# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a2014221_ac55
_database_code_depnum_ccdc_archive 'CCDC 1411373'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;

_audit_creation_date             2014-10-24T13:31:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   6.1168(3)
_cell_length_b                   12.5792(10)
_cell_length_c                   13.3742(10)
_cell_angle_alpha                113.132(7)
_cell_angle_beta                 92.441(5)
_cell_angle_gamma                103.376(5)
_cell_volume                     910.36(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3787
_cell_measurement_theta_min      4.106
_cell_measurement_theta_max      76.455
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.62653
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_ub_11      0.2180576
_diffrn_orient_matrix_ub_12      0.005749
_diffrn_orient_matrix_ub_13      -0.0534875
_diffrn_orient_matrix_ub_21      0.0252752
_diffrn_orient_matrix_ub_22      -0.1128696
_diffrn_orient_matrix_ub_23      0.0135201
_diffrn_orient_matrix_ub_31      -0.1426718
_diffrn_orient_matrix_ub_32      -0.0797368
_diffrn_orient_matrix_ub_33      -0.1140329
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_number            6540
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         68.99
_diffrn_reflns_theta_full        68.99
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3381
_reflns_number_gt                3103
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -37.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756   19.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega -107.00  -35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  111.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega -111.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   61.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   79.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 63

#__ type_ start__ end____ width___ exp.time_
  8 omega   86.00  152.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00  147.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega   83.00  158.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   34.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   47.00   97.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 22 omega   90.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   44.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
 24 omega   95.00  122.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   80.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 26 omega   24.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   60.0000 55

;

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

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.1288P)²+1.3754P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3381
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2314
_refine_ls_wR_factor_gt          0.2286
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.116

