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_7157848
_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         'C15 H27 N O2 S'
_chemical_formula_sum            'C15 H27 N O2 S'
_chemical_formula_weight         285.43
_chemical_melting_point          361
_chemical_name_systematic        1-thia-5-azacycloheptadecane-4,17-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc26h4nj
_audit_creation_date             2019-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-23 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.940(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1158(2)
_cell_length_b                   9.9322(3)
_cell_length_c                   34.9595(9)
_cell_measurement_reflns_used    4859
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.8520
_cell_measurement_theta_min      5.5780
_cell_volume                     3161.07(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     -3.00  33.00   1.00    2.50    --    0.00  57.00-150.00   36
  2  \w     26.00  67.00   1.00    2.50    --    0.00  19.00-120.00   41
  3  \w    -36.00  -8.00   1.00    2.50    --    0.00  19.00-120.00   28
  4  \w     31.00 104.00   1.00   10.00    --   54.00-125.00 120.00   73
  5  \w    -15.00  30.00   1.00   10.00    --   54.00 -57.00-150.00   45
  6  \w     23.00  65.00   1.00   10.00    --   54.00-125.00 -30.00   42
  7  \w     39.00 123.00   1.00   10.00    --   54.00  57.00   0.00   84
  8  \w     50.00 104.00   1.00   10.00    --   54.00  57.00 150.00   54
  9  \w    143.00 172.00   1.00   15.00    --  108.00 111.00  60.00   29
 10  \w    102.00 161.00   1.00   15.00    --  108.00  63.00-180.00   59
 11  \w    101.00 137.00   1.00   15.00    --  108.00 111.00  60.00   36
 12  \w     42.00 108.00   1.00   15.00    --  108.00-111.00-180.00   66
 13  \w     38.00  65.00   1.00   15.00    --  108.00-111.00 -90.00   27
 14  \w     84.00 111.00   1.00   15.00    --  108.00-111.00 -90.00   27
 15  \w     71.00 117.00   1.00   15.00    --  108.00 -63.00 120.00   46
 16  \w     78.00 175.00   1.00   15.00    --  108.00  77.00 -60.00   97
 17  \w     39.00 104.00   1.00   15.00    --  108.00-111.00  30.00   65
 18  \w     40.00 134.00   1.00   15.00    --  108.00 -37.00 -30.00   94
 19  \w    -50.00 -25.00   1.00    2.50    --    0.00 -37.00 -30.00   25
 20  \w     60.00  87.00   1.00   10.00    --   54.00  57.00 -60.00   27
 21  \w    100.00 130.00   1.00   15.00    --  108.00 -63.00   0.00   30
;
_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      0.0892375000
_diffrn_orient_matrix_UB_12      -0.0984773000
_diffrn_orient_matrix_UB_13      0.0260552000
_diffrn_orient_matrix_UB_21      -0.0894178000
_diffrn_orient_matrix_UB_22      -0.1187740000
_diffrn_orient_matrix_UB_23      -0.0173562000
_diffrn_orient_matrix_UB_31      0.1125390000
_diffrn_orient_matrix_UB_32      -0.0162931000
_diffrn_orient_matrix_UB_33      -0.0310856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            6764
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.123
_diffrn_reflns_theta_max         67.123
_diffrn_reflns_theta_min         4.629
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane, DCM'
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0089P)^2^+5.9058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6168
_reflns_number_total             6764
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9938\% 
 around [0.98 -0.00 -0.19] (reciprocal) or [1.00 0.00 0.00] (direct)
;
_cod_data_source_file            d0ob02502j2.cif
_cod_data_source_block           wpu1906_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7157847--7157849.cif.'
_cod_original_cell_volume        3161.06(15)
_cod_database_code               7157848
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H27 N1 O2 S1'
_chemical_oxdiff_usercomment     'Kleo Palate KP195_F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6144(11)
 0.3856(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
3.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),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
  C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B),
 C30(H30A,H30B)
;
_shelx_res_checksum              29098
_olex2_date_sample_submission    2019-09-04
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id KP195_F
_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 2.199
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2