# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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data_hmimcf30514

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 F6 N2 S'
_chemical_formula_weight         312.24

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4302(5)
_cell_length_b                   23.8152(15)
_cell_length_c                   36.666(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7361.4(8)
_cell_formula_units_Z            24
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9181
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      32.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             3744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            117976
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         1.402
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             22429
_reflns_number_gt                21428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+3.1799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.34(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         22429
_refine_ls_number_parameters     1247
_refine_ls_number_restraints     670
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00373(7) 0.67954(2) -0.44773(2) 0.02084(10) Uani 1 1 d . . . . .
S2 S -0.64233(7) 0.49822(2) -0.55631(2) 0.02117(10) Uani 1 1 d . . . . .
S3 S -0.30343(7) 0.67159(2) -0.54610(2) 0.02047(10) Uani 1 1 d . . . . .
S4 S -0.33464(7) 0.50849(2) -0.45983(2) 0.01968(10) Uani 1 1 d . . . . .
S5 S 0.12980(7) 0.86139(3) -0.04060(2) 0.02319(11) Uani 1 1 d . . . . .
S6 S -0.21538(10) 0.84844(3) 0.04732(2) 0.03240(15) Uani 1 1 d . . . . .
F11 F -0.1503(2) 0.72885(9) -0.24630(4) 0.0380(4) Uani 1 1 d . U . . .
F12 F -0.3273(2) 0.78075(8) -0.27129(4) 0.0379(4) Uani 1 1 d . U . . .
F13 F -0.3386(2) 0.69145(8) -0.27747(5) 0.0410(4) Uani 1 1 d . U . . .
F14 F 0.3444(2) 0.76183(10) -0.30636(5) 0.0474(5) Uani 1 1 d . U . . .
F15 F 0.35737(19) 0.71538(7) -0.35626(5) 0.0357(4) Uani 1 1 d . U . . .
F16 F 0.33530(19) 0.80437(6) -0.35799(5) 0.0328(3) Uani 1 1 d . U . . .
F21 F -0.2832(7) 0.4240(8) -0.7265(2) 0.097(4) Uani 0.64(2) 1 d D U P A 1
F22 F -0.4910(13) 0.3920(4) -0.7530(3) 0.0590(19) Uani 0.64(2) 1 d D U P A 1
F23 F -0.4649(11) 0.4796(3) -0.74403(18) 0.0597(17) Uani 0.64(2) 1 d D U P A 1
F21A F -0.393(3) 0.4773(4) -0.7390(5) 0.085(5) Uani 0.36(2) 1 d D U P A 2
F22A F -0.2990(13) 0.3984(6) -0.7257(3) 0.052(3) Uani 0.36(2) 1 d D U P A 2
F23A F -0.5117(15) 0.4031(9) -0.7564(4) 0.061(4) Uani 0.36(2) 1 d D U P A 2
F24 F -1.0061(2) 0.39642(11) -0.69160(5) 0.0536(6) Uani 1 1 d . U . . .
F25 F -0.98121(19) 0.35980(7) -0.63844(5) 0.0369(4) Uani 1 1 d . U . . .
F26 F -1.0156(2) 0.44819(7) -0.64380(5) 0.0364(4) Uani 1 1 d . U . . .
F31 F 0.0306(9) 0.6088(4) -0.7030(2) 0.0449(19) Uani 0.467(4) 1 d D U P B 1
F32 F -0.1599(11) 0.5811(4) -0.7361(2) 0.051(2) Uani 0.467(4) 1 d D U P B 1
F33 F -0.0114(16) 0.5215(5) -0.7080(4) 0.058(3) Uani 0.467(4) 1 d D U P B 1
F31A F -0.129(3) 0.6100(8) -0.7289(5) 0.045(5) Uani 0.114(4) 1 d D U P B 2
F32A F -0.130(3) 0.5206(8) -0.7242(7) 0.055(5) Uani 0.114(4) 1 d D U P B 2
F33A F 0.0588(16) 0.5675(13) -0.7003(5) 0.051(5) Uani 0.114(4) 1 d D U P B 2
F31B F -0.0120(14) 0.6161(4) -0.7130(3) 0.061(3) Uani 0.419(4) 1 d D U P B 3
F32B F -0.1663(13) 0.5531(5) -0.7367(2) 0.053(3) Uani 0.419(4) 1 d D U P B 3
F33B F 0.0271(14) 0.5303(5) -0.7027(4) 0.038(2) Uani 0.419(4) 1 d D U P B 3
F34 F -0.6960(2) 0.61683(8) -0.62274(5) 0.0386(4) Uani 1 1 d . U . . .
F35 F -0.6585(2) 0.62727(8) -0.68014(5) 0.0390(4) Uani 1 1 d . U . . .
F36 F -0.6992(2) 0.54491(7) -0.65788(6) 0.0411(4) Uani 1 1 d . U . . .
F41 F -0.6599(2) 0.63209(8) -0.29470(5) 0.0422(4) Uani 1 1 d . U . . .
F42 F -0.6871(2) 0.54430(8) -0.30440(5) 0.0385(4) Uani 1 1 d . U . . .
F43 F -0.5045(2) 0.57329(11) -0.26832(4) 0.0508(6) Uani 1 1 d . U . . .
F44 F 0.04074(18) 0.62118(7) -0.33971(5) 0.0354(4) Uani 1 1 d . U . . .
F45 F -0.00044(19) 0.53493(7) -0.32590(4) 0.0306(3) Uani 1 1 d . U . . .
F46 F 0.04410(19) 0.55778(8) -0.38150(5) 0.0356(4) Uani 1 1 d . U . . .
F51 F -0.1862(13) 0.9329(3) -0.2255(3) 0.055(2) Uani 0.54(2) 1 d D U P C 1
F52 F -0.2112(13) 0.8489(4) -0.2068(2) 0.053(2) Uani 0.54(2) 1 d D U P C 1
F53 F -0.0199(9) 0.8702(6) -0.24204(18) 0.047(2) Uani 0.54(2) 1 d D U P C 1
F51A F -0.105(2) 0.9324(3) -0.2375(2) 0.057(3) Uani 0.46(2) 1 d D U P C 2
F52A F -0.2426(8) 0.8699(6) -0.2095(3) 0.048(2) Uani 0.46(2) 1 d D U P C 2
F53A F -0.0246(11) 0.8481(5) -0.2355(3) 0.047(2) Uani 0.46(2) 1 d D U P C 2
F54 F 0.4967(2) 0.87850(7) -0.14476(6) 0.0465(5) Uani 1 1 d . U . . .
F55 F 0.4717(2) 0.93797(10) -0.18857(5) 0.0490(5) Uani 1 1 d . U . . .
F56 F 0.47680(19) 0.96598(7) -0.13345(5) 0.0353(4) Uani 1 1 d . U . . .
F61 F -0.1310(19) 0.7884(3) 0.2192(3) 0.086(5) Uani 0.356(10) 1 d D U P D 1
F62 F -0.2596(11) 0.7148(5) 0.2291(2) 0.068(3) Uani 0.356(10) 1 d D U P D 1
F63 F -0.0387(12) 0.7081(6) 0.20547(17) 0.079(4) Uani 0.356(10) 1 d D U P D 1
F61A F -0.2127(9) 0.7830(3) 0.22915(15) 0.0740(18) Uani 0.644(10) 1 d D U P D 2
F62A F -0.1675(11) 0.69685(19) 0.22340(15) 0.090(3) Uani 0.644(10) 1 d D U P D
2
F63A F -0.0002(5) 0.7564(3) 0.20490(9) 0.075(2) Uani 0.644(10) 1 d D U P D 2
F64 F -0.7186(3) 0.71125(10) 0.14032(12) 0.1102(15) Uani 1 1 d . U . . .
F65 F -0.6980(2) 0.77190(10) 0.09742(7) 0.0571(6) Uani 1 1 d . U . . .
F66 F -0.7033(3) 0.79889(10) 0.15286(6) 0.0576(6) Uani 1 1 d . U . . .
N11 N -0.2811(2) 0.73142(9) -0.46558(5) 0.0206(4) Uani 1 1 d . . . . .
H11 H -0.284(4) 0.7169(13) -0.4863(9) 0.027(8) Uiso 1 1 d . . . . .
N12 N -0.2109(2) 0.74765(8) -0.40977(5) 0.0170(3) Uani 1 1 d . . . . .
N21 N -0.3619(2) 0.44776(9) -0.53926(5) 0.0222(4) Uani 1 1 d . . . . .
H21 H -0.355(4) 0.4623(13) -0.5187(9) 0.023(7) Uiso 1 1 d . . . . .
N22 N -0.4359(2) 0.42978(8) -0.59447(5) 0.0161(3) Uani 1 1 d . . . . .
N31 N -0.0879(2) 0.59883(9) -0.51751(5) 0.0202(4) Uani 1 1 d . . . . .
H31 H -0.081(4) 0.6167(14) -0.4995(9) 0.028(8) Uiso 1 1 d . . . . .
N32 N -0.1544(2) 0.57636(8) -0.57252(5) 0.0179(3) Uani 1 1 d . . . . .
N41 N -0.5517(2) 0.58178(8) -0.48794(5) 0.0199(4) Uani 1 1 d . . . . .
H41 H -0.557(4) 0.5647(14) -0.5089(9) 0.029(8) Uiso 1 1 d . . . . .
N42 N -0.4915(2) 0.60077(8) -0.43186(5) 0.0177(3) Uani 1 1 d . . . . .
N51 N -0.1497(3) 0.91436(9) -0.02741(5) 0.0247(4) Uani 1 1 d . . . . .
H51 H -0.156(6) 0.9009(17) -0.0066(11) 0.056(12) Uiso 1 1 d . . . . .
N52 N -0.0721(2) 0.92519(8) -0.08316(5) 0.0181(3) Uani 1 1 d . . . . .
N61 N -0.0074(3) 0.76987(9) 0.02198(6) 0.0281(4) Uani 1 1 d . . . . .
H61 H 0.020(4) 0.7901(14) 0.0043(9) 0.033(9) Uiso 1 1 d . . . . .
N62 N -0.1209(2) 0.74519(8) 0.07238(5) 0.0209(4) Uani 1 1 d . . . . .
C11 C -0.1661(2) 0.72002(9) -0.44104(5) 0.0169(4) Uani 1 1 d . . . . .
C12 C -0.3987(3) 0.76465(10) -0.45042(7) 0.0236(4) Uani 1 1 d . . . . .
H12A H -0.4921 0.7776 -0.4623 0.028 Uiso 1 1 calc R U . . .
C13 C -0.3557(3) 0.77508(10) -0.41576(6) 0.0213(4) Uani 1 1 d . . . . .
H13A H -0.4128 0.7970 -0.3985 0.026 Uiso 1 1 calc R U . . .
C14 C -0.1304(3) 0.74662(9) -0.37546(5) 0.0155(4) Uani 1 1 d . . . . .
C15 C -0.2181(3) 0.73860(9) -0.34375(6) 0.0173(4) Uani 1 1 d . . . . .
H15A H -0.3294 0.7326 -0.3449 0.021 Uiso 1 1 calc R U . . .
C16 C -0.1403(3) 0.73954(9) -0.31028(5) 0.0173(4) Uani 1 1 d . . . . .
C17 C 0.0231(3) 0.74603(9) -0.30817(6) 0.0170(4) Uani 1 1 d . . . . .
H17A H 0.0759 0.7456 -0.2853 0.020 Uiso 1 1 calc R U . . .
C18 C 0.1077(2) 0.75320(9) -0.34043(6) 0.0156(4) Uani 1 1 d . . . . .
C19 C 0.0333(2) 0.75452(9) -0.37421(5) 0.0157(4) Uani 1 1 d . . . . .
H19A H 0.0924 0.7606 -0.3959 0.019 Uiso 1 1 calc R U . . .
C21 C -0.4797(3) 0.45804(9) -0.56339(5) 0.0171(4) Uani 1 1 d . . . . .
C22 C -0.2451(3) 0.41444(11) -0.55437(7) 0.0248(5) Uani 1 1 d . . . . .
H22A H -0.1510 0.4019 -0.5427 0.030 Uiso 1 1 calc R U . . .
C23 C -0.2904(3) 0.40313(10) -0.58886(6) 0.0211(4) Uani 1 1 d . . . . .
H23A H -0.2339 0.3811 -0.6061 0.025 Uiso 1 1 calc R U . . .
C24 C -0.5221(3) 0.42651(9) -0.62787(5) 0.0157(4) Uani 1 1 d . . . . .
C25 C -0.4398(3) 0.43022(10) -0.66077(6) 0.0192(4) Uani 1 1 d . . . . .
H25A H -0.3287 0.4367 -0.6610 0.023 Uiso 1 1 calc R U . . .
C26 C -0.5237(3) 0.42421(11) -0.69321(6) 0.0230(4) Uani 1 1 d . . . . .
C27 C -0.6864(3) 0.41588(10) -0.69363(6) 0.0223(4) Uani 1 1 d . . . . .
H27A H -0.7424 0.4124 -0.7160 0.027 Uiso 1 1 calc R U . . .
C28 C -0.7650(3) 0.41273(9) -0.66050(6) 0.0177(4) Uani 1 1 d . . . . .
C29 C -0.6848(3) 0.41717(9) -0.62747(6) 0.0174(4) Uani 1 1 d . . . . .
H29A H -0.7403 0.4139 -0.6050 0.021 Uiso 1 1 calc R U . . .
C31 C -0.1831(3) 0.61473(9) -0.54531(5) 0.0168(4) Uani 1 1 d . . . . .
C32 C 0.0006(3) 0.55195(10) -0.52688(6) 0.0229(4) Uani 1 1 d . . . . .
H32A H 0.0751 0.5331 -0.5118 0.028 Uiso 1 1 calc R U . . .
C33 C -0.0389(3) 0.53804(10) -0.56136(7) 0.0229(4) Uani 1 1 d . . . . .
H33A H 0.0037 0.5080 -0.5753 0.027 Uiso 1 1 calc R U . . .
C34 C -0.2236(3) 0.57709(9) -0.60812(6) 0.0173(4) Uani 1 1 d . . . . .
C35 C -0.1262(3) 0.57096(9) -0.63833(6) 0.0179(4) Uani 1 1 d . . . . .
H35A H -0.0152 0.5657 -0.6354 0.021 Uiso 1 1 calc R U . . .
C36 C -0.1931(3) 0.57260(10) -0.67307(6) 0.0213(4) Uani 1 1 d . . . . .
C37 C -0.3549(3) 0.58072(10) -0.67762(6) 0.0215(4) Uani 1 1 d . . . . .
H37A H -0.3999 0.5824 -0.7013 0.026 Uiso 1 1 calc R U . . .
C38 C -0.4499(3) 0.58639(9) -0.64682(6) 0.0195(4) Uani 1 1 d . . . . .
C39 C -0.3864(3) 0.58437(9) -0.61188(6) 0.0186(4) Uani 1 1 d . . . . .
H39A H -0.4526 0.5879 -0.5910 0.022 Uiso 1 1 calc R U . . .
C41 C -0.4582(2) 0.56434(9) -0.46006(6) 0.0164(4) Uani 1 1 d . . . . .
C42 C -0.6430(3) 0.62737(10) -0.47764(6) 0.0236(4) Uani 1 1 d . . . . .
H42A H -0.7173 0.6468 -0.4925 0.028 Uiso 1 1 calc R U . . .
C43 C -0.6074(3) 0.63916(10) -0.44272(6) 0.0221(4) Uani 1 1 d . . . . .
H43A H -0.6525 0.6681 -0.4282 0.027 Uiso 1 1 calc R U . . .
C44 C -0.4279(2) 0.59597(9) -0.39588(6) 0.0155(4) Uani 1 1 d . . . . .
C45 C -0.5300(3) 0.59531(9) -0.36623(6) 0.0170(4) Uani 1 1 d . . . . .
H45A H -0.6410 0.5999 -0.3696 0.020 Uiso 1 1 calc R U . . .
C46 C -0.4670(3) 0.58785(9) -0.33140(6) 0.0184(4) Uani 1 1 d . . . . .
C47 C -0.3052(3) 0.58063(9) -0.32622(6) 0.0194(4) Uani 1 1 d . . . . .
H47A H -0.2632 0.5750 -0.3025 0.023 Uiso 1 1 calc R U . . .
C48 C -0.2052(3) 0.58180(9) -0.35655(6) 0.0169(4) Uani 1 1 d . . . . .
C49 C -0.2645(2) 0.59010(9) -0.39159(6) 0.0166(4) Uani 1 1 d . . . . .
H49A H -0.1954 0.5917 -0.4120 0.020 Uiso 1 1 calc R U . . .
C51 C -0.0313(3) 0.90083(9) -0.05059(6) 0.0184(4) Uani 1 1 d . . . . .
C52 C -0.2661(3) 0.94552(11) -0.04464(7) 0.0259(5) Uani 1 1 d . . . . .
H52A H -0.3614 0.9592 -0.0340 0.031 Uiso 1 1 calc R U . . .
C53 C -0.2181(3) 0.95268(11) -0.07941(6) 0.0233(4) Uani 1 1 d . . . . .
H53A H -0.2731 0.9727 -0.0979 0.028 Uiso 1 1 calc R U . . .
C54 C 0.0085(3) 0.91903(9) -0.11702(5) 0.0163(4) Uani 1 1 d . . . . .
C55 C -0.0803(3) 0.90632(9) -0.14781(6) 0.0178(4) Uani 1 1 d . . . . .
H55A H -0.1918 0.9014 -0.1460 0.021 Uiso 1 1 calc R U . . .
C56 C -0.0048(3) 0.90086(9) -0.18140(6) 0.0187(4) Uani 1 1 d . . . . .
C57 C 0.1585(3) 0.90719(9) -0.18420(6) 0.0197(4) Uani 1 1 d . . . . .
H57A H 0.2102 0.9030 -0.2071 0.024 Uiso 1 1 calc R U . . .
C58 C 0.2449(3) 0.91967(9) -0.15306(6) 0.0174(4) Uani 1 1 d . . . . .
C59 C 0.1719(3) 0.92612(9) -0.11920(6) 0.0173(4) Uani 1 1 d . . . . .
H59A H 0.2324 0.9351 -0.0981 0.021 Uiso 1 1 calc R U . . .
C61 C -0.1136(3) 0.78728(10) 0.04706(6) 0.0233(4) Uani 1 1 d . . . . .
C62 C 0.0535(3) 0.71779(12) 0.03128(8) 0.0312(5) Uani 1 1 d . . . . .
