# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 978263'
_audit_update_record             
;
2014-11-25 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N3 O6, C N S, C H4 O'
_chemical_formula_sum            'C22 H30 N4 O7 S1'
_chemical_formula_weight         494.56
_chemical_compound_source        'chemical synthesis'

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

_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                   8.0072(5)
_cell_length_b                   11.8432(9)
_cell_length_c                   13.3307(9)
_cell_angle_alpha                96.449(6)
_cell_angle_beta                 106.074(6)
_cell_angle_gamma                97.869(6)
_cell_volume                     1188.22(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8861
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.1408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4543
_reflns_number_gt                2443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0702P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4543
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.1878(5) 0.0445(4) 0.8001(3) 0.0303(11) Uani 1 1 d . . .
C1M C 0.2542(6) -0.0438(5) 0.4936(5) 0.0697(19) Uani 1 1 d . . .
H1M1 H 0.2686 -0.1123 0.5280 0.105 Uiso 1 1 calc R . .
H1M2 H 0.2930 -0.0522 0.4301 0.105 Uiso 1 1 calc R . .
H1M3 H 0.1296 -0.0357 0.4739 0.105 Uiso 1 1 calc R . .
O1M O 0.3620(5) 0.0600(3) 0.5675(3) 0.0633(11) Uani 1 1 d . . .
H1M H 0.3564 0.0546 0.6289 0.095 Uiso 1 1 calc R . .
N1A N 0.3065(5) 0.0369(3) 0.7659(3) 0.0419(10) Uani 1 1 d . . .
S1A S 0.02519(13) 0.05490(11) 0.85090(10) 0.0370(3) Uani 1 1 d . . .
C1 C 1.1149(5) 0.5970(4) 0.6585(3) 0.0245(10) Uani 1 1 d . . .
C2 C 1.0906(5) 0.3888(4) 0.6330(3) 0.0293(10) Uani 1 1 d . . .
C3 C 1.2001(7) 0.2973(5) 0.6480(4) 0.0625(17) Uani 1 1 d . . .
H3A H 1.3253 0.3327 0.6721 0.094 Uiso 0.50 1 calc PR . .
H3B H 1.1750 0.2457 0.5808 0.094 Uiso 0.50 1 calc PR . .
H3C H 1.1725 0.2530 0.7009 0.094 Uiso 0.50 1 calc PR . .
H3D H 1.1232 0.2216 0.6304 0.094 Uiso 0.50 1 calc PR . .
H3E H 1.2736 0.3086 0.7218 0.094 Uiso 0.50 1 calc PR . .
H3F H 1.2760 0.3012 0.6016 0.094 Uiso 0.50 1 calc PR . .
C4 C 0.9146(4) 0.3734(3) 0.6007(3) 0.0167(8) Uani 1 1 d . . .
H4 H 0.8490 0.2971 0.5796 0.020 Uiso 1 1 calc R . .
C5 C 0.8225(4) 0.4682(3) 0.5971(3) 0.0190(9) Uani 1 1 d . . .
C6 C 0.9260(4) 0.5831(4) 0.6242(3) 0.0189(9) Uani 1 1 d . . .
C7 C 0.8425(4) 0.6825(4) 0.6206(3) 0.0198(9) Uani 1 1 d . . .
C8 C 0.9425(5) 0.8023(4) 0.6326(3) 0.0268(10) Uani 1 1 d . . .
H8A H 0.8610 0.8574 0.6280 0.040 Uiso 0.50 1 calc PR . .
H8B H 0.9986 0.8069 0.5762 0.040 Uiso 0.50 1 calc PR . .
H8C H 1.0333 0.8208 0.7014 0.040 Uiso 0.50 1 calc PR . .
H8D H 1.0676 0.7993 0.6424 0.040 Uiso 0.50 1 calc PR . .
H8E H 0.9300 0.8499 0.6942 0.040 Uiso 0.50 1 calc PR . .
H8F H 0.8953 0.8359 0.5690 0.040 Uiso 0.50 1 calc PR . .
C9 C 0.5639(5) 0.7604(3) 0.6022(3) 0.0219(9) Uani 1 1 d . . .
H9A H 0.4376 0.7244 0.5761 0.026 Uiso 1 1 calc R . .
H9B H 0.5876 0.8103 0.5511 0.026 Uiso 1 1 calc R . .
C10 C 0.5981(4) 0.8352(3) 0.7082(3) 0.0222(9) Uani 1 1 d . . .
H10A H 0.7212 0.8777 0.7316 0.027 Uiso 1 1 calc R . .
H10B H 0.5182 0.8926 0.7008 0.027 Uiso 1 1 calc R . .
C11 C 0.5822(5) 0.8369(3) 0.8915(3) 0.0222(9) Uani 1 1 d . . .
H11A H 0.4853 0.8822 0.8801 0.027 Uiso 1 1 calc R . .
H11B H 0.6955 0.8919 0.9154 0.027 Uiso 1 1 calc R . .
C12 C 0.5711(4) 0.7631(4) 0.9771(3) 0.0230(9) Uani 1 1 d . . .
H12A H 0.6778 0.7270 0.9955 0.028 Uiso 1 1 calc R . .
H12B H 0.5709 0.8138 1.0414 0.028 Uiso 1 1 calc R . .
C13 C 0.2492(5) 0.6856(4) 0.9338(3) 0.0194(9) Uani 1 1 d . . .
C14 C 0.2130(5) 0.8045(4) 0.9569(3) 0.0266(10) Uani 1 1 d . . .
H14A H 0.3241 0.8599 0.9782 0.040 Uiso 0.50 1 calc PR . .
H14B H 0.1583 0.8082 1.0142 0.040 Uiso 0.50 1 calc PR . .
H14C H 0.1328 0.8234 0.8934 0.040 Uiso 0.50 1 calc PR . .
H14D H 0.0861 0.8011 0.9456 0.040 Uiso 0.50 1 calc PR . .
H14E H 0.2518 0.8528 0.9097 0.040 Uiso 0.50 1 calc PR . .
H14F H 0.2773 0.8376 1.0305 0.040 Uiso 0.50 1 calc PR . .
C15 C 0.1146(4) 0.5847(4) 0.9008(3) 0.0207(9) Uani 1 1 d . . .
C16 C -0.0673(5) 0.5974(4) 0.8699(3) 0.0247(10) Uani 1 1 d . . .
C17 C -0.1545(5) 0.3904(4) 0.8367(3) 0.0270(10) Uani 1 1 d . . .
C18 C -0.3135(5) 0.3001(4) 0.7951(4) 0.0438(14) Uani 1 1 d . . .
H18A H -0.4191 0.3360 0.7820 0.066 Uiso 0.50 1 calc PR . .
H18B H -0.3163 0.2478 0.8468 0.066 Uiso 0.50 1 calc PR . .
H18C H -0.3107 0.2564 0.7288 0.066 Uiso 0.50 1 calc PR . .
H18D H -0.2783 0.2241 0.7898 0.066 Uiso 0.50 1 calc PR . .
H18E H -0.3811 0.3123 0.7250 0.066 Uiso 0.50 1 calc PR . .
H18F H -0.3867 0.3037 0.8430 0.066 Uiso 0.50 1 calc PR . .
C19 C 0.0133(4) 0.3744(3) 0.8638(3) 0.0189(9) Uani 1 1 d . . .
H19 H 0.0377 0.2980 0.8624 0.023 Uiso 1 1 calc R . .
C20 C 0.1580(4) 0.4706(4) 0.8952(3) 0.0221(9) Uani 1 1 d . . .
O1 O 1.2208(3) 0.6879(3) 0.6894(2) 0.0297(7) Uani 1 1 d . . .
O2 O 1.1898(3) 0.4989(3) 0.6590(2) 0.0377(8) Uani 1 1 d . . .
O3 O 0.6574(3) 0.4486(2) 0.5721(2) 0.0262(7) Uani 1 1 d . . .
O4 O -0.1237(3) 0.6888(3) 0.8646(2) 0.0284(7) Uani 1 1 d . . .
O5 O -0.1948(3) 0.4996(3) 0.8406(2) 0.0311(8) Uani 1 1 d . . .
O6 O 0.3132(3) 0.4511(2) 0.9150(2) 0.0258(7) Uani 1 1 d . . .
N1 N 0.6710(3) 0.6693(3) 0.6049(2) 0.0191(8) Uani 1 1 d . . .
H1 H 0.6143 0.5980 0.5949 0.023 Uiso 1 1 calc R . .
N2 N 0.5694(3) 0.7643(3) 0.7898(2) 0.0183(7) Uani 1 1 d . . .
H2A H 0.4596 0.7184 0.7645 0.022 Uiso 1 1 calc R . .
H2B H 0.6522 0.7167 0.8020 0.022 Uiso 1 1 calc R . .
N3 N 0.4143(3) 0.6720(3) 0.9461(2) 0.0206(8) Uani 1 1 d . . .
H3 H 0.4322 0.6007 0.9344 0.025 Uiso 1 1 calc R . .


_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
C1A N1A 1.172(5) . ?
C1A S1A 1.638(5) . ?
C1M O1M 1.481(7) . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O1M H1M 0.8400 . ?
C1 O1 1.227(5) . ?
C1 O2 1.378(5) . ?
C1 C6 1.434(5) . ?
C2 C4 1.334(5) . ?
C2 O2 1.383(5) . ?
C2 C3 1.482(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 H3F 0.9800 . ?
C4 C5 1.424(5) . ?
C4 H4 0.9500 . ?
C5 O3 1.252(4) . ?
C5 C6 1.444(5) . ?
C6 C7 1.430(5) . ?
C7 N1 1.315(4) . ?
C7 C8 1.499(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8F 0.9800 . ?
C9 N1 1.465(5) . ?
C9 C10 1.515(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.494(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.491(5) . ?
C11 C12 1.528(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N3 1.467(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N3 1.321(4) . ?
C13 C15 1.432(5) . ?
C13 C14 1.491(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C15 C16 1.433(5) . ?
C15 C20 1.439(5) . ?
C16 O4 1.231(5) . ?
C16 O5 1.374(5) . ?
C17 C19 1.338(5) . ?
C17 O5 1.374(5) . ?
C17 C18 1.475(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C19 C20 1.442(5) . ?
C19 H19 0.9500 . ?
C20 O6 1.256(4) . ?
N1 H1 0.8800 . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N3 H3 0.8800 . ?

