# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_a_sq
_audit_creation_date             2014-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        anti-5g
_chemical_formula_moiety         'C14 H14 N4 O4'
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_weight         302.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   18.769(4)
_cell_length_b                   12.495(3)
_cell_length_c                   13.680(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3208.1(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4732
_cell_measurement_theta_min      1.4886
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26174
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.714
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             7581
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0162
_diffrn_orient_matrix_UB_12      -0.0334
_diffrn_orient_matrix_UB_13      -0.0709
_diffrn_orient_matrix_UB_21      0.0009
_diffrn_orient_matrix_UB_22      0.0662
_diffrn_orient_matrix_UB_23      -0.0310
_diffrn_orient_matrix_UB_31      0.0522
_diffrn_orient_matrix_UB_32      0.0040
_diffrn_orient_matrix_UB_33      0.0101
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6526
_reflns_number_total             7275
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 2080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0873P)²+2.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2014
_refine_ls_wR_factor_ref         0.2066
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5A(H5A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C13A(H13A,H13B), C2(H2A,H2B), C3(H3A,H3B),
 C13(H13C,H13D)
2.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1A O 0.44527(17) 0.1122(3) 0.1498(2) 0.0286(7) Uani 1 1 d . . . . .
O2A O 0.53516(19) 0.1243(3) 0.0437(3) 0.0387(9) Uani 1 1 d . . . . .
O3A O 0.2841(2) 0.2505(3) 0.4405(3) 0.0418(9) Uani 1 1 d . . . . .
O4A O 0.3067(2) 0.3664(3) 0.3172(3) 0.0416(9) Uani 1 1 d . . . . .
N1A N 0.2810(3) 0.2566(4) 0.1275(3) 0.0384(10) Uani 1 1 d . . . . .
N2A N 0.2801(3) 0.3552(4) 0.1153(3) 0.0395(10) Uani 1 1 d . . . . .
N3A N 0.2721(3) 0.4427(4) 0.0969(4) 0.0526(14) Uani 1 1 d . . . . .
N4A N 0.3146(2) 0.1930(3) 0.2868(3) 0.0347(10) Uani 1 1 d . . . . .
C1A C 0.3671(3) 0.1072(4) 0.1489(3) 0.0304(10) Uani 1 1 d . . . . .
C2A C 0.3482(3) 0.0797(4) 0.0431(4) 0.0334(11) Uani 1 1 d . . . . .
H2AA H 0.3050 0.1162 0.0228 0.040 Uiso 1 1 calc R . . . .
H2AB H 0.3417 0.0032 0.0350 0.040 Uiso 1 1 calc R . . . .
C3A C 0.4127(3) 0.1194(4) -0.0152(4) 0.0346(11) Uani 1 1 d . . . . .
H3AA H 0.4233 0.0716 -0.0691 0.042 Uiso 1 1 calc R . . . .
H3AB H 0.4044 0.1908 -0.0407 0.042 Uiso 1 1 calc R . . . .
C4A C 0.4716(3) 0.1195(4) 0.0579(4) 0.0311(10) Uani 1 1 d . . . . .
C5A C 0.3403(2) 0.2180(4) 0.1886(3) 0.0288(10) Uani 1 1 d . . . . .
H5A H 0.3792 0.2704 0.1908 0.035 Uiso 1 1 calc R . . . .
C6A C 0.3120(3) 0.0809(4) 0.3032(3) 0.0274(10) Uani 1 1 d . . . . .
C7A C 0.3434(3) 0.0280(4) 0.2241(4) 0.0320(10) Uani 1 1 d . . . . .
C8A C 0.3494(3) -0.0810(4) 0.2225(5) 0.0427(13) Uani 1 1 d . . . . .
H8A H 0.3716 -0.1159 0.1707 0.051 Uiso 1 1 calc R . . . .
C9A C 0.3210(4) -0.1387(4) 0.3013(5) 0.0498(15) Uani 1 1 d . . . . .
H9A H 0.3235 -0.2130 0.3011 0.060 Uiso 1 1 calc R . . . .
C10A C 0.2896(3) -0.0877(5) 0.3784(5) 0.0460(14) Uani 1 1 d . . . . .
H10A H 0.2710 -0.1276 0.4299 0.055 Uiso 1 1 calc R . . . .
C11A C 0.2851(3) 0.0241(4) 0.3807(4) 0.0398(12) Uani 1 1 d . . . . .
H11A H 0.2644 0.0590 0.4335 0.048 Uiso 1 1 calc R . . . .
C12A C 0.3005(3) 0.2690(4) 0.3568(4) 0.0351(11) Uani 1 1 d . . . . .
C13A C 0.2927(3) 0.4550(4) 0.3842(4) 0.0417(13) Uani 1 1 d . . . . .
H13A H 0.3278 0.4554 0.4362 0.050 Uiso 1 1 calc R . . . .
H13B H 0.2459 0.4468 0.4133 0.050 Uiso 1 1 calc R . . . .
C14A C 0.2962(4) 0.5584(5) 0.3278(6) 0.0600(18) Uani 1 1 d . . . . .
H14A H 0.2598 0.5589 0.2785 0.090 Uiso 1 1 calc GR . . . .
H14B H 0.3421 0.5648 0.2974 0.090 Uiso 1 1 calc GR . . . .
H14C H 0.2890 0.6174 0.3716 0.090 Uiso 1 1 calc GR . . . .
O1 O 0.51710(18) 0.3533(3) 0.9212(3) 0.0334(8) Uani 1 1 d . . . . .
O2 O 0.4495(2) 0.3708(3) 1.0528(3) 0.0445(10) Uani 1 1 d . . . . .
O3 O 0.5950(3) 0.4832(3) 0.5781(3) 0.0494(10) Uani 1 1 d . . . . .
O4 O 0.5975(2) 0.6044(3) 0.7018(3) 0.0419(9) Uani 1 1 d . . . . .
N1 N 0.6816(2) 0.4960(4) 0.8634(3) 0.0378(10) Uani 1 1 d . . . . .
N2 N 0.6873(2) 0.5942(4) 0.8744(3) 0.0361(10) Uani 1 1 d . . . . .
N3 N 0.7009(3) 0.6807(4) 0.8865(4) 0.0554(14) Uani 1 1 d . . . . .
N4 N 0.6023(3) 0.4311(4) 0.7377(3) 0.0371(10) Uani 1 1 d . . . . .
C1 C 0.5927(2) 0.3511(4) 0.8941(4) 0.0286(10) Uani 1 1 d . . . . .
C2 C 0.6313(3) 0.3305(4) 0.9919(4) 0.0337(11) Uani 1 1 d . . . . .
H2A H 0.6419 0.2550 0.9996 0.040 Uiso 1 1 calc R . . . .
H2B H 0.6754 0.3708 0.9951 0.040 Uiso 1 1 calc R . . . .
C3 C 0.5798(3) 0.3677(4) 1.0694(4) 0.0391(12) Uani 1 1 d . . . . .
H3A H 0.5808 0.3203 1.1255 0.047 Uiso 1 1 calc R . . . .
H3B H 0.5911 0.4398 1.0907 0.047 Uiso 1 1 calc R . . . .
C4 C 0.5087(3) 0.3642(4) 1.0199(4) 0.0345(11) Uani 1 1 d . . . . .
C5 C 0.6076(3) 0.4583(4) 0.8418(3) 0.0313(10) Uani 1 1 d . . . . .
H5 H 0.5723 0.5126 0.8599 0.038 Uiso 1 1 calc R . . . .
C6 C 0.6052(3) 0.3182(4) 0.7238(4) 0.0353(11) Uani 1 1 d . . . . .
C7 C 0.6015(3) 0.2694(4) 0.8150(4) 0.0344(11) Uani 1 1 d . . . . .
C8 C 0.6027(3) 0.1576(5) 0.8217(5) 0.0453(13) Uani 1 1 d . . . . .
H8 H 0.6001 0.1236 0.8821 0.054 Uiso 1 1 calc R . . . .
C9 C 0.6080(4) 0.0992(5) 0.7367(5) 0.0493(15) Uani 1 1 d . . . . .
H9 H 0.6094 0.0249 0.7397 0.059 Uiso 1 1 calc R . . . .
C10 C 0.6112(4) 0.1500(5) 0.6468(5) 0.0521(15) Uani 1 1 d . . . . .
H10 H 0.6142 0.1083 0.5906 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6100(3) 0.2618(5) 0.6372(5) 0.0459(14) Uani 1 1 d . . . . .
H11 H 0.6123 0.2956 0.5767 0.055 Uiso 1 1 calc R . . . .
C12 C 0.5986(3) 0.5058(5) 0.6651(4) 0.0372(11) Uani 1 1 d . . . . .
C13 C 0.5910(4) 0.6902(5) 0.6309(5) 0.0504(15) Uani 1 1 d . . . . .
H13C H 0.5466 0.6834 0.5951 0.060 Uiso 1 1 calc R . . . .
H13D H 0.6300 0.6872 0.5845 0.060 Uiso 1 1 calc R . . . .
C14 C 0.5925(5) 0.7936(5) 0.6850(5) 0.0624(19) Uani 1 1 d . . . . .
H14D H 0.5860 0.8517 0.6399 0.094 Uiso 1 1 calc GR . . . .
H14E H 0.6376 0.8013 0.7174 0.094 Uiso 1 1 calc GR . . . .
H14F H 0.5549 0.7945 0.7325 0.094 Uiso 1 1 calc GR . . . .


_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
O1A C1A 1.468(6) . ?
O1A C4A 1.353(6) . ?
O2A C4A 1.211(6) . ?
O3A C12A 1.209(6) . ?
O4A C12A 1.336(7) . ?
O4A C13A 1.461(6) . ?
N1A N2A 1.243(6) . ?
N1A C5A 1.473(6) . ?
N2A N3A 1.131(7) . ?
N4A C5A 1.461(6) . ?
N4A C6A 1.419(6) . ?
N4A C12A 1.375(7) . ?
C1A C2A 1.530(7) . ?
C1A C5A 1.570(7) . ?
C1A C7A 1.496(7) . ?
C2A C3A 1.532(7) . ?
C3A C4A 1.491(7) . ?
C6A C7A 1.399(7) . ?
C6A C11A 1.371(7) . ?
C7A C8A 1.367(7) . ?
C8A C9A 1.402(9) . ?
C9A C10A 1.366(9) . ?
C10A C11A 1.399(8) . ?
C13A C14A 1.506(9) . ?
O1 C1 1.467(5) . ?
O1 C4 1.366(6) . ?
O2 C4 1.201(6) . ?
O3 C12 1.224(6) . ?
O4 C12 1.331(7) . ?
O4 C13 1.451(7) . ?
N1 N2 1.240(7) . ?
N1 C5 1.496(7) . ?
N2 N3 1.124(7) . ?
N4 C5 1.467(6) . ?
N4 C6 1.425(7) . ?
N4 C12 1.364(7) . ?
C1 C2 1.543(7) . ?
C1 C5 1.544(7) . ?
C1 C7 1.497(7) . ?
C2 C3 1.508(8) . ?
C3 C4 1.498(8) . ?
C6 C7 1.390(8) . ?
C6 C11 1.381(8) . ?
C7 C8 1.400(8) . ?
C8 C9 1.376(9) . ?
C9 C10 1.385(10) . ?
C10 C11 1.404(9) . ?
C13 C14 1.489(9) . ?

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
C4A O1A C1A 111.1(4) . . ?
C12A O4A C13A 114.8(4) . . ?
N2A N1A C5A 114.2(4) . . ?
N3A N2A N1A 171.3(6) . . ?
C6A N4A C5A 111.6(4) . . ?
C12A N4A C5A 123.8(4) . . ?
C12A N4A C6A 124.4(4) . . ?
O1A C1A C2A 104.5(4) . . ?
O1A C1A C5A 106.3(4) . . ?
O1A C1A C7A 108.6(4) . . ?
C2A C1A C5A 116.8(4) . . ?
C7A C1A C2A 115.7(4) . . ?
C7A C1A C5A 104.5(4) . . ?
C1A C2A C3A 103.6(4) . . ?
C4A C3A C2A 103.7(4) . . ?
O1A C4A C3A 110.6(4) . . ?
O2A C4A O1A 120.8(5) . . ?
O2A C4A C3A 128.5(5) . . ?
N1A C5A C1A 109.5(4) . . ?
N4A C5A N1A 110.0(4) . . ?
N4A C5A C1A 103.6(4) . . ?
C7A C6A N4A 109.2(4) . . ?
C11A C6A N4A 130.3(5) . . ?
C11A C6A C7A 120.5(5) . . ?
C6A C7A C1A 110.2(4) . . ?
C8A C7A C1A 128.6(5) . . ?
C8A C7A C6A 121.2(5) . . ?
C7A C8A C9A 117.9(6) . . ?
C10A C9A C8A 121.2(5) . . ?
C9A C10A C11A 120.5(5) . . ?
C6A C11A C10A 118.6(5) . . ?
O3A C12A O4A 125.5(5) . . ?
O3A C12A N4A 125.2(5) . . ?
O4A C12A N4A 109.3(4) . . ?
O4A C13A C14A 108.7(5) . . ?
C4 O1 C1 111.4(4) . . ?
C12 O4 C13 115.7(4) . . ?
N2 N1 C5 114.5(4) . . ?
N3 N2 N1 171.6(6) . . ?
C6 N4 C5 110.9(4) . . ?
C12 N4 C5 123.5(4) . . ?
C12 N4 C6 125.6(4) . . ?
O1 C1 C2 103.7(4) . . ?
O1 C1 C5 106.1(4) . . ?
O1 C1 C7 107.6(4) . . ?
C2 C1 C5 117.5(4) . . ?
C7 C1 C2 117.4(4) . . ?
C7 C1 C5 103.7(4) . . ?
C3 C2 C1 104.9(4) . . ?
C4 C3 C2 104.1(4) . . ?
O1 C4 C3 110.3(4) . . ?
O2 C4 O1 119.0(5) . . ?
O2 C4 C3 130.8(5) . . ?
N1 C5 C1 110.5(4) . . ?
N4 C5 N1 109.1(4) . . ?
N4 C5 C1 103.7(4) . . ?
C7 C6 N4 108.2(5) . . ?
C11 C6 N4 128.4(5) . . ?
C11 C6 C7 123.3(5) . . ?
C6 C7 C1 110.8(4) . . ?
C6 C7 C8 119.7(5) . . ?
C8 C7 C1 129.4(5) . . ?
