Synthesis of chiral seven-membered β-substituted lactams via Rh-catalyzed asymmetric hydrogenation.
Huang, Yi; Li, Pan; Dong, Xiu-Qin; Zhang, Xumu; Organic & biomolecular chemistry 16 (2018) 8819–8823; doi:10.1039/c8ob02231c

data_7156563
_publ_section_title
;
 Synthesis of chiral seven-membered \b-substituted lactams via
 Rh-catalyzed asymmetric hydrogenation.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8819
_journal_page_last               8823
_journal_paper_doi               10.1039/c8ob02231c
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H20 Cl N O3'
_chemical_formula_sum            'C20 H20 Cl N O3'
_chemical_formula_weight         357.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.32172(3)
_cell_length_b                   11.65514(5)
_cell_length_c                   28.13606(11)
_cell_measurement_reflns_used    31842
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6140
_cell_measurement_theta_min      3.1380
_cell_volume                     1745.150(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -26.00  22.00   0.50    0.50    --    0.00 -57.00  30.00   96
  2  \w     42.00  75.00   0.50    0.50    --    0.00  38.00  90.00   66
  3  \w     -3.00  29.00   0.50    0.50    --    0.00 -77.00 -90.00   64
  4  \w     57.00  88.00   0.50    0.50    --    0.00  38.00   0.00   62
  5  \w    -14.00  21.00   0.50    0.50    --    0.00  38.00-180.00   70
  6  \w     34.00  86.00   0.50    0.50    --    0.00  57.00  30.00  104
  7  \w    -13.00  37.00   0.50    0.50    --    0.00  38.00  90.00  100
  8  \w     36.00  82.00   0.50    0.50    --    0.00  38.00-180.00   92
  9  \w    -16.00  20.00   0.50    0.50    --    0.00  57.00  30.00   72
 10  \w    -17.00  39.00   0.50    0.50    --    0.00  38.00   0.00  112
 11  \w    -81.00 -55.00   0.50    0.50    --    0.00 -57.00  30.00   52
 12  \w    -21.00  35.00   0.50    0.50    --    0.00  57.00 -90.00  112
 13  \w    -38.00 -13.00   0.50    0.50    --    0.00 -77.00 -90.00   50
 14  \w     69.00 113.00   0.50    0.50    --   94.60  67.00-117.46   88
 15  \w     71.00 100.00   0.50    0.50    --   94.60  60.00 -22.75   58
 16  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 -55.20   50
 17  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  90.28   52
 18  \w     68.00 183.00   0.50    0.50    --   94.60  70.00  67.50  230
 19  \w     76.00 184.00   0.50    0.50    --   94.60  43.00  14.65  216
 20  \w    121.00 183.00   0.50    0.50    --   94.60  47.00 -50.05  124
 21  \w     67.00 102.00   0.50    0.50    --   94.60  73.00   3.81   70
 22  \w     70.00 104.00   0.50    0.50    --   94.60  63.00 110.14   68
 23  \w     66.00  92.00   0.50    0.50    --   94.60  74.00 -17.74   52
 24  \w    142.00 171.00   0.50    0.50    --   94.60  74.00 -17.74   58
 25  \w     78.00 125.00   0.50    0.50    --   94.60 -82.00-120.00   94
 26  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-180.00   50
 27  \w     53.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  146
 28  \w     71.00 101.00   0.50    0.50    --   94.60  61.00 -90.00   60
 29  \w    110.00 184.00   0.50    0.50    --   94.60  61.00 -90.00  148
 30  \w    122.00 172.00   0.50    0.50    --   94.60  50.00 -60.30  100
 31  \w    108.00 184.00   0.50    0.50    --   94.60  73.00 132.12  152
 32  \w     67.00  96.00   0.50    0.50    --   94.60  73.00 132.12   58
 33  \w     74.00 100.00   0.50    0.50    --   94.60  50.00 -60.30   52
 34  \w     67.00 183.00   0.50    0.50    --   94.60  72.00-146.78  232
 35  \w     75.00 115.00   0.50    0.50    --   94.60  45.00 150.00   80
 36  \w     12.00 125.00   0.50    0.50    --   94.60 -82.00   0.00  226
 37  \w     69.00 154.00   0.50    0.50    --   94.60  68.00 156.16  170
 38  \w     66.00 183.00   0.50    0.50    --   94.60  75.00  15.92  234
 39  \w     67.00  92.00   0.50    0.50    --   94.60  71.00  50.42   50
 40  \w     74.00 184.00   0.50    0.50    --   94.60  53.00  56.86  220
 41  \w     72.00  98.00   0.50    0.50    --   94.60  61.00-120.00   52
 42  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  90.00   52
 43  \w    142.00 176.00   0.50    0.50    --   94.60  61.00  90.00   68
 44  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -60.00   52
 45  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-150.00   50
 46  \w     72.00  98.00   0.50    0.50    --   94.60  58.00-171.63   52
 47  \w     28.00 104.00   0.50    0.50    --   94.60 -82.00  30.00  152
 48  \w     68.00  94.00   0.50    0.50    --   94.60  70.00 -50.36   52
 49  \w     25.00 125.00   0.50    0.50    --   94.60 -82.00-180.00  200
 50  \w     25.00  51.00   0.50    0.50    --   94.60 -82.00-120.00   52
 51  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 117.03   50
 52  \w    159.00 184.00   0.50    0.50    --   94.60  67.00 -55.20   50
 53  \w     68.00  93.00   0.50    0.50    --   94.60  69.00   6.63   50
 54  \w     76.00 114.00   0.50    0.50    --   94.60  47.00 -50.05   76
 55  \w     71.00 184.00   0.50    0.50    --   94.60  61.00-163.99  226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0784864000
_diffrn_orient_matrix_UB_12      -0.0794759000
_diffrn_orient_matrix_UB_13      -0.0411536000
_diffrn_orient_matrix_UB_21      0.0148878000
_diffrn_orient_matrix_UB_22      0.1042656000
_diffrn_orient_matrix_UB_23      -0.0335444000
_diffrn_orient_matrix_UB_31      0.2782148000
_diffrn_orient_matrix_UB_32      0.0168542000
_diffrn_orient_matrix_UB_33      0.0134040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            37085
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.829
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0342P)^2^+0.3963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0616
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3525
_reflns_number_total             3529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02231c2.cif
_cod_data_source_block           20180706-1
_cod_depositor_comments          'Adding full bibliography for 7156563.cif.'
_cod_original_cell_volume        1745.151(13)
_cod_database_code               7156563
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.744
_shelx_estimated_absorpt_t_min   0.488
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00N(H00N,H00O), C00O(H00P,H00Q), C00P(H00R,H00S)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00C), C00C(H00D), C00E(H00E), C00G(H00G), C00H(H00H),
 C00J(H00J), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00L(H00F,H00I,H00L)
;
_shelx_res_checksum              56897
_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.489