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
N1A C1A S1A 178.6(4) . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C1M O1M H1M 109.5 . . ?
O1 C1 O2 114.8(3) . . ?
O1 C1 C6 127.2(4) . . ?
O2 C1 C6 118.0(4) . . ?
C4 C2 O2 120.5(4) . . ?
C4 C2 C3 126.5(5) . . ?
O2 C2 C3 113.0(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3D 109.5 . . ?
H3A C3 H3D 141.1 . . ?
H3B C3 H3D 56.3 . . ?
H3C C3 H3D 56.3 . . ?
C2 C3 H3E 109.5 . . ?
H3A C3 H3E 56.3 . . ?
H3B C3 H3E 141.1 . . ?
H3C C3 H3E 56.3 . . ?
H3D C3 H3E 109.5 . . ?
C2 C3 H3F 109.5 . . ?
H3A C3 H3F 56.3 . . ?
H3B C3 H3F 56.3 . . ?
H3C C3 H3F 141.1 . . ?
H3D C3 H3F 109.5 . . ?
H3E C3 H3F 109.5 . . ?
C2 C4 C5 121.7(4) . . ?
C2 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
O3 C5 C4 119.0(4) . . ?
O3 C5 C6 123.2(4) . . ?
C4 C5 C6 117.7(3) . . ?
C7 C6 C1 120.0(4) . . ?
C7 C6 C5 120.9(3) . . ?
C1 C6 C5 119.1(4) . . ?
N1 C7 C6 119.3(3) . . ?
N1 C7 C8 118.1(4) . . ?
C6 C7 C8 122.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8D 109.5 . . ?
H8A C8 H8D 141.1 . . ?
H8B C8 H8D 56.3 . . ?
H8C C8 H8D 56.3 . . ?
C7 C8 H8E 109.5 . . ?
H8A C8 H8E 56.3 . . ?
H8B C8 H8E 141.1 . . ?
H8C C8 H8E 56.3 . . ?
H8D C8 H8E 109.5 . . ?
C7 C8 H8F 109.5 . . ?
H8A C8 H8F 56.3 . . ?
H8B C8 H8F 56.3 . . ?
H8C C8 H8F 141.1 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
N1 C9 C10 114.0(3) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C9 111.3(3) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 C12 111.4(3) . . ?
N2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 C11 113.7(3) . . ?
N3 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N3 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N3 C13 C15 118.0(4) . . ?
N3 C13 C14 118.5(4) . . ?
C15 C13 C14 123.5(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14D 109.5 . . ?
H14A C14 H14D 141.1 . . ?
H14B C14 H14D 56.3 . . ?
H14C C14 H14D 56.3 . . ?
C13 C14 H14E 109.5 . . ?
H14A C14 H14E 56.3 . . ?
H14B C14 H14E 141.1 . . ?
H14C C14 H14E 56.3 . . ?
H14D C14 H14E 109.5 . . ?
C13 C14 H14F 109.5 . . ?
H14A C14 H14F 56.3 . . ?
H14B C14 H14F 56.3 . . ?
H14C C14 H14F 141.1 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C13 C15 C16 119.4(4) . . ?
C13 C15 C20 121.4(3) . . ?
C16 C15 C20 119.2(4) . . ?
O4 C16 O5 115.0(3) . . ?
O4 C16 C15 126.4(4) . . ?
O5 C16 C15 118.6(4) . . ?
C19 C17 O5 120.9(4) . . ?
C19 C17 C18 126.7(4) . . ?
O5 C17 C18 112.3(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C17 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C17 C19 C20 121.3(4) . . ?
C17 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
O6 C20 C15 123.8(3) . . ?
O6 C20 C19 119.0(4) . . ?
C15 C20 C19 117.3(3) . . ?
C1 O2 C2 122.7(3) . . ?
C17 O5 C16 122.6(3) . . ?
C7 N1 C9 127.1(3) . . ?
C7 N1 H1 116.4 . . ?
C9 N1 H1 116.4 . . ?
C11 N2 C10 112.3(3) . . ?
C11 N2 H2A 109.1 . . ?
C10 N2 H2A 109.1 . . ?
C11 N2 H2B 109.1 . . ?
C10 N2 H2B 109.1 . . ?
H2A N2 H2B 107.9 . . ?
C13 N3 C12 127.0(4) . . ?
C13 N3 H3 116.5 . . ?
C12 N3 H3 116.5 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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 978264'
_audit_update_record             
;
2014-11-25 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N3 O6, C N S'
_chemical_formula_sum            'C21 H26 N4 O6 S'
_chemical_formula_weight         462.53
_chemical_compound_source        'chemical synthesis'


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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_int_tables_number      15

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

_cell_length_a                   33.554(7)
_cell_length_b                   13.996(3)
_cell_length_c                   18.645(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.54(3)
_cell_angle_gamma                90.00
_cell_volume                     8608(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4460
_cell_measurement_theta_min      3.7181
_cell_measurement_theta_max      28.5553

