Ring Expansion of 2-Azido-2-phenyl-indan-1,3-dione for the Generation of Heterocyclic Scaffolds.
Mittendorf, Fabia; Mohr, Fabian; Kirsch, Stefan F.; The Journal of organic chemistry 85 (2020) 12760–12769; doi:10.1021/acs.joc.0c01586

data_4038824
_publ_section_title
;
 Ring Expansion of 2-Azido-2-phenyl-indan-1,3-dione for the Generation of
 Heterocyclic Scaffolds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12760
_journal_page_last               12769
_journal_paper_doi               10.1021/acs.joc.0c01586
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C23 H20 N2 O3'
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.273(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0463(10)
_cell_length_b                   12.6415(9)
_cell_length_c                   22.773(2)
_cell_measurement_reflns_used    7287
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2680
_cell_measurement_theta_min      2.6180
_cell_volume                     3623.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2705
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.837
_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    -81.00 -56.00   1.00  117.50    --   -8.50 178.00  90.00   25
  2  \w     33.00  70.00   1.00  117.50    --   15.66-126.00  66.00   37
  3  \w    -17.00  32.00   1.00  117.50    --   15.66 -77.00 150.00   49
  4  \w    -11.00  38.00   1.00  117.50    --   15.66  77.00 -30.00   49
  5  \w    -44.00  82.00   1.00  117.50    --   15.66   0.00 -30.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0254891000
_diffrn_orient_matrix_UB_12      0.0453067000
_diffrn_orient_matrix_UB_13      0.0079752000
_diffrn_orient_matrix_UB_21      -0.0244302000
_diffrn_orient_matrix_UB_22      0.0098298000
_diffrn_orient_matrix_UB_23      -0.0312024000
_diffrn_orient_matrix_UB_31      -0.0440035000
_diffrn_orient_matrix_UB_32      -0.0315575000
_diffrn_orient_matrix_UB_33      0.0018564000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21374
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.587
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         8523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0460P)^2^+0.7553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6449
_reflns_number_total             8523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01586_si_002.cif
_cod_data_source_block           ocmf103
_cod_depositor_comments
'Adding full bibliography for 4038823--4038824.cif.'
_cod_original_cell_volume        3623.1(5)
_cod_database_code               4038824
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C21H20N2O3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.35
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C19(H19), C22(H22), C12(H12), C23(H23), C15(H15), C46(H46),
 C16(H16), C41(H41), C21(H21), C20(H20), C45(H45), C34(H34), C42(H42), C6(H6),
 C38(H38), C26(H26), C36(H36), C35(H35), C37(H37), C29(H29), C3(H3), C5(H5),
 C27(H27), C4(H4), C28(H28)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              25117
_shelx_hkl_checksum              46717
_olex2_date_sample_data_collection 2020-05-26
_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 1.086
_oxdiff_exptl_absorpt_empirical_full_min 0.888