . . . ?
C24 C23 C28 C27 0.9(6) . . . . ?
C2 C23 C28 C27 -175.4(3) . . . . ?
N1 C4 C29 C34 157.7(4) . . . . ?
C3 C4 C29 C34 -86.0(5) . . . . ?
N1 C4 C29 C30 -24.5(5) . . . . ?
C3 C4 C29 C30 91.7(4) . . . . ?
C34 C29 C30 C31 0.5(6) . . . . ?
C4 C29 C30 C31 -177.2(4) . . . . ?
C29 C30 C31 C32 -0.4(6) . . . . ?
C30 C31 C32 C33 0.0(6) . . . . ?
C30 C31 C32 CL1 -178.8(3) . . . . ?
C31 C32 C33 C34 0.3(6) . . . . ?
CL1 C32 C33 C34 179.1(3) . . . . ?
C30 C29 C34 C33 -0.2(6) . . . . ?
C4 C29 C34 C33 177.6(4) . . . . ?
C32 C33 C34 C29 -0.2(6) . . . . ?
O2 C5 N1 C1 169.3(4) . . . . ?
O1 C5 N1 C1 -12.7(5) . . . . ?
O2 C5 N1 C4 13.2(6) . . . . ?
O1 C5 N1 C4 -168.9(3) . . . . ?
C13 C1 N1 C5 -57.7(5) . . . . ?
C2 C1 N1 C5 -176.8(3) . . . . ?
C13 C1 N1 C4 99.8(4) . . . . ?
C2 C1 N1 C4 -19.2(4) . . . . ?
C29 C4 N1 C5 -84.9(4) . . . . ?
C3 C4 N1 C5 152.9(3) . . . . ?
C29 C4 N1 C1 117.1(4) . . . . ?
C3 C4 N1 C1 -5.1(4) . . . . ?
O3 C13 N2 C14 -1.5(6) . . . . ?
C1 C13 N2 C14 175.9(3) . . . . ?
C15 C14 N2 C13 -9.4(6) . . . . ?
C19 C14 N2 C13 170.1(4) . . . . ?
C21 C22 N3 C19 -0.8(6) . . . . ?
C18 C19 N3 C22 1.5(6) . . . . ?
C14 C19 N3 C22 -179.0(4) . . . . ?
O2 C5 O1 C6 -2.6(6) . . . . ?
N1 C5 O1 C6 179.5(3) . . . . ?
C7 C6 O1 C5 -135.0(3) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_xr15lt
_database_code_depnum_ccdc_archive 'CCDC 1851080'
loop_
_audit_author_name
_audit_author_address
'Eduard '
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2018-06-22 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 N3 O3, Cl O4, 2 (H2 O)'
_chemical_formula_sum            'C33 H38 Cl N3 O9'
_chemical_formula_weight         656.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.871(3)
_cell_length_b                   10.770(5)
_cell_length_c                   21.856(11)
_cell_angle_alpha                94.578(10)
_cell_angle_beta                 94.404(10)
_cell_angle_gamma                102.422(13)
_cell_volume                     1567.1(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      21.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19136
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             5509
_reflns_number_gt                2871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²+0.8375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5509
_refine_ls_number_parameters     455
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2077
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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 0.42092(18) 0.97335(11) 0.60144(6) 0.0407(4) Uani 1 1 d . . . . .
O4 O 0.2517(5) 0.9513(3) 0.55552(17) 0.0542(10) Uani 1 1 d . . . . .
O5 O 0.5853(5) 1.0617(3) 0.58347(19) 0.0657(12) Uani 1 1 d . . . . .
O6 O 0.4772(6) 0.8560(3) 0.60966(19) 0.0594(11) Uani 1 1 d . . . . .
O7 O 0.3638(5) 1.0250(4) 0.65835(17) 0.0587(11) Uani 1 1 d . . . . .
H82 H 0.363(6) 0.646(5) 0.694(3) 0.06(2) Uiso 1 1 d D . . . .
