#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228743.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_2228743
loop_
_publ_author_name
'Li, Yan'
'Kong, Xue'
'Chen, Guan-Hong'
'Chi, Jian-Guo'
'Wang, Jia-Ning'
_publ_section_title
;
 4-Bromo-2-[1-(4-ethoxyphenyl)-1-methylethyl]-1-methylbenzene
;
_journal_coeditor_code           HG2759
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o21
_journal_paper_doi               10.1107/S1600536810049445
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H21 Br O'
_chemical_formula_moiety         'C18 H21 Br O'
_chemical_formula_sum            'C18 H21 Br O'
_chemical_formula_weight         333.26
_chemical_name_systematic
;
4-Bromo-2-[1-(4-ethoxyphenyl)-1-methylethyl]-1-methylbenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 110.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.164(2)
_cell_length_b                   9.5142(19)
_cell_length_c                   16.135(3)
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.097
_cell_measurement_theta_min      2.141
_cell_volume                     1608.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13056
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.550
_exptl_absorpt_correction_T_max  0.8220
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.393
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2101
_reflns_number_total             2839
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2759.cif
_cod_data_source_block           I
_cod_original_cell_volume        1608.2(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228743
_cod_database_fobs_code          2228743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.02586(4) 0.72212(4) 0.15240(3) 0.0665(3) Uani d . 1 . .
O O1 0.1869(3) -0.2600(3) 0.39327(19) 0.0644(8) Uani d . 1 . .
C C1 -0.1877(4) 0.1214(4) 0.1522(3) 0.0751(13) Uani d . 1 . .
H H1A -0.2276 0.0963 0.0912 0.113 Uiso calc R 1 . .
H H1B -0.2496 0.1180 0.1812 0.113 Uiso calc R 1 . .
H H1C -0.1198 0.0566 0.1802 0.113 Uiso calc R 1 . .
C C2 -0.1338(4) 0.2691(4) 0.1586(3) 0.0545(10) Uani d . 1 . .
C C3 -0.1463(4) 0.3354(5) 0.0805(3) 0.0647(11) Uani d . 1 . .
H H3 -0.1872 0.2878 0.0279 0.078 Uiso calc R 1 . .
C C4 -0.1010(4) 0.4700(4) 0.0762(3) 0.0635(11) Uani d . 1 . .
H H4 -0.1120 0.5129 0.0222 0.076 Uiso calc R 1 . .
C C5 -0.0388(3) 0.5377(4) 0.1551(2) 0.0497(9) Uani d . 1 . .
C C6 -0.0249(3) 0.4749(4) 0.2352(2) 0.0491(9) Uani d . 1 . .
H H6 0.0166 0.5236 0.2872 0.059 Uiso calc R 1 . .
C C7 -0.0716(3) 0.3405(4) 0.2397(2) 0.0467(8) Uani d . 1 . .
C C8 -0.0623(4) 0.2769(4) 0.3297(3) 0.0501(9) Uani d . 1 . .
C C9 -0.1980(4) 0.2698(4) 0.3348(3) 0.0736(13) Uani d . 1 . .
H H9A -0.2450 0.1953 0.2975 0.110 Uiso calc R 1 . .
H H9B -0.2410 0.3575 0.3153 0.110 Uiso calc R 1 . .
H H9C -0.1921 0.2522 0.3946 0.110 Uiso calc R 1 . .
C C10 0.0203(4) 0.3690(4) 0.4079(3) 0.0723(12) Uani d . 1 . .
H H10A 0.0296 0.3226 0.4626 0.108 Uiso calc R 1 . .
H H10B -0.0206 0.4583 0.4062 0.108 Uiso calc R 1 . .
H H10C 0.1029 0.3831 0.4034 0.108 Uiso calc R 1 . .
C C11 0.0025(3) 0.1309(4) 0.3436(2) 0.0471(9) Uani d . 1 . .
C C12 -0.0460(4) 0.0150(4) 0.3738(2) 0.0575(10) Uani d . 1 . .
H H12 -0.1226 0.0235 0.3843 0.069 Uiso calc R 1 . .
C C13 0.0171(4) -0.1130(4) 0.3887(3) 0.0628(11) Uani d . 1 . .
H H13 -0.0187 -0.1895 0.4075 0.075 Uiso calc R 1 . .
C C14 0.1324(4) -0.1283(4) 0.3759(2) 0.0513(9) Uani d . 1 . .
C C15 0.1832(3) -0.0141(4) 0.3464(2) 0.0525(9) Uani d . 1 . .
H H15 0.2603 -0.0225 0.3367 0.063 Uiso calc R 1 . .
C C16 0.1182(3) 0.1130(4) 0.3314(2) 0.0543(10) Uani d . 1 . .
H H16 0.1539 0.1893 0.3123 0.065 Uiso calc R 1 . .
C C17 0.3065(4) -0.2787(4) 0.3818(3) 0.0673(12) Uani d . 1 . .
H H17A 0.3699 -0.2168 0.4211 0.081 Uiso calc R 1 . .
H H17B 0.2990 -0.2568 0.3215 0.081 Uiso calc R 1 . .
C C18 0.3460(4) -0.4312(5) 0.4026(3) 0.0896(15) Uani d . 1 . .
H H18A 0.3480 -0.4533 0.4611 0.134 Uiso calc R 1 . .
