Conformation-controlled catalytic asymmetric synthesis of Swaminathan ketones
Krishna, Anugam V.; Sanwal, Shyam D.; Rath, Sibani; Lakshmi, P. R.; Ramachary, Dhevalapally B.; Green Chemistry 26 (2024) 771–784; doi:10.1039/D3GC02975A

data_7247378
_publ_section_title
;
 Conformation-controlled catalytic asymmetric synthesis of Swaminathan
 ketones
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              771
_journal_page_last               784
_journal_paper_doi               10.1039/D3GC02975A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C18 H22 O3'
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6941(4)
_cell_length_b                   17.9069(10)
_cell_length_c                   10.1924(5)
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      22.0080
_cell_measurement_theta_min      2.2690
_cell_volume                     1586.80(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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_environment      air
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -20.00   9.00   0.50   11.17    --  -15.60 -45.00  60.00   58
  2  \w      8.00  44.00   0.50   11.17    --   16.22 -94.00  30.00   72
  3  \w     11.00  72.00   0.50   11.17    --   16.22-127.00  87.00  122
  4  \w    -37.00   4.00   0.50   11.17    --   16.22 -94.00  30.00   82
  5  \w    -74.00 -28.00   0.50   11.17    --  -15.60 -45.00  60.00   92
  6  \w    -51.00 -10.00   0.50   11.17    --  -15.60 125.00  30.00   82
  7  \w    -86.00 -24.00   0.50   11.17    --  -15.60 151.00  57.00  124
  8  \w    -70.00 -26.00   0.50   11.17    --  -15.60 125.00 150.00   88
  9  \w    -97.00  63.00   0.50   11.17    --  -15.60  -9.00 -80.00  320
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, 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      0.0629045000
_diffrn_orient_matrix_UB_12      -0.0112128000
_diffrn_orient_matrix_UB_13      0.0244118000
_diffrn_orient_matrix_UB_21      0.0505886000
_diffrn_orient_matrix_UB_22      -0.0012810000
_diffrn_orient_matrix_UB_23      -0.0310715000
_diffrn_orient_matrix_UB_31      0.0112399000
_diffrn_orient_matrix_UB_32      0.0686543000
_diffrn_orient_matrix_UB_33      0.0033869000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9467
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0574P)^2^+0.0363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.749
_reflns_number_gt                1948
_reflns_number_total             2473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02975a4.cif
_cod_data_source_block           dbr54
_cod_depositor_comments
'Adding full bibliography for 7247377--7247381.cif.'
_cod_database_code               7247378
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.89
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C2(H2A,H2B), C8(H8A,H8B), C5(H5A,H5B), C15(H15A,H15B), C3(H3A,
 H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              11797
_shelx_hkl_checksum              13788
_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 1.690
_oxdiff_exptl_absorpt_empirical_full_min 0.553