C9 C8 C7 118.3(6) . . ?
C8 C9 C10 120.7(6) . . ?
C9 C10 C11 122.6(6) . . ?
C6 C11 C10 115.3(6) . . ?
O3 C12 O4 125.3(5) . . ?
O3 C12 N4 123.6(5) . . ?
O4 C12 N4 111.1(4) . . ?
O4 C13 C14 107.9(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
O1A C1A C2A C3A -24.3(5) . . . . ?
O1A C1A C5A N1A 136.1(4) . . . . ?
O1A C1A C5A N4A -106.5(4) . . . . ?
O1A C1A C7A C6A 108.7(5) . . . . ?
O1A C1A C7A C8A -71.1(7) . . . . ?
N2A N1A C5A N4A 102.9(5) . . . . ?
N2A N1A C5A C1A -143.9(5) . . . . ?
N4A C6A C7A C1A -1.4(6) . . . . ?
N4A C6A C7A C8A 178.4(5) . . . . ?
N4A C6A C11A C10A -179.8(6) . . . . ?
C1A O1A C4A O2A -179.9(4) . . . . ?
C1A O1A C4A C3A -0.4(5) . . . . ?
C1A C2A C3A C4A 23.9(5) . . . . ?
C1A C7A C8A C9A -178.2(5) . . . . ?
C2A C1A C5A N1A 20.1(6) . . . . ?
C2A C1A C5A N4A 137.4(4) . . . . ?
C2A C1A C7A C6A -134.3(5) . . . . ?
C2A C1A C7A C8A 45.9(8) . . . . ?
C2A C3A C4A O1A -15.3(5) . . . . ?
C2A C3A C4A O2A 164.1(5) . . . . ?
C4A O1A C1A C2A 16.1(5) . . . . ?
C4A O1A C1A C5A -108.1(4) . . . . ?
C4A O1A C1A C7A 140.0(4) . . . . ?
C5A N4A C6A C7A 7.3(6) . . . . ?
C5A N4A C6A C11A -173.1(5) . . . . ?
C5A N4A C12A O3A -174.5(5) . . . . ?
C5A N4A C12A O4A 6.6(7) . . . . ?
C5A C1A C2A C3A 92.7(5) . . . . ?
C5A C1A C7A C6A -4.4(5) . . . . ?
C5A C1A C7A C8A 175.7(6) . . . . ?
C6A N4A C5A N1A 107.4(5) . . . . ?
C6A N4A C5A C1A -9.7(5) . . . . ?
C6A N4A C12A O3A -0.2(9) . . . . ?
C6A N4A C12A O4A -179.1(5) . . . . ?
C6A C7A C8A C9A 2.0(9) . . . . ?
C7A C1A C2A C3A -143.6(4) . . . . ?
C7A C1A C5A N1A -109.1(4) . . . . ?
C7A C1A C5A N4A 8.2(5) . . . . ?
C7A C6A C11A C10A -0.3(8) . . . . ?
C7A C8A C9A C10A -1.3(10) . . . . ?
C8A C9A C10A C11A -0.1(11) . . . . ?
C9A C10A C11A C6A 0.9(10) . . . . ?
C11A C6A C7A C1A 179.0(5) . . . . ?
C11A C6A C7A C8A -1.2(8) . . . . ?
C12A O4A C13A C14A -175.8(5) . . . . ?
C12A N4A C5A N1A -77.7(6) . . . . ?
C12A N4A C5A C1A 165.3(5) . . . . ?
C12A N4A C6A C7A -167.6(5) . . . . ?
C12A N4A C6A C11A 12.0(9) . . . . ?
C13A O4A C12A O3A 0.8(8) . . . . ?
C13A O4A C12A N4A 179.7(5) . . . . ?
O1 C1 C2 C3 -22.9(5) . . . . ?
O1 C1 C5 N1 145.9(4) . . . . ?
O1 C1 C5 N4 -97.3(4) . . . . ?
O1 C1 C7 C6 100.4(5) . . . . ?
O1 C1 C7 C8 -76.3(7) . . . . ?
N2 N1 C5 N4 104.6(5) . . . . ?
N2 N1 C5 C1 -142.0(5) . . . . ?
N4 C6 C7 C1 2.4(6) . . . . ?
N4 C6 C7 C8 179.5(5) . . . . ?
N4 C6 C11 C10 -179.4(6) . . . . ?
C1 O1 C4 O2 177.6(4) . . . . ?
C1 O1 C4 C3 -1.5(6) . . . . ?
C1 C2 C3 C4 22.0(5) . . . . ?
C1 C7 C8 C9 176.7(5) . . . . ?
C2 C1 C5 N1 30.5(6) . . . . ?
C2 C1 C5 N4 147.3(4) . . . . ?
C2 C1 C7 C6 -143.2(5) . . . . ?
C2 C1 C7 C8 40.1(8) . . . . ?
C2 C3 C4 O1 -13.5(6) . . . . ?
C2 C3 C4 O2 167.6(5) . . . . ?
C4 O1 C1 C2 15.4(5) . . . . ?
C4 O1 C1 C5 -109.0(4) . . . . ?
C4 O1 C1 C7 140.5(4) . . . . ?
C5 N4 C6 C7 8.8(6) . . . . ?
C5 N4 C6 C11 -172.0(6) . . . . ?
C5 N4 C12 O3 179.1(6) . . . . ?
C5 N4 C12 O4 -2.6(8) . . . . ?
C5 C1 C2 C3 93.8(5) . . . . ?
C5 C1 C7 C6 -11.7(5) . . . . ?
C5 C1 C7 C8 171.6(6) . . . . ?
C6 N4 C5 N1 102.2(5) . . . . ?
C6 N4 C5 C1 -15.6(6) . . . . ?
C6 N4 C12 O3 2.4(9) . . . . ?
C6 N4 C12 O4 -179.3(5) . . . . ?
C6 C7 C8 C9 0.3(9) . . . . ?
C7 C1 C2 C3 -141.4(4) . . . . ?
C7 C1 C5 N1 -100.9(4) . . . . ?
C7 C1 C5 N4 15.9(5) . . . . ?
C7 C6 C11 C10 -0.2(9) . . . . ?
C7 C8 C9 C10 -0.7(10) . . . . ?
C8 C9 C10 C11 0.7(11) . . . . ?
C9 C10 C11 C6 -0.2(10) . . . . ?
C11 C6 C7 C1 -176.9(5) . . . . ?
C11 C6 C7 C8 0.2(8) . . . . ?
C12 O4 C13 C14 -178.6(6) . . . . ?
C12 N4 C5 N1 -74.9(6) . . . . ?
C12 N4 C5 C1 167.3(5) . . . . ?
C12 N4 C6 C7 -174.2(5) . . . . ?
C12 N4 C6 C11 5.1(10) . . . . ?
C13 O4 C12 O3 0.4(9) . . . . ?
C13 O4 C12 N4 -177.9(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1015318'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mx2910
_audit_creation_date             2014-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        syn-5a
_chemical_formula_moiety         'C H2 Cl2, C21 H23 N5 O4 S'
_chemical_formula_sum            'C22 H25 Cl2 N5 O4 S'
_chemical_formula_weight         526.43
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8728(15)
_cell_length_b                   14.6282(18)
_cell_length_c                   16.068(2)
_cell_angle_alpha                73.171(6)
_cell_angle_beta                 81.536(7)
_cell_angle_gamma                77.112(7)
_cell_volume                     2375.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7891
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4845
_cell_measurement_theta_min      1.3292
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23787
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.707
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             10813
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0121
_diffrn_orient_matrix_UB_12      -0.0844
_diffrn_orient_matrix_UB_13      -0.0413
_diffrn_orient_matrix_UB_21      -0.0263
_diffrn_orient_matrix_UB_22      0.0444
_diffrn_orient_matrix_UB_23      -0.0513
_diffrn_orient_matrix_UB_31      0.0648
_diffrn_orient_matrix_UB_32      0.0010
_diffrn_orient_matrix_UB_33      -0.0077
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9349
_reflns_number_total             10808
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         10808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+1.9209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5A(H5A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C22A(H22A,H22B), C22(H22C,H22D), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,
 H4AB), C20A(H20A,H20B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C20(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C16A(H16A),
 C17A(H17A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C21A(H21A,H21B,H21C), C18(H18D,H18E,H18F), C21(H21D,
 H21E,H21F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1A Cl 0.89910(7) 0.84159(5) 0.47315(5) 0.03958(17) Uani 1 1 d . . . . .
Cl2A Cl 0.63087(8) 0.86856(8) 0.45358(6) 0.0613(3) Uani 1 1 d . . . . .
C22A C 0.7813(3) 0.8806(2) 0.39948(18) 0.0382(7) Uani 1 1 d . . . . .
H22A H 0.7805 0.9482 0.3681 0.046 Uiso 1 1 calc R . . . .
H22B H 0.8011 0.8425 0.3572 0.046 Uiso 1 1 calc R . . . .
Cl1 Cl 0.52970(8) 0.35443(9) 0.49814(6) 0.0665(3) Uani 1 1 d . . . . .
Cl2 Cl 0.79290(7) 0.34794(7) 0.51613(5) 0.0485(2) Uani 1 1 d . . . . .
C22 C 0.6760(3) 0.3782(3) 0.44353(19) 0.0464(8) Uani 1 1 d . . . . .
H22C H 0.7019 0.3410 0.4007 0.056 Uiso 1 1 calc R . . . .
H22D H 0.6668 0.4467 0.4128 0.056 Uiso 1 1 calc R . . . .
S1A S 0.64224(5) 0.87301(4) 0.15323(4) 0.02160(13) Uani 1 1 d . . . . .
O1A O 0.70140(16) 0.87329(12) 0.22678(11) 0.0269(4) Uani 1 1 d . . . . .
O2A O 0.65461(16) 0.94655(12) 0.07268(11) 0.0284(4) Uani 1 1 d . . . . .
O3A O 1.18360(16) 0.71188(14) 0.07425(12) 0.0324(4) Uani 1 1 d . . . . .
O4A O 1.22072(15) 0.64524(13) 0.21629(11) 0.0281(4) Uani 1 1 d . . . . .
N1A N 0.68697(17) 0.76385(14) 0.13719(12) 0.0203(4) Uani 1 1 d . . . . .
N2A N 1.02189(18) 0.67823(15) 0.17791(13) 0.0242(4) Uani 1 1 d . . . . .
N3A N 0.91743(19) 0.83307(15) 0.09571(13) 0.0256(4) Uani 1 1 d . . . . .
N4A N 0.9662(2) 0.87327(15) 0.02397(14) 0.0272(5) Uani 1 1 d . . . . .
N5A N 1.0064(3) 0.91982(17) -0.03882(16) 0.0428(6) Uani 1 1 d . . . . .
C1A C 0.8044(2) 0.69539(16) 0.16379(14) 0.0197(4) Uani 1 1 d . . . . .
C2A C 0.7852(2) 0.60657(17) 0.13763(15) 0.0233(5) Uani 1 1 d . . . . .
H2AA H 0.8658 0.5645 0.1288 0.028 Uiso 1 1 calc R . . . .
H2AB H 0.7318 0.5694 0.1823 0.028 Uiso 1 1 calc R . . . .
C3A C 0.7216(2) 0.64913(18) 0.05290(16) 0.0266(5) Uani 1 1 d . . . . .
H3AA H 0.6651 0.6085 0.0479 0.032 Uiso 1 1 calc R . . . .
H3AB H 0.7843 0.6547 0.0030 0.032 Uiso 1 1 calc R . . . .
C4A C 0.6473(2) 0.74960(18) 0.05819(16) 0.0269(5) Uani 1 1 d . . . . .
H4AA H 0.6684 0.7995 0.0066 0.032 Uiso 1 1 calc R . . . .
H4AB H 0.5568 0.7513 0.0638 0.032 Uiso 1 1 calc R . . . .
C5A C 0.9290(2) 0.72715(17) 0.11413(15) 0.0219(5) Uani 1 1 d . . . . .
H5A H 0.9515 0.7055 0.0606 0.026 Uiso 1 1 calc R . . . .
C6A C 0.9601(2) 0.65610(17) 0.26369(15) 0.0222(5) Uani 1 1 d . . . . .
C7A C 1.0104(2) 0.62517(18) 0.34380(16) 0.0263(5) Uani 1 1 d . . . . .
H7A H 1.0971 0.6158 0.3475 0.032 Uiso 1 1 calc R . . . .
C8A C 0.9271(2) 0.60863(18) 0.41834(16) 0.0279(5) Uani 1 1 d . . . . .
H8A H 0.9586 0.5887 0.4728 0.033 Uiso 1 1 calc R . . . .
C9A C 0.7982(2) 0.62104(18) 0.41352(16) 0.0274(5) Uani 1 1 d . . . . .
H9A H 0.7444 0.6091 0.4645 0.033 Uiso 1 1 calc R . . . .
C10A C 0.7488(2) 0.65136(17) 0.33282(15) 0.0244(5) Uani 1 1 d . . . . .
H10A H 0.6623 0.6592 0.3291 0.029 Uiso 1 1 calc R . . . .
C11A C 0.8306(2) 0.66965(16) 0.25826(15) 0.0213(5) Uani 1 1 d . . . . .
C12A C 0.4780(2) 0.87994(17) 0.18253(15) 0.0241(5) Uani 1 1 d . . . . .
C13A C 0.3943(2) 0.91888(18) 0.11842(16) 0.0274(5) Uani 1 1 d . . . . .
H13A H 0.4245 0.9412 0.0604 0.033 Uiso 1 1 calc R . . . .
C14A C 0.2656(3) 0.92448(19) 0.14117(18) 0.0323(6) Uani 1 1 d . . . . .
H14A H 0.2097 0.9502 0.0979 0.039 Uiso 1 1 calc R . . . .
C15A C 0.2183(2) 0.89223(18) 0.22770(18) 0.0302(6) Uani 1 1 d . . . . .
C16A C 0.3045(3) 0.85400(19) 0.29078(17) 0.0317(6) Uani 1 1 d . . . . .
H16A H 0.2745 0.8323 0.3489 0.038 Uiso 1 1 calc R . . . .
C17A C 0.4332(2) 0.84746(18) 0.26925(16) 0.0278(5) Uani 1 1 d . . . . .
H17A H 0.4892 0.8216 0.3124 0.033 Uiso 1 1 calc R . . . .
C18A C 0.0784(3) 0.8995(2) 0.2525(2) 0.0423(7) Uani 1 1 d . . . . .
