# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_c32652p
_database_code_depnum_ccdc_archive 'CCDC 1896798'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica USP Sao Carlos
Brazil
;


_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Carbon nanotube-ruthenium hybrids towards mild oxidation of sulfides to sulfones: Efficient synthesis of sulfonyl compounds with potential biological aplications.'



_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H11 Br O4 S'
_chemical_formula_sum            'C20 H11 Br O4 S'
_chemical_formula_weight         427.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H11 Br O4 S'
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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7841(4)
_cell_length_b                   12.2780(7)
_cell_length_c                   11.6933(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.570(7)
_cell_angle_gamma                90
_cell_volume                     810.52(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2680
_cell_measurement_theta_min      3.5390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4868
_diffrn_reflns_point_group_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.606
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.519
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 113.00   1.00   84.16    --   27.63  54.00-180.00  182
  2  ω     74.00 109.00   1.00   84.16    --   27.63  54.00  60.00   35
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0441141000
_diffrn_orient_matrix_UB_12      0.0336015000
_diffrn_orient_matrix_UB_13      0.0493409000
_diffrn_orient_matrix_UB_21      0.0076835000
_diffrn_orient_matrix_UB_22      0.0444045000
_diffrn_orient_matrix_UB_23      -0.0377644000
_diffrn_orient_matrix_UB_31      -0.1173154000
_diffrn_orient_matrix_UB_32      0.0155584000
_diffrn_orient_matrix_UB_33      0.0015040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.336
_reflns_Friedel_fraction_full    0.475
_reflns_Friedel_fraction_max     0.317
_reflns_number_gt                3388
_reflns_number_total             4171
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.020(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.1062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.92727(6) 0.08392(4) 0.19171(3) 0.05416(12) Uani 1 1 d . . . . .
S002 S 0.55038(13) 0.48201(7) 0.44658(6) 0.03812(16) Uani 1 1 d . . . . .
O003 O 0.2534(4) 0.4970(2) 0.2062(2) 0.0468(5) Uani 1 1 d . . . . .
O004 O 0.3044(4) 0.4770(3) 0.4481(2) 0.0490(6) Uani 1 1 d . . . . .
O005 O 0.7154(5) 0.4776(3) 0.5568(2) 0.0586(7) Uani 1 1 d . . . . .
O006 O 0.3542(7) 0.9171(3) 0.1439(4) 0.0746(9) Uani 1 1 d . . . . .
C007 C 0.2509(5) 0.5954(3) 0.2103(2) 0.0346(5) Uani 1 1 d . . . . .
C008 C 0.6086(5) 0.6061(2) 0.3791(2) 0.0355(6) Uani 1 1 d . . . . .
C009 C 0.4494(5) 0.6562(2) 0.2864(2) 0.0331(5) Uani 1 1 d . . . . .
