Access to sulfonylated furans or imidazo[1,2-a]pyridines via a metal-free three-component, domino reaction
Cui, Zhiming; Zhu, Baofu; Li, Xuechen; Cao, Hua; Organic Chemistry Frontiers 5 (2018) 2219–; doi:10.1039/C8QO00443A

data_1554344
_publ_section_title
;
 Access to sulfonylated furans or imidazo[1,2-a]pyridines via a metal-free
 three-component, domino reaction
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2219
_journal_paper_doi               10.1039/C8QO00443A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C24 H24 O5 S'
_chemical_formula_sum            'C24 H24 O5 S'
_chemical_formula_weight         424.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                112.533(10)
_cell_angle_beta                 98.978(11)
_cell_angle_gamma                94.422(9)
_cell_formula_units_Z            2
_cell_length_a                   5.5872(7)
_cell_length_b                   13.9109(13)
_cell_length_c                   14.4106(18)
_cell_measurement_reflns_used    2937
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.8810
_cell_measurement_theta_min      2.6420
_cell_volume                     1010.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00  40.00   1.00    4.00    --   11.74 -57.00  90.00  100
  2  \w    -21.00  88.00   1.00    4.00    --   11.74  77.00   0.00  109
  3  \w    -16.00  85.00   1.00    4.00    --   11.74  57.00-120.00  101
  4  \w     34.00  99.00   1.00    4.00    --   11.74-178.00  90.00   65
  5  \w    -16.00   9.00   1.00    4.00    --   11.74  57.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054798000
_diffrn_orient_matrix_UB_12      -0.0515980000
_diffrn_orient_matrix_UB_13      -0.0012348000
_diffrn_orient_matrix_UB_21      -0.0047925000
_diffrn_orient_matrix_UB_22      -0.0206276000
_diffrn_orient_matrix_UB_23      -0.0536499000
_diffrn_orient_matrix_UB_31      0.1297929000
_diffrn_orient_matrix_UB_32      0.0054514000
_diffrn_orient_matrix_UB_33      0.0089492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9360
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.650
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0891P)^2^+0.3972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2897
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00443a2.cif
_cod_data_source_block           e13
_cod_database_code               1554344
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C15(H15), C18(H18), C17(H17), C21(H21), C20(H20), C14(H14),
 C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.807