H62A H 0.1303 0.6970 0.0180 0.037 Uiso 1 1 calc R U . . .
C63 C -0.0166(3) 0.70232(11) 0.06265(7) 0.0271(5) Uani 1 1 d . . . . .
H63A H 0.0016 0.6685 0.0757 0.033 Uiso 1 1 calc R U . . .
C64 C -0.2159(3) 0.74647(9) 0.10454(6) 0.0193(4) Uani 1 1 d . . . . .
C65 C -0.1429(3) 0.74293(9) 0.13821(6) 0.0205(4) Uani 1 1 d . . . . .
H65A H -0.0310 0.7390 0.1399 0.025 Uiso 1 1 calc R U . . .
C66 C -0.2353(3) 0.74520(11) 0.16956(6) 0.0249(5) Uani 1 1 d . . . . .
C67 C -0.3989(3) 0.75072(11) 0.16752(7) 0.0290(5) Uani 1 1 d . . . . .
H67A H -0.4615 0.7523 0.1890 0.035 Uiso 1 1 calc R U . . .
C68 C -0.4689(3) 0.75393(10) 0.13341(8) 0.0262(5) Uani 1 1 d . . . . .
C69 C -0.3796(3) 0.75199(10) 0.10164(7) 0.0232(4) Uani 1 1 d . . . . .
H69A H -0.4292 0.7544 0.0784 0.028 Uiso 1 1 calc R U . . .
C110 C -0.2386(3) 0.73489(11) -0.27627(6) 0.0226(4) Uani 1 1 d . . . . .
C120 C 0.2853(3) 0.75915(10) -0.33967(6) 0.0199(4) Uani 1 1 d . . . . .
C210 C -0.4369(3) 0.42844(16) -0.72892(7) 0.0388(7) Uani 1 1 d D U . . .
C220 C -0.9410(3) 0.40384(11) -0.65920(7) 0.0244(5) Uani 1 1 d . . . . .
C310 C -0.0869(3) 0.56898(12) -0.70598(7) 0.0304(5) Uani 1 1 d D U . . .
C320 C -0.6259(3) 0.59376(10) -0.65186(7) 0.0236(4) Uani 1 1 d . . . . .
C410 C -0.5783(3) 0.58451(12) -0.29945(6) 0.0248(5) Uani 1 1 d . . . . .
C420 C -0.0301(3) 0.57418(10) -0.35092(6) 0.0206(4) Uani 1 1 d . . . . .
C510 C -0.1014(3) 0.88836(12) -0.21481(6) 0.0275(5) Uani 1 1 d D U . . .
C520 C 0.4217(3) 0.92557(11) -0.15530(7) 0.0228(4) Uani 1 1 d . . . . .
C610 C -0.1558(4) 0.74302(13) 0.20643(7) 0.0381(6) Uani 1 1 d D U . . .
C620 C -0.6477(4) 0.75839(13) 0.13097(11) 0.0442(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.692(2) . ?
S2 C21 1.692(2) . ?
S3 C31 1.692(2) . ?
S4 C41 1.689(2) . ?
S5 C51 1.692(2) . ?
S6 C61 1.690(2) . ?
F11 C110 1.335(3) . ?
F12 C110 1.336(3) . ?
F13 C110 1.335(3) . ?
F14 C120 1.320(3) . ?
F15 C120 1.351(3) . ?
F16 C120 1.337(3) . ?
F21 C210 1.303(6) . ?
F22 C210 1.318(7) . ?
F23 C210 1.359(7) . ?
F21A C210 1.276(10) . ?
F22A C210 1.370(9) . ?
F23A C210 1.332(11) . ?
F24 C220 1.321(3) . ?
F25 C220 1.340(3) . ?
F26 C220 1.353(3) . ?
F31 C310 1.376(8) . ?
F32 C310 1.298(7) . ?
F33 C310 1.300(10) . ?
F31A C310 1.336(13) . ?
F32A C310 1.381(14) . ?
F33A C310 1.246(13) . ?
F31B C310 1.314(8) . ?
F32B C310 1.364(8) . ?
F33B C310 1.337(9) . ?
F34 C320 1.338(3) . ?
F35 C320 1.337(3) . ?
F36 C320 1.336(3) . ?
F41 C410 1.337(3) . ?
F42 C410 1.338(3) . ?
F43 C410 1.327(3) . ?
F44 C420 1.334(3) . ?
F45 C420 1.333(3) . ?
F46 C420 1.342(3) . ?
F51 C510 1.339(5) . ?
F52 C510 1.350(6) . ?
F53 C510 1.287(7) . ?
F51A C510 1.340(6) . ?
F52A C510 1.283(8) . ?
F53A C510 1.384(7) . ?
F54 C520 1.344(3) . ?
F55 C520 1.324(3) . ?
F56 C520 1.336(3) . ?
F61 C610 1.196(8) . ?
F62 C610 1.382(8) . ?
F63 C610 1.291(7) . ?
F61A C610 1.354(5) . ?
F62A C610 1.267(5) . ?
F63A C610 1.350(5) . ?
F64 C620 1.317(4) . ?
F65 C620 1.340(4) . ?
F66 C620 1.339(4) . ?
N11 C11 1.350(3) . ?
N11 C12 1.385(3) . ?
N12 C11 1.375(3) . ?
N12 C13 1.402(3) . ?
N12 C14 1.429(3) . ?
N21 C21 1.352(3) . ?
N21 C22 1.380(3) . ?
N22 C21 1.374(3) . ?
N22 C23 1.396(3) . ?
N22 C24 1.426(3) . ?
N31 C31 1.352(3) . ?
N31 C32 1.386(3) . ?
N32 C31 1.375(3) . ?
N32 C33 1.396(3) . ?
N32 C34 1.430(3) . ?
N41 C41 1.356(3) . ?
N41 C42 1.384(3) . ?
N42 C41 1.379(3) . ?
N42 C43 1.396(3) . ?
N42 C44 1.429(3) . ?
N51 C51 1.350(3) . ?
N51 C52 1.383(3) . ?
N52 C51 1.372(3) . ?
N52 C53 1.401(3) . ?
N52 C54 1.423(3) . ?
N61 C61 1.349(3) . ?
N61 C62 1.385(3) . ?
N62 C61 1.367(3) . ?
N62 C63 1.394(3) . ?
N62 C64 1.426(3) . ?
C12 C13 1.345(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.388(3) . ?
C16 C110 1.501(3) . ?
C17 C18 1.392(3) . ?
C18 C19 1.389(3) . ?
C18 C120 1.504(3) . ?
C22 C23 1.348(3) . ?
C24 C29 1.390(3) . ?
C24 C25 1.394(3) . ?
C25 C26 1.391(3) . ?
C26 C27 1.386(3) . ?
C26 C210 1.503(3) . ?
C27 C28 1.386(3) . ?
C28 C29 1.391(3) . ?
C28 C220 1.499(3) . ?
C32 C33 1.349(3) . ?
C34 C35 1.387(3) . ?
C34 C39 1.390(3) . ?
C35 C36 1.394(3) . ?
C36 C37 1.387(3) . ?
C36 C310 1.505(3) . ?
C37 C38 1.391(3) . ?
C38 C39 1.390(3) . ?
C38 C320 1.506(3) . ?
C42 C43 1.345(3) . ?
C44 C45 1.387(3) . ?
C44 C49 1.393(3) . ?
C45 C46 1.394(3) . ?
C46 C47 1.388(3) . ?
C46 C410 1.503(3) . ?
C47 C48 1.395(3) . ?
C48 C49 1.393(3) . ?
C48 C420 1.501(3) . ?
C52 C53 1.349(3) . ?
C54 C55 1.388(3) . ?
C54 C59 1.390(3) . ?
C55 C56 1.393(3) . ?
C56 C57 1.389(3) . ?
C56 C510 1.501(3) . ?
C57 C58 1.387(3) . ?
C58 C59 1.394(3) . ?
C58 C520 1.499(3) . ?
C62 C63 1.345(4) . ?
C64 C65 1.383(3) . ?
C64 C69 1.390(3) . ?
C65 C66 1.390(3) . ?
C66 C67 1.387(4) . ?
C66 C610 1.510(4) . ?
C67 C68 1.385(4) . ?
C68 C69 1.388(4) . ?
C68 C620 1.514(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
C11 N11 C12 111.18(18) . . ?
C11 N12 C13 109.34(17) . . ?
C11 N12 C14 126.54(18) . . ?
C13 N12 C14 124.02(18) . . ?
C21 N21 C22 111.43(19) . . ?
C21 N22 C23 109.67(17) . . ?
C21 N22 C24 127.01(18) . . ?
C23 N22 C24 123.32(18) . . ?
C31 N31 C32 110.99(19) . . ?
C31 N32 C33 110.16(18) . . ?
C31 N32 C34 125.64(18) . . ?
C33 N32 C34 124.08(18) . . ?
C41 N41 C42 110.97(19) . . ?
C41 N42 C43 109.93(18) . . ?
C41 N42 C44 124.44(18) . . ?
C43 N42 C44 125.36(18) . . ?
C51 N51 C52 111.41(19) . . ?
C51 N52 C53 109.42(18) . . ?
C51 N52 C54 126.62(18) . . ?
C53 N52 C54 123.60(18) . . ?
C61 N61 C62 110.7(2) . . ?
C61 N62 C63 109.57(19) . . ?
C61 N62 C64 124.79(19) . . ?
C63 N62 C64 125.6(2) . . ?
N11 C11 N12 105.23(18) . . ?
N11 C11 S1 126.77(16) . . ?
N12 C11 S1 127.99(16) . . ?
C13 C12 N11 106.9(2) . . ?
C12 C13 N12 107.29(19) . . ?
C15 C14 C19 121.16(19) . . ?
C15 C14 N12 119.04(19) . . ?
C19 C14 N12 119.79(18) . . ?
C14 C15 C16 118.97(19) . . ?
C17 C16 C15 121.23(19) . . ?
C17 C16 C110 120.64(19) . . ?
C15 C16 C110 118.1(2) . . ?
C16 C17 C18 118.35(19) . . ?
C19 C18 C17 121.95(19) . . ?
C19 C18 C120 117.67(19) . . ?
C17 C18 C120 120.38(19) . . ?
C18 C19 C14 118.28(19) . . ?
N21 C21 N22 104.85(19) . . ?
N21 C21 S2 126.67(16) . . ?
N22 C21 S2 128.47(16) . . ?
C23 C22 N21 106.8(2) . . ?
C22 C23 N22 107.22(19) . . ?
C29 C24 C25 120.69(19) . . ?
C29 C24 N22 120.17(18) . . ?
C25 C24 N22 119.07(19) . . ?
C26 C25 C24 118.7(2) . . ?
C27 C26 C25 121.8(2) . . ?
C27 C26 C210 118.8(2) . . ?
C25 C26 C210 119.4(2) . . ?
C26 C27 C28 118.1(2) . . ?
C27 C28 C29 121.8(2) . . ?
C27 C28 C220 120.6(2) . . ?
C29 C28 C220 117.6(2) . . ?
C24 C29 C28 118.86(19) . . ?
N31 C31 N32 104.87(18) . . ?
N31 C31 S3 126.39(16) . . ?
N32 C31 S3 128.69(16) . . ?
C33 C32 N31 107.3(2) . . ?
C32 C33 N32 106.6(2) . . ?
C35 C34 C39 121.2(2) . . ?
C35 C34 N32 119.08(19) . . ?
C39 C34 N32 119.7(2) . . ?
C34 C35 C36 119.2(2) . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 C310 119.8(2) . . ?
C35 C36 C310 119.3(2) . . ?
C36 C37 C38 118.8(2) . . ?
C39 C38 C37 121.5(2) . . ?
C39 C38 C320 119.8(2) . . ?
C37 C38 C320 118.7(2) . . ?
C34 C39 C38 118.5(2) . . ?
N41 C41 N42 104.72(18) . . ?
N41 C41 S4 127.11(17) . . ?
N42 C41 S4 128.13(16) . . ?
C43 C42 N41 107.4(2) . . ?
C42 C43 N42 106.9(2) . . ?
C45 C44 C49 121.61(19) . . ?
C45 C44 N42 119.43(19) . . ?
C49 C44 N42 118.92(19) . . ?
C44 C45 C46 118.86(19) . . ?
C47 C46 C45 121.0(2) . . ?
C47 C46 C410 120.0(2) . . ?
C45 C46 C410 118.85(19) . . ?
C46 C47 C48 118.8(2) . . ?
C49 C48 C47 121.4(2) . . ?
C49 C48 C420 119.8(2) . . ?
C47 C48 C420 118.8(2) . . ?
C48 C49 C44 118.24(19) . . ?
N51 C51 N52 105.19(19) . . ?
N51 C51 S5 126.14(17) . . ?
N52 C51 S5 128.66(17) . . ?
C53 C52 N51 106.7(2) . . ?
C52 C53 N52 107.3(2) . . ?
C55 C54 C59 120.94(19) . . ?
C55 C54 N52 118.35(19) . . ?
C59 C54 N52 120.71(19) . . ?
C54 C55 C56 119.6(2) . . ?
C57 C56 C55 120.6(2) . . ?
C57 C56 C510 120.0(2) . . ?
C55 C56 C510 119.5(2) . . ?
C58 C57 C56 118.89(19) . . ?
C57 C58 C59 121.7(2) . . ?
C57 C58 C520 119.8(2) . . ?
C59 C58 C520 118.5(2) . . ?
C54 C59 C58 118.37(19) . . ?
N61 C61 N62 105.5(2) . . ?
N61 C61 S6 127.26(19) . . ?
N62 C61 S6 127.24(18) . . ?
C63 C62 N61 107.0(2) . . ?
C62 C63 N62 107.2(2) . . ?
C65 C64 C69 121.1(2) . . ?
C65 C64 N62 119.1(2) . . ?
C69 C64 N62 119.8(2) . . ?
C64 C65 C66 119.1(2) . . ?
C67 C66 C65 121.1(2) . . ?
C67 C66 C610 119.5(2) . . ?
C65 C66 C610 119.3(2) . . ?
C68 C67 C66 118.5(2) . . ?
C67 C68 C69 121.6(2) . . ?
C67 C68 C620 118.8(3) . . ?
C69 C68 C620 119.6(3) . . ?
C68 C69 C64 118.5(2) . . ?
F13 C110 F11 107.2(2) . . ?
F13 C110 F12 106.5(2) . . ?
F11 C110 F12 106.72(19) . . ?
F13 C110 C16 112.22(19) . . ?
F11 C110 C16 112.6(2) . . ?
F12 C110 C16 111.2(2) . . ?
F14 C120 F16 107.9(2) . . ?
F14 C120 F15 106.5(2) . . ?
F16 C120 F15 104.69(19) . . ?
F14 C120 C18 113.40(19) . . ?
F16 C120 C18 112.33(19) . . ?
F15 C120 C18 111.49(19) . . ?
F21 C210 F22 109.6(7) . . ?
F21A C210 F23A 109.4(10) . . ?
F21 C210 F23 105.8(6) . . ?
F22 C210 F23 104.9(5) . . ?
F21A C210 F22A 104.7(9) . . ?
F23A C210 F22A 103.3(8) . . ?
F21A C210 C26 117.0(6) . . ?
F21 C210 C26 114.9(4) . . ?
F22 C210 C26 111.7(5) . . ?
F23A C210 C26 113.4(7) . . ?
F23 C210 C26 109.3(4) . . ?
F22A C210 C26 107.6(6) . . ?
F24 C220 F25 107.5(2) . . ?
F24 C220 F26 106.7(2) . . ?
F25 C220 F26 104.9(2) . . ?
F24 C220 C28 113.7(2) . . ?
F25 C220 C28 112.3(2) . . ?
F26 C220 C28 111.3(2) . . ?
F32 C310 F33 112.2(7) . . ?
F33A C310 F31A 112.7(13) . . ?
F31B C310 F33B 105.2(8) . . ?
F31B C310 F32B 108.1(6) . . ?
F33B C310 F32B 103.6(7) . . ?
F32 C310 F31 104.7(5) . . ?
F33 C310 F31 104.6(7) . . ?
F33A C310 F32A 108.4(13) . . ?
F31A C310 F32A 103.6(11) . . ?
F33A C310 C36 117.1(9) . . ?
F32 C310 C36 112.9(5) . . ?
F33 C310 C36 112.7(8) . . ?
F31B C310 C36 113.2(6) . . ?
F31A C310 C36 107.7(10) . . ?
F33B C310 C36 113.2(8) . . ?
F32B C310 C36 112.7(5) . . ?
F31 C310 C36 109.0(5) . . ?
F32A C310 C36 106.2(9) . . ?
F36 C320 F35 107.3(2) . . ?
F36 C320 F34 106.6(2) . . ?
F35 C320 F34 106.4(2) . . ?
F36 C320 C38 112.00(19) . . ?
F35 C320 C38 111.5(2) . . ?
F34 C320 C38 112.6(2) . . ?
F43 C410 F41 107.4(2) . . ?
F43 C410 F42 107.1(2) . . ?
F41 C410 F42 105.8(2) . . ?
F43 C410 C46 112.9(2) . . ?
F41 C410 C46 112.2(2) . . ?
F42 C410 C46 111.1(2) . . ?
F45 C420 F44 106.98(19) . . ?
F45 C420 F46 106.47(19) . . ?
F44 C420 F46 107.0(2) . . ?
F45 C420 C48 111.3(2) . . ?
F44 C420 C48 112.41(19) . . ?
F46 C420 C48 112.26(19) . . ?
F53 C510 F51 108.9(4) . . ?
F52A C510 F51A 109.9(5) . . ?
F53 C510 F52 107.5(5) . . ?
F51 C510 F52 104.4(4) . . ?
F52A C510 F53A 106.2(6) . . ?
F51A C510 F53A 102.3(5) . . ?
F52A C510 C56 116.7(5) . . ?
F53 C510 C56 114.2(4) . . ?
F51 C510 C56 111.9(3) . . ?
F51A C510 C56 111.4(3) . . ?
F52 C510 C56 109.4(4) . . ?
F53A C510 C56 109.3(5) . . ?
F55 C520 F56 106.3(2) . . ?
F55 C520 F54 107.5(2) . . ?
F56 C520 F54 105.4(2) . . ?
F55 C520 C58 112.8(2) . . ?
F56 C520 C58 112.4(2) . . ?
F54 C520 C58 112.0(2) . . ?
F61 C610 F63 117.3(8) . . ?
F62A C610 F63A 107.5(5) . . ?
F62A C610 F61A 106.3(5) . . ?
F63A C610 F61A 101.8(4) . . ?
F61 C610 F62 108.3(8) . . ?
F63 C610 F62 100.8(6) . . ?
F61 C610 C66 113.5(5) . . ?
F62A C610 C66 115.8(3) . . ?
F63 C610 C66 109.7(4) . . ?
F63A C610 C66 112.7(3) . . ?
F61A C610 C66 111.7(4) . . ?
F62 C610 C66 105.9(4) . . ?
F64 C620 F66 107.4(3) . . ?
F64 C620 F65 107.5(3) . . ?
F66 C620 F65 105.5(2) . . ?
F64 C620 C68 112.1(2) . . ?
F66 C620 C68 111.3(3) . . ?
F65 C620 C68 112.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 S3 0.84(3) 2.45(3) 3.284(2) 178(3) .
N31 H31 S1 0.79(3) 2.50(4) 3.278(2) 168(3) .
N21 H21 S4 0.83(3) 2.43(3) 3.260(2) 178(3) .
N41 H41 S2 0.87(3) 2.46(3) 3.291(2) 160(3) .
N51 H51 S6 0.83(4) 2.39(4) 3.206(2) 167(4) .
N61 H61 S5 0.84(4) 2.54(4) 3.370(2) 170(3) .

