Synthesis of chiral pyrimidine-substituted diester D-A cyclopropanes <i>via</i> asymmetric cyclopropanation of phenyliodonium ylides.
Wang, Hai-Xia; Li, Wen-Peng; Zhang, Mi-Mi; Xie, Ming-Sheng; Qu, Gui-Rong; Guo, Hai-Ming; Chemical communications (Cambridge, England) 56 (2020) 11649–11652; doi:10.1039/d0cc04536e

data_7127084
_publ_section_title
;
 Synthesis of chiral pyrimidine-substituted diester D-A cyclopropanes
 <i>via</i> asymmetric cyclopropanation of phenyliodonium ylides.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11649
_journal_page_last               11652
_journal_paper_doi               10.1039/d0cc04536e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N2 O7'
_chemical_formula_sum            'C18 H16 N2 O7'
_chemical_formula_weight         372.33
_chemical_name_systematic        lwp
_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     iterative
_audit_creation_date             2020-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.48180(10)
_cell_length_b                   10.0714(2)
_cell_length_c                   23.3470(3)
_cell_measurement_reflns_used    15045
_cell_measurement_temperature    292.7(2)
_cell_measurement_theta_max      70.8470
_cell_measurement_theta_min      4.7620
_cell_volume                     1759.25(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.7(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_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    -57.00  31.00   1.00    1.00    --  -35.62  67.00-123.00   88
  2  \w    -31.00  57.00   1.00    1.00    --   35.62 -67.00 102.00   88
  3  \w     41.00 128.00   1.00    3.11    --  107.12 -67.00 102.00   87
  4  \w     39.00 134.00   1.00    3.11    --  107.12 -78.00 -15.00   95
  5  \w     40.00 134.00   1.00    3.11    --  107.12 -77.00-129.00   94
  6  \w    -62.00  32.00   1.00    1.00    --  -35.62  77.00  -4.00   94
  7  \w   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-180.00   73
  8  \w     19.00 103.00   1.00    1.00    --   35.62  57.00 -60.00   84
  9  \w     55.00 108.00   1.00    1.00    --   35.62-178.00 150.00   53
 10  \w     90.00 176.00   1.00    3.11    --  107.12  45.00 150.00   86
 11  \w     90.00 176.00   1.00    3.11    --  107.12  45.00-180.00   86
 12  \w     89.00 174.00   1.00    3.11    --  107.12  61.00  90.00   85
 13  \w     37.00 113.00   1.00    3.11    --  107.12-111.00-120.00   76
 14  \w    100.00 177.00   1.00    3.11    --  107.12 111.00 -60.00   77
 15  \w      9.00 103.00   1.00    1.00    --   35.62  77.00 -30.00   94
 16  \w     19.00 103.00   1.00    1.00    --   35.62  57.00  90.00   84
 17  \w      9.00 103.00   1.00    1.00    --   35.62  77.00 120.00   94
 18  \w     19.00 103.00   1.00    1.00    --   35.62  57.00-120.00   84
 19  \w     19.00 103.00   1.00    1.00    --   35.62  57.00  30.00   84
 20  \w     86.00 177.00   1.00    3.11    --  107.12  30.00  30.00   91
 21  \w     37.00 113.00   1.00    3.11    --  107.12-111.00  60.00   76
 22  \w     86.00 177.00   1.00    3.11    --  107.12  30.00 -90.00   91
 23  \w     80.00 175.00   1.00    3.11    --  107.12  77.00 -90.00   95
 24  \w     89.00 174.00   1.00    3.11    --  107.12  61.00  60.00   85
 25  \w     80.00 175.00   1.00    3.11    --  107.12  77.00-150.00   95
 26  \w     80.00 175.00   1.00    3.11    --  107.12  77.00  30.00   95
 27  \w     80.00 175.00   1.00    3.11    --  107.12  77.00 -30.00   95
 28  \w     90.00 176.00   1.00    3.11    --  107.12  45.00 120.00   86
 29  \w     86.00 177.00   1.00    3.11    --  107.12  30.00 -30.00   91
 30  \w      6.00 107.00   1.00    1.00    --   35.62  19.00  30.00  101
 31  \w      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
 32  \w      9.00 103.00   1.00    1.00    --   35.62  77.00-180.00   94
 33  \w    -24.00  63.00   1.00    1.00    --   35.62 -78.00 -15.00   87
 34  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
 35  \w     80.00 175.00   1.00    3.11    --  107.12  77.00  60.00   95
 36  \w     89.00 174.00   1.00    3.11    --  107.12  61.00 120.00   85
 37  \w     80.00 175.00   1.00    3.11    --  107.12  77.00-180.00   95
 38  \w     89.00 174.00   1.00    3.11    --  107.12  61.00 150.00   85
 39  \w     80.00 175.00   1.00    3.11    --  107.12  77.00 -60.00   95
 40  \w     80.00 175.00   1.00    3.11    --  107.12  77.00-120.00   95
 41  \w     89.00 174.00   1.00    3.11    --  107.12  61.00 -30.00   85
 42  \w     86.00 161.00   1.00    3.11    --  107.12  30.00 -60.00   75
 43  \w     80.00 175.00   1.00    3.11    --  107.12  77.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684099000
_diffrn_orient_matrix_UB_12      0.0874939000
_diffrn_orient_matrix_UB_13      -0.0494708000
_diffrn_orient_matrix_UB_21      0.1585519000
_diffrn_orient_matrix_UB_22      0.0954644000
_diffrn_orient_matrix_UB_23      0.0089350000
_diffrn_orient_matrix_UB_31      0.1121038000
_diffrn_orient_matrix_UB_32      -0.0814388000
_diffrn_orient_matrix_UB_33      -0.0428104000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31254
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.663
_diffrn_reflns_theta_min         3.787
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.406
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0695P)^2^+0.1171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3259
_reflns_number_total             3434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04536e2.cif
_cod_data_source_block           lwp-20191021
_cod_depositor_comments          'Adding full bibliography for 7127084.cif.'
_cod_database_code               7127084
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.814
_diffrn_oxdiff_digest_frames
;
01806c757ea229f8624f476f2fc4e0b91a0003727d6
;
_diffrn_oxdiff_digest_hkl
;
01db0e53f227bad8a4054566ca4302ffd0715a
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C2(H2), C3(H3), C26(H26), C24(H24), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              1243
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.783