C00A C 0.0610(6) 0.6592(3) 0.1351(2) 0.0373(6) Uani 1 1 d . . . . .
C00B C 0.8177(6) 0.3895(3) 0.3085(3) 0.0401(6) Uani 1 1 d . . . . .
H00B H 0.8875 0.4577 0.3078 0.048 Uiso 1 1 calc R . . . .
C00C C 0.6303(5) 0.3752(3) 0.3628(3) 0.0348(6) Uani 1 1 d . . . . .
C00D C -0.1498(6) 0.6075(3) 0.0826(3) 0.0461(8) Uani 1 1 d . . . . .
H00D H -0.1730 0.5344 0.0973 0.055 Uiso 1 1 calc R . . . .
C00E C 0.9002(6) 0.3024(3) 0.2556(3) 0.0421(7) Uani 1 1 d . . . . .
H00E H 1.0255 0.3115 0.2183 0.051 Uiso 1 1 calc R . . . .
C00F C 0.7982(5) 0.2020(3) 0.2578(3) 0.0380(6) Uani 1 1 d . . . . .
C00G C 0.6075(6) 0.1865(3) 0.3111(3) 0.0466(7) Uani 1 1 d . . . . .
H00G H 0.5382 0.1182 0.3118 0.056 Uiso 1 1 calc R . . . .
C00H C 0.6957(7) 0.8160(3) 0.3150(3) 0.0502(8) Uani 1 1 d . . . . .
H00H H 0.7224 0.8878 0.2959 0.060 Uiso 1 1 calc R . . . .
C00I C 0.8142(6) 0.6602(3) 0.4329(3) 0.0461(8) Uani 1 1 d . . . . .
H00I H 0.9227 0.6264 0.4927 0.055 Uiso 1 1 calc R . . . .
C00J C 0.4894(6) 0.7637(3) 0.2579(3) 0.0395(6) Uani 1 1 d . . . . .
C00K C 0.8579(7) 0.7642(4) 0.3977(4) 0.0529(9) Uani 1 1 d . . . . .
H00K H 0.9997 0.7987 0.4311 0.063 Uiso 1 1 calc R . . . .
C00L C 0.0946(6) 0.7691(3) 0.1135(3) 0.0424(7) Uani 1 1 d . . . . .
C00M C -0.0841(8) 0.8253(4) 0.0363(3) 0.0549(10) Uani 1 1 d . . . . .
H00M H -0.0624 0.8981 0.0193 0.066 Uiso 1 1 calc R . . . .
C00N C 0.5242(6) 0.2747(3) 0.3626(3) 0.0451(7) Uani 1 1 d . . . . .
H00N H 0.3954 0.2664 0.3976 0.054 Uiso 1 1 calc R . . . .
C00O C 0.3144(7) 0.8240(3) 0.1680(3) 0.0468(7) Uani 1 1 d . . . . .
C00P C -0.2897(8) 0.7741(4) -0.0143(3) 0.0629(12) Uani 1 1 d . . . . .
H00P H -0.4082 0.8125 -0.0648 0.076 Uiso 1 1 calc R . . . .
C00Q C -0.3238(7) 0.6662(4) 0.0085(3) 0.0587(11) Uani 1 1 d . . . . .
H00Q H -0.4655 0.6325 -0.0263 0.070 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
Br01 C00F 1.874(3) . ?
S002 O004 1.428(2) . ?
S002 O005 1.428(2) . ?
S002 C008 1.781(3) . ?
S002 C00C 1.758(3) . ?
O003 C007 1.209(4) . ?
O006 C00O 1.211(5) . ?
C007 C009 1.490(4) . ?
C007 C00A 1.474(4) . ?
C008 C009 1.403(4) . ?
C008 C00I 1.387(4) . ?
C009 C00J 1.393(4) . ?
C00A C00D 1.393(5) . ?
C00A C00L 1.395(5) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.381(4) . ?
C00B C00E 1.372(5) . ?
C00C C00N 1.379(5) . ?
C00D H00D 0.9300 . ?
C00D C00Q 1.380(5) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.369(5) . ?
C00F C00G 1.393(5) . ?
C00G H00G 0.9300 . ?
C00G C00N 1.377(6) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.391(5) . ?
C00H C00K 1.351(6) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.382(6) . ?
C00J C00O 1.488(5) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.397(5) . ?
C00L C00O 1.457(6) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.361(7) . ?
C00N H00N 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.373(8) . ?
C00Q H00Q 0.9300 . ?

