#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/88/2018824.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_2018824
loop_
_publ_author_name
'Yufit, Dmitry S.'
_publ_section_title
;
 The low-melting compounds 1,4-diethyl-, 1,2-diethyl- and ethylbenzene
;
_journal_coeditor_code           GZ3229
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              273
_journal_page_last               276
_journal_paper_doi               10.1107/S0108270113003041
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H14'
_chemical_formula_moiety         'C10 H14'
_chemical_formula_sum            'C10 H14'
_chemical_formula_weight         134.21
_chemical_name_systematic
;
1,4-Diethylbenzene
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2-beta
(compiled Nov  5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.986(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0919(9)
_cell_length_b                   6.0956(6)
_cell_length_c                   8.9673(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    220
_cell_measurement_theta_max      23.422
_cell_measurement_theta_min      2.471
_cell_volume                     450.46(8)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      220
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART 6000 CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4711
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.155766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0706
_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)+(0.1400P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2391
_refine_ls_wR_factor_ref         0.2771
_reflns_number_gt                630
_reflns_number_total             977
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL 14DEB in P2(1)/c
CELL 0.71073 9.0919 6.0956 8.9673 90 114.986 90
ZERR 2 0.0009 0.0006 0.0009 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H
UNIT 20 28
EQIV $1 1-X,0.5+Y,0.5-Z
EQIV $2 +X,0.5-Y,-0.5+Z
L.S. 9
PLAN  5
HTAB C1 C2_$1
HTAB C4 C1_$2
CONF
BOND $h
fmap 2
acta
OMIT -2 54
REM <HKL>Q:\JIJI\YuLS_EtBz\YLS_14deb\14deb.hkl</HKL>
WGHT    0.140000    0.080000
FVAR       0.55048
C1    1    0.505556    0.189176    0.424270    11.00000    0.09457    0.07173 =
         0.09003    0.01609    0.04623   -0.00202
C2    1    0.373740    0.055124    0.346824    11.00000    0.07740    0.08158 =
         0.06547   -0.00348    0.03161    0.00684
C3    1    0.370890   -0.135150    0.427248    11.00000    0.07696    0.07862 =
         0.10022   -0.00845    0.03237   -0.01793
C4    1    0.239964    0.115319    0.181839    11.00000    0.11261    0.14603 =
         0.07515   -0.00581    0.02514    0.03190
AFIX  23
H4A   2    0.288460    0.177456    0.113554    11.00000   -1.20000
H4B   2    0.183328   -0.017450    0.128486    11.00000   -1.20000
AFIX   0
C5    1    0.122578    0.270345    0.190590    11.00000    0.10554    0.12373 =
         0.10396   -0.00483    0.01737    0.02398
AFIX 137
H5A   2    0.076223    0.212666    0.260787    11.00000   -1.50000
H5B   2    0.038272    0.293784    0.082344    11.00000   -1.50000
H5C   2    0.175641    0.407066    0.234425    11.00000   -1.50000
AFIX   0
H1    2    0.510173    0.316538    0.374406    11.00000    0.11258
H3    2    0.281964   -0.236550    0.364755    11.00000    0.12277
HKLF 4
REM  14DEB in P2(1)/c
REM R1 =  0.0706 for    630 Fo > 4sig(Fo)  and  0.0993 for all    977 data
REM     55 parameters refined using      0 restraints
END
WGHT      0.1105      0.1070
REM Highest difference peak  0.140,  deepest hole -0.183,  1-sigma level  0.036
Q1    1   0.2444  0.0510  0.0703  11.00000  0.05    0.14
Q2    1   0.1380  0.3946  0.3019  11.00000  0.05    0.12
Q3    1   0.3563  0.0082  0.4127  11.00000  0.05    0.12
Q4    1   0.3991  0.1561  0.4144  11.00000  0.05    0.11
Q5    1   0.2793  0.2785  0.2211  11.00000  0.05    0.11
;
_cod_data_source_file            gz3229.cif
_cod_data_source_block           I
_cod_database_code               2018824
_cod_database_fobs_code          2018824
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
_atom_site_symmetry_multiplicity
C C1 0.5056(3) 0.1892(4) 0.4243(3) 0.0830(9) Uani d . 1 1
C C2 0.3737(3) 0.0551(4) 0.3468(3) 0.0743(8) Uani d . 1 1
C C3 0.3709(3) -0.1352(5) 0.4272(4) 0.0870(9) Uani d . 1 1
C C4 0.2400(4) 0.1153(7) 0.1818(4) 0.1162(13) Uani d . 1 1
H H4A 0.2885 0.1775 0.1136 0.139 Uiso calc R 1 1
H H4B 0.1833 -0.0175 0.1285 0.139 Uiso calc R 1 1
C C5 0.1226(4) 0.2703(7) 0.1906(4) 0.1203(13) Uani d . 1 1
H H5A 0.0762 0.2127 0.2608 0.180 Uiso calc R 1 1
H H5B 0.0383 0.2938 0.0823 0.180 Uiso calc R 1 1
H H5C 0.1756 0.4071 0.2344 0.180 Uiso calc R 1 1
H H1 0.510(4) 0.317(6) 0.374(4) 0.113(10) Uiso d . 1 1
H H3 0.282(4) -0.237(6) 0.365(4) 0.123(11) Uiso d . 1 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
C1 0.0946(17) 0.0717(15) 0.0900(18) -0.0020(14) 0.0462(15) 0.0161(13)
C2 0.0774(15) 0.0816(16) 0.0655(13) 0.0068(12) 0.0316(11) -0.0035(10)
C3 0.0770(16) 0.0786(17) 0.1002(19) -0.0179(13) 0.0324(14) -0.0085(14)
C4 0.113(2) 0.146(3) 0.0752(18) 0.032(2) 0.0251(17) -0.0058(17)
C5 0.106(2) 0.124(3) 0.104(2) 0.0240(19) 0.0174(19) -0.0048(19)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C3 . 3_656 122.0(2)
C2 C1 H1 . . 118(2)
C3 C1 H1 3_656 . 120(2)
C3 C2 C1 . . 116.3(2)
C3 C2 C4 . . 122.3(3)
C1 C2 C4 . . 121.4(3)
C2 C3 C1 . 3_656 121.6(2)
C2 C3 H3 . . 115(2)
C1 C3 H3 3_656 . 123(2)
C5 C4 C2 . . 114.3(2)
C5 C4 H4A . . 108.7
C2 C4 H4A . . 108.7
C5 C4 H4B . . 108.7
C2 C4 H4B . . 108.7
H4A C4 H4B . . 107.6
C4 C5 H5A . . 109.5
C4 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C4 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.372(4)
C1 C3 3_656 1.371(4)
C1 H1 . 0.91(3)
C2 C3 . 1.372(4)
C2 C4 . 1.511(4)
C3 C1 3_656 1.371(4)
C3 H3 . 0.98(3)
C4 C5 . 1.452(5)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 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
C1 H1 C2 2_655 0.91(3) 2.99(3) 3.787(3) 148(3)
C4 H4A C1 4_565 0.97 3.20 4.159(5) 168.3
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C3 3_656 . 0.9(4)
C3 C1 C2 C4 3_656 . -179.0(2)
C1 C2 C3 C1 . 3_656 -0.9(4)
C4 C2 C3 C1 . 3_656 179.0(2)
C3 C2 C4 C5 . . 99.3(4)
C1 C2 C4 C5 . . -80.8(4)
