Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates
Luque-Agudo, V.; Albarrán-Velo, J.; Fernández-Bolaños, J. G.; López, O.; Light, M. E.; Padrón, J. M.; Lagunes, I.; Román, E.; Serrano, J. A.; Gil, M. V.; New J. Chem. 41 (2017) 3154–; doi:10.1039/C6NJ03940E

data_7056056
_publ_section_title
;
 Synthesis and antiproliferative activity of sulfa-Michael adducts and
 thiochromenes derived from carbohydrates
;
_journal_issue                   8
_journal_name_full               'New J. Chem.'
_journal_page_first              3154
_journal_paper_doi               10.1039/C6NJ03940E
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 N O12 S'
_chemical_formula_sum            'C24 H27 N O12 S'
_chemical_formula_weight         553.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5095)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.839(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.50613(16)
_cell_length_b                   14.4909(4)
_cell_length_c                   12.0626(3)
_cell_measurement_reflns_used    10597
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.4340
_cell_measurement_theta_min      3.6740
_cell_volume                     1302.72(6)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_detector_type            'Rigaku HG Saturn944+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -63.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   40.0000 -150.0000 136

  2 omega -107.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   60.0000  120.0000 169

  3 omega   33.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   40.0000 -180.0000 39

  4 omega   52.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   40.0000 -120.0000 20

  5 omega   51.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   30.0000   60.0000 20

  6 omega    3.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   30.0000  150.0000 20

  7 omega   38.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   30.0000 -180.0000 21

  8 omega -179.00   -1.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  -60.0000 178

  9 omega -114.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000 -150.0000 114

 10 omega -126.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  -30.0000 126

 11 omega -115.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  -90.0000 115

 12 omega -166.00  -44.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -180.0000 122

 13 omega -135.00   -1.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -120.0000 134

 14 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000    0.0000 20

 15 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000  -30.0000 20

 16 omega  -80.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000  -60.0000 80

 17 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000  -90.0000 20

 18 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -150.0000 20

 19 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000 -120.0000 20

 20 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000 -180.0000 20

 21 omega  -20.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   40.0000 -120.0000 20

 22 omega  -27.00   -7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   40.0000  -90.0000 20

 23 omega -179.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   50.0000    0.0000 179

 24 omega -162.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  -60.0000 162

 25 omega -162.00    0.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000   60.0000 162
;
_diffrn_measurement_device       'three-circle quarter \c goniometer'
_diffrn_measurement_device_type  'Rigaku AFC11 007-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.1976264000
_diffrn_orient_matrix_UB_12      -0.0012095000
_diffrn_orient_matrix_UB_13      0.0230310000
_diffrn_orient_matrix_UB_21      0.0603809000
_diffrn_orient_matrix_UB_22      0.0111432000
_diffrn_orient_matrix_UB_23      0.1258380000
_diffrn_orient_matrix_UB_31      -0.0087323000
_diffrn_orient_matrix_UB_32      0.1056904000
_diffrn_orient_matrix_UB_33      -0.0130065000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18371
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        66.575
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    1.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       fragment
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0373
_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/[\s^2^(Fo^2^)+(0.0466P)^2^+0.6980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                4173
_reflns_number_total             4372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03940e1.cif
_cod_data_source_block           2015acc0017_d_100k
_cod_depositor_comments
'Adding full bibliography for 7056056--7056057.cif.'
_cod_database_code               7056056
_diffrn_measurement_device_type2 'Rigaku AFC11'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.47
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C16(H16), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              10538
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-09-16
_olex2_date_sample_submission    2015-07-23
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id /30
_olex2_submission_special_instructions 'No special instructions were received'