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_7247379
_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_absolute_configuration rm
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_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
_audit_creation_date             2023-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-23 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.788(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9700(5)
_cell_length_b                   11.1812(6)
_cell_length_c                   7.9888(4)
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    299.0(2)
_cell_measurement_theta_max      25.6050
_cell_measurement_theta_min      2.7100
_cell_volume                     665.57(7)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.956
_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    -54.00  41.00   0.50    7.00    --   16.22 -45.00   0.00  190
  2  \w     10.00  71.00   0.50    7.00    --   16.22-125.00   0.00  122
  3  \w    -37.00  21.00   0.50    7.00    --  -15.60 -94.00 -60.00  116
  4  \w    -31.00  21.00   0.50    7.00    --  -15.60 -96.00-109.00  104
  5  \w    -40.00  55.00   0.50    7.00    --  -15.60  45.00-103.00  190
  6  \w    -37.00  53.00   0.50    7.00    --   16.22 -94.00-180.00  180
  7  \w     10.00  71.00   0.50    7.00    --   16.22-125.00-150.00  122
  8  \w     10.00  71.00   0.50    7.00    --   16.22-125.00-120.00  122
  9  \w    -70.00 -10.00   0.50    7.00    --  -15.60 125.00 -90.00  120
 10  \w    -89.00 -36.00   0.50    7.00    --  -15.60 -30.00  90.00  106
 11  \w    -54.00  41.00   0.50    7.00    --   16.22 -45.00 106.00  190
 12  \w    -37.00  21.00   0.50    7.00    --  -15.60 -94.00 150.00  116
 13  \w    -17.00  45.00   0.50    7.00    --   16.22  87.00 104.00  124
;
_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      -0.0203180000
_diffrn_orient_matrix_UB_12      0.0356860000
_diffrn_orient_matrix_UB_13      -0.0780932000
_diffrn_orient_matrix_UB_21      -0.0912145000
_diffrn_orient_matrix_UB_22      0.0025479000
_diffrn_orient_matrix_UB_23      -0.0071280000
_diffrn_orient_matrix_UB_31      0.0182902000
_diffrn_orient_matrix_UB_32      0.0524028000
_diffrn_orient_matrix_UB_33      0.0535366000
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7906
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.009
_diffrn_reflns_theta_min         2.727
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50160
_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    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0445P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                2006
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02975a4.cif
_cod_data_source_block           dbr56
_cod_depositor_comments
'Adding full bibliography for 7247377--7247381.cif.'
_cod_database_code               7247379
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.03
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C5(H5A,H5B), C2(H2A,H2B), C12(H12A,H12B), C9(H9A,H9B), C4(H4A,
 H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              33910
_shelx_hkl_checksum              33676
_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 4.092
_oxdiff_exptl_absorpt_empirical_full_min 0.454