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_7063670
_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         'C17 H22 O5'
_chemical_formula_sum            'C17 H22 O5'
_chemical_formula_weight         306.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.79460(10)
_cell_length_b                   9.88250(10)
_cell_length_c                   22.9394(3)
_cell_measurement_reflns_used    6577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3430
_cell_measurement_theta_min      3.8430
_cell_volume                     1540.33(3)
_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     19.00  78.00   0.50    0.21    --   40.83-106.00  74.00  118
  2  \w    -59.00  27.00   0.50    0.21    --  -40.83  52.00 -54.00  172
  3  \w    -59.00 -15.00   0.50    0.84    --  -82.50  52.00 -54.00   88
  4  \w    -93.00 -13.00   0.50    0.84    --  -82.50  73.00  88.00  160
  5  \w    -47.00 -15.00   0.50    0.84    --  -82.50  42.00  60.00   64
  6  \w    -66.00  28.00   0.50    0.21    --  -40.83  73.00  88.00  188
  7  \w    -27.00  67.00   0.50    0.21    --   40.83 -73.00 -40.00  188
  8  \w    -26.00  59.00   0.50    0.21    --   40.83 -52.00 160.00  170
  9  \w    -31.00  28.00   0.50    0.21    --   40.83 -21.00 -30.00  118
 10  \w    -35.00  24.00   0.50    0.21    --   40.83 -11.00-120.00  118
 11  \w     21.00 109.00   0.50    0.21    --   40.83  52.00 -54.00  176
 12  \w     99.00 155.00   0.50    0.84    --   96.04 117.00-180.00  112
 13  \w    106.00 132.00   0.50    0.84    --   96.04  96.00-180.00   52
 14  \w     76.00 163.00   0.50    0.84    --   96.04  52.00 -54.00  174
 15  \w     70.00 164.00   0.50    0.84    --   96.04  73.00  88.00  188
 16  \w    115.00 169.00   0.50    0.84    --   96.04  96.00 150.00  108
 17  \w    104.00 165.00   0.50    0.84    --   96.04 106.00 174.00  122
 18  \w     29.00  55.00   0.50    0.84    --   96.04 -50.00  60.00   52
 19  \w     51.00  77.00   0.50    0.84    --   96.04 -68.00 150.00   52
 20  \w     28.00  67.00   0.50    0.84    --   96.04 -59.00 120.00   78
 21  \w     28.00  59.00   0.50    0.84    --   96.04 -52.00 160.00   62
 22  \w     49.00  74.00   0.50    0.84    --   96.04 -73.00 -40.00   50
 23  \w     29.00  67.00   0.50    0.84    --   96.04 -59.00 -90.00   76
 24  \w     28.00  68.00   0.50    0.84    --   96.04 -59.00-120.00   80
 25  \w     32.00  57.00   0.50    0.84    --   96.04 -50.00-180.00   50
 26  \w     29.00  54.00   0.50    0.84    --   96.04 -50.00 -30.00   50
 27  \w     29.00  54.00   0.50    0.84    --   96.04 -50.00  90.00   50
 28  \w    -78.00   3.00   0.50    0.21    --  -40.83 106.00 174.00  162
 29  \w    -83.00 -14.00   0.50    0.84    --  -82.50 106.00 174.00  138
 30  \w   -150.00 -63.00   0.50    0.84    --  -82.50 -52.00 160.00  174
 31  \w   -109.00 -15.00   0.50    0.21    --  -40.83 -73.00 -40.00  188
 32  \w   -152.00 -57.00   0.50    0.84    --  -82.50 -73.00 -40.00  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      0.1244227000
_diffrn_orient_matrix_UB_12      0.0586251000
_diffrn_orient_matrix_UB_13      -0.0501432000
_diffrn_orient_matrix_UB_21      -0.1806271000
_diffrn_orient_matrix_UB_22      0.0790631000
_diffrn_orient_matrix_UB_23      -0.0222043000
_diffrn_orient_matrix_UB_31      0.0574530000
_diffrn_orient_matrix_UB_32      0.1208342000
_diffrn_orient_matrix_UB_33      0.0387950000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10601
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.114
_diffrn_reflns_theta_min         3.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89493
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0566
_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^)+(0.1408P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.486
_reflns_Friedel_fraction_full    0.691
_reflns_Friedel_fraction_max     0.685
_reflns_number_gt                2173
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj05468g2.cif
_cod_data_source_block           sk10a_autored
_cod_depositor_comments
'Adding full bibliography for 7063669--7063670.cif.'
_cod_database_code               7063670
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O '
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.897
_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, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C5-H1A
 2.22 with sigma of 0.04
 C4-H4
 1.9 with sigma of 0.04
3. Rigid bond restraints
 C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H1D(0.5) H1E(0.5) H1F(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4A)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C9(H9), C3(H3)
5.d Disordered Me refined with riding coordinates:
 C1(H1A,H1B,H1C,H1D,H1E,H1F)
5.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C2(H2A,H2B,H2C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              25134
_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 1.095
_oxdiff_exptl_absorpt_empirical_full_min 0.910