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
O004 S002 C008 109.11(16) . . ?
O004 S002 C00C 110.98(16) . . ?
O005 S002 O004 117.36(17) . . ?
O005 S002 C008 106.18(17) . . ?
O005 S002 C00C 105.61(17) . . ?
C00C S002 C008 107.05(14) . . ?
O003 C007 C009 120.6(3) . . ?
O003 C007 C00A 121.4(3) . . ?
C00A C007 C009 117.9(3) . . ?
C009 C008 S002 124.2(2) . . ?
C00I C008 S002 115.8(2) . . ?
C00I C008 C009 119.6(3) . . ?
C008 C009 C007 122.2(3) . . ?
C00J C009 C007 118.6(3) . . ?
C00J C009 C008 119.0(3) . . ?
C00D C00A C007 119.2(3) . . ?
C00D C00A C00L 120.3(3) . . ?
C00L C00A C007 120.5(3) . . ?
C00C C00B H00B 120.2 . . ?
C00E C00B H00B 120.2 . . ?
C00E C00B C00C 119.5(3) . . ?
C00B C00C S002 119.3(3) . . ?
C00N C00C S002 119.8(2) . . ?
C00N C00C C00B 120.5(3) . . ?
C00A C00D H00D 120.4 . . ?
C00Q C00D C00A 119.2(4) . . ?
C00Q C00D H00D 120.4 . . ?
C00B C00E H00E 120.0 . . ?
C00F C00E C00B 120.0(3) . . ?
C00F C00E H00E 120.0 . . ?
C00E C00F Br01 118.5(2) . . ?
C00E C00F C00G 121.3(3) . . ?
C00G C00F Br01 120.3(3) . . ?
C00F C00G H00G 120.8 . . ?
C00N C00G C00F 118.3(3) . . ?
C00N C00G H00G 120.8 . . ?
C00J C00H H00H 119.5 . . ?
C00K C00H H00H 119.5 . . ?
C00K C00H C00J 121.1(4) . . ?
C008 C00I H00I 119.9 . . ?
C00K C00I C008 120.1(3) . . ?
C00K C00I H00I 119.9 . . ?
C009 C00J C00O 121.2(3) . . ?
C00H C00J C009 119.5(3) . . ?
C00H C00J C00O 119.4(3) . . ?
C00H C00K C00I 120.3(3) . . ?
C00H C00K H00K 119.8 . . ?
C00I C00K H00K 119.8 . . ?
C00A C00L C00M 118.8(4) . . ?
C00A C00L C00O 120.7(3) . . ?
C00M C00L C00O 120.5(4) . . ?
C00L C00M H00M 119.8 . . ?
C00P C00M C00L 120.4(4) . . ?
C00P C00M H00M 119.8 . . ?
C00C C00N H00N 119.8 . . ?
C00G C00N C00C 120.5(3) . . ?
C00G C00N H00N 119.8 . . ?
O006 C00O C00J 119.9(4) . . ?
O006 C00O C00L 121.8(4) . . ?
C00L C00O C00J 118.3(3) . . ?
C00M C00P H00P 119.7 . . ?
C00M C00P C00Q 120.6(4) . . ?
C00Q C00P H00P 119.7 . . ?
C00D C00Q H00Q 119.7 . . ?
C00P C00Q C00D 120.6(4) . . ?
C00P C00Q H00Q 119.7 . . ?

