Low catalyst loading enabled organocatalytic synthesis of chiral bis-heterocyclic frameworks containing pyrazole and isoxazole.
Kaur, Banni Preet; Sharma, Vivek; Sahoo, Subash Chandra; Chimni, Swapandeep Singh; Organic & biomolecular chemistry 19 (2021) 9910–9924; doi:10.1039/d1ob01313k

data_7158385
_publ_section_title
;
 Low catalyst loading enabled organocatalytic synthesis of chiral
 bis-heterocyclic frameworks containing pyrazole and isoxazole.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9910
_journal_page_last               9924
_journal_paper_doi               10.1039/d1ob01313k
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H20 Cl N3 O4'
_chemical_formula_sum            'C22 H20 Cl N3 O4'
_chemical_formula_weight         425.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2019-09-05 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.009(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7803(2)
_cell_length_b                   9.3559(3)
_cell_length_c                   14.8204(4)
_cell_measurement_reflns_used    9512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7420
_cell_measurement_theta_min      3.4770
_cell_volume                     1078.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.947
_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    -17.00  11.00   0.50    8.00    --   -9.95 -90.00   5.00   56
  2  \w    -21.00   6.00   0.50    8.00    --   -9.95  90.00 120.00   54
  3  \w    -28.00  37.00   0.50    8.00    --   10.22 -90.00   5.00  130
  4  \w     -9.00  31.00   0.50    8.00    --   10.22  90.00 120.00   80
  5  \w    -74.00   4.00   0.50    8.00    --   -9.95 -38.00   0.00  156
  6  \w    -58.00 -15.00   0.50    8.00    --   -9.95 125.00-120.00   86
  7  \w     -6.00  31.00   0.50    8.00    --   -9.95  38.00 -90.00   74
  8  \w    -38.00  -6.00   0.50    8.00    --   10.22 125.00-121.60   64
  9  \w    -23.00   3.00   0.50    8.00    --   10.22 118.00  -3.63   52
 10  \w    -54.00 -16.00   0.50    8.00    --   10.22 -19.00 120.00   76
 11  \w    -13.00  42.00   0.50    8.00    --   10.22 -99.00-150.00  110
 12  \w    -54.00 -24.00   0.50    8.00    --   10.22 -77.00-150.00   60
 13  \w    -19.00  36.00   0.50    8.00    --   10.22 -77.00-150.00  110
 14  \w     -9.00  16.00   0.50    8.00    --   10.22 -99.00 120.00   50
 15  \w    -54.00  17.00   0.50    8.00    --   10.22 -38.00 -90.00  142
 16  \w    -14.00  12.00   0.50    8.00    --   10.22 -99.00-180.00   52
 17  \w    -34.00  12.00   0.50    8.00    --   10.22 -38.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0125347000
_diffrn_orient_matrix_UB_12      0.0687071000
_diffrn_orient_matrix_UB_13      0.0191862000
_diffrn_orient_matrix_UB_21      0.0368114000
_diffrn_orient_matrix_UB_22      -0.0319258000
_diffrn_orient_matrix_UB_23      0.0388755000
_diffrn_orient_matrix_UB_31      0.0824229000
_diffrn_orient_matrix_UB_32      0.0037400000
_diffrn_orient_matrix_UB_33      -0.0202535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14001
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         3.406
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0907P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                3095
_reflns_number_total             4537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01313k2.cif
_cod_data_source_block           sub-gndu2
_cod_depositor_comments          'Adding full bibliography for 7158385.cif.'
_cod_database_code               7158385
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O Cl'
_diffrn_oxdiff_ac3_digest_frames
;
014a5aeb4633fd442ac092326057c5eaec0144486b9
;
_diffrn_oxdiff_ac3_digest_hkl
;
015746d478f9845665fb65ce4a4b48c709fbcc
;
_reflns_odcompleteness_completeness 99.70
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C18(H18), C20(H20), C19(H19), C22(H22), C6(H6), C8(H8),
 C21(H21), C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 2.189
_oxdiff_exptl_absorpt_empirical_full_min 0.726