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 991539'
#######################################################################
#
#                 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_hmimcl3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H5 Cl3 N2 S'
_chemical_formula_weight         279.56

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.4408(8)
_cell_length_b                   20.454(2)
_cell_length_c                   7.1759(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0376(14)
_cell_angle_gamma                90.00
_cell_volume                     1091.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      32.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5601
_exptl_absorpt_correction_T_max  0.8734
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17407
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         30.51
_reflns_number_total             3337
_reflns_number_gt                3242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0305P)²+0.6285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3337
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.002
_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
S S 0.83964(4) 0.593811(16) 0.45724(4) 0.02130(8) Uani 1 1 d . . .
Cl1 Cl 0.33309(4) 0.564151(15) 0.64757(4) 0.02121(8) Uani 1 1 d . . .
Cl2 Cl 0.27082(5) 0.825475(17) 0.71431(5) 0.02896(9) Uani 1 1 d . . .
Cl3 Cl 0.88152(4) 0.705261(17) 0.93391(5) 0.02567(8) Uani 1 1 d . . .
N1 N 0.86919(14) 0.50214(5) 0.73565(14) 0.01692(19) Uani 1 1 d . . .
H1 H 0.941(2) 0.4783(9) 0.678(3) 0.020 Uiso 1 1 d . . .
N2 N 0.69870(13) 0.58356(5) 0.80428(14) 0.01488(18) Uani 1 1 d . . .
C1 C 0.80397(15) 0.55897(6) 0.66660(16) 0.0150(2) Uani 1 1 d . . .
C2 C 0.80571(17) 0.49064(6) 0.91283(17) 0.0183(2) Uani 1 1 d . . .
H2A H 0.8322 0.4538 0.9889 0.022 Uiso 1 1 calc R . .
C3 C 0.69939(16) 0.54148(6) 0.95745(17) 0.0180(2) Uani 1 1 d . . .
H3A H 0.6373 0.5475 1.0707 0.022 Uiso 1 1 calc R . .
C4 C 0.59600(15) 0.64158(6) 0.78545(15) 0.01432(19) Uani 1 1 d . . .
C5 C 0.42077(15) 0.63899(6) 0.71304(16) 0.0153(2) Uani 1 1 d . . .
C6 C 0.31728(16) 0.69519(6) 0.69251(16) 0.0175(2) Uani 1 1 d . . .
H6A H 0.1974 0.6932 0.6450 0.021 Uiso 1 1 calc R . .
C7 C 0.39498(17) 0.75430(6) 0.74376(17) 0.0179(2) Uani 1 1 d . . .
C8 C 0.56853(17) 0.75923(6) 0.81743(17) 0.0185(2) Uani 1 1 d . . .
H8A H 0.6179 0.8004 0.8522 0.022 Uiso 1 1 calc R . .
C9 C 0.66728(15) 0.70201(6) 0.83851(17) 0.0165(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C1 1.6881(12) . ?
Cl1 C5 1.7258(12) . ?
Cl2 C7 1.7351(12) . ?
Cl3 C9 1.7247(12) . ?
N1 C1 1.3505(15) . ?
N1 C2 1.3845(16) . ?
N2 C1 1.3677(14) . ?
N2 C3 1.3961(15) . ?
N2 C4 1.4166(14) . ?
C2 C3 1.3485(17) . ?
C4 C9 1.3952(16) . ?
C4 C5 1.3958(15) . ?
C5 C6 1.3899(16) . ?
C6 C7 1.3870(17) . ?
C7 C8 1.3901(18) . ?
C8 C9 1.3888(17) . ?