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3904
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_min  0.97028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20162
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.1237
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         26.00
_reflns_number_total             8419
_reflns_number_gt                4099
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8419
_refine_ls_number_parameters     595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_restrained_S_all      0.841
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.14920(9) 0.9451(2) 0.19242(16) 0.0364(8) Uani 1 1 d . . .
C12 C 0.14963(7) 1.0761(2) 0.27719(14) 0.0223(7) Uani 1 1 d . . .
C13 C 0.15044(8) 1.1816(2) 0.27681(14) 0.0308(8) Uani 1 1 d . . .
H13A H 0.1502 1.2050 0.3251 0.046 Uiso 1 1 calc R . .
H13B H 0.1270 1.2052 0.2441 0.046 Uiso 1 1 calc R . .
H13C H 0.1746 1.2031 0.2609 0.046 Uiso 1 1 calc R . .
C14 C 0.14963(7) 1.0170(2) 0.33254(14) 0.0199(7) Uani 1 1 d . . .
H14 H 0.1490 1.0423 0.3785 0.024 Uiso 1 1 calc R . .
C15 C 0.15055(7) 0.9159(2) 0.32414(14) 0.0211(7) Uani 1 1 d . . .
C16 C 0.15036(8) 0.8793(2) 0.25130(13) 0.0223(7) Uani 1 1 d . . .
C17 C 0.15287(7) 0.7799(2) 0.23805(14) 0.0221(7) Uani 1 1 d . . .
C18 C 0.15139(8) 0.7335(2) 0.16512(12) 0.0303(8) Uani 1 1 d . . .
H18A H 0.1749 0.6938 0.1666 0.045 Uiso 1 1 calc R . .
H18B H 0.1510 0.7819 0.1285 0.045 Uiso 1 1 calc R . .
H18C H 0.1274 0.6951 0.1536 0.045 Uiso 1 1 calc R . .
C19 C 0.16190(8) 0.6191(2) 0.29461(14) 0.0291(7) Uani 1 1 d . . .
H19A H 0.1880 0.6028 0.2826 0.035 Uiso 1 1 calc R . .
H19B H 0.1408 0.5899 0.2587 0.035 Uiso 1 1 calc R . .
C110 C 0.15936(7) 0.5841(2) 0.36914(13) 0.0255(7) Uani 1 1 d . . .
H11B H 0.1659 0.5165 0.3724 0.031 Uiso 1 1 calc R . .
H11A H 0.1793 0.6175 0.4047 0.031 Uiso 1 1 calc R . .
C111 C 0.09013(8) 0.5192(2) 0.36288(13) 0.0271(7) Uani 1 1 d . . .
H11D H 0.0993 0.4625 0.3910 0.033 Uiso 1 1 calc R . .
H11C H 0.0903 0.5054 0.3120 0.033 Uiso 1 1 calc R . .
C112 C 0.04736(8) 0.5427(2) 0.37201(13) 0.0285(7) Uani 1 1 d . . .
H11E H 0.0364 0.5915 0.3370 0.034 Uiso 1 1 calc R . .
H11F H 0.0306 0.4861 0.3616 0.034 Uiso 1 1 calc R . .
C113 C 0.04905(8) 0.5255(2) 0.50591(15) 0.0256(7) Uani 1 1 d . . .
C114 C 0.05481(8) 0.4208(2) 0.50188(14) 0.0314(8) Uani 1 1 d . . .
H11H H 0.0525 0.4020 0.4518 0.047 Uiso 1 1 calc R . .
H11I H 0.0345 0.3887 0.5230 0.047 Uiso 1 1 calc R . .
H11G H 0.0812 0.4040 0.5282 0.047 Uiso 1 1 calc R . .
C115 C 0.04772(7) 0.5745(2) 0.57276(14) 0.0234(7) Uani 1 1 d . . .
C116 C 0.05214(8) 0.5206(2) 0.63920(16) 0.0286(7) Uani 1 1 d . . .
C117 C 0.05060(8) 0.6693(2) 0.70484(15) 0.0285(7) Uani 1 1 d . . .
C118 C 0.05415(9) 0.7049(2) 0.78100(14) 0.0352(8) Uani 1 1 d . . .
H11K H 0.0520 0.7733 0.7806 0.053 Uiso 1 1 calc R . .
H11J H 0.0799 0.6864 0.8089 0.053 Uiso 1 1 calc R . .
H11L H 0.0328 0.6780 0.8026 0.053 Uiso 1 1 calc R . .
C119 C 0.04713(7) 0.7212(2) 0.64471(14) 0.0267(7) Uani 1 1 d . . .
H119 H 0.0463 0.7875 0.6481 0.032 Uiso 1 1 calc R . .
C120 C 0.04462(7) 0.6775(2) 0.57453(15) 0.0235(7) Uani 1 1 d . . .
N11 N 0.15673(6) 0.72190(17) 0.29454(11) 0.0233(6) Uani 1 1 d . . .
H11 H 0.1561 0.7480 0.3361 0.028 Uiso 1 1 calc R . .
N12 N 0.11835(6) 0.59884(16) 0.38708(10) 0.0248(6) Uani 1 1 d . . .
H12A H 0.1208 0.6059 0.4357 0.030 Uiso 1 1 calc R . .
H12B H 0.1078 0.6532 0.3659 0.030 Uiso 1 1 calc R . .
N13 N 0.04536(6) 0.57633(17) 0.44536(11) 0.0257(6) Uani 1 1 d . . .
H13 H 0.0413 0.6365 0.4497 0.031 Uiso 1 1 calc R . .
O11 O 0.14847(8) 0.92890(17) 0.12908(10) 0.0772(9) Uani 1 1 d . . .
O12 O 0.14964(5) 1.04160(14) 0.20831(9) 0.0277(5) Uani 1 1 d . . .
O13 O 0.15137(5) 0.86249(13) 0.37929(9) 0.0232(5) Uani 1 1 d . . .
O14 O 0.05501(6) 0.43567(16) 0.64844(10) 0.0368(5) Uani 1 1 d . . .
O15 O 0.05132(5) 0.57205(15) 0.70345(9) 0.0288(5) Uani 1 1 d . . .
O16 O 0.04047(5) 0.72864(14) 0.51816(9) 0.0293(5) Uani 1 1 d . . .
C21 C 0.24876(8) 0.4846(2) 0.19986(15) 0.0259(7) Uani 1 1 d . . .
C22 C 0.24729(8) 0.3430(2) 0.27334(15) 0.0249(7) Uani 1 1 d . . .
C23 C 0.24520(8) 0.3147(2) 0.34936(13) 0.0339(8) Uani 1 1 d . . .
H23A H 0.2453 0.2462 0.3530 0.051 Uiso 1 1 calc R . .
H23B H 0.2207 0.3393 0.3622 0.051 Uiso 1 1 calc R . .
H23C H 0.2682 0.3401 0.3820 0.051 Uiso 1 1 calc R . .
C24 C 0.25003(7) 0.2854(2) 0.21821(13) 0.0229(7) Uani 1 1 d . . .
H24 H 0.2490 0.2197 0.2250 0.027 Uiso 1 1 calc R . .
C25 C 0.25459(7) 0.3216(2) 0.14812(14) 0.0227(7) Uani 1 1 d . . .
C26 C 0.25305(7) 0.4238(2) 0.13884(13) 0.0225(7) Uani 1 1 d . . .
C27 C 0.25673(7) 0.4667(2) 0.07077(14) 0.0232(7) Uani 1 1 d . . .
C28 C 0.25031(9) 0.5700(2) 0.05578(14) 0.0416(9) Uani 1 1 d . . .
H28A H 0.2742 0.6047 0.0772 0.062 Uiso 1 1 calc R . .
H28B H 0.2277 0.5918 0.0764 0.062 Uiso 1 1 calc R . .
H28C H 0.2448 0.5805 0.0040 0.062 Uiso 1 1 calc R . .
C29 C 0.27449(8) 0.4365(2) -0.05179(12) 0.0254(7) Uani 1 1 d . . .
H29A H 0.2789 0.5049 -0.0535 0.030 Uiso 1 1 calc R . .
H29B H 0.2515 0.4205 -0.0895 0.030 Uiso 1 1 calc R . .
C210 C 0.31178(7) 0.3844(2) -0.06622(13) 0.0246(7) Uani 1 1 d . . .
H21A H 0.3095 0.3171 -0.0552 0.030 Uiso 1 1 calc R . .
H21B H 0.3133 0.3900 -0.1175 0.030 Uiso 1 1 calc R . .
C211 C 0.38653(7) 0.3823(2) -0.04359(13) 0.0247(7) Uani 1 1 d . . .
H21D H 0.3843 0.3883 -0.0960 0.030 Uiso 1 1 calc R . .
H21C H 0.3884 0.3149 -0.0315 0.030 Uiso 1 1 calc R . .
C212 C 0.42440(8) 0.4320(2) -0.00609(12) 0.0257(7) Uani 1 1 d . . .
H21E H 0.4470 0.4139 -0.0290 0.031 Uiso 1 1 calc R . .
H21F H 0.4209 0.5007 -0.0107 0.031 Uiso 1 1 calc R . .
C213 C 0.44419(8) 0.4603(2) 0.12789(14) 0.0238(7) Uani 1 1 d . . .
C214 C 0.45432(8) 0.5617(2) 0.11592(14) 0.0363(8) Uani 1 1 d . . .
H21G H 0.4631 0.5677 0.0699 0.055 Uiso 1 1 calc R . .
H21I H 0.4757 0.5822 0.1544 0.055 Uiso 1 1 calc R . .
H21H H 0.4308 0.6008 0.1157 0.055 Uiso 1 1 calc R . .
C215 C 0.44718(7) 0.4178(2) 0.19898(13) 0.0209(7) Uani 1 1 d . . .
C216 C 0.45100(8) 0.4797(2) 0.26124(15) 0.0265(7) Uani 1 1 d . . .
C217 C 0.45267(8) 0.3395(2) 0.33734(15) 0.0273(7) Uani 1 1 d . . .
C218 C 0.45634(9) 0.3132(2) 0.41509(13) 0.0375(8) Uani 1 1 d . . .
H21K H 0.4568 0.2448 0.4197 0.056 Uiso 1 1 calc R . .
H21L H 0.4336 0.3383 0.4337 0.056 Uiso 1 1 calc R . .
H21J H 0.4810 0.3393 0.4424 0.056 Uiso 1 1 calc R . .
C219 C 0.44759(7) 0.2816(2) 0.28037(14) 0.0267(7) Uani 1 1 d . . .
H219 H 0.4471 0.2160 0.2880 0.032 Uiso 1 1 calc R . .
C220 C 0.44283(7) 0.3170(2) 0.20766(14) 0.0226(7) Uani 1 1 d . . .
N21 N 0.26561(6) 0.41063(16) 0.01927(11) 0.0247(6) Uani 1 1 d . . .
H21 H 0.2662 0.3505 0.0289 0.030 Uiso 1 1 calc R . .
N22 N 0.34956(6) 0.42326(16) -0.02162(10) 0.0226(5) Uani 1 1 d . . .
H22A H 0.3499 0.4100 0.0257 0.027 Uiso 1 1 calc R . .
H22B H 0.3498 0.4872 -0.0266 0.027 Uiso 1 1 calc R . .
N23 N 0.43293(6) 0.40564(16) 0.07081(11) 0.0248(6) Uani 1 1 d . . .
H23 H 0.4302 0.3460 0.0799 0.030 Uiso 1 1 calc R . .
O21 O 0.24789(5) 0.57066(15) 0.20234(9) 0.0338(5) Uani 1 1 d . . .
O22 O 0.24777(5) 0.43986(14) 0.26640(9) 0.0265(5) Uani 1 1 d . . .
O23 O 0.25967(5) 0.26403(13) 0.09845(9) 0.0265(5) Uani 1 1 d . . .
O24 O 0.45106(6) 0.56564(15) 0.26373(9) 0.0353(5) Uani 1 1 d . . .
O25 O 0.45413(5) 0.43633(14) 0.32970(9) 0.0286(5) Uani 1 1 d . . .
O26 O 0.43461(5) 0.25940(13) 0.15436(9) 0.0268(5) Uani 1 1 d . . .
C31 C 0.14570(8) 0.3889(2) 0.09169(16) 0.0299(8) Uani 1 1 d . . .
N31 N 0.14225(7) 0.3674(2) 0.03040(13) 0.0427(7) Uani 1 1 d . . .
S31 S 0.14972(2) 0.41409(7) 0.17770(4) 0.0401(2) Uani 1 1 d . . .
C41 C 0.14760(11) 0.2070(3) 0.47531(15) 0.0389(9) Uani 1 1 d . . .
N41A N 0.154(2) 0.1261(10) 0.4881(11) 0.055(8) Uani 0.53(8) 1 d P A 1
N41B N 0.1334(12) 0.1278(10) 0.4776(9) 0.031(5) Uani 0.47(8) 1 d P A 2
S41 S 0.15269(2) 0.32080(6) 0.46387(4) 0.0416(2) Uani 1 1 d . A .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C11 O11 1.199(3) . ?
C11 O12 1.382(3) . ?
C11 C16 1.428(4) . ?
C12 C14 1.322(3) . ?
C12 O12 1.372(3) . ?
C12 C13 1.477(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.425(4) . ?
C14 H14 0.9300 . ?
C15 O13 1.267(3) . ?
C15 C16 1.450(3) . ?
C16 C17 1.417(4) . ?
C17 N11 1.318(3) . ?
C17 C18 1.500(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N11 1.449(3) . ?
C19 C110 1.490(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C110 N12 1.489(3) . ?
C110 H11B 0.9700 . ?
C110 H11A 0.9700 . ?
C111 N12 1.479(3) . ?
C111 C112 1.512(3) . ?
C111 H11D 0.9700 . ?
C111 H11C 0.9700 . ?
C112 N13 1.459(3) . ?
C112 H11E 0.9700 . ?
C112 H11F 0.9700 . ?
C113 N13 1.321(3) . ?
C113 C115 1.430(4) . ?
C113 C114 1.481(4) . ?
C114 H11H 0.9600 . ?
C114 H11I 0.9600 . ?
C114 H11G 0.9600 . ?
C115 C116 1.434(4) . ?
C115 C120 1.447(4) . ?
C116 O14 1.203(3) . ?
C116 O15 1.402(3) . ?
C117 C119 1.323(4) . ?
C117 O15 1.362(3) . ?
C117 C118 1.489(4) . ?
C118 H11K 0.9600 . ?
C118 H11J 0.9600 . ?
C118 H11L 0.9600 . ?
C119 C120 1.433(3) . ?
C119 H119 0.9300 . ?
C120 O16 1.258(3) . ?
N11 H11 0.8600 . ?
N12 H12A 0.9000 . ?
N12 H12B 0.9000 . ?
N13 H13 0.8600 . ?
C21 O21 1.206(3) . ?
C21 O22 1.395(3) . ?
C21 C26 1.449(4) . ?
C22 C24 1.322(3) . ?
C22 O22 1.362(3) . ?
C22 C23 1.486(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.435(3) . ?
C24 H24 0.9300 . ?
C25 O23 1.262(3) . ?
C25 C26 1.441(4) . ?
C26 C27 1.429(3) . ?
C27 N21 1.316(3) . ?
C27 C28 1.481(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N21 1.456(3) . ?
C29 C210 1.514(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C210 N22 1.486(3) . ?
C210 H21A 0.9700 . ?
C210 H21B 0.9700 . ?
C211 N22 1.490(3) . ?
C211 C212 1.504(3) . ?
C211 H21D 0.9700 . ?
C211 H21C 0.9700 . ?
C212 N23 1.458(3) . ?
C212 H21E 0.9700 . ?
C212 H21F 0.9700 . ?
C213 N23 1.309(3) . ?
C213 C215 1.439(3) . ?
C213 C214 1.487(4) . ?
C214 H21G 0.9600 . ?
C214 H21I 0.9600 . ?
C214 H21H 0.9600 . ?
C215 C220 1.431(4) . ?
C215 C216 1.435(4) . ?
C216 O24 1.204(3) . ?
C216 O25 1.400(3) . ?
C217 C219 1.322(4) . ?
C217 O25 1.364(3) . ?
C217 C218 1.479(3) . ?
C218 H21K 0.9600 . ?
C218 H21L 0.9600 . ?
C218 H21J 0.9600 . ?
C219 C220 1.425(3) . ?
C219 H219 0.9300 . ?
C220 O26 1.270(3) . ?
N21 H21 0.8600 . ?
N22 H22A 0.9000 . ?
N22 H22B 0.9000 . ?
N23 H23 0.8600 . ?
C31 N31 1.167(3) . ?
C31 S31 1.623(3) . ?
C41 N41A 1.17(2) . ?
C41 N41B 1.21(2) . ?
C41 S41 1.620(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 C11 O12 113.2(3) . . ?
O11 C11 C16 128.9(3) . . ?
O12 C11 C16 117.9(2) . . ?
C14 C12 O12 120.7(3) . . ?
C14 C12 C13 129.1(3) . . ?
O12 C12 C13 110.1(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.1(3) . . ?
C12 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
O13 C15 C14 119.6(2) . . ?
O13 C15 C16 123.2(3) . . ?
C14 C15 C16 117.2(2) . . ?
C17 C16 C11 119.5(2) . . ?
C17 C16 C15 121.3(3) . . ?
C11 C16 C15 119.1(3) . . ?
N11 C17 C16 117.8(2) . . ?
N11 C17 C18 116.1(3) . . ?
C16 C17 C18 126.2(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N11 C19 C110 107.4(2) . . ?
N11 C19 H19A 110.2 . . ?
C110 C19 H19A 110.2 . . ?
N11 C19 H19B 110.2 . . ?
C110 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N12 C110 C19 112.1(2) . . ?
N12 C110 H11B 109.2 . . ?
C19 C110 H11B 109.2 . . ?
N12 C110 H11A 109.2 . . ?
C19 C110 H11A 109.2 . . ?
H11B C110 H11A 107.9 . . ?
N12 C111 C112 111.7(2) . . ?
N12 C111 H11D 109.3 . . ?
C112 C111 H11D 109.3 . . ?
N12 C111 H11C 109.3 . . ?
C112 C111 H11C 109.3 . . ?
H11D C111 H11C 107.9 . . ?
N13 C112 C111 112.5(2) . . ?
N13 C112 H11E 109.1 . . ?
C111 C112 H11E 109.1 . . ?
N13 C112 H11F 109.1 . . ?
C111 C112 H11F 109.1 . . ?
H11E C112 H11F 107.8 . . ?
N13 C113 C115 118.3(3) . . ?
N13 C113 C114 118.8(3) . . ?
C115 C113 C114 122.9(3) . . ?
C113 C114 H11H 109.5 . . ?
C113 C114 H11I 109.5 . . ?
H11H C114 H11I 109.5 . . ?
C113 C114 H11G 109.5 . . ?
H11H C114 H11G 109.5 . . ?
H11I C114 H11G 109.5 . . ?
C113 C115 C116 119.1(3) . . ?
C113 C115 C120 120.7(2) . . ?
C116 C115 C120 120.0(3) . . ?
O14 C116 O15 113.5(3) . . ?
O14 C116 C115 129.5(3) . . ?
O15 C116 C115 117.0(3) . . ?
C119 C117 O15 122.2(3) . . ?
C119 C117 C118 127.1(3) . . ?
O15 C117 C118 110.8(2) . . ?
C117 C118 H11K 109.5 . . ?
C117 C118 H11J 109.5 . . ?
H11K C118 H11J 109.5 . . ?
C117 C118 H11L 109.5 . . ?
H11K C118 H11L 109.5 . . ?
H11J C118 H11L 109.5 . . ?
C117 C119 C120 121.4(3) . . ?
C117 C119 H119 119.3 . . ?
C120 C119 H119 119.3 . . ?
O16 C120 C119 120.0(3) . . ?
O16 C120 C115 123.0(3) . . ?
C119 C120 C115 117.0(3) . . ?
C17 N11 C19 127.4(2) . . ?
C17 N11 H11 116.3 . . ?
C19 N11 H11 116.3 . . ?
C111 N12 C110 113.2(2) . . ?
C111 N12 H12A 108.9 . . ?
C110 N12 H12A 108.9 . . ?
C111 N12 H12B 108.9 . . ?
C110 N12 H12B 108.9 . . ?
H12A N12 H12B 107.8 . . ?
C113 N13 C112 127.9(2) . . ?
C113 N13 H13 116.1 . . ?
C112 N13 H13 116.1 . . ?
C12 O12 C11 122.8(2) . . ?
C117 O15 C116 122.2(2) . . ?
O21 C21 O22 114.2(3) . . ?
O21 C21 C26 128.5(3) . . ?
O22 C21 C26 117.2(3) . . ?
C24 C22 O22 121.9(2) . . ?
C24 C22 C23 126.9(3) . . ?
O22 C22 C23 111.1(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 C25 121.8(3) . . ?
C22 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
O23 C25 C24 119.6(3) . . ?
O23 C25 C26 123.5(2) . . ?
C24 C25 C26 116.9(3) . . ?
C27 C26 C25 121.1(2) . . ?
C27 C26 C21 119.2(3) . . ?
C25 C26 C21 119.7(2) . . ?
N21 C27 C26 117.8(3) . . ?
N21 C27 C28 119.3(2) . . ?
C26 C27 C28 123.0(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N21 C29 C210 110.8(2) . . ?
N21 C29 H29A 109.5 . . ?
C210 C29 H29A 109.5 . . ?
N21 C29 H29B 109.5 . . ?
C210 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
N22 C210 C29 111.9(2) . . ?
N22 C210 H21A 109.2 . . ?
C29 C210 H21A 109.2 . . ?
N22 C210 H21B 109.2 . . ?
C29 C210 H21B 109.2 . . ?
H21A C210 H21B 107.9 . . ?
N22 C211 C212 111.7(2) . . ?
N22 C211 H21D 109.3 . . ?
C212 C211 H21D 109.3 . . ?
N22 C211 H21C 109.3 . . ?
C212 C211 H21C 109.3 . . ?
H21D C211 H21C 107.9 . . ?
N23 C212 C211 109.7(2) . . ?
N23 C212 H21E 109.7 . . ?
C211 C212 H21E 109.7 . . ?
N23 C212 H21F 109.7 . . ?
C211 C212 H21F 109.7 . . ?
H21E C212 H21F 108.2 . . ?
N23 C213 C215 118.0(3) . . ?
N23 C213 C214 118.4(2) . . ?
C215 C213 C214 123.6(3) . . ?
C213 C214 H21G 109.5 . . ?
C213 C214 H21I 109.5 . . ?
H21G C214 H21I 109.5 . . ?
C213 C214 H21H 109.5 . . ?
H21G C214 H21H 109.5 . . ?
H21I C214 H21H 109.5 . . ?
C220 C215 C216 120.0(2) . . ?
C220 C215 C213 121.3(2) . . ?
C216 C215 C213 118.5(3) . . ?
O24 C216 O25 113.5(3) . . ?
O24 C216 C215 129.3(3) . . ?
O25 C216 C215 117.2(3) . . ?
C219 C217 O25 121.8(3) . . ?
C219 C217 C218 127.6(3) . . ?
O25 C217 C218 110.6(3) . . ?
C217 C218 H21K 109.5 . . ?
C217 C218 H21L 109.5 . . ?
H21K C218 H21L 109.5 . . ?
C217 C218 H21J 109.5 . . ?
H21K C218 H21J 109.5 . . ?
H21L C218 H21J 109.5 . . ?
C217 C219 C220 121.8(3) . . ?
C217 C219 H219 119.1 . . ?
C220 C219 H219 119.1 . . ?
O26 C220 C219 119.6(3) . . ?
O26 C220 C215 123.3(2) . . ?
C219 C220 C215 117.0(3) . . ?
C27 N21 C29 128.8(2) . . ?
C27 N21 H21 115.6 . . ?
C29 N21 H21 115.6 . . ?
C210 N22 C211 111.92(19) . . ?
C210 N22 H22A 109.2 . . ?
C211 N22 H22A 109.2 . . ?
C210 N22 H22B 109.2 . . ?
C211 N22 H22B 109.2 . . ?
H22A N22 H22B 107.9 . . ?
C213 N23 C212 128.9(2) . . ?
C213 N23 H23 115.6 . . ?
C212 N23 H23 115.6 . . ?
C22 O22 C21 122.2(2) . . ?
C217 O25 C216 121.9(2) . . ?
N31 C31 S31 177.4(3) . . ?
N41A C41 N41B 33.8(15) . . ?
N41A C41 S41 163(3) . . ?
N41B C41 S41 163.1(19) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 978265'
_audit_update_record             
;
2014-11-25 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N3 O6, Br'
_chemical_formula_sum            'C20 H26 Br N3 O6'
_chemical_formula_weight         484.34
_chemical_compound_source        'chemical synthesis'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.9370(5)
_cell_length_b                   12.8236(10)
_cell_length_c                   13.4836(10)
_cell_angle_alpha                79.804(6)
_cell_angle_beta                 76.806(6)
_cell_angle_gamma                78.841(6)
_cell_volume                     1298.15(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      4.1962
_cell_measurement_theta_max      29.3084