H81 H 0.332(9) 0.740(4) 0.673(3) 0.09(3) Uiso 1 1 d D . . . .
H91 H 0.899(7) 0.878(5) 0.6901(18) 0.061(19) Uiso 1 1 d D . . . .
H92 H 1.078(5) 0.927(4) 0.672(3) 0.08(2) Uiso 1 1 d D . . . .
O9 O 0.9717(6) 0.8753(4) 0.6622(2) 0.0621(12) Uani 1 1 d D . . . .
O8 O 0.2727(5) 0.6844(4) 0.6931(2) 0.0478(10) Uani 1 1 d D . . . .
N1 N 0.6932(6) 0.6830(4) 0.80408(18) 0.0392(10) Uani 1 1 d . . . . .
N2 N 0.8639(5) 0.5803(3) 0.66111(18) 0.0291(9) Uani 1 1 d D . . . .
N3 N 0.8329(5) 0.7273(3) 0.55973(19) 0.0300(9) Uani 1 1 d D . . . .
O1 O 0.7162(5) 0.8539(3) 0.74870(17) 0.0491(10) Uani 1 1 d . . . . .
O2 O 0.5224(6) 0.8307(3) 0.82774(16) 0.0501(10) Uani 1 1 d . . . . .
O3 O 0.5520(4) 0.5307(3) 0.69213(14) 0.0339(8) Uani 1 1 d . . . . .
C1 C 0.8256(7) 0.6242(4) 0.7689(2) 0.0370(12) Uani 1 1 d . . . . .
H1 H 0.956739 0.685708 0.767924 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8533(7) 0.5119(5) 0.8078(2) 0.0424(13) Uani 1 1 d . . . . .
H2A H 0.963534 0.548125 0.841146 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6580(9) 0.4796(5) 0.8393(2) 0.0447(14) Uani 1 1 d . . . . .
H3A H 0.551(8) 0.432(5) 0.804(2) 0.058(16) Uiso 1 1 d . . . . .
C4 C 0.6154(9) 0.6107(5) 0.8547(2) 0.0516(15) Uani 1 1 d . . . . .
H4A H 0.469994 0.605179 0.855721 0.062 Uiso 1 1 calc R U . . .
H4B H 0.685724 0.650715 0.895019 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6490(8) 0.7944(5) 0.7900(2) 0.0416(13) Uani 1 1 d . . . . .
C6A C 0.4478(14) 0.9399(7) 0.8084(4) 0.046(2) Uani 0.839(6) 1 d . . P A 1
H6A1 H 0.400265 0.924852 0.763943 0.056 Uiso 0.839(6) 1 calc R U P A 1
H6A2 H 0.557028 1.017758 0.814860 0.056 Uiso 0.839(6) 1 calc R U P A 1
C7A C 0.2802(11) 0.9580(6) 0.8450(3) 0.0406(16) Uani 0.839(6) 1 d . . P A 1
C8A C 0.2135(10) 0.8860(6) 0.8920(3) 0.0516(19) Uani 0.839(6) 1 d . . P A 1
H8A H 0.277832 0.820664 0.903704 0.062 Uiso 0.839(6) 1 calc R U P A 1
C9A C 0.0537(11) 0.9092(7) 0.9215(3) 0.062(2) Uani 0.839(6) 1 d . . P A 1
H9A H 0.008399 0.859969 0.953905 0.074 Uiso 0.839(6) 1 calc R U P A 1
C10A C -0.0398(11) 1.0018(8) 0.9049(3) 0.064(2) Uani 0.839(6) 1 d . . P A 1
H10A H -0.149950 1.017114 0.925762 0.077 Uiso 0.839(6) 1 calc R U P A 1
C11A C 0.0233(12) 1.0727(8) 0.8587(4) 0.063(2) Uani 0.839(6) 1 d . . P A 1
H11A H -0.043093 1.137382 0.847217 0.076 Uiso 0.839(6) 1 calc R U P A 1
C12A C 0.1827(14) 1.0514(8) 0.8283(5) 0.050(2) Uani 0.839(6) 1 d . . P A 1
