# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1550183'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-08-25T13:57:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C23 H27 Cl N4 O3'
_chemical_formula_moiety         'C23 H23 N4 O3, CL, 2(H2 O)'
_chemical_formula_weight         442.93

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5146(2)
_cell_length_b                   18.6958(3)
_cell_length_c                   30.8781(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4338.11(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    121(2)
_cell_measurement_reflns_used    20449
_cell_measurement_theta_min      4.727
_cell_measurement_theta_max      71.183

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1872

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#


_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_absorpt_coefficient_mu    1.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.59295
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.914

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      121(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0015124
_diffrn_orient_matrix_ub_12      0.0754012
_diffrn_orient_matrix_ub_13      0.0201171
_diffrn_orient_matrix_ub_21      -0.0122533
_diffrn_orient_matrix_ub_22      -0.0331922
_diffrn_orient_matrix_ub_23      0.0455696
_diffrn_orient_matrix_ub_31      0.2046356
_diffrn_orient_matrix_ub_32      -0.0014305
_diffrn_orient_matrix_ub_33      0.0028797
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_number            63365
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.731
_diffrn_reflns_theta_max         72.087
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_coverage         0
_reflns_number_total             4202
_reflns_number_gt                3808
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+6.7662P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
O10 O 0.2355(2) 0.07892(9) 0.24767(5) 0.0275(4) Uani 1 1 d . . . . .
N1 N 0.1086(3) -0.01499(10) 0.28206(6) 0.0222(4) Uani 1 1 d . . . . .
N71 N 0.1109(3) -0.10761(10) 0.13111(6) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.1486(3) 0.09766(12) 0.32176(7) 0.0218(5) Uani 1 1 d . . . . .
N2 N 0.0747(3) -0.04954(11) 0.32149(6) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.1037(3) 0.16833(12) 0.40101(8) 0.0257(5) Uani 1 1 d . . . . .
H14 H 0.0896 0.19 0.4286 0.031 Uiso 1 1 calc R U . . .
N74 N -0.1398(3) -0.04422(10) 0.07048(6) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.0304(3) -0.11504(13) 0.31091(8) 0.0250(5) Uani 1 1 d . . . . .
H3 H -0.0012 -0.1507 0.3314 0.03 Uiso 1 1 calc R U . . .
C8 C 0.1057(3) -0.05176(12) 0.20277(7) 0.0218(5) Uani 1 1 d . . . . .
H8 H 0.137 -0.0064 0.1912 0.026 Uiso 1 1 calc R U . . .
C76 C 0.1454(3) -0.03871(13) 0.11029(8) 0.0267(5) Uani 1 1 d . . . . .
H76A H 0.2127 -0.0466 0.0831 0.032 Uiso 1 1 calc R U . . .
H76B H 0.2193 -0.0088 0.1297 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0870(3) -0.06183(12) 0.24719(7) 0.0215(5) Uani 1 1 d . . . . .
C16 C 0.4109(4) 0.21594(12) 0.39672(8) 0.0289(6) Uani 1 1 d . . . . .
H16 H 0.3973 0.238 0.4242 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2917(3) 0.14112(11) 0.33790(7) 0.0220(5) Uani 1 1 d . . . . .
C15 C 0.2673(3) 0.17518(12) 0.37898(7) 0.0238(5) Uani 1 1 d . . . . .
C13 C -0.0346(4) 0.13105(13) 0.38327(8) 0.0272(5) Uani 1 1 d . . . . .
H13 H -0.1462 0.1292 0.3977 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0348(3) -0.12703(12) 0.26549(7) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.1709(3) 0.05573(12) 0.28099(7) 0.0222(5) Uani 1 1 d . . . . .
C72 C 0.0082(4) -0.15210(12) 0.10091(7) 0.0258(5) Uani 1 1 d . . . . .
H72A H -0.0139 -0.1994 0.1142 0.031 Uiso 1 1 calc R U . . .
H72B H 0.0783 -0.1597 0.0742 0.031 Uiso 1 1 calc R U . . .
C73 C -0.1682(3) -0.11760(12) 0.08941(8) 0.0257(5) Uani 1 1 d . . . . .
H73A H -0.2319 -0.148 0.0682 0.031 Uiso 1 1 calc R U . . .
H73B H -0.2429 -0.1138 0.1157 0.031 Uiso 1 1 calc R U . . .
C12 C -0.0109(3) 0.09525(12) 0.34341(8) 0.0246(5) Uani 1 1 d . . . . .
H12 H -0.1071 0.069 0.3314 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5890(4) 0.19052(13) 0.33420(9) 0.0293(5) Uani 1 1 d . . . . .
H18 H 0.6978 0.1966 0.319 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0767(3) -0.11093(12) 0.17566(7) 0.0227(5) Uani 1 1 d . . . . .
C19 C 0.4566(3) 0.14988(12) 0.31636(8) 0.0251(5) Uani 1 1 d . . . . .
H19 H 0.4755 0.1273 0.2892 0.03 Uiso 1 1 calc R U . . .
C6 C 0.0224(3) -0.17731(12) 0.19439(8) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.0002 -0.217 0.1759 0.031 Uiso 1 1 calc R U . . .
C75 C -0.0279(4) 0.00054(12) 0.10006(8) 0.0268(5) Uani 1 1 d . . . . .
H75A H -0.0937 0.0101 0.1272 0.032 Uiso 1 1 calc R U . . .
H75B H -0.0011 0.0469 0.0861 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0013(3) -0.18544(12) 0.23815(8) 0.0265(5) Uani 1 1 d . . . . .
H5 H -0.0355 -0.23 0.2499 0.032 Uiso 1 1 calc R U . . .
C77 C -0.3141(4) -0.00964(15) 0.06117(9) 0.0336(6) Uani 1 1 d . . . . .
H77A H -0.381 -0.004 0.0882 0.05 Uiso 1 1 calc R U . . .
H77B H -0.3822 -0.0396 0.0411 0.05 Uiso 1 1 calc R U . . .
H77C H -0.2939 0.0374 0.0481 0.05 Uiso 1 1 calc R U . . .
C17 C 0.5662(4) 0.22354(13) 0.37488(9) 0.0315(6) Uani 1 1 d . . . . .
H17 H 0.6599 0.2512 0.387 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.12293(9) 0.15469(3) 0.52091(2) 0.03204(17) Uani 1 1 d . . . . .
O1W O 0.0082(3) -0.08808(10) -0.00696(6) 0.0292(4) Uani 1 1 d . . . . .
O2W O -0.2514(3) -0.18471(12) -0.02297(7) 0.0407(5) Uani 1 1 d . . . . .
H74 H -0.076(4) -0.0515(15) 0.0445(9) 0.030(7) Uiso 1 1 d . . . . .
H2W H 0.113(6) -0.106(2) -0.0018(12) 0.055(11) Uiso 1 1 d . . . . .
H4W H -0.351(7) -0.190(2) -0.0076(14) 0.080(14) Uiso 1 1 d . . . . .
H1W H -0.069(5) -0.117(2) -0.0138(12) 0.051(11) Uiso 1 1 d . . . . .
H3W H -0.217(7) -0.233(3) -0.0168(15) 0.096(16) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O10 C10 1.217(3) . ?
N1 C9 1.398(3) . ?
N1 N2 1.401(3) . ?
N1 C10 1.403(3) . ?
N71 C7 1.401(3) . ?
N71 C76 1.463(3) . ?
N71 C72 1.469(3) . ?
C11 C12 1.373(3) . ?
C11 C20 1.437(3) . ?
C11 C10 1.493(3) . ?
N2 C3 1.310(3) . ?
C14 C13 1.366(4) . ?
C14 C15 1.410(4) . ?
C14 H14 0.95 . ?
N74 C77 1.489(3) . ?
N74 C75 1.497(3) . ?
N74 C73 1.506(3) . ?
N74 H74 0.95(3) . ?
C3 C4 1.421(3) . ?
C3 H3 0.95 . ?
C8 C9 1.391(3) . ?
C8 C7 1.404(3) . ?
C8 H8 0.95 . ?
C76 C75 1.528(4) . ?
C76 H76A 0.99 . ?
C76 H76B 0.99 . ?
C9 C4 1.400(3) . ?
C16 C17 1.355(4) . ?
C16 C15 1.430(3) . ?
C16 H16 0.95 . ?
C20 C19 1.416(4) . ?
C20 C15 1.431(3) . ?
C13 C12 1.412(3) . ?
C13 H13 0.95 . ?
C4 C5 1.403(3) . ?
C72 C73 1.516(4) . ?
C72 H72A 0.99 . ?
C72 H72B 0.99 . ?
C73 H73A 0.99 . ?
C73 H73B 0.99 . ?
C12 H12 0.95 . ?
C18 C19 1.368(3) . ?
C18 C17 1.410(4) . ?
C18 H18 0.95 . ?
C7 C6 1.429(3) . ?
C19 H19 0.95 . ?
C6 C5 1.369(3) . ?
C6 H6 0.95 . ?
C75 H75A 0.99 . ?
C75 H75B 0.99 . ?
C5 H5 0.95 . ?
C77 H77A 0.98 . ?
C77 H77B 0.98 . ?
C77 H77C 0.98 . ?
C17 H17 0.95 . ?
O1W H2W 0.87(4) . ?
O1W H1W 0.82(4) . ?
O2W H4W 0.89(5) . ?
O2W H3W 0.96(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 N2 111.06(18) . . ?
C9 N1 C10 127.66(19) . . ?
N2 N1 C10 121.04(18) . . ?
C7 N71 C76 120.21(19) . . ?
C7 N71 C72 120.1(2) . . ?
C76 N71 C72 108.23(18) . . ?
C12 C11 C20 120.2(2) . . ?
C12 C11 C10 119.4(2) . . ?
C20 C11 C10 120.4(2) . . ?
C3 N2 N1 105.10(18) . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C77 N74 C75 111.68(19) . . ?
C77 N74 C73 110.23(19) . . ?
C75 N74 C73 110.60(18) . . ?
C77 N74 H74 110.2(18) . . ?
C75 N74 H74 108.3(18) . . ?
C73 N74 H74 105.7(17) . . ?
N2 C3 C4 112.8(2) . . ?
N2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
C9 C8 C7 117.7(2) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
N71 C76 C75 111.3(2) . . ?
N71 C76 H76A 109.4 . . ?
C75 C76 H76A 109.4 . . ?
N71 C76 H76B 109.4 . . ?
C75 C76 H76B 109.4 . . ?
H76A C76 H76B 108 . . ?
C8 C9 N1 131.5(2) . . ?
C8 C9 C4 123.0(2) . . ?
N1 C9 C4 105.5(2) . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C19 C20 C15 118.5(2) . . ?
C19 C20 C11 123.9(2) . . ?
C15 C20 C11 117.6(2) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 C20 119.9(2) . . ?
C16 C15 C20 118.6(2) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C9 C4 C5 119.0(2) . . ?
C9 C4 C3 105.5(2) . . ?
C5 C4 C3 135.5(2) . . ?
O10 C10 N1 119.3(2) . . ?
O10 C10 C11 124.8(2) . . ?
N1 C10 C11 115.94(19) . . ?
N71 C72 C73 111.54(19) . . ?
N71 C72 H72A 109.3 . . ?
C73 C72 H72A 109.3 . . ?
N71 C72 H72B 109.3 . . ?
C73 C72 H72B 109.3 . . ?
H72A C72 H72B 108 . . ?
N74 C73 C72 110.76(19) . . ?
N74 C73 H73A 109.5 . . ?
C72 C73 H73A 109.5 . . ?
N74 C73 H73B 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 108.1 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
N71 C7 C8 121.5(2) . . ?
N71 C7 C6 119.2(2) . . ?
C8 C7 C6 119.2(2) . . ?
C18 C19 C20 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119 . . ?
C7 C6 H6 119 . . ?
N74 C75 C76 109.66(19) . . ?
N74 C75 H75A 109.7 . . ?
C76 C75 H75A 109.7 . . ?
N74 C75 H75B 109.7 . . ?
C76 C75 H75B 109.7 . . ?
H75A C75 H75B 108.2 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N74 C77 H77A 109.5 . . ?
N74 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
N74 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
H2W O1W H1W 116(4) . . ?
H4W O2W H3W 91(4) . . ?

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
C9 N1 N2 C3 -1.2(3) . . . . ?
C10 N1 N2 C3 -176.0(2) . . . . ?
N1 N2 C3 C4 0.7(3) . . . . ?
C7 N71 C76 C75 -81.8(3) . . . . ?
C72 N71 C76 C75 61.6(2) . . . . ?
C7 C8 C9 N1 179.0(2) . . . . ?
C7 C8 C9 C4 -2.4(4) . . . . ?
N2 N1 C9 C8 179.9(2) . . . . ?
C10 N1 C9 C8 -5.7(4) . . . . ?
N2 N1 C9 C4 1.1(3) . . . . ?
C10 N1 C9 C4 175.5(2) . . . . ?
C12 C11 C20 C19 -176.3(2) . . . . ?
C10 C11 C20 C19 2.7(3) . . . . ?
C12 C11 C20 C15 6.1(3) . . . . ?
C10 C11 C20 C15 -174.9(2) . . . . ?
C13 C14 C15 C16 178.1(2) . . . . ?
C13 C14 C15 C20 -1.7(3) . . . . ?
C17 C16 C15 C14 -178.5(2) . . . . ?
C17 C16 C15 C20 1.3(3) . . . . ?
C19 C20 C15 C14 179.1(2) . . . . ?
C11 C20 C15 C14 -3.2(3) . . . . ?
C19 C20 C15 C16 -0.7(3) . . . . ?
C11 C20 C15 C16 177.1(2) . . . . ?
C15 C14 C13 C12 3.7(3) . . . . ?
C8 C9 C4 C5 0.7(4) . . . . ?
N1 C9 C4 C5 179.6(2) . . . . ?
C8 C9 C4 C3 -179.6(2) . . . . ?
N1 C9 C4 C3 -0.7(3) . . . . ?
N2 C3 C4 C9 0.0(3) . . . . ?
N2 C3 C4 C5 179.6(3) . . . . ?
C9 N1 C10 O10 -9.9(4) . . . . ?
N2 N1 C10 O10 164.0(2) . . . . ?
C9 N1 C10 C11 169.0(2) . . . . ?
N2 N1 C10 C11 -17.1(3) . . . . ?
C12 C11 C10 O10 133.3(3) . . . . ?
C20 C11 C10 O10 -45.7(3) . . . . ?
C12 C11 C10 N1 -45.5(3) . . . . ?
C20 C11 C10 N1 135.5(2) . . . . ?
C7 N71 C72 C73 83.2(3) . . . . ?
C76 N71 C72 C73 -60.3(3) . . . . ?
C77 N74 C73 C72 -177.5(2) . . . . ?
C75 N74 C73 C72 -53.5(2) . . . . ?
N71 C72 C73 N74 57.0(3) . . . . ?
C20 C11 C12 C13 -4.4(3) . . . . ?
C10 C11 C12 C13 176.6(2) . . . . ?
C14 C13 C12 C11 -0.6(4) . . . . ?
C76 N71 C7 C8 -11.6(4) . . . . ?
C72 N71 C7 C8 -150.8(2) . . . . ?
C76 N71 C7 C6 172.5(2) . . . . ?
C72 N71 C7 C6 33.3(3) . . . . ?
C9 C8 C7 N71 -173.2(2) . . . . ?
C9 C8 C7 C6 2.7(3) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C15 C20 C19 C18 -0.6(3) . . . . ?
C11 C20 C19 C18 -178.2(2) . . . . ?
N71 C7 C6 C5 174.5(2) . . . . ?
C8 C7 C6 C5 -1.4(4) . . . . ?
C77 N74 C75 C76 177.38(19) . . . . ?
C73 N74 C75 C76 54.2(2) . . . . ?
N71 C76 C75 N74 -59.5(2) . . . . ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C19 C18 C17 C16 -0.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O10 0.95 2.48 2.974(3) 112.6 .
C72 H72B Cl1 0.99 2.78 3.713(3) 156.5 2_554
C73 H73B N2 0.99 2.66 3.595(3) 157.2 6_556
C75 H75B O1W 0.99 2.56 3.311(3) 132.5 5
C77 H77B Cl1 0.98 2.88 3.779(3) 153.1 2_454
N74 H74 O1W 0.95(3) 1.84(3) 2.762(3) 164(3) .
O1W H2W Cl1 0.87(4) 2.30(4) 3.158(2) 173(3) 2_554
O2W H4W Cl1 0.89(5) 2.32(5) 3.154(2) 155(4) 2_454
O1W H1W O2W 0.82(4) 1.89(4) 2.705(3) 174(4) .
O2W H3W Cl1 0.96(5) 2.21(5) 3.155(2) 165(4) 4_545
C8 H8 O10 0.95 2.48 2.974(3) 112.6 .
C72 H72B Cl1 0.99 2.78 3.713(3) 156.5 2_554
C73 H73B N2 0.99 2.66 3.595(3) 157.2 6_556
C75 H75B O1W 0.99 2.56 3.311(3) 132.5 5
C77 H77B Cl1 0.98 2.88 3.779(3) 153.1 2_454
N74 H74 O1W 0.95(3) 1.84(3) 2.762(3) 164(3) .
O1W H2W Cl1 0.87(4) 2.30(4) 3.158(2) 173(3) 2_554
O2W H4W Cl1 0.89(5) 2.32(5) 3.154(2) 155(4) 2_454
O1W H1W O2W 0.82(4) 1.89(4) 2.705(3) 174(4) .
O2W H3W Cl1 0.96(5) 2.21(5) 3.155(2) 165(4) 4_545

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1550191'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-08-25T17:30:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H26 N2 O5'
_chemical_formula_moiety         'C20 H25 N2 O3, C2 H O4'
_chemical_formula_weight         398.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1897(4)
_cell_length_b                   11.1766(6)
_cell_length_c                   11.9074(7)
_cell_angle_alpha                114.544(5)
_cell_angle_beta                 92.599(4)
_cell_angle_gamma                112.821(5)
_cell_volume                     993.84(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6022
_cell_measurement_theta_min      3.4117
_cell_measurement_theta_max      28.6452

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             424

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.88442
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.0820425
_diffrn_orient_matrix_ub_12      0.0549641
_diffrn_orient_matrix_ub_13      0.0228588
_diffrn_orient_matrix_ub_21      -0.0164036
_diffrn_orient_matrix_ub_22      0.0290783
_diffrn_orient_matrix_ub_23      -0.0391458
_diffrn_orient_matrix_ub_31      -0.0215594
_diffrn_orient_matrix_ub_32      0.0471149
_diffrn_orient_matrix_ub_33      0.0501008
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_number            13992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.419
_diffrn_reflns_theta_max         28.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.9
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.9
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.9
_reflns_Friedel_coverage         0
_reflns_number_total             4623
_reflns_number_gt                3571
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.3921P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4623
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.046
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O31 O 0.03016(15) 0.12982(13) 0.44718(12) 0.0447(3) Uani 1 1 d . . . . .
O32 O -0.16070(16) 0.04165(14) 0.53932(14) 0.0544(4) Uani 1 1 d . . . . .
C30 C -0.04193(19) 0.04753(16) 0.49869(15) 0.0350(3) Uani 1 1 d . . . . .
H31 H -0.012(3) 0.203(3) 0.454(2) 0.096(8) Uiso 1 1 d . . . . .
O22 O -0.07536(14) 0.31663(12) 0.46732(13) 0.0469(3) Uani 1 1 d . . . . .
N33 N 0.40567(17) 0.72454(14) 0.49189(12) 0.0348(3) Uani 1 1 d . . . . .
O21 O 0.16944(15) 0.46839(13) 0.46877(13) 0.0507(3) Uani 1 1 d . . . . .
C9 C 0.17470(18) 0.61679(17) -0.04713(16) 0.0375(4) Uani 1 1 d . . . . .
N1 N 0.14629(17) 0.72826(15) 0.03985(14) 0.0419(3) Uani 1 1 d . . . . .
C5 C 0.27427(19) 0.44474(18) -0.04610(15) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.3165 0.4078 -0.0031 0.046 Uiso 1 1 calc R U . . .
O61 O 0.27260(18) 0.26746(16) -0.25453(12) 0.0599(4) Uani 1 1 d . . . . .
C20 C 0.02847(19) 0.43843(16) 0.48101(15) 0.0344(3) Uani 1 1 d . . . . .
C4 C 0.23622(18) 0.56179(16) 0.02020(15) 0.0346(3) Uani 1 1 d . . . . .
C6 C 0.2472(2) 0.38615(19) -0.17684(16) 0.0434(4) Uani 1 1 d . . . . .
C32 C 0.3681(2) 0.75394(17) 0.38492(15) 0.0367(3) Uani 1 1 d . . . . .
H32B H 0.4673 0.8265 0.3821 0.044 Uiso 1 1 calc R U . . .
H32A H 0.2913 0.7953 0.4017 0.044 Uiso 1 1 calc R U . . .
C3 C 0.24388(19) 0.64387(17) 0.15173(15) 0.0358(3) Uani 1 1 d . . . . .
C11 C 0.17995(19) 0.96880(18) 0.06270(16) 0.0386(4) Uani 1 1 d . . . . .
C31 C 0.2976(2) 0.61765(18) 0.25664(15) 0.0407(4) Uani 1 1 d . . . . .
H31B H 0.3789 0.5823 0.2358 0.049 Uiso 1 1 calc R U . . .
H31A H 0.2051 0.5415 0.262 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1546(2) 0.5605(2) -0.17870(17) 0.0465(4) Uani 1 1 d . . . . .
H8 H 0.1179 0.5999 -0.2222 0.056 Uiso 1 1 calc R U . . .
C10 C 0.0693(2) 0.8076(2) 0.0108(2) 0.0502(4) Uani 1 1 d . . . . .
H10A H -0.0257 0.7963 0.0456 0.06 Uiso 1 1 calc R U . . .
H10B H 0.0323 0.7636 -0.081 0.06 Uiso 1 1 calc R U . . .
C35 C 0.5321(2) 0.6713(2) 0.47918(18) 0.0502(4) Uani 1 1 d . . . . .
H35C H 0.4987 0.5852 0.3983 0.075 Uiso 1 1 calc R U . . .
H35B H 0.6333 0.7468 0.4846 0.075 Uiso 1 1 calc R U . . .
H35A H 0.5461 0.6475 0.5464 0.075 Uiso 1 1 calc R U . . .
C2 C 0.1871(2) 0.74225(18) 0.15868(16) 0.0410(4) Uani 1 1 d . . . . .
H2 H 0.1774 0.8093 0.2333 0.049 Uiso 1 1 calc R U . . .
C7 C 0.1906(2) 0.4451(2) -0.24185(17) 0.0485(4) Uani 1 1 d . . . . .
H7 H 0.1772 0.4054 -0.3296 0.058 Uiso 1 1 calc R U . . .
C34 C 0.4560(3) 0.8578(2) 0.61663(17) 0.0520(5) Uani 1 1 d . . . . .
H34B H 0.3738 0.8916 0.6242 0.078 Uiso 1 1 calc R U . . .
H34C H 0.4699 0.8344 0.6841 0.078 Uiso 1 1 calc R U . . .
H34A H 0.5571 0.9336 0.6223 0.078 Uiso 1 1 calc R U . . .
C62 C 0.3138(2) 0.1935(2) -0.19728(19) 0.0546(5) Uani 1 1 d . . . . .
H62C H 0.3282 0.1137 -0.2605 0.082 Uiso 1 1 calc R U . . .
H62B H 0.4132 0.2607 -0.132 0.082 Uiso 1 1 calc R U . . .
H62A H 0.228 0.1555 -0.1603 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3122(2) 1.0156(2) 0.0148(2) 0.0545(5) Uani 1 1 d . . . . .
H12 H 0.3333 0.9471 -0.0506 0.065 Uiso 1 1 calc R U . . .
C16 C 0.1520(2) 1.0739(2) 0.15948(18) 0.0531(5) Uani 1 1 d . . . . .
H16 H 0.0642 1.0444 0.194 0.064 Uiso 1 1 calc R U . . .
C15 C 0.2528(3) 1.2226(2) 0.2058(2) 0.0699(7) Uani 1 1 d . . . . .
H15 H 0.2312 1.2922 0.2696 0.084 Uiso 1 1 calc R U . . .
C14 C 0.3831(3) 1.2663(2) 0.1578(3) 0.0764(7) Uani 1 1 d . . . . .
H14 H 0.4515 1.3659 0.1894 0.092 Uiso 1 1 calc R U . . .
C13 C 0.4142(3) 1.1645(3) 0.0636(3) 0.0711(7) Uani 1 1 d . . . . .
H13 H 0.5044 1.1951 0.0317 0.085 Uiso 1 1 calc R U . . .
H6 H 0.314(2) 0.652(2) 0.4903(17) 0.046(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O31 C30 1.3015(18) . ?
O31 H31 1.01(3) . ?
O32 C30 1.2035(19) . ?
C30 C30 1.544(3) 2_556 ?
O22 C20 1.2586(18) . ?
N33 C34 1.485(2) . ?
N33 C35 1.485(2) . ?
N33 C32 1.498(2) . ?
N33 H6 0.908(19) . ?
O21 C20 1.2381(19) . ?
C9 N1 1.378(2) . ?
C9 C8 1.396(2) . ?
C9 C4 1.406(2) . ?
N1 C2 1.375(2) . ?
N1 C10 1.458(2) . ?
C5 C6 1.381(2) . ?
C5 C4 1.407(2) . ?
C5 H5 0.93 . ?
O61 C6 1.382(2) . ?
O61 C62 1.407(2) . ?
C20 C20 1.561(3) 2_566 ?
C4 C3 1.430(2) . ?
C6 C7 1.399(3) . ?
C32 C31 1.512(2) . ?
C32 H32B 0.97 . ?
C32 H32A 0.97 . ?
C3 C2 1.364(2) . ?
C3 C31 1.500(2) . ?
C11 C12 1.376(3) . ?
C11 C16 1.382(2) . ?
C11 C10 1.503(2) . ?
C31 H31B 0.97 . ?
C31 H31A 0.97 . ?
C8 C7 1.373(3) . ?
C8 H8 0.93 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C35 H35C 0.96 . ?
C35 H35B 0.96 . ?
C35 H35A 0.96 . ?
C2 H2 0.93 . ?
C7 H7 0.93 . ?
C34 H34B 0.96 . ?
C34 H34C 0.96 . ?
C34 H34A 0.96 . ?
C62 H62C 0.96 . ?
C62 H62B 0.96 . ?
C62 H62A 0.96 . ?
C12 C13 1.386(3) . ?
C12 H12 0.93 . ?
C16 C15 1.387(3) . ?
C16 H16 0.93 . ?
C15 C14 1.356(4) . ?
C15 H15 0.93 . ?
C14 C13 1.362(4) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?

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
C30 O31 H31 113.9(15) . . ?
O32 C30 O31 126.00(14) . . ?
O32 C30 C30 122.09(18) . 2_556 ?
O31 C30 C30 111.90(16) . 2_556 ?
C34 N33 C35 109.95(14) . . ?
C34 N33 C32 110.71(13) . . ?
C35 N33 C32 112.77(13) . . ?
C34 N33 H6 108.2(11) . . ?
C35 N33 H6 106.8(12) . . ?
C32 N33 H6 108.2(12) . . ?
N1 C9 C8 130.98(16) . . ?
N1 C9 C4 107.60(14) . . ?
C8 C9 C4 121.41(16) . . ?
C2 N1 C9 108.36(13) . . ?
C2 N1 C10 125.02(15) . . ?
C9 N1 C10 126.30(15) . . ?
C6 C5 C4 118.15(15) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C6 O61 C62 117.27(14) . . ?
O21 C20 O22 126.03(14) . . ?
O21 C20 C20 118.31(16) . 2_566 ?
O22 C20 C20 115.65(17) . 2_566 ?
C9 C4 C5 119.72(14) . . ?
C9 C4 C3 107.32(14) . . ?
C5 C4 C3 132.96(15) . . ?
C5 C6 O61 124.42(16) . . ?
C5 C6 C7 121.34(16) . . ?
O61 C6 C7 114.23(15) . . ?
N33 C32 C31 113.09(12) . . ?
N33 C32 H32B 109 . . ?
C31 C32 H32B 109 . . ?
N33 C32 H32A 109 . . ?
C31 C32 H32A 109 . . ?
H32B C32 H32A 107.8 . . ?
C2 C3 C4 106.28(14) . . ?
C2 C3 C31 128.68(15) . . ?
C4 C3 C31 124.98(14) . . ?
C12 C11 C16 118.21(17) . . ?
C12 C11 C10 120.68(17) . . ?
C16 C11 C10 121.11(17) . . ?
C3 C31 C32 113.05(13) . . ?
C3 C31 H31B 109 . . ?
C32 C31 H31B 109 . . ?
C3 C31 H31A 109 . . ?
C32 C31 H31A 109 . . ?
H31B C31 H31A 107.8 . . ?
C7 C8 C9 117.94(16) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
N1 C10 C11 113.55(14) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N33 C35 H35C 109.5 . . ?
N33 C35 H35B 109.5 . . ?
H35C C35 H35B 109.5 . . ?
N33 C35 H35A 109.5 . . ?
H35C C35 H35A 109.5 . . ?
H35B C35 H35A 109.5 . . ?
C3 C2 N1 110.43(15) . . ?
C3 C2 H2 124.8 . . ?
N1 C2 H2 124.8 . . ?
C8 C7 C6 121.34(16) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N33 C34 H34B 109.5 . . ?
N33 C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N33 C34 H34A 109.5 . . ?
H34B C34 H34A 109.5 . . ?
H34C C34 H34A 109.5 . . ?
O61 C62 H62C 109.5 . . ?
O61 C62 H62B 109.5 . . ?
H62C C62 H62B 109.5 . . ?
O61 C62 H62A 109.5 . . ?
H62C C62 H62A 109.5 . . ?
H62B C62 H62A 109.5 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C11 C16 C15 121.0(2) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C9 N1 C2 -179.42(17) . . . . ?
C4 C9 N1 C2 -0.61(17) . . . . ?
C8 C9 N1 C10 6.9(3) . . . . ?
C4 C9 N1 C10 -174.31(15) . . . . ?
N1 C9 C4 C5 179.20(13) . . . . ?
C8 C9 C4 C5 -1.9(2) . . . . ?
N1 C9 C4 C3 0.14(17) . . . . ?
C8 C9 C4 C3 179.08(15) . . . . ?
C6 C5 C4 C9 -0.9(2) . . . . ?
C6 C5 C4 C3 177.87(16) . . . . ?
C4 C5 C6 O61 -177.26(15) . . . . ?
C4 C5 C6 C7 2.9(2) . . . . ?
C62 O61 C6 C5 6.3(3) . . . . ?
C62 O61 C6 C7 -173.81(16) . . . . ?
C34 N33 C32 C31 -173.38(15) . . . . ?
C35 N33 C32 C31 62.96(19) . . . . ?
C9 C4 C3 C2 0.38(17) . . . . ?
C5 C4 C3 C2 -178.51(16) . . . . ?
C9 C4 C3 C31 177.91(15) . . . . ?
C5 C4 C3 C31 -1.0(3) . . . . ?
C2 C3 C31 C32 -29.9(2) . . . . ?
C4 C3 C31 C32 153.13(15) . . . . ?
N33 C32 C31 C3 173.99(13) . . . . ?
N1 C9 C8 C7 -178.76(16) . . . . ?
C4 C9 C8 C7 2.6(2) . . . . ?
C2 N1 C10 C11 70.7(2) . . . . ?
C9 N1 C10 C11 -116.62(18) . . . . ?
C12 C11 C10 N1 67.9(2) . . . . ?
C16 C11 C10 N1 -112.14(19) . . . . ?
C4 C3 C2 N1 -0.77(18) . . . . ?
C31 C3 C2 N1 -178.18(15) . . . . ?
C9 N1 C2 C3 0.88(19) . . . . ?
C10 N1 C2 C3 174.68(15) . . . . ?
C9 C8 C7 C6 -0.6(3) . . . . ?
C5 C6 C7 C8 -2.2(3) . . . . ?
O61 C6 C7 C8 177.93(16) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C10 C11 C12 C13 -179.71(18) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C10 C11 C16 C15 -178.99(17) . . . . ?
C11 C16 C15 C14 -1.5(3) . . . . ?
C16 C15 C14 C13 0.6(3) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 O22 1.01(3) 1.55(3) 2.5560(16) 179(3) .
C32 H32A O32 0.97 2.44 3.3893(19) 165.3 2_566
C2 H2 O32 0.93 2.57 3.485(2) 166.8 2_566
C34 H34B O22 0.96 2.61 3.132(2) 114.8 2_566
N33 H6 O22 0.908(19) 2.391(18) 2.9829(18) 122.9(14) 2_566
N33 H6 O21 0.908(19) 1.86(2) 2.7304(18) 159.6(17) .
O31 H31 O22 1.01(3) 1.55(3) 2.5560(16) 179(3) .
C32 H32A O32 0.97 2.44 3.3893(19) 165.3 2_566
C2 H2 O32 0.93 2.57 3.485(2) 166.8 2_566
C34 H34B O22 0.96 2.61 3.132(2) 114.8 2_566
N33 H6 O22 0.908(19) 2.391(18) 2.9829(18) 122.9(14) 2_566
N33 H6 O21 0.908(19) 1.86(2) 2.7304(18) 159.6(17) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1550190'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-09-23T16:45:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C42 H45.92 Br0.08 N6 O12 S2'
_chemical_formula_moiety         
'C19 H21.92 Br0.08 N3 O2 S, C19 H22 N3 O2 S, C2 O4, C2 H2 O4'
_chemical_formula_weight         897.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.3674(3)
_cell_length_b                   11.15040(10)
_cell_length_c                   23.6192(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.303(2)
_cell_angle_gamma                90
_cell_volume                     4316.81(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    14390
_cell_measurement_theta_min      2.9151
_cell_measurement_theta_max      28.7409

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1883

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.85972
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.974