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.3191(3) 0.11166(17) 0.08749(16) 0.0227(5) Uani 1 1 d . . .
O2 O 0.0252(3) 0.40425(19) 0.31393(16) 0.0262(5) Uani 1 1 d . . .
O3 O 0.4244(3) 0.20939(19) -0.10419(18) 0.0278(5) Uani 1 1 d . . .
O4 O 0.1559(3) 0.03335(18) -0.16502(16) 0.0221(5) Uani 1 1 d . . .
N1 N 0.1909(4) 0.2527(2) 0.22249(19) 0.0196(5) Uani 1 1 d . . .
N2 N 0.1191(4) 0.3339(2) 0.00682(19) 0.0193(5) Uani 1 1 d . . .
C1 C 0.1842(4) 0.1709(2) 0.1168(2) 0.0180(6) Uani 1 1 d . . .
C2 C 0.0350(4) 0.3216(2) 0.2310(2) 0.0187(6) Uani 1 1 d . . .
C3 C -0.1101(4) 0.2718(2) 0.1197(2) 0.0192(6) Uani 1 1 d . . .
H3 H -0.2742 0.2426 0.1246 0.023 Uiso 1 1 calc R . .
C4 C -0.0764(4) 0.3605(2) 0.0631(2) 0.0195(6) Uani 1 1 d . . .
H4 H -0.2117 0.3347 0.006 0.023 Uiso 1 1 calc R . .
C5 C 0.0509(4) 0.2035(2) -0.0493(2) 0.0187(6) Uani 1 1 d . . .
H5 H -0.0864 0.178 -0.1051 0.022 Uiso 1 1 calc R . .
C6 C -0.0197(4) 0.1679(2) 0.0452(2) 0.0180(6) Uani 1 1 d . . .
H6 H -0.1376 0.089 0.0177 0.022 Uiso 1 1 calc R . .
C7 C 0.3448(4) 0.2698(3) 0.3154(2) 0.0212(6) Uani 1 1 d . . .
C8 C 0.3139(5) 0.1809(3) 0.3537(2) 0.0272(7) Uani 1 1 d . . .
H8 H 0.1954 0.1088 0.3178 0.033 Uiso 1 1 calc R . .
C9 C 0.4580(6) 0.1981(3) 0.4453(3) 0.0336(7) Uani 1 1 d . . .
H9 H 0.4391 0.1376 0.4724 0.04 Uiso 1 1 calc R . .
C10 C 0.6305(5) 0.3048(3) 0.4972(3) 0.0340(8) Uani 1 1 d . . .
H10 H 0.7282 0.3172 0.5602 0.041 Uiso 1 1 calc R . .
C11 C 0.6602(5) 0.3923(3) 0.4578(3) 0.0320(7) Uani 1 1 d . . .
H11 H 0.7791 0.4643 0.4931 0.038 Uiso 1 1 calc R . .
C12 C 0.5163(5) 0.3753(3) 0.3660(2) 0.0264(6) Uani 1 1 d . . .
H12 H 0.5358 0.4356 0.3386 0.032 Uiso 1 1 calc R . .
C13 C -0.0435(5) 0.4906(2) 0.1380(2) 0.0199(6) Uani 1 1 d . . .
C14 C -0.2314(5) 0.5263(3) 0.1827(2) 0.0233(6) Uani 1 1 d . . .
H14 H -0.3757 0.4692 0.1624 0.028 Uiso 1 1 calc R . .
C15 C -0.2100(5) 0.6431(3) 0.2555(2) 0.0258(6) Uani 1 1 d . . .
H15 H -0.3389 0.6647 0.2862 0.031 Uiso 1 1 calc R . .
C16 C -0.0022(5) 0.7303(3) 0.2849(2) 0.0240(6) Uani 1 1 d . . .
C17 C 0.1829(5) 0.6956(3) 0.2368(2) 0.0225(6) Uani 1 1 d . . .
H17 H 0.3247 0.7539 0.253 0.027 Uiso 1 1 calc R . .
C18 C 0.1628(4) 0.5773(3) 0.1658(2) 0.0207(6) Uani 1 1 d . . .
H18 H 0.292 0.5554 0.1359 0.025 Uiso 1 1 calc R . .
C19 C 0.0228(6) 0.8574(3) 0.3663(3) 0.0320(7) Uani 1 1 d . . .
H19A H -0.1098 0.8832 0.3515 0.048 Uiso 1 1 calc R . .
H19B H 0.1607 0.9104 0.3592 0.048 Uiso 1 1 calc R . .
H19C H 0.0337 0.8614 0.441 0.048 Uiso 1 1 calc R . .
C20 C 0.2355(4) 0.1520(2) -0.1063(2) 0.0194(6) Uani 1 1 d . . .
C21 C 0.3188(5) -0.0259(3) -0.2216(3) 0.0268(6) Uani 1 1 d . . .
H21A H 0.2417 -0.1101 -0.2688 0.04 Uiso 1 1 calc R . .
H21B H 0.4374 -0.022 -0.1676 0.04 Uiso 1 1 calc R . .
H21C H 0.3878 0.0141 -0.2669 0.04 Uiso 1 1 calc R . .
H2 H 0.138(6) 0.369(3) -0.043(3) 0.016(7) Uiso 1 1 d . . .



