#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/18/2211859.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_2211859
loop_
_publ_author_name
'Pinkus, A.G.'
'Klausmeyer, Kevin K.'
'Kalyanam, Nagabushanam '
_publ_section_title
;
 1,3-Dipropionyl-2,4,6-trimethylbenzene
;
_journal_coeditor_code           HK2176
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o277
_journal_page_last               o278
_journal_paper_doi               10.1107/S1600536806053256
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H20 O2'
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_name_systematic
;
1,3-Dipropionyl-2,4,6-trimethylbenzene
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 111.989(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9058(10)
_cell_length_b                   21.191(3)
_cell_length_c                   8.8305(13)
_cell_measurement_reflns_used    733
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.94
_cell_volume                     1371.8(3)
_computing_cell_refinement       APEX-2
_computing_data_collection       'APEX-2 (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6948
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1399
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0327
_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)+(0.0613P)²+0.257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                1336
_reflns_number_total             1399
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2176.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2211859
_cod_database_fobs_code          2211859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 O1 0.1681(2) 0.02752(8) 0.5303(2) 0.0464(5) Uani d . 1
O O2 0.1919(2) 0.31685(7) 0.63961(17) 0.0354(4) Uani d . 1
C C1 0.1349(2) 0.17944(9) 0.4597(2) 0.0238(4) Uani d . 1
C C2 0.2089(3) 0.12502(9) 0.4178(2) 0.0241(4) Uani d . 1
C C3 0.3659(2) 0.12825(9) 0.3810(2) 0.0269(4) Uani d . 1
C C4 0.4494(3) 0.18665(10) 0.3888(2) 0.0286(4) Uani d . 1
H H4 0.5570 0.1891 0.3652 0.034 Uiso calc R 1
C C5 0.3805(3) 0.24139(9) 0.4298(2) 0.0283(4) Uani d . 1
C C6 0.2204(3) 0.23725(9) 0.4623(2) 0.0247(4) Uani d . 1
C C7 -0.0262(3) 0.17426(10) 0.5111(2) 0.0295(4) Uani d . 1
H H7A -0.1203 0.1478 0.4329 0.044 Uiso calc R 1
H H7B -0.0759 0.2164 0.5139 0.044 Uiso calc R 1
H H7C 0.0130 0.1552 0.6200 0.044 Uiso calc R 1
C C8 0.4480(3) 0.06955(10) 0.3381(3) 0.0356(5) Uani d . 1
H H8A 0.4818 0.0398 0.4296 0.053 Uiso calc R 1
H H8B 0.5569 0.0811 0.3165 0.053 Uiso calc R 1
H H8C 0.3585 0.0498 0.2407 0.053 Uiso calc R 1
C C9 0.4812(3) 0.30334(11) 0.4466(3) 0.0388(5) Uani d . 1
H H9A 0.5385 0.3146 0.5624 0.058 Uiso calc R 1
H H9B 0.3950 0.3365 0.3882 0.058 Uiso calc R 1
H H9C 0.5754 0.2991 0.4000 0.058 Uiso calc R 1
C C10 0.1181(3) 0.06224(9) 0.4130(2) 0.0271(4) Uani d . 1
C C11 -0.0338(3) 0.04441(9) 0.2563(3) 0.0310(4) Uani d . 1
H H11A 0.0148 0.0430 0.1680 0.037 Uiso calc R 1
H H11B -0.1285 0.0777 0.2280 0.037 Uiso calc R 1
C C12 -0.1220(4) -0.01857(11) 0.2628(3) 0.0440(6) Uani d . 1
H H12A -0.0294 -0.0519 0.2909 0.066 Uiso calc R 1
H H12B -0.2169 -0.0276 0.1559 0.066 Uiso calc R 1
H H12C -0.1766 -0.0169 0.3456 0.066 Uiso calc R 1
C C13 0.1411(3) 0.29658(9) 0.5020(2) 0.0264(4) Uani d . 1
C C14 -0.0026(3) 0.32901(10) 0.3603(3) 0.0377(5) Uani d . 1
H H14A -0.1052 0.2994 0.3101 0.045 Uiso calc R 1
H H14B 0.0495 0.3390 0.2772 0.045 Uiso calc R 1
C C15 -0.0768(4) 0.38961(11) 0.4050(3) 0.0493(7) Uani d . 1
H H15A -0.1327 0.3801 0.4845 0.074 Uiso calc R 1
H H15B -0.1686 0.4079 0.3066 0.074 Uiso calc R 1
H H15C 0.0232 0.4197 0.4527 0.074 Uiso calc R 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 0.0000 '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 0.0000 '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
C6 C1 C2 118.62(16) ?
C6 C1 C7 121.14(17) ?
C2 C1 C7 120.11(17) ?
C3 C2 C1 120.99(17) ?
C3 C2 C10 119.53(16) ?
C1 C2 C10 119.47(17) ?
C4 C3 C2 118.57(17) ?
C4 C3 C8 120.16(17) ?
C2 C3 C8 121.25(17) ?
C5 C4 C3 122.07(17) ?
C5 C4 H4 119.0 ?
C3 C4 H4 119.0 ?
C4 C5 C6 118.34(17) ?
C4 C5 C9 120.47(18) ?
C6 C5 C9 121.12(18) ?
C1 C6 C5 121.36(16) ?
C1 C6 C13 119.81(16) ?
C5 C6 C13 118.83(16) ?
C1 C7 H7A 109.5 ?
C1 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C1 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C3 C8 H8A 109.5 ?
C3 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C3 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C5 C9 H9A 109.5 ?
C5 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C5 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O1 C10 C11 121.89(18) yes
O1 C10 C2 120.94(18) yes
C11 C10 C2 117.16(16) yes
C10 C11 C12 113.98(17) ?
C10 C11 H11A 108.8 ?
C12 C11 H11A 108.8 ?
C10 C11 H11B 108.8 ?
C12 C11 H11B 108.8 ?
H11A C11 H11B 107.7 ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
O2 C13 C6 121.42(17) yes
O2 C13 C14 122.52(18) yes
C6 C13 C14 116.06(16) yes
C13 C14 C15 114.44(18) ?
C13 C14 H14A 108.6 ?
C15 C14 H14A 108.6 ?
C13 C14 H14B 108.6 ?
C15 C14 H14B 108.6 ?
H14A C14 H14B 107.6 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.210(2) yes
O2 C13 1.207(2) yes
C1 C7 1.508(3) ?
C2 C3 1.397(3) ?
C2 C1 1.404(3) ?
C2 C10 1.505(3) yes
C3 C4 1.392(3) ?
C3 C8 1.515(3) ?
C4 C5 1.387(3) ?
C4 H4 0.9500 ?
C5 C9 1.514(3) ?
C6 C1 1.395(3) ?
C6 C5 1.402(3) ?
C6 C13 1.503(3) yes
C7 H7A 0.9800 ?
C7 H7B 0.9800 ?
C7 H7C 0.9800 ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 0.9800 ?
C10 C11 1.502(3) yes
C11 C12 1.517(3) ?
C11 H11A 0.9900 ?
C11 H11B 0.9900 ?
C12 H12A 0.9800 ?
C12 H12B 0.9800 ?
C12 H12C 0.9800 ?
C14 C13 1.504(3) yes
C14 C15 1.524(3) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 202222
