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

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

data_aslamintermediate
_database_code_depnum_ccdc_archive 'CCDC 1824190'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C F3 O3 S, C26 H18 N O'
_chemical_formula_sum            'C27 H18 F3 N O4 S'
_chemical_formula_weight         509.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N10 O10 S10 F10'
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'
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'

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

_cell_length_a                   8.9248(5)
_cell_length_b                   11.0144(6)
_cell_length_c                   12.8073(7)
_cell_angle_alpha                107.950(5)
_cell_angle_beta                 91.426(4)
_cell_angle_gamma                100.556(4)
_cell_volume                     1172.96(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.8990
_cell_measurement_theta_min      3.4170
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             533
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10186
_diffrn_reflns_theta_full        29.10
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8503
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  56.00   1.00   19.11    --   19.75  37.00  90.00   64
  2  ω     39.00  89.00   1.00   19.11    --   19.75  57.00  90.00   50
  3  ω     12.00  41.00   1.00   19.11    --   19.75 -57.00 150.00   29
  4  ω    -45.00 -19.00   1.00   19.11    --   19.75 -57.00 150.00   26
  5  ω    -49.00  29.00   1.00   19.11    --   19.75 -57.00 -60.00   78
  6  ω    -20.00  63.00   1.00   19.11    --   19.75 -99.00-180.00   83
  7  ω      6.00  71.00   1.00   19.11    --   19.75  77.00-120.00   65
  8  ω     50.00  75.00   1.00   19.11    --   19.75 178.00 -90.00   25
  9  ω    -82.00 -53.00   1.00   19.11    --  -20.06 131.00 -55.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284561000
_diffrn_orient_matrix_UB_12      -0.0648285000
_diffrn_orient_matrix_UB_13      -0.0008504000
_diffrn_orient_matrix_UB_21      -0.0084058000
_diffrn_orient_matrix_UB_22      -0.0207771000
_diffrn_orient_matrix_UB_23      -0.0584153000
_diffrn_orient_matrix_UB_31      0.0755320000
_diffrn_orient_matrix_UB_32      -0.0118375000
_diffrn_orient_matrix_UB_33      -0.0013608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3204
_reflns_number_total             5354
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0988
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1365P)²+1.4542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2859
_refine_ls_wR_factor_ref         0.3199
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H28 of C28, H22 of C22, H32 of C32, H21 of C21, H31 of C31, H30 of C30, H34
  of C34, H27 of C27, H29 of C29, H24 of C24, H14 of C14, H13 of C13, H15 of
  C15, H33 of C33, H12 of C12
 At 1.5 times of:
  {H36A,H36B,H36C} of C36
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C33(H33), C15(H15), C13(H13), C31(H31), C30(H30), C34(H34),
 C27(H27), C29(H29), C24(H24), C14(H14), C28(H28), C21(H21), C32(H32), C22(H22)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S3 S 0.71364(14) 0.64146(13) 0.23697(11) 0.0745(5) Uani 1 1 d . . .
O35 O 0.1068(4) 0.0069(4) 0.1562(4) 0.0877(11) Uani 1 1 d . . .
C11 C 0.9396(5) 0.3013(4) 0.2112(4) 0.0543(10) Uani 1 1 d . . .
C12 C 1.0200(5) 0.3202(4) 0.3101(4) 0.0654(12) Uani 1 1 d . . .
H12 H 0.9716 0.2984 0.3673 0.079 Uiso 1 1 calc R . .
C33 C 0.7724(8) 0.3034(5) -0.1322(4) 0.0802(15) Uani 1 1 d . . .
H33 H 0.7745 0.3191 -0.1996 0.096 Uiso 1 1 calc R . .
C15 C 1.1715(6) 0.3870(5) 0.1392(5) 0.0761(15) Uani 1 1 d . . .
H15 H 1.2222 0.4080 0.0825 0.091 Uiso 1 1 calc R . .
