Metal-free syntheses of new azocines via addition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols
Mousavi, S. Hekmat; Mohammadizadeh, Mohammad Reza; Arimitsu, Satoru; Saberi, Dariush; Poorsadeghi, Samira; Genta, Kojya; RSC Advances 10 (2020) 20552–20557; doi:10.1039/D0RA02852E

data_7240591
_publ_section_title
;
 Metal-free syntheses of new azocines via addition reactions of enaminones
 with acenaphthoquinone followed by oxidative cleavages of the
 corresponding vicinal diols
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              20552
_journal_page_last               20557
_journal_paper_doi               10.1039/D0RA02852E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-01-09 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.347(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4024(2)
_cell_length_b                   11.0210(3)
_cell_length_c                   17.2462(3)
_cell_measurement_reflns_used    13381
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.0980
_cell_measurement_theta_min      1.7900
_cell_volume                     2167.22(8)
_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      113
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_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   -110.00  70.00   0.50   32.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50   32.00    --  -20.00  45.00  90.00  360
  3  \w   -110.00  70.00   0.50   32.00    --  -20.00  45.00  45.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn724Plus with AFC10'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162647000
_diffrn_orient_matrix_UB_12      -0.0444085000
_diffrn_orient_matrix_UB_13      0.0276924000
_diffrn_orient_matrix_UB_21      0.0470844000
_diffrn_orient_matrix_UB_22      0.0184996000
_diffrn_orient_matrix_UB_23      0.0243300000
_diffrn_orient_matrix_UB_31      -0.0372500000
_diffrn_orient_matrix_UB_32      0.0427680000
_diffrn_orient_matrix_UB_33      0.0182344000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.162
_diffrn_reflns_theta_min         1.786
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_preparation
'It has been crysalized from a acetonitrile solusion'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         6555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0400P)^2^+0.9820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4869
_reflns_number_total             6555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02852e2.cif
_cod_data_source_block           191008irai
_cod_depositor_comments          'Adding full bibliography for 7240591.cif.'
_cod_database_code               7240591
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H23 N1 O4'
_reflns_odcompleteness_completeness 93.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.09
_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:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C6(H6), C1(H1), C19(H19), C4(H4), C3(H3), C2(H2), C17(H17),
 C18(H18), C5(H5)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              27127
_olex2_date_sample_data_collection 2019-10-08
_olex2_date_sample_submission    2019-10-08
_olex2_exptl_crystal_mounting_method 'Mitegen Micromount'
_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 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.843