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

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

data_CNX-L-Pro
_database_code_depnum_ccdc_archive 'CCDC 1850498'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-08-14 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         'C13 H11 Cl N2 O2, C5 H9 N O2'
_chemical_formula_sum            'C18 H20 Cl N3 O4'
_chemical_formula_weight         377.82

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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   5.7789(3)
_cell_length_b                   12.3293(7)
_cell_length_c                   24.9401(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1776.98(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.19

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.6492
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42221
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4100
_reflns_number_gt                3404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4100
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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
Cl1 Cl 1.52932(15) 0.79681(7) 0.25777(3) 0.0421(2) Uani 1 1 d . . . . .
O1 O 0.3820(3) 0.65443(16) 0.04789(8) 0.0296(5) Uani 1 1 d . . . . .
H1 H 0.3994 0.5873 0.0522 0.044 Uiso 1 1 d R U . . .
O2 O 0.7059(4) 0.66079(16) 0.09671(9) 0.0349(5) Uani 1 1 d . . . . .
N1 N 0.6160(4) 1.00512(18) 0.10662(10) 0.0279(5) Uani 1 1 d . . . . .
N2 N 0.8335(4) 0.85489(18) 0.13456(9) 0.0257(5) Uani 1 1 d . . . . .
H2A H 0.8547 0.7850 0.1297 0.031 Uiso 1 1 d R U . . .
C1 C 0.5041(5) 0.8257(2) 0.07712(10) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.6519(5) 0.8973(2) 0.10627(11) 0.0233(6) Uani 1 1 d . . . . .
C3 C 0.4310(6) 1.0431(2) 0.08073(13) 0.0306(7) Uani 1 1 d . . . . .
H3B H 0.4065 1.1193 0.0811 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2724(6) 0.9803(2) 0.05343(11) 0.0283(6) Uani 1 1 d . . . . .
H4A H 0.1408 1.0116 0.0367 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3131(5) 0.8700(2) 0.05147(11) 0.0263(6) Uani 1 1 d . . . . .
H5A H 0.2096 0.8242 0.0325 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5431(5) 0.7071(2) 0.07517(11) 0.0245(6) Uani 1 1 d . . . . .
C7 C 0.9913(5) 0.9028(2) 0.16993(10) 0.0235(6) Uani 1 1 d . . . . .
C8 C 1.1592(5) 0.8329(2) 0.19247(11) 0.0258(6) Uani 1 1 d . . . . .
C9 C 1.3196(6) 0.8784(2) 0.22729(11) 0.0297(6) Uani 1 1 d . . . . .
C10 C 1.3241(6) 0.9884(3) 0.24011(12) 0.0329(7) Uani 1 1 d . . . . .
H10A H 1.4391 1.0173 0.2633 0.039 Uiso 1 1 calc R U . . .
C11 C 1.1558(6) 1.0535(2) 0.21802(12) 0.0332(7) Uani 1 1 d . . . . .
H11A H 1.1539 1.1286 0.2266 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9894(6) 1.0128(2) 0.18362(11) 0.0300(6) Uani 1 1 d . . . . .
H12A H 0.8740 1.0595 0.1693 0.036 Uiso 1 1 calc R U . . .
C13 C 1.1582(6) 0.7140(2) 0.17859(13) 0.0341(7) Uani 1 1 d . . . . .
H13A H 1.0127 0.6813 0.1906 0.051 Uiso 1 1 calc R U . . .
H13B H 1.2884 0.6781 0.1964 0.051 Uiso 1 1 calc R U . . .
H13C H 1.1729 0.7054 0.1397 0.051 Uiso 1 1 calc R U . . .
O3 O 0.4294(3) 0.44738(15) 0.04949(9) 0.0275(5) Uani 1 1 d . . . . .
O4 O 0.2652(3) 0.28837(15) 0.03003(8) 0.0258(4) Uani 1 1 d . . . . .
N3 N -0.1561(4) 0.34488(17) 0.05905(9) 0.0210(5) Uani 1 1 d . . . . .
H3 H -0.1164 0.3019 0.0309 0.025 Uiso 1 1 d R U . . .
H3A H -0.2901 0.3798 0.0508 0.025 Uiso 1 1 d R U . . .
C14 C 0.0317(4) 0.4255(2) 0.06977(10) 0.0185(5) Uani 1 1 d . . . . .
H14A H -0.0076 0.4977 0.0540 0.022 Uiso 1 1 calc R U . . .
C15 C 0.0391(5) 0.4316(2) 0.13094(11) 0.0252(6) Uani 1 1 d . . . . .
H15A H -0.0839 0.4797 0.1450 0.030 Uiso 1 1 calc R U . . .
H15B H 0.1913 0.4579 0.1437 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0019(5) 0.3138(2) 0.14758(11) 0.0283(6) Uani 1 1 d . . . . .
H16A H 0.1405 0.2700 0.1434 0.034 Uiso 1 1 calc R U . . .
H16B H -0.0553 0.3092 0.1852 0.034 Uiso 1 1 calc R U . . .
C17 C -0.1897(6) 0.2766(2) 0.10889(12) 0.0305(6) Uani 1 1 d . . . . .
H17A H -0.1721 0.1985 0.1005 0.037 Uiso 1 1 calc R U . . .
H17B H -0.3453 0.2887 0.1244 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2593(4) 0.3827(2) 0.04695(10) 0.0188(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.749(3) . ?
O1 C6 1.324(3) . ?
O1 H1 0.8403 . ?
O2 C6 1.225(4) . ?
N1 C3 1.334(4) . ?
N1 C2 1.345(3) . ?
N2 C2 1.368(4) . ?
N2 C7 1.399(3) . ?
N2 H2A 0.8793 . ?
C1 C5 1.388(4) . ?
C1 C2 1.427(4) . ?
C1 C6 1.481(4) . ?
C3 C4 1.379(4) . ?
C3 H3B 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C7 C12 1.400(4) . ?
C7 C8 1.414(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.506(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.377(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O3 C18 1.268(3) . ?
O4 C18 1.237(3) . ?
N3 C14 1.496(3) . ?
N3 C17 1.514(4) . ?
N3 H3 0.9093 . ?
N3 H3A 0.9098 . ?
C14 C18 1.527(3) . ?
C14 C15 1.528(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.529(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 109.5 . . ?
C3 N1 C2 117.8(3) . . ?
C2 N2 C7 131.6(2) . . ?
C2 N2 H2A 114.3 . . ?
C7 N2 H2A 114.2 . . ?
C5 C1 C2 117.9(2) . . ?
C5 C1 C6 119.6(2) . . ?
C2 C1 C6 122.4(2) . . ?
N1 C2 N2 119.5(3) . . ?
N1 C2 C1 121.5(3) . . ?
N2 C2 C1 119.0(2) . . ?
N1 C3 C4 125.1(3) . . ?
N1 C3 H3B 117.5 . . ?
C4 C3 H3B 117.5 . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 H4A 121.4 . . ?
C5 C4 H4A 121.4 . . ?
C4 C5 C1 120.4(3) . . ?
C4 C5 H5A 119.8 . . ?
C1 C5 H5A 119.8 . . ?
O2 C6 O1 122.5(2) . . ?
O2 C6 C1 124.3(3) . . ?
O1 C6 C1 113.2(2) . . ?
N2 C7 C12 123.9(3) . . ?
N2 C7 C8 116.2(2) . . ?
C12 C7 C8 120.0(3) . . ?
C9 C8 C7 117.4(2) . . ?
C9 C8 C13 122.6(3) . . ?
C7 C8 C13 119.9(3) . . ?
C8 C9 C10 123.3(3) . . ?
C8 C9 Cl1 120.2(2) . . ?
C10 C9 Cl1 116.6(2) . . ?
C11 C10 C9 117.6(3) . . ?
C11 C10 H10A 121.2 . . ?
C9 C10 H10A 121.2 . . ?
C10 C11 C12 121.9(3) . . ?
C10 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
C11 C12 C7 119.8(3) . . ?
C11 C12 H12A 120.1 . . ?
C7 C12 H12A 120.1 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 N3 C17 108.4(2) . . ?
C14 N3 H3 110.0 . . ?
C17 N3 H3 110.0 . . ?
C14 N3 H3A 110.1 . . ?
C17 N3 H3A 109.9 . . ?
H3 N3 H3A 108.4 . . ?
N3 C14 C18 109.17(19) . . ?
N3 C14 C15 103.4(2) . . ?
C18 C14 C15 111.4(2) . . ?
N3 C14 H14A 110.9 . . ?
C18 C14 H14A 110.9 . . ?
C15 C14 H14A 110.9 . . ?
C14 C15 C16 102.7(2) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 C15 103.0(2) . . ?
C17 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
N3 C17 C16 105.1(2) . . ?
N3 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
N3 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
O4 C18 O3 125.9(2) . . ?
O4 C18 C14 118.4(2) . . ?
O3 C18 C14 115.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 N2 -176.8(3) . . . . ?
C3 N1 C2 C1 3.0(4) . . . . ?
C7 N2 C2 N1 6.3(4) . . . . ?
C7 N2 C2 C1 -173.5(3) . . . . ?
C5 C1 C2 N1 -3.7(4) . . . . ?
C6 C1 C2 N1 178.6(3) . . . . ?
C5 C1 C2 N2 176.1(2) . . . . ?
C6 C1 C2 N2 -1.6(4) . . . . ?
C2 N1 C3 C4 0.0(5) . . . . ?
N1 C3 C4 C5 -2.1(5) . . . . ?
C3 C4 C5 C1 1.2(4) . . . . ?
C2 C1 C5 C4 1.5(4) . . . . ?
C6 C1 C5 C4 179.2(3) . . . . ?
C5 C1 C6 O2 -179.7(3) . . . . ?
C2 C1 C6 O2 -2.1(4) . . . . ?
C5 C1 C6 O1 -0.2(4) . . . . ?
C2 C1 C6 O1 177.4(2) . . . . ?
C2 N2 C7 C12 0.1(5) . . . . ?
C2 N2 C7 C8 179.8(3) . . . . ?
N2 C7 C8 C9 179.4(3) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
N2 C7 C8 C13 -1.0(4) . . . . ?
C12 C7 C8 C13 178.8(3) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C13 C8 C9 C10 179.4(3) . . . . ?
C7 C8 C9 Cl1 178.8(2) . . . . ?
C13 C8 C9 Cl1 -0.9(4) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
Cl1 C9 C10 C11 -177.8(2) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
N2 C7 C12 C11 -178.5(3) . . . . ?
C8 C7 C12 C11 1.8(4) . . . . ?
C17 N3 C14 C18 97.7(2) . . . . ?
C17 N3 C14 C15 -21.0(3) . . . . ?
N3 C14 C15 C16 38.2(3) . . . . ?
C18 C14 C15 C16 -79.0(3) . . . . ?
C14 C15 C16 C17 -41.1(3) . . . . ?
C14 N3 C17 C16 -4.5(3) . . . . ?
C15 C16 C17 N3 28.1(3) . . . . ?
N3 C14 C18 O4 -8.5(3) . . . . ?
C15 C14 C18 O4 105.0(3) . . . . ?
N3 C14 C18 O3 174.5(2) . . . . ?
C15 C14 C18 O3 -72.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.84 1.74 2.568(3) 170.4 .
N2 H2A O2 0.88 1.94 2.676(3) 140.4 .
N3 H3 O4 0.91 2.00 2.800(3) 145.4 3_455
N3 H3A O3 0.91 1.82 2.719(3) 167.8 1_455
C12 H12A N1 0.95 2.26 2.890(4) 122.9 .
C13 H13B Cl1 0.98 2.53 3.089(3) 115.7 .
C11 H11A Cl1 0.95 2.79 3.560(3) 138.3 4_855
C3 H3B O4 0.95 2.58 3.415(4) 147.4 1_565
C4 H4A O3 0.95 2.52 3.363(4) 147.6 3_465

