# 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 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_7680-11822_sp-10
_database_code_depnum_ccdc_archive 'CCDC 1898534'
loop_
_audit_author_name
_audit_author_address
'Olesya V. Khoroshilova'
;Centre for X-ray Diffraction Studies of Research park of St.Petersburg State University
Russia
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-01-30
_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_name_systematic        ?
_chemical_formula_moiety         'C28 H33 N4 O4 S2, B F4'
_chemical_formula_sum            'C28 H33 B F4 N4 O4 S2'
_chemical_formula_weight         640.51
_chemical_melting_point          'decomp. above 215 deg.C'
_chemical_oxdiff_formula         'B F4 N4 S2 O4 C28'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.09480(10)
_cell_length_b                   12.45500(10)
_cell_length_c                   22.3878(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.1510(10)
_cell_angle_gamma                90
_cell_volume                     3069.61(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17650
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      72.6550
_cell_measurement_theta_min      3.9630
_shelx_estimated_absorpt_T_max   0.687
_shelx_estimated_absorpt_T_min   0.489
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29610
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.872
_diffrn_reflns_theta_min         3.980
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  66.00   0.50    0.28    --   38.95 -83.00-130.00   96
  2  ω    -28.00   9.00   0.50    0.28    --   38.95 -83.00-130.00   74
  3  ω     72.00 112.00   0.50    1.11    --  104.92 -83.00-130.00   80
  4  ω     86.00 156.00   0.50    1.11    --  104.92  83.00  -9.00  140
  5  ω    -49.00 -20.00   0.50    0.28    --  -38.95 -21.00  30.00   58
  6  ω    -56.00 -13.00   0.50    0.28    --  -38.95  43.00 -30.00   86
  7  ω    -51.00 -18.00   0.50    0.28    --  -38.95  83.00  -9.00   66
  8  ω     -8.00  29.00   0.50    0.28    --  -38.95  83.00  -9.00   74
  9  ω   -100.00 -57.00   0.50    0.28    --  -38.95 -21.00  30.00   86
 10  ω     -8.00  27.00   0.50    0.28    --  -38.95  43.00 -30.00   70
 11  ω     22.00  61.00   0.50    0.28    --   38.95  21.00 -30.00   78
 12  ω     26.00  52.00   0.50    0.28    --   38.95  32.00 150.00   52
 13  ω     86.00 111.00   0.50    0.28    --   38.95  21.00 -30.00   50
 14  ω    -22.00  51.00   0.50    0.28    --   38.95 -32.00 120.00  146
 15  ω     70.00  96.00   0.50    0.28    --   38.95  65.00   0.00   52
 16  ω     22.00  48.00   0.50    0.28    --   38.95-138.00 -60.00   52
 17  ω     16.00  66.00   0.50    0.28    --   38.95  65.00   0.00  100
 18  ω     79.00 106.00   0.50    0.28    --   38.95  32.00 -60.00   54
 19  ω     76.00 101.00   0.50    0.28    --   38.95  65.00 -30.00   50
 20  ω     26.00  63.00   0.50    0.28    --   38.95  65.00 -30.00   74
 21  ω     37.00  87.00   0.50    0.28    --   38.95  43.00  90.00  100
 22  ω     69.00  94.00   0.50    0.28    --   38.95  32.00 150.00   50
 23  ω     40.00  82.00   0.50    1.11    --  104.92 -61.00 -30.00   84
 24  ω     91.00 157.00   0.50    1.11    --  104.92  22.00 120.00  132
 25  ω     40.00 119.00   0.50    1.11    --  104.92 -45.00  60.00  158
 26  ω     54.00  94.00   0.50    1.11    --  104.92 -61.00 -90.00   80
 27  ω     82.00 114.00   0.50    1.11    --  104.92-111.00 -90.00   64
 28  ω     41.00 109.00   0.50    1.11    --  104.92 -45.00-180.00  136
 29  ω     86.00 157.00   0.50    1.11    --  104.92  53.00 -90.00  142
 30  ω     44.00  78.00   0.50    1.11    --  104.92-111.00 -90.00   68
 31  ω    102.00 157.00   0.50    1.11    --  104.92  45.00 150.00  110
 32  ω     99.00 124.00   0.50    1.11    --  104.92  30.00-150.00   50
 33  ω    121.00 155.00   0.50    1.11    --  104.92 111.00  90.00   68
 34  ω    132.00 157.00   0.50    1.11    --  104.92  93.00 -60.00   50
 35  ω     88.00 154.00   0.50    1.11    --  104.92  61.00  30.00  132
 36  ω     91.00 118.00   0.50    1.11    --  104.92  37.00 -30.00   54
 37  ω     97.00 122.00   0.50    1.11    --  104.92  53.00 -60.00   50
 38  ω     88.00 127.00   0.50    1.11    --  104.92 -61.00 -30.00   78
 39  ω     87.00 144.00   0.50    1.11    --  104.92  22.00 -90.00  114
 40  ω     87.00 117.00   0.50    1.11    --  104.92  93.00 -60.00   60