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.0195675
_diffrn_orient_matrix_ub_12      0.006968
_diffrn_orient_matrix_ub_13      -0.0218569
_diffrn_orient_matrix_ub_21      -0.0384146
_diffrn_orient_matrix_ub_22      0.0107656
_diffrn_orient_matrix_ub_23      -0.022289
_diffrn_orient_matrix_ub_31      0.0044374
_diffrn_orient_matrix_ub_32      0.0623757
_diffrn_orient_matrix_ub_33      0.0062871
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_number            58928
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.975
_diffrn_reflns_theta_max         28.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_reflns_Friedel_coverage         0
_reflns_number_total             10491
_reflns_number_gt                7261
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+3.5385P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10491
_refine_ls_number_parameters     618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S10 S 0.73389(4) 0.81645(5) 0.01692(2) 0.03039(13) Uani 1 1 d . . . . .
N54 N 0.33620(11) 0.96569(16) 0.17104(8) 0.0273(4) Uani 1 1 d . . . . .
O10 O 0.70631(10) 0.74233(14) -0.03527(6) 0.0370(4) Uani 1 1 d . . . . .
O11 O 0.78286(10) 0.91987(13) 0.01793(7) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.65009(11) 0.86422(15) 0.02843(8) 0.0285(4) Uani 1 1 d . . . . .
N51 N 0.46593(11) 1.00305(14) 0.12165(7) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.78357(13) 0.72633(18) 0.07927(9) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.56734(13) 0.93954(17) 0.07630(9) 0.0244(4) Uani 1 1 d . . . . .
C56 C 0.44595(14) 1.09325(18) 0.15963(10) 0.0301(5) Uani 1 1 d . . . . .
H56A H 0.4581 1.174 0.1474 0.036 Uiso 1 1 calc R U . . .
H56B H 0.4806 1.0805 0.2018 0.036 Uiso 1 1 calc R U . . .
C55 C 0.35770(15) 1.08751(18) 0.15530(10) 0.0318(5) Uani 1 1 d . . . . .
H55A H 0.3471 1.1472 0.1829 0.038 Uiso 1 1 calc R U . . .
H55B H 0.3229 1.1078 0.1139 0.038 Uiso 1 1 calc R U . . .
C5 C 0.54547(13) 1.01207(17) 0.11780(9) 0.0248(4) Uani 1 1 d . . . . .
C52 C 0.44506(13) 0.88301(17) 0.13842(9) 0.0261(5) Uani 1 1 d . . . . .
H52A H 0.4782 0.8659 0.1806 0.031 Uiso 1 1 calc R U . . .
H52B H 0.4582 0.8218 0.1126 0.031 Uiso 1 1 calc R U . . .
C3 C 0.52271(13) 0.85348(18) 0.03178(9) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.467 0.8325 0.023 0.032 Uiso 1 1 calc R U . . .
C16 C 0.76090(15) 0.60678(19) 0.07806(10) 0.0333(5) Uani 1 1 d . . . . .
H16 H 0.7208 0.574 0.0438 0.04 Uiso 1 1 calc R U . . .
C12 C 0.84305(14) 0.7752(2) 0.12884(10) 0.0354(5) Uani 1 1 d . . . . .
H12 H 0.8587 0.8568 0.1288 0.042 Uiso 1 1 calc R U . . .
C9 C 0.64667(13) 0.94620(18) 0.07337(9) 0.0265(5) Uani 1 1 d . . . . .
C2 C 0.57343(13) 0.80829(18) 0.00499(9) 0.0289(5) Uani 1 1 d . . . . .
H2 H 0.5597 0.748 -0.0251 0.035 Uiso 1 1 calc R U . . .
C7 C 0.68221(15) 1.0966(2) 0.14724(10) 0.0374(6) Uani 1 1 d . . . . .
H7 H 0.7205 1.1523 0.1715 0.045 Uiso 1 1 calc R U . . .
C8 C 0.70557(15) 1.02404(19) 0.10847(10) 0.0333(5) Uani 1 1 d . . . . .
H8 H 0.759 1.0272 0.1059 0.04 Uiso 1 1 calc R U . . .
C53 C 0.35624(13) 0.87528(19) 0.13157(9) 0.0293(5) Uani 1 1 d . . . . .
H53A H 0.3229 0.8903 0.0892 0.035 Uiso 1 1 calc R U . . .
H53B H 0.3434 0.7938 0.1425 0.035 Uiso 1 1 calc R U . . .
C13 C 0.87913(15) 0.7032(2) 0.17823(11) 0.0405(6) Uani 1 1 d . . . . .
H13 H 0.9196 0.7354 0.2125 0.049 Uiso 1 1 calc R U . . .
C6 C 0.60438(15) 1.09128(19) 0.15210(10) 0.0324(5) Uani 1 1 d . . . . .
H6 H 0.5913 1.1431 0.1795 0.039 Uiso 1 1 calc R U . . .
C57 C 0.25022(15) 0.9584(2) 0.16860(12) 0.0448(6) Uani 1 1 d . . . . .
H57A H 0.2397 1.02 0.1947 0.067 Uiso 1 1 calc R U . . .
H57B H 0.2396 0.8789 0.1822 0.067 Uiso 1 1 calc R U . . .
H57C H 0.2143 0.9714 0.1273 0.067 Uiso 1 1 calc R U . . .
C15 C 0.79799(17) 0.5361(2) 0.12792(10) 0.0430(6) Uani 1 1 d . . . . .
H15 H 0.7832 0.4541 0.1278 0.052 Uiso 1 1 calc R U . . .
C14 C 0.85631(16) 0.5840(2) 0.17771(11) 0.0436(6) Uani 1 1 d . . . . .
H14 H 0.8809 0.5349 0.2118 0.052 Uiso 1 1 calc R U . . .
O62 O -0.05503(10) 0.79778(12) -0.15345(6) 0.0312(4) Uani 1 1 d . . . . .
O61 O -0.08609(11) 0.50304(12) -0.20577(6) 0.0372(4) Uani 1 1 d . . . . .
O70 O -0.08267(11) 0.99798(12) -0.19798(6) 0.0370(4) Uani 1 1 d . . . . .
N54A N -0.00013(11) 0.75285(15) -0.02678(8) 0.0279(4) Uani 1 1 d . . . . .
N51A N 0.17316(11) 0.70540(14) 0.01581(7) 0.0276(4) Uani 1 1 d . . . . .
C70 C -0.06453(13) 1.08551(17) -0.16153(9) 0.0229(4) Uani 1 1 d . . . . .
O63 O -0.11020(11) 0.72853(13) -0.24698(7) 0.0403(4) Uani 1 1 d . . . . .
O60 O -0.04761(11) 0.57325(12) -0.11171(6) 0.0378(4) Uani 1 1 d . . . . .
O73 O -0.05164(12) 1.29648(13) -0.15921(7) 0.0432(5) Uani 1 1 d . . . . .
C4A C 0.29669(14) 0.59332(17) 0.06900(9) 0.0287(5) Uani 1 1 d . . . . .
C71 C -0.09079(13) 1.20852(17) -0.19185(9) 0.0231(4) Uani 1 1 d . . . . .
C61 C -0.08076(13) 0.71433(17) -0.19305(9) 0.0254(4) Uani 1 1 d . . . . .
C52A C 0.11303(13) 0.60938(17) 0.01172(9) 0.0276(5) Uani 1 1 d . . . . .
H2AA H 0.1371 0.5483 0.043 0.033 Uiso 1 1 calc R U . . .
H2AB H 0.0989 0.5698 -0.0279 0.033 Uiso 1 1 calc R U . . .
O71 O -0.03450(13) 1.07899(14) -0.10789(7) 0.0552(6) Uani 1 1 d . . . . .
O72 O -0.14422(12) 1.21858(14) -0.23917(7) 0.0499(5) Uani 1 1 d . . . . .
C53A C 0.03681(14) 0.66010(18) 0.01991(9) 0.0296(5) Uani 1 1 d . . . . .
H3AA H -0.003 0.5948 0.0168 0.035 Uiso 1 1 calc R U . . .
H3AB H 0.0505 0.6964 0.0603 0.035 Uiso 1 1 calc R U . . .
C56A C 0.13751(14) 0.79578(18) -0.03033(9) 0.0295(5) Uani 1 1 d . . . . .
H6AA H 0.1237 0.7585 -0.0705 0.035 Uiso 1 1 calc R U . . .
H6AB H 0.1779 0.8602 -0.0275 0.035 Uiso 1 1 calc R U . . .
C12A C 0.55315(14) 0.62282(19) 0.24091(10) 0.0323(5) Uani 1 1 d . . . . .
H2P H 0.5183 0.5882 0.2601 0.039 Uiso 1 1 calc R U . . .
C3A C 0.28156(17) 0.5557(2) 0.12321(10) 0.0344(5) Uani 1 1 d . . . . .
N1A N 0.40520(12) 0.48853(16) 0.12722(8) 0.0350(5) Uani 1 1 d . . . . .
C55A C 0.06161(14) 0.84895(18) -0.02287(10) 0.0308(5) Uani 1 1 d . . . . .
H5AA H 0.0757 0.8896 0.0165 0.037 Uiso 1 1 calc R U . . .
H5AB H 0.0382 0.9095 -0.0546 0.037 Uiso 1 1 calc R U . . .
C6A C 0.28866(14) 0.69126(18) -0.02320(9) 0.0305(5) Uani 1 1 d . . . . .
H6A H 0.2603 0.7405 -0.0564 0.037 Uiso 1 1 calc R U . . .
C5A C 0.25160(13) 0.66355(17) 0.01922(9) 0.0270(5) Uani 1 1 d . . . . .
C9A C 0.37457(14) 0.55281(18) 0.07267(9) 0.0311(5) Uani 1 1 d . . . . .
C11A C 0.55814(14) 0.57424(19) 0.18806(10) 0.0313(5) Uani 1 1 d . . . . .
C13A C 0.60008(14) 0.72306(19) 0.26514(10) 0.0342(5) Uani 1 1 d . . . . .
H3P H 0.5973 0.7578 0.3011 0.041 Uiso 1 1 calc R U . . .
C60 C -0.07014(14) 0.58570(17) -0.16677(9) 0.0281(5) Uani 1 1 d . . . . .
C8A C 0.41073(15) 0.57765(19) 0.02924(10) 0.0348(5) Uani 1 1 d . . . . .
H8A H 0.463 0.5473 0.0322 0.042 Uiso 1 1 calc R U . . .
C15A C 0.65511(15) 0.7221(2) 0.18419(11) 0.0425(6) Uani 1 1 d . . . . .
H5P H 0.6903 0.756 0.1651 0.051 Uiso 1 1 calc R U . . .
C57A C -0.07696(15) 0.8018(2) -0.02162(10) 0.0373(5) Uani 1 1 d . . . . .
H7AA H -0.1174 0.7373 -0.0282 0.056 Uiso 1 1 calc R U . . .
H7AB H -0.098 0.8647 -0.0518 0.056 Uiso 1 1 calc R U . . .
H7AC H -0.0663 0.8356 0.0185 0.056 Uiso 1 1 calc R U . . .
C14A C 0.65068(14) 0.7721(2) 0.23688(11) 0.0379(6) Uani 1 1 d . . . . .
H4P H 0.6827 0.8405 0.2536 0.046 Uiso 1 1 calc R U . . .
C7A C 0.36623(14) 0.6488(2) -0.01844(10) 0.0345(5) Uani 1 1 d . . . . .
H7A H 0.389 0.6693 -0.0486 0.041 Uiso 1 1 calc R U . . .
C2A C 0.34757(16) 0.4948(2) 0.15722(10) 0.0378(6) Uani 1 1 d . . . . .
H2A H 0.3542 0.4612 0.1955 0.045 Uiso 1 1 calc R U . . .
C16A C 0.60816(15) 0.6227(2) 0.15951(11) 0.0394(6) Uani 1 1 d . . . . .
H6P H 0.6105 0.5884 0.1233 0.047 Uiso 1 1 calc R U . . .
Br3A Br 0.22713(18) 0.5927(3) 0.16100(12) 0.0329(11) Uani 0.0838(14) 1 d . . P
A 1
S10A S 0.4978(2) 0.4430(2) 0.15946(12) 0.0228(12) Uani 0.63(3) 1 d . . P B 3
O10A O 0.4962(6) 0.3690(13) 0.2098(6) 0.0308(15) Uani 0.63(3) 1 d . . P B 3
O11A O 0.5230(5) 0.3952(5) 0.1139(4) 0.0313(16) Uani 0.63(3) 1 d . . P B 3
S10B S 0.5101(11) 0.4472(7) 0.1564(4) 0.077(3) Uani 0.37(3) 1 d . . P B 4
O11B O 0.5375(15) 0.4046(16) 0.1053(10) 0.084(6) Uani 0.37(3) 1 d . . P B 4
O10B O 0.5112(18) 0.369(2) 0.2030(13) 0.069(6) Uani 0.37(3) 1 d . . P B 4
H3A H 0.233(3) 0.569(4) 0.136(2) 0.083 Uiso 0.9162(14) 1 d . U P A 2
H70 H -0.066(2) 0.901(3) -0.1736(15) 0.098(12) Uiso 1 1 d . . . . .
H73 H -0.068(2) 1.378(3) -0.1777(15) 0.094(11) Uiso 1 1 d . . . . .
H54A H -0.0131(15) 0.715(2) -0.0635(11) 0.040(7) Uiso 1 1 d . . . . .
H54 H 0.3672(14) 0.951(2) 0.2078(11) 0.031(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S10 O11 1.4284(16) . ?
S10 O10 1.4288(16) . ?
S10 N1 1.6544(19) . ?
S10 C11 1.756(2) . ?
N54 C57 1.477(3) . ?
N54 C55 1.488(3) . ?
N54 C53 1.490(3) . ?
N54 H54 0.87(2) . ?
N1 C2 1.407(3) . ?
N1 C9 1.417(3) . ?
N51 C5 1.418(3) . ?
N51 C56 1.464(3) . ?
N51 C52 1.475(2) . ?
C11 C16 1.388(3) . ?
C11 C12 1.391(3) . ?
C4 C9 1.404(3) . ?
C4 C5 1.416(3) . ?
C4 C3 1.445(3) . ?
C56 C55 1.503(3) . ?
C56 H56A 0.99 . ?
C56 H56B 0.99 . ?
C55 H55A 0.99 . ?
C55 H55B 0.99 . ?
C5 C6 1.391(3) . ?
C52 C53 1.499(3) . ?
C52 H52A 0.99 . ?
C52 H52B 0.99 . ?
C3 C2 1.341(3) . ?
C3 H3 0.95 . ?
C16 C15 1.386(3) . ?
C16 H16 0.95 . ?
C12 C13 1.384(3) . ?
C12 H12 0.95 . ?
C9 C8 1.388(3) . ?
C2 H2 0.95 . ?
C7 C8 1.380(3) . ?
C7 C6 1.395(3) . ?
C7 H7 0.95 . ?
C8 H8 0.95 . ?
C53 H53A 0.99 . ?
C53 H53B 0.99 . ?
C13 C14 1.386(3) . ?
C13 H13 0.95 . ?
C6 H6 0.95 . ?
C57 H57A 0.98 . ?
C57 H57B 0.98 . ?
C57 H57C 0.98 . ?
C15 C14 1.381(3) . ?
C15 H15 0.95 . ?
C14 H14 0.95 . ?
O62 C61 1.290(2) . ?
O62 H70 1.24(4) . ?
O61 C60 1.267(2) . ?
O70 C70 1.270(2) . ?
O70 H70 1.21(4) . ?
N54A C57A 1.483(3) . ?
N54A C53A 1.493(3) . ?
N54A C55A 1.497(3) . ?
N54A H54A 0.92(2) . ?
N51A C5A 1.417(3) . ?
N51A C56A 1.463(2) . ?
N51A C52A 1.476(3) . ?
C70 O71 1.202(2) . ?
C70 C71 1.545(3) . ?
O63 C61 1.216(2) . ?
O60 C60 1.236(2) . ?
O73 C71 1.293(2) . ?
O73 H73 1.01(4) . ?
C4A C9A 1.401(3) . ?
C4A C5A 1.414(3) . ?
C4A C3A 1.452(3) . ?
C71 O72 1.199(2) . ?
C61 C60 1.549(3) . ?
C52A C53A 1.510(3) . ?
C52A H2AA 0.99 . ?
C52A H2AB 0.99 . ?
C53A H3AA 0.99 . ?
C53A H3AB 0.99 . ?
C56A C55A 1.508(3) . ?
C56A H6AA 0.99 . ?
C56A H6AB 0.99 . ?
C12A C11A 1.389(3) . ?
C12A C13A 1.390(3) . ?
C12A H2P 0.95 . ?
C3A C2A 1.346(3) . ?
C3A Br3A 1.555(4) . ?
C3A H3A 0.99(5) . ?
N1A C2A 1.406(3) . ?
N1A C9A 1.415(3) . ?
N1A S10A 1.617(4) . ?
N1A S10B 1.782(16) . ?
C55A H5AA 0.99 . ?
C55A H5AB 0.99 . ?
C6A C5A 1.393(3) . ?
C6A C7A 1.397(3) . ?
C6A H6A 0.95 . ?
C9A C8A 1.396(3) . ?
C11A C16A 1.374(3) . ?
C11A S10B 1.688(11) . ?
C11A S10A 1.797(3) . ?
C13A C14A 1.380(3) . ?
C13A H3P 0.95 . ?
C8A C7A 1.386(3) . ?
C8A H8A 0.95 . ?
C15A C16A 1.385(4) . ?
C15A C14A 1.389(3) . ?
C15A H5P 0.95 . ?
C57A H7AA 0.98 . ?
C57A H7AB 0.98 . ?
C57A H7AC 0.98 . ?
C14A H4P 0.95 . ?
C7A H7A 0.95 . ?
C2A H2A 0.95 . ?
C16A H6P 0.95 . ?
S10A O11A 1.395(7) . ?
S10A O10A 1.454(13) . ?
S10B O10B 1.40(2) . ?
S10B O11B 1.511(16) . ?

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
O11 S10 O10 120.62(10) . . ?
O11 S10 N1 106.77(9) . . ?
O10 S10 N1 105.41(10) . . ?
O11 S10 C11 108.86(10) . . ?
O10 S10 C11 108.91(10) . . ?
N1 S10 C11 105.16(9) . . ?
C57 N54 C55 111.98(18) . . ?
C57 N54 C53 112.36(18) . . ?
C55 N54 C53 109.35(16) . . ?
C57 N54 H54 108.1(15) . . ?
C55 N54 H54 107.4(15) . . ?
C53 N54 H54 107.4(15) . . ?
C2 N1 C9 108.18(17) . . ?
C2 N1 S10 124.19(15) . . ?
C9 N1 S10 126.01(15) . . ?
C5 N51 C56 115.08(16) . . ?
C5 N51 C52 114.39(16) . . ?
C56 N51 C52 109.27(16) . . ?
C16 C11 C12 121.3(2) . . ?
C16 C11 S10 118.36(17) . . ?
C12 C11 S10 120.28(17) . . ?
C9 C4 C5 119.73(18) . . ?
C9 C4 C3 107.36(18) . . ?
C5 C4 C3 132.9(2) . . ?
N51 C56 C55 111.83(17) . . ?
N51 C56 H56A 109.2 . . ?
C55 C56 H56A 109.2 . . ?
N51 C56 H56B 109.2 . . ?
C55 C56 H56B 109.2 . . ?
H56A C56 H56B 107.9 . . ?
N54 C55 C56 110.87(17) . . ?
N54 C55 H55A 109.5 . . ?
C56 C55 H55A 109.5 . . ?
N54 C55 H55B 109.5 . . ?
C56 C55 H55B 109.5 . . ?
H55A C55 H55B 108.1 . . ?
C6 C5 C4 116.9(2) . . ?
C6 C5 N51 123.54(19) . . ?
C4 C5 N51 119.59(18) . . ?
N51 C52 C53 111.01(17) . . ?
N51 C52 H52A 109.4 . . ?
C53 C52 H52A 109.4 . . ?
N51 C52 H52B 109.4 . . ?
C53 C52 H52B 109.4 . . ?
H52A C52 H52B 108 . . ?
C2 C3 C4 108.35(19) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
C15 C16 C11 118.7(2) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C8 C9 C4 123.0(2) . . ?
C8 C9 N1 130.2(2) . . ?
C4 C9 N1 106.72(18) . . ?
C3 C2 N1 109.36(18) . . ?
C3 C2 H2 125.3 . . ?
N1 C2 H2 125.3 . . ?
C8 C7 C6 122.3(2) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 116.3(2) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
N54 C53 C52 109.77(17) . . ?
N54 C53 H53A 109.7 . . ?
C52 C53 H53A 109.7 . . ?
N54 C53 H53B 109.7 . . ?
C52 C53 H53B 109.7 . . ?
H53A C53 H53B 108.2 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N54 C57 H57A 109.5 . . ?
N54 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
N54 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C61 O62 H70 114.9(16) . . ?
C70 O70 H70 113.2(16) . . ?
C57A N54A C53A 111.88(17) . . ?
C57A N54A C55A 112.16(17) . . ?
C53A N54A C55A 109.04(16) . . ?
C57A N54A H54A 107.3(15) . . ?
C53A N54A H54A 106.9(15) . . ?
C55A N54A H54A 109.4(15) . . ?
C5A N51A C56A 115.55(17) . . ?
C5A N51A C52A 114.26(16) . . ?
C56A N51A C52A 109.55(16) . . ?
O71 C70 O70 126.29(18) . . ?
O71 C70 C71 120.06(17) . . ?
O70 C70 C71 113.51(16) . . ?
C71 O73 H73 114(2) . . ?
C9A C4A C5A 119.2(2) . . ?
C9A C4A C3A 107.7(2) . . ?
C5A C4A C3A 132.9(2) . . ?
O72 C71 O73 125.26(19) . . ?
O72 C71 C70 122.29(18) . . ?
O73 C71 C70 112.37(17) . . ?
O63 C61 O62 126.21(18) . . ?
O63 C61 C60 119.56(17) . . ?
O62 C61 C60 114.23(17) . . ?
N51A C52A C53A 110.56(17) . . ?
N51A C52A H2AA 109.5 . . ?
C53A C52A H2AA 109.5 . . ?
N51A C52A H2AB 109.5 . . ?
C53A C52A H2AB 109.5 . . ?
H2AA C52A H2AB 108.1 . . ?
N54A C53A C52A 110.23(17) . . ?
N54A C53A H3AA 109.6 . . ?
C52A C53A H3AA 109.6 . . ?
N54A C53A H3AB 109.6 . . ?
C52A C53A H3AB 109.6 . . ?
H3AA C53A H3AB 108.1 . . ?
N51A C56A C55A 110.78(17) . . ?
N51A C56A H6AA 109.5 . . ?
C55A C56A H6AA 109.5 . . ?
N51A C56A H6AB 109.5 . . ?
C55A C56A H6AB 109.5 . . ?
H6AA C56A H6AB 108.1 . . ?
C11A C12A C13A 118.7(2) . . ?
C11A C12A H2P 120.6 . . ?
C13A C12A H2P 120.6 . . ?
C2A C3A C4A 107.8(2) . . ?
C2A C3A Br3A 110.5(2) . . ?
C4A C3A Br3A 138.7(2) . . ?
C2A C3A H3A 123(3) . . ?
C4A C3A H3A 130(3) . . ?
C2A N1A C9A 108.52(19) . . ?
C2A N1A S10A 122.75(19) . . ?
C9A N1A S10A 127.1(2) . . ?
C2A N1A S10B 128.7(6) . . ?
C9A N1A S10B 120.7(6) . . ?
N54A C55A C56A 110.33(16) . . ?
N54A C55A H5AA 109.6 . . ?
C56A C55A H5AA 109.6 . . ?
N54A C55A H5AB 109.6 . . ?
C56A C55A H5AB 109.6 . . ?
H5AA C55A H5AB 108.1 . . ?
C5A C6A C7A 122.0(2) . . ?
C5A C6A H6A 119 . . ?
C7A C6A H6A 119 . . ?
C6A C5A C4A 117.4(2) . . ?
C6A C5A N51A 123.39(18) . . ?
C4A C5A N51A 119.17(19) . . ?
C8A C9A C4A 123.4(2) . . ?
C8A C9A N1A 130.1(2) . . ?
C4A C9A N1A 106.5(2) . . ?
C16A C11A C12A 121.7(2) . . ?
C16A C11A S10B 114.3(7) . . ?
C12A C11A S10B 123.9(7) . . ?
C16A C11A S10A 121.4(2) . . ?
C12A C11A S10A 117.0(2) . . ?
C14A C13A C12A 120.0(2) . . ?
C14A C13A H3P 120 . . ?
C12A C13A H3P 120 . . ?
O60 C60 O61 126.89(18) . . ?
O60 C60 C61 118.68(17) . . ?
O61 C60 C61 114.43(17) . . ?
C7A C8A C9A 116.4(2) . . ?
C7A C8A H8A 121.8 . . ?
C9A C8A H8A 121.8 . . ?
C16A C15A C14A 119.9(2) . . ?
C16A C15A H5P 120 . . ?
C14A C15A H5P 120 . . ?
N54A C57A H7AA 109.5 . . ?
N54A C57A H7AB 109.5 . . ?
H7AA C57A H7AB 109.5 . . ?
N54A C57A H7AC 109.5 . . ?
H7AA C57A H7AC 109.5 . . ?
H7AB C57A H7AC 109.5 . . ?
C13A C14A C15A 120.5(2) . . ?
C13A C14A H4P 119.8 . . ?
C15A C14A H4P 119.8 . . ?
C8A C7A C6A 121.6(2) . . ?
C8A C7A H7A 119.2 . . ?
C6A C7A H7A 119.2 . . ?
C3A C2A N1A 109.4(2) . . ?
C3A C2A H2A 125.3 . . ?
N1A C2A H2A 125.3 . . ?
C11A C16A C15A 119.2(2) . . ?
C11A C16A H6P 120.4 . . ?
C15A C16A H6P 120.4 . . ?
O11A S10A O10A 120.6(6) . . ?
O11A S10A N1A 105.9(4) . . ?
O10A S10A N1A 106.2(4) . . ?
O11A S10A C11A 107.9(3) . . ?
O10A S10A C11A 108.7(6) . . ?
N1A S10A C11A 106.70(17) . . ?
O10B S10B O11B 120.5(12) . . ?
O10B S10B C11A 107.2(12) . . ?
O11B S10B C11A 112.2(9) . . ?
O10B S10B N1A 102.1(10) . . ?
O11B S10B N1A 108.9(8) . . ?
C11A S10B N1A 104.3(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
O11 S10 N1 C2 149.55(17) . . . . ?
O10 S10 N1 C2 20.14(19) . . . . ?
C11 S10 N1 C2 -94.89(18) . . . . ?
O11 S10 N1 C9 -46.74(19) . . . . ?
O10 S10 N1 C9 -176.16(16) . . . . ?
C11 S10 N1 C9 68.81(18) . . . . ?
O11 S10 C11 C16 -160.66(18) . . . . ?
O10 S10 C11 C16 -27.3(2) . . . . ?
N1 S10 C11 C16 85.23(19) . . . . ?
O11 S10 C11 C12 20.5(2) . . . . ?
O10 S10 C11 C12 153.80(18) . . . . ?
N1 S10 C11 C12 -93.62(19) . . . . ?
C5 N51 C56 C55 172.83(17) . . . . ?
C52 N51 C56 C55 -56.9(2) . . . . ?
C57 N54 C55 C56 178.58(19) . . . . ?
C53 N54 C55 C56 -56.2(2) . . . . ?
N51 C56 C55 N54 56.7(2) . . . . ?
C9 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C6 -176.3(2) . . . . ?
C9 C4 C5 N51 -178.49(17) . . . . ?
C3 C4 C5 N51 2.4(3) . . . . ?
C56 N51 C5 C6 6.8(3) . . . . ?
C52 N51 C5 C6 -121.0(2) . . . . ?
C56 N51 C5 C4 -171.78(17) . . . . ?
C52 N51 C5 C4 60.5(2) . . . . ?
C5 N51 C52 C53 -170.54(17) . . . . ?
C56 N51 C52 C53 58.8(2) . . . . ?
C9 C4 C3 C2 1.8(2) . . . . ?
C5 C4 C3 C2 -179.0(2) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
S10 C11 C16 C15 -177.93(19) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
S10 C11 C12 C13 177.68(18) . . . . ?
C5 C4 C9 C8 -1.9(3) . . . . ?
C3 C4 C9 C8 177.41(19) . . . . ?
C5 C4 C9 N1 179.87(17) . . . . ?
C3 C4 C9 N1 -0.8(2) . . . . ?
C2 N1 C9 C8 -178.5(2) . . . . ?
S10 N1 C9 C8 15.6(3) . . . . ?
C2 N1 C9 C4 -0.4(2) . . . . ?
S10 N1 C9 C4 -166.30(14) . . . . ?
C4 C3 C2 N1 -2.1(2) . . . . ?
C9 N1 C2 C3 1.6(2) . . . . ?
S10 N1 C2 C3 167.81(15) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C4 C9 C8 C7 -0.2(3) . . . . ?
N1 C9 C8 C7 177.6(2) . . . . ?
C57 N54 C53 C52 -177.10(18) . . . . ?
C55 N54 C53 C52 57.9(2) . . . . ?
N51 C52 C53 N54 -60.1(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
N51 C5 C6 C7 179.5(2) . . . . ?
C8 C7 C6 C5 -0.1(4) . . . . ?
C11 C16 C15 C14 0.0(4) . . . . ?
C16 C15 C14 C13 -0.7(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
O71 C70 C71 O72 -153.2(2) . . . . ?
O70 C70 C71 O72 22.7(3) . . . . ?
O71 C70 C71 O73 23.8(3) . . . . ?
O70 C70 C71 O73 -160.37(19) . . . . ?
C5A N51A C52A C53A 169.45(16) . . . . ?
C56A N51A C52A C53A -59.1(2) . . . . ?
C57A N54A C53A C52A 177.90(17) . . . . ?
C55A N54A C53A C52A -57.4(2) . . . . ?
N51A C52A C53A N54A 58.9(2) . . . . ?
C5A N51A C56A C55A -170.15(16) . . . . ?
C52A N51A C56A C55A 59.1(2) . . . . ?
C9A C4A C3A C2A -0.4(2) . . . . ?
C5A C4A C3A C2A -176.6(2) . . . . ?
C9A C4A C3A Br3A 157.0(3) . . . . ?
C5A C4A C3A Br3A -19.2(5) . . . . ?
C57A N54A C55A C56A -178.16(17) . . . . ?
C53A N54A C55A C56A 57.4(2) . . . . ?
N51A C56A C55A N54A -59.0(2) . . . . ?
C7A C6A C5A C4A 2.0(3) . . . . ?
C7A C6A C5A N51A 179.79(19) . . . . ?
C9A C4A C5A C6A -1.6(3) . . . . ?
C3A C4A C5A C6A 174.2(2) . . . . ?
C9A C4A C5A N51A -179.42(17) . . . . ?
C3A C4A C5A N51A -3.6(3) . . . . ?
C56A N51A C5A C6A -9.2(3) . . . . ?
C52A N51A C5A C6A 119.3(2) . . . . ?
C56A N51A C5A C4A 168.56(17) . . . . ?
C52A N51A C5A C4A -63.0(2) . . . . ?
C5A C4A C9A C8A -0.3(3) . . . . ?
C3A C4A C9A C8A -177.07(19) . . . . ?
C5A C4A C9A N1A 178.53(17) . . . . ?
C3A C4A C9A N1A 1.8(2) . . . . ?
C2A N1A C9A C8A 176.3(2) . . . . ?
S10A N1A C9A C8A 10.5(3) . . . . ?
S10B N1A C9A C8A 11.2(4) . . . . ?
C2A N1A C9A C4A -2.4(2) . . . . ?
S10A N1A C9A C4A -168.22(18) . . . . ?
S10B N1A C9A C4A -167.5(3) . . . . ?
C13A C12A C11A C16A 0.1(3) . . . . ?
C13A C12A C11A S10B 175.4(5) . . . . ?
C13A C12A C11A S10A 178.8(2) . . . . ?
C11A C12A C13A C14A -0.3(3) . . . . ?
O63 C61 C60 O60 -173.0(2) . . . . ?
O62 C61 C60 O60 8.0(3) . . . . ?
O63 C61 C60 O61 7.1(3) . . . . ?
O62 C61 C60 O61 -171.9(2) . . . . ?
C4A C9A C8A C7A 1.7(3) . . . . ?
N1A C9A C8A C7A -176.8(2) . . . . ?
C12A C13A C14A C15A 0.1(3) . . . . ?
C16A C15A C14A C13A 0.3(3) . . . . ?
C9A C8A C7A C6A -1.3(3) . . . . ?
C5A C6A C7A C8A -0.6(3) . . . . ?
C4A C3A C2A N1A -1.1(2) . . . . ?
Br3A C3A C2A N1A -165.40(19) . . . . ?
C9A N1A C2A C3A 2.2(2) . . . . ?
S10A N1A C2A C3A 168.77(19) . . . . ?
S10B N1A C2A C3A 165.7(4) . . . . ?
C12A C11A C16A C15A 0.3(3) . . . . ?
S10B C11A C16A C15A -175.4(4) . . . . ?
S10A C11A C16A C15A -178.3(2) . . . . ?
C14A C15A C16A C11A -0.5(3) . . . . ?
C2A N1A S10A O11A 152.4(3) . . . . ?
C9A N1A S10A O11A -43.7(4) . . . . ?
C2A N1A S10A O10A 23.1(6) . . . . ?
C9A N1A S10A O10A -173.0(6) . . . . ?
C2A N1A S10A C11A -92.8(2) . . . . ?
C9A N1A S10A C11A 71.2(2) . . . . ?
C16A C11A S10A O11A 10.2(5) . . . . ?
C12A C11A S10A O11A -168.5(4) . . . . ?
C16A C11A S10A O10A 142.6(5) . . . . ?
C12A C11A S10A O10A -36.1(5) . . . . ?
C16A C11A S10A N1A -103.3(2) . . . . ?
C12A C11A S10A N1A 78.0(2) . . . . ?
C16A C11A S10B O10B 139.6(9) . . . . ?
C12A C11A S10B O10B -36.0(10) . . . . ?
C16A C11A S10B O11B 5.2(10) . . . . ?
C12A C11A S10B O11B -170.4(8) . . . . ?
C16A C11A S10B N1A -112.5(8) . . . . ?
C12A C11A S10B N1A 71.9(6) . . . . ?
C2A N1A S10B O10B 28.3(13) . . . . ?
C9A N1A S10B O10B -169.9(11) . . . . ?
C2A N1A S10B O11B 156.8(7) . . . . ?
C9A N1A S10B O11B -41.4(8) . . . . ?
C2A N1A S10B C11A -83.2(9) . . . . ?
C9A N1A S10B C11A 78.5(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C56 H56A O10A 0.99 2.59 3.307(14) 129.6 1_565
C56 H56A O10B 0.99 2.55 3.32(3) 134.5 1_565
C55 H55A O72 0.99 2.34 3.308(3) 166.1 4_686
C55 H55B O10 0.99 2.42 3.285(3) 144.9 3_675
C2 H2 O11A 0.95 2.65 3.568(6) 162.7 3_665
C8 H8 O11 0.95 2.55 3.102(3) 117.4 .
C53 H53B O63 0.99 2.48 2.967(3) 110.2 4_676
C52A H2AA Br3A 0.99 2.75 3.431(3) 126.2 .
C52A H2AB O60 0.99 2.66 3.327(3) 125.1 .
C53A H3AB O73 0.99 2.33 3.251(3) 154.1 3_575
C56A H6AB O11 0.99 2.54 3.433(3) 150.6 3_675
C12A H2P O70 0.95 2.47 3.422(3) 174.9 4_676
C55A H5AA O71 0.99 2.51 3.371(3) 144.9 3_575
C55A H5AB O71 0.99 2.39 3.344(3) 162.1 .
C8A H8A O11A 0.95 2.52 3.060(9) 116 .
C8A H8A O11B 0.95 2.39 3.030(18) 124.5 .
C57A H7AC O71 0.98 2.45 3.310(3) 146.9 3_575
C2A H2A O70 0.95 2.43 3.230(3) 141.5 4_676
C2A H2A O72 0.95 2.52 3.382(3) 150.2 4_676
O62 H70 O71 1.24(4) 2.46(3) 3.296(2) 122(2) .
O70 H70 O62 1.21(4) 1.24(4) 2.4467(19) 173(3) .
O70 H70 O63 1.21(4) 2.54(3) 3.198(2) 112(2) .
O73 H73 O61 1.01(4) 1.53(4) 2.537(2) 176(3) 1_565
O73 H73 O60 1.01(4) 2.63(3) 3.277(2) 122(2) 1_565
N54A H54A O62 0.92(2) 2.21(2) 2.868(2) 128.0(19) .
N54A H54A O60 0.92(2) 1.93(2) 2.761(2) 150(2) .
N54 H54 O61 0.87(2) 2.00(2) 2.795(2) 151(2) 4_676
N54 H54 O63 0.87(2) 2.24(2) 2.848(2) 126.7(19) 4_676
C56 H56A O10A 0.99 2.59 3.307(14) 129.6 1_565
C56 H56A O10B 0.99 2.55 3.32(3) 134.5 1_565
C55 H55A O72 0.99 2.34 3.308(3) 166.1 4_686
C55 H55B O10 0.99 2.42 3.285(3) 144.9 3_675
C2 H2 O11A 0.95 2.65 3.568(6) 162.7 3_665
C8 H8 O11 0.95 2.55 3.102(3) 117.4 .
C53 H53B O63 0.99 2.48 2.967(3) 110.2 4_676
C52A H2AA Br3A 0.99 2.75 3.431(3) 126.2 .
C52A H2AB O60 0.99 2.66 3.327(3) 125.1 .
C53A H3AB O73 0.99 2.33 3.251(3) 154.1 3_575
C56A H6AB O11 0.99 2.54 3.433(3) 150.6 3_675
C12A H2P O70 0.95 2.47 3.422(3) 174.9 4_676
C55A H5AA O71 0.99 2.51 3.371(3) 144.9 3_575
C55A H5AB O71 0.99 2.39 3.344(3) 162.1 .
C8A H8A O11A 0.95 2.52 3.060(9) 116 .
C8A H8A O11B 0.95 2.39 3.030(18) 124.5 .
C57A H7AC O71 0.98 2.45 3.310(3) 146.9 3_575
C2A H2A O70 0.95 2.43 3.230(3) 141.5 4_676
C2A H2A O72 0.95 2.52 3.382(3) 150.2 4_676
O62 H70 O71 1.24(4) 2.46(3) 3.296(2) 122(2) .
O70 H70 O62 1.21(4) 1.24(4) 2.4467(19) 173(3) .
O70 H70 O63 1.21(4) 2.54(3) 3.198(2) 112(2) .
O73 H73 O61 1.01(4) 1.53(4) 2.537(2) 176(3) 1_565
O73 H73 O60 1.01(4) 2.63(3) 3.277(2) 122(2) 1_565
N54A H54A O62 0.92(2) 2.21(2) 2.868(2) 128.0(19) .
N54A H54A O60 0.92(2) 1.93(2) 2.761(2) 150(2) .
N54 H54 O61 0.87(2) 2.00(2) 2.795(2) 151(2) 4_676
N54 H54 O63 0.87(2) 2.24(2) 2.848(2) 126.7(19) 4_676

