Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
Aksenov, Nicolai A.; Aksenov, Dmitrii A.; Arutiunov, Nikolai A.; Aksenova, Daria S.; Aksenov, Alexander V.; Rubin, Michael; RSC Advances 10 (2020) 18440–18450; doi:10.1039/D0RA03520C

data_7240542
_publ_section_title
;
 Unexpected cyclization of ortho-nitrochalcones into
 2-alkylideneindolin-3-ones
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              18440
_journal_page_last               18450
_journal_paper_doi               10.1039/D0RA03520C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 N2 O'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_chemical_name_systematic
(E)-2-(4-ethylphenyl)-2-(3-oxoindolin-2-ylidene)acetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6798(2)
_cell_length_b                   11.21770(10)
_cell_length_c                   12.58050(10)
_cell_measurement_reflns_used    10550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1480
_cell_measurement_theta_min      4.3530
_cell_volume                     2845.54(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -116.00 -17.00   1.00    2.63    --  -41.72 -38.00-150.00   99
  2  \w    -87.00  -6.00   1.00    2.63    --  -41.72 125.00 150.00   81
  3  \w      6.00  83.00   1.00    2.63    --   41.72 -99.00  90.00   77
  4  \w      8.00  42.00   1.00    2.63    --   41.72  81.00 -41.72   34
  5  \w     30.00 106.00   1.00   10.53    --  112.00 -95.00  30.00   76
  6  \w     86.00 178.00   1.00   10.53    --  112.00  45.00-150.00   92
  7  \w     86.00 178.00   1.00   10.53    --  112.00  45.00-120.00   92
  8  \w     61.00 146.00   1.00   10.53    --  112.00 178.00   0.00   85
  9  \w    104.00 178.00   1.00   10.53    --  112.00 111.00 -30.00   74
 10  \w     36.00 109.00   1.00   10.53    --  112.00-111.00   0.00   73
 11  \w     30.00 106.00   1.00   10.53    --  112.00 -95.00   0.00   76
 12  \w     36.00 109.00   1.00   10.53    --  112.00-111.00 -30.00   73
 13  \w     40.00 141.00   1.00   10.53    --  112.00 -61.00   0.00  101
 14  \w     40.00 141.00   1.00   10.53    --  112.00 -61.00  60.00  101
 15  \w    103.00 178.00   1.00   10.53    --  112.00  77.00 120.00   75
 16  \w    104.00 178.00   1.00   10.53    --  112.00 111.00  30.00   74
 17  \w     36.00 140.00   1.00   10.53    --  112.00 -30.00-150.00  104
 18  \w    104.00 178.00   1.00   10.53    --  112.00 111.00 150.00   74
 19  \w     86.00 178.00   1.00   10.53    --  112.00  45.00 120.00   92
 20  \w     37.00 144.00   1.00   10.53    --  112.00 -74.00 -73.03  107
 21  \w   -114.00 -42.00   1.00    2.63    --  -41.72 -57.00 120.00   72
 22  \w      8.00  42.00   1.00    2.63    --   41.72  82.00  74.19   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124894000
_diffrn_orient_matrix_UB_12      -0.1325839000
_diffrn_orient_matrix_UB_13      0.0202701000
_diffrn_orient_matrix_UB_21      0.0743605000
_diffrn_orient_matrix_UB_22      -0.0170833000
_diffrn_orient_matrix_UB_23      0.0508493000
_diffrn_orient_matrix_UB_31      -0.0123512000
_diffrn_orient_matrix_UB_32      0.0314582000
_diffrn_orient_matrix_UB_33      0.1130357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.345
_diffrn_reflns_theta_min         4.386
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0609P)^2^+0.9312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2786
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra03520c2.cif
_cod_data_source_block           anna1120_isat(da_final)_3
_cod_depositor_comments          'Adding full bibliography for 7240542.cif.'
_cod_original_cell_volume        2845.53(5)
_cod_database_code               7240542
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C7(H7), C13(H13), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              31390
_olex2_exptl_crystal_mounting_method
'Mounted by 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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.603