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

_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
O1 C1 1.213(3) . ?
O2 C2 1.201(3) . ?
O3 C20 1.205(3) . ?
O4 C20 1.338(3) . ?
O4 C21 1.444(3) . ?
N1 C1 1.376(4) . ?
N1 C2 1.410(3) . ?
N1 C7 1.440(3) . ?
N2 C5 1.455(3) . ?
N2 C4 1.474(3) . ?
N2 H2 0.93(3) . ?
C1 C6 1.524(3) . ?
C2 C3 1.515(4) . ?
C3 C6 1.538(4) . ?
C3 C4 1.559(4) . ?
C3 H3 1 . ?
C4 C13 1.504(4) . ?
C4 H4 1 . ?
C5 C20 1.517(4) . ?
C5 C6 1.544(4) . ?
C5 H5 1 . ?
C6 H6 1 . ?
C7 C8 1.381(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.393(4) . ?
C8 H8 0.95 . ?
C9 C10 1.395(5) . ?
C9 H9 0.95 . ?
C10 C11 1.376(5) . ?
C10 H10 0.95 . ?
C11 C12 1.394(4) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C18 1.387(4) . ?
C13 C14 1.402(4) . ?
C14 C15 1.379(4) . ?
C14 H14 0.95 . ?
C15 C16 1.395(4) . ?
C15 H15 0.95 . ?
C16 C17 1.398(4) . ?
C16 C19 1.507(4) . ?
C17 C18 1.388(4) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O4 C21 115.3(2) . . ?
C1 N1 C2 113.2(2) . . ?
C1 N1 C7 124.1(2) . . ?
C2 N1 C7 122.7(2) . . ?
C5 N2 C4 102.9(2) . . ?
C5 N2 H2 111.6(19) . . ?
C4 N2 H2 109(2) . . ?
O1 C1 N1 124.8(2) . . ?
O1 C1 C6 126.8(2) . . ?
N1 C1 C6 108.4(2) . . ?
O2 C2 N1 124.0(2) . . ?
O2 C2 C3 128.2(2) . . ?
N1 C2 C3 107.8(2) . . ?
C2 C3 C6 105.2(2) . . ?
C2 C3 C4 113.8(2) . . ?
C6 C3 C4 104.4(2) . . ?
C2 C3 H3 111 . . ?
C6 C3 H3 111 . . ?
C4 C3 H3 111 . . ?
N2 C4 C13 114.7(2) . . ?
N2 C4 C3 100.7(2) . . ?
C13 C4 C3 115.9(2) . . ?
N2 C4 H4 108.4 . . ?
C13 C4 H4 108.4 . . ?
C3 C4 H4 108.4 . . ?
N2 C5 C20 113.2(2) . . ?
N2 C5 C6 101.6(2) . . ?
C20 C5 C6 115.2(2) . . ?
N2 C5 H5 108.9 . . ?
C20 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C1 C6 C3 104.7(2) . . ?
C1 C6 C5 112.2(2) . . ?
C3 C6 C5 103.6(2) . . ?
C1 C6 H6 111.9 . . ?
C3 C6 H6 111.9 . . ?
C5 C6 H6 111.9 . . ?
C8 C7 C12 121.4(3) . . ?
C8 C7 N1 118.9(2) . . ?
C12 C7 N1 119.7(3) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C7 C12 C11 119.1(3) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C4 123.7(2) . . ?
C14 C13 C4 118.3(2) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 117.8(3) . . ?
C15 C16 C19 121.2(3) . . ?