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 1550193'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-09-23T23:36:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H25 N3 O4'
_chemical_formula_moiety         'C20 H24 N3, C2 H O4'
_chemical_formula_weight         395.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9809(4)
_cell_length_b                   11.1869(3)
_cell_length_c                   14.9549(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.115(3)
_cell_angle_gamma                90
_cell_volume                     1984.32(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4665
_cell_measurement_theta_min      2.9648
_cell_measurement_theta_max      29.5203

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cube
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             840

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.66522
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.973

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.032274
_diffrn_orient_matrix_ub_12      0.0151053
_diffrn_orient_matrix_ub_13      -0.0346393
_diffrn_orient_matrix_ub_21      -0.0494232
_diffrn_orient_matrix_ub_22      -0.0019939
_diffrn_orient_matrix_ub_23      -0.0322317
_diffrn_orient_matrix_ub_31      -0.0095357
_diffrn_orient_matrix_ub_32      0.0615637
_diffrn_orient_matrix_ub_33      0.0074739
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_number            28581
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         29.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_reflns_Friedel_coverage         0
_reflns_number_total             5258
_reflns_number_gt                3280
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.8228P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5258
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O61 O 0.10255(11) 0.43985(12) 0.06274(9) 0.0256(3) Uani 1 1 d . . . . .
O63 O -0.01010(11) 0.63516(13) 0.10259(10) 0.0271(3) Uani 1 1 d . . . . .
O60 O 0.20195(12) 0.43721(13) 0.20148(10) 0.0306(4) Uani 1 1 d . . . . .
N51 N 0.50485(12) 0.55911(13) 0.36851(11) 0.0198(4) Uani 1 1 d . . . . .
O62 O 0.09927(12) 0.65076(12) 0.23369(10) 0.0301(4) Uani 1 1 d . . . . .
N54 N 0.26800(13) 0.51907(14) 0.37154(12) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.61698(15) 0.57829(17) 0.35109(13) 0.0202(4) Uani 1 1 d . . . . .
C55 C 0.31916(15) 0.64128(17) 0.37886(14) 0.0225(4) Uani 1 1 d . . . . .
H55A H 0.3426 0.6615 0.4432 0.027 Uiso 1 1 calc R U . . .
H55B H 0.2627 0.701 0.3528 0.027 Uiso 1 1 calc R U . . .
N1 N 0.81194(13) 0.82298(14) 0.38770(11) 0.0230(4) Uani 1 1 d . . . . .
C56 C 0.41976(15) 0.64500(17) 0.32911(13) 0.0214(4) Uani 1 1 d . . . . .
H56A H 0.3961 0.6256 0.2646 0.026 Uiso 1 1 calc R U . . .
H56B H 0.4523 0.7265 0.3327 0.026 Uiso 1 1 calc R U . . .
C4 C 0.66926(15) 0.68978(16) 0.37508(12) 0.0189(4) Uani 1 1 d . . . . .
C14 C 1.15993(17) 0.78020(17) 0.62372(15) 0.0270(5) Uani 1 1 d . . . . .
H14 H 1.2126 0.7615 0.6754 0.032 Uiso 1 1 calc R U . . .
C52 C 0.45868(16) 0.43856(17) 0.35495(14) 0.0230(4) Uani 1 1 d . . . . .
H52B H 0.5161 0.3792 0.3797 0.028 Uiso 1 1 calc R U . . .
H52A H 0.4382 0.4228 0.2896 0.028 Uiso 1 1 calc R U . . .
C60 C 0.13142(16) 0.47962(17) 0.14014(14) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.78171(16) 0.70847(17) 0.35955(13) 0.0211(4) Uani 1 1 d . . . . .
C61 C 0.07253(16) 0.59671(17) 0.16422(13) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.68147(16) 0.49167(18) 0.31643(13) 0.0245(4) Uani 1 1 d . . . . .
H6 H 0.6492 0.4154 0.3016 0.029 Uiso 1 1 calc R U . . .
C15 C 1.19712(16) 0.81754(17) 0.54520(14) 0.0256(5) Uani 1 1 d . . . . .
H15 H 1.2757 0.8239 0.5427 0.031 Uiso 1 1 calc R U . . .
C11 C 1.00496(15) 0.83771(16) 0.47270(13) 0.0212(4) Uani 1 1 d . . . . .
C16 C 1.12043(16) 0.84584(17) 0.46985(14) 0.0238(4) Uani 1 1 d . . . . .
H16 H 1.1468 0.871 0.4159 0.029 Uiso 1 1 calc R U . . .
C8 C 0.84522(16) 0.62162(18) 0.32336(13) 0.0258(5) Uani 1 1 d . . . . .
H8 H 0.9206 0.6362 0.3135 0.031 Uiso 1 1 calc R U . . .
C53 C 0.35536(16) 0.42653(18) 0.40195(14) 0.0248(4) Uani 1 1 d . . . . .
H53A H 0.3222 0.3461 0.3897 0.03 Uiso 1 1 calc R U . . .
H53B H 0.3781 0.4339 0.468 0.03 Uiso 1 1 calc R U . . .
C2 C 0.72347(16) 0.87363(18) 0.42327(14) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.7239 0.9515 0.4487 0.031 Uiso 1 1 calc R U . . .
C10 C 0.92402(16) 0.87402(18) 0.39067(14) 0.0260(5) Uani 1 1 d . . . . .
H10A H 0.9176 0.9623 0.3895 0.031 Uiso 1 1 calc R U . . .
H10B H 0.9555 0.8491 0.3358 0.031 Uiso 1 1 calc R U . . .
C3 C 0.63533(16) 0.79632(17) 0.41690(13) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.5644 0.8103 0.4365 0.027 Uiso 1 1 calc R U . . .
C7 C 0.79341(17) 0.51344(19) 0.30249(14) 0.0274(5) Uani 1 1 d . . . . .
H7 H 0.8343 0.4517 0.278 0.033 Uiso 1 1 calc R U . . .
C12 C 0.96836(17) 0.79889(18) 0.55203(14) 0.0269(5) Uani 1 1 d . . . . .
H12 H 0.8899 0.7921 0.5549 0.032 Uiso 1 1 calc R U . . .
C13 C 1.04531(17) 0.77010(18) 0.62685(14) 0.0288(5) Uani 1 1 d . . . . .
H13 H 1.0194 0.7433 0.6806 0.035 Uiso 1 1 calc R U . . .
C57 C 0.17083(17) 0.5103(2) 0.42388(15) 0.0312(5) Uani 1 1 d . . . . .
H57A H 0.1391 0.4295 0.4179 0.047 Uiso 1 1 calc R U . . .
H57C H 0.1969 0.5273 0.4877 0.047 Uiso 1 1 calc R U . . .
H57B H 0.1129 0.5685 0.4004 0.047 Uiso 1 1 calc R U . . .
H54 H 0.2395(18) 0.5024(19) 0.3082(16) 0.037(6) Uiso 1 1 d . . . . .
H63 H -0.017(2) 0.586(2) 0.0533(18) 0.051(8) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O61 C60 1.243(2) . ?
O63 C61 1.325(2) . ?
O63 H63 0.92(3) . ?
O60 C60 1.250(2) . ?
N51 C5 1.420(2) . ?
N51 C52 1.461(2) . ?
N51 C56 1.463(2) . ?
O62 C61 1.206(2) . ?
N54 C57 1.495(2) . ?
N54 C55 1.496(2) . ?
N54 C53 1.496(2) . ?
N54 H54 0.98(2) . ?
C5 C6 1.385(3) . ?
C5 C4 1.419(3) . ?
C55 C56 1.504(3) . ?
C55 H55A 0.99 . ?
C55 H55B 0.99 . ?
N1 C2 1.374(2) . ?
N1 C9 1.381(2) . ?
N1 C10 1.454(2) . ?
C56 H56A 0.99 . ?
C56 H56B 0.99 . ?
C4 C9 1.415(3) . ?
C4 C3 1.431(3) . ?
C14 C15 1.378(3) . ?
C14 C13 1.385(3) . ?
C14 H14 0.95 . ?
C52 C53 1.513(3) . ?
C52 H52B 0.99 . ?
C52 H52A 0.99 . ?
C60 C61 1.554(3) . ?
C9 C8 1.390(3) . ?
C6 C7 1.407(3) . ?
C6 H6 0.95 . ?
C15 C16 1.386(3) . ?
C15 H15 0.95 . ?
C11 C12 1.391(3) . ?
C11 C16 1.393(3) . ?
C11 C10 1.508(3) . ?
C16 H16 0.95 . ?
C8 C7 1.376(3) . ?
C8 H8 0.95 . ?
C53 H53A 0.99 . ?
C53 H53B 0.99 . ?
C2 C3 1.358(3) . ?
C2 H2 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C3 H3 0.95 . ?
C7 H7 0.95 . ?
C12 C13 1.384(3) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C57 H57A 0.98 . ?
C57 H57C 0.98 . ?
C57 H57B 0.98 . ?

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
C61 O63 H63 110.0(16) . . ?
C5 N51 C52 117.61(15) . . ?
C5 N51 C56 116.76(15) . . ?
C52 N51 C56 108.76(14) . . ?
C57 N54 C55 111.26(15) . . ?
C57 N54 C53 111.02(16) . . ?
C55 N54 C53 110.38(14) . . ?
C57 N54 H54 107.6(13) . . ?
C55 N54 H54 109.2(13) . . ?
C53 N54 H54 107.2(13) . . ?
C6 C5 C4 117.39(17) . . ?
C6 C5 N51 123.71(17) . . ?
C4 C5 N51 118.79(16) . . ?
N54 C55 C56 109.74(15) . . ?
N54 C55 H55A 109.7 . . ?
C56 C55 H55A 109.7 . . ?
N54 C55 H55B 109.7 . . ?
C56 C55 H55B 109.7 . . ?
H55A C55 H55B 108.2 . . ?
C2 N1 C9 108.50(15) . . ?
C2 N1 C10 125.87(17) . . ?
C9 N1 C10 125.10(16) . . ?
N51 C56 C55 110.13(16) . . ?
N51 C56 H56A 109.6 . . ?
C55 C56 H56A 109.6 . . ?
N51 C56 H56B 109.6 . . ?
C55 C56 H56B 109.6 . . ?
H56A C56 H56B 108.1 . . ?
C9 C4 C5 119.02(17) . . ?
C9 C4 C3 106.53(16) . . ?
C5 C4 C3 134.43(17) . . ?
C15 C14 C13 119.66(19) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N51 C52 C53 109.65(16) . . ?
N51 C52 H52B 109.7 . . ?
C53 C52 H52B 109.7 . . ?
N51 C52 H52A 109.7 . . ?
C53 C52 H52A 109.7 . . ?
H52B C52 H52A 108.2 . . ?
O61 C60 O60 128.20(18) . . ?
O61 C60 C61 116.22(17) . . ?
O60 C60 C61 115.59(17) . . ?
N1 C9 C8 129.25(18) . . ?
N1 C9 C4 107.58(16) . . ?
C8 C9 C4 123.16(18) . . ?
O62 C61 O63 121.19(18) . . ?
O62 C61 C60 123.25(18) . . ?
O63 C61 C60 115.56(17) . . ?
C5 C6 C7 121.88(19) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C14 C15 C16 120.32(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C12 C11 C16 118.72(18) . . ?
C12 C11 C10 122.27(17) . . ?
C16 C11 C10 119.00(18) . . ?
C15 C16 C11 120.48(19) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C7 C8 C9 116.68(18) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
N54 C53 C52 112.35(16) . . ?
N54 C53 H53A 109.1 . . ?
C52 C53 H53A 109.1 . . ?
N54 C53 H53B 109.1 . . ?
C52 C53 H53B 109.1 . . ?
H53A C53 H53B 107.9 . . ?
C3 C2 N1 110.19(17) . . ?
C3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
N1 C10 C11 113.83(16) . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C2 C3 C4 107.16(17) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C8 C7 C6 121.84(19) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C13 C12 C11 120.53(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N54 C57 H57A 109.5 . . ?
N54 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
N54 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57C C57 H57B 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
C52 N51 C5 C6 4.5(3) . . . . ?
C56 N51 C5 C6 -127.6(2) . . . . ?
C52 N51 C5 C4 -171.65(17) . . . . ?
C56 N51 C5 C4 56.3(2) . . . . ?
C57 N54 C55 C56 177.35(16) . . . . ?
C53 N54 C55 C56 53.6(2) . . . . ?
C5 N51 C56 C55 -159.42(16) . . . . ?
C52 N51 C56 C55 64.6(2) . . . . ?
N54 C55 C56 N51 -60.7(2) . . . . ?
C6 C5 C4 C9 2.3(3) . . . . ?
N51 C5 C4 C9 178.74(17) . . . . ?
C6 C5 C4 C3 -175.4(2) . . . . ?
N51 C5 C4 C3 1.0(3) . . . . ?
C5 N51 C52 C53 163.38(16) . . . . ?
C56 N51 C52 C53 -61.0(2) . . . . ?
C2 N1 C9 C8 -176.7(2) . . . . ?
C10 N1 C9 C8 -4.7(3) . . . . ?
C2 N1 C9 C4 2.3(2) . . . . ?
C10 N1 C9 C4 174.38(17) . . . . ?
C5 C4 C9 N1 179.48(16) . . . . ?
C3 C4 C9 N1 -2.2(2) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C3 C4 C9 C8 176.94(18) . . . . ?
O61 C60 C61 O62 -173.28(19) . . . . ?
O60 C60 C61 O62 6.9(3) . . . . ?
O61 C60 C61 O63 6.3(2) . . . . ?
O60 C60 C61 O63 -173.54(17) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
N51 C5 C6 C7 -178.22(18) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C10 C11 C16 C15 177.53(18) . . . . ?
N1 C9 C8 C7 178.93(19) . . . . ?
C4 C9 C8 C7 0.0(3) . . . . ?
C57 N54 C53 C52 -175.90(16) . . . . ?
C55 N54 C53 C52 -52.0(2) . . . . ?
N51 C52 C53 N54 55.8(2) . . . . ?
C9 N1 C2 C3 -1.6(2) . . . . ?
C10 N1 C2 C3 -173.55(18) . . . . ?
C2 N1 C10 C11 90.2(2) . . . . ?
C9 N1 C10 C11 -80.5(2) . . . . ?
C12 C11 C10 N1 -22.8(3) . . . . ?
C16 C11 C10 N1 158.75(18) . . . . ?
N1 C2 C3 C4 0.2(2) . . . . ?
C9 C4 C3 C2 1.3(2) . . . . ?
C5 C4 C3 C2 179.2(2) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C10 C11 C12 C13 -177.86(19) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C55 H55B O62 0.99 2.52 3.170(2) 123.2 .
C8 H8 O62 0.95 2.6 3.510(2) 160.9 1_655
C53 H53B N51 0.99 2.64 3.604(3) 163.9 3_666
C3 H3 O61 0.95 2.47 3.322(2) 149.1 2
C57 H57B O62 0.98 2.64 3.256(3) 121.1 .
N54 H54 O60 0.98(2) 1.76(2) 2.714(2) 166(2) .
N54 H54 O62 0.98(2) 2.51(2) 3.055(2) 115.2(16) .
O63 H63 O61 0.92(3) 2.17(2) 2.6791(19) 114.5(19) .
O63 H63 O61 0.92(3) 1.91(3) 2.697(2) 143(2) 3_565
C55 H55B O62 0.99 2.52 3.170(2) 123.2 .
C8 H8 O62 0.95 2.6 3.510(2) 160.9 1_655
C53 H53B N51 0.99 2.64 3.604(3) 163.9 3_666
C3 H3 O61 0.95 2.47 3.322(2) 149.1 2
C57 H57B O62 0.98 2.64 3.256(3) 121.1 .
N54 H54 O60 0.98(2) 1.76(2) 2.714(2) 166(2) .
N54 H54 O62 0.98(2) 2.51(2) 3.055(2) 115.2(16) .
O63 H63 O61 0.92(3) 2.17(2) 2.6791(19) 114.5(19) .
O63 H63 O61 0.92(3) 1.91(3) 2.697(2) 143(2) 3_565

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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 1550184'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2017-02-23T23:32:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C25 H26 N4 O4'
_chemical_formula_moiety         'C23 H25 N4, C2HO4'
_chemical_formula_weight         446.5
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I a'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.5126(19)
_cell_length_b                   22.934(16)
_cell_length_c                   11.454(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.85(3)
_cell_angle_gamma                90
_cell_volume                     2196.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    2209
_cell_measurement_theta_min      3.2166
_cell_measurement_theta_max      28.6339

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.35
_exptl_crystal_F_000             944

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.30665
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0230206
_diffrn_orient_matrix_ub_12      -0.0264485
_diffrn_orient_matrix_ub_13      -0.0305057
_diffrn_orient_matrix_ub_21      0.0120381
_diffrn_orient_matrix_ub_22      -0.0150794
_diffrn_orient_matrix_ub_23      0.0550818
_diffrn_orient_matrix_ub_31      -0.0807148
_diffrn_orient_matrix_ub_32      0.005274
_diffrn_orient_matrix_ub_33      0.0044576
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.175
_diffrn_reflns_av_unetI/netI     0.2016
_diffrn_reflns_number            13886
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_max         28.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.9
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_coverage         0.916
_reflns_number_total             5103
_reflns_number_gt                1906
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5103
_refine_ls_number_parameters     307
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2077
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O32 O 0.3594(9) 0.2523(4) 0.4547(7) 0.075(2) Uani 1 1 d . . . . .
C11 C 0.2075(9) 0.0111(4) 0.6606(8) 0.048(2) Uani 1 1 d . . . . .
O31 O 0.4784(8) 0.2600(3) 0.6884(6) 0.078(2) Uani 1 1 d . . . . .
O30 O 0.2313(7) 0.2558(3) 0.7265(6) 0.0650(18) Uani 1 1 d . . . . .
C15 C 0.0774(10) 0.0105(4) 0.8331(8) 0.054(2) Uani 1 1 d . . . . .
C20 C 0.1408(10) -0.0207(4) 0.7452(8) 0.048(2) Uani 1 1 d . . . . .
N1 N 0.1670(8) -0.0497(3) 0.4752(6) 0.0520(19) Uani 1 1 d . . . . .
C9 C 0.0594(10) -0.0239(4) 0.3854(8) 0.047(2) Uani 1 1 d . . . . .
N71 N -0.1227(8) 0.1075(3) 0.2280(6) 0.0490(18) Uani 1 1 d . . . . .
C19 C 0.1351(10) -0.0820(4) 0.7472(8) 0.058(2) Uani 1 1 d . . . . .
H19 H 0.1767 -0.1033 0.691 0.069 Uiso 1 1 calc R U . . .
C5 C -0.1397(11) -0.0537(4) 0.2165(8) 0.056(2) Uani 1 1 d . . . . .
H5 H -0.1965 -0.0823 0.1684 0.068 Uiso 1 1 calc R U . . .
N74 N -0.1086(9) 0.2264(3) 0.1514(7) 0.0509(18) Uani 1 1 d . . . . .
O33 O 0.1202(8) 0.2714(4) 0.4909(6) 0.096(3) Uani 1 1 d . . . . .
C12 C 0.2101(10) 0.0703(4) 0.6641(9) 0.057(2) Uani 1 1 d . . . . .
H12 H 0.2545 0.0906 0.6079 0.068 Uiso 1 1 calc R U . . .
C6 C -0.1682(10) 0.0038(4) 0.1922(8) 0.053(2) Uani 1 1 d . . . . .
H6 H -0.2473 0.0138 0.1277 0.064 Uiso 1 1 calc R U . . .
C8 C 0.0347(10) 0.0343(4) 0.3587(8) 0.052(2) Uani 1 1 d . . . . .
H8 H 0.0942 0.0631 0.4041 0.063 Uiso 1 1 calc R U . . .
C75 C -0.1242(11) 0.2113(4) 0.2751(8) 0.055(2) Uani 1 1 d . . . . .
H75A H -0.2363 0.2102 0.2811 0.066 Uiso 1 1 calc R U . . .
H75B H -0.0717 0.2407 0.3297 0.066 Uiso 1 1 calc R U . . .
C7 C -0.0839(10) 0.0485(4) 0.2600(8) 0.049(2) Uani 1 1 d . . . . .
C32 C 0.2600(11) 0.2615(4) 0.5255(8) 0.057(3) Uani 1 1 d . . . . .
C17 C 0.0072(12) -0.0800(6) 0.9190(9) 0.070(3) Uani 1 1 d . . . . .
H17 H -0.0359 -0.1001 0.9762 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2808(11) -0.0208(4) 0.5660(8) 0.059(3) Uani 1 1 d . . . . .
H10A H 0.3405 0.0071 0.5281 0.07 Uiso 1 1 calc R U . . .
H10B H 0.3562 -0.0496 0.6054 0.07 Uiso 1 1 calc R U . . .
C14 C 0.0813(11) 0.0723(5) 0.8329(10) 0.068(3) Uani 1 1 d . . . . .
H14 H 0.0383 0.0929 0.8893 0.082 Uiso 1 1 calc R U . . .
N2 N 0.1590(10) -0.1096(3) 0.4688(7) 0.061(2) Uani 1 1 d . . . . .
C77 C -0.1785(10) 0.2844(4) 0.1170(8) 0.060(3) Uani 1 1 d . . . . .
H77A H -0.1676 0.2931 0.037 0.091 Uiso 1 1 calc R U . . .
H77B H -0.1235 0.3135 0.1697 0.091 Uiso 1 1 calc R U . . .
H77C H -0.2898 0.2844 0.1222 0.091 Uiso 1 1 calc R U . . .
C31 C 0.3335(11) 0.2580(4) 0.6603(8) 0.053(2) Uani 1 1 d . . . . .
C18 C 0.0687(10) -0.1104(5) 0.8311(9) 0.063(3) Uani 1 1 d . . . . .
H18 H 0.0642 -0.1509 0.8299 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1473(11) 0.1019(4) 0.7506(9) 0.065(3) Uani 1 1 d . . . . .
H13 H 0.1509 0.1424 0.7516 0.078 Uiso 1 1 calc R U . . .
C4 C -0.0202(11) -0.0697(4) 0.3178(8) 0.055(2) Uani 1 1 d . . . . .
C16 C 0.0117(11) -0.0209(5) 0.9190(8) 0.067(3) Uani 1 1 d . . . . .
H16 H -0.0292 -0.0005 0.9768 0.08 Uiso 1 1 calc R U . . .
C76 C -0.0483(11) 0.1522(4) 0.3077(8) 0.056(2) Uani 1 1 d . . . . .
H76A H 0.0647 0.1541 0.3049 0.068 Uiso 1 1 calc R U . . .
H76B H -0.0585 0.1424 0.3883 0.068 Uiso 1 1 calc R U . . .
C72 C -0.1126(11) 0.1209(4) 0.1041(7) 0.053(2) Uani 1 1 d . . . . .
H72A H -0.1681 0.0911 0.052 0.064 Uiso 1 1 calc R U . . .
H72B H -0.0015 0.1211 0.0953 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0443(12) -0.1210(4) 0.3729(9) 0.062(3) Uani 1 1 d . . . . .
H3 H 0.0123 -0.1583 0.3469 0.074 Uiso 1 1 calc R U . . .
C73 C -0.1869(11) 0.1795(4) 0.0699(8) 0.056(2) Uani 1 1 d . . . . .
H73A H -0.1764 0.1886 -0.011 0.067 Uiso 1 1 calc R U . . .
H73B H -0.3 0.1781 0.0727 0.067 Uiso 1 1 calc R U . . .
H74 H 0.026(9) 0.233(3) 0.159(7) 0.05(2) Uiso 1 1 d . . . . .
H32 H 0.312(15) 0.251(5) 0.376(13) 0.11(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O32 C32 1.295(10) . ?
O32 H32 0.92(14) . ?
C11 C12 1.359(11) . ?
C11 C20 1.414(11) . ?
C11 C10 1.534(12) . ?
O31 C31 1.216(10) . ?
O30 C31 1.258(9) . ?
C15 C16 1.417(13) . ?
C15 C14 1.417(13) . ?
C15 C20 1.421(11) . ?
C20 C19 1.407(12) . ?
N1 N2 1.376(10) . ?
N1 C9 1.376(11) . ?
N1 C10 1.443(11) . ?
C9 C8 1.376(12) . ?
C9 C4 1.402(12) . ?
N71 C7 1.424(11) . ?
N71 C76 1.438(11) . ?
N71 C72 1.470(10) . ?
C19 C18 1.369(12) . ?
C19 H19 0.93 . ?
C5 C6 1.360(11) . ?
C5 C4 1.439(13) . ?
C5 H5 0.93 . ?
N74 C77 1.481(10) . ?
N74 C75 1.488(10) . ?
N74 C73 1.496(11) . ?
N74 H74 1.14(8) . ?
O33 C32 1.203(11) . ?
C12 C13 1.410(12) . ?
C12 H12 0.93 . ?
C6 C7 1.401(12) . ?
C6 H6 0.93 . ?
C8 C7 1.405(11) . ?
C8 H8 0.93 . ?
C75 C76 1.517(12) . ?
C75 H75A 0.97 . ?
C75 H75B 0.97 . ?
C32 C31 1.555(12) . ?
C17 C16 1.356(14) . ?
C17 C18 1.404(13) . ?
C17 H17 0.93 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C14 C13 1.366(14) . ?
C14 H14 0.93 . ?
N2 C3 1.350(12) . ?
C77 H77A 0.96 . ?
C77 H77B 0.96 . ?
C77 H77C 0.96 . ?
C18 H18 0.93 . ?
C13 H13 0.93 . ?
C4 C3 1.398(13) . ?
C16 H16 0.93 . ?
C76 H76A 0.97 . ?
C76 H76B 0.97 . ?
C72 C73 1.506(11) . ?
C72 H72A 0.97 . ?
C72 H72B 0.97 . ?
C3 H3 0.93 . ?
C73 H73A 0.97 . ?
C73 H73B 0.97 . ?

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
C32 O32 H32 114(8) . . ?
C12 C11 C20 120.1(8) . . ?
C12 C11 C10 119.4(8) . . ?
C20 C11 C10 120.5(8) . . ?
C16 C15 C14 121.5(9) . . ?
C16 C15 C20 119.2(10) . . ?
C14 C15 C20 119.3(9) . . ?
C19 C20 C11 123.1(8) . . ?
C19 C20 C15 118.2(8) . . ?
C11 C20 C15 118.7(9) . . ?
N2 N1 C9 111.8(8) . . ?
N2 N1 C10 121.1(8) . . ?
C9 N1 C10 127.0(8) . . ?
C8 C9 N1 129.6(9) . . ?
C8 C9 C4 124.5(9) . . ?
N1 C9 C4 105.9(9) . . ?
C7 N71 C76 117.5(7) . . ?
C7 N71 C72 113.1(7) . . ?
C76 N71 C72 111.4(7) . . ?
C18 C19 C20 120.5(9) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C6 C5 C4 118.9(9) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C77 N74 C75 111.1(7) . . ?
C77 N74 C73 111.8(7) . . ?
C75 N74 C73 108.5(7) . . ?
C77 N74 H74 104(4) . . ?
C75 N74 H74 103(4) . . ?
C73 N74 H74 118(4) . . ?
C11 C12 C13 121.8(9) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C5 C6 C7 122.9(9) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C9 C8 C7 117.4(9) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
N74 C75 C76 109.4(7) . . ?
N74 C75 H75A 109.8 . . ?
C76 C75 H75A 109.8 . . ?
N74 C75 H75B 109.8 . . ?
C76 C75 H75B 109.8 . . ?
H75A C75 H75B 108.2 . . ?
C6 C7 C8 119.5(8) . . ?
C6 C7 N71 118.9(8) . . ?
C8 C7 N71 121.6(8) . . ?
O33 C32 O32 123.2(9) . . ?
O33 C32 C31 121.7(7) . . ?
O32 C32 C31 115.1(8) . . ?
C16 C17 C18 118.7(10) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N1 C10 C11 114.9(7) . . ?
N1 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C13 C14 C15 120.8(9) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C3 N2 N1 104.9(8) . . ?
N74 C77 H77A 109.5 . . ?
N74 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
N74 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
O31 C31 O30 128.6(9) . . ?
O31 C31 C32 117.4(7) . . ?
O30 C31 C32 114.0(7) . . ?
C19 C18 C17 121.8(10) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C14 C13 C12 119.3(10) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C3 C4 C9 105.9(8) . . ?
C3 C4 C5 137.4(10) . . ?
C9 C4 C5 116.7(9) . . ?
C17 C16 C15 121.6(9) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
N71 C76 C75 111.4(8) . . ?
N71 C76 H76A 109.4 . . ?
C75 C76 H76A 109.4 . . ?
N71 C76 H76B 109.4 . . ?
C75 C76 H76B 109.4 . . ?
H76A C76 H76B 108 . . ?
N71 C72 C73 109.8(7) . . ?
N71 C72 H72A 109.7 . . ?
C73 C72 H72A 109.7 . . ?
N71 C72 H72B 109.7 . . ?
C73 C72 H72B 109.7 . . ?
H72A C72 H72B 108.2 . . ?
N2 C3 C4 111.6(9) . . ?
N2 C3 H3 124.2 . . ?
C4 C3 H3 124.2 . . ?
N74 C73 C72 111.3(7) . . ?
N74 C73 H73A 109.4 . . ?
C72 C73 H73A 109.4 . . ?
N74 C73 H73B 109.4 . . ?
C72 C73 H73B 109.4 . . ?
H73A C73 H73B 108 . . ?

