#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:21:25 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301009 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/99/7249995.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249995
loop_
_publ_author_name
'Rath, Sibani'
'Lamba, Pinki'
'Sravan Kumar Reddy, P.'
'Krishna, Anugam V.'
'Ramachary, Dhevalapally B.'
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.1088P)²+0.4820P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0526(3) 0.35880(13) 0.07418(11) 0.0593(5) Uani 1 1 d . . . . .
H1 H -0.064601 0.399698 0.035112 0.089 Uiso 1 1 calc GR . . . .
O2 O -0.0449(3) 0.56339(13) 0.07980(10) 0.0614(5) Uani 1 1 d . . . . .
O4 O 0.3793(3) 0.32834(15) 0.55211(11) 0.0676(5) Uani 1 1 d . . . . .
H4 H 0.344949 0.373203 0.517181 0.101 Uiso 1 1 calc GR . . . .
O6 O 0.5317(3) 0.31709(14) 0.86116(12) 0.0681(5) Uani 1 1 d . . . . .
O3 O 0.0933(3) 0.38247(15) 0.38518(12) 0.0743(6) Uani 1 1 d . . . . .
O5 O 0.3841(3) 0.53194(15) 0.57387(11) 0.0693(5) Uani 1 1 d . . . . .
C1 C -0.0185(3) 0.41279(18) 0.15427(14) 0.0452(5) Uani 1 1 d . . . . .
C29 C 0.4685(3) 0.54741(17) 0.73435(13) 0.0389(5) Uani 1 1 d . . . . .
C20 C 0.5080(3) 0.48562(17) 0.80733(13) 0.0405(5) Uani 1 1 d . . . . .
C4 C 0.0516(3) 0.54228(18) 0.31770(13) 0.0422(5) Uani 1 1 d . . . . .
C14 C -0.0165(3) 0.52980(17) 0.15324(13) 0.0419(5) Uani 1 1 d . . . . .
C17 C 0.4222(3) 0.37344(18) 0.63573(15) 0.0479(5) Uani 1 1 d . . . . .
C30 C 0.4231(3) 0.49066(18) 0.64426(14) 0.0450(5) Uani 1 1 d . . . . .
C13 C 0.0183(3) 0.59533(17) 0.23899(13) 0.0395(5) Uani 1 1 d . . . . .
C28 C 0.4737(3) 0.65817(17) 0.74855(14) 0.0427(5) Uani 1 1 d . . . . .
C19 C 0.5019(3) 0.36799(18) 0.79583(15) 0.0462(5) Uani 1 1 d . . . . .
C12 C 0.0206(3) 0.70635(17) 0.24381(13) 0.0413(5) Uani 1 1 d . . . . .
C23 C 0.5144(3) 0.70521(18) 0.83688(15) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.0551(3) 0.42590(19) 0.31572(15) 0.0493(5) Uani 1 1 d . . . . .
C7 C 0.0614(3) 0.76278(19) 0.32886(14) 0.0477(5) Uani 1 1 d . . . . .
C21 C 0.5528(3) 0.53378(19) 0.89330(14) 0.0487(5) Uani 1 1 d . . . . .
H21 H 0.582336 0.493378 0.941808 0.058 Uiso 1 1 calc R . . . .
C5 C 0.0842(3) 0.5998(2) 0.39988(14) 0.0523(6) Uani 1 1 d . . . . .
H5 H 0.102947 0.565629 0.452021 0.063 Uiso 1 1 calc R . . . .
C18 C 0.4606(3) 0.31714(19) 0.70634(16) 0.0504(5) Uani 1 1 d . . . . .
H18 H 0.460637 0.244311 0.697771 0.060 Uiso 1 1 calc R . . . .
C6 C 0.0890(3) 0.7073(2) 0.40459(15) 0.0541(6) Uani 1 1 d . . . . .
H6 H 0.111566 0.744635 0.460541 0.065 Uiso 1 1 calc R . . . .
C2 C 0.0132(3) 0.36511(18) 0.22994(16) 0.0494(5) Uani 1 1 d . . . . .
H2 H 0.008375 0.292216 0.227436 0.059 Uiso 1 1 calc R . . . .
C22 C 0.5538(3) 0.6412(2) 0.90726(15) 0.0521(6) Uani 1 1 d . . . . .
H22 H 0.581628 0.672178 0.965634 0.063 Uiso 1 1 calc R . . . .