 41  ω     16.00  41.00   0.50    0.28    --   38.95 -83.00-130.00   50
 42  ω    -20.00  16.00   0.50    0.28    --  -38.95 104.00  90.00   72
 43  ω    -37.00 -11.00   0.50    0.28    --  -38.95  32.00 150.00   52
 44  ω    -76.00 -50.00   0.50    0.28    --  -38.95 104.00  90.00   52
 45  ω     32.00  58.00   0.50    0.28    --   38.95  32.00  90.00   52
 46  ω     13.00  39.00   0.50    0.28    --   38.95 -43.00-120.00   52
 47  ω     13.00  39.00   0.50    0.28    --   38.95-138.00 -60.00   52
 48  ω      9.00  48.00   0.50    0.28    --   38.95 -32.00 -90.00   78
 49  ω     79.00 104.00   0.50    0.28    --   38.95  54.00 150.00   50
 50  ω    -24.00   8.00   0.50    0.28    --   38.95 -43.00-120.00   64
 51  ω     83.00 108.00   0.50    0.28    --   38.95  32.00  90.00   50
 52  ω    -28.00  -2.00   0.50    0.28    --   38.95 -32.00 -90.00   52
 53  ω     48.00  74.00   0.50    0.28    --   38.95-138.00 -60.00   52
 54  ω     39.00  64.00   0.50    0.28    --   38.95  54.00 150.00   50
 55  ω     79.00 105.00   0.50    1.11    --  104.92  77.00  90.00   52
 56  ω     93.00 123.00   0.50    1.11    --  104.92 -86.00 -90.00   60
 57  ω     89.00 114.00   0.50    1.11    --  104.92-111.00 -30.00   50
 58  ω     58.00  84.00   0.50    1.11    --  104.92 -86.00 -90.00   52
 59  ω    101.00 127.00   0.50    1.11    --  104.92  69.00-120.00   52
 60  ω     37.00  64.00   0.50    1.11    --  104.92-111.00 -30.00   54
 61  ω    123.00 157.00   0.50    1.11    --  104.92  69.00 120.00   68
 62  ω     83.00 108.00   0.50    1.11    --  104.92  61.00  90.00   50
 63  ω     34.00  81.00   0.50    1.11    --  104.92   0.00-180.00   94
 64  ω     74.00 124.00   0.50    1.11    --  104.92 -22.00  90.00  100
 65  ω    132.00 157.00   0.50    1.11    --  104.92  69.00-120.00   50
 66  ω     54.00 120.00   0.50    1.11    --  104.92-133.00 -90.00  132
 67  ω     35.00  60.00   0.50    1.11    --  104.92 -22.00  90.00   50
 68  ω     89.00 115.00   0.50    1.11    --  104.92  53.00 120.00   52
 69  ω    119.00 157.00   0.50    1.11    --  104.92  15.00   0.00   76
 70  ω     86.00 120.00   0.50    1.11    --  104.92  53.00  60.00   68
 71  ω     38.00 108.00   0.50    1.11    --  104.92 -37.00 -60.00  140
 72  ω     88.00 128.00   0.50    1.11    --  104.92 -77.00-180.00   80
 73  ω     38.00  64.00   0.50    1.11    --  104.92 -77.00-180.00   52
 74  ω     86.00 136.00   0.50    1.11    --  104.92  93.00 -90.00  100
 75  ω    129.00 157.00   0.50    1.11    --  104.92  77.00  90.00   56
 76  ω     96.00 122.00   0.50    1.11    --  104.92  37.00  90.00   52
 77  ω     36.00  90.50   0.50    1.11    --  104.92 -22.00-180.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0363605000
_diffrn_orient_matrix_UB_12      -0.0371417000
_diffrn_orient_matrix_UB_13      -0.0609089000
_diffrn_orient_matrix_UB_21      -0.0576714000
_diffrn_orient_matrix_UB_22      0.1020909000
_diffrn_orient_matrix_UB_23      -0.0301181000
_diffrn_orient_matrix_UB_31      0.1222136000
_diffrn_orient_matrix_UB_32      0.0591965000
_diffrn_orient_matrix_UB_33      0.0138101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5577
_reflns_number_total             6112
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (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         0.914
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.047
_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)+(0.0800P)²+2.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Ternary CH refined with riding coordinates:
 N1(H1)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3A), C23(H23), C8(H8), C2(H2), C24(H24), C16(H16), C20(H20),
 C27(H27), C26(H26), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C28(H28A,H28B,H28C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.27229(4) 0.26293(4) 0.24336(2) 0.02621(14) Uani 1 1 d . . . . .
S2 S 0.25279(4) 0.49481(4) 0.41131(2) 0.02666(14) Uani 1 1 d . . . . .
O2 O 0.34229(13) 0.17829(11) 0.22051(6) 0.0294(3) Uani 1 1 d . . . . .
O3 O 0.12429(13) 0.48294(12) 0.39568(7) 0.0351(3) Uani 1 1 d . . . . .
O4 O 0.32180(15) 0.41197(12) 0.44429(7) 0.0357(3) Uani 1 1 d . . . . .
O1 O 0.14814(13) 0.24333(13) 0.25073(7) 0.0346(3) Uani 1 1 d . . . . .
F2 F 0.68186(14) 0.52984(12) 0.13343(9) 0.0550(4) Uani 1 1 d . . . . .
F4 F 0.86505(14) 0.47165(15) 0.17610(8) 0.0576(4) Uani 1 1 d . . . . .
