One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine.
Aksenov, Alexander V.; Aksenov, Dmitrii A.; Orazova, Naila A.; Aksenov, Nicolai A.; Griaznov, Georgii D.; De Carvalho, Annelise; Kiss, Robert; Mathieu, Véronique; Kornienko, Alexander; Rubin, Michael; The Journal of organic chemistry 82 (2017) 3011–3018; doi:10.1021/acs.joc.6b03084

data_4032372
_publ_section_title
;
 One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of
 Isocryptolepine.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3011
_journal_page_last               3018
_journal_paper_doi               10.1021/acs.joc.6b03084
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_name_systematic        2-methoxy-11H-indolo[3,2-c]quinoline
_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     direct
_audit_creation_date             2016-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.383(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1053(3)
_cell_length_b                   18.1238(12)
_cell_length_c                   12.8535(7)
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    292.96(15)
_cell_measurement_theta_max      72.5180
_cell_measurement_theta_min      4.2490
_cell_volume                     1187.23(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.96(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9895
_diffrn_measured_fraction_theta_max 0.9635
_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    -51.00  -4.00   1.00    1.00    --   36.82 -77.00 150.00   47
  2  \w     14.00  53.00   1.00    1.00    --   36.82 -57.00-120.00   39
  3  \w      0.00 123.00   1.00    1.00    --   36.82  77.00 150.00  123
  4  \w     28.00  70.00   1.00    1.00    --   36.82 -77.00 150.00   42
  5  \w      3.00  29.00   1.00    1.00    --   36.82  77.00 -60.00   26
  6  \w     41.00 118.00   1.00    1.00    --   36.82  57.00  90.00   77
  7  \w     21.00  72.00   1.00    1.00    --   36.82 -57.00-180.00   51
  8  \w    -32.00  -2.00   1.00    1.00    --   36.82 -57.00  30.00   30
  9  \w     -4.00  65.00   1.00    1.00    --   36.82 -77.00   0.00   69
 10  \w    -49.00 -12.00   1.00    1.00    --   36.82 -77.00   0.00   37
 11  \w    -29.00   1.00   1.00    1.00    --   36.82 -57.00-120.00   30
 12  \w     79.00 178.00   1.00    9.61    --  110.40  45.00  30.00   99
 13  \w     60.00 117.00   1.00    9.61    --  110.40 -80.00  22.12   57
 14  \w    123.00 149.00   1.00    9.61    --  110.40 -79.00 118.54   26
 15  \w     71.00 100.00   1.00    9.61    --  110.40 -79.00 -43.82   29
 16  \w     76.00 150.00   1.00    9.61    --  110.40  45.00  90.00   74
 17  \w     59.00  87.00   1.00    9.61    --  110.40 -45.00  90.00   28
 18  \w     20.00 118.00   1.00    9.61    --  110.40 -79.00 118.54   98
 19  \w     73.00 171.00   1.00    9.61    --  110.40  77.00 -30.00   98
 20  \w     76.00 176.00   1.00    9.61    --  110.40  45.00 -60.00  100
 21  \w    109.00 134.00   1.00    9.61    --  110.40 -45.00  90.00   25
 22  \w     67.00 149.00   1.00    9.61    --  110.40 -79.00 -85.94   82
 23  \w    116.00 149.00   1.00    9.61    --  110.40 -79.00 -43.82   33
 24  \w     35.00  61.00   1.00    9.61    --  110.40 -79.00 -43.82   26
 25  \w     66.00 133.00   1.00    9.61    --  110.40 -80.00-161.95   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281482000
_diffrn_orient_matrix_UB_12      0.0843206000
_diffrn_orient_matrix_UB_13      0.0103207000
_diffrn_orient_matrix_UB_21      -0.1197332000
_diffrn_orient_matrix_UB_22      -0.0031634000
_diffrn_orient_matrix_UB_23      0.1071894000
_diffrn_orient_matrix_UB_31      0.2762176000
_diffrn_orient_matrix_UB_32      -0.0098855000
_diffrn_orient_matrix_UB_33      0.0531580000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7012
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.832
_diffrn_reflns_theta_min         4.222
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method 'recrystallized from EtOH'
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0689P)^2^+0.1500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1959
_reflns_number_total             2319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03084_si_002.cif
_cod_data_source_block           anna_ded_alk_mrbutin_20
_cod_depositor_comments
'Adding full bibliography for 4032372--4032373.cif.'
_cod_original_cell_volume        1187.22(13)
_cod_database_code               4032372
_chemical_oxdiff_formula         C16H12N2O1
_reflns_odcompleteness_completeness 98.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'acrylic glue on the glass stick'
_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 2.082
_oxdiff_exptl_absorpt_empirical_full_min 0.482
_shelx_res_checksum              54552
_shelx_hkl_checksum              52694