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_4034263
_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         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_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             2018-10-30
_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                 93.784(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0927(2)
_cell_length_b                   18.9606(7)
_cell_length_c                   10.0748(2)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      71.6920
_cell_measurement_theta_min      4.6610
_cell_volume                     1733.14(8)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -47.00 -22.00   0.50    3.70    --  -38.95  -5.00 149.00   50
  2  \w   -108.00 -82.00   0.50    3.70    --  -38.95  -5.00 149.00   52
  3  \w    -28.00   1.00   0.50    3.70    --   38.95  -5.00 149.00   58
  4  \w     11.00  60.00   0.50    3.70    --   38.95  -5.00 149.00   98
  5  \w     26.00  52.00   0.50   14.81    --  104.29  -5.00 149.00   52
  6  \w     82.00 151.00   0.50   14.81    --  104.29   5.00 -34.00  138
  7  \w    -77.00 -51.00   0.50    3.70    --  -38.95 104.00-180.00   52
  8  \w   -103.00 -58.00   0.50    3.70    --  -38.95 -65.00  30.00   90
  9  \w    -94.00 -59.00   0.50    3.70    --  -38.95 138.00 -60.00   70
 10  \w    -52.00 -27.00   0.50    3.70    --  -38.95 138.00 -60.00   50
 11  \w    -52.00 -23.00   0.50    3.70    --  -38.95 -65.00  30.00   58
 12  \w      4.00  37.00   0.50    3.70    --  -38.95   5.00 -34.00   66
 13  \w    -25.00  14.00   0.50    3.70    --  -38.95 104.00-180.00   78
 14  \w    -58.00  22.00   0.50    3.70    --  -38.95  77.00 -30.00  160
 15  \w    -50.00  21.00   0.50    3.70    --  -38.95  32.00 -30.00  142
 16  \w     14.00  54.00   0.50    3.70    --   38.95 -54.00  30.00   80
 17  \w     26.00  70.00   0.50    3.70    --   38.95 -89.00-180.00   88
 18  \w    -31.00  19.00   0.50    3.70    --   38.95 -89.00-180.00  100
 19  \w     67.00 115.00   0.50    3.70    --   38.95   5.00 -34.00   96
 20  \w     37.00  88.00   0.50   14.81    --  104.29 -86.00   0.00  102
 21  \w     88.00 114.00   0.50   14.81    --  104.29-133.00-150.00   52
 22  \w     35.00  93.00   0.50   14.81    --  104.29 -30.00-150.00  116
 23  \w    103.00 154.00   0.50   14.81    --  104.29  37.00 -30.00  102
 24  \w     42.00  68.00   0.50   14.81    --  104.29-133.00-150.00   52
 25  \w     36.00 101.00   0.50   14.81    --  104.29 -93.00-150.00  130
 26  \w     43.00 125.00   0.50   14.81    --  104.29 -69.00-150.00  164
 27  \w     68.00 115.00   0.50   14.81    --  104.29-133.00  30.00   94
 28  \w    124.00 157.00   0.50   14.81    --  104.29  22.00  60.00   66
 29  \w     35.00 115.00   0.50   14.81    --  104.29 -30.00 -60.00  160
 30  \w     92.00 120.00   0.50   14.81    --  104.29  22.00  60.00   56
 31  \w     44.00  70.00   0.50   14.81    --  104.29-133.00 120.00   52
 32  \w     97.00 123.00   0.50   14.81    --  104.29-133.00 120.00   52
 33  \w    102.00 127.00   0.50   14.81    --  104.29 -86.00   0.00   50
 34  \w    102.00 150.00   0.50   14.81    --  104.29  30.00   0.00   96
 35  \w     41.00 122.00   0.50   14.81    --  104.29 -45.00-150.00  162
 36  \w     73.00  98.00   0.50   14.81    --  104.29  -5.00 149.00   50
 37  \w    -48.00 -14.00   0.50    3.70    --  -38.95 -77.00 -60.00   68
 38  \w    -54.00 -17.00   0.50    3.70    --  -38.95 -65.00  90.00   74
 39  \w    -47.00 -12.00   0.50    3.70    --  -38.95 -77.00   0.00   70
 40  \w    -39.00 -12.00   0.50    3.70    --  -38.95 -77.00  60.00   54
 41  \w    -78.00 -53.00   0.50    3.70    --  -38.95 -54.00 120.00   50
 42  \w    -46.00 -16.00   0.50    3.70    --  -38.95 -65.00  60.00   60
 43  \w    -40.00 -14.00   0.50    3.70    --  -38.95 -77.00  30.00   52
 44  \w     20.00  46.00   0.50    3.70    --   38.95  21.00  90.00   52
 45  \w     18.00  78.00   0.50    3.70    --   38.95  77.00  90.00  120
 46  \w     13.00  39.00   0.50    3.70    --   38.95  77.00 120.00   52
 47  \w     13.00  39.00   0.50    3.70    --   38.95  78.00 132.66   52
 48  \w     53.00  79.00   0.50    3.70    --   38.95  77.00 120.00   52
 49  \w     18.00  44.00   0.50    3.70    --   38.95 -65.00  30.00   52
 50  \w     17.00  43.00   0.50    3.70    --   38.95  77.00  30.00   52
 51  \w     11.00  36.00   0.50    3.70    --   38.95  82.00  76.76   50
 52  \w     13.00  39.00   0.50    3.70    --   38.95  77.00  60.00   52
 53  \w     47.00  73.00   0.50    3.70    --   38.95  65.00  60.00   52
