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_4035060
_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 H18 F N3 O5 S'
_chemical_formula_sum            'C22 H18 F N3 O5 S'
_chemical_formula_weight         455.45
_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_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9586(2)
_cell_length_b                   15.7174(6)
_cell_length_c                   30.9471(10)
_cell_measurement_reflns_used    8536
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8160
_cell_measurement_theta_min      2.7620
_cell_volume                     3871.1(2)
_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 1.000
_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    -70.00 -12.00   0.50    1.07    --  -41.35 140.00  84.00  116
  2  \w    -65.00 -36.00   0.50    1.07    --  -41.35 -27.00  58.00   58
  3  \w    -36.00 -11.00   0.50    1.07    --  -41.35  27.00-139.00   50
  4  \w     84.00 109.00   0.50    1.07    --   41.35  27.00-139.00   50
  5  \w      0.00  47.00   0.50    1.07    --   41.35 -27.00  58.00   94
  6  \w     40.00  67.00   0.50    1.07    --   41.35-140.00  25.00   54
  7  \w     23.00  58.00   0.50    1.07    --   41.35 -96.00 -88.00   70
  8  \w     50.00  75.00   0.50    1.07    --   41.35-129.00-161.00   50
  9  \w     81.00 106.00   0.50    4.27    --  101.00 -96.00 -88.00   50
 10  \w     46.00  72.00   0.50    4.27    --  101.00 -96.00 -88.00   52
 11  \w    101.00 126.00   0.50    4.27    --  101.00  27.00-139.00   50
 12  \w     44.00 107.00   0.50    4.27    --  101.00 -27.00  58.00  126
 13  \w    113.00 157.00   0.50    4.27    --  101.00  96.00  20.00   88
 14  \w     79.00 154.00   0.50    4.27    --  101.00 140.00  84.00  150
 15  \w   -106.00 -38.00   0.50    1.07    --  -41.35 -32.00   0.00  136
 16  \w    -69.00 -42.00   0.50    1.07    --  -41.35  96.00  20.00   54
 17  \w     52.00  95.00   0.50    1.07    --   41.35  21.00 -30.00   86
 18  \w     33.00  94.00   0.50    1.07    --   41.35  54.00-120.00  122
 19  \w     99.00 157.00   0.50    4.27    --  101.00  25.00-150.00  116
 20  \w     40.00  78.00   0.50    4.27    --  101.00 -87.00-180.00   76
 21  \w     44.00  95.00   0.50    4.27    --  101.00 -33.00 -90.00  102
 22  \w     67.00 105.00   0.50    4.27    --  101.00 -42.00-150.00   76
 23  \w     99.00 124.00   0.50    4.27    --  101.00 -87.00-180.00   50
 24  \w     42.00 119.00   0.50    4.27    --  101.00-133.00 120.00  154
 25  \w    100.00 147.00   0.50    4.27    --  101.00  25.00 -60.00   94
 26  \w     32.00  58.00   0.50    1.07    --   41.35-140.00  25.00   52
;
_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      -0.0509503000
_diffrn_orient_matrix_UB_12      -0.0551974000
_diffrn_orient_matrix_UB_13      -0.0389588000
_diffrn_orient_matrix_UB_21      0.0424046000
_diffrn_orient_matrix_UB_22      -0.0809791000
_diffrn_orient_matrix_UB_23      0.0258928000
_diffrn_orient_matrix_UB_31      -0.1818968000
_diffrn_orient_matrix_UB_32      -0.0033787000
_diffrn_orient_matrix_UB_33      0.0169408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.929
_diffrn_reflns_theta_min         2.856
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33804
_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    1.563
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0538P)^2^+2.5772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3286
_reflns_number_total             3671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01210_si_005.cif
_cod_data_source_block           sav632
_cod_database_code               4035060
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 N3 F1 S1 O6'
_shelx_estimated_absorpt_t_max   0.757
_shelx_estimated_absorpt_t_min   0.719
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C14(H14),
 C11(H11), C12(H12), C22(H22), C13(H13)
;
_shelx_res_checksum              96432
_shelx_hkl_checksum              90705
_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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.465