# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1880544'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H43 Cl2 N4 O6'
_chemical_formula_weight         734.67

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

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

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

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

_cell_length_a                   10.0070(5)
_cell_length_b                   13.2653(7)
_cell_length_c                   15.0577(8)
_cell_angle_alpha                80.234(2)
_cell_angle_beta                 71.193(2)
_cell_angle_gamma                70.137(2)
_cell_volume                     1775.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             774
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.087
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8212
_exptl_absorpt_correction_T_max  0.8898
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            24164
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.551
_diffrn_reflns_theta_max         78.792
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7255
_reflns_number_gt                5938
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0941P)²+2.4878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7255
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.3962(3) 0.1684(2) 0.25000(18) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.3679(3) 0.2762(2) 0.19017(18) 0.0214(5) Uani 1 1 d . . . . .
H2A H 0.461795 0.279242 0.142569 0.026 Uiso 1 1 calc R U . . .
H2B H 0.334906 0.336076 0.231275 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2492(3) 0.2908(2) 0.13983(19) 0.0247(5) Uani 1 1 d . . . . .
C4 C 0.3011(3) 0.1964(2) 0.0764(2) 0.0300(6) Uani 1 1 d . . . . .
H4A H 0.225137 0.204005 0.044723 0.036 Uiso 1 1 calc R U . . .
H4B H 0.394353 0.197902 0.027335 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3264(4) 0.0888(2) 0.1356(2) 0.0345(7) Uani 1 1 d . . . . .
H5 H 0.360617 0.028394 0.093886 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4448(3) 0.0771(2) 0.1840(2) 0.0283(6) Uani 1 1 d . . . . .
H6A H 0.538805 0.078321 0.135667 0.034 Uiso 1 1 calc R U . . .
H6B H 0.462860 0.006971 0.220802 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1057(3) 0.2855(3) 0.2152(2) 0.0344(7) Uani 1 1 d . . . . .
H7A H 0.027796 0.294344 0.184847 0.041 Uiso 1 1 calc R U . . .
H7B H 0.071109 0.344801 0.257132 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1312(3) 0.1774(3) 0.2735(2) 0.0398(8) Uani 1 1 d . . . . .
H8 H 0.036017 0.175352 0.321795 0.048 Uiso 1 1 calc R U . . .
C9 C 0.2483(3) 0.1665(3) 0.3235(2) 0.0338(7) Uani 1 1 d . . . . .
H9A H 0.213392 0.226354 0.364855 0.041 Uiso 1 1 calc R U . . .
H9B H 0.263052 0.098168 0.363030 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1835(4) 0.0853(3) 0.2099(3) 0.0443(9) Uani 1 1 d . . . . .
H10A H 0.199922 0.015812 0.247749 0.053 Uiso 1 1 calc R U . . .
H10B H 0.106663 0.091626 0.179356 0.053 Uiso 1 1 calc R U . . .
C11 C 0.5135(3) 0.1539(2) 0.30005(18) 0.0239(5) Uani 1 1 d . . . . .
C12 C 0.5647(3) 0.0546(2) 0.34734(19) 0.0254(5) Uani 1 1 d . . . . .
H12 H 0.528515 -0.002724 0.346483 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6686(3) 0.0394(2) 0.39562(18) 0.0256(5) Uani 1 1 d . . . . .
C14 C 0.7206(3) 0.1235(2) 0.39692(18) 0.0263(6) Uani 1 1 d . . . . .
C15 C 0.6712(3) 0.2223(2) 0.35039(19) 0.0268(6) Uani 1 1 d . . . . .
C16 C 0.5686(3) 0.2372(2) 0.30128(18) 0.0248(5) Uani 1 1 d . . . . .
H16 H 0.535996 0.304340 0.268412 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6880(3) -0.1459(2) 0.4361(2) 0.0346(7) Uani 1 1 d . . . . .
H17A H 0.716215 -0.158817 0.369409 0.052 Uiso 1 1 calc R U . . .
H17B H 0.581154 -0.133662 0.463386 0.052 Uiso 1 1 calc R U . . .
H17C H 0.741996 -0.208559 0.469275 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7833(3) 0.1431(2) 0.52942(19) 0.0261(6) Uani 1 1 d . . . . .
C19 C 0.6058(4) 0.2160(3) 0.6572(2) 0.0435(8) Uani 1 1 d . . . . .
H19 H 0.503132 0.245529 0.687554 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8380(4) 0.1724(3) 0.6599(2) 0.0368(7) Uani 1 1 d . . . . .
C21 C 0.8924(3) 0.1349(2) 0.5710(2) 0.0320(6) Uani 1 1 d . . . . .
H21 H 0.995351 0.106180 0.540859 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6881(4) 0.3997(3) 0.3084(2) 0.0372(7) Uani 1 1 d . . . . .
H22A H 0.741466 0.445547 0.316687 0.056 Uiso 1 1 calc R U . . .
H22B H 0.581141 0.433720 0.333196 0.056 Uiso 1 1 calc R U . . .
H22C H 0.712511 0.389723 0.241371 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2307(3) 0.3980(2) 0.08035(19) 0.0239(5) Uani 1 1 d . . . . .
C24 C 0.3492(3) 0.4135(2) 0.00535(18) 0.0230(5) Uani 1 1 d . . . . .
H24 H 0.440582 0.357320 -0.008976 0.028 Uiso 1 1 calc R U . . .
C25 C 0.3347(3) 0.5109(2) -0.04867(18) 0.0236(5) Uani 1 1 d . . . . .
C26 C 0.2007(3) 0.5935(2) -0.02667(19) 0.0249(5) Uani 1 1 d . . . . .
C27 C 0.0833(3) 0.5793(2) 0.0475(2) 0.0268(6) Uani 1 1 d . . . . .
C28 C 0.0975(3) 0.4815(2) 0.10090(19) 0.0256(5) Uani 1 1 d . . . . .
H28 H 0.016023 0.471762 0.151635 0.031 Uiso 1 1 calc R U . . .
C29 C 0.5754(3) 0.4474(2) -0.1557(2) 0.0303(6) Uani 1 1 d . . . . .
H29A H 0.549797 0.389741 -0.172911 0.046 Uiso 1 1 calc R U . . .
H29B H 0.623999 0.419946 -0.105684 0.046 Uiso 1 1 calc R U . . .
H29C H 0.642748 0.473235 -0.210843 0.046 Uiso 1 1 calc R U . . .
C30 C -0.1660(3) 0.6556(3) 0.1386(2) 0.0365(7) Uani 1 1 d . . . . .
H30A H -0.249791 0.721244 0.139897 0.055 Uiso 1 1 calc R U . . .
H30B H -0.141020 0.643584 0.198104 0.055 Uiso 1 1 calc R U . . .
H30C H -0.193112 0.594340 0.129806 0.055 Uiso 1 1 calc R U . . .
C31 C 0.1980(3) 0.7742(2) -0.05112(19) 0.0233(5) Uani 1 1 d . . . . .
C32 C 0.2538(3) 0.8458(2) 0.0522(2) 0.0334(6) Uani 1 1 d . . . . .
H32 H 0.287527 0.835362 0.106268 0.040 Uiso 1 1 calc R U . . .
C33 C 0.1787(3) 0.9552(2) -0.0637(2) 0.0296(6) Uani 1 1 d . . . . .
C34 C 0.1636(3) 0.8734(2) -0.1010(2) 0.0262(5) Uani 1 1 d . . . . .
H34 H 0.132396 0.883665 -0.156050 0.031 Uiso 1 1 calc R U . . .
C35 C 0.7523(6) 0.4524(4) 0.5604(5) 0.0831(16) Uani 1 1 d . . . . .
H35A H 0.658600 0.452023 0.609483 0.100 Uiso 1 1 calc R U . . .
H35B H 0.787037 0.387259 0.525293 0.100 Uiso 1 1 calc R U . . .
C36 C 0.7234(6) 0.5521(4) 0.4932(4) 0.0738(13) Uani 1 1 d . . . . .
H36A H 0.681036 0.617459 0.528750 0.089 Uiso 1 1 calc R U . . .
H36B H 0.650968 0.550390 0.461996 0.089 Uiso 1 1 calc R U . . .
C37 C 0.8702(6) 0.5553(4) 0.4183(4) 0.0722(13) Uani 1 1 d . . . . .
H37A H 0.906740 0.493721 0.378649 0.087 Uiso 1 1 calc R U . . .
H37B H 0.852055 0.622206 0.377147 0.087 Uiso 1 1 calc R U . . .
C38 C 0.9885(5) 0.5508(3) 0.4642(3) 0.0613(11) Uani 1 1 d . . . . .
H38 H 0.952284 0.616343 0.500165 0.074 Uiso 1 1 calc R U . . .
C39 C 1.1329(6) 0.5502(4) 0.3934(3) 0.0762(14) Uani 1 1 d . . . . .
H39A H 1.117653 0.615176 0.349869 0.091 Uiso 1 1 calc R U . . .
H39B H 1.169663 0.486569 0.356108 0.091 Uiso 1 1 calc R U . . .
N1 N 0.2443(3) 0.75868(19) 0.02445(16) 0.0270(5) Uani 1 1 d . . . . .
N2 N 0.2218(3) 0.9446(2) 0.01343(19) 0.0352(6) Uani 1 1 d . . . . .
N3 N 0.6398(3) 0.1828(2) 0.57155(18) 0.0351(6) Uani 1 1 d . . . . .
N4 N 0.6977(3) 0.2129(2) 0.70517(19) 0.0427(7) Uani 1 1 d . . . . .
O1 O 0.1838(2) 0.69033(14) -0.08350(13) 0.0272(4) Uani 1 1 d . . . . .
O2 O -0.0414(2) 0.66667(15) 0.06300(15) 0.0321(5) Uani 1 1 d . . . . .
O3 O 0.4432(2) 0.53409(15) -0.12324(13) 0.0267(4) Uani 1 1 d . . . . .
O4 O 0.8289(2) 0.10652(16) 0.44273(13) 0.0288(4) Uani 1 1 d . . . . .
O5 O 0.7241(2) -0.05340(16) 0.44519(14) 0.0315(5) Uani 1 1 d . . . . .
O6 O 0.7306(2) 0.29806(17) 0.35773(15) 0.0331(5) Uani 1 1 d . . . . .
Cl1 Cl 0.14186(9) 1.08369(5) -0.11743(6) 0.0406(2) Uani 1 1 d . . . . .
Cl2 Cl 0.96254(11) 0.16198(10) 0.72139(6) 0.0582(3) Uani 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 C11 1.534(3) . ?
C1 C9 1.541(4) . ?
C1 C2 1.545(3) . ?
C1 C6 1.546(4) . ?
C2 C3 1.549(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.532(4) . ?
C3 C23 1.534(3) . ?
C3 C4 1.547(4) . ?
C4 C5 1.538(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.515(5) . ?
C5 C6 1.533(4) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.536(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.525(5) . ?
C8 C9 1.542(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.397(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 O5 1.368(3) . ?
C13 C14 1.388(4) . ?
C14 C15 1.387(4) . ?
C14 O4 1.402(3) . ?
C15 O6 1.364(3) . ?
C15 C16 1.393(4) . ?
C16 H16 0.9500 . ?
C17 O5 1.430(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N3 1.324(4) . ?
C18 O4 1.352(3) . ?
C18 C21 1.391(4) . ?
C19 N4 1.327(4) . ?
C19 N3 1.334(4) . ?
C19 H19 0.9500 . ?
C20 N4 1.312(5) . ?
C20 C21 1.381(4) . ?
C20 Cl2 1.736(3) . ?
C21 H21 0.9500 . ?
C22 O6 1.422(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.395(4) . ?
C23 C24 1.396(4) . ?
C24 C25 1.394(3) . ?
C24 H24 0.9500 . ?
C25 O3 1.363(3) . ?
C25 C26 1.395(4) . ?
C26 C27 1.376(4) . ?
C26 O1 1.409(3) . ?
C27 O2 1.370(3) . ?
C27 C28 1.394(4) . ?
C28 H28 0.9500 . ?
C29 O3 1.432(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 O2 1.423(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 N1 1.322(3) . ?
C31 O1 1.354(3) . ?
C31 C34 1.392(4) . ?
C32 N2 1.318(4) . ?
C32 N1 1.336(4) . ?
C32 H32 0.9500 . ?
C33 N2 1.335(4) . ?
C33 C34 1.374(4) . ?
C33 Cl1 1.730(3) . ?
C34 H34 0.9500 . ?
C35 C39 1.512(8) 2_766 ?
C35 C36 1.527(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.546(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.531(7) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.492(7) . ?
C38 C38 1.578(8) 2_766 ?
C38 H38 1.0000 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C9 109.6(2) . . ?
C11 C1 C2 112.2(2) . . ?
C9 C1 C2 107.9(2) . . ?
C11 C1 C6 110.8(2) . . ?
C9 C1 C6 108.6(2) . . ?
C2 C1 C6 107.7(2) . . ?
C1 C2 C3 112.1(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C7 C3 C23 112.8(2) . . ?
C7 C3 C4 108.2(2) . . ?
C23 C3 C4 110.3(2) . . ?
C7 C3 C2 107.9(2) . . ?
C23 C3 C2 108.8(2) . . ?
C4 C3 C2 108.8(2) . . ?
C5 C4 C3 110.1(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 109.1(3) . . ?
C10 C5 C4 109.9(3) . . ?
C6 C5 C4 109.4(2) . . ?
C10 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C5 C6 C1 111.3(2) . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C3 C7 C8 110.5(2) . . ?
C3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C10 C8 C7 110.1(3) . . ?
C10 C8 C9 110.2(3) . . ?
C7 C8 C9 109.0(2) . . ?
C10 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C1 C9 C8 109.9(2) . . ?
C1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C1 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 C8 109.5(2) . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10B 109.8 . . ?
C8 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 119.2(2) . . ?
C16 C11 C1 122.0(2) . . ?
C12 C11 C1 118.8(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O5 C13 C14 115.3(2) . . ?
O5 C13 C12 125.2(2) . . ?
C14 C13 C12 119.5(2) . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 O4 119.9(2) . . ?
C13 C14 O4 119.2(2) . . ?
O6 C15 C14 114.8(2) . . ?
O6 C15 C16 125.5(2) . . ?
C14 C15 C16 119.7(3) . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 O4 119.9(2) . . ?
N3 C18 C21 122.9(3) . . ?
O4 C18 C21 117.1(3) . . ?
N4 C19 N3 128.0(3) . . ?
N4 C19 H19 116.0 . . ?
N3 C19 H19 116.0 . . ?
N4 C20 C21 125.9(3) . . ?
N4 C20 Cl2 115.4(2) . . ?
C21 C20 Cl2 118.7(3) . . ?
C20 C21 C18 114.1(3) . . ?
C20 C21 H21 123.0 . . ?
C18 C21 H21 123.0 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 119.1(2) . . ?
C28 C23 C3 121.1(2) . . ?
C24 C23 C3 119.9(2) . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
O3 C25 C24 125.1(2) . . ?
O3 C25 C26 115.5(2) . . ?
C24 C25 C26 119.4(2) . . ?
C27 C26 C25 120.6(2) . . ?
C27 C26 O1 119.9(2) . . ?
C25 C26 O1 119.5(2) . . ?
O2 C27 C26 115.1(2) . . ?
O2 C27 C28 124.9(3) . . ?
C26 C27 C28 120.0(3) . . ?
C27 C28 C23 120.5(3) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O3 C29 H29A 109.5 . . ?
O3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 C31 O1 119.5(2) . . ?
N1 C31 C34 123.4(2) . . ?
O1 C31 C34 117.2(2) . . ?
N2 C32 N1 127.6(3) . . ?
N2 C32 H32 116.2 . . ?
N1 C32 H32 116.2 . . ?
N2 C33 C34 125.0(3) . . ?
N2 C33 Cl1 114.7(2) . . ?
C34 C33 Cl1 120.3(2) . . ?
C33 C34 C31 114.1(2) . . ?
C33 C34 H34 122.9 . . ?
C31 C34 H34 122.9 . . ?
C39 C35 C36 111.3(4) 2_766 . ?
C39 C35 H35A 109.4 2_766 . ?
C36 C35 H35A 109.4 . . ?
C39 C35 H35B 109.4 2_766 . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 C37 109.7(4) . . ?
C35 C36 H36A 109.7 . . ?
C37 C36 H36A 109.7 . . ?
C35 C36 H36B 109.7 . . ?
C37 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C38 C37 C36 111.2(4) . . ?
C38 C37 H37A 109.4 . . ?
C36 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
C36 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C39 C38 C37 112.3(4) . . ?
C39 C38 C38 109.9(5) . 2_766 ?
C37 C38 C38 110.5(5) . 2_766 ?
C39 C38 H38 108.0 . . ?
C37 C38 H38 108.0 . . ?
C38 C38 H38 108.0 2_766 . ?
C38 C39 C35 111.7(4) . 2_766 ?
C38 C39 H39A 109.3 . . ?
C35 C39 H39A 109.3 2_766 . ?
C38 C39 H39B 109.3 . . ?
C35 C39 H39B 109.3 2_766 . ?
H39A C39 H39B 107.9 . . ?
C31 N1 C32 115.6(2) . . ?
C32 N2 C33 114.2(2) . . ?
C18 N3 C19 115.5(3) . . ?
C20 N4 C19 113.6(3) . . ?
C31 O1 C26 117.0(2) . . ?
C27 O2 C30 117.2(2) . . ?
C25 O3 C29 117.1(2) . . ?
C18 O4 C14 117.4(2) . . ?
C13 O5 C17 117.0(2) . . ?
C15 O6 C22 117.3(2) . . ?