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 N1 C2 110.90(10) . . ?
C1 N2 C3 110.36(10) . . ?
C1 N2 C4 123.66(10) . . ?
C3 N2 C4 125.87(10) . . ?
N1 C1 N2 104.96(10) . . ?
N1 C1 S 128.95(9) . . ?
N2 C1 S 126.08(9) . . ?
C3 C2 N1 107.37(10) . . ?
C2 C3 N2 106.40(10) . . ?
C9 C4 C5 118.89(10) . . ?
C9 C4 N2 120.95(10) . . ?
C5 C4 N2 120.16(10) . . ?
C6 C5 C4 121.34(11) . . ?
C6 C5 Cl1 119.91(9) . . ?
C4 C5 Cl1 118.75(9) . . ?
C7 C6 C5 117.73(11) . . ?
C6 C7 C8 122.95(11) . . ?
C6 C7 Cl2 118.73(10) . . ?
C8 C7 Cl2 118.32(10) . . ?
C9 C8 C7 117.80(11) . . ?
C8 C9 C4 121.27(11) . . ?
C8 C9 Cl3 119.61(9) . . ?
C4 C9 Cl3 119.12(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S 0.842(19) 2.413(19) 3.2511(11) 174.1(17) 3_766

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 991540'
#######################################################################
#
#                 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_hmimome3ph

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O3 S'
_chemical_formula_weight         266.31

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                   7.2383(6)
_cell_length_b                   7.9459(7)
_cell_length_c                   22.324(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0750(10)
_cell_angle_gamma                90.00
_cell_volume                     1282.12(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5910
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.53

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7575
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         30.61
_reflns_number_total             3945
_reflns_number_gt                2649
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0417P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
S S 0.22236(6) 0.36594(6) 0.45132(2) 0.02677(12) Uani 1 1 d . . .
N1 N -0.15151(18) 0.33228(18) 0.45326(6) 0.0240(3) Uani 1 1 d . . .
H1 H -0.162(3) 0.411(3) 0.4828(9) 0.039(6) Uiso 1 1 d . . .
N2 N -0.03361(17) 0.17068(16) 0.38823(6) 0.0198(3) Uani 1 1 d . . .
O1 O 0.49482(15) -0.18911(15) 0.35457(5) 0.0254(3) Uani 1 1 d . . .
O2 O 0.41567(16) -0.17837(14) 0.23741(5) 0.0244(3) Uani 1 1 d . . .
O3 O 0.15106(16) 0.02225(14) 0.18957(5) 0.0248(3) Uani 1 1 d . . .
C1 C 0.0914(2) 0.08927(19) 0.34967(7) 0.0195(3) Uani 1 1 d . . .
C2 C 0.2354(2) -0.00648(19) 0.37473(7) 0.0201(3) Uani 1 1 d . . .
H2A H 0.2565 -0.0140 0.4170 0.024 Uiso 1 1 calc R . .
C3 C 0.3483(2) -0.09126(19) 0.33631(7) 0.0199(3) Uani 1 1 d . . .
C4 C 0.3148(2) -0.08098(19) 0.27426(7) 0.0201(3) Uani 1 1 d . . .
C5 C 0.1708(2) 0.01921(19) 0.25043(7) 0.0199(3) Uani 1 1 d . . .
C6 C 0.0568(2) 0.10535(19) 0.28843(7) 0.0207(3) Uani 1 1 d . . .
H6A H -0.0422 0.1734 0.2726 0.025 Uiso 1 1 calc R . .
C7 C 0.5180(3) -0.2288(2) 0.41683(8) 0.0329(4) Uani 1 1 d . . .
H7A H 0.6208 -0.3082 0.4232 0.049 Uiso 1 1 calc R . .
H7B H 0.4042 -0.2799 0.4303 0.049 Uiso 1 1 calc R . .
H7C H 0.5450 -0.1257 0.4397 0.049 Uiso 1 1 calc R . .
C8 C 0.5650(2) -0.0924(2) 0.21140(9) 0.0334(4) Uani 1 1 d . . .
H8A H 0.6193 -0.1653 0.1816 0.050 Uiso 1 1 calc R . .
H8B H 0.6594 -0.0638 0.2429 0.050 Uiso 1 1 calc R . .
H8C H 0.5187 0.0109 0.1919 0.050 Uiso 1 1 calc R . .
C9 C 0.0244(3) 0.1417(2) 0.16352(8) 0.0293(4) Uani 1 1 d . . .
H9A H 0.0317 0.1406 0.1198 0.044 Uiso 1 1 calc R . .
H9B H 0.0558 0.2542 0.1789 0.044 Uiso 1 1 calc R . .
H9C H -0.1015 0.1126 0.1739 0.044 Uiso 1 1 calc R . .
C10 C 0.0110(2) 0.2879(2) 0.43107(7) 0.0207(3) Uani 1 1 d . . .
C11 C -0.2966(2) 0.2467(2) 0.42464(8) 0.0280(4) Uani 1 1 d . . .
H11A H -0.4240 0.2570 0.4323 0.034 Uiso 1 1 calc R . .
C12 C -0.2238(2) 0.1464(2) 0.38399(8) 0.0263(4) Uani 1 1 d . . .
H12A H -0.2899 0.0723 0.3572 0.032 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
S C10 1.6895(16) . ?
N1 C10 1.348(2) . ?
N1 C11 1.379(2) . ?
N2 C10 1.362(2) . ?
N2 C12 1.388(2) . ?
N2 C1 1.4357(19) . ?
O1 C3 1.3595(18) . ?
O1 C7 1.426(2) . ?
O2 C4 1.3688(18) . ?
O2 C8 1.428(2) . ?
O3 C5 1.3586(18) . ?
O3 C9 1.4221(19) . ?
C1 C6 1.382(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.395(2) . ?
C11 C12 1.337(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C11 111.04(14) . . ?
C10 N2 C12 109.87(13) . . ?
C10 N2 C1 126.59(13) . . ?
C12 N2 C1 123.43(13) . . ?
C3 O1 C7 117.90(13) . . ?
C4 O2 C8 114.46(12) . . ?
C5 O3 C9 116.87(12) . . ?
C6 C1 C2 122.88(14) . . ?
C6 C1 N2 117.70(14) . . ?
C2 C1 N2 119.37(14) . . ?
C1 C2 C3 118.16(15) . . ?
O1 C3 C2 124.54(15) . . ?
O1 C3 C4 114.99(14) . . ?
C2 C3 C4 120.46(14) . . ?
O2 C4 C5 120.36(14) . . ?
O2 C4 C3 119.55(14) . . ?
C5 C4 C3 119.94(14) . . ?
O3 C5 C4 115.37(14) . . ?
O3 C5 C6 124.44(14) . . ?
C4 C5 C6 120.18(15) . . ?
C1 C6 C5 118.33(14) . . ?
N1 C10 N2 104.96(13) . . ?
N1 C10 S 126.98(12) . . ?
N2 C10 S 128.04(12) . . ?
C12 C11 N1 106.86(14) . . ?
C11 C12 N2 107.25(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S 0.91(2) 2.36(2) 3.2662(15) 171.2(17) 3_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.61
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 991541'
#######################################################################
#
#                 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_hmimomeno2ph

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N3 O3 S'
_chemical_formula_weight         251.26

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   C2/c

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

_cell_length_a                   13.747(5)
_cell_length_b                   12.625(4)
_cell_length_c                   13.632(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.496(5)
_cell_angle_gamma                90.00
_cell_volume                     2268.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6816
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.85

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8944
_exptl_absorpt_correction_T_max  0.9504
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12681
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2330
_reflns_number_gt                1962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0257P)²+4.8130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2330
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
S S 0.10157(4) 0.97882(5) 0.64738(5) 0.02604(18) Uani 1 1 d . . .
N1 N 0.13036(16) 1.03702(18) 0.84760(16) 0.0271(5) Uani 1 1 d . . .
H1 H 0.068(2) 1.015(2) 0.847(2) 0.033 Uiso 1 1 d . . .
N2 N 0.25266(15) 1.08671(17) 0.78755(15) 0.0246(4) Uani 1 1 d . . .
N3 N 0.35825(16) 0.91443(17) 0.71347(16) 0.0291(5) Uani 1 1 d . . .
O1 O 0.35411(15) 0.89826(16) 0.80081(14) 0.0377(5) Uani 1 1 d . . .
O2 O 0.36145(17) 0.84373(16) 0.65199(16) 0.0455(5) Uani 1 1 d . . .
O3 O 0.47677(12) 1.16352(13) 0.50992(13) 0.0264(4) Uani 1 1 d . . .
C1 C 0.16113(17) 1.03503(18) 0.76187(17) 0.0222(5) Uani 1 1 d . . .
C2 C 0.2012(2) 1.0879(2) 0.92662(19) 0.0321(6) Uani 1 1 d . . .
H2A H 0.1966 1.0990 0.9941 0.039 Uiso 1 1 calc R . .
C3 C 0.2772(2) 1.1186(2) 0.89006(19) 0.0321(6) Uani 1 1 d . . .
H3A H 0.3368 1.1552 0.9268 0.038 Uiso 1 1 calc R . .
C4 C 0.31304(17) 1.10594(19) 0.71935(18) 0.0235(5) Uani 1 1 d . . .
C5 C 0.36095(17) 1.02558(19) 0.68001(18) 0.0221(5) Uani 1 1 d . . .
C6 C 0.41464(17) 1.04586(19) 0.60999(17) 0.0234(5) Uani 1 1 d . . .
H6A H 0.4455 0.9897 0.5834 0.028 Uiso 1 1 calc R . .
C7 C 0.42270(17) 1.15047(19) 0.57913(18) 0.0233(5) Uani 1 1 d . . .
C8 C 0.3777(2) 1.2320(2) 0.6197(2) 0.0321(6) Uani 1 1 d . . .
H8A H 0.3847 1.3033 0.6005 0.039 Uiso 1 1 calc R . .
C9 C 0.3226(2) 1.2092(2) 0.6880(2) 0.0323(6) Uani 1 1 d . . .
H9A H 0.2909 1.2652 0.7139 0.039 Uiso 1 1 calc R . .
C10 C 0.4711(2) 1.2666(2) 0.4625(2) 0.0315(6) Uani 1 1 d . . .
H10A H 0.5054 1.2644 0.4086 0.047 Uiso 1 1 calc R . .
H10B H 0.5041 1.3192 0.5141 0.047 Uiso 1 1 calc R . .
H10C H 0.3998 1.2861 0.4326 0.047 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
S C1 1.698(2) . ?
N1 C1 1.351(3) . ?
N1 C2 1.388(3) . ?
N2 C1 1.372(3) . ?
N2 C3 1.400(3) . ?
N2 C4 1.432(3) . ?
N3 O1 1.225(3) . ?
N3 O2 1.234(3) . ?
N3 C5 1.479(3) . ?
O3 C7 1.367(3) . ?
O3 C10 1.446(3) . ?
C2 C3 1.336(4) . ?
C4 C9 1.390(4) . ?
C4 C5 1.397(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.386(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
C1 N1 C2 110.9(2) . . ?
C1 N2 C3 109.6(2) . . ?
C1 N2 C4 125.02(19) . . ?
C3 N2 C4 125.4(2) . . ?
O1 N3 O2 124.1(2) . . ?
O1 N3 C5 118.0(2) . . ?
O2 N3 C5 117.9(2) . . ?
C7 O3 C10 116.50(19) . . ?
N1 C1 N2 105.1(2) . . ?
N1 C1 S 127.95(19) . . ?
N2 C1 S 126.96(18) . . ?
C3 C2 N1 107.2(2) . . ?
C2 C3 N2 107.2(2) . . ?
C9 C4 C5 117.8(2) . . ?
C9 C4 N2 118.8(2) . . ?
C5 C4 N2 123.3(2) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 N3 116.9(2) . . ?
C4 C5 N3 121.0(2) . . ?
C5 C6 C7 119.0(2) . . ?
O3 C7 C8 125.1(2) . . ?
O3 C7 C6 115.2(2) . . ?
C8 C7 C6 119.7(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C4 121.2(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
N1 H1 S 0.91(3) 2.39(3) 3.292(2) 173(3) 2_556

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 991542'
#######################################################################
#
#                 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_tdacf30514

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 F6 N2 O2 S'
_chemical_formula_weight         404.37

