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_7247377
_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         'C14 H13 N O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-16
_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                 101.713(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3019(4)
_cell_length_b                   6.9207(3)
_cell_length_c                   16.2735(6)
_cell_measurement_reflns_used    7823
_cell_measurement_temperature    299.03
_cell_measurement_theta_max      26.7090
_cell_measurement_theta_min      2.0850
_cell_volume                     1246.36(9)
_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      299.03
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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     24.00  50.00   0.50    3.00    --   16.22  18.00 -24.00   52
  2  \w     69.00  94.00   0.50    3.00    --   16.22  18.00 -24.00   50
  3  \w    -37.00  22.00   0.50    3.00    --  -14.97 -94.00-120.00  118
  4  \w    -61.00  63.00   0.50    3.00    --  -14.97  18.00 -24.00  248
  5  \w    -39.00  49.00   0.50    3.00    --  -14.97  45.00 -30.00  176
  6  \w    -69.00 -10.00   0.50    3.00    --  -14.97 125.00  90.00  118
  7  \w    -63.00 -12.00   0.50    3.00    --  -14.97 125.00   0.00  102
  8  \w    -57.00  12.00   0.50    3.00    --   16.22 -30.00 120.00  138
  9  \w    -62.00  59.00   0.50    3.00    --   16.22 -18.00 167.00  242
 10  \w    -70.00  10.00   0.50    3.00    --  -14.97 -30.00 150.00  160
 11  \w    -85.00  -2.00   0.50    3.00    --  -14.97 -61.00 120.00  166
 12  \w    -93.00   7.00   0.50    3.00    --  -14.97 -18.00 167.00  200
;
_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      0.0457897000
_diffrn_orient_matrix_UB_12      0.0078411000
_diffrn_orient_matrix_UB_13      0.0368148000
_diffrn_orient_matrix_UB_21      0.0426512000
_diffrn_orient_matrix_UB_22      0.0239511000
_diffrn_orient_matrix_UB_23      -0.0248252000
_diffrn_orient_matrix_UB_31      -0.0138760000
_diffrn_orient_matrix_UB_32      0.0993795000
_diffrn_orient_matrix_UB_33      0.0031042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.849
_diffrn_reflns_theta_min         2.445
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60390
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0765
_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^)+(0.1084P)^2^+0.9247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2144
_refine_ls_wR_factor_ref         0.2262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1982
_reflns_number_total             2593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02975a4.cif
_cod_data_source_block           dbr61
_cod_depositor_comments
'Adding full bibliography for 7247377--7247381.cif.'
_cod_database_code               7247377
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 99.53
_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:
 C13(H13A,H13B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C3(H3), C2(H2)
;
_shelx_res_checksum              85070
_shelx_hkl_checksum              78620
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.546