H12A H 0.225707 1.100882 0.795712 0.061 Uiso 0.839(6) 1 calc R U P A 1
C6B C 0.508(6) 0.967(4) 0.8262(18) 0.025(11) Uiso 0.161(6) 1 d . . P A 2
H6B1 H 0.472794 0.982190 0.783189 0.030 Uiso 0.161(6) 1 calc R U P A 2
H6B2 H 0.640592 1.022801 0.840457 0.030 Uiso 0.161(6) 1 calc R U P A 2
C7B C 0.362(4) 0.999(3) 0.8641(9) 0.045(11) Uiso 0.161(6) 1 d G . P A 2
C8B C 0.407(3) 0.985(2) 0.9260(10) 0.040(8) Uiso 0.161(6) 1 d G . P A 2
H8B H 0.509946 0.942956 0.937792 0.048 Uiso 0.161(6) 1 calc R U P A 2
C9B C 0.301(3) 1.033(2) 0.9705(8) 0.053(10) Uiso 0.161(6) 1 d G . P A 2
H9B H 0.331845 1.023495 1.012805 0.063 Uiso 0.161(6) 1 calc R U P A 2
C10B C 0.151(3) 1.095(2) 0.9533(11) 0.050(9) Uiso 0.161(6) 1 d G . P A 2
H10B H 0.078230 1.127416 0.983720 0.060 Uiso 0.161(6) 1 calc R U P A 2
C11B C 0.106(4) 1.109(3) 0.8914(12) 0.064(12) Uiso 0.161(6) 1 d G . P A 2
H11B H 0.002715 1.150797 0.879622 0.077 Uiso 0.161(6) 1 calc R U P A 2
C12B C 0.211(5) 1.061(3) 0.8469(9) 0.05(2) Uiso 0.161(6) 1 d G . P A 2
H12B H 0.180815 1.070258 0.804608 0.059 Uiso 0.161(6) 1 calc R U P A 2
C13 C 0.7322(6) 0.5749(4) 0.7035(2) 0.0292(11) Uani 1 1 d . . . . .
C14 C 0.8104(6) 0.5209(4) 0.5992(2) 0.0275(11) Uani 1 1 d . . . . .
C15 C 0.7725(6) 0.3910(4) 0.5875(2) 0.0306(11) Uani 1 1 d . . . . .
H15 H 0.778150 0.339532 0.620665 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7249(6) 0.3333(4) 0.5266(2) 0.0327(12) Uani 1 1 d . . . . .
H16 H 0.698335 0.242836 0.519093 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7165(6) 0.4042(4) 0.4787(2) 0.0330(11) Uani 1 1 d . . . . .
H17 H 0.686061 0.363364 0.437855 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7526(6) 0.5385(4) 0.4887(2) 0.0290(11) Uani 1 1 d . . . . .
C19 C 0.8003(6) 0.5967(4) 0.5499(2) 0.0268(10) Uani 1 1 d . . . . .
C20 C 0.7425(6) 0.6179(4) 0.4406(2) 0.0343(11) Uani 1 1 d . . . . .
H20 H 0.712533 0.581094 0.399104 0.041 Uiso 1 1 calc R U . . .
C21 C 0.7756(7) 0.7468(4) 0.4536(2) 0.0347(12) Uani 1 1 d . . . . .
H21 H 0.767530 0.800019 0.421261 0.042 Uiso 1 1 calc R U . . .
C22 C 0.8209(6) 0.7995(4) 0.5139(2) 0.0360(12) Uani 1 1 d . . . . .
H22 H 0.844048 0.889541 0.522851 0.043 Uiso 1 1 calc R U . . .
C23 C 0.9140(7) 0.4031(4) 0.7722(2) 0.0376(12) Uani 1 1 d . . . . .
C24 C 0.7764(7) 0.2889(4) 0.7501(2) 0.0379(12) Uani 1 1 d . . . . .