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_min  0.82880
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4551
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4551
_reflns_number_gt                2847
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4551
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.1041
_refine_ls_wR_factor_ref         0.3386
_refine_ls_wR_factor_gt          0.3058
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69295(13) 0.50775(8) 0.12591(9) 0.0648(5) Uani 1 1 d . . .
O6 O 0.6836(6) -0.0531(4) 0.4283(4) 0.0261(11) Uani 1 1 d . . .
O1 O -0.2297(5) 0.1554(4) 0.1441(4) 0.0249(11) Uani 1 1 d . . .
O2 O -0.1974(6) -0.0197(4) 0.1640(4) 0.0294(12) Uani 1 1 d . . .
O4 O 1.1264(6) 0.1654(5) 0.3130(4) 0.0354(13) Uani 1 1 d . . .
O3 O 0.3326(6) -0.0581(4) 0.0900(4) 0.0232(11) Uani 1 1 d . . .
N1 N 0.3144(7) 0.1476(4) 0.0607(4) 0.0166(11) Uani 1 1 d . . .
H1 H 0.3713 0.0816 0.0679 0.020 Uiso 1 1 calc R . .
C5 C 0.1692(9) -0.0426(5) 0.1097(5) 0.0204(15) Uani 1 1 d . . .
N3 N 0.5907(6) 0.1526(4) 0.3981(4) 0.0169(12) Uani 1 1 d . . .
H3 H 0.5694 0.0863 0.4092 0.020 Uiso 1 1 calc R . .
O5 O 1.1910(6) -0.0077(5) 0.3439(4) 0.0392(14) Uani 1 1 d . . .
N2 N 0.4315(6) 0.2332(4) 0.2179(4) 0.0128(11) Uani 1 1 d . . .
H2A H 0.5407 0.1920 0.2053 0.015 Uiso 1 1 calc R . .
H2B H 0.3499 0.1879 0.2422 0.015 Uiso 1 1 calc R . .
C8 C 0.0424(8) 0.2675(5) 0.0557(5) 0.0215(15) Uani 1 1 d . . .
H8A H -0.0056 0.2959 0.1210 0.032 Uiso 1 1 calc R . .
H8B H -0.0538 0.2648 0.0222 0.032 Uiso 1 1 calc R . .
H8C H 0.1211 0.3143 0.0108 0.032 Uiso 1 1 calc R . .
C20 C 0.8399(9) -0.0347(6) 0.4038(5) 0.0232(15) Uani 1 1 d . . .
C4 C 0.0739(9) -0.1332(6) 0.1380(5) 0.0226(15) Uani 1 1 d . . .
H4 H 0.1375 -0.2040 0.1366 0.027 Uiso 1 1 calc R . .
C11 C 0.4241(8) 0.3048(5) 0.2978(5) 0.0187(14) Uani 1 1 d . . .
H11A H 0.5214 0.3471 0.2751 0.022 Uiso 1 1 calc R . .
H11B H 0.3123 0.3556 0.3045 0.022 Uiso 1 1 calc R . .
C14 C 0.7957(10) 0.2760(6) 0.3683(6) 0.0276(16) Uani 1 1 d . . .
H14A H 0.8335 0.3017 0.2951 0.041 Uiso 1 1 calc R . .
H14B H 0.8891 0.2763 0.4048 0.041 Uiso 1 1 calc R . .
H14C H 0.6898 0.3233 0.3970 0.041 Uiso 1 1 calc R . .
C15 C 0.8847(8) 0.0715(5) 0.3774(5) 0.0189(14) Uani 1 1 d . . .
C1 C -0.1241(9) 0.0724(6) 0.1371(5) 0.0242(16) Uani 1 1 d . . .
C7 C 0.1409(8) 0.1582(5) 0.0753(5) 0.0154(13) Uani 1 1 d . . .
C6 C 0.0602(8) 0.0630(5) 0.1052(5) 0.0186(14) Uani 1 1 d . . .
C2 C -0.0987(11) -0.1195(6) 0.1653(5) 0.0326(18) Uani 1 1 d . . .
C13 C 0.7573(8) 0.1651(5) 0.3804(5) 0.0194(14) Uani 1 1 d . . .
C10 C 0.3949(8) 0.3010(5) 0.1208(5) 0.0182(14) Uani 1 1 d . . .
H10A H 0.4752 0.3547 0.0988 0.022 Uiso 1 1 calc R . .
H10B H 0.2732 0.3400 0.1332 0.022 Uiso 1 1 calc R . .
C16 C 1.0684(9) 0.0832(7) 0.3442(5) 0.0275(17) Uani 1 1 d . . .
C19 C 0.9808(9) -0.1243(6) 0.4005(5) 0.0236(15) Uani 1 1 d . . .
H19 H 0.9554 -0.1954 0.4201 0.028 Uiso 1 1 calc R . .
C9 C 0.4192(8) 0.2314(5) 0.0347(5) 0.0175(14) Uani 1 1 d . . .
H9A H 0.3897 0.2783 -0.0276 0.021 Uiso 1 1 calc R . .
H9B H 0.5442 0.1989 0.0178 0.021 Uiso 1 1 calc R . .
C12 C 0.4380(8) 0.2383(5) 0.4011(5) 0.0207(14) Uani 1 1 d . . .
H12A H 0.4437 0.2865 0.4497 0.025 Uiso 1 1 calc R . .
H12B H 0.3303 0.2057 0.4281 0.025 Uiso 1 1 calc R . .
C17 C 1.1460(10) -0.1082(7) 0.3704(5) 0.0349(19) Uani 1 1 d . . .
C3 C -0.2110(13) -0.2070(7) 0.2035(7) 0.049(2) Uani 1 1 d . . .
H3A H -0.1375 -0.2772 0.1963 0.073 Uiso 1 1 calc R . .
H3B H -0.3022 -0.1965 0.1628 0.073 Uiso 1 1 calc R . .
H3C H -0.2658 -0.2040 0.2760 0.073 Uiso 1 1 calc R . .
C18 C 1.3074(13) -0.1945(10) 0.3569(8) 0.068(3) Uani 1 1 d . . .
H18A H 1.3760 -0.1821 0.2868 0.102 Uiso 1 1 calc R . .
H18B H 1.2709 -0.2652 0.3689 0.102 Uiso 1 1 calc R . .
H18C H 1.3793 -0.1918 0.4064 0.102 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O6 C20 1.266(8) . ?
O1 C1 1.224(8) . ?
O2 C2 1.364(10) . ?
O2 C1 1.372(9) . ?
O4 C16 1.200(9) . ?
O3 C5 1.247(8) . ?
N1 C7 1.329(8) . ?
N1 C9 1.432(8) . ?
N1 H1 0.8800 . ?
C5 C4 1.456(9) . ?
C5 C6 1.459(9) . ?
N3 C13 1.325(8) . ?
N3 C12 1.468(8) . ?
N3 H3 0.8800 . ?
O5 C16 1.367(9) . ?
O5 C17 1.369(10) . ?
N2 C10 1.493(8) . ?
N2 C11 1.519(8) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C8 C7 1.479(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C20 C15 1.437(9) . ?
C20 C19 1.439(10) . ?
C4 C2 1.320(10) . ?
C4 H4 0.9500 . ?
C11 C12 1.514(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 C13 1.485(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C13 1.412(10) . ?
C15 C16 1.453(9) . ?
C1 C6 1.415(9) . ?
C7 C6 1.441(9) . ?
C2 C3 1.514(10) . ?
C10 C9 1.541(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C19 C17 1.326(10) . ?
C19 H19 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C17 C18 1.522(11) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 122.4(5) . . ?
C7 N1 C9 127.4(5) . . ?
C7 N1 H1 116.3 . . ?
C9 N1 H1 116.3 . . ?
O3 C5 C4 120.3(6) . . ?
O3 C5 C6 124.4(6) . . ?
C4 C5 C6 115.3(6) . . ?
C13 N3 C12 126.6(5) . . ?
C13 N3 H3 116.7 . . ?
C12 N3 H3 116.7 . . ?
C16 O5 C17 122.3(6) . . ?
C10 N2 C11 109.5(5) . . ?
C10 N2 H2A 109.8 . . ?
C11 N2 H2A 109.8 . . ?
C10 N2 H2B 109.8 . . ?
C11 N2 H2B 109.8 . . ?
H2A N2 H2B 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C20 C15 123.4(6) . . ?
O6 C20 C19 118.7(6) . . ?
C15 C20 C19 117.9(6) . . ?
C2 C4 C5 121.6(7) . . ?
C2 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C12 C11 N2 110.7(5) . . ?
C12 C11 H11A 109.5 . . ?
N2 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C20 122.7(5) . . ?
C13 C15 C16 118.5(6) . . ?
C20 C15 C16 118.8(6) . . ?
O1 C1 O2 114.5(6) . . ?
O1 C1 C6 127.1(6) . . ?
O2 C1 C6 118.4(6) . . ?
N1 C7 C6 118.6(5) . . ?
N1 C7 C8 117.7(5) . . ?
C6 C7 C8 123.7(5) . . ?
C1 C6 C7 119.8(6) . . ?
C1 C6 C5 120.1(6) . . ?
C7 C6 C5 119.9(5) . . ?
C4 C2 O2 121.8(6) . . ?
C4 C2 C3 126.4(8) . . ?
O2 C2 C3 111.8(7) . . ?
N3 C13 C15 117.4(6) . . ?
N3 C13 C14 117.6(6) . . ?
C15 C13 C14 124.9(6) . . ?
N2 C10 C9 110.8(5) . . ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O4 C16 O5 115.0(6) . . ?
O4 C16 C15 126.9(7) . . ?
O5 C16 C15 118.1(6) . . ?
C17 C19 C20 120.3(7) . . ?
C17 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
N1 C9 C10 114.0(5) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N3 C12 C11 114.2(5) . . ?
N3 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C19 C17 O5 122.5(7) . . ?
C19 C17 C18 126.3(9) . . ?
O5 C17 C18 111.2(8) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.197