C27 C 0.4357(4) 0.7257(2) 0.67028(16) 0.0598(6) Uani 1 1 d . . . . .
H27A H 0.513849 0.700432 0.627598 0.072 Uiso 1 1 calc R . . . .
H27B H 0.295667 0.718496 0.640609 0.072 Uiso 1 1 calc R . . . .
C11 C -0.0198(4) 0.76430(19) 0.16011(15) 0.0574(6) Uani 1 1 d . . . . .
H11A H 0.093127 0.756633 0.131513 0.069 Uiso 1 1 calc R . . . .
H11B H -0.136236 0.732177 0.118887 0.069 Uiso 1 1 calc R . . . .
C8 C 0.0738(4) 0.8830(2) 0.34230(17) 0.0612(6) Uani 1 1 d . . . . .
C24 C 0.5193(4) 0.8245(2) 0.85995(18) 0.0608(6) Uani 1 1 d . . . . .
C15 C 0.2699(5) 0.9197(3) 0.4087(2) 0.0891(10) Uani 1 1 d . . . . .
H15A H 0.280858 0.994899 0.413744 0.134 Uiso 1 1 calc GR . . . .
H15B H 0.381607 0.891044 0.387328 0.134 Uiso 1 1 calc GR . . . .
H15C H 0.269031 0.895812 0.466248 0.134 Uiso 1 1 calc GR . . . .
C16 C -0.1008(5) 0.9238(3) 0.3818(2) 0.0854(10) Uani 1 1 d . . . . .
H16A H -0.099108 0.893341 0.436951 0.128 Uiso 1 1 calc GR . . . .
H16B H -0.224464 0.904875 0.340330 0.128 Uiso 1 1 calc GR . . . .
H16C H -0.088233 0.998808 0.392717 0.128 Uiso 1 1 calc GR . . . .
C32 C 0.7319(5) 0.8621(2) 0.9042(2) 0.0873(10) Uani 1 1 d . . . . .
H32A H 0.818866 0.845604 0.863954 0.131 Uiso 1 1 calc GR . . . .
H32B H 0.776053 0.827801 0.957956 0.131 Uiso 1 1 calc GR . . . .
H32C H 0.734700 0.936668 0.918685 0.131 Uiso 1 1 calc GR . . . .
C31 C 0.3837(6) 0.8527(3) 0.9253(3) 0.1055(13) Uani 1 1 d . . . . .
H31A H 0.443070 0.830450 0.982924 0.158 Uiso 1 1 calc GR . . . .
H31B H 0.255487 0.818006 0.903585 0.158 Uiso 1 1 calc GR . . . .
H31C H 0.367608 0.927249 0.930181 0.158 Uiso 1 1 calc GR . . . .
C9 C 0.0735(7) 0.9309(3) 0.2542(2) 0.0993(12) Uani 1 1 d . . . . .
H9A H 0.035357 1.003543 0.260186 0.119 Uiso 1 1 calc R . . . .
H9B H 0.208786 0.930832 0.244396 0.119 Uiso 1 1 calc R . . . .
C25 C 0.4435(7) 0.8811(3) 0.7770(3) 0.1078(13) Uani 1 1 d . . . . .
H25 H 0.369452 0.941359 0.779437 0.129 Uiso 1 1 calc R . . . .
C26 C 0.4879(8) 0.8405(3) 0.6979(3) 0.1203(16) Uani 1 1 d . . . . .
H26A H 0.630196 0.851094 0.702250 0.144 Uiso 1 1 calc R . . . .
H26B H 0.419105 0.880850 0.650456 0.144 Uiso 1 1 calc R . . . .
C10 C -0.0548(8) 0.8796(3) 0.1776(2) 0.1172(15) Uani 1 1 d . . . . .
H10A H -0.039914 0.914748 0.125693 0.141 Uiso 1 1 calc R . . . .
H10B H -0.191815 0.887627 0.183988 0.141 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C14 115.49(19) . . ?
O1 C1 C2 121.9(2) . . ?
C2 C1 C14 122.6(2) . . ?
C20 C29 C30 116.64(19) . . ?
C20 C29 C28 120.43(18) . . ?
C28 C29 C30 122.93(18) . . ?
C29 C20 C19 122.46(19) . . ?
C21 C20 C29 119.5(2) . . ?
C21 C20 C19 117.99(18) . . ?
C13 C4 C3 122.37(19) . . ?
C5 C4 C13 119.3(2) . . ?