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.5507(13)
_cell_length_b                   13.4265(14)
_cell_length_c                   21.715(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.920(2)
_cell_angle_gamma                90
_cell_volume                     3615.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9585
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.200
_exptl_crystal_size_mid          0.780
_exptl_crystal_size_min          0.680
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7539
_exptl_absorpt_correction_T_max  0.8487
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55289
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.789
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10539
_reflns_number_gt                7066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+1.9419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10539
_refine_ls_number_parameters     713
_refine_ls_number_restraints     802
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.057
_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_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
F11 F 0.1876(7) 0.0975(5) 0.0110(3) 0.0713(18) Uani 0.450(3) 1 d D U P A 1
F12 F 0.1641(7) 0.2387(5) -0.0351(4) 0.089(2) Uani 0.450(3) 1 d D U P A 1
F13 F 0.2488(6) 0.1229(7) -0.0746(3) 0.090(2) Uani 0.450(3) 1 d D U P A 1
F14 F 0.7107(12) 0.2272(10) 0.0335(6) 0.063(3) Uani 0.343(3) 1 d D U P B 1
F15 F 0.6649(10) 0.0901(8) 0.0719(5) 0.077(3) Uani 0.343(3) 1 d D U P B 1
F16 F 0.626(2) 0.1160(11) -0.0258(5) 0.064(3) Uani 0.343(3) 1 d D U P B 1
F21 F 0.4947(7) -0.0587(4) 0.4164(4) 0.083(2) Uani 0.480(3) 1 d D U P C 1
F22 F 0.4942(11) 0.0880(6) 0.4561(2) 0.119(3) Uani 0.480(3) 1 d D U P C 1
F23 F 0.3505(5) 0.0261(6) 0.4051(3) 0.0917(17) Uani 0.480(3) 1 d D U P C 1
F24 F 0.5820(8) -0.0261(11) 0.1645(8) 0.072(3) Uani 0.462(3) 1 d D U P D 1
F25 F 0.4302(8) 0.0433(10) 0.1345(5) 0.071(3) Uani 0.462(3) 1 d D U P D 1
F26 F 0.4388(10) -0.0888(7) 0.1890(9) 0.059(3) Uani 0.462(3) 1 d D U P D 1
F11A F 0.2026(11) 0.0789(6) -0.0112(6) 0.093(3) Uani 0.346(3) 1 d D U P A 2
F12A F 0.1432(7) 0.2253(7) -0.0121(4) 0.0587(17) Uani 0.346(3) 1 d D U P A 2
F13A F 0.2326(7) 0.1815(10) -0.0831(3) 0.094(3) Uani 0.346(3) 1 d D U P A 2
F14A F 0.6943(7) 0.2378(6) 0.0142(4) 0.0676(18) Uani 0.606(3) 1 d D U P B 2
F15A F 0.6923(5) 0.1230(5) 0.0812(3) 0.0732(15) Uani 0.606(3) 1 d D U P B 2
F16A F 0.6298(13) 0.0944(7) -0.0143(3) 0.073(2) Uani 0.606(3) 1 d D U P B 2
F21A F 0.4438(13) -0.0612(7) 0.4091(6) 0.074(3) Uani 0.273(3) 1 d D U P C 2
F22A F 0.5494(6) 0.0515(8) 0.4532(4) 0.0538(19) Uani 0.273(3) 1 d D U P C 2
F23A F 0.3810(8) 0.0797(10) 0.4277(5) 0.082(3) Uani 0.273(3) 1 d D U P C 2
F24A F 0.5688(11) 0.0134(15) 0.1513(11) 0.073(4) Uani 0.337(3) 1 d D U P D 2
F25A F 0.3990(10) 0.0178(12) 0.1455(9) 0.074(4) Uani 0.337(3) 1 d D U P D 2
F26A F 0.4880(13) -0.0993(8) 0.1961(10) 0.102(6) Uani 0.337(3) 1 d D U P D 2
F11B F 0.2450(11) 0.0839(7) -0.0520(7) 0.071(3) Uani 0.204(3) 1 d D U P A 3
F12B F 0.1521(10) 0.1697(17) 0.0053(7) 0.109(4) Uani 0.204(3) 1 d D U P A 3
F13B F 0.2142(13) 0.2374(8) -0.0715(7) 0.088(3) Uani 0.204(3) 1 d D U P A 3
F14B F 0.657(3) 0.204(2) -0.0215(11) 0.077(7) Uani 0.051(3) 1 d D U P B 3
F15B F 0.7138(19) 0.180(2) 0.0751(11) 0.052(6) Uani 0.051(3) 1 d D U P B 3
F16B F 0.629(3) 0.0642(11) 0.0200(15) 0.060(6) Uani 0.051(3) 1 d D U P B 3
F21B F 0.3765(11) -0.0255(10) 0.4025(5) 0.079(3) Uani 0.247(3) 1 d D U P C 3
F22B F 0.5425(8) -0.0049(13) 0.4412(5) 0.087(3) Uani 0.247(3) 1 d D U P C 3
F23B F 0.4260(10) 0.1101(7) 0.4462(5) 0.061(2) Uani 0.247(3) 1 d D U P C 3
F24B F 0.5791(13) -0.003(2) 0.1591(12) 0.049(4) Uani 0.201(3) 1 d D U P D 3
F25B F 0.4130(15) 0.0364(16) 0.1404(11) 0.044(4) Uani 0.201(3) 1 d D U P D 3
F26B F 0.462(2) -0.0964(11) 0.1902(12) 0.044(4) Uani 0.201(3) 1 d D U P D 3
S1 S 0.26504(4) 0.30381(4) 0.19786(3) 0.04354(13) Uani 1 1 d . . . . .
S2 S 0.73064(4) 0.30491(4) 0.23142(3) 0.04340(13) Uani 1 1 d . . . . .
N11 N 0.42452(13) 0.38146(12) 0.14369(8) 0.0370(3) Uani 1 1 d . . . . .
H11 H 0.4736(19) 0.4211(17) 0.1457(10) 0.044 Uiso 1 1 d . U . . .
N12 N 0.36780(13) 0.47681(13) 0.21759(8) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.4087(19) 0.5175(17) 0.2085(10) 0.045 Uiso 1 1 d . U . . .
N21 N 0.62546(13) 0.46501(12) 0.26219(8) 0.0384(4) Uani 1 1 d . . . . .
H21 H 0.5763(19) 0.4902(17) 0.2798(10) 0.046 Uiso 1 1 d . U . . .
N22 N 0.55894(13) 0.31921(12) 0.29009(8) 0.0371(3) Uani 1 1 d . . . . .
H22 H 0.5201(18) 0.3557(17) 0.3105(10) 0.045 Uiso 1 1 d . U . . .
O11 O 0.41615(11) 0.44331(11) 0.35468(7) 0.0471(3) Uani 1 1 d . . . . .
O12 O 0.45200(13) 0.59336(12) 0.31605(7) 0.0521(4) Uani 1 1 d . . . . .
O21 O 0.53873(11) 0.61290(9) 0.18290(6) 0.0393(3) Uani 1 1 d . . . . .
O22 O 0.62157(11) 0.50738(10) 0.12574(7) 0.0456(3) Uani 1 1 d . . . . .
C11 C 0.36896(17) 0.53054(16) 0.32550(10) 0.0452(5) Uani 1 1 d . . . . .
H11A H 0.3233 0.5636 0.3534 0.054 Uiso 1 1 calc R U . . .
C12 C 0.30244(16) 0.51013(17) 0.26314(10) 0.0447(5) Uani 1 1 d . . . . .
H12A H 0.2480 0.4585 0.2680 0.054 Uiso 1 1 calc R U . . .
H12B H 0.2635 0.5716 0.2477 0.054 Uiso 1 1 calc R U . . .
C13 C 0.35434(14) 0.39103(14) 0.18582(8) 0.0341(4) Uani 1 1 d . . . . .
C14 C 0.42449(14) 0.30692(13) 0.09837(8) 0.0330(4) Uani 1 1 d . . . . .
C15 C 0.33005(16) 0.27370(15) 0.06209(9) 0.0393(4) Uani 1 1 d . . . . .
H15A H 0.2622 0.2991 0.0689 0.047 Uiso 1 1 calc R U . . .
C16 C 0.33547(17) 0.20399(16) 0.01637(9) 0.0434(5) Uani 1 1 d . . . . .
C17 C 0.43290(18) 0.16576(16) 0.00472(9) 0.0435(5) Uani 1 1 d . . . . .
H17A H 0.4354 0.1171 -0.0268 0.052 Uiso 1 1 calc R U . . .
C18 C 0.52587(16) 0.20032(15) 0.04020(9) 0.0394(4) Uani 1 1 d . . . . .
C19 C 0.52253(15) 0.27050(14) 0.08683(8) 0.0348(4) Uani 1 1 d . . . . .
H19A H 0.5876 0.2935 0.1108 0.042 Uiso 1 1 calc R U . . .
C21 C 0.64025(15) 0.57758(14) 0.17479(10) 0.0397(4) Uani 1 1 d . . . . .
H21A H 0.6846 0.6338 0.1624 0.048 Uiso 1 1 calc R U . . .
C22 C 0.69466(15) 0.53378(14) 0.23560(10) 0.0426(5) Uani 1 1 d . . . . .
H22A H 0.7610 0.4985 0.2285 0.051 Uiso 1 1 calc R U . . .
H22B H 0.7161 0.5884 0.2656 0.051 Uiso 1 1 calc R U . . .
C23 C 0.63434(14) 0.36560(13) 0.26194(9) 0.0355(4) Uani 1 1 d . . . . .
C24 C 0.53687(14) 0.21640(13) 0.29092(8) 0.0336(4) Uani 1 1 d . . . . .
C25 C 0.51352(16) 0.17580(15) 0.34574(9) 0.0394(4) Uani 1 1 d . . . . .
H25A H 0.5182 0.2159 0.3821 0.047 Uiso 1 1 calc R U . . .
C26 C 0.48335(17) 0.07712(15) 0.34776(9) 0.0425(5) Uani 1 1 d . . . . .
C27 C 0.47711(16) 0.01659(15) 0.29600(9) 0.0400(4) Uani 1 1 d . . . . .
H27A H 0.4575 -0.0515 0.2978 0.048 Uiso 1 1 calc R U . . .
C28 C 0.50031(14) 0.05807(14) 0.24136(9) 0.0344(4) Uani 1 1 d . . . . .
C29 C 0.52971(14) 0.15713(14) 0.23846(8) 0.0341(4) Uani 1 1 d . . . . .
H29A H 0.5450 0.1843 0.2004 0.041 Uiso 1 1 calc R U . . .
C111 C 0.34650(18) 0.3859(2) 0.38697(12) 0.0572(6) Uani 1 1 d . . . . .
H11B H 0.3314 0.3209 0.3659 0.069 Uiso 1 1 calc R U . . .
H11C H 0.2772 0.4214 0.3863 0.069 Uiso 1 1 calc R U . . .
C112 C 0.3974(2) 0.3697(3) 0.45179(13) 0.0850(10) Uani 1 1 d . . . . .
H11D H 0.3528 0.3243 0.4723 0.128 Uiso 1 1 calc R U . . .
H11E H 0.4044 0.4335 0.4740 0.128 Uiso 1 1 calc R U . . .
H11F H 0.4691 0.3404 0.4523 0.128 Uiso 1 1 calc R U . . .
C121 C 0.4996(3) 0.6454(2) 0.37143(12) 0.0810(9) Uani 1 1 d . . . . .
H12C H 0.4421 0.6693 0.3943 0.097 Uiso 1 1 calc R U . . .
H12D H 0.5467 0.5994 0.3991 0.097 Uiso 1 1 calc R U . . .
C122 C 0.5612(3) 0.7275(2) 0.35560(17) 0.0898(10) Uani 1 1 d . . . . .
H12E H 0.5842 0.7680 0.3928 0.135 Uiso 1 1 calc R U . . .
H12F H 0.5170 0.7682 0.3239 0.135 Uiso 1 1 calc R U . . .
H12G H 0.6247 0.7032 0.3391 0.135 Uiso 1 1 calc R U . . .
C161 C 0.2337(2) 0.1692(2) -0.02213(12) 0.0659(7) Uani 1 1 d D U . . .
C181 C 0.6332(2) 0.16146(19) 0.03006(11) 0.0541(5) Uani 1 1 d D U . . .
C211 C 0.49490(19) 0.68406(16) 0.13597(11) 0.0516(5) Uani 1 1 d . . . . .
H21B H 0.5004 0.6580 0.0939 0.062 Uiso 1 1 calc R U . . .
H21C H 0.5357 0.7474 0.1419 0.062 Uiso 1 1 calc R U . . .
C212 C 0.3792(2) 0.70148(18) 0.14199(13) 0.0620(7) Uani 1 1 d . . . . .
H21D H 0.3504 0.7561 0.1144 0.093 Uiso 1 1 calc R U . . .
H21E H 0.3738 0.7190 0.1852 0.093 Uiso 1 1 calc R U . . .
H21F H 0.3376 0.6408 0.1304 0.093 Uiso 1 1 calc R U . . .
C221 C 0.7113(2) 0.4893(2) 0.09383(13) 0.0623(7) Uani 1 1 d . . . . .
H22C H 0.7481 0.4269 0.1093 0.075 Uiso 1 1 calc R U . . .
H22D H 0.7638 0.5446 0.1018 0.075 Uiso 1 1 calc R U . . .
C222 C 0.6718(3) 0.4810(3) 0.02554(15) 0.0861(10) Uani 1 1 d . . . . .
H22E H 0.7320 0.4632 0.0038 0.129 Uiso 1 1 calc R U . . .
H22F H 0.6414 0.5450 0.0098 0.129 Uiso 1 1 calc R U . . .
H22G H 0.6161 0.4294 0.0182 0.129 Uiso 1 1 calc R U . . .
C261 C 0.4596(2) 0.03587(19) 0.40777(11) 0.0609(6) Uani 1 1 d D U . . .
C281 C 0.48874(17) -0.00243(16) 0.18331(10) 0.0443(5) Uani 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F11 C161 1.381(6) . ?
F12 C161 1.280(6) . ?
F13 C161 1.337(6) . ?
F14 C181 1.308(9) . ?
F15 C181 1.339(8) . ?
F16 C181 1.349(10) . ?
F21 C261 1.347(6) . ?
F22 C261 1.280(5) . ?
F23 C261 1.368(6) . ?
F24 C281 1.336(8) . ?
F25 C281 1.341(7) . ?
F26 C281 1.332(8) . ?
F11A C161 1.307(8) . ?
F12A C161 1.408(7) . ?
F13A C161 1.332(7) . ?
F14A C181 1.357(6) . ?
F15A C181 1.339(5) . ?
F16A C181 1.315(7) . ?
F21A C261 1.320(8) . ?
F22A C261 1.394(7) . ?
F23A C261 1.280(8) . ?
F24A C281 1.325(10) . ?
F25A C281 1.315(10) . ?
F26A C281 1.330(10) . ?
F11B C161 1.335(9) . ?
F12B C161 1.263(9) . ?
F13B C161 1.402(9) . ?
F14B C181 1.331(13) . ?
F15B C181 1.318(13) . ?
F16B C181 1.324(13) . ?
F21B C261 1.320(8) . ?
F22B C261 1.295(7) . ?
F23B C261 1.406(8) . ?
F24B C281 1.321(12) . ?
F25B C281 1.330(12) . ?
F26B C281 1.320(12) . ?
S1 C13 1.6693(19) . ?
S2 C23 1.677(2) . ?
N11 C13 1.371(2) . ?
N11 C14 1.403(2) . ?
N11 O22 3.070(2) . ?
N12 C13 1.340(2) . ?
N12 C12 1.450(2) . ?
N12 O21 3.002(2) . ?
N21 C23 1.339(2) . ?
N21 C22 1.448(2) . ?
N21 O12 3.141(2) . ?
N22 C23 1.355(2) . ?
N22 C24 1.409(2) . ?
N22 O11 2.955(2) . ?
O11 C11 1.417(3) . ?
O11 C111 1.428(2) . ?
O12 C11 1.381(2) . ?
O12 C121 1.438(3) . ?
O21 C21 1.396(2) . ?
O21 C211 1.442(2) . ?
O22 C21 1.414(2) . ?
O22 C221 1.432(3) . ?
C11 C12 1.502(3) . ?
C14 C19 1.383(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.374(3) . ?
C16 C17 1.385(3) . ?
C16 C161 1.489(3) . ?
C17 C18 1.375(3) . ?
C18 C19 1.389(3) . ?
C18 C181 1.492(3) . ?
C21 C22 1.509(3) . ?
C24 C29 1.381(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.380(3) . ?
C26 C27 1.379(3) . ?
C26 C261 1.488(3) . ?
C27 C28 1.382(3) . ?
C28 C29 1.384(3) . ?
C28 C281 1.488(3) . ?
C111 C112 1.469(4) . ?
C121 C122 1.419(4) . ?
C211 C212 1.497(3) . ?
C221 C222 1.493(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
C13 N11 C14 127.19(16) . . ?
C13 N11 O22 130.29(12) . . ?
C14 N11 O22 102.50(11) . . ?
C13 N12 C12 125.24(17) . . ?
C13 N12 O21 115.60(12) . . ?
C12 N12 O21 119.03(13) . . ?
C23 N21 C22 125.34(18) . . ?
C23 N21 O12 127.67(13) . . ?
C22 N21 O12 106.97(12) . . ?
C23 N22 C24 127.49(17) . . ?
C23 N22 O11 118.18(12) . . ?
C24 N22 O11 114.30(12) . . ?
C11 O11 C111 114.86(16) . . ?
C11 O11 N22 119.73(12) . . ?
C111 O11 N22 113.02(14) . . ?
C11 O12 C121 113.46(17) . . ?
C11 O12 N21 107.63(12) . . ?
C121 O12 N21 110.84(18) . . ?
C21 O21 C211 113.04(15) . . ?
C21 O21 N12 121.79(11) . . ?
C211 O21 N12 111.81(12) . . ?
C21 O22 C221 115.23(16) . . ?
C21 O22 N11 108.31(11) . . ?
C221 O22 N11 132.67(13) . . ?
O12 C11 O11 107.37(17) . . ?
O12 C11 C12 107.73(17) . . ?
O11 C11 C12 112.82(18) . . ?
N12 C12 C11 112.16(16) . . ?
N12 C13 N11 112.43(16) . . ?
N12 C13 S1 123.82(14) . . ?
N11 C13 S1 123.72(15) . . ?
C19 C14 C15 119.21(18) . . ?
C19 C14 N11 118.41(16) . . ?
C15 C14 N11 122.23(17) . . ?
C16 C15 C14 119.64(19) . . ?
C15 C16 C17 121.90(18) . . ?
C15 C16 C161 119.0(2) . . ?
C17 C16 C161 119.1(2) . . ?
C18 C17 C16 117.97(19) . . ?
C17 C18 C19 121.23(19) . . ?
C17 C18 C181 120.41(19) . . ?
C19 C18 C181 118.35(19) . . ?
C14 C19 C18 120.04(17) . . ?
O21 C21 O22 105.86(15) . . ?
O21 C21 C22 108.66(16) . . ?
O22 C21 C22 113.52(16) . . ?
N21 C22 C21 112.32(15) . . ?
N21 C23 N22 113.06(17) . . ?
N21 C23 S2 123.46(15) . . ?
N22 C23 S2 123.47(14) . . ?
C29 C24 C25 119.21(17) . . ?
C29 C24 N22 122.81(17) . . ?
C25 C24 N22 117.79(17) . . ?
C26 C25 C24 120.13(18) . . ?
C27 C26 C25 121.38(18) . . ?
C27 C26 C261 120.03(19) . . ?
C25 C26 C261 118.57(19) . . ?
C26 C27 C28 117.98(18) . . ?
C27 C28 C29 121.29(18) . . ?
C27 C28 C281 120.10(17) . . ?
C29 C28 C281 118.54(17) . . ?
C24 C29 C28 119.99(17) . . ?
O11 C111 C112 110.0(2) . . ?
C122 C121 O12 110.3(2) . . ?
F11A C161 F13A 109.8(6) . . ?
F12B C161 F11B 112.9(8) . . ?
F12 C161 F13 109.5(5) . . ?
F12 C161 F11 107.2(5) . . ?
F13 C161 F11 104.2(4) . . ?
F12B C161 F13B 107.4(8) . . ?
F11B C161 F13B 102.0(6) . . ?
F11A C161 F12A 101.4(6) . . ?
F13A C161 F12A 101.7(5) . . ?
F12B C161 C16 114.9(6) . . ?
F12 C161 C16 113.1(4) . . ?
F11A C161 C16 116.3(6) . . ?
F13A C161 C16 113.3(5) . . ?
F11B C161 C16 113.3(6) . . ?
F13 C161 C16 113.7(4) . . ?
F11 C161 C16 108.6(4) . . ?
F13B C161 C16 104.9(5) . . ?
F12A C161 C16 112.8(5) . . ?
F15B C181 F16B 108.5(12) . . ?
F15B C181 F14B 107.2(12) . . ?
F16B C181 F14B 107.0(12) . . ?
F14 C181 F15 107.7(7) . . ?
F16A C181 F15A 107.1(6) . . ?
F14 C181 F16 107.6(10) . . ?
F15 C181 F16 105.0(9) . . ?
F16A C181 F14A 106.6(6) . . ?
F15A C181 F14A 103.9(4) . . ?
F14 C181 C18 115.8(9) . . ?
F16A C181 C18 114.9(7) . . ?
F15B C181 C18 115.5(12) . . ?
F16B C181 C18 110.8(13) . . ?
F14B C181 C18 107.4(14) . . ?
F15 C181 C18 109.3(7) . . ?
F15A C181 C18 114.1(4) . . ?
F16 C181 C18 110.8(11) . . ?
F14A C181 C18 109.4(5) . . ?
O21 C211 C212 108.10(18) . . ?
O22 C221 C222 109.1(2) . . ?
F23A C261 F21A 108.7(6) . . ?
F22B C261 F21B 109.9(6) . . ?
F22 C261 F21 109.9(5) . . ?
F22 C261 F23 107.3(6) . . ?
F21 C261 F23 102.7(4) . . ?
F23A C261 F22A 105.8(6) . . ?
F21A C261 F22A 103.9(6) . . ?
F22B C261 F23B 104.9(6) . . ?
F21B C261 F23B 100.8(6) . . ?
F22 C261 C26 115.2(3) . . ?
F23A C261 C26 113.3(4) . . ?
F22B C261 C26 113.3(5) . . ?
F21A C261 C26 116.0(6) . . ?
F21B C261 C26 114.8(5) . . ?
F21 C261 C26 111.5(4) . . ?
F23 C261 C26 109.5(3) . . ?
F22A C261 C26 108.3(4) . . ?
F23B C261 C26 112.1(5) . . ?
F26B C281 F24B 106.8(12) . . ?
F25A C281 F24A 106.5(10) . . ?
F25A C281 F26A 107.4(9) . . ?
F24A C281 F26A 107.3(10) . . ?
F26B C281 F25B 106.6(11) . . ?
F24B C281 F25B 106.8(11) . . ?
F26 C281 F24 105.5(7) . . ?
F26 C281 F25 105.3(7) . . ?
F24 C281 F25 105.5(7) . . ?
F25A C281 C28 112.2(10) . . ?
F26B C281 C28 114.8(11) . . ?
F24B C281 C28 111.2(12) . . ?
F24A C281 C28 112.0(11) . . ?
F26A C281 C28 111.1(9) . . ?
F25B C281 C28 110.2(12) . . ?
F26 C281 C28 112.5(9) . . ?
F24 C281 C28 114.4(9) . . ?
F25 C281 C28 112.9(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O22 0.81(2) 2.29(2) 3.070(2) 163(2) .
N12 H12 O21 0.80(2) 2.21(2) 3.002(2) 172(2) .
N21 H21 O12 0.85(2) 2.31(2) 3.141(2) 166(2) .
N22 H22 O11 0.86(2) 2.10(2) 2.955(2) 176(2) .

