#------------------------------------------------------------------------------
#$Date: 2018-11-10 05:38:07 +0200 (Sat, 10 Nov 2018) $
#$Revision: 211891 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242726.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_2242726
loop_
_publ_author_name
'Melo Ottoni, Flaviano'
'Isidório, Raquel Geralda'
'Alves, Ricardo José'
'Speziali, Nivaldo Lúcio'
_publ_section_title
;
 Two polymorphs of 2-(prop-2-yn-1-yloxy)naphthalene-1,4-dione:
 solvent-dependent crystallization
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1731
_journal_page_last               1734
_journal_paper_doi               10.1107/S2056989018015438
_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_name_systematic
;
2-(Prop-2-yn-1-yloxy)naphthalene-1,4-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.174(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0911(7)
_cell_length_b                   4.8021(3)
_cell_length_c                   20.8939(15)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6410
_cell_measurement_theta_min      3.8760
_cell_volume                     1012.27(12)
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_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_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10652
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.777
_diffrn_reflns_theta_min         2.778
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0585
_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)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                1765
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5501sup1.cif
_cod_data_source_block           Monoclinic
_cod_database_code               2242726
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 O1 0.08336(12) 0.4803(2) 0.34723(5) 0.0512(3) Uani d 1
O O2 0.50658(13) 1.0905(3) 0.41264(6) 0.0646(4) Uani d 1
O O3 0.19024(11) 0.3978(2) 0.46005(5) 0.0493(3) Uani d 1
C C1 0.17768(15) 0.6268(3) 0.36127(7) 0.0381(4) Uani d 1
C C2 0.24795(16) 0.5949(3) 0.42459(7) 0.0390(4) Uani d 1
C C3 0.35379(16) 0.7492(3) 0.44063(7) 0.0434(4) Uani d 1
H H3 0.3937 0.7248 0.4807 0.052 Uiso calc 1
C C4 0.40849(16) 0.9546(3) 0.39706(8) 0.0419(4) Uani d 1
C C5 0.38922(16) 1.1922(3) 0.29135(8) 0.0445(4) Uani d 1
H H5 0.4645 1.2953 0.3021 0.053 Uiso calc 1
C C6 0.32525(17) 1.2340(4) 0.23311(8) 0.0495(4) Uani d 1
H H6 0.3576 1.3651 0.2046 0.059 Uiso calc 1
C C7 0.21324(18) 1.0817(4) 0.21695(8) 0.0528(5) Uani d 1
H H7 0.1701 1.1116 0.1778 0.063 Uiso calc 1
C C8 0.16518(16) 0.8854(4) 0.25877(8) 0.0460(4) Uani d 1
H H8 0.0899 0.7832 0.2477 0.055 Uiso calc 1
C C9 0.22882(15) 0.8402(3) 0.31716(7) 0.0362(3) Uani d 1
C C10 0.34126(15) 0.9961(3) 0.33397(7) 0.0363(4) Uani d 1
C C11 0.24569(19) 0.3468(3) 0.52323(7) 0.0488(4) Uani d 1
H H11A 0.2477 0.5175 0.5480 0.059 Uiso calc 1
H H11B 0.3354 0.2761 0.5204 0.059 Uiso calc 1
C C12 0.16027(19) 0.1408(4) 0.55324(8) 0.0510(5) Uani d 1
C C13 0.0907(2) -0.0220(4) 0.57682(9) 0.0649(6) Uani d 1
H H13 0.0352 -0.1518 0.5956 0.078 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
O1 C1 C9 122.19(14)
O1 C1 C2 120.61(14)
O2 C4 C10 121.15(15)
O2 C4 C3 120.59(15)
O3 C2 C1 110.92(14)
O3 C11 H11A 110.4
O3 C11 H11B 110.4
O3 C11 C12 106.62(14)
C2 O3 C11 117.37(13)
C2 C3 C4 121.94(14)
C2 C3 H3 119.0
C3 C2 O3 127.29(15)
C3 C2 C1 121.78(14)
C3 C4 C10 118.26(14)
C4 C3 H3 119.0
C5 C6 H6 119.9
C5 C6 C7 120.24(15)
C5 C10 C9 119.55(14)
C5 C10 C4 120.10(15)
C6 C5 C10 120.05(16)
C6 C5 H5 120.0
C6 C7 H7 119.9
C7 C8 C9 120.16(16)
C7 C6 H6 119.9
C7 C8 H8 119.9
C8 C9 C10 119.80(14)
C8 C9 C1 119.77(14)
C8 C7 C6 120.20(16)
C8 C7 H7 119.9
C9 C10 C4 120.35(14)
C9 C1 C2 117.20(14)
C9 C8 H8 119.9
C10 C9 C1 120.42(14)
C10 C5 H5 120.0
H11A C11 H11B 108.6
C12 C11 H11A 110.4
C12 C11 H11B 110.4
C12 C13 H13 180.0
C13 C12 C11 179.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2145(18)
O2 C4 1.2241(18)
O3 C2 1.3423(18)
O3 C11 1.4442(19)
C1 C2 1.496(2)
C2 C3 1.337(2)
C3 H3 0.9300
C4 C3 1.458(2)
C5 C6 1.380(2)
C5 H5 0.9300
C6 C7 1.382(2)
C6 H6 0.9300
C7 H7 0.9300
C8 C7 1.380(2)
C8 H8 0.9300
C9 C10 1.398(2)
C9 C1 1.478(2)
C9 C8 1.384(2)
C10 C4 1.483(2)
C10 C5 1.390(2)
C11 C12 1.462(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.167(2)
C13 H13 0.9300
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
O1 C1 C2 O3 -1.5(2)
O1 C1 C2 C3 178.50(10)
O2 C4 C3 C2 -179.0(2)
O3 C2 C3 C4 178.90(10)
C1 C9 C8 C7 -179.2(2)
C1 C9 C10 C5 178.80(10)
C1 C9 C10 C4 -1.7(2)
C1 C2 C3 C4 -1.0(2)
C2 O3 C11 C12 175.90(10)
C5 C10 C4 O2 -0.1(2)
C5 C6 C7 C8 -0.5(3)
C8 C9 C1 O1 2.7(2)
C8 C9 C10 C5 -1.0(2)
C8 C9 C10 C4 178.50(10)
C8 C9 C1 C2 -177.90(10)
C9 C1 C2 O3 179.10(10)
C9 C10 C4 O2 -179.6(2)
C9 C10 C5 C6 0.6(2)
C9 C8 C7 C6 0.1(3)
C9 C1 C2 C3 -1.0(2)
C9 C10 C4 C3 -0.3(2)
C10 C9 C1 O1 -177.10(10)
C10 C5 C6 C7 0.1(3)
C10 C9 C8 C7 0.7(2)
C10 C9 C1 C2 2.3(2)
C10 C4 C3 C2 1.7(2)
C11 O3 C2 C3 1.2(2)
C11 O3 C2 C1 -178.80(10)
