Combined prioritization and dereplication-based rapid identification of new 8-alkylated coumarins: podurins A and B from the leaves of Murraya paniculata and cytotoxic evaluation
Kumari, Sanju; Saini, Vaishali; Chakrabarty, Sanheeta; Kumar, Sanjay; Jha, Hem Chandra; Ronickom, Jac Fredo Agastinose; Kumar, Sanjeev; Jain, Shreyans K.; New Journal of Chemistry 49 (2025) 4842–4848; doi:10.1039/D4NJ05468G

data_7063669
_publ_section_title
;
 Combined prioritization and dereplication-based rapid identification of
 new 8-alkylated coumarins: podurins A and B from the leaves of Murraya
 paniculata and cytotoxic evaluation
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4842
_journal_page_last               4848
_journal_paper_doi               10.1039/D4NJ05468G
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C14 H14 O6'
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25
_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             2024-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.7462(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.78624(14)
_cell_length_b                   14.74804(17)
_cell_length_c                   10.33498(15)
_cell_measurement_reflns_used    9403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8290
_cell_measurement_theta_min      2.9930
_cell_volume                     1354.65(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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    -27.00  37.00   0.50    0.20    --   40.83 -32.00-180.00  128
  2  \w     28.00  83.00   0.50    0.20    --   96.04 -68.00-180.00  110
  3  \w     28.00  83.00   0.50    0.20    --   96.04 -68.00 -60.00  110
  4  \w     28.00  68.00   0.50    0.20    --   96.04 -59.00 -60.00   80
  5  \w     28.00  58.00   0.50    0.20    --   96.04 -51.00 -55.00   60
  6  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00 -30.00   56
  7  \w    -26.00  58.00   0.50    0.20    --   40.83 -51.00 -55.00  168
  8  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00-180.00   56
  9  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00  30.00   56
 10  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00  60.00   56
 11  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00 120.00   56
 12  \w    -35.00  24.00   0.50    0.20    --   40.83 -11.00 120.00  118
 13  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00-150.00   56
 14  \w     23.00 106.00   0.50    0.20    --   96.04 -96.00 -60.00  166
 15  \w     41.00 100.00   0.50    0.20    --   40.83-138.00-180.00  118
 16  \w     18.00  78.00   0.50    0.20    --   40.83-104.00-120.00  120
 17  \w     18.00  78.00   0.50    0.20    --   40.83-104.00 150.00  120
 18  \w    105.00 170.00   0.50    0.20    --   96.04  96.00   0.00  130
 19  \w     99.00 160.00   0.50    0.20    --   96.04 117.00 -30.00  122
 20  \w    105.00 170.00   0.50    0.20    --   96.04  96.00 -90.00  130
 21  \w     99.00 160.00   0.50    0.20    --   96.04 117.00-120.00  122
 22  \w    105.00 170.00   0.50    0.20    --   96.04  96.00 150.00  130
 23  \w     72.00 164.00   0.50    0.20    --   96.04  68.00  30.00  184
 24  \w     74.00 163.00   0.50    0.20    --   96.04  59.00-180.00  178
 25  \w     79.00 162.00   0.50    0.20    --   96.04  42.00-120.00  166
 26  \w     79.00 162.00   0.50    0.20    --   96.04  42.00  60.00  166
 27  \w     77.00 163.00   0.50    0.20    --   96.04  51.00  90.00  172
 28  \w     14.00 110.00   0.50    0.20    --   40.83  77.00   0.00  192
 29  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  30.00  192
 30  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  90.00  192
 31  \w     18.00 109.00   0.50    0.20    --   40.83  65.00 150.00  182
 32  \w     22.00 109.00   0.50    0.20    --   40.83  51.00  90.00  174
 33  \w     21.00 108.00   0.50    0.20    --   40.83  54.00 -90.00  174
 34  \w     14.00 110.00   0.50    0.20    --   40.83  77.00-150.00  192
 35  \w     14.00 110.00   0.50    0.20    --   40.83  77.00 -60.00  192
 36  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00 150.00  118
 37  \w    -58.00  27.00   0.50    0.20    --  -40.83  51.00  90.00  170
 38  \w    -58.00 -15.00   0.50    0.20    --  -82.50  51.00  90.00   86
 39  \w    -68.00 -14.00   0.50    0.20    --  -82.50  59.00  30.00  108
 40  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -30.00   64
 41  \w    -57.00 -16.00   0.50    0.20    --  -82.50  50.00 -90.00   82
 42  \w   -107.00 -21.00   0.50    0.20    --  -40.83 -51.00 -55.00  172
 43  \w   -150.00 -63.00   0.50    0.20    --  -82.50 -51.00 -55.00  174
 44  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00-180.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054352000
_diffrn_orient_matrix_UB_12      -0.0627353000
_diffrn_orient_matrix_UB_13      -0.1212860000
_diffrn_orient_matrix_UB_21      -0.1670687000
_diffrn_orient_matrix_UB_22      -0.0202731000
_diffrn_orient_matrix_UB_23      -0.0388584000
_diffrn_orient_matrix_UB_31      -0.0459667000
_diffrn_orient_matrix_UB_32      0.0809816000
_diffrn_orient_matrix_UB_33      -0.1035824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.110
_diffrn_reflns_theta_min         5.229
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0599
_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^)+(0.1085P)^2^+0.5813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2137
_reflns_number_total             2459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj05468g2.cif
_cod_data_source_block           sk5c_auto
_cod_depositor_comments
'Adding full bibliography for 7063669--7063670.cif.'
_cod_database_code               7063669
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.860
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C00H, O00J
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C008(H008), C00B(H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
3.c Idealised Me refined as rotating group:
 C00I(H00A,H00C,H00H), C00K(H00I,H00J,H00K)
3.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), O004(H004)
;
_shelx_res_checksum              77470
_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 6.391
_oxdiff_exptl_absorpt_empirical_full_min 0.694