H18A H 0.0480 0.9508 0.2808 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.0626 0.8390 0.2916 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.0353 0.9134 0.2009 0.063 Uiso 1 1 calc GR . . . .
C19A C 1.1471(2) 0.68096(18) 0.15051(16) 0.0243(5) Uani 1 1 d . . . . .
C20A C 1.3550(2) 0.64618(19) 0.19223(18) 0.0299(6) Uani 1 1 d . . . . .
H20A H 1.3682 0.7122 0.1658 0.036 Uiso 1 1 calc R . . . .
H20B H 1.3883 0.6079 0.1509 0.036 Uiso 1 1 calc R . . . .
C21A C 1.4199(2) 0.6031(2) 0.27496(19) 0.0345(6) Uani 1 1 d . . . . .
H21A H 1.5094 0.6012 0.2619 0.052 Uiso 1 1 calc GR . . . .
H21B H 1.4047 0.5383 0.3010 0.052 Uiso 1 1 calc GR . . . .
H21C H 1.3872 0.6424 0.3148 0.052 Uiso 1 1 calc GR . . . .
S1 S 0.54660(5) 0.38393(4) 0.19286(4) 0.02187(13) Uani 1 1 d . . . . .
O1 O 0.60812(16) 0.38231(13) 0.26610(11) 0.0276(4) Uani 1 1 d . . . . .
O2 O 0.55296(16) 0.46120(12) 0.11423(11) 0.0279(4) Uani 1 1 d . . . . .
O3 O 1.09103(17) 0.22601(14) 0.11261(12) 0.0326(4) Uani 1 1 d . . . . .
O4 O 1.12799(15) 0.14306(13) 0.25175(11) 0.0290(4) Uani 1 1 d . . . . .
N1 N 0.59500(18) 0.27809(14) 0.17181(13) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.92908(18) 0.18721(15) 0.21368(12) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.8260(2) 0.34587(15) 0.13873(13) 0.0265(4) Uani 1 1 d . . . . .
N4 N 0.8644(2) 0.39057(15) 0.06575(14) 0.0304(5) Uani 1 1 d . . . . .
N5 N 0.8968(3) 0.44011(19) 0.00256(17) 0.0574(8) Uani 1 1 d . . . . .
C1 C 0.7111(2) 0.20770(17) 0.19808(14) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.6915(2) 0.12102(17) 0.16854(16) 0.0256(5) Uani 1 1 d . . . . .
H2A H 0.7720 0.0793 0.1586 0.031 Uiso 1 1 calc R . . . .
H2B H 0.6380 0.0828 0.2121 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6278(3) 0.16711(19) 0.08397(17) 0.0303(6) Uani 1 1 d . . . . .
H3A H 0.5719 0.1272 0.0769 0.036 Uiso 1 1 calc R . . . .
H3B H 0.6905 0.1750 0.0341 0.036 Uiso 1 1 calc R . . . .
C4 C 0.5526(2) 0.26604(18) 0.09280(16) 0.0273(5) Uani 1 1 d . . . . .
H4A H 0.5711 0.3176 0.0418 0.033 Uiso 1 1 calc R . . . .
H4B H 0.4623 0.2667 0.0999 0.033 Uiso 1 1 calc R . . . .
C5 C 0.8358(2) 0.24087(17) 0.15146(15) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.8581 0.2235 0.0959 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8668(2) 0.16000(17) 0.29908(15) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.9171(2) 0.12180(18) 0.37931(16) 0.0263(5) Uani 1 1 d . . . . .
H7 H 1.0039 0.1099 0.3833 0.032 Uiso 1 1 calc R . . . .
C8 C 0.8335(2) 0.10197(19) 0.45321(16) 0.0296(5) Uani 1 1 d . . . . .
H8 H 0.8650 0.0774 0.5077 0.035 Uiso 1 1 calc R . . . .
C9 C 0.7041(2) 0.11778(19) 0.44793(16) 0.0302(6) Uani 1 1 d . . . . .
H9 H 0.6501 0.1033 0.4985 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6545(2) 0.15535(18) 0.36700(16) 0.0263(5) Uani 1 1 d . . . . .
H10 H 0.5678 0.1657 0.3629 0.032 Uiso 1 1 calc R . . . .
C11 C 0.7367(2) 0.17681(16) 0.29303(15) 0.0214(5) Uani 1 1 d . . . . .
C12 C 0.3841(2) 0.38474(16) 0.22565(15) 0.0219(5) Uani 1 1 d . . . . .
C13 C 0.2952(2) 0.42133(17) 0.16444(16) 0.0247(5) Uani 1 1 d . . . . .
H13 H 0.3203 0.4464 0.1058 0.030 Uiso 1 1 calc R . . . .
C14 C 0.1683(2) 0.41991(18) 0.19204(16) 0.0262(5) Uani 1 1 d . . . . .
H14 H 0.1087 0.4434 0.1511 0.031 Uiso 1 1 calc R . . . .
C15 C 0.1283(2) 0.38415(17) 0.27949(17) 0.0260(5) Uani 1 1 d . . . . .
C16 C 0.2193(2) 0.34918(18) 0.33985(16) 0.0284(5) Uani 1 1 d . . . . .
H16 H 0.1940 0.3260 0.3987 0.034 Uiso 1 1 calc R . . . .
C17 C 0.3461(2) 0.34843(18) 0.31367(16) 0.0260(5) Uani 1 1 d . . . . .
H17 H 0.4058 0.3239 0.3544 0.031 Uiso 1 1 calc R . . . .
C18 C -0.0098(2) 0.3840(2) 0.30879(18) 0.0331(6) Uani 1 1 d . . . . .
H18D H -0.0450 0.4387 0.3320 0.050 Uiso 1 1 calc GR . . . .
H18E H -0.0182 0.3249 0.3531 0.050 Uiso 1 1 calc GR . . . .
H18F H -0.0541 0.3883 0.2599 0.050 Uiso 1 1 calc GR . . . .
C19 C 1.0544(2) 0.18836(18) 0.18695(16) 0.0253(5) Uani 1 1 d . . . . .
C20 C 1.2632(2) 0.1409(2) 0.22975(19) 0.0335(6) Uani 1 1 d . . . . .
H20C H 1.2793 0.2065 0.2054 0.040 Uiso 1 1 calc R . . . .
H20D H 1.2955 0.1041 0.1871 0.040 Uiso 1 1 calc R . . . .
C21 C 1.3260(3) 0.0934(2) 0.3126(2) 0.0404(7) Uani 1 1 d . . . . .
H21D H 1.4161 0.0884 0.3004 0.061 Uiso 1 1 calc GR . . . .
H21E H 1.3068 0.0295 0.3371 0.061 Uiso 1 1 calc GR . . . .
H21F H 1.2955 0.1317 0.3535 0.061 Uiso 1 1 calc GR . . . .


_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
Cl1A C22A 1.760(3) . ?
Cl2A C22A 1.756(3) . ?
Cl1 C22 1.755(3) . ?
Cl2 C22 1.749(3) . ?
S1A O1A 1.4277(16) . ?
S1A O2A 1.4345(17) . ?
S1A N1A 1.6456(19) . ?
S1A C12A 1.767(3) . ?
O3A C19A 1.217(3) . ?
O4A C19A 1.332(3) . ?
O4A C20A 1.457(3) . ?
N1A C1A 1.469(3) . ?
N1A C4A 1.482(3) . ?
N2A C5A 1.463(3) . ?
N2A C6A 1.422(3) . ?
N2A C19A 1.373(3) . ?
N3A N4A 1.234(3) . ?
N3A C5A 1.471(3) . ?
N4A N5A 1.130(3) . ?
C1A C2A 1.540(3) . ?
C1A C5A 1.560(3) . ?
C1A C11A 1.509(3) . ?
C2A C3A 1.521(3) . ?
C3A C4A 1.530(3) . ?
C6A C7A 1.386(3) . ?
C6A C11A 1.389(3) . ?
C7A C8A 1.387(4) . ?
C8A C9A 1.383(3) . ?
C9A C10A 1.390(3) . ?
C10A C11A 1.380(3) . ?
C12A C13A 1.385(3) . ?
C12A C17A 1.387(3) . ?
C13A C14A 1.384(4) . ?
C14A C15A 1.392(4) . ?
C15A C16A 1.391(4) . ?
C15A C18A 1.502(4) . ?
C16A C17A 1.380(4) . ?
C20A C21A 1.502(4) . ?
S1 O1 1.4288(17) . ?
S1 O2 1.4356(18) . ?
S1 N1 1.636(2) . ?
S1 C12 1.767(2) . ?
O3 C19 1.211(3) . ?
O4 C19 1.331(3) . ?
O4 C20 1.456(3) . ?
N1 C1 1.469(3) . ?
N1 C4 1.481(3) . ?
N2 C5 1.461(3) . ?
N2 C6 1.425(3) . ?
N2 C19 1.369(3) . ?
N3 N4 1.229(3) . ?
N3 C5 1.471(3) . ?
N4 N5 1.124(3) . ?
C1 C2 1.542(3) . ?
C1 C5 1.555(3) . ?
C1 C11 1.509(3) . ?
C2 C3 1.523(3) . ?
C3 C4 1.530(3) . ?
C6 C7 1.388(3) . ?
C6 C11 1.394(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.385(4) . ?
C9 C10 1.394(3) . ?
C10 C11 1.381(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.397(3) . ?
C15 C18 1.506(3) . ?
C16 C17 1.379(3) . ?
C20 C21 1.498(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2A C22A Cl1A 111.49(16) . . ?
Cl2 C22 Cl1 111.50(16) . . ?
O1A S1A O2A 119.77(11) . . ?
O1A S1A N1A 107.68(10) . . ?
O1A S1A C12A 108.73(11) . . ?
O2A S1A N1A 110.58(10) . . ?
O2A S1A C12A 106.22(11) . . ?
N1A S1A C12A 102.49(10) . . ?
C19A O4A C20A 115.3(2) . . ?
C1A N1A S1A 125.55(15) . . ?
C1A N1A C4A 110.75(18) . . ?
C4A N1A S1A 117.06(15) . . ?
C6A N2A C5A 110.29(18) . . ?
C19A N2A C5A 117.6(2) . . ?
C19A N2A C6A 130.3(2) . . ?
N4A N3A C5A 115.6(2) . . ?
N5A N4A N3A 172.0(3) . . ?
N1A C1A C2A 100.18(17) . . ?
N1A C1A C5A 115.23(18) . . ?
N1A C1A C11A 117.84(19) . . ?
C2A C1A C5A 108.97(18) . . ?
C11A C1A C2A 111.80(18) . . ?
C11A C1A C5A 102.88(17) . . ?
C3A C2A C1A 104.85(18) . . ?
C2A C3A C4A 105.14(18) . . ?
N1A C4A C3A 104.55(18) . . ?
N2A C5A N3A 109.31(18) . . ?
N2A C5A C1A 102.52(18) . . ?
N3A C5A C1A 110.38(18) . . ?
C7A C6A N2A 129.9(2) . . ?
C7A C6A C11A 121.1(2) . . ?
C11A C6A N2A 109.0(2) . . ?
C6A C7A C8A 117.7(2) . . ?
C9A C8A C7A 121.5(2) . . ?
C8A C9A C10A 120.3(2) . . ?
C11A C10A C9A 118.7(2) . . ?
C6A C11A C1A 109.5(2) . . ?
C10A C11A C1A 129.6(2) . . ?
C10A C11A C6A 120.7(2) . . ?
C13A C12A S1A 119.51(19) . . ?
C13A C12A C17A 120.3(2) . . ?
C17A C12A S1A 120.19(19) . . ?
C14A C13A C12A 119.7(2) . . ?
C13A C14A C15A 121.1(2) . . ?
C14A C15A C18A 121.1(3) . . ?
C16A C15A C14A 118.0(2) . . ?
C16A C15A C18A 120.9(3) . . ?
C17A C16A C15A 121.7(2) . . ?
C16A C17A C12A 119.3(2) . . ?
O3A C19A O4A 125.4(2) . . ?
O3A C19A N2A 122.4(2) . . ?
O4A C19A N2A 112.2(2) . . ?
O4A C20A C21A 106.6(2) . . ?
O1 S1 O2 119.75(11) . . ?
O1 S1 N1 107.70(10) . . ?
O1 S1 C12 108.60(11) . . ?
O2 S1 N1 110.52(10) . . ?
O2 S1 C12 106.44(11) . . ?
N1 S1 C12 102.45(10) . . ?
C19 O4 C20 115.9(2) . . ?
C1 N1 S1 126.83(15) . . ?
C1 N1 C4 111.24(18) . . ?
C4 N1 S1 117.24(15) . . ?
C6 N2 C5 109.76(18) . . ?
C19 N2 C5 118.2(2) . . ?
C19 N2 C6 130.5(2) . . ?
N4 N3 C5 115.3(2) . . ?
N5 N4 N3 172.4(3) . . ?
N1 C1 C2 100.51(17) . . ?
N1 C1 C5 114.53(19) . . ?
N1 C1 C11 118.54(19) . . ?
C2 C1 C5 109.95(19) . . ?
C11 C1 C2 110.97(19) . . ?
C11 C1 C5 102.46(17) . . ?
C3 C2 C1 104.78(19) . . ?
C2 C3 C4 105.19(19) . . ?
N1 C4 C3 104.59(19) . . ?
N2 C5 N3 109.20(18) . . ?
N2 C5 C1 103.12(18) . . ?
N3 C5 C1 110.92(19) . . ?
C7 C6 N2 129.9(2) . . ?
C7 C6 C11 121.1(2) . . ?
C11 C6 N2 109.1(2) . . ?
C8 C7 C6 117.8(2) . . ?
C9 C8 C7 121.6(2) . . ?
C8 C9 C10 120.2(2) . . ?
C11 C10 C9 118.7(2) . . ?
C6 C11 C1 109.3(2) . . ?
C10 C11 C1 129.7(2) . . ?
C10 C11 C6 120.6(2) . . ?
C13 C12 S1 120.38(19) . . ?
C13 C12 C17 120.4(2) . . ?
C17 C12 S1 119.18(18) . . ?
C14 C13 C12 119.1(2) . . ?
C13 C14 C15 121.5(2) . . ?
C14 C15 C16 118.3(2) . . ?
C14 C15 C18 121.0(2) . . ?
C16 C15 C18 120.7(2) . . ?
C17 C16 C15 121.2(2) . . ?
C16 C17 C12 119.5(2) . . ?