C17 C16 C19 121.0(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C13 C18 C17 120.9(3) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 O4 124.1(2) . . ?
O3 C20 C5 125.4(3) . . ?
O4 C20 C5 110.4(2) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 171.3(2) . . . . ?
C7 N1 C1 O1 -7.0(4) . . . . ?
C2 N1 C1 C6 -9.1(3) . . . . ?
C7 N1 C1 C6 172.6(2) . . . . ?
C1 N1 C2 O2 -173.9(3) . . . . ?
C7 N1 C2 O2 4.4(4) . . . . ?
C1 N1 C2 C3 6.3(3) . . . . ?
C7 N1 C2 C3 -175.4(2) . . . . ?
O2 C2 C3 C6 179.4(3) . . . . ?
N1 C2 C3 C6 -0.8(3) . . . . ?
O2 C2 C3 C4 65.7(4) . . . . ?
N1 C2 C3 C4 -114.5(2) . . . . ?
C5 N2 C4 C13 174.3(2) . . . . ?
C5 N2 C4 C3 49.1(2) . . . . ?
C2 C3 C4 N2 86.4(2) . . . . ?
C6 C3 C4 N2 -27.8(2) . . . . ?
C2 C3 C4 C13 -38.0(3) . . . . ?
C6 C3 C4 C13 -152.1(2) . . . . ?
C4 N2 C5 C20 -174.9(2) . . . . ?
C4 N2 C5 C6 -50.9(2) . . . . ?
O1 C1 C6 C3 -172.4(3) . . . . ?
N1 C1 C6 C3 7.9(3) . . . . ?
O1 C1 C6 C5 -60.7(3) . . . . ?
N1 C1 C6 C5 119.7(2) . . . . ?
C2 C3 C6 C1 -4.1(3) . . . . ?
C4 C3 C6 C1 116.0(2) . . . . ?
C2 C3 C6 C5 -121.9(2) . . . . ?
C4 C3 C6 C5 -1.7(2) . . . . ?
N2 C5 C6 C1 -81.2(2) . . . . ?
C20 C5 C6 C1 41.5(3) . . . . ?
N2 C5 C6 C3 31.2(2) . . . . ?
C20 C5 C6 C3 153.9(2) . . . . ?
C1 N1 C7 C8 -70.1(4) . . . . ?
C2 N1 C7 C8 111.8(3) . . . . ?
C1 N1 C7 C12 111.5(3) . . . . ?
C2 N1 C7 C12 -66.7(4) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
N1 C7 C8 C9 -178.2(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C8 C7 C12 C11 -0.2(4) . . . . ?
N1 C7 C12 C11 178.2(3) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
N2 C4 C13 C18 -9.0(4) . . . . ?
C3 C4 C13 C18 107.7(3) . . . . ?
N2 C4 C13 C14 171.3(2) . . . . ?
C3 C4 C13 C14 -72.0(3) . . . . ?
C18 C13 C14 C15 -2.5(4) . . . . ?
C4 C13 C14 C15 177.2(2) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C14 C15 C16 C19 -178.7(3) . . . . ?
C15 C16 C17 C18 -2.7(4) . . . . ?
C19 C16 C17 C18 176.9(3) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
C4 C13 C18 C17 -179.0(2) . . . . ?
C16 C17 C18 C13 1.9(4) . . . . ?
C21 O4 C20 O3 4.4(4) . . . . ?
C21 O4 C20 C5 -178.9(2) . . . . ?
N2 C5 C20 O3 2.7(4) . . . . ?
C6 C5 C20 O3 -113.6(3) . . . . ?
N2 C5 C20 O4 -174.0(2) . . . . ?
C6 C5 C20 O4 69.7(3) . . . . ?

