Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers.
Guranova, Natalia I.; Dar'in, Dmitry; Kantin, Grigory; Novikov, Alexander S.; Bakulina, Olga; Krasavin, Mikhail; The Journal of organic chemistry 84 (2019) 4534–4542; doi:10.1021/acs.joc.9b00245

data_4034265
_publ_section_title
;
 Rh(II)-Catalyzed Spirocyclization of \a-Diazo Homophthalimides with
 Cyclic Ethers.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4534
_journal_page_last               4542
_journal_paper_doi               10.1021/acs.joc.9b00245
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 F N O3'
_chemical_formula_sum            'C24 H18 F N O3'
_chemical_formula_weight         387.39
_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             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-12 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9068(2)
_cell_length_b                   10.31520(10)
_cell_length_c                   26.2389(4)
_cell_measurement_reflns_used    7545
_cell_measurement_temperature    113.6(3)
_cell_measurement_theta_max      72.2130
_cell_measurement_theta_min      3.4010
_cell_volume                     3721.87(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      113.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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    -21.00  26.00   0.50    0.20    --    0.00  29.00-153.00   94
  2  \w    -58.00  -4.00   0.50    0.20    --    0.00 -29.00  44.00  108
  3  \w   -136.00 -18.00   0.50    0.47    --  -56.30 -29.00  44.00  236
  4  \w    -59.00 -33.00   0.50    0.47    --  -56.30  29.00-153.00   52
  5  \w     11.00  36.00   0.50    0.47    --   56.30 -29.00  44.00   50
  6  \w     42.00  79.00   0.50    0.47    --   56.30  29.00-153.00   74
  7  \w    106.00 154.00   0.50    0.47    --  112.60  29.00-153.00   96
  8  \w     38.00 123.00   0.50    0.47    --  112.60 -29.00  44.00  170
  9  \w     14.00  74.00   0.50    0.20    --    0.00  57.00-150.00  120
 10  \w    -69.00 -36.00   0.50    0.20    --    0.00 178.00-180.00   66
 11  \w    -46.00 -14.00   0.50    0.47    --  -56.30 144.00 120.00   64
 12  \w   -123.00 -91.00   0.50    0.47    --  -56.30 144.00 120.00   64
 13  \w    -91.00  20.00   0.50    0.47    --  -56.30  68.00 -60.00  222
 14  \w    -22.00  84.00   0.50    0.47    --   56.30 -50.00  30.00  212
 15  \w     79.00 133.00   0.50    0.47    --   56.30 117.00 150.00  108
 16  \w     42.00 135.00   0.50    0.47    --   56.30  50.00 -60.00  186
 17  \w     78.00 106.00   0.50    0.47    --   56.30 117.00 120.00   56
 18  \w     69.00 136.00   0.50    0.47    --   56.30 144.00  90.00  134
 19  \w    121.00 146.00   0.50    0.47    --  112.60 -57.00  30.00   50
 20  \w     34.00  96.00   0.50    0.47    --  112.60 -57.00  30.00  124
 21  \w     82.00 111.00   0.50    0.47    --  112.60  57.00-120.00   58
 22  \w     33.00  90.00   0.50    0.47    --  112.60 -63.00 120.00  114
 23  \w     35.00 130.00   0.50    0.47    --  112.60 -44.00-180.00  190
 24  \w     86.00 128.00   0.50    0.47    --  112.60  37.00-120.00   84
 25  \w     76.00 150.00   0.50    0.47    --  112.60 -31.00 150.00  148
 26  \w    112.00 157.00   0.50    0.47    --  112.60  25.00 120.00   90
 27  \w     80.00 130.00   0.50    0.47    --  112.60  57.00   0.00  100
 28  \w     68.00 101.00   0.50    0.47    --  112.60  25.00 120.00   66
 29  \w     69.00  94.00   0.50    0.47    --  112.60 138.00  60.00   50
 30  \w    111.00 157.00   0.50    0.47    --  112.60 138.00  60.00   92
