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_7157765
_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         '4(C38 H25 Cl3 N2 O2), S'
_chemical_formula_sum            'C152 H108 Cl12 N8 O8 S'
_chemical_formula_weight         2631.92
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc23yp70
_audit_creation_date             2019-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-11 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.67440(10)
_cell_length_b                   26.67440(10)
_cell_length_c                   18.17960(10)
_cell_measurement_reflns_used    49236
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7780
_cell_measurement_theta_min      2.9310
_cell_volume                     12935.21(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -65.00   2.00   0.50    0.40    --  -46.37  69.00 -58.00  134
  2  \w   -114.00 -40.00   0.50    1.50    -- -100.00  53.00 112.00  148
  3  \w     63.00  89.00   0.50    1.50    --  105.44-119.00  96.00   52
  4  \w   -117.00 -77.00   0.50    0.40    --  -46.37-125.00 -60.00   80
  5  \w    -99.00 -71.00   0.50    0.40    --  -46.37-125.00-120.00   56
  6  \w   -100.00 -28.00   0.50    1.50    -- -100.00  45.00 -60.00  144
  7  \w    107.00 176.00   0.50    1.50    --  105.44  45.00-120.00  138
  8  \w     35.00  88.00   0.50    1.50    --  105.44 -94.00 150.00  106
  9  \w   -151.00-126.00   0.50    2.00    -- -100.00 -68.00 168.00   50
 10  \w   -115.00 -74.00   0.50    1.00    --  -46.37-125.00 150.00   82
 11  \w   -116.00 -31.00   0.50    1.00    --  -46.37 -57.00-150.00  170
 12  \w     47.00  76.00   0.50    1.00    --   46.37  57.00 150.00   58
 13  \w   -121.00 -82.00   0.50    2.00    -- -100.00 -61.00-129.12   78
 14  \w   -171.00-119.00   0.50    2.00    -- -100.00 -71.00-139.63  104
 15  \w   -109.00 -83.00   0.50    2.00    -- -100.00 -54.00-158.29   52
 16  \w   -160.00-134.00   0.50    2.00    -- -100.00 -71.00-120.64   52
 17  \w   -104.00 -79.00   0.50    2.00    -- -100.00 -71.00-120.64   50
 18  \w     64.00 131.00   0.50    2.00    --  107.00 -77.00-150.00  134
 19  \w     90.00 151.00   0.50    2.00    --  107.00  61.00  60.00  122
 20  \w    104.00 170.00   0.50    2.00    --  107.00  61.00 120.00  132
 21  \w     86.00 123.00   0.50    2.00    --  107.00 -61.00 -90.00   74
 22  \w     84.00 128.00   0.50    2.00    --  107.00  77.00-150.00   88
 23  \w     41.00  67.00   0.50    2.00    --  107.00 -94.00-180.00   52
 24  \w    151.00 177.00   0.50    2.00    --  107.00  30.00-180.00   52
 25  \w     92.00 143.00   0.50    2.00    --  107.00  30.00-180.00  102
 26  \w     38.00  70.00   0.50    2.00    --  107.00 -61.00 -90.00   64
 27  \w   -118.00 -23.00   0.50    1.00    --  -46.37 -77.00  90.00  190
 28  \w   -118.00 -30.00   0.50    1.00    --  -46.37 -57.00 -90.00  176
 29  \w   -118.00 -31.00   0.50    1.00    --  -46.37 -53.00 -31.00  174
 30  \w   -108.00 -83.00   0.50    1.00    --  -46.37-157.00 -58.00   50
;
_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      -0.0255851000
_diffrn_orient_matrix_UB_12      0.0434056000
_diffrn_orient_matrix_UB_13      -0.0415274000
_diffrn_orient_matrix_UB_21      -0.0368529000
_diffrn_orient_matrix_UB_22      -0.0374039000
_diffrn_orient_matrix_UB_23      -0.0352717000
_diffrn_orient_matrix_UB_31      -0.0364063000
_diffrn_orient_matrix_UB_32      0.0074024000
_diffrn_orient_matrix_UB_33      0.0648220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.023
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             5440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.607
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0770
_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^)+(0.0884P)^2^+58.7554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6576
_reflns_number_total             6752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02189j2.cif
_cod_data_source_block           yinxr_191104
_cod_depositor_comments
'Adding full bibliography for 7157764--7157766.cif.'
_cod_original_cell_volume        12935.22(12)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7157765
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOS
_shelx_estimated_absorpt_t_max   0.584
_shelx_estimated_absorpt_t_min   0.465
_diffrn_oxdiff_digest_frames
;
01b9d4ded89acc49e21c7901af7c5e9ced00858cc1e
;
_diffrn_oxdiff_digest_hkl
;
01f39682fdd39129fde409f01a82a95cc5b2df
;
_reflns_odcompleteness_completeness 100.00
_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 N(H) groups
2. Others
 Sof(Cl2A)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00I(H00I)
3.b Aromatic/amide H refined with riding coordinates:
 N008(H008), C00D(H00D), C00H(H00H), C00K(H00K), C00N(H00N), C00O(H00O),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A)
;
_shelx_res_checksum              94254
_shelx_hkl_checksum              53093
_shelx_fab_checksum              3449
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.857