Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
Martínez-Cabrera, Miguel A.; Macías, Mario A.; Ferreira, Francisco; Pandolfi, Enrique; Barúa, Javier; Suescun, Leopoldo; Acta Crystallographica Section E 75 (2019) 1362–1366; doi:10.1107/S2056989019011393

data_2243062
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of lapachol acetate 80
 years after its first synthesis
;
_journal_coeditor_code           EX2023
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1362
_journal_page_last               1366
_journal_paper_doi               10.1107/S2056989019011393
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C17 H16 O4'
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_chemical_melting_point          352.0(10)
_chemical_name_common            'lapachol acetate'
_chemical_name_systematic
;
3-(3-Methylbut-2-enyl)-1,4-dioxonaphthalen-2-yl acetate
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.943(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0914(8)
_cell_length_b                   9.4741(6)
_cell_length_c                   12.7761(9)
_cell_measurement_reflns_used    7958
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      75.657
_cell_measurement_theta_min      4.9115
_cell_volume                     1461.64(17)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       '\j and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7496
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.204
_diffrn_reflns_theta_min         4.911
_diffrn_source                   'Cu Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0530P)^2^+0.3463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                1972
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ex2023sup1.cif
_cod_data_source_block           I
_cod_database_code               2243062
_cod_database_fobs_code          2243062
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.879
_shelx_hkl_checksum              49233
_shelx_res_checksum              25793