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_CLX-L-Pro
_database_code_depnum_ccdc_archive 'CCDC 1850500'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-08-14 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         'C17 H14 F3 N3 O2 S, 2(C5 H9 N O2)'
_chemical_formula_sum            'C27 H32 F3 N5 O6 S'
_chemical_formula_weight         611.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'

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

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

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

_cell_length_a                   9.5641(7)
_cell_length_b                   20.0364(10)
_cell_length_c                   30.4887(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5842.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4627
_cell_measurement_theta_min      3.2110
_cell_measurement_theta_max      21.7540

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_T_min  0.78811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            28262
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_full        25.194
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10336
_reflns_number_gt                6750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.07(13)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         10336
_refine_ls_number_parameters     796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.006
_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
S1 S 0.12336(17) 0.62952(8) 0.62865(5) 0.0394(4) Uani 1 1 d . . . . .
S2 S 0.64644(18) 0.60974(8) 0.61220(6) 0.0465(5) Uani 1 1 d . . . . .
O1 O 0.2722(4) 0.6284(2) 0.62687(15) 0.0598(14) Uani 1 1 d . . . . .
O2 O 0.0510(5) 0.5735(2) 0.64753(15) 0.0554(13) Uani 1 1 d . . . . .
O3 O 0.6272(5) 0.6700(2) 0.63669(15) 0.0599(13) Uani 1 1 d . . . . .
O4 O 0.7738(5) 0.5991(3) 0.58788(17) 0.0643(14) Uani 1 1 d . . . . .
O5 O 0.6403(5) 0.2129(2) 0.48156(16) 0.0572(13) Uani 1 1 d . . . . .
O6 O 0.8672(4) 0.18815(19) 0.48290(15) 0.0493(12) Uani 1 1 d . . . . .
O7 O 0.7393(5) 0.4459(2) 0.49026(14) 0.0490(12) Uani 1 1 d . . . . .
O8 O 0.5644(4) 0.4826(2) 0.53299(15) 0.0445(11) Uani 1 1 d . . . . .
O9 O 0.0626(5) 0.5306(3) 0.46955(18) 0.0708(16) Uani 1 1 d . . . . .
O10 O 0.2712(5) 0.5490(2) 0.49903(18) 0.0645(14) Uani 1 1 d . . . . .
O11 O 0.3804(4) 0.80786(19) 0.50954(14) 0.0439(11) Uani 1 1 d . . . . .
O12 O 0.1859(5) 0.7622(2) 0.53605(15) 0.0553(13) Uani 1 1 d . . . . .
N1 N 0.0682(6) 0.6386(3) 0.57944(17) 0.0376(13) Uani 1 1 d . . . . .
H1A H -0.036(7) 0.630(3) 0.580(2) 0.06(2) Uiso 1 1 d . . . . .
H1B H 0.104(5) 0.672(3) 0.5650(16) 0.016(15) Uiso 1 1 d . . . . .
N2 N -0.0089(5) 0.8756(2) 0.72947(18) 0.0429(13) Uani 1 1 d . . . . .
N3 N 0.0247(6) 0.9341(3) 0.70953(18) 0.0503(15) Uani 1 1 d . . . . .
N4 N 0.5202(5) 0.6047(3) 0.57797(16) 0.0440(14) Uani 1 1 d . . . . .
H4A H 0.4577 0.6356 0.5771 0.053 Uiso 1 1 d R U . . .
H4B H 0.5149 0.5713 0.5604 0.053 Uiso 1 1 d R U . . .
N5 N 0.5761(5) 0.3779(2) 0.73247(18) 0.0396(13) Uani 1 1 d . . . . .
N6 N 0.6081(6) 0.3177(3) 0.71474(17) 0.0444(14) Uani 1 1 d . . . . .
N7 N 0.6640(5) 0.3260(2) 0.52690(15) 0.0323(12) Uani 1 1 d . . . . .
H7B H 0.6048 0.3001 0.5160 0.039 Uiso 1 1 d R U . . .
H7C H 0.6698 0.3641 0.5140 0.039 Uiso 1 1 d R U . . .
N8 N 0.7948(5) 0.5710(2) 0.45983(15) 0.0321(12) Uani 1 1 d . . . . .
H8B H 0.8522 0.5401 0.4679 0.039 Uiso 1 1 d R U . . .
H8C H 0.8202 0.6071 0.4719 0.039 Uiso 1 1 d R U . . .
N9 N 0.2845(5) 0.4342(2) 0.54162(15) 0.0319(12) Uani 1 1 d . . . . .
H9B H 0.3409 0.4638 0.5350 0.038 Uiso 1 1 d R U . . .
H9C H 0.3199 0.3928 0.5329 0.038 Uiso 1 1 d R U . . .
N10 N 0.1661(5) 0.6722(2) 0.46971(15) 0.0342(12) Uani 1 1 d . . . . .
H10B H 0.1944 0.6309 0.4790 0.041 Uiso 1 1 d R U . . .
H10C H 0.0974 0.6869 0.4890 0.041 Uiso 1 1 d R U . . .
C1 C 0.0797(6) 0.7022(3) 0.65903(19) 0.0326(15) Uani 1 1 d . . . . .
C2 C 0.1731(7) 0.7547(3) 0.6584(2) 0.0455(17) Uani 1 1 d . . . . .
H2A H 0.2554 0.7517 0.6422 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1425(7) 0.8117(3) 0.6820(2) 0.0463(17) Uani 1 1 d . . . . .
H3A H 0.2045 0.8475 0.6821 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0192(6) 0.8151(3) 0.70555(19) 0.0338(15) Uani 1 1 d . . . . .
C5 C -0.0742(6) 0.7626(3) 0.70607(19) 0.0365(15) Uani 1 1 d . . . . .
H5A H -0.1572 0.7655 0.7219 0.044 Uiso 1 1 calc R U . . .
C6 C -0.0418(6) 0.7057(3) 0.68270(19) 0.0357(15) Uani 1 1 d . . . . .
H6A H -0.1028 0.6695 0.6830 0.043 Uiso 1 1 calc R U . . .
C7 C -0.0727(6) 0.8847(3) 0.7696(2) 0.0396(16) Uani 1 1 d . . . . .
C8 C -0.0816(7) 0.9528(3) 0.7750(2) 0.0459(17) Uani 1 1 d . . . . .
H8A H -0.1201 0.9757 0.7986 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0204(8) 0.9800(3) 0.7374(2) 0.0518(19) Uani 1 1 d . . . . .
C10 C 0.0007(12) 1.0513(4) 0.7269(3) 0.074(2) Uani 1 1 d . . . . .
C11 C -0.1098(7) 0.8291(3) 0.79913(19) 0.0377(15) Uani 1 1 d . . . . .
C12 C -0.2376(7) 0.8253(4) 0.8178(2) 0.0470(17) Uani 1 1 d . . . . .
H12A H -0.3046 0.8572 0.8107 0.056 Uiso 1 1 calc R U . . .
C13 C -0.0092(7) 0.7813(3) 0.8100(2) 0.0443(17) Uani 1 1 d . . . . .
H13A H 0.0795 0.7832 0.7976 0.053 Uiso 1 1 calc R U . . .
C14 C -0.0419(8) 0.7319(4) 0.8390(2) 0.0520(19) Uani 1 1 d . . . . .
H14A H 0.0259 0.7003 0.8460 0.062 Uiso 1 1 calc R U . . .
C15 C -0.2713(8) 0.7752(4) 0.8470(2) 0.060(2) Uani 1 1 d . . . . .
H15A H -0.3603 0.7736 0.8592 0.072 Uiso 1 1 calc R U . . .
C16 C -0.1724(9) 0.7270(4) 0.8584(2) 0.0529(19) Uani 1 1 d . . . . .
C17 C -0.2068(12) 0.6727(5) 0.8916(3) 0.108(4) Uani 1 1 d . . . . .
H17A H -0.3055 0.6727 0.8973 0.162 Uiso 1 1 calc R U . . .
H17B H -0.1571 0.6811 0.9184 0.162 Uiso 1 1 calc R U . . .
H17C H -0.1794 0.6301 0.8801 0.162 Uiso 1 1 calc R U . . .
C18 C 0.6308(6) 0.5418(3) 0.64894(18) 0.0346(14) Uani 1 1 d . . . . .
C19 C 0.5120(6) 0.5377(3) 0.67515(19) 0.0363(15) Uani 1 1 d . . . . .
H19A H 0.4451 0.5713 0.6742 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4938(6) 0.4840(3) 0.7024(2) 0.0384(16) Uani 1 1 d . . . . .
H20A H 0.4128 0.4801 0.7191 0.046 Uiso 1 1 calc R U . . .
C21 C 0.5972(6) 0.4353(3) 0.70490(19) 0.0346(15) Uani 1 1 d . . . . .
C22 C 0.7164(7) 0.4402(3) 0.6798(2) 0.0466(17) Uani 1 1 d . . . . .
H22A H 0.7855 0.4077 0.6818 0.056 Uiso 1 1 calc R U . . .
C23 C 0.7323(7) 0.4935(3) 0.6517(2) 0.0456(17) Uani 1 1 d . . . . .
H23A H 0.8124 0.4968 0.6346 0.055 Uiso 1 1 calc R U . . .
C24 C 0.5101(7) 0.3724(3) 0.7722(2) 0.0390(15) Uani 1 1 d . . . . .
C25 C 0.5011(7) 0.3047(3) 0.7803(2) 0.0459(17) Uani 1 1 d . . . . .
H25A H 0.4635 0.2838 0.8048 0.055 Uiso 1 1 calc R U . . .
C26 C 0.5610(7) 0.2747(3) 0.7435(2) 0.0466(18) Uani 1 1 d . . . . .
C27 C 0.5801(12) 0.2008(4) 0.7355(4) 0.069(2) Uani 1 1 d . . . . .
C28 C 0.4729(7) 0.4292(3) 0.8000(2) 0.0422(16) Uani 1 1 d . . . . .
C29 C 0.5625(8) 0.4819(4) 0.8073(2) 0.0537(19) Uani 1 1 d . . . . .
H29A H 0.6490 0.4830 0.7933 0.064 Uiso 1 1 calc R U . . .
C30 C 0.3445(9) 0.4298(4) 0.8209(2) 0.060(2) Uani 1 1 d . . . . .
H30A H 0.2823 0.3949 0.8162 0.072 Uiso 1 1 calc R U . . .
C31 C 0.3074(10) 0.4809(4) 0.8484(3) 0.072(2) Uani 1 1 d . . . . .