H24 H 0.640404 0.277978 0.758423 0.046 Uiso 1 1 calc R U . . .
C25 C 0.8368(7) 0.1933(4) 0.7168(2) 0.0394(12) Uani 1 1 d . . . . .
H25 H 0.742707 0.115528 0.703468 0.047 Uiso 1 1 calc R U . . .
C26 C 1.0297(8) 0.2076(4) 0.7022(2) 0.0438(13) Uani 1 1 d . . . . .
H26 H 1.068541 0.140989 0.678347 0.053 Uiso 1 1 calc R U . . .
C27 C 1.1684(8) 0.3198(5) 0.7226(3) 0.0479(14) Uani 1 1 d . . . . .
H27 H 1.302664 0.331041 0.712383 0.058 Uiso 1 1 calc R U . . .
C28 C 1.1102(7) 0.4149(5) 0.7576(3) 0.0452(14) Uani 1 1 d . . . . .
H28 H 1.206806 0.490701 0.772295 0.054 Uiso 1 1 calc R U . . .
C29A C 0.6375(16) 0.4073(12) 0.8975(7) 0.067(5) Uiso 0.5 1 d D . P B 1
H29A H 0.718573 0.469303 0.931343 0.080 Uiso 0.5 1 calc R U P B 1
C30A C 0.4336(16) 0.3677(10) 0.9208(4) 0.037(3) Uiso 0.5 1 d D . P B 1
H30A H 0.391552 0.443366 0.939465 0.044 Uiso 0.5 1 calc R U P B 1
H30B H 0.332818 0.325800 0.886434 0.044 Uiso 0.5 1 calc R U P B 1
C31A C 0.4519(15) 0.2757(10) 0.9686(5) 0.047(3) Uiso 0.5 1 d D . P B 1
H31A H 0.414394 0.306665 1.008909 0.056 Uiso 0.5 1 calc R U P B 1
H31B H 0.368215 0.189479 0.955146 0.056 Uiso 0.5 1 calc R U P B 1
C32A C 0.6723(17) 0.2759(18) 0.9714(7) 0.118(6) Uiso 0.5 1 d D . P B 1
H32A H 0.700096 0.196076 0.985823 0.142 Uiso 0.5 1 calc R U P B 1
H32B H 0.754086 0.350181 0.998208 0.142 Uiso 0.5 1 calc R U P B 1
C33A C 0.708(3) 0.2857(13) 0.9039(7) 0.110(6) Uiso 0.5 1 d D . P B 1
H33A H 0.850401 0.294788 0.896940 0.132 Uiso 0.5 1 calc R U P B 1
H33B H 0.624531 0.212680 0.876604 0.132 Uiso 0.5 1 calc R U P B 1
C29B C 0.6850(18) 0.3949(15) 0.8889(5) 0.069(5) Uiso 0.5 1 d D . P B 2
H29B H 0.693464 0.309075 0.869654 0.083 Uiso 0.5 1 calc R U P B 2
C30B C 0.518(2) 0.3791(15) 0.9306(7) 0.082(5) Uiso 0.5 1 d D . P B 2
H30C H 0.389289 0.336204 0.906616 0.098 Uiso 0.5 1 calc R U P B 2
H30D H 0.504476 0.463781 0.948686 0.098 Uiso 0.5 1 calc R U P B 2
C31B C 0.566(2) 0.2995(16) 0.9811(8) 0.113(6) Uiso 0.5 1 d D . P B 2
H31C H 0.488408 0.308896 1.016816 0.136 Uiso 0.5 1 calc R U P B 2
H31D H 0.544879 0.207965 0.966008 0.136 Uiso 0.5 1 calc R U P B 2
C32B C 0.784(2) 0.3610(16) 0.9960(7) 0.120(6) Uiso 0.5 1 d D . P B 2
H32C H 0.864162 0.295409 1.000553 0.144 Uiso 0.5 1 calc R U P B 2
H32D H 0.805757 0.418334 1.034782 0.144 Uiso 0.5 1 calc R U P B 2
C33B C 0.8436(17) 0.4362(12) 0.9423(5) 0.068(3) Uiso 0.5 1 d D . P B 2
H33C H 0.860148 0.528551 0.954696 0.081 Uiso 0.5 1 calc R U P B 2
H33D H 0.973131 0.421608 0.929899 0.081 Uiso 0.5 1 calc R U P B 2
H2 H 0.996(2) 0.613(5) 0.670(2) 0.066(18) Uiso 1 1 d D . . . .