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

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

data_a2014220_ac53
_database_code_depnum_ccdc_archive 'CCDC 1411372'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;

_audit_creation_date             2014-11-18T14:02:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O4 S1'
_chemical_formula_sum            'C18 H16 N2 O4 S'
_chemical_formula_weight         356.39
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   6.58750(10)
_cell_length_b                   25.7074(3)
_cell_length_c                   10.05520(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.2450(10)
_cell_angle_gamma                90
_cell_volume                     1670.13(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8343
_cell_measurement_theta_min      4.783
_cell_measurement_theta_max      76.427
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5837
_exptl_crystal_size_mid          0.1874
_exptl_crystal_size_min          0.1214
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0633
4 3 -2 0.2908
0 1 0 0.0814
0 2 1 0.084
0 -1 1 0.0704
2 3 0 0.2862
-1 -2 0 0.2726
1 -7 -1 0.1174
-1 6 -6 0.0607
0 4 -3 0.0471
-2 13 3 0.0951

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.954
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_T_max  0.827

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_ub_11      -0.110845
_diffrn_orient_matrix_ub_12      0.0368431
_diffrn_orient_matrix_ub_13      -0.1117975
_diffrn_orient_matrix_ub_21      0.0384655
_diffrn_orient_matrix_ub_22      -0.038881
_diffrn_orient_matrix_ub_23      -0.1090747
_diffrn_orient_matrix_ub_31      -0.207506
_diffrn_orient_matrix_ub_32      -0.0268733
_diffrn_orient_matrix_ub_33      0.0044406
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_number            13442
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.8
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_full        72.49
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3306
_reflns_number_gt                3105
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   37.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega -122.00  -96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -86.0000 -105.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -37.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -63.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  102.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   82.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 75

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   30.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256 -125.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 17 omega   31.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256    0.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 18 omega  -36.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 19 omega -167.00 -141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -94.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   56.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   34.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   62.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
 26 omega   53.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 27 omega   43.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 28 omega   43.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
 29 omega   54.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 42