H31A H 0.2208 0.4800 0.8622 0.086 Uiso 1 1 calc R U . . .
C32 C 0.5249(11) 0.5328(4) 0.8350(3) 0.069(2) Uani 1 1 d . . . . .
H32A H 0.5873 0.5676 0.8397 0.082 Uiso 1 1 calc R U . . .
C33 C 0.3974(12) 0.5338(4) 0.8560(2) 0.078(3) Uani 1 1 d . . . . .
C34 C 0.3639(13) 0.5925(4) 0.8871(2) 0.100(4) Uani 1 1 d . . . . .
H34A H 0.4343 0.5952 0.9095 0.150 Uiso 1 1 calc R U . . .
H34B H 0.2742 0.5855 0.9005 0.150 Uiso 1 1 calc R U . . .
H34C H 0.3624 0.6334 0.8707 0.150 Uiso 1 1 calc R U . . .
C35 C 0.7641(6) 0.2236(3) 0.4920(2) 0.0348(15) Uani 1 1 d . . . . .
C36 C 0.7943(6) 0.2827(3) 0.5215(2) 0.0311(14) Uani 1 1 d . . . . .
H36A H 0.8695 0.3096 0.5086 0.037 Uiso 1 1 calc R U . . .
C37 C 0.8335(7) 0.2634(4) 0.5682(2) 0.0498(18) Uani 1 1 d . . . . .
H37A H 0.8175 0.2162 0.5729 0.060 Uiso 1 1 calc R U . A 1
H37B H 0.9314 0.2729 0.5737 0.060 Uiso 1 1 calc R U . A 1
C38 C 0.7481(13) 0.3016(8) 0.5964(3) 0.167(7) Uani 1 1 d . . . B 1
H38A H 0.8048 0.3359 0.6101 0.200 Uiso 1 1 calc R U . B 1
H38B H 0.7124 0.2730 0.6194 0.200 Uiso 1 1 calc R U . B 1
C39 C 0.6354(7) 0.3320(4) 0.5751(2) 0.0496(17) Uani 1 1 d . . . . .
H39A H 0.6282 0.3785 0.5835 0.060 Uiso 1 1 calc R U . B 1
H39B H 0.5486 0.3097 0.5826 0.060 Uiso 1 1 calc R U . B 1
C40 C 0.6539(6) 0.4890(3) 0.5026(2) 0.0353(14) Uani 1 1 d . . . . .
C41 C 0.6524(6) 0.5550(3) 0.4785(2) 0.0374(15) Uani 1 1 d . . . . .
H41A H 0.6214 0.5909 0.4981 0.045 Uiso 1 1 calc R U . . .
C42 C 0.5605(7) 0.5522(5) 0.4382(2) 0.070(2) Uani 1 1 d . . . . .
H42A H 0.4909 0.5173 0.4411 0.084 Uiso 1 1 calc R U . C 1
H42B H 0.5130 0.5945 0.4338 0.084 Uiso 1 1 calc R U . C 1
C43 C 0.6542(10) 0.5381(5) 0.4019(2) 0.090(3) Uani 1 1 d . . . D 1
H43A H 0.6704 0.4905 0.3994 0.108 Uiso 1 1 calc R U . D 1
H43B H 0.6146 0.5541 0.3746 0.108 Uiso 1 1 calc R U . D 1
C44 C 0.7858(7) 0.5733(4) 0.4117(2) 0.0500(18) Uani 1 1 d . . . . .
H44A H 0.8649 0.5508 0.3983 0.060 Uiso 1 1 calc R U . D 1
H44B H 0.7827 0.6190 0.4013 0.060 Uiso 1 1 calc R U . D 1
C45 C 0.1626(9) 0.5150(3) 0.4937(2) 0.0506(19) Uani 1 1 d . . . . .
C46 C 0.1519(6) 0.4501(3) 0.51841(18) 0.0319(14) Uani 1 1 d . . . . .
H46A H 0.1297 0.4140 0.4979 0.038 Uiso 1 1 calc R U . . .
C47 C 0.0406(6) 0.4526(3) 0.55451(19) 0.0384(15) Uani 1 1 d . . . . .
H47A H 0.0143 0.4983 0.5607 0.046 Uiso 1 1 calc R U . . .
H47B H -0.0422 0.4281 0.5457 0.046 Uiso 1 1 calc R U . . .
C48 C 0.1065(6) 0.4208(3) 0.5942(2) 0.0426(17) Uani 1 1 d . . . . .
H48A H 0.0962 0.3726 0.5936 0.051 Uiso 1 1 calc R U . . .
H48B H 0.0661 0.4380 0.6211 0.051 Uiso 1 1 calc R U . . .
C49 C 0.2577(7) 0.4410(3) 0.5897(2) 0.0448(17) Uani 1 1 d . . . . .
H49A H 0.2720 0.4865 0.5995 0.054 Uiso 1 1 calc R U . . .
H49B H 0.3181 0.4116 0.6065 0.054 Uiso 1 1 calc R U . . .
C50 C 0.2866(7) 0.7633(3) 0.5104(2) 0.0380(16) Uani 1 1 d . . . . .
C51 C 0.3036(6) 0.7072(3) 0.47744(19) 0.0316(14) Uani 1 1 d . . . . .
H51A H 0.3705 0.6748 0.4892 0.038 Uiso 1 1 calc R U . . .
C52 C 0.3511(6) 0.7275(3) 0.43176(19) 0.0380(15) Uani 1 1 d . . . . .
H52A H 0.3299 0.7741 0.4263 0.046 Uiso 1 1 calc R U . . .
H52B H 0.4511 0.7208 0.4285 0.046 Uiso 1 1 calc R U . . .
C53 C 0.2711(6) 0.6830(3) 0.40037(19) 0.0403(16) Uani 1 1 d . . . . .
H53A H 0.2633 0.7032 0.3716 0.048 Uiso 1 1 calc R U . . .
H53B H 0.3152 0.6396 0.3976 0.048 Uiso 1 1 calc R U . . .
C54 C 0.1312(7) 0.6776(3) 0.42219(19) 0.0432(16) Uani 1 1 d . . . . .
H54A H 0.0748 0.7168 0.4164 0.052 Uiso 1 1 calc R U . . .
H54B H 0.0812 0.6383 0.4122 0.052 Uiso 1 1 calc R U . . .
F1 F -0.0924(7) 1.0902(2) 0.7437(2) 0.114(2) Uani 1 1 d . . . . .
F2 F 0.1189(7) 1.0746(2) 0.7443(3) 0.137(3) Uani 1 1 d . . . . .
F3 F 0.0088(11) 1.0628(2) 0.68493(19) 0.166(4) Uani 1 1 d . . . . .
F4 F 0.634(2) 0.1694(5) 0.7684(5) 0.083(6) Uani 0.66(4) 1 d . . P E 1
F5 F 0.455(2) 0.1714(10) 0.7323(12) 0.144(13) Uani 0.66(4) 1 d . . P E 1
F6 F 0.652(4) 0.1874(5) 0.7013(6) 0.122(11) Uani 0.66(4) 1 d . . P E 1
F4A F 0.703(4) 0.184(2) 0.737(4) 0.20(4) Uani 0.34(4) 1 d . . P E 2
F5A F 0.500(11) 0.1666(16) 0.757(3) 0.26(5) Uani 0.34(4) 1 d . . P E 2
F6A F 0.525(7) 0.1854(16) 0.6980(17) 0.14(2) Uani 0.34(4) 1 d . . P E 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
S1 O1 1.425(4) . ?
S1 O2 1.438(5) . ?
S1 N1 1.601(6) . ?
S1 C1 1.776(6) . ?
S2 O3 1.432(5) . ?
S2 O4 1.442(5) . ?
S2 N4 1.599(5) . ?
S2 C18 1.769(6) . ?
O5 C35 1.245(7) . ?
O6 C35 1.247(7) . ?
O7 C40 1.248(7) . ?
O8 C40 1.268(7) . ?
O9 C45 1.247(8) . ?
O10 C45 1.252(9) . ?
O11 C50 1.265(7) . ?
O12 C50 1.241(7) . ?
N1 H1A 1.01(7) . ?
N1 H1B 0.86(5) . ?
N2 N3 1.359(7) . ?
N2 C7 1.379(8) . ?
N2 C4 1.441(7) . ?
N3 C9 1.324(8) . ?
N4 H4A 0.8610 . ?
N4 H4B 0.8595 . ?
N5 N6 1.356(7) . ?
N5 C24 1.371(8) . ?
N5 C21 1.440(7) . ?
N6 C26 1.309(8) . ?
N7 C39 1.499(7) . ?
N7 C36 1.527(7) . ?
N7 H7B 0.8371 . ?
N7 H7C 0.8608 . ?
N8 C44 1.471(7) . ?
N8 C41 1.510(7) . ?
N8 H8B 0.8635 . ?
N8 H8C 0.8474 . ?
N9 C46 1.486(7) . ?
N9 C49 1.495(7) . ?
N9 H9B 0.8271 . ?
N9 H9C 0.9342 . ?
N10 C54 1.490(7) . ?
N10 C51 1.509(7) . ?
N10 H10B 0.9156 . ?
N10 H10C 0.9298 . ?
C1 C6 1.370(8) . ?
C1 C2 1.380(8) . ?
C2 C3 1.382(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(8) . ?
C5 C6 1.380(8) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.376(9) . ?
C7 C11 1.476(9) . ?
C8 C9 1.398(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.476(10) . ?
C10 F1 1.289(10) . ?
C10 F3 1.304(9) . ?
C10 F2 1.333(11) . ?
C11 C12 1.350(9) . ?
C11 C13 1.398(9) . ?
C12 C15 1.380(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.363(9) . ?
C13 H13A 0.9300 . ?
C14 C16 1.384(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.397(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.522(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.373(9) . ?
C18 C19 1.392(8) . ?
C19 C20 1.370(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.391(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.376(8) . ?
C22 C23 1.377(9) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C25 1.381(8) . ?
C24 C28 1.463(9) . ?
C25 C26 1.396(9) . ?
C25 H25A 0.9300 . ?
C26 C27 1.511(11) . ?
C27 F5A 1.22(4) . ?
C27 F6 1.280(16) . ?
C27 F4A 1.22(3) . ?
C27 F6A 1.30(3) . ?
C27 F4 1.291(15) . ?
C27 F5 1.34(2) . ?
C28 C29 1.378(9) . ?
C28 C30 1.383(10) . ?
C29 C32 1.372(10) . ?
C29 H29A 0.9300 . ?
C30 C31 1.370(10) . ?
C30 H30A 0.9300 . ?
C31 C33 1.384(12) . ?
C31 H31A 0.9300 . ?
C32 C33 1.377(12) . ?
C32 H32A 0.9300 . ?
C33 C34 1.546(10) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.514(8) . ?
C36 C37 1.524(8) . ?
C36 H36A 0.9800 . ?
C37 C38 1.411(10) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.398(11) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.513(8) . ?
C41 C42 1.512(9) . ?
C41 H41A 0.9800 . ?
C42 C43 1.452(11) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.473(10) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.507(8) . ?
C46 C47 1.532(8) . ?
C46 H46A 0.9800 . ?
C47 C48 1.505(8) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.507(8) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.517(8) . ?
C51 C52 1.520(8) . ?
C51 H51A 0.9800 . ?
C52 C53 1.516(8) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.498(8) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?