_olex2_submission_original_sample_id C32652p
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.873
####################################################################### 
# 
# 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_C3265-2-R
_database_code_depnum_ccdc_archive 'CCDC 1898341'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica USP Sao Carlos
Brazil
;



_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Carbon nanotube-ruthenium hybrids towards mild oxidation of sulfides to sulfones: Efficient synthesis of sulfonyl compounds with potential biological aplications.'


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 Br O2 S'
_chemical_formula_weight         395.26

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'
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'
Br Br -0.2901 2.4595 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0446(8)
_cell_length_b                   9.3059(9)
_cell_length_c                   11.5017(15)
_cell_angle_alpha                106.280(10)
_cell_angle_beta                 102.659(10)
_cell_angle_gamma                90.396(8)
_cell_volume                     804.28(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1973
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      31.6

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.694
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  1.39
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            7235
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         34.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5790
_reflns_number_gt                3064
_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_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'


_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)+(0.0586P)²+0.0697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5790
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Br Br 0.27795(5) 1.12449(5) 0.39348(5) 0.0912(2) Uani 1 1 d . . . . .
S S 0.11510(8) 0.66406(9) 0.68455(7) 0.0508(2) Uani 1 1 d . . . . .
O2 O 0.0465(2) 0.4776(2) 0.8076(2) 0.0529(5) Uani 1 1 d . . . . .
O1 O 0.6602(3) 0.2669(3) 0.9182(3) 0.0756(7) Uani 1 1 d . . . . .
C2 C 0.3292(3) 0.4754(3) 0.7842(2) 0.0372(5) Uani 1 1 d . . . . .
C4 C 0.2175(3) 0.3287(3) 0.9120(2) 0.0400(5) Uani 1 1 d . . . . .
C14 C 0.3079(3) 0.5741(3) 0.7106(2) 0.0406(5) Uani 1 1 d . . . . .
C3 C 0.1878(3) 0.4323(3) 0.8334(2) 0.0386(5) Uani 1 1 d . . . . .
C9 C 0.3774(3) 0.2721(3) 0.9410(2) 0.0410(5) Uani 1 1 d . . . . .
C1 C 0.4888(3) 0.4145(3) 0.8108(2) 0.0402(5) Uani 1 1 d . . . . .
C13 C 0.4431(3) 0.6030(3) 0.6595(3) 0.0493(6) Uani 1 1 d . . . . .
H13 H 0.4288 0.6646 0.6074 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5198(3) 0.3146(3) 0.8921(3) 0.0455(6) Uani 1 1 d . . . . .
C5 C 0.0850(4) 0.2864(3) 0.9586(3) 0.0494(6) Uani 1 1 d . . . . .
H5 H -0.0213 0.3244 0.9414 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1669(3) 0.7900(3) 0.6041(3) 0.0453(6) Uani 1 1 d . . . . .
C8 C 0.4015(4) 0.1755(3) 1.0144(3) 0.0521(7) Uani 1 1 d . . . . .
H8 H 0.5083 0.1395 1.0347 0.063 Uiso 1 1 calc R U . . .
C11 C 0.6213(3) 0.4497(3) 0.7622(3) 0.0500(7) Uani 1 1 d . . . . .
H11 H 0.7269 0.4113 0.7816 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1108(4) 0.1887(4) 1.0299(3) 0.0610(8) Uani 1 1 d . . . . .
H6 H 0.0212 0.1601 1.0597 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1548(4) 0.8498(4) 0.4131(3) 0.0586(8) Uani 1 1 d . . . . .
H17 H 0.1239 0.8228 0.3266 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1224(4) 0.7498(4) 0.4756(3) 0.0541(7) Uani 1 1 d . . . . .
H16 H 0.0704 0.6549 0.4310 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2684(4) 0.1323(4) 1.0577(3) 0.0618(8) Uani 1 1 d . . . . .
H7 H 0.2845 0.0656 1.1055 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5975(4) 0.5407(4) 0.6857(3) 0.0557(7) Uani 1 1 d . . . . .
H12 H 0.6860 0.5609 0.6511 0.067 Uiso 1 1 calc R U . . .
C20 C 0.2421(5) 0.9309(4) 0.6687(3) 0.0631(8) Uani 1 1 d . . . . .
H20 H 0.2703 0.9596 0.7552 0.076 Uiso 1 1 calc R U . . .
C18 C 0.2323(4) 0.9884(4) 0.4788(3) 0.0533(7) Uani 1 1 d . . . . .
C19 C 0.2760(5) 1.0301(4) 0.6065(4) 0.0689(9) Uani 1 1 d . . . . .
H19 H 0.3283 1.1250 0.6507 0.083 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C18 1.884(3) . ?
S C14 1.775(3) . ?
S C15 1.782(3) . ?
O2 C3 1.219(3) . ?
O1 C10 1.223(3) . ?
C2 C14 1.401(3) . ?
C2 C1 1.414(3) . ?
C2 C3 1.476(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.401(3) . ?
C4 C3 1.484(3) . ?
C14 C13 1.401(3) . ?
C9 C8 1.384(4) . ?
C9 C10 1.479(4) . ?
C1 C11 1.382(4) . ?
C1 C10 1.480(4) . ?
C13 C12 1.383(4) . ?
C13 H13 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C15 C20 1.372(4) . ?
C15 C16 1.382(4) . ?
C8 C7 1.377(4) . ?
C8 H8 0.9300 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C17 C18 1.364(5) . ?
C17 C16 1.380(4) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C20 C19 1.375(5) . ?
C20 H20 0.9300 . ?
C18 C19 1.373(5) . ?
C19 H19 0.9300 . ?

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 S C15 101.88(12) . . ?
C14 C2 C1 119.4(2) . . ?
C14 C2 C3 121.3(2) . . ?
C1 C2 C3 119.3(2) . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 119.9(2) . . ?
C9 C4 C3 121.2(2) . . ?
C2 C14 C13 118.8(2) . . ?
C2 C14 S 120.87(18) . . ?
C13 C14 S 120.4(2) . . ?
O2 C3 C2 120.9(2) . . ?
O2 C3 C4 119.9(2) . . ?
C2 C3 C4 119.2(2) . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 C10 120.1(2) . . ?
C4 C9 C10 119.9(2) . . ?
C11 C1 C2 120.2(2) . . ?
C11 C1 C10 118.4(2) . . ?
C2 C1 C10 121.4(2) . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O1 C10 C9 120.2(3) . . ?
O1 C10 C1 120.9(2) . . ?
C9 C10 C1 118.9(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C20 C15 C16 119.2(3) . . ?
C20 C15 S 120.6(2) . . ?
C16 C15 S 120.1(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C12 C11 C1 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C1 C11 H11 119.9 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C15 C20 C19 120.6(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 Br 119.7(2) . . ?
C19 C18 Br 119.7(3) . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_ensj787
_database_code_depnum_ccdc_archive 'CCDC 1896800'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica USP Sao Carlos
Brazil
;


_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

#=====================================================================

_chemical_name_systematic        
'Carbon nanotube-ruthenium hybrids towards mild oxidation of sulfides to sulfones: Efficient synthesis of sulfonyl compounds with potential biological aplications.'





