#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/99/2009993.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_2009993
loop_
_publ_author_name
'Müller, Gerhard'
'Lutz, Martin'
'Lachmann, Joachim'
_publ_section_title
;
 2-Acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1318
_journal_page_last               1320
_journal_paper_doi               10.1107/S0108270194001435
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_melting_point          454.15
_chemical_name_systematic
;
 2-Acetyl-1,8-dihydroxy-3,6-dimethylnaphthalene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                88.770(10)
_cell_angle_beta                 73.900(10)
_cell_angle_gamma                76.200(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2690(10)
_cell_length_b                   7.5170(10)
_cell_length_c                   10.7000(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      15.55
_cell_volume                     544.89(12)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976); SCHAKAL92 (Keller,1992)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      215(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4 4-circle'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4992
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_restrained_S_obs      1.081
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_obs          0.0431
_refine_ls_shift/esd_max         0.105
_refine_ls_shift/esd_mean        0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0924P)² +0.0697P] where P=(Fo² + 2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1446
_refine_ls_wR_factor_obs         0.1277
_reflns_number_observed          1851
_reflns_number_total             2494
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            se1049.cif
_cod_data_source_block           k11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '181_C' was changed to '454.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '181_C' was changed to '454.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' calc
w=1/[\s^2^(Fo^2^)+(0.0924P)^2^ +0.0697P] where P=(Fo^2^ +
2F~c~^2^)/3' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w=1/[\s^2^(Fo^2^)+(0.0924P)^2^ +0.0697P] where P=(Fo^2^ +
2F~c~^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        544.90(10)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2009993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.08420(15) 0.22690(13) 0.26192(10) 0.0352(3) Uani d . 1 . O
O2 0.31151(14) 0.17657(11) 0.02530(9) 0.0323(3) Uani d . 1 . O
O3 0.5229(2) 0.12292(12) -0.19287(10) 0.0388(3) Uani d . 1 . O
C1 0.2776(2) 0.3567(2) 0.00836(11) 0.0231(3) Uani d . 1 . C
C2 0.3658(2) 0.4263(2) -0.11163(11) 0.0230(3) Uani d . 1 . C
C3 0.3241(2) 0.6231(2) -0.12258(12) 0.0238(3) Uani d . 1 . C
C4 0.2046(2) 0.7333(2) -0.01798(12) 0.0254(3) Uani d . 1 . C
C5 -0.0055(2) 0.7866(2) 0.20885(12) 0.0284(3) Uani d . 1 . C
C6 -0.0904(2) 0.7207(2) 0.32626(12) 0.0306(3) Uani d . 1 . C
C7 -0.0583(2) 0.5307(2) 0.33980(12) 0.0302(3) Uani d . 1 . C
C8 0.0594(2) 0.4079(2) 0.23872(12) 0.0259(3) Uani d . 1 . C
C9 0.1503(2) 0.47396(15) 0.11669(11) 0.0226(3) Uani d . 1 . C
C10 0.1150(2) 0.6657(2) 0.10301(11) 0.0238(3) Uani d . 1 . C
C11 0.4930(2) 0.2910(2) -0.21394(12) 0.0275(3) Uani d . 1 . C
C12 0.5968(2) 0.3349(2) -0.34810(14) 0.0375(3) Uani d . 1 . C
C13 0.4053(2) 0.7178(2) -0.24392(13) 0.0318(3) Uani d . 1 . C
C14 -0.2129(3) 0.8508(2) 0.4403(2) 0.0446(4) Uani d . 1 . C
H1O 0.172(3) 0.163(3) 0.188(2) 0.074(7) Uiso d . 1 . H
H2O 0.410(4) 0.120(3) -0.066(3) 0.085(7) Uiso d . 1 . H
H4 0.180(2) 0.864(2) -0.0223(15) 0.033(4) Uiso d . 1 . H
H5 -0.023(2) 0.916(2) 0.1983(16) 0.041(4) Uiso d . 1 . H
H7 -0.114(3) 0.482(2) 0.4239(18) 0.049(5) Uiso d . 1 . H
H121 0.503(3) 0.406(2) -0.3927(16) 0.046(5) Uiso d . 1 . H
H122 0.667(3) 0.224(3) -0.3996(18) 0.052(5) Uiso d . 1 . H
H123 0.696(3) 0.408(2) -0.3454(17) 0.049(5) Uiso d . 1 . H
H131 0.360(3) 0.688(2) -0.3167(17) 0.046(5) Uiso d . 1 . H
H132 0.554(3) 0.684(2) -0.2765(16) 0.042(4) Uiso d . 1 . H
H133 0.360(2) 0.850(2) -0.2250(15) 0.039(4) Uiso d . 1 . H
H141 -0.172(4) 0.827(4) 0.518(3) 0.111(9) Uiso d . 1 . H
H142 -0.198(4) 0.966(4) 0.426(3) 0.113(10) Uiso d . 1 . H
H143 -0.348(5) 0.853(4) 0.462(3) 0.118(10) Uiso d . 1 . H
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_publ_flag
C8 O1 H1O 107.0(14) ?