O3 C19 O4 125.5(2) . . ?
O3 C19 N2 122.7(2) . . ?
O4 C19 N2 111.9(2) . . ?
O4 C20 C21 106.9(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
S1A N1A C1A C2A 175.67(16) . . . . ?
S1A N1A C1A C5A -67.6(2) . . . . ?
S1A N1A C1A C11A 54.2(3) . . . . ?
S1A N1A C4A C3A 170.18(16) . . . . ?
S1A C12A C13A C14A -180.0(2) . . . . ?
S1A C12A C17A C16A 179.67(19) . . . . ?
O1A S1A N1A C1A -25.2(2) . . . . ?
O1A S1A N1A C4A -173.88(17) . . . . ?
O1A S1A C12A C13A 154.32(19) . . . . ?
O1A S1A C12A C17A -25.1(2) . . . . ?
O2A S1A N1A C1A 107.32(19) . . . . ?
O2A S1A N1A C4A -41.3(2) . . . . ?
O2A S1A C12A C13A 24.2(2) . . . . ?
O2A S1A C12A C17A -155.19(19) . . . . ?
N1A S1A C12A C13A -91.9(2) . . . . ?
N1A S1A C12A C17A 88.7(2) . . . . ?
N1A C1A C2A C3A 37.5(2) . . . . ?
N1A C1A C5A N2A 152.71(18) . . . . ?
N1A C1A C5A N3A 36.4(2) . . . . ?
N1A C1A C11A C6A -145.4(2) . . . . ?
N1A C1A C11A C10A 40.6(3) . . . . ?
N2A C6A C7A C8A -179.9(2) . . . . ?
N2A C6A C11A C1A 4.2(3) . . . . ?
N2A C6A C11A C10A 178.9(2) . . . . ?
N4A N3A C5A N2A 106.6(2) . . . . ?
N4A N3A C5A C1A -141.4(2) . . . . ?
C1A N1A C4A C3A 17.1(3) . . . . ?
C1A C2A C3A C4A -28.5(2) . . . . ?
C2A C1A C5A N2A -95.7(2) . . . . ?
C2A C1A C5A N3A 147.99(18) . . . . ?
C2A C1A C11A C6A 99.4(2) . . . . ?
C2A C1A C11A C10A -74.6(3) . . . . ?
C2A C3A C4A N1A 7.9(3) . . . . ?
C4A N1A C1A C2A -34.0(2) . . . . ?
C4A N1A C1A C5A 82.7(2) . . . . ?
C4A N1A C1A C11A -155.5(2) . . . . ?
C5A N2A C6A C7A -168.2(2) . . . . ?
C5A N2A C6A C11A 12.1(3) . . . . ?
C5A N2A C19A O3A -8.8(3) . . . . ?
C5A N2A C19A O4A 171.96(19) . . . . ?
C5A C1A C2A C3A -83.8(2) . . . . ?
C5A C1A C11A C6A -17.4(2) . . . . ?
C5A C1A C11A C10A 168.6(2) . . . . ?
C6A N2A C5A N3A 94.9(2) . . . . ?
C6A N2A C5A C1A -22.2(2) . . . . ?
C6A N2A C19A O3A -171.5(2) . . . . ?
C6A N2A C19A O4A 9.3(4) . . . . ?
C6A C7A C8A C9A 0.9(4) . . . . ?
C7A C6A C11A C1A -175.5(2) . . . . ?
C7A C6A C11A C10A -0.8(4) . . . . ?
C7A C8A C9A C10A -0.4(4) . . . . ?
C8A C9A C10A C11A -0.7(4) . . . . ?
C9A C10A C11A C1A 174.7(2) . . . . ?
C9A C10A C11A C6A 1.3(4) . . . . ?
C11A C1A C2A C3A 163.20(19) . . . . ?
C11A C1A C5A N2A 23.1(2) . . . . ?
C11A C1A C5A N3A -93.2(2) . . . . ?
C11A C6A C7A C8A -0.3(4) . . . . ?
C12A S1A N1A C1A -139.81(19) . . . . ?
C12A S1A N1A C4A 71.55(19) . . . . ?
C12A C13A C14A C15A 0.5(4) . . . . ?
C13A C12A C17A C16A 0.3(4) . . . . ?
C13A C14A C15A C16A -0.1(4) . . . . ?
C13A C14A C15A C18A 179.2(3) . . . . ?
C14A C15A C16A C17A -0.2(4) . . . . ?
C15A C16A C17A C12A 0.1(4) . . . . ?
C17A C12A C13A C14A -0.6(4) . . . . ?
C18A C15A C16A C17A -179.5(2) . . . . ?
C19A O4A C20A C21A -179.9(2) . . . . ?
C19A N2A C5A N3A -71.1(3) . . . . ?
C19A N2A C5A C1A 171.79(19) . . . . ?
C19A N2A C6A C7A -4.5(4) . . . . ?
C19A N2A C6A C11A 175.8(2) . . . . ?
C20A O4A C19A O3A 1.1(3) . . . . ?
C20A O4A C19A N2A -179.7(2) . . . . ?
S1 N1 C1 C2 173.30(17) . . . . ?
S1 N1 C1 C5 -68.9(2) . . . . ?
S1 N1 C1 C11 52.3(3) . . . . ?
S1 N1 C4 C3 171.96(17) . . . . ?
S1 C12 C13 C14 179.23(18) . . . . ?
S1 C12 C17 C16 179.72(19) . . . . ?
O1 S1 N1 C1 -21.0(2) . . . . ?
O1 S1 N1 C4 -174.45(17) . . . . ?
O1 S1 C12 C13 156.25(19) . . . . ?
O1 S1 C12 C17 -23.6(2) . . . . ?
O2 S1 N1 C1 111.5(2) . . . . ?
O2 S1 N1 C4 -41.9(2) . . . . ?
O2 S1 C12 C13 26.1(2) . . . . ?
O2 S1 C12 C17 -153.78(19) . . . . ?
N1 S1 C12 C13 -90.0(2) . . . . ?
N1 S1 C12 C17 90.2(2) . . . . ?
N1 C1 C2 C3 36.7(2) . . . . ?
N1 C1 C5 N2 154.06(18) . . . . ?
N1 C1 C5 N3 37.3(3) . . . . ?
N1 C1 C11 C6 -146.2(2) . . . . ?
N1 C1 C11 C10 41.1(3) . . . . ?
N2 C6 C7 C8 179.8(2) . . . . ?
N2 C6 C11 C1 5.8(3) . . . . ?
N2 C6 C11 C10 179.3(2) . . . . ?
N4 N3 C5 N2 112.8(2) . . . . ?
N4 N3 C5 C1 -134.2(2) . . . . ?
C1 N1 C4 C3 14.5(3) . . . . ?
C1 C2 C3 C4 -29.2(3) . . . . ?
C2 C1 C5 N2 -93.7(2) . . . . ?
C2 C1 C5 N3 149.54(19) . . . . ?
C2 C1 C11 C6 98.3(2) . . . . ?
C2 C1 C11 C10 -74.4(3) . . . . ?
C2 C3 C4 N1 9.8(3) . . . . ?
C4 N1 C1 C2 -31.9(2) . . . . ?
C4 N1 C1 C5 85.9(2) . . . . ?
C4 N1 C1 C11 -152.9(2) . . . . ?
C5 N2 C6 C7 -169.2(2) . . . . ?
C5 N2 C6 C11 11.3(3) . . . . ?
C5 N2 C19 O3 -5.3(4) . . . . ?
C5 N2 C19 O4 175.20(19) . . . . ?
C5 C1 C2 C3 -84.4(2) . . . . ?
C5 C1 C11 C6 -19.0(2) . . . . ?
C5 C1 C11 C10 168.3(2) . . . . ?
C6 N2 C5 N3 95.5(2) . . . . ?
C6 N2 C5 C1 -22.5(2) . . . . ?
C6 N2 C19 O3 -169.6(2) . . . . ?
C6 N2 C19 O4 11.0(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C6 C11 C1 -173.8(2) . . . . ?
C7 C6 C11 C10 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C1 172.9(2) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
C11 C1 C2 C3 162.9(2) . . . . ?
C11 C1 C5 N2 24.4(2) . . . . ?
C11 C1 C5 N3 -92.4(2) . . . . ?
C11 C6 C7 C8 -0.7(4) . . . . ?
C12 S1 N1 C1 -135.4(2) . . . . ?
C12 S1 N1 C4 71.14(19) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C12 C17 C16 -0.1(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C18 179.3(2) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C12 1.1(4) . . . . ?
C17 C12 C13 C14 -0.9(4) . . . . ?
C18 C15 C16 C17 179.6(2) . . . . ?
C19 O4 C20 C21 176.1(2) . . . . ?
C19 N2 C5 N3 -71.9(3) . . . . ?
C19 N2 C5 C1 170.12(19) . . . . ?
C19 N2 C6 C7 -3.9(4) . . . . ?
C19 N2 C6 C11 176.5(2) . . . . ?
C20 O4 C19 O3 0.9(4) . . . . ?
C20 O4 C19 N2 -179.7(2) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1015319'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sa3259
_audit_creation_date             2014-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        syn-5g
_chemical_formula_moiety         'C14 H14 N4 O4'
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_weight         302.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.764(3)
_cell_length_b                   9.345(4)
_cell_length_c                   20.472(9)
_cell_angle_alpha                80.083(16)
_cell_angle_beta                 86.694(16)
_cell_angle_gamma                79.180(13)
_cell_volume                     1436.7(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4713
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4764
_cell_measurement_theta_min      2.0204
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5105
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.010
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             6486
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0287
_diffrn_orient_matrix_UB_12      0.0689
_diffrn_orient_matrix_UB_13      0.1078
_diffrn_orient_matrix_UB_21      -0.0005
_diffrn_orient_matrix_UB_22      0.0805
_diffrn_orient_matrix_UB_23      -0.0756
_diffrn_orient_matrix_UB_31      -0.0482
_diffrn_orient_matrix_UB_32      -0.0006
_diffrn_orient_matrix_UB_33      0.0116
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4174
_reflns_number_total             5105
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5105
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.1109
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1509P)²+3.7230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3066
_refine_ls_wR_factor_ref         0.3194
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N3B) \\sim Ueq, Uanis(N3A) \\sim Ueq, Uanis(N4A) \\sim Ueq, Uanis(N4B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(N3B)=Sof(N4B)=1-FVAR(1)
 Sof(N3A)=Sof(N4A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C13A(H13A,H13B), C9(H9A,H9B), C10(H10C,H10D),
  C13(H13C,H13D)
4.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C5(H5), C6(H6), C7(H7), C8(H8)
4.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1A O 0.1920(5) 0.3522(4) 0.81536(19) 0.0321(9) Uani 1 1 d . . . . .
O2A O 0.1867(7) 0.5424(6) 0.7330(2) 0.0540(13) Uani 1 1 d . . . . .
O3A O -0.0511(5) 0.3220(4) 1.0574(2) 0.0354(10) Uani 1 1 d . . . . .
O4A O 0.0871(5) 0.0859(4) 1.08664(18) 0.0297(9) Uani 1 1 d . . . . .
N1A N 0.1326(6) 0.2055(5) 0.9849(2) 0.0288(10) Uani 1 1 d . . . . .
N2A N -0.0718(6) 0.3444(5) 0.9052(3) 0.0335(11) Uani 1 1 d . . . . .
N3A N -0.1479(15) 0.4667(14) 0.8769(9) 0.039(3) Uani 0.478(16) 1 d . U P A 1
N4A N -0.2207(19) 0.5724(15) 0.8495(9) 0.068(5) Uani 0.478(16) 1 d . U P A 1
C1A C 0.2542(7) 0.3089(6) 0.8820(3) 0.0263(12) Uani 1 1 d . . . . .
C2A C 0.1002(7) 0.3372(6) 0.9334(3) 0.0272(12) Uani 1 1 d . . . . .
H2A H 0.1034 0.4268 0.9518 0.033 Uiso 1 1 calc R . . . .
C3A C 0.2473(7) 0.0891(6) 0.9599(3) 0.0252(11) Uani 1 1 d . . . . .
C4A C 0.3158(7) 0.1449(6) 0.8980(3) 0.0266(11) Uani 1 1 d . . . . .
C5A C 0.4329(7) 0.0530(6) 0.8636(3) 0.0311(12) Uani 1 1 d . . . . .
H5A H 0.4812 0.0903 0.8231 0.037 Uiso 1 1 calc R . . . .
C6A C 0.4774(8) -0.0944(7) 0.8898(3) 0.0358(14) Uani 1 1 d . . . . .
H6A H 0.5541 -0.1575 0.8664 0.043 Uiso 1 1 calc R . . . .
C7A C 0.4078(8) -0.1497(7) 0.9516(3) 0.0331(13) Uani 1 1 d . . . . .
H7A H 0.4411 -0.2491 0.9692 0.040 Uiso 1 1 calc R . . . .
C8A C 0.2899(7) -0.0587(6) 0.9870(3) 0.0285(12) Uani 1 1 d . . . . .
H8A H 0.2413 -0.0959 1.0275 0.034 Uiso 1 1 calc R . . . .
C9A C 0.3945(7) 0.4016(6) 0.8864(3) 0.0289(12) Uani 1 1 d . . . . .
H9AA H 0.3944 0.4274 0.9303 0.035 Uiso 1 1 calc R . . . .
H9AB H 0.5102 0.3493 0.8760 0.035 Uiso 1 1 calc R . . . .
C10A C 0.3395(8) 0.5388(6) 0.8344(3) 0.0323(13) Uani 1 1 d . . . . .
H10A H 0.2686 0.6178 0.8544 0.039 Uiso 1 1 calc R . . . .
H10B H 0.4411 0.5736 0.8121 0.039 Uiso 1 1 calc R . . . .
C11A C 0.2346(8) 0.4850(7) 0.7872(3) 0.0367(14) Uani 1 1 d . . . . .
C12A C 0.0489(7) 0.2111(6) 1.0451(3) 0.0265(11) Uani 1 1 d . . . . .
C13A C -0.0042(8) 0.0834(7) 1.1515(3) 0.0338(13) Uani 1 1 d . . . . .
H13A H -0.1300 0.0977 1.1463 0.041 Uiso 1 1 calc R . . . .
H13B H 0.0212 0.1614 1.1731 0.041 Uiso 1 1 calc R . . . .
C14A C 0.0607(9) -0.0638(7) 1.1914(3) 0.0379(14) Uani 1 1 d . . . . .