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 297 65 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1035947'
_audit_update_record             
;
2014-11-25 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H26 N3 O6), 2(Cl O3), 3(C H4 O)'
_chemical_formula_sum            'C43 H64 Cl2 N6 O21'
_chemical_formula_weight         1071.90
_chemical_compound_source        'chemical synthesis'

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

_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                   15.9465(6)
_cell_length_b                   18.9851(4)
_cell_length_c                   17.1610(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.552(4)
_cell_angle_gamma                90.00
_cell_volume                     4832.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    28515
_cell_measurement_theta_min      3.8320
_cell_measurement_theta_max      32.0763

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2264
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_min  0.90339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54110
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8484
_reflns_number_gt                6653
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1019P)²+9.7676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8484
_refine_ls_number_parameters     668
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1859
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.3211(2) 0.80496(19) 0.8473(2) 0.0370(8) Uani 1 1 d . . .
C12 C 0.4545(2) 0.73529(19) 0.8685(2) 0.0337(8) Uani 1 1 d . . .
C13 C 0.4812(3) 0.6613(2) 0.8646(3) 0.0440(9) Uani 1 1 d . . .
H13A H 0.4289 0.6316 0.8497 0.066 Uiso 0.50 1 calc PR . .
H13B H 0.5238 0.6473 0.9183 0.066 Uiso 0.50 1 calc PR . .
H13C H 0.5083 0.6568 0.8233 0.066 Uiso 0.50 1 calc PR . .
H13D H 0.5451 0.6588 0.8779 0.066 Uiso 0.50 1 calc PR . .
H13E H 0.4502 0.6432 0.8092 0.066 Uiso 0.50 1 calc PR . .
H13F H 0.4657 0.6337 0.9043 0.066 Uiso 0.50 1 calc PR . .
C14 C 0.5075(2) 0.79172(19) 0.8871(2) 0.0335(8) Uani 1 1 d . . .
H14 H 0.5689 0.7864 0.8987 0.040 Uiso 1 1 calc R . .
C15 C 0.4718(2) 0.86100(17) 0.8897(2) 0.0287(7) Uani 1 1 d . . .
C16 C 0.3761(2) 0.86621(17) 0.8711(2) 0.0290(7) Uani 1 1 d . . .
C17 C 0.3343(2) 0.93267(18) 0.8724(2) 0.0292(7) Uani 1 1 d . . .
C18 C 0.2353(2) 0.94117(19) 0.8503(2) 0.0353(8) Uani 1 1 d . . .
H18A H 0.2218 0.9898 0.8555 0.053 Uiso 1 1 calc R . .
H18B H 0.2164 0.9133 0.8876 0.053 Uiso 1 1 calc R . .
H18C H 0.2040 0.9259 0.7937 0.053 Uiso 1 1 calc R . .
C19 C 0.3590(3) 1.06055(18) 0.9003(2) 0.0360(8) Uani 1 1 d . . .
H19A H 0.4117 1.0878 0.9330 0.043 Uiso 1 1 calc R . .
H19B H 0.3180 1.0606 0.9303 0.043 Uiso 1 1 calc R . .
C110 C 0.3134(2) 1.09618(18) 0.8164(2) 0.0344(8) Uani 1 1 d . . .
H11A H 0.2558 1.0736 0.7871 0.041 Uiso 1 1 calc R . .
H11B H 0.3020 1.1451 0.8254 0.041 Uiso 1 1 calc R . .
C111 C 0.3384(2) 1.14693(18) 0.6959(2) 0.0345(8) Uani 1 1 d . . .
H11C H 0.3451 1.1933 0.7213 0.041 Uiso 1 1 calc R . .
H11D H 0.2748 1.1398 0.6634 0.041 Uiso 1 1 calc R . .
C112 C 0.3899(2) 1.14453(18) 0.6383(2) 0.0325(8) Uani 1 1 d . . .
H11E H 0.3773 1.1003 0.6079 0.039 Uiso 1 1 calc R . .
H11F H 0.3689 1.1822 0.5976 0.039 Uiso 1 1 calc R . .
C113 C 0.5347(2) 1.20935(16) 0.70271(19) 0.0259(7) Uani 1 1 d . . .
C114 C 0.4864(2) 1.27838(17) 0.6929(2) 0.0310(7) Uani 1 1 d . . .
H11G H 0.4225 1.2703 0.6714 0.047 Uiso 1 1 calc R . .
H11H H 0.5020 1.3077 0.6547 0.047 Uiso 1 1 calc R . .
H11I H 0.5038 1.3013 0.7464 0.047 Uiso 1 1 calc R . .
C115 C 0.6316(2) 1.20414(16) 0.73365(19) 0.0249(7) Uani 1 1 d . . .
C116 C 0.6851(2) 1.26724(17) 0.7507(2) 0.0295(7) Uani 1 1 d . . .
C117 C 0.8192(2) 1.19527(16) 0.77843(19) 0.0265(7) Uani 1 1 d . . .
C118 C 0.9170(2) 1.20337(18) 0.7986(2) 0.0332(8) Uani 1 1 d . . .
H11J H 0.9322 1.2525 0.8031 0.050 Uiso 0.50 1 calc PR . .
H11K H 0.9329 1.1825 0.7549 0.050 Uiso 0.50 1 calc PR . .
H11L H 0.9495 1.1803 0.8508 0.050 Uiso 0.50 1 calc PR . .
H11M H 0.9442 1.1577 0.8028 0.050 Uiso 0.50 1 calc PR . .
H11N H 0.9435 1.2277 0.8510 0.050 Uiso 0.50 1 calc PR . .
H11O H 0.9269 1.2299 0.7551 0.050 Uiso 0.50 1 calc PR . .
C119 C 0.7723(2) 1.13586(16) 0.76688(19) 0.0265(7) Uani 1 1 d . . .
H119 H 0.8023 1.0929 0.7747 0.032 Uiso 1 1 calc R . .
C120 C 0.6760(2) 1.13695(16) 0.74257(19) 0.0243(7) Uani 1 1 d . . .
N11 N 0.3866(2) 0.98855(15) 0.89388(17) 0.0314(6) Uani 1 1 d . . .
H11 H 0.4432 0.9817 0.9053 0.038 Uiso 1 1 calc R . .
N12 N 0.36919(18) 1.09274(14) 0.76350(17) 0.0290(6) Uani 1 1 d . . .
H12A H 0.3645 1.0496 0.7405 0.035 Uiso 1 1 calc R . .
H12B H 0.4275 1.1002 0.7955 0.035 Uiso 1 1 calc R . .
N13 N 0.48751(18) 1.15140(14) 0.68184(17) 0.0285(6) Uani 1 1 d . . .
H13 H 0.5173 1.1127 0.6953 0.034 Uiso 1 1 calc R . .
O11 O 0.23953(18) 0.80074(15) 0.8251(2) 0.0577(9) Uani 1 1 d . . .
O12 O 0.36327(16) 0.74056(13) 0.84938(18) 0.0403(6) Uani 1 1 d . . .
O13 O 0.52417(16) 0.91291(13) 0.90820(15) 0.0356(6) Uani 1 1 d . . .
O14 O 0.66157(17) 1.32802(12) 0.74887(19) 0.0457(7) Uani 1 1 d . . .
O15 O 0.77787(15) 1.25952(11) 0.77163(15) 0.0307(5) Uani 1 1 d . . .
O16 O 0.63308(15) 1.07886(11) 0.72936(14) 0.0281(5) Uani 1 1 d . . .
C21 C 0.7162(2) 1.20067(17) 0.5635(2) 0.0285(7) Uani 1 1 d . . .
C22 C 0.5811(2) 1.27185(18) 0.5274(2) 0.0302(7) Uani 1 1 d . . .
C23 C 0.5529(2) 1.34668(18) 0.5187(3) 0.0363(8) Uani 1 1 d . . .
H23A H 0.6052 1.3763 0.5330 0.054 Uiso 0.50 1 calc PR . .
H23B H 0.5214 1.3565 0.5555 0.054 Uiso 0.50 1 calc PR . .
H23C H 0.5139 1.3557 0.4618 0.054 Uiso 0.50 1 calc PR . .
H23D H 0.4884 1.3494 0.5006 0.054 Uiso 0.50 1 calc PR . .
H23E H 0.5722 1.3692 0.4780 0.054 Uiso 0.50 1 calc PR . .
H23F H 0.5797 1.3700 0.5717 0.054 Uiso 0.50 1 calc PR . .
C24 C 0.5279(2) 1.21522(17) 0.5136(2) 0.0273(7) Uani 1 1 d . . .
H24 H 0.4657 1.2212 0.4943 0.033 Uiso 1 1 calc R . .
C25 C 0.5651(2) 1.14494(17) 0.52800(19) 0.0265(7) Uani 1 1 d . . .
C26 C 0.6618(2) 1.13853(16) 0.5505(2) 0.0262(7) Uani 1 1 d . . .
C27 C 0.7038(2) 1.07057(17) 0.5656(2) 0.0269(7) Uani 1 1 d . . .
C28 C 0.7992(2) 1.05854(19) 0.5723(2) 0.0355(8) Uani 1 1 d . . .
H28A H 0.8138 1.0095 0.5823 0.053 Uiso 0.50 1 calc PR . .
H28B H 0.8393 1.0859 0.6179 0.053 Uiso 0.50 1 calc PR . .
H28C H 0.8056 1.0726 0.5210 0.053 Uiso 0.50 1 calc PR . .
H28D H 0.8253 1.1025 0.5651 0.053 Uiso 0.50 1 calc PR . .
H28E H 0.7998 1.0261 0.5296 0.053 Uiso 0.50 1 calc PR . .
H28F H 0.8335 1.0394 0.6265 0.053 Uiso 0.50 1 calc PR . .
C29 C 0.6864(2) 0.94338(17) 0.5934(2) 0.0300(7) Uani 1 1 d . . .
H29A H 0.7517 0.9421 0.6186 0.036 Uiso 1 1 calc R . .
H29B H 0.6678 0.9147 0.5431 0.036 Uiso 1 1 calc R . .
C210 C 0.6468(2) 0.91353(16) 0.6542(2) 0.0273(7) Uani 1 1 d . . .
H21A H 0.5830 0.9246 0.6345 0.033 Uiso 1 1 calc R . .
H21B H 0.6530 0.8627 0.6558 0.033 Uiso 1 1 calc R . .
C211 C 0.6621(2) 0.90729(16) 0.8037(2) 0.0280(7) Uani 1 1 d . . .
H21C H 0.6715 0.8569 0.8023 0.034 Uiso 1 1 calc R . .
H21D H 0.5982 0.9155 0.7892 0.034 Uiso 1 1 calc R . .
C212 C 0.7133(2) 0.93469(16) 0.8915(2) 0.0281(7) Uani 1 1 d . . .
H21E H 0.7022 0.9041 0.9320 0.034 Uiso 1 1 calc R . .
H21F H 0.7775 0.9339 0.9026 0.034 Uiso 1 1 calc R . .
C213 C 0.7385(2) 1.05991(17) 0.93746(19) 0.0260(7) Uani 1 1 d . . .
C214 C 0.8376(2) 1.04611(18) 0.9781(2) 0.0314(7) Uani 1 1 d . . .
H21G H 0.8496 0.9976 0.9702 0.047 Uiso 0.50 1 calc PR . .
H21H H 0.8570 1.0561 1.0369 0.047 Uiso 0.50 1 calc PR . .
H21I H 0.8696 1.0758 0.9532 0.047 Uiso 0.50 1 calc PR . .
H21J H 0.8679 1.0887 1.0033 0.047 Uiso 0.50 1 calc PR . .
H21K H 0.8605 1.0302 0.9366 0.047 Uiso 0.50 1 calc PR . .
H21L H 0.8479 1.0106 1.0204 0.047 Uiso 0.50 1 calc PR . .
C215 C 0.6987(2) 1.12763(17) 0.9382(2) 0.0263(7) Uani 1 1 d . . .
C216 C 0.7559(2) 1.18917(17) 0.9639(2) 0.0309(7) Uani 1 1 d . . .
C217 C 0.6230(2) 1.26095(17) 0.9388(2) 0.0300(7) Uani 1 1 d . . .
C218 C 0.5965(3) 1.33575(19) 0.9421(3) 0.0407(9) Uani 1 1 d . . .
H21M H 0.6496 1.3645 0.9634 0.061 Uiso 0.50 1 calc PR . .
H21N H 0.5629 1.3397 0.9783 0.061 Uiso 0.50 1 calc PR . .
H21O H 0.5598 1.3513 0.8868 0.061 Uiso 0.50 1 calc PR . .
H21P H 0.5319 1.3392 0.9223 0.061 Uiso 0.50 1 calc PR . .
H21Q H 0.6187 1.3639 0.9074 0.061 Uiso 0.50 1 calc PR . .
H21R H 0.6217 1.3524 0.9989 0.061 Uiso 0.50 1 calc PR . .
C219 C 0.5682(2) 1.20608(17) 0.9129(2) 0.0297(7) Uani 1 1 d . . .
H219 H 0.5063 1.2127 0.8972 0.036 Uiso 1 1 calc R . .
C220 C 0.6023(2) 1.13668(17) 0.90859(19) 0.0264(7) Uani 1 1 d . . .
N21 N 0.65632(18) 1.01602(14) 0.57136(16) 0.0263(6) Uani 1 1 d . . .
H21 H 0.6001 1.0238 0.5608 0.032 Uiso 1 1 calc R . .
N22 N 0.69216(18) 0.94238(13) 0.74059(16) 0.0260(6) Uani 1 1 d . . .
H22A H 0.7522 0.9370 0.7561 0.031 Uiso 1 1 calc R . .
H22B H 0.6806 0.9888 0.7400 0.031 Uiso 1 1 calc R . .
N23 N 0.68568(18) 1.00684(14) 0.90151(16) 0.0268(6) Uani 1 1 d . . .
H23 H 0.6287 1.0152 0.8816 0.032 Uiso 1 1 calc R . .
O21 O 0.79746(16) 1.20514(13) 0.58603(17) 0.0396(6) Uani 1 1 d . . .
O22 O 0.67314(15) 1.26576(12) 0.55304(15) 0.0328(5) Uani 1 1 d . . .
O23 O 0.51344(15) 1.09309(11) 0.52047(14) 0.0299(5) Uani 1 1 d . . .
O24 O 0.83663(16) 1.19345(13) 0.98500(18) 0.0409(6) Uani 1 1 d . . .
O25 O 0.71387(16) 1.25423(12) 0.96297(15) 0.0344(6) Uani 1 1 d . . .
O26 O 0.54707(15) 1.08649(12) 0.87851(15) 0.0316(5) Uani 1 1 d . . .
O31 O 0.46609(18) 0.98677(14) 0.68361(19) 0.0487(7) Uani 1 1 d . . .
O32 O 0.31957(18) 0.96224(14) 0.68066(18) 0.0447(7) Uani 1 1 d . . .
O33 O 0.4207(2) 0.86788(14) 0.68792(19) 0.0524(7) Uani 1 1 d . . .
Cl31 Cl 0.39060(6) 0.93607(5) 0.64977(5) 0.0371(2) Uani 1 1 d . . .
Cl4A Cl 0.96284(6) 0.97152(4) 0.79711(7) 0.0414(3) Uani 1 1 d D . .
O41A O 0.8765(2) 0.98240(17) 0.8097(4) 0.0406(11) Uani 0.813(10) 1 d P A 1
O42A O 0.9469(4) 0.9580(3) 0.7137(3) 0.086(2) Uani 0.813(10) 1 d P A 1
O43A O 1.0140(4) 1.0368(2) 0.8260(6) 0.107(3) Uani 0.813(10) 1 d P A 1
O41B O 0.8641(6) 0.9816(10) 0.7679(14) 0.052(6) Uiso 0.187(10) 1 d PD A 2
O42B O 0.9904(9) 1.0385(6) 0.7666(10) 0.040(5) Uiso 0.187(10) 1 d PD A 2
O43B O 0.9954(19) 0.9795(18) 0.8872(6) 0.32(4) Uiso 0.187(10) 1 d PD A 2
C51 C 0.1589(4) 0.1811(3) 0.8700(4) 0.0700(14) Uani 1 1 d . . .
H51A H 0.1045 0.2006 0.8726 0.105 Uiso 1 1 calc R . .
H51B H 0.1608 0.1896 0.8154 0.105 Uiso 1 1 calc R . .
H51C H 0.2101 0.2030 0.9117 0.105 Uiso 1 1 calc R . .
O51 O 0.1612(2) 0.10685(19) 0.8850(3) 0.0711(10) Uani 1 1 d . . .
H51 H 0.1102 0.0906 0.8632 0.107 Uiso 1 1 calc R . .
C61 C 0.1682(5) 0.8072(4) 0.5967(5) 0.104(2) Uani 1 1 d . . .
H61A H 0.1385 0.8518 0.5814 0.157 Uiso 1 1 calc R . .
H61B H 0.1551 0.7785 0.5475 0.157 Uiso 1 1 calc R . .
H61C H 0.2321 0.8144 0.6222 0.157 Uiso 1 1 calc R . .
O61 O 0.1382(2) 0.7742(2) 0.6520(2) 0.0738(10) Uani 1 1 d . . .
H61 H 0.1708 0.7846 0.7000 0.111 Uiso 1 1 calc R . .
O71 O 0.1517(3) 0.0261(2) 0.6043(3) 0.0944(13) Uani 1 1 d . . .
H71 H 0.1988 0.0035 0.6213 0.142 Uiso 1 1 calc R . .
C71 C 0.0809(5) -0.0153(3) 0.6118(6) 0.121(3) Uani 1 1 d . . .
H71A H 0.0818 -0.0119 0.6679 0.182 Uiso 1 1 calc R . .
H71B H 0.0889 -0.0636 0.5994 0.182 Uiso 1 1 calc R . .
H71C H 0.0241 0.0015 0.5731 0.182 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C11 O11 1.217(4) . ?
C11 O12 1.389(4) . ?
C11 C16 1.423(5) . ?
C12 C14 1.328(5) . ?
C12 O12 1.373(4) . ?