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 S1 O2 118.9(3) . . ?
O1 S1 N1 107.2(3) . . ?
O2 S1 N1 107.8(3) . . ?
O1 S1 C1 105.5(3) . . ?
O2 S1 C1 108.5(3) . . ?
N1 S1 C1 108.5(3) . . ?
O3 S2 O4 120.1(3) . . ?
O3 S2 N4 107.2(3) . . ?
O4 S2 N4 107.0(3) . . ?
O3 S2 C18 108.0(3) . . ?
O4 S2 C18 106.4(3) . . ?
N4 S2 C18 107.5(3) . . ?
S1 N1 H1A 107(4) . . ?
S1 N1 H1B 116(3) . . ?
H1A N1 H1B 122(5) . . ?
N3 N2 C7 112.8(5) . . ?
N3 N2 C4 117.1(5) . . ?
C7 N2 C4 130.0(5) . . ?
C9 N3 N2 103.6(5) . . ?
S2 N4 H4A 120.0 . . ?
S2 N4 H4B 120.1 . . ?
H4A N4 H4B 119.9 . . ?
N6 N5 C24 112.7(5) . . ?
N6 N5 C21 116.5(5) . . ?
C24 N5 C21 130.1(5) . . ?
C26 N6 N5 103.9(5) . . ?
C39 N7 C36 107.5(4) . . ?
C39 N7 H7B 108.4 . . ?
C36 N7 H7B 99.0 . . ?
C39 N7 H7C 112.9 . . ?
C36 N7 H7C 113.6 . . ?
H7B N7 H7C 114.3 . . ?
C44 N8 C41 109.3(5) . . ?
C44 N8 H8B 110.2 . . ?
C41 N8 H8B 108.3 . . ?
C44 N8 H8C 115.1 . . ?
C41 N8 H8C 106.0 . . ?
H8B N8 H8C 107.8 . . ?
C46 N9 C49 107.6(4) . . ?
C46 N9 H9B 106.6 . . ?
C49 N9 H9B 106.7 . . ?
C46 N9 H9C 111.3 . . ?
C49 N9 H9C 114.8 . . ?
H9B N9 H9C 109.3 . . ?
C54 N10 C51 108.3(4) . . ?
C54 N10 H10B 115.6 . . ?
C51 N10 H10B 96.5 . . ?
C54 N10 H10C 115.7 . . ?
C51 N10 H10C 111.7 . . ?
H10B N10 H10C 107.4 . . ?
C6 C1 C2 121.2(6) . . ?
C6 C1 S1 121.0(5) . . ?
C2 C1 S1 117.7(5) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 N2 117.6(5) . . ?
C5 C4 N2 121.0(5) . . ?
C6 C5 C4 118.6(6) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C1 C6 C5 120.3(6) . . ?
C1 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
N2 C7 C8 105.3(6) . . ?
N2 C7 C11 123.2(6) . . ?
C8 C7 C11 131.3(6) . . ?
C7 C8 C9 105.3(6) . . ?
C7 C8 H8A 127.4 . . ?
C9 C8 H8A 127.4 . . ?
N3 C9 C8 113.0(6) . . ?
N3 C9 C10 119.3(7) . . ?
C8 C9 C10 127.7(7) . . ?
F1 C10 F3 108.8(8) . . ?
F1 C10 F2 102.5(7) . . ?
F3 C10 F2 106.1(9) . . ?
F1 C10 C9 113.9(8) . . ?
F3 C10 C9 113.0(7) . . ?
F2 C10 C9 111.7(8) . . ?
C12 C11 C13 118.9(6) . . ?
C12 C11 C7 121.1(6) . . ?
C13 C11 C7 119.8(6) . . ?
C11 C12 C15 121.6(7) . . ?
C11 C12 H12A 119.2 . . ?
C15 C12 H12A 119.2 . . ?
C14 C13 C11 119.6(7) . . ?
C14 C13 H13A 120.2 . . ?
C11 C13 H13A 120.2 . . ?
C13 C14 C16 122.3(7) . . ?
C13 C14 H14A 118.8 . . ?
C16 C14 H14A 118.8 . . ?
C12 C15 C16 120.4(7) . . ?
C12 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C14 C16 C15 117.1(7) . . ?
C14 C16 C17 122.0(8) . . ?
C15 C16 C17 120.9(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 120.0(6) . . ?
C23 C18 S2 121.5(5) . . ?
C19 C18 S2 118.6(5) . . ?
C20 C19 C18 120.0(6) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C19 C20 C21 119.5(6) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C22 C21 C20 120.6(6) . . ?
C22 C21 N5 119.8(5) . . ?
C20 C21 N5 119.5(5) . . ?
C21 C22 C23 119.5(6) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C18 C23 C22 120.4(6) . . ?
C18 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
N5 C24 C25 105.3(6) . . ?
N5 C24 C28 124.2(5) . . ?
C25 C24 C28 130.2(6) . . ?
C24 C25 C26 104.8(6) . . ?
C24 C25 H25A 127.6 . . ?
C26 C25 H25A 127.6 . . ?
N6 C26 C25 113.3(6) . . ?
N6 C26 C27 119.7(7) . . ?
C25 C26 C27 127.0(7) . . ?
F5A C27 F4A 116(4) . . ?
F5A C27 F6A 95(4) . . ?
F4A C27 F6A 110(3) . . ?
F6 C27 F4 108.2(13) . . ?
F6 C27 F5 109.3(18) . . ?
F4 C27 F5 101.6(15) . . ?
F5A C27 C26 112.9(18) . . ?
F6 C27 C26 113.7(9) . . ?
F4A C27 C26 112.7(17) . . ?
F6A C27 C26 109.0(16) . . ?
F4 C27 C26 113.6(9) . . ?
F5 C27 C26 109.6(12) . . ?
C29 C28 C30 118.1(7) . . ?
C29 C28 C24 122.5(6) . . ?
C30 C28 C24 119.3(6) . . ?
C32 C29 C28 120.3(8) . . ?
C32 C29 H29A 119.8 . . ?
C28 C29 H29A 119.8 . . ?
C31 C30 C28 121.2(8) . . ?
C31 C30 H30A 119.4 . . ?
C28 C30 H30A 119.4 . . ?
C30 C31 C33 120.8(8) . . ?
C30 C31 H31A 119.6 . . ?
C33 C31 H31A 119.6 . . ?
C29 C32 C33 122.0(8) . . ?
C29 C32 H32A 119.0 . . ?
C33 C32 H32A 119.0 . . ?
C32 C33 C31 117.5(8) . . ?
C32 C33 C34 118.7(9) . . ?
C31 C33 C34 123.8(9) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O5 C35 O6 126.6(6) . . ?
O5 C35 C36 117.9(5) . . ?
O6 C35 C36 115.3(5) . . ?
N7 C36 C35 110.7(5) . . ?
N7 C36 C37 104.1(5) . . ?
C35 C36 C37 113.8(5) . . ?
N7 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C37 C36 H36A 109.4 . . ?
C38 C37 C36 106.8(6) . . ?
C38 C37 H37A 110.4 . . ?
C36 C37 H37A 110.4 . . ?
C38 C37 H37B 110.4 . . ?
C36 C37 H37B 110.4 . . ?
H37A C37 H37B 108.6 . . ?
C37 C38 C39 113.5(7) . . ?
C37 C38 H38A 108.9 . . ?
C39 C38 H38A 108.9 . . ?
C37 C38 H38B 108.9 . . ?
C39 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 N7 106.3(6) . . ?
C38 C39 H39A 110.5 . . ?
N7 C39 H39A 110.5 . . ?
C38 C39 H39B 110.5 . . ?
N7 C39 H39B 110.5 . . ?
H39A C39 H39B 108.7 . . ?
O7 C40 O8 126.3(6) . . ?
O7 C40 C41 117.7(6) . . ?
O8 C40 C41 116.0(6) . . ?
C40 C41 C42 111.6(6) . . ?
C40 C41 N8 111.1(5) . . ?
C42 C41 N8 103.1(5) . . ?
C40 C41 H41A 110.3 . . ?
C42 C41 H41A 110.3 . . ?
N8 C41 H41A 110.3 . . ?
C43 C42 C41 105.5(6) . . ?
C43 C42 H42A 110.6 . . ?
C41 C42 H42A 110.6 . . ?
C43 C42 H42B 110.6 . . ?
C41 C42 H42B 110.6 . . ?
H42A C42 H42B 108.8 . . ?
C44 C43 C42 106.3(7) . . ?
C44 C43 H43A 110.5 . . ?
C42 C43 H43A 110.5 . . ?
C44 C43 H43B 110.5 . . ?
C42 C43 H43B 110.5 . . ?
H43A C43 H43B 108.7 . . ?
N8 C44 C43 103.7(6) . . ?
N8 C44 H44A 111.0 . . ?
C43 C44 H44A 111.0 . . ?
N8 C44 H44B 111.0 . . ?
C43 C44 H44B 111.0 . . ?
H44A C44 H44B 109.0 . . ?
O9 C45 O10 125.2(7) . . ?
O9 C45 C46 117.3(7) . . ?
O10 C45 C46 117.4(7) . . ?
N9 C46 C45 111.4(5) . . ?
N9 C46 C47 104.9(4) . . ?
C45 C46 C47 112.3(5) . . ?
N9 C46 H46A 109.4 . . ?
C45 C46 H46A 109.4 . . ?
C47 C46 H46A 109.4 . . ?
C48 C47 C46 105.8(5) . . ?
C48 C47 H47A 110.6 . . ?
C46 C47 H47A 110.6 . . ?
C48 C47 H47B 110.6 . . ?
C46 C47 H47B 110.6 . . ?
H47A C47 H47B 108.7 . . ?
C47 C48 C49 102.5(5) . . ?
C47 C48 H48A 111.3 . . ?
C49 C48 H48A 111.3 . . ?
C47 C48 H48B 111.3 . . ?
C49 C48 H48B 111.3 . . ?
H48A C48 H48B 109.2 . . ?
N9 C49 C48 103.2(5) . . ?
N9 C49 H49A 111.1 . . ?
C48 C49 H49A 111.1 . . ?
N9 C49 H49B 111.1 . . ?
C48 C49 H49B 111.1 . . ?
H49A C49 H49B 109.1 . . ?
O12 C50 O11 125.2(6) . . ?
O12 C50 C51 119.1(5) . . ?
O11 C50 C51 115.7(6) . . ?
N10 C51 C50 110.8(5) . . ?
N10 C51 C52 104.0(4) . . ?
C50 C51 C52 116.2(5) . . ?
N10 C51 H51A 108.6 . . ?
C50 C51 H51A 108.6 . . ?
C52 C51 H51A 108.6 . . ?
C53 C52 C51 105.7(5) . . ?
