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_7249994
_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_absolute_configuration syn
_chemical_formula_moiety         'C17 H11 Cl O2'
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2023-12-15
_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                103.743(2)
_cell_angle_beta                 98.978(2)
_cell_angle_gamma                97.252(2)
_cell_formula_units_Z            1
_cell_length_a                   4.9955(2)
_cell_length_b                   5.9148(3)
_cell_length_c                   11.7073(7)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.47
_cell_volume                     327.06(3)
_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      298.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10940
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.227
_diffrn_reflns_theta_min         1.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1519 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
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    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             146
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2512
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06053a3.cif
_cod_data_source_block           dbr026_0m_a
_cod_depositor_comments
'Adding full bibliography for 7249990--7249995.cif.'
_cod_database_code               7249994
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.947
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C12(H12), C13(H13), C14(H14), C2(H2), C15(H15), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              32617
_shelx_hkl_checksum              81809
_olex2_submission_special_instructions 'No special instructions were received'