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_7157766
_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         'C33 H21 Cl3 N2 O4'
_chemical_formula_sum            'C33 H21 Cl3 N2 O4'
_chemical_formula_weight         615.87
_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
_audit_creation_date             2020-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-02 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.176(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0142(4)
_cell_length_b                   21.0380(5)
_cell_length_c                   9.3503(3)
_cell_measurement_reflns_used    12233
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6830
_cell_measurement_theta_min      3.7620
_cell_volume                     2756.74(14)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.986
_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    -19.00  44.00   0.50    0.50    --   46.37-100.00-104.00  126
  2  \w   -113.00 -36.00   0.50    0.50    -- -100.00  53.00 -92.00  154
  3  \w   -151.00 -98.00   0.50    0.50    -- -100.00-100.00-104.00  106
  4  \w     90.00 173.00   0.50    0.50    --  105.44  75.00 114.00  166
  5  \w   -107.00 -82.00   0.50    0.50    --  -46.37-125.00-120.00   50
  6  \w    -59.00  19.00   0.50    0.50    --  -46.37  38.00   0.00  156
  7  \w   -116.00 -73.00   0.50    0.50    --  -46.37-125.00 -90.00   86
  8  \w     34.00 106.00   0.50    0.50    --  105.44 -94.00 -30.00  144
  9  \w     92.00 155.00   0.50    0.50    --  105.44  30.00  90.00  126
 10  \w   -117.00 -26.00   0.50    0.50    --  -46.37 -75.00 -12.00  182
 11  \w    -55.00 -30.00   0.50    0.50    --  -46.37 -57.00  90.00   50
 12  \w   -118.00 -93.00   0.50    0.50    --  -46.37-125.00-180.00   50
 13  \w    -45.00  23.00   0.50    0.50    --  -46.37  38.00 120.00  136
 14  \w    -99.00 -49.00   0.50    0.50    --  -46.37 -38.00-120.00  100
 15  \w   -114.00 -85.00   0.50    0.50    --  -46.37 -57.00  90.00   58
 16  \w   -134.00 -84.00   0.50    0.80    -- -100.00 -94.00-150.00  100
 17  \w   -116.00 -90.00   0.50    0.80    -- -100.00 -30.00  60.00   52
 18  \w   -145.00 -85.00   0.50    0.80    -- -100.00 -30.00-150.00  120
 19  \w   -175.00-101.00   0.50    0.80    -- -100.00 -30.00 -90.00  148
 20  \w   -172.00-146.00   0.50    0.80    -- -100.00 -30.00-150.00   52
 21  \w     52.00 131.00   0.50    0.80    --  107.00 -77.00   0.00  158
 22  \w     95.00 146.00   0.50    0.80    --  107.00  45.00-120.00  102
 23  \w     96.00 122.00   0.50    0.80    --  107.00 -15.00 -30.00   52
 24  \w     67.00 128.00   0.50    0.80    --  107.00 -77.00-150.00  122
 25  \w     48.00  74.00   0.50    0.80    --  107.00 -94.00   0.00   52
 26  \w     93.00 124.00   0.50    0.80    --  107.00  45.00-150.00   62
 27  \w     63.00 116.00   0.50    0.80    --  107.00-125.00 -30.00  106
 28  \w     79.00 123.00   0.50    0.80    --  107.00 -30.00-120.00   88
 29  \w    126.00 176.00   0.50    0.80    --  107.00  45.00  90.00  100
 30  \w     95.00 121.00   0.50    0.80    --  107.00  45.00  90.00   52
 31  \w    109.00 166.00   0.50    0.80    --  107.00  61.00  30.00  114
 32  \w     84.00 145.00   0.50    0.80    --  107.00  77.00 120.00  122
 33  \w     40.00  72.00   0.50    0.80    --  107.00 -30.00-120.00   64
 34  \w     66.00 123.00   0.50    0.80    --  107.00 -30.00 -30.00  114
 35  \w     84.00 109.00   0.50    0.80    --  107.00 -94.00   0.00   50
 36  \w     36.00  83.00   0.50    0.80    --  107.00 -15.00 -30.00   94
 37  \w     39.00  65.00   0.50    0.80    --  107.00 -30.00 -30.00   52
 38  \w     35.00  67.00   0.50    0.80    --  107.00 -94.00-150.00   64
 39  \w     92.00 169.00   0.50    0.80    --  107.00  61.00 -90.00  154
 40  \w     73.00 125.00   0.50    0.80    --  107.00 -61.00   0.00  104
 41  \w   -118.00 -23.00   0.50    0.50    --  -46.37 -77.00  60.00  190
 42  \w   -118.00 -30.00   0.50    0.50    --  -46.37 -57.00-120.00  176
 43  \w   -118.00 -23.00   0.50    0.50    --  -46.37 -77.00-150.00  190
 44  \w   -118.00 -23.00   0.50    0.50    --  -46.37 -77.00 150.00  190
 45  \w     23.00 118.00   0.50    0.50    --   46.37  77.00 -60.00  190
 46  \w     23.00 118.00   0.50    0.50    --   46.37  77.00   0.00  190
 47  \w     15.00  95.00   0.50    0.50    --   46.37-125.00-180.00  160
 48  \w     15.00  95.00   0.50    0.50    --   46.37-125.00 -60.00  160
 49  \w     93.00 166.00   0.50    0.80    --  107.00  45.00  30.00  146
 50  \w     34.00 117.00   0.50    0.80    --  107.00-125.00-180.00  166
 51  \w     89.00 178.00   0.50    0.80    --  107.00  15.00   0.00  178
 52  \w    -45.00 -20.00   0.50    0.50    --  -46.37  75.00 114.00   50
 53  \w    -45.00 -20.00   0.50    0.50    --  -46.37  75.00 114.00   50
 54  \w     -2.00  23.00   0.50    0.50    --   46.37 -75.00 -12.00   50
 55  \w    -95.00 -70.00   0.50    0.50    --  -46.37 -75.00 -12.00   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      -0.1021323000
_diffrn_orient_matrix_UB_12      0.0382177000
_diffrn_orient_matrix_UB_13      0.0642069000
_diffrn_orient_matrix_UB_21      -0.0279326000
_diffrn_orient_matrix_UB_22      0.0468433000
_diffrn_orient_matrix_UB_23      -0.0824956000
_diffrn_orient_matrix_UB_31      -0.1261951000
_diffrn_orient_matrix_UB_32      -0.0413270000
_diffrn_orient_matrix_UB_33      -0.0340538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            55473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.979
_diffrn_reflns_theta_min         3.153
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75460
_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    1.484
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0462P)^2^+3.0188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4720
_reflns_number_total             5747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02189j2.cif
_cod_data_source_block           yinxr_191223_2
_cod_depositor_comments
'Adding full bibliography for 7157764--7157766.cif.'
_cod_database_code               7157766
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOCl
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.431
_diffrn_oxdiff_digest_frames
;
0124191b226be6e8714d281e1966b77fff01114e892
;
_diffrn_oxdiff_digest_hkl
;
01995ee3e9433ebc1ac0d15f37f825746e791b
;
_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 C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 N31(H31), C36(H36), C10(H10), C38(H38), C30(H30), C23(H23), C9(H9), C5(H5),
 C19(H19), C24(H24), C8(H8), C4(H4), C15(H15), C7(H7), C18(H18), C16(H16),
 C17(H17)
;
_shelx_res_checksum              6000
_shelx_hkl_checksum              73714
_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 2.009
_oxdiff_exptl_absorpt_empirical_full_min 0.655