;

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

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          disorder
_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)+(0.0435P)²+0.7213P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3306
_refine_ls_number_parameters     250
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.045

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.18704(15) 0.43881(4) 0.44781(10) 0.0205(2) Uani 1 1 d . . .
O2 O 0.63130(15) 0.33621(4) 0.27762(10) 0.0226(2) Uani 1 1 d . . .
O3 O 1.24807(15) 0.50112(4) 0.19025(10) 0.0212(2) Uani 1 1 d . . .
O4 O 1.15881(15) 0.55504(4) 0.34472(10) 0.0192(2) Uani 1 1 d . . .
N1 N 0.93078(17) 0.37772(4) 0.38169(12) 0.0167(2) Uani 1 1 d . . .
N2 N 0.84518(18) 0.46850(5) 0.10498(12) 0.0190(3) Uani 1 1 d . . .
C6 C 0.8397(2) 0.46547(5) 0.33594(13) 0.0165(3) Uani 1 1 d . . .
H6 H 0.7945 0.4863 0.409 0.02 Uiso 1 1 calc R . .
C13 C 1.1198(2) 0.51807(5) 0.24961(13) 0.0174(3) Uani 1 1 d . . .
C2 C 0.7302(2) 0.37573(5) 0.30305(13) 0.0173(3) Uani 1 1 d . . .
C5 C 0.8951(2) 0.50131(5) 0.22477(13) 0.0170(3) Uani 1 1 d . . .
H5 H 0.8034 0.5326 0.2135 0.02 Uiso 1 1 calc R . .
C4 C 0.6454(2) 0.44399(5) 0.10861(14) 0.0182(3) Uani 1 1 d . A .
H4 H 0.5338 0.4706 0.0825 0.022 Uiso 1 1 calc R . .
C1 C 1.0107(2) 0.42789(5) 0.39490(13) 0.0169(3) Uani 1 1 d . . .
C3 C 0.6630(2) 0.43081(5) 0.26224(14) 0.0173(3) Uani 1 1 d . . .
H3 H 0.5308 0.4394 0.2922 0.021 Uiso 1 1 calc R . .
C7 C 1.0390(2) 0.33312(5) 0.44593(14) 0.0181(3) Uani 1 1 d . . .
C8 C 1.2317(2) 0.32058(6) 0.41959(15) 0.0225(3) Uani 1 1 d . . .
H8 H 1.2912 0.3407 0.3578 0.027 Uiso 1 1 calc R . .
C11 C 1.0556(3) 0.26093(6) 0.59876(16) 0.0279(3) Uani 1 1 d . . .
H11 H 0.9949 0.2403 0.6591 0.033 Uiso 1 1 calc R . .
C12 C 0.9497(2) 0.30380(6) 0.53536(15) 0.0233(3) Uani 1 1 d . . .
H12 H 0.8178 0.3129 0.553 0.028 Uiso 1 1 calc R . .
C15 C 0.6050(2) 0.40001(5) 0.01052(14) 0.0218(3) Uani 1 1 d D . .
C9 C 1.3368(2) 0.27803(6) 0.48511(17) 0.0288(4) Uani 1 1 d . . .
H9 H 1.4699 0.2693 0.4687 0.035 Uiso 1 1 calc R . .
C10 C 1.2494(3) 0.24821(6) 0.57411(17) 0.0296(4) Uani 1 1 d . . .
H10 H 1.3222 0.2191 0.6181 0.036 Uiso 1 1 calc R . .
C18A C 0.6352(3) 0.32484(7) -0.1372(2) 0.0363(5) Uani 0.905(2) 1 d PDU A 1
H18A H 0.6767 0.2965 -0.1865 0.044 Uiso 0.905(2) 1 calc PR A 1
C17A C 0.4340(3) 0.33904(9) -0.1422(2) 0.0369(5) Uani 0.905(2) 1 d PDU A 1
H17A H 0.319 0.322 -0.1963 0.044 Uiso 0.905(2) 1 calc PR A 1
C14 C 1.3748(2) 0.57062(6) 0.37912(15) 0.0238(3) Uani 1 1 d . . .
H14A H 1.4219 0.5814 0.2967 0.036 Uiso 1 1 calc R . .
H14B H 1.4587 0.5412 0.4206 0.036 Uiso 1 1 calc R . .
H14C H 1.3895 0.5997 0.4432 0.036 Uiso 1 1 calc R . .
S1A S 0.80388(8) 0.36447(2) -0.03087(6) 0.02828(17) Uani 0.905(2) 1 d PDU A 1
C16A C 0.4165(3) 0.38235(10) -0.0570(3) 0.0249(5) Uani 0.905(2) 1 d PDU A 1
H16A H 0.2882 0.3974 -0.0478 0.03 Uiso 0.905(2) 1 calc PR A 1
S1B S 0.3718(8) 0.3767(4) -0.0726(11) 0.043(2) Uani 0.095(2) 1 d PDU A 2
C16B C 0.770(2) 0.3718(10) -0.014(3) 0.043(2) Uani 0.095(2) 1 d PDU A 2
H16B H 0.9108 0.378 0.0274 0.052 Uiso 0.095(2) 1 calc PR A 2
C18B C 0.490(2) 0.3292(10) -0.150(3) 0.043(2) Uani 0.095(2) 1 d PDU A 2
H18B H 0.4196 0.3044 -0.2119 0.052 Uiso 0.095(2) 1 calc PR A 2
C17B C 0.7009(19) 0.3318(9) -0.109(3) 0.043(2) Uani 0.095(2) 1 d PDU A 2
H17B H 0.7927 0.3088 -0.1418 0.052 Uiso 0.095(2) 1 calc PR A 2
H2 H 0.841(3) 0.4856(8) 0.030(2) 0.029(5) Uiso 1 1 d . . .



