Iodine-catalyzed oxidative annulation of 3-cyanoacetylindoles with benzylamines: facile access to 5-(3-indolyl)oxazoles.
Liu, Xiaozu; Zhou, Yuxiang; Chen, Guojun; Yang, Zhongqin; Li, Qin; Liu, Peijun; Organic & biomolecular chemistry 16 (2018) 3572–3575; doi:10.1039/c8ob00833g

data_7156233
_publ_section_title
;
 Iodine-catalyzed oxidative annulation of 3-cyanoacetylindoles with
 benzylamines: facile access to 5-(3-indolyl)oxazoles.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3572
_journal_page_last               3575
_journal_paper_doi               10.1039/c8ob00833g
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C18 H11 N3 O'
_chemical_formula_sum            'C18 H11 N3 O'
_chemical_formula_weight         285.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-01 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.544(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8242(5)
_cell_length_b                   5.6357(2)
_cell_length_c                   20.6262(8)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.9020
_cell_measurement_theta_min      3.7770
_cell_volume                     1355.46(9)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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    -64.00  25.00   1.00    1.00    --  -40.98  57.00 -30.00   89
  2  \w     83.00 110.00   1.00    1.00    --   40.98  38.00 -90.00   27
  3  \w     95.00 176.00   1.00    1.00    --  106.95  30.00 -60.00   81
  4  \w    121.00 161.00   1.00    1.00    --  106.95 125.00 -90.00   40
  5  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 120.00  104
  6  \w     34.00  87.00   1.00    1.00    --  106.95 -95.00 -30.00   53
  7  \w     91.00 118.00   1.00    1.00    --  106.95-125.00 -90.00   27
  8  \w     34.00 119.00   1.00    1.00    --  106.95 -45.00 -30.00   85
  9  \w   -111.00 -14.00   1.00    1.00    --  -40.98 -57.00-180.00   97
;
_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      -0.1086137000
_diffrn_orient_matrix_UB_12      -0.0557491000
_diffrn_orient_matrix_UB_13      0.0294337000
_diffrn_orient_matrix_UB_21      -0.0709338000
_diffrn_orient_matrix_UB_22      -0.0090235000
_diffrn_orient_matrix_UB_23      -0.0697058000
_diffrn_orient_matrix_UB_31      0.0250266000
_diffrn_orient_matrix_UB_32      -0.2673628000
_diffrn_orient_matrix_UB_33      -0.0037486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4637
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.649
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.406
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69282
_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            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.564
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.565
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.1363
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3392
_refine_ls_wR_factor_ref         0.3537
_reflns_Friedel_coverage         0.335
_reflns_Friedel_fraction_full    0.359
_reflns_Friedel_fraction_max     0.326
_reflns_number_gt                3164
_reflns_number_total             3529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00833g2.cif
_cod_data_source_block           exp_1202
_cod_depositor_comments          'Adding full bibliography for 7156233.cif.'
_cod_database_code               7156233
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.899
_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 N(H) groups
2. Rigid bond restraints
 C00B, C010, C013
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C00R, C010
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C00B \\sim C010 \\sim C013: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
C00R \\sim C010: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C17(H17), N00E(H00E), C3(H3), C00J(H00J), C00K(H00K), C2(H2),
 C00M(H00M), N1(H1), C5(H5), C13(H13), C00S(H00S), C00T(H00T), C00U(H00U),
 C4(H4), C15(H15), C011(H011), C013(H013), C014(H014), C16(H16), C7(H7),
 C14(H14)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.811