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_1545322
_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_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                72.828(5)
_cell_angle_beta                 89.259(4)
_cell_angle_gamma                77.332(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4785(4)
_cell_length_b                   10.0969(5)
_cell_length_c                   11.6506(6)
_cell_measurement_reflns_used    5765
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.7140
_cell_measurement_theta_min      2.1530
_cell_volume                     818.79(8)
_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_temperature      98
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -68.00  55.00   0.50   35.00    --  -35.00  70.00 270.00  246
  2  \w    -68.00  36.00   0.50   35.00    --  -35.00  70.00  90.00  208
  3  \w    -52.00 -14.00   0.50   35.00    --  -35.00  70.00 180.00   76
  4  \w   -125.00 -91.00   0.50   35.00    --  -35.00   0.00   0.00   68
  5  \w    -65.00 -34.00   0.50   35.00    --  -35.00   0.00  90.00   62
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0929517000
_diffrn_orient_matrix_UB_12      0.0042432000
_diffrn_orient_matrix_UB_13      -0.0081966000
_diffrn_orient_matrix_UB_21      -0.0238171000
_diffrn_orient_matrix_UB_22      0.0728740000
_diffrn_orient_matrix_UB_23      -0.0027028000
_diffrn_orient_matrix_UB_31      0.0164919000
_diffrn_orient_matrix_UB_32      -0.0191657000
_diffrn_orient_matrix_UB_33      0.0632342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6248
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.832
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_recrystallization_method
'slow evaporation of hexane and dichloromethane'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0543P)^2^+0.2612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3488
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00119_si_002.cif
_cod_data_source_block           cd1527a
_cod_depositor_comments
'Adding full bibliography for 1545321--1545322.cif.'
_cod_database_code               1545322
_reflns_odcompleteness_completeness 99.76
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C17(H17), C14(H14), C10(H10), C19(H19), C13(H13), C20(H20),
 C11(H11), C12(H12), C18(H18)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.168
_oxdiff_exptl_absorpt_empirical_full_min 0.869