C13 C 1.1755(6) 0.3727(5) 0.3215(5) 0.0792(15) Uani 1 1 d . . .
H13 H 1.2322 0.3869 0.3876 0.095 Uiso 1 1 calc R . .
C26 C 0.6621(4) 0.1892(4) 0.3264(3) 0.0508(9) Uani 1 1 d . . .
C31 C 0.7008(6) 0.0803(5) 0.3419(4) 0.0701(13) Uani 1 1 d . . .
H31 H 0.7288 0.0174 0.2828 0.084 Uiso 1 1 calc R . .
C30 C 0.6987(8) 0.0634(7) 0.4434(5) 0.0960(18) Uani 1 1 d . . .
H30 H 0.7251 -0.0104 0.4534 0.115 Uiso 1 1 calc R . .
O4 O 0.7546(9) 0.7627(5) 0.2172(6) 0.175(3) Uani 1 1 d . . .
C34 C 0.9070(7) 0.3319(5) -0.0661(4) 0.0776(15) Uani 1 1 d . . .
H34 H 0.9992 0.3637 -0.0898 0.093 Uiso 1 1 calc R . .
C27 C 0.6211(6) 0.2824(5) 0.4144(4) 0.0775(14) Uani 1 1 d . . .
H27 H 0.5942 0.3563 0.4051 0.093 Uiso 1 1 calc R . .
C16 C 1.0121(5) 0.3361(4) 0.1257(4) 0.0625(12) Uani 1 1 d . . .
N18 N 0.7626(4) 0.2614(3) 0.0646(3) 0.0561(9) Uani 1 1 d . . .
C29 C 0.6573(8) 0.1563(8) 0.5304(5) 0.100(2) Uani 1 1 d . . .
H29 H 0.6544 0.1446 0.5992 0.120 Uiso 1 1 calc R . .
C24 C 0.3782(5) 0.1036(4) 0.1885(4) 0.0564(10) Uani 1 1 d . . .
H24 H 0.3852 0.0935 0.2578 0.068 Uiso 1 1 calc R . .
C9 C 0.6526(5) 0.2025(4) 0.2149(3) 0.0506(9) Uani 1 1 d . . .
C25 C 0.5086(5) 0.1601(4) 0.1484(3) 0.0513(9) Uani 1 1 d . . .
C17 C 0.9037(6) 0.3129(4) 0.0349(4) 0.0622(11) Uani 1 1 d . . .
C2 C 0.8416(10) 0.6697(7) 0.3547(6) 0.103(2) Uani 1 1 d . . .
C14 C 1.2475(6) 0.4041(5) 0.2362(6) 0.0842(17) Uani 1 1 d . . .
H14 H 1.3521 0.4383 0.2464 0.101 Uiso 1 1 calc R . .
C19 C 0.6306(5) 0.2297(4) 0.0009(4) 0.0584(11) Uani 1 1 d . . .
C10 C 0.7785(5) 0.2513(4) 0.1725(3) 0.0517(9) Uani 1 1 d . . .
F1 F 0.8242(8) 0.7629(5) 0.4397(4) 0.177(2) Uani 1 1 d . . .
C28 C 0.6206(8) 0.2648(7) 0.5173(5) 0.100(2) Uani 1 1 d . . .
H28 H 0.5949 0.3278 0.5773 0.120 Uiso 1 1 calc R . .
C20 C 0.4971(5) 0.1755(4) 0.0429(4) 0.0580(10) Uani 1 1 d . . .
C36 C 0.1058(6) -0.0032(6) 0.2633(6) 0.0931(18) Uani 1 1 d . . .
H36A H 0.1765 -0.0562 0.2720 0.140 Uiso 1 1 calc R . .
H36B H 0.0048 -0.0425 0.2745 0.140 Uiso 1 1 calc R . .
H36C H 0.1354 0.0820 0.3165 0.140 Uiso 1 1 calc R . .
C21 C 0.3539(6) 0.1329(5) -0.0182(4) 0.0716(13) Uani 1 1 d . . .
