Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.
Marichev, Kostiantyn O.; Ramey, Justin T.; Arman, Hadi; Doyle, Michael P.; Organic letters 19 (2017) 1306–1309; doi:10.1021/acs.orglett.7b00119

data_1545677
_publ_section_title
;
 Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed
 Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1306
_journal_page_last               1309
_journal_paper_doi               10.1021/acs.orglett.7b00119
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H18 O2'
_chemical_formula_sum            'C21 H18 O2'
_chemical_formula_weight         302.37
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
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_cell_measurement_temperature    98
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_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)'
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_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 330
               Slice: -125.0000 - 40.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 34.5186
              2theta: -34.7387
scan:
    Number of images: 108
               Slice: -68.0000 - -14.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 34.5186
              2theta: -34.7387
scan:
    Number of images: 102
               Slice: -66.0000 - -15.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 270.0000
                 XTD: 34.5186
              2theta: -34.7387
scan:
    Number of images: 60
               Slice: -55.0000 - -25.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 90.0000
                 XTD: 34.5186
              2theta: -34.7387
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
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_diffrn_orient_matrix_UB_21      -0.015432
_diffrn_orient_matrix_UB_22      0.023772
_diffrn_orient_matrix_UB_23      -0.078408
_diffrn_orient_matrix_UB_31      0.072051
_diffrn_orient_matrix_UB_32      -0.004913
_diffrn_orient_matrix_UB_33      -0.015670
_diffrn_radiation_monochromator  'Graphite Monochromator'
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_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10010
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.674
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.650
_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    1.255
_exptl_crystal_description       plank
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     279
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3185
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00119_si_004.cif
_cod_data_source_block           cd1505a
_cod_original_cell_volume        1600.6(5)
_cod_original_formula_sum        'C21 H18 O2 '
_cod_database_code               1545677
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'