N4 N 0.30735(15) 0.50426(13) 0.34593(7) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.267(2) 0.550(2) 0.3240(11) 0.028 Uiso 1 1 d R . . . .
N3 N 0.33802(15) 0.29525(13) 0.31089(7) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.2978 0.3456 0.3257 0.032 Uiso 1 1 d R . . . .
N1 N 0.84892(15) 0.35567(14) 0.35701(8) 0.0300(4) Uani 1 1 d . . . . .
H1 H 0.8660 0.4344 0.3606 0.036 Uiso 1 1 calc R . . . .
F3 F 0.69404(17) 0.39499(19) 0.20302(9) 0.0768(6) Uani 1 1 d . . . . .
N2 N 0.82088(15) 0.55638(14) 0.36712(8) 0.0300(4) Uani 1 1 d . . . . .
F1 F 0.7462(2) 0.36622(14) 0.11078(10) 0.0807(6) Uani 1 1 d . . . . .
C6 C 0.43785(17) 0.51401(15) 0.34756(8) 0.0226(4) Uani 1 1 d . . . . .
C10 C 0.64137(17) 0.43560(15) 0.34781(8) 0.0237(4) Uani 1 1 d . . . . .
C4 C 0.46498(17) 0.31656(15) 0.32258(8) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.51150(16) 0.42151(14) 0.33938(8) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.48900(18) 0.61315(15) 0.35831(9) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.4379 0.6732 0.3624 0.032 Uiso 1 1 calc R . . . .
C15 C 0.27953(18) 0.37679(16) 0.19743(9) 0.0278(4) Uani 1 1 d . . . . .
C9 C 0.68922(17) 0.54140(16) 0.35964(9) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.54259(18) 0.23136(15) 0.31821(9) 0.0266(4) Uani 1 1 d . . . . .
H3A H 0.5101 0.1624 0.3076 0.032 Uiso 1 1 calc R . . . .
C1 C 0.71646(17) 0.34354(16) 0.34343(9) 0.0259(4) Uani 1 1 d . . . . .
C23 C 0.20803(18) 0.70525(16) 0.43145(9) 0.0277(4) Uani 1 1 d . . . . .
H23 H 0.1403 0.6980 0.4013 0.033 Uiso 1 1 calc R . . . .
C8 C 0.61475(18) 0.62816(16) 0.36338(9) 0.0286(4) Uani 1 1 d . . . . .
H8 H 0.6483 0.6981 0.3694 0.034 Uiso 1 1 calc R . . . .
C2 C 0.66855(18) 0.24502(16) 0.32919(9) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.7208 0.1852 0.3267 0.033 Uiso 1 1 calc R . . . .
C24 C 0.2357(2) 0.80358(17) 0.45857(9) 0.0321(4) Uani 1 1 d . . . . .
H24 H 0.1852 0.8637 0.4474 0.038 Uiso 1 1 calc R . . . .
C22 C 0.28123(18) 0.61695(16) 0.44913(9) 0.0274(4) Uani 1 1 d . . . . .
C16 C 0.17291(19) 0.43076(18) 0.17631(10) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.0969 0.4073 0.1869 0.040 Uiso 1 1 calc R . . . .
C20 C 0.39168(18) 0.41189(17) 0.18309(10) 0.0311(4) Uani 1 1 d . . . . .
H20 H 0.4640 0.3746 0.1978 0.037 Uiso 1 1 calc R . . . .
C27 C 0.38087(19) 0.62710(19) 0.49304(9) 0.0347(5) Uani 1 1 d . . . . .
H27 H 0.4298 0.5665 0.5053 0.042 Uiso 1 1 calc R . . . .
C25 C 0.3362(2) 0.81619(18) 0.50199(9) 0.0338(5) Uani 1 1 d . . . . .
C26 C 0.4078(2) 0.7267(2) 0.51868(10) 0.0369(5) Uani 1 1 d . . . . .
H26 H 0.4765 0.7342 0.5483 0.044 Uiso 1 1 calc R . . . .
C18 C 0.2899(2) 0.55616(17) 0.12417(10) 0.0371(5) Uani 1 1 d . . . . .
C17 C 0.1797(2) 0.51945(19) 0.13953(11) 0.0378(5) Uani 1 1 d . . . . .
H17 H 0.1071 0.5561 0.1245 0.045 Uiso 1 1 calc R . . . .
C19 C 0.3962(2) 0.50165(17) 0.14713(11) 0.0359(5) Uani 1 1 d . . . . .
H19 H 0.4726 0.5268 0.1378 0.043 Uiso 1 1 calc R . . . .
C11 C 0.9178(2) 0.3140(2) 0.30934(11) 0.0415(5) Uani 1 1 d . . . . .
H11A H 0.9078 0.2359 0.3063 0.062 Uiso 1 1 calc GR . . . .
H11B H 1.0040 0.3314 0.3194 0.062 Uiso 1 1 calc GR . . . .
H11C H 0.8869 0.3471 0.2707 0.062 Uiso 1 1 calc GR . . . .
C12 C 0.8949(2) 0.3061(2) 0.41641(11) 0.0388(5) Uani 1 1 d . . . . .
H12A H 0.8499 0.3354 0.4477 0.058 Uiso 1 1 calc GR . . . .
H12B H 0.9815 0.3223 0.4264 0.058 Uiso 1 1 calc GR . . . .