H21 H 0.3446 0.1425 -0.0876 0.086 Uiso 1 1 calc R . .
C23 C 0.2399(5) 0.0631(4) 0.1259(4) 0.0655(12) Uani 1 1 d . . .
C32 C 0.6375(7) 0.2531(5) -0.1009(4) 0.0732(13) Uani 1 1 d . . .
H32 H 0.5485 0.2338 -0.1472 0.088 Uiso 1 1 calc R . .
C22 C 0.2292(6) 0.0784(5) 0.0214(5) 0.0745(14) Uani 1 1 d . . .
H22 H 0.1357 0.0508 -0.0209 0.089 Uiso 1 1 calc R . .
O5 O 0.7637(7) 0.5447(5) 0.1557(4) 0.1254(17) Uani 1 1 d . . .
F7 F 0.8243(13) 0.5710(7) 0.3904(5) 0.254(5) Uani 1 1 d . . .
F8 F 0.9801(7) 0.6829(10) 0.3348(6) 0.239(4) Uani 1 1 d . . .
O6 O 0.5737(7) 0.6241(12) 0.2679(6) 0.269(6) 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
S3 O4 1.420(6) . ?
S3 C2 1.780(8) . ?
S3 O5 1.390(4) . ?
S3 O6 1.318(5) . ?
O35 C36 1.411(7) . ?
O35 C23 1.359(6) . ?
C11 C12 1.378(6) . ?
C11 C16 1.402(6) . ?
C11 C10 1.457(6) . ?
C12 C13 1.388(6) . ?
C33 C34 1.380(8) . ?
C33 C32 1.355(8) . ?
C15 C16 1.416(7) . ?
C15 C14 1.344(9) . ?
C13 C14 1.383(8) . ?
C26 C31 1.376(6) . ?
C26 C27 1.380(6) . ?
C26 C9 1.482(6) . ?
C31 C30 1.369(8) . ?
C30 C29 1.371(9) . ?
C34 C17 1.373(7) . ?
C27 C28 1.389(8) . ?
C16 C17 1.423(7) . ?
N18 C17 1.396(6) . ?
N18 C19 1.343(6) . ?
N18 C10 1.426(5) . ?
C29 C28 1.351(10) . ?
C24 C25 1.402(6) . ?
C24 C23 1.376(6) . ?
C9 C25 1.440(5) . ?
C9 C10 1.354(5) . ?
C25 C20 1.417(6) . ?
C2 F1 1.281(8) . ?
C2 F7 1.291(8) . ?
C2 F8 1.260(9) . ?
C19 C20 1.427(6) . ?
C19 C32 1.405(6) . ?
C20 C21 1.403(6) . ?
C21 C22 1.352(8) . ?
C23 C22 1.403(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S3 C2 100.3(3) . . ?
O5 S3 O4 110.1(4) . . ?
O5 S3 C2 103.7(4) . . ?
O6 S3 O4 111.4(7) . . ?
O6 S3 C2 107.1(5) . . ?
O6 S3 O5 121.7(5) . . ?
C23 O35 C36 118.1(4) . . ?
C12 C11 C16 121.1(4) . . ?
C12 C11 C10 132.1(4) . . ?
C16 C11 C10 106.8(4) . . ?
C11 C12 C13 117.7(5) . . ?
C32 C33 C34 121.2(5) . . ?
C14 C15 C16 118.0(5) . . ?
C14 C13 C12 121.1(6) . . ?
C31 C26 C27 119.4(4) . . ?
C31 C26 C9 120.7(4) . . ?
C27 C26 C9 119.7(4) . . ?
C30 C31 C26 120.7(5) . . ?
C31 C30 C29 119.4(6) . . ?
C17 C34 C33 119.6(5) . . ?
C26 C27 C28 119.3(6) . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 C17 110.3(4) . . ?
C15 C16 C17 129.9(5) . . ?
C17 N18 C10 110.5(4) . . ?
C19 N18 C17 124.1(4) . . ?