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
C12 C11 C20 C19 -179.6(8) . . . . ?
C10 C11 C20 C19 -1.0(13) . . . . ?
C12 C11 C20 C15 -0.1(13) . . . . ?
C10 C11 C20 C15 178.5(7) . . . . ?
C16 C15 C20 C19 0.2(12) . . . . ?
C14 C15 C20 C19 -179.8(8) . . . . ?
C16 C15 C20 C11 -179.4(8) . . . . ?
C14 C15 C20 C11 0.7(13) . . . . ?
N2 N1 C9 C8 -177.4(7) . . . . ?
C10 N1 C9 C8 1.0(12) . . . . ?
N2 N1 C9 C4 -0.5(8) . . . . ?
C10 N1 C9 C4 177.9(7) . . . . ?
C11 C20 C19 C18 -179.9(8) . . . . ?
C15 C20 C19 C18 0.6(13) . . . . ?
C20 C11 C12 C13 -0.1(14) . . . . ?
C10 C11 C12 C13 -178.7(8) . . . . ?
C4 C5 C6 C7 1.4(12) . . . . ?
N1 C9 C8 C7 179.4(7) . . . . ?
C4 C9 C8 C7 3.1(11) . . . . ?
C77 N74 C75 C76 -178.8(7) . . . . ?
C73 N74 C75 C76 57.9(9) . . . . ?
C5 C6 C7 C8 -0.8(11) . . . . ?
C5 C6 C7 N71 -179.7(7) . . . . ?
C9 C8 C7 C6 -1.5(10) . . . . ?
C9 C8 C7 N71 177.4(7) . . . . ?
C76 N71 C7 C6 172.4(7) . . . . ?
C72 N71 C7 C6 -55.5(10) . . . . ?
C76 N71 C7 C8 -6.5(10) . . . . ?
C72 N71 C7 C8 125.6(8) . . . . ?
N2 N1 C10 C11 -110.6(8) . . . . ?
C9 N1 C10 C11 71.1(10) . . . . ?
C12 C11 C10 N1 -110.7(10) . . . . ?
C20 C11 C10 N1 70.7(11) . . . . ?
C16 C15 C14 C13 178.9(9) . . . . ?
C20 C15 C14 C13 -1.1(14) . . . . ?
C9 N1 N2 C3 0.1(9) . . . . ?
C10 N1 N2 C3 -178.4(7) . . . . ?
O33 C32 C31 O31 -165.1(10) . . . . ?
O32 C32 C31 O31 15.8(14) . . . . ?
O33 C32 C31 O30 12.0(15) . . . . ?
O32 C32 C31 O30 -167.1(8) . . . . ?
C20 C19 C18 C17 -1.2(14) . . . . ?
C16 C17 C18 C19 1.1(15) . . . . ?
C15 C14 C13 C12 0.9(14) . . . . ?
C11 C12 C13 C14 -0.4(14) . . . . ?
C8 C9 C4 C3 177.7(7) . . . . ?
N1 C9 C4 C3 0.7(8) . . . . ?
C8 C9 C4 C5 -2.5(11) . . . . ?
N1 C9 C4 C5 -179.5(7) . . . . ?
C6 C5 C4 C3 179.8(9) . . . . ?
C6 C5 C4 C9 0.1(11) . . . . ?
C18 C17 C16 C15 -0.3(15) . . . . ?
C14 C15 C16 C17 179.6(10) . . . . ?
C20 C15 C16 C17 -0.3(14) . . . . ?
C7 N71 C76 C75 -169.0(7) . . . . ?
C72 N71 C76 C75 58.2(9) . . . . ?
N74 C75 C76 N71 -59.1(9) . . . . ?
C7 N71 C72 C73 168.5(7) . . . . ?
C76 N71 C72 C73 -56.6(9) . . . . ?
N1 N2 C3 C4 0.3(9) . . . . ?
C9 C4 C3 N2 -0.7(9) . . . . ?
C5 C4 C3 N2 179.6(9) . . . . ?
C77 N74 C73 C72 178.8(7) . . . . ?
C75 N74 C73 C72 -58.4(9) . . . . ?
N71 C72 C73 N74 57.1(9) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1550189'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-08-25T22:24:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C45 H54 N6 O9'
_chemical_formula_moiety         '2(C20 H24 N3), C2 O4, C2 H2 O4, C H4 O'
_chemical_formula_weight         822.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0646(2)
_cell_length_b                   25.5172(4)
_cell_length_c                   15.8131(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.833(2)
_cell_angle_gamma                90
_cell_volume                     4250.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    20798
_cell_measurement_theta_min      3.0721
_cell_measurement_theta_max      28.6504

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1752

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.86471
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0047625
_diffrn_orient_matrix_ub_12      0.021841
_diffrn_orient_matrix_ub_13      0.0265386
_diffrn_orient_matrix_ub_21      0.0005296
_diffrn_orient_matrix_ub_22      -0.0171082
_diffrn_orient_matrix_ub_23      0.0354553
_diffrn_orient_matrix_ub_31      0.0671847
_diffrn_orient_matrix_ub_32      0.0016834
_diffrn_orient_matrix_ub_33      0.0160902
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_number            58649
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         28.714
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.95
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.95
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.95
_reflns_Friedel_coverage         0
_reflns_number_total             10446
_reflns_number_gt                8163
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+2.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10446
_refine_ls_number_parameters     561
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O60 O 0.57726(9) 0.19240(4) 1.05509(7) 0.0236(2) Uani 1 1 d D . . . .
O61 O 0.55613(10) 0.25133(5) 1.15445(8) 0.0332(3) Uani 1 1 d . . . . .
C60 C 0.51294(13) 0.22048(6) 1.09479(9) 0.0204(3) Uani 1 1 d . . . . .
O63 O 0.30432(10) 0.23193(5) 1.10146(8) 0.0353(3) Uani 1 1 d D . . . .
O62 O 0.32562(10) 0.18668(6) 0.98726(8) 0.0491(4) Uani 1 1 d . . . . .
C61 C 0.36803(13) 0.21129(6) 1.05545(10) 0.0236(3) Uani 1 1 d . . . . .
O71 O 0.39569(14) 0.10004(6) 0.90547(10) 0.0503(4) Uani 1 1 d . . . . .
C70 C 0.5163(2) 0.08493(11) 0.90448(16) 0.0655(7) Uani 1 1 d . . . . .
H70A H 0.5697 0.1161 0.9088 0.098 Uiso 1 1 calc R U . . .
H70B H 0.5096 0.0664 0.849 0.098 Uiso 1 1 calc R U . . .
H70C H 0.5545 0.0617 0.955 0.098 Uiso 1 1 calc R U . . .
H34 H 0.9103(15) 0.2127(6) 0.8915(12) 0.023(4) Uiso 1 1 d . . . . .
H60 H 0.6614(11) 0.2010(9) 1.0745(16) 0.071(8) Uiso 1 1 d D . . . .
H63 H 0.2188(10) 0.2265(11) 1.0781(17) 0.086(9) Uiso 1 1 d D . . . .
H71 H 0.399(3) 0.1321(14) 0.947(2) 0.129 Uiso 1 1 d . U . . .
H4AA H -0.0625(16) 0.2294(7) 0.2425(12) 0.025(4) Uiso 1 1 d . . . . .
O53 O 0.81705(9) 0.21416(5) 0.97248(7) 0.0259(2) Uani 1 1 d . . . . .
O50 O 1.07253(9) 0.22043(4) 1.03716(7) 0.0260(2) Uani 1 1 d . . . . .
O52 O 0.80757(9) 0.21388(4) 1.11135(7) 0.0227(2) Uani 1 1 d . . . . .
O51 O 1.05710(9) 0.23340(4) 1.17322(7) 0.0263(2) Uani 1 1 d . . . . .
N34 N 0.92449(11) 0.21425(5) 0.83873(8) 0.0185(2) Uani 1 1 d . . . . .
N31 N 0.93509(10) 0.10239(5) 0.81548(8) 0.0192(2) Uani 1 1 d . . . . .
C50 C 1.01174(12) 0.22455(5) 1.09334(9) 0.0174(3) Uani 1 1 d . . . . .
C51 C 0.86544(12) 0.21696(5) 1.05384(9) 0.0173(3) Uani 1 1 d . . . . .
C32 C 1.04015(13) 0.13182(6) 0.87724(9) 0.0204(3) Uani 1 1 d . . . . .
H32A H 1.1213 0.1137 0.8828 0.024 Uiso 1 1 calc R U . . .
H32B H 1.028 0.1326 0.9367 0.024 Uiso 1 1 calc R U . . .
N1 N 0.86472(12) -0.02541(5) 0.89044(9) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.93025(13) 0.04998(6) 0.84472(9) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.83192(14) 0.02556(6) 0.86411(10) 0.0247(3) Uani 1 1 d . . . . .
H2 H 0.7526 0.0414 0.86 0.03 Uiso 1 1 calc R U . . .
C33 C 1.04694(13) 0.18716(6) 0.84556(9) 0.0194(3) Uani 1 1 d . . . . .
H33A H 1.1183 0.206 0.8879 0.023 Uiso 1 1 calc R U . . .
H33B H 1.0615 0.1868 0.7868 0.023 Uiso 1 1 calc R U . . .
C35 C 0.82084(13) 0.18557(6) 0.77168(9) 0.0214(3) Uani 1 1 d . . . . .
H35B H 0.8376 0.1855 0.7137 0.026 Uiso 1 1 calc R U . . .
H35A H 0.7387 0.2034 0.764 0.026 Uiso 1 1 calc R U . . .
C36 C 0.81429(13) 0.12993(6) 0.80261(9) 0.0211(3) Uani 1 1 d . . . . .
H36A H 0.7936 0.1303 0.8593 0.025 Uiso 1 1 calc R U . . .
H36B H 0.7457 0.1109 0.7581 0.025 Uiso 1 1 calc R U . . .
C8 C 1.05948(15) -0.07994(6) 0.90755(10) 0.0273(3) Uani 1 1 d . . . . .
H8 H 1.0274 -0.1112 0.9254 0.033 Uiso 1 1 calc R U . . .
C37 C 0.92819(15) 0.27086(6) 0.81919(10) 0.0255(3) Uani 1 1 d . . . . .
H37A H 0.9978 0.2875 0.8653 0.038 Uiso 1 1 calc R U . . .
H37B H 0.9417 0.2754 0.7612 0.038 Uiso 1 1 calc R U . . .
H37C H 0.8475 0.2871 0.8182 0.038 Uiso 1 1 calc R U . . .
C4 C 1.03116(13) 0.01217(6) 0.85943(9) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.66783(14) -0.07723(6) 0.83101(10) 0.0240(3) Uani 1 1 d . . . . .
C9 C 0.98568(14) -0.03457(6) 0.88801(9) 0.0230(3) Uani 1 1 d . . . . .
C6 C 1.22685(15) -0.03210(6) 0.87233(11) 0.0306(4) Uani 1 1 d . . . . .
H6 H 1.3105 -0.0318 0.8678 0.037 Uiso 1 1 calc R U . . .
C5 C 1.15372(14) 0.01254(6) 0.85139(10) 0.0246(3) Uani 1 1 d . . . . .
H5 H 1.186 0.0432 0.8318 0.03 Uiso 1 1 calc R U . . .
C10 C 0.77908(15) -0.06314(7) 0.91117(10) 0.0290(3) Uani 1 1 d . . . . .
H10A H 0.7465 -0.0484 0.9579 0.035 Uiso 1 1 calc R U . . .
H10B H 0.8271 -0.0954 0.9352 0.035 Uiso 1 1 calc R U . . .
C16 C 0.55040(15) -0.08745(6) 0.84136(11) 0.0290(3) Uani 1 1 d . . . . .
H16 H 0.5396 -0.0848 0.8985 0.035 Uiso 1 1 calc R U . . .
C12 C 0.68173(17) -0.08105(7) 0.74690(11) 0.0329(4) Uani 1 1 d . . . . .
H12 H 0.7621 -0.0744 0.739 0.04 Uiso 1 1 calc R U . . .
C13 C 0.57915(18) -0.09448(7) 0.67429(11) 0.0370(4) Uani 1 1 d . . . . .
H13 H 0.5893 -0.0966 0.6169 0.044 Uiso 1 1 calc R U . . .
C14 C 0.46229(16) -0.10478(7) 0.68539(12) 0.0356(4) Uani 1 1 d . . . . .
H14 H 0.392 -0.114 0.6357 0.043 Uiso 1 1 calc R U . . .
C7 C 1.18036(16) -0.07796(6) 0.90017(11) 0.0312(4) Uani 1 1 d . . . . .
H7 H 1.233 -0.1081 0.9142 0.037 Uiso 1 1 calc R U . . .
C15 C 0.44824(16) -0.10153(7) 0.76893(13) 0.0371(4) Uani 1 1 d . . . . .
H15 H 0.3683 -0.109 0.7769 0.045 Uiso 1 1 calc R U . . .
N31A N 0.00972(11) 0.14894(5) 0.39917(8) 0.0218(3) Uani 1 1 d . . . . .
N34A N -0.07961(11) 0.23992(5) 0.29203(8) 0.0201(2) Uani 1 1 d . . . . .
C3A C 0.06322(13) 0.09852(6) 0.42427(9) 0.0223(3) Uani 1 1 d . . . . .
C32A C 0.09967(13) 0.18609(6) 0.38041(10) 0.0243(3) Uani 1 1 d . . . . .
H2AA H 0.1208 0.1746 0.3268 0.029 Uiso 1 1 calc R U . . .
H2AB H 0.1791 0.1866 0.4309 0.029 Uiso 1 1 calc R U . . .
C33A C 0.04332(13) 0.24044(6) 0.36572(10) 0.0244(3) Uani 1 1 d . . . . .
H3AA H 0.0288 0.2531 0.421 0.029 Uiso 1 1 calc R U . . .
H3AB H 0.1034 0.2647 0.3506 0.029 Uiso 1 1 calc R U . . .
C4A C 0.14114(13) 0.08524(6) 0.51223(10) 0.0224(3) Uani 1 1 d . . . . .
C10A C 0.10170(15) -0.04193(6) 0.39954(11) 0.0286(3) Uani 1 1 d . . . . .
H1AB H 0.0512 -0.0445 0.3361 0.034 Uiso 1 1 calc R U . . .
H1AA H 0.0559 -0.0616 0.4342 0.034 Uiso 1 1 calc R U . . .
N1A N 0.10961(12) 0.01271(5) 0.42620(9) 0.0271(3) Uani 1 1 d . . . . .
C36A C -0.10721(14) 0.14764(6) 0.32462(10) 0.0255(3) Uani 1 1 d . . . . .
H6AB H -0.1665 0.1217 0.3365 0.031 Uiso 1 1 calc R U . . .
H6AA H -0.088 0.1369 0.27 0.031 Uiso 1 1 calc R U . . .
C11A C 0.22918(14) -0.06745(6) 0.41240(10) 0.0260(3) Uani 1 1 d . . . . .
C37A C -0.13685(15) 0.29291(6) 0.27451(11) 0.0279(3) Uani 1 1 d . . . . .
H7AB H -0.0758 0.3172 0.2621 0.042 Uiso 1 1 calc R U . . .
H7AA H -0.2137 0.2915 0.2232 0.042 Uiso 1 1 calc R U . . .
H7AC H -0.1589 0.3051 0.3267 0.042 Uiso 1 1 calc R U . . .
C9A C 0.16689(14) 0.03112(6) 0.51095(10) 0.0241(3) Uani 1 1 d . . . . .
C2A C 0.04669(14) 0.05364(6) 0.37454(10) 0.0263(3) Uani 1 1 d . . . . .
H2A H -0.0011 0.0511 0.3135 0.032 Uiso 1 1 calc R U . . .
C7A C 0.27572(16) 0.03238(7) 0.66557(11) 0.0312(4) Uani 1 1 d . . . . .
H6A H 0.3221 0.015 0.7187 0.037 Uiso 1 1 calc R U . . .
C5A C 0.18423(15) 0.11302(6) 0.59243(10) 0.0262(3) Uani 1 1 d . . . . .
H8A H 0.1681 0.1495 0.5946 0.031 Uiso 1 1 calc R U . . .
C35A C -0.16821(13) 0.20112(6) 0.31148(10) 0.0247(3) Uani 1 1 d . . . . .
H5AA H -0.2482 0.2 0.2615 0.03 Uiso 1 1 calc R U . . .
H5AB H -0.1887 0.2117 0.3658 0.03 Uiso 1 1 calc R U . . .
C8A C 0.23458(15) 0.00405(6) 0.58762(10) 0.0276(3) Uani 1 1 d . . . . .
H7A H 0.2516 -0.0324 0.5862 0.033 Uiso 1 1 calc R U . . .
C6A C 0.25079(16) 0.08610(7) 0.66827(10) 0.0305(4) Uani 1 1 d . . . . .
H5A H 0.2801 0.1043 0.7232 0.037 Uiso 1 1 calc R U . . .
C16A C 0.24586(18) -0.11985(7) 0.43530(11) 0.0371(4) Uani 1 1 d . . . . .
H6P H 0.1784 -0.1391 0.4459 0.045 Uiso 1 1 calc R U . . .
C12A C 0.33003(17) -0.03986(8) 0.39909(13) 0.0403(4) Uani 1 1 d . . . . .
H2P H 0.3209 -0.0037 0.384 0.048 Uiso 1 1 calc R U . . .
C13A C 0.44445(19) -0.06523(12) 0.40790(16) 0.0647(7) Uani 1 1 d . . . . .
H3P H 0.5135 -0.0462 0.3992 0.078 Uiso 1 1 calc R U . . .
C14A C 0.4583(2) -0.11739(13) 0.42909(16) 0.0736(9) Uani 1 1 d . . . . .
H4P H 0.5363 -0.1346 0.4341 0.088 Uiso 1 1 calc R U . . .
C15A C 0.3602(2) -0.14455(10) 0.44290(14) 0.0608(7) Uani 1 1 d . . . . .
H5P H 0.3702 -0.1807 0.4578 0.073 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O60 C60 1.2990(17) . ?
O60 H60 0.914(10) . ?
O61 C60 1.2092(18) . ?
C60 C61 1.5498(19) . ?
O63 C61 1.2719(18) . ?
O63 H63 0.915(10) . ?
O62 C61 1.2114(19) . ?
O71 C70 1.394(3) . ?
O71 H71 1.05(4) . ?
C70 H70A 0.98 . ?
C70 H70B 0.98 . ?
C70 H70C 0.98 . ?
O53 C51 1.2350(17) . ?
O50 C50 1.2723(16) . ?
O52 C51 1.2649(16) . ?
O51 C50 1.2288(17) . ?
N34 C37 1.4805(19) . ?
N34 C35 1.4934(18) . ?
N34 C33 1.4952(17) . ?
N34 H34 0.896(18) . ?
N31 C3 1.4214(19) . ?
N31 C36 1.4680(17) . ?
N31 C32 1.4743(17) . ?
C50 C51 1.5585(18) . ?
C32 C33 1.508(2) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
N1 C9 1.371(2) . ?
N1 C2 1.380(2) . ?
N1 C10 1.4568(19) . ?
C3 C2 1.368(2) . ?
C3 C4 1.440(2) . ?
C2 H2 0.95 . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C35 C36 1.511(2) . ?
C35 H35B 0.99 . ?
C35 H35A 0.99 . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C8 C7 1.379(2) . ?
C8 C9 1.396(2) . ?
C8 H8 0.95 . ?
C37 H37A 0.98 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C4 C5 1.400(2) . ?
C4 C9 1.421(2) . ?
C11 C16 1.383(2) . ?
C11 C12 1.388(2) . ?
C11 C10 1.515(2) . ?
C6 C5 1.378(2) . ?
C6 C7 1.402(2) . ?
C6 H6 0.95 . ?
C5 H5 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C16 C15 1.388(2) . ?
C16 H16 0.95 . ?
C12 C13 1.388(2) . ?
C12 H12 0.95 . ?
C13 C14 1.382(3) . ?
C13 H13 0.95 . ?
C14 C15 1.379(3) . ?
C14 H14 0.95 . ?
C7 H7 0.95 . ?
C15 H15 0.95 . ?
N31A C3A 1.4212(19) . ?
N31A C36A 1.4597(18) . ?
N31A C32A 1.4690(18) . ?
N34A C37A 1.4826(19) . ?
N34A C35A 1.4901(18) . ?
N34A C33A 1.4958(18) . ?
N34A H4AA 0.901(18) . ?
C3A C2A 1.369(2) . ?
C3A C4A 1.435(2) . ?
C32A C33A 1.509(2) . ?
C32A H2AA 0.99 . ?
C32A H2AB 0.99 . ?
C33A H3AA 0.99 . ?
C33A H3AB 0.99 . ?
C4A C5A 1.403(2) . ?
C4A C9A 1.411(2) . ?
C10A N1A 1.452(2) . ?
C10A C11A 1.510(2) . ?
C10A H1AB 0.99 . ?
C10A H1AA 0.99 . ?
N1A C2A 1.376(2) . ?
N1A C9A 1.3778(19) . ?
C36A C35A 1.508(2) . ?
C36A H6AB 0.99 . ?
C36A H6AA 0.99 . ?
C11A C16A 1.383(2) . ?
C11A C12A 1.389(2) . ?
C37A H7AB 0.98 . ?
C37A H7AA 0.98 . ?
C37A H7AC 0.98 . ?
C9A C8A 1.397(2) . ?
C2A H2A 0.95 . ?
C7A C8A 1.380(2) . ?
C7A C6A 1.402(2) . ?
C7A H6A 0.95 . ?
C5A C6A 1.383(2) . ?
C5A H8A 0.95 . ?
C35A H5AA 0.99 . ?
C35A H5AB 0.99 . ?
C8A H7A 0.95 . ?
C6A H5A 0.95 . ?
C16A C15A 1.386(3) . ?
C16A H6P 0.95 . ?
C12A C13A 1.390(3) . ?
C12A H2P 0.95 . ?
C13A C14A 1.370(4) . ?
C13A H3P 0.95 . ?
C14A C15A 1.360(4) . ?
C14A H4P 0.95 . ?
C15A H5P 0.95 . ?

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
C60 O60 H60 111.0(16) . . ?
O61 C60 O60 126.31(13) . . ?
O61 C60 C61 121.65(13) . . ?
O60 C60 C61 112.03(12) . . ?
C61 O63 H63 113.0(17) . . ?
O62 C61 O63 126.32(13) . . ?
O62 C61 C60 120.46(13) . . ?
O63 C61 C60 113.23(12) . . ?
C70 O71 H71 112(2) . . ?
O71 C70 H70A 109.5 . . ?
O71 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
O71 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C37 N34 C35 113.22(11) . . ?
C37 N34 C33 112.57(11) . . ?
C35 N34 C33 107.85(11) . . ?
C37 N34 H34 105.1(11) . . ?
C35 N34 H34 109.0(11) . . ?
C33 N34 H34 109.0(11) . . ?
C3 N31 C36 111.84(11) . . ?
C3 N31 C32 111.36(11) . . ?
C36 N31 C32 110.35(11) . . ?
O51 C50 O50 126.60(12) . . ?
O51 C50 C51 118.81(12) . . ?
O50 C50 C51 114.59(12) . . ?
O53 C51 O52 126.30(12) . . ?
O53 C51 C50 119.37(12) . . ?
O52 C51 C50 114.33(12) . . ?
N31 C32 C33 111.48(11) . . ?
N31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108 . . ?
C9 N1 C2 108.73(12) . . ?
C9 N1 C10 126.98(13) . . ?
C2 N1 C10 124.17(13) . . ?
C2 C3 N31 127.84(13) . . ?
C2 C3 C4 106.81(13) . . ?
N31 C3 C4 125.34(12) . . ?
C3 C2 N1 110.08(13) . . ?
C3 C2 H2 125 . . ?
N1 C2 H2 125 . . ?
N34 C33 C32 108.70(11) . . ?
N34 C33 H33A 109.9 . . ?
C32 C33 H33A 109.9 . . ?
N34 C33 H33B 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
N34 C35 C36 109.46(11) . . ?
N34 C35 H35B 109.8 . . ?
C36 C35 H35B 109.8 . . ?
N34 C35 H35A 109.8 . . ?
C36 C35 H35A 109.8 . . ?
H35B C35 H35A 108.2 . . ?
N31 C36 C35 111.27(11) . . ?
N31 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
N31 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108 . . ?
C7 C8 C9 117.89(14) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
N34 C37 H37A 109.5 . . ?
N34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C5 C4 C9 118.79(13) . . ?
C5 C4 C3 134.87(14) . . ?
C9 C4 C3 106.33(12) . . ?
C16 C11 C12 118.94(15) . . ?
C16 C11 C10 119.85(14) . . ?
C12 C11 C10 121.21(14) . . ?
N1 C9 C8 130.19(14) . . ?
N1 C9 C4 108.04(13) . . ?
C8 C9 C4 121.77(14) . . ?
C5 C6 C7 121.37(15) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C5 C4 119.11(14) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C10 C11 112.73(12) . . ?
N1 C10 H10A 109 . . ?
C11 C10 H10A 109 . . ?
N1 C10 H10B 109 . . ?
C11 C10 H10B 109 . . ?
H10A C10 H10B 107.8 . . ?
C11 C16 C15 120.55(16) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C13 C12 C11 120.50(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.11(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.63(15) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C8 C7 C6 121.05(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C14 C15 C16 120.26(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C3A N31A C36A 113.29(12) . . ?
C3A N31A C32A 113.00(11) . . ?
C36A N31A C32A 109.84(11) . . ?
C37A N34A C35A 111.97(12) . . ?
C37A N34A C33A 111.84(11) . . ?
C35A N34A C33A 110.11(11) . . ?
C37A N34A H4AA 107.5(11) . . ?
C35A N34A H4AA 107.9(11) . . ?
C33A N34A H4AA 107.3(11) . . ?
C2A C3A N31A 128.74(13) . . ?
C2A C3A C4A 107.11(13) . . ?
N31A C3A C4A 124.05(13) . . ?
N31A C32A C33A 110.52(12) . . ?
N31A C32A H2AA 109.5 . . ?
C33A C32A H2AA 109.5 . . ?
N31A C32A H2AB 109.5 . . ?
C33A C32A H2AB 109.5 . . ?
H2AA C32A H2AB 108.1 . . ?
N34A C33A C32A 110.24(12) . . ?
N34A C33A H3AA 109.6 . . ?
C32A C33A H3AA 109.6 . . ?
N34A C33A H3AB 109.6 . . ?
C32A C33A H3AB 109.6 . . ?
H3AA C33A H3AB 108.1 . . ?
C5A C4A C9A 119.55(14) . . ?
C5A C4A C3A 133.95(15) . . ?
C9A C4A C3A 106.33(13) . . ?
N1A C10A C11A 113.86(13) . . ?
N1A C10A H1AB 108.8 . . ?
C11A C10A H1AB 108.8 . . ?
N1A C10A H1AA 108.8 . . ?
C11A C10A H1AA 108.8 . . ?
H1AB C10A H1AA 107.7 . . ?
C2A N1A C9A 108.48(13) . . ?
C2A N1A C10A 125.59(13) . . ?
C9A N1A C10A 125.37(13) . . ?
N31A C36A C35A 109.83(12) . . ?
N31A C36A H6AB 109.7 . . ?
C35A C36A H6AB 109.7 . . ?
N31A C36A H6AA 109.7 . . ?
C35A C36A H6AA 109.7 . . ?
H6AB C36A H6AA 108.2 . . ?
C16A C11A C12A 118.75(17) . . ?
C16A C11A C10A 119.77(15) . . ?
C12A C11A C10A 121.45(16) . . ?
N34A C37A H7AB 109.5 . . ?
N34A C37A H7AA 109.5 . . ?
H7AB C37A H7AA 109.5 . . ?
N34A C37A H7AC 109.5 . . ?
H7AB C37A H7AC 109.5 . . ?
H7AA C37A H7AC 109.5 . . ?
N1A C9A C8A 129.81(15) . . ?
N1A C9A C4A 108.22(13) . . ?
C8A C9A C4A 121.89(14) . . ?
C3A C2A N1A 109.84(13) . . ?
C3A C2A H2A 125.1 . . ?
N1A C2A H2A 125.1 . . ?
C8A C7A C6A 121.69(15) . . ?
C8A C7A H6A 119.2 . . ?
C6A C7A H6A 119.2 . . ?
C6A C5A C4A 118.45(15) . . ?
C6A C5A H8A 120.8 . . ?
C4A C5A H8A 120.8 . . ?
N34A C35A C36A 109.56(12) . . ?
N34A C35A H5AA 109.8 . . ?
C36A C35A H5AA 109.8 . . ?
N34A C35A H5AB 109.8 . . ?
C36A C35A H5AB 109.8 . . ?
H5AA C35A H5AB 108.2 . . ?
C7A C8A C9A 117.28(15) . . ?
C7A C8A H7A 121.4 . . ?
C9A C8A H7A 121.4 . . ?
C5A C6A C7A 121.13(15) . . ?
C5A C6A H5A 119.4 . . ?
C7A C6A H5A 119.4 . . ?
C11A C16A C15A 120.5(2) . . ?
C11A C16A H6P 119.7 . . ?
C15A C16A H6P 119.7 . . ?
C11A C12A C13A 119.9(2) . . ?
C11A C12A H2P 120.1 . . ?
C13A C12A H2P 120.1 . . ?
C14A C13A C12A 120.5(2) . . ?
C14A C13A H3P 119.8 . . ?
C12A C13A H3P 119.8 . . ?
C15A C14A C13A 120.0(2) . . ?
C15A C14A H4P 120 . . ?
C13A C14A H4P 120 . . ?
C14A C15A C16A 120.4(2) . . ?
C14A C15A H5P 119.8 . . ?
C16A C15A H5P 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O61 C60 C61 O62 168.42(17) . . . . ?
O60 C60 C61 O62 -10.4(2) . . . . ?
O61 C60 C61 O63 -11.4(2) . . . . ?
O60 C60 C61 O63 169.83(14) . . . . ?
O51 C50 C51 O53 171.60(14) . . . . ?
O50 C50 C51 O53 -8.78(19) . . . . ?
O51 C50 C51 O52 -8.86(19) . . . . ?
O50 C50 C51 O52 170.75(12) . . . . ?
C3 N31 C32 C33 179.00(11) . . . . ?
C36 N31 C32 C33 -56.17(15) . . . . ?
C36 N31 C3 C2 -2.9(2) . . . . ?
C32 N31 C3 C2 121.11(16) . . . . ?
C36 N31 C3 C4 177.04(13) . . . . ?
C32 N31 C3 C4 -58.97(18) . . . . ?
N31 C3 C2 N1 -179.91(13) . . . . ?
C4 C3 C2 N1 0.16(17) . . . . ?
C9 N1 C2 C3 -0.20(17) . . . . ?
C10 N1 C2 C3 -176.49(14) . . . . ?
C37 N34 C33 C32 172.64(11) . . . . ?
C35 N34 C33 C32 -61.75(14) . . . . ?
N31 C32 C33 N34 59.83(15) . . . . ?
C37 N34 C35 C36 -173.23(11) . . . . ?
C33 N34 C35 C36 61.53(14) . . . . ?
C3 N31 C36 C35 179.92(11) . . . . ?
C32 N31 C36 C35 55.37(15) . . . . ?
N34 C35 C36 N31 -58.94(15) . . . . ?
C2 C3 C4 C5 179.67(16) . . . . ?
N31 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C9 -0.06(16) . . . . ?
N31 C3 C4 C9 -179.99(13) . . . . ?
C2 N1 C9 C8 -179.16(15) . . . . ?
C10 N1 C9 C8 -3.0(3) . . . . ?
C2 N1 C9 C4 0.16(16) . . . . ?
C10 N1 C9 C4 176.31(14) . . . . ?
C7 C8 C9 N1 -179.38(15) . . . . ?
C7 C8 C9 C4 1.4(2) . . . . ?
C5 C4 C9 N1 -179.84(13) . . . . ?
C3 C4 C9 N1 -0.06(16) . . . . ?
C5 C4 C9 C8 -0.5(2) . . . . ?
C3 C4 C9 C8 179.33(13) . . . . ?
C7 C6 C5 C4 0.9(2) . . . . ?
C9 C4 C5 C6 -0.7(2) . . . . ?
C3 C4 C5 C6 179.58(16) . . . . ?
C9 N1 C10 C11 -110.14(17) . . . . ?
C2 N1 C10 C11 65.5(2) . . . . ?
C16 C11 C10 N1 -145.35(15) . . . . ?
C12 C11 C10 N1 35.8(2) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C10 C11 C16 C15 -178.58(15) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C10 C11 C12 C13 179.39(16) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C9 C8 C7 C6 -1.2(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C11 C16 C15 C14 -0.9(3) . . . . ?
C36A N31A C3A C2A 23.0(2) . . . . ?
C32A N31A C3A C2A -102.77(17) . . . . ?
C36A N31A C3A C4A -152.84(14) . . . . ?
C32A N31A C3A C4A 81.43(17) . . . . ?
C3A N31A C32A C33A -172.74(12) . . . . ?
C36A N31A C32A C33A 59.69(16) . . . . ?
C37A N34A C33A C32A -178.97(12) . . . . ?
C35A N34A C33A C32A 55.86(16) . . . . ?
N31A C32A C33A N34A -56.86(16) . . . . ?
C2A C3A C4A C5A -175.86(16) . . . . ?
N31A C3A C4A C5A 0.7(3) . . . . ?
C2A C3A C4A C9A -0.73(16) . . . . ?
N31A C3A C4A C9A 175.84(13) . . . . ?
C11A C10A N1A C2A 127.59(16) . . . . ?
C11A C10A N1A C9A -62.0(2) . . . . ?
C3A N31A C36A C35A 171.27(12) . . . . ?
C32A N31A C36A C35A -61.32(16) . . . . ?
N1A C10A C11A C16A 146.31(15) . . . . ?
N1A C10A C11A C12A -35.7(2) . . . . ?
C2A N1A C9A C8A 175.75(16) . . . . ?
C10A N1A C9A C8A 3.9(3) . . . . ?
C2A N1A C9A C4A -1.02(17) . . . . ?
C10A N1A C9A C4A -172.85(14) . . . . ?
C5A C4A C9A N1A 177.05(13) . . . . ?
C3A C4A C9A N1A 1.08(16) . . . . ?
C5A C4A C9A C8A 0.0(2) . . . . ?
C3A C4A C9A C8A -176.01(14) . . . . ?
N31A C3A C2A N1A -176.24(14) . . . . ?
C4A C3A C2A N1A 0.12(17) . . . . ?
C9A N1A C2A C3A 0.56(18) . . . . ?
C10A N1A C2A C3A 172.36(14) . . . . ?
C9A C4A C5A C6A -0.2(2) . . . . ?
C3A C4A C5A C6A 174.43(16) . . . . ?
C37A N34A C35A C36A 177.46(12) . . . . ?
C33A N34A C35A C36A -57.44(15) . . . . ?
N31A C36A C35A N34A 60.35(16) . . . . ?
C6A C7A C8A C9A 0.1(2) . . . . ?
N1A C9A C8A C7A -176.32(16) . . . . ?
C4A C9A C8A C7A 0.1(2) . . . . ?
C4A C5A C6A C7A 0.4(2) . . . . ?
C8A C7A C6A C5A -0.4(3) . . . . ?
C12A C11A C16A C15A -1.4(2) . . . . ?
C10A C11A C16A C15A 176.67(16) . . . . ?
C16A C11A C12A C13A 0.7(3) . . . . ?
C10A C11A C12A C13A -177.29(17) . . . . ?
C11A C12A C13A C14A 0.4(3) . . . . ?
C12A C13A C14A C15A -0.9(3) . . . . ?
C13A C14A C15A C16A 0.3(3) . . . . ?
C11A C16A C15A C14A 0.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N34 H34 O53 0.896(18) 1.874(18) 2.7251(16) 157.7(15) .
N34 H34 O50 0.896(18) 2.456(17) 3.0668(16) 125.7(13) .
O60 H60 O52 0.914(10) 1.576(10) 2.4894(13) 177(3) .
O63 H63 O50 0.915(10) 1.556(10) 2.4698(14) 177(3) 1_455
O71 H71 O62 1.05(4) 1.82(4) 2.788(2) 152(3) .
N34A H4AA O52 0.901(18) 2.168(18) 2.8247(16) 129.2(14) 1_454
N34A H4AA O51 0.901(18) 1.962(18) 2.7543(16) 145.7(15) 1_454
C33 H33A O62 0.99 2.4 3.2089(18) 138.3 1_655
C33 H33A O50 0.99 2.59 3.0750(17) 110.4 .
C33 H33B O61 0.99 2.61 3.4344(18) 140.9 4_665
C35 H35A O51 0.99 2.63 3.5260(17) 150.1 4_565
C37 H37B O61 0.98 2.5 3.3720(19) 148.7 4_665
C37 H37B O63 0.98 2.53 3.2936(19) 135.2 4_665
C33A H3AA O60 0.99 2.45 3.3698(18) 153.7 4_565
C33A H3AB O53 0.99 2.61 3.1989(17) 118.4 4_565
C37A H7AA O61 0.98 2.65 3.5099(19) 146.6 1_454
C37A H7AC O62 0.98 2.6 3.552(2) 162.6 4_565
C35A H5AA O61 0.99 2.65 3.5315(19) 148.5 1_454
N34 H34 O53 0.896(18) 1.874(18) 2.7251(16) 157.7(15) .
N34 H34 O50 0.896(18) 2.456(17) 3.0668(16) 125.7(13) .
O60 H60 O52 0.914(10) 1.576(10) 2.4894(13) 177(3) .
O63 H63 O50 0.915(10) 1.556(10) 2.4698(14) 177(3) 1_455
O71 H71 O62 1.05(4) 1.82(4) 2.788(2) 152(3) .
N34A H4AA O52 0.901(18) 2.168(18) 2.8247(16) 129.2(14) 1_454
N34A H4AA O51 0.901(18) 1.962(18) 2.7543(16) 145.7(15) 1_454
C33 H33A O62 0.99 2.4 3.2089(18) 138.3 1_655
C33 H33A O50 0.99 2.59 3.0750(17) 110.4 .
C33 H33B O61 0.99 2.61 3.4344(18) 140.9 4_665
C35 H35A O51 0.99 2.63 3.5260(17) 150.1 4_565
C37 H37B O61 0.98 2.5 3.3720(19) 148.7 4_665
C37 H37B O63 0.98 2.53 3.2936(19) 135.2 4_665
C33A H3AA O60 0.99 2.45 3.3698(18) 153.7 4_565
C33A H3AB O53 0.99 2.61 3.1989(17) 118.4 4_565
C37A H7AA O61 0.98 2.65 3.5099(19) 146.6 1_454
C37A H7AC O62 0.98 2.6 3.552(2) 162.6 4_565
C35A H5AA O61 0.99 2.65 3.5315(19) 148.5 1_454