H12C H 0.8834 0.2281 0.4141 0.058 Uiso 1 1 calc GR . . . .
C28 C 0.3656(3) 0.9241(2) 0.52997(12) 0.0491(6) Uani 1 1 d . . . . .
H28A H 0.4348 0.9554 0.5129 0.074 Uiso 1 1 calc GR . . . .
H28B H 0.3862 0.9159 0.5736 0.074 Uiso 1 1 calc GR . . . .
H28C H 0.2950 0.9715 0.5217 0.074 Uiso 1 1 calc GR . . . .
C14 C 0.8665(2) 0.6095(2) 0.42602(11) 0.0428(5) Uani 1 1 d . . . . .
H14A H 0.8428 0.6853 0.4245 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.9553 0.6040 0.4331 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.8313 0.5737 0.4588 0.064 Uiso 1 1 calc GR . . . .
C21 C 0.2962(3) 0.6514(2) 0.08325(13) 0.0502(6) Uani 1 1 d . . . . .
H21A H 0.2139 0.6779 0.0703 0.075 Uiso 1 1 calc GR . . . .
H21B H 0.3343 0.6299 0.0479 0.075 Uiso 1 1 calc GR . . . .
H21C H 0.3444 0.7084 0.1049 0.075 Uiso 1 1 calc GR . . . .
C13 C 0.8631(2) 0.6159(2) 0.31661(12) 0.0437(6) Uani 1 1 d . . . . .
H13A H 0.8327 0.5808 0.2786 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.9521 0.6168 0.3214 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.8325 0.6898 0.3164 0.066 Uiso 1 1 calc GR . . . .
B1 B 0.7471(3) 0.4403(2) 0.15659(13) 0.0403(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
S1 O2 1.4405(14) . ?
S1 O1 1.4285(15) . ?
S1 N3 1.6447(17) . ?
S1 C15 1.759(2) . ?
S2 O3 1.4327(16) . ?
S2 O4 1.4336(15) . ?
S2 N4 1.6563(17) . ?
S2 C22 1.751(2) . ?
F2 B1 1.394(3) . ?
F4 B1 1.383(3) . ?
N4 C6 1.449(2) . ?
N3 C4 1.425(2) . ?
N1 C1 1.471(2) . ?
N1 C11 1.481(3) . ?
N1 C12 1.497(3) . ?
F3 B1 1.378(3) . ?
N2 C9 1.461(2) . ?
N2 C14 1.506(3) . ?
N2 C13 1.477(3) . ?
F1 B1 1.379(3) . ?
C6 C5 1.437(2) . ?
C6 C7 1.368(3) . ?
C10 C5 1.440(3) . ?
C10 C9 1.433(3) . ?
C10 C1 1.428(3) . ?
C4 C5 1.438(3) . ?
C4 C3 1.378(3) . ?
C7 C8 1.398(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.394(3) . ?
C9 C8 1.369(3) . ?
C3 C2 1.399(3) . ?
C1 C2 1.359(3) . ?
C23 C24 1.384(3) . ?
C23 C22 1.395(3) . ?
C24 C25 1.394(3) . ?
C22 C27 1.391(3) . ?
C16 C17 1.385(3) . ?
C20 C19 1.382(3) . ?
C27 C26 1.384(3) . ?
C25 C26 1.392(3) . ?
C25 C28 1.502(3) . ?
C18 C17 1.389(3) . ?
C18 C19 1.402(3) . ?
C18 C21 1.505(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
O2 S1 N3 107.98(9) . . ?
O2 S1 C15 108.45(9) . . ?
O1 S1 O2 119.09(9) . . ?
O1 S1 N3 105.03(9) . . ?
O1 S1 C15 108.66(10) . . ?
N3 S1 C15 107.02(9) . . ?
O3 S2 O4 120.20(10) . . ?
O3 S2 N4 104.69(9) . . ?
O3 S2 C22 108.77(9) . . ?
O4 S2 N4 106.01(9) . . ?
O4 S2 C22 108.89(10) . . ?
N4 S2 C22 107.58(9) . . ?
C6 N4 S2 117.24(13) . . ?
C4 N3 S1 121.97(13) . . ?
C1 N1 C11 113.99(17) . . ?
C1 N1 C12 111.25(16) . . ?
C11 N1 C12 110.24(17) . . ?
C9 N2 C14 112.27(16) . . ?
C9 N2 C13 112.59(17) . . ?
C13 N2 C14 110.24(18) . . ?
C5 C6 N4 120.78(16) . . ?
C7 C6 N4 118.13(16) . . ?
C7 C6 C5 121.07(17) . . ?
C9 C10 C5 118.54(16) . . ?
C1 C10 C5 118.41(17) . . ?
C1 C10 C9 123.04(17) . . ?
N3 C4 C5 122.11(16) . . ?
C3 C4 N3 117.11(17) . . ?
C3 C4 C5 120.77(17) . . ?
C6 C5 C10 117.45(16) . . ?
C6 C5 C4 124.80(17) . . ?
C4 C5 C10 117.75(16) . . ?
C6 C7 C8 121.53(17) . . ?
C16 C15 S1 119.30(16) . . ?
C16 C15 C20 121.1(2) . . ?
C20 C15 S1 119.64(16) . . ?