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
C11 C1 C2 C3 -179.9(2) . . . . ?
C9 C1 C2 C3 -59.1(3) . . . . ?
C6 C1 C2 C3 57.9(3) . . . . ?
C1 C2 C3 C7 58.8(3) . . . . ?
C1 C2 C3 C23 -178.6(2) . . . . ?
C1 C2 C3 C4 -58.4(3) . . . . ?
C7 C3 C4 C5 -58.8(3) . . . . ?
C23 C3 C4 C5 177.4(2) . . . . ?
C2 C3 C4 C5 58.2(3) . . . . ?
C3 C4 C5 C10 60.2(3) . . . . ?
C3 C4 C5 C6 -59.6(3) . . . . ?
C10 C5 C6 C1 -59.8(3) . . . . ?
C4 C5 C6 C1 60.5(3) . . . . ?
C11 C1 C6 C5 178.4(2) . . . . ?
C9 C1 C6 C5 58.0(3) . . . . ?
C2 C1 C6 C5 -58.6(3) . . . . ?
C23 C3 C7 C8 -179.1(2) . . . . ?
C4 C3 C7 C8 58.6(3) . . . . ?
C2 C3 C7 C8 -59.0(3) . . . . ?
C3 C7 C8 C10 -59.6(3) . . . . ?
C3 C7 C8 C9 61.4(4) . . . . ?
C11 C1 C9 C8 -178.2(2) . . . . ?
C2 C1 C9 C8 59.4(3) . . . . ?
C6 C1 C9 C8 -57.1(3) . . . . ?
C10 C8 C9 C1 59.6(3) . . . . ?
C7 C8 C9 C1 -61.3(3) . . . . ?
C6 C5 C10 C8 60.3(3) . . . . ?
C4 C5 C10 C8 -59.7(3) . . . . ?
C7 C8 C10 C5 59.3(3) . . . . ?
C9 C8 C10 C5 -60.9(3) . . . . ?
C9 C1 C11 C16 -110.7(3) . . . . ?
C2 C1 C11 C16 9.1(4) . . . . ?
C6 C1 C11 C16 129.6(3) . . . . ?
C9 C1 C11 C12 68.2(3) . . . . ?
C2 C1 C11 C12 -172.0(2) . . . . ?
C6 C1 C11 C12 -51.6(3) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C1 C11 C12 C13 -178.4(2) . . . . ?
C11 C12 C13 O5 178.9(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
O5 C13 C14 C15 -179.1(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
O5 C13 C14 O4 3.5(4) . . . . ?
C12 C13 C14 O4 -177.7(2) . . . . ?
C13 C14 C15 O6 179.7(2) . . . . ?
O4 C14 C15 O6 -3.0(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
O4 C14 C15 C16 177.0(2) . . . . ?
O6 C15 C16 C11 -178.9(3) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 -1.2(4) . . . . ?
C1 C11 C16 C15 177.6(2) . . . . ?
N4 C20 C21 C18 0.0(5) . . . . ?
Cl2 C20 C21 C18 177.5(2) . . . . ?
N3 C18 C21 C20 -0.2(4) . . . . ?
O4 C18 C21 C20 -179.2(2) . . . . ?
C7 C3 C23 C28 4.5(4) . . . . ?
C4 C3 C23 C28 125.6(3) . . . . ?
C2 C3 C23 C28 -115.1(3) . . . . ?
C7 C3 C23 C24 -176.7(2) . . . . ?
C4 C3 C23 C24 -55.6(3) . . . . ?
C2 C3 C23 C24 63.7(3) . . . . ?
C28 C23 C24 C25 -0.4(4) . . . . ?
C3 C23 C24 C25 -179.3(2) . . . . ?
C23 C24 C25 O3 -179.8(2) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
O3 C25 C26 C27 -179.8(2) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
O3 C25 C26 O1 3.0(3) . . . . ?
C24 C25 C26 O1 -177.4(2) . . . . ?
C25 C26 C27 O2 179.0(2) . . . . ?
O1 C26 C27 O2 -3.7(4) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
O1 C26 C27 C28 176.8(2) . . . . ?
O2 C27 C28 C23 -178.8(2) . . . . ?
C26 C27 C28 C23 0.6(4) . . . . ?
C24 C23 C28 C27 -0.2(4) . . . . ?
C3 C23 C28 C27 178.6(2) . . . . ?
N2 C33 C34 C31 -0.1(4) . . . . ?
Cl1 C33 C34 C31 179.5(2) . . . . ?
N1 C31 C34 C33 -1.4(4) . . . . ?
O1 C31 C34 C33 179.2(2) . . . . ?
C39 C35 C36 C37 57.1(6) 2_766 . . . ?
C35 C36 C37 C38 -55.8(5) . . . . ?
C36 C37 C38 C39 178.1(4) . . . . ?
C36 C37 C38 C38 55.0(6) . . . 2_766 ?
C37 C38 C39 C35 179.0(4) . . . 2_766 ?
C38 C38 C39 C35 -57.5(6) 2_766 . . 2_766 ?
O1 C31 N1 C32 -179.3(2) . . . . ?
C34 C31 N1 C32 1.3(4) . . . . ?
N2 C32 N1 C31 0.3(5) . . . . ?
N1 C32 N2 C33 -1.7(5) . . . . ?
C34 C33 N2 C32 1.5(4) . . . . ?
Cl1 C33 N2 C32 -178.1(2) . . . . ?
O4 C18 N3 C19 179.5(3) . . . . ?
C21 C18 N3 C19 0.6(4) . . . . ?
N4 C19 N3 C18 -0.8(5) . . . . ?
C21 C20 N4 C19 -0.1(5) . . . . ?
Cl2 C20 N4 C19 -177.7(3) . . . . ?
N3 C19 N4 C20 0.6(5) . . . . ?
N1 C31 O1 C26 8.3(4) . . . . ?
C34 C31 O1 C26 -172.3(2) . . . . ?
C27 C26 O1 C31 82.1(3) . . . . ?
C25 C26 O1 C31 -100.6(3) . . . . ?
C26 C27 O2 C30 179.6(2) . . . . ?
C28 C27 O2 C30 -1.0(4) . . . . ?
C24 C25 O3 C29 8.3(4) . . . . ?
C26 C25 O3 C29 -172.1(2) . . . . ?
N3 C18 O4 C14 6.8(4) . . . . ?
C21 C18 O4 C14 -174.2(2) . . . . ?
C15 C14 O4 C18 81.3(3) . . . . ?
C13 C14 O4 C18 -101.3(3) . . . . ?
C14 C13 O5 C17 -172.4(2) . . . . ?
C12 C13 O5 C17 8.9(4) . . . . ?
C14 C15 O6 C22 177.7(3) . . . . ?
C16 C15 O6 C22 -2.3(4) . . . . ?

_refine_diff_density_max         0.946
_refine_diff_density_min         -1.096
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1880548'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37.50 H40 Cl2 N4 O6'
_chemical_formula_weight         713.63

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

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

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

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

_cell_length_a                   9.9312(5)
_cell_length_b                   13.0381(7)
_cell_length_c                   14.9669(8)
_cell_angle_alpha                78.504(2)
_cell_angle_beta                 71.545(2)
_cell_angle_gamma                71.592(2)
_cell_volume                     1733.59(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             750
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            23329
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.501
_diffrn_reflns_theta_max         79.399
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7107
_reflns_number_gt                5375
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0855P)²+0.8772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7107
_refine_ls_number_parameters     482
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.2593(2) 0.27465(17) 0.13500(16) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.1151(3) 0.26132(19) 0.20858(17) 0.0245(5) Uani 1 1 d . . . . .
H2A H 0.076944 0.319754 0.250744 0.029 Uiso 1 1 calc R U . . .
H2B H 0.040076 0.268199 0.175607 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1413(3) 0.1501(2) 0.26808(17) 0.0256(5) Uani 1 1 d . . . . .
H3 H 0.046440 0.143220 0.315158 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2551(3) 0.1415(2) 0.32074(17) 0.0248(5) Uani 1 1 d . . . . .
H4A H 0.270902 0.070586 0.360418 0.030 Uiso 1 1 calc R U . . .
H4B H 0.217058 0.199779 0.363009 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4032(2) 0.15176(18) 0.24965(16) 0.0204(4) Uani 1 1 d . . . . .
C6 C 0.3741(2) 0.26238(18) 0.18913(16) 0.0206(4) Uani 1 1 d . . . . .
H6A H 0.467813 0.270349 0.142965 0.025 Uiso 1 1 calc R U . . .
H6B H 0.337969 0.321253 0.230689 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3151(3) 0.18195(18) 0.07106(16) 0.0212(5) Uani 1 1 d . . . . .
H7A H 0.241039 0.187900 0.037606 0.025 Uiso 1 1 calc R U . . .
H7B H 0.407849 0.188541 0.022869 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4572(3) 0.06192(18) 0.18269(16) 0.0218(5) Uani 1 1 d . . . . .
H8A H 0.551102 0.068260 0.135774 0.026 Uiso 1 1 calc R U . . .
H8B H 0.476168 -0.010354 0.220001 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3425(3) 0.07113(18) 0.13053(17) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.379968 0.011974 0.088151 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1984(3) 0.05969(19) 0.20339(18) 0.0265(5) Uani 1 1 d . . . . .
H10A H 0.124044 0.064537 0.170448 0.032 Uiso 1 1 calc R U . . .
H10B H 0.215557 -0.012104 0.241606 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2394(3) 0.38605(18) 0.07613(16) 0.0206(4) Uani 1 1 d . . . . .
C12 C 0.3571(3) 0.40659(17) 0.00051(16) 0.0212(4) Uani 1 1 d . . . . .
H12 H 0.447380 0.351266 -0.014182 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3424(3) 0.50791(18) -0.05339(16) 0.0219(5) Uani 1 1 d . . . . .
C14 C 0.2099(3) 0.58836(17) -0.03123(16) 0.0225(5) Uani 1 1 d . . . . .
C15 C 0.0934(3) 0.56969(18) 0.04453(18) 0.0240(5) Uani 1 1 d . . . . .
C16 C 0.1080(3) 0.46802(18) 0.09753(17) 0.0236(5) Uani 1 1 d . . . . .
H16 H 0.027673 0.454490 0.148719 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5822(3) 0.4521(2) -0.15990(18) 0.0295(5) Uani 1 1 d . . . . .
H17A H 0.558127 0.392941 -0.177692 0.044 Uiso 1 1 calc R U . . .
H17B H 0.629786 0.423951 -0.108413 0.044 Uiso 1 1 calc R U . . .
H17C H 0.649290 0.481888 -0.214797 0.044 Uiso 1 1 calc R U . . .
C18 C 0.1979(2) 0.77495(18) -0.05630(17) 0.0224(5) Uani 1 1 d . . . . .
C19 C 0.2417(3) 0.8508(2) 0.05049(19) 0.0296(5) Uani 1 1 d . . . . .
H19 H 0.270002 0.841791 0.107137 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1710(3) 0.96030(19) -0.0710(2) 0.0295(6) Uani 1 1 d . . . . .
C21 C 0.1623(3) 0.87503(19) -0.10839(18) 0.0263(5) Uani 1 1 d . . . . .
H21 H 0.134152 0.884176 -0.165154 0.032 Uiso 1 1 calc R U . . .
C22 C -0.1495(3) 0.6418(2) 0.1394(2) 0.0329(6) Uani 1 1 d . . . . .
H22A H -0.231220 0.708287 0.142268 0.049 Uiso 1 1 calc R U . . .
H22B H -0.118368 0.626660 0.197720 0.049 Uiso 1 1 calc R U . . .
H22C H -0.181958 0.580746 0.132782 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5175(2) 0.14006(19) 0.30258(15) 0.0214(5) Uani 1 1 d . . . . .
C24 C 0.5691(3) 0.2273(2) 0.30517(16) 0.0258(5) Uani 1 1 d . . . . .
H24 H 0.534762 0.296196 0.272197 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6705(3) 0.2139(2) 0.35570(17) 0.0273(5) Uani 1 1 d . . . . .
C26 C 0.7214(3) 0.1137(2) 0.40305(16) 0.0247(5) Uani 1 1 d . . . . .
C27 C 0.6741(2) 0.02523(19) 0.39993(15) 0.0231(5) Uani 1 1 d . . . . .
C28 C 0.5710(3) 0.03892(19) 0.35069(16) 0.0235(5) Uani 1 1 d . . . . .
H28 H 0.536565 -0.020913 0.349667 0.028 Uiso 1 1 calc R U . . .
C29 C 0.6778(4) 0.3986(2) 0.3182(2) 0.0495(8) Uani 1 1 d . . . . .
H29A H 0.706830 0.395405 0.249650 0.074 Uiso 1 1 calc R U . . .
H29B H 0.722356 0.448633 0.332181 0.074 Uiso 1 1 calc R U . . .
H29C H 0.570110 0.424487 0.340942 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7818(3) 0.1470(2) 0.53286(16) 0.0265(5) Uani 1 1 d . . . . .
C31 C 0.6007(4) 0.2285(3) 0.6531(2) 0.0467(7) Uani 1 1 d . . . . .
H31 H 0.498067 0.253421 0.682645 0.056 Uiso 1 1 calc R U . . .
C32 C 0.8318(4) 0.2037(2) 0.6533(2) 0.0395(7) Uani 1 1 d . . . . .
C33 C 0.8888(3) 0.1526(2) 0.57150(18) 0.0334(6) Uani 1 1 d . . . . .
H33 H 0.991530 0.124058 0.544331 0.040 Uiso 1 1 calc R U . . .
C34 C 0.6888(3) -0.1630(2) 0.4457(2) 0.0321(6) Uani 1 1 d . . . . .
H34A H 0.714196 -0.177963 0.379836 0.048 Uiso 1 1 calc R U . . .
H34B H 0.581891 -0.148731 0.473299 0.048 Uiso 1 1 calc R U . . .
H34C H 0.739343 -0.226029 0.482156 0.048 Uiso 1 1 calc R U . . .
N1 N 0.2395(2) 0.76059(16) 0.02244(14) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.2088(2) 0.95188(17) 0.00840(17) 0.0325(5) Uani 1 1 d . . . . .
N3 N 0.6381(3) 0.1835(2) 0.57266(16) 0.0370(5) Uani 1 1 d . . . . .
N4 N 0.6901(3) 0.2421(2) 0.69611(18) 0.0455(6) Uani 1 1 d . . . . .
O1 O 0.44940(19) 0.53608(13) -0.12884(11) 0.0259(4) Uani 1 1 d . . . . .
O2 O 0.1919(2) 0.68762(12) -0.08946(12) 0.0263(4) Uani 1 1 d . . . . .
O3 O -0.02933(19) 0.65578(13) 0.06034(13) 0.0302(4) Uani 1 1 d . . . . .
O4 O 0.7267(2) 0.29405(16) 0.36410(13) 0.0361(4) Uani 1 1 d . . . . .
O5 O 0.82759(18) 0.09932(15) 0.45158(11) 0.0275(4) Uani 1 1 d . . . . .
O6 O 0.73386(19) -0.06986(14) 0.44810(12) 0.0291(4) Uani 1 1 d . . . . .
Cl1 Cl 0.13385(8) 1.09001(5) -0.12925(6) 0.0436(2) Uani 1 1 d . . . . .
Cl2 Cl 0.94837(11) 0.22367(10) 0.70816(6) 0.0657(3) Uani 1 1 d . . . . .
C35 C -0.1674(18) 0.4598(11) 0.5035(8) 0.087(3) Uani 0.5 1 d . U P A -1
H35 H -0.251047 0.448317 0.493312 0.105 Uiso 0.5 1 calc R U P A -1
C36 C -0.1790(15) 0.5094(13) 0.5736(8) 0.077(3) Uani 0.5 1 d . U P A -1
H36 H -0.277270 0.539624 0.609057 0.092 Uiso 0.5 1 calc R U P A -1
C37 C -0.0639(17) 0.5265(15) 0.6072(11) 0.068(3) Uani 0.5 1 d . U P A -1
H37A H -0.003404 0.454221 0.626916 0.081 Uiso 0.5 1 calc R U P A -1
H37B H -0.113446 0.565176 0.664454 0.081 Uiso 0.5 1 calc R U P A -1
C38 C 0.0383(13) 0.5881(8) 0.5397(10) 0.057(3) Uani 0.5 1 d . U P A -1
H38A H 0.081576 0.622257 0.573162 0.068 Uiso 0.5 1 calc R U P A -1
H38B H -0.010764 0.644065 0.496263 0.068 Uiso 0.5 1 calc R U P A -1
C39 C 0.157(2) 0.491(2) 0.486(2) 0.196(13) Uani 0.5 1 d . U P A -1
H39A H 0.251336 0.510303 0.458140 0.235 Uiso 0.5 1 calc R U P A -1
H39B H 0.174148 0.425899 0.533160 0.235 Uiso 0.5 1 calc R U P A -1
C40 C 0.114(3) 0.461(2) 0.4106(16) 0.166(10) Uani 0.5 1 d . U P A -1
H40A H 0.196721 0.402826 0.378863 0.200 Uiso 0.5 1 calc R U P A -1
H40B H 0.100803 0.525366 0.362775 0.200 Uiso 0.5 1 calc R U P A -1
C41 C -0.024(3) 0.424(2) 0.4428(18) 0.178(11) Uani 0.5 1 d . U P A -1
H41A H -0.042929 0.419936 0.382603 0.213 Uiso 0.5 1 calc R U P A -1
H41B H 0.009959 0.347000 0.468923 0.213 Uiso 0.5 1 calc R U P A -1


_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 C11 1.531(3) . ?
C1 C2 1.541(3) . ?
C1 C7 1.545(3) . ?
C1 C6 1.549(3) . ?
C2 C3 1.535(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.528(4) . ?
C3 C4 1.536(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.546(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C23 1.533(3) . ?
C5 C6 1.538(3) . ?
C5 C8 1.547(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.532(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.536(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.531(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.392(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.364(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.386(3) . ?
C14 O2 1.403(3) . ?
C15 O3 1.364(3) . ?
C15 C16 1.393(3) . ?
C16 H16 0.9500 . ?
C17 O1 1.434(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.329(3) . ?
C18 O2 1.354(3) . ?
C18 C21 1.383(3) . ?
C19 N2 1.330(3) . ?
C19 N1 1.334(3) . ?
C19 H19 0.9500 . ?
C20 N2 1.329(4) . ?
C20 C21 1.377(4) . ?
C20 Cl1 1.726(2) . ?
C21 H21 0.9500 . ?
C22 O3 1.420(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.399(3) . ?
C23 C28 1.400(3) . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 O4 1.373(3) . ?
C25 C26 1.380(4) . ?
C26 C27 1.389(3) . ?
C26 O5 1.407(3) . ?
C27 O6 1.363(3) . ?
C27 C28 1.390(3) . ?
C28 H28 0.9500 . ?
C29 O4 1.409(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.328(4) . ?
C30 O5 1.358(3) . ?
C30 C33 1.387(4) . ?
C31 N4 1.320(4) . ?
C31 N3 1.339(4) . ?
C31 H31 0.9500 . ?
C32 N4 1.324(4) . ?
C32 C33 1.382(4) . ?
C32 Cl2 1.720(3) . ?
C33 H33 0.9500 . ?
C34 O6 1.431(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.297(17) . ?
C35 C41 1.41(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.475(14) . ?
C36 H36 0.9500 . ?
C37 C38 1.496(17) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.58(2) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.48(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.51(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 112.58(18) . . ?
C11 C1 C7 111.11(18) . . ?
C2 C1 C7 107.78(18) . . ?
C11 C1 C6 108.29(17) . . ?
C2 C1 C6 107.94(18) . . ?
C7 C1 C6 109.04(18) . . ?
C3 C2 C1 110.79(19) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C10 C3 C2 109.65(19) . . ?
C10 C3 C4 109.9(2) . . ?
C2 C3 C4 109.03(19) . . ?
C10 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C3 C4 C5 110.60(18) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C23 C5 C6 111.85(18) . . ?
C23 C5 C4 110.33(18) . . ?
C6 C5 C4 108.01(18) . . ?
C23 C5 C8 110.52(18) . . ?
C6 C5 C8 107.71(18) . . ?
C4 C5 C8 108.30(18) . . ?
C5 C6 C1 112.19(17) . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C9 C7 C1 110.37(18) . . ?
C9 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C9 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C5 111.18(18) . . ?
C9 C8 H8A 109.4 . . ?
C5 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C5 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C7 109.61(19) . . ?
C10 C9 C8 109.15(19) . . ?
C7 C9 C8 109.62(17) . . ?
C10 C9 H9 109.5 . . ?
C7 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C3 C10 C9 109.42(18) . . ?
C3 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C3 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 119.4(2) . . ?
C16 C11 C1 121.4(2) . . ?
C12 C11 C1 119.2(2) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O1 C13 C14 115.56(19) . . ?
O1 C13 C12 125.0(2) . . ?
C14 C13 C12 119.4(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 O2 119.8(2) . . ?
C13 C14 O2 119.3(2) . . ?
O3 C15 C14 115.3(2) . . ?
O3 C15 C16 125.2(2) . . ?
C14 C15 C16 119.5(2) . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O2 119.2(2) . . ?
N1 C18 C21 123.6(2) . . ?
O2 C18 C21 117.2(2) . . ?
N2 C19 N1 127.6(2) . . ?
N2 C19 H19 116.2 . . ?
N1 C19 H19 116.2 . . ?
N2 C20 C21 125.2(2) . . ?
N2 C20 Cl1 115.01(19) . . ?
C21 C20 Cl1 119.8(2) . . ?
C20 C21 C18 114.3(2) . . ?
C20 C21 H21 122.9 . . ?
C18 C21 H21 122.9 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 118.9(2) . . ?
C24 C23 C5 122.2(2) . . ?
C28 C23 C5 118.9(2) . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
O4 C25 C26 114.9(2) . . ?
O4 C25 C24 125.2(2) . . ?
C26 C25 C24 119.9(2) . . ?
C25 C26 C27 120.8(2) . . ?
C25 C26 O5 119.8(2) . . ?
C27 C26 O5 119.3(2) . . ?
O6 C27 C26 115.5(2) . . ?
O6 C27 C28 125.1(2) . . ?
C26 C27 C28 119.4(2) . . ?
C27 C28 C23 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 O5 119.0(2) . . ?
N3 C30 C33 123.2(2) . . ?
O5 C30 C33 117.8(2) . . ?
N4 C31 N3 127.4(3) . . ?
N4 C31 H31 116.3 . . ?
N3 C31 H31 116.3 . . ?
N4 C32 C33 126.0(3) . . ?
N4 C32 Cl2 113.8(2) . . ?
C33 C32 Cl2 120.2(3) . . ?
C32 C33 C30 113.6(3) . . ?
C32 C33 H33 123.2 . . ?
C30 C33 H33 123.2 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 N1 C19 115.4(2) . . ?
C20 N2 C19 114.0(2) . . ?
C30 N3 C31 115.9(3) . . ?
C31 N4 C32 113.9(3) . . ?
C13 O1 C17 117.18(17) . . ?
C18 O2 C14 117.45(18) . . ?
C15 O3 C22 117.27(19) . . ?
C25 O4 C29 117.6(2) . . ?
C30 O5 C26 116.98(19) . . ?
C27 O6 C34 117.03(18) . . ?
C36 C35 C41 116.6(15) . . ?
C36 C35 H35 121.7 . . ?
C41 C35 H35 121.7 . . ?
C35 C36 C37 130.4(14) . . ?
C35 C36 H36 114.8 . . ?
C37 C36 H36 114.8 . . ?
C36 C37 C38 117.7(12) . . ?
C36 C37 H37A 107.9 . . ?
C38 C37 H37A 107.9 . . ?
C36 C37 H37B 107.9 . . ?
C38 C37 H37B 107.9 . . ?
H37A C37 H37B 107.2 . . ?
C37 C38 C39 99.0(12) . . ?
C37 C38 H38A 112.0 . . ?
C39 C38 H38A 112.0 . . ?
C37 C38 H38B 112.0 . . ?
C39 C38 H38B 112.0 . . ?
H38A C38 H38B 109.7 . . ?
C40 C39 C38 114(2) . . ?
C40 C39 H39A 108.8 . . ?
C38 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
C38 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C39 C40 C41 115.4(17) . . ?
C39 C40 H40A 108.4 . . ?
C41 C40 H40A 108.4 . . ?
C39 C40 H40B 108.4 . . ?
C41 C40 H40B 108.4 . . ?
H40A C40 H40B 107.5 . . ?
C35 C41 C40 136(2) . . ?
C35 C41 H41A 103.3 . . ?
C40 C41 H41A 103.3 . . ?
C35 C41 H41B 103.3 . . ?
C40 C41 H41B 103.3 . . ?
H41A C41 H41B 105.2 . . ?

