#------------------------------------------------------------------------------
#$Date: 2018-08-25 05:18:41 +0300 (Sat, 25 Aug 2018) $
#$Revision: 210134 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/26/2242612.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242612
loop_
_publ_author_name
'Raquel Geralda, Isidório'
'Flaviano Melo, Ottoni'
'Ricardo José, Alves'
'Nivaldo Lúcio, Speziali'
_publ_section_title
;
 Crystal structure of 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione
;
_journal_coeditor_code           IS5498
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1319
_journal_page_last               1321
_journal_paper_doi               10.1107/S2056989018011647
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H8 O3'
_chemical_formula_moiety         'C13 H8 O3'
_chemical_formula_sum            'C13 H8 O3'
_chemical_formula_weight         212.19
_chemical_melting_point_gt       396.8
_chemical_melting_point_lt       397.5
_chemical_name_common            ' C-propargyl lawsone'
_chemical_name_systematic
;
2-Hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                96.814(7)
_cell_angle_beta                 93.432(7)
_cell_angle_gamma                102.977(7)
_cell_formula_units_Z            2
_cell_length_a                   5.3695(4)
_cell_length_b                   9.5278(8)
_cell_length_c                   10.2972(9)
_cell_measurement_reflns_used    1721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6890
_cell_measurement_theta_min      3.1570
_cell_volume                     507.68(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.590
_diffrn_reflns_theta_min         2.775
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0512
_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)+(0.0639P)²+0.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                1563
_reflns_number_total             2508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5498sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        507.68(8)
_cod_database_code               2242612
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O3 0.6461(3) 0.33269(14) 0.01419(12) 0.0536(4) Uani d 1
H H3 0.796(5) 0.389(3) 0.002(3) 0.104(10) Uiso d 1
O O1 0.9195(2) 0.59305(13) 0.12532(12) 0.0518(3) Uani d 1
O O2 0.0447(3) 0.36386(14) 0.31887(13) 0.0647(4) Uani d 1
C C1 0.7232(3) 0.54469(17) 0.17533(15) 0.0388(4) Uani d 1
C C2 0.5615(3) 0.39989(17) 0.11881(15) 0.0403(4) Uani d 1
C C3 0.3415(3) 0.33844(17) 0.16560(15) 0.0419(4) Uani d 1
C C4 0.2483(3) 0.41556(18) 0.27733(16) 0.0431(4) Uani d 1
C C5 0.3230(4) 0.6358(2) 0.44404(17) 0.0511(4) Uani d 1
H H5 0.1693 0.5951 0.4767 0.061 Uiso calc 1
C C6 0.4664(4) 0.7695(2) 0.50175(19) 0.0586(5) Uani d 1
H H6 0.4109 0.8182 0.5740 0.070 Uiso calc 1
C C7 0.6917(4) 0.8311(2) 0.4525(2) 0.0642(6) Uani d 1
