#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220228.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_2220228
loop_
_publ_author_name
'Hu, Yong-Hong'
'Zhao, Xiao-Lei'
'Yang, Wen-Ge'
'Yao, Jin-Feng'
'Lu, Xiu-Tao'
_publ_section_title
;
 1-(4-Methyl-1-naphthyl)ethanone
;
_journal_coeditor_code           HK2564
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2307
_journal_paper_doi               10.1107/S1600536808035812
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H12 O'
_chemical_formula_moiety         'C13 H12 O'
_chemical_formula_sum            'C13 H12 O'
_chemical_formula_weight         184.23
_chemical_name_systematic
;
1-(4-Methyl-1-naphthyl)ethanone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.449(3)
_cell_length_b                   7.8290(16)
_cell_length_c                   16.755(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2026.5(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1932
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.05P)²+0.8P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                905
_reflns_number_total             1846
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2564.cif
_cod_data_source_block           I
_cod_database_code               2220228
_cod_database_fobs_code          2220228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_refinement_flags
_atom_site_occupancy
O O 0.72633(18) -0.0605(3) 0.52877(14) 0.1022(9) Uani d . 1
C C1 0.4927(2) 0.1819(5) 0.5918(2) 0.0830(11) Uani d . 1
H H1A 0.4590 0.1827 0.5457 0.100 Uiso calc R 1
C C2 0.5750(2) 0.1221(4) 0.58895(18) 0.0665(9) Uani d . 1
H H2A 0.5973 0.0829 0.5407 0.080 Uiso calc R 1
C C3 0.62766(19) 0.1181(3) 0.65824(17) 0.0498(7) Uani d . 1
C C4 0.7163(2) 0.0658(3) 0.65707(18) 0.0573(8) Uani d . 1
C C5 0.7619(2) 0.0651(4) 0.7276(2) 0.0679(9) Uani d . 1
H H5A 0.8198 0.0326 0.7272 0.082 Uiso calc R 1
C C6 0.7234(2) 0.1121(4) 0.79985(19) 0.0710(10) Uani d . 1
H H6A 0.7554 0.1034 0.8467 0.085 Uiso calc R 1
C C7 0.6410(2) 0.1698(4) 0.80342(17) 0.0611(8) Uani d . 1
C C8 0.59134(18) 0.1753(3) 0.73121(18) 0.0531(7) Uani d . 1
C C9 0.5063(2) 0.2390(5) 0.7314(2) 0.0731(10) Uani d . 1
H H9A 0.4825 0.2794 0.7787 0.088 Uiso calc R 1
C C10 0.4583(2) 0.2424(4) 0.6633(3) 0.0829(11) Uani d . 1
H H10A 0.4022 0.2854 0.6645 0.100 Uiso calc R 1
C C11 0.6043(3) 0.2281(5) 0.88156(17) 0.0941(13) Uani d . 1
H H11A 0.6474 0.2163 0.9225 0.141 Uiso calc R 1
H H11B 0.5548 0.1597 0.8948 0.141 Uiso calc R 1
H H11C 0.5873 0.3457 0.8775 0.141 Uiso calc R 1
C C12 0.7628(3) 0.0157(4) 0.5827(2) 0.0733(10) Uani d . 1
C C13 0.8571(2) 0.0651(4) 0.5755(2) 0.0961(13) Uani d . 1
H H13A 0.8794 0.0259 0.5253 0.144 Uiso calc R 1
H H13B 0.8893 0.0137 0.6183 0.144 Uiso calc R 1
H H13C 0.8625 0.1871 0.5786 0.144 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O 0.127(2) 0.098(2) 0.0814(16) -0.0038(18) 0.0255(17) -0.0239(15)
