Synthesis of cyano-substituted γ-lactams through a copper-catalyzed cascade cyclization/cyanation reaction.
Liu, Wen; Wang, Liang; Mu, Haiping; Zhang, Qian; Fang, Zeguo; Li, Dong; Organic & biomolecular chemistry  (2023) –; doi:10.1039/d2ob02086f

data_7159081
_publ_section_title
;
 Synthesis of cyano-substituted &#x3b3;-lactams through a copper-catalyzed
 cascade cyclization/cyanation reaction.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d2ob02086f
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2b'
_space_group_name_H-M_alt        'P b c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-25 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.03944(15)
_cell_length_b                   12.8249(3)
_cell_length_c                   27.8674(8)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7220
_cell_measurement_theta_min      4.6760
_cell_volume                     2158.48(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -71.00  -6.00   1.00    1.50    --  -33.50 -77.00 -30.00   65
  2  \w   -101.00 -59.00   1.00    1.50    --  -33.50 -77.00  90.00   42
  3  \w     33.00  59.00   1.00    1.50    --   36.47 -37.00-150.00   26
  4  \w     62.00 110.00   1.00    1.50    --   36.47 178.00-180.00   48
  5  \w    -32.00  -6.00   1.00    1.50    --   36.47 -37.00-150.00   26
  6  \w     60.00  99.00   1.00    1.00    --   36.47 178.00-120.00   39
  7  \w     51.00 108.00   1.00    4.00    --  108.00 -94.00  90.00   57
  8  \w     42.00 129.00   1.00    4.00    --  108.00 -30.00  90.00   87
  9  \w     55.00  91.00   1.00    4.00    --  108.00 -61.00  90.00   36
 10  \w     87.00 178.00   1.00    4.00    --  108.00  30.00  90.00   91
 11  \w    127.00 170.00   1.00    4.00    --  108.00 111.00  90.00   43
 12  \w    -87.00 -61.00   1.00    1.00    --  -33.50 -57.00  90.00   26
 13  \w    -54.00 -21.00   1.00    1.00    --  -33.50 -57.00  90.00   33
 14  \w    -85.00 -41.00   1.00    1.00    --  -33.50 178.00 -30.00   44
 15  \w     76.00 103.00   1.00    1.00    --   36.47 178.00  90.00   27
 16  \w     57.00  95.00   1.00    4.00    --  108.00 178.00-180.00   38
 17  \w     45.00 105.00   1.00    4.00    --  108.00 -94.00-120.00   60
 18  \w     90.00 127.00   1.00    4.00    --  108.00 -61.00-180.00   37
 19  \w    105.00 141.00   1.00    4.00    --  108.00 111.00  30.00   36
 20  \w     10.00  36.00   1.00    1.00    --  -33.50  37.00 -90.00   26
 21  \w     12.00  37.00   1.00    1.00    --  -33.50  37.00 -90.00   25
 22  \w     12.00  37.00   1.00    1.00    --  -33.50  37.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0944305000
_diffrn_orient_matrix_UB_12      0.0830483000
_diffrn_orient_matrix_UB_13      -0.0343422000
_diffrn_orient_matrix_UB_21      -0.0503565000
_diffrn_orient_matrix_UB_22      -0.0713307000
_diffrn_orient_matrix_UB_23      -0.0431063000
_diffrn_orient_matrix_UB_31      -0.2315078000
_diffrn_orient_matrix_UB_32      0.0493532000
_diffrn_orient_matrix_UB_33      -0.0046031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.904
_diffrn_reflns_theta_min         6.353
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0638P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.700
_reflns_Friedel_fraction_max     0.668
_reflns_number_gt                2712
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02086f2.cif
_cod_data_source_block           20220331
_cod_original_cell_volume        2158.47(10)
_cod_database_code               7159081
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.91
_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 C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
 C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C2'(H2'), C3'(H3'), C4'(H4'),
 C5'(H5'), C6'(H6')
;
_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.881