H H7 0.7871 0.9218 0.4915 0.077 Uiso calc 1
C C8 0.7782(3) 0.7597(2) 0.34557(18) 0.0530(5) Uani d 1
H H8 0.9302 0.8021 0.3123 0.064 Uiso calc 1
C C9 0.6345(3) 0.62361(16) 0.28851(15) 0.0389(4) Uani d 1
C C10 0.4061(3) 0.56178(17) 0.33796(15) 0.0397(4) Uani d 1
C C11 0.1798(4) 0.19019(18) 0.10516(18) 0.0536(5) Uani d 1
H H11A 0.0054 0.1811 0.1290 0.064 Uiso calc 1
H H11B 0.1751 0.1833 0.0103 0.064 Uiso calc 1
C C12 0.2779(4) 0.07067(19) 0.14761(17) 0.0552(5) Uani d 1
C C13 0.3566(5) -0.0258(2) 0.1781(2) 0.0829(7) Uani d 1
H H13 0.4196 -0.1030 0.2026 0.099 Uiso calc 1
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
C2 O3 H3 106.5(17)
O1 C1 C2 118.90(14)
O1 C1 C9 123.40(15)
C9 C1 C2 117.69(14)
O3 C2 C1 115.90(14)
C3 C2 O3 120.71(15)
C3 C2 C1 123.38(14)
C2 C3 C4 119.88(15)
C2 C3 C11 122.10(15)
C4 C3 C11 118.01(15)
O2 C4 C3 121.03(16)
O2 C4 C10 120.40(15)
C3 C4 C10 118.56(14)
C6 C5 H5 119.8
C6 C5 C10 120.37(17)
C10 C5 H5 119.8
C5 C6 H6 120.0
C7 C6 C5 119.98(17)
C7 C6 H6 120.0
C6 C7 H7 119.6
C6 C7 C8 120.80(18)
C8 C7 H7 119.6
C7 C8 H8 120.5
C7 C8 C9 119.08(17)
C9 C8 H8 120.5
C8 C9 C1 120.23(15)
C10 C9 C1 119.71(14)
C10 C9 C8 120.07(15)
C5 C10 C4 119.53(15)
C5 C10 C9 119.69(15)
C9 C10 C4 120.78(14)
C3 C11 H11A 109.1
C3 C11 H11B 109.1
H11A C11 H11B 107.8
C12 C11 C3 112.70(14)
C12 C11 H11A 109.1
C12 C11 H11B 109.1
C13 C12 C11 178.3(2)
C12 C13 H13 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 H3 0.88(3)
O3 C2 1.3426(19)
O1 C1 1.2217(18)
O2 C4 1.2189(19)
C1 C2 1.485(2)
C1 C9 1.473(2)
C2 C3 1.340(2)
C3 C4 1.465(2)
C3 C11 1.521(2)
C4 C10 1.499(2)
C5 H5 0.9300
C5 C6 1.376(3)
C5 C10 1.381(2)
C6 H6 0.9300
C6 C7 1.375(3)
C7 H7 0.9300
C7 C8 1.384(3)
C8 H8 0.9300
C8 C9 1.392(2)
C9 C10 1.390(2)
C11 H11A 0.9700
C11 H11B 0.9700
C11 C12 1.458(3)
C12 C13 1.161(3)
C13 H13 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 2_765 0.89(3) 2.06(3) 2.8118(19) 142(3)
C5 H5 O2 2_566 0.93 2.49 3.231(2) 137
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 O3 -0.4(2) no
O1 C1 C2 C3 -179.15(16) no
C9 C1 C2 O3 178.72(14) no
C9 C1 C2 C3 -0.1(2) no
O1 C1 C9 C8 -1.0(2) no
O1 C1 C9 C10 178.81(15) no
C2 C1 C9 C8 179.98(14) no
C2 C1 C9 C10 -0.2(2) no
O3 C2 C3 C4 -178.09(15) no
O3 C2 C3 C11 1.0(2) no
C1 C2 C3 C4 0.7(2) no
C1 C2 C3 C11 179.77(15) no
C2 C3 C4 O2 177.64(16) no
C2 C3 C4 C10 -0.9(2) no
C11 C3 C4 O2 -1.5(2) no
C11 C3 C4 C10 179.92(15) no
C2 C3 C11 C12 79.9(2) no
C4 C3 C11 C12 -100.96(19) no
O2 C4 C10 C5 2.0(3) no
O2 C4 C10 C9 -177.93(16) no
C3 C4 C10 C5 -179.45(16) no
C3 C4 C10 C9 0.7(2) no
C10 C5 C6 C7 1.0(3) no
C6 C5 C10 C4 179.40(17) no
C6 C5 C10 C9 -0.7(3) no
C5 C6 C7 C8 -0.5(3) no
C6 C7 C8 C9 -0.4(3) no
C7 C8 C9 C1 -179.48(16) no
C7 C8 C9 C10 0.7(3) no
C1 C9 C10 C4 -0.1(2) no
C1 C9 C10 C5 -180.00(16) no
C8 C9 C10 C4 179.73(15) no
C8 C9 C10 C5 -0.2(2) no