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 991543'
#######################################################################
#
#                 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_tdacl3ph

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 Cl3 N2 O2 S'
_chemical_formula_weight         371.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   6.769(2)
_cell_length_b                   23.886(8)
_cell_length_c                   10.834(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.947(5)
_cell_angle_gamma                90.00
_cell_volume                     1751.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7188
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      30.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8347
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27726
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         30.67
_reflns_number_total             5411
_reflns_number_gt                3388
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0457P)²+0.3947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5411
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
S S 1.02163(9) 0.70609(2) 0.12598(5) 0.03116(14) Uani 1 1 d . . .
Cl1 Cl 1.10210(9) 0.89541(3) 0.31011(6) 0.03949(16) Uani 1 1 d . . .
Cl2 Cl 0.47855(10) 0.75569(3) 0.32420(7) 0.04959(19) Uani 1 1 d . . .
Cl3 Cl 0.51582(12) 0.93393(3) 0.62503(6) 0.0587(2) Uani 1 1 d . . .
N1 N 0.9780(3) 0.72967(8) 0.36292(16) 0.0239(4) Uani 1 1 d . . .
H1 H 0.956(3) 0.7517(9) 0.419(2) 0.028(6) Uiso 1 1 d . . .
N2 N 0.8642(3) 0.79626(8) 0.22864(16) 0.0269(4) Uani 1 1 d . . .
H2 H 0.849(3) 0.8075(9) 0.160(2) 0.026(6) Uiso 1 1 d . . .
O1 O 1.0017(2) 0.57829(6) 0.41743(13) 0.0291(3) Uani 1 1 d . . .
O2 O 0.7763(2) 0.64000(6) 0.49418(12) 0.0258(3) Uani 1 1 d . . .
C1 C 0.6188(4) 0.89295(11) 0.5100(2) 0.0355(6) Uani 1 1 d . . .
C2 C 0.7957(4) 0.90952(10) 0.4605(2) 0.0327(5) Uani 1 1 d . . .
H2B H 0.8602 0.9427 0.4880 0.039 Uiso 1 1 calc R . .
C3 C 0.8769(3) 0.87623(9) 0.36907(19) 0.0258(4) Uani 1 1 d . . .
C4 C 0.7821(3) 0.82852(9) 0.32519(18) 0.0246(4) Uani 1 1 d . . .
C5 C 0.6034(3) 0.81401(10) 0.3785(2) 0.0305(5) Uani 1 1 d . . .
C6 C 0.5222(3) 0.84517(10) 0.4723(2) 0.0355(6) Uani 1 1 d . . .
H6A H 0.4027 0.8339 0.5098 0.043 Uiso 1 1 calc R . .
C7 C 0.9511(3) 0.74597(9) 0.24647(18) 0.0235(4) Uani 1 1 d . . .
C8 C 1.0620(3) 0.67641(9) 0.39904(18) 0.0244(4) Uani 1 1 d . . .
H8A H 1.1206 0.6797 0.4831 0.029 Uiso 1 1 calc R . .
H8B H 1.1690 0.6665 0.3418 0.029 Uiso 1 1 calc R . .
C9 C 0.9083(3) 0.63027(9) 0.39778(18) 0.0248(4) Uani 1 1 d . . .
H9A H 0.8352 0.6300 0.3168 0.030 Uiso 1 1 calc R . .
C10 C 0.5937(3) 0.61035(10) 0.47625(19) 0.0288(5) Uani 1 1 d . . .
H10A H 0.6207 0.5702 0.4616 0.035 Uiso 1 1 calc R . .
H10B H 0.5218 0.6254 0.4032 0.035 Uiso 1 1 calc R . .
C11 C 0.4703(3) 0.61704(11) 0.5893(2) 0.0368(6) Uani 1 1 d . . .
H11A H 0.3442 0.5975 0.5770 0.055 Uiso 1 1 calc R . .
H11B H 0.4454 0.6569 0.6039 0.055 Uiso 1 1 calc R . .
H11C H 0.5407 0.6011 0.6609 0.055 Uiso 1 1 calc R . .
C12 C 1.0521(4) 0.55017(10) 0.3046(2) 0.0354(5) Uani 1 1 d . . .
H12A H 1.1132 0.5769 0.2467 0.042 Uiso 1 1 calc R . .
H12B H 0.9317 0.5345 0.2645 0.042 Uiso 1 1 calc R . .
C13 C 1.1942(4) 0.50413(10) 0.3359(2) 0.0362(5) Uani 1 1 d . . .
H13A H 1.2317 0.4846 0.2602 0.054 Uiso 1 1 calc R . .
H13B H 1.1317 0.4776 0.3921 0.054 Uiso 1 1 calc R . .
H13C H 1.3125 0.5200 0.3759 0.054 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
S C7 1.691(2) . ?
Cl1 C3 1.725(2) . ?
Cl2 C5 1.727(2) . ?
Cl3 C1 1.740(2) . ?
N1 C7 1.330(3) . ?
N1 C8 1.445(3) . ?
N2 C7 1.350(3) . ?
N2 C4 1.420(3) . ?
O1 C9 1.408(3) . ?
O1 C12 1.441(3) . ?
O2 C9 1.405(2) . ?
O2 C10 1.435(2) . ?
C1 C6 1.374(3) . ?
C1 C2 1.378(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.381(3) . ?
C8 C9 1.516(3) . ?
C10 C11 1.503(3) . ?
C12 C13 1.497(3) . ?