 54  \w    -17.00   9.00   0.50    3.70    --   38.95 -65.00  30.00   52
 55  \w     16.00  41.00   0.50    3.70    --   38.95  65.00  60.00   50
 56  \w     25.00  50.00   0.50    3.70    --   38.95  65.00-180.00   50
 57  \w     14.00  56.00   0.50    3.70    --   38.95  77.00-180.00   84
 58  \w     33.00  69.00   0.50    3.70    --   38.95  21.00  30.00   72
 59  \w     20.00  46.00   0.50    3.70    --   38.95  54.00 -90.00   52
 60  \w     78.00 104.00   0.50   14.81    --  104.29  75.00 128.14   52
 61  \w     80.00 106.00   0.50   14.81    --  104.29  69.00 120.00   52
 62  \w     78.00 104.00   0.50   14.81    --  104.29  77.00  90.00   52
 63  \w     81.00 109.00   0.50   14.81    --  104.29  69.00  60.00   56
 64  \w     80.00 114.00   0.50   14.81    --  104.29  69.00   0.00   68
 65  \w    132.00 157.00   0.50   14.81    --  104.29  69.00   0.00   50
 66  \w     80.00 105.00   0.50   14.81    --  104.29  70.00 135.71   50
 67  \w     80.00 123.00   0.50   14.81    --  104.29  69.00  90.00   86
 68  \w    132.00 157.00   0.50   14.81    --  104.29  69.00  30.00   50
 69  \w     83.00 117.00   0.50   14.81    --  104.29  61.00 120.00   68
 70  \w     79.00 112.00   0.50   14.81    --  104.29  77.00  30.00   66
 71  \w    132.00 157.00   0.50   14.81    --  104.29  74.00  15.26   50
 72  \w     80.00 105.00   0.50   14.81    --  104.29  69.00  30.00   50
 73  \w     79.00 119.00   0.50   14.81    --  104.29  74.00  15.26   80
 74  \w     80.00 105.00   0.50   14.81    --  104.29  69.00 -30.00   50
 75  \w     78.00 103.00   0.50   14.81    --  104.29  77.00 -30.00   50
 76  \w     80.00 105.00   0.50   14.81    --  104.29  77.00   0.00   50
 77  \w     84.00 109.00   0.50   14.81    --  104.29  53.00   0.00   50
 78  \w     84.00 110.00   0.50   14.81    --  104.29  53.00  60.00   52
 79  \w     86.00 111.00   0.50   14.81    --  104.29  53.00 120.00   50
 80  \w     85.00 111.00   0.50   14.81    --  104.29  61.00  30.00   52
 81  \w    116.00 142.00   0.50   14.81    --  104.29  61.00 150.00   52
 82  \w    120.00 146.00   0.50   14.81    --  104.29  93.00 -90.00   52
 83  \w     84.00 109.00   0.50   14.81    --  104.29  53.00  30.00   50
 84  \w     78.00 104.00   0.50   14.81    --  104.29  77.00 120.00   52
 85  \w    127.00 153.00   0.50   14.81    --  104.29  61.00   0.00   52
 86  \w     83.00 108.00   0.50   14.81    --  104.29  61.00   0.00   50
 87  \w    111.00 138.00   0.50   14.81    --  104.29  61.00  60.00   54
 88  \w    129.00 154.00   0.50   14.81    --  104.29  77.00 150.00   50
 89  \w     78.00 104.00   0.50   14.81    --  104.29  77.00 150.00   52
 90  \w     78.00 104.00   0.50   14.81    --  104.29  77.00  60.00   52
 91  \w    124.00 156.00   0.50   14.81    --  104.29  93.00 -30.00   64
 92  \w     82.00 108.00   0.50   14.81    --  104.29  61.00  90.00   52
 93  \w     82.00 108.00   0.50   14.81    --  104.29  61.00  60.00   52
 94  \w    131.00 157.00   0.50   14.81    --  104.29  61.00 120.00   52
 95  \w     86.00  98.50   0.50   14.81    --  104.29  53.00  90.00   25
;
_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      -0.1654501000
_diffrn_orient_matrix_UB_12      -0.0033546000
_diffrn_orient_matrix_UB_13      -0.0435576000
_diffrn_orient_matrix_UB_21      0.0378105000
_diffrn_orient_matrix_UB_22      -0.0052287000
_diffrn_orient_matrix_UB_23      -0.1464976000
_diffrn_orient_matrix_UB_31      0.0042610000
_diffrn_orient_matrix_UB_32      -0.0810259000
_diffrn_orient_matrix_UB_33      0.0112194000
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.496
_diffrn_reflns_theta_min         4.664
_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    0.759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69963
_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    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.9707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             3422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00245_si_002.cif
_cod_data_source_block           zra-882
_cod_database_code               4034263
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 N O4'
_reflns_odcompleteness_completeness 99.80
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C20(H20), C6(H6), C3(H3), C19(H19), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              53322
_shelx_hkl_checksum              40931
_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 1.802
_oxdiff_exptl_absorpt_empirical_full_min 0.636