H H18B 0.4292 -0.4454 0.3991 0.134 Uiso calc R 1 . .
H H18C 0.2856 -0.4913 0.3608 0.134 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 0.0016 '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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C14 O1 C17 . . 117.1(3) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C7 . . 119.2(3) ?
C3 C2 C1 . . 116.8(3) ?
C7 C2 C1 . . 124.1(3) ?
C2 C3 C4 . . 123.2(4) ?
C2 C3 H3 . . 118.4 ?
C4 C3 H3 . . 118.4 ?
C5 C4 C3 . . 117.4(3) ?
C5 C4 H4 . . 121.3 ?
C3 C4 H4 . . 121.3 ?
C4 C5 C6 . . 121.3(3) ?
C4 C5 Br1 . . 118.8(3) ?
C6 C5 Br1 . . 119.9(3) ?
C5 C6 C7 . . 121.5(3) ?
C5 C6 H6 . . 119.3 ?
C7 C6 H6 . . 119.3 ?
C6 C7 C2 . . 117.6(3) ?
C6 C7 C8 . . 120.3(3) ?
C2 C7 C8 . . 122.0(3) ?
C7 C8 C11 . . 111.5(3) ?
C7 C8 C9 . . 108.5(3) ?
C11 C8 C9 . . 111.8(3) ?
C7 C8 C10 . . 111.8(3) ?
C11 C8 C10 . . 105.8(3) ?
C9 C8 C10 . . 107.4(3) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C16 C11 C12 . . 116.7(3) ?
C16 C11 C8 . . 120.2(3) ?
C12 C11 C8 . . 123.0(3) ?
C13 C12 C11 . . 121.5(3) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C14 C13 C12 . . 120.8(4) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
O1 C14 C13 . . 115.8(3) ?
O1 C14 C15 . . 125.4(3) ?
C13 C14 C15 . . 118.9(3) ?
C14 C15 C16 . . 119.5(3) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C11 C16 C15 . . 122.7(3) ?
C11 C16 H16 . . 118.6 ?
C15 C16 H16 . . 118.6 ?
O1 C17 C18 . . 107.7(4) ?
O1 C17 H17A . . 110.2 ?
C18 C17 H17A . . 110.2 ?
O1 C17 H17B . . 110.2 ?
C18 C17 H17B . . 110.2 ?
H17A C17 H17B . . 108.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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
Br1 C5 . 1.904(4) ?
O1 C14 . 1.379(4) ?
O1 C17 . 1.421(6) ?
C1 C2 . 1.518(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.373(5) ?
C2 C7 . 1.423(5) ?
C3 C4 . 1.388(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(5) ?
C6 C7 . 1.393(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.543(5) ?
C8 C11 . 1.545(5) ?
C8 C9 . 1.546(6) ?
C8 C10 . 1.552(6) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C16 . 1.384(5) ?
C11 C12 . 1.389(5) ?
C12 C13 . 1.386(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.385(5) ?
C15 C16 . 1.388(5) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.520(5) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 0.1(6) ?
C1 C2 C3 C4 . . . . -179.6(4) ?
C2 C3 C4 C5 . . . . 1.0(6) ?
C3 C4 C5 C6 . . . . -1.4(6) ?
C3 C4 C5 Br1 . . . . 179.7(3) ?
C4 C5 C6 C7 . . . . 0.7(5) ?
Br1 C5 C6 C7 . . . . 179.6(3) ?
C5 C6 C7 C2 . . . . 0.4(5) ?
C5 C6 C7 C8 . . . . -176.1(3) ?
C3 C2 C7 C6 . . . . -0.8(6) ?
C1 C2 C7 C6 . . . . 178.8(4) ?
C3 C2 C7 C8 . . . . 175.7(4) ?
C1 C2 C7 C8 . . . . -4.7(6) ?
C6 C7 C8 C11 . . . . -127.0(4) ?
C2 C7 C8 C11 . . . . 56.7(5) ?
C6 C7 C8 C9 . . . . 109.5(4) ?
C2 C7 C8 C9 . . . . -66.8(4) ?
C6 C7 C8 C10 . . . . -8.8(5) ?
C2 C7 C8 C10 . . . . 174.9(4) ?
C7 C8 C11 C16 . . . . 50.9(5) ?
C9 C8 C11 C16 . . . . 172.5(4) ?
C10 C8 C11 C16 . . . . -70.9(4) ?
C7 C8 C11 C12 . . . . -133.2(4) ?
C9 C8 C11 C12 . . . . -11.6(5) ?
C10 C8 C11 C12 . . . . 105.0(4) ?
C16 C11 C12 C13 . . . . -1.6(6) ?
C8 C11 C12 C13 . . . . -177.6(4) ?
C11 C12 C13 C14 . . . . 1.6(6) ?
C17 O1 C14 C13 . . . . -179.2(4) ?
C17 O1 C14 C15 . . . . 1.6(5) ?
C12 C13 C14 O1 . . . . 179.6(4) ?
C12 C13 C14 C15 . . . . -1.2(6) ?
O1 C14 C15 C16 . . . . 179.9(3) ?
C13 C14 C15 C16 . . . . 0.8(5) ?
C12 C11 C16 C15 . . . . 1.2(5) ?
C8 C11 C16 C15 . . . . 177.3(3) ?
C14 C15 C16 C11 . . . . -0.8(6) ?
C14 O1 C17 C18 . . . . -178.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656422