C53 C52 H52A 110.6 . . ?
C51 C52 H52A 110.6 . . ?
C53 C52 H52B 110.6 . . ?
C51 C52 H52B 110.6 . . ?
H52A C52 H52B 108.7 . . ?
C54 C53 C52 102.3(5) . . ?
C54 C53 H53A 111.3 . . ?
C52 C53 H53A 111.3 . . ?
C54 C53 H53B 111.3 . . ?
C52 C53 H53B 111.3 . . ?
H53A C53 H53B 109.2 . . ?
N10 C54 C53 103.7(5) . . ?
N10 C54 H54A 111.0 . . ?
C53 C54 H54A 111.0 . . ?
N10 C54 H54B 111.0 . . ?
C53 C54 H54B 111.0 . . ?
H54A C54 H54B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 -0.8(7) . . . . ?
C4 N2 N3 C9 176.0(5) . . . . ?
C24 N5 N6 C26 0.4(7) . . . . ?
C21 N5 N6 C26 -171.1(5) . . . . ?
O1 S1 C1 C6 -152.2(5) . . . . ?
O2 S1 C1 C6 -23.8(6) . . . . ?
N1 S1 C1 C6 93.1(5) . . . . ?
O1 S1 C1 C2 27.0(6) . . . . ?
O2 S1 C1 C2 155.5(5) . . . . ?
N1 S1 C1 C2 -87.6(6) . . . . ?
C6 C1 C2 C3 -0.1(9) . . . . ?
S1 C1 C2 C3 -179.4(5) . . . . ?
C1 C2 C3 C4 -0.4(10) . . . . ?
C2 C3 C4 C5 0.2(10) . . . . ?
C2 C3 C4 N2 -179.6(5) . . . . ?
N3 N2 C4 C3 40.2(8) . . . . ?
C7 N2 C4 C3 -143.6(7) . . . . ?
N3 N2 C4 C5 -139.6(6) . . . . ?
C7 N2 C4 C5 36.6(9) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
N2 C4 C5 C6 -179.8(5) . . . . ?
C2 C1 C6 C5 0.8(9) . . . . ?
S1 C1 C6 C5 -179.9(4) . . . . ?
C4 C5 C6 C1 -0.9(9) . . . . ?
N3 N2 C7 C8 0.9(7) . . . . ?
C4 N2 C7 C8 -175.4(6) . . . . ?
N3 N2 C7 C11 -175.3(6) . . . . ?
C4 N2 C7 C11 8.3(10) . . . . ?
N2 C7 C8 C9 -0.6(7) . . . . ?
C11 C7 C8 C9 175.2(7) . . . . ?
N2 N3 C9 C8 0.4(8) . . . . ?
N2 N3 C9 C10 178.8(7) . . . . ?
C7 C8 C9 N3 0.1(8) . . . . ?
C7 C8 C9 C10 -178.2(8) . . . . ?
N3 C9 C10 F1 151.6(8) . . . . ?
C8 C9 C10 F1 -30.2(13) . . . . ?
N3 C9 C10 F3 26.7(13) . . . . ?
C8 C9 C10 F3 -155.1(9) . . . . ?
N3 C9 C10 F2 -92.9(10) . . . . ?
C8 C9 C10 F2 85.3(11) . . . . ?
N2 C7 C11 C12 -132.4(7) . . . . ?
C8 C7 C11 C12 52.4(10) . . . . ?
N2 C7 C11 C13 51.0(9) . . . . ?
C8 C7 C11 C13 -124.1(7) . . . . ?
C13 C11 C12 C15 -0.4(9) . . . . ?
C7 C11 C12 C15 -177.0(6) . . . . ?
C12 C11 C13 C14 0.2(9) . . . . ?
C7 C11 C13 C14 176.8(5) . . . . ?
C11 C13 C14 C16 0.0(10) . . . . ?
C11 C12 C15 C16 0.5(10) . . . . ?
C13 C14 C16 C15 0.1(10) . . . . ?
C13 C14 C16 C17 -178.4(6) . . . . ?
C12 C15 C16 C14 -0.3(10) . . . . ?
C12 C15 C16 C17 178.2(6) . . . . ?
O3 S2 C18 C23 -127.3(6) . . . . ?
O4 S2 C18 C23 2.9(6) . . . . ?
N4 S2 C18 C23 117.3(6) . . . . ?
O3 S2 C18 C19 53.1(6) . . . . ?
O4 S2 C18 C19 -176.7(5) . . . . ?
N4 S2 C18 C19 -62.3(5) . . . . ?
C23 C18 C19 C20 -2.7(9) . . . . ?
S2 C18 C19 C20 176.9(5) . . . . ?
C18 C19 C20 C21 2.6(9) . . . . ?
C19 C20 C21 C22 -1.0(9) . . . . ?
C19 C20 C21 N5 -178.0(5) . . . . ?
N6 N5 C21 C22 -43.0(8) . . . . ?
C24 N5 C21 C22 147.3(6) . . . . ?
N6 N5 C21 C20 134.1(6) . . . . ?
C24 N5 C21 C20 -35.7(9) . . . . ?
C20 C21 C22 C23 -0.5(9) . . . . ?
N5 C21 C22 C23 176.5(5) . . . . ?
C19 C18 C23 C22 1.2(10) . . . . ?
S2 C18 C23 C22 -178.4(5) . . . . ?
C21 C22 C23 C18 0.4(10) . . . . ?
N6 N5 C24 C25 0.6(7) . . . . ?
C21 N5 C24 C25 170.6(6) . . . . ?
N6 N5 C24 C28 175.4(6) . . . . ?
C21 N5 C24 C28 -14.5(10) . . . . ?
N5 C24 C25 C26 -1.3(7) . . . . ?
C28 C24 C25 C26 -175.7(7) . . . . ?
N5 N6 C26 C25 -1.3(8) . . . . ?
N5 N6 C26 C27 -178.9(7) . . . . ?
C24 C25 C26 N6 1.7(8) . . . . ?
C24 C25 C26 C27 179.0(8) . . . . ?
N6 C26 C27 F5A -160(7) . . . . ?
C25 C26 C27 F5A 23(7) . . . . ?
N6 C26 C27 F6 5(2) . . . . ?
C25 C26 C27 F6 -172(2) . . . . ?
N6 C26 C27 F4A 67(6) . . . . ?
C25 C26 C27 F4A -111(6) . . . . ?
N6 C26 C27 F6A -56(4) . . . . ?
C25 C26 C27 F6A 126(4) . . . . ?
N6 C26 C27 F4 129.2(15) . . . . ?
C25 C26 C27 F4 -48.0(18) . . . . ?
N6 C26 C27 F5 -118(2) . . . . ?
C25 C26 C27 F5 65(2) . . . . ?
N5 C24 C28 C29 -43.3(9) . . . . ?
C25 C24 C28 C29 130.2(8) . . . . ?
N5 C24 C28 C30 138.5(7) . . . . ?
C25 C24 C28 C30 -48.0(10) . . . . ?
C30 C28 C29 C32 0.7(10) . . . . ?
C24 C28 C29 C32 -177.4(6) . . . . ?
C29 C28 C30 C31 -0.6(10) . . . . ?
C24 C28 C30 C31 177.7(6) . . . . ?
C28 C30 C31 C33 0.3(11) . . . . ?
C28 C29 C32 C33 -0.7(11) . . . . ?
C29 C32 C33 C31 0.5(12) . . . . ?
C29 C32 C33 C34 179.2(7) . . . . ?
C30 C31 C33 C32 -0.3(12) . . . . ?
C30 C31 C33 C34 -179.0(7) . . . . ?
C39 N7 C36 C35 124.3(5) . . . . ?
C39 N7 C36 C37 1.7(6) . . . . ?
O5 C35 C36 N7 -9.4(7) . . . . ?
O6 C35 C36 N7 174.8(5) . . . . ?
O5 C35 C36 C37 107.3(6) . . . . ?
O6 C35 C36 C37 -68.5(7) . . . . ?
N7 C36 C37 C38 -9.1(10) . . . . ?
C35 C36 C37 C38 -129.6(9) . . . . ?
C36 C37 C38 C39 14.3(15) . . . . ?
C37 C38 C39 N7 -13.0(15) . . . . ?
C36 N7 C39 C38 6.3(10) . . . . ?
O7 C40 C41 C42 85.7(7) . . . . ?
O8 C40 C41 C42 -92.5(6) . . . . ?
O7 C40 C41 N8 -28.6(7) . . . . ?
O8 C40 C41 N8 153.1(5) . . . . ?
C44 N8 C41 C40 116.6(6) . . . . ?
C44 N8 C41 C42 -3.0(7) . . . . ?
C40 C41 C42 C43 -96.1(8) . . . . ?
N8 C41 C42 C43 23.1(8) . . . . ?
C41 C42 C43 C44 -35.4(10) . . . . ?
C41 N8 C44 C43 -17.7(8) . . . . ?
C42 C43 C44 N8 32.7(9) . . . . ?
C49 N9 C46 C45 110.8(5) . . . . ?
C49 N9 C46 C47 -10.9(6) . . . . ?
O9 C45 C46 N9 173.4(5) . . . . ?
O10 C45 C46 N9 -6.6(8) . . . . ?
O9 C45 C46 C47 -69.2(8) . . . . ?
O10 C45 C46 C47 110.7(6) . . . . ?
N9 C46 C47 C48 -14.4(6) . . . . ?
C45 C46 C47 C48 -135.5(6) . . . . ?
C46 C47 C48 C49 33.7(6) . . . . ?
C46 N9 C49 C48 32.0(6) . . . . ?
C47 C48 C49 N9 -40.0(6) . . . . ?
C54 N10 C51 C50 120.9(5) . . . . ?
C54 N10 C51 C52 -4.6(6) . . . . ?
O12 C50 C51 N10 21.6(7) . . . . ?
O11 C50 C51 N10 -159.3(5) . . . . ?
O12 C50 C51 C52 139.9(6) . . . . ?
O11 C50 C51 C52 -41.1(7) . . . . ?
N10 C51 C52 C53 -20.1(6) . . . . ?
C50 C51 C52 C53 -142.0(5) . . . . ?
C51 C52 C53 C54 37.1(6) . . . . ?
C51 N10 C54 C53 27.7(6) . . . . ?
C52 C53 C54 N10 -39.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O12 0.86(5) 2.17(6) 3.024(8) 172(5) .
N4 H4A O1 0.86 2.34 2.841(7) 117.4 .
N4 H4B O8 0.86 2.02 2.838(7) 158.4 .
N7 H7B O5 0.84 2.07 2.664(6) 128.0 .
N7 H7C O7 0.86 1.91 2.746(6) 163.0 .
N8 H8B O7 0.86 2.28 2.725(6) 112.2 .
N9 H9B O8 0.83 2.17 2.859(6) 140.6 .
N9 H9B O10 0.83 2.13 2.644(6) 119.7 .
N10 H10B O9 0.92 2.39 3.005(7) 124.5 .
N10 H10B O10 0.92 1.90 2.811(6) 174.3 .
N10 H10C O12 0.93 2.25 2.716(6) 110.5 .
N1 H1A O4 1.01(7) 1.94(7) 2.937(8) 168(6) 1_455
N7 H7B O6 0.84 2.28 2.868(6) 127.1 3_456
N9 H9C O6 0.93 1.75 2.683(6) 173.6 3_456
N8 H8B O9 0.86 2.02 2.702(7) 135.0 1_655
N8 H8C O11 0.85 1.89 2.727(6) 171.7 3_566
N10 H10C O11 0.93 2.08 2.833(6) 137.3 3_466