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
C11 C1 C2 C3 -178.12(19) . . . . ?
C7 C1 C2 C3 59.0(2) . . . . ?
C6 C1 C2 C3 -58.7(2) . . . . ?
C1 C2 C3 C10 -59.9(2) . . . . ?
C1 C2 C3 C4 60.5(3) . . . . ?
C10 C3 C4 C5 59.8(2) . . . . ?
C2 C3 C4 C5 -60.4(3) . . . . ?
C3 C4 C5 C23 -178.53(19) . . . . ?
C3 C4 C5 C6 58.9(2) . . . . ?
C3 C4 C5 C8 -57.4(2) . . . . ?
C23 C5 C6 C1 179.71(18) . . . . ?
C4 C5 C6 C1 -58.7(2) . . . . ?
C8 C5 C6 C1 58.1(2) . . . . ?
C11 C1 C6 C5 -179.26(18) . . . . ?
C2 C1 C6 C5 58.6(2) . . . . ?
C7 C1 C6 C5 -58.2(2) . . . . ?
C11 C1 C7 C9 176.87(18) . . . . ?
C2 C1 C7 C9 -59.3(2) . . . . ?
C6 C1 C7 C9 57.6(2) . . . . ?
C23 C5 C8 C9 178.88(17) . . . . ?
C6 C5 C8 C9 -58.7(2) . . . . ?
C4 C5 C8 C9 57.9(2) . . . . ?
C1 C7 C9 C10 60.7(2) . . . . ?
C1 C7 C9 C8 -59.1(2) . . . . ?
C5 C8 C9 C10 -59.8(2) . . . . ?
C5 C8 C9 C7 60.2(2) . . . . ?
C2 C3 C10 C9 59.3(2) . . . . ?
C4 C3 C10 C9 -60.5(2) . . . . ?
C7 C9 C10 C3 -59.9(2) . . . . ?
C8 C9 C10 C3 60.2(2) . . . . ?
C2 C1 C11 C16 7.3(3) . . . . ?
C7 C1 C11 C16 128.4(2) . . . . ?
C6 C1 C11 C16 -111.9(2) . . . . ?
C2 C1 C11 C12 -174.1(2) . . . . ?
C7 C1 C11 C12 -53.1(3) . . . . ?
C6 C1 C11 C12 66.6(3) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C1 C11 C12 C13 -179.1(2) . . . . ?
C11 C12 C13 O1 -179.4(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
O1 C13 C14 C15 -179.4(2) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
O1 C13 C14 O2 3.9(3) . . . . ?
C12 C13 C14 O2 -175.64(19) . . . . ?
C13 C14 C15 O3 178.5(2) . . . . ?
O2 C14 C15 O3 -4.8(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
O2 C14 C15 C16 175.0(2) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C1 C11 C16 C15 178.4(2) . . . . ?
O3 C15 C16 C11 -179.0(2) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
N2 C20 C21 C18 -0.5(4) . . . . ?
Cl1 C20 C21 C18 178.55(17) . . . . ?
N1 C18 C21 C20 -1.0(3) . . . . ?
O2 C18 C21 C20 -179.8(2) . . . . ?
C6 C5 C23 C24 9.0(3) . . . . ?
C4 C5 C23 C24 -111.2(2) . . . . ?
C8 C5 C23 C24 129.0(2) . . . . ?
C6 C5 C23 C28 -171.5(2) . . . . ?
C4 C5 C23 C28 68.2(3) . . . . ?
C8 C5 C23 C28 -51.5(3) . . . . ?
C28 C23 C24 C25 -0.8(4) . . . . ?
C5 C23 C24 C25 178.6(2) . . . . ?
C23 C24 C25 O4 -179.0(2) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
O4 C25 C26 C27 -179.6(2) . . . . ?
C24 C25 C26 C27 0.9(4) . . . . ?
O4 C25 C26 O5 -2.5(3) . . . . ?
C24 C25 C26 O5 177.9(2) . . . . ?
C25 C26 C27 O6 178.9(2) . . . . ?
O5 C26 C27 O6 1.9(3) . . . . ?
C25 C26 C27 C28 -1.9(4) . . . . ?
O5 C26 C27 C28 -178.9(2) . . . . ?
O6 C27 C28 C23 -179.4(2) . . . . ?
C26 C27 C28 C23 1.5(3) . . . . ?
C24 C23 C28 C27 -0.2(3) . . . . ?
C5 C23 C28 C27 -179.6(2) . . . . ?
N4 C32 C33 C30 2.2(4) . . . . ?
Cl2 C32 C33 C30 -177.06(19) . . . . ?
N3 C30 C33 C32 -2.5(4) . . . . ?
O5 C30 C33 C32 179.2(2) . . . . ?
O2 C18 N1 C19 -179.6(2) . . . . ?
C21 C18 N1 C19 1.6(3) . . . . ?
N2 C19 N1 C18 -0.8(4) . . . . ?
C21 C20 N2 C19 1.2(4) . . . . ?
Cl1 C20 N2 C19 -177.87(18) . . . . ?
N1 C19 N2 C20 -0.5(4) . . . . ?
O5 C30 N3 C31 179.3(2) . . . . ?
C33 C30 N3 C31 1.0(4) . . . . ?
N4 C31 N3 C30 1.2(5) . . . . ?
N3 C31 N4 C32 -1.5(5) . . . . ?
C33 C32 N4 C31 -0.4(4) . . . . ?
Cl2 C32 N4 C31 178.9(2) . . . . ?
C14 C13 O1 C17 -173.8(2) . . . . ?
C12 C13 O1 C17 5.7(3) . . . . ?
N1 C18 O2 C14 8.9(3) . . . . ?
C21 C18 O2 C14 -172.3(2) . . . . ?
C15 C14 O2 C18 78.1(3) . . . . ?
C13 C14 O2 C18 -105.1(2) . . . . ?
C14 C15 O3 C22 -177.7(2) . . . . ?
C16 C15 O3 C22 2.5(3) . . . . ?
C26 C25 O4 C29 -179.3(3) . . . . ?
C24 C25 O4 C29 0.2(4) . . . . ?
N3 C30 O5 C26 14.2(3) . . . . ?
C33 C30 O5 C26 -167.4(2) . . . . ?
C25 C26 O5 C30 71.8(3) . . . . ?
C27 C26 O5 C30 -111.0(2) . . . . ?
C26 C27 O6 C34 -179.4(2) . . . . ?
C28 C27 O6 C34 1.5(3) . . . . ?
C41 C35 C36 C37 -6(2) . . . . ?
C35 C36 C37 C38 60(2) . . . . ?
C36 C37 C38 C39 -85.9(16) . . . . ?
C37 C38 C39 C40 81(2) . . . . ?
C38 C39 C40 C41 -61(3) . . . . ?
C36 C35 C41 C40 -30(4) . . . . ?
C39 C40 C41 C35 46(5) . . . . ?

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1880550'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 Cl2 N4 O6'
_chemical_formula_weight         665.55

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.6020(17)
_cell_length_b                   10.4596(9)
_cell_length_c                   15.8952(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.358(2)
_cell_angle_gamma                90
_cell_volume                     3110.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.324
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7454
_exptl_absorpt_correction_T_max  0.8364
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            19081
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.727
_diffrn_reflns_theta_max         79.226
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3239
_reflns_number_gt                3092
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0899P)²+4.8503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3239
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.46344(10) 0.28729(17) 0.30489(12) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.40749(11) 0.20077(19) 0.24158(14) 0.0315(4) Uani 1 1 d . . . . .
H2A H 0.384215 0.146004 0.275792 0.038 Uiso 1 1 calc R U . . .
H2B H 0.370190 0.254257 0.201154 0.038 Uiso 1 1 calc R U . . .
C3 C 0.44339(12) 0.11646(19) 0.18786(15) 0.0347(5) Uani 1 1 d . . . . .
H3 H 0.406458 0.061200 0.146962 0.042 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.0317(3) 0.250000 0.0408(8) Uani 1 2 d S T P . .
H4A H 0.477401 -0.023710 0.284582 0.049 Uiso 0.5 1 calc R U P . .
H4B H 0.522600 -0.023703 0.215416 0.049 Uiso 0.5 1 calc R U P . .
C5 C 0.500000 0.3701(2) 0.250000 0.0233(5) Uani 1 2 d S T P . .
H5A H 0.536204 0.425832 0.290155 0.028 Uiso 0.5 1 calc R U P . .
H5B H 0.463795 0.425831 0.209845 0.028 Uiso 0.5 1 calc R U P . .
C6 C 0.52115(11) 0.20140(18) 0.36628(14) 0.0307(4) Uani 1 1 d . . . . .
H6A H 0.557874 0.255447 0.407098 0.037 Uiso 1 1 calc R U . . .
H6B H 0.499075 0.146840 0.401930 0.037 Uiso 1 1 calc R U . . .
C7 C 0.42629(10) 0.37279(16) 0.35621(13) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.37550(10) 0.46279(18) 0.31113(13) 0.0274(4) Uani 1 1 d . . . . .
H8 H 0.366560 0.474668 0.249525 0.033 Uiso 1 1 calc R U . . .
C9 C 0.33796(10) 0.53512(18) 0.35667(14) 0.0278(4) Uani 1 1 d . . . . .
C10 C 0.35118(10) 0.51686(18) 0.44652(13) 0.0279(4) Uani 1 1 d . . . . .
C11 C 0.40135(10) 0.42904(18) 0.49176(13) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.43970(10) 0.35839(17) 0.44663(13) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.475307 0.299901 0.478000 0.031 Uiso 1 1 calc R U . . .
C13 C 0.27874(12) 0.6603(2) 0.23044(15) 0.0406(5) Uani 1 1 d . . . . .
H13A H 0.263948 0.585966 0.191763 0.061 Uiso 1 1 calc R U . . .
H13B H 0.324486 0.692518 0.225998 0.061 Uiso 1 1 calc R U . . .
H13C H 0.242431 0.727500 0.212503 0.061 Uiso 1 1 calc R U . . .
C14 C 0.45951(12) 0.3269(2) 0.62831(13) 0.0360(5) Uani 1 1 d . . . . .
H14A H 0.451036 0.242649 0.600105 0.054 Uiso 1 1 calc R U . . .
H14B H 0.456320 0.320426 0.688527 0.054 Uiso 1 1 calc R U . . .
H14C H 0.507217 0.357161 0.630031 0.054 Uiso 1 1 calc R U . . .
C15 C 0.25568(10) 0.53532(17) 0.50654(13) 0.0261(4) Uani 1 1 d . . . . .
C16 C 0.18146(12) 0.37028(18) 0.49562(17) 0.0367(5) Uani 1 1 d . . . . .
H16 H 0.170367 0.283639 0.479256 0.044 Uiso 1 1 calc R U . . .
C17 C 0.15610(11) 0.54973(19) 0.55656(14) 0.0307(4) Uani 1 1 d . . . . .
C18 C 0.21594(11) 0.60916(18) 0.54835(13) 0.0281(4) Uani 1 1 d . . . . .
H18 H 0.229338 0.693332 0.569259 0.034 Uiso 1 1 calc R U . . .
N1 N 0.23863(9) 0.41588(16) 0.48045(12) 0.0323(4) Uani 1 1 d . . . . .
N2 N 0.13604(10) 0.43084(17) 0.53168(14) 0.0377(4) Uani 1 1 d . . . . .
O1 O 0.28650(8) 0.62395(14) 0.31915(10) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.31373(7) 0.59013(13) 0.49260(9) 0.0294(3) Uani 1 1 d . . . . .
O3 O 0.40715(8) 0.41463(14) 0.57930(9) 0.0310(3) Uani 1 1 d . . . . .
Cl1 Cl 0.09986(3) 0.63216(5) 0.60388(4) 0.0437(2) Uani 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 C7 1.533(2) . ?
C1 C2 1.541(3) . ?
C1 C6 1.543(3) . ?
C1 C5 1.549(2) . ?
C2 C3 1.536(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.529(3) . ?
C3 C6 1.540(3) 2_655 ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.390(3) . ?
C7 C8 1.402(3) . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 O1 1.370(2) . ?
C9 C10 1.386(3) . ?
C10 C11 1.381(3) . ?
C10 O2 1.408(2) . ?
C11 O3 1.370(2) . ?
C11 C12 1.396(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.424(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O3 1.423(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.327(3) . ?
C15 O2 1.350(2) . ?
C15 C18 1.398(3) . ?
C16 N1 1.305(3) . ?
C16 N2 1.352(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.328(3) . ?
C17 C18 1.368(3) . ?
C17 Cl1 1.738(2) . ?
C18 H18 0.9500 . ?

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
C7 C1 C2 109.36(15) . . ?
C7 C1 C6 112.22(15) . . ?
C2 C1 C6 108.40(16) . . ?
C7 C1 C5 110.27(14) . . ?
C2 C1 C5 108.63(14) . . ?
C6 C1 C5 107.88(13) . . ?
C3 C2 C1 110.19(16) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.76(17) . . ?
C4 C3 C6 109.51(16) . 2_655 ?
C2 C3 C6 109.73(16) . 2_655 ?
C4 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C6 C3 H3 109.3 2_655 . ?
C3 C4 C3 109.2(2) 2_655 . ?
C3 C4 H4A 109.8 2_655 . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 2_655 . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C1 C5 C1 111.96(19) . 2_655 ?
C1 C5 H5A 109.2 . . ?
C1 C5 H5A 109.2 2_655 . ?
C1 C5 H5B 109.2 . . ?
C1 C5 H5B 109.2 2_655 . ?
H5A C5 H5B 107.9 . . ?
C3 C6 C1 110.52(16) 2_655 . ?
C3 C6 H6A 109.5 2_655 . ?
C1 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 2_655 . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C12 C7 C8 119.19(16) . . ?
C12 C7 C1 120.91(16) . . ?
C8 C7 C1 119.83(17) . . ?
C9 C8 C7 120.11(18) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O1 C9 C10 115.39(16) . . ?
O1 C9 C8 125.04(18) . . ?
C10 C9 C8 119.56(18) . . ?
C11 C10 C9 120.88(17) . . ?
C11 C10 O2 119.47(17) . . ?
C9 C10 O2 119.64(17) . . ?
O3 C11 C10 115.63(16) . . ?
O3 C11 C12 124.72(18) . . ?
C10 C11 C12 119.59(18) . . ?
C7 C12 C11 120.63(18) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 O2 119.62(16) . . ?
N1 C15 C18 123.00(18) . . ?
O2 C15 C18 117.38(16) . . ?
N1 C16 N2 128.15(19) . . ?
N1 C16 H16 115.9 . . ?
N2 C16 H16 115.9 . . ?
N2 C17 C18 125.67(18) . . ?
N2 C17 Cl1 115.07(15) . . ?
C18 C17 Cl1 119.25(16) . . ?
C17 C18 C15 114.19(18) . . ?
C17 C18 H18 122.9 . . ?
C15 C18 H18 122.9 . . ?
C16 N1 C15 115.87(17) . . ?
C17 N2 C16 113.02(17) . . ?
C9 O1 C13 117.35(16) . . ?
C15 O2 C10 116.73(14) . . ?
C11 O3 C14 117.03(15) . . ?

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
C7 C1 C2 C3 178.66(16) . . . . ?
C6 C1 C2 C3 -58.7(2) . . . . ?
C5 C1 C2 C3 58.3(2) . . . . ?
C1 C2 C3 C4 60.4(2) . . . . ?
C1 C2 C3 C6 -60.0(2) . . . 2_655 ?
C2 C3 C4 C3 -60.46(12) . . . 2_655 ?
C6 C3 C4 C3 60.05(12) 2_655 . . 2_655 ?
C7 C1 C5 C1 -178.49(17) . . . 2_655 ?
C2 C1 C5 C1 -58.67(12) . . . 2_655 ?
C6 C1 C5 C1 58.64(11) . . . 2_655 ?
C7 C1 C6 C3 179.52(15) . . . 2_655 ?
C2 C1 C6 C3 58.6(2) . . . 2_655 ?
C5 C1 C6 C3 -58.8(2) . . . 2_655 ?
C2 C1 C7 C12 113.24(19) . . . . ?
C6 C1 C7 C12 -7.1(2) . . . . ?
C5 C1 C7 C12 -127.37(16) . . . . ?
C2 C1 C7 C8 -63.7(2) . . . . ?
C6 C1 C7 C8 175.99(16) . . . . ?
C5 C1 C7 C8 55.7(2) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C1 C7 C8 C9 175.74(16) . . . . ?
C7 C8 C9 O1 -178.89(17) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
O1 C9 C10 C11 179.38(17) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
O1 C9 C10 O2 -1.6(3) . . . . ?
C8 C9 C10 O2 179.63(16) . . . . ?
C9 C10 C11 O3 -176.77(17) . . . . ?
O2 C10 C11 O3 4.2(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
O2 C10 C11 C12 -178.54(16) . . . . ?
C8 C7 C12 C11 2.3(3) . . . . ?
C1 C7 C12 C11 -174.60(16) . . . . ?
O3 C11 C12 C7 175.01(17) . . . . ?
C10 C11 C12 C7 -2.0(3) . . . . ?
N2 C17 C18 C15 2.7(3) . . . . ?
Cl1 C17 C18 C15 -177.82(14) . . . . ?
N1 C15 C18 C17 -2.8(3) . . . . ?
O2 C15 C18 C17 177.07(17) . . . . ?
N2 C16 N1 C15 2.6(4) . . . . ?
O2 C15 N1 C16 -179.41(19) . . . . ?
C18 C15 N1 C16 0.4(3) . . . . ?
C18 C17 N2 C16 -0.2(3) . . . . ?
Cl1 C17 N2 C16 -179.74(16) . . . . ?
N1 C16 N2 C17 -2.7(4) . . . . ?
C10 C9 O1 C13 170.58(18) . . . . ?
C8 C9 O1 C13 -10.7(3) . . . . ?
N1 C15 O2 C10 2.9(3) . . . . ?
C18 C15 O2 C10 -176.93(17) . . . . ?
C11 C10 O2 C15 -83.7(2) . . . . ?
C9 C10 O2 C15 97.2(2) . . . . ?
C10 C11 O3 C14 -178.64(17) . . . . ?
C12 C11 O3 C14 4.2(3) . . . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1880547'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H42 Cl2 N4 O6'
_chemical_formula_weight         721.65