H14A H 0.0486 -0.1399 1.1669 0.057 Uiso 1 1 calc GR . . . .
H14B H -0.0065 -0.0751 1.2322 0.057 Uiso 1 1 calc GR . . . .
H14C H 0.1821 -0.0714 1.2010 0.057 Uiso 1 1 calc GR . . . .
O1 O 0.6579(5) 0.2145(4) 0.68333(19) 0.0311(9) Uani 1 1 d . . . . .
O2 O 0.6310(7) 0.3631(6) 0.7593(2) 0.0505(13) Uani 1 1 d . . . . .
O3 O 0.4744(5) 0.3668(4) 0.4382(2) 0.0315(9) Uani 1 1 d . . . . .
O4 O 0.6165(5) 0.1534(4) 0.40845(19) 0.0306(9) Uani 1 1 d . . . . .
N1 N 0.6382(6) 0.1937(5) 0.5126(2) 0.0260(10) Uani 1 1 d . . . . .
N2 N 0.4155(6) 0.2766(5) 0.5917(3) 0.0308(11) Uani 1 1 d . . . . .
N3 N 0.3046(6) 0.3887(6) 0.5742(3) 0.0331(11) Uani 1 1 d . . . . .
N4 N 0.1920(7) 0.4828(6) 0.5616(3) 0.0485(15) Uani 1 1 d . . . . .
C1 C 0.7335(7) 0.2116(6) 0.6180(3) 0.0261(12) Uani 1 1 d . . . . .
C2 C 0.5951(7) 0.2849(6) 0.5644(3) 0.0235(11) Uani 1 1 d . . . . .
H2 H 0.6070 0.3874 0.5476 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7371(6) 0.0544(6) 0.5391(3) 0.0240(11) Uani 1 1 d . . . . .
C4 C 0.7886(7) 0.0579(6) 0.6025(3) 0.0280(12) Uani 1 1 d . . . . .
C5 C 0.8864(8) -0.0640(6) 0.6391(3) 0.0326(13) Uani 1 1 d . . . . .
H5 H 0.9213 -0.0606 0.6814 0.039 Uiso 1 1 calc R . . . .
C6 C 0.9327(8) -0.1931(6) 0.6117(3) 0.0339(13) Uani 1 1 d . . . . .
H6 H 0.9970 -0.2774 0.6361 0.041 Uiso 1 1 calc R . . . .
C7 C 0.8826(7) -0.1953(6) 0.5483(3) 0.0306(12) Uani 1 1 d . . . . .
H7 H 0.9166 -0.2814 0.5302 0.037 Uiso 1 1 calc R . . . .
C8 C 0.7835(7) -0.0736(6) 0.5108(3) 0.0281(12) Uani 1 1 d . . . . .
H8 H 0.7492 -0.0769 0.4683 0.034 Uiso 1 1 calc R . . . .
C9 C 0.8857(7) 0.2980(6) 0.6148(3) 0.0284(12) Uani 1 1 d . . . . .
H9A H 0.9938 0.2331 0.6298 0.034 Uiso 1 1 calc R . . . .
H9B H 0.9044 0.3484 0.5701 0.034 Uiso 1 1 calc R . . . .
C10 C 0.8211(8) 0.4077(6) 0.6619(3) 0.0344(13) Uani 1 1 d . . . . .
H10C H 0.9173 0.4248 0.6859 0.041 Uiso 1 1 calc R . . . .
H10D H 0.7620 0.5013 0.6380 0.041 Uiso 1 1 calc R . . . .
C11 C 0.6962(8) 0.3325(7) 0.7076(3) 0.0347(14) Uani 1 1 d . . . . .
C12 C 0.5682(7) 0.2467(6) 0.4512(3) 0.0260(11) Uani 1 1 d . . . . .
C13 C 0.5488(9) 0.2048(7) 0.3425(3) 0.0386(14) Uani 1 1 d . . . . .
H13C H 0.5838 0.2981 0.3238 0.046 Uiso 1 1 calc R . . . .
H13D H 0.4217 0.2192 0.3440 0.046 Uiso 1 1 calc R . . . .
C14 C 0.6234(10) 0.0889(8) 0.3010(3) 0.0465(17) Uani 1 1 d . . . . .
H14D H 0.5774 0.1176 0.2573 0.070 Uiso 1 1 calc GR . . . .
H14E H 0.5918 -0.0036 0.3210 0.070 Uiso 1 1 calc GR . . . .
H14F H 0.7489 0.0787 0.2984 0.070 Uiso 1 1 calc GR . . . .
N3B N -0.1764(14) 0.4517(12) 0.9177(8) 0.037(3) Uani 0.522(16) 1 d . U P A 2
N4B N -0.2907(16) 0.5422(14) 0.9274(8) 0.067(5) Uani 0.522(16) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.438(7) . ?
O1A C11A 1.367(7) . ?
O2A C11A 1.193(8) . ?
O3A C12A 1.227(7) . ?
O4A C12A 1.317(7) . ?
O4A C13A 1.468(7) . ?
N1A C2A 1.469(7) . ?
N1A C3A 1.420(7) . ?
N1A C12A 1.364(7) . ?
N2A N3A 1.245(14) . ?
N2A C2A 1.470(7) . ?
N2A N3B 1.220(12) . ?
N3A N4A 1.116(17) . ?
C1A C2A 1.563(8) . ?
C1A C4A 1.502(7) . ?
C1A C9A 1.529(7) . ?
C3A C4A 1.399(8) . ?
C3A C8A 1.382(8) . ?
C4A C5A 1.379(8) . ?
C5A C6A 1.376(8) . ?
C6A C7A 1.399(9) . ?
C7A C8A 1.389(8) . ?
C9A C10A 1.529(8) . ?
C10A C11A 1.504(9) . ?
C13A C14A 1.488(8) . ?
O1 C1 1.432(6) . ?
O1 C11 1.371(7) . ?
O2 C11 1.203(7) . ?
O3 C12 1.214(7) . ?
O4 C12 1.330(6) . ?
O4 C13 1.447(7) . ?
N1 C2 1.458(7) . ?
N1 C3 1.416(7) . ?
N1 C12 1.372(7) . ?
N2 N3 1.239(7) . ?
N2 C2 1.482(7) . ?
N3 N4 1.124(7) . ?
C1 C2 1.558(7) . ?
C1 C4 1.502(8) . ?
C1 C9 1.544(7) . ?
C3 C4 1.389(8) . ?
C3 C8 1.396(8) . ?
C4 C5 1.371(8) . ?
C5 C6 1.395(8) . ?
C6 C7 1.382(9) . ?
C7 C8 1.384(8) . ?
C9 C10 1.525(8) . ?
C10 C11 1.496(9) . ?
C13 C14 1.501(9) . ?
N3B N4B 1.139(15) . ?

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
C11A O1A C1A 110.8(4) . . ?
C12A O4A C13A 115.0(4) . . ?
C3A N1A C2A 110.3(4) . . ?
C12A N1A C2A 118.4(4) . . ?
C12A N1A C3A 131.3(5) . . ?
N3A N2A C2A 117.7(7) . . ?
N3B N2A C2A 111.4(7) . . ?
N4A N3A N2A 176.3(14) . . ?
O1A C1A C2A 110.6(4) . . ?
O1A C1A C4A 111.4(4) . . ?
O1A C1A C9A 105.4(4) . . ?
C4A C1A C2A 102.8(4) . . ?
C4A C1A C9A 114.8(5) . . ?
C9A C1A C2A 112.0(5) . . ?
N1A C2A N2A 108.1(4) . . ?
N1A C2A C1A 103.6(4) . . ?
N2A C2A C1A 112.2(5) . . ?
C4A C3A N1A 108.9(5) . . ?
C8A C3A N1A 129.6(5) . . ?
C8A C3A C4A 121.5(5) . . ?
C3A C4A C1A 110.3(5) . . ?
C5A C4A C1A 129.5(5) . . ?
C5A C4A C3A 120.1(5) . . ?
C6A C5A C4A 119.4(6) . . ?
C5A C6A C7A 120.3(5) . . ?
C8A C7A C6A 121.1(6) . . ?
C3A C8A C7A 117.7(5) . . ?
C10A C9A C1A 103.2(4) . . ?
C11A C10A C9A 103.3(5) . . ?
O1A C11A C10A 110.0(5) . . ?
O2A C11A O1A 120.6(6) . . ?
O2A C11A C10A 129.4(6) . . ?
O3A C12A O4A 125.3(5) . . ?
O3A C12A N1A 122.2(5) . . ?
O4A C12A N1A 112.5(5) . . ?
O4A C13A C14A 106.7(5) . . ?
C11 O1 C1 109.8(4) . . ?
C12 O4 C13 115.0(4) . . ?
C3 N1 C2 110.1(4) . . ?
C12 N1 C2 118.3(4) . . ?
C12 N1 C3 131.3(4) . . ?
N3 N2 C2 114.6(5) . . ?
N4 N3 N2 173.1(6) . . ?
O1 C1 C2 110.8(4) . . ?
O1 C1 C4 113.0(4) . . ?
O1 C1 C9 104.7(4) . . ?
C4 C1 C2 103.0(4) . . ?
C4 C1 C9 113.8(4) . . ?
C9 C1 C2 111.6(4) . . ?
N1 C2 N2 110.2(4) . . ?
N1 C2 C1 103.1(4) . . ?
N2 C2 C1 110.4(4) . . ?
C4 C3 N1 109.6(5) . . ?
C4 C3 C8 120.8(5) . . ?
C8 C3 N1 129.7(5) . . ?
C3 C4 C1 109.3(5) . . ?
C5 C4 C1 129.5(5) . . ?
C5 C4 C3 121.0(5) . . ?
C4 C5 C6 119.0(6) . . ?
C7 C6 C5 119.7(5) . . ?
C6 C7 C8 122.1(5) . . ?
C7 C8 C3 117.4(5) . . ?
C10 C9 C1 102.6(4) . . ?
C11 C10 C9 103.1(5) . . ?
O1 C11 C10 110.9(5) . . ?
O2 C11 O1 120.3(6) . . ?
O2 C11 C10 128.8(6) . . ?
O3 C12 O4 124.7(5) . . ?
O3 C12 N1 122.7(5) . . ?
O4 C12 N1 112.6(4) . . ?
O4 C13 C14 107.2(5) . . ?
N4B N3B N2A 170.9(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A N1A 138.4(4) . . . . ?
O1A C1A C2A N2A 22.1(6) . . . . ?
O1A C1A C4A C3A -133.1(5) . . . . ?
O1A C1A C4A C5A 51.8(8) . . . . ?
O1A C1A C9A C10A 26.4(5) . . . . ?
N1A C3A C4A C1A 3.7(6) . . . . ?
N1A C3A C4A C5A 179.4(5) . . . . ?
N1A C3A C8A C7A -179.8(5) . . . . ?
N3A N2A C2A N1A 158.0(10) . . . . ?
N3A N2A C2A C1A -88.4(11) . . . . ?
C1A O1A C11A O2A -176.5(6) . . . . ?
C1A O1A C11A C10A 2.4(6) . . . . ?
C1A C4A C5A C6A 176.5(5) . . . . ?
C1A C9A C10A C11A -24.4(5) . . . . ?
C2A N1A C3A C4A 10.0(6) . . . . ?
C2A N1A C3A C8A -168.4(5) . . . . ?
C2A N1A C12A O3A -0.4(8) . . . . ?
C2A N1A C12A O4A 179.2(5) . . . . ?
C2A C1A C4A C3A -14.7(6) . . . . ?
C2A C1A C4A C5A 170.2(6) . . . . ?
C2A C1A C9A C10A -93.9(5) . . . . ?
C3A N1A C2A N2A 100.7(5) . . . . ?
C3A N1A C2A C1A -18.6(6) . . . . ?
C3A N1A C12A O3A -177.8(5) . . . . ?
C3A N1A C12A O4A 1.8(8) . . . . ?
C3A C4A C5A C6A 1.8(9) . . . . ?
C4A C1A C2A N1A 19.4(5) . . . . ?
C4A C1A C2A N2A -97.0(5) . . . . ?
C4A C1A C9A C10A 149.4(5) . . . . ?
C4A C3A C8A C7A 1.9(8) . . . . ?
C4A C5A C6A C7A -1.5(9) . . . . ?
C5A C6A C7A C8A 1.5(9) . . . . ?
C6A C7A C8A C3A -1.7(8) . . . . ?
C8A C3A C4A C1A -177.7(5) . . . . ?
C8A C3A C4A C5A -2.1(8) . . . . ?
C9A C1A C2A N1A -104.3(5) . . . . ?
C9A C1A C2A N2A 139.3(5) . . . . ?
C9A C1A C4A C3A 107.3(5) . . . . ?
C9A C1A C4A C5A -67.8(8) . . . . ?
C9A C10A C11A O1A 14.6(6) . . . . ?
C9A C10A C11A O2A -166.6(6) . . . . ?
C11A O1A C1A C2A 102.7(5) . . . . ?
C11A O1A C1A C4A -143.6(5) . . . . ?
C11A O1A C1A C9A -18.5(6) . . . . ?
C12A O4A C13A C14A -178.1(5) . . . . ?
C12A N1A C2A N2A -77.2(6) . . . . ?
C12A N1A C2A C1A 163.5(5) . . . . ?
C12A N1A C3A C4A -172.5(6) . . . . ?
C12A N1A C3A C8A 9.1(10) . . . . ?
C13A O4A C12A O3A 1.7(8) . . . . ?
C13A O4A C12A N1A -177.9(5) . . . . ?
O1 C1 C2 N1 -142.8(4) . . . . ?
O1 C1 C2 N2 -25.1(6) . . . . ?
O1 C1 C4 C3 136.2(5) . . . . ?
O1 C1 C4 C5 -48.9(8) . . . . ?
O1 C1 C9 C10 -29.8(5) . . . . ?
N1 C3 C4 C1 -4.6(6) . . . . ?
N1 C3 C4 C5 180.0(5) . . . . ?
N1 C3 C8 C7 179.9(5) . . . . ?
N3 N2 C2 N1 -106.3(5) . . . . ?
N3 N2 C2 C1 140.5(5) . . . . ?
C1 O1 C11 O2 172.9(5) . . . . ?
C1 O1 C11 C10 -6.8(6) . . . . ?
C1 C4 C5 C6 -174.9(5) . . . . ?
C1 C9 C10 C11 25.2(6) . . . . ?