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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 1550187'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-08-25T14:12:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H26 N4 O4 S'
_chemical_formula_moiety         'C22 H22 N4 O2 S, 2(H2 O)'
_chemical_formula_weight         442.53

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1583(6)
_cell_length_b                   10.1568(8)
_cell_length_c                   12.0609(9)
_cell_angle_alpha                101.718(6)
_cell_angle_beta                 100.729(6)
_cell_angle_gamma                100.020(6)
_cell_volume                     1052.83(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3076
_cell_measurement_theta_min      3.846
_cell_measurement_theta_max      71.046

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             468

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.88009
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.85

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0637921
_diffrn_orient_matrix_ub_12      0.0793883
_diffrn_orient_matrix_ub_13      0.0961762
_diffrn_orient_matrix_ub_21      -0.1619488
_diffrn_orient_matrix_ub_22      -0.0514077
_diffrn_orient_matrix_ub_23      -0.0783226
_diffrn_orient_matrix_ub_31      -0.0225376
_diffrn_orient_matrix_ub_32      -0.1275659
_diffrn_orient_matrix_ub_33      0.0508058
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_number            14911
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.846
_diffrn_reflns_theta_max         71.213
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_coverage         0
_reflns_number_total             4025
_reflns_number_gt                2991
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4025
_refine_ls_number_parameters     286
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S10 S 0.20840(8) 0.38925(7) 0.60365(6) 0.0325(2) Uani 1 1 d . . . . .
N71 N 0.2639(3) 0.8993(2) 0.4592(2) 0.0311(5) Uani 1 1 d . . . . .
O11 O 0.2253(3) 0.4023(2) 0.49071(17) 0.0381(5) Uani 1 1 d . . . . .
C21 C 0.4244(3) 0.3774(3) 0.7997(2) 0.0291(6) Uani 1 1 d . . . . .
N2 N 0.0874(3) 0.5227(3) 0.7583(2) 0.0377(6) Uani 1 1 d . . . . .
C6 C 0.1881(3) 0.9282(3) 0.6434(3) 0.0327(6) Uani 1 1 d . . . . .
H6 H 0.2 1.0238 0.6467 0.039 Uiso 1 1 calc R U . . .
O10 O 0.1175(3) 0.2673(2) 0.61681(19) 0.0407(5) Uani 1 1 d . . . . .
N74 N 0.3109(3) 0.9984(3) 0.2587(2) 0.0357(6) Uani 1 1 d D . . . .
C15 C 0.5782(3) 0.4192(3) 0.8663(2) 0.0307(6) Uani 1 1 d . . . . .
C9 C 0.1610(3) 0.6530(3) 0.6339(2) 0.0296(6) Uani 1 1 d . . . . .
N1 N 0.1293(3) 0.5199(3) 0.6517(2) 0.0335(6) Uani 1 1 d . . . . .
C18 C 0.3657(4) 0.2435(3) 0.9376(3) 0.0364(7) Uani 1 1 d . . . . .
H18 H 0.2938 0.1839 0.9628 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3909(3) 0.4284(3) 0.6972(2) 0.0296(6) Uani 1 1 d . . . . .
C12 C 0.5016(4) 0.5140(3) 0.6657(3) 0.0360(7) Uani 1 1 d . . . . .
H12 H 0.476 0.5463 0.5975 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1434(3) 0.8800(3) 0.7326(3) 0.0338(7) Uani 1 1 d . . . . .
H5 H 0.1226 0.9404 0.796 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2173(3) 0.8404(3) 0.5460(3) 0.0308(6) Uani 1 1 d . . . . .
C14 C 0.6889(3) 0.5081(3) 0.8313(3) 0.0361(7) Uani 1 1 d . . . . .
H14 H 0.7905 0.536 0.8769 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3191(3) 0.2888(3) 0.8403(2) 0.0323(6) Uani 1 1 d . . . . .
H19 H 0.2153 0.2608 0.7993 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6213(4) 0.3707(3) 0.9666(3) 0.0366(7) Uani 1 1 d . . . . .
H16 H 0.7236 0.3993 1.0107 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1290(3) 0.7390(3) 0.7278(3) 0.0324(6) Uani 1 1 d . . . . .
C8 C 0.2048(3) 0.6997(3) 0.5412(2) 0.0295(6) Uani 1 1 d . . . . .
H8 H 0.2252 0.6389 0.4778 0.035 Uiso 1 1 calc R U . . .
C76 C 0.3060(4) 0.8120(3) 0.3630(3) 0.0342(7) Uani 1 1 d . . . . .
H76B H 0.213 0.7542 0.3068 0.041 Uiso 1 1 calc R U . . .
H76A H 0.3673 0.7503 0.3933 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5180(4) 0.2836(3) 1.0010(3) 0.0395(7) Uani 1 1 d . . . . .
H17 H 0.5488 0.2499 1.0676 0.047 Uiso 1 1 calc R U . . .
C75 C 0.3976(4) 0.9023(3) 0.3030(3) 0.0355(7) Uani 1 1 d . . . . .
H75A H 0.4932 0.9558 0.3586 0.043 Uiso 1 1 calc R U . . .
H75B H 0.4248 0.8433 0.2374 0.043 Uiso 1 1 calc R U . . .
C3 C 0.0846(3) 0.6518(3) 0.7998(3) 0.0377(7) Uani 1 1 d . . . . .
H3 H 0.0559 0.6837 0.8706 0.045 Uiso 1 1 calc R U . . .
C72 C 0.1760(4) 0.9934(3) 0.4155(3) 0.0361(7) Uani 1 1 d . . . . .
H72A H 0.1478 1.0517 0.481 0.043 Uiso 1 1 calc R U . . .
H72B H 0.081 0.9395 0.3594 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6520(4) 0.5544(3) 0.7331(3) 0.0363(7) Uani 1 1 d . . . . .
H13 H 0.7274 0.6134 0.7106 0.044 Uiso 1 1 calc R U . . .
C77 C 0.4029(4) 1.0848(4) 0.2005(3) 0.0449(8) Uani 1 1 d . . . . .
H77A H 0.4295 1.0256 0.1358 0.067 Uiso 1 1 calc R U . . .
H77B H 0.344 1.1471 0.1706 0.067 Uiso 1 1 calc R U . . .
H77C H 0.4963 1.1391 0.2564 0.067 Uiso 1 1 calc R U . . .
C73 C 0.2688(4) 1.0843(3) 0.3565(3) 0.0362(7) Uani 1 1 d . . . . .
H73A H 0.2085 1.1474 0.3275 0.043 Uiso 1 1 calc R U . . .
H73B H 0.362 1.1408 0.4133 0.043 Uiso 1 1 calc R U . . .
O1W O 0.0404(3) 0.9036(3) 0.0681(2) 0.0488(6) Uani 1 1 d D . . . .
O2W O -0.0028(4) 0.6207(4) 0.0696(3) 0.0807(10) Uani 1 1 d D . . . .
H3W H 0.031(14) 0.714(4) 0.073(11) 0.121 Uiso 0.5 1 d D U P . .
H4W H 0 0.5 0 0.121 Uiso 0.5 2 d S U P . .
H5W H -0.026(7) 0.607(5) 0.140(3) 0.121 Uiso 1 1 d D U . . .
H1W H 0.0791 0.9203 0.1387 0.121 Uiso 1 1 d D U . . .
H6W H -0.0127 0.9403 0.0302 0.121 Uiso 0.5 1 d D U P . .
H2W H 0.0499 0.8173 0.0748 0.121 Uiso 0.75 1 d D U P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S10 O10 1.422(2) . ?
S10 O11 1.429(2) . ?
S10 N1 1.674(3) . ?
S10 C11 1.763(3) . ?
N71 C7 1.403(4) . ?
N71 C76 1.465(4) . ?
N71 C72 1.467(4) . ?
C21 C19 1.425(4) . ?
C21 C15 1.429(4) . ?
C21 C11 1.437(4) . ?
N2 C3 1.311(4) . ?
N2 N1 1.404(3) . ?
C6 C5 1.368(4) . ?
C6 C7 1.421(4) . ?
C6 H6 0.95 . ?
N74 C73 1.473(4) . ?
N74 C77 1.479(4) . ?
N74 C75 1.481(4) . ?
C15 C16 1.413(4) . ?
C15 C14 1.420(4) . ?
C9 C4 1.394(4) . ?
C9 C8 1.397(4) . ?
C9 N1 1.401(4) . ?
C18 C19 1.369(4) . ?
C18 C17 1.405(4) . ?
C18 H18 0.95 . ?
C11 C12 1.379(4) . ?
C12 C13 1.405(5) . ?
C12 H12 0.95 . ?
C5 C4 1.404(4) . ?
C5 H5 0.95 . ?
C7 C8 1.402(4) . ?
C14 C13 1.367(4) . ?
C14 H14 0.95 . ?
C19 H19 0.95 . ?
C16 C17 1.361(4) . ?
C16 H16 0.95 . ?
C4 C3 1.422(4) . ?
C8 H8 0.95 . ?
C76 C75 1.515(4) . ?
C76 H76B 0.99 . ?
C76 H76A 0.99 . ?
C17 H17 0.95 . ?
C75 H75A 0.99 . ?
C75 H75B 0.99 . ?
C3 H3 0.95 . ?
C72 C73 1.516(4) . ?
C72 H72A 0.99 . ?
C72 H72B 0.99 . ?
C13 H13 0.95 . ?
C77 H77A 0.98 . ?
C77 H77B 0.98 . ?
C77 H77C 0.98 . ?
C73 H73A 0.99 . ?
C73 H73B 0.99 . ?
O1W H1W 0.829(2) . ?
O1W H6W 0.796(2) . ?
O1W H2W 0.914(2) . ?
O2W H3W 0.93(2) . ?
O2W H4W 1.345(4) . ?
O2W H5W 0.936(19) . ?

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
O10 S10 O11 120.11(14) . . ?
O10 S10 N1 107.05(13) . . ?
O11 S10 N1 104.38(12) . . ?
O10 S10 C11 110.79(13) . . ?
O11 S10 C11 108.62(14) . . ?
N1 S10 C11 104.62(13) . . ?
C7 N71 C76 118.9(2) . . ?
C7 N71 C72 117.3(2) . . ?
C76 N71 C72 110.2(2) . . ?
C19 C21 C15 117.3(3) . . ?
C19 C21 C11 126.2(3) . . ?
C15 C21 C11 116.5(3) . . ?
C3 N2 N1 105.0(2) . . ?
C5 C6 C7 122.4(3) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C73 N74 C77 110.9(2) . . ?
C73 N74 C75 109.0(2) . . ?
C77 N74 C75 110.2(2) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 C21 120.0(3) . . ?
C14 C15 C21 120.4(3) . . ?
C4 C9 C8 123.1(3) . . ?
C4 C9 N1 105.7(3) . . ?
C8 C9 N1 131.0(3) . . ?
C9 N1 N2 110.8(2) . . ?
C9 N1 S10 126.6(2) . . ?
N2 N1 S10 115.67(19) . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C12 C11 C21 121.5(3) . . ?
C12 C11 S10 114.9(2) . . ?
C21 C11 S10 123.6(2) . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C8 C7 N71 121.9(3) . . ?
C8 C7 C6 119.7(3) . . ?
N71 C7 C6 118.4(3) . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C18 C19 C21 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C21 C19 H19 119.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C9 C4 C5 119.5(3) . . ?
C9 C4 C3 105.5(3) . . ?
C5 C4 C3 134.9(3) . . ?
C9 C8 C7 116.9(3) . . ?
C9 C8 H8 121.5 . . ?
C7 C8 H8 121.5 . . ?
N71 C76 C75 109.4(2) . . ?
N71 C76 H76B 109.8 . . ?
C75 C76 H76B 109.8 . . ?
N71 C76 H76A 109.8 . . ?
C75 C76 H76A 109.8 . . ?
H76B C76 H76A 108.2 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
N74 C75 C76 111.4(2) . . ?
N74 C75 H75A 109.3 . . ?
C76 C75 H75A 109.3 . . ?
N74 C75 H75B 109.3 . . ?
C76 C75 H75B 109.3 . . ?
H75A C75 H75B 108 . . ?
N2 C3 C4 112.9(3) . . ?
N2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
N71 C72 C73 110.4(2) . . ?
N71 C72 H72A 109.6 . . ?
C73 C72 H72A 109.6 . . ?
N71 C72 H72B 109.6 . . ?
C73 C72 H72B 109.6 . . ?
H72A C72 H72B 108.1 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N74 C77 H77A 109.5 . . ?
N74 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
N74 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
N74 C73 C72 110.0(2) . . ?
N74 C73 H73A 109.7 . . ?
C72 C73 H73A 109.7 . . ?
N74 C73 H73B 109.7 . . ?
C72 C73 H73B 109.7 . . ?
H73A C73 H73B 108.2 . . ?
H1W O1W H6W 132.7(3) . . ?
H1W O1W H2W 80.0(2) . . ?
H6W O1W H2W 140.2(3) . . ?
H3W O2W H4W 136(8) . . ?
H3W O2W H5W 112(9) . . ?
H4W O2W H5W 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C21 C15 C16 1.1(4) . . . . ?
C11 C21 C15 C16 -178.4(3) . . . . ?
C19 C21 C15 C14 -179.6(3) . . . . ?
C11 C21 C15 C14 0.9(4) . . . . ?
C4 C9 N1 N2 -3.7(3) . . . . ?
C8 C9 N1 N2 -179.2(3) . . . . ?
C4 C9 N1 S10 -153.0(2) . . . . ?
C8 C9 N1 S10 31.5(4) . . . . ?
C3 N2 N1 C9 3.8(3) . . . . ?
C3 N2 N1 S10 156.7(2) . . . . ?
O10 S10 N1 C9 -166.0(2) . . . . ?
O11 S10 N1 C9 -37.7(3) . . . . ?
C11 S10 N1 C9 76.3(3) . . . . ?
O10 S10 N1 N2 46.0(2) . . . . ?
O11 S10 N1 N2 174.3(2) . . . . ?
C11 S10 N1 N2 -71.6(2) . . . . ?
C19 C21 C11 C12 180.0(3) . . . . ?
C15 C21 C11 C12 -0.6(4) . . . . ?
C19 C21 C11 S10 0.7(4) . . . . ?
C15 C21 C11 S10 -179.9(2) . . . . ?
O10 S10 C11 C12 159.5(2) . . . . ?
O11 S10 C11 C12 25.5(3) . . . . ?
N1 S10 C11 C12 -85.5(2) . . . . ?
O10 S10 C11 C21 -21.2(3) . . . . ?
O11 S10 C11 C21 -155.1(2) . . . . ?
N1 S10 C11 C21 93.9(2) . . . . ?
C21 C11 C12 C13 0.2(4) . . . . ?
S10 C11 C12 C13 179.5(2) . . . . ?
C7 C6 C5 C4 1.2(4) . . . . ?
C76 N71 C7 C8 -2.3(4) . . . . ?
C72 N71 C7 C8 134.5(3) . . . . ?
C76 N71 C7 C6 175.2(3) . . . . ?
C72 N71 C7 C6 -48.0(4) . . . . ?
C5 C6 C7 C8 -1.9(4) . . . . ?
C5 C6 C7 N71 -179.5(3) . . . . ?
C16 C15 C14 C13 178.4(3) . . . . ?
C21 C15 C14 C13 -0.8(4) . . . . ?
C17 C18 C19 C21 0.5(5) . . . . ?
C15 C21 C19 C18 -1.5(4) . . . . ?
C11 C21 C19 C18 177.9(3) . . . . ?
C14 C15 C16 C17 -178.9(3) . . . . ?
C21 C15 C16 C17 0.4(4) . . . . ?
C8 C9 C4 C5 -1.3(4) . . . . ?
N1 C9 C4 C5 -177.2(2) . . . . ?
C8 C9 C4 C3 178.1(3) . . . . ?
N1 C9 C4 C3 2.2(3) . . . . ?
C6 C5 C4 C9 0.4(4) . . . . ?
C6 C5 C4 C3 -178.8(3) . . . . ?
C4 C9 C8 C7 0.6(4) . . . . ?
N1 C9 C8 C7 175.4(3) . . . . ?
N71 C7 C8 C9 178.5(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 N71 C76 C75 -162.2(2) . . . . ?
C72 N71 C76 C75 58.2(3) . . . . ?
C15 C16 C17 C18 -1.5(5) . . . . ?
C19 C18 C17 C16 1.1(5) . . . . ?
C73 N74 C75 C76 58.2(3) . . . . ?
C77 N74 C75 C76 -179.9(3) . . . . ?
N71 C76 C75 N74 -58.3(3) . . . . ?
N1 N2 C3 C4 -2.4(3) . . . . ?
C9 C4 C3 N2 0.2(4) . . . . ?
C5 C4 C3 N2 179.4(3) . . . . ?
C7 N71 C72 C73 160.3(3) . . . . ?
C76 N71 C72 C73 -59.4(3) . . . . ?
C15 C14 C13 C12 0.4(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C77 N74 C73 C72 -179.4(3) . . . . ?
C75 N74 C73 C72 -57.9(3) . . . . ?
N71 C72 C73 N74 59.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O11 0.95 2.44 3.004(3) 117.9 .
C72 H72A O10 0.99 2.55 3.490(4) 159.5 1_565
C72 H72B O10 0.99 2.63 3.332(4) 128.2 2_566
O2W H3W O1W 0.93(2) 1.93(4) 2.835(4) 164(12) .
O2W H4W O2W 1.345(4) 1.345(4) 2.691(7) 180.0(3) 2_565
O2W H5W N2 0.936(19) 2.06(3) 2.910(4) 150(5) 2_566
O1W H1W N74 0.829(2) 2.244(3) 2.915(3) 138.27(18) .
O1W H6W O1W 0.796(2) 2.186(2) 2.905(5) 150.53(13) 2_575
O1W H2W O2W 0.914(2) 1.956(4) 2.835(4) 160.95(18) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1550185'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2016-06-23T13:30:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C19 H23 Cl N2 O3 S'
_chemical_formula_moiety         'C19 H23 N2 O3 S, Cl'
_chemical_formula_weight         394.9

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7820(2)
_cell_length_b                   7.29780(10)
_cell_length_c                   24.7359(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.1360(10)
_cell_angle_gamma                90
_cell_volume                     1945.96(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10453
_cell_measurement_theta_min      2.9044
_cell_measurement_theta_max      28.5826

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             832

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.87573
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.909

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0653833
_diffrn_orient_matrix_ub_12      -0.0103188
_diffrn_orient_matrix_ub_13      -0.0017293
_diffrn_orient_matrix_ub_21      0.0003698
_diffrn_orient_matrix_ub_22      0.0302795
_diffrn_orient_matrix_ub_23      -0.0272351
_diffrn_orient_matrix_ub_31      0.0074722
_diffrn_orient_matrix_ub_32      -0.0917881
_diffrn_orient_matrix_ub_33      -0.0087978
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            26277
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         28.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             4748
_reflns_number_gt                3782
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.5639P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4748
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S10 S 0.12635(4) 0.46726(5) 0.40264(2) 0.04321(12) Uani 1 1 d . . . . .
Cl1 Cl 0.70118(5) -0.14844(6) 0.27576(2) 0.05825(15) Uani 1 1 d . . . . .
O10 O 0.12135(12) 0.55632(17) 0.35134(5) 0.0570(3) Uani 1 1 d . . . . .
C9 C 0.33074(14) 0.3623(2) 0.46350(6) 0.0382(3) Uani 1 1 d . . . . .
O11 O 0.08168(12) 0.55625(17) 0.44970(5) 0.0562(3) Uani 1 1 d . . . . .
C5 C 0.53037(15) 0.2369(2) 0.49115(6) 0.0401(3) Uani 1 1 d . . . . .
H5 H 0.6105 0.2002 0.483 0.048 Uiso 1 1 calc R U . . .
N1 N 0.27459(12) 0.42322(18) 0.41454(5) 0.0409(3) Uani 1 1 d . . . . .
C32 C 0.57850(14) 0.3431(2) 0.30719(6) 0.0404(4) Uani 1 1 d . . . . .
H32B H 0.5006 0.3096 0.2896 0.048 Uiso 1 1 calc R U . . .
H32A H 0.5825 0.4758 0.3086 0.048 Uiso 1 1 calc R U . . .
O61 O 0.55741(13) 0.16059(19) 0.58610(5) 0.0583(3) Uani 1 1 d . . . . .
C4 C 0.45007(14) 0.3035(2) 0.45084(6) 0.0362(3) Uani 1 1 d . . . . .
N33 N 0.68298(13) 0.2739(2) 0.27401(5) 0.0409(3) Uani 1 1 d . . . . .
C3 C 0.46527(14) 0.3214(2) 0.39328(6) 0.0376(3) Uani 1 1 d . . . . .
C8 C 0.28804(16) 0.3531(2) 0.51616(7) 0.0452(4) Uani 1 1 d . . . . .
H8 H 0.2086 0.392 0.5246 0.054 Uiso 1 1 calc R U . . .
C2 C 0.35864(14) 0.3899(2) 0.37254(6) 0.0410(3) Uani 1 1 d . . . . .
H2 H 0.3427 0.412 0.336 0.049 Uiso 1 1 calc R U . . .
C12 C 0.06832(16) 0.1521(3) 0.34959(8) 0.0506(4) Uani 1 1 d . . . . .
H12 H 0.119 0.1945 0.3223 0.061 Uiso 1 1 calc R U . . .
C11 C 0.05296(14) 0.2531(2) 0.39639(7) 0.0411(3) Uani 1 1 d . . . . .
C7 C 0.36785(17) 0.2842(2) 0.55537(7) 0.0485(4) Uani 1 1 d . . . . .
H7 H 0.3411 0.2756 0.5908 0.058 Uiso 1 1 calc R U . . .
C31 C 0.58046(15) 0.2689(2) 0.36403(6) 0.0436(4) Uani 1 1 d . . . . .
H31B H 0.5873 0.1364 0.3629 0.052 Uiso 1 1 calc R U . . .
H31A H 0.6525 0.3163 0.3835 0.052 Uiso 1 1 calc R U . . .
C6 C 0.48815(17) 0.2266(2) 0.54324(6) 0.0440(4) Uani 1 1 d . . . . .
C16 C -0.02102(17) 0.1924(3) 0.43735(8) 0.0537(4) Uani 1 1 d . . . . .
H16 H -0.0298 0.2613 0.4687 0.064 Uiso 1 1 calc R U . . .
C62 C 0.68044(18) 0.1036(3) 0.57503(8) 0.0570(5) Uani 1 1 d . . . . .
H62A H 0.7199 0.0603 0.6077 0.085 Uiso 1 1 calc R U . . .
H62C H 0.6781 0.0068 0.5487 0.085 Uiso 1 1 calc R U . . .
H62B H 0.7264 0.2053 0.5611 0.085 Uiso 1 1 calc R U . . .
C14 C -0.06808(19) -0.0740(3) 0.38473(10) 0.0648(6) Uani 1 1 d . . . . .
H14 H -0.1097 -0.1849 0.3806 0.078 Uiso 1 1 calc R U . . .
C15 C -0.0823(2) 0.0261(3) 0.43104(9) 0.0665(6) Uani 1 1 d . . . . .
H15 H -0.1329 -0.0173 0.4582 0.08 Uiso 1 1 calc R U . . .
C34 C 0.80510(16) 0.3402(3) 0.29410(8) 0.0616(5) Uani 1 1 d . . . . .
H34C H 0.8168 0.3049 0.3312 0.092 Uiso 1 1 calc R U . . .
H34A H 0.8695 0.2873 0.2728 0.092 Uiso 1 1 calc R U . . .
H34B H 0.8082 0.4713 0.2912 0.092 Uiso 1 1 calc R U . . .
C13 C 0.00678(18) -0.0127(3) 0.34439(9) 0.0613(5) Uani 1 1 d . . . . .
H13 H 0.0161 -0.0827 0.3133 0.074 Uiso 1 1 calc R U . . .
C35 C 0.66263(19) 0.3271(3) 0.21637(7) 0.0582(5) Uani 1 1 d . . . . .
H35B H 0.5831 0.2832 0.2039 0.087 Uiso 1 1 calc R U . . .
H35C H 0.6652 0.4581 0.2132 0.087 Uiso 1 1 calc R U . . .
H35A H 0.7265 0.2741 0.1948 0.087 Uiso 1 1 calc R U . . .
H33 H 0.6834(18) 0.146(3) 0.2753(8) 0.058(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S10 O11 1.4251(12) . ?
S10 O10 1.4257(13) . ?
S10 N1 1.6510(14) . ?
S10 C11 1.7570(16) . ?
C9 C8 1.392(2) . ?
C9 C4 1.398(2) . ?
C9 N1 1.415(2) . ?
C5 C6 1.377(2) . ?
C5 C4 1.395(2) . ?
C5 H5 0.93 . ?
N1 C2 1.4132(19) . ?
C32 N33 1.4946(19) . ?
C32 C31 1.506(2) . ?
C32 H32B 0.97 . ?
C32 H32A 0.97 . ?
O61 C6 1.372(2) . ?
O61 C62 1.422(2) . ?
C4 C3 1.442(2) . ?
N33 C34 1.479(2) . ?
N33 C35 1.490(2) . ?
N33 H33 0.93(2) . ?
C3 C2 1.346(2) . ?
C3 C31 1.500(2) . ?
C8 C7 1.379(3) . ?
C8 H8 0.93 . ?
C2 H2 0.93 . ?
C12 C13 1.378(3) . ?
C12 C11 1.385(2) . ?
C12 H12 0.93 . ?
C11 C16 1.375(2) . ?
C7 C6 1.402(3) . ?
C7 H7 0.93 . ?
C31 H31B 0.97 . ?
C31 H31A 0.97 . ?
C16 C15 1.389(3) . ?
C16 H16 0.93 . ?
C62 H62A 0.96 . ?
C62 H62C 0.96 . ?
C62 H62B 0.96 . ?
C14 C15 1.370(3) . ?
C14 C13 1.371(3) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C34 H34C 0.96 . ?
C34 H34A 0.96 . ?
C34 H34B 0.96 . ?
C13 H13 0.93 . ?
C35 H35B 0.96 . ?
C35 H35C 0.96 . ?
C35 H35A 0.96 . ?

