An entry to vinylcyclopropane through palladium-catalyzed intramolecular cyclopropanation of alkenes with unstabilized allylic tosylhydrazones
Yang Yang; Jinpeng Li; Biao Du; Changchun Yuan; Bo Liu; Song Qin; Chem.Commun. 51 (2015) 6179–; doi:10.1039/C5cc00235D

data_7116876
_publ_section_title
;
 An entry to vinylcyclopropane through palladium-catalyzed intramolecular
 cyclopropanation of alkenes with unstabilized allylic tosylhydrazones
;
_journal_name_full               Chem.Commun.
_journal_page_first              6179
_journal_paper_doi               10.1039/C5cc00235D
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H18 Cl O2'
_chemical_formula_sum            'C19 H18 Cl O2'
_chemical_formula_weight         313.78
_chemical_name_systematic        h003-w6
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-01-10 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.6351(6)
_cell_length_b                   11.6351(6)
_cell_length_c                   48.952(3)
_cell_measurement_reflns_used    5178
_cell_measurement_temperature    292.23(10)
_cell_measurement_theta_max      71.6490
_cell_measurement_theta_min      3.8960
_cell_volume                     6626.9(6)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  120.0000 74

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

  4 omega   14.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  -90.0000 27

  5 omega   70.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  -90.0000 26

  6 omega   -9.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 62

  7 omega   63.00   88.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 25

  8 omega   43.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 53

  9 omega   66.00   93.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 27

 10 omega   54.00  132.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 78

 11 omega   38.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 12 omega   44.00   80.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -33.0000   18.0000 36

 13 omega   44.00   71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 27

 14 omega   39.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0698781000
_diffrn_orient_matrix_UB_12      -0.0073503000
_diffrn_orient_matrix_UB_13      -0.0266462000
_diffrn_orient_matrix_UB_21      0.1037417000
_diffrn_orient_matrix_UB_22      0.0555123000
_diffrn_orient_matrix_UB_23      0.0145134000
_diffrn_orient_matrix_UB_31      0.0440693000
_diffrn_orient_matrix_UB_32      -0.1198052000
_diffrn_orient_matrix_UB_33      0.0083108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            19825
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.106
_diffrn_reflns_theta_min         4.668
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25881
_exptl_absorpt_correction_type   multi-scan
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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
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_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             2632
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       0.00045(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0954
_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^)+(0.1454P)^2^+4.3966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2674
_refine_ls_wR_factor_ref         0.2926
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                4355
_reflns_number_total             6436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc00235d2.cif
_cod_data_source_block           lb-h0003-w6
_cod_original_cell_volume        6626.9(8)
_cod_database_code               7116876
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H007(0.068) H008(0.076) H00G(0.079) H00H(0.073) H00J(0.079)
 H00K(0.077) H00L(0.081) H00O(0.081) H00I(0.074) H00A(0.082) H00B(0.082)
 H00M(0.086) H00N(0.083) H00C(0.086) H00D(0.086) H00P(0.085) H00Q(0.082)
 H00E(0.09) H00F(0.09) H00T(0.081) H00U(0.079) H00V(0.088) H00X(0.095)
 H00Y(0.098) H00R(0.093) H00S(0.093) H01C(0.091) H01D(0.091) H011(0.091)
 H012(0.102) H01A(0.129) H01B(0.129) H015(0.117) H017(0.128) H018(0.17)
 Fixed X: H007(0.4204) H008(0.747) H00G(0.6843) H00H(0.5871) H00J(0.6457)
 H00K(0.8194) H00L(0.7588) H00O(0.7083) H00I(0.6207) H00A(0.3198) H00B(0.4355)
 H00M(0.3239) H00N(0.632) H00C(0.5579) H00D(0.6719) H00P(0.6044) H00Q(0.2632)
 H00E(0.5713) H00F(0.5254) H00T(0.449) H00U(0.4522) H00V(0.7685) H00X(0.9932)
 H00Y(0.8886) H00R(0.6078) H00S(0.4817) H01C(0.4531) H01D(0.5028) H011(0.5333)
 H012(0.4701) H01A(0.1957) H01B(0.3097) H015(0.3837) H017(0.5577) H018(0.2362)
 Fixed Y: H007(0.9055) H008(0.7424) H00G(0.3801) H00H(0.5792) H00J(0.6826)
 H00K(0.5462) H00L(0.5687) H00O(0.683) H00I(0.807) H00A(0.7836) H00B(0.7321)
 H00M(0.8593) H00N(0.7221) H00C(1.0392) H00D(0.9879) H00P(0.5479) H00Q(0.7625)
 H00E(0.88) H00F(1.0062) H00T(0.8903) H00U(0.6737) H00V(0.3618) H00X(0.5181)
 H00Y(0.4489) H00R(0.4374) H00S(0.4846) H01C(0.446) H01D(0.3333) H011(0.5988)
 H012(0.5012) H01A(1.0478) H01B(1.1012) H015(0.7604) H017(0.7848) H018(0.9388)
 Fixed Z: H007(0.645) H008(0.971) H00G(0.8287) H00H(0.8519) H00J(0.9331)
 H00K(0.8661) H00L(0.8114) H00O(0.8236) H00I(0.6671) H00A(0.6741) H00B(0.6852)
 H00M(0.5618) H00N(0.6068) H00C(0.6697) H00D(0.6818) H00P(0.8969) H00Q(0.5231)
 H00E(0.7133) H00F(0.7157) H00T(0.5996) H00U(0.6304) H00V(0.8886) H00X(0.9537)
 H00Y(0.9169) H00R(0.7822) H00S(0.781) H01C(0.827) H01D(0.8139) H011(0.5806)
 H012(0.5424) H01A(0.7073) H01B(0.7192) H015(0.7836) H017(0.7515) H018(0.7489)
;
_shelx_res_checksum              54846
_shelx_hkl_checksum              38624
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'