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_7249995
_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         'C16 H16 O3, C16 H15 O3'
_chemical_formula_sum            'C32 H31 O6'
_chemical_formula_weight         511.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-04-05
_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                94.719(3)
_cell_angle_beta                 102.333(3)
_cell_angle_gamma                90.643(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8522(5)
_cell_length_b                   12.7911(11)
_cell_length_c                   15.3647(12)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.19
_cell_volume                     1310.56(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      301.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59611
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         1.362
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1492 before and 0.0796 after correction. The Ratio of minimum to maximum transmission is 0.8851. The \l/2 correction factor is Not present.'
_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    1.296
_exptl_crystal_description       plate
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0795
_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^)+(0.1088P)^2^+0.4820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2310
_refine_ls_wR_factor_ref         0.2523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3965
_reflns_number_total             6530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06053a3.cif
_cod_data_source_block           dbr047_0m_a
_cod_depositor_comments
'Adding full bibliography for 7249990--7249995.cif.'
_cod_database_code               7249995
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C11(H11A,H11B), C9(H9A,H9B), C26(H26A,H26B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C5(H5), C18(H18), C6(H6), C2(H2), C22(H22), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C31(H31A,H31B,
 H31C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              52935
_shelx_hkl_checksum              67315
_olex2_submission_special_instructions 'No special instructions were received'