An isocyanide insertion approach to substituted pyrrolo[2,3-b]quinolines under metal-free and azide-free conditions
Liu, Cheng-Guo; Gu, Zheng-Yang; Bai, Hui-Wen; Wang, Shun-Yi; Ji, Shun-Jun; Organic Chemistry Frontiers 3 (2016) 1299–; doi:10.1039/C6QO00373G

data_1553503
_publ_section_title
;
 An isocyanide insertion approach to substituted pyrrolo[2,3-b]quinolines
 under metal-free and azide-free conditions
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1299
_journal_paper_doi               10.1039/C6QO00373G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C23 H24 N2'
_chemical_formula_sum            'C23 H24 N2'
_chemical_formula_weight         328.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-27
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_audit_update_record
;
2016-07-19 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                75.057(10)
_cell_angle_beta                 85.343(8)
_cell_angle_gamma                84.132(7)
_cell_formula_units_Z            2
_cell_length_a                   6.2020(5)
_cell_length_b                   10.1690(10)
_cell_length_c                   14.7158(18)
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    283(10)
_cell_measurement_theta_max      28.7940
_cell_measurement_theta_min      3.5270
_cell_volume                     890.56(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      283(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_details
;
  1 omega  -28.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -77.0000 -150.0000 75

  2 omega  -53.00   41.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -57.0000  -30.0000 94

  3 omega  -52.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -77.0000   90.0000 99

  4 omega  -97.00  -71.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000   30.0000 26

  5 omega  -72.00  -40.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  126.0000  -80.0000 32

  6 omega   -9.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -99.0000  -60.0000 31
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0375546000
_diffrn_orient_matrix_UB_12      0.0644716000
_diffrn_orient_matrix_UB_13      -0.0231116000
_diffrn_orient_matrix_UB_21      -0.0056933000
_diffrn_orient_matrix_UB_22      -0.0148560000
_diffrn_orient_matrix_UB_23      -0.0442231000
_diffrn_orient_matrix_UB_31      -0.1087106000
_diffrn_orient_matrix_UB_32      0.0295287000
_diffrn_orient_matrix_UB_33      -0.0026484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7574
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2576
_reflns_number_total             3640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00373g2.cif
_cod_data_source_block           g160627a
_cod_database_code               1553503
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_date_sample_data_collection 2016-06-27
_olex2_submission_special_instructions 'No special instructions were received'