#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/88/2018825.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_2018825
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
;
1,2-Diethylbenzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.556(3)
_cell_length_b                   15.931(3)
_cell_length_c                   7.7562(16)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.518
_cell_measurement_theta_min      2.557
_cell_volume                     1675.0(6)
_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      120
_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  0.0216
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5125
_diffrn_reflns_theta_full        29.47
_diffrn_reflns_theta_max         29.47
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.793651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.171
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   6(10)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression
'Fc^*^ = kFc[1 + 0.001Fc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0351
_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)+(0.0800P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                618
_reflns_number_total             625
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL 120s in Fdd2
CELL 0.71073 13.5562 15.9306 7.7562 90 90 90
ZERR 8 0.0027 0.0032 0.0016 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SFAC C H
UNIT 80 112
L.S. 15
PLAN  5
CONF C2 C1 C4 C5
EQIV $1 0.25+x, 1.25-y, 0.25+z
EQIV $2 1.25-x, 0.25+y, 0.25+z
HTAB C2 C3_$1
HTAB C4 C1_$2
BOND $h
fmap 2
acta
MERG 3
OMIT -2 59
REM <HKL>Q:\JIJI\YuLS_EtBz\YLS_12deb\120\120s.hkl</HKL>
WGHT    0.080000    0.150000
EXTI    0.014476
FVAR       0.21247
C1    1    0.537841    0.530148    0.277019    11.00000    0.01810    0.01800 =
         0.02130   -0.00078   -0.00065    0.00060
C2    1    0.574562    0.558845    0.119203    11.00000    0.02313    0.02228 =
         0.02609    0.00216    0.00301   -0.00074
C3    1    0.537742    0.529456   -0.036568    11.00000    0.03179    0.02878 =
         0.02073    0.00324    0.00385    0.00422
C4    1    0.583067    0.563225    0.441096    11.00000    0.02429    0.02494 =
         0.02480   -0.00405   -0.00361   -0.00027
C5    1    0.668547    0.509073    0.504401    11.00000    0.02800    0.03705 =
         0.03067   -0.00070   -0.00884    0.00275
H2    2    0.629978    0.600282    0.120261    11.00000    0.02653
H3    2    0.566137    0.546728   -0.141589    11.00000    0.03577
H4A   2    0.533715    0.566413    0.534874    11.00000    0.04125
H4B   2    0.607553    0.620483    0.425166    11.00000    0.04100
H5A   2    0.648376    0.453828    0.529074    11.00000    0.04095
H5B   2    0.696856    0.532822    0.606425    11.00000    0.04229
H5C   2    0.725337    0.504670    0.413284    11.00000    0.04976
HKLF 4
REM  120s in Fdd2
REM R1 =  0.0351 for    618 Fo > 4sig(Fo)  and  0.0353 for all    625 data
REM     75 parameters refined using      1 restraints
END
WGHT      0.0784      0.1433
REM Highest difference peak  0.277,  deepest hole -0.171,  1-sigma level  0.043
Q1    1   0.5526  0.5440  0.0418  11.00000  0.05    0.28
Q2    1   0.5516  0.5468  0.1998  11.00000  0.05    0.26
Q3    1   0.5588  0.5473  0.3633  11.00000  0.05    0.25
Q4    1   0.5000  0.5000  0.2716  10.50000  0.05    0.20
Q5    1   0.5000  0.5000 -0.0252  10.50000  0.05    0.17
REM The information below was added by Olex2.