C2 N1 C3 C4 -10.6(6) . . . . ?
C2 N1 C3 C8 169.3(5) . . . . ?
C2 N1 C12 O3 1.1(8) . . . . ?
C2 N1 C12 O4 -179.7(4) . . . . ?
C2 C1 C4 C3 16.6(6) . . . . ?
C2 C1 C4 C5 -168.5(6) . . . . ?
C2 C1 C9 C10 90.1(5) . . . . ?
C3 N1 C2 N2 -97.5(5) . . . . ?
C3 N1 C2 C1 20.3(5) . . . . ?
C3 N1 C12 O3 174.2(5) . . . . ?
C3 N1 C12 O4 -6.6(8) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C1 C2 N1 -21.7(5) . . . . ?
C4 C1 C2 N2 96.0(5) . . . . ?
C4 C1 C9 C10 -153.8(5) . . . . ?
C4 C3 C8 C7 -0.2(8) . . . . ?
C4 C5 C6 C7 1.3(9) . . . . ?
C5 C6 C7 C8 -1.5(9) . . . . ?
C6 C7 C8 C3 0.9(9) . . . . ?
C8 C3 C4 C1 175.5(5) . . . . ?
C8 C3 C4 C5 0.1(8) . . . . ?
C9 C1 C2 N1 100.9(5) . . . . ?
C9 C1 C2 N2 -141.5(4) . . . . ?
C9 C1 C4 C3 -104.5(5) . . . . ?
C9 C1 C4 C5 70.4(7) . . . . ?
C9 C10 C11 O1 -12.7(6) . . . . ?
C9 C10 C11 O2 167.6(6) . . . . ?
C11 O1 C1 C2 -97.2(5) . . . . ?
C11 O1 C1 C4 147.8(5) . . . . ?
C11 O1 C1 C9 23.3(6) . . . . ?
C12 O4 C13 C14 177.5(5) . . . . ?
C12 N1 C2 N2 77.0(6) . . . . ?
C12 N1 C2 C1 -165.2(4) . . . . ?
C12 N1 C3 C4 175.8(5) . . . . ?
C12 N1 C3 C8 -4.2(9) . . . . ?
C13 O4 C12 O3 0.1(8) . . . . ?
C13 O4 C12 N1 -179.0(5) . . . . ?
N3B N2A C2A N1A 114.2(9) . . . . ?
N3B N2A C2A C1A -132.2(9) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1015320'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        5h
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N8 O4'
_chemical_formula_sum            'C14 H14 N8 O4'
_chemical_formula_weight         358.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   13.410(3)
_cell_length_b                   6.5061(13)
_cell_length_c                   18.689(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.61(3)
_cell_angle_gamma                90.00
_cell_volume                     1625.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5295
_cell_measurement_theta_min      1.0931
_cell_measurement_theta_max      27.4832

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7854
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9426
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2850
_reflns_number_gt                2669
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1490P)²+0.3759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2850
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.2237
_refine_ls_wR_factor_gt          0.1803
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.87349(12) 0.5990(3) 0.14623(9) 0.0275(5) Uani 1 1 d . . .
O2 O 0.96017(14) 0.7008(3) 0.05822(10) 0.0335(5) Uani 1 1 d . . .
O3 O 0.55547(13) 0.8462(3) 0.25449(10) 0.0333(5) Uani 1 1 d . . .
O4 O 0.52184(12) 0.6832(3) 0.14945(9) 0.0256(5) Uani 1 1 d . . .
N1 N 0.64767(15) 0.2954(3) 0.16822(12) 0.0283(5) Uani 1 1 d . . .
N2 N 0.57160(16) 0.2688(3) 0.12634(12) 0.0301(6) Uani 1 1 d . . .
N3 N 0.50270(18) 0.2240(4) 0.09127(14) 0.0411(6) Uani 1 1 d . . .
N4 N 0.68853(15) 0.5404(3) 0.08086(10) 0.0271(5) Uani 1 1 d . . .
N5 N 0.68139(15) 0.7252(4) 0.06682(11) 0.0274(5) Uani 1 1 d . . .
N6 N 0.6719(2) 0.8876(4) 0.04773(14) 0.0445(7) Uani 1 1 d . . .
N7 N 0.67530(14) 0.6487(3) 0.20659(10) 0.0249(5) Uani 1 1 d . . .
N8 N 0.91137(16) 0.3685(3) 0.05762(12) 0.0317(6) Uani 1 1 d . . .
H8 H 0.9435 0.3437 0.0193 0.038 Uiso 1 1 calc R . .
C1 C 0.91691(17) 0.5565(4) 0.08438(13) 0.0261(6) Uani 1 1 d . . .
C2 C 0.8560(2) 0.1987(4) 0.08668(16) 0.0345(7) Uani 1 1 d . . .
H2B H 0.8891 0.0666 0.0771 0.041 Uiso 1 1 calc R . .
H2A H 0.7871 0.1947 0.0634 0.041 Uiso 1 1 calc R . .
C3 C 0.8531(2) 0.2294(4) 0.16625(16) 0.0342(7) Uani 1 1 d . . .
H3B H 0.9210 0.2103 0.1902 0.041 Uiso 1 1 calc R . .
H3A H 0.8084 0.1257 0.1856 0.041 Uiso 1 1 calc R . .
C4 C 0.81568(17) 0.4430(4) 0.18188(13) 0.0264(6) Uani 1 1 d . . .
C5 C 0.70205(17) 0.4869(4) 0.15683(12) 0.0244(6) Uani 1 1 d . . .
C6 C 0.82110(18) 0.5094(4) 0.25887(14) 0.0287(6) Uani 1 1 d . . .
C7 C 0.89275(18) 0.4647(5) 0.31467(15) 0.0348(7) Uani 1 1 d . . .
H7 H 0.9460 0.3725 0.3075 0.042 Uiso 1 1 calc R . .
C8 C 0.8854(2) 0.5560(5) 0.38045(15) 0.0381(7) Uani 1 1 d . . .
H8A H 0.9325 0.5236 0.4195 0.046 Uiso 1 1 calc R . .
C9 C 0.8089(2) 0.6958(5) 0.38972(15) 0.0387(7) Uani 1 1 d . . .
H9 H 0.8067 0.7628 0.4347 0.046 Uiso 1 1 calc R . .
C10 C 0.73633(19) 0.7399(4) 0.33533(14) 0.0328(6) Uani 1 1 d . . .
H10 H 0.6842 0.8350 0.3422 0.039 Uiso 1 1 calc R . .
C11 C 0.74244(17) 0.6394(4) 0.26986(13) 0.0271(6) Uani 1 1 d . . .
C12 C 0.58000(17) 0.7350(4) 0.20794(13) 0.0238(6) Uani 1 1 d . . .
C13 C 0.41919(18) 0.7610(4) 0.14816(14) 0.0276(6) Uani 1 1 d . . .
H13B H 0.4195 0.9116 0.1559 0.033 Uiso 1 1 calc R . .
H13A H 0.3835 0.6954 0.1865 0.033 Uiso 1 1 calc R . .
C14 C 0.3690(2) 0.7104(5) 0.07648(15) 0.0391(7) Uani 1 1 d . . .
H14C H 0.4024 0.7832 0.0392 0.059 Uiso 1 1 calc R . .
H14B H 0.2987 0.7527 0.0747 0.059 Uiso 1 1 calc R . .
H14A H 0.3728 0.5619 0.0683 0.059 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.364(3) . ?
O1 C4 1.469(3) . ?
O2 C1 1.226(3) . ?
O3 C12 1.197(3) . ?
O4 C12 1.334(3) . ?
O4 C13 1.465(3) . ?
N1 N2 1.247(3) . ?
N1 C5 1.468(3) . ?
N2 N3 1.127(3) . ?
N4 N5 1.232(3) . ?
N4 C5 1.459(3) . ?
N5 N6 1.119(3) . ?
N7 C12 1.398(3) . ?
N7 C11 1.429(3) . ?
N7 C5 1.468(3) . ?
N8 C1 1.321(3) . ?
N8 C2 1.460(3) . ?
N8 H8 0.8800 . ?
C2 C3 1.504(4) . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.514(4) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C6 1.498(4) . ?
C4 C5 1.584(3) . ?
C6 C11 1.380(4) . ?
C6 C7 1.391(4) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(4) . ?
C10 H10 0.9500 . ?
C13 C14 1.487(4) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 H14C 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 121.41(18) . . ?
C12 O4 C13 114.36(18) . . ?
N2 N1 C5 114.7(2) . . ?
N3 N2 N1 172.6(3) . . ?
N5 N4 C5 116.21(19) . . ?
N6 N5 N4 173.5(3) . . ?
C12 N7 C11 121.21(19) . . ?
C12 N7 C5 124.75(19) . . ?
C11 N7 C5 108.90(19) . . ?
C1 N8 C2 125.1(2) . . ?
C1 N8 H8 117.5 . . ?
C2 N8 H8 117.5 . . ?
O2 C1 N8 124.9(2) . . ?
O2 C1 O1 115.5(2) . . ?
N8 C1 O1 119.6(2) . . ?
N8 C2 C3 108.8(2) . . ?
N8 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
N8 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
H2B C2 H2A 108.3 . . ?
C2 C3 C4 110.4(2) . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
H3B C3 H3A 108.1 . . ?
O1 C4 C6 104.46(19) . . ?
O1 C4 C3 110.57(19) . . ?
C6 C4 C3 117.3(2) . . ?
O1 C4 C5 105.78(18) . . ?
C6 C4 C5 101.72(19) . . ?
C3 C4 C5 115.8(2) . . ?
N4 C5 N1 108.63(19) . . ?
N4 C5 N7 115.3(2) . . ?
N1 C5 N7 111.54(19) . . ?
N4 C5 C4 111.84(19) . . ?
N1 C5 C4 106.36(19) . . ?
N7 C5 C4 102.74(18) . . ?
C11 C6 C7 120.4(2) . . ?
C11 C6 C4 109.9(2) . . ?
C7 C6 C4 129.6(2) . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 117.4(2) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C6 C11 C10 121.1(2) . . ?
C6 C11 N7 109.9(2) . . ?
C10 C11 N7 128.9(2) . . ?
O3 C12 O4 124.8(2) . . ?
O3 C12 N7 124.1(2) . . ?
O4 C12 N7 111.0(2) . . ?
O4 C13 C14 107.1(2) . . ?
O4 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
O4 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
H13B C13 H13A 108.5 . . ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 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
C5 N1 N2 N3 169(2) . . . . ?
C5 N4 N5 N6 -167(2) . . . . ?
C2 N8 C1 O2 -177.0(3) . . . . ?
C2 N8 C1 O1 4.0(4) . . . . ?
C4 O1 C1 O2 177.5(2) . . . . ?
C4 O1 C1 N8 -3.4(3) . . . . ?
C1 N8 C2 C3 -29.2(3) . . . . ?
N8 C2 C3 C4 51.9(3) . . . . ?
C1 O1 C4 C6 155.4(2) . . . . ?
C1 O1 C4 C3 28.3(3) . . . . ?
C1 O1 C4 C5 -97.7(2) . . . . ?
C2 C3 C4 O1 -52.4(3) . . . . ?
C2 C3 C4 C6 -172.0(2) . . . . ?
C2 C3 C4 C5 67.8(3) . . . . ?
N5 N4 C5 N1 143.9(2) . . . . ?
N5 N4 C5 N7 17.9(3) . . . . ?
N5 N4 C5 C4 -99.0(2) . . . . ?
N2 N1 C5 N4 -30.4(3) . . . . ?
N2 N1 C5 N7 97.8(2) . . . . ?
N2 N1 C5 C4 -150.9(2) . . . . ?
C12 N7 C5 N4 60.6(3) . . . . ?
C11 N7 C5 N4 -144.7(2) . . . . ?
C12 N7 C5 N1 -63.9(3) . . . . ?
C11 N7 C5 N1 90.8(2) . . . . ?
C12 N7 C5 C4 -177.5(2) . . . . ?
C11 N7 C5 C4 -22.7(2) . . . . ?
O1 C4 C5 N4 40.6(3) . . . . ?
C6 C4 C5 N4 149.4(2) . . . . ?
C3 C4 C5 N4 -82.2(3) . . . . ?
O1 C4 C5 N1 159.02(18) . . . . ?
C6 C4 C5 N1 -92.1(2) . . . . ?
C3 C4 C5 N1 36.2(3) . . . . ?
O1 C4 C5 N7 -83.7(2) . . . . ?
C6 C4 C5 N7 25.2(2) . . . . ?
C3 C4 C5 N7 153.5(2) . . . . ?
O1 C4 C6 C11 89.8(2) . . . . ?
C3 C4 C6 C11 -147.4(2) . . . . ?
C5 C4 C6 C11 -20.1(3) . . . . ?
O1 C4 C6 C7 -87.5(3) . . . . ?
C3 C4 C6 C7 35.3(4) . . . . ?
C5 C4 C6 C7 162.6(3) . . . . ?
C11 C6 C7 C8 -1.6(4) . . . . ?
C4 C6 C7 C8 175.4(3) . . . . ?
C6 C7 C8 C9 -2.1(4) . . . . ?
C7 C8 C9 C10 3.1(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C7 C6 C11 C10 4.4(4) . . . . ?
C4 C6 C11 C10 -173.2(2) . . . . ?
C7 C6 C11 N7 -175.6(2) . . . . ?
C4 C6 C11 N7 6.8(3) . . . . ?
C9 C10 C11 C6 -3.4(4) . . . . ?
C9 C10 C11 N7 176.6(3) . . . . ?
C12 N7 C11 C6 166.8(2) . . . . ?
C5 N7 C11 C6 11.1(3) . . . . ?
C12 N7 C11 C10 -13.2(4) . . . . ?
C5 N7 C11 C10 -168.9(3) . . . . ?
C13 O4 C12 O3 -4.6(3) . . . . ?
C13 O4 C12 N7 177.66(19) . . . . ?
C11 N7 C12 O3 17.7(4) . . . . ?
C5 N7 C12 O3 169.5(2) . . . . ?
C11 N7 C12 O4 -164.5(2) . . . . ?
C5 N7 C12 O4 -12.7(3) . . . . ?
C12 O4 C13 C14 173.6(2) . . . . ?

