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_4035058
_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         'C22 H19 N2.98 O4 S'
_chemical_formula_sum            'C22 H19 N3 O4 S'
_chemical_formula_weight         421.46
_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   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_length_c                   14.8908(5)
_cell_measurement_reflns_used    3144
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.7060
_cell_measurement_theta_min      3.2410
_cell_volume                     1898.74(12)
_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)
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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
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  1 omega  -63.00  -37.00   1.0000   12.3100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -120.0000 26

  2 omega    1.00   88.00   1.0000   12.3100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  -60.0000 87

  3 omega   45.00   82.00   1.0000   12.3100
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -142.0000 -139.0000 37

  4 omega    2.00   96.00   1.0000   12.3100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000 -150.0000 94

  5 omega  -81.00  -56.00   1.0000   12.3100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      0.0177734000
_diffrn_orient_matrix_UB_12      0.0154035000
_diffrn_orient_matrix_UB_13      -0.0383544000
_diffrn_orient_matrix_UB_21      0.0442072000
_diffrn_orient_matrix_UB_22      -0.0105608000
_diffrn_orient_matrix_UB_23      0.0291497000
_diffrn_orient_matrix_UB_31      -0.0023697000
_diffrn_orient_matrix_UB_32      -0.0805753000
_diffrn_orient_matrix_UB_33      -0.0111472000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10617
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.492
_diffrn_reflns_theta_min         2.739
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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_density_diffrn    1.474
_exptl_crystal_description
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_exptl_crystal_F_000             880
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0400P)^2^+0.9630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                4016
_reflns_number_total             4805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01210_si_004.cif
_cod_data_source_block           1103-428-7359_sav-965
_cod_database_code               4035058
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C22 H19 N3 O4 S'
_reflns_odcompleteness_completeness 99.86
_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
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C21(H21), C18(H18), C19(H19), C1(H1), C13(H13), C11(H11), C10(H10),
 C3(H3), C5(H5), C12(H12), C4(H4), C2(H2A)
;
_shelx_res_checksum              7686
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_olex2_submission_special_instructions 'No special instructions were received'