Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE).
Osipyan, Angelina; Sapegin, Alexander; Novikov, Alexander S.; Krasavin, Mikhail; The Journal of organic chemistry 83 (2018) 9707–9717; doi:10.1021/acs.joc.8b01210

data_4035059
_publ_section_title
;
 Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring
 Expansion (HIRE).
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9707
_journal_page_last               9717
_journal_paper_doi               10.1021/acs.joc.8b01210
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H13 N3 O4 S'
_chemical_formula_sum            'C16 H13 N3 O4 S'
_chemical_formula_weight         343.35
_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             2018-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.885(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0862(3)
_cell_length_b                   13.6933(5)
_cell_length_c                   13.5470(4)
_cell_measurement_reflns_used    9228
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3690
_cell_measurement_theta_min      4.5320
_cell_volume                     1489.20(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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 plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_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   -109.00 -33.00   0.50    0.20    --  -41.22 -26.00-157.00  152
  2  \w    -47.00  26.00   0.50    0.20    --  -41.22  26.00   5.00  146
  3  \w     -3.00  46.00   0.50    0.20    --   41.22 -26.00-157.00   98
  4  \w     57.00  83.00   0.50    0.20    --   41.22  26.00   5.00   52
  5  \w     92.00 127.00   0.50    0.20    --  100.29  26.00   5.00   70
  6  \w     36.00 109.00   0.50    0.20    --  100.29 -26.00-157.00  146
  7  \w    -57.00 -19.00   0.50    0.20    --  -41.22  54.00  90.00   76
  8  \w     -4.00  22.00   0.50    0.20    --  -41.22  43.00-150.00   52
  9  \w    -54.00  -6.00   0.50    0.20    --  -41.22  43.00-150.00   96
 10  \w    -22.00  23.00   0.50    0.20    --   41.22 -54.00  60.00   90
 11  \w     26.00  52.00   0.50    0.20    --   41.22 -54.00  60.00   52
 12  \w     67.00  99.00   0.50    0.20    --   41.22  43.00  30.00   64
 13  \w     29.00  60.00   0.50    0.20    --   41.22  43.00  30.00   62
 14  \w    -11.00  32.00   0.50    0.20    --   41.22 -43.00  60.00   86
 15  \w     24.00  56.00   0.50    0.20    --   41.22 -65.00  30.00   64
 16  \w     39.00  64.00   0.50    0.20    --   41.22  32.00 -90.00   50
 17  \w     57.00  82.00   0.50    0.20    --   41.22  32.00 -30.00   50
 18  \w     95.00 155.00   0.50    0.20    --  100.29  42.00  90.00  120
 19  \w     70.00 156.00   0.50    0.20    --  100.29   8.00-150.00  172
 20  \w     69.00 109.00   0.50    0.20    --  100.29 -96.00  30.00   80
 21  \w     88.00 155.00   0.50    0.20    --  100.29  17.00 -90.00  134
 22  \w     32.00 106.00   0.50    0.20    --  100.29 -25.00  60.00  148
 23  \w     40.00  70.00   0.50    0.20    --  100.29 -50.00 120.00   60
 24  \w     50.00  86.00   0.50    0.20    --  100.29-117.00 150.00   72
 25  \w     72.00 108.00   0.50    0.20    --  100.29 -96.00 -30.00   72
 26  \w     38.00 110.00   0.50    0.20    --  100.29 -42.00   0.00  144
 27  \w     41.00  77.00   0.50    0.20    --  100.29-145.00  90.00   72
 28  \w     34.00  60.00   0.50    0.20    --  100.29 -96.00 -30.00   52
 29  \w     87.00 117.00   0.50    0.20    --  100.29 -50.00 120.00   60
 30  \w     42.00  67.00   0.50    0.20    --  100.29 -17.00 -30.00   50
 31  \w     53.00 118.00   0.50    0.20    --  100.29 -68.00   0.00  130
 32  \w     57.00  83.00   0.50    0.20    --   41.22  77.00-180.00   52