C19 N18 C10 125.3(4) . . ?
C28 C29 C30 120.8(6) . . ?
C23 C24 C25 120.4(4) . . ?
C25 C9 C26 120.0(4) . . ?
C10 C9 C26 121.1(4) . . ?
C10 C9 C25 118.8(4) . . ?
C24 C25 C9 119.9(4) . . ?
C24 C25 C20 119.5(4) . . ?
C20 C25 C9 120.6(4) . . ?
C34 C17 C16 136.0(5) . . ?
C34 C17 N18 117.6(5) . . ?
N18 C17 C16 106.4(4) . . ?
F1 C2 S3 115.2(6) . . ?
F1 C2 F7 102.9(7) . . ?
F7 C2 S3 112.1(7) . . ?
F8 C2 S3 113.4(6) . . ?
F8 C2 F1 110.0(8) . . ?
F8 C2 F7 101.9(9) . . ?
C15 C14 C13 122.2(5) . . ?
N18 C19 C20 116.9(4) . . ?
N18 C19 C32 116.7(4) . . ?
C32 C19 C20 126.3(5) . . ?
N18 C10 C11 106.0(3) . . ?
C9 C10 C11 135.3(4) . . ?
C9 C10 N18 118.6(4) . . ?
C29 C28 C27 120.3(6) . . ?
C25 C20 C19 119.5(4) . . ?
C21 C20 C25 118.3(4) . . ?
C21 C20 C19 122.2(5) . . ?
C22 C21 C20 121.6(5) . . ?
O35 C23 C24 125.4(5) . . ?
O35 C23 C22 114.7(4) . . ?
C24 C23 C22 119.9(5) . . ?
C33 C32 C19 120.7(5) . . ?
C21 C22 C23 120.4(4) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.530
_oxdiff_exptl_absorpt_empirical_full_min 0.478
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aslambhai2
_database_code_depnum_ccdc_archive 'CCDC 1824191'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;
_audit_creation_date             2017-11-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C F3 O3 S, C30 H20 N O'
_chemical_formula_sum            'C31 H21 F3 N3 O3 S'
_chemical_formula_weight         559.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N10 O10 S10 F10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        C2/c
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.0551(3)
_cell_length_b                   29.5519(9)
_cell_length_c                   20.7844(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.425(3)
_cell_angle_gamma                90.00
_cell_volume                     5486.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5147
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.2420
_cell_measurement_theta_min      3.8520
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6269
_diffrn_reflns_theta_full        29.30
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.8330
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  49.00   1.00   38.16    --   19.75 -77.00 -60.00   26
  2  ω    -31.00  -5.00   1.00   38.16    --  -20.06 -57.00-150.00   26
  3  ω    -50.00  -3.00   1.00   38.16    --   19.75 -77.00-150.00   47
  4  ω     -4.00  91.00   1.00   38.16    --   19.75  77.00  60.00   95
  5  ω     -5.00  37.00   1.00   38.16    --   19.75  77.00-180.00   42
  6  ω    -74.00 -46.00   1.00   38.16    --  -20.06 164.00 112.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0179827000
_diffrn_orient_matrix_UB_12      -0.0041931000
_diffrn_orient_matrix_UB_13      -0.0339836000
_diffrn_orient_matrix_UB_21      -0.0136451000
_diffrn_orient_matrix_UB_22      0.0234294000
_diffrn_orient_matrix_UB_23      -0.0056072000
_diffrn_orient_matrix_UB_31      0.0761324000
_diffrn_orient_matrix_UB_32      0.0032042000
_diffrn_orient_matrix_UB_33      -0.0031284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4464
_reflns_number_total             6269
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1176P)²+2.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2198
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
S3 S 0.09648(7) 0.36677(2) 0.43703(3) 0.0469(2) Uani 1 1 d . . .
N9 N 0.4965(2) 0.63646(6) 0.44190(10) 0.0411(4) Uani 1 1 d . . .