 31  \w     33.00  76.00   0.50    0.47    --  112.60-119.00-150.00   86
 32  \w     30.00 111.00   0.50    0.47    --  112.60-104.00   0.00  162
 33  \w    114.00 139.00   0.50    0.47    --  112.60 -12.00 -90.00   50
 34  \w     27.00  73.00   0.50    0.47    --  112.60 -12.00 -90.00   92
 35  \w     88.00 145.00   0.50    0.47    --  112.60 178.00  90.00  114
 36  \w    127.00 156.00   0.50    0.47    --  112.60  57.00-120.00   58
 37  \w     53.00  79.00   0.50    0.47    --  112.60-104.00 -90.00   52
 38  \w    117.00 142.00   0.50    0.47    --  112.60 -63.00 120.00   50
 39  \w     33.00  88.00   0.50    0.47    --  112.60-119.00   0.00  110
 40  \w     36.00  61.00   0.50    0.47    --  112.60 178.00  90.00   50
 41  \w     40.00  66.00   0.50    0.47    --  112.60 -31.00 150.00   52
 42  \w     29.00  86.00   0.50    0.47    --  112.60-104.00  30.00  114
 43  \w     58.00  84.00   0.50    0.20    --    0.00 178.00-150.00   52
 44  \w    -84.00 -49.00   0.50    0.20    --    0.00-178.00-120.00   70
 45  \w    -53.00 -21.00   0.50    0.47    --  -56.30 -77.00 -90.00   64
 46  \w    -47.00 -20.00   0.50    0.47    --  -56.30 -77.00 -60.00   54
 47  \w    -93.00 -39.00   0.50    0.47    --  -56.30 -77.00-120.00  108
 48  \w    -84.00 -55.00   0.50    0.47    --  -56.30  77.00 150.00   58
 49  \w   -112.00 -86.00   0.50    0.47    --  -56.30 -77.00 -90.00   52
 50  \w    -48.00 -22.00   0.50    0.47    --  -56.30 -77.00 -65.70   52
 51  \w    -50.00 -21.00   0.50    0.47    --  -56.30 -77.00 -30.00   58
 52  \w    -29.00  -3.00   0.50    0.47    --  -56.30  77.00 150.00   52
 53  \w     91.00 117.00   0.50    0.47    --   56.30  77.00 -90.00   52
 54  \w     20.00 104.00   0.50    0.47    --   56.30  77.00 -17.90  168
 55  \w     34.00  67.00   0.50    0.47    --   56.30  50.00 -90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1037897000
_diffrn_orient_matrix_UB_12      -0.0321246000
_diffrn_orient_matrix_UB_13      0.0263446000
_diffrn_orient_matrix_UB_21      -0.0264536000
_diffrn_orient_matrix_UB_22      0.0457931000
_diffrn_orient_matrix_UB_23      0.0520506000
_diffrn_orient_matrix_UB_31      -0.0328404000
_diffrn_orient_matrix_UB_32      -0.1384654000
_diffrn_orient_matrix_UB_33      0.0110963000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19352
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.422
_diffrn_reflns_theta_min         3.406
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0575
_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^)+(0.1001P)^2^+0.7769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6202
_reflns_number_total             7327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00245_si_003.cif
_cod_data_source_block           zra-896
_cod_database_code               4034265
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 F1 N1 O3'
_shelx_estimated_absorpt_t_max   0.855
_shelx_estimated_absorpt_t_min   0.643
_reflns_odcompleteness_completeness 99.75
_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:
 C33(H33A,H33B), C18(H18A,H18B), C41(H41A,H41B), C10(H10A,H10B), C17(H17A,
 H17B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C27(H27), C30(H30), C6(H6), C35(H35), C43(H43), C44(H44), C4(H4),
 C28(H28), C47(H47), C24(H24), C29(H29), C5(H5), C36(H36), C46(H46), C38(H38),
 C20(H20), C15(H15), C37(H37), C23(H23), C12(H12), C21(H21), C13(H13), C14(H14)
;
_shelx_res_checksum              96504
_shelx_hkl_checksum              85174
_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 2.501
_oxdiff_exptl_absorpt_empirical_full_min 0.448