Access to π-conjugated azaindole derivatives via rhodium(iii)-catalyzed cascade reaction of azaindoles and diazo compounds.
Liu, Chen-Fei; Zhang, Guo-Tai; Sun, Jun-Shu; Dong, Lin; Organic & biomolecular chemistry 15 (2017) 2902–2905; doi:10.1039/c7ob00059f

data_7155520
_publ_section_title
;
 Access to \p-conjugated azaindole derivatives via rhodium(iii)-catalyzed
 cascade reaction of azaindoles and diazo compounds.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2902
_journal_page_last               2905
_journal_paper_doi               10.1039/c7ob00059f
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.49(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.820(4)
_cell_length_b                   17.17(2)
_cell_length_c                   10.534(5)
_cell_measurement_reflns_used    1087
_cell_measurement_temperature    290.55(10)
_cell_measurement_theta_max      24.5470
_cell_measurement_theta_min      3.9920
_cell_volume                     1886(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9629
_diffrn_measured_fraction_theta_max 0.7931
_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    -47.00  -7.00   1.00   15.95    --   16.50 -57.00 150.00   40
  2  \w    -52.00  78.00   1.00   15.95    --   16.50   0.00 -30.00  130
  3  \w     57.00  89.00   1.00   15.95    --   16.50 178.00 -90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0518960000
_diffrn_orient_matrix_UB_12      0.0143941000
_diffrn_orient_matrix_UB_13      -0.0499049000
_diffrn_orient_matrix_UB_21      0.0385624000
_diffrn_orient_matrix_UB_22      0.0322917000
_diffrn_orient_matrix_UB_23      -0.0107537000
_diffrn_orient_matrix_UB_31      0.0196818000
_diffrn_orient_matrix_UB_32      -0.0228727000
_diffrn_orient_matrix_UB_33      -0.0467991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6890
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     205
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0760
_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^)+(0.1220P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1995
_reflns_number_total             3716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00059f2.cif
_cod_data_source_block           xhl-12-12
_cod_depositor_comments          'Adding full bibliography for 7155520.cif.'
_cod_original_cell_volume        1886(3)
_cod_database_code               7155520
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 96.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C23, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.05
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.05
Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23) \\sim Ueq: with sigma of 0.0025 and sigma for terminal atoms of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 3.779
_oxdiff_exptl_absorpt_empirical_full_min 0.388