Sustainable construction of value-added naphthoquinones for pharmaceuticals
Rath, Sibani; Lamba, Pinki; Sravan Kumar Reddy, P.; Krishna, Anugam V.; Ramachary, Dhevalapally B.; Green Chemistry 27 (2025) 3465–3476; doi:10.1039/D4GC06053A

data_7249991
_publ_section_title
;
 Sustainable construction of value-added naphthoquinones for
 pharmaceuticals
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3465
_journal_page_last               3476
_journal_paper_doi               10.1039/D4GC06053A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_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             2023-09-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-11-04 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.593(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.42680(10)
_cell_length_b                   10.2243(2)
_cell_length_c                   22.7209(5)
_cell_measurement_reflns_used    8443
_cell_measurement_temperature    298.7
_cell_measurement_theta_max      26.4340
_cell_measurement_theta_min      2.1760
_cell_volume                     1256.63(4)
_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      298.7
_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 0.969
_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    -18.00  22.00   0.50    7.00    --  -14.97 -94.00 -60.00   80
  2  \w      9.00  70.00   0.50    7.00    --   16.22-124.00 -17.00  122
  3  \w     14.00  71.00   0.50    7.00    --   16.22-125.00   0.00  114
  4  \w      7.00  33.00   0.50    7.00    --   16.22 -15.00 -90.00   52
  5  \w     -6.00  85.00   0.50    7.00    --   16.22  45.00 -90.00  182
  6  \w    -37.00  18.00   0.50    7.00    --  -14.97 -94.00-180.00  110
  7  \w    -43.00 -18.00   0.50    7.00    --   16.22 -15.00 -90.00   50
  8  \w    -85.00  10.00   0.50    7.00    --  -14.97 -45.00 -60.00  190
  9  \w    -85.00  10.00   0.50    7.00    --  -14.97 -45.00-150.00  190
 10  \w    -83.00 -23.00   0.50    7.00    --  -14.97 148.00-133.00  120
 11  \w    -63.00 -34.00   0.50    7.00    --  -14.97 125.00  30.00   58
 12  \w    -69.00  -9.00   0.50    7.00    --  -14.97 124.00  62.00  120
 13  \w    -41.00  59.00   0.50    7.00    --  -14.97  30.00 120.00  200
 14  \w    -57.00  40.00   0.50    7.00    --   16.22 -30.00 120.00  194
 15  \w     23.00  85.00   0.50    7.00    --   16.22-148.00 178.00  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      -0.0089740000
_diffrn_orient_matrix_UB_12      0.0633510000
_diffrn_orient_matrix_UB_13      0.0123659000
_diffrn_orient_matrix_UB_21      -0.0206831000
_diffrn_orient_matrix_UB_22      0.0268842000
_diffrn_orient_matrix_UB_23      -0.0287574000
_diffrn_orient_matrix_UB_31      -0.1291380000
_diffrn_orient_matrix_UB_32      -0.0087323000
_diffrn_orient_matrix_UB_33      0.0012089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.881
_diffrn_reflns_theta_min         2.185
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48608
_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    1.312
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.1333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2057
_reflns_number_total             2616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06053a3.cif
_cod_data_source_block           dbr74
_cod_depositor_comments
'Adding full bibliography for 7249990--7249995.cif.'
_cod_database_code               7249991
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.63
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C17(H17), C13(H13), C2(H2), C15(H15), C16(H16), C4(H4),
 C14(H14), C3(H3)
;
_shelx_res_checksum              42518
_shelx_hkl_checksum              80497
_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.561