Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne.
Liu, Qi-Sheng; Wang, De-Yin; Yang, Zhi-Jun; Luan, Yu-Xin; Yang, Jin-Fei; Li, Jiang-Fei; Pu, You-Ge; Ye, Mengchun; Journal of the American Chemical Society 139 (2017) 18150–18153; doi:10.1021/jacs.7b09947

data_4131747
_publ_section_title
;
 Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl
 Carboxamide with Alkyne.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18150
_journal_page_last               18153
_journal_paper_doi               10.1021/jacs.7b09947
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C22 H23 N O2'
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.0800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9392(2)
_cell_length_b                   10.7960(2)
_cell_length_c                   32.3003(4)
_cell_measurement_reflns_used    34154
_cell_measurement_temperature    80(1)
_cell_measurement_theta_max      74.1210
_cell_measurement_theta_min      4.2920
_cell_volume                     3446.44(10)
_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      80(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -89.00  21.00   0.50    0.50    --    0.00 -38.00-120.00  220
  2  \w    -21.00  89.00   0.50    0.50    --    0.00  38.00-150.00  220
  3  \w    -33.00  89.00   0.50    0.50    --    0.00  82.00   0.00  244
  4  \w      6.00 117.00   0.50    3.50    --   95.80 -30.00 -90.00  222
  5  \w      6.00 118.00   0.50    3.50    --   95.80 -45.00 150.00  224
  6  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00-150.00  246
  7  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00-180.00  246
  8  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00 120.00  246
  9  \w     74.00 185.00   0.50    3.50    --   95.80  30.00-150.00  222
 10  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00 -90.00  246
 11  \w     69.00 185.00   0.50    3.50    --   95.80  61.00   0.00  232
 12  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00   0.00  246
 13  \w      6.00 117.00   0.50    3.50    --   95.80 -30.00   0.00  222
 14  \w      6.00 127.00   0.50    3.50    --   95.80 -77.00  60.00  242
 15  \w      6.00 129.00   0.50    3.50    --   95.80 -82.00  90.00  246
 16  \w      6.00 122.00   0.50    3.50    --   95.80 -61.00 -90.00  232
 17  \w      6.00 118.00   0.50    3.50    --   95.80 -45.00  60.00  224
 18  \w    -21.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  220
 19  \w    -89.00  33.00   0.50    0.50    --    0.00 -82.00-180.00  244
 20  \w    -89.00  28.00   0.50    0.50    --    0.00 -19.00 -90.00  234
 21  \w     69.00 185.00   0.50    3.50    --   95.80  61.00  30.00  232
 22  \w     69.00 185.00   0.50    3.50    --   95.80  61.00 -60.00  232
 23  \w     73.00 185.00   0.50    3.50    --   95.80  45.00 150.00  224
 24  \w     63.00 185.00   0.50    3.50    --   95.80  15.00 -60.00  244
 25  \w     64.00 185.00   0.50    3.50    --   95.80  77.00  90.00  242
 26  \w     62.00 185.00   0.50    3.50    --   95.80  82.00-120.00  246
 27  \w     62.00 185.00   0.50    3.50    --   95.80  82.00-180.00  246
 28  \w     62.00 185.00   0.50    3.50    --   95.80  82.00 -60.00  246
 29  \w     62.00 185.00   0.50    3.50    --   95.80  82.00  60.00  246
 30  \w     62.00 185.00   0.50    3.50    --   95.80  82.00-150.00  246
 31  \w     69.00 185.00   0.50    3.50    --   95.80  61.00 150.00  232
 32  \w     63.00 185.00   0.50    3.50    --   95.80  15.00 120.00  244
 33  \w    -89.00  31.00   0.50    0.50    --    0.00 -77.00 -60.00  240
 34  \w    -89.00  25.00   0.50    0.50    --    0.00 -57.00-180.00  228
 35  \w    -25.00  89.00   0.50    0.50    --    0.00  57.00  90.00  228
 36  \w     62.00 185.00   0.50    3.50    --   95.80  82.00 150.00  246
 37  \w     64.00 185.00   0.50    3.50    --   95.80  77.00 -30.00  242
 38  \w     64.00 185.00   0.50    3.50    --   95.80  77.00 -90.00  242
 39  \w     67.00 185.00   0.50    3.50    --   95.80  68.00-145.55  236
 40  \w     64.00 185.00   0.50    3.50    --   95.80  77.00   0.00  242
 41  \w     66.00 185.00   0.50    3.50    --   95.80  72.00  89.01  238
 42  \w     64.00 113.00   0.50    3.50    --   95.80  77.00-120.00   98
 43  \w     69.00 185.00   0.50    3.50    --   95.80  61.00  60.00  232
;
_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      -0.0122429000
_diffrn_orient_matrix_UB_12      -0.1315249000
_diffrn_orient_matrix_UB_13      0.0177270000
_diffrn_orient_matrix_UB_21      0.0130318000
_diffrn_orient_matrix_UB_22      0.0532400000
_diffrn_orient_matrix_UB_23      0.0444826000
_diffrn_orient_matrix_UB_31      -0.1548687000
_diffrn_orient_matrix_UB_32      0.0149324000
_diffrn_orient_matrix_UB_33      -0.0027605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            65204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.648
_diffrn_reflns_theta_min         4.320
_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  0.67120
_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_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0418P)^2^+2.6542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3292
_reflns_number_total             3505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09947_si_002.cif
_cod_data_source_block           lyx-4-160
_cod_database_code               4131747
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.88
_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. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N2)
Uanis(C20) = Uanis(C23)
Uanis(C21) = Uanis(C24)
Uanis(C19) = Uanis(C25)
Uanis(C22) = Uanis(C26)
3. Others
 Sof(N2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=1-FVAR(1)
 Sof(N1)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
 C26(H26A,H26B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18)
;
_shelx_res_checksum              71996
_shelx_hkl_checksum              14831
_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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.792