C5 C4 C3 118.3(2) . . ?
O2 C14 C1 116.13(19) . . ?
O2 C14 C13 124.9(2) . . ?
C13 C14 C1 118.93(18) . . ?
O4 C17 C30 115.4(2) . . ?
C18 C17 O4 121.9(2) . . ?
C18 C17 C30 122.7(2) . . ?
O5 C30 C29 125.2(2) . . ?
O5 C30 C17 115.6(2) . . ?
C29 C30 C17 119.19(18) . . ?
C4 C13 C14 116.91(19) . . ?
C4 C13 C12 120.63(18) . . ?
C12 C13 C14 122.46(18) . . ?
C29 C28 C27 120.90(19) . . ?
C23 C28 C29 118.87(18) . . ?
C23 C28 C27 120.2(2) . . ?
O6 C19 C20 120.4(2) . . ?
O6 C19 C18 121.3(2) . . ?
C18 C19 C20 118.34(19) . . ?
C13 C12 C11 121.27(18) . . ?
C7 C12 C13 118.58(19) . . ?
C7 C12 C11 120.1(2) . . ?
C28 C23 C24 123.2(2) . . ?
C22 C23 C28 118.9(2) . . ?
C22 C23 C24 117.9(2) . . ?
O3 C3 C4 120.8(2) . . ?
O3 C3 C2 120.7(2) . . ?
C2 C3 C4 118.56(19) . . ?
C12 C7 C8 123.2(2) . . ?
C6 C7 C12 118.8(2) . . ?
C6 C7 C8 118.0(2) . . ?
C22 C21 C20 120.1(2) . . ?
C6 C5 C4 120.0(2) . . ?
C17 C18 C19 120.6(2) . . ?
C5 C6 C7 122.5(2) . . ?
C1 C2 C3 120.5(2) . . ?
C21 C22 C23 122.2(2) . . ?
C26 C27 C28 113.0(2) . . ?
C10 C11 C12 113.5(2) . . ?
C7 C8 C15 109.9(2) . . ?
C16 C8 C7 110.0(2) . . ?
C16 C8 C15 107.9(2) . . ?
C16 C8 C9 110.2(3) . . ?
C9 C8 C7 111.2(2) . . ?
C9 C8 C15 107.6(3) . . ?
C32 C24 C23 109.6(2) . . ?
C32 C24 C31 108.4(3) . . ?
C31 C24 C23 110.3(2) . . ?
C25 C24 C23 110.9(2) . . ?
C25 C24 C32 110.3(3) . . ?
C25 C24 C31 107.3(3) . . ?
C10 C9 C8 115.4(3) . . ?
C26 C25 C24 117.9(3) . . ?
C25 C26 C27 116.9(3) . . ?
C9 C10 C11 115.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.334(3) . ?
O2 C14 1.218(2) . ?
O4 C17 1.335(3) . ?
O6 C19 1.223(3) . ?
O3 C3 1.224(3) . ?
O5 C30 1.222(3) . ?
C1 C14 1.498(3) . ?
C1 C2 1.335(3) . ?
C29 C20 1.406(3) . ?
C29 C30 1.478(3) . ?
C29 C28 1.415(3) . ?
C20 C19 1.500(3) . ?
C20 C21 1.381(3) . ?
C4 C13 1.413(3) . ?
C4 C3 1.487(3) . ?
C4 C5 1.382(3) . ?
C14 C13 1.475(3) . ?
C17 C30 1.494(3) . ?
C17 C18 1.332(3) . ?
C13 C12 1.416(3) . ?
C28 C23 1.408(3) . ?
C28 C27 1.518(3) . ?
C19 C18 1.441(3) . ?
C12 C7 1.411(3) . ?
C12 C11 1.513(3) . ?
C23 C22 1.393(3) . ?
C23 C24 1.536(3) . ?
C3 C2 1.445(3) . ?
C7 C6 1.392(3) . ?
C7 C8 1.533(3) . ?
C21 C22 1.372(3) . ?
C5 C6 1.370(4) . ?
C27 C26 1.511(4) . ?
C11 C10 1.509(4) . ?
C8 C15 1.545(4) . ?
C8 C16 1.530(4) . ?
C8 C9 1.532(4) . ?
C24 C32 1.524(4) . ?
C24 C31 1.532(4) . ?
C24 C25 1.515(4) . ?
C9 C10 1.416(5) . ?
C25 C26 1.378(5) . ?
