Preparation of Optically Active cis-Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes.
Su, Yan; Li, Qing-Fang; Zhao, Yu-Ming; Gu, Peiming; Organic letters 18 (2016) 4356–4359; doi:10.1021/acs.orglett.6b02117

data_1555695
_publ_section_title
;
 Preparation of Optically Active cis-Cyclopropane Carboxylates:
 Cyclopropanation of \a-Silyl Stryenes with Aryldiazoacetates and
 Desilylation of the Resulting Silyl Cyclopropanes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4356
_journal_page_last               4359
_journal_paper_doi               10.1021/acs.orglett.6b02117
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 Cl O3'
_chemical_formula_sum            'C19 H19 Cl O3'
_chemical_formula_weight         330.79
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-18
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4147(7)
_cell_length_b                   9.8374(10)
_cell_length_c                   20.9238(19)
_cell_measurement_reflns_used    1296
_cell_measurement_temperature    290.53(10)
_cell_measurement_theta_max      23.9980
_cell_measurement_theta_min      4.1290
_cell_volume                     1732.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.53(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -45.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8805   77.0000   60.0000 32

  2 omega  -30.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4117   19.0000 -120.0000 120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0462154000
_diffrn_orient_matrix_UB_12      0.0456493000
_diffrn_orient_matrix_UB_13      -0.0183638000
_diffrn_orient_matrix_UB_21      0.0071648000
_diffrn_orient_matrix_UB_22      0.0439532000
_diffrn_orient_matrix_UB_23      0.0268411000
_diffrn_orient_matrix_UB_31      0.0700728000
_diffrn_orient_matrix_UB_32      -0.0345634000
_diffrn_orient_matrix_UB_33      0.0094990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4382
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.331
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0557P)^2^+0.0228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.588
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                2116
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02117_si_003.cif
_cod_data_source_block           sn07105
_cod_database_code               1555695
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-16
_olex2_submission_special_instructions 'No special instructions were received'