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

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

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

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

_cell_length_a                   9.9249(9)
_cell_length_b                   13.0873(12)
_cell_length_c                   15.1023(14)
_cell_angle_alpha                78.486(3)
_cell_angle_beta                 71.671(3)
_cell_angle_gamma                71.466(3)
_cell_volume                     1754.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.102
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7631
_exptl_absorpt_correction_T_max  0.8757
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            22489
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.584
_diffrn_reflns_theta_max         79.163
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7155
_reflns_number_gt                5802
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0995P)²+1.1457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7155
_refine_ls_number_parameters     491
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.2591(2) 0.27512(17) 0.13443(15) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.1153(2) 0.26179(19) 0.20638(17) 0.0303(5) Uani 1 1 d . . . . .
H2A H 0.040787 0.268227 0.173272 0.036 Uiso 1 1 calc R U . . .
H2B H 0.076201 0.320179 0.248037 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1422(3) 0.1510(2) 0.26550(17) 0.0327(5) Uani 1 1 d . . . . .
H3 H 0.047217 0.144212 0.311830 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2552(3) 0.1421(2) 0.31853(17) 0.0317(5) Uani 1 1 d . . . . .
H4A H 0.271309 0.071239 0.357574 0.038 Uiso 1 1 calc R U . . .
H4B H 0.216571 0.200003 0.360639 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4026(2) 0.15282(18) 0.24861(15) 0.0265(5) Uani 1 1 d . . . . .
C6 C 0.3735(2) 0.26333(17) 0.18836(15) 0.0254(4) Uani 1 1 d . . . . .
H6A H 0.467285 0.271226 0.142892 0.030 Uiso 1 1 calc R U . . .
H6B H 0.336872 0.322128 0.229444 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4574(3) 0.06315(18) 0.18213(16) 0.0282(5) Uani 1 1 d . . . . .
H7A H 0.551317 0.069544 0.135882 0.034 Uiso 1 1 calc R U . . .
H7B H 0.476592 -0.008939 0.219077 0.034 Uiso 1 1 calc R U . . .
C8 C 0.3430(3) 0.07239(18) 0.13017(17) 0.0296(5) Uani 1 1 d . . . . .
H8 H 0.380869 0.013429 0.088175 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3152(3) 0.18303(17) 0.07094(16) 0.0273(5) Uani 1 1 d . . . . .
H9A H 0.240999 0.188992 0.037715 0.033 Uiso 1 1 calc R U . . .
H9B H 0.407838 0.189629 0.023322 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1990(3) 0.06083(19) 0.20155(18) 0.0340(5) Uani 1 1 d . . . . .
H10A H 0.216196 -0.010800 0.239387 0.041 Uiso 1 1 calc R U . . .
H10B H 0.124819 0.065939 0.168613 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2391(2) 0.38655(17) 0.07556(15) 0.0255(4) Uani 1 1 d . . . . .
C12 C 0.3568(2) 0.40728(17) 0.00104(15) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.447397 0.352191 -0.013025 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3424(2) 0.50803(17) -0.05281(15) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.2102(3) 0.58874(17) -0.03111(16) 0.0275(5) Uani 1 1 d . . . . .
C15 C 0.0939(3) 0.57033(17) 0.04328(17) 0.0291(5) Uani 1 1 d . . . . .
C16 C 0.1076(3) 0.46866(18) 0.09636(16) 0.0280(5) Uani 1 1 d . . . . .
H16 H 0.026912 0.455577 0.146805 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5817(3) 0.45207(19) -0.15776(17) 0.0340(5) Uani 1 1 d . . . . .
H17A H 0.557160 0.392365 -0.173669 0.051 Uiso 1 1 calc R U . . .
H17B H 0.630864 0.425340 -0.107286 0.051 Uiso 1 1 calc R U . . .
H17C H 0.647772 0.481037 -0.213189 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1984(2) 0.77462(18) -0.05576(17) 0.0280(5) Uani 1 1 d . . . . .
C19 C 0.2423(3) 0.8501(2) 0.0505(2) 0.0378(6) Uani 1 1 d . . . . .
H19 H 0.270977 0.840561 0.106648 0.045 Uiso 1 1 calc R U . . .
C20 C 0.1716(3) 0.95994(19) -0.0698(2) 0.0384(6) Uani 1 1 d . . . . .
C21 C 0.1626(3) 0.87512(18) -0.10776(19) 0.0332(5) Uani 1 1 d . . . . .
H21 H 0.134554 0.884637 -0.164141 0.040 Uiso 1 1 calc R U . . .
C22 C -0.1490(3) 0.6426(2) 0.1361(2) 0.0396(6) Uani 1 1 d . . . . .
H22A H -0.230994 0.708785 0.138595 0.059 Uiso 1 1 calc R U . . .
H22B H -0.118338 0.627683 0.194162 0.059 Uiso 1 1 calc R U . . .
H22C H -0.180838 0.581568 0.129394 0.059 Uiso 1 1 calc R U . . .
C23 C 0.5167(2) 0.14108(19) 0.30142(15) 0.0278(5) Uani 1 1 d . . . . .
C24 C 0.5688(3) 0.2281(2) 0.30308(16) 0.0307(5) Uani 1 1 d . . . . .
H24 H 0.534689 0.296401 0.269712 0.037 Uiso 1 1 calc R U . . .
C25 C 0.6705(3) 0.2152(2) 0.35346(17) 0.0328(5) Uani 1 1 d . . . . .
C26 C 0.7209(3) 0.1154(2) 0.40131(16) 0.0323(5) Uani 1 1 d . . . . .
C27 C 0.6725(2) 0.0273(2) 0.39955(16) 0.0301(5) Uani 1 1 d . . . . .
C28 C 0.5696(3) 0.04066(19) 0.35022(16) 0.0299(5) Uani 1 1 d . . . . .
H28 H 0.534860 -0.018938 0.349661 0.036 Uiso 1 1 calc R U . . .
C29 C 0.6769(4) 0.3992(3) 0.3153(2) 0.0560(8) Uani 1 1 d . . . . .
H29A H 0.703430 0.395621 0.247526 0.084 Uiso 1 1 calc R U . . .
H29B H 0.722877 0.449011 0.327678 0.084 Uiso 1 1 calc R U . . .
H29C H 0.569361 0.425348 0.339044 0.084 Uiso 1 1 calc R U . . .
C30 C 0.7829(3) 0.1473(2) 0.53023(17) 0.0333(5) Uani 1 1 d . . . . .
C31 C 0.6053(4) 0.2299(3) 0.6496(2) 0.0556(8) Uani 1 1 d . . . . .
H31 H 0.502971 0.257738 0.678183 0.067 Uiso 1 1 calc R U . . .
C32 C 0.8374(4) 0.1967(3) 0.6516(2) 0.0480(7) Uani 1 1 d . . . . .
C33 C 0.8915(3) 0.1486(2) 0.56939(18) 0.0395(6) Uani 1 1 d . . . . .
H33 H 0.993829 0.118998 0.542015 0.047 Uiso 1 1 calc R U . . .
C34 C 0.6866(3) -0.1599(2) 0.4468(2) 0.0407(6) Uani 1 1 d . . . . .
H34A H 0.715054 -0.176671 0.381911 0.061 Uiso 1 1 calc R U . . .
H34B H 0.579267 -0.145185 0.472207 0.061 Uiso 1 1 calc R U . . .
H34C H 0.735206 -0.221856 0.484876 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2396(2) 0.76043(16) 0.02216(14) 0.0311(4) Uani 1 1 d . . . . .
N2 N 0.2094(2) 0.95091(18) 0.00909(18) 0.0423(5) Uani 1 1 d . . . . .
N3 N 0.6405(3) 0.1873(2) 0.56914(17) 0.0454(6) Uani 1 1 d . . . . .
N4 N 0.6968(4) 0.2378(2) 0.69385(19) 0.0558(7) Uani 1 1 d . . . . .
O1 O 0.44932(18) 0.53599(12) -0.12731(11) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.19249(19) 0.68807(12) -0.08893(12) 0.0312(4) Uani 1 1 d . . . . .
O3 O -0.02864(19) 0.65649(13) 0.05837(13) 0.0356(4) Uani 1 1 d . . . . .
O4 O 0.7272(2) 0.29484(16) 0.36083(14) 0.0425(5) Uani 1 1 d . . . . .
O5 O 0.82734(18) 0.10128(15) 0.44937(12) 0.0349(4) Uani 1 1 d . . . . .
O6 O 0.73061(19) -0.06655(15) 0.44886(13) 0.0371(4) Uani 1 1 d . . . . .
Cl1 Cl 0.13466(8) 1.08954(5) -0.12706(6) 0.0558(2) Uani 1 1 d . . . . .
Cl2 Cl 0.95509(13) 0.20613(12) 0.70964(7) 0.0878(4) Uani 1 1 d . . . . .
C35 C -0.0785(15) 0.5319(10) 0.4000(6) 0.095(3) Uani 0.5 1 d . . P A -1
H35A H -0.112167 0.515568 0.350602 0.114 Uiso 0.5 1 calc R U P A -1
H35B H -0.099582 0.611771 0.394034 0.114 Uiso 0.5 1 calc R U P A -1
C36 C -0.1775(16) 0.5012(18) 0.4904(14) 0.127(9) Uani 0.5 1 d . . P A -1
H36A H -0.274284 0.554324 0.490609 0.152 Uiso 0.5 1 calc R U P A -1
H36B H -0.187931 0.431267 0.482017 0.152 Uiso 0.5 1 calc R U P A -1
C37 C -0.173(3) 0.4889(14) 0.5761(14) 0.101(6) Uani 0.5 1 d . U P A -1
H37A H -0.121548 0.411854 0.590903 0.121 Uiso 0.5 1 calc R U P A -1
H37B H -0.275759 0.501271 0.616071 0.121 Uiso 0.5 1 calc R U P A -1
C38 C -0.107(2) 0.5512(14) 0.6043(16) 0.118(6) Uani 0.5 1 d . U P A -1
H38A H -0.097794 0.515821 0.667236 0.142 Uiso 0.5 1 calc R U P A -1
H38B H -0.184484 0.620753 0.615216 0.142 Uiso 0.5 1 calc R U P A -1
C39 C 0.0405(11) 0.5854(7) 0.5567(6) 0.071(2) Uani 0.5 1 d . U P A -1
H39A H 0.012806 0.653012 0.515435 0.085 Uiso 0.5 1 calc R U P A -1
H39B H 0.063882 0.606866 0.608158 0.085 Uiso 0.5 1 calc R U P A -1
C40 C 0.164(3) 0.5306(16) 0.5087(15) 0.125(9) Uani 0.5 1 d . . P A -1
H40A H 0.207419 0.474800 0.554354 0.150 Uiso 0.5 1 calc R U P A -1
H40B H 0.227392 0.580578 0.485501 0.150 Uiso 0.5 1 calc R U P A -1
C41 C 0.1885(18) 0.4670(11) 0.4186(9) 0.065(3) Uani 0.5 1 d . . P A -1
H41A H 0.273977 0.482544 0.368278 0.077 Uiso 0.5 1 calc R U P A -1
H41B H 0.214420 0.388025 0.438272 0.077 Uiso 0.5 1 calc R U P A -1
C42 C 0.0585(19) 0.4957(16) 0.3777(10) 0.103(5) Uani 0.5 1 d . . P A -1
H42A H 0.087761 0.545887 0.321483 0.123 Uiso 0.5 1 calc R U P A -1
H42B H 0.072646 0.427503 0.352835 0.123 Uiso 0.5 1 calc R U P A -1


_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 C2 1.535(3) . ?
C1 C11 1.538(3) . ?
C1 C9 1.543(3) . ?
C1 C6 1.547(3) . ?
C2 C3 1.535(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.527(4) . ?
C3 C4 1.535(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C23 1.533(3) . ?
C5 C6 1.542(3) . ?
C5 C7 1.550(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.535(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.526(3) . ?
C8 C9 1.535(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.394(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.363(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.381(4) . ?
C14 O2 1.408(3) . ?
C15 O3 1.363(3) . ?
C15 C16 1.400(3) . ?
C16 H16 0.9500 . ?
C17 O1 1.431(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.324(3) . ?
C18 O2 1.351(3) . ?
C18 C21 1.393(3) . ?
C19 N2 1.328(4) . ?
C19 N1 1.337(3) . ?
C19 H19 0.9500 . ?
C20 N2 1.331(4) . ?
C20 C21 1.385(4) . ?
C20 Cl1 1.726(3) . ?
C21 H21 0.9500 . ?
C22 O3 1.418(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.399(3) . ?
C23 C28 1.401(3) . ?
C24 C25 1.396(3) . ?
C24 H24 0.9500 . ?
C25 O4 1.369(3) . ?
C25 C26 1.383(3) . ?
C26 C27 1.391(4) . ?
C26 O5 1.408(3) . ?
C27 O6 1.360(3) . ?
C27 C28 1.393(3) . ?
C28 H28 0.9500 . ?
C29 O4 1.413(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.321(4) . ?
C30 O5 1.355(3) . ?
C30 C33 1.388(4) . ?
C31 N4 1.323(5) . ?
C31 N3 1.338(4) . ?
C31 H31 0.9500 . ?
C32 N4 1.320(5) . ?
C32 C33 1.380(4) . ?
C32 Cl2 1.710(3) . ?
C33 H33 0.9500 . ?
C34 O6 1.431(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C42 1.246(19) . ?
C35 C36 1.48(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.29(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.39(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.58(2) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.28(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.65(2) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.51(2) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?

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
C2 C1 C11 112.63(18) . . ?
C2 C1 C9 107.63(18) . . ?
C11 C1 C9 110.79(17) . . ?
C2 C1 C6 108.16(18) . . ?
C11 C1 C6 108.18(17) . . ?
C9 C1 C6 109.37(17) . . ?
C1 C2 C3 110.61(18) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C10 C3 C4 110.21(19) . . ?
C10 C3 C2 109.6(2) . . ?
C4 C3 C2 109.50(19) . . ?
C10 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C3 C4 C5 110.22(19) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C23 C5 C4 110.27(18) . . ?
C23 C5 C6 111.83(18) . . ?
C4 C5 C6 108.33(18) . . ?
C23 C5 C7 110.45(18) . . ?
C4 C5 C7 108.21(18) . . ?
C6 C5 C7 107.64(17) . . ?
C5 C6 C1 111.95(17) . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C5 111.10(18) . . ?
C8 C7 H7A 109.4 . . ?
C5 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C5 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C10 C8 C7 109.33(19) . . ?
C10 C8 C9 109.62(19) . . ?
C7 C8 C9 109.75(18) . . ?
C10 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C8 C9 C1 110.11(18) . . ?
C8 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C8 C10 C3 108.99(19) . . ?
C8 C10 H10A 109.9 . . ?
C3 C10 H10A 109.9 . . ?
C8 C10 H10B 109.9 . . ?
C3 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 119.1(2) . . ?
C16 C11 C1 121.5(2) . . ?
C12 C11 C1 119.39(19) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C14 115.35(19) . . ?
O1 C13 C12 125.3(2) . . ?
C14 C13 C12 119.4(2) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 O2 119.8(2) . . ?
C13 C14 O2 119.4(2) . . ?
O3 C15 C14 115.0(2) . . ?
O3 C15 C16 125.1(2) . . ?
C14 C15 C16 119.8(2) . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O2 119.5(2) . . ?
N1 C18 C21 123.4(2) . . ?
O2 C18 C21 117.1(2) . . ?
N2 C19 N1 127.4(3) . . ?
N2 C19 H19 116.3 . . ?
N1 C19 H19 116.3 . . ?
N2 C20 C21 125.3(2) . . ?
N2 C20 Cl1 114.9(2) . . ?
C21 C20 Cl1 119.7(2) . . ?
C20 C21 C18 113.9(2) . . ?
C20 C21 H21 123.1 . . ?
C18 C21 H21 123.1 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 118.9(2) . . ?
C24 C23 C5 121.91(19) . . ?
C28 C23 C5 119.2(2) . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
O4 C25 C26 115.0(2) . . ?
O4 C25 C24 125.4(2) . . ?
C26 C25 C24 119.6(2) . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 O5 119.7(2) . . ?
C27 C26 O5 119.3(2) . . ?
O6 C27 C26 115.5(2) . . ?
O6 C27 C28 125.3(2) . . ?
C26 C27 C28 119.3(2) . . ?
C27 C28 C23 120.7(2) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 O5 119.7(2) . . ?
N3 C30 C33 122.9(2) . . ?
O5 C30 C33 117.5(2) . . ?
N4 C31 N3 127.4(3) . . ?
N4 C31 H31 116.3 . . ?
N3 C31 H31 116.3 . . ?
N4 C32 C33 125.9(3) . . ?
N4 C32 Cl2 113.5(2) . . ?
C33 C32 Cl2 120.6(3) . . ?
C32 C33 C30 114.0(3) . . ?
C32 C33 H33 123.0 . . ?
C30 C33 H33 123.0 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 N1 C19 115.9(2) . . ?
C19 N2 C20 114.1(2) . . ?
C30 N3 C31 116.1(3) . . ?
C32 N4 C31 113.7(3) . . ?
C13 O1 C17 117.05(17) . . ?
C18 O2 C14 117.39(17) . . ?
C15 O3 C22 117.02(19) . . ?
C25 O4 C29 117.5(2) . . ?
C30 O5 C26 117.63(19) . . ?
C27 O6 C34 117.19(19) . . ?
C42 C35 C36 124.6(14) . . ?
C42 C35 H35A 106.2 . . ?
C36 C35 H35A 106.2 . . ?
C42 C35 H35B 106.2 . . ?
C36 C35 H35B 106.2 . . ?
H35A C35 H35B 106.4 . . ?
C37 C36 C35 133.4(18) . . ?
C37 C36 H36A 103.9 . . ?
C35 C36 H36A 103.9 . . ?
C37 C36 H36B 103.9 . . ?
C35 C36 H36B 103.9 . . ?
H36A C36 H36B 105.4 . . ?
C36 C37 C38 120(2) . . ?
C36 C37 H37A 107.3 . . ?
C38 C37 H37A 107.3 . . ?
C36 C37 H37B 107.3 . . ?
C38 C37 H37B 107.3 . . ?
H37A C37 H37B 106.9 . . ?
C37 C38 C39 131.7(17) . . ?
C37 C38 H38A 104.3 . . ?
C39 C38 H38A 104.3 . . ?
C37 C38 H38B 104.3 . . ?
C39 C38 H38B 104.3 . . ?
H38A C38 H38B 105.6 . . ?
C40 C39 C38 128.8(10) . . ?
C40 C39 H39A 105.1 . . ?
C38 C39 H39A 105.1 . . ?
C40 C39 H39B 105.1 . . ?
C38 C39 H39B 105.1 . . ?
H39A C39 H39B 105.9 . . ?
C39 C40 C41 126.0(17) . . ?
C39 C40 H40A 105.8 . . ?
C41 C40 H40A 105.8 . . ?
C39 C40 H40B 105.8 . . ?
C41 C40 H40B 105.8 . . ?
H40A C40 H40B 106.2 . . ?
C42 C41 C40 115.9(14) . . ?
C42 C41 H41A 108.3 . . ?
C40 C41 H41A 108.3 . . ?
C42 C41 H41B 108.3 . . ?
C40 C41 H41B 108.3 . . ?
H41A C41 H41B 107.4 . . ?
C35 C42 C41 140.9(12) . . ?
C35 C42 H42A 101.8 . . ?
C41 C42 H42A 101.8 . . ?
C35 C42 H42B 101.8 . . ?
C41 C42 H42B 101.8 . . ?
H42A C42 H42B 104.7 . . ?