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_FC-L-Pro
_database_code_depnum_ccdc_archive 'CCDC 1850499'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-08-14 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         'C4 H4 F N3 O, C5 H9 N O2'
_chemical_formula_sum            'C9 H13 F N4 O3'
_chemical_formula_weight         244.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   5.5932(3)
_cell_length_b                   6.0945(4)
_cell_length_c                   16.8563(8)
_cell_angle_alpha                97.308(4)
_cell_angle_beta                 94.713(4)
_cell_angle_gamma                107.291(5)
_cell_volume                     539.79(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3878
_cell_measurement_theta_min      5.3240
_cell_measurement_theta_max      73.6680

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.082
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            5933
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.334
_diffrn_reflns_theta_max         73.921
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_point_group_measured_fraction_full 0.758
_reflns_number_total             3167
_reflns_number_gt                3081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.491
_reflns_Friedel_fraction_max     0.476
_reflns_Friedel_fraction_full    0.517

_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_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)+(0.0909P)²+0.0387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 981 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     339
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
F1 F 0.6569(4) 0.6806(3) 0.06624(12) 0.0460(5) Uani 1 1 d . . . . .
F2 F 0.7646(4) 0.7650(3) 0.53118(11) 0.0444(5) Uani 1 1 d . . . . .
O1 O 1.0985(4) 1.0517(4) 0.36599(13) 0.0366(5) Uani 1 1 d . . . . .
O2 O 0.4086(4) 0.3664(4) 0.22698(12) 0.0351(5) Uani 1 1 d . . . . .
O3 O 0.7640(4) 0.2345(4) 0.98502(14) 0.0395(5) Uani 1 1 d . . . . .
O4 O 0.6020(5) 0.2487(7) 0.86354(16) 0.0681(10) Uani 1 1 d . . . . .
O5 O 0.0483(4) 0.4661(4) 0.64158(15) 0.0417(5) Uani 1 1 d . . . . .
O6 O 0.1943(6) 0.3859(6) 0.75650(17) 0.0628(8) Uani 1 1 d . . . . .
N1 N 0.8266(4) 1.0478(4) 0.25765(15) 0.0320(5) Uani 1 1 d . . . . .
H1A H 0.7903 1.1647 0.2843 0.038 Uiso 1 1 d R U . . .
N2 N 1.0677(4) 0.7915(4) 0.25254(15) 0.0288(5) Uani 1 1 d . . . . .
N3 N 1.0195(5) 0.5218(5) 0.13934(17) 0.0363(6) Uani 1 1 d . . . . .
H3A H 1.131(7) 0.462(6) 0.166(2) 0.032(8) Uiso 1 1 d . . . . .
H3B H 0.942(8) 0.456(7) 0.099(3) 0.037(10) Uiso 1 1 d . . . . .
N4 N 0.4124(4) 0.6307(4) 0.33440(15) 0.0302(5) Uani 1 1 d . . . . .
H4A H 0.2940 0.6610 0.3150 0.036 Uiso 1 1 d R U . . .
N5 N 0.6690(4) 0.3893(4) 0.34095(15) 0.0309(5) Uani 1 1 d . . . . .
N6 N 0.9233(5) 0.4094(5) 0.45787(17) 0.0371(6) Uani 1 1 d . . . . .
H6A H 0.967(7) 0.303(7) 0.429(2) 0.034(9) Uiso 1 1 d . . . . .
H6B H 0.996(8) 0.483(8) 0.510(3) 0.043(10) Uiso 1 1 d . . . . .
N7 N 0.1290(4) 0.1578(4) 0.89511(16) 0.0312(5) Uani 1 1 d . . . . .
H7A H 0.202(7) 0.234(7) 0.856(2) 0.036(9) Uiso 1 1 d . . . . .
H7B H 0.004(8) 0.199(7) 0.914(2) 0.035(9) Uiso 1 1 d . . . . .
N8 N 0.6013(5) 0.3073(4) 0.70415(17) 0.0301(5) Uani 1 1 d . . . . .
H8A H 0.740(10) 0.360(8) 0.696(3) 0.057(13) Uiso 1 1 d . . . . .
H8B H 0.566(8) 0.335(7) 0.750(3) 0.039(10) Uiso 1 1 d . . . . .
C1 C 0.7096(5) 0.9550(5) 0.18208(19) 0.0336(6) Uani 1 1 d . . . . .
H1B H 0.5883 1.0118 0.1588 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7703(5) 0.7817(5) 0.14167(17) 0.0316(6) Uani 1 1 d . . . . .
C3 C 0.9552(5) 0.6951(5) 0.17835(16) 0.0286(6) Uani 1 1 d . . . . .
C4 C 1.0036(5) 0.9668(5) 0.29545(17) 0.0291(6) Uani 1 1 d . . . . .
C5 C 0.4996(5) 0.7361(5) 0.41143(17) 0.0311(6) Uani 1 1 d . . . . .
H5A H 0.4442 0.8562 0.4345 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6675(5) 0.6642(5) 0.45388(17) 0.0310(6) Uani 1 1 d . . . . .
C7 C 0.7552(5) 0.4843(5) 0.41701(16) 0.0278(6) Uani 1 1 d . . . . .
C8 C 0.4922(5) 0.4565(5) 0.29768(17) 0.0285(6) Uani 1 1 d . . . . .
C9 C 0.5853(5) 0.2275(5) 0.93464(18) 0.0318(6) Uani 1 1 d . . . . .
C10 C 0.3260(5) 0.1809(6) 0.96346(18) 0.0354(6) Uani 1 1 d . . . . .
H10A H 0.3279 0.3078 1.0057 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2360(7) -0.0472(9) 0.9931(3) 0.0625(13) Uani 1 1 d . . . . .
H11A H 0.3728 -0.0779 1.0243 0.075 Uiso 1 1 calc R U . . .
H11B H 0.1013 -0.0499 1.0262 0.075 Uiso 1 1 calc R U . . .
C12 C 0.1445(10) -0.2162(8) 0.9191(4) 0.0782(15) Uani 1 1 d . . . . .
H12A H 0.0224 -0.3569 0.9294 0.094 Uiso 1 1 calc R U . . .
H12B H 0.2832 -0.2566 0.8968 0.094 Uiso 1 1 calc R U . . .
C13 C 0.0194(7) -0.0933(7) 0.8602(3) 0.0526(9) Uani 1 1 d . . . . .
H13A H 0.0617 -0.1232 0.8061 0.063 Uiso 1 1 calc R U . . .
H13B H -0.1628 -0.1447 0.8587 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2075(5) 0.4151(5) 0.68560(19) 0.0325(6) Uani 1 1 d . . . . .
C15 C 0.4358(5) 0.3860(5) 0.64681(18) 0.0298(6) Uani 1 1 d . . . . .
H15A H 0.5320 0.5332 0.6312 0.036 Uiso 1 1 calc R U . . .
C16 C 0.3635(6) 0.1924(6) 0.57433(19) 0.0381(6) Uani 1 1 d . . . . .
H16A H 0.4956 0.2120 0.5395 0.046 Uiso 1 1 calc R U . . .
H16B H 0.2072 0.1865 0.5433 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3322(6) -0.0246(5) 0.6136(2) 0.0387(6) Uani 1 1 d . . . . .
H17A H 0.1723 -0.0695 0.6352 0.046 Uiso 1 1 calc R U . . .
H17C H 0.3418 -0.1539 0.5754 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5510(6) 0.0502(5) 0.6802(2) 0.0384(6) Uani 1 1 d . . . . .
H18C H 0.5076 -0.0309 0.7254 0.046 Uiso 1 1 calc R U . . .
H18A H 0.6981 0.0184 0.6610 0.046 Uiso 1 1 calc R U . . .


_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
F1 C2 1.354(3) . ?
F2 C6 1.361(3) . ?
O1 C4 1.241(4) . ?
O2 C8 1.237(3) . ?
O3 C9 1.244(4) . ?
O4 O4 0.000(5) 1 ?
O4 C9 1.230(4) . ?
O5 C14 1.247(4) . ?
O6 O6 0.000(11) 1 ?
O6 C14 1.235(4) . ?
N1 C1 1.353(4) . ?
N1 C4 1.377(3) . ?
N1 H1A 0.8773 . ?
N2 C3 1.330(4) . ?
N2 C4 1.366(4) . ?
N3 C3 1.329(4) . ?
N3 H3A 0.93(4) . ?
N3 H3B 0.77(5) . ?
N4 C5 1.354(4) . ?
N4 C8 1.367(4) . ?
N4 H4A 0.7949 . ?
N5 C7 1.325(4) . ?
N5 C8 1.370(3) . ?
N6 C7 1.340(4) . ?
N6 H6A 0.86(4) . ?
N6 H6B 0.94(5) . ?
N7 C13 1.489(4) . ?
N7 C10 1.490(3) . ?
N7 H7A 0.91(4) . ?
N7 H7B 0.88(4) . ?
N8 C15 1.502(3) . ?
N8 C18 1.502(4) . ?
N8 H8A 0.78(6) . ?
N8 H8B 0.82(5) . ?
C1 C2 1.327(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.426(4) . ?
C5 C6 1.341(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.423(4) . ?
C9 O4 1.230(4) 1 ?
C9 C10 1.525(4) . ?
C10 C11 1.496(5) . ?
C10 H10A 0.9800 . ?
C11 C12 1.462(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.557(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O6 1.235(4) 1 ?
C14 C15 1.527(4) . ?
C15 C16 1.522(4) . ?
C15 H15A 0.9800 . ?
C16 C17 1.524(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.509(4) . ?
C17 H17A 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18A 0.9700 . ?