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
C7 N1 C8 124.18(18) . . ?
C7 N2 C4 123.53(18) . . ?
C9 O1 C12 113.26(16) . . ?
C9 O2 C10 111.99(15) . . ?
C6 C1 C2 122.4(2) . . ?
C6 C1 Cl3 119.04(19) . . ?
C2 C1 Cl3 118.6(2) . . ?
C1 C2 C3 118.0(2) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 Cl1 119.84(16) . . ?
C2 C3 Cl1 118.30(18) . . ?
C3 C4 C5 117.52(19) . . ?
C3 C4 N2 120.93(19) . . ?
C5 C4 N2 121.5(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 Cl2 119.12(18) . . ?
C4 C5 Cl2 118.88(17) . . ?
C1 C6 C5 118.2(2) . . ?
N1 C7 N2 116.66(19) . . ?
N1 C7 S 122.10(17) . . ?
N2 C7 S 121.24(15) . . ?
N1 C8 C9 111.76(17) . . ?
O2 C9 O1 108.86(16) . . ?
O2 C9 C8 108.53(16) . . ?
O1 C9 C8 109.46(17) . . ?
O2 C10 C11 109.06(18) . . ?
O1 C12 C13 108.08(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S 0.82(2) 2.49(2) 3.246(2) 153(2) 4_576
N2 H2 O2 0.80(2) 2.24(2) 3.012(2) 164(2) 4_575

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.67
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 991544'
#######################################################################
#
#                 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_tdaome3ph

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N2 O5 S'
_chemical_formula_weight         358.45

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.344(3)
_cell_length_b                   12.952(4)
_cell_length_c                   13.814(4)
_cell_angle_alpha                95.357(4)
_cell_angle_beta                 95.836(4)
_cell_angle_gamma                92.996(4)
_cell_volume                     1829.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7195
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8603
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28972
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         30.36
_reflns_number_total             10893
_reflns_number_gt                6156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0514P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10893
_refine_ls_number_parameters     458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.47503(5) 0.29658(4) 0.10556(3) 0.02658(12) Uani 1 1 d . . .
S2 S -0.02902(5) 0.79140(4) 0.09734(3) 0.02630(12) Uani 1 1 d . . .
N11 N 0.53432(14) 0.17837(11) 0.25080(11) 0.0216(3) Uani 1 1 d . . .
H11 H 0.5835(19) 0.1607(15) 0.2951(14) 0.030(6) Uiso 1 1 d . . .
N12 N 0.69194(14) 0.30221(12) 0.22608(11) 0.0230(3) Uani 1 1 d . . .
H12 H 0.7153(19) 0.3546(15) 0.1920(14) 0.033(6) Uiso 1 1 d . . .
N21 N 0.02937(14) 0.68124(11) 0.24857(11) 0.0218(3) Uani 1 1 d . . .
H21 H 0.0745(19) 0.6723(15) 0.3023(15) 0.033(6) Uiso 1 1 d . . .
N22 N 0.17928(15) 0.81124(12) 0.22708(11) 0.0219(3) Uani 1 1 d . . .
H22 H 0.1957(18) 0.8610(14) 0.1952(13) 0.025(5) Uiso 1 1 d . . .
O11 O 0.47721(12) -0.04395(9) 0.19813(8) 0.0247(3) Uani 1 1 d . . .
O12 O 0.26970(11) -0.00998(9) 0.13771(9) 0.0251(3) Uani 1 1 d . . .
O13 O 0.91487(12) 0.39171(9) 0.55434(8) 0.0258(3) Uani 1 1 d . . .
O14 O 1.02180(12) 0.20960(9) 0.54872(9) 0.0262(3) Uani 1 1 d . . .
O15 O 0.98303(12) 0.07133(9) 0.38936(9) 0.0290(3) Uani 1 1 d . . .
O21 O -0.02069(12) 0.45537(9) 0.20389(9) 0.0246(3) Uani 1 1 d . . .
O22 O -0.22606(11) 0.48448(9) 0.13564(8) 0.0237(3) Uani 1 1 d . . .
O25 O 0.52602(13) 0.61129(10) 0.36607(9) 0.0312(3) Uani 1 1 d . . .
O24 O 0.55992(12) 0.75025(9) 0.53007(9) 0.0268(3) Uani 1 1 d . . .
O23 O 0.40557(12) 0.90434(9) 0.55382(8) 0.0245(3) Uani 1 1 d . . .
C1 C 0.77862(16) 0.27852(13) 0.30776(12) 0.0204(4) Uani 1 1 d . . .
C2 C 0.80251(17) 0.35060(13) 0.38962(12) 0.0219(4) Uani 1 1 d . . .
H2A H 0.7624 0.4150 0.3912 0.026 Uiso 1 1 calc R . .
C3 C 0.88562(16) 0.32750(13) 0.46912(12) 0.0200(4) Uani 1 1 d . . .
C4 C 0.94582(16) 0.23294(13) 0.46691(12) 0.0207(4) Uani 1 1 d . . .
C5 C 0.92181(17) 0.16163(13) 0.38372(13) 0.0218(4) Uani 1 1 d . . .
C6 C 0.83844(17) 0.18428(13) 0.30352(13) 0.0223(4) Uani 1 1 d . . .
H6A H 0.8226 0.1361 0.2468 0.027 Uiso 1 1 calc R . .
C7 C 0.8464(2) 0.48522(14) 0.56447(14) 0.0315(5) Uani 1 1 d . . .
H7A H 0.8742 0.5233 0.6285 0.047 Uiso 1 1 calc R . .
H7B H 0.7525 0.4673 0.5590 0.047 Uiso 1 1 calc R . .
H7C H 0.8656 0.5288 0.5128 0.047 Uiso 1 1 calc R . .
C8 C 1.15965(18) 0.22231(15) 0.54088(15) 0.0342(5) Uani 1 1 d . . .
H8A H 1.2082 0.2045 0.6011 0.051 Uiso 1 1 calc R . .
H8B H 1.1827 0.2946 0.5310 0.051 Uiso 1 1 calc R . .
H8C H 1.1816 0.1764 0.4852 0.051 Uiso 1 1 calc R . .
C9 C 0.9635(2) -0.00431(15) 0.30539(14) 0.0335(5) Uani 1 1 d . . .
H9A H 1.0031 -0.0685 0.3215 0.050 Uiso 1 1 calc R . .
H9B H 1.0040 0.0229 0.2511 0.050 Uiso 1 1 calc R . .
H9C H 0.8699 -0.0188 0.2864 0.050 Uiso 1 1 calc R . .
C10 C 0.57118(17) 0.25542(13) 0.19919(12) 0.0196(4) Uani 1 1 d . . .
C11 C 0.40654(16) 0.12379(13) 0.23468(13) 0.0222(4) Uani 1 1 d . . .
H11A H 0.3412 0.1724 0.2131 0.027 Uiso 1 1 calc R . .
H11B H 0.3836 0.0999 0.2971 0.027 Uiso 1 1 calc R . .
C12 C 0.40128(17) 0.03112(13) 0.15860(13) 0.0216(4) Uani 1 1 d . . .
H12A H 0.4354 0.0522 0.0977 0.026 Uiso 1 1 calc R . .
C13 C 0.49679(18) -0.13055(14) 0.12882(14) 0.0288(4) Uani 1 1 d . . .
H13A H 0.5162 -0.1053 0.0661 0.035 Uiso 1 1 calc R . .
H13B H 0.4170 -0.1775 0.1164 0.035 Uiso 1 1 calc R . .
C14 C 0.6087(2) -0.18781(15) 0.17049(15) 0.0368(5) Uani 1 1 d . . .
H14A H 0.6208 -0.2487 0.1254 0.055 Uiso 1 1 calc R . .
H14B H 0.5901 -0.2103 0.2337 0.055 Uiso 1 1 calc R . .
H14C H 0.6881 -0.1418 0.1795 0.055 Uiso 1 1 calc R . .
C15 C 0.20095(18) 0.02523(14) 0.05164(13) 0.0272(4) Uani 1 1 d . . .
H15A H 0.2344 0.0967 0.0438 0.033 Uiso 1 1 calc R . .
H15B H 0.1073 0.0274 0.0604 0.033 Uiso 1 1 calc R . .
C16 C 0.2163(2) -0.04456(16) -0.03951(14) 0.0378(5) Uani 1 1 d . . .
H16A H 0.1678 -0.0185 -0.0959 0.057 Uiso 1 1 calc R . .
H16B H 0.1825 -0.1152 -0.0324 0.057 Uiso 1 1 calc R . .
H16C H 0.3087 -0.0453 -0.0495 0.057 Uiso 1 1 calc R . .
C17 C 0.26963(16) 0.79005(13) 0.30776(12) 0.0195(4) Uani 1 1 d . . .
C18 C 0.34409(17) 0.70444(13) 0.29771(13) 0.0234(4) Uani 1 1 d . . .
H18A H 0.3294 0.6567 0.2406 0.028 Uiso 1 1 calc R . .
C19 C 0.44065(17) 0.68899(13) 0.37213(13) 0.0227(4) Uani 1 1 d . . .
C20 C 0.45927(16) 0.75706(13) 0.45770(12) 0.0205(4) Uani 1 1 d . . .
C21 C 0.38087(16) 0.84192(13) 0.46747(12) 0.0192(4) Uani 1 1 d . . .
C22 C 0.28685(16) 0.85924(13) 0.39215(12) 0.0204(4) Uani 1 1 d . . .
H22A H 0.2351 0.9175 0.3983 0.024 Uiso 1 1 calc R . .
C23 C 0.34241(18) 1.00091(13) 0.56023(13) 0.0265(4) Uani 1 1 d . . .
H23A H 0.3717 1.0407 0.6232 0.040 Uiso 1 1 calc R . .
H23B H 0.2479 0.9865 0.5548 0.040 Uiso 1 1 calc R . .
H23C H 0.3648 1.0412 0.5070 0.040 Uiso 1 1 calc R . .
C24 C 0.56033(19) 0.65629(15) 0.57793(14) 0.0318(5) Uani 1 1 d . . .
H24A H 0.6253 0.6651 0.6354 0.048 Uiso 1 1 calc R . .
H24B H 0.5820 0.5986 0.5325 0.048 Uiso 1 1 calc R . .
H24C H 0.4740 0.6412 0.5985 0.048 Uiso 1 1 calc R . .
C25 C 0.5149(2) 0.54438(15) 0.27673(14) 0.0346(5) Uani 1 1 d . . .
H25A H 0.5834 0.4950 0.2798 0.052 Uiso 1 1 calc R . .
H25B H 0.5241 0.5861 0.2219 0.052 Uiso 1 1 calc R . .
H25C H 0.4294 0.5063 0.2673 0.052 Uiso 1 1 calc R . .
C26 C 0.06410(16) 0.75841(12) 0.19613(12) 0.0192(4) Uani 1 1 d . . .
C27 C -0.09644(16) 0.62322(13) 0.23107(12) 0.0221(4) Uani 1 1 d . . .
H27A H -0.1628 0.6691 0.2057 0.026 Uiso 1 1 calc R . .
H27B H -0.1215 0.6016 0.2938 0.026 Uiso 1 1 calc R . .
C28 C -0.09536(16) 0.52773(13) 0.15887(12) 0.0208(4) Uani 1 1 d . . .
H28A H -0.0581 0.5465 0.0983 0.025 Uiso 1 1 calc R . .
C29 C -0.29201(18) 0.51844(14) 0.04824(13) 0.0276(4) Uani 1 1 d . . .
H29A H -0.2585 0.5898 0.0402 0.033 Uiso 1 1 calc R . .
H29B H -0.3863 0.5203 0.0550 0.033 Uiso 1 1 calc R . .
C30 C -0.2727(2) 0.44756(17) -0.04123(14) 0.0407(5) Uani 1 1 d . . .
H30A H -0.3149 0.4748 -0.0995 0.061 Uiso 1 1 calc R . .
H30B H -0.3112 0.3779 -0.0355 0.061 Uiso 1 1 calc R . .
H30C H -0.1793 0.4438 -0.0469 0.061 Uiso 1 1 calc R . .
C31 C 0.00525(19) 0.36731(14) 0.13854(14) 0.0308(4) Uani 1 1 d . . .
H31A H 0.0347 0.3911 0.0779 0.037 Uiso 1 1 calc R . .
H31B H -0.0750 0.3216 0.1207 0.037 Uiso 1 1 calc R . .
C32 C 0.1096(2) 0.30867(16) 0.18960(16) 0.0415(5) Uani 1 1 d . . .
H32A H 0.1254 0.2466 0.1474 0.062 Uiso 1 1 calc R . .
H32B H 0.0811 0.2880 0.2509 0.062 Uiso 1 1 calc R . .
H32C H 0.1900 0.3533 0.2037 0.062 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 C10 1.6938(17) . ?
S2 C26 1.6904(17) . ?
N11 C10 1.341(2) . ?
N11 C11 1.452(2) . ?
N12 C10 1.360(2) . ?
N12 C1 1.435(2) . ?
N21 C26 1.343(2) . ?
N21 C27 1.455(2) . ?
N22 C26 1.352(2) . ?
N22 C17 1.436(2) . ?
O11 C12 1.397(2) . ?
O11 C13 1.442(2) . ?
O12 C12 1.426(2) . ?
O12 C15 1.446(2) . ?
O13 C3 1.374(2) . ?
O13 C7 1.438(2) . ?
O14 C4 1.3763(19) . ?
O14 C8 1.443(2) . ?
O15 C5 1.364(2) . ?
O15 C9 1.437(2) . ?
O21 C28 1.396(2) . ?
O21 C31 1.441(2) . ?
O22 C28 1.4296(19) . ?
O22 C29 1.442(2) . ?
O25 C19 1.375(2) . ?
O25 C25 1.431(2) . ?
O24 C20 1.380(2) . ?
O24 C24 1.438(2) . ?
O23 C21 1.3704(19) . ?
O23 C23 1.441(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.396(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.402(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.396(2) . ?
C11 C12 1.515(2) . ?
C13 C14 1.501(3) . ?
C15 C16 1.507(3) . ?
C17 C18 1.387(2) . ?
C17 C22 1.393(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.397(2) . ?
C20 C21 1.404(2) . ?
C21 C22 1.393(2) . ?
C27 C28 1.516(2) . ?
C29 C30 1.506(3) . ?
C31 C32 1.507(3) . ?