C12 C13 1.477(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C14 C15 1.440(5) . ?
C14 H14 0.9300 . ?
C15 O13 1.255(4) . ?
C15 C16 1.444(5) . ?
C16 C17 1.431(5) . ?
C17 N11 1.315(4) . ?
C17 C18 1.490(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N11 1.452(4) . ?
C19 C110 1.514(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C110 N12 1.488(4) . ?
C110 H11A 0.9700 . ?
C110 H11B 0.9700 . ?
C111 N12 1.492(4) . ?
C111 C112 1.501(5) . ?
C111 H11C 0.9700 . ?
C111 H11D 0.9700 . ?
C112 N13 1.464(4) . ?
C112 H11E 0.9700 . ?
C112 H11F 0.9700 . ?
C113 N13 1.307(4) . ?
C113 C115 1.441(5) . ?
C113 C114 1.498(4) . ?
C114 H11G 0.9600 . ?
C114 H11H 0.9600 . ?
C114 H11I 0.9600 . ?
C115 C116 1.437(4) . ?
C115 C120 1.440(4) . ?
C116 O14 1.210(4) . ?
C116 O15 1.396(4) . ?
C117 C119 1.327(5) . ?
C117 O15 1.371(4) . ?
C117 C118 1.476(5) . ?
C118 H11J 0.9600 . ?
C118 H11K 0.9600 . ?
C118 H11L 0.9600 . ?
C118 H11M 0.9600 . ?
C118 H11N 0.9600 . ?
C118 H11O 0.9600 . ?
C119 C120 1.436(5) . ?
C119 H119 0.9300 . ?
C120 O16 1.274(4) . ?
N11 H11 0.8600 . ?
N12 H12A 0.9000 . ?
N12 H12B 0.9000 . ?
N13 H13 0.8600 . ?
C21 O21 1.211(4) . ?
C21 O22 1.393(4) . ?
C21 C26 1.433(4) . ?
C22 C24 1.336(5) . ?
C22 O22 1.374(4) . ?
C22 C23 1.481(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23D 0.9600 . ?
C23 H23E 0.9600 . ?
C23 H23F 0.9600 . ?
C24 C25 1.444(4) . ?
C24 H24 0.9300 . ?
C25 O23 1.260(4) . ?
C25 C26 1.450(4) . ?
C26 C27 1.433(4) . ?
C27 N21 1.307(4) . ?
C27 C28 1.501(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28 H28D 0.9600 . ?
C28 H28E 0.9600 . ?
C28 H28F 0.9600 . ?
C29 N21 1.463(4) . ?
C29 C210 1.514(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C210 N22 1.495(4) . ?
C210 H21A 0.9700 . ?
C210 H21B 0.9700 . ?
C211 N22 1.492(4) . ?
C211 C212 1.519(5) . ?
C211 H21C 0.9700 . ?
C211 H21D 0.9700 . ?
C212 N23 1.468(4) . ?
C212 H21E 0.9700 . ?
C212 H21F 0.9700 . ?
C213 N23 1.313(4) . ?
C213 C215 1.435(4) . ?
C213 C214 1.498(5) . ?
C214 H21G 0.9600 . ?
C214 H21H 0.9600 . ?
C214 H21I 0.9600 . ?
C214 H21J 0.9600 . ?
C214 H21K 0.9600 . ?
C214 H21L 0.9600 . ?
C215 C220 1.442(5) . ?
C215 C216 1.448(5) . ?
C216 O24 1.205(4) . ?
C216 O25 1.403(4) . ?
C217 C219 1.327(5) . ?
C217 O25 1.359(4) . ?
C217 C218 1.489(5) . ?
C218 H21M 0.9600 . ?
C218 H21N 0.9600 . ?
C218 H21O 0.9600 . ?
C218 H21P 0.9600 . ?
C218 H21Q 0.9600 . ?
C218 H21R 0.9600 . ?
C219 C220 1.438(4) . ?
C219 H219 0.9300 . ?
C220 O26 1.271(4) . ?
N21 H21 0.8600 . ?
N22 H22A 0.9000 . ?
N22 H22B 0.9000 . ?
N23 H23 0.8600 . ?
O31 Cl31 1.483(3) . ?
O32 Cl31 1.501(3) . ?
O33 Cl31 1.451(3) . ?
Cl4A O42A 1.382(5) . ?
Cl4A O43B 1.446(10) . ?
Cl4A O43A 1.466(4) . ?
Cl4A O41B 1.480(9) . ?
Cl4A O41A 1.484(3) . ?
Cl4A O42B 1.501(8) . ?
C51 O51 1.431(6) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
O51 H51 0.8200 . ?
C61 O61 1.361(6) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
O61 H61 0.8200 . ?
O71 C71 1.421(8) . ?
O71 H71 0.8200 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 C11 O12 113.7(3) . . ?
O11 C11 C16 128.2(3) . . ?
O12 C11 C16 118.1(3) . . ?
C14 C12 O12 121.5(3) . . ?
C14 C12 C13 127.6(3) . . ?
O12 C12 C13 110.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13D 109.5 . . ?
H13A C13 H13D 141.1 . . ?
H13B C13 H13D 56.3 . . ?
H13C C13 H13D 56.3 . . ?
C12 C13 H13E 109.5 . . ?
H13A C13 H13E 56.3 . . ?
H13B C13 H13E 141.1 . . ?
H13C C13 H13E 56.3 . . ?
H13D C13 H13E 109.5 . . ?
C12 C13 H13F 109.5 . . ?
H13A C13 H13F 56.3 . . ?
H13B C13 H13F 56.3 . . ?
H13C C13 H13F 141.1 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C12 C14 C15 121.4(3) . . ?
C12 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
O13 C15 C14 119.5(3) . . ?
O13 C15 C16 123.6(3) . . ?
C14 C15 C16 116.9(3) . . ?
C11 C16 C17 118.9(3) . . ?
C11 C16 C15 119.8(3) . . ?
C17 C16 C15 121.2(3) . . ?
N11 C17 C16 117.7(3) . . ?
N11 C17 C18 119.1(3) . . ?
C16 C17 C18 123.2(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N11 C19 C110 113.6(3) . . ?
N11 C19 H19A 108.8 . . ?
C110 C19 H19A 108.8 . . ?
N11 C19 H19B 108.8 . . ?
C110 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
N12 C110 C19 112.0(3) . . ?
N12 C110 H11A 109.2 . . ?
C19 C110 H11A 109.2 . . ?
N12 C110 H11B 109.2 . . ?
C19 C110 H11B 109.2 . . ?
H11A C110 H11B 107.9 . . ?
N12 C111 C112 112.8(3) . . ?
N12 C111 H11C 109.0 . . ?
C112 C111 H11C 109.0 . . ?
N12 C111 H11D 109.0 . . ?
C112 C111 H11D 109.0 . . ?
H11C C111 H11D 107.8 . . ?
N13 C112 C111 113.4(3) . . ?
N13 C112 H11E 108.9 . . ?
C111 C112 H11E 108.9 . . ?
N13 C112 H11F 108.9 . . ?
C111 C112 H11F 108.9 . . ?
H11E C112 H11F 107.7 . . ?
N13 C113 C115 118.4(3) . . ?
N13 C113 C114 119.0(3) . . ?
C115 C113 C114 122.6(3) . . ?
C113 C114 H11G 109.5 . . ?
C113 C114 H11H 109.5 . . ?
H11G C114 H11H 109.5 . . ?
C113 C114 H11I 109.5 . . ?
H11G C114 H11I 109.5 . . ?
H11H C114 H11I 109.5 . . ?
C116 C115 C120 119.0(3) . . ?
C116 C115 C113 119.6(3) . . ?
C120 C115 C113 121.3(3) . . ?
O14 C116 O15 113.3(3) . . ?
O14 C116 C115 129.4(3) . . ?
O15 C116 C115 117.3(3) . . ?
C119 C117 O15 121.1(3) . . ?
C119 C117 C118 127.8(3) . . ?
O15 C117 C118 111.2(3) . . ?
C117 C118 H11J 109.5 . . ?
C117 C118 H11K 109.5 . . ?
H11J C118 H11K 109.5 . . ?
C117 C118 H11L 109.5 . . ?
H11J C118 H11L 109.5 . . ?
H11K C118 H11L 109.5 . . ?
C117 C118 H11M 109.5 . . ?
H11J C118 H11M 141.1 . . ?
H11K C118 H11M 56.3 . . ?
H11L C118 H11M 56.3 . . ?
C117 C118 H11N 109.5 . . ?
H11J C118 H11N 56.3 . . ?
H11K C118 H11N 141.1 . . ?
H11L C118 H11N 56.3 . . ?
H11M C118 H11N 109.5 . . ?
C117 C118 H11O 109.5 . . ?
H11J C118 H11O 56.3 . . ?
H11K C118 H11O 56.3 . . ?
H11L C118 H11O 141.1 . . ?
H11M C118 H11O 109.5 . . ?
H11N C118 H11O 109.5 . . ?
C117 C119 C120 121.0(3) . . ?
C117 C119 H119 119.5 . . ?
C120 C119 H119 119.5 . . ?
O16 C120 C119 119.1(3) . . ?
O16 C120 C115 122.5(3) . . ?
C119 C120 C115 118.4(3) . . ?
C17 N11 C19 127.0(3) . . ?
C17 N11 H11 116.5 . . ?
C19 N11 H11 116.5 . . ?
C110 N12 C111 110.1(3) . . ?
C110 N12 H12A 109.6 . . ?
C111 N12 H12A 109.6 . . ?
C110 N12 H12B 109.6 . . ?
C111 N12 H12B 109.6 . . ?
H12A N12 H12B 108.1 . . ?
C113 N13 C112 127.8(3) . . ?
C113 N13 H13 116.1 . . ?
C112 N13 H13 116.1 . . ?
C12 O12 C11 122.0(3) . . ?
C117 O15 C116 123.1(2) . . ?
O21 C21 O22 113.5(3) . . ?
O21 C21 C26 128.6(3) . . ?
O22 C21 C26 117.9(3) . . ?
C24 C22 O22 121.5(3) . . ?
C24 C22 C23 127.2(3) . . ?
O22 C22 C23 111.2(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C23 H23D 109.5 . . ?
H23A C23 H23D 141.1 . . ?
H23B C23 H23D 56.3 . . ?
H23C C23 H23D 56.3 . . ?
C22 C23 H23E 109.5 . . ?
H23A C23 H23E 56.3 . . ?
H23B C23 H23E 141.1 . . ?
H23C C23 H23E 56.3 . . ?
H23D C23 H23E 109.5 . . ?
C22 C23 H23F 109.5 . . ?
H23A C23 H23F 56.3 . . ?
H23B C23 H23F 56.3 . . ?
H23C C23 H23F 141.1 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 109.5 . . ?
C22 C24 C25 121.3(3) . . ?
C22 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
O23 C25 C24 119.5(3) . . ?
O23 C25 C26 123.6(3) . . ?
C24 C25 C26 116.9(3) . . ?
C27 C26 C21 119.8(3) . . ?
C27 C26 C25 120.3(3) . . ?
C21 C26 C25 119.8(3) . . ?
N21 C27 C26 118.8(3) . . ?
N21 C27 C28 118.2(3) . . ?
C26 C27 C28 123.0(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28 H28D 109.5 . . ?
H28A C28 H28D 141.1 . . ?
H28B C28 H28D 56.3 . . ?
H28C C28 H28D 56.3 . . ?
C27 C28 H28E 109.5 . . ?
H28A C28 H28E 56.3 . . ?
H28B C28 H28E 141.1 . . ?
H28C C28 H28E 56.3 . . ?
H28D C28 H28E 109.5 . . ?
C27 C28 H28F 109.5 . . ?
H28A C28 H28F 56.3 . . ?
H28B C28 H28F 56.3 . . ?
H28C C28 H28F 141.1 . . ?
H28D C28 H28F 109.5 . . ?
H28E C28 H28F 109.5 . . ?
N21 C29 C210 110.5(3) . . ?
N21 C29 H29A 109.5 . . ?
C210 C29 H29A 109.5 . . ?
N21 C29 H29B 109.5 . . ?
C210 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
N22 C210 C29 112.0(3) . . ?
N22 C210 H21A 109.2 . . ?
C29 C210 H21A 109.2 . . ?
N22 C210 H21B 109.2 . . ?
C29 C210 H21B 109.2 . . ?
H21A C210 H21B 107.9 . . ?
N22 C211 C212 111.6(3) . . ?
N22 C211 H21C 109.3 . . ?
C212 C211 H21C 109.3 . . ?
N22 C211 H21D 109.3 . . ?
C212 C211 H21D 109.3 . . ?
H21C C211 H21D 108.0 . . ?
N23 C212 C211 111.1(3) . . ?
N23 C212 H21E 109.4 . . ?
C211 C212 H21E 109.4 . . ?
N23 C212 H21F 109.4 . . ?
C211 C212 H21F 109.4 . . ?
H21E C212 H21F 108.0 . . ?
N23 C213 C215 118.9(3) . . ?
N23 C213 C214 118.0(3) . . ?
C215 C213 C214 123.1(3) . . ?
C213 C214 H21G 109.5 . . ?
C213 C214 H21H 109.5 . . ?
H21G C214 H21H 109.5 . . ?
C213 C214 H21I 109.5 . . ?
H21G C214 H21I 109.5 . . ?
H21H C214 H21I 109.5 . . ?
C213 C214 H21J 109.5 . . ?
H21G C214 H21J 141.1 . . ?
H21H C214 H21J 56.3 . . ?
H21I C214 H21J 56.3 . . ?
C213 C214 H21K 109.5 . . ?
H21G C214 H21K 56.3 . . ?
H21H C214 H21K 141.1 . . ?
H21I C214 H21K 56.3 . . ?
H21J C214 H21K 109.5 . . ?
C213 C214 H21L 109.5 . . ?
H21G C214 H21L 56.3 . . ?
H21H C214 H21L 56.3 . . ?
H21I C214 H21L 141.1 . . ?
H21J C214 H21L 109.5 . . ?
H21K C214 H21L 109.5 . . ?
C213 C215 C220 121.4(3) . . ?
C213 C215 C216 119.7(3) . . ?
C220 C215 C216 118.8(3) . . ?
O24 C216 O25 113.4(3) . . ?
O24 C216 C215 129.0(3) . . ?
O25 C216 C215 117.5(3) . . ?
C219 C217 O25 121.7(3) . . ?
C219 C217 C218 126.9(3) . . ?
O25 C217 C218 111.3(3) . . ?
C217 C218 H21M 109.5 . . ?
C217 C218 H21N 109.5 . . ?
H21M C218 H21N 109.5 . . ?
C217 C218 H21O 109.5 . . ?
H21M C218 H21O 109.5 . . ?
H21N C218 H21O 109.5 . . ?
C217 C218 H21P 109.5 . . ?
H21M C218 H21P 141.1 . . ?
H21N C218 H21P 56.3 . . ?
H21O C218 H21P 56.3 . . ?
C217 C218 H21Q 109.5 . . ?
H21M C218 H21Q 56.3 . . ?
H21N C218 H21Q 141.1 . . ?
H21O C218 H21Q 56.3 . . ?
H21P C218 H21Q 109.5 . . ?
C217 C218 H21R 109.5 . . ?
H21M C218 H21R 56.3 . . ?
H21N C218 H21R 56.3 . . ?
H21O C218 H21R 141.1 . . ?
H21P C218 H21R 109.5 . . ?
H21Q C218 H21R 109.5 . . ?
C217 C219 C220 121.4(3) . . ?
C217 C219 H219 119.3 . . ?
C220 C219 H219 119.3 . . ?
O26 C220 C219 119.3(3) . . ?
O26 C220 C215 122.9(3) . . ?
C219 C220 C215 117.8(3) . . ?
C27 N21 C29 128.5(3) . . ?
C27 N21 H21 115.8 . . ?
C29 N21 H21 115.8 . . ?
C211 N22 C210 112.9(2) . . ?
C211 N22 H22A 109.0 . . ?
C210 N22 H22A 109.0 . . ?
C211 N22 H22B 109.0 . . ?
C210 N22 H22B 109.0 . . ?
H22A N22 H22B 107.8 . . ?
C213 N23 C212 127.1(3) . . ?
C213 N23 H23 116.5 . . ?
C212 N23 H23 116.5 . . ?
C22 O22 C21 122.3(2) . . ?
C217 O25 C216 122.6(3) . . ?
O33 Cl31 O31 108.43(18) . . ?
O33 Cl31 O32 107.67(18) . . ?
O31 Cl31 O32 104.85(15) . . ?
O42A Cl4A O43B 169.4(15) . . ?
O42A Cl4A O43A 112.0(5) . . ?
O43B Cl4A O43A 67.3(10) . . ?
O42A Cl4A O41B 84.6(9) . . ?
O43B Cl4A O41B 105.5(9) . . ?
O43A Cl4A O41B 113.3(8) . . ?
O42A Cl4A O41A 110.4(3) . . ?
O43B Cl4A O41A 79.5(12) . . ?
O43A Cl4A O41A 105.3(3) . . ?
O41B Cl4A O41A 26.1(8) . . ?
O42A Cl4A O42B 76.3(7) . . ?
O43B Cl4A O42B 104.3(9) . . ?
O43A Cl4A O42B 37.2(5) . . ?
O41B Cl4A O42B 100.6(7) . . ?
O41A Cl4A O42B 109.8(6) . . ?
O51 C51 H51A 109.5 . . ?
O51 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O51 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C51 O51 H51 109.5 . . ?
O61 C61 H61A 109.5 . . ?
O61 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O61 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C61 O61 H61 109.5 . . ?
C71 O71 H71 109.5 . . ?
O71 C71 H71A 109.5 . . ?
O71 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O71 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.192
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.078