_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_formula_moiety         'C32 H29 B F2 N2 O S2'
_chemical_formula_sum            'C32 H29 B F2 N2 O S2'
_chemical_formula_weight         570.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H29 B F2 N2 O S2'
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'
B B 0.0013 0.0007 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   18.217(3)
_cell_length_b                   7.6976(8)
_cell_length_c                   20.1851(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.631(11)
_cell_angle_gamma                90
_cell_volume                     2798.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1624
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9400
_cell_measurement_theta_min      3.2590
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7979
_diffrn_reflns_point_group_measured_fraction_full 0.537
_diffrn_reflns_point_group_measured_fraction_max 0.461
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.500
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00 118.00   1.00  131.51    --   27.63  54.00   0.00  185
  2  ω    -68.00 -35.00   1.00  131.51    --   27.63  54.00 120.00   33
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0390699000
_diffrn_orient_matrix_UB_12      0.0077837000
_diffrn_orient_matrix_UB_13      -0.0090893000
_diffrn_orient_matrix_UB_21      0.0030563000
_diffrn_orient_matrix_UB_22      -0.0285300000
_diffrn_orient_matrix_UB_23      -0.0328503000
_diffrn_orient_matrix_UB_31      -0.0044425000
_diffrn_orient_matrix_UB_32      -0.0871669000
_diffrn_orient_matrix_UB_33      0.0100178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.043
_reflns_Friedel_fraction_full    0.075
_reflns_Friedel_fraction_max     0.038
_reflns_number_gt                2881
_reflns_number_total             5467
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5467
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0736
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1319P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010),
 C012(H012), C013(H013)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00C,H00D), C00I(H00E,H00F,H00G), C00Y(H00H,H00I,H00J), C011(H01A,
 H01B,H01C), C014(H01D,H01E,H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.47257(7) 0.6615(2) 0.26152(6) 0.0600(4) Uani 1 1 d . . . . .
S002 S 0.42432(7) 0.3415(2) 0.74154(6) 0.0590(4) Uani 1 1 d . . . . .
F003 F 0.3943(3) 0.8062(4) 0.5238(2) 0.0800(11) Uani 1 1 d . . . . .
F004 F 0.3125(2) 0.6051(5) 0.47873(18) 0.0716(9) Uani 1 1 d . . . . .
C005 C 0.4874(3) 0.4800(7) 0.4454(2) 0.0427(10) Uani 1 1 d . . . . .
C006 C 0.4694(3) 0.3924(6) 0.5584(3) 0.0433(10) Uani 1 1 d . . . . .
C007 C 0.5132(3) 0.4850(7) 0.3838(2) 0.0495(12) Uani 1 1 d . . . . .
C008 C 0.4730(3) 0.6150(8) 0.3463(3) 0.0546(14) Uani 1 1 d . . . . .
C009 C 0.6864(4) 0.1158(7) 0.5040(4) 0.0625(15) Uani 1 1 d . . . . .