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
O11 S10 O10 120.78(8) . . ?
O11 S10 N1 106.55(8) . . ?
O10 S10 N1 105.47(7) . . ?
O11 S10 C11 108.56(8) . . ?
O10 S10 C11 108.55(8) . . ?
N1 S10 C11 105.98(7) . . ?
C8 C9 C4 121.19(15) . . ?
C8 C9 N1 132.26(15) . . ?
C4 C9 N1 106.56(13) . . ?
C6 C5 C4 118.40(16) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C2 N1 C9 107.79(13) . . ?
C2 N1 S10 122.36(12) . . ?
C9 N1 S10 127.59(10) . . ?
N33 C32 C31 113.23(13) . . ?
N33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
N33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
H32B C32 H32A 107.7 . . ?
C6 O61 C62 116.70(14) . . ?
C5 C4 C9 120.53(14) . . ?
C5 C4 C3 131.01(15) . . ?
C9 C4 C3 108.44(14) . . ?
C34 N33 C35 110.47(14) . . ?
C34 N33 C32 112.38(14) . . ?
C35 N33 C32 109.83(13) . . ?
C34 N33 H33 108.2(12) . . ?
C35 N33 H33 107.0(12) . . ?
C32 N33 H33 108.8(12) . . ?
C2 C3 C4 107.29(13) . . ?
C2 C3 C31 128.34(14) . . ?
C4 C3 C31 124.37(14) . . ?
C7 C8 C9 117.56(16) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C3 C2 N1 109.82(14) . . ?
C3 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
C13 C12 C11 118.51(18) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C16 C11 C12 121.65(16) . . ?
C16 C11 S10 119.25(13) . . ?
C12 C11 S10 119.08(13) . . ?
C8 C7 C6 121.73(15) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C3 C31 C32 111.24(13) . . ?
C3 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C3 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
H31B C31 H31A 108 . . ?
O61 C6 C5 123.86(17) . . ?
O61 C6 C7 115.56(15) . . ?
C5 C6 C7 120.57(16) . . ?
C11 C16 C15 118.71(18) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
O61 C62 H62A 109.5 . . ?
O61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
O61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62C C62 H62B 109.5 . . ?
C15 C14 C13 120.80(19) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
N33 C34 H34C 109.5 . . ?
N33 C34 H34A 109.5 . . ?
H34C C34 H34A 109.5 . . ?
N33 C34 H34B 109.5 . . ?
H34C C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C14 C13 C12 120.41(19) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N33 C35 H35B 109.5 . . ?
N33 C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N33 C35 H35A 109.5 . . ?
H35B C35 H35A 109.5 . . ?
H35C C35 H35A 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
C8 C9 N1 C2 -176.16(16) . . . . ?
C4 C9 N1 C2 3.41(16) . . . . ?
C8 C9 N1 S10 -13.2(2) . . . . ?
C4 C9 N1 S10 166.39(11) . . . . ?
O11 S10 N1 C2 -159.51(12) . . . . ?
O10 S10 N1 C2 -30.00(15) . . . . ?
C11 S10 N1 C2 85.00(14) . . . . ?
O11 S10 N1 C9 39.76(15) . . . . ?
O10 S10 N1 C9 169.27(13) . . . . ?
C11 S10 N1 C9 -75.74(15) . . . . ?
C6 C5 C4 C9 1.5(2) . . . . ?
C6 C5 C4 C3 -176.53(15) . . . . ?
C8 C9 C4 C5 -1.2(2) . . . . ?
N1 C9 C4 C5 179.19(13) . . . . ?
C8 C9 C4 C3 177.25(14) . . . . ?
N1 C9 C4 C3 -2.38(16) . . . . ?
C31 C32 N33 C34 -66.26(19) . . . . ?
C31 C32 N33 C35 170.34(15) . . . . ?
C5 C4 C3 C2 178.63(15) . . . . ?
C9 C4 C3 C2 0.42(17) . . . . ?
C5 C4 C3 C31 -0.7(3) . . . . ?
C9 C4 C3 C31 -178.92(15) . . . . ?
C4 C9 C8 C7 0.1(2) . . . . ?
N1 C9 C8 C7 179.65(15) . . . . ?
C4 C3 C2 N1 1.76(18) . . . . ?
C31 C3 C2 N1 -178.94(15) . . . . ?
C9 N1 C2 C3 -3.27(18) . . . . ?
S10 N1 C2 C3 -167.33(11) . . . . ?
C13 C12 C11 C16 0.4(3) . . . . ?
C13 C12 C11 S10 -177.75(14) . . . . ?
O11 S10 C11 C16 -7.14(17) . . . . ?
O10 S10 C11 C16 -140.14(14) . . . . ?
N1 S10 C11 C16 106.98(15) . . . . ?
O11 S10 C11 C12 171.05(13) . . . . ?
O10 S10 C11 C12 38.05(15) . . . . ?
N1 S10 C11 C12 -74.83(14) . . . . ?
C9 C8 C7 C6 0.6(2) . . . . ?
C2 C3 C31 C32 13.8(2) . . . . ?
C4 C3 C31 C32 -167.02(14) . . . . ?
N33 C32 C31 C3 -172.33(14) . . . . ?
C62 O61 C6 C5 1.2(2) . . . . ?
C62 O61 C6 C7 -179.17(15) . . . . ?
C4 C5 C6 O61 178.77(14) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C8 C7 C6 O61 -179.85(15) . . . . ?
C8 C7 C6 C5 -0.2(2) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
S10 C11 C16 C15 177.58(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C11 C16 C15 C14 0.2(3) . . . . ?
C15 C14 C13 C12 -0.6(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32B Cl1 0.97 2.7 3.6140(16) 157 2_655
C8 H8 O11 0.93 2.58 3.115(2) 117.3 .
C2 H2 Cl1 0.93 2.83 3.7224(17) 161 2_655
C16 H16 O11 0.93 2.49 3.416(2) 172.9 3_566
C62 H62B S10 0.96 3 3.796(2) 141.6 3_666
C35 H35A O10 0.96 2.57 3.506(2) 165.3 2_645
N33 H33 Cl1 0.93(2) 2.16(2) 3.0887(15) 174.9(17) .
C32 H32B Cl1 0.97 2.7 3.6140(16) 157 2_655
C8 H8 O11 0.93 2.58 3.115(2) 117.3 .
C2 H2 Cl1 0.93 2.83 3.7224(17) 161 2_655
C16 H16 O11 0.93 2.49 3.416(2) 172.9 3_566
C62 H62B S10 0.96 3 3.796(2) 141.6 3_666
C35 H35A O10 0.96 2.57 3.506(2) 165.3 2_645
N33 H33 Cl1 0.93(2) 2.16(2) 3.0887(15) 174.9(17) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1550188'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-11-23T20:20:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C21 H23 N3 O6 S'
_chemical_formula_moiety         'C19 H22 N3 O2, C2 H O4'
_chemical_formula_weight         445.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1025(2)
_cell_length_b                   25.7392(4)
_cell_length_c                   10.5439(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.355(2)
_cell_angle_gamma                90
_cell_volume                     2074.67(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11958
_cell_measurement_theta_min      3.0932
_cell_measurement_theta_max      28.651

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             936

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.60514
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.98

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.0657397
_diffrn_orient_matrix_ub_12      -0.0193665
_diffrn_orient_matrix_ub_13      0.0212168
_diffrn_orient_matrix_ub_21      -0.0651716
_diffrn_orient_matrix_ub_22      -0.0195912
_diffrn_orient_matrix_ub_23      -0.0187173
_diffrn_orient_matrix_ub_31      0.0064127
_diffrn_orient_matrix_ub_32      -0.0006784
_diffrn_orient_matrix_ub_33      -0.0654539
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_number            28278
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         28.714
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.945
_reflns_Friedel_coverage         0
_reflns_number_total             5061
_reflns_number_gt                4160
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+1.0629P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5061
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S10 S 0.45405(5) 0.41981(2) 0.82229(4) 0.02047(10) Uani 1 1 d . . . . .
N34 N 0.37439(17) 0.70969(5) 0.64001(12) 0.0153(2) Uani 1 1 d . . . . .
N31 N 0.29066(16) 0.60111(5) 0.61749(12) 0.0168(3) Uani 1 1 d . . . . .
O10 O 0.57599(15) 0.44329(4) 0.93920(11) 0.0265(3) Uani 1 1 d . . . . .
O11 O 0.50496(15) 0.37633(4) 0.75989(12) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.39553(18) 0.46618(5) 0.70869(13) 0.0212(3) Uani 1 1 d . . . . .
C32 C 0.3840(2) 0.62508(6) 0.53452(15) 0.0190(3) Uani 1 1 d . . . . .
H32B H 0.3547 0.6064 0.4477 0.023 Uiso 1 1 calc R U . . .
H32A H 0.5117 0.6221 0.5809 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3160(2) 0.54698(6) 0.62969(15) 0.0180(3) Uani 1 1 d . . . . .
C33 C 0.3344(2) 0.68169(6) 0.50895(14) 0.0185(3) Uani 1 1 d . . . . .
H33A H 0.4008 0.6976 0.4552 0.022 Uiso 1 1 calc R U . . .
H33B H 0.2081 0.6847 0.4574 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4053(2) 0.51971(6) 0.74144(16) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.4645 0.5341 0.8275 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2634(2) 0.40337(6) 0.85754(15) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.2418(2) 0.51055(6) 0.52159(15) 0.0181(3) Uani 1 1 d . . . . .
C35 C 0.27856(19) 0.68432(6) 0.72223(15) 0.0171(3) Uani 1 1 d . . . . .
H35B H 0.151 0.6864 0.6745 0.02 Uiso 1 1 calc R U . . .
H35A H 0.3048 0.7026 0.8093 0.02 Uiso 1 1 calc R U . . .
C8 C 0.2288(2) 0.41584(6) 0.49761(17) 0.0215(3) Uani 1 1 d . . . . .
H8 H 0.2595 0.3822 0.5349 0.026 Uiso 1 1 calc R U . . .
C36 C 0.3336(2) 0.62814(6) 0.74640(15) 0.0184(3) Uani 1 1 d . . . . .
H36A H 0.4611 0.626 0.7947 0.022 Uiso 1 1 calc R U . . .
H36B H 0.2723 0.6114 0.8027 0.022 Uiso 1 1 calc R U . . .
C9 C 0.28910(19) 0.46038(6) 0.57323(15) 0.0187(3) Uani 1 1 d . . . . .
C37 C 0.3330(2) 0.76589(6) 0.61879(16) 0.0216(3) Uani 1 1 d . . . . .
H37B H 0.3985 0.7809 0.5645 0.032 Uiso 1 1 calc R U . . .
H37C H 0.2073 0.7703 0.5719 0.032 Uiso 1 1 calc R U . . .
H37A H 0.3658 0.7836 0.706 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1223(2) 0.42254(6) 0.36611(17) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.0806 0.3929 0.3111 0.03 Uiso 1 1 calc R U . . .
C5 C 0.1331(2) 0.51634(6) 0.38865(16) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.0998 0.5499 0.3514 0.027 Uiso 1 1 calc R U . . .
C12 C 0.1756(2) 0.35775(6) 0.80530(17) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.2189 0.3354 0.7519 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2014(2) 0.43693(6) 0.93497(16) 0.0252(3) Uani 1 1 d . . . . .
H16 H 0.2624 0.468 0.9703 0.03 Uiso 1 1 calc R U . . .
C14 C -0.0386(2) 0.37831(7) 0.90875(18) 0.0292(4) Uani 1 1 d . . . . .
H14 H -0.1425 0.3697 0.9269 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0745(2) 0.47213(7) 0.31214(17) 0.0266(4) Uani 1 1 d . . . . .
H6 H 0.0005 0.4755 0.2214 0.032 Uiso 1 1 calc R U . . .
C13 C 0.0243(2) 0.34527(6) 0.83204(17) 0.0266(4) Uani 1 1 d . . . . .
H13 H -0.0363 0.314 0.7977 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0491(2) 0.42397(7) 0.95930(18) 0.0310(4) Uani 1 1 d . . . . .
H15 H 0.0041 0.4466 1.0112 0.037 Uiso 1 1 calc R U . . .
O23 O 0.26825(13) 0.28800(4) 0.29076(10) 0.0199(2) Uani 1 1 d . . . . .
O20 O 0.14162(14) 0.22552(4) -0.02026(11) 0.0225(2) Uani 1 1 d . . . . .
O21 O 0.38872(15) 0.26883(5) 0.08295(11) 0.0277(3) Uani 1 1 d . . . . .
O22 O 0.00140(14) 0.26493(5) 0.15621(11) 0.0293(3) Uani 1 1 d . . . . .
C21 C 0.15868(19) 0.27073(6) 0.18183(14) 0.0174(3) Uani 1 1 d . . . . .
C20 C 0.24304(19) 0.25491(6) 0.07456(14) 0.0167(3) Uani 1 1 d . . . . .
H34 H 0.488(3) 0.7074(7) 0.6831(19) 0.029(5) Uiso 1 1 d . . . . .
H20 H 0.196(3) 0.2197(10) -0.088(3) 0.062(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S10 O11 1.4266(11) . ?
S10 O10 1.4330(12) . ?
S10 N1 1.6453(13) . ?
S10 C11 1.7559(16) . ?
N34 C37 1.4851(18) . ?
N34 C35 1.4923(18) . ?
N34 C33 1.4957(18) . ?
N34 H34 0.88(2) . ?
N31 C3 1.4080(18) . ?
N31 C36 1.4625(18) . ?
N31 C32 1.4683(18) . ?
N1 C9 1.410(2) . ?
N1 C2 1.4164(19) . ?
C32 C33 1.512(2) . ?
C32 H32B 0.99 . ?
C32 H32A 0.99 . ?
C3 C2 1.356(2) . ?
C3 C4 1.444(2) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C2 H2 0.95 . ?
C11 C12 1.389(2) . ?
C11 C16 1.392(2) . ?
C4 C5 1.395(2) . ?
C4 C9 1.404(2) . ?
C35 C36 1.510(2) . ?
C35 H35B 0.99 . ?
C35 H35A 0.99 . ?
C8 C7 1.380(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.95 . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C37 H37A 0.98 . ?
C7 C6 1.399(2) . ?
C7 H7 0.95 . ?
C5 C6 1.385(2) . ?
C5 H5 0.95 . ?
C12 C13 1.384(2) . ?
C12 H12 0.95 . ?
C16 C15 1.382(2) . ?
C16 H16 0.95 . ?
C14 C13 1.382(2) . ?
C14 C15 1.385(3) . ?
C14 H14 0.95 . ?
C6 H6 0.95 . ?
C13 H13 0.95 . ?
C15 H15 0.95 . ?
O23 C21 1.2764(18) . ?
O20 C20 1.3049(18) . ?
O20 H20 0.96(3) . ?
O21 C20 1.2084(18) . ?
O22 C21 1.2211(18) . ?
C21 C20 1.557(2) . ?

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
O11 S10 O10 120.34(7) . . ?
O11 S10 N1 106.91(7) . . ?
O10 S10 N1 105.70(7) . . ?
O11 S10 C11 108.51(7) . . ?
O10 S10 C11 108.88(7) . . ?
N1 S10 C11 105.52(7) . . ?
C37 N34 C35 112.24(11) . . ?
C37 N34 C33 111.18(11) . . ?
C35 N34 C33 109.33(11) . . ?
C37 N34 H34 106.8(12) . . ?
C35 N34 H34 109.0(12) . . ?
C33 N34 H34 108.2(12) . . ?
C3 N31 C36 113.78(12) . . ?
C3 N31 C32 112.44(11) . . ?
C36 N31 C32 110.05(12) . . ?
C9 N1 C2 108.41(12) . . ?
C9 N1 S10 126.33(10) . . ?
C2 N1 S10 123.28(11) . . ?
N31 C32 C33 110.64(12) . . ?
N31 C32 H32B 109.5 . . ?
C33 C32 H32B 109.5 . . ?
N31 C32 H32A 109.5 . . ?
C33 C32 H32A 109.5 . . ?
H32B C32 H32A 108.1 . . ?
C2 C3 N31 127.67(14) . . ?
C2 C3 C4 108.20(13) . . ?
N31 C3 C4 124.09(13) . . ?
N34 C33 C32 109.65(12) . . ?
N34 C33 H33A 109.7 . . ?
C32 C33 H33A 109.7 . . ?
N34 C33 H33B 109.7 . . ?
C32 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C3 C2 N1 108.73(13) . . ?
C3 C2 H2 125.6 . . ?
N1 C2 H2 125.6 . . ?
C12 C11 C16 121.35(15) . . ?
C12 C11 S10 119.39(12) . . ?
C16 C11 S10 119.25(12) . . ?
C5 C4 C9 119.24(14) . . ?
C5 C4 C3 133.06(14) . . ?
C9 C4 C3 107.60(13) . . ?
N34 C35 C36 109.60(11) . . ?
N34 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
N34 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
H35B C35 H35A 108.2 . . ?
C7 C8 C9 117.23(14) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
N31 C36 C35 109.43(12) . . ?
N31 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
N31 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C8 C9 C4 122.49(14) . . ?
C8 C9 N1 130.48(14) . . ?
C4 C9 N1 106.98(13) . . ?
N34 C37 H37B 109.5 . . ?
N34 C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N34 C37 H37A 109.5 . . ?
H37B C37 H37A 109.5 . . ?
H37C C37 H37A 109.5 . . ?
C8 C7 C6 121.29(15) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C6 C5 C4 118.55(15) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C13 C12 C11 119.18(15) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C15 C16 C11 118.53(15) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C13 C14 C15 120.38(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C5 C6 C7 121.18(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C14 C13 C12 119.98(16) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C16 C15 C14 120.58(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C20 O20 H20 109.1(15) . . ?
O22 C21 O23 127.25(14) . . ?
O22 C21 C20 118.98(13) . . ?
O23 C21 C20 113.76(12) . . ?
O21 C20 O20 125.44(14) . . ?
O21 C20 C21 121.51(13) . . ?
O20 C20 C21 113.05(12) . . ?

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
O11 S10 N1 C9 44.58(15) . . . . ?
O10 S10 N1 C9 173.92(13) . . . . ?
C11 S10 N1 C9 -70.82(14) . . . . ?
O11 S10 N1 C2 -153.33(13) . . . . ?
O10 S10 N1 C2 -24.00(14) . . . . ?
C11 S10 N1 C2 91.27(14) . . . . ?
C3 N31 C32 C33 172.54(12) . . . . ?
C36 N31 C32 C33 -59.49(16) . . . . ?
C36 N31 C3 C2 -14.3(2) . . . . ?
C32 N31 C3 C2 111.68(17) . . . . ?
C36 N31 C3 C4 163.06(14) . . . . ?
C32 N31 C3 C4 -70.97(18) . . . . ?
C37 N34 C33 C32 178.07(12) . . . . ?
C35 N34 C33 C32 -57.46(15) . . . . ?
N31 C32 C33 N34 57.77(16) . . . . ?
N31 C3 C2 N1 179.21(14) . . . . ?
C4 C3 C2 N1 1.52(17) . . . . ?
C9 N1 C2 C3 -2.90(17) . . . . ?
S10 N1 C2 C3 -167.77(11) . . . . ?
O11 S10 C11 C12 -10.01(15) . . . . ?
O10 S10 C11 C12 -142.66(13) . . . . ?
N1 S10 C11 C12 104.28(13) . . . . ?
O11 S10 C11 C16 171.36(12) . . . . ?
O10 S10 C11 C16 38.71(14) . . . . ?
N1 S10 C11 C16 -74.35(14) . . . . ?
C2 C3 C4 C5 176.57(16) . . . . ?
N31 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C9 0.41(17) . . . . ?
N31 C3 C4 C9 -177.38(13) . . . . ?
C37 N34 C35 C36 -176.95(12) . . . . ?
C33 N34 C35 C36 59.20(15) . . . . ?
C3 N31 C36 C35 -172.21(12) . . . . ?
C32 N31 C36 C35 60.57(15) . . . . ?
N34 C35 C36 N31 -60.76(15) . . . . ?
C7 C8 C9 C4 1.7(2) . . . . ?
C7 C8 C9 N1 178.75(15) . . . . ?
C5 C4 C9 C8 -1.3(2) . . . . ?
C3 C4 C9 C8 175.48(14) . . . . ?
C5 C4 C9 N1 -178.95(13) . . . . ?
C3 C4 C9 N1 -2.17(16) . . . . ?
C2 N1 C9 C8 -174.29(15) . . . . ?
S10 N1 C9 C8 -10.0(2) . . . . ?
C2 N1 C9 C4 3.10(16) . . . . ?
S10 N1 C9 C4 167.38(11) . . . . ?
C9 C8 C7 C6 -1.2(2) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C5 C6 -175.47(16) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
S10 C11 C12 C13 -179.24(12) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
S10 C11 C16 C15 178.58(13) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C8 C7 C6 C5 0.3(3) . . . . ?
C15 C14 C13 C12 0.0(3) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C16 C15 C14 0.7(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
O22 C21 C20 O21 165.39(15) . . . . ?
O23 C21 C20 O21 -15.8(2) . . . . ?
O22 C21 C20 O20 -15.4(2) . . . . ?
O23 C21 C20 O20 163.45(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C33 H33A O21 0.99 2.62 3.5273(19) 151.7 2_655
C2 H2 O10 0.95 2.65 3.454(2) 142.4 3_667
C35 H35B O20 0.99 2.59 3.5276(18) 157.4 2
C35 H35A O21 0.99 2.48 3.0448(18) 116.2 3_666
C8 H8 O11 0.95 2.55 3.096(2) 117.2 .
C37 H37C O22 0.98 2.44 3.247(2) 139 2
C37 H37A O11 0.98 2.58 3.2138(18) 122.1 2_656
C16 H16 O10 0.95 2.65 3.596(2) 177.8 3_667
N34 H34 O23 0.88(2) 1.91(2) 2.7422(16) 157.5(18) 3_666
N34 H34 O21 0.88(2) 2.414(19) 2.9676(17) 121.1(15) 3_666
O20 H20 O23 0.96(3) 1.59(3) 2.5493(14) 174(2) 4_565

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1550192'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-09-23T16:30:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         
'4(C20 H22 N3 O), C2 O4, 2(C2 H O4), C2 H2 O4, 2(H2 O)'
_chemical_formula_sum            'C88 H96 N12 O22'
_chemical_formula_weight         1673.76
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.3613(2)
_cell_length_b                   39.3723(9)
_cell_length_c                   14.2823(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.867(3)
_cell_angle_gamma                90
_cell_volume                     4089.99(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13369
_cell_measurement_theta_min      2.8422
_cell_measurement_theta_max      29.4709

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.59601
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.98