C1 O2 H2O 102.9(13) ?
C11 O3 H2O 103.2(10) ?
O2 C1 C2 121.03(10) yes
O2 C1 C9 116.77(11) yes
C2 C1 C9 122.20(11) yes
C1 C2 C3 118.02(10) yes
C1 C2 C11 116.41(11) yes
C3 C2 C11 125.57(11) yes
C4 C3 C2 119.18(11) yes
C4 C3 C13 116.51(11) yes
C2 C3 C13 124.31(11) yes
C3 C4 C10 123.46(11) yes
C3 C4 H4 120.3(9) ?
C10 C4 H4 116.2(9) ?
C6 C5 C10 120.87(12) yes
C6 C5 H5 120.5(10) ?
C10 C5 H5 118.6(10) ?
C5 C6 C7 119.32(11) yes
C5 C6 C14 120.52(13) yes
C7 C6 C14 120.15(13) yes
C8 C7 C6 121.55(12) yes
C8 C7 H7 118.2(10) ?
C6 C7 H7 120.2(10) ?
O1 C8 C7 117.20(11) yes
O1 C8 C9 122.94(11) yes
C7 C8 C9 119.86(11) yes
C10 C9 C1 118.21(11) yes
C10 C9 C8 118.33(11) yes
C1 C9 C8 123.45(11) yes
C5 C10 C9 120.06(11) yes
C5 C10 C4 121.02(11) yes
C9 C10 C4 118.92(10) yes
O3 C11 C2 120.31(11) yes
O3 C11 C12 114.71(11) yes
C2 C11 C12 124.98(11) yes
C11 C12 H121 111.5(10) ?
C11 C12 H122 110.2(11) ?
H121 C12 H122 107.6(15) ?
C11 C12 H123 110.9(10) ?
H121 C12 H123 108.7(14) ?
H122 C12 H123 107.7(15) ?
C3 C13 H131 112.0(10) ?
C3 C13 H132 113.8(9) ?
H131 C13 H132 105.6(13) ?
C3 C13 H133 108.2(9) ?
H131 C13 H133 108.4(13) ?
H132 C13 H133 108.7(13) ?
C6 C14 H141 114.2(16) ?
C6 C14 H142 112.(2) ?
H141 C14 H142 101.(2) ?
C6 C14 H143 113.1(17) ?
H141 C14 H143 107.(2) ?
H142 C14 H143 109.(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.3560(15) yes
O1 H1O . 0.92(2) ?
O2 C1 . 1.3352(14) yes
O2 H2O . 1.07(2) ?
O3 C11 . 1.256(2) yes
O3 H2O . 1.38(3) ?
C1 C2 . 1.417(2) yes
C1 C9 . 1.427(2) yes
C2 C3 . 1.446(2) yes
C2 C11 . 1.458(2) yes
C3 C4 . 1.361(2) yes
C3 C13 . 1.509(2) yes
C4 C10 . 1.421(2) yes
C4 H4 . 0.96(2) ?
C5 C6 . 1.376(2) yes
C5 C10 . 1.411(2) yes
C5 H5 . 0.96(2) ?
C6 C7 . 1.402(2) yes
C6 C14 . 1.507(2) yes
C7 C8 . 1.381(2) yes
C7 H7 . 0.98(2) ?
C8 C9 . 1.428(2) yes
C9 C10 . 1.414(2) yes
C11 C12 . 1.496(2) yes
C12 H121 . 0.99(2) ?
C12 H122 . 0.96(2) ?
C12 H123 . 1.01(2) ?
C13 H131 . 0.98(2) ?
C13 H132 . 1.01(2) ?
C13 H133 . 0.97(2) ?
C14 H141 . 0.96(3) ?
C14 H142 . 0.90(3) ?
C14 H143 . 0.94(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 250158