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
C11 C1 C2 C3 -178.06(19) . . . . ?
C9 C1 C2 C3 59.5(2) . . . . ?
C6 C1 C2 C3 -58.6(2) . . . . ?
C1 C2 C3 C10 -60.5(2) . . . . ?
C1 C2 C3 C4 60.4(3) . . . . ?
C10 C3 C4 C5 60.3(2) . . . . ?
C2 C3 C4 C5 -60.3(3) . . . . ?
C3 C4 C5 C23 -178.58(19) . . . . ?
C3 C4 C5 C6 58.7(2) . . . . ?
C3 C4 C5 C7 -57.7(2) . . . . ?
C23 C5 C6 C1 179.60(18) . . . . ?
C4 C5 C6 C1 -58.7(2) . . . . ?
C7 C5 C6 C1 58.1(2) . . . . ?
C2 C1 C6 C5 58.5(2) . . . . ?
C11 C1 C6 C5 -179.20(18) . . . . ?
C9 C1 C6 C5 -58.4(2) . . . . ?
C23 C5 C7 C8 178.86(17) . . . . ?
C4 C5 C7 C8 58.1(2) . . . . ?
C6 C5 C7 C8 -58.8(2) . . . . ?
C5 C7 C8 C10 -59.9(2) . . . . ?
C5 C7 C8 C9 60.3(2) . . . . ?
C10 C8 C9 C1 61.1(2) . . . . ?
C7 C8 C9 C1 -59.0(2) . . . . ?
C2 C1 C9 C8 -59.7(2) . . . . ?
C11 C1 C9 C8 176.79(17) . . . . ?
C6 C1 C9 C8 57.6(2) . . . . ?
C7 C8 C10 C3 60.1(2) . . . . ?
C9 C8 C10 C3 -60.2(2) . . . . ?
C4 C3 C10 C8 -60.8(2) . . . . ?
C2 C3 C10 C8 59.7(2) . . . . ?
C2 C1 C11 C16 7.9(3) . . . . ?
C9 C1 C11 C16 128.5(2) . . . . ?
C6 C1 C11 C16 -111.7(2) . . . . ?
C2 C1 C11 C12 -174.02(19) . . . . ?
C9 C1 C11 C12 -53.4(3) . . . . ?
C6 C1 C11 C12 66.5(2) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C1 C11 C12 C13 -179.20(19) . . . . ?
C11 C12 C13 O1 -179.2(2) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
O1 C13 C14 C15 -179.6(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
O1 C13 C14 O2 3.9(3) . . . . ?
C12 C13 C14 O2 -176.11(19) . . . . ?
C13 C14 C15 O3 178.8(2) . . . . ?
O2 C14 C15 O3 -4.7(3) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
O2 C14 C15 C16 175.09(19) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C1 C11 C16 C15 178.1(2) . . . . ?
O3 C15 C16 C11 -179.0(2) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
N2 C20 C21 C18 -0.4(4) . . . . ?
Cl1 C20 C21 C18 178.56(17) . . . . ?
N1 C18 C21 C20 -1.0(3) . . . . ?
O2 C18 C21 C20 -179.8(2) . . . . ?
C4 C5 C23 C24 -112.2(2) . . . . ?
C6 C5 C23 C24 8.4(3) . . . . ?
C7 C5 C23 C24 128.3(2) . . . . ?
C4 C5 C23 C28 67.2(3) . . . . ?
C6 C5 C23 C28 -172.2(2) . . . . ?
C7 C5 C23 C28 -52.3(3) . . . . ?
C28 C23 C24 C25 -0.7(4) . . . . ?
C5 C23 C24 C25 178.7(2) . . . . ?
C23 C24 C25 O4 -179.2(2) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
O4 C25 C26 C27 -179.8(2) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
O4 C25 C26 O5 -2.5(3) . . . . ?
C24 C25 C26 O5 177.7(2) . . . . ?
C25 C26 C27 O6 179.6(2) . . . . ?
O5 C26 C27 O6 2.3(3) . . . . ?
C25 C26 C27 C28 -1.2(4) . . . . ?
O5 C26 C27 C28 -178.6(2) . . . . ?
O6 C27 C28 C23 -179.9(2) . . . . ?
C26 C27 C28 C23 1.1(3) . . . . ?
C24 C23 C28 C27 -0.1(3) . . . . ?
C5 C23 C28 C27 -179.5(2) . . . . ?
N4 C32 C33 C30 1.1(4) . . . . ?
Cl2 C32 C33 C30 -179.7(2) . . . . ?
N3 C30 C33 C32 -0.9(4) . . . . ?
O5 C30 C33 C32 -179.9(2) . . . . ?
O2 C18 N1 C19 -179.9(2) . . . . ?
C21 C18 N1 C19 1.4(3) . . . . ?
N2 C19 N1 C18 -0.5(4) . . . . ?
N1 C19 N2 C20 -0.8(4) . . . . ?
C21 C20 N2 C19 1.2(4) . . . . ?
Cl1 C20 N2 C19 -177.80(18) . . . . ?
O5 C30 N3 C31 179.0(3) . . . . ?
C33 C30 N3 C31 0.1(4) . . . . ?
N4 C31 N3 C30 0.9(5) . . . . ?
C33 C32 N4 C31 -0.3(5) . . . . ?
Cl2 C32 N4 C31 -179.5(2) . . . . ?
N3 C31 N4 C32 -0.8(5) . . . . ?
C14 C13 O1 C17 -174.0(2) . . . . ?
C12 C13 O1 C17 6.1(3) . . . . ?
N1 C18 O2 C14 9.0(3) . . . . ?
C21 C18 O2 C14 -172.2(2) . . . . ?
C15 C14 O2 C18 78.0(3) . . . . ?
C13 C14 O2 C18 -105.4(2) . . . . ?
C14 C15 O3 C22 -177.8(2) . . . . ?
C16 C15 O3 C22 2.4(3) . . . . ?
C26 C25 O4 C29 -178.5(3) . . . . ?
C24 C25 O4 C29 1.3(4) . . . . ?
N3 C30 O5 C26 11.2(3) . . . . ?
C33 C30 O5 C26 -169.8(2) . . . . ?
C25 C26 O5 C30 73.2(3) . . . . ?
C27 C26 O5 C30 -109.4(3) . . . . ?
C26 C27 O6 C34 -178.4(2) . . . . ?
C28 C27 O6 C34 2.5(3) . . . . ?
C42 C35 C36 C37 44(3) . . . . ?
C35 C36 C37 C38 32(3) . . . . ?
C36 C37 C38 C39 -43(3) . . . . ?
C37 C38 C39 C40 -36(3) . . . . ?
C38 C39 C40 C41 51(3) . . . . ?
C39 C40 C41 C42 13(2) . . . . ?
C36 C35 C42 C41 -41(4) . . . . ?
C40 C41 C42 C35 -25(4) . . . . ?

_refine_diff_density_max         0.720
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 1880549'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H41 Cl2 N4 O6'
_chemical_formula_weight         720.65

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

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

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

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

_cell_length_a                   9.9494(7)
_cell_length_b                   13.0577(10)
_cell_length_c                   15.0470(11)
_cell_angle_alpha                78.907(2)
_cell_angle_beta                 71.437(2)
_cell_angle_gamma                70.820(2)
_cell_volume                     1741.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             758
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.117
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7671
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            23211
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         78.761
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7110
_reflns_number_gt                6160
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0681P)²+0.9776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7110
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25626(18) 0.27725(13) 0.13689(12) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.37148(18) 0.26499(13) 0.19003(12) 0.0204(3) Uani 1 1 d . . . . .
H2A H 0.465348 0.271736 0.143865 0.024 Uiso 1 1 calc R U . . .
H2B H 0.335090 0.324584 0.231310 0.024 Uiso 1 1 calc R U . . .
C3 C 0.40113(18) 0.15462(13) 0.25018(12) 0.0215(3) Uani 1 1 d . . . . .
C4 C 0.25257(19) 0.14659(15) 0.32146(13) 0.0262(4) Uani 1 1 d . . . . .
H4A H 0.268564 0.076113 0.361043 0.031 Uiso 1 1 calc R U . . .
H4B H 0.214426 0.205799 0.363283 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1386(2) 0.15563(15) 0.26930(13) 0.0276(4) Uani 1 1 d . . . . .
H5 H 0.043517 0.149991 0.316305 0.033 Uiso 1 1 calc R U . . .
C6 C 0.11161(19) 0.26652(15) 0.21037(13) 0.0258(4) Uani 1 1 d . . . . .
H6A H 0.073625 0.325635 0.252279 0.031 Uiso 1 1 calc R U . . .
H6B H 0.036049 0.273899 0.177961 0.031 Uiso 1 1 calc R U . . .
C7 C 0.45502(19) 0.06375(14) 0.18384(12) 0.0233(3) Uani 1 1 d . . . . .
H7A H 0.549070 0.068703 0.136892 0.028 Uiso 1 1 calc R U . . .
H7B H 0.474296 -0.008241 0.220960 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3399(2) 0.07331(14) 0.13264(13) 0.0248(4) Uani 1 1 d . . . . .
H8 H 0.377484 0.013380 0.090597 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3125(2) 0.18364(13) 0.07340(12) 0.0230(3) Uani 1 1 d . . . . .
H9A H 0.238297 0.189969 0.040219 0.028 Uiso 1 1 calc R U . . .
H9B H 0.405607 0.188843 0.025444 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1957(2) 0.06403(15) 0.20523(14) 0.0297(4) Uani 1 1 d . . . . .
H10A H 0.121090 0.069177 0.172768 0.036 Uiso 1 1 calc R U . . .
H10B H 0.213158 -0.007434 0.243286 0.036 Uiso 1 1 calc R U . . .
C11 C 0.23607(19) 0.38817(13) 0.07780(12) 0.0210(3) Uani 1 1 d . . . . .
C12 C 0.10343(19) 0.47104(14) 0.09873(12) 0.0236(3) Uani 1 1 d . . . . .
H12 H 0.022645 0.458759 0.149543 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0888(2) 0.57192(14) 0.04538(13) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.2056(2) 0.58943(13) -0.02956(12) 0.0236(3) Uani 1 1 d . . . . .
C15 C 0.33956(19) 0.50778(14) -0.05126(12) 0.0223(3) Uani 1 1 d . . . . .
C16 C 0.35430(19) 0.40728(13) 0.00269(12) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.445313 0.351270 -0.011601 0.026 Uiso 1 1 calc R U . . .
C17 C -0.1569(2) 0.64596(16) 0.13890(15) 0.0340(4) Uani 1 1 d . . . . .
H17A H -0.240414 0.712086 0.140565 0.051 Uiso 1 1 calc R U . . .
H17B H -0.127736 0.633206 0.197376 0.051 Uiso 1 1 calc R U . . .
H17C H -0.186174 0.583631 0.132521 0.051 Uiso 1 1 calc R U . . .
C18 C 0.19626(18) 0.77470(14) -0.05446(13) 0.0230(3) Uani 1 1 d . . . . .
C19 C 0.2439(2) 0.85006(16) 0.05054(14) 0.0310(4) Uani 1 1 d . . . . .
H19 H 0.273962 0.840492 0.106254 0.037 Uiso 1 1 calc R U . . .
C20 C 0.1723(2) 0.95966(14) -0.06895(15) 0.0304(4) Uani 1 1 d . . . . .
C21 C 0.16160(19) 0.87554(14) -0.10641(14) 0.0270(4) Uani 1 1 d . . . . .
H21 H 0.133103 0.885284 -0.162729 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5809(2) 0.45016(15) -0.15620(13) 0.0299(4) Uani 1 1 d . . . . .
H22A H 0.648194 0.479071 -0.210661 0.045 Uiso 1 1 calc R U . . .
H22B H 0.558074 0.390665 -0.173957 0.045 Uiso 1 1 calc R U . . .
H22C H 0.628035 0.422683 -0.104822 0.045 Uiso 1 1 calc R U . . .
C23 C 0.51566(19) 0.14240(14) 0.30241(12) 0.0229(3) Uani 1 1 d . . . . .
C24 C 0.5676(2) 0.22939(15) 0.30425(12) 0.0251(4) Uani 1 1 d . . . . .
H24 H 0.533093 0.297964 0.271176 0.030 Uiso 1 1 calc R U . . .
C25 C 0.6693(2) 0.21599(16) 0.35421(13) 0.0267(4) Uani 1 1 d . . . . .
C26 C 0.72064(19) 0.11547(16) 0.40144(12) 0.0255(4) Uani 1 1 d . . . . .
C27 C 0.67245(19) 0.02759(15) 0.39905(12) 0.0250(4) Uani 1 1 d . . . . .
C28 C 0.56929(19) 0.04162(15) 0.35035(12) 0.0246(4) Uani 1 1 d . . . . .
H28 H 0.534782 -0.017872 0.349589 0.029 Uiso 1 1 calc R U . . .
C29 C 0.6754(3) 0.40038(19) 0.31679(17) 0.0450(6) Uani 1 1 d . . . . .
H29A H 0.724977 0.448986 0.326990 0.067 Uiso 1 1 calc R U . . .
H29B H 0.568197 0.429176 0.342887 0.067 Uiso 1 1 calc R U . . .
H29C H 0.698317 0.395711 0.249093 0.067 Uiso 1 1 calc R U . . .
C30 C 0.6900(2) -0.16050(16) 0.44331(15) 0.0338(4) Uani 1 1 d . . . . .
H30A H 0.742576 -0.223849 0.478416 0.051 Uiso 1 1 calc R U . . .
H30B H 0.715641 -0.174807 0.377473 0.051 Uiso 1 1 calc R U . . .
H30C H 0.583042 -0.146824 0.471236 0.051 Uiso 1 1 calc R U . . .
C31 C 0.7806(2) 0.14708(15) 0.53113(12) 0.0268(4) Uani 1 1 d . . . . .
C32 C 0.6005(3) 0.2294(2) 0.65166(17) 0.0472(6) Uani 1 1 d . . . . .
H32 H 0.497651 0.257245 0.680617 0.057 Uiso 1 1 calc R U . . .
C33 C 0.8327(3) 0.19711(18) 0.65338(15) 0.0390(5) Uani 1 1 d . . . . .
C34 C 0.8884(2) 0.14878(16) 0.57024(13) 0.0305(4) Uani 1 1 d . . . . .
H34 H 0.991296 0.119335 0.542332 0.037 Uiso 1 1 calc R U . . .
N1 N 0.23926(17) 0.75999(12) 0.02284(11) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.21161(18) 0.95066(13) 0.00947(13) 0.0337(4) Uani 1 1 d . . . . .
N3 N 0.6369(2) 0.18626(16) 0.57073(13) 0.0378(4) Uani 1 1 d . . . . .
N4 N 0.6908(2) 0.23788(17) 0.69632(14) 0.0460(5) Uani 1 1 d . . . . .
O1 O 0.18768(15) 0.68829(9) -0.08720(9) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.44694(14) 0.53493(10) -0.12579(9) 0.0267(3) Uani 1 1 d . . . . .
O3 O -0.03552(15) 0.65897(10) 0.06093(10) 0.0304(3) Uani 1 1 d . . . . .
O4 O 0.82695(14) 0.10073(11) 0.44923(9) 0.0280(3) Uani 1 1 d . . . . .
O5 O 0.72567(16) 0.29545(11) 0.36212(10) 0.0337(3) Uani 1 1 d . . . . .
O6 O 0.73199(14) -0.06711(11) 0.44740(9) 0.0303(3) Uani 1 1 d . . . . .
Cl1 Cl 0.13565(6) 1.08973(4) -0.12603(4) 0.04392(16) Uani 1 1 d . . . . .
Cl2 Cl 0.95120(8) 0.20566(8) 0.71138(5) 0.0707(2) Uani 1 1 d . . . . .
C35 C -0.0961(10) 0.5262(6) 0.4039(4) 0.0726(19) Uani 0.5 1 d . . P A -1
H35 H -0.162068 0.577143 0.371584 0.087 Uiso 0.5 1 calc R U P A -1
C36 C 0.046(3) 0.5168(17) 0.3678(12) 0.070(4) Uani 0.5 1 d . . P A -1
H36 H 0.074945 0.550122 0.305595 0.084 Uiso 0.5 1 calc R U P A -1
C37 C 0.1661(15) 0.4596(10) 0.4137(9) 0.075(5) Uani 0.5 1 d . . P A -1
H37A H 0.148014 0.390438 0.447633 0.090 Uiso 0.5 1 calc R U P A -1
H37B H 0.260925 0.440795 0.363924 0.090 Uiso 0.5 1 calc R U P A -1
C38 C 0.1830(11) 0.5203(10) 0.4805(9) 0.062(3) Uani 0.5 1 d . . P A -1
H38A H 0.236382 0.573465 0.443380 0.075 Uiso 0.5 1 calc R U P A -1
H38B H 0.247511 0.468069 0.517465 0.075 Uiso 0.5 1 calc R U P A -1
C39 C 0.0441(7) 0.5817(4) 0.5496(4) 0.0498(12) Uani 0.5 1 d . . P A -1
H39A H -0.014732 0.641618 0.513988 0.060 Uiso 0.5 1 calc R U P A -1
H39B H 0.073478 0.614814 0.591728 0.060 Uiso 0.5 1 calc R U P A -1
C40 C -0.053(3) 0.5105(16) 0.6098(11) 0.071(5) Uani 0.5 1 d . . P A -1
H40A H 0.009666 0.433958 0.611297 0.086 Uiso 0.5 1 calc R U P A -1
H40B H -0.088181 0.531071 0.675089 0.086 Uiso 0.5 1 calc R U P A -1
C41 C -0.1860(18) 0.5144(13) 0.5809(11) 0.079(5) Uani 0.5 1 d . . P A -1
H41A H -0.241853 0.591990 0.571626 0.094 Uiso 0.5 1 calc R U P A -1
H41B H -0.250172 0.480123 0.634495 0.094 Uiso 0.5 1 calc R U P A -1
C42 C -0.1636(19) 0.4618(12) 0.4937(10) 0.095(6) Uani 0.5 1 d . . P A -1
H42A H -0.260082 0.457989 0.491217 0.113 Uiso 0.5 1 calc R U P A -1
H42B H -0.097532 0.386515 0.497381 0.113 Uiso 0.5 1 calc R U P A -1


_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 C11 1.535(2) . ?
C1 C6 1.540(2) . ?
C1 C9 1.542(2) . ?
C1 C2 1.547(2) . ?
C2 C3 1.540(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C23 1.531(2) . ?
C3 C7 1.546(2) . ?
C3 C4 1.548(2) . ?
C4 C5 1.536(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.527(3) . ?
C5 C6 1.535(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.533(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.527(3) . ?
C8 C9 1.532(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.393(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 O3 1.368(2) . ?
C13 C14 1.384(3) . ?
C14 C15 1.394(3) . ?
C14 O1 1.402(2) . ?
C15 O2 1.363(2) . ?
C15 C16 1.394(2) . ?
C16 H16 0.9500 . ?
C17 O3 1.421(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.323(2) . ?
C18 O1 1.352(2) . ?
C18 C21 1.393(2) . ?
C19 N2 1.322(3) . ?
C19 N1 1.340(2) . ?
C19 H19 0.9500 . ?
C20 N2 1.330(3) . ?
C20 C21 1.374(3) . ?
C20 Cl1 1.7280(19) . ?
C21 H21 0.9500 . ?
C22 O2 1.431(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.398(2) . ?
C23 C24 1.402(3) . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 O5 1.371(2) . ?
C25 C26 1.386(3) . ?
C26 C27 1.392(3) . ?
C26 O4 1.404(2) . ?
C27 O6 1.362(2) . ?
C27 C28 1.389(2) . ?
C28 H28 0.9500 . ?
C29 O5 1.414(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 O6 1.430(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 N3 1.325(3) . ?
C31 O4 1.356(2) . ?
C31 C34 1.385(3) . ?
C32 N4 1.323(3) . ?
C32 N3 1.334(3) . ?
C32 H32 0.9500 . ?
C33 N4 1.324(3) . ?
C33 C34 1.379(3) . ?
C33 Cl2 1.716(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.32(3) . ?
C35 C42 1.529(15) . ?
C35 H35 0.9500 . ?
C36 C37 1.48(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.471(17) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.521(10) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.53(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.50(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.517(16) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C6 112.47(14) . . ?
C11 C1 C9 110.80(13) . . ?
C6 C1 C9 108.10(14) . . ?
C11 C1 C2 108.22(13) . . ?
C6 C1 C2 108.06(13) . . ?
C9 C1 C2 109.11(13) . . ?
C3 C2 C1 111.94(13) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C23 C3 C2 111.88(13) . . ?
C23 C3 C7 110.61(14) . . ?
C2 C3 C7 107.78(13) . . ?
C23 C3 C4 110.14(14) . . ?
C2 C3 C4 107.95(13) . . ?
C7 C3 C4 108.35(14) . . ?
C5 C4 C3 110.33(14) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 109.87(15) . . ?
C10 C5 C4 110.02(15) . . ?
C6 C5 C4 109.05(14) . . ?
C10 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 C1 110.43(14) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C3 111.27(14) . . ?
C8 C7 H7A 109.4 . . ?
C3 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C3 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C10 C8 C9 109.72(15) . . ?
C10 C8 C7 109.22(15) . . ?
C9 C8 C7 109.46(13) . . ?
C10 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
C8 C9 C1 110.27(14) . . ?
C8 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C5 C10 C8 109.38(14) . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10B 109.8 . . ?
C8 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 119.34(15) . . ?
C12 C11 C1 121.26(15) . . ?
C16 C11 C1 119.39(15) . . ?
C11 C12 C13 120.22(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O3 C13 C14 115.19(15) . . ?
O3 C13 C12 124.83(17) . . ?
C14 C13 C12 119.98(16) . . ?
C13 C14 C15 120.67(15) . . ?
C13 C14 O1 120.01(15) . . ?
C15 C14 O1 119.25(16) . . ?
O2 C15 C16 125.39(16) . . ?
O2 C15 C14 115.38(15) . . ?
C16 C15 C14 119.23(16) . . ?
C15 C16 C11 120.55(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O1 119.45(15) . . ?
N1 C18 C21 123.36(16) . . ?
O1 C18 C21 117.17(16) . . ?
N2 C19 N1 127.64(19) . . ?
N2 C19 H19 116.2 . . ?
N1 C19 H19 116.2 . . ?
N2 C20 C21 125.49(17) . . ?
N2 C20 Cl1 114.75(14) . . ?
C21 C20 Cl1 119.76(16) . . ?
C20 C21 C18 114.04(18) . . ?
C20 C21 H21 123.0 . . ?
C18 C21 H21 123.0 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 118.97(16) . . ?
C28 C23 C3 119.02(15) . . ?
C24 C23 C3 122.01(15) . . ?
C25 C24 C23 120.45(16) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
O5 C25 C26 114.90(16) . . ?
O5 C25 C24 125.49(17) . . ?
C26 C25 C24 119.61(17) . . ?
C25 C26 C27 120.79(16) . . ?
C25 C26 O4 119.72(16) . . ?
C27 C26 O4 119.43(16) . . ?
O6 C27 C28 125.21(17) . . ?
O6 C27 C26 115.31(16) . . ?
C28 C27 C26 119.47(16) . . ?
C27 C28 C23 120.68(16) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
O5 C29 H29A 109.5 . . ?
O5 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O5 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N3 C31 O4 119.47(17) . . ?
N3 C31 C34 123.20(18) . . ?
O4 C31 C34 117.31(17) . . ?
N4 C32 N3 127.7(2) . . ?
N4 C32 H32 116.2 . . ?
N3 C32 H32 116.2 . . ?
N4 C33 C34 125.8(2) . . ?
N4 C33 Cl2 114.26(17) . . ?
C34 C33 Cl2 119.97(18) . . ?
C33 C34 C31 113.92(19) . . ?
C33 C34 H34 123.0 . . ?
C31 C34 H34 123.0 . . ?
C18 N1 C19 115.49(16) . . ?
C19 N2 C20 113.95(16) . . ?
C31 N3 C32 115.74(19) . . ?
C32 N4 C33 113.70(19) . . ?
C18 O1 C14 117.21(13) . . ?
C15 O2 C22 117.06(13) . . ?
C13 O3 C17 117.25(14) . . ?
C31 O4 C26 117.16(14) . . ?
C25 O5 C29 117.55(15) . . ?
C27 O6 C30 116.98(14) . . ?
C36 C35 C42 125.3(11) . . ?
C36 C35 H35 117.3 . . ?
C42 C35 H35 117.3 . . ?
C35 C36 C37 127.0(13) . . ?
C35 C36 H36 116.5 . . ?
C37 C36 H36 116.5 . . ?
C38 C37 C36 115.9(12) . . ?
C38 C37 H37A 108.3 . . ?
C36 C37 H37A 108.3 . . ?
C38 C37 H37B 108.3 . . ?
C36 C37 H37B 108.3 . . ?
H37A C37 H37B 107.4 . . ?
C37 C38 C39 118.3(9) . . ?
C37 C38 H38A 107.7 . . ?
C39 C38 H38A 107.7 . . ?
C37 C38 H38B 107.7 . . ?
C39 C38 H38B 107.7 . . ?
H38A C38 H38B 107.1 . . ?
C38 C39 C40 113.8(11) . . ?
C38 C39 H39A 108.8 . . ?
C40 C39 H39A 108.8 . . ?
C38 C39 H39B 108.8 . . ?
C40 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C41 C40 C39 117.7(12) . . ?
C41 C40 H40A 107.9 . . ?
C39 C40 H40A 107.9 . . ?
C41 C40 H40B 107.9 . . ?
C39 C40 H40B 107.9 . . ?
H40A C40 H40B 107.2 . . ?
C40 C41 C42 119.2(15) . . ?
C40 C41 H41A 107.5 . . ?
C42 C41 H41A 107.5 . . ?
C40 C41 H41B 107.5 . . ?
C42 C41 H41B 107.5 . . ?
H41A C41 H41B 107.0 . . ?
C41 C42 C35 111.3(10) . . ?
C41 C42 H42A 109.4 . . ?
C35 C42 H42A 109.4 . . ?
C41 C42 H42B 109.4 . . ?
C35 C42 H42B 109.4 . . ?
H42A C42 H42B 108.0 . . ?

