Directed Cu(I)-Catalyzed Carbomagnesiation of 1-Arylcycloprop-2-ene-1-carboxamides En Route to Densely Substituted Functionalized Cyclopropanes.
Edwards, Andrew; Rubin, Michael; The Journal of organic chemistry 83 (2018) 8426–8448; doi:10.1021/acs.joc.8b01063

data_4035578
_publ_section_title
;
 Directed Cu(I)-Catalyzed Carbomagnesiation of
 1-Arylcycloprop-2-ene-1-carboxamides En Route to Densely Substituted
 Functionalized Cyclopropanes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8426
_journal_page_last               8448
_journal_paper_doi               10.1021/acs.joc.8b01063
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.2748(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9999(2)
_cell_length_b                   7.56312(8)
_cell_length_c                   17.9960(3)
_cell_measurement_reflns_used    10033
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8670
_cell_measurement_theta_min      5.3620
_cell_volume                     1875.43(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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     53.00  78.00   1.00    2.00    --   41.72 -89.00  -7.00   25
  2  \w     36.00  78.00   1.00    2.00    --   41.72-125.00 -60.00   42
  3  \w     37.00  63.00   1.00    8.00    --  112.00 -95.00-180.00   26
  4  \w     31.00 108.00   1.00    8.00    --  112.00 -95.00-150.00   77
  5  \w     68.00 140.00   1.00    8.00    --  112.00 -61.00 -30.00   72
  6  \w     77.00 103.00   1.00    8.00    --  112.00 -89.00  -7.00   26
  7  \w     40.00 139.00   1.00    8.00    --  112.00 -30.00   0.00   99
  8  \w    123.00 149.00   1.00    8.00    --  112.00  48.00  -4.00   26
  9  \w    111.00 137.00   1.00    8.00    --  112.00  77.00   0.00   26
 10  \w    139.00 164.00   1.00    8.00    --  112.00  89.00 108.00   25
 11  \w    107.00 177.00   1.00    8.00    --  112.00 111.00 120.00   70
 12  \w     96.00 173.00   1.00    8.00    --  112.00  77.00 150.00   77
 13  \w    149.00 174.00   1.00    8.00    --  112.00 111.00-120.00   25
 14  \w    112.00 138.00   1.00    8.00    --  112.00  89.00-149.00   26
 15  \w     91.00 141.00   1.00    8.00    --  112.00  61.00-150.00   50
 16  \w    -10.00  29.00   1.00    2.00    --   41.72 -89.00  -7.00   39
 17  \w    -20.00  33.00   1.00    2.00    --  -41.72  89.00-149.00   53
 18  \w    -88.00  -2.00   1.00    2.00    --  -41.72 125.00   0.00   86
 19  \w    153.00 178.00   1.00    8.00    --  112.00  49.00  -4.00   25
 20  \w     66.00  92.00   1.00    2.00    --   41.85-125.00 -60.00   26
 21  \w    -27.00  -1.00   1.00    2.00    --   41.85 -38.00   0.00   26
 22  \w     59.00  85.00   1.00    8.00    --  112.00 -95.00  60.00   26
 23  \w     54.00 115.00   1.00    8.00    --  112.00-111.00 -60.00   61
 24  \w    147.00 174.00   1.00    8.00    --  112.00  45.00-120.00   27
 25  \w     41.00 140.00   1.00    8.00    --  112.00 -30.00-180.00   99
 26  \w     59.00  97.00   1.00    8.00    --  112.00-111.00 -30.00   38
 27  \w     60.00  89.00   1.00    8.00    --  112.00 -49.00-151.00   29
 28  \w     84.00 109.00   1.00    8.00    --  112.00 -95.00   0.00   25
 29  \w    114.00 140.00   1.00    8.00    --  112.00 111.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207928000
_diffrn_orient_matrix_UB_12      0.0261511000
_diffrn_orient_matrix_UB_13      0.0765709000
_diffrn_orient_matrix_UB_21      -0.0896646000
_diffrn_orient_matrix_UB_22      -0.1207640000
_diffrn_orient_matrix_UB_23      -0.0359950000
_diffrn_orient_matrix_UB_31      0.0634081000
_diffrn_orient_matrix_UB_32      -0.1619042000
_diffrn_orient_matrix_UB_33      0.0391589000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13759
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.158
_diffrn_reflns_theta_min         4.924
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.252
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0457P)^2^+0.6327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3661
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01063_si_003.cif
_cod_data_source_block           anna_29092017_ae453_2
_cod_database_code               4035578
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.92
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H00P)=Sof(H00Q)=Sof(C00Q)=Sof(H00Z)=Sof(HA)=Sof(HB)=1-FVAR(1)
 Sof(H00N)=Sof(H00O)=Sof(C00P)=Sof(H00X)=Sof(H00Y)=Sof(H)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C006(H006), C007(H007), C00A(H00A)
3.b Secondary CH2 refined with riding coordinates:
 C00L(H00N,H00O), C00L(H00P,H00Q), C00N(H00S,H00T)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00I), C00H(H00J),
 C00I(H00K), C00J(H00L), C00K(H00M), C00M(H00R)
3.d Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00O(H00U,H00V,H00W), C00P(H00X,H00Y,H), C00Q(H00Z,HA,HB)
;
_shelx_res_checksum              8371
_shelx_hkl_checksum              31647
_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 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.607