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_4034261
_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         'C23 H17 N O3'
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-11-12 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.990(3)
_cell_angle_beta                 93.798(3)
_cell_angle_gamma                99.922(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6488(3)
_cell_length_b                   9.3013(4)
_cell_length_c                   11.1317(4)
_cell_measurement_reflns_used    4791
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.7680
_cell_measurement_theta_min      3.9230
_cell_volume                     879.19(6)
_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_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.933
_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    -18.00  28.00   0.50    0.69    --  -41.35  23.00-130.00   92
  2  \w    -77.00 -33.00   0.50    0.69    --  -41.35 -23.00  64.00   88
  3  \w     47.00  72.00   0.50    0.69    --   41.35  23.00-130.00   50
  4  \w      3.00  46.00   0.50    0.69    --   41.35 -23.00  64.00   86
  5  \w     54.00  90.00   0.50    2.78    --  100.29 -23.00  64.00   72
  6  \w     99.00 124.00   0.50    2.78    --  100.29  23.00-130.00   50
  7  \w    -26.00   8.00   0.50    0.69    --    8.00 101.00-118.29   68
  8  \w    -13.00  12.00   0.50    0.69    --   24.00 106.00-107.29   50
  9  \w    -10.00  16.00   0.50    0.69    --   24.00 104.00 135.35   52
 10  \w     -1.00  25.00   0.50    0.69    --   28.00  90.00-144.70   52
 11  \w     -3.00  22.00   0.50    0.69    --   28.00  94.00  38.62   50
 12  \w      5.00  30.00   0.50    0.69    --   32.00  86.00 -58.50   50
 13  \w      5.00  30.00   0.50    0.69    --   32.00  86.00 124.23   50
 14  \w      9.00  34.00   0.50    0.69    --   36.00  85.00  17.23   50
 15  \w      9.00  34.00   0.50    0.69    --   36.00  85.00  58.95   50
 16  \w     14.00  42.00   0.50    0.69    --   40.00  82.00 -13.25   56
 17  \w     15.00  40.00   0.50    0.69    --   40.00  79.00 140.62   50
 18  \w     14.00  41.00   0.50    0.69    --   40.00  82.00 -94.27   54
 19  \w    -61.00 -21.00   0.50    0.69    --  -41.35  65.00  30.00   80
 20  \w    -11.00  19.00   0.50    0.69    --  -41.35  65.00  30.00   60
 21  \w    -90.00 -16.00   0.50    0.69    --  -41.35 138.00-150.00  148
 22  \w     16.00  41.00   0.50    0.69    --   41.35  82.00-125.65   50
 23  \w     29.00  79.00   0.50    0.69    --   41.35-138.00  60.00  100
 24  \w    -10.00  75.00   0.50    0.69    --   41.35-104.00 150.00  170
 25  \w     14.00  77.00   0.50    0.69    --   41.35-138.00 150.00  126
 26  \w     19.00  44.00   0.50    0.69    --   44.00  79.00 -98.11   50
 27  \w     19.00  44.00   0.50    0.69    --   44.00  79.00 -37.05   50
 28  \w     19.00  44.00   0.50    0.69    --   44.00  81.00  96.28   50
 29  \w     18.00  43.00   0.50    0.69    --   44.00  82.00  73.86   50
 30  \w     75.00 104.00   0.50    0.69    --   48.00  76.00 138.15   58
 31  \w     26.00  52.00   0.50    0.69    --   48.00  76.00 138.15   52
 32  \w     32.00  58.00   0.50    0.69    --   52.00  75.00   3.75   52
 33  \w     28.00  54.00   0.50    0.69    --   52.00  76.00 -76.89   52
 34  \w     83.00 112.00   0.50    0.69    --   52.00  75.00 101.54   58
 35  \w     32.00  78.00   0.50    0.69    --   52.00  75.00 101.54   92
 36  \w     27.00  53.00   0.50    0.69    --   52.00  76.00-175.11   52
 37  \w     31.00  94.00   0.50    0.69    --   56.00  77.00  35.73  126
 38  \w     86.00 112.00   0.50    0.69    --   56.00  76.00 -41.77   52
 39  \w     31.00  66.00   0.50    0.69    --   56.00  76.00 -41.77   70
 40  \w     37.00  62.00   0.50    0.69    --   56.00  66.00-159.87   50
 41  \w     33.00  59.00   0.50    0.69    --   56.00  77.00-119.92   52
 42  \w     40.00  71.00   0.50    0.69    --   60.00  74.00 149.11   62
 43  \w     98.00 124.00   0.50    0.69    --   60.00  74.00 149.11   52
 44  \w     39.00  80.00   0.50    0.69    --   60.00  76.00  72.40   82
 45  \w     44.00 120.00   0.50    0.69    --   64.00  63.00-144.45  152
 46  \w     81.00 107.00   0.50    0.69    --   68.00  61.00 -77.74   52
 47  \w     50.00  78.00   0.50    0.69    --   68.00  61.00 -77.74   56
 48  \w     45.00 120.00   0.50    0.69    --   68.00  74.00-121.36  150
 49  \w     97.00 128.00   0.50    0.69    --   68.00  62.00  65.75   62
 50  \w     64.00  92.00   0.50    0.69    --   68.00  62.00  65.75   56
 51  \w     48.00  74.00   0.50    2.78    --   72.00  75.00   4.26   52
 52  \w     55.00  99.00   0.50    2.78    --   76.00  69.00 -30.67   88