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0045305
_diffrn_orient_matrix_ub_12      0.002966
_diffrn_orient_matrix_ub_13      0.0485513
_diffrn_orient_matrix_ub_21      -0.0055223
_diffrn_orient_matrix_ub_22      0.0177338
_diffrn_orient_matrix_ub_23      -0.0087379
_diffrn_orient_matrix_ub_31      -0.0972853
_diffrn_orient_matrix_ub_32      -0.0011435
_diffrn_orient_matrix_ub_33      -0.0095229
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_number            57362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         29.536
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.881
_reflns_Friedel_coverage         0.911
_reflns_number_total             20842
_reflns_number_gt                14999
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.6003P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         20842
_refine_ls_number_parameters     1149
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.123
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O82 O 0.5406(4) 0.68091(7) 1.0480(2) 0.0286(6) Uani 1 1 d . . . . .
O73 O 1.1293(4) 0.40140(7) 0.65519(19) 0.0266(6) Uani 1 1 d . . . . .
O63 O 0.3285(4) 0.26219(6) 0.72404(18) 0.0284(6) Uani 1 1 d . . . . .
O83 O 0.6189(4) 0.70755(6) 1.18399(18) 0.0243(6) Uani 1 1 d . . . . .
O81 O 0.5390(4) 0.74848(7) 0.9715(2) 0.0310(6) Uani 1 1 d . . . . .
O72 O 1.0303(4) 0.43041(6) 0.52540(19) 0.0265(6) Uani 1 1 d . . . . .
O61 O 0.2958(4) 0.32014(7) 0.6258(2) 0.0327(7) Uani 1 1 d . . . . .
O62 O 0.1593(4) 0.28433(7) 0.8260(2) 0.0325(7) Uani 1 1 d . . . . .
N51A N 1.0019(4) 0.64267(7) 0.9071(2) 0.0203(7) Uani 1 1 d . . . . .
O60 O 0.1592(4) 0.34424(6) 0.73847(19) 0.0298(7) Uani 1 1 d . . . . .
O71 O 0.8220(4) 0.35955(7) 0.5720(2) 0.0348(7) Uani 1 1 d . . . . .
O92 O 0.0550(4) 0.81495(6) 0.7456(2) 0.0298(7) Uani 1 1 d . . . . .
O91 O 0.3147(4) 0.78538(7) 0.8692(2) 0.0281(6) Uani 1 1 d D . . . .
N51C N 0.4891(4) 0.46272(7) 0.3704(2) 0.0211(7) Uani 1 1 d . . . . .
N51B N 0.8298(5) 0.72697(8) 0.5670(2) 0.0266(7) Uani 1 1 d . . . . .
N51 N 0.2515(5) 0.37672(8) 1.0201(2) 0.0253(7) Uani 1 1 d . . . . .
N54 N -0.0317(5) 0.34344(8) 0.8886(3) 0.0281(8) Uani 1 1 d . . . . .
O10 O 0.8894(4) 0.48183(7) 1.2209(2) 0.0331(7) Uani 1 1 d . . . . .
O93 O 0.2589(4) 0.82410(7) 0.6467(2) 0.0295(6) Uani 1 1 d . . . . .
O80 O 0.3593(4) 0.75526(7) 1.0834(2) 0.0331(7) Uani 1 1 d . . . . .
N1A N 0.8636(4) 0.52626(7) 0.8903(2) 0.0211(7) Uani 1 1 d . . . . .
N54A N 0.9156(4) 0.71420(8) 0.8915(2) 0.0206(7) Uani 1 1 d . . . . .
C71 C 1.0389(5) 0.40408(9) 0.5689(3) 0.0207(8) Uani 1 1 d . . . . .
O90 O 0.5196(4) 0.79331(7) 0.7698(2) 0.0306(7) Uani 1 1 d . . . . .
N1 N 0.6115(4) 0.47196(8) 1.1305(2) 0.0244(7) Uani 1 1 d . . . . .
N1C N 0.4113(5) 0.58068(7) 0.3905(2) 0.0268(7) Uani 1 1 d . . . . .
C9 C 0.6278(5) 0.43691(9) 1.1161(3) 0.0227(8) Uani 1 1 d . . . . .
O70 O 0.9644(4) 0.36397(7) 0.44443(19) 0.0337(7) Uani 1 1 d . . . . .
C5A C 1.0387(5) 0.61001(9) 0.9502(3) 0.0202(8) Uani 1 1 d . . . . .
N54B N 0.5370(5) 0.76237(8) 0.4469(2) 0.0281(8) Uani 1 1 d . . . . .
N54C N 0.3466(4) 0.39456(7) 0.3476(2) 0.0194(7) Uani 1 1 d . . . . .
O10A O 0.9060(4) 0.48018(6) 0.9872(2) 0.0299(6) Uani 1 1 d . . . . .
C91 C 0.2073(5) 0.81304(9) 0.7244(3) 0.0237(8) Uani 1 1 d . . . . .
O10C O 0.5915(5) 0.62663(7) 0.4362(3) 0.0495(9) Uani 1 1 d . . . . .
O10B O 1.4213(4) 0.62246(8) 0.7940(2) 0.0453(8) Uani 1 1 d . . . . .
C11 C 0.7183(5) 0.53070(10) 1.1636(3) 0.0274(9) Uani 1 1 d . . . . .
C90 C 0.3669(6) 0.79584(9) 0.7906(3) 0.0244(8) Uani 1 1 d . . . . .
C11A C 0.7535(5) 0.46980(9) 0.8321(3) 0.0218(8) Uani 1 1 d . . . . .
N1B N 1.1793(4) 0.62964(8) 0.6750(2) 0.0260(7) Uani 1 1 d . . . . .
C60 C 0.2311(5) 0.31981(9) 0.7007(3) 0.0229(8) Uani 1 1 d . . . . .
C10 C 0.7506(5) 0.49337(10) 1.1748(3) 0.0264(9) Uani 1 1 d . . . . .
C8 C 0.7813(6) 0.41626(10) 1.1365(3) 0.0269(9) Uani 1 1 d . . . . .
H8 H 0.8991 0.4252 1.1607 0.032 Uiso 1 1 calc R U . . .
C3B C 0.9010(5) 0.64878(9) 0.6090(3) 0.0247(8) Uani 1 1 d . . . . .
H3B H 0.7743 0.6494 0.5828 0.03 Uiso 1 1 calc R U . . .
C3 C 0.3258(5) 0.45283(9) 1.0735(3) 0.0246(8) Uani 1 1 d . . . . .
H3 H 0.1971 0.4521 1.052 0.03 Uiso 1 1 calc R U . . .
C10A C 0.8464(5) 0.49169(9) 0.9098(3) 0.0228(8) Uani 1 1 d . . . . .
C81 C 0.5531(5) 0.70708(9) 1.0934(3) 0.0197(8) Uani 1 1 d . . . . .
C52B C 0.7492(6) 0.71363(10) 0.4734(3) 0.0279(9) Uani 1 1 d . . . . .
H2BA H 0.7559 0.6885 0.4742 0.033 Uiso 1 1 calc R U . . .
H2BB H 0.821 0.722 0.4249 0.033 Uiso 1 1 calc R U . . .
C52 C 0.1797(6) 0.39151(10) 0.9269(3) 0.0282(9) Uani 1 1 d . . . . .
H52A H 0.2565 0.3839 0.8798 0.034 Uiso 1 1 calc R U . . .
H52B H 0.1876 0.4166 0.931 0.034 Uiso 1 1 calc R U . . .
C55C C 0.2240(5) 0.42505(9) 0.3411(3) 0.0229(8) Uani 1 1 d . . . . .
H5CA H 0.1062 0.419 0.3622 0.027 Uiso 1 1 calc R U . . .
H5CB H 0.1971 0.4328 0.2745 0.027 Uiso 1 1 calc R U . . .
C3A C 0.8117(5) 0.57771(9) 0.8218(3) 0.0209(8) Uani 1 1 d . . . . .
H3A H 0.765 0.5953 0.7794 0.025 Uiso 1 1 calc R U . . .
C5B C 1.0038(6) 0.71283(10) 0.6041(3) 0.0255(9) Uani 1 1 d . . . . .
C80 C 0.4782(5) 0.74059(9) 1.0470(3) 0.0229(8) Uani 1 1 d . . . . .
C4C C 0.4624(5) 0.52403(9) 0.3889(3) 0.0234(8) Uani 1 1 d . . . . .
C2B C 0.9973(5) 0.62082(10) 0.6410(3) 0.0238(8) Uani 1 1 d . . . . .
H2B H 0.9485 0.5985 0.6406 0.029 Uiso 1 1 calc R U . . .
C55A C 0.7733(5) 0.68740(9) 0.8650(3) 0.0236(8) Uani 1 1 d . . . . .
H5AB H 0.7643 0.6822 0.7966 0.028 Uiso 1 1 calc R U . . .
H5AA H 0.6522 0.6959 0.8765 0.028 Uiso 1 1 calc R U . . .
C53C C 0.5298(5) 0.40392(9) 0.3236(3) 0.0215(8) Uani 1 1 d . . . . .
H3CA H 0.5164 0.4098 0.2555 0.026 Uiso 1 1 calc R U . . .
H3CB H 0.613 0.3841 0.3347 0.026 Uiso 1 1 calc R U . . .
C55 C 0.0406(6) 0.32856(10) 0.9832(3) 0.0315(10) Uani 1 1 d . . . . .
H55A H 0.0346 0.3035 0.9794 0.038 Uiso 1 1 calc R U . . .
H55B H -0.0364 0.3361 1.0303 0.038 Uiso 1 1 calc R U . . .
C11B C 1.2853(5) 0.57186(10) 0.7257(3) 0.0296(9) Uani 1 1 d . . . . .
C52C C 0.6148(5) 0.43358(9) 0.3817(3) 0.0228(8) Uani 1 1 d . . . . .
H2CB H 0.641 0.427 0.4494 0.027 Uiso 1 1 calc R U . . .
H2CA H 0.7324 0.4399 0.3608 0.027 Uiso 1 1 calc R U . . .
C4B C 1.0242(5) 0.67746(9) 0.6214(3) 0.0228(8) Uani 1 1 d . . . . .
C9B C 1.1970(6) 0.66483(10) 0.6636(3) 0.0263(9) Uani 1 1 d . . . . .
C4A C 0.9435(5) 0.58166(9) 0.9076(3) 0.0199(8) Uani 1 1 d . . . . .
C56C C 0.3161(5) 0.45310(9) 0.4024(3) 0.0227(8) Uani 1 1 d . . . . .
H6CA H 0.2335 0.4731 0.3991 0.027 Uiso 1 1 calc R U . . .
H6CB H 0.3413 0.4454 0.4691 0.027 Uiso 1 1 calc R U . . .
C56A C 0.8203(5) 0.65538(9) 0.9216(3) 0.0236(8) Uani 1 1 d . . . . .
H6AA H 0.8209 0.6601 0.9897 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.7259 0.6378 0.9016 0.028 Uiso 1 1 calc R U . . .
C53B C 0.5518(6) 0.72458(10) 0.4476(3) 0.0295(9) Uani 1 1 d . . . . .
H3BB H 0.5012 0.7156 0.3842 0.035 Uiso 1 1 calc R U . . .
H3BA H 0.4785 0.7151 0.494 0.035 Uiso 1 1 calc R U . . .
C56B C 0.8201(6) 0.76418(9) 0.5644(3) 0.0293(9) Uani 1 1 d . . . . .
H6BB H 0.8925 0.7728 0.5166 0.035 Uiso 1 1 calc R U . . .
H6BA H 0.8749 0.7734 0.6269 0.035 Uiso 1 1 calc R U . . .
C15A C 0.5450(6) 0.42410(10) 0.7862(3) 0.0344(10) Uani 1 1 d . . . . .
H5PA H 0.457 0.4082 0.8015 0.041 Uiso 1 1 calc R U . . .
C9A C 0.9715(5) 0.54961(9) 0.9500(3) 0.0209(8) Uani 1 1 d . . . . .
C5 C 0.4280(6) 0.38946(9) 1.0579(3) 0.0237(8) Uani 1 1 d . . . . .
C9C C 0.5371(6) 0.55517(10) 0.4256(3) 0.0278(9) Uani 1 1 d . . . . .
C2C C 0.2632(5) 0.56534(10) 0.3319(3) 0.0247(8) Uani 1 1 d . . . . .
H2C H 0.1595 0.577 0.2991 0.03 Uiso 1 1 calc R U . . .
C52A C 1.1418(5) 0.66833(9) 0.9390(3) 0.0223(8) Uani 1 1 d . . . . .
H2AA H 1.2648 0.6596 0.9313 0.027 Uiso 1 1 calc R U . . .
H2AB H 1.1422 0.6734 1.0069 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7534(6) 0.38211(10) 1.1198(3) 0.0290(9) Uani 1 1 d . . . . .
H7 H 0.8543 0.367 1.1356 0.035 Uiso 1 1 calc R U . . .
C61 C 0.2393(5) 0.28571(9) 0.7561(3) 0.0227(8) Uani 1 1 d . . . . .
C5C C 0.5646(5) 0.49394(9) 0.4089(3) 0.0234(8) Uani 1 1 d . . . . .
C3C C 0.2907(5) 0.53158(9) 0.3295(3) 0.0240(8) Uani 1 1 d . . . . .
H3C H 0.2108 0.5155 0.2946 0.029 Uiso 1 1 calc R U . . .
C8B C 1.3500(6) 0.68521(11) 0.6888(3) 0.0317(10) Uani 1 1 d . . . . .
H8B H 1.4653 0.6759 0.7157 0.038 Uiso 1 1 calc R U . . .
C7A C 1.1855(5) 0.57232(9) 1.0726(3) 0.0247(8) Uani 1 1 d . . . . .
H7A H 1.2706 0.5695 1.1292 0.03 Uiso 1 1 calc R U . . .
C57A C 0.8730(6) 0.74554(9) 0.8340(3) 0.0277(9) Uani 1 1 d . . . . .
H7AC H 0.8624 0.7399 0.7665 0.042 Uiso 1 1 calc R U . . .
H7AB H 0.9718 0.7622 0.8507 0.042 Uiso 1 1 calc R U . . .
H7AA H 0.7566 0.7552 0.8469 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4520(5) 0.42452(9) 1.0784(3) 0.0225(8) Uani 1 1 d . . . . .
C12A C 0.7972(6) 0.47052(10) 0.7413(3) 0.0270(9) Uani 1 1 d . . . . .
H2PA H 0.8836 0.4866 0.7253 0.032 Uiso 1 1 calc R U . . .
C8A C 1.0892(5) 0.54416(10) 1.0335(3) 0.0242(8) Uani 1 1 d . . . . .
H8A H 1.1036 0.5224 1.0624 0.029 Uiso 1 1 calc R U . . .
C2A C 0.7672(5) 0.54445(9) 0.8131(3) 0.0221(8) Uani 1 1 d . . . . .
H2A H 0.6839 0.5348 0.7627 0.027 Uiso 1 1 calc R U . . .
C7B C 1.3284(6) 0.71916(11) 0.6734(3) 0.0335(10) Uani 1 1 d . . . . .
H7B H 1.4297 0.7339 0.6916 0.04 Uiso 1 1 calc R U . . .
C53A C 1.1009(5) 0.70039(9) 0.8812(3) 0.0218(8) Uani 1 1 d . . . . .
H3AB H 1.1961 0.7177 0.9026 0.026 Uiso 1 1 calc R U . . .
H3AA H 1.105 0.6954 0.8137 0.026 Uiso 1 1 calc R U . . .
C57C C 0.2624(6) 0.36644(10) 0.2862(3) 0.0289(9) Uani 1 1 d . . . . .
H7CC H 0.3458 0.3469 0.2923 0.043 Uiso 1 1 calc R U . . .
H7CA H 0.2403 0.374 0.22 0.043 Uiso 1 1 calc R U . . .
H7CB H 0.1454 0.3599 0.3058 0.043 Uiso 1 1 calc R U . . .
C55B C 0.6243(6) 0.77634(10) 0.5404(3) 0.0315(10) Uani 1 1 d . . . . .
H5BB H 0.5534 0.769 0.5904 0.038 Uiso 1 1 calc R U . . .
H5BA H 0.6222 0.8015 0.5381 0.038 Uiso 1 1 calc R U . . .
C15B C 1.2896(6) 0.51699(12) 0.7982(4) 0.0392(11) Uani 1 1 d . . . . .
H5PB H 1.2911 0.5033 0.8532 0.047 Uiso 1 1 calc R U . . .
C16A C 0.6281(6) 0.44593(10) 0.8548(3) 0.0292(9) Uani 1 1 d . . . . .
H6PA H 0.6 0.4447 0.9175 0.035 Uiso 1 1 calc R U . . .
C10B C 1.3031(5) 0.60933(11) 0.7364(3) 0.0304(9) Uani 1 1 d . . . . .
C53 C -0.0168(6) 0.38124(10) 0.8943(3) 0.0279(9) Uani 1 1 d . . . . .
H53A H -0.0954 0.39 0.9393 0.033 Uiso 1 1 calc R U . . .
H53B H -0.0606 0.3913 0.8313 0.033 Uiso 1 1 calc R U . . .
C12C C 0.3402(6) 0.66031(9) 0.2828(3) 0.0271(9) Uani 1 1 d . . . . .
H2PC H 0.4602 0.6602 0.2661 0.033 Uiso 1 1 calc R U . . .
C70 C 0.9330(5) 0.37243(9) 0.5261(3) 0.0241(8) Uani 1 1 d . . . . .
C11C C 0.2967(6) 0.63821(9) 0.3514(3) 0.0260(9) Uani 1 1 d . . . . .
C6B C 1.1590(6) 0.73285(10) 0.6309(3) 0.0322(10) Uani 1 1 d . . . . .
H6B H 1.1502 0.7566 0.6201 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4255(5) 0.48051(10) 1.1053(3) 0.0261(9) Uani 1 1 d . . . . .
H2 H 0.3764 0.5026 1.1098 0.031 Uiso 1 1 calc R U . . .
C56 C 0.2376(6) 0.33960(10) 1.0146(3) 0.0309(10) Uani 1 1 d . . . . .
H56B H 0.2835 0.3297 1.0775 0.037 Uiso 1 1 calc R U . . .
H56A H 0.3155 0.331 0.9691 0.037 Uiso 1 1 calc R U . . .
C6A C 1.1621(5) 0.60461(10) 1.0321(3) 0.0251(8) Uani 1 1 d . . . . .
H6A H 1.232 0.6231 1.0612 0.03 Uiso 1 1 calc R U . . .
C6 C 0.5825(6) 0.36862(10) 1.0807(3) 0.0299(9) Uani 1 1 d . . . . .
H6 H 0.5712 0.3449 1.0693 0.036 Uiso 1 1 calc R U . . .
C14A C 0.5875(6) 0.42493(10) 0.6956(3) 0.0326(10) Uani 1 1 d . . . . .
H4PA H 0.5286 0.4098 0.6487 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6462(5) 0.54550(10) 1.0772(3) 0.0307(9) Uani 1 1 d . . . . .
H12 H 0.605 0.5316 1.0238 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6348(6) 0.58053(11) 1.0693(4) 0.0373(11) Uani 1 1 d . . . . .
H13 H 0.5908 0.5907 1.0097 0.045 Uiso 1 1 calc R U . . .
C13C C 0.2092(6) 0.68257(11) 0.2386(3) 0.0347(10) Uani 1 1 d . . . . .
H3PC H 0.2397 0.6977 0.1917 0.042 Uiso 1 1 calc R U . . .
C8C C 0.7068(6) 0.55757(10) 0.4819(3) 0.0382(11) Uani 1 1 d . . . . .
H8C H 0.7531 0.5786 0.5078 0.046 Uiso 1 1 calc R U . . .
C10C C 0.4455(6) 0.61551(10) 0.3974(3) 0.0319(10) Uani 1 1 d . . . . .
C12B C 1.2779(6) 0.55662(11) 0.6370(3) 0.0351(10) Uani 1 1 d . . . . .
H2PB H 1.2714 0.5701 0.5815 0.042 Uiso 1 1 calc R U . . .
C16B C 1.2949(5) 0.55214(11) 0.8061(3) 0.0337(10) Uani 1 1 d . . . . .
H6PB H 1.3051 0.5626 0.8667 0.04 Uiso 1 1 calc R U . . .
C13A C 0.7149(6) 0.44768(10) 0.6734(3) 0.0330(10) Uani 1 1 d . . . . .
H3PA H 0.7471 0.4479 0.6115 0.04 Uiso 1 1 calc R U . . .
C6C C 0.7389(6) 0.49660(10) 0.4627(3) 0.0317(10) Uani 1 1 d . . . . .
H6C H 0.8131 0.4769 0.4749 0.038 Uiso 1 1 calc R U . . .
C14B C 1.2821(6) 0.50187(11) 0.7105(4) 0.0391(11) Uani 1 1 d . . . . .
H4PB H 1.2783 0.4778 0.7054 0.047 Uiso 1 1 calc R U . . .
C16C C 0.1217(6) 0.63875(10) 0.3763(3) 0.0359(11) Uani 1 1 d . . . . .
H6PC H 0.0912 0.6239 0.424 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7533(6) 0.58610(11) 1.2339(4) 0.0421(12) Uani 1 1 d . . . . .
H15 H 0.7862 0.6001 1.288 0.05 Uiso 1 1 calc R U . . .
C14C C 0.0344(6) 0.68286(11) 0.2622(4) 0.0382(11) Uani 1 1 d . . . . .
H4PC H -0.0557 0.698 0.2312 0.046 Uiso 1 1 calc R U . . .
C13B C 1.2801(6) 0.52132(12) 0.6309(4) 0.0410(11) Uani 1 1 d . . . . .
H3PB H 1.2803 0.5107 0.5712 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7722(6) 0.55104(10) 1.2421(3) 0.0321(10) Uani 1 1 d . . . . .
H16 H 0.8218 0.5411 1.3011 0.039 Uiso 1 1 calc R U . . .
C57 C -0.2225(6) 0.33231(11) 0.8525(4) 0.0403(11) Uani 1 1 d . . . . .
H57C H -0.3065 0.3416 0.8929 0.061 Uiso 1 1 calc R U . . .
H57B H -0.2286 0.3074 0.8532 0.061 Uiso 1 1 calc R U . . .
H57A H -0.2583 0.3405 0.7875 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6871(6) 0.60064(11) 1.1475(4) 0.0429(12) Uani 1 1 d . . . . .
H14 H 0.6775 0.6246 1.142 0.052 Uiso 1 1 calc R U . . .
C7C C 0.8056(6) 0.52784(11) 0.4988(3) 0.0415(12) Uani 1 1 d . . . . .
H7C H 0.9236 0.5287 0.5366 0.05 Uiso 1 1 calc R U . . .
C15C C -0.0086(6) 0.66118(11) 0.3306(4) 0.0421(12) Uani 1 1 d . . . . .
H5PC H -0.1289 0.6615 0.347 0.05 Uiso 1 1 calc R U . . .
O2W O 0.4473(5) 0.36611(7) 0.5191(2) 0.0294(7) Uani 1 1 d . . . . .
O1W O 0.9933(4) 0.73681(8) 1.0719(2) 0.0310(7) Uani 1 1 d . . . . .
C57B C 0.3443(6) 0.77391(11) 0.4199(3) 0.0366(11) Uani 1 1 d . . . . .
H7BA H 0.2686 0.7647 0.4646 0.055 Uiso 1 1 calc R U . . .
H7BC H 0.2969 0.7659 0.3558 0.055 Uiso 1 1 calc R U . . .
H7BB H 0.34 0.7988 0.4213 0.055 Uiso 1 1 calc R U . . .
H54B H 0.605(6) 0.7711(11) 0.400(3) 0.038(12) Uiso 1 1 d . . . . .
H54C H 0.371(5) 0.3866(10) 0.411(3) 0.025(11) Uiso 1 1 d . . . . .
H2W H 0.940(8) 0.7509(15) 1.101(4) 0.069(19) Uiso 1 1 d . . . . .
H54 H 0.041(6) 0.3368(11) 0.849(3) 0.035(13) Uiso 1 1 d . . . . .
H4W H 0.391(8) 0.3536(14) 0.553(4) 0.061(18) Uiso 1 1 d . . . . .
H54A H 0.913(7) 0.7197(12) 0.956(4) 0.047(14) Uiso 1 1 d . . . . .
H91 H 0.409(6) 0.7722(11) 0.908(3) 0.061(16) Uiso 1 1 d D . . . .
H3W H 0.569(8) 0.3614(13) 0.538(4) 0.055(16) Uiso 1 1 d . . . . .
H93 H 0.158(7) 0.8378(13) 0.604(4) 0.062(16) Uiso 1 1 d . . . . .
H1W H 1.117(9) 0.7439(17) 1.081(5) 0.092 Uiso 1 1 d . U . . .
H73 H 1.132(7) 0.3785(13) 0.675(4) 0.053(15) Uiso 1 1 d . . . . .
H83 H 0.631(8) 0.7287(15) 1.215(4) 0.079 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O82 C81 1.213(4) . ?
O73 C71 1.312(5) . ?
O73 H73 0.95(5) . ?
O63 C61 1.262(4) . ?
O83 C81 1.311(4) . ?
O83 H83 0.94(6) . ?
O81 C80 1.268(5) . ?
O72 C71 1.205(4) . ?
O61 C60 1.237(4) . ?
O62 C61 1.236(4) . ?
N51A C5A 1.433(5) . ?
N51A C52A 1.464(5) . ?
N51A C56A 1.472(5) . ?
O60 C60 1.259(4) . ?
O71 C70 1.233(5) . ?
O92 C91 1.208(5) . ?
O91 C90 1.308(5) . ?
O91 H91 0.97(3) . ?
N51C C5C 1.424(5) . ?
N51C C52C 1.467(5) . ?
N51C C56C 1.467(5) . ?
N51B C5B 1.422(5) . ?
N51B C56B 1.467(5) . ?
N51B C52B 1.473(5) . ?
N51 C5 1.420(5) . ?
N51 C56 1.466(5) . ?
N51 C52 1.475(5) . ?
N54 C57 1.485(6) . ?
N54 C55 1.493(5) . ?
N54 C53 1.494(5) . ?
N54 H54 0.88(4) . ?
O10 C10 1.215(5) . ?
O93 C91 1.301(5) . ?
O93 H93 1.04(6) . ?
O80 C80 1.229(4) . ?
N1A C10A 1.399(5) . ?
N1A C2A 1.411(5) . ?
N1A C9A 1.412(5) . ?
N54A C57A 1.489(5) . ?
N54A C55A 1.494(5) . ?
N54A C53A 1.496(5) . ?
N54A H54A 0.95(5) . ?
C71 C70 1.545(5) . ?
O90 C90 1.210(5) . ?
N1 C10 1.400(5) . ?
N1 C2 1.402(5) . ?
N1 C9 1.403(5) . ?
N1C C10C 1.395(5) . ?
N1C C2C 1.404(5) . ?
N1C C9C 1.406(5) . ?
C9 C8 1.386(5) . ?
C9 C4 1.410(5) . ?
O70 C70 1.268(5) . ?
C5A C6A 1.383(5) . ?
C5A C4A 1.405(5) . ?
N54B C57B 1.483(5) . ?
N54B C53B 1.492(5) . ?
N54B C55B 1.495(5) . ?
N54B H54B 0.96(5) . ?
N54C C57C 1.487(5) . ?
N54C C53C 1.488(5) . ?
N54C C55C 1.496(5) . ?
N54C H54C 0.95(4) . ?
O10A C10A 1.213(5) . ?
C91 C90 1.547(5) . ?
O10C C10C 1.213(5) . ?
O10B C10B 1.217(5) . ?
C11 C16 1.385(6) . ?
C11 C12 1.393(6) . ?
C11 C10 1.494(5) . ?
C11A C12A 1.384(5) . ?
C11A C16A 1.390(5) . ?
C11A C10A 1.486(5) . ?
N1B C2B 1.397(5) . ?
N1B C9B 1.403(5) . ?
N1B C10B 1.411(5) . ?
C60 C61 1.555(5) . ?
C8 C7 1.375(6) . ?
C8 H8 0.95 . ?
C3B C2B 1.351(5) . ?
C3B C4B 1.442(5) . ?
C3B H3B 0.95 . ?
C3 C2 1.353(6) . ?
C3 C4 1.446(5) . ?
C3 H3 0.95 . ?
C81 C80 1.540(5) . ?
C52B C53B 1.506(6) . ?
C52B H2BA 0.99 . ?
C52B H2BB 0.99 . ?
C52 C53 1.505(6) . ?
C52 H52A 0.99 . ?
C52 H52B 0.99 . ?
C55C C56C 1.504(5) . ?
C55C H5CA 0.99 . ?
C55C H5CB 0.99 . ?
C3A C2A 1.351(5) . ?
C3A C4A 1.450(5) . ?
C3A H3A 0.95 . ?
C5B C6B 1.392(6) . ?
C5B C4B 1.418(5) . ?
C4C C5C 1.409(5) . ?
C4C C9C 1.411(5) . ?
C4C C3C 1.441(5) . ?
C2B H2B 0.95 . ?
C55A C56A 1.509(5) . ?
C55A H5AB 0.99 . ?
C55A H5AA 0.99 . ?
C53C C52C 1.511(5) . ?
C53C H3CA 0.99 . ?
C53C H3CB 0.99 . ?
C55 C56 1.514(6) . ?
C55 H55A 0.99 . ?
C55 H55B 0.99 . ?
C11B C16B 1.379(6) . ?
C11B C12B 1.396(6) . ?
C11B C10B 1.487(6) . ?
C52C H2CB 0.99 . ?
C52C H2CA 0.99 . ?
C4B C9B 1.411(6) . ?
C9B C8B 1.385(5) . ?
C4A C9A 1.401(5) . ?
C56C H6CA 0.99 . ?
C56C H6CB 0.99 . ?
C56A H6AA 0.99 . ?
C56A H6AB 0.99 . ?
C53B H3BB 0.99 . ?
C53B H3BA 0.99 . ?
C56B C55B 1.507(6) . ?
C56B H6BB 0.99 . ?
C56B H6BA 0.99 . ?
C15A C16A 1.374(6) . ?
C15A C14A 1.379(6) . ?
C15A H5PA 0.95 . ?
C9A C8A 1.378(5) . ?
C5 C6 1.400(5) . ?
C5 C4 1.416(5) . ?
C9C C8C 1.381(6) . ?
C2C C3C 1.346(5) . ?
C2C H2C 0.95 . ?
C52A C53A 1.512(5) . ?
C52A H2AA 0.99 . ?
C52A H2AB 0.99 . ?
C7 C6 1.400(6) . ?
C7 H7 0.95 . ?
C5C C6C 1.394(5) . ?
C3C H3C 0.95 . ?
C8B C7B 1.360(6) . ?
C8B H8B 0.95 . ?
C7A C8A 1.386(5) . ?
C7A C6A 1.396(5) . ?
C7A H7A 0.95 . ?
C57A H7AC 0.98 . ?
C57A H7AB 0.98 . ?
C57A H7AA 0.98 . ?
C12A C13A 1.391(6) . ?
C12A H2PA 0.95 . ?
C8A H8A 0.95 . ?
C2A H2A 0.95 . ?
C7B C6B 1.407(6) . ?
C7B H7B 0.95 . ?
C53A H3AB 0.99 . ?
C53A H3AA 0.99 . ?
C57C H7CC 0.98 . ?
C57C H7CA 0.98 . ?
C57C H7CB 0.98 . ?
C55B H5BB 0.99 . ?
C55B H5BA 0.99 . ?
C15B C14B 1.380(7) . ?
C15B C16B 1.388(6) . ?
C15B H5PB 0.95 . ?
C16A H6PA 0.95 . ?
C53 H53A 0.99 . ?
C53 H53B 0.99 . ?
C12C C13C 1.381(6) . ?
C12C C11C 1.385(5) . ?
C12C H2PC 0.95 . ?
C11C C16C 1.388(6) . ?
C11C C10C 1.486(6) . ?
C6B H6B 0.95 . ?
C2 H2 0.95 . ?
C56 H56B 0.99 . ?
C56 H56A 0.99 . ?
C6A H6A 0.95 . ?
C6 H6 0.95 . ?
C14A C13A 1.369(6) . ?
C14A H4PA 0.95 . ?
C12 C13 1.385(6) . ?
C12 H12 0.95 . ?
C13 C14 1.374(7) . ?
C13 H13 0.95 . ?
C13C C14C 1.380(6) . ?
C13C H3PC 0.95 . ?
C8C C7C 1.380(6) . ?
C8C H8C 0.95 . ?
C12B C13B 1.393(6) . ?
C12B H2PB 0.95 . ?
C16B H6PB 0.95 . ?
C13A H3PA 0.95 . ?
C6C C7C 1.394(6) . ?
C6C H6C 0.95 . ?
C14B C13B 1.369(7) . ?
C14B H4PB 0.95 . ?
C16C C15C 1.390(7) . ?
C16C H6PC 0.95 . ?
C15 C14 1.379(7) . ?
C15 C16 1.390(6) . ?
C15 H15 0.95 . ?
C14C C15C 1.371(7) . ?
C14C H4PC 0.95 . ?
C13B H3PB 0.95 . ?
C16 H16 0.95 . ?
C57 H57C 0.98 . ?
C57 H57B 0.98 . ?
C57 H57A 0.98 . ?
C14 H14 0.95 . ?
C7C H7C 0.95 . ?
C15C H5PC 0.95 . ?
O2W H4W 0.84(6) . ?
O2W H3W 0.91(6) . ?
O1W H2W 0.83(6) . ?
O1W H1W 0.94(7) . ?
C57B H7BA 0.98 . ?
C57B H7BC 0.98 . ?
C57B H7BB 0.98 . ?