H3 H 0.867(6) 0.763(4) 0.5992(8) 0.032(13) Uiso 1 1 d 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
CL1 O5 1.415(4) . ?
CL1 O6 1.420(3) . ?
CL1 O7 1.439(4) . ?
CL1 O4 1.442(4) . ?
N1 C5 1.353(6) . ?
N1 C1 1.447(6) . ?
N1 C4 1.471(6) . ?
N2 C13 1.341(5) . ?
N2 C14 1.434(6) . ?
N3 C22 1.323(6) . ?
N3 C19 1.373(5) . ?
O1 C5 1.211(6) . ?
O2 C5 1.340(6) . ?
O2 C6B 1.49(4) . ?
O2 C6A 1.459(8) . ?
O3 C13 1.225(5) . ?
C1 C13 1.526(7) . ?
C1 C2 1.568(7) . ?
C2 C23 1.506(7) . ?
C2 C3 1.540(7) . ?
C3 C29B 1.499(14) . ?
C3 C4 1.520(7) . ?
C3 C29A 1.545(14) . ?
C6A C7A 1.490(10) . ?
C7A C12A 1.380(9) . ?
C7A C8A 1.382(8) . ?
C8A C9A 1.373(9) . ?
C9A C10A 1.355(9) . ?
C10A C11A 1.357(10) . ?
C11A C12A 1.374(10) . ?
C6B C7B 1.43(5) . ?
C7B C8B 1.3900 . ?
C7B C12B 1.3900 . ?
C8B C9B 1.3900 . ?
C9B C10B 1.3900 . ?
C10B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C14 C15 1.366(6) . ?
C14 C19 1.409(6) . ?
C15 C16 1.407(6) . ?
C16 C17 1.350(6) . ?
C17 C18 1.410(6) . ?
C18 C20 1.413(6) . ?
C18 C19 1.414(6) . ?
C20 C21 1.360(6) . ?
C21 C22 1.379(7) . ?
C23 C28 1.390(7) . ?
C23 C24 1.405(6) . ?
C24 C25 1.369(6) . ?
C25 C26 1.366(7) . ?
C26 C27 1.386(7) . ?
C27 C28 1.376(7) . ?
C29A C33A 1.503(5) . ?
C29A C30A 1.513(5) . ?
C30A C31A 1.511(5) . ?
C31A C32A 1.510(5) . ?
C32A C33A 1.520(5) . ?
C29B C33B 1.503(5) . ?
C29B C30B 1.510(5) . ?
C30B C31B 1.512(5) . ?
C31B C32B 1.502(5) . ?
C32B C33B 1.509(5) . ?

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
O5 CL1 O6 109.4(2) . . ?
O5 CL1 O7 108.7(2) . . ?
O6 CL1 O7 110.0(3) . . ?
O5 CL1 O4 110.9(3) . . ?
O6 CL1 O4 109.3(2) . . ?
O7 CL1 O4 108.5(2) . . ?
C5 N1 C1 121.2(4) . . ?
C5 N1 C4 124.9(4) . . ?
C1 N1 C4 114.0(4) . . ?
C13 N2 C14 122.8(4) . . ?
C22 N3 C19 122.1(4) . . ?
C5 O2 C6B 114.3(17) . . ?
C5 O2 C6A 112.9(5) . . ?
N1 C1 C13 111.9(4) . . ?
N1 C1 C2 101.9(4) . . ?
C13 C1 C2 111.6(4) . . ?