# start Validation Reply Form
_vrf_PLAT413_exp_260             
;
PROBLEM: Short Inter XH3 .. XHn     H61A   ..  H71B    ..       1.87 Ang.  
RESPONSE: The data was collected at room temperature and the positions 
of all hydrogen atoms were determined on stereochemical grounds. 
The positions of hydrogen atoms in methanol molecules were 
modelled using HFIX 137 and 147. These solvent molecules have higher 
thermal parameters (refined isotropically) than the rest 
of the structure and probably, hydrogen atoms are not 
at the optimal positions.
;
_vrf_PLAT412_exp_260             
;
PROBLEM: Short Intra XH3 .. XHn     H21F   ..  H21G    ..       1.77 Ang.  
RESPONSE: The data was collected at room temperature and the positions 
of all hydrogen atoms were determined on stereochemical grounds. 
In some cases it was possible to model methyl groups in 
two positions (HFIX 123), but obviously hydrogen atoms were not 
at the optimal positions.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1051952'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N3 O6, Br, C H2 O0.5'
_chemical_formula_sum            'C20.50 H28 Br N3 O6.50'
_chemical_formula_weight         500.37
_chemical_compound_source        'chemical synthesis'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9370(5)
_cell_length_b                   12.8240(10)
_cell_length_c                   13.4850(10)
_cell_angle_alpha                79.800(6)
_cell_angle_beta                 76.802(6)
_cell_angle_gamma                78.839(6)
_cell_volume                     1298.28(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      4.1962
_cell_measurement_theta_max      29.3084