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

_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
O1 C1 1.2127(17) . ?
O2 C2 1.2071(17) . ?
O3 C13 1.2071(17) . ?
O4 C13 1.3372(17) . ?
O4 C14 1.4534(17) . ?
N1 C1 1.3896(18) . ?
N1 C2 1.4023(17) . ?
N1 C7 1.4354(17) . ?
N2 C5 1.4547(17) . ?
N2 C4 1.4662(18) . ?
N2 H2 0.87(2) . ?
C6 C1 1.5142(18) . ?
C6 C3 1.5367(18) . ?
C6 C5 1.5464(18) . ?
C6 H6 1 . ?
C13 C5 1.5146(19) . ?
C2 C3 1.5162(19) . ?
C5 H5 1 . ?
C4 C15 1.4899(19) . ?
C4 C3 1.5635(18) . ?
C4 H4 1 . ?
C3 H3 1 . ?
C7 C8 1.385(2) . ?
C7 C12 1.389(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.95 . ?
C11 C10 1.387(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C15 C16B 1.369(2) . ?
C15 C16A 1.3707(18) . ?
C15 S1B 1.707(2) . ?
C15 S1A 1.7137(13) . ?
C9 C10 1.386(2) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C18A C17A 1.3660(18) . ?
C18A S1A 1.7184(15) . ?
C18A H18A 0.95 . ?
C17A C16A 1.4233(19) . ?
C17A H17A 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C16A H16A 0.95 . ?
S1B C18B 1.715(2) . ?
C16B C17B 1.419(2) . ?
C16B H16B 0.95 . ?
C18B C17B 1.369(2) . ?
C18B H18B 0.95 . ?
C17B H17B 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 C14 114.12(11) . . ?
C1 N1 C2 112.67(11) . . ?
C1 N1 C7 123.56(11) . . ?
C2 N1 C7 123.73(11) . . ?
C5 N2 C4 106.73(11) . . ?
C5 N2 H2 113.0(13) . . ?
C4 N2 H2 111.2(13) . . ?
C1 C6 C3 104.75(11) . . ?
C1 C6 C5 113.62(11) . . ?
C3 C6 C5 105.09(10) . . ?
C1 C6 H6 111 . . ?
C3 C6 H6 111 . . ?
C5 C6 H6 111 . . ?
O3 C13 O4 123.70(13) . . ?
O3 C13 C5 124.86(13) . . ?
O4 C13 C5 111.43(11) . . ?
O2 C2 N1 124.09(13) . . ?
O2 C2 C3 127.72(12) . . ?
N1 C2 C3 108.17(11) . . ?
N2 C5 C13 110.95(11) . . ?
N2 C5 C6 101.88(11) . . ?
C13 C5 C6 114.28(11) . . ?
N2 C5 H5 109.8 . . ?
C13 C5 H5 109.8 . . ?
C6 C5 H5 109.8 . . ?
N2 C4 C15 110.79(11) . . ?
N2 C4 C3 102.93(10) . . ?
C15 C4 C3 117.32(12) . . ?
N2 C4 H4 108.5 . . ?
C15 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
O1 C1 N1 124.71(13) . . ?
O1 C1 C6 126.86(12) . . ?
N1 C1 C6 108.41(11) . . ?
C2 C3 C6 104.90(10) . . ?
C2 C3 C4 115.55(11) . . ?
C6 C3 C4 104.72(11) . . ?
C2 C3 H3 110.4 . . ?
C6 C3 H3 110.4 . . ?
C4 C3 H3 110.4 . . ?
C8 C7 C12 121.15(13) . . ?
C8 C7 N1 119.55(13) . . ?
C12 C7 N1 119.29(13) . . ?
C7 C8 C9 118.88(15) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C11 C12 120.12(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.30(14) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C16B C15 C16A 114.3(8) . . ?
C16B C15 C4 118.3(9) . . ?
C16A C15 C4 127.34(14) . . ?
C16B C15 S1B 113.5(10) . . ?
C16A C15 S1B 1.2(5) . . ?
C4 C15 S1B 128.1(3) . . ?
C16B C15 S1A 3.8(12) . . ?
C16A C15 S1A 111.40(14) . . ?
C4 C15 S1A 121.26(10) . . ?
S1B C15 S1A 110.6(3) . . ?
C10 C9 C8 120.68(15) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.86(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C17A C18A S1A 111.68(13) . . ?
C17A C18A H18A 124.2 . . ?
S1A C18A H18A 124.2 . . ?
C18A C17A C16A 112.25(17) . . ?
C18A C17A H17A 123.9 . . ?
C16A C17A H17A 123.9 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 S1A C18A 91.99(8) . . ?
C15 C16A C17A 112.7(2) . . ?
