Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans
Chang, Meng-Yang; Chen, Kuan-Ting; RSC Advances 13 (2023) 29894–29903; doi:10.1039/D3RA06370D

data_7247513
_publ_section_title
;
 Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              29894
_journal_page_last               29903
_journal_paper_doi               10.1039/D3RA06370D
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C20 H22 O4 S'
_chemical_formula_sum            'C20 H22 O4 S'
_chemical_formula_weight         358.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.892(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4097(3)
_cell_length_b                   9.8815(2)
_cell_length_c                   14.6434(3)
_cell_measurement_reflns_used    13390
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9350
_cell_measurement_theta_min      2.0400
_cell_volume                     1774.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_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    -79.00  36.00   0.50   11.00    --   10.60 -77.00   0.00  230
  2  \w    -79.00  38.00   0.50   11.00    --   10.60 -82.00 -60.00  234
  3  \w    -17.00 100.00   0.50   11.00    --   10.60  82.00  30.00  234
  4  \w    -79.00  41.00   0.50   11.00    --   10.60 -57.00 -30.00  240
  5  \w    -53.00  36.00   0.50   11.00    --   10.60 -77.00 -90.00  178
  6  \w    -18.00   7.00   0.50   11.00    --   10.60  57.00-120.00   50
  7  \w     50.00  85.00   0.50   11.00    --   10.60  57.00-120.00   70
  8  \w     -2.00  78.00   0.50   11.00    --  -10.90  77.00-120.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0204782000
_diffrn_orient_matrix_UB_12      -0.0595180000
_diffrn_orient_matrix_UB_13      0.0182088000
_diffrn_orient_matrix_UB_21      -0.0017083000
_diffrn_orient_matrix_UB_22      0.0337675000
_diffrn_orient_matrix_UB_23      0.0425105000
_diffrn_orient_matrix_UB_31      -0.0541193000
_diffrn_orient_matrix_UB_32      0.0214923000
_diffrn_orient_matrix_UB_33      -0.0162659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.062
_diffrn_reflns_theta_min         2.004
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0406P)^2^+0.7425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3241
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra06370d2.cif
_cod_data_source_block           k10905-myc-d
_cod_database_code               7247513
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 O4 S1'
_diffrn_oxdiff_digest_frames
;
01aeb87c56d10dc0c9f510e92ec437a88400025c263
;
_diffrn_oxdiff_digest_hkl
;
0165852c569663e229b6fa5cc3e27ce42dda8b
;
_reflns_odcompleteness_completeness 99.69
_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:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
2.d X=CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              45909
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.708