C10 C9 N2 118.72(17) . . ?
C8 C9 N2 119.64(18) . . ?
C8 C9 C10 121.63(18) . . ?
C4 C3 C2 120.89(18) . . ?
C10 C1 N1 118.67(17) . . ?
C2 C1 N1 119.51(17) . . ?
C2 C1 C10 121.78(18) . . ?
C24 C23 C22 118.92(19) . . ?
C9 C8 C7 119.56(18) . . ?
C1 C2 C3 120.26(18) . . ?
C23 C24 C25 121.3(2) . . ?
C23 C22 S2 118.97(15) . . ?
C27 C22 S2 120.04(16) . . ?
C27 C22 C23 120.83(19) . . ?
C17 C16 C15 118.7(2) . . ?
C19 C20 C15 119.1(2) . . ?
C26 C27 C22 119.1(2) . . ?
C24 C25 C28 120.3(2) . . ?
C26 C25 C24 118.5(2) . . ?
C26 C25 C28 121.2(2) . . ?
C27 C26 C25 121.3(2) . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 C21 121.3(2) . . ?
C19 C18 C21 120.3(2) . . ?
C16 C17 C18 121.6(2) . . ?
C20 C19 C18 121.0(2) . . ?
F4 B1 F2 108.6(2) . . ?
F3 B1 F2 110.9(2) . . ?
F3 B1 F4 110.7(2) . . ?
F3 B1 F1 108.8(2) . . ?
F1 B1 F2 107.7(2) . . ?
F1 B1 F4 110.0(2) . . ?

_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.666
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_s51
_database_code_depnum_ccdc_archive 'CCDC 1898535'
loop_
_audit_author_name
_audit_author_address
'Olesya V. Khoroshilova'
;Centre for X-ray Diffraction Studies of Research park of St.Petersburg State University
Russia
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            
'4,5-Bis(dimethylamino)-1,8-bis(p-toluenesulfonamido)naphthalene, zwitterion'
_chemical_melting_point          '219-220 deg.C'
_chemical_formula_moiety         'C28 H32 N4 O4 S2, C2 H3 N'
_chemical_formula_sum            'C30 H35 N5 O4 S2'
_chemical_formula_weight         593.75

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'

_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                   9.6465(18)
_cell_length_b                   16.788(3)
_cell_length_c                   18.275(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.406(3)
_cell_angle_gamma                90
_cell_volume                     2958.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.83

_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68326
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.647
_diffrn_reflns_theta_max         28.873
_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             7756
_reflns_number_gt                6586
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0540P)²+1.8166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7756
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_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 0.01917(3) 0.11827(2) 0.22744(2) 0.02064(9) Uani 1 1 d . . . . .
S2 S 0.46238(4) 0.10847(2) 0.10850(2) 0.01963(9) Uani 1 1 d . . . . .
O1 O 0.00903(12) 0.07519(7) 0.15881(6) 0.0287(2) Uani 1 1 d . . . . .
O2 O -0.09332(11) 0.17292(7) 0.24261(7) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.35723(12) 0.07896(7) 0.05834(6) 0.0273(2) Uani 1 1 d . . . . .
O4 O 0.58947(12) 0.13925(7) 0.07990(6) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.40984(13) 0.33477(7) 0.46601(6) 0.0196(2) Uani 1 1 d . . . . .
H1 H 0.4964 0.3416 0.4497 0.024 Uiso 0.56(3) 1 d R U P A 1
N2 N 0.64196(12) 0.32996(7) 0.40242(6) 0.0195(2) Uani 1 1 d . . . . .
H2 H 0.5762 0.3377 0.4358 0.023 Uiso 0.44(3) 1 d R U P A 2
N3 N 0.16786(12) 0.15850(7) 0.22951(6) 0.0204(2) Uani 1 1 d . . . . .
N4 N 0.38540(12) 0.17796(7) 0.15545(6) 0.0187(2) Uani 1 1 d . . . . .
C1 C 0.34494(14) 0.29316(8) 0.40315(7) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.20763(15) 0.27225(8) 0.40447(8) 0.0213(3) Uani 1 1 d . . . . .
H2A H 0.1536 0.2875 0.4449 0.026 Uiso 1 1 calc R U . . .
C3 C 0.14588(14) 0.22875(8) 0.34704(8) 0.0211(3) Uani 1 1 d . . . . .
H3A H 0.0507 0.2146 0.3496 0.025 Uiso 1 1 calc R U . . .
C4 C 0.22040(13) 0.20556(8) 0.28620(7) 0.0170(2) Uani 1 1 d . . . . .
C5 C 0.36458(13) 0.23102(7) 0.28118(7) 0.0151(2) Uani 1 1 d . . . . .
C6 C 0.44830(14) 0.21497(8) 0.21817(7) 0.0170(2) Uani 1 1 d . . . . .
C7 C 0.58509(14) 0.23856(9) 0.21727(8) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.6377 0.2293 0.1748 0.026 Uiso 1 1 calc R U . . .
C8 C 0.64734(14) 0.27597(9) 0.27804(8) 0.0220(3) Uani 1 1 d . . . . .
H8A H 0.7429 0.2896 0.2772 0.026 Uiso 1 1 calc R U . . .