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
C10 N11 C11 123.73(15) . . ?
C10 N12 C1 124.82(15) . . ?
C26 N21 C27 123.44(15) . . ?
C26 N22 C17 126.32(15) . . ?
C12 O11 C13 113.98(13) . . ?
C12 O12 C15 114.30(13) . . ?
C3 O13 C7 117.30(13) . . ?
C4 O14 C8 113.40(14) . . ?
C5 O15 C9 117.47(14) . . ?
C28 O21 C31 113.90(13) . . ?
C28 O22 C29 113.93(13) . . ?
C19 O25 C25 117.03(14) . . ?
C20 O24 C24 116.56(14) . . ?
C21 O23 C23 116.86(13) . . ?
C2 C1 C6 121.11(16) . . ?
C2 C1 N12 119.22(15) . . ?
C6 C1 N12 119.67(15) . . ?
C3 C2 C1 119.33(16) . . ?
O13 C3 C2 124.54(15) . . ?
O13 C3 C4 114.89(14) . . ?
C2 C3 C4 120.57(16) . . ?
O14 C4 C5 121.14(15) . . ?
O14 C4 C3 119.31(15) . . ?
C5 C4 C3 119.45(15) . . ?
O15 C5 C6 124.66(15) . . ?
O15 C5 C4 115.01(15) . . ?
C6 C5 C4 120.32(16) . . ?
C1 C6 C5 119.22(16) . . ?
N11 C10 N12 116.75(15) . . ?
N11 C10 S1 123.40(13) . . ?
N12 C10 S1 119.85(13) . . ?
N11 C11 C12 112.24(14) . . ?
O11 C12 O12 109.24(13) . . ?
O11 C12 C11 107.88(14) . . ?
O12 C12 C11 108.84(14) . . ?
O11 C13 C14 108.46(15) . . ?
O12 C15 C16 111.99(15) . . ?
C18 C17 C22 121.18(15) . . ?
C18 C17 N22 119.22(15) . . ?
C22 C17 N22 119.47(15) . . ?
C17 C18 C19 119.48(16) . . ?
O25 C19 C18 123.92(15) . . ?
O25 C19 C20 115.69(15) . . ?
C18 C19 C20 120.34(16) . . ?
O24 C20 C19 122.63(15) . . ?
O24 C20 C21 117.77(15) . . ?
C19 C20 C21 119.33(15) . . ?
O23 C21 C22 124.16(15) . . ?
O23 C21 C20 115.36(14) . . ?
C22 C21 C20 120.47(15) . . ?
C17 C22 C21 119.16(16) . . ?
N21 C26 N22 116.35(15) . . ?
N21 C26 S2 123.32(13) . . ?
N22 C26 S2 120.32(13) . . ?
N21 C27 C28 112.47(14) . . ?
O21 C28 O22 108.93(13) . . ?
O21 C28 C27 108.18(14) . . ?
O22 C28 C27 108.42(14) . . ?
O22 C29 C30 111.64(15) . . ?
O21 C31 C32 108.39(16) . . ?

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
N11 H11 O23 0.813(19) 2.32(2) 3.015(2) 144.3(18) 2_666
N12 H12 O22 0.90(2) 2.01(2) 2.900(2) 171.3(17) 1_655
N21 H21 O13 0.86(2) 2.21(2) 2.976(2) 148.5(18) 2_666
N22 H22 O12 0.833(19) 2.061(19) 2.882(2) 168.1(18) 1_565

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.36
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 991545'
#######################################################################
#
#                 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_tdaomeno2ph

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 N3 O5 S'
_chemical_formula_weight         343.40

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                   13.241(4)
_cell_length_b                   15.160(4)
_cell_length_c                   8.398(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.009(4)
_cell_angle_gamma                90.00
_cell_volume                     1654.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2336
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.55

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8040
_diffrn_reflns_av_R_equivalents  0.1117
_diffrn_reflns_av_sigmaI/netI    0.1482
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4104
_reflns_number_gt                1820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
S S 0.81190(6) 0.12435(5) 0.09685(9) 0.0305(2) Uani 1 1 d . . .
N1 N 0.7634(2) 0.19677(17) -0.1964(3) 0.0299(6) Uani 1 1 d . . .
H1 H 0.764(2) 0.2411(18) -0.258(3) 0.049(11) Uiso 1 1 d . . .
N2 N 0.8863(2) 0.27008(16) -0.0227(3) 0.0279(6) Uani 1 1 d . . .
H2 H 0.877(2) 0.3057(17) -0.092(3) 0.025(9) Uiso 1 1 d . . .
N3 N 0.92879(19) 0.44339(16) 0.1200(3) 0.0332(6) Uani 1 1 d . . .
O1 O 0.92252(16) 0.50180(13) 0.2185(3) 0.0450(6) Uani 1 1 d . . .
O2 O 0.88568(16) 0.44665(13) -0.0230(3) 0.0438(6) Uani 1 1 d . . .
O4 O 0.50075(15) 0.12340(13) -0.3277(2) 0.0355(5) Uani 1 1 d . . .
O5 O 0.57160(14) 0.26204(12) -0.3396(2) 0.0296(5) Uani 1 1 d . . .
O3 O 1.22319(14) 0.31689(12) 0.4799(2) 0.0329(5) Uani 1 1 d . . .
C1 C 0.9690(2) 0.28363(18) 0.1083(3) 0.0242(7) Uani 1 1 d . . .
C2 C 1.0327(2) 0.21467(18) 0.1739(3) 0.0284(7) Uani 1 1 d . . .
H2B H 1.0187 0.1569 0.1317 0.034 Uiso 1 1 calc R . .
C3 C 1.1149(2) 0.22757(18) 0.2971(3) 0.0289(7) Uani 1 1 d . . .
H3B H 1.1562 0.1788 0.3405 0.035 Uiso 1 1 calc R . .
C4 C 1.1386(2) 0.3114(2) 0.3595(3) 0.0282(7) Uani 1 1 d . . .
C5 C 1.0762(2) 0.38168(19) 0.3006(3) 0.0280(7) Uani 1 1 d . . .
H5A H 1.0899 0.4392 0.3444 0.034 Uiso 1 1 calc R . .
C6 C 0.9931(2) 0.36619(18) 0.1758(3) 0.0245(7) Uani 1 1 d . . .
C7 C 1.2477(2) 0.40117(17) 0.5525(3) 0.0382(8) Uani 1 1 d . . .
H7A H 1.3055 0.3953 0.6440 0.057 Uiso 1 1 calc R . .
H7B H 1.1877 0.4245 0.5915 0.057 Uiso 1 1 calc R . .
H7C H 1.2665 0.4417 0.4721 0.057 Uiso 1 1 calc R . .
C8 C 0.6784(2) 0.13724(18) -0.2518(3) 0.0294(7) Uani 1 1 d . . .
H8A H 0.6849 0.0849 -0.1800 0.035 Uiso 1 1 calc R . .
H8B H 0.6811 0.1169 -0.3629 0.035 Uiso 1 1 calc R . .
C9 C 0.5761(2) 0.18214(18) -0.2517(3) 0.0291(7) Uani 1 1 d . . .
H9A H 0.5674 0.1938 -0.1379 0.035 Uiso 1 1 calc R . .
C10 C 0.5518(2) 0.33843(18) -0.2508(4) 0.0373(8) Uani 1 1 d . . .
H10A H 0.6127 0.3523 -0.1662 0.045 Uiso 1 1 calc R . .
H10B H 0.4926 0.3275 -0.1971 0.045 Uiso 1 1 calc R . .
C11 C 0.5287(2) 0.41377(18) -0.3664(3) 0.0386(8) Uani 1 1 d . . .
H11A H 0.5101 0.4657 -0.3088 0.058 Uiso 1 1 calc R . .
H11B H 0.4712 0.3980 -0.4537 0.058 Uiso 1 1 calc R . .
H11C H 0.5895 0.4271 -0.4127 0.058 Uiso 1 1 calc R . .
C12 C 0.3980(2) 0.1540(2) -0.3337(4) 0.0473(9) Uani 1 1 d . . .
H12A H 0.3868 0.2096 -0.3963 0.057 Uiso 1 1 calc R . .
H12B H 0.3866 0.1656 -0.2225 0.057 Uiso 1 1 calc R . .
C13 C 0.3245(3) 0.0848(2) -0.4130(4) 0.0709(12) Uani 1 1 d . . .
H13A H 0.2539 0.1070 -0.4254 0.106 Uiso 1 1 calc R . .
H13B H 0.3320 0.0316 -0.3455 0.106 Uiso 1 1 calc R . .
H13C H 0.3394 0.0707 -0.5199 0.106 Uiso 1 1 calc R . .
C14 C 0.8209(2) 0.19976(18) -0.0470(3) 0.0253(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C14 1.684(3) . ?
N1 C14 1.339(3) . ?
N1 C8 1.448(3) . ?
N2 C14 1.364(3) . ?
N2 C1 1.412(3) . ?
N3 O1 1.226(3) . ?
N3 O2 1.228(3) . ?
N3 C6 1.470(3) . ?
O4 C9 1.397(3) . ?
O4 C12 1.429(3) . ?
O5 C9 1.414(3) . ?
O5 C10 1.428(3) . ?
O3 C4 1.360(3) . ?
O3 C7 1.426(3) . ?
C1 C6 1.386(4) . ?
C1 C2 1.389(3) . ?
C2 C3 1.365(3) . ?
C3 C4 1.387(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.387(3) . ?
C8 C9 1.516(4) . ?
C10 C11 1.492(4) . ?
C12 C13 1.497(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
C14 N1 C8 126.2(3) . . ?
C14 N2 C1 127.3(3) . . ?
O1 N3 O2 123.5(3) . . ?
O1 N3 C6 118.0(2) . . ?
O2 N3 C6 118.5(2) . . ?
C9 O4 C12 113.7(2) . . ?
C9 O5 C10 114.6(2) . . ?
C4 O3 C7 117.4(2) . . ?
C6 C1 C2 116.3(3) . . ?
C6 C1 N2 122.3(3) . . ?
C2 C1 N2 121.4(3) . . ?
C3 C2 C1 121.9(3) . . ?
C2 C3 C4 120.5(3) . . ?
O3 C4 C5 124.8(3) . . ?
O3 C4 C3 115.6(3) . . ?
C5 C4 C3 119.7(3) . . ?
C4 C5 C6 118.3(3) . . ?
C1 C6 C5 123.3(3) . . ?
C1 C6 N3 121.0(2) . . ?
C5 C6 N3 115.7(3) . . ?
N1 C8 C9 111.1(2) . . ?
O4 C9 O5 110.6(2) . . ?
O4 C9 C8 105.9(2) . . ?
O5 C9 C8 109.5(2) . . ?
O5 C10 C11 108.4(2) . . ?
O4 C12 C13 108.8(3) . . ?
N1 C14 N2 113.4(3) . . ?
N1 C14 S 123.0(2) . . ?
N2 C14 S 123.6(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
N1 H1 S 0.85(3) 2.52(3) 3.348(3) 166(3) 4_565
N2 H2 S 0.78(2) 2.80(2) 3.541(3) 158(2) 4_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 991546'