C15 C16A H16A 123.7 . . ?
C17A C16A H16A 123.7 . . ?
C15 S1B C18B 91.5(5) . . ?
C15 C16B C17B 109.9(11) . . ?
C15 C16B H16B 125 . . ?
C17B C16B H16B 125 . . ?
C17B C18B S1B 110.7(3) . . ?
C17B C18B H18B 124.6 . . ?
S1B C18B H18B 124.6 . . ?
C18B C17B C16B 114.3(7) . . ?
C18B C17B H17B 122.8 . . ?
C16B C17B H17B 122.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O4 C13 O3 -4.61(18) . . . . ?
C14 O4 C13 C5 176.50(11) . . . . ?
C1 N1 C2 O2 179.58(13) . . . . ?
C7 N1 C2 O2 -2.7(2) . . . . ?
C1 N1 C2 C3 -2.20(15) . . . . ?
C7 N1 C2 C3 175.57(12) . . . . ?
C4 N2 C5 C13 166.13(11) . . . . ?
C4 N2 C5 C6 44.09(13) . . . . ?
O3 C13 C5 N2 -9.44(19) . . . . ?
O4 C13 C5 N2 169.43(11) . . . . ?
O3 C13 C5 C6 105.04(15) . . . . ?
O4 C13 C5 C6 -76.08(14) . . . . ?
C1 C6 C5 N2 83.77(13) . . . . ?
C3 C6 C5 N2 -30.17(13) . . . . ?
C1 C6 C5 C13 -35.94(16) . . . . ?
C3 C6 C5 C13 -149.88(11) . . . . ?
C5 N2 C4 C15 -165.92(11) . . . . ?
C5 N2 C4 C3 -39.71(13) . . . . ?
C2 N1 C1 O1 -173.18(13) . . . . ?
C7 N1 C1 O1 9.0(2) . . . . ?
C2 N1 C1 C6 8.28(15) . . . . ?
C7 N1 C1 C6 -169.49(12) . . . . ?
C3 C6 C1 O1 170.86(13) . . . . ?
C5 C6 C1 O1 56.72(18) . . . . ?
C3 C6 C1 N1 -10.65(14) . . . . ?
C5 C6 C1 N1 -124.79(12) . . . . ?
O2 C2 C3 C6 173.52(13) . . . . ?
N1 C2 C3 C6 -4.63(14) . . . . ?
O2 C2 C3 C4 -71.73(18) . . . . ?
N1 C2 C3 C4 110.13(13) . . . . ?
C1 C6 C3 C2 9.03(13) . . . . ?
C5 C6 C3 C2 129.03(11) . . . . ?
C1 C6 C3 C4 -113.07(11) . . . . ?
C5 C6 C3 C4 6.94(13) . . . . ?
N2 C4 C3 C2 -96.24(13) . . . . ?
C15 C4 C3 C2 25.67(17) . . . . ?
N2 C4 C3 C6 18.62(13) . . . . ?
C15 C4 C3 C6 140.52(12) . . . . ?
C1 N1 C7 C8 -58.13(19) . . . . ?
C2 N1 C7 C8 124.34(15) . . . . ?
C1 N1 C7 C12 120.76(15) . . . . ?
C2 N1 C7 C12 -56.77(19) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
N1 C7 C8 C9 178.44(13) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
N1 C7 C12 C11 -179.29(13) . . . . ?
C10 C11 C12 C7 0.9(2) . . . . ?
N2 C4 C15 C16B 32.5(18) . . . . ?
C3 C4 C15 C16B -85.2(18) . . . . ?
N2 C4 C15 C16A -150.3(2) . . . . ?
C3 C4 C15 C16A 92.0(2) . . . . ?
N2 C4 C15 S1B -151.4(5) . . . . ?
C3 C4 C15 S1B 90.9(6) . . . . ?
N2 C4 C15 S1A 29.75(16) . . . . ?
C3 C4 C15 S1A -87.99(14) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C12 C11 C10 C9 -0.6(2) . . . . ?
S1A C18A C17A C16A -0.8(3) . . . . ?
C16B C15 S1A C18A 14E1(2) . . . . ?
C16A C15 S1A C18A -0.94(19) . . . . ?
C4 C15 S1A C18A 179.04(13) . . . . ?
S1B C15 S1A C18A 0.0(5) . . . . ?
C17A C18A S1A C15 0.98(19) . . . . ?
C16B C15 C16A C17A -2.0(18) . . . . ?
C4 C15 C16A C17A -179.30(19) . . . . ?
S1B C15 C16A C17A -5E1(2) . . . . ?
S1A C15 C16A C17A 0.7(3) . . . . ?
C18A C17A C16A C15 0.1(3) . . . . ?
C16B C15 S1B C18B -2(2) . . . . ?
C16A C15 S1B C18B 13E1(2) . . . . ?
C4 C15 S1B C18B -178.6(13) . . . . ?
S1A C15 S1B C18B 0.3(14) . . . . ?
C16A C15 C16B C17B 2(3) . . . . ?
C4 C15 C16B C17B 179.8(19) . . . . ?
S1B C15 C16B C17B 3(3) . . . . ?
S1A C15 C16B C17B -39(18) . . . . ?
C15 S1B C18B C17B 1(3) . . . . ?
S1B C18B C17B C16B 1(4) . . . . ?
C15 C16B C17B C18B -3(4) . . . . ?

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

# END of CIF