O6 O 0.0288(3) 0.32544(7) 0.45276(12) 0.0721(6) Uani 1 1 d . . .
F1 F 0.1002(3) 0.33525(7) 0.32067(10) 0.0981(8) Uani 1 1 d . . .
O5 O 0.0310(3) 0.40670(7) 0.45969(11) 0.0710(6) Uani 1 1 d . . .
F8 F 0.1020(3) 0.40765(7) 0.32652(10) 0.0928(7) Uani 1 1 d . . .
C18 C 0.5646(2) 0.60123(7) 0.41284(11) 0.0389(5) Uani 1 1 d . . .
O4 O 0.2552(2) 0.36640(9) 0.44644(12) 0.0812(7) Uani 1 1 d . . .
C17 C 0.6900(3) 0.60980(7) 0.38644(11) 0.0391(5) Uani 1 1 d . . .
F7 F -0.0973(3) 0.37135(10) 0.32994(14) 0.1256(10) Uani 1 1 d . . .
C36 C 0.7106(3) 0.56537(10) 0.28720(13) 0.0539(6) Uani 1 1 d . . .
H36 H 0.6533 0.5873 0.2625 0.065 Uiso 1 1 calc R . .
O33 O 1.2892(3) 0.70501(10) 0.30495(13) 0.0859(8) Uani 1 1 d . . .
C24 C 0.4754(3) 0.56108(8) 0.42015(11) 0.0424(5) Uani 1 1 d . . .
C16 C 0.7509(2) 0.65488(7) 0.38833(11) 0.0389(5) Uani 1 1 d . . .
C14 C 0.5423(3) 0.67999(8) 0.44282(12) 0.0435(5) Uani 1 1 d . . .
C28 C 1.1560(3) 0.69519(12) 0.32437(13) 0.0618(8) Uani 1 1 d . . .
C40 C 0.8349(3) 0.53728(9) 0.38962(13) 0.0515(6) Uani 1 1 d . . .
H40 H 0.8630 0.5407 0.4344 0.062 Uiso 1 1 calc R . .
C15 C 0.6701(3) 0.69007(8) 0.41347(11) 0.0428(5) Uani 1 1 d . . .
C27 C 1.1249(3) 0.64964(12) 0.33007(15) 0.0616(7) Uani 1 1 d . . .
H27 H 1.1930 0.6282 0.3204 0.074 Uiso 1 1 calc R . .
C29 C 1.0588(3) 0.72702(11) 0.34000(15) 0.0615(7) Uani 1 1 d . . .
H29 H 1.0796 0.7576 0.3362 0.074 Uiso 1 1 calc R . .
C22 C 0.3809(3) 0.48586(10) 0.41680(14) 0.0594(7) Uani 1 1 d . . .
H22 H 0.3875 0.4557 0.4047 0.071 Uiso 1 1 calc R . .
C35 C 0.7491(2) 0.57040(7) 0.35390(11) 0.0394(5) Uani 1 1 d . . .
C26 C 0.9946(3) 0.63570(9) 0.34988(14) 0.0524(6) Uani 1 1 d . . .
H26 H 0.9759 0.6049 0.3529 0.063 Uiso 1 1 calc R . .
C39 C 0.8785(3) 0.49952(10) 0.35908(16) 0.0629(8) Uani 1 1 d . . .
H39 H 0.9342 0.4771 0.3834 0.076 Uiso 1 1 calc R . .
C23 C 0.4861(3) 0.51602(9) 0.40150(13) 0.0516(6) Uani 1 1 d . . .
H23 H 0.5620 0.5066 0.3794 0.062 Uiso 1 1 calc R . .
C31 C 0.8324(3) 0.74709(9) 0.38222(15) 0.0596(7) Uani 1 1 d . . .
H31 H 0.8542 0.7775 0.3768 0.072 Uiso 1 1 calc R . .
C13 C 0.4610(3) 0.71085(10) 0.47561(15) 0.0571(7) Uani 1 1 d . . .