C1 0.081(3) 0.079(3) 0.090(3) -0.011(2) -0.028(2) 0.017(2)
C2 0.078(2) 0.061(2) 0.061(2) -0.0079(19) -0.0101(18) 0.0077(16)
C3 0.0557(18) 0.0421(16) 0.0516(16) -0.0036(14) 0.0025(15) 0.0035(14)
C4 0.066(2) 0.0455(17) 0.0601(18) -0.0005(16) 0.0093(18) 0.0039(15)
C5 0.063(2) 0.060(2) 0.081(2) 0.0066(17) -0.005(2) 0.0095(18)
C6 0.079(3) 0.074(2) 0.061(2) 0.000(2) -0.0125(18) 0.0105(17)
C7 0.073(2) 0.0565(19) 0.0535(18) -0.0008(18) 0.0024(18) 0.0037(15)
C8 0.0516(18) 0.0464(16) 0.0614(18) -0.0009(15) 0.0018(16) 0.0054(14)
C9 0.066(2) 0.074(2) 0.079(2) 0.005(2) 0.010(2) 0.0109(19)
C10 0.053(2) 0.072(2) 0.124(3) -0.0011(19) 0.000(2) 0.021(2)
C11 0.122(3) 0.101(3) 0.059(2) 0.013(3) 0.011(2) -0.004(2)
C12 0.095(3) 0.0495(19) 0.076(2) 0.0060(19) 0.021(2) 0.0012(18)
C13 0.079(3) 0.081(3) 0.128(3) 0.007(2) 0.046(2) 0.004(2)
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 C1 C10 120.3(3)
C2 C1 H1A 119.9
C10 C1 H1A 119.9
C1 C2 C3 121.1(3)
C1 C2 H2A 119.4
C3 C2 H2A 119.4
C8 C3 C2 118.2(3)
C8 C3 C4 118.8(3)
C2 C3 C4 123.0(3)
C5 C4 C3 118.7(3)
C5 C4 C12 118.1(3)
C3 C4 C12 123.2(3)
C4 C5 C6 121.7(3)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C7 C6 C5 121.8(3)
C7 C6 H6A 119.1
C5 C6 H6A 119.1
C6 C7 C8 118.5(3)
C6 C7 C11 119.8(3)
C8 C7 C11 121.7(3)
C9 C8 C3 118.9(3)
C9 C8 C7 120.6(3)
C3 C8 C7 120.4(3)
C10 C9 C8 121.0(3)
C10 C9 H9A 119.5
C8 C9 H9A 119.5
C9 C10 C1 120.5(3)
C9 C10 H10A 119.8
C1 C10 H10A 119.8
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O C12 C4 121.7(3)
O C12 C13 120.8(3)
C4 C12 C13 117.5(3)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C12 1.220(4)
C1 C2 1.357(4)
C1 C10 1.394(5)
C1 H1A 0.9300
C2 C3 1.418(4)
C2 H2A 0.9300
C3 C8 1.418(4)
C3 C4 1.430(4)
C4 C5 1.376(4)
C4 C12 1.491(4)
C5 C6 1.398(4)
C5 H5A 0.9300
C6 C7 1.352(4)
C6 H6A 0.9300
C7 C8 1.434(4)
C7 C11 1.498(4)
C8 C9 1.405(4)
C9 C10 1.360(4)
C9 H9A 0.9300
C10 H10A 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.513(5)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C2 H2A O . 0.93 2.30 2.920(4) 124.00
C13 H13C O 7_765 0.96 2.55 3.296(4) 135.00
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
C10 C1 C2 C3 0.5(5)
C1 C2 C3 C8 1.3(4)
C1 C2 C3 C4 -176.1(3)
C8 C3 C4 C5 3.1(4)
C2 C3 C4 C5 -179.6(3)
C8 C3 C4 C12 -175.4(3)
C2 C3 C4 C12 2.0(4)
C3 C4 C5 C6 0.8(5)
C12 C4 C5 C6 179.3(3)
C4 C5 C6 C7 -3.9(5)
C5 C6 C7 C8 2.7(5)
C5 C6 C7 C11 -176.5(3)
C2 C3 C8 C9 -2.3(4)
C4 C3 C8 C9 175.2(3)
C2 C3 C8 C7 178.4(3)
C4 C3 C8 C7 -4.1(4)
C6 C7 C8 C9 -178.1(3)
C11 C7 C8 C9 1.1(5)
C6 C7 C8 C3 1.2(4)
C11 C7 C8 C3 -179.5(3)
C3 C8 C9 C10 1.6(5)
C7 C8 C9 C10 -179.1(3)
C8 C9 C10 C1 0.2(5)
C2 C1 C10 C9 -1.3(5)
C5 C4 C12 O 146.1(3)
C3 C4 C12 O -35.4(5)
C5 C4 C12 C13 -34.8(4)
C3 C4 C12 C13 143.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 88133
