Condensation of acrylonitrile and aryl acetonitrile: construction of α-amino-β-cyano cyclohexene skeletons
Zhang, Wei; Tang, Chuan-Su; Xiang, Shi-Qun; RSC Advances 12 (2022) 29840–29843; doi:10.1039/D2RA04936H

data_7245686
_publ_section_title
;
 Condensation of acrylonitrile and aryl acetonitrile: construction of
 \a-amino-\b-cyano cyclohexene skeletons
;
_journal_issue                   46
_journal_name_full               'RSC Advances'
_journal_page_first              29840
_journal_page_last               29843
_journal_paper_doi               10.1039/D2RA04936H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C14 H13 N3'
_chemical_formula_sum            'C14 H13 N3'
_chemical_formula_weight         223.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-01-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-03-12 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                67.011(3)
_cell_angle_beta                 80.092(3)
_cell_angle_gamma                77.442(3)
_cell_formula_units_Z            8
_cell_length_a                   11.5840(4)
_cell_length_b                   13.3019(4)
_cell_length_c                   16.7992(5)
_cell_measurement_reflns_used    7807
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.3300
_cell_measurement_theta_min      3.7050
_cell_volume                     2315.01(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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   -112.00 -38.00   1.00    1.00    --  -41.33 -42.00 -12.00   74
  2  \w    -67.00  32.00   1.00    1.00    --  -41.33  42.00 139.00   99
  3  \w     -7.00  18.00   1.00    1.00    --   41.33 -42.00 -12.00   25
  4  \w     79.00 108.00   1.00    1.00    --   41.33  42.00 139.00   29
  5  \w     35.00 111.00   1.00    1.00    --  107.56 -42.00 -12.00   76
  6  \w     82.00 167.00   1.00    1.00    --  107.56  42.00 139.00   85
  7  \w    -32.00  -2.00   1.00    1.00    --  -41.33 125.00-150.00   30
  8  \w    -67.00  -7.00   1.00    1.00    --  -41.33 125.00 150.00   60
  9  \w      2.00  31.00   1.00    1.00    --   41.33 -99.00 -90.00   29
 10  \w     24.00  95.00   1.00    1.00    --   41.33-125.00 -30.00   71
 11  \w     54.00  86.00   1.00    1.00    --   41.33-125.00-150.00   32
 12  \w    102.00 165.00   1.00    1.00    --  107.56 111.00  60.00   63
 13  \w     51.00 108.00   1.00    1.00    --  107.56-111.00 120.00   57
 14  \w     26.00  75.00   1.00    1.00    --  107.56 -94.00 -30.00   49
 15  \w     51.00 128.00   1.00    1.00    --  107.56 -45.00 150.00   77
 16  \w     82.00 110.00   1.00    1.00    --  107.56  45.00  30.00   28
 17  \w     59.00 178.00   1.00    1.00    --  107.56  15.00-120.00  119
 18  \w     29.00 105.00   1.00    1.00    --  107.56 -94.00   0.00   76
 19  \w    122.00 172.00   1.00    1.00    --  107.56 111.00 -90.00   50
 20  \w    150.00 175.00   1.00    1.00    --  107.56 111.00-180.00   25
 21  \w     37.00 105.00   1.00    1.00    --  107.56-111.00-150.00   68
 22  \w     42.00  67.00   1.00    1.00    --  107.56 -45.00  90.00   25
 23  \w     52.00  79.00   1.00    1.00    --  107.56-143.00  -8.74   27
 24  \w     91.00 131.00   1.00    1.00    --  107.56-143.00  -8.74   40
 25  \w    113.00 138.00   1.00    1.00    --  107.56 178.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18767
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.593
_diffrn_reflns_theta_min         3.660
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00175(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.4996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7456
_reflns_number_total             9191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04936h2.cif
_cod_data_source_block           3a
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H52 N12'
_cod_original_formula_weight         893.09
_cod_original_formula_moiety         '4(C14 H13 N3)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2315.02(14)
_cod_database_code               7245686
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.876
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C18(H18A,H18B), C1C(H1CA,H1CB), C1D(H1DA,H1DB), C10(H10A,H10B),
 C1Q(H1QA,H1QB), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
  C29(H29A,H29B), C2A(H2AA,H2AB)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C1(H1), C2(H2), C13(H13), C4(H4), C5(H5), C6(H6), C7(H7), C16(H16),
 C19(H19), C1I(H1I), C1J(H1J), C1K(H1K), C1L(H1L), C1R(H1R), C1V(H1V), C1W(H1W),
  C1X(H1X), C1Y(H1Y), C21(H21)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N6(H6A,H6B), N10(H10C,H10D)
;
_shelx_res_checksum              37639
_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
;