REM
REM R1 = 0.0351 for 618 Fo > 4sig(Fo) and n/a for all 5675 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.28, deepest hole -0.17
REM Mean Shift 0, Max Shift 0.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = n/a
REM R1_gt = 0.0351
REM wR_ref = 0.0906
REM GOOF = 1.057
REM Shift_max = 0
REM Shift_mean = 0
REM Reflections_all = 5675
REM Reflections_gt = 618
REM Parameters = n/a
REM Hole = 0.28
REM Peak = -0.17
REM Flack = n/a
;
_cod_data_source_file            gz3229.cif
_cod_data_source_block           II
_cod_database_code               2018825
_cod_database_fobs_code          2018825
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x+1/4, -y+1/4, z+1/4'
4 '-x+1/4, y+1/4, z+1/4'
5 'x, y+1/2, z+1/2'
6 '-x, -y+1/2, z+1/2'
7 'x+1/4, -y+3/4, z+3/4'
8 '-x+1/4, y+3/4, z+3/4'
9 'x+1/2, y, z+1/2'
10 '-x+1/2, -y, z+1/2'
11 'x+3/4, -y+1/4, z+3/4'
12 '-x+3/4, y+1/4, z+3/4'
13 'x+1/2, y+1/2, z'
14 '-x+1/2, -y+1/2, z'
15 'x+3/4, -y+3/4, z+1/4'
16 '-x+3/4, y+3/4, z+1/4'
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
_atom_site_symmetry_multiplicity
C C1 0.53784(6) 0.53015(5) 0.27702(10) 0.0191(3) Uani d 1 1
C C2 0.57456(7) 0.55885(6) 0.11920(13) 0.0238(3) Uani d 1 1
C C3 0.53774(8) 0.52946(6) -0.03657(12) 0.0271(3) Uani d 1 1
C C4 0.58307(8) 0.56323(6) 0.44110(14) 0.0247(3) Uani d 1 1
C C5 0.66855(9) 0.50907(8) 0.50440(19) 0.0319(3) Uani d 1 1
H H2 0.6300(10) 0.6003(9) 0.120(2) 0.027(3) Uiso d 1 1
H H3 0.5661(13) 0.5467(12) -0.142(3) 0.036(4) Uiso d 1 1
H H4A 0.5337(13) 0.5664(14) 0.535(3) 0.041(5) Uiso d 1 1
H H4B 0.6076(13) 0.6205(11) 0.425(3) 0.041(4) Uiso d 1 1
H H5A 0.6484(15) 0.4538(13) 0.529(3) 0.041(5) Uiso d 1 1
H H5B 0.6969(14) 0.5328(13) 0.606(3) 0.042(5) Uiso d 1 1
H H5C 0.7253(15) 0.5047(14) 0.413(3) 0.050(6) 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 0.0181(4) 0.0180(5) 0.0213(4) 0.0006(3) -0.0007(3) -0.0008(3)
C2 0.0231(4) 0.0223(5) 0.0261(6) -0.0007(3) 0.0030(4) 0.0022(3)
C3 0.0318(6) 0.0288(6) 0.0207(5) 0.0042(4) 0.0039(4) 0.0032(4)
C4 0.0243(5) 0.0249(5) 0.0248(5) -0.0003(3) -0.0036(3) -0.0040(3)
C5 0.0280(5) 0.0371(6) 0.0307(5) 0.0027(4) -0.0088(4) -0.0007(4)
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
C1 C1 C4 2_665 . 122.39(5)
C2 C1 C1 . 2_665 118.90(5)
C2 C1 C4 . . 118.68(8)
C1 C2 H2 . . 118.4(11)
C3 C2 C1 . . 121.57(8)
C3 C2 H2 . . 120.0(11)
C2 C3 H3 . . 120.5(12)
C3 C3 C2 2_665 . 119.53(6)
C3 C3 H3 2_665 . 119.9(12)
C1 C4 C5 . . 112.51(9)
C1 C4 H4A . . 111.3(12)
C1 C4 H4B . . 110.9(14)
C5 C4 H4A . . 107.8(13)
C5 C4 H4B . . 108.1(11)
H4A C4 H4B . . 105.9(18)
C4 C5 H5A . . 111.9(13)
C4 C5 H5B . . 110.3(12)
C4 C5 H5C . . 112.3(12)
H5A C5 H5B . . 108.5(19)
H5A C5 H5C . . 106.7(19)
H5B C5 H5C . . 106.8(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C1 2_665 1.4054(17)
C1 C2 . 1.3982(13)
C1 C4 . 1.5077(13)
C2 C3 . 1.3885(15)
C2 H2 . 1.000(14)
C3 C3 2_665 1.388(2)
C3 H3 . 0.94(2)
C4 C5 . 1.5258(15)
C4 H4A . 0.99(2)
C4 H4B . 0.978(18)
C5 H5A . 0.94(2)
C5 H5B . 0.96(2)
C5 H5C . 1.05(2)
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 H2 C3 3_565 1.000(14) 2.961(14) 3.9397(15) 166.3(14)
C4 H4B C1 4_655 0.978(18) 3.017(18) 3.9305(14) 155.8(18)
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
C2 C1 C4 C5 -90.88(11)