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.621
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_T_min  0.82880
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            8796
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.204
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4551
_reflns_number_gt                2689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4551
_refine_ls_number_parameters     319
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.1052
_refine_ls_wR_factor_ref         0.3421
_refine_ls_wR_factor_gt          0.3065
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3784(9) 0.0722(6) 0.1366(5) 0.0365(17) Uani 1 1 d . . . . .
C2 C 0.4045(11) -0.1217(6) 0.1655(5) 0.0421(19) Uani 1 1 d . . . . .
C3 C 0.2940(13) -0.2086(8) 0.2025(7) 0.068(3) Uani 1 1 d . . . . .
H3A H 0.1726 -0.1770 0.2174 0.103 Uiso 1 1 calc R U . . .
H3B H 0.3123 -0.2538 0.1501 0.103 Uiso 1 1 calc R U . . .
H3C H 0.3261 -0.2507 0.2637 0.103 Uiso 1 1 calc R U . . .
C4 C 0.5736(9) -0.1337(6) 0.1382(5) 0.0359(17) Uani 1 1 d . . . . .
H4 H 0.6366 -0.2027 0.1367 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6693(9) -0.0427(6) 0.1098(5) 0.0336(16) Uani 1 1 d . . . . .
C6 C 0.5611(8) 0.0622(5) 0.1054(5) 0.0300(15) Uani 1 1 d . . . . .
C7 C 0.6426(8) 0.1578(5) 0.0753(5) 0.0294(15) Uani 1 1 d . . . . .
C8 C 0.5422(9) 0.2666(6) 0.0573(6) 0.0366(17) Uani 1 1 d . . . . .
H8A H 0.4195 0.2625 0.0705 0.055 Uiso 1 1 calc R U . . .
H8B H 0.5630 0.3106 0.1026 0.055 Uiso 1 1 calc R U . . .
H8C H 0.5790 0.2975 -0.0128 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9211(9) 0.2330(6) 0.0350(5) 0.0334(16) Uani 1 1 d . . . . .
H9A H 0.8923 0.2797 -0.0258 0.040 Uiso 1 1 calc R U . . .
H9B H 1.0435 0.2010 0.0183 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8965(9) 0.2991(5) 0.1201(5) 0.0362(17) Uani 1 1 d . . . . .
H10A H 0.9738 0.3525 0.0985 0.043 Uiso 1 1 calc R U . . .
H10B H 0.7769 0.3367 0.1319 0.043 Uiso 1 1 calc R U . . .
C11 C 0.9231(9) 0.3047(5) 0.2975(5) 0.0341(16) Uani 1 1 d . . . . .
H11A H 0.8130 0.3539 0.3040 0.041 Uiso 1 1 calc R U . . .
H11B H 1.0174 0.3469 0.2756 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9374(9) 0.2385(6) 0.4019(6) 0.0382(17) Uani 1 1 d . . . . .
H12A H 0.9432 0.2862 0.4490 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8320 0.2066 0.4288 0.046 Uiso 1 1 calc R U . . .
C13 C 1.2578(9) 0.1637(6) 0.3808(5) 0.0322(16) Uani 1 1 d . . . . .
C14 C 1.2955(10) 0.2756(7) 0.3678(6) 0.046(2) Uani 1 1 d . . . . .
H14A H 1.4200 0.2742 0.3549 0.069 Uiso 1 1 calc R U . . .
H14B H 1.2493 0.3177 0.3108 0.069 Uiso 1 1 calc R U . . .
H14C H 1.2416 0.3069 0.4293 0.069 Uiso 1 1 calc R U . . .
C15 C 1.3865(8) 0.0705(6) 0.3778(5) 0.0333(17) Uani 1 1 d . . . . .
C16 C 1.5673(9) 0.0825(7) 0.3442(5) 0.0408(19) Uani 1 1 d . . . . .
C17 C 1.6469(11) -0.1088(8) 0.3700(6) 0.050(2) Uani 1 1 d . . . . .
C18 C 1.8040(13) -0.1934(10) 0.3583(7) 0.090(4) Uani 1 1 d . . . . .
H18A H 1.9076 -0.1605 0.3351 0.135 Uiso 1 1 calc R U . . .
H18B H 1.8091 -0.2374 0.4233 0.135 Uiso 1 1 calc R U . . .
H18C H 1.7970 -0.2371 0.3088 0.135 Uiso 1 1 calc R U . . .
C19 C 1.4782(9) -0.1236(6) 0.4009(5) 0.0366(17) Uani 1 1 d . . . . .
H19 H 1.4517 -0.1927 0.4211 0.044 Uiso 1 1 calc R U . . .
C20 C 1.3408(9) -0.0344(6) 0.4030(5) 0.0358(17) Uani 1 1 d . . . . .
N1 N 0.8124(7) 0.1472(4) 0.0613(4) 0.0322(13) Uani 1 1 d . . . . .
H1 H 0.8677 0.0825 0.0682 0.039 Uiso 1 1 calc R U . . .
N2 N 0.9323(7) 0.2351(4) 0.2176(4) 0.0304(13) Uani 1 1 d . . . . .
H2A H 1.0384 0.1958 0.2059 0.037 Uiso 1 1 calc R U . . .
H2B H 0.8545 0.1905 0.2411 0.037 Uiso 1 1 calc R U . . .
N3 N 1.0909(7) 0.1526(5) 0.3991(4) 0.0333(14) Uani 1 1 d . . . . .
H3 H 1.0694 0.0878 0.4107 0.040 Uiso 1 1 calc R U . . .
O1 O 0.2708(6) 0.1543(4) 0.1443(4) 0.0433(13) Uani 1 1 d . . . . .
O2 O 0.3026(7) -0.0205(5) 0.1637(4) 0.0499(15) Uani 1 1 d . . . . .
O3 O 0.8321(6) -0.0583(4) 0.0898(4) 0.0393(13) Uani 1 1 d . . . . .
O4 O 1.6264(6) 0.1662(5) 0.3123(4) 0.0514(15) Uani 1 1 d . . . . .
O5 O 1.6913(7) -0.0077(5) 0.3435(4) 0.0564(16) Uani 1 1 d . . . . .
O6 O 1.1842(6) -0.0539(4) 0.4283(4) 0.0440(13) Uani 1 1 d . . . . .
Br1A Br 0.19289(15) 0.50763(10) 0.12619(10) 0.0476(5) Uani 0.636(2) 1 d . . P A
1
Br1B Br 0.5388(13) 0.4840(9) 0.2299(9) 0.102(4) Uani 0.128(3) 1 d . . P B 2
Br1C Br 0.7820(11) -0.4071(7) 0.0899(8) 0.090(4) Uani 0.131(3) 1 d . . P C 3
Br1D Br 0.5000 0.5000 0.5000 0.098(4) Uani 0.211(4) 2 d S . P D 4
O1MA O 0.0124(19) 0.5346(13) 0.4123(12) 0.024(4) Uiso 0.25 1 d D . P E -1
H1MA H -0.0175 0.5230 0.3615 0.036 Uiso 0.25 1 calc R U P E -1
C1MA C 0.197(2) 0.540(3) 0.388(3) 0.062(10) Uiso 0.25 1 d D . P E -1
H1M1 H 0.2465 0.5117 0.4483 0.093 Uiso 0.25 1 calc R U P E -1
H1M2 H 0.2145 0.6133 0.3669 0.093 Uiso 0.25 1 calc R U P E -1
H1M3 H 0.2543 0.4983 0.3339 0.093 Uiso 0.25 1 calc R U P E -1
O1MB O 0.265(3) 0.5101(18) 0.4916(15) 0.046(5) Uiso 0.25 1 d D . P F -2
H1MB H 0.3534 0.5299 0.4543 0.069 Uiso 0.25 1 calc R U P F -2
C1MB C 0.117(4) 0.549(3) 0.442(3) 0.068(11) Uiso 0.25 1 d D . P F -2
H1M4 H 0.0191 0.5157 0.4797 0.102 Uiso 0.25 1 calc R U P F -2
H1M5 H 0.1475 0.5322 0.3731 0.102 Uiso 0.25 1 calc R U P F -2
H1M6 H 0.0874 0.6255 0.4406 0.102 Uiso 0.25 1 calc R U P F -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.224(9) . ?
C1 O2 1.390(9) . ?
C1 C6 1.402(9) . ?
C2 C4 1.294(10) . ?
C2 O2 1.389(10) . ?
C2 C3 1.497(10) . ?
C4 C5 1.462(9) . ?
C5 O3 1.242(8) . ?
C5 C6 1.448(10) . ?
C6 C7 1.449(9) . ?
C7 N1 1.301(8) . ?
C7 C8 1.475(10) . ?
C9 N1 1.473(8) . ?
C9 C10 1.500(9) . ?
C10 N2 1.477(8) . ?
C11 N2 1.498(8) . ?
C11 C12 1.526(10) . ?
C12 N3 1.475(9) . ?
C13 N3 1.322(8) . ?
C13 C15 1.415(10) . ?
C13 C14 1.494(10) . ?
C15 C20 1.424(10) . ?
C15 C16 1.433(9) . ?
C16 O4 1.223(9) . ?
C16 O5 1.366(10) . ?
C17 C19 1.348(11) . ?
C17 O5 1.374(11) . ?
C17 C18 1.485(12) . ?
C19 C20 1.418(10) . ?
C20 O6 1.273(8) . ?
O1MA C1MA 1.442(2) . ?
O1MB C1MB 1.443(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
O1 C1 O2 113.0(6) . . ?
O1 C1 C6 128.4(7) . . ?
O2 C1 C6 118.6(7) . . ?
C4 C2 O2 121.4(7) . . ?
C4 C2 C3 127.1(8) . . ?
O2 C2 C3 111.5(7) . . ?
C2 C4 C5 122.4(7) . . ?
O3 C5 C6 124.5(6) . . ?
O3 C5 C4 120.2(6) . . ?
C6 C5 C4 115.3(6) . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 C7 119.5(6) . . ?
C5 C6 C7 119.9(6) . . ?
N1 C7 C6 118.5(6) . . ?
N1 C7 C8 118.5(6) . . ?
C6 C7 C8 123.0(6) . . ?
N1 C9 C10 113.2(5) . . ?
N2 C10 C9 113.5(6) . . ?
N2 C11 C12 111.8(5) . . ?
N3 C12 C11 114.1(6) . . ?
N3 C13 C15 118.6(6) . . ?
N3 C13 C14 116.6(7) . . ?
C15 C13 C14 124.8(6) . . ?
C13 C15 C20 121.9(6) . . ?
C13 C15 C16 118.7(6) . . ?
C20 C15 C16 119.4(7) . . ?
O4 C16 O5 114.3(6) . . ?
O4 C16 C15 127.1(8) . . ?
O5 C16 C15 118.5(7) . . ?
C19 C17 O5 121.4(7) . . ?
C19 C17 C18 126.9(10) . . ?
O5 C17 C18 111.7(8) . . ?
C17 C19 C20 120.5(7) . . ?
O6 C20 C19 117.4(7) . . ?
O6 C20 C15 124.4(7) . . ?
C19 C20 C15 118.2(6) . . ?
C7 N1 C9 127.6(6) . . ?
C10 N2 C11 111.9(5) . . ?
C13 N3 C12 127.4(6) . . ?
C2 O2 C1 121.4(6) . . ?
C16 O5 C17 121.9(6) . . ?

_refine_diff_density_max         1.217
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.127

