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_4035057
_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         'C24 H22 N2 O3 S'
_chemical_formula_sum            'C24 H22 N2 O3 S'
_chemical_formula_weight         418.49
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-21
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_cell_angle_alpha                90
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_cell_length_b                   13.77300(10)
_cell_length_c                   17.8139(2)
_cell_measurement_reflns_used    19469
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.7860
_cell_measurement_theta_min      2.9810
_cell_volume                     4146.26(7)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -93.00  -36.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -180.0000 57

  2 omega   47.00   86.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -30.0000 39

  3 omega  -34.00   24.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -38.0000   30.0000 58

  4 omega  -44.00  -18.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000   30.0000 26

  5 omega    9.00   39.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000   30.0000 30

  6 omega   17.00   73.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -60.0000 56

  7 omega  -52.00   30.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000    0.0000 82

  8 omega  -21.00    5.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000 -120.0000 26

  9 omega   40.00   67.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -102.0000  113.0000 27

 10 omega    5.00   75.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 70

 11 omega    2.00   94.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000 -180.0000 92

 12 omega  -93.00    4.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000   90.0000 97

 13 omega  -66.00  -31.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  102.0000 -142.0000 35

 14 omega    2.00   53.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   60.0000 51

 15 omega  -25.00   25.00   1.0000   32.5800
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  150.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_13      -0.0369090000
_diffrn_orient_matrix_UB_21      0.0352669000
_diffrn_orient_matrix_UB_22      0.0250168000
_diffrn_orient_matrix_UB_23      0.0095781000
_diffrn_orient_matrix_UB_31      0.0226419000
_diffrn_orient_matrix_UB_32      -0.0407663000
_diffrn_orient_matrix_UB_33      -0.0114629000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            67167
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
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_exptl_crystal_F_000             1760
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5248
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+2.7200P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01210_si_002.cif
_cod_data_source_block           0103-428-7274_sav953
_cod_database_code               4035057
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C24 H22 N2 O3 S'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C4(H4), C24(H24), C10(H10), C13(H13), C23(H23),
 C12(H12), C11(H11), C20(H20), C22(H22), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
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_shelx_hkl_checksum              61634
_olex2_submission_special_instructions 'No special instructions were received'