H009 H 0.737020 0.136837 0.506458 0.075 Uiso 1 1 calc R . . . .
N00A N 0.4326(3) 0.6079(6) 0.4453(2) 0.0507(11) Uani 1 1 d . . . . .
C00B C 0.3078(4) 0.1314(9) 0.6854(3) 0.0655(17) Uani 1 1 d . . . . .
H00B H 0.322502 0.149305 0.643793 0.079 Uiso 1 1 calc R . . . .
O00C O 0.7000(4) -0.1945(6) 0.4976(4) 0.0947(15) Uani 1 1 d . . . . .
C00D C 0.3457(3) 0.2041(8) 0.7415(3) 0.0525(13) Uani 1 1 d . . . . .
N00E N 0.4140(2) 0.5140(7) 0.5583(2) 0.0510(11) Uani 1 1 d . . . . .
C00F C 0.4814(3) 0.3073(8) 0.6203(3) 0.0511(13) Uani 1 1 d . . . . .
C00G C 0.3701(5) 0.8283(9) 0.3662(4) 0.080(2) Uani 1 1 d . . . . .
H00A H 0.380415 0.883553 0.325930 0.121 Uiso 1 1 calc GR . . . .
H00C H 0.373700 0.912182 0.401681 0.121 Uiso 1 1 calc GR . . . .
H00D H 0.320898 0.780394 0.358663 0.121 Uiso 1 1 calc GR . . . .
C00H C 0.5612(3) 0.2253(6) 0.5013(2) 0.0475(10) Uani 1 1 d . . . . .
C00I C 0.5705(4) 0.3749(11) 0.3587(3) 0.0671(17) Uani 1 1 d . . . . .
H00E H 0.617142 0.388317 0.387504 0.101 Uiso 1 1 calc GR . . . .
H00F H 0.575895 0.410179 0.314037 0.101 Uiso 1 1 calc GR . . . .
H00G H 0.555488 0.255340 0.358322 0.101 Uiso 1 1 calc GR . . . .
C00J C 0.5060(3) 0.3723(7) 0.5021(3) 0.0451(11) Uani 1 1 d . . . . .
B00K B 0.3864(4) 0.6388(8) 0.5021(3) 0.0449(13) Uani 1 1 d . . . . .
C00L C 0.4241(4) 0.6886(7) 0.3848(3) 0.0557(14) Uani 1 1 d . . . . .
C00M C 0.5839(4) -0.0794(8) 0.4946(3) 0.0687(15) Uani 1 1 d . . . . .
H00M H 0.565429 -0.192126 0.490337 0.082 Uiso 1 1 calc R . . . .
C00N C 0.5363(4) 0.0574(8) 0.4968(3) 0.0645(14) Uani 1 1 d . . . . .
H00N H 0.485791 0.035720 0.495185 0.077 Uiso 1 1 calc R . . . .
C00O C 0.4289(3) 0.3804(8) 0.6571(3) 0.0513(13) Uani 1 1 d . . . . .
C00P C 0.3882(3) 0.5089(8) 0.6189(3) 0.0528(13) Uani 1 1 d . . . . .
C00Q C 0.2254(4) -0.0049(12) 0.7519(4) 0.082(2) Uani 1 1 d . . . . .
H00Q H 0.184392 -0.074251 0.755443 0.099 Uiso 1 1 calc R . . . .
C00R C 0.2457(4) 0.0286(10) 0.6919(4) 0.079(2) Uani 1 1 d . . . . .
H00R H 0.217825 -0.017727 0.653597 0.095 Uiso 1 1 calc R . . . .
C00S C 0.6360(3) 0.2558(8) 0.5056(3) 0.0560(12) Uani 1 1 d . . . . .
H00S H 0.653755 0.369105 0.509673 0.067 Uiso 1 1 calc R . . . .
C00T C 0.5715(5) 0.8188(11) 0.1959(4) 0.077(2) Uani 1 1 d . . . . .
H00T H 0.543389 0.771731 0.157899 0.092 Uiso 1 1 calc R . . . .
C00U C 0.6596(4) -0.0502(8) 0.4986(3) 0.0634(14) Uani 1 1 d . . . . .
C00V C 0.5519(3) 0.7904(8) 0.2597(3) 0.0518(13) Uani 1 1 d . . . . .
C00W C 0.3255(4) 0.1734(8) 0.8034(3) 0.0581(14) Uani 1 1 d . . . . .
H00W H 0.351272 0.224727 0.841735 0.070 Uiso 1 1 calc R . . . .
C00X C 0.6336(5) 0.9186(10) 0.1911(5) 0.087(2) Uani 1 1 d . . . . .
H00X H 0.647956 0.935551 0.149281 0.105 Uiso 1 1 calc R . . . .
C00Y C 0.3289(4) 0.6173(11) 0.6369(3) 0.0715(18) Uani 1 1 d . . . . .
H00H H 0.334188 0.733347 0.620825 0.107 Uiso 1 1 calc GR . . . .