C9 C 0.57287(14) 0.29314(8) 0.33861(7) 0.0179(2) Uani 1 1 d . . . . .
C10 C 0.42841(13) 0.27345(7) 0.34197(7) 0.0154(2) Uani 1 1 d . . . . .
C11 C 0.35621(16) 0.41699(8) 0.47757(8) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.3737 0.4495 0.4342 0.037 Uiso 1 1 calc R U . . .
H11B H 0.4034 0.4407 0.5204 0.037 Uiso 1 1 calc R U . . .
H11C H 0.2563 0.4148 0.4858 0.037 Uiso 1 1 calc R U . . .
C12 C 0.40566(18) 0.28648(9) 0.53435(8) 0.0291(3) Uani 1 1 d . . . . .
H12A H 0.4428 0.2332 0.5250 0.044 Uiso 1 1 calc R U . . .
H12B H 0.3096 0.2820 0.5501 0.044 Uiso 1 1 calc R U . . .
H12C H 0.4618 0.3125 0.5728 0.044 Uiso 1 1 calc R U . . .
C13 C 0.70407(17) 0.40882(9) 0.38620(9) 0.0269(3) Uani 1 1 d . . . . .
H13A H 0.6335 0.4434 0.3633 0.040 Uiso 1 1 calc R U . . .
H13B H 0.7811 0.4019 0.3528 0.040 Uiso 1 1 calc R U . . .
H13C H 0.7386 0.4332 0.4318 0.040 Uiso 1 1 calc R U . . .
C14 C 0.74681(17) 0.27613(10) 0.43688(9) 0.0302(3) Uani 1 1 d . . . . .
H14A H 0.7033 0.2251 0.4485 0.045 Uiso 1 1 calc R U . . .
H14B H 0.7839 0.3005 0.4820 0.045 Uiso 1 1 calc R U . . .
H14C H 0.8224 0.2673 0.4029 0.045 Uiso 1 1 calc R U . . .
C15 C 0.01651(14) 0.04463(8) 0.29741(8) 0.0209(3) Uani 1 1 d . . . . .
C16 C -0.06272(16) 0.05432(9) 0.35943(8) 0.0245(3) Uani 1 1 d . . . . .
H16A H -0.1131 0.1022 0.3666 0.029 Uiso 1 1 calc R U . . .
C17 C -0.06748(17) -0.00704(9) 0.41114(8) 0.0278(3) Uani 1 1 d . . . . .
H17A H -0.1224 -0.0006 0.4532 0.033 Uiso 1 1 calc R U . . .
C18 C 0.00675(18) -0.07732(9) 0.40210(9) 0.0288(3) Uani 1 1 d . . . . .
C19 C 0.08739(18) -0.08529(9) 0.33985(9) 0.0306(3) Uani 1 1 d . . . . .
H19A H 0.1401 -0.1325 0.3333 0.037 Uiso 1 1 calc R U . . .
C20 C 0.09162(16) -0.02555(9) 0.28768(9) 0.0273(3) Uani 1 1 d . . . . .
H20A H 0.1455 -0.0323 0.2453 0.033 Uiso 1 1 calc R U . . .
C21 C 0.0001(2) -0.14410(10) 0.45752(10) 0.0423(5) Uani 1 1 d . . . . .
H21A H -0.0704 -0.1317 0.4935 0.063 Uiso 1 1 calc R U . . .
H21B H 0.0906 -0.1499 0.4825 0.063 Uiso 1 1 calc R U . . .
H21C H -0.0242 -0.1940 0.4324 0.063 Uiso 1 1 calc R U . . .
C22 C 0.50272(14) 0.03280(8) 0.17234(7) 0.0196(3) Uani 1 1 d . . . . .
C23 C 0.61948(15) 0.03909(9) 0.21869(9) 0.0257(3) Uani 1 1 d . . . . .
H23A H 0.6839 0.0813 0.2131 0.031 Uiso 1 1 calc R U . . .
C24 C 0.63949(17) -0.01788(10) 0.27339(9) 0.0298(3) Uani 1 1 d . . . . .
H24A H 0.7181 -0.0137 0.3055 0.036 Uiso 1 1 calc R U . . .
C25 C 0.54753(17) -0.08061(9) 0.28226(8) 0.0272(3) Uani 1 1 d . . . . .
C26 C 0.43367(17) -0.08671(9) 0.23426(9) 0.0283(3) Uani 1 1 d . . . . .
H26A H 0.3711 -0.1300 0.2388 0.034 Uiso 1 1 calc R U . . .
C27 C 0.41059(16) -0.03023(9) 0.17975(8) 0.0251(3) Uani 1 1 d . . . . .
H27A H 0.3321 -0.0347 0.1476 0.030 Uiso 1 1 calc R U . . .
C28 C 0.5690(2) -0.14013(11) 0.34353(10) 0.0395(4) Uani 1 1 d . . . . .
H28A H 0.6620 -0.1333 0.3654 0.059 Uiso 1 1 calc R U . . .
H28B H 0.5595 -0.1943 0.3240 0.059 Uiso 1 1 calc R U . . .
H28C H 0.4995 -0.1314 0.3809 0.059 Uiso 1 1 calc R U . . .
N1S N 0.6041(2) 0.08622(11) 0.46336(11) 0.0517(4) Uani 1 1 d . . . . .