C23 C2 C3 117.0(4) . . ?
C23 C2 C1 114.5(4) . . ?
C3 C2 C1 103.9(4) . . ?
C29B C3 C4 120.9(7) . . ?
C29B C3 C2 108.9(6) . . ?
C4 C3 C2 102.4(4) . . ?
C4 C3 C29A 108.0(6) . . ?
C2 C3 C29A 123.6(6) . . ?
N1 C4 C3 103.5(4) . . ?
O1 C5 O2 124.5(5) . . ?
O1 C5 N1 124.2(5) . . ?
O2 C5 N1 111.3(4) . . ?
O2 C6A C7A 109.3(6) . . ?
C12A C7A C8A 119.1(7) . . ?
C12A C7A C6A 116.0(7) . . ?
C8A C7A C6A 124.9(6) . . ?
C9A C8A C7A 119.8(6) . . ?
C10A C9A C8A 120.6(7) . . ?
C9A C10A C11A 120.3(7) . . ?
C10A C11A C12A 120.3(7) . . ?
C11A C12A C7A 120.0(8) . . ?
O2 C6B C7B 112(3) . . ?
C8B C7B C12B 120.0 . . ?
C8B C7B C6B 112(2) . . ?
C12B C7B C6B 126(2) . . ?
C9B C8B C7B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C11B C12B C7B 120.0 . . ?
O3 C13 N2 123.8(4) . . ?
O3 C13 C1 121.7(4) . . ?
N2 C13 C1 114.4(4) . . ?
C15 C14 C19 119.6(4) . . ?
C15 C14 N2 120.3(4) . . ?
C19 C14 N2 120.1(4) . . ?
C14 C15 C16 120.2(4) . . ?
C17 C16 C15 121.1(4) . . ?
C16 C17 C18 120.5(4) . . ?
C17 C18 C20 123.3(4) . . ?
C17 C18 C19 118.4(4) . . ?
C20 C18 C19 118.3(4) . . ?
N3 C19 C14 121.5(4) . . ?
N3 C19 C18 118.4(4) . . ?
C14 C19 C18 120.2(4) . . ?
C21 C20 C18 120.3(4) . . ?
C20 C21 C22 119.4(5) . . ?
N3 C22 C21 121.4(4) . . ?
C28 C23 C24 117.2(4) . . ?
C28 C23 C2 120.4(4) . . ?
C24 C23 C2 122.3(5) . . ?
C25 C24 C23 120.6(5) . . ?
C26 C25 C24 121.2(4) . . ?
C25 C26 C27 119.6(5) . . ?
C28 C27 C26 119.5(5) . . ?
C27 C28 C23 121.9(5) . . ?
C33A C29A C30A 98.6(10) . . ?
C33A C29A C3 123.1(11) . . ?
C30A C29A C3 119.4(9) . . ?
C31A C30A C29A 107.2(9) . . ?
C32A C31A C30A 101.6(9) . . ?
C31A C32A C33A 100.3(11) . . ?
C29A C33A C32A 96.9(12) . . ?
C3 C29B C33B 122.2(10) . . ?
C3 C29B C30B 112.7(11) . . ?
C33B C29B C30B 92.7(11) . . ?
C29B C30B C31B 108.3(13) . . ?
C32B C31B C30B 98.8(13) . . ?
C31B C32B C33B 105.7(12) . . ?
C29B C33B C32B 109.7(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H82 O3 0.817(10) 1.980(14) 2.791(5) 172(6) .
O8 H81 O6 0.822(10) 2.107(16) 2.920(6) 171(6) .
O9 H91 O1 0.820(10) 1.856(15) 2.667(5) 170(6) .
N3 H3 O9 0.906(10) 1.759(18) 2.629(6) 160(4) .
O9 H92 O7_$1 0.817(11) 2.08(3) 2.838(5) 154(6) 1_655
N2 H2 O8_$1 0.897(10) 1.906(12) 2.802(5) 177(5) 1_655

_refine_diff_density_max         0.987
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.071