H13 H 0.4875 0.7413 0.4781 0.068 Uiso 1 1 calc R . .
C30 C 0.9269(3) 0.71335(9) 0.36189(13) 0.0499(6) Uani 1 1 d . . .
C32 C 0.7128(3) 0.73597(9) 0.40905(15) 0.0551(7) Uani 1 1 d . . .
H32 H 0.6571 0.7586 0.4250 0.066 Uiso 1 1 calc R . .
C25 C 0.8892(3) 0.66695(8) 0.36563(11) 0.0423(5) Uani 1 1 d . . .
C12 C 0.3435(4) 0.69587(11) 0.50357(16) 0.0670(8) Uani 1 1 d . . .
H12 H 0.2936 0.7164 0.5262 0.080 Uiso 1 1 calc R . .
C20 C 0.2541(3) 0.54281(11) 0.46841(14) 0.0592(7) Uani 1 1 d . . .
H20 H 0.1778 0.5518 0.4906 0.071 Uiso 1 1 calc R . .
C19 C 0.3592(3) 0.57371(9) 0.45363(12) 0.0484(6) Uani 1 1 d . . .
C37 C 0.7583(4) 0.52728(13) 0.25727(16) 0.0773(10) Uani 1 1 d . . .
H37 H 0.7339 0.5239 0.2123 0.093 Uiso 1 1 calc R . .
C38 C 0.8404(4) 0.49485(11) 0.29341(18) 0.0740(9) Uani 1 1 d . . .
H38 H 0.8706 0.4693 0.2730 0.089 Uiso 1 1 calc R . .
C21 C 0.2662(4) 0.49854(11) 0.44928(15) 0.0647(8) Uani 1 1 d . . .
H21 H 0.1970 0.4772 0.4582 0.078 Uiso 1 1 calc R . .
C2 C 0.0479(4) 0.37035(10) 0.34964(15) 0.0623(8) Uani 1 1 d . . .
C34 C 1.3312(5) 0.75116(16) 0.3008(2) 0.1025(14) Uani 1 1 d . . .
H34A H 1.2554 0.7669 0.2715 0.154 Uiso 1 1 calc R . .
H34B H 1.4246 0.7529 0.2848 0.154 Uiso 1 1 calc R . .
H34C H 1.3419 0.7648 0.3432 0.154 Uiso 1 1 calc R . .
C11 C 0.2958(3) 0.65144(11) 0.49946(15) 0.0616(7) Uani 1 1 d . . .
H11 H 0.2131 0.6423 0.5174 0.074 Uiso 1 1 calc R . .
C10 C 0.3746(3) 0.62100(9) 0.46796(12) 0.0477(6) 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
S3 O6 1.428(2) . ?
S3 O5 1.434(2) . ?
S3 O4 1.419(2) . ?
S3 C2 1.800(3) . ?
N9 C18 1.396(3) . ?
N9 C14 1.351(3) . ?
N9 C10 1.385(3) . ?
F1 C2 1.325(4) . ?
F8 C2 1.328(4) . ?
C18 C17 1.364(3) . ?
C18 C24 1.457(3) . ?
C17 C16 1.440(3) . ?
C17 C35 1.489(3) . ?
F7 C2 1.312(4) . ?
C36 C35 1.381(3) . ?
C36 C37 1.389(4) . ?
O33 C28 1.364(4) . ?
O33 C34 1.422(5) . ?
C24 C23 1.395(3) . ?
C24 C19 1.403(4) . ?
C16 C15 1.419(3) . ?
C16 C25 1.453(3) . ?
C14 C15 1.426(4) . ?
C14 C13 1.415(4) . ?
C28 C27 1.384(5) . ?
C28 C29 1.364(5) . ?
C40 C35 1.387(3) . ?
C40 C39 1.374(4) . ?
C15 C32 1.417(3) . ?
C27 C26 1.374(4) . ?
C29 C30 1.405(4) . ?
C22 C23 1.380(4) . ?
C22 C21 1.380(5) . ?