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
O4 O4 C9 0(10) 1 . ?
O6 O6 C14 0(10) 1 . ?
C1 N1 C4 122.7(2) . . ?
C1 N1 H1A 119.7 . . ?
C4 N1 H1A 117.6 . . ?
C3 N2 C4 121.3(2) . . ?
C3 N3 H3A 119(2) . . ?
C3 N3 H3B 119(3) . . ?
H3A N3 H3B 121(4) . . ?
C5 N4 C8 122.5(2) . . ?
C5 N4 H4A 114.7 . . ?
C8 N4 H4A 121.9 . . ?
C7 N5 C8 121.3(3) . . ?
C7 N6 H6A 113(3) . . ?
C7 N6 H6B 120(3) . . ?
H6A N6 H6B 126(4) . . ?
C13 N7 C10 108.3(3) . . ?
C13 N7 H7A 108(2) . . ?
C10 N7 H7A 109(2) . . ?
C13 N7 H7B 106(3) . . ?
C10 N7 H7B 109(3) . . ?
H7A N7 H7B 116(4) . . ?
C15 N8 C18 108.4(2) . . ?
C15 N8 H8A 107(4) . . ?
C18 N8 H8A 103(4) . . ?
C15 N8 H8B 109(3) . . ?
C18 N8 H8B 110(3) . . ?
H8A N8 H8B 119(5) . . ?
C2 C1 N1 119.1(2) . . ?
C2 C1 H1B 120.5 . . ?
N1 C1 H1B 120.5 . . ?
C1 C2 F1 121.5(2) . . ?
C1 C2 C3 119.9(3) . . ?
F1 C2 C3 118.6(3) . . ?
N3 C3 N2 119.4(2) . . ?
N3 C3 C2 121.2(3) . . ?
N2 C3 C2 119.4(3) . . ?
O1 C4 N2 122.2(2) . . ?
O1 C4 N1 120.3(3) . . ?
N2 C4 N1 117.5(2) . . ?
C6 C5 N4 118.8(3) . . ?
C6 C5 H5A 120.6 . . ?
N4 C5 H5A 120.6 . . ?
C5 C6 F2 121.6(3) . . ?
C5 C6 C7 119.9(3) . . ?
F2 C6 C7 118.5(2) . . ?
N5 C7 N6 119.5(3) . . ?
N5 C7 C6 119.4(2) . . ?
N6 C7 C6 121.2(3) . . ?
O2 C8 N4 120.3(2) . . ?
O2 C8 N5 121.6(3) . . ?
N4 C8 N5 118.1(3) . . ?
O4 C9 O4 0.00(3) 1 . ?
O4 C9 O3 124.8(3) 1 . ?
O4 C9 O3 124.8(3) . . ?
O4 C9 C10 118.3(2) 1 . ?
O4 C9 C10 118.3(2) . . ?
O3 C9 C10 116.8(3) . . ?
N7 C10 C11 103.0(3) . . ?
N7 C10 C9 110.6(2) . . ?
C11 C10 C9 113.5(3) . . ?
N7 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C12 C11 C10 103.6(3) . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C11 C12 C13 105.3(4) . . ?
C11 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
N7 C13 C12 103.4(3) . . ?
N7 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
N7 C13 H13B 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
O6 C14 O6 0.0(6) 1 . ?
O6 C14 O5 125.6(3) 1 . ?
O6 C14 O5 125.6(3) . . ?
O6 C14 C15 118.4(3) 1 . ?
O6 C14 C15 118.4(3) . . ?
O5 C14 C15 115.9(3) . . ?
N8 C15 C16 103.3(2) . . ?
N8 C15 C14 110.3(2) . . ?
C16 C15 C14 112.8(2) . . ?
N8 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
C14 C15 H15A 110.1 . . ?
C15 C16 C17 102.4(2) . . ?
C15 C16 H16A 111.3 . . ?
C17 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
C17 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C18 C17 C16 103.3(2) . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17C 111.1 . . ?
C16 C17 H17C 111.1 . . ?
H17A C17 H17C 109.1 . . ?
N8 C18 C17 105.1(2) . . ?
N8 C18 H18C 110.7 . . ?
C17 C18 H18C 110.7 . . ?
N8 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
H18C C18 H18A 108.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B F1 0.77(5) 2.46(4) 2.762(3) 105(4) .
N6 H6B F2 0.94(5) 2.45(4) 2.767(4) 100(3) .
N7 H7A O4 0.91(4) 2.21(4) 2.650(3) 109(3) .
N8 H8B O6 0.82(5) 2.20(4) 2.657(4) 115(4) .
N1 H1A N5 0.88 1.89 2.762(3) 172.5 1_565
N3 H3A O2 0.93(4) 2.05(4) 2.978(3) 173(3) 1_655
N3 H3B O3 0.77(5) 2.18(5) 2.936(4) 171(4) 1_554
N4 H4A N2 0.79 1.98 2.759(3) 164.8 1_455
N6 H6A O1 0.86(4) 2.10(5) 2.962(4) 176(4) 1_545
N6 H6B O5 0.94(5) 2.23(5) 3.070(4) 149(4) 1_655
N7 H7A O6 0.91(4) 2.02(4) 2.862(4) 154(3) 1
N7 H7B O4 0.88(4) 2.45(4) 3.173(4) 139(3) 1_455
N8 H8A O5 0.78(6) 1.99(6) 2.749(3) 164(5) 1_655
N8 H8B O4 0.82(5) 2.06(4) 2.755(4) 142(4) 1

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_SMZ-L-Pro
_database_code_depnum_ccdc_archive 'CCDC 1850501'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-08-14 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         'C9 H10 N4 O2 S2, C5 H9 N O2'
_chemical_formula_sum            'C14 H19 N5 O4 S2'
_chemical_formula_weight         385.46

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.1850(9)
_cell_length_b                   8.9191(9)
_cell_length_c                   17.2838(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.393(9)
_cell_angle_gamma                90
_cell_volume                     1713.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2176
_cell_measurement_theta_min      3.9390
_cell_measurement_theta_max      27.0090