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
C11 C1 C2 C3 -178.99(13) . . . . ?
C6 C1 C2 C3 58.96(17) . . . . ?
C9 C1 C2 C3 -58.35(17) . . . . ?
C1 C2 C3 C23 179.76(14) . . . . ?
C1 C2 C3 C7 57.94(17) . . . . ?
C1 C2 C3 C4 -58.90(18) . . . . ?
C23 C3 C4 C5 -178.44(14) . . . . ?
C2 C3 C4 C5 59.14(18) . . . . ?
C7 C3 C4 C5 -57.32(18) . . . . ?
C3 C4 C5 C10 59.75(18) . . . . ?
C3 C4 C5 C6 -60.80(19) . . . . ?
C10 C5 C6 C1 -59.79(18) . . . . ?
C4 C5 C6 C1 60.87(19) . . . . ?
C11 C1 C6 C5 -178.46(14) . . . . ?
C9 C1 C6 C5 58.90(18) . . . . ?
C2 C1 C6 C5 -59.07(18) . . . . ?
C23 C3 C7 C8 178.71(13) . . . . ?
C2 C3 C7 C8 -58.68(17) . . . . ?
C4 C3 C7 C8 57.89(17) . . . . ?
C3 C7 C8 C10 -59.84(18) . . . . ?
C3 C7 C8 C9 60.31(18) . . . . ?
C10 C8 C9 C1 60.52(18) . . . . ?
C7 C8 C9 C1 -59.32(18) . . . . ?
C11 C1 C9 C8 177.04(13) . . . . ?
C6 C1 C9 C8 -59.30(17) . . . . ?
C2 C1 C9 C8 57.99(17) . . . . ?
C6 C5 C10 C8 59.41(18) . . . . ?
C4 C5 C10 C8 -60.66(18) . . . . ?
C9 C8 C10 C5 -59.82(18) . . . . ?
C7 C8 C10 C5 60.17(18) . . . . ?
C6 C1 C11 C12 6.7(2) . . . . ?
C9 C1 C11 C12 127.82(16) . . . . ?
C2 C1 C11 C12 -112.59(17) . . . . ?
C6 C1 C11 C16 -174.72(15) . . . . ?
C9 C1 C11 C16 -53.6(2) . . . . ?
C2 C1 C11 C16 65.98(19) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C1 C11 C12 C13 178.54(15) . . . . ?
C11 C12 C13 O3 -178.96(16) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
O3 C13 C14 C15 178.54(15) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
O3 C13 C14 O1 -4.4(2) . . . . ?
C12 C13 C14 O1 175.66(15) . . . . ?
C13 C14 C15 O2 -179.21(15) . . . . ?
O1 C14 C15 O2 3.7(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
O1 C14 C15 C16 -176.22(14) . . . . ?
O2 C15 C16 C11 -179.81(15) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C1 C11 C16 C15 -179.11(15) . . . . ?
N2 C20 C21 C18 0.0(3) . . . . ?
Cl1 C20 C21 C18 179.00(13) . . . . ?
N1 C18 C21 C20 -1.6(3) . . . . ?
O1 C18 C21 C20 179.84(15) . . . . ?
C2 C3 C23 C28 -171.79(15) . . . . ?
C7 C3 C23 C28 -51.6(2) . . . . ?
C4 C3 C23 C28 68.1(2) . . . . ?
C2 C3 C23 C24 8.7(2) . . . . ?
C7 C3 C23 C24 128.89(17) . . . . ?
C4 C3 C23 C24 -111.36(18) . . . . ?
C28 C23 C24 C25 -0.9(3) . . . . ?
C3 C23 C24 C25 178.55(16) . . . . ?
C23 C24 C25 O5 -178.93(17) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
O5 C25 C26 C27 -179.87(16) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
O5 C25 C26 O4 -2.4(2) . . . . ?
C24 C25 C26 O4 177.85(16) . . . . ?
C25 C26 C27 O6 179.37(16) . . . . ?
O4 C26 C27 O6 1.9(2) . . . . ?
C25 C26 C27 C28 -1.4(3) . . . . ?
O4 C26 C27 C28 -178.84(15) . . . . ?
O6 C27 C28 C23 -179.63(16) . . . . ?
C26 C27 C28 C23 1.2(3) . . . . ?
C24 C23 C28 C27 0.0(3) . . . . ?
C3 C23 C28 C27 -179.56(15) . . . . ?
N4 C33 C34 C31 1.2(3) . . . . ?
Cl2 C33 C34 C31 179.80(15) . . . . ?
N3 C31 C34 C33 -1.3(3) . . . . ?
O4 C31 C34 C33 -179.96(17) . . . . ?
O1 C18 N1 C19 -179.68(15) . . . . ?
C21 C18 N1 C19 1.8(3) . . . . ?
N2 C19 N1 C18 -0.4(3) . . . . ?
N1 C19 N2 C20 -0.9(3) . . . . ?
C21 C20 N2 C19 1.1(3) . . . . ?
Cl1 C20 N2 C19 -177.89(13) . . . . ?
O4 C31 N3 C32 179.27(19) . . . . ?
C34 C31 N3 C32 0.6(3) . . . . ?
N4 C32 N3 C31 0.4(4) . . . . ?
N3 C32 N4 C33 -0.5(4) . . . . ?
C34 C33 N4 C32 -0.3(3) . . . . ?
Cl2 C33 N4 C32 -179.06(18) . . . . ?
N1 C18 O1 C14 8.6(2) . . . . ?
C21 C18 O1 C14 -172.76(15) . . . . ?
C13 C14 O1 C18 79.6(2) . . . . ?
C15 C14 O1 C18 -103.31(19) . . . . ?
C16 C15 O2 C22 6.0(2) . . . . ?
C14 C15 O2 C22 -173.95(15) . . . . ?
C14 C13 O3 C17 -178.15(16) . . . . ?
C12 C13 O3 C17 1.8(3) . . . . ?
N3 C31 O4 C26 11.9(2) . . . . ?
C34 C31 O4 C26 -169.34(16) . . . . ?
C25 C26 O4 C31 73.6(2) . . . . ?
C27 C26 O4 C31 -108.95(19) . . . . ?
C26 C25 O5 C29 -178.92(18) . . . . ?
C24 C25 O5 C29 0.8(3) . . . . ?
C28 C27 O6 C30 3.4(3) . . . . ?
C26 C27 O6 C30 -177.42(16) . . . . ?
C42 C35 C36 C37 -12(3) . . . . ?
C35 C36 C37 C38 -80(3) . . . . ?
C36 C37 C38 C39 43.6(18) . . . . ?
C37 C38 C39 C40 55.5(15) . . . . ?
C38 C39 C40 C41 -99.7(17) . . . . ?
C39 C40 C41 C42 72(2) . . . . ?
C40 C41 C42 C35 -70.4(17) . . . . ?
C36 C35 C42 C41 83.9(19) . . . . ?

_refine_diff_density_max         0.789
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1880545'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H42 Cl2 N4 O6'
_chemical_formula_weight         721.65

