Synthesis of macrocyclic and medium-sized ring thiolactones <i>via</i> the ring expansion of lactams.
Palate, Kleopas Y.; Epton, Ryan G.; Whitwood, Adrian C.; Lynam, Jason M.; Unsworth, William P.; Organic & biomolecular chemistry 19 (2021) 1404–1411; doi:10.1039/d0ob02502j

data_7157849
_publ_section_title
;
 Synthesis of macrocyclic and medium-sized ring thiolactones <i>via</i>
 the ring expansion of lactams.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1404
_journal_page_last               1411
_journal_paper_doi               10.1039/d0ob02502j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C10 H17 N O2 S'
_chemical_formula_sum            'C10 H17 N O2 S'
_chemical_formula_weight         215.30
_chemical_name_systematic        1-thia-5-azacyclododecane-4,12-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc22h5yq
_audit_creation_date             2019-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.03030(10)
_cell_length_b                   9.6259(2)
_cell_length_c                   27.8070(6)
_cell_measurement_reflns_used    3734
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.7430
_cell_measurement_theta_min      6.3530
_cell_volume                     2149.45(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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    -21.00  69.00   1.00    1.00    --    0.00  57.00-180.00   90
  2  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00 150.00   90
  3  \w     33.00 123.00   1.00    2.00    --   54.00  57.00-150.00   90
  4  \w      1.00  96.00   1.00    2.00    --   54.00 -99.00  90.00   95
  5  \w    -15.00  75.00   1.00    2.00    --   54.00 -57.00  90.00   90
  6  \w     33.00 123.00   1.00    2.00    --   54.00  57.00-120.00   90
  7  \w    100.00 178.00   1.00    3.00    --  108.00 111.00 -60.00   78
  8  \w    100.00 178.00   1.00    3.00    --  108.00 111.00  30.00   78
  9  \w    100.00 178.00   1.00    3.00    --  108.00 111.00-180.00   78
 10  \w    100.00 178.00   1.00    3.00    --  108.00 111.00 -30.00   78
 11  \w     36.00 134.00   1.00    3.00    --  108.00 -37.00  30.00   98
 12  \w     36.00 113.00   1.00    3.00    --  108.00-111.00 -30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0160631000
_diffrn_orient_matrix_UB_12      0.0003790000
_diffrn_orient_matrix_UB_13      -0.0552130000
_diffrn_orient_matrix_UB_21      0.0298765000
_diffrn_orient_matrix_UB_22      -0.1580671000
_diffrn_orient_matrix_UB_23      -0.0008317000
_diffrn_orient_matrix_UB_31      -0.1887892000
_diffrn_orient_matrix_UB_32      -0.0250739000
_diffrn_orient_matrix_UB_33      0.0046074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.155
_diffrn_reflns_theta_min         6.365
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method hexane/DCM
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.8694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1860
_reflns_number_total             2044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02502j2.cif
_cod_data_source_block           wpu1902
_cod_depositor_comments
'Adding full bibliography for 7157847--7157849.cif.'
_cod_database_code               7157849
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C10 H17 N O2 S'
_chemical_oxdiff_usercomment     'Kleopas Palate KP151-B'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B)
;
_olex2_date_sample_data_collection 2019-04-25
_olex2_date_sample_submission    2019-04-17
_olex2_exptl_crystal_mounting_method 'oil on micromount'
_olex2_submission_original_sample_id KP151_B
_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 1.416
_oxdiff_exptl_absorpt_empirical_full_min 0.696