H00I H 0.331608 0.619264 0.684770 0.107 Uiso 1 1 calc GR . . . .
H00J H 0.281799 0.570942 0.617056 0.107 Uiso 1 1 calc GR . . . .
C00Z C 0.6534(5) 0.9676(11) 0.3081(4) 0.084(2) Uani 1 1 d . . . . .
H00Z H 0.679698 1.020130 0.345864 0.101 Uiso 1 1 calc R . . . .
C010 C 0.2663(4) 0.0647(12) 0.8074(4) 0.083(2) Uani 1 1 d . . . . .
H010 H 0.253852 0.038275 0.849266 0.100 Uiso 1 1 calc R . . . .
C011 C 0.5375(5) 0.1740(9) 0.6458(4) 0.0735(18) Uani 1 1 d . . . . .
H01A H 0.516723 0.060257 0.636877 0.110 Uiso 1 1 calc GR . . . .
H01B H 0.551723 0.188620 0.693196 0.110 Uiso 1 1 calc GR . . . .
H01C H 0.580374 0.186918 0.623743 0.110 Uiso 1 1 calc GR . . . .
C012 C 0.5946(4) 0.8669(10) 0.3149(4) 0.0676(17) Uani 1 1 d . . . . .
H012 H 0.582350 0.847962 0.357398 0.081 Uiso 1 1 calc R . . . .
C013 C 0.6754(5) 0.9947(13) 0.2474(5) 0.086(2) Uani 1 1 d . . . . .
H013 H 0.716973 1.061873 0.243483 0.104 Uiso 1 1 calc R . . . .
C014 C 0.7784(6) -0.1689(14) 0.4901(5) 0.113(3) Uani 1 1 d . . . . .
H01D H 0.781283 -0.115490 0.447627 0.170 Uiso 1 1 calc GR . . . .
H01E H 0.803163 -0.279309 0.492398 0.170 Uiso 1 1 calc GR . . . .
H01F H 0.801815 -0.095313 0.525488 0.170 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C008 1.747(6) . ?
S001 C00V 1.758(6) . ?
S002 C00D 1.780(6) . ?
S002 C00O 1.744(5) . ?
F003 B00K 1.362(7) . ?
F004 B00K 1.383(8) . ?
C005 C007 1.394(7) . ?
C005 N00A 1.402(7) . ?
C005 C00J 1.412(7) . ?
C006 N00E 1.377(7) . ?
C006 C00F 1.399(8) . ?
C006 C00J 1.409(7) . ?
C007 C008 1.395(9) . ?
C007 C00I 1.491(9) . ?
C008 C00L 1.389(9) . ?
C009 H009 0.9300 . ?
C009 C00S 1.420(8) . ?
C009 C00U 1.367(8) . ?
N00A B00K 1.538(8) . ?
N00A C00L 1.358(8) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.355(9) . ?
C00B C00R 1.402(9) . ?
O00C C00U 1.336(8) . ?
O00C C014 1.470(13) . ?
C00D C00W 1.376(8) . ?
N00E B00K 1.514(8) . ?
N00E C00P 1.374(6) . ?
C00F C00O 1.413(8) . ?
C00F C011 1.485(9) . ?
C00G H00A 0.9600 . ?
C00G H00C 0.9600 . ?
C00G H00D 0.9600 . ?
C00G C00L 1.467(10) . ?
C00H C00J 1.515(8) . ?
C00H C00N 1.369(8) . ?
C00H C00S 1.371(7) . ?
C00I H00E 0.9600 . ?
C00I H00F 0.9600 . ?
C00I H00G 0.9600 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.369(9) . ?
C00M C00U 1.387(10) . ?
C00N H00N 0.9300 . ?
C00O C00P 1.398(8) . ?
C00P C00Y 1.454(9) . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.344(11) . ?
C00Q C010 1.357(12) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00T C00V 1.402(9) . ?
C00T C00X 1.384(12) . ?
C00V C012 1.391(10) . ?
C00W H00W 0.9300 . ?
C00W C010 1.377(10) . ?
C00X H00X 0.9300 . ?
C00X C013 1.398(14) . ?
C00Y H00H 0.9600 . ?
C00Y H00I 0.9600 . ?
C00Y H00J 0.9600 . ?
C00Z H00Z 0.9300 . ?
C00Z C012 1.345(10) . ?
C00Z C013 1.361(12) . ?
C010 H010 0.9300 . ?
C011 H01A 0.9600 . ?
C011 H01B 0.9600 . ?
C011 H01C 0.9600 . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C014 H01D 0.9600 . ?
C014 H01E 0.9600 . ?
C014 H01F 0.9600 . ?