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

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

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

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

_cell_length_a                   9.9163(5)
_cell_length_b                   13.1401(7)
_cell_length_c                   14.9925(8)
_cell_angle_alpha                78.987(2)
_cell_angle_beta                 71.536(2)
_cell_angle_gamma                71.106(2)
_cell_volume                     1744.60(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.114
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            23873
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.573
_diffrn_reflns_theta_max         79.254
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7105
_reflns_number_gt                5520
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0629P)²+0.7444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7105
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4028(2) 0.15598(15) 0.24983(13) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.3725(2) 0.26610(15) 0.19026(13) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.466223 0.273295 0.143789 0.024 Uiso 1 1 calc R U . . .
H2B H 0.336840 0.324670 0.232177 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2561(2) 0.27930(15) 0.13722(13) 0.0199(4) Uani 1 1 d . . . . .
C4 C 0.1121(2) 0.26782(16) 0.21142(14) 0.0242(4) Uani 1 1 d . . . . .
H4A H 0.075053 0.325993 0.253871 0.029 Uiso 1 1 calc R U . . .
H4B H 0.035568 0.275526 0.179373 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1393(2) 0.15718(17) 0.26992(15) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.044430 0.151277 0.317373 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2550(2) 0.14674(17) 0.32168(14) 0.0245(4) Uani 1 1 d . . . . .
H6A H 0.271556 0.076076 0.360277 0.029 Uiso 1 1 calc R U . . .
H6B H 0.217874 0.204410 0.364637 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3110(2) 0.18674(15) 0.07305(14) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.235612 0.193170 0.040395 0.026 Uiso 1 1 calc R U . . .
H7B H 0.403573 0.192435 0.024422 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1951(2) 0.06678(17) 0.20485(16) 0.0271(4) Uani 1 1 d . . . . .
H8A H 0.212403 -0.004458 0.242522 0.032 Uiso 1 1 calc R U . . .
H8B H 0.119651 0.072492 0.172487 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4552(2) 0.06663(15) 0.18285(14) 0.0221(4) Uani 1 1 d . . . . .
H9A H 0.549266 0.071745 0.135644 0.027 Uiso 1 1 calc R U . . .
H9B H 0.474322 -0.005029 0.219713 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3395(2) 0.07654(16) 0.13172(14) 0.0232(4) Uani 1 1 d . . . . .
H10 H 0.376497 0.017533 0.089134 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5180(2) 0.14330(16) 0.30212(13) 0.0218(4) Uani 1 1 d . . . . .
C12 C 0.5710(2) 0.04277(17) 0.35027(14) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.535901 -0.016090 0.349181 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6744(2) 0.02838(17) 0.39957(14) 0.0249(4) Uani 1 1 d . . . . .
C14 C 0.7237(2) 0.11490(18) 0.40220(14) 0.0261(4) Uani 1 1 d . . . . .
C15 C 0.6735(2) 0.21488(18) 0.35465(14) 0.0263(4) Uani 1 1 d . . . . .
C16 C 0.5715(2) 0.22902(17) 0.30388(14) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.538255 0.297073 0.270404 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6893(3) -0.15822(19) 0.44400(17) 0.0342(5) Uani 1 1 d . . . . .
H17A H 0.716013 -0.173057 0.378035 0.051 Uiso 1 1 calc R U . . .
H17B H 0.581798 -0.143582 0.470990 0.051 Uiso 1 1 calc R U . . .
H17C H 0.739828 -0.221093 0.480145 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7810(2) 0.14481(17) 0.53399(14) 0.0255(4) Uani 1 1 d . . . . .
C19 C 0.5981(3) 0.2195(2) 0.65721(18) 0.0422(6) Uani 1 1 d . . . . .
H19 H 0.494938 0.241588 0.687870 0.051 Uiso 1 1 calc R U . . .
C20 C 0.8293(3) 0.2006(2) 0.65618(17) 0.0355(5) Uani 1 1 d . . . . .
C21 C 0.8867(3) 0.15232(18) 0.57277(15) 0.0299(5) Uani 1 1 d . . . . .
H21 H 0.990171 0.126419 0.544310 0.036 Uiso 1 1 calc R U . . .
C22 C 0.6965(3) 0.3938(2) 0.30734(17) 0.0373(5) Uani 1 1 d . . . . .
H22A H 0.725822 0.381244 0.240596 0.056 Uiso 1 1 calc R U . . .
H22B H 0.750310 0.440454 0.315666 0.056 Uiso 1 1 calc R U . . .
H22C H 0.589661 0.428831 0.327474 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2359(2) 0.38969(15) 0.07884(13) 0.0206(4) Uani 1 1 d . . . . .
C24 C 0.1033(2) 0.47193(16) 0.10095(14) 0.0240(4) Uani 1 1 d . . . . .
H24 H 0.022931 0.459204 0.152184 0.029 Uiso 1 1 calc R U . . .
C25 C 0.0879(2) 0.57278(16) 0.04828(15) 0.0238(4) Uani 1 1 d . . . . .
C26 C 0.2043(2) 0.59061(15) -0.02715(14) 0.0228(4) Uani 1 1 d . . . . .
C27 C 0.3373(2) 0.50971(16) -0.05028(14) 0.0217(4) Uani 1 1 d . . . . .
C28 C 0.3530(2) 0.40942(15) 0.00302(13) 0.0213(4) Uani 1 1 d . . . . .
H28 H 0.443906 0.354077 -0.012297 0.026 Uiso 1 1 calc R U . . .
C29 C -0.1570(2) 0.64524(18) 0.14269(17) 0.0333(5) Uani 1 1 d . . . . .
H29A H -0.240719 0.710632 0.144573 0.050 Uiso 1 1 calc R U . . .
H29B H -0.128006 0.632235 0.201486 0.050 Uiso 1 1 calc R U . . .
H29C H -0.186245 0.583345 0.135728 0.050 Uiso 1 1 calc R U . . .
C30 C 0.1958(2) 0.77520(15) -0.05198(14) 0.0209(4) Uani 1 1 d . . . . .
C31 C 0.2453(2) 0.85008(17) 0.05252(15) 0.0279(4) Uani 1 1 d . . . . .
H31 H 0.275884 0.841099 0.108201 0.034 Uiso 1 1 calc R U . . .
C32 C 0.1726(2) 0.95878(16) -0.06777(16) 0.0261(4) Uani 1 1 d . . . . .
C33 C 0.1611(2) 0.87486(16) -0.10443(15) 0.0238(4) Uani 1 1 d . . . . .
H33 H 0.131980 0.883991 -0.160706 0.029 Uiso 1 1 calc R U . . .
C34 C 0.5760(2) 0.45269(17) -0.15873(15) 0.0278(4) Uani 1 1 d . . . . .
H34A H 0.549918 0.393106 -0.173334 0.042 Uiso 1 1 calc R U . . .
H34B H 0.628475 0.426408 -0.109659 0.042 Uiso 1 1 calc R U . . .
H34C H 0.640109 0.480841 -0.215837 0.042 Uiso 1 1 calc R U . . .
N1 N 0.6365(2) 0.17761(17) 0.57499(14) 0.0349(4) Uani 1 1 d . . . . .
N2 N 0.6869(2) 0.23374(18) 0.70098(15) 0.0423(5) Uani 1 1 d . . . . .
N3 N 0.23984(19) 0.76055(13) 0.02552(12) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.2129(2) 0.95026(15) 0.01053(14) 0.0305(4) Uani 1 1 d . . . . .
O1 O 0.73332(16) -0.06617(12) 0.44811(11) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.82920(16) 0.10046(13) 0.45119(10) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.73086(19) 0.29342(13) 0.36277(11) 0.0346(4) Uani 1 1 d . . . . .
O4 O -0.03564(16) 0.65900(11) 0.06494(11) 0.0302(3) Uani 1 1 d . . . . .
O5 O 0.18522(16) 0.68949(11) -0.08433(10) 0.0250(3) Uani 1 1 d . . . . .
O6 O 0.44382(16) 0.53701(11) -0.12568(10) 0.0252(3) Uani 1 1 d . . . . .
Cl1 Cl 0.94519(9) 0.22140(7) 0.71080(5) 0.0572(2) Uani 1 1 d . . . . .
Cl2 Cl 0.13563(6) 1.08773(4) -0.12576(5) 0.03806(16) Uani 1 1 d . . . . .
C35 C 0.1390(7) 0.5268(7) 0.4813(5) 0.081(2) Uani 0.671(6) 1 d . . P A 1
H35 H 0.093731 0.605552 0.465665 0.098 Uiso 0.671(6) 1 calc R U P A 1
C36 C 0.0483(6) 0.5099(5) 0.5792(3) 0.0599(15) Uani 0.671(6) 1 d . . P A 1
H36A H 0.053207 0.562159 0.616814 0.072 Uiso 0.671(6) 1 calc R U P A 1
H36B H 0.093609 0.436480 0.606093 0.072 Uiso 0.671(6) 1 calc R U P A 1
C37 C 0.1109(11) 0.4789(6) 0.4089(6) 0.061(2) Uani 0.671(6) 1 d . . P A 1
H37A H 0.165619 0.401056 0.410468 0.073 Uiso 0.671(6) 1 calc R U P A 1
H37B H 0.151775 0.513525 0.345688 0.073 Uiso 0.671(6) 1 calc R U P A 1
C38 C 0.2980(5) 0.5226(4) 0.4589(3) 0.0536(13) Uani 0.671(6) 1 d . . P A 1
H38A H 0.357108 0.447419 0.467739 0.080 Uiso 0.671(6) 1 calc R U P A 1
H38B H 0.309731 0.565747 0.500969 0.080 Uiso 0.671(6) 1 calc R U P A 1
H38C H 0.331800 0.551670 0.393107 0.080 Uiso 0.671(6) 1 calc R U P A 1
C39 C 0.1436(10) 0.4448(9) 0.5228(7) 0.049(3) Uani 0.329(6) 1 d . . P A 2
H39 H 0.094357 0.394205 0.570523 0.059 Uiso 0.329(6) 1 calc R U P A 2
C40 C 0.0267(11) 0.5871(9) 0.5382(7) 0.058(3) Uani 0.329(6) 1 d . . P A 2
H40A H 0.043252 0.618349 0.587506 0.069 Uiso 0.329(6) 1 calc R U P A 2
H40B H 0.038093 0.634993 0.478329 0.069 Uiso 0.329(6) 1 calc R U P A 2
C41 C 0.1251(17) 0.4423(8) 0.4290(9) 0.034(2) Uani 0.329(6) 1 d . . P A 2
H41A H 0.206510 0.386080 0.392851 0.040 Uiso 0.329(6) 1 calc R U P A 2
H41B H 0.117507 0.513342 0.391045 0.040 Uiso 0.329(6) 1 calc R U P A 2
C42 C 0.2977(12) 0.4271(8) 0.5317(8) 0.065(3) Uani 0.329(6) 1 d . . P A 2
H42A H 0.369986 0.376942 0.486755 0.097 Uiso 0.329(6) 1 calc R U P A 2
H42B H 0.301515 0.396632 0.596154 0.097 Uiso 0.329(6) 1 calc R U P A 2
H42C H 0.321380 0.496317 0.518038 0.097 Uiso 0.329(6) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.530(3) . ?
C1 C2 1.541(2) . ?
C1 C9 1.543(3) . ?
C1 C6 1.545(3) . ?
C2 C3 1.547(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C23 1.532(3) . ?
C3 C4 1.538(3) . ?
C3 C7 1.545(3) . ?
C4 C5 1.538(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C8 1.531(3) . ?
C5 C6 1.536(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.535(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.530(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C11 C16 1.399(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.367(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.387(3) . ?
C14 O2 1.406(2) . ?
C15 O3 1.369(3) . ?
C15 C16 1.396(3) . ?
C16 H16 0.9500 . ?
C17 O1 1.430(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.327(3) . ?
C18 O2 1.352(3) . ?
C18 C21 1.386(3) . ?
C19 N2 1.328(3) . ?
C19 N1 1.339(3) . ?
C19 H19 0.9500 . ?
C20 N2 1.322(3) . ?
C20 C21 1.381(3) . ?
C20 Cl1 1.718(2) . ?
C21 H21 0.9500 . ?
C22 O3 1.419(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.395(3) . ?
C23 C28 1.398(3) . ?
C24 C25 1.396(3) . ?
C24 H24 0.9500 . ?
C25 O4 1.365(2) . ?
C25 C26 1.383(3) . ?
C26 C27 1.391(3) . ?
C26 O5 1.406(2) . ?
C27 O6 1.363(2) . ?
C27 C28 1.394(3) . ?
C28 H28 0.9500 . ?
C29 O4 1.419(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.327(3) . ?
C30 O5 1.353(2) . ?
C30 C33 1.392(3) . ?
C31 N4 1.330(3) . ?
C31 N3 1.337(3) . ?
C31 H31 0.9500 . ?
C32 N4 1.330(3) . ?
C32 C33 1.373(3) . ?
C32 Cl2 1.732(2) . ?
C33 H33 0.9500 . ?
C34 O6 1.431(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.476(8) . ?
C35 C38 1.488(7) . ?
C35 C37 1.490(11) . ?
C35 H35 1.0000 . ?
C36 C37 1.492(11) 2_566 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C41 1.482(17) . ?
C39 C42 1.515(14) . ?
C39 C40 1.867(14) . ?
C39 H39 1.0000 . ?
C40 C41 1.578(19) 2_566 ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 112.06(16) . . ?
C11 C1 C9 110.81(16) . . ?
C2 C1 C9 107.84(15) . . ?
C11 C1 C6 109.82(15) . . ?
C2 C1 C6 108.14(15) . . ?
C9 C1 C6 108.05(16) . . ?
C1 C2 C3 112.25(15) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C23 C3 C4 112.68(16) . . ?
C23 C3 C7 111.03(16) . . ?
C4 C3 C7 107.95(16) . . ?
C23 C3 C2 108.34(15) . . ?
C4 C3 C2 107.74(15) . . ?
C7 C3 C2 109.00(16) . . ?
C5 C4 C3 110.61(16) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C8 C5 C6 109.76(17) . . ?
C8 C5 C4 109.82(17) . . ?
C6 C5 C4 109.39(17) . . ?
C8 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 C1 110.30(16) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C10 C7 C3 110.47(16) . . ?
C10 C7 H7A 109.6 . . ?
C3 C7 H7A 109.6 . . ?
C10 C7 H7B 109.6 . . ?
C3 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 C8 C5 109.23(16) . . ?
C10 C8 H8A 109.8 . . ?
C5 C8 H8A 109.8 . . ?
C10 C8 H8B 109.8 . . ?
C5 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C1 111.48(16) . . ?
C10 C9 H9A 109.3 . . ?
C1 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C8 C10 C9 109.16(16) . . ?
C8 C10 C7 109.38(16) . . ?
C9 C10 C7 109.70(16) . . ?
C8 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
C7 C10 H10 109.5 . . ?
C16 C11 C12 118.97(19) . . ?
C16 C11 C1 122.04(17) . . ?
C12 C11 C1 118.99(18) . . ?
C13 C12 C11 120.71(19) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O1 C13 C14 115.33(18) . . ?
O1 C13 C12 125.18(19) . . ?
C14 C13 C12 119.48(19) . . ?
C13 C14 C15 120.83(19) . . ?
C13 C14 O2 119.68(19) . . ?
C15 C14 O2 119.47(19) . . ?
O3 C15 C14 115.04(18) . . ?
O3 C15 C16 125.2(2) . . ?
C14 C15 C16 119.8(2) . . ?
C15 C16 C11 120.23(19) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O2 119.24(19) . . ?
N1 C18 C21 123.0(2) . . ?
O2 C18 C21 117.74(19) . . ?
N2 C19 N1 127.7(2) . . ?
N2 C19 H19 116.1 . . ?
N1 C19 H19 116.1 . . ?
N2 C20 C21 125.3(2) . . ?
N2 C20 Cl1 114.30(19) . . ?
C21 C20 Cl1 120.4(2) . . ?
C20 C21 C18 114.5(2) . . ?
C20 C21 H21 122.8 . . ?
C18 C21 H21 122.8 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 119.16(17) . . ?
C24 C23 C3 121.19(17) . . ?
C28 C23 C3 119.64(17) . . ?
C23 C24 C25 120.44(19) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
O4 C25 C26 115.20(17) . . ?
O4 C25 C24 125.11(19) . . ?
C26 C25 C24 119.68(18) . . ?
C25 C26 C27 120.74(17) . . ?
C25 C26 O5 119.68(17) . . ?
C27 C26 O5 119.49(18) . . ?
O6 C27 C26 115.35(17) . . ?
O6 C27 C28 125.15(18) . . ?
C26 C27 C28 119.49(18) . . ?
C27 C28 C23 120.48(18) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 O5 119.46(17) . . ?
N3 C30 C33 123.72(19) . . ?
O5 C30 C33 116.81(18) . . ?
N4 C31 N3 127.6(2) . . ?
N4 C31 H31 116.2 . . ?
N3 C31 H31 116.2 . . ?
N4 C32 C33 125.25(19) . . ?
N4 C32 Cl2 114.97(16) . . ?
C33 C32 Cl2 119.78(17) . . ?
C32 C33 C30 114.15(19) . . ?
C32 C33 H33 122.9 . . ?
C30 C33 H33 122.9 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 N1 C19 115.5(2) . . ?
C20 N2 C19 113.9(2) . . ?
C30 N3 C31 115.11(18) . . ?
C32 N4 C31 114.13(19) . . ?
C13 O1 C17 116.88(17) . . ?
C18 O2 C14 117.06(16) . . ?
C15 O3 C22 117.53(17) . . ?
C25 O4 C29 117.29(16) . . ?
C30 O5 C26 117.60(15) . . ?
C27 O6 C34 117.17(15) . . ?
C36 C35 C38 122.2(6) . . ?
C36 C35 C37 115.6(6) . . ?
C38 C35 C37 111.6(5) . . ?
C36 C35 H35 101.0 . . ?
C38 C35 H35 101.0 . . ?
C37 C35 H35 101.0 . . ?
C35 C36 C37 116.1(5) . 2_566 ?
C35 C36 H36A 108.3 . . ?
C37 C36 H36A 108.3 2_566 . ?
C35 C36 H36B 108.3 . . ?
C37 C36 H36B 108.3 2_566 . ?
H36A C36 H36B 107.4 . . ?
C35 C37 C36 114.9(6) . 2_566 ?
C35 C37 H37A 108.5 . . ?
C36 C37 H37A 108.5 2_566 . ?
C35 C37 H37B 108.5 . . ?
C36 C37 H37B 108.5 2_566 . ?
H37A C37 H37B 107.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C41 C39 C42 119.0(10) . . ?
C41 C39 C40 95.7(8) . . ?
C42 C39 C40 112.1(8) . . ?
C41 C39 H39 109.7 . . ?
C42 C39 H39 109.7 . . ?
C40 C39 H39 109.7 . . ?
C41 C40 C39 94.7(7) 2_566 . ?
C41 C40 H40A 112.8 2_566 . ?
C39 C40 H40A 112.8 . . ?
C41 C40 H40B 112.8 2_566 . ?
C39 C40 H40B 112.8 . . ?
H40A C40 H40B 110.3 . . ?
C39 C41 H41A 111.9 . . ?
C40 C41 H41A 111.9 2_566 . ?
C39 C41 H41B 111.9 . . ?
C40 C41 H41B 111.9 2_566 . ?
H41A C41 H41B 109.6 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 179.99(15) . . . . ?
C9 C1 C2 C3 57.8(2) . . . . ?
C6 C1 C2 C3 -58.8(2) . . . . ?
C1 C2 C3 C23 -178.91(15) . . . . ?
C1 C2 C3 C4 58.9(2) . . . . ?
C1 C2 C3 C7 -58.0(2) . . . . ?
C23 C3 C4 C5 -178.32(17) . . . . ?
C7 C3 C4 C5 58.7(2) . . . . ?
C2 C3 C4 C5 -58.9(2) . . . . ?
C3 C4 C5 C8 -59.8(2) . . . . ?
C3 C4 C5 C6 60.7(2) . . . . ?
C8 C5 C6 C1 60.4(2) . . . . ?
C4 C5 C6 C1 -60.2(2) . . . . ?
C11 C1 C6 C5 -178.92(16) . . . . ?
C2 C1 C6 C5 58.5(2) . . . . ?
C9 C1 C6 C5 -58.0(2) . . . . ?
C23 C3 C7 C10 176.64(16) . . . . ?
C4 C3 C7 C10 -59.4(2) . . . . ?
C2 C3 C7 C10 57.4(2) . . . . ?
C6 C5 C8 C10 -60.7(2) . . . . ?
C4 C5 C8 C10 59.6(2) . . . . ?
C11 C1 C9 C10 178.64(15) . . . . ?
C2 C1 C9 C10 -58.4(2) . . . . ?
C6 C1 C9 C10 58.3(2) . . . . ?
C5 C8 C10 C9 59.9(2) . . . . ?
C5 C8 C10 C7 -60.1(2) . . . . ?
C1 C9 C10 C8 -59.9(2) . . . . ?
C1 C9 C10 C7 59.9(2) . . . . ?
C3 C7 C10 C8 60.9(2) . . . . ?
C3 C7 C10 C9 -58.8(2) . . . . ?
C2 C1 C11 C16 8.0(3) . . . . ?
C9 C1 C11 C16 128.49(19) . . . . ?
C6 C1 C11 C16 -112.2(2) . . . . ?
C2 C1 C11 C12 -172.40(17) . . . . ?
C9 C1 C11 C12 -51.9(2) . . . . ?
C6 C1 C11 C12 67.4(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C1 C11 C12 C13 -179.22(18) . . . . ?
C11 C12 C13 O1 -179.61(18) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
O1 C13 C14 C15 179.16(18) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
O1 C13 C14 O2 1.1(3) . . . . ?
C12 C13 C14 O2 -179.40(17) . . . . ?
C13 C14 C15 O3 -179.90(19) . . . . ?
O2 C14 C15 O3 -1.9(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
O2 C14 C15 C16 178.39(18) . . . . ?
O3 C15 C16 C11 -178.66(19) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C1 C11 C16 C15 178.19(18) . . . . ?
N2 C20 C21 C18 3.1(3) . . . . ?
Cl1 C20 C21 C18 -177.20(16) . . . . ?
N1 C18 C21 C20 -2.3(3) . . . . ?
O2 C18 C21 C20 178.65(19) . . . . ?
C4 C3 C23 C24 6.7(3) . . . . ?
C7 C3 C23 C24 127.91(19) . . . . ?
C2 C3 C23 C24 -112.4(2) . . . . ?
C4 C3 C23 C28 -174.46(18) . . . . ?
C7 C3 C23 C28 -53.2(2) . . . . ?
C2 C3 C23 C28 66.4(2) . . . . ?
C28 C23 C24 C25 -0.3(3) . . . . ?
C3 C23 C24 C25 178.60(18) . . . . ?
C23 C24 C25 O4 -178.80(19) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
O4 C25 C26 C27 178.79(18) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
O4 C25 C26 O5 -4.7(3) . . . . ?
C24 C25 C26 O5 175.46(18) . . . . ?
C25 C26 C27 O6 -179.71(18) . . . . ?
O5 C26 C27 O6 3.8(3) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
O5 C26 C27 C28 -176.14(17) . . . . ?
O6 C27 C28 C23 -179.57(18) . . . . ?
C26 C27 C28 C23 0.4(3) . . . . ?
C24 C23 C28 C27 -0.4(3) . . . . ?
C3 C23 C28 C27 -179.30(18) . . . . ?
N4 C32 C33 C30 0.1(3) . . . . ?
Cl2 C32 C33 C30 179.08(14) . . . . ?
N3 C30 C33 C32 -1.6(3) . . . . ?
O5 C30 C33 C32 179.48(17) . . . . ?
O2 C18 N1 C19 179.3(2) . . . . ?
C21 C18 N1 C19 0.2(3) . . . . ?
N2 C19 N1 C18 1.5(4) . . . . ?
C21 C20 N2 C19 -1.7(4) . . . . ?
Cl1 C20 N2 C19 178.60(19) . . . . ?
N1 C19 N2 C20 -0.8(4) . . . . ?
O5 C30 N3 C31 -179.33(17) . . . . ?
C33 C30 N3 C31 1.8(3) . . . . ?
N4 C31 N3 C30 -0.5(3) . . . . ?
C33 C32 N4 C31 1.0(3) . . . . ?
Cl2 C32 N4 C31 -178.00(15) . . . . ?
N3 C31 N4 C32 -0.9(3) . . . . ?
C14 C13 O1 C17 -177.70(18) . . . . ?
C12 C13 O1 C17 2.9(3) . . . . ?
N1 C18 O2 C14 14.7(3) . . . . ?
C21 C18 O2 C14 -166.15(18) . . . . ?
C13 C14 O2 C18 -107.3(2) . . . . ?
C15 C14 O2 C18 74.6(2) . . . . ?
C14 C15 O3 C22 173.2(2) . . . . ?
C16 C15 O3 C22 -7.1(3) . . . . ?
C26 C25 O4 C29 -178.88(19) . . . . ?
C24 C25 O4 C29 0.9(3) . . . . ?
N3 C30 O5 C26 7.7(3) . . . . ?
C33 C30 O5 C26 -173.33(17) . . . . ?
C25 C26 O5 C30 80.1(2) . . . . ?
C27 C26 O5 C30 -103.3(2) . . . . ?
C26 C27 O6 C34 -172.95(17) . . . . ?
C28 C27 O6 C34 7.0(3) . . . . ?
C38 C35 C36 C37 177.5(6) . . . 2_566 ?
C37 C35 C36 C37 -41.1(11) . . . 2_566 ?
C36 C35 C37 C36 40.5(10) . . . 2_566 ?
C38 C35 C37 C36 -174.0(6) . . . 2_566 ?
C41 C39 C40 C41 80.2(9) . . . 2_566 ?
C42 C39 C40 C41 -155.3(9) . . . 2_566 ?
C42 C39 C41 C40 156.5(9) . . . 2_566 ?
C40 C39 C41 C40 -84.3(8) . . . 2_566 ?

_refine_diff_density_max         0.826
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1880546'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37.50 H41 Cl2 N4 O6'
_chemical_formula_weight         714.64

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

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

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

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

_cell_length_a                   9.9369(5)
_cell_length_b                   13.0256(7)
_cell_length_c                   14.9773(8)
_cell_angle_alpha                78.670(3)
_cell_angle_beta                 71.719(3)
_cell_angle_gamma                71.595(3)
_cell_volume                     1736.34(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.119
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            21375
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.126
_diffrn_reflns_theta_max         79.363
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7109
_reflns_number_gt                3731
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.1265P)²+0.7637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7109
_refine_ls_number_parameters     482
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2603
_refine_ls_wR_factor_gt          0.2211
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.044
_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 0.4025(5) 0.1533(4) 0.2492(3) 0.0282(10) Uani 1 1 d . . . . .
C2 C 0.2561(5) 0.1416(4) 0.3200(3) 0.0346(11) Uani 1 1 d . . . . .
H2A H 0.217721 0.199325 0.363047 0.042 Uiso 1 1 calc R U . . .
H2AB H 0.272801 0.070196 0.358708 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1424(5) 0.1510(4) 0.2660(3) 0.0350(11) Uani 1 1 d . . . . .
H3 H 0.047557 0.144214 0.312678 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1161(5) 0.2613(4) 0.2075(3) 0.0322(10) Uani 1 1 d . . . . .
H4A H 0.078023 0.319723 0.249806 0.039 Uiso 1 1 calc R U . . .
H4AB H 0.041058 0.268237 0.174522 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2595(5) 0.2745(4) 0.1345(3) 0.0278(10) Uani 1 1 d . . . . .
C6 C 0.3731(5) 0.2625(3) 0.1895(3) 0.0285(10) Uani 1 1 d . . . . .
H6A H 0.466790 0.270832 0.143910 0.034 Uiso 1 1 calc R U . . .
H6AB H 0.336156 0.321534 0.231108 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3144(5) 0.1829(3) 0.0709(3) 0.0292(10) Uani 1 1 d . . . . .
H7A H 0.240168 0.189180 0.037454 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.406847 0.189581 0.022875 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3420(5) 0.0723(4) 0.1292(3) 0.0327(11) Uani 1 1 d . . . . .
H8 H 0.379208 0.013279 0.086680 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4568(5) 0.0626(4) 0.1825(3) 0.0321(10) Uani 1 1 d . . . . .
H9A H 0.551084 0.068217 0.136215 0.039 Uiso 1 1 calc R U . . .
H9AB H 0.474676 -0.009509 0.220097 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1987(5) 0.0609(4) 0.2021(4) 0.0394(12) Uani 1 1 d . . . . .
H10A H 0.124134 0.065402 0.169469 0.047 Uiso 1 1 calc R U . . .
H10B H 0.216423 -0.010823 0.240305 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5167(5) 0.1408(4) 0.3026(3) 0.0292(10) Uani 1 1 d . . . . .
C12 C 0.5695(5) 0.0400(4) 0.3508(3) 0.0331(11) Uani 1 1 d . . . . .
H12 H 0.534259 -0.019610 0.350062 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6727(5) 0.0260(4) 0.3997(3) 0.0342(11) Uani 1 1 d . . . . .
C14 C 0.7210(5) 0.1145(4) 0.4016(3) 0.0349(11) Uani 1 1 d . . . . .
C15 C 0.6694(5) 0.2145(4) 0.3558(3) 0.0366(11) Uani 1 1 d . . . . .
C16 C 0.5681(5) 0.2278(4) 0.3056(3) 0.0348(11) Uani 1 1 d . . . . .
H16 H 0.533324 0.296794 0.272966 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6877(6) -0.1635(4) 0.4451(4) 0.0466(13) Uani 1 1 d . . . . .
H17A H 0.580814 -0.148972 0.471685 0.070 Uiso 1 1 calc R U . . .
H17B H 0.737390 -0.225775 0.482624 0.070 Uiso 1 1 calc R U . . .
H17C H 0.714596 -0.179833 0.379603 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7842(6) 0.1460(4) 0.5327(3) 0.0379(11) Uani 1 1 d . . . . .
C19 C 0.6048(8) 0.2296(5) 0.6536(4) 0.0663(18) Uani 1 1 d . . . . .
H19 H 0.502655 0.257119 0.682555 0.080 Uiso 1 1 calc R U . . .
C20 C 0.8383(8) 0.2003(5) 0.6519(4) 0.0581(16) Uani 1 1 d . . . . .
C21 C 0.8923(6) 0.1498(4) 0.5705(4) 0.0471(13) Uani 1 1 d . . . . .
H21 H 0.994509 0.120245 0.542884 0.057 Uiso 1 1 calc R U . . .
C22 C 0.6753(8) 0.3996(5) 0.3201(5) 0.0656(18) Uani 1 1 d . . . . .
H22A H 0.720326 0.449476 0.333979 0.098 Uiso 1 1 calc R U . . .
H22B H 0.567939 0.424835 0.344247 0.098 Uiso 1 1 calc R U . . .
H22C H 0.701879 0.397680 0.251531 0.098 Uiso 1 1 calc R U . . .
C23 C 0.2400(5) 0.3859(3) 0.0761(3) 0.0275(10) Uani 1 1 d . . . . .
C24 C 0.1086(5) 0.4685(4) 0.0969(3) 0.0317(10) Uani 1 1 d . . . . .
H24 H 0.027713 0.455506 0.147569 0.038 Uiso 1 1 calc R U . . .
C25 C 0.0957(5) 0.5701(4) 0.0434(4) 0.0331(11) Uani 1 1 d . . . . .
C26 C 0.2101(5) 0.5882(3) -0.0317(3) 0.0308(10) Uani 1 1 d . . . . .
C27 C 0.3423(5) 0.5065(3) -0.0534(3) 0.0289(10) Uani 1 1 d . . . . .
C28 C 0.3574(5) 0.4063(3) 0.0003(3) 0.0280(10) Uani 1 1 d . . . . .
H28 H 0.447788 0.351027 -0.014288 0.034 Uiso 1 1 calc R U . . .
C29 C -0.1484(5) 0.6431(4) 0.1381(4) 0.0454(13) Uani 1 1 d . . . . .
H29A H -0.118648 0.630844 0.196666 0.068 Uiso 1 1 calc R U . . .
H29B H -0.179128 0.580663 0.132713 0.068 Uiso 1 1 calc R U . . .
H29C H -0.230615 0.709094 0.139083 0.068 Uiso 1 1 calc R U . . .
C30 C 0.1979(5) 0.7745(3) -0.0573(3) 0.0280(10) Uani 1 1 d . . . . .
C31 C 0.2399(5) 0.8531(4) 0.0483(4) 0.0418(12) Uani 1 1 d . . . . .
H31 H 0.268326 0.845268 0.104718 0.050 Uiso 1 1 calc R U . . .
C32 C 0.1704(5) 0.9601(4) -0.0738(4) 0.0422(13) Uani 1 1 d . . . . .
C33 C 0.1619(5) 0.8734(3) -0.1099(4) 0.0367(11) Uani 1 1 d . . . . .
H33 H 0.133617 0.881318 -0.166370 0.044 Uiso 1 1 calc R U . . .
C34 C 0.5820(5) 0.4518(4) -0.1595(3) 0.0391(12) Uani 1 1 d . . . . .
H34A H 0.558017 0.389563 -0.172189 0.059 Uiso 1 1 calc R U . . .
H34B H 0.633773 0.428499 -0.109919 0.059 Uiso 1 1 calc R U . . .
H34C H 0.645197 0.480052 -0.217334 0.059 Uiso 1 1 calc R U . . .
N1 N 0.6413(5) 0.1839(4) 0.5731(3) 0.0502(12) Uani 1 1 d . . . . .
N2 N 0.6972(7) 0.2400(4) 0.6966(4) 0.0703(15) Uani 1 1 d . . . . .
N3 N 0.2388(4) 0.7610(3) 0.0213(3) 0.0333(9) Uani 1 1 d . . . . .
N4 N 0.2065(5) 0.9527(3) 0.0064(3) 0.0459(11) Uani 1 1 d . . . . .
O1 O 0.7326(3) -0.0687(3) 0.4470(2) 0.0388(8) Uani 1 1 d . . . . .
O2 O 0.8276(3) 0.0991(3) 0.4514(2) 0.0388(8) Uani 1 1 d . . . . .
O3 O 0.7268(4) 0.2943(3) 0.3640(2) 0.0492(10) Uani 1 1 d . . . . .
O4 O -0.0275(3) 0.6559(3) 0.0594(2) 0.0401(8) Uani 1 1 d . . . . .
O5 O 0.1927(3) 0.6869(2) -0.0901(2) 0.0339(8) Uani 1 1 d . . . . .
O6 O 0.4496(3) 0.5349(2) -0.1289(2) 0.0349(8) Uani 1 1 d . . . . .
Cl1 Cl 0.9492(2) 0.2213(2) 0.70882(14) 0.1009(8) Uani 1 1 d . . . . .
Cl2 Cl 0.13303(15) 1.08898(10) -0.13114(12) 0.0644(5) Uani 1 1 d . . . . .
C35 C -0.173(4) 0.495(3) 0.533(3) 0.130(14) Uani 0.5 1 d . U P A -1
H35A H -0.242405 0.556153 0.505634 0.156 Uiso 0.5 1 calc R U P A -1
H35B H -0.227901 0.443480 0.572533 0.156 Uiso 0.5 1 calc R U P A -1
C36 C -0.113(3) 0.538(3) 0.5938(17) 0.100(9) Uani 0.5 1 d . U P A -1
H36A H -0.081294 0.478394 0.641297 0.120 Uiso 0.5 1 calc R U P A -1
H36B H -0.193923 0.595036 0.628660 0.120 Uiso 0.5 1 calc R U P A -1
C37 C 0.027(4) 0.5911(19) 0.539(2) 0.063(6) Uani 0.5 1 d . U P A -1
H37A H 0.003532 0.642110 0.484505 0.076 Uiso 0.5 1 calc R U P A -1
H37B H 0.038141 0.633942 0.583231 0.076 Uiso 0.5 1 calc R U P A -1
C38 C 0.159(4) 0.517(3) 0.5082(15) 0.082(6) Uani 0.5 1 d . U P A -1
H38A H 0.162884 0.450317 0.552911 0.098 Uiso 0.5 1 calc R U P A -1
H38B H 0.238633 0.547130 0.509115 0.098 Uiso 0.5 1 calc R U P A -1
C39 C 0.187(3) 0.489(2) 0.4152(13) 0.083(6) Uani 0.5 1 d . U P A -1
H39A H 0.260401 0.417601 0.409419 0.099 Uiso 0.5 1 calc R U P A -1
H39B H 0.232319 0.543044 0.369481 0.099 Uiso 0.5 1 calc R U P A -1
C40 C 0.053(3) 0.484(2) 0.3843(18) 0.091(7) Uani 0.5 1 d . U P A -1
H40A H -0.002753 0.559455 0.368567 0.109 Uiso 0.5 1 calc R U P A -1
H40B H 0.093211 0.448341 0.325148 0.109 Uiso 0.5 1 calc R U P A -1
C41 C -0.042(6) 0.432(3) 0.445(3) 0.122(11) Uani 0.5 1 d . U P A -1
H41A H 0.015805 0.364682 0.473728 0.147 Uiso 0.5 1 calc R U P A -1
H41B H -0.092268 0.409848 0.407314 0.147 Uiso 0.5 1 calc R U P A -1


