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_7247380
_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 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-15
_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                 112.011(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4952(7)
_cell_length_b                   5.8210(3)
_cell_length_c                   14.2222(7)
_cell_measurement_reflns_used    4751
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      24.2260
_cell_measurement_theta_min      2.6510
_cell_volume                     1266.06(11)
_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      293.00(10)
_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 0.964
_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     25.00  58.00   0.50    4.00    --  -14.97  30.00 -60.00   66
  2  \w     25.00  94.00   0.50    4.00    --   16.22  10.00-113.00  138
  3  \w     21.00  54.00   0.50    4.00    --   16.22-125.00-180.00   66
  4  \w    -37.00  22.00   0.50    4.00    --  -14.97 -94.00-120.00  118
  5  \w     23.00  49.00   0.50    4.00    --   16.22-125.00 -60.00   52
  6  \w     19.00  45.00   0.50    4.00    --   16.22 -94.00   0.00   52
  7  \w    -37.00   1.00   0.50    4.00    --   16.22 -94.00   0.00   76
  8  \w    -65.00  94.00   0.50    4.00    --   16.22 -10.00  73.00  318
  9  \w    -15.00  17.00   0.50    4.00    --  -14.97  30.00 -60.00   64
 10  \w     -9.00  88.00   0.50    4.00    --   16.22  30.00 -90.00  194
 11  \w    -53.00 -12.00   0.50    4.00    --  -14.97 125.00  60.00   82
 12  \w    -38.00 -13.00   0.50    4.00    --  -14.97 125.00 150.00   50
 13  \w    -96.00  63.00   0.50    4.00    --  -14.97 -10.00  73.00  318
 14  \w    -68.00 -11.00   0.50    4.00    --  -14.97 125.00 -60.00  114
 15  \w    -92.00  66.00   0.50    4.00    --  -14.97  10.00-113.00  316
;
_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      -0.0454850000
_diffrn_orient_matrix_UB_12      -0.0151804000
_diffrn_orient_matrix_UB_13      -0.0122111000
_diffrn_orient_matrix_UB_21      -0.0072911000
_diffrn_orient_matrix_UB_22      0.0048362000
_diffrn_orient_matrix_UB_23      -0.0523948000
_diffrn_orient_matrix_UB_31      0.0054215000
_diffrn_orient_matrix_UB_32      -0.1207667000
_diffrn_orient_matrix_UB_33      -0.0005153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.903
_diffrn_reflns_theta_min         2.664
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72612
_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    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0692
_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^)+(0.1215P)^2^+0.0625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1651
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02975a4.cif
_cod_data_source_block           dbr44
_cod_depositor_comments
'Adding full bibliography for 7247377--7247381.cif.'
_cod_database_code               7247380
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.72
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 1.12
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 1.12
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.12A with sigma of 0.04 and
sigma for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1.12A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3), C2(H2)
;
_shelx_res_checksum              18269
_shelx_hkl_checksum              94159
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.545