Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones.
Cheng, Qing-Qing; Yedoyan, Julietta; Arman, Hadi; Doyle, Michael P.; Journal of the American Chemical Society 138 (2016) 44–47; doi:10.1021/jacs.5b10860

data_4129841
_publ_section_title
;
 Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with
 Nitrones.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              44
_journal_page_last               47
_journal_paper_doi               10.1021/jacs.5b10860
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H37 Cl N2 O3 Si'
_chemical_formula_sum            'C28 H37 Cl N2 O3 Si'
_chemical_formula_weight         513.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.174(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.520(4)
_cell_length_b                   18.360(10)
_cell_length_c                   12.283(7)
_cell_measurement_reflns_used    4483
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.1
_cell_measurement_theta_min      2.0
_cell_volume                     1451.6(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
	Number of images: 248
	           Slice: -125.0000 - -1.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.0024
	          2theta: -34.9854
scan:
	Number of images: 114
	           Slice: -67.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 35.0024
	          2theta: -34.9854
scan:
	Number of images: 114
	           Slice: -68.0000 - -11.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.0024
	          2theta: -34.9854
scan:
	Number of images: 62
	           Slice: -65.0000 - -34.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.0024
	          2theta: -34.9854
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.147257
_diffrn_orient_matrix_UB_12      -0.039430
_diffrn_orient_matrix_UB_13      0.030002
_diffrn_orient_matrix_UB_21      0.009069
_diffrn_orient_matrix_UB_22      -0.049578
_diffrn_orient_matrix_UB_23      -0.020645
_diffrn_orient_matrix_UB_31      0.009680
_diffrn_orient_matrix_UB_32      -0.029967
_diffrn_orient_matrix_UB_33      0.076219
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.770
_diffrn_reflns_theta_full        25.036
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+2.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.502
_reflns_Friedel_fraction_full    0.533
_reflns_Friedel_fraction_max     0.533
_reflns_number_gt                3205
_reflns_number_total             3975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10860_si_002.cif
_cod_data_source_block           cd1356a
_cod_original_cell_volume        1451.5(15)
_cod_database_code               4129841
_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. Restrained distances
 C8-C7
 1.4 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C16(H16A,H16B), C15(H15A,H15B), C13(H13A,H13B),
 C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C22(H22), C19(H19), C28(H28), C24(H24), C26(H26),
 C25(H25), C27(H27)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C),
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              23311
_shelx_hkl_checksum              54938
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'