Asymmetric synthesis of pharmaceutically relevant 1-aryl-2-heteroaryl- and 1,2-diheteroarylcyclopropane-1-carboxylates
Sharland, Jack C.; Wei, Bo; Hardee, David J.; Hodges, Timothy R.; Gong, Wei; Voight, Eric A.; Davies, Huw M. L.; Chemical Science  (2021) –; doi:10.1039/D1SC02474D

data_1564264
_publ_section_title
;
 Asymmetric synthesis of pharmaceutically relevant 1-aryl-2-heteroaryl-
 and 1,2-diheteroarylcyclopropane-1-carboxylates
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02474D
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 Cl N O3'
_chemical_formula_sum            'C18 H18 Cl N O3'
_chemical_formula_weight         331.801
_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_Int_Tables_number      19
_audit_creation_date             2020-01-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.77283(16)
_cell_length_b                   12.4768(2)
_cell_length_c                   15.4124(3)
_cell_measurement_reflns_used    28796
_cell_measurement_temperature    102(3)
_cell_measurement_theta_max      38.1440
_cell_measurement_theta_min      2.0930
_cell_volume                     1686.99(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      102(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9563
_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     33.00  80.00   0.50    7.00    --   25.69-165.00 160.00   94
  2  \w    -42.00 -10.00   0.50    7.00    --  -25.84  56.00 -36.00   64
  3  \w     42.00  93.00   0.50    7.00    --   25.69 178.00 -60.00  102
  4  \w     46.00  72.00   0.50    7.00    --   25.69 178.00-120.00   52
  5  \w    -14.00  59.00   0.50    7.00    --   25.69 -99.00 120.00  146
  6  \w    -99.00 -11.00   0.50    7.00    --  -25.84 -38.00-180.00  176
  7  \w      6.00  36.00   0.50    9.00    --  -25.84  56.00 -36.00   60
  8  \w     44.00  84.00   0.50    9.00    --   25.84  56.00 -36.00   80
  9  \w    -79.00 -19.00   0.50    9.00    --  -25.84 -77.00 150.00  120
 10  \w     43.00  98.00   0.50    9.00    --   25.84 178.00 -30.00  110
 11  \w     74.00  99.00   0.50    9.00    --   25.84  57.00-180.00   50
 12  \w    -40.00  -2.00   0.50    9.00    --   25.84 -38.00-120.00   76
 13  \w    -47.00  -8.00   0.50    9.00    --   25.84 -38.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0792154000
_diffrn_orient_matrix_UB_12      -0.0108024000
_diffrn_orient_matrix_UB_13      0.0031742000
_diffrn_orient_matrix_UB_21      -0.0147992000
_diffrn_orient_matrix_UB_22      -0.0394847000
_diffrn_orient_matrix_UB_23      0.0320716000
_diffrn_orient_matrix_UB_31      -0.0068000000
_diffrn_orient_matrix_UB_32      -0.0394360000
_diffrn_orient_matrix_UB_33      -0.0328459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9563
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42004
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9420
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         38.16
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             696.923
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.514
_exptl_crystal_size_min          0.303
_refine_diff_density_max         0.3291
_refine_diff_density_min         -0.2258
_refine_diff_density_rms         0.0339
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_d_res_high            0.5752
_refine_ls_d_res_low             9.6975
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0429
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     371
_refine_ls_number_reflns         8753
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.0381
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.0026
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.0499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0642
_reflns_Friedel_coverage         0.924
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                8164
_reflns_number_total             8753
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1sc02474d2.cif
_cod_data_source_block           JCS-ELN46-0036
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1564264
_chemical_oxdiff_formula         'C72  H72  Cl4  N4  O12  '
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C17, H17c, H17a, H17b, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, H13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, H14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, H16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, C10, H10c, H10a, H10b
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, H3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, H4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, H5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id JCS-ELN46-0036
_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 1.863
_oxdiff_exptl_absorpt_empirical_full_min 0.544