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_4032373
_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_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_chemical_name_systematic        2,3-dimethoxy-11H-indolo[3,2-c]quinoline
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   20.00573(15)
_cell_length_b                   20.00573(15)
_cell_length_c                   13.20742(18)
_cell_measurement_reflns_used    7787
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9470
_cell_measurement_theta_min      4.3900
_cell_volume                     5286.00(9)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.8482
_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    -60.00 -14.00   1.00    7.18    --  -42.10 -57.00  30.00   46
  2  \w    -44.00 -11.00   1.00    7.18    --  -42.10 -77.00   0.00   33
  3  \f    245.00 272.00   1.00    7.18 -42.10 -42.10 -60.00    --    27
  4  \w    -66.00  29.00   1.00    7.18    --  -42.10  57.00 120.00   95
  5  \w   -115.00 -83.00   1.00    7.18    --  -42.10 -77.00   0.00   32
  6  \f    335.00 360.00   1.00    7.18 -42.10 -42.10 -60.00    --    25
  7  \w    137.00 164.00   1.00   32.48    --  107.59  61.00 -30.00   27
  8  \w     76.00 103.00   1.00   32.48    --  107.59  77.00 -30.00   27
  9  \w     78.00 104.00   1.00   32.48    --  107.59  61.00 -30.00   26
 10  \w     78.00 105.00   1.00   32.48    --  107.59  61.00  30.00   27
 11  \w     78.00 104.00   1.00   32.48    --  107.59  61.00   0.00   26
 12  \w     75.00 101.00   1.00   32.48    --  107.59  77.00  30.00   26
 13  \w     82.00 109.00   1.00   32.48    --  107.59  45.00  30.00   27
 14  \w    114.00 140.00   1.00   32.48    --  107.59 -77.00 -30.00   26
 15  \w     79.00 104.00   1.00   32.48    --  107.59  61.00  60.00   25
 16  \w     84.00 109.00   1.00   32.48    --  107.59  45.00   0.00   25
 17  \w     33.00  94.00   1.00   32.48    --  107.59 -77.00 -30.00   61
 18  \w     76.00 178.00   1.00   32.48    --  107.59  77.00   0.00  102
 19  \w     96.00 176.00   1.00   32.48    --  107.59  61.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0703417000
_diffrn_orient_matrix_UB_12      -0.0280752000
_diffrn_orient_matrix_UB_13      -0.0213440000
_diffrn_orient_matrix_UB_21      -0.0278149000
_diffrn_orient_matrix_UB_22      0.0716198000
_diffrn_orient_matrix_UB_23      -0.0058617000
_diffrn_orient_matrix_UB_31      0.0145889000
_diffrn_orient_matrix_UB_32      0.0015599000
_diffrn_orient_matrix_UB_33      -0.1145820000
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11191
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.072
_diffrn_reflns_theta_min         4.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46705
_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            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       prism
_exptl_crystal_F_000             2336
_exptl_crystal_recrystallization_method 'Recrystallized from EtOH'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0558P)^2^+2.3325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                2374
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.8715\% 
 around [1.00 0.01 0.06] (reciprocal) or [0.99 0.01 0.13] (direct)
;
_cod_data_source_file            jo6b03084_si_002.cif
_cod_data_source_block           anna_ded_alkaloid_59_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 4032372--4032373.cif.'
_cod_original_cell_volume        5286.00(11)
_cod_database_code               4032373
_chemical_oxdiff_formula         'C11 H10 N O'
_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:
 C8(H8), C3(H3), C4(H4), C13(H13), C1(H1A), C11(H11), C2(H2)
2.b Fitted pentagon refined as free rotating group:
 C14(C15,C5,N1,C6)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 2.336
_oxdiff_exptl_absorpt_empirical_full_min 0.661
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_shelx_res_checksum              54606
_shelx_hkl_checksum              22407