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
C008 S001 C00V 104.7(3) . . ?
C00O S002 C00D 105.0(3) . . ?
C007 C005 N00A 108.4(4) . . ?
C007 C005 C00J 131.8(5) . . ?
N00A C005 C00J 119.8(4) . . ?
N00E C006 C00F 109.5(4) . . ?
N00E C006 C00J 120.7(5) . . ?
C00F C006 C00J 129.8(5) . . ?
C005 C007 C008 106.5(5) . . ?
C005 C007 C00I 129.4(5) . . ?
C008 C007 C00I 124.1(5) . . ?
C007 C008 S001 127.1(5) . . ?
C00L C008 S001 123.8(5) . . ?
C00L C008 C007 108.5(5) . . ?
C00S C009 H009 120.5 . . ?
C00U C009 H009 120.5 . . ?
C00U C009 C00S 119.1(6) . . ?
C005 N00A B00K 125.2(4) . . ?
C00L N00A C005 107.9(5) . . ?
C00L N00A B00K 126.7(5) . . ?
C00D C00B H00B 120.9 . . ?
C00D C00B C00R 118.2(6) . . ?
C00R C00B H00B 120.9 . . ?
C00U O00C C014 115.9(6) . . ?
C00B C00D S002 123.7(5) . . ?
C00B C00D C00W 121.0(6) . . ?
C00W C00D S002 115.3(5) . . ?
C006 N00E B00K 126.3(4) . . ?
C00P N00E C006 109.2(5) . . ?
C00P N00E B00K 124.5(5) . . ?
C006 C00F C00O 104.9(5) . . ?
C006 C00F C011 129.8(5) . . ?
C00O C00F C011 125.3(5) . . ?
H00A C00G H00C 109.5 . . ?
H00A C00G H00D 109.5 . . ?
H00C C00G H00D 109.5 . . ?
C00L C00G H00A 109.5 . . ?
C00L C00G H00C 109.5 . . ?
C00L C00G H00D 109.5 . . ?
C00N C00H C00J 119.4(5) . . ?
C00N C00H C00S 118.8(5) . . ?
C00S C00H C00J 121.8(5) . . ?
C007 C00I H00E 109.5 . . ?
C007 C00I H00F 109.5 . . ?
C007 C00I H00G 109.5 . . ?
H00E C00I H00F 109.5 . . ?
H00E C00I H00G 109.5 . . ?
H00F C00I H00G 109.5 . . ?
C005 C00J C00H 120.6(4) . . ?
C006 C00J C005 120.3(5) . . ?
C006 C00J C00H 119.0(5) . . ?
F003 B00K F004 109.7(5) . . ?
F003 B00K N00A 110.1(5) . . ?
F003 B00K N00E 110.6(5) . . ?
F004 B00K N00A 109.3(5) . . ?
F004 B00K N00E 109.4(5) . . ?
N00E B00K N00A 107.7(5) . . ?
C008 C00L C00G 128.1(6) . . ?
N00A C00L C008 108.7(5) . . ?
N00A C00L C00G 123.2(6) . . ?
C00N C00M H00M 119.9 . . ?
C00N C00M C00U 120.2(6) . . ?
C00U C00M H00M 119.9 . . ?
C00H C00N C00M 121.5(6) . . ?
C00H C00N H00N 119.2 . . ?
C00M C00N H00N 119.2 . . ?
C00F C00O S002 125.6(5) . . ?
C00P C00O S002 124.2(4) . . ?
C00P C00O C00F 109.6(5) . . ?
N00E C00P C00O 106.7(5) . . ?
N00E C00P C00Y 124.9(5) . . ?
C00O C00P C00Y 128.4(5) . . ?
C00R C00Q H00Q 120.8 . . ?
C00R C00Q C010 118.5(7) . . ?
C010 C00Q H00Q 120.8 . . ?
C00B C00R H00R 119.1 . . ?
C00Q C00R C00B 121.8(7) . . ?
C00Q C00R H00R 119.1 . . ?
C009 C00S H00S 119.7 . . ?
C00H C00S C009 120.6(5) . . ?
C00H C00S H00S 119.7 . . ?
C00V C00T H00T 120.8 . . ?
C00X C00T H00T 120.8 . . ?
C00X C00T C00V 118.3(8) . . ?
C009 C00U C00M 119.8(6) . . ?
O00C C00U C009 126.0(7) . . ?
O00C C00U C00M 114.2(6) . . ?
C00T C00V S001 115.5(6) . . ?
C012 C00V S001 125.8(4) . . ?
C012 C00V C00T 118.7(7) . . ?
C00D C00W H00W 120.8 . . ?
C00D C00W C010 118.4(7) . . ?
C010 C00W H00W 120.8 . . ?
C00T C00X H00X 119.1 . . ?
C00T C00X C013 121.8(7) . . ?
C013 C00X H00X 119.1 . . ?
C00P C00Y H00H 109.5 . . ?
C00P C00Y H00I 109.5 . . ?
C00P C00Y H00J 109.5 . . ?
H00H C00Y H00I 109.5 . . ?
H00H C00Y H00J 109.5 . . ?
H00I C00Y H00J 109.5 . . ?
C012 C00Z H00Z 119.1 . . ?
C012 C00Z C013 121.8(9) . . ?
C013 C00Z H00Z 119.1 . . ?
C00Q C010 C00W 122.0(7) . . ?
C00Q C010 H010 119.0 . . ?
C00W C010 H010 119.0 . . ?
C00F C011 H01A 109.5 . . ?
C00F C011 H01B 109.5 . . ?
C00F C011 H01C 109.5 . . ?
H01A C011 H01B 109.5 . . ?
H01A C011 H01C 109.5 . . ?
H01B C011 H01C 109.5 . . ?
C00V C012 H012 119.3 . . ?
C00Z C012 C00V 121.3(7) . . ?
C00Z C012 H012 119.3 . . ?
C00X C013 H013 121.0 . . ?
C00Z C013 C00X 118.0(8) . . ?
C00Z C013 H013 121.0 . . ?
O00C C014 H01D 109.5 . . ?
O00C C014 H01E 109.5 . . ?
O00C C014 H01F 109.5 . . ?
H01D C014 H01E 109.5 . . ?
H01D C014 H01F 109.5 . . ?
H01E C014 H01F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.763
_oxdiff_exptl_absorpt_empirical_full_min 0.686