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
N8 H8 O2 0.88 2.04 2.908(3) 170.0 3_765

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.158
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1015373'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        anti-5a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N5 O4 S'
_chemical_formula_sum            'C21 H23 N5 O4 S'
_chemical_formula_weight         441.50

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   18.126(5)
_cell_length_b                   14.074(4)
_cell_length_c                   16.468(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.045(4)
_cell_angle_gamma                90.00
_cell_volume                     4185(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12773
_cell_measurement_theta_min      1.24
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30549
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.48
_reflns_number_total             9533
_reflns_number_gt                8420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0377P)²+4.2874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9533
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.05058(4) 0.44684(5) 0.38017(4) 0.02998(17) Uani 1 1 d . . .
S2 S 0.42775(4) 0.28135(5) 0.15272(4) 0.03114(18) Uani 1 1 d . . .
O1 O -0.15863(15) 0.29045(16) 0.23422(14) 0.0472(6) Uani 1 1 d . . .
O2 O -0.19475(12) 0.33152(15) 0.35827(13) 0.0362(5) Uani 1 1 d . . .
O3 O -0.00277(12) 0.37316(15) 0.36352(13) 0.0367(5) Uani 1 1 d . . .
O4 O 0.09931(12) 0.44403(17) 0.45368(12) 0.0398(5) Uani 1 1 d . . .
O5 O 0.64208(16) 0.45575(18) 0.27123(17) 0.0589(7) Uani 1 1 d . . .
O6 O 0.67061(14) 0.39581(16) 0.15044(15) 0.0475(6) Uani 1 1 d . . .
O7 O 0.38126(12) 0.28195(17) 0.07760(12) 0.0405(5) Uani 1 1 d . . .
O8 O 0.47828(12) 0.35824(15) 0.17163(14) 0.0388(5) Uani 1 1 d . . .
N1 N -0.14084(14) 0.43997(17) 0.28554(14) 0.0302(5) Uani 1 1 d . . .
N2 N 0.00632(13) 0.54676(17) 0.38328(14) 0.0290(5) Uani 1 1 d . . .
N3 N -0.19674(13) 0.55259(18) 0.37121(15) 0.0332(6) Uani 1 1 d . . .
N4 N -0.23306(14) 0.51900(19) 0.42440(16) 0.0346(6) Uani 1 1 d . . .
N5 N -0.27170(16) 0.4957(2) 0.47123(19) 0.0485(7) Uani 1 1 d . . .
N6 N 0.62629(14) 0.29868(18) 0.24016(14) 0.0317(5) Uani 1 1 d . . .
N7 N 0.47694(13) 0.18525(17) 0.15059(14) 0.0299(5) Uani 1 1 d . . .
N8 N 0.67594(15) 0.1707(2) 0.16291(17) 0.0409(6) Uani 1 1 d . . .
N9 N 0.71715(15) 0.2032(2) 0.11379(16) 0.0407(6) Uani 1 1 d . . .
N10 N 0.75927(18) 0.2235(3) 0.07094(19) 0.0595(9) Uani 1 1 d . . .
C1 C -0.12829(15) 0.5001(2) 0.35819(16) 0.0271(6) Uani 1 1 d . . .
H1 H -0.1117 0.4611 0.4072 0.033 Uiso 1 1 calc R . .
C2 C -0.06655(15) 0.5708(2) 0.33762(17) 0.0285(6) Uani 1 1 d . . .
C3 C -0.07741(17) 0.6731(2) 0.36828(19) 0.0340(7) Uani 1 1 d . . .
H3A H -0.1073 0.7110 0.3268 0.041 Uiso 1 1 calc R . .
H3B H -0.1025 0.6728 0.4193 0.041 Uiso 1 1 calc R . .
C4 C 0.00059(18) 0.7132(2) 0.3831(2) 0.0433(8) Uani 1 1 d . . .
H4A H 0.0184 0.7369 0.3317 0.052 Uiso 1 1 calc R . .
H4B H 0.0020 0.7660 0.4230 0.052 Uiso 1 1 calc R . .
C5 C 0.04675(18) 0.6313(2) 0.4161(2) 0.0401(8) Uani 1 1 d . . .
H5A H 0.0971 0.6339 0.3973 0.048 Uiso 1 1 calc R . .
H5B H 0.0509 0.6310 0.4765 0.048 Uiso 1 1 calc R . .
C6 C -0.06699(16) 0.5606(2) 0.24553(17) 0.0300(6) Uani 1 1 d . . .
C7 C -0.03385(17) 0.6152(2) 0.18924(18) 0.0365(7) Uani 1 1 d . . .
H7 H -0.0065 0.6704 0.2062 0.044 Uiso 1 1 calc R . .
C8 C -0.04079(18) 0.5888(3) 0.10747(19) 0.0431(8) Uani 1 1 d . . .
H8 H -0.0186 0.6264 0.0684 0.052 Uiso 1 1 calc R . .
C9 C -0.08006(18) 0.5076(3) 0.08296(18) 0.0421(8) Uani 1 1 d . . .
H9 H -0.0834 0.4895 0.0272 0.050 Uiso 1 1 calc R . .
C10 C -0.11438(18) 0.4525(2) 0.13806(18) 0.0375(7) Uani 1 1 d . . .
H10 H -0.1415 0.3971 0.1212 0.045 Uiso 1 1 calc R . .
C11 C -0.10778(16) 0.4813(2) 0.21919(17) 0.0308(6) Uani 1 1 d . . .
C12 C -0.16390(17) 0.3481(2) 0.28776(18) 0.0352(7) Uani 1 1 d . . .
C13 C -0.21092(18) 0.2322(2) 0.3743(2) 0.0378(7) Uani 1 1 d . . .
H13A H -0.2259 0.1992 0.3224 0.045 Uiso 1 1 calc R . .
H13B H -0.2524 0.2281 0.4095 0.045 Uiso 1 1 calc R . .
C14 C -0.1439(2) 0.1858(3) 0.4155(2) 0.0491(9) Uani 1 1 d . . .
H14A H -0.1044 0.1851 0.3786 0.074 Uiso 1 1 calc R . .
H14B H -0.1559 0.1204 0.4301 0.074 Uiso 1 1 calc R . .
H14C H -0.1273 0.2213 0.4650 0.074 Uiso 1 1 calc R . .
C15 C 0.10769(16) 0.4505(2) 0.29826(17) 0.0288(6) Uani 1 1 d . . .
C16 C 0.17887(17) 0.4857(2) 0.3112(2) 0.0397(7) Uani 1 1 d . . .
H16 H 0.1973 0.5080 0.3635 0.048 Uiso 1 1 calc R . .
C17 C 0.22301(18) 0.4878(3) 0.2465(2) 0.0431(8) Uani 1 1 d . . .
H17 H 0.2716 0.5134 0.2548 0.052 Uiso 1 1 calc R . .
C18 C 0.19789(18) 0.4536(2) 0.16995(19) 0.0374(7) Uani 1 1 d . . .
C19 C 0.12633(18) 0.4185(2) 0.15901(19) 0.0379(7) Uani 1 1 d . . .
H19 H 0.1080 0.3953 0.1069 0.045 Uiso 1 1 calc R . .
C20 C 0.08108(17) 0.4164(2) 0.22216(18) 0.0342(7) Uani 1 1 d . . .
H20 H 0.0322 0.3918 0.2136 0.041 Uiso 1 1 calc R . .
C21 C 0.2476(2) 0.4542(3) 0.1016(2) 0.0533(9) Uani 1 1 d . . .
H21A H 0.2819 0.5081 0.1084 0.080 Uiso 1 1 calc R . .
H21B H 0.2176 0.4601 0.0494 0.080 Uiso 1 1 calc R . .
H21C H 0.2759 0.3948 0.1023 0.080 Uiso 1 1 calc R . .
C22 C 0.61025(16) 0.2298(2) 0.17446(17) 0.0300(6) Uani 1 1 d . . .
H22 H 0.5930 0.2630 0.1226 0.036 Uiso 1 1 calc R . .
C23 C 0.54667(16) 0.1655(2) 0.20377(16) 0.0275(6) Uani 1 1 d . . .
C24 C 0.55491(18) 0.0580(2) 0.19193(18) 0.0350(7) Uani 1 1 d . . .
H24A H 0.6078 0.0400 0.1940 0.042 Uiso 1 1 calc R . .
H24B H 0.5315 0.0226 0.2348 0.042 Uiso 1 1 calc R . .
C25 C 0.5159(2) 0.0370(2) 0.10840(19) 0.0407(8) Uani 1 1 d . . .
H25A H 0.5473 0.0545 0.0645 0.049 Uiso 1 1 calc R . .
H25B H 0.5024 -0.0310 0.1030 0.049 Uiso 1 1 calc R . .
C26 C 0.44765(19) 0.0994(2) 0.1066(2) 0.0397(8) Uani 1 1 d . . .
H26A H 0.4283 0.1147 0.0500 0.048 Uiso 1 1 calc R . .
H26B H 0.4080 0.0689 0.1351 0.048 Uiso 1 1 calc R . .
C27 C 0.54561(16) 0.1945(2) 0.29190(16) 0.0302(6) Uani 1 1 d . . .
C28 C 0.50717(19) 0.1534(3) 0.35180(19) 0.0409(8) Uani 1 1 d . . .
H28 H 0.4767 0.0993 0.3403 0.049 Uiso 1 1 calc R . .
C29 C 0.5144(2) 0.1934(3) 0.4295(2) 0.0513(9) Uani 1 1 d . . .
H29 H 0.4883 0.1667 0.4716 0.062 Uiso 1 1 calc R . .
C30 C 0.5591(2) 0.2713(3) 0.44565(19) 0.0498(9) Uani 1 1 d . . .
H30 H 0.5628 0.2976 0.4990 0.060 Uiso 1 1 calc R . .
C31 C 0.59852(19) 0.3124(2) 0.38719(19) 0.0410(8) Uani 1 1 d . . .
H31 H 0.6295 0.3659 0.3992 0.049 Uiso 1 1 calc R . .
C32 C 0.59105(17) 0.2720(2) 0.30968(17) 0.0327(7) Uani 1 1 d . . .
C33 C 0.64585(18) 0.3909(2) 0.2246(2) 0.0400(7) Uani 1 1 d . . .
C34 C 0.6798(2) 0.4910(3) 0.1162(3) 0.0617(11) Uani 1 1 d . . .
H34A H 0.7306 0.4985 0.0997 0.074 Uiso 1 1 calc R . .
H34B H 0.6715 0.5400 0.1576 0.074 Uiso 1 1 calc R . .
C35 C 0.6252(3) 0.5024(3) 0.0446(3) 0.0699(13) Uani 1 1 d . . .
H35A H 0.6353 0.4557 0.0028 0.105 Uiso 1 1 calc R . .
H35B H 0.6289 0.5666 0.0224 0.105 Uiso 1 1 calc R . .
H35C H 0.5751 0.4923 0.0611 0.105 Uiso 1 1 calc R . .
C36 C 0.36870(16) 0.2736(2) 0.23253(17) 0.0306(6) Uani 1 1 d . . .
C37 C 0.30398(17) 0.2213(2) 0.22110(19) 0.0363(7) Uani 1 1 d . . .
H37 H 0.2906 0.1909 0.1704 0.044 Uiso 1 1 calc R . .
C38 C 0.25893(18) 0.2139(2) 0.2845(2) 0.0397(7) Uani 1 1 d . . .
H38 H 0.2149 0.1771 0.2771 0.048 Uiso 1 1 calc R . .
C39 C 0.27674(17) 0.2593(2) 0.35887(19) 0.0364(7) Uani 1 1 d . . .
C40 C 0.34166(18) 0.3117(2) 0.3683(2) 0.0407(8) Uani 1 1 d . . .
H40 H 0.3548 0.3429 0.4186 0.049 Uiso 1 1 calc R . .
C41 C 0.38786(17) 0.3194(2) 0.30601(19) 0.0356(7) Uani 1 1 d . . .
H41 H 0.4322 0.3556 0.3135 0.043 Uiso 1 1 calc R . .
C42 C 0.2268(2) 0.2511(3) 0.4274(2) 0.0496(9) Uani 1 1 d . . .
H42A H 0.1985 0.3100 0.4311 0.074 Uiso 1 1 calc R . .
H42B H 0.2570 0.2402 0.4789 0.074 Uiso 1 1 calc R . .
H42C H 0.1926 0.1978 0.4166 0.074 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.428(2) . ?
S1 O4 1.435(2) . ?
S1 N2 1.622(2) . ?
S1 C15 1.772(3) . ?
S2 O7 1.434(2) . ?
S2 O8 1.434(2) . ?
S2 N7 1.622(3) . ?
S2 C36 1.770(3) . ?
O1 C12 1.208(4) . ?
O2 C12 1.353(4) . ?
O2 C13 1.457(4) . ?
O5 C33 1.198(4) . ?
O6 C33 1.339(4) . ?
O6 C34 1.468(4) . ?
N1 C12 1.360(4) . ?
N1 C11 1.416(4) . ?
N1 C1 1.467(3) . ?
N2 C5 1.475(4) . ?
N2 C2 1.500(3) . ?
N3 N4 1.235(4) . ?
N3 C1 1.476(4) . ?
N4 N5 1.135(4) . ?
N6 C33 1.376(4) . ?
N6 C32 1.410(4) . ?
N6 C22 1.463(4) . ?
N7 C26 1.483(4) . ?
N7 C23 1.499(3) . ?
N8 N9 1.236(4) . ?
N8 C22 1.479(4) . ?
N9 N10 1.121(4) . ?
C1 C2 1.557(4) . ?
C1 H1 1.0000 . ?
C2 C6 1.523(4) . ?
C2 C3 1.543(4) . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.499(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.382(4) . ?
C6 C11 1.387(4) . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C13 C14 1.489(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.381(4) . ?
C15 C20 1.388(4) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(5) . ?
C18 C21 1.503(5) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.574(4) . ?
C22 H22 1.0000 . ?
C23 C27 1.509(4) . ?
C23 C24 1.534(4) . ?
C24 C25 1.519(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.516(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.384(4) . ?
C27 C28 1.384(4) . ?
C28 C29 1.394(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(4) . ?
C31 H31 0.9500 . ?
C34 C35 1.481(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.384(4) . ?
C36 C41 1.388(4) . ?
C37 C38 1.384(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.394(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.386(5) . ?
C39 C42 1.512(5) . ?
C40 C41 1.384(4) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.88(14) . . ?
O3 S1 N2 107.88(13) . . ?
O4 S1 N2 105.47(13) . . ?
O3 S1 C15 107.82(14) . . ?
O4 S1 C15 106.60(14) . . ?
N2 S1 C15 108.81(13) . . ?