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
C71 O73 H73 110(3) . . ?
C81 O83 H83 118(4) . . ?
C5A N51A C52A 114.1(3) . . ?
C5A N51A C56A 111.1(3) . . ?
C52A N51A C56A 109.4(3) . . ?
C90 O91 H91 112(3) . . ?
C5C N51C C52C 115.5(3) . . ?
C5C N51C C56C 114.1(3) . . ?
C52C N51C C56C 109.1(3) . . ?
C5B N51B C56B 116.0(3) . . ?
C5B N51B C52B 114.4(3) . . ?
C56B N51B C52B 108.8(3) . . ?
C5 N51 C56 115.1(3) . . ?
C5 N51 C52 112.6(3) . . ?
C56 N51 C52 109.4(3) . . ?
C57 N54 C55 112.6(3) . . ?
C57 N54 C53 111.8(3) . . ?
C55 N54 C53 109.2(3) . . ?
C57 N54 H54 109(3) . . ?
C55 N54 H54 108(3) . . ?
C53 N54 H54 106(3) . . ?
C91 O93 H93 114(3) . . ?
C10A N1A C2A 126.9(3) . . ?
C10A N1A C9A 124.9(3) . . ?
C2A N1A C9A 108.1(3) . . ?
C57A N54A C55A 111.4(3) . . ?
C57A N54A C53A 111.4(3) . . ?
C55A N54A C53A 109.4(3) . . ?
C57A N54A H54A 108(3) . . ?
C55A N54A H54A 107(3) . . ?
C53A N54A H54A 109(3) . . ?
O72 C71 O73 122.2(3) . . ?
O72 C71 C70 120.5(3) . . ?
O73 C71 C70 117.3(3) . . ?
C10 N1 C2 126.1(3) . . ?
C10 N1 C9 125.8(3) . . ?
C2 N1 C9 107.5(3) . . ?
C10C N1C C2C 125.5(3) . . ?
C10C N1C C9C 125.1(3) . . ?
C2C N1C C9C 108.3(3) . . ?
C8 C9 N1 129.2(4) . . ?
C8 C9 C4 123.2(4) . . ?
N1 C9 C4 107.6(3) . . ?
C6A C5A C4A 117.6(3) . . ?
C6A C5A N51A 123.8(3) . . ?
C4A C5A N51A 118.6(3) . . ?
C57B N54B C53B 111.9(3) . . ?
C57B N54B C55B 112.5(3) . . ?
C53B N54B C55B 109.9(3) . . ?
C57B N54B H54B 107(3) . . ?
C53B N54B H54B 108(3) . . ?
C55B N54B H54B 107(3) . . ?
C57C N54C C53C 111.1(3) . . ?
C57C N54C C55C 111.6(3) . . ?
C53C N54C C55C 110.3(3) . . ?
C57C N54C H54C 109(2) . . ?
C53C N54C H54C 105(2) . . ?
C55C N54C H54C 110(2) . . ?
O92 C91 O93 126.7(4) . . ?
O92 C91 C90 121.3(4) . . ?
O93 C91 C90 112.0(3) . . ?
C16 C11 C12 119.8(4) . . ?
C16 C11 C10 117.5(4) . . ?
C12 C11 C10 122.6(4) . . ?
O90 C90 O91 126.3(4) . . ?
O90 C90 C91 122.1(4) . . ?
O91 C90 C91 111.5(3) . . ?
C12A C11A C16A 119.4(4) . . ?
C12A C11A C10A 122.8(3) . . ?
C16A C11A C10A 117.6(3) . . ?
C2B N1B C9B 107.8(3) . . ?
C2B N1B C10B 124.6(3) . . ?
C9B N1B C10B 124.7(3) . . ?
O61 C60 O60 127.3(4) . . ?
O61 C60 C61 117.4(3) . . ?
O60 C60 C61 115.3(3) . . ?
O10 C10 N1 121.0(4) . . ?
O10 C10 C11 122.2(4) . . ?
N1 C10 C11 116.8(3) . . ?
C7 C8 C9 116.2(4) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
C2B C3B C4B 108.0(3) . . ?
C2B C3B H3B 126 . . ?
C4B C3B H3B 126 . . ?
C2 C3 C4 107.0(3) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
O10A C10A N1A 121.0(3) . . ?
O10A C10A C11A 121.6(3) . . ?
N1A C10A C11A 117.4(3) . . ?
O82 C81 O83 121.7(3) . . ?
O82 C81 C80 120.4(3) . . ?
O83 C81 C80 117.8(3) . . ?
N51B C52B C53B 111.0(3) . . ?
N51B C52B H2BA 109.4 . . ?
C53B C52B H2BA 109.4 . . ?
N51B C52B H2BB 109.4 . . ?
C53B C52B H2BB 109.4 . . ?
H2BA C52B H2BB 108 . . ?
N51 C52 C53 111.5(3) . . ?
N51 C52 H52A 109.3 . . ?
C53 C52 H52A 109.3 . . ?
N51 C52 H52B 109.3 . . ?
C53 C52 H52B 109.3 . . ?
H52A C52 H52B 108 . . ?
N54C C55C C56C 109.9(3) . . ?
N54C C55C H5CA 109.7 . . ?
C56C C55C H5CA 109.7 . . ?
N54C C55C H5CB 109.7 . . ?
C56C C55C H5CB 109.7 . . ?
H5CA C55C H5CB 108.2 . . ?
C2A C3A C4A 107.7(3) . . ?
C2A C3A H3A 126.2 . . ?
C4A C3A H3A 126.2 . . ?
C6B C5B C4B 116.6(4) . . ?
C6B C5B N51B 122.3(4) . . ?
C4B C5B N51B 121.0(3) . . ?
O80 C80 O81 127.8(4) . . ?
O80 C80 C81 116.9(3) . . ?
O81 C80 C81 115.2(3) . . ?
C5C C4C C9C 119.3(3) . . ?
C5C C4C C3C 133.3(3) . . ?
C9C C4C C3C 107.2(3) . . ?
C3B C2B N1B 109.9(3) . . ?
C3B C2B H2B 125 . . ?
N1B C2B H2B 125 . . ?
N54A C55A C56A 111.1(3) . . ?
N54A C55A H5AB 109.4 . . ?
C56A C55A H5AB 109.4 . . ?
N54A C55A H5AA 109.4 . . ?
C56A C55A H5AA 109.4 . . ?
H5AB C55A H5AA 108 . . ?
N54C C53C C52C 112.2(3) . . ?
N54C C53C H3CA 109.2 . . ?
C52C C53C H3CA 109.2 . . ?
N54C C53C H3CB 109.2 . . ?
C52C C53C H3CB 109.2 . . ?
H3CA C53C H3CB 107.9 . . ?
N54 C55 C56 110.3(3) . . ?
N54 C55 H55A 109.6 . . ?
C56 C55 H55A 109.6 . . ?
N54 C55 H55B 109.6 . . ?
C56 C55 H55B 109.6 . . ?
H55A C55 H55B 108.1 . . ?
C16B C11B C12B 120.3(4) . . ?
C16B C11B C10B 118.8(4) . . ?
C12B C11B C10B 120.7(4) . . ?
N51C C52C C53C 110.1(3) . . ?
N51C C52C H2CB 109.6 . . ?
C53C C52C H2CB 109.6 . . ?
N51C C52C H2CA 109.6 . . ?
C53C C52C H2CA 109.6 . . ?
H2CB C52C H2CA 108.2 . . ?
C9B C4B C5B 119.0(4) . . ?
C9B C4B C3B 106.5(3) . . ?
C5B C4B C3B 134.4(4) . . ?
C8B C9B N1B 128.9(4) . . ?
C8B C9B C4B 123.4(4) . . ?
N1B C9B C4B 107.7(3) . . ?
C9A C4A C5A 119.9(3) . . ?
C9A C4A C3A 107.7(3) . . ?
C5A C4A C3A 132.4(3) . . ?
N51C C56C C55C 110.1(3) . . ?
N51C C56C H6CA 109.6 . . ?
C55C C56C H6CA 109.6 . . ?
N51C C56C H6CB 109.6 . . ?
C55C C56C H6CB 109.6 . . ?
H6CA C56C H6CB 108.2 . . ?
N51A C56A C55A 110.3(3) . . ?
N51A C56A H6AA 109.6 . . ?
C55A C56A H6AA 109.6 . . ?
N51A C56A H6AB 109.6 . . ?
C55A C56A H6AB 109.6 . . ?
H6AA C56A H6AB 108.1 . . ?
N54B C53B C52B 110.7(3) . . ?
N54B C53B H3BB 109.5 . . ?
C52B C53B H3BB 109.5 . . ?
N54B C53B H3BA 109.5 . . ?
C52B C53B H3BA 109.5 . . ?
H3BB C53B H3BA 108.1 . . ?
N51B C56B C55B 111.4(3) . . ?
N51B C56B H6BB 109.4 . . ?
C55B C56B H6BB 109.4 . . ?
N51B C56B H6BA 109.4 . . ?
C55B C56B H6BA 109.4 . . ?
H6BB C56B H6BA 108 . . ?
C16A C15A C14A 120.9(4) . . ?
C16A C15A H5PA 119.5 . . ?
C14A C15A H5PA 119.5 . . ?
C8A C9A C4A 123.0(3) . . ?
C8A C9A N1A 129.9(3) . . ?
C4A C9A N1A 107.1(3) . . ?
C6 C5 C4 116.9(4) . . ?
C6 C5 N51 123.0(4) . . ?
C4 C5 N51 120.1(3) . . ?
C8C C9C N1C 130.2(4) . . ?
C8C C9C C4C 122.8(4) . . ?
N1C C9C C4C 106.9(3) . . ?
C3C C2C N1C 109.5(3) . . ?
C3C C2C H2C 125.2 . . ?
N1C C2C H2C 125.2 . . ?
N51A C52A C53A 109.6(3) . . ?
N51A C52A H2AA 109.8 . . ?
C53A C52A H2AA 109.8 . . ?
N51A C52A H2AB 109.8 . . ?
C53A C52A H2AB 109.8 . . ?
H2AA C52A H2AB 108.2 . . ?
C8 C7 C6 122.7(4) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
O62 C61 O63 126.9(3) . . ?
O62 C61 C60 117.6(3) . . ?
O63 C61 C60 115.5(3) . . ?
C6C C5C C4C 117.8(3) . . ?
C6C C5C N51C 123.3(3) . . ?
C4C C5C N51C 118.9(3) . . ?
C2C C3C C4C 108.1(3) . . ?
C2C C3C H3C 126 . . ?
C4C C3C H3C 126 . . ?
C7B C8B C9B 117.2(4) . . ?
C7B C8B H8B 121.4 . . ?
C9B C8B H8B 121.4 . . ?
C8A C7A C6A 122.6(4) . . ?
C8A C7A H7A 118.7 . . ?
C6A C7A H7A 118.7 . . ?
N54A C57A H7AC 109.5 . . ?
N54A C57A H7AB 109.5 . . ?
H7AC C57A H7AB 109.5 . . ?
N54A C57A H7AA 109.5 . . ?
H7AC C57A H7AA 109.5 . . ?
H7AB C57A H7AA 109.5 . . ?
C9 C4 C5 119.6(3) . . ?
C9 C4 C3 107.3(3) . . ?
C5 C4 C3 133.0(4) . . ?
C11A C12A C13A 120.1(4) . . ?
C11A C12A H2PA 120 . . ?
C13A C12A H2PA 120 . . ?
C9A C8A C7A 116.0(3) . . ?
C9A C8A H8A 122 . . ?
C7A C8A H8A 122 . . ?
C3A C2A N1A 109.5(3) . . ?
C3A C2A H2A 125.2 . . ?
N1A C2A H2A 125.2 . . ?
C8B C7B C6B 121.3(4) . . ?
C8B C7B H7B 119.3 . . ?
C6B C7B H7B 119.3 . . ?
N54A C53A C52A 111.0(3) . . ?
N54A C53A H3AB 109.4 . . ?
C52A C53A H3AB 109.4 . . ?
N54A C53A H3AA 109.4 . . ?
C52A C53A H3AA 109.4 . . ?
H3AB C53A H3AA 108 . . ?
N54C C57C H7CC 109.5 . . ?
N54C C57C H7CA 109.5 . . ?
H7CC C57C H7CA 109.5 . . ?
N54C C57C H7CB 109.5 . . ?
H7CC C57C H7CB 109.5 . . ?
H7CA C57C H7CB 109.5 . . ?
N54B C55B C56B 110.5(3) . . ?
N54B C55B H5BB 109.5 . . ?
C56B C55B H5BB 109.5 . . ?
N54B C55B H5BA 109.5 . . ?
C56B C55B H5BA 109.5 . . ?
H5BB C55B H5BA 108.1 . . ?
C14B C15B C16B 120.1(5) . . ?
C14B C15B H5PB 120 . . ?
C16B C15B H5PB 120 . . ?
C15A C16A C11A 119.7(4) . . ?
C15A C16A H6PA 120.2 . . ?
C11A C16A H6PA 120.2 . . ?
O10B C10B N1B 120.3(4) . . ?
O10B C10B C11B 122.2(4) . . ?
N1B C10B C11B 117.4(3) . . ?
N54 C53 C52 110.1(3) . . ?
N54 C53 H53A 109.6 . . ?
C52 C53 H53A 109.6 . . ?
N54 C53 H53B 109.6 . . ?
C52 C53 H53B 109.6 . . ?
H53A C53 H53B 108.2 . . ?
C13C C12C C11C 120.1(4) . . ?
C13C C12C H2PC 120 . . ?
C11C C12C H2PC 120 . . ?
O71 C70 O70 127.7(4) . . ?
O71 C70 C71 117.2(3) . . ?
O70 C70 C71 115.1(3) . . ?
C12C C11C C16C 119.7(4) . . ?
C12C C11C C10C 117.1(4) . . ?
C16C C11C C10C 123.1(4) . . ?
C5B C6B C7B 122.5(4) . . ?
C5B C6B H6B 118.8 . . ?
C7B C6B H6B 118.8 . . ?
C3 C2 N1 110.6(3) . . ?
C3 C2 H2 124.7 . . ?
N1 C2 H2 124.7 . . ?
N51 C56 C55 111.0(3) . . ?
N51 C56 H56B 109.4 . . ?
C55 C56 H56B 109.4 . . ?
N51 C56 H56A 109.4 . . ?
C55 C56 H56A 109.4 . . ?
H56B C56 H56A 108 . . ?
C5A C6A C7A 120.9(4) . . ?
C5A C6A H6A 119.6 . . ?
C7A C6A H6A 119.6 . . ?
C5 C6 C7 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C13A C14A C15A 119.7(4) . . ?
C13A C14A H4PA 120.1 . . ?
C15A C14A H4PA 120.1 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C14C C13C C12C 120.3(4) . . ?
C14C C13C H3PC 119.8 . . ?
C12C C13C H3PC 119.8 . . ?
C7C C8C C9C 116.7(4) . . ?
C7C C8C H8C 121.7 . . ?
C9C C8C H8C 121.7 . . ?
O10C C10C N1C 121.7(4) . . ?
O10C C10C C11C 121.7(4) . . ?
N1C C10C C11C 116.6(4) . . ?
C13B C12B C11B 119.1(4) . . ?
C13B C12B H2PB 120.5 . . ?
C11B C12B H2PB 120.5 . . ?
C11B C16B C15B 119.7(4) . . ?
C11B C16B H6PB 120.1 . . ?
C15B C16B H6PB 120.1 . . ?
C14A C13A C12A 120.1(4) . . ?
C14A C13A H3PA 119.9 . . ?
C12A C13A H3PA 119.9 . . ?
C7C C6C C5C 120.8(4) . . ?
C7C C6C H6C 119.6 . . ?
C5C C6C H6C 119.6 . . ?
C13B C14B C15B 120.4(4) . . ?
C13B C14B H4PB 119.8 . . ?
C15B C14B H4PB 119.8 . . ?
C11C C16C C15C 119.4(4) . . ?
C11C C16C H6PC 120.3 . . ?
C15C C16C H6PC 120.3 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.9 . . ?
C15C C14C C13C 119.7(4) . . ?
C15C C14C H4PC 120.1 . . ?
C13C C14C H4PC 120.1 . . ?
C14B C13B C12B 120.4(4) . . ?
C14B C13B H3PB 119.8 . . ?
C12B C13B H3PB 119.8 . . ?
C11 C16 C15 119.6(4) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N54 C57 H57C 109.5 . . ?
N54 C57 H57B 109.5 . . ?
H57C C57 H57B 109.5 . . ?
N54 C57 H57A 109.5 . . ?
H57C C57 H57A 109.5 . . ?
H57B C57 H57A 109.5 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C8C C7C C6C 122.5(4) . . ?
C8C C7C H7C 118.7 . . ?
C6C C7C H7C 118.7 . . ?
C14C C15C C16C 120.7(4) . . ?
C14C C15C H5PC 119.6 . . ?
C16C C15C H5PC 119.6 . . ?
H4W O2W H3W 105(5) . . ?
H2W O1W H1W 105(5) . . ?
N54B C57B H7BA 109.5 . . ?
N54B C57B H7BC 109.5 . . ?
H7BA C57B H7BC 109.5 . . ?
N54B C57B H7BB 109.5 . . ?
H7BA C57B H7BB 109.5 . . ?
H7BC C57B H7BB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C9 C8 -3.8(6) . . . . ?
C2 N1 C9 C8 -175.4(4) . . . . ?
C10 N1 C9 C4 173.9(3) . . . . ?
C2 N1 C9 C4 2.3(4) . . . . ?
C52A N51A C5A C6A 17.4(5) . . . . ?
C56A N51A C5A C6A -106.9(4) . . . . ?
C52A N51A C5A C4A -163.1(3) . . . . ?
C56A N51A C5A C4A 72.6(4) . . . . ?
O92 C91 C90 O90 178.9(4) . . . . ?
O93 C91 C90 O90 -0.4(5) . . . . ?
O92 C91 C90 O91 -1.8(5) . . . . ?
O93 C91 C90 O91 178.8(3) . . . . ?
C2 N1 C10 O10 155.8(4) . . . . ?
C9 N1 C10 O10 -14.3(6) . . . . ?
C2 N1 C10 C11 -23.3(6) . . . . ?
C9 N1 C10 C11 166.6(3) . . . . ?
C16 C11 C10 O10 -39.4(6) . . . . ?
C12 C11 C10 O10 137.1(4) . . . . ?
C16 C11 C10 N1 139.7(4) . . . . ?
C12 C11 C10 N1 -43.7(5) . . . . ?
N1 C9 C8 C7 176.1(4) . . . . ?
C4 C9 C8 C7 -1.3(6) . . . . ?
C2A N1A C10A O10A -164.5(4) . . . . ?
C9A N1A C10A O10A 10.0(6) . . . . ?
C2A N1A C10A C11A 15.7(5) . . . . ?
C9A N1A C10A C11A -169.7(3) . . . . ?
C12A C11A C10A O10A -131.5(4) . . . . ?
C16A C11A C10A O10A 43.4(5) . . . . ?
C12A C11A C10A N1A 48.2(5) . . . . ?
C16A C11A C10A N1A -136.9(4) . . . . ?
C5B N51B C52B C53B 169.1(3) . . . . ?
C56B N51B C52B C53B -59.5(4) . . . . ?
C5 N51 C52 C53 -172.4(3) . . . . ?
C56 N51 C52 C53 58.2(4) . . . . ?
C57C N54C C55C C56C -178.7(3) . . . . ?
C53C N54C C55C C56C -54.8(4) . . . . ?
C56B N51B C5B C6B -4.0(5) . . . . ?
C52B N51B C5B C6B 123.9(4) . . . . ?
C56B N51B C5B C4B 171.8(3) . . . . ?
C52B N51B C5B C4B -60.3(5) . . . . ?
O82 C81 C80 O80 121.0(4) . . . . ?
O83 C81 C80 O80 -54.7(5) . . . . ?
O82 C81 C80 O81 -54.5(5) . . . . ?
O83 C81 C80 O81 129.8(4) . . . . ?
C4B C3B C2B N1B 0.4(4) . . . . ?
C9B N1B C2B C3B 0.1(4) . . . . ?
C10B N1B C2B C3B 161.5(4) . . . . ?
C57A N54A C55A C56A 178.4(3) . . . . ?
C53A N54A C55A C56A 54.7(4) . . . . ?
C57C N54C C53C C52C 177.3(3) . . . . ?
C55C N54C C53C C52C 53.0(4) . . . . ?
C57 N54 C55 C56 177.7(3) . . . . ?
C53 N54 C55 C56 -57.6(4) . . . . ?
C5C N51C C52C C53C -170.1(3) . . . . ?
C56C N51C C52C C53C 59.8(4) . . . . ?
N54C C53C C52C N51C -55.8(4) . . . . ?
C6B C5B C4B C9B -0.1(5) . . . . ?
N51B C5B C4B C9B -176.2(3) . . . . ?
C6B C5B C4B C3B 176.8(4) . . . . ?
N51B C5B C4B C3B 0.7(6) . . . . ?
C2B C3B C4B C9B -0.8(4) . . . . ?
C2B C3B C4B C5B -178.0(4) . . . . ?
C2B N1B C9B C8B 178.4(4) . . . . ?
C10B N1B C9B C8B 17.0(6) . . . . ?
C2B N1B C9B C4B -0.6(4) . . . . ?
C10B N1B C9B C4B -162.0(4) . . . . ?
C5B C4B C9B C8B -0.5(6) . . . . ?
C3B C4B C9B C8B -178.3(4) . . . . ?
C5B C4B C9B N1B 178.5(3) . . . . ?
C3B C4B C9B N1B 0.8(4) . . . . ?
C6A C5A C4A C9A 1.9(5) . . . . ?
N51A C5A C4A C9A -177.6(3) . . . . ?
C6A C5A C4A C3A -177.7(4) . . . . ?
N51A C5A C4A C3A 2.8(6) . . . . ?
C2A C3A C4A C9A -1.3(4) . . . . ?
C2A C3A C4A C5A 178.3(4) . . . . ?
C5C N51C C56C C55C 166.1(3) . . . . ?
C52C N51C C56C C55C -63.0(4) . . . . ?
N54C C55C C56C N51C 60.5(4) . . . . ?
C5A N51A C56A C55A -172.4(3) . . . . ?
C52A N51A C56A C55A 60.7(4) . . . . ?
N54A C55A C56A N51A -57.8(4) . . . . ?
C57B N54B C53B C52B 178.9(3) . . . . ?
C55B N54B C53B C52B -55.5(4) . . . . ?
N51B C52B C53B N54B 58.4(4) . . . . ?
C5B N51B C56B C55B -169.9(3) . . . . ?
C52B N51B C56B C55B 59.5(4) . . . . ?
C5A C4A C9A C8A 0.4(6) . . . . ?
C3A C4A C9A C8A -179.9(3) . . . . ?
C5A C4A C9A N1A -178.0(3) . . . . ?
C3A C4A C9A N1A 1.7(4) . . . . ?
C10A N1A C9A C8A 4.9(6) . . . . ?
C2A N1A C9A C8A -179.7(4) . . . . ?
C10A N1A C9A C4A -176.8(3) . . . . ?
C2A N1A C9A C4A -1.4(4) . . . . ?
C56 N51 C5 C6 5.5(5) . . . . ?
C52 N51 C5 C6 -120.9(4) . . . . ?
C56 N51 C5 C4 -171.6(3) . . . . ?
C52 N51 C5 C4 62.0(4) . . . . ?
C10C N1C C9C C8C 8.3(7) . . . . ?
C2C N1C C9C C8C 176.6(5) . . . . ?
C10C N1C C9C C4C -169.3(4) . . . . ?
C2C N1C C9C C4C -0.9(4) . . . . ?
C5C C4C C9C C8C -0.9(6) . . . . ?
C3C C4C C9C C8C -176.6(4) . . . . ?
C5C C4C C9C N1C 176.9(4) . . . . ?
C3C C4C C9C N1C 1.1(4) . . . . ?
C10C N1C C2C C3C 168.6(4) . . . . ?
C9C N1C C2C C3C 0.3(4) . . . . ?
C5A N51A C52A C53A 173.5(3) . . . . ?
C56A N51A C52A C53A -61.2(4) . . . . ?
C9 C8 C7 C6 2.7(6) . . . . ?
O61 C60 C61 O62 -173.2(4) . . . . ?
O60 C60 C61 O62 7.2(5) . . . . ?
O61 C60 C61 O63 6.9(5) . . . . ?
O60 C60 C61 O63 -172.7(4) . . . . ?
C9C C4C C5C C6C -1.7(6) . . . . ?
C3C C4C C5C C6C 172.7(4) . . . . ?
C9C C4C C5C N51C -179.1(4) . . . . ?
C3C C4C C5C N51C -4.7(7) . . . . ?
C52C N51C C5C C6C -6.6(5) . . . . ?
C56C N51C C5C C6C 121.0(4) . . . . ?
C52C N51C C5C C4C 170.7(3) . . . . ?
C56C N51C C5C C4C -61.7(4) . . . . ?
N1C C2C C3C C4C 0.4(5) . . . . ?
C5C C4C C3C C2C -175.9(4) . . . . ?
C9C C4C C3C C2C -1.0(5) . . . . ?
N1B C9B C8B C7B -177.3(4) . . . . ?
C4B C9B C8B C7B 1.6(6) . . . . ?
C8 C9 C4 C5 -1.3(6) . . . . ?
N1 C9 C4 C5 -179.2(3) . . . . ?
C8 C9 C4 C3 175.8(4) . . . . ?
N1 C9 C4 C3 -2.1(4) . . . . ?
C6 C5 C4 C9 2.6(5) . . . . ?
N51 C5 C4 C9 179.9(3) . . . . ?
C6 C5 C4 C3 -173.6(4) . . . . ?
N51 C5 C4 C3 3.7(6) . . . . ?
C2 C3 C4 C9 1.1(4) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
C16A C11A C12A C13A 0.5(6) . . . . ?
C10A C11A C12A C13A 175.3(4) . . . . ?
C4A C9A C8A C7A -2.2(5) . . . . ?
N1A C9A C8A C7A 175.9(4) . . . . ?
C6A C7A C8A C9A 1.7(6) . . . . ?
C4A C3A C2A N1A 0.5(4) . . . . ?
C10A N1A C2A C3A 175.8(3) . . . . ?
C9A N1A C2A C3A 0.6(4) . . . . ?
C9B C8B C7B C6B -1.9(6) . . . . ?
C57A N54A C53A C52A -179.3(3) . . . . ?
C55A N54A C53A C52A -55.6(4) . . . . ?
N51A C52A C53A N54A 59.5(4) . . . . ?
C57B N54B C55B C56B -179.5(3) . . . . ?
C53B N54B C55B C56B 55.1(4) . . . . ?
N51B C56B C55B N54B -58.2(4) . . . . ?
C14A C15A C16A C11A 1.6(6) . . . . ?
C12A C11A C16A C15A -2.0(6) . . . . ?
C10A C11A C16A C15A -177.1(4) . . . . ?
C2B N1B C10B O10B -147.8(4) . . . . ?
C9B N1B C10B O10B 10.5(6) . . . . ?
C2B N1B C10B C11B 33.6(6) . . . . ?
C9B N1B C10B C11B -168.0(4) . . . . ?
C16B C11B C10B O10B 45.5(6) . . . . ?
C12B C11B C10B O10B -128.1(5) . . . . ?
C16B C11B C10B N1B -136.0(4) . . . . ?
C12B C11B C10B N1B 50.4(5) . . . . ?
C57 N54 C53 C52 -177.4(3) . . . . ?
C55 N54 C53 C52 57.3(4) . . . . ?
N51 C52 C53 N54 -58.5(4) . . . . ?
O72 C71 C70 O71 -122.3(4) . . . . ?
O73 C71 C70 O71 54.4(5) . . . . ?
O72 C71 C70 O70 53.9(5) . . . . ?
O73 C71 C70 O70 -129.4(4) . . . . ?
C13C C12C C11C C16C -0.6(6) . . . . ?
C13C C12C C11C C10C -178.7(4) . . . . ?
C4B C5B C6B C7B -0.3(6) . . . . ?
N51B C5B C6B C7B 175.7(4) . . . . ?
C8B C7B C6B C5B 1.4(6) . . . . ?
C4 C3 C2 N1 0.3(5) . . . . ?
C10 N1 C2 C3 -173.2(4) . . . . ?
C9 N1 C2 C3 -1.6(4) . . . . ?
C5 N51 C56 C55 174.0(3) . . . . ?
C52 N51 C56 C55 -58.0(4) . . . . ?
N54 C55 C56 N51 58.8(4) . . . . ?
C4A C5A C6A C7A -2.3(5) . . . . ?
N51A C5A C6A C7A 177.1(3) . . . . ?
C8A C7A C6A C5A 0.6(6) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
N51 C5 C6 C7 -178.6(4) . . . . ?
C8 C7 C6 C5 -1.4(6) . . . . ?
C16A C15A C14A C13A 0.3(7) . . . . ?
C16 C11 C12 C13 2.3(6) . . . . ?
C10 C11 C12 C13 -174.2(4) . . . . ?
C11 C12 C13 C14 -2.8(6) . . . . ?
C11C C12C C13C C14C -0.2(7) . . . . ?
N1C C9C C8C C7C -175.0(4) . . . . ?
C4C C9C C8C C7C 2.1(7) . . . . ?
C2C N1C C10C O10C -166.9(4) . . . . ?
C9C N1C C10C O10C -0.5(7) . . . . ?
C2C N1C C10C C11C 10.8(6) . . . . ?
C9C N1C C10C C11C 177.2(4) . . . . ?
C12C C11C C10C O10C 55.6(6) . . . . ?
C16C C11C C10C O10C -122.5(5) . . . . ?
C12C C11C C10C N1C -122.1(4) . . . . ?
C16C C11C C10C N1C 59.9(6) . . . . ?
C16B C11B C12B C13B 0.0(6) . . . . ?
C10B C11B C12B C13B 173.5(4) . . . . ?
C12B C11B C16B C15B -2.6(6) . . . . ?
C10B C11B C16B C15B -176.2(4) . . . . ?
C14B C15B C16B C11B 2.6(6) . . . . ?
C15A C14A C13A C12A -1.8(6) . . . . ?
C11A C12A C13A C14A 1.4(6) . . . . ?
C4C C5C C6C C7C 2.8(6) . . . . ?
N51C C5C C6C C7C -179.8(4) . . . . ?
C16B C15B C14B C13B 0.1(7) . . . . ?
C12C C11C C16C C15C 1.0(6) . . . . ?
C10C C11C C16C C15C 179.0(4) . . . . ?
C12C C13C C14C C15C 0.7(7) . . . . ?
C15B C14B C13B C12B -2.7(7) . . . . ?
C11B C12B C13B C14B 2.6(7) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
C10 C11 C16 C15 176.8(4) . . . . ?
C14 C15 C16 C11 -2.2(7) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C16 C15 C14 C13 1.7(7) . . . . ?
C9C C8C C7C C6C -0.9(7) . . . . ?
C5C C6C C7C C8C -1.6(7) . . . . ?
C13C C14C C15C C16C -0.3(7) . . . . ?
C11C C16C C15C C14C -0.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O10 0.95 2.4 2.908(5) 113.5 .
C3B H3B O10C 0.95 2.48 3.210(5) 134 .
C3 H3 O10A 0.95 2.46 3.325(5) 151.1 1_455
C52 H52A O60 0.99 2.56 3.256(5) 126.9 .
C55C H5CA O72 0.99 2.52 3.188(5) 124.6 1_455
C53C H3CB O93 0.99 2.54 3.503(5) 163.7 2_646
C56A H6AA O82 0.99 2.48 3.107(5) 120.9 .
C56A H6AB O10B 0.99 2.59 3.461(5) 147.1 1_455
C56B H6BA O92 0.99 2.57 3.508(5) 157.5 1_655
C52A H2AA O82 0.99 2.56 3.143(4) 117.5 1_655
C8B H8B O10B 0.95 2.43 2.898(6) 110.3 .
C57A H7AB O91 0.98 2.66 3.576(5) 155.7 1_655
C57A H7AA O81 0.98 2.59 3.377(5) 138 .
C57A H7AA O90 0.98 2.43 3.226(5) 137.7 .
C8A H8A O10A 0.95 2.36 2.886(5) 114.7 .
C57C H7CC O90 0.98 2.55 3.450(5) 153 2_646
C57C H7CB O92 0.98 2.35 3.074(5) 130.3 2_546
C57C H7CB O70 0.98 2.56 3.385(5) 142.2 1_455
C6 H6 O91 0.95 2.6 3.415(5) 144.6 2_647
C8C H8C O10C 0.95 2.38 2.893(5) 113.6 .
C6C H6C O72 0.95 2.46 3.406(5) 171.7 .
C57 H57B O80 0.98 2.5 3.367(5) 147.8 2_547
N54B H54B O63 0.96(5) 1.94(5) 2.772(4) 144(4) 2_656
N54B H54B O61 0.96(5) 2.12(4) 2.857(4) 133(4) 2_656
N54C H54C O2W 0.95(4) 1.75(4) 2.692(4) 168(4) .
O1W H2W O62 0.83(6) 1.89(6) 2.719(4) 174(6) 2_657
N54 H54 O62 0.88(4) 2.29(4) 2.929(4) 130(4) .
N54 H54 O60 0.88(4) 1.94(4) 2.739(4) 151(4) .
O2W H4W O61 0.84(6) 1.88(6) 2.714(4) 170(5) .
N54A H54A O1W 0.95(5) 1.80(5) 2.702(4) 158(4) .
O91 H91 O81 0.97(3) 1.53(3) 2.496(4) 173(5) .
O2W H3W O71 0.91(6) 1.85(6) 2.758(4) 170(5) .
O93 H93 O70 1.04(6) 1.47(6) 2.490(4) 167(5) 2_656
O1W H1W O80 0.94(7) 1.84(7) 2.771(4) 173(6) 1_655
O73 H73 O60 0.95(5) 1.62(5) 2.539(4) 163(5) 1_655
O83 H83 O63 0.94(6) 1.58(6) 2.519(4) 173(6) 2_657

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1550186'
_audit_update_record             
;
2017-05-15 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_date             2015-08-25T17:24:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H23 Cl N2 O2'
_chemical_formula_moiety         'C20 H23 N2 O2, Cl'
_chemical_formula_weight         358.85

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1893(4)
_cell_length_b                   11.0732(6)
_cell_length_c                   12.4016(9)
_cell_angle_alpha                101.763(5)
_cell_angle_beta                 96.088(6)
_cell_angle_gamma                105.598(5)
_cell_volume                     917.30(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2743
_cell_measurement_theta_min      3.885
_cell_measurement_theta_max      28.011

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             380

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.87181
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0081507
_diffrn_orient_matrix_ub_12      -0.0062123
_diffrn_orient_matrix_ub_13      -0.0585075
_diffrn_orient_matrix_ub_21      0.0421052
_diffrn_orient_matrix_ub_22      0.0677759
_diffrn_orient_matrix_ub_23      0.0094166
_diffrn_orient_matrix_ub_31      0.094698
_diffrn_orient_matrix_ub_32      -0.0082118
_diffrn_orient_matrix_ub_33      0.0018816
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_number            6563
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.047
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.848
_reflns_Friedel_coverage         0
_reflns_number_total             3963
_reflns_number_gt                2940
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.3017P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3963
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.125
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N33 N 0.1704(3) 0.31473(17) 0.02257(14) 0.0411(4) Uani 1 1 d . . . . .
C32 C 0.2849(3) 0.42704(18) 0.11660(15) 0.0368(4) Uani 1 1 d . . . . .
H32A H 0.276 0.5064 0.0979 0.044 Uiso 1 1 calc R U . . .
H32B H 0.4217 0.4297 0.1256 0.044 Uiso 1 1 calc R U . . .
C35 C 0.2208(4) 0.3367(3) -0.08645(19) 0.0686(8) Uani 1 1 d . . . . .
H35C H 0.2031 0.4172 -0.0952 0.103 Uiso 1 1 calc R U . . .
H35B H 0.3549 0.3394 -0.0886 0.103 Uiso 1 1 calc R U . . .
H35A H 0.1369 0.2675 -0.146 0.103 Uiso 1 1 calc R U . . .
C34 C 0.1970(4) 0.1905(2) 0.0374(2) 0.0623(7) Uani 1 1 d . . . . .
H34A H 0.1641 0.1773 0.108 0.094 Uiso 1 1 calc R U . . .
H34B H 0.1131 0.121 -0.0219 0.094 Uiso 1 1 calc R U . . .
H34C H 0.331 0.1928 0.0356 0.094 Uiso 1 1 calc R U . . .
Cl1 Cl -0.25795(9) 0.30336(6) 0.00749(5) 0.0565(2) Uani 1 1 d . . . . .
N1 N 0.4783(2) 0.74373(15) 0.41411(13) 0.0346(4) Uani 1 1 d . . . . .
O10 O 0.6797(2) 0.92527(15) 0.53500(12) 0.0515(4) Uani 1 1 d . . . . .
O61 O 0.1415(2) 0.41673(15) 0.66835(12) 0.0501(4) Uani 1 1 d . . . . .
C5 C 0.2125(3) 0.45726(19) 0.48877(16) 0.0347(4) Uani 1 1 d . . . . .
H5 H 0.144 0.3731 0.4497 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4093(3) 0.67425(18) 0.49282(15) 0.0329(4) Uani 1 1 d . . . . .
C3 C 0.3108(3) 0.53974(18) 0.31650(15) 0.0321(4) Uani 1 1 d . . . . .
C4 C 0.3044(3) 0.54815(18) 0.43372(15) 0.0319(4) Uani 1 1 d . . . . .
C6 C 0.2262(3) 0.4960(2) 0.60363(16) 0.0368(5) Uani 1 1 d . . . . .
C31 C 0.2128(3) 0.41990(19) 0.22555(16) 0.0384(5) Uani 1 1 d . . . . .
H31A H 0.0724 0.4065 0.2142 0.046 Uiso 1 1 calc R U . . .
H31B H 0.2366 0.3462 0.2489 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3289(3) 0.6230(2) 0.66187(16) 0.0411(5) Uani 1 1 d . . . . .
H7 H 0.3347 0.647 0.7388 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4146(3) 0.65690(18) 0.30762(16) 0.0353(4) Uani 1 1 d . . . . .
H2 H 0.4408 0.6778 0.2408 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6427(3) 0.93284(19) 0.34548(17) 0.0405(5) Uani 1 1 d . . . . .
C10 C 0.6026(3) 0.86986(19) 0.43908(17) 0.0376(5) Uani 1 1 d . . . . .
C8 C 0.4216(3) 0.7134(2) 0.60796(16) 0.0384(5) Uani 1 1 d . . . . .
H8 H 0.4899 0.7976 0.6472 0.046 Uiso 1 1 calc R U . . .
C16 C 0.4994(4) 0.9285(2) 0.25956(19) 0.0503(6) Uani 1 1 d . . . . .
H16 H 0.3705 0.8794 0.2552 0.06 Uiso 1 1 calc R U . . .
C62 C 0.0326(3) 0.2876(2) 0.6127(2) 0.0497(6) Uani 1 1 d . . . . .
H62C H -0.019 0.2421 0.6663 0.074 Uiso 1 1 calc R U . . .
H62B H -0.0735 0.2879 0.5589 0.074 Uiso 1 1 calc R U . . .
H62A H 0.1166 0.2454 0.5753 0.074 Uiso 1 1 calc R U . . .
C12 C 0.8346(4) 1.0073(2) 0.3497(2) 0.0531(6) Uani 1 1 d . . . . .
H12 H 0.9322 1.0114 0.4071 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7390(5) 1.0713(2) 0.1857(2) 0.0685(8) Uani 1 1 d . . . . .
H14 H 0.7707 1.1184 0.1326 0.082 Uiso 1 1 calc R U . . .
C15 C 0.5488(5) 0.9976(2) 0.1802(2) 0.0627(7) Uani 1 1 d . . . . .
H15 H 0.4524 0.9942 0.1224 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8811(5) 1.0747(2) 0.2700(2) 0.0687(8) Uani 1 1 d . . . . .
H13 H 1.0101 1.123 0.2732 0.082 Uiso 1 1 calc R U . . .
H33 H 0.035(4) 0.311(2) 0.020(2) 0.060(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N33 C34 1.483(3) . ?
N33 C35 1.486(3) . ?
N33 C32 1.496(2) . ?
N33 H33 0.96(2) . ?
C32 C31 1.507(3) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C35 H35C 0.96 . ?
C35 H35B 0.96 . ?
C35 H35A 0.96 . ?
C34 H34A 0.96 . ?
C34 H34B 0.96 . ?
C34 H34C 0.96 . ?
N1 C10 1.392(3) . ?
N1 C9 1.412(2) . ?
N1 C2 1.413(2) . ?
O10 C10 1.216(2) . ?
O61 C6 1.374(2) . ?
O61 C62 1.420(3) . ?
C5 C6 1.386(3) . ?
C5 C4 1.390(3) . ?
C5 H5 0.93 . ?
C9 C8 1.391(3) . ?
C9 C4 1.398(3) . ?
C3 C2 1.344(3) . ?
C3 C4 1.444(3) . ?
C3 C31 1.499(3) . ?
C6 C7 1.399(3) . ?
C31 H31A 0.97 . ?
C31 H31B 0.97 . ?
C7 C8 1.380(3) . ?
C7 H7 0.93 . ?
C2 H2 0.93 . ?
C11 C16 1.385(3) . ?
C11 C12 1.394(3) . ?
C11 C10 1.486(3) . ?
C8 H8 0.93 . ?
C16 C15 1.384(3) . ?
C16 H16 0.93 . ?
C62 H62C 0.96 . ?
C62 H62B 0.96 . ?
C62 H62A 0.96 . ?
C12 C13 1.371(3) . ?
C12 H12 0.93 . ?
C14 C13 1.369(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C13 H13 0.93 . ?

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
C34 N33 C35 110.14(19) . . ?
C34 N33 C32 112.74(18) . . ?
C35 N33 C32 110.89(17) . . ?
C34 N33 H33 109.9(14) . . ?
C35 N33 H33 106.5(14) . . ?
C32 N33 H33 106.4(15) . . ?
N33 C32 C31 112.52(16) . . ?
N33 C32 H32A 109.1 . . ?
C31 C32 H32A 109.1 . . ?
N33 C32 H32B 109.1 . . ?
C31 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
N33 C35 H35C 109.5 . . ?
N33 C35 H35B 109.5 . . ?
H35C C35 H35B 109.5 . . ?
N33 C35 H35A 109.5 . . ?
H35C C35 H35A 109.5 . . ?
H35B C35 H35A 109.5 . . ?
N33 C34 H34A 109.5 . . ?
N33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C10 N1 C9 125.79(16) . . ?
C10 N1 C2 126.91(16) . . ?
C9 N1 C2 106.99(15) . . ?
C6 O61 C62 117.20(16) . . ?
C6 C5 C4 117.97(19) . . ?
C6 C5 H5 121 . . ?
C4 C5 H5 121 . . ?
C8 C9 C4 121.13(18) . . ?
C8 C9 N1 131.27(18) . . ?
C4 C9 N1 107.48(16) . . ?
C2 C3 C4 107.21(17) . . ?
C2 C3 C31 128.75(17) . . ?
C4 C3 C31 124.03(17) . . ?
C5 C4 C9 120.90(17) . . ?
C5 C4 C3 131.24(18) . . ?
C9 C4 C3 107.84(17) . . ?
O61 C6 C5 124.13(19) . . ?
O61 C6 C7 115.12(18) . . ?
C5 C6 C7 120.74(19) . . ?
C3 C31 C32 112.57(16) . . ?
C3 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C3 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C8 C7 C6 121.62(18) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C3 C2 N1 110.47(17) . . ?
C3 C2 H2 124.8 . . ?
N1 C2 H2 124.8 . . ?
C16 C11 C12 118.7(2) . . ?
C16 C11 C10 123.9(2) . . ?
C12 C11 C10 117.2(2) . . ?
O10 C10 N1 120.39(19) . . ?
O10 C10 C11 121.21(19) . . ?
N1 C10 C11 118.37(17) . . ?
C7 C8 C9 117.63(19) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C15 C16 C11 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O61 C62 H62C 109.5 . . ?
O61 C62 H62B 109.5 . . ?
H62C C62 H62B 109.5 . . ?
O61 C62 H62A 109.5 . . ?
H62C C62 H62A 109.5 . . ?
H62B C62 H62A 109.5 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?

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
C34 N33 C32 C31 -66.3(2) . . . . ?
C35 N33 C32 C31 169.7(2) . . . . ?
C10 N1 C9 C8 9.5(3) . . . . ?
C2 N1 C9 C8 -176.6(2) . . . . ?
C10 N1 C9 C4 -174.50(17) . . . . ?
C2 N1 C9 C4 -0.6(2) . . . . ?
C6 C5 C4 C9 0.8(3) . . . . ?
C6 C5 C4 C3 -177.29(18) . . . . ?
C8 C9 C4 C5 -1.4(3) . . . . ?
N1 C9 C4 C5 -177.90(16) . . . . ?
C8 C9 C4 C3 177.10(17) . . . . ?
N1 C9 C4 C3 0.6(2) . . . . ?
C2 C3 C4 C5 177.88(19) . . . . ?
C31 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C9 -0.4(2) . . . . ?
C31 C3 C4 C9 -179.24(17) . . . . ?
C62 O61 C6 C5 -0.4(3) . . . . ?
C62 O61 C6 C7 178.84(17) . . . . ?
C4 C5 C6 O61 179.48(17) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C2 C3 C31 C32 16.3(3) . . . . ?
C4 C3 C31 C32 -165.14(17) . . . . ?
N33 C32 C31 C3 -173.05(17) . . . . ?
O61 C6 C7 C8 179.95(17) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C4 C3 C2 N1 0.0(2) . . . . ?
C31 C3 C2 N1 178.82(18) . . . . ?
C10 N1 C2 C3 174.18(18) . . . . ?
C9 N1 C2 C3 0.3(2) . . . . ?
C9 N1 C10 O10 8.5(3) . . . . ?
C2 N1 C10 O10 -164.28(19) . . . . ?
C9 N1 C10 C11 -173.34(17) . . . . ?
C2 N1 C10 C11 13.9(3) . . . . ?
C16 C11 C10 O10 -136.4(2) . . . . ?
C12 C11 C10 O10 39.2(3) . . . . ?
C16 C11 C10 N1 45.4(3) . . . . ?
C12 C11 C10 N1 -138.99(19) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C4 C9 C8 C7 0.9(3) . . . . ?
N1 C9 C8 C7 176.45(18) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C10 C11 C16 C15 175.5(2) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C13 -176.1(2) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C11 C16 C15 C14 -0.3(3) . . . . ?
C15 C14 C13 C12 -1.2(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32A Cl1 0.97 2.72 3.666(2) 165.3 2_565
C35 H35C Cl1 0.96 2.97 3.834(3) 151.2 2_565
C34 H34C Cl1 0.96 2.97 3.862(3) 155.9 1_655
C8 H8 O10 0.93 2.44 2.940(3) 113.6 .
N33 H33 Cl1 0.96(2) 2.07(3) 3.032(2) 177(2) .

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# END of CIF
