A Rh(ii)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition.
Yin, Xinru; Xu, Aimin; Hu, Jidi; Bao, Ming; Hu, Wenhao; Qian, Yu; Organic & biomolecular chemistry 18 (2020) 9805–9809; doi:10.1039/d0ob02189j

data_7157764
_publ_section_title
;
 A Rh(ii)/phosphoric acid co-catalyzed three-component reaction of
 diazo-ketones with alcohols and azonaphthalenes: access to indole
 derivatives via a formal [3 + 2]-cycloaddition.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9805
_journal_page_last               9809
_journal_paper_doi               10.1039/d0ob02189j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C28 H26 N2 O4'
_chemical_formula_sum            'C30 H26 N0.25 O4'
_chemical_formula_weight         454.01
_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_block_doi                 10.5517/ccdc.csd.cc23z7dr
_audit_creation_date             2019-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-13 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.58250(10)
_cell_length_b                   10.9351(2)
_cell_length_c                   20.5330(3)
_cell_measurement_reflns_used    10266
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8890
_cell_measurement_theta_min      4.1920
_cell_volume                     2369.50(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_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    -97.00 -71.00   0.50    0.05    --  -46.62 -67.00  45.00   52
  2  \w    -65.00  25.00   0.50    0.05    --  -46.62  67.00 179.00  180
  3  \w    -13.00  53.00   0.50    0.05    --   46.62 -67.00  45.00  132
  4  \w     68.00  97.00   0.50    0.05    --   46.62  67.00 179.00   58
  5  \w   -166.00-138.00   0.50    0.10    -- -100.00 -67.00  45.00   56
  6  \w    -74.00 -49.00   0.50    0.10    -- -100.00  67.00 179.00   50
  7  \w     35.00 127.00   0.50    0.10    --  107.00 -67.00  45.00  184
  8  \w     88.00 170.00   0.50    0.10    --  107.00  67.00 179.00  164
  9  \w   -112.00 -75.00   0.50    0.05    --  -46.62-125.00-180.00   74
 10  \w   -117.00 -72.00   0.50    0.05    --  -46.62-125.00 120.00   90
 11  \w   -118.00 -74.00   0.50    0.05    --  -46.62-125.00 -60.00   88
 12  \w   -120.00 -27.00   0.50    0.10    -- -100.00  77.00   0.00  186
 13  \w   -154.00-128.00   0.50    0.10    -- -100.00 -30.00  90.00   52
 14  \w   -126.00 -90.00   0.50    0.10    -- -100.00 -30.00  90.00   72
 15  \w   -176.00 -86.00   0.50    0.10    -- -100.00 -15.00 120.00  180
 16  \w   -150.00 -91.00   0.50    0.10    -- -100.00 -94.00 120.00  118
 17  \w     38.00  68.00   0.50    0.10    --  107.00 -94.00  30.00   60
 18  \w     40.00  92.00   0.50    0.10    --  107.00 -94.00-120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1388764000
_diffrn_orient_matrix_UB_12      -0.0411523000
_diffrn_orient_matrix_UB_13      -0.0128168000
_diffrn_orient_matrix_UB_21      -0.0210163000
_diffrn_orient_matrix_UB_22      0.0995474000
_diffrn_orient_matrix_UB_23      -0.0527517000
_diffrn_orient_matrix_UB_31      0.0396908000
_diffrn_orient_matrix_UB_32      -0.0907796000
_diffrn_orient_matrix_UB_33      -0.0521223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15335
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.542
_diffrn_reflns_theta_min         4.189
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             959
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.783
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.783
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0429
_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^)+(0.1008P)^2^+1.8378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4214
_reflns_number_total             4708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02189j2.cif
_cod_data_source_block           yinxr_190314_2
_cod_depositor_comments
'Adding full bibliography for 7157764--7157766.cif.'
_cod_database_code               7157764
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11), C10(H10), C28(H28), C2(H2), C8(H8), C3(H3), C5(H5), C6(H6), C7(H7),
 C34(H34), C24(H24), C27(H27), C30(H30), C26(H26), C32(H32), C25(H25), C33(H33),
  C31(H31)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              59483
_shelx_hkl_checksum              55465
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.560