 33  \w   -105.00 -41.00   0.50    0.20    --  -41.22 -77.00  30.00  128
 34  \w    -47.00 -19.00   0.50    0.20    --  -41.22 -77.00  90.00   56
 35  \w    -57.00 -28.00   0.50    0.20    --  -41.22 -43.00  90.00   58
 36  \w    -52.00 -26.00   0.50    0.20    --  -41.22 -77.00  60.00   52
 37  \w     21.00  51.00   0.50    0.20    --   41.22  77.00 120.00   60
 38  \w     24.00  65.00   0.50    0.20    --   41.22  56.00 116.35   82
 39  \w     30.00  57.00   0.50    0.20    --   41.22  65.00 150.00   54
 40  \w     17.00  81.00   0.50    0.20    --   41.22  77.00 150.00  128
 41  \w     18.00  45.00   0.50    0.20    --   41.22  77.00  90.00   54
 42  \w     21.00  47.00   0.50    0.20    --   41.22  65.00  90.00   52
 43  \w     60.00  85.00   0.50    0.20    --   41.22  77.00  90.00   50
 44  \w    118.00 144.00   0.50    0.20    --  100.29  25.00 -60.00   52
 45  \w     75.00 101.00   0.50    0.20    --  100.29  77.00  90.00   52
 46  \w     86.00 111.00   0.50    0.20    --  100.29  50.00 120.00   50
 47  \w     87.00 112.00   0.50    0.20    --  100.29  50.00  90.00   50
 48  \w    120.00 156.00   0.50    0.20    --  100.29  25.00 -30.00   72
 49  \w     76.00 102.00   0.50    0.20    --  100.29  77.00  60.00   52
 50  \w    125.00 151.00   0.50    0.20    --  100.29  77.00 150.00   52
 51  \w     55.00 104.00   0.50    0.20    --  100.29 -25.00  30.00   98
 52  \w     84.00 111.00   0.50    0.20    --  100.29  59.00-180.00   54
 53  \w     79.00 127.00   0.50    0.20    --  100.29  68.00 120.00   96
 54  \w     79.00 105.00   0.50    0.20    --  100.29  68.00  60.00   52
 55  \w     64.00  96.00   0.50    0.20    --  100.29 -59.00-180.00   64
 56  \w    127.00 155.00   0.50    0.20    --  100.29  25.00-150.00   56
 57  \w     83.00 119.00   0.50    0.20    --  100.29  59.00  30.00   72
 58  \w     80.00 105.00   0.50    0.20    --  100.29  68.00 150.00   50
 59  \w     82.00 108.00   0.50    0.20    --  100.29  59.00 150.00   52
 60  \w     85.00 112.00   0.50    0.20    --  100.29  50.00-180.00   54
 61  \w     75.00 101.00   0.50    0.20    --  100.29  77.00 120.00   52
 62  \w     83.00 110.00   0.50    0.20    --  100.29  59.00  90.00   54
 63  \w     79.00 106.00   0.50    0.20    --  100.29  68.00  90.00   54
 64  \w     79.00 104.00   0.50    0.20    --  100.29  68.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014386000
_diffrn_orient_matrix_UB_12      0.0091394000
_diffrn_orient_matrix_UB_13      0.1131792000
_diffrn_orient_matrix_UB_21      -0.1805905000
_diffrn_orient_matrix_UB_22      -0.0381123000
_diffrn_orient_matrix_UB_23      -0.0106215000
_diffrn_orient_matrix_UB_31      0.0650706000
_diffrn_orient_matrix_UB_32      -0.1054838000
_diffrn_orient_matrix_UB_33      0.0136160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13637
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.487
_diffrn_reflns_theta_min         4.608
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.531
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0577P)^2^+0.7897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2757
_reflns_number_total             2891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01210_si_003.cif
_cod_data_source_block           9370_sav-373
_cod_database_code               4035059
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.633
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C1(H1), C4(H4), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              11750
_shelx_hkl_checksum              64243
_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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.640