C1S C 0.3670(2) 0.05508(11) 0.39843(11) 0.0405(4) Uani 1 1 d . . . . .
H1SA H 0.3308 0.0048 0.4173 0.061 Uiso 1 1 calc R U . . .
H1SB H 0.3797 0.0505 0.3456 0.061 Uiso 1 1 calc R U . . .
H1SC H 0.3011 0.0981 0.4081 0.061 Uiso 1 1 calc R U . . .
C2S C 0.4997(2) 0.07287(10) 0.43463(10) 0.0362(4) Uani 1 1 d . . . . .
H4 H 0.303(2) 0.1633(13) 0.1664(12) 0.041(6) Uiso 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 O1 1.4490(12) . ?
S1 O2 1.4530(11) . ?
S1 N3 1.5851(12) . ?
S1 C15 1.7792(15) . ?
S2 O3 1.4384(11) . ?
S2 O4 1.4404(11) . ?
S2 N4 1.6371(12) . ?
S2 C22 1.7618(14) . ?
N1 C1 1.4711(17) . ?
N1 C12 1.4903(18) . ?
N1 C11 1.4910(18) . ?
N1 H1 0.9000 . ?
N2 C9 1.4656(17) . ?
N2 C14 1.4850(19) . ?
N2 C13 1.4860(18) . ?
N2 H2 0.8999 . ?
N3 C4 1.3888(17) . ?
N4 C6 1.4262(17) . ?
N4 H4 0.86(2) . ?
C1 C2 1.3711(19) . ?
C1 C10 1.4326(17) . ?
C2 C3 1.400(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3942(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4601(17) . ?
C5 C10 1.4447(17) . ?
C5 C6 1.4479(17) . ?
C6 C7 1.3781(19) . ?
C7 C8 1.3986(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3651(19) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4349(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.392(2) . ?
C15 C20 1.397(2) . ?
C16 C17 1.399(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.392(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.400(2) . ?
C18 C21 1.513(2) . ?
C19 C20 1.385(2) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.3907(19) . ?
C22 C23 1.397(2) . ?
C23 C24 1.394(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24A 0.9500 . ?
C25 C26 1.392(2) . ?
C25 C28 1.511(2) . ?
C26 C27 1.389(2) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1S C2S 1.147(3) . ?
C1S C2S 1.458(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.45(7) . . ?
O1 S1 N3 105.97(6) . . ?
O2 S1 N3 113.95(7) . . ?
O1 S1 C15 105.87(7) . . ?
O2 S1 C15 106.12(7) . . ?
N3 S1 C15 107.94(6) . . ?
O3 S2 O4 119.04(7) . . ?
O3 S2 N4 104.93(7) . . ?
O4 S2 N4 109.61(6) . . ?
O3 S2 C22 108.34(7) . . ?
O4 S2 C22 108.84(7) . . ?
N4 S2 C22 105.21(6) . . ?
C1 N1 C12 112.11(11) . . ?
C1 N1 C11 114.06(11) . . ?
C12 N1 C11 111.60(11) . . ?
C1 N1 H1 100.5 . . ?
C12 N1 H1 113.0 . . ?
C11 N1 H1 104.9 . . ?
C9 N2 C14 111.87(11) . . ?
C9 N2 C13 113.26(11) . . ?
C14 N2 C13 110.67(12) . . ?
C9 N2 H2 106.6 . . ?
C14 N2 H2 106.5 . . ?
C13 N2 H2 107.5 . . ?
C4 N3 S1 125.00(10) . . ?
C6 N4 S2 122.83(10) . . ?
C6 N4 H4 108.3(15) . . ?
S2 N4 H4 110.6(15) . . ?
C2 C1 C10 121.08(12) . . ?
C2 C1 N1 120.05(12) . . ?
C10 C1 N1 118.85(12) . . ?
C1 C2 C3 120.93(12) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 121.70(12) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
N3 C4 C3 124.61(12) . . ?
N3 C4 C5 116.77(11) . . ?
C3 C4 C5 118.62(12) . . ?
C10 C5 C6 117.90(11) . . ?
C10 C5 C4 118.99(11) . . ?
C6 C5 C4 123.11(11) . . ?
C7 C6 N4 120.28(12) . . ?
C7 C6 C5 120.59(12) . . ?
N4 C6 C5 119.06(12) . . ?
C6 C7 C8 120.81(12) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C9 C8 C7 120.97(13) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 121.13(12) . . ?
C8 C9 N2 119.74(12) . . ?
C10 C9 N2 119.10(11) . . ?
C1 C10 C9 123.04(12) . . ?
C1 C10 C5 118.49(12) . . ?
C9 C10 C5 118.47(11) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.94(14) . . ?
C16 C15 S1 121.46(11) . . ?
C20 C15 S1 118.55(11) . . ?
C15 C16 C17 119.45(14) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C18 C17 C16 121.21(15) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 C19 118.37(14) . . ?
C17 C18 C21 121.20(16) . . ?
C19 C18 C21 120.43(15) . . ?
C20 C19 C18 121.09(15) . . ?
C20 C19 H19A 119.5 . . ?
C18 C19 H19A 119.5 . . ?
C19 C20 C15 119.94(15) . . ?
C19 C20 H20A 120.0 . . ?
C15 C20 H20A 120.0 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 120.41(13) . . ?