 53  \w    106.00 140.00   0.50    2.78    --   76.00  69.00 -30.67   68
 54  \w     59.00 107.00   0.50    2.78    --   80.00  71.00 -77.02   96
 55  \w    112.00 139.00   0.50    2.78    --   80.00  75.00  23.17   54
 56  \w     57.00  94.00   0.50    2.78    --   80.00  75.00  23.17   74
 57  \w    113.00 145.00   0.50    2.78    --   80.00  77.00  -4.85   64
 58  \w     55.00  84.00   0.50    2.78    --   80.00  77.00  -4.85   58
 59  \w    116.00 153.00   0.50    2.78    --  100.29  77.00 -30.00   74
 60  \w     77.00 112.00   0.50    2.78    --  100.29  77.00 -30.00   70
 61  \w     35.00  62.00   0.50    2.78    --  100.29 -33.00 -30.00   54
 62  \w    131.00 157.00   0.50    2.78    --  100.29  59.00-180.00   52
 63  \w     83.00 112.00   0.50    2.78    --  100.29  59.00-180.00   58
 64  \w     36.00  87.00   0.50    2.78    --  100.29-117.00-150.00  102
 65  \w    130.00 156.00   0.50    2.78    --  100.29  77.00-120.00   52
 66  \w     75.00 101.00   0.50    2.78    --  100.29  77.00-120.00   52
 67  \w     75.00 122.00   0.50    2.78    --  100.29  77.00-180.00   94
 68  \w     75.00 156.00   0.50    2.78    --  100.29  77.00-150.00  162
 69  \w    121.00 157.00   0.50    2.78    --  100.29  77.00  60.00   72
 70  \w     30.00 109.00   0.50    2.78    --  100.29 -96.00-120.00  158
 71  \w     38.00  94.00   0.50    2.78    --  100.29 -42.00  60.00  112
 72  \w     75.00 100.00   0.50    2.78    --  100.29  77.00  60.00   50
 73  \w     79.00 118.00   0.50    2.78    --  100.29  68.00   0.00   78
 74  \w     80.00 155.00   0.50    2.78    --  100.29  68.00 -90.00  150
 75  \w     88.00 148.00   0.50    2.78    --  100.29  50.00 120.00  120
 76  \w     75.00 100.00   0.50    2.78    --  100.29  77.00 -60.00   50
 77  \w     37.00 109.00   0.50    2.78    --  100.29 -68.00  60.00  144
 78  \w    113.00 157.00   0.50    2.78    --  100.29  77.00  30.00   88
 79  \w     82.00 143.00   0.50    2.78    --  100.29  59.00  30.00  122
 80  \w     75.00 101.00   0.50    2.78    --  100.29  77.00  30.00   52
 81  \w    122.00 148.00   0.50    2.78    --  100.29  59.00 -30.00   52
 82  \w     84.00 117.00   0.50    2.78    --  100.29  59.00 -30.00   66
 83  \w     82.00 148.00   0.50    2.78    --  100.29  59.00 -60.00  132
 84  \w     78.00 107.00   0.50    2.78    --  100.29 -59.00 -60.00   58
 85  \w     80.00 129.00   0.50    2.78    --  100.29  68.00  60.00   98
 86  \w     37.00  73.00   0.50    2.78    --  100.29 -59.00 -60.00   72
 87  \w     42.00  95.00   0.50    2.78    --  100.29 -50.00-150.00  106
 88  \w    120.00 155.00   0.50    2.78    --  100.29  77.00 150.00   70
 89  \w     77.00 103.00   0.50    2.78    --  100.29  77.00 150.00   52
 90  \w     82.00 109.00   0.50    2.78    --  100.29-117.00-180.00   54
 91  \w     83.00 109.00   0.50    2.78    --  100.29 -96.00 -30.00   52
 92  \w     33.00  69.00   0.50    2.78    --  100.29 -96.00 -30.00   72
 93  \w     82.00 136.00   0.50    2.78    --  100.29  59.00 150.00  108
 94  \w    116.00 156.00   0.50    2.78    --  100.29  77.00  90.00   80
 95  \w     91.00 116.00   0.50    2.78    --  100.29-117.00  30.00   50
 96  \w     75.00  97.00   0.50    2.78    --  100.29  77.00  90.00   44
;
_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      -0.1384544000
_diffrn_orient_matrix_UB_12      0.0732595000
_diffrn_orient_matrix_UB_13      0.0348728000
_diffrn_orient_matrix_UB_21      -0.1128514000
_diffrn_orient_matrix_UB_22      -0.1471946000
_diffrn_orient_matrix_UB_23      -0.0225682000
_diffrn_orient_matrix_UB_31      0.0311593000
_diffrn_orient_matrix_UB_32      -0.0360749000
_diffrn_orient_matrix_UB_33      0.1324924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12333
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.012
_diffrn_reflns_theta_min         3.984
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91745
_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            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0635P)^2^+0.2469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2660
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00245_si_005.cif
_cod_data_source_block           10243-zra-794
_cod_database_code               4034261
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C23 H17 N1 O3'
_reflns_odcompleteness_completeness 96.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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:
 C00F(H00B,H00C), C00I(H00F,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R)
;
_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 3.298
_oxdiff_exptl_absorpt_empirical_full_min 0.420