C26 C25 1.405(4) . ?
C39 C38 1.359(5) . ?
C31 C30 1.422(4) . ?
C31 C32 1.338(4) . ?
C13 C12 1.367(4) . ?
C30 C25 1.418(3) . ?
C12 C11 1.380(5) . ?
C20 C19 1.389(4) . ?
C20 C21 1.377(4) . ?
C19 C10 1.431(4) . ?
C37 C38 1.361(5) . ?
C11 C10 1.378(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
O6 S3 O5 114.37(14) . . ?
O6 S3 C2 103.78(14) . . ?
O5 S3 C2 103.72(14) . . ?
O4 S3 O6 115.15(15) . . ?
O4 S3 O5 115.14(15) . . ?
O4 S3 C2 102.37(16) . . ?
C14 N9 C18 124.1(2) . . ?
C14 N9 C10 124.8(2) . . ?
C10 N9 C18 111.1(2) . . ?
N9 C18 C24 105.7(2) . . ?
C17 C18 N9 119.4(2) . . ?
C17 C18 C24 134.9(2) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 C35 114.98(19) . . ?
C16 C17 C35 124.9(2) . . ?
C35 C36 C37 119.4(2) . . ?
C28 O33 C34 118.7(3) . . ?
C23 C24 C18 133.1(2) . . ?
C23 C24 C19 119.0(2) . . ?
C19 C24 C18 107.9(2) . . ?
C17 C16 C25 124.4(2) . . ?
C15 C16 C17 118.1(2) . . ?
C15 C16 C25 117.6(2) . . ?
N9 C14 C15 117.5(2) . . ?
N9 C14 C13 116.0(2) . . ?
C13 C14 C15 126.5(2) . . ?
O33 C28 C27 115.8(3) . . ?
O33 C28 C29 124.1(3) . . ?
C29 C28 C27 120.1(3) . . ?
C39 C40 C35 120.3(2) . . ?
C16 C15 C14 120.5(2) . . ?
C32 C15 C16 121.0(2) . . ?
C32 C15 C14 118.5(2) . . ?
C26 C27 C28 120.9(3) . . ?
C28 C29 C30 119.7(3) . . ?
C23 C22 C21 122.7(3) . . ?
C36 C35 C17 119.3(2) . . ?
C36 C35 C40 119.2(2) . . ?
C40 C35 C17 121.3(2) . . ?
C27 C26 C25 121.4(3) . . ?
C38 C39 C40 120.1(3) . . ?
C22 C23 C24 118.1(3) . . ?
C32 C31 C30 121.3(2) . . ?
C12 C13 C14 119.9(3) . . ?
C29 C30 C31 118.6(3) . . ?
C29 C30 C25 121.4(3) . . ?
C25 C30 C31 120.0(2) . . ?
C31 C32 C15 120.7(3) . . ?
C26 C25 C16 124.7(2) . . ?
C26 C25 C30 116.4(2) . . ?
C30 C25 C16 118.9(2) . . ?
C13 C12 C11 122.6(3) . . ?
C21 C20 C19 118.1(3) . . ?
C24 C19 C10 107.9(2) . . ?
C20 C19 C24 122.1(3) . . ?
C20 C19 C10 130.0(3) . . ?
C38 C37 C36 120.4(3) . . ?
C39 C38 C37 120.6(3) . . ?
C20 C21 C22 120.1(3) . . ?
F1 C2 S3 111.5(2) . . ?
F1 C2 F8 107.7(3) . . ?
F8 C2 S3 111.7(2) . . ?
F7 C2 S3 112.5(3) . . ?
F7 C2 F1 106.9(3) . . ?
F7 C2 F8 106.2(3) . . ?
C10 C11 C12 118.0(3) . . ?
N9 C10 C19 107.3(2) . . ?
C11 C10 N9 118.6(3) . . ?
C11 C10 C19 134.1(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.619
_oxdiff_exptl_absorpt_empirical_full_min 0.586