C27 C22 S2 118.81(11) . . ?
C23 C22 S2 120.59(11) . . ?
C24 C23 C22 118.60(14) . . ?
C24 C23 H23A 120.7 . . ?
C22 C23 H23A 120.7 . . ?
C25 C24 C23 121.77(14) . . ?
C25 C24 H24A 119.1 . . ?
C23 C24 H24A 119.1 . . ?
C24 C25 C26 118.58(14) . . ?
C24 C25 C28 120.76(15) . . ?
C26 C25 C28 120.65(15) . . ?
C27 C26 C25 120.76(14) . . ?
C27 C26 H26A 119.6 . . ?
C25 C26 H26A 119.6 . . ?
C26 C27 C22 119.84(14) . . ?
C26 C27 H27A 120.1 . . ?
C22 C27 H27A 120.1 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
N1S C2S C1S 179.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N3 C4 -179.92(11) . . . . ?
O2 S1 N3 C4 50.73(14) . . . . ?
C15 S1 N3 C4 -66.87(13) . . . . ?
O3 S2 N4 C6 171.07(11) . . . . ?
O4 S2 N4 C6 -60.00(12) . . . . ?
C22 S2 N4 C6 56.87(12) . . . . ?
C12 N1 C1 C2 61.03(17) . . . . ?
C11 N1 C1 C2 -67.04(16) . . . . ?
C12 N1 C1 C10 -117.46(14) . . . . ?
C11 N1 C1 C10 114.48(14) . . . . ?
C10 C1 C2 C3 2.1(2) . . . . ?
N1 C1 C2 C3 -176.40(12) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
S1 N3 C4 C3 -4.8(2) . . . . ?
S1 N3 C4 C5 174.32(10) . . . . ?
C2 C3 C4 N3 176.06(13) . . . . ?
C2 C3 C4 C5 -3.1(2) . . . . ?
N3 C4 C5 C10 -174.04(11) . . . . ?
C3 C4 C5 C10 5.14(18) . . . . ?
N3 C4 C5 C6 5.20(18) . . . . ?
C3 C4 C5 C6 -175.62(12) . . . . ?
S2 N4 C6 C7 44.04(17) . . . . ?
S2 N4 C6 C5 -139.10(11) . . . . ?
C10 C5 C6 C7 1.02(19) . . . . ?
C4 C5 C6 C7 -178.22(12) . . . . ?
C10 C5 C6 N4 -175.83(11) . . . . ?
C4 C5 C6 N4 4.93(19) . . . . ?
N4 C6 C7 C8 179.05(13) . . . . ?
C5 C6 C7 C8 2.2(2) . . . . ?
C6 C7 C8 C9 -2.8(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 N2 177.97(13) . . . . ?
C14 N2 C9 C8 -65.37(17) . . . . ?
C13 N2 C9 C8 60.54(17) . . . . ?
C14 N2 C9 C10 112.68(14) . . . . ?
C13 N2 C9 C10 -121.41(13) . . . . ?
C2 C1 C10 C9 -179.13(13) . . . . ?
N1 C1 C10 C9 -0.66(19) . . . . ?
C2 C1 C10 C5 0.17(19) . . . . ?
N1 C1 C10 C5 178.64(11) . . . . ?
C8 C9 C10 C1 -177.44(13) . . . . ?
N2 C9 C10 C1 4.54(19) . . . . ?
C8 C9 C10 C5 3.27(19) . . . . ?
N2 C9 C10 C5 -174.75(11) . . . . ?
C6 C5 C10 C1 176.99(11) . . . . ?
C4 C5 C10 C1 -3.73(17) . . . . ?
C6 C5 C10 C9 -3.68(17) . . . . ?
C4 C5 C10 C9 175.59(11) . . . . ?
O1 S1 C15 C16 -136.34(12) . . . . ?
O2 S1 C15 C16 -12.00(14) . . . . ?
N3 S1 C15 C16 110.53(12) . . . . ?
O1 S1 C15 C20 41.01(13) . . . . ?
O2 S1 C15 C20 165.35(11) . . . . ?
N3 S1 C15 C20 -72.12(13) . . . . ?
C20 C15 C16 C17 -0.7(2) . . . . ?
S1 C15 C16 C17 176.58(11) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C16 C17 C18 C21 -179.18(15) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C21 C18 C19 C20 178.27(16) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
S1 C15 C20 C19 -177.55(12) . . . . ?
O3 S2 C22 C27 -17.35(13) . . . . ?
O4 S2 C22 C27 -148.15(11) . . . . ?
N4 S2 C22 C27 94.45(12) . . . . ?
O3 S2 C22 C23 167.62(12) . . . . ?
O4 S2 C22 C23 36.82(14) . . . . ?
N4 S2 C22 C23 -80.59(13) . . . . ?
C27 C22 C23 C24 -1.6(2) . . . . ?
S2 C22 C23 C24 173.40(12) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C23 C24 C25 C28 -178.00(15) . . . . ?
C24 C25 C26 C27 -1.5(2) . . . . ?
C28 C25 C26 C27 177.35(15) . . . . ?
C25 C26 C27 C22 0.7(2) . . . . ?
C23 C22 C27 C26 0.9(2) . . . . ?
S2 C22 C27 C26 -174.12(12) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