O7 S2 O8 119.89(14) . . ?
O7 S2 N7 105.59(13) . . ?
O8 S2 N7 106.99(13) . . ?
O7 S2 C36 107.05(14) . . ?
O8 S2 C36 107.54(14) . . ?
N7 S2 C36 109.53(14) . . ?
C12 O2 C13 115.3(2) . . ?
C33 O6 C34 117.1(3) . . ?
C12 N1 C11 124.2(3) . . ?
C12 N1 C1 123.5(2) . . ?
C11 N1 C1 110.3(2) . . ?
C5 N2 C2 112.9(2) . . ?
C5 N2 S1 118.65(19) . . ?
C2 N2 S1 126.61(19) . . ?
N4 N3 C1 114.8(2) . . ?
N5 N4 N3 172.7(3) . . ?
C33 N6 C32 123.0(3) . . ?
C33 N6 C22 121.7(3) . . ?
C32 N6 C22 110.5(2) . . ?
C26 N7 C23 112.4(2) . . ?
C26 N7 S2 121.1(2) . . ?
C23 N7 S2 125.38(19) . . ?
N9 N8 C22 114.6(3) . . ?
N10 N9 N8 172.0(4) . . ?
N1 C1 N3 109.6(2) . . ?
N1 C1 C2 104.7(2) . . ?
N3 C1 C2 109.9(2) . . ?
N1 C1 H1 110.8 . . ?
N3 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
N2 C2 C6 113.9(2) . . ?
N2 C2 C3 100.3(2) . . ?
C6 C2 C3 115.1(2) . . ?
N2 C2 C1 111.4(2) . . ?
C6 C2 C1 102.4(2) . . ?
C3 C2 C1 114.2(2) . . ?
C4 C3 C2 104.8(2) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 104.7(3) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N2 C5 C4 104.1(2) . . ?
N2 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
N2 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C11 119.3(3) . . ?
C7 C6 C2 130.6(3) . . ?
C11 C6 C2 110.1(3) . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 117.5(3) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C6 C11 C10 122.2(3) . . ?
C6 C11 N1 109.8(2) . . ?
C10 C11 N1 128.0(3) . . ?
O1 C12 O2 125.1(3) . . ?
O1 C12 N1 125.1(3) . . ?
O2 C12 N1 109.8(3) . . ?
O2 C13 C14 109.6(3) . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.6(3) . . ?
C16 C15 S1 119.6(2) . . ?
C20 C15 S1 119.8(2) . . ?
C15 C16 C17 118.9(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 118.1(3) . . ?
C19 C18 C21 121.4(3) . . ?
C17 C18 C21 120.5(3) . . ?
C20 C19 C18 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C15 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 N8 111.0(2) . . ?
N6 C22 C23 104.9(2) . . ?
N8 C22 C23 109.6(2) . . ?
N6 C22 H22 110.4 . . ?
N8 C22 H22 110.4 . . ?
C23 C22 H22 110.4 . . ?
N7 C23 C27 115.5(2) . . ?
N7 C23 C24 101.3(2) . . ?
C27 C23 C24 113.5(2) . . ?
N7 C23 C22 108.5(2) . . ?
C27 C23 C22 102.2(2) . . ?
C24 C23 C22 116.5(2) . . ?
C25 C24 C23 105.3(2) . . ?
C25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
C26 C25 C24 102.6(3) . . ?
C26 C25 H25A 111.2 . . ?
C24 C25 H25A 111.2 . . ?
C26 C25 H25B 111.2 . . ?
C24 C25 H25B 111.2 . . ?
H25A C25 H25B 109.2 . . ?
N7 C26 C25 101.9(2) . . ?
N7 C26 H26A 111.4 . . ?
C25 C26 H26A 111.4 . . ?
N7 C26 H26B 111.4 . . ?
C25 C26 H26B 111.4 . . ?
H26A C26 H26B 109.3 . . ?
C32 C27 C28 120.4(3) . . ?
C32 C27 C23 111.0(3) . . ?
C28 C27 C23 128.5(3) . . ?
C27 C28 C29 118.3(3) . . ?
C27 C28 H28 120.9 . . ?
C29 C28 H28 120.9 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 122.3(3) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C32 117.1(3) . . ?
C30 C31 H31 121.5 . . ?
C32 C31 H31 121.5 . . ?
C27 C32 C31 121.6(3) . . ?
C27 C32 N6 110.0(2) . . ?
C31 C32 N6 128.4(3) . . ?
O5 C33 O6 126.0(3) . . ?
O5 C33 N6 124.6(3) . . ?
O6 C33 N6 109.3(3) . . ?
O6 C34 C35 108.4(3) . . ?
O6 C34 H34A 110.0 . . ?
C35 C34 H34A 110.0 . . ?
O6 C34 H34B 110.0 . . ?
C35 C34 H34B 110.0 . . ?
H34A C34 H34B 108.4 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C41 120.6(3) . . ?
C37 C36 S2 119.5(2) . . ?
C41 C36 S2 119.8(2) . . ?
C36 C37 C38 119.1(3) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C37 C38 C39 121.5(3) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C40 C39 C38 118.1(3) . . ?
C40 C39 C42 121.0(3) . . ?
C38 C39 C42 120.9(3) . . ?
C41 C40 C39 121.5(3) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C36 119.2(3) . . ?
C40 C41 H41 120.4 . . ?
C36 C41 H41 120.4 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N2 C5 167.5(2) . . . . ?
O4 S1 N2 C5 38.2(3) . . . . ?
C15 S1 N2 C5 -75.8(2) . . . . ?
O3 S1 N2 C2 -29.2(3) . . . . ?
O4 S1 N2 C2 -158.4(2) . . . . ?
C15 S1 N2 C2 87.5(3) . . . . ?
C1 N3 N4 N5 -178(100) . . . . ?
O7 S2 N7 C26 -30.2(3) . . . . ?
O8 S2 N7 C26 -158.9(2) . . . . ?
C36 S2 N7 C26 84.8(3) . . . . ?
O7 S2 N7 C23 162.9(2) . . . . ?
O8 S2 N7 C23 34.1(3) . . . . ?
C36 S2 N7 C23 -82.2(3) . . . . ?
C22 N8 N9 N10 -178(100) . . . . ?
C12 N1 C1 N3 -91.6(3) . . . . ?
C11 N1 C1 N3 103.7(3) . . . . ?
C12 N1 C1 C2 150.5(3) . . . . ?
C11 N1 C1 C2 -14.2(3) . . . . ?
N4 N3 C1 N1 101.0(3) . . . . ?
N4 N3 C1 C2 -144.4(2) . . . . ?
C5 N2 C2 C6 106.8(3) . . . . ?
S1 N2 C2 C6 -57.4(3) . . . . ?
C5 N2 C2 C3 -16.7(3) . . . . ?
S1 N2 C2 C3 179.1(2) . . . . ?
C5 N2 C2 C1 -138.0(3) . . . . ?
S1 N2 C2 C1 57.8(3) . . . . ?
N1 C1 C2 N2 -106.3(2) . . . . ?
N3 C1 C2 N2 136.1(2) . . . . ?
N1 C1 C2 C6 15.8(3) . . . . ?
N3 C1 C2 C6 -101.8(2) . . . . ?
N1 C1 C2 C3 141.0(2) . . . . ?
N3 C1 C2 C3 23.3(3) . . . . ?
N2 C2 C3 C4 32.0(3) . . . . ?
C6 C2 C3 C4 -90.7(3) . . . . ?
C1 C2 C3 C4 151.2(2) . . . . ?
C2 C3 C4 C5 -37.0(3) . . . . ?
C2 N2 C5 C4 -5.3(3) . . . . ?
S1 N2 C5 C4 160.2(2) . . . . ?
C3 C4 C5 N2 25.8(3) . . . . ?
N2 C2 C6 C7 -71.8(4) . . . . ?
C3 C2 C6 C7 43.3(4) . . . . ?
C1 C2 C6 C7 167.9(3) . . . . ?
N2 C2 C6 C11 107.4(3) . . . . ?
C3 C2 C6 C11 -137.5(3) . . . . ?
C1 C2 C6 C11 -12.9(3) . . . . ?
C11 C6 C7 C8 -1.2(5) . . . . ?
C2 C6 C7 C8 178.0(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C7 C6 C11 C10 2.4(5) . . . . ?
C2 C6 C11 C10 -176.9(3) . . . . ?
C7 C6 C11 N1 -175.9(3) . . . . ?
C2 C6 C11 N1 4.8(3) . . . . ?
C9 C10 C11 C6 -1.6(5) . . . . ?
C9 C10 C11 N1 176.4(3) . . . . ?
C12 N1 C11 C6 -158.2(3) . . . . ?
C1 N1 C11 C6 6.4(3) . . . . ?
C12 N1 C11 C10 23.6(5) . . . . ?
C1 N1 C11 C10 -171.8(3) . . . . ?
C13 O2 C12 O1 10.5(4) . . . . ?
C13 O2 C12 N1 -170.5(2) . . . . ?
C11 N1 C12 O1 0.6(5) . . . . ?
C1 N1 C12 O1 -162.0(3) . . . . ?
C11 N1 C12 O2 -178.3(2) . . . . ?
C1 N1 C12 O2 19.1(4) . . . . ?
C12 O2 C13 C14 86.1(3) . . . . ?
O3 S1 C15 C16 -154.4(2) . . . . ?
O4 S1 C15 C16 -24.5(3) . . . . ?
N2 S1 C15 C16 88.9(3) . . . . ?
O3 S1 C15 C20 24.4(3) . . . . ?
O4 S1 C15 C20 154.3(2) . . . . ?
N2 S1 C15 C20 -92.4(3) . . . . ?
C20 C15 C16 C17 1.1(5) . . . . ?
S1 C15 C16 C17 179.8(3) . . . . ?
C15 C16 C17 C18 -1.5(5) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C16 C17 C18 C21 -178.2(3) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C21 C18 C19 C20 178.8(3) . . . . ?
C18 C19 C20 C15 0.2(5) . . . . ?
C16 C15 C20 C19 -0.5(5) . . . . ?
S1 C15 C20 C19 -179.2(2) . . . . ?
C33 N6 C22 N8 96.9(3) . . . . ?
C32 N6 C22 N8 -107.1(3) . . . . ?
C33 N6 C22 C23 -144.8(3) . . . . ?
C32 N6 C22 C23 11.2(3) . . . . ?
N9 N8 C22 N6 -89.8(3) . . . . ?
N9 N8 C22 C23 154.7(3) . . . . ?
C26 N7 C23 C27 -126.1(3) . . . . ?
S2 N7 C23 C27 41.8(3) . . . . ?
C26 N7 C23 C24 -3.1(3) . . . . ?
S2 N7 C23 C24 164.8(2) . . . . ?
C26 N7 C23 C22 120.0(3) . . . . ?
S2 N7 C23 C22 -72.1(3) . . . . ?
N6 C22 C23 N7 111.1(2) . . . . ?
N8 C22 C23 N7 -129.7(2) . . . . ?
N6 C22 C23 C27 -11.3(3) . . . . ?
N8 C22 C23 C27 107.9(3) . . . . ?
N6 C22 C23 C24 -135.6(2) . . . . ?
N8 C22 C23 C24 -16.3(3) . . . . ?
N7 C23 C24 C25 26.6(3) . . . . ?
C27 C23 C24 C25 151.0(3) . . . . ?
C22 C23 C24 C25 -90.7(3) . . . . ?
C23 C24 C25 C26 -40.5(3) . . . . ?
C23 N7 C26 C25 -21.3(3) . . . . ?
S2 N7 C26 C25 170.2(2) . . . . ?
C24 C25 C26 N7 36.8(3) . . . . ?
N7 C23 C27 C32 -109.3(3) . . . . ?
C24 C23 C27 C32 134.4(3) . . . . ?
C22 C23 C27 C32 8.2(3) . . . . ?
N7 C23 C27 C28 71.4(4) . . . . ?
C24 C23 C27 C28 -44.9(4) . . . . ?
C22 C23 C27 C28 -171.1(3) . . . . ?
C32 C27 C28 C29 1.3(5) . . . . ?
C23 C27 C28 C29 -179.5(3) . . . . ?
C27 C28 C29 C30 -0.4(5) . . . . ?
C28 C29 C30 C31 -0.5(6) . . . . ?
C29 C30 C31 C32 0.5(5) . . . . ?
C28 C27 C32 C31 -1.3(5) . . . . ?
C23 C27 C32 C31 179.3(3) . . . . ?
C28 C27 C32 N6 177.7(3) . . . . ?
C23 C27 C32 N6 -1.7(3) . . . . ?
C30 C31 C32 C27 0.4(5) . . . . ?
C30 C31 C32 N6 -178.4(3) . . . . ?
C33 N6 C32 C27 149.3(3) . . . . ?
C22 N6 C32 C27 -6.4(3) . . . . ?
C33 N6 C32 C31 -31.8(5) . . . . ?
C22 N6 C32 C31 172.5(3) . . . . ?
C34 O6 C33 O5 -13.3(5) . . . . ?
C34 O6 C33 N6 167.9(3) . . . . ?
C32 N6 C33 O5 7.8(5) . . . . ?
C22 N6 C33 O5 160.8(3) . . . . ?
C32 N6 C33 O6 -173.2(3) . . . . ?
C22 N6 C33 O6 -20.3(4) . . . . ?
C33 O6 C34 C35 -113.3(4) . . . . ?
O7 S2 C36 C37 34.6(3) . . . . ?
O8 S2 C36 C37 164.6(2) . . . . ?
N7 S2 C36 C37 -79.5(3) . . . . ?
O7 S2 C36 C41 -145.9(3) . . . . ?
O8 S2 C36 C41 -15.8(3) . . . . ?
N7 S2 C36 C41 100.1(3) . . . . ?
C41 C36 C37 C38 -1.0(5) . . . . ?
S2 C36 C37 C38 178.6(2) . . . . ?
C36 C37 C38 C39 1.1(5) . . . . ?
C37 C38 C39 C40 -0.7(5) . . . . ?
C37 C38 C39 C42 179.6(3) . . . . ?
C38 C39 C40 C41 0.1(5) . . . . ?
C42 C39 C40 C41 179.8(3) . . . . ?
C39 C40 C41 C36 0.0(5) . . . . ?
C37 C36 C41 C40 0.5(5) . . . . ?
S2 C36 C41 C40 -179.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.145
_database_code_depnum_ccdc_archive 'CCDC 1015375'