_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 C6 1.520(6) . ?
C1 C11 1.535(6) . ?
C1 C2 1.540(6) . ?
C1 C9 1.551(6) . ?
C2 C3 1.547(6) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C10 1.516(7) . ?
C3 C4 1.521(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.536(6) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C23 1.529(6) . ?
C5 C7 1.530(6) . ?
C5 C6 1.548(5) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.523(6) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.528(6) . ?
C8 C9 1.548(6) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.396(6) . ?
C11 C12 1.396(6) . ?
C12 C13 1.387(6) . ?
C12 H12 0.9500 . ?
C13 O1 1.355(5) . ?
C13 C14 1.389(7) . ?
C14 C15 1.370(6) . ?
C14 O2 1.421(5) . ?
C15 O3 1.375(5) . ?
C15 C16 1.386(6) . ?
C16 H16 0.9500 . ?
C17 O1 1.447(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.327(6) . ?
C18 O2 1.356(5) . ?
C18 C21 1.380(7) . ?
C19 N2 1.326(8) . ?
C19 N1 1.346(7) . ?
C19 H19 0.9500 . ?
C20 N2 1.331(8) . ?
C20 C21 1.374(8) . ?
C20 Cl1 1.700(6) . ?
C21 H21 0.9500 . ?
C22 O3 1.410(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.396(6) . ?
C23 C28 1.403(6) . ?
C24 C25 1.397(6) . ?
C24 H24 0.9500 . ?
C25 O4 1.365(5) . ?
C25 C26 1.369(6) . ?
C26 C27 1.396(6) . ?
C26 O5 1.401(5) . ?
C27 O6 1.372(5) . ?
C27 C28 1.383(6) . ?
C28 H28 0.9500 . ?
C29 O4 1.422(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.325(5) . ?
C30 O5 1.349(5) . ?
C30 C33 1.377(6) . ?
C31 N4 1.314(6) . ?
C31 N3 1.343(6) . ?
C31 H31 0.9500 . ?
C32 N4 1.335(7) . ?
C32 C33 1.379(7) . ?
C32 Cl2 1.713(5) . ?
C33 H33 0.9500 . ?
C34 O6 1.425(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.51(4) . ?
C35 C41 1.66(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.66(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.36(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.43(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.56(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.34(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?

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 C1 C11 112.5(3) . . ?
C6 C1 C2 108.6(4) . . ?
C11 C1 C2 109.9(3) . . ?
C6 C1 C9 107.9(3) . . ?
C11 C1 C9 110.1(4) . . ?
C2 C1 C9 107.8(4) . . ?
C1 C2 C3 109.8(4) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2AB 109.7 . . ?
C3 C2 H2AB 109.7 . . ?
H2A C2 H2AB 108.2 . . ?
C10 C3 C4 110.0(4) . . ?
C10 C3 C2 110.0(4) . . ?
C4 C3 C2 109.5(4) . . ?
C10 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C3 C4 C5 110.7(4) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.1 . . ?
C23 C5 C7 111.0(3) . . ?
C23 C5 C4 112.7(4) . . ?
C7 C5 C4 107.8(4) . . ?
C23 C5 C6 108.2(3) . . ?
C7 C5 C6 109.6(4) . . ?
C4 C5 C6 107.5(3) . . ?
C1 C6 C5 112.5(3) . . ?
C1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C1 C6 H6AB 109.1 . . ?
C5 C6 H6AB 109.1 . . ?
H6A C6 H6AB 107.8 . . ?
C8 C7 C5 110.5(4) . . ?
C8 C7 H7A 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C8 C7 H7AB 109.5 . . ?
C5 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
C7 C8 C10 109.6(4) . . ?
C7 C8 C9 109.7(3) . . ?
C10 C8 C9 108.4(4) . . ?
C7 C8 H8 109.7 . . ?
C10 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
C8 C9 C1 111.0(4) . . ?
C8 C9 H9A 109.4 . . ?
C1 C9 H9A 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
C1 C9 H9AB 109.4 . . ?
H9A C9 H9AB 108.0 . . ?
C3 C10 C8 109.4(4) . . ?
C3 C10 H10A 109.8 . . ?
C8 C10 H10A 109.8 . . ?
C3 C10 H10B 109.8 . . ?
C8 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 118.8(4) . . ?
C16 C11 C1 121.9(4) . . ?
C12 C11 C1 119.3(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C12 125.2(4) . . ?
O1 C13 C14 115.8(4) . . ?
C12 C13 C14 119.0(4) . . ?
C15 C14 C13 121.3(4) . . ?
C15 C14 O2 120.2(4) . . ?
C13 C14 O2 118.5(4) . . ?
C14 C15 O3 114.9(4) . . ?
C14 C15 C16 119.6(4) . . ?
O3 C15 C16 125.5(4) . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 O2 119.1(4) . . ?
N1 C18 C21 123.1(5) . . ?
O2 C18 C21 117.7(5) . . ?
N2 C19 N1 126.5(6) . . ?
N2 C19 H19 116.7 . . ?
N1 C19 H19 116.7 . . ?
N2 C20 C21 126.7(6) . . ?
N2 C20 Cl1 110.6(5) . . ?
C21 C20 Cl1 122.8(5) . . ?
C20 C21 C18 113.7(5) . . ?
C20 C21 H21 123.2 . . ?
C18 C21 H21 123.2 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 119.0(4) . . ?
C24 C23 C5 121.6(4) . . ?
C28 C23 C5 119.4(4) . . ?
C23 C24 C25 120.1(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
O4 C25 C26 115.5(4) . . ?
O4 C25 C24 124.2(4) . . ?
C26 C25 C24 120.2(4) . . ?
C25 C26 C27 120.3(4) . . ?
C25 C26 O5 120.1(4) . . ?
C27 C26 O5 119.5(4) . . ?
O6 C27 C28 125.1(4) . . ?
O6 C27 C26 114.9(4) . . ?
C28 C27 C26 120.0(4) . . ?
C27 C28 C23 120.3(4) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 O5 119.2(4) . . ?
N3 C30 C33 124.0(4) . . ?
O5 C30 C33 116.7(4) . . ?
N4 C31 N3 128.1(5) . . ?
N4 C31 H31 115.9 . . ?
N3 C31 H31 115.9 . . ?
N4 C32 C33 124.6(5) . . ?
N4 C32 Cl2 114.5(4) . . ?
C33 C32 Cl2 120.9(4) . . ?
C30 C33 C32 114.5(5) . . ?
C30 C33 H33 122.8 . . ?
C32 C33 H33 122.8 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 N1 C19 116.5(5) . . ?
C19 N2 C20 113.5(5) . . ?
C30 N3 C31 114.6(4) . . ?
C31 N4 C32 114.2(4) . . ?
C13 O1 C17 117.6(4) . . ?
C18 O2 C14 118.0(4) . . ?
C15 O3 C22 117.5(4) . . ?
C25 O4 C29 118.1(4) . . ?
C30 O5 C26 117.5(3) . . ?
C27 O6 C34 117.3(3) . . ?
C36 C35 C41 113(3) . . ?
C36 C35 H35A 108.9 . . ?
C41 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C41 C35 H35B 108.9 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 C37 117(2) . . ?
C35 C36 H36A 108.1 . . ?
C37 C36 H36A 108.1 . . ?
C35 C36 H36B 108.1 . . ?
C37 C36 H36B 108.1 . . ?
H36A C36 H36B 107.3 . . ?
C38 C37 C36 115(2) . . ?
C38 C37 H37A 108.5 . . ?
C36 C37 H37A 108.5 . . ?
C38 C37 H37B 108.5 . . ?
C36 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C37 C38 C39 115(3) . . ?
C37 C38 H38A 108.6 . . ?
C39 C38 H38A 108.6 . . ?
C37 C38 H38B 108.6 . . ?
C39 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
C38 C39 C40 118(3) . . ?
C38 C39 H39A 107.8 . . ?
C40 C39 H39A 107.8 . . ?
C38 C39 H39B 107.8 . . ?
C40 C39 H39B 107.8 . . ?
H39A C39 H39B 107.2 . . ?
C41 C40 C39 118(3) . . ?
C41 C40 H40A 107.7 . . ?
C39 C40 H40A 107.7 . . ?
C41 C40 H40B 107.7 . . ?
C39 C40 H40B 107.7 . . ?
H40A C40 H40B 107.1 . . ?
C40 C41 C35 120(3) . . ?
C40 C41 H41A 107.3 . . ?
C35 C41 H41A 107.3 . . ?
C40 C41 H41B 107.3 . . ?
C35 C41 H41B 107.3 . . ?
H41A C41 H41B 106.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 58.2(5) . . . . ?
C11 C1 C2 C3 -178.4(4) . . . . ?
C9 C1 C2 C3 -58.5(5) . . . . ?
C1 C2 C3 C10 61.0(5) . . . . ?
C1 C2 C3 C4 -59.9(5) . . . . ?
C10 C3 C4 C5 -60.0(5) . . . . ?
C2 C3 C4 C5 60.9(5) . . . . ?
C3 C4 C5 C23 -178.0(4) . . . . ?
C3 C4 C5 C7 59.2(4) . . . . ?
C3 C4 C5 C6 -58.9(5) . . . . ?
C11 C1 C6 C5 179.2(4) . . . . ?
C2 C1 C6 C5 -59.0(5) . . . . ?
C9 C1 C6 C5 57.5(5) . . . . ?
C23 C5 C6 C1 -179.2(4) . . . . ?
C7 C5 C6 C1 -58.0(5) . . . . ?
C4 C5 C6 C1 58.9(5) . . . . ?
C23 C5 C7 C8 176.7(3) . . . . ?
C4 C5 C7 C8 -59.4(4) . . . . ?
C6 C5 C7 C8 57.3(5) . . . . ?
C5 C7 C8 C10 60.4(5) . . . . ?
C5 C7 C8 C9 -58.6(5) . . . . ?
C7 C8 C9 C1 59.4(5) . . . . ?
C10 C8 C9 C1 -60.4(5) . . . . ?
C6 C1 C9 C8 -57.9(4) . . . . ?
C11 C1 C9 C8 179.0(3) . . . . ?
C2 C1 C9 C8 59.2(4) . . . . ?
C4 C3 C10 C8 59.1(5) . . . . ?
C2 C3 C10 C8 -61.6(5) . . . . ?
C7 C8 C10 C3 -59.2(5) . . . . ?
C9 C8 C10 C3 60.6(5) . . . . ?
C6 C1 C11 C16 9.1(6) . . . . ?
C2 C1 C11 C16 -112.0(5) . . . . ?
C9 C1 C11 C16 129.5(5) . . . . ?
C6 C1 C11 C12 -171.9(4) . . . . ?
C2 C1 C11 C12 67.0(5) . . . . ?
C9 C1 C11 C12 -51.5(5) . . . . ?
C16 C11 C12 C13 -0.9(7) . . . . ?
C1 C11 C12 C13 -180.0(4) . . . . ?
C11 C12 C13 O1 -178.7(4) . . . . ?
C11 C12 C13 C14 1.2(7) . . . . ?
O1 C13 C14 C15 179.5(4) . . . . ?
C12 C13 C14 C15 -0.4(7) . . . . ?
O1 C13 C14 O2 0.3(6) . . . . ?
C12 C13 C14 O2 -179.6(4) . . . . ?
C13 C14 C15 O3 179.9(4) . . . . ?
O2 C14 C15 O3 -1.0(6) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
O2 C14 C15 C16 178.5(4) . . . . ?
C14 C15 C16 C11 0.9(7) . . . . ?
O3 C15 C16 C11 -179.7(4) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
C1 C11 C16 C15 178.8(4) . . . . ?
N2 C20 C21 C18 2.6(9) . . . . ?
Cl1 C20 C21 C18 -176.7(4) . . . . ?
N1 C18 C21 C20 -2.4(7) . . . . ?
O2 C18 C21 C20 179.0(4) . . . . ?
C7 C5 C23 C24 128.0(4) . . . . ?
C4 C5 C23 C24 7.0(5) . . . . ?
C6 C5 C23 C24 -111.7(4) . . . . ?
C7 C5 C23 C28 -52.7(5) . . . . ?
C4 C5 C23 C28 -173.7(4) . . . . ?
C6 C5 C23 C28 67.6(5) . . . . ?
C28 C23 C24 C25 -0.8(6) . . . . ?
C5 C23 C24 C25 178.5(4) . . . . ?
C23 C24 C25 O4 -179.1(4) . . . . ?
C23 C24 C25 C26 2.2(6) . . . . ?
O4 C25 C26 C27 179.0(4) . . . . ?
C24 C25 C26 C27 -2.2(6) . . . . ?
O4 C25 C26 O5 -4.4(6) . . . . ?
C24 C25 C26 O5 174.5(4) . . . . ?
C25 C26 C27 O6 -178.8(4) . . . . ?
O5 C26 C27 O6 4.5(5) . . . . ?
C25 C26 C27 C28 0.8(6) . . . . ?
O5 C26 C27 C28 -175.9(4) . . . . ?
O6 C27 C28 C23 -179.9(4) . . . . ?
C26 C27 C28 C23 0.6(6) . . . . ?
C24 C23 C28 C27 -0.6(6) . . . . ?
C5 C23 C28 C27 -179.9(4) . . . . ?
N3 C30 C33 C32 -0.5(7) . . . . ?
O5 C30 C33 C32 -179.4(4) . . . . ?
N4 C32 C33 C30 -1.5(7) . . . . ?
Cl2 C32 C33 C30 178.7(3) . . . . ?
O2 C18 N1 C19 180.0(5) . . . . ?
C21 C18 N1 C19 1.4(8) . . . . ?
N2 C19 N1 C18 -0.3(9) . . . . ?
N1 C19 N2 C20 0.4(10) . . . . ?
C21 C20 N2 C19 -1.7(9) . . . . ?
Cl1 C20 N2 C19 177.7(5) . . . . ?
O5 C30 N3 C31 -179.8(4) . . . . ?
C33 C30 N3 C31 1.4(6) . . . . ?
N4 C31 N3 C30 -0.4(7) . . . . ?
N3 C31 N4 C32 -1.5(7) . . . . ?
C33 C32 N4 C31 2.4(7) . . . . ?
Cl2 C32 N4 C31 -177.8(3) . . . . ?
C12 C13 O1 C17 1.2(7) . . . . ?
C14 C13 O1 C17 -178.6(4) . . . . ?
N1 C18 O2 C14 14.1(6) . . . . ?
C21 C18 O2 C14 -167.2(4) . . . . ?
C15 C14 O2 C18 70.7(6) . . . . ?
C13 C14 O2 C18 -110.2(5) . . . . ?
C14 C15 O3 C22 -178.6(5) . . . . ?
C16 C15 O3 C22 2.0(8) . . . . ?
C26 C25 O4 C29 -178.1(4) . . . . ?
C24 C25 O4 C29 3.0(6) . . . . ?
N3 C30 O5 C26 9.2(6) . . . . ?
C33 C30 O5 C26 -171.9(4) . . . . ?
C25 C26 O5 C30 77.3(5) . . . . ?
C27 C26 O5 C30 -106.0(5) . . . . ?
C28 C27 O6 C34 5.9(6) . . . . ?
C26 C27 O6 C34 -174.6(4) . . . . ?
C41 C35 C36 C37 38(4) . . . . ?
C35 C36 C37 C38 -74(3) . . . . ?
C36 C37 C38 C39 88(3) . . . . ?
C37 C38 C39 C40 -35(4) . . . . ?
C38 C39 C40 C41 -45(4) . . . . ?
C39 C40 C41 C35 80(5) . . . . ?
C36 C35 C41 C40 -55(5) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.084