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.342
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            8982
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.155
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5096
_reflns_number_gt                3522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.05(17)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5096
_refine_ls_number_parameters     456
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.976
_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
S1 S 1.2700(2) 0.4762(3) 0.69893(14) 0.0393(6) Uani 1 1 d . . . . .
S2 S 0.50157(18) -0.2097(3) 0.79108(11) 0.0348(6) Uani 1 1 d . . . . .
S3 S 0.99958(17) 0.6235(3) 0.70475(11) 0.0334(5) Uani 1 1 d . . . . .
S4 S 0.2311(2) -0.0687(3) 0.80155(14) 0.0415(6) Uani 1 1 d . . . . .
O1 O 0.5941(5) -0.2852(7) 0.7546(3) 0.0444(16) Uani 1 1 d . . . . .
O2 O 0.4158(5) -0.3031(7) 0.8251(3) 0.0437(17) Uani 1 1 d . . . . .
O3 O 0.9098(5) 0.7058(7) 0.7413(3) 0.0384(15) Uani 1 1 d . . . . .
O4 O 1.0872(5) 0.7101(7) 0.6680(3) 0.0400(16) Uani 1 1 d . . . . .
O5 O 0.9612(6) 0.3101(10) 1.0327(4) 0.072(2) Uani 1 1 d . . . . .
O6 O 1.0800(6) 0.3513(9) 0.9445(4) 0.073(2) Uani 1 1 d . . . . .
O7 O 0.5070(5) 0.1200(8) 0.4518(3) 0.0448(15) Uani 1 1 d . . . . .
O8 O 0.4285(5) 0.1037(8) 0.5655(3) 0.0448(15) Uani 1 1 d . . . . .
N1 N 0.7399(6) 0.1602(9) 1.0466(4) 0.046(2) Uani 1 1 d . . . . .
H1B H 0.7014 0.1677 1.0936 0.069 Uiso 1 1 d R U . . .
H1A H 0.8044 0.2017 1.0376 0.069 Uiso 1 1 d R U . . .
N2 N 0.4378(6) -0.1020(9) 0.7246(4) 0.0345(18) Uani 1 1 d . . . . .
N3 N 0.2755(7) 0.0426(9) 0.6755(4) 0.038(2) Uani 1 1 d D . . . .
N4 N 0.1628(6) 0.0981(10) 0.6837(4) 0.0429(19) Uani 1 1 d . . . . .
N5 N 0.7454(6) 0.2590(10) 0.4535(4) 0.047(2) Uani 1 1 d . . . . .
H5B H 0.7725 0.2488 0.4120 0.070 Uiso 1 1 d R U . . .
H5A H 0.6764 0.2322 0.4535 0.070 Uiso 1 1 d R U . . .
N6 N 1.0617(6) 0.5179(8) 0.7720(4) 0.0339(18) Uani 1 1 d . . . . .
N7 N 1.2222(6) 0.3770(8) 0.8267(4) 0.0376(19) Uani 1 1 d D . . . .
H7A H 1.1947 0.3501 0.8624 0.045 Uiso 1 1 d DR U . . .
N8 N 1.3358(6) 0.3243(9) 0.8219(4) 0.0411(19) Uani 1 1 d . . . . .
N9 N 1.0980(5) 0.0802(8) 1.0991(4) 0.0403(19) Uani 1 1 d . . . . .
H9D H 1.0389 0.0275 1.0707 0.048 Uiso 1 1 calc R U . . .
H9E H 1.0663 0.1252 1.1395 0.048 Uiso 1 1 calc R U . . .
N10 N 0.4041(5) 0.3757(8) 0.4082(3) 0.0313(17) Uani 1 1 d . . . . .
H10A H 0.4594 0.4503 0.4168 0.038 Uiso 1 1 calc R U . . .
H10B H 0.4351 0.3031 0.3793 0.038 Uiso 1 1 calc R U . . .
C1 C 0.6853(8) 0.0775(11) 0.9858(5) 0.041(2) Uani 1 1 d . . . . .
C2 C 0.7287(8) 0.0705(10) 0.9147(5) 0.038(2) Uani 1 1 d . . . . .
H2A H 0.7982 0.1271 0.9065 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6744(7) -0.0163(10) 0.8549(4) 0.035(2) Uani 1 1 d . . . . .
H3B H 0.7074 -0.0216 0.8067 0.042 Uiso 1 1 calc R U . . .
C4 C 0.5712(7) -0.0958(10) 0.8658(4) 0.034(2) Uani 1 1 d . . . . .
C5 C 0.5235(7) -0.0880(12) 0.9362(5) 0.043(2) Uani 1 1 d . . . . .
H5C H 0.4523 -0.1420 0.9433 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5788(7) -0.0026(11) 0.9955(5) 0.044(2) Uani 1 1 d . . . . .
H6A H 0.5454 0.0029 1.0436 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3299(8) -0.0466(11) 0.7299(5) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.1281(8) 0.0469(11) 0.7483(6) 0.043(3) Uani 1 1 d . . . . .
C9 C 0.0093(7) 0.0863(14) 0.7729(6) 0.059(3) Uani 1 1 d . . . . .
H9A H -0.0002 0.0373 0.8226 0.089 Uiso 1 1 calc R U . . .
H9B H 0.0039 0.1952 0.7790 0.089 Uiso 1 1 calc R U . . .
H9C H -0.0546 0.0524 0.7333 0.089 Uiso 1 1 calc R U . . .
C10 C 0.8031(7) 0.3401(10) 0.5124(5) 0.030(2) Uani 1 1 d . . . . .
C11 C 0.7507(7) 0.3710(10) 0.5813(5) 0.037(2) Uani 1 1 d . . . . .
H11A H 0.6726 0.3336 0.5870 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8107(7) 0.4540(11) 0.6402(5) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.7741 0.4735 0.6862 0.047 Uiso 1 1 calc R U . . .
C13 C 0.9255(7) 0.5100(10) 0.6326(4) 0.031(2) Uani 1 1 d . . . . .
C14 C 0.9760(7) 0.4805(11) 0.5649(4) 0.036(2) Uani 1 1 d . . . . .
H14A H 1.0539 0.5184 0.5590 0.043 Uiso 1 1 calc R U . . .
C15 C 0.9164(7) 0.3979(11) 0.5064(5) 0.039(2) Uani 1 1 d . . . . .
H15A H 0.9535 0.3797 0.4605 0.047 Uiso 1 1 calc R U . . .
C16 C 1.1719(7) 0.4614(10) 0.7685(5) 0.030(2) Uani 1 1 d . . . . .
C17 C 1.3706(8) 0.3650(11) 0.7576(5) 0.039(2) Uani 1 1 d . . . . .
C18 C 1.4937(7) 0.3298(13) 0.7352(6) 0.058(3) Uani 1 1 d . . . . .
H18A H 1.5015 0.3714 0.6835 0.087 Uiso 1 1 calc R U . . .
H18B H 1.5549 0.3741 0.7733 0.087 Uiso 1 1 calc R U . . .
H18C H 1.5047 0.2208 0.7340 0.087 Uiso 1 1 calc R U . . .
C19 C 1.0556(8) 0.2895(11) 1.0040(5) 0.043(2) Uani 1 1 d . . . . .
C20 C 1.1499(6) 0.1937(9) 1.0499(4) 0.0371(18) Uani 1 1 d . . . . .
H20A H 1.1999 0.2625 1.0859 0.044 Uiso 1 1 calc R U . . .
C21 C 1.2352(8) 0.1037(13) 1.0079(5) 0.054(3) Uani 1 1 d . . . . .
H21A H 1.2978 0.1682 0.9888 0.064 Uiso 1 1 calc R U . . .
H21B H 1.1923 0.0488 0.9634 0.064 Uiso 1 1 calc R U . . .
C22 C 1.2905(8) -0.0059(12) 1.0719(6) 0.049(3) Uani 1 1 d . . . . .
H22A H 1.3069 -0.1043 1.0488 0.059 Uiso 1 1 calc R U . . .
H22B H 1.3670 0.0348 1.0979 0.059 Uiso 1 1 calc R U . . .
C23 C 1.2003(7) -0.0221(12) 1.1289(5) 0.043(2) Uani 1 1 d . . . . .
H23A H 1.2353 0.0086 1.1817 0.051 Uiso 1 1 calc R U . . .
H23B H 1.1723 -0.1272 1.1310 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4424(7) 0.1638(10) 0.5014(5) 0.032(2) Uani 1 1 d . . . . .
C25A C 0.3751(6) 0.3117(8) 0.4846(4) 0.0329(17) Uani 1 1 d . . . . .
H25A H 0.4019 0.3845 0.5270 0.039 Uiso 1 1 calc R U . . .
C26 C 0.2400(6) 0.3020(11) 0.4767(5) 0.037(2) Uani 1 1 d . . . . .
H26A H 0.2094 0.3119 0.5280 0.044 Uiso 1 1 calc R U . . .
H26B H 0.2118 0.2056 0.4528 0.044 Uiso 1 1 calc R U . . .
C27 C 0.1991(7) 0.4326(11) 0.4242(5) 0.040(2) Uani 1 1 d . . . . .
H27A H 0.1169 0.4156 0.3980 0.048 Uiso 1 1 calc R U . . .
H27B H 0.2002 0.5274 0.4540 0.048 Uiso 1 1 calc R U . . .
C28 C 0.2903(7) 0.4360(12) 0.3659(5) 0.045(2) Uani 1 1 d . . . . .
H28A H 0.2633 0.3728 0.3202 0.054 Uiso 1 1 calc R U . . .
H28B H 0.3022 0.5398 0.3480 0.054 Uiso 1 1 calc R U . . .
H3A H 0.314(7) 0.062(10) 0.634(3) 0.08(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C16 1.721(9) . ?
S1 C17 1.739(10) . ?
S2 O1 1.438(6) . ?
S2 O2 1.444(6) . ?
S2 N2 1.603(7) . ?
S2 C4 1.755(9) . ?
S3 O3 1.445(5) . ?
S3 O4 1.449(6) . ?
S3 N6 1.594(7) . ?
S3 C13 1.742(8) . ?
S4 C8 1.733(10) . ?
S4 C7 1.760(9) . ?
O5 C19 1.230(9) . ?
O6 C19 1.223(10) . ?
O7 C24 1.245(9) . ?
O8 C24 1.256(9) . ?
N1 C1 1.370(10) . ?
N1 H1B 0.9630 . ?
N1 H1A 0.8407 . ?
N2 C7 1.317(10) . ?
N3 C7 1.326(10) . ?
N3 N4 1.377(9) . ?
N3 H3A 0.88(3) . ?
N4 C8 1.304(11) . ?
N5 C10 1.353(10) . ?
N5 H5B 0.8143 . ?
N5 H5A 0.8083 . ?
N6 C16 1.339(10) . ?
N7 C16 1.331(10) . ?
N7 N8 1.366(9) . ?
N7 H7A 0.7589 . ?
N8 C17 1.271(10) . ?
N9 C20 1.482(9) . ?
N9 C23 1.508(10) . ?
N9 H9D 0.9100 . ?
N9 H9E 0.9100 . ?
N10 C28 1.495(9) . ?
N10 C25A 1.507(8) . ?
N10 H10A 0.9100 . ?
N10 H10B 0.9100 . ?
C1 C2 1.372(12) . ?
C1 C6 1.415(11) . ?
C2 C3 1.378(11) . ?
C2 H2A 0.9500 . ?
C3 C4 1.385(11) . ?
C3 H3B 0.9500 . ?
C4 C5 1.384(10) . ?
C5 C6 1.369(12) . ?
C5 H5C 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C9 1.483(11) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.383(10) . ?
C10 C11 1.412(11) . ?
C11 C12 1.372(11) . ?
C11 H11A 0.9500 . ?
C12 C13 1.398(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.380(10) . ?
C14 C15 1.364(11) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 C18 1.504(11) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.512(11) . ?
C20 C21 1.495(11) . ?
C20 H20A 1.0000 . ?
C21 C22 1.552(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.495(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25A 1.530(11) . ?
C25A C26 1.505(9) . ?
C25A H25A 1.0000 . ?
C26 C27 1.515(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.511(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C17 88.3(4) . . ?
O1 S2 O2 116.8(4) . . ?
O1 S2 N2 104.5(4) . . ?
O2 S2 N2 112.0(4) . . ?
O1 S2 C4 108.1(4) . . ?
O2 S2 C4 107.2(4) . . ?
N2 S2 C4 107.8(4) . . ?
O3 S3 O4 117.2(4) . . ?
O3 S3 N6 104.4(4) . . ?
O4 S3 N6 111.9(3) . . ?
O3 S3 C13 108.1(4) . . ?
O4 S3 C13 106.6(4) . . ?
N6 S3 C13 108.2(4) . . ?
C8 S4 C7 89.5(5) . . ?
C1 N1 H1B 118.8 . . ?
C1 N1 H1A 114.4 . . ?
H1B N1 H1A 126.8 . . ?
C7 N2 S2 120.9(6) . . ?
C7 N3 N4 119.7(7) . . ?
C7 N3 H3A 118(6) . . ?
N4 N3 H3A 123(6) . . ?
C8 N4 N3 109.0(8) . . ?
C10 N5 H5B 122.0 . . ?
C10 N5 H5A 122.2 . . ?
H5B N5 H5A 114.6 . . ?
C16 N6 S3 121.2(6) . . ?
C16 N7 N8 117.8(7) . . ?
C16 N7 H7A 128.2 . . ?
N8 N7 H7A 113.9 . . ?
C17 N8 N7 109.5(8) . . ?
C20 N9 C23 106.2(6) . . ?
C20 N9 H9D 110.5 . . ?
C23 N9 H9D 110.5 . . ?
C20 N9 H9E 110.5 . . ?
C23 N9 H9E 110.5 . . ?
H9D N9 H9E 108.7 . . ?
C28 N10 C25A 108.1(5) . . ?
C28 N10 H10A 110.1 . . ?
C25A N10 H10A 110.1 . . ?
C28 N10 H10B 110.1 . . ?
C25A N10 H10B 110.1 . . ?
H10A N10 H10B 108.4 . . ?
N1 C1 C2 122.6(9) . . ?
N1 C1 C6 119.4(8) . . ?
C2 C1 C6 118.0(9) . . ?
C1 C2 C3 121.8(9) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C2 C3 C4 119.4(7) . . ?
C2 C3 H3B 120.3 . . ?
C4 C3 H3B 120.3 . . ?
C5 C4 C3 120.1(8) . . ?
C5 C4 S2 119.5(7) . . ?
C3 C4 S2 120.3(6) . . ?
C6 C5 C4 120.0(8) . . ?
C6 C5 H5C 120.0 . . ?
C4 C5 H5C 120.0 . . ?
C5 C6 C1 120.6(8) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N2 C7 N3 121.8(8) . . ?
N2 C7 S4 131.2(7) . . ?
N3 C7 S4 107.0(7) . . ?
N4 C8 C9 121.6(9) . . ?
N4 C8 S4 114.8(7) . . ?
C9 C8 S4 123.6(7) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 C15 120.4(7) . . ?
N5 C10 C11 122.1(7) . . ?
C15 C10 C11 117.4(8) . . ?
C12 C11 C10 121.1(8) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 120.1(8) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C14 C13 C12 118.6(8) . . ?
C14 C13 S3 120.7(6) . . ?
C12 C13 S3 120.6(6) . . ?
C15 C14 C13 121.3(8) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C10 121.5(7) . . ?
C14 C15 H15A 119.3 . . ?
C10 C15 H15A 119.3 . . ?
N7 C16 N6 119.5(7) . . ?
N7 C16 S1 108.8(6) . . ?
N6 C16 S1 131.7(7) . . ?
N8 C17 C18 123.0(9) . . ?
N8 C17 S1 115.5(7) . . ?
C18 C17 S1 121.3(7) . . ?
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 . . ?
O6 C19 O5 123.6(10) . . ?
O6 C19 C20 119.2(9) . . ?
O5 C19 C20 116.9(8) . . ?
N9 C20 C21 103.0(7) . . ?
N9 C20 C19 113.1(6) . . ?
C21 C20 C19 119.6(7) . . ?
N9 C20 H20A 106.8 . . ?
C21 C20 H20A 106.8 . . ?
C19 C20 H20A 106.8 . . ?
C20 C21 C22 102.5(7) . . ?
C20 C21 H21A 111.3 . . ?
C22 C21 H21A 111.3 . . ?
C20 C21 H21B 111.3 . . ?
C22 C21 H21B 111.3 . . ?
H21A C21 H21B 109.2 . . ?
C23 C22 C21 106.6(7) . . ?
C23 C22 H22A 110.4 . . ?
C21 C22 H22A 110.4 . . ?
C23 C22 H22B 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
C22 C23 N9 105.0(7) . . ?
C22 C23 H23A 110.8 . . ?
N9 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
N9 C23 H23B 110.8 . . ?
H23A C23 H23B 108.8 . . ?
O7 C24 O8 127.8(8) . . ?
O7 C24 C25A 116.8(7) . . ?
O8 C24 C25A 115.4(7) . . ?
N10 C25A C26 104.7(6) . . ?
N10 C25A C24 110.1(6) . . ?
C26 C25A C24 115.8(6) . . ?
N10 C25A H25A 108.7 . . ?
C26 C25A H25A 108.7 . . ?
C24 C25A H25A 108.7 . . ?
C25A C26 C27 104.1(7) . . ?
C25A C26 H26A 110.9 . . ?
C27 C26 H26A 110.9 . . ?
C25A C26 H26B 110.9 . . ?
C27 C26 H26B 110.9 . . ?
H26A C26 H26B 109.0 . . ?
C28 C27 C26 103.5(7) . . ?
C28 C27 H27A 111.1 . . ?
C26 C27 H27A 111.1 . . ?
C28 C27 H27B 111.1 . . ?
C26 C27 H27B 111.1 . . ?
H27A C27 H27B 109.0 . . ?
N10 C28 C27 105.5(6) . . ?
N10 C28 H28A 110.6 . . ?
C27 C28 H28A 110.6 . . ?
N10 C28 H28B 110.6 . . ?
C27 C28 H28B 110.6 . . ?
H28A C28 H28B 108.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O5 0.84 2.01 2.847(10) 171.5 .
N1 H1B O2 0.96 2.04 2.987(9) 166.1 2_657
N3 H3A O8 0.88(3) 1.88(3) 2.749(9) 166(8) .
N5 H5A O7 0.81 2.14 2.938(9) 169.3 .
N5 H5B O4 0.81 2.23 2.996(9) 156.8 2_746
N7 H7A O6 0.76 2.02 2.729(9) 156.7 .
N9 H9D O6 0.91 2.06 2.893(10) 152.2 2_747
N9 H9E O3 0.91 2.17 2.987(8) 148.9 2_747
N9 H9E N6 0.91 2.41 3.058(9) 128.5 2_747
N10 H10A O8 0.91 1.86 2.767(9) 179.5 2_656
N10 H10B O7 0.91 2.16 2.628(9) 111.1 .
N10 H10B O1 0.91 2.43 3.161(8) 137.2 2_656
N10 H10B N2 0.91 2.56 3.055(9) 115.2 2_656

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.068

