#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229944.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_2229944
loop_
_publ_author_name
'Wang, Ling'
'Chang, Ziqian'
'Ding, Chunlei'
'Shao, Hua'
'Sun, Jianzi'
_publ_section_title
;
 (5-Bromo-2-methoxyphenyl)(4-ethylcyclohexyl)methanone
;
_journal_coeditor_code           BX2347
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1173
_journal_paper_doi               10.1107/S1600536811013687
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H21 Br O2'
_chemical_formula_moiety         'C16 H21 Br O2'
_chemical_formula_sum            'C16 H21 Br O2'
_chemical_formula_weight         325.24
_chemical_name_systematic
;
(5-Bromo-2-methoxyphenyl)(4-ethylcyclohexyl)methanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.329(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.204(3)
_cell_length_b                   11.276(2)
_cell_length_c                   9.604(2)
_cell_measurement_reflns_used    5413
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.2
_cell_volume                     1502.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13836
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.732
_exptl_absorpt_correction_T_max  0.6111
_exptl_absorpt_correction_T_min  0.5369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0243
_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)+(0.0260P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                2581
_reflns_number_total             3588
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2347.cif
_cod_data_source_block           I
_cod_original_cell_volume        1502.8(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229944
_cod_database_fobs_code          2229944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.359389(12) 1.039199(15) 0.078211(19) 0.02887(7) Uani d . 1 . .
O O1 0.67370(8) 1.14977(9) 0.58965(11) 0.0236(3) Uani d . 1 . .
O O2 0.71492(8) 0.90082(11) 0.30034(13) 0.0339(3) Uani d . 1 . .
C C1 0.66083(12) 1.24071(14) 0.68801(17) 0.0272(4) Uani d . 1 . .
H H1A 0.6506 1.3170 0.6382 0.041 Uiso calc R 1 . .
H H1B 0.7184 1.2455 0.7650 0.041 Uiso calc R 1 . .
H H1C 0.6047 1.2219 0.7281 0.041 Uiso calc R 1 . .
C C2 0.59954(11) 1.12527(13) 0.47931(16) 0.0176(3) Uani d . 1 . .
C C3 0.51379(11) 1.19027(13) 0.45009(17) 0.0202(4) Uani d . 1 . .
H H3 0.5046 1.2526 0.5124 0.024 Uiso calc R 1 . .
C C4 0.44236(11) 1.16512(13) 0.33205(17) 0.0212(4) Uani d . 1 . .
H H4 0.3845 1.2102 0.3123 0.025 Uiso calc R 1 . .
C C5 0.45613(11) 1.07334(14) 0.24293(17) 0.0193(4) Uani d . 1 . .
C C6 0.54008(11) 1.00793(14) 0.26967(17) 0.0181(3) Uani d . 1 . .
H H6 0.5482 0.9459 0.2063 0.022 Uiso calc R 1 . .
C C7 0.61305(11) 1.03146(12) 0.38797(16) 0.0160(3) Uani d . 1 . .
C C8 0.70157(11) 0.95429(13) 0.40477(17) 0.0192(3) Uani d . 1 . .
C C9 0.77081(11) 0.93956(12) 0.54697(17) 0.0170(3) Uani d . 1 . .
H H9 0.7377 0.9641 0.6244 0.020 Uiso calc R 1 . .
C C10 0.80398(11) 0.81086(13) 0.57217(17) 0.0205(4) Uani d . 1 . .
H H10A 0.7474 0.7589 0.5690 0.025 Uiso calc R 1 . .
H H10B 0.8367 0.7853 0.4960 0.025 Uiso calc R 1 . .
C C11 0.87275(11) 0.79932(13) 0.71633(17) 0.0208(4) Uani d . 1 . .
H H11A 0.8930 0.7155 0.7317 0.025 Uiso calc R 1 . .
H H11B 0.8386 0.8217 0.7921 0.025 Uiso calc R 1 . .
C C12 0.96177(11) 0.87687(13) 0.72848(17) 0.0205(4) Uani d . 1 . .
H H12 0.9971 0.8502 0.6545 0.025 Uiso calc R 1 . .
C C13 0.93087(11) 1.00610(14) 0.69645(18) 0.0232(4) Uani d . 1 . .
H H13A 0.9005 1.0362 0.7731 0.028 Uiso calc R 1 . .
H H13B 0.9887 1.0550 0.6959 0.028 Uiso calc R 1 . .
C C14 0.86004(10) 1.01921(14) 0.55324(17) 0.0205(4) Uani d . 1 . .
H H14A 0.8924 0.9971 0.4753 0.025 Uiso calc R 1 . .
H H14B 0.8394 1.1030 0.5393 0.025 Uiso calc R 1 . .
C C15 1.02894(11) 0.86209(15) 0.87409(18) 0.0268(4) Uani d . 1 . .
H H15A 0.9958 0.8927 0.9476 0.032 Uiso calc R 1 . .
H H15B 1.0405 0.7763 0.8923 0.032 Uiso calc R 1 . .
C C16 1.12570(12) 0.92389(19) 0.8919(2) 0.0430(5) Uani d . 1 . .
H H16A 1.1575 0.8988 0.8157 0.064 Uiso calc R 1 . .
H H16B 1.1662 0.9029 0.9846 0.064 Uiso calc R 1 . .
H H16C 1.1159 1.0099 0.8870 0.064 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
C2 O1 C1 . . 118.36(12) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 123.32(14) ?
O1 C2 C7 . . 116.91(14) ?
C3 C2 C7 . . 119.73(15) ?
C4 C3 C2 . . 120.91(15) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.06(15) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C6 C5 C4 . . 121.06(15) ?
C6 C5 Br1 . . 119.32(12) ?
C4 C5 Br1 . . 119.61(12) ?
C5 C6 C7 . . 120.96(15) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C6 C7 C2 . . 118.28(14) ?
C6 C7 C8 . . 115.86(14) ?
C2 C7 C8 . . 125.85(14) ?
O2 C8 C7 . . 118.01(14) ?
O2 C8 C9 . . 120.22(14) ?
C7 C8 C9 . . 121.75(14) ?
C8 C9 C10 . . 111.48(13) ?
C8 C9 C14 . . 109.97(13) ?
C10 C9 C14 . . 108.86(13) ?
C8 C9 H9 . . 108.8 ?
C10 C9 H9 . . 108.8 ?
C14 C9 H9 . . 108.8 ?
C11 C10 C9 . . 109.99(12) ?
C11 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
C11 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
C10 C11 C12 . . 112.50(13) ?
C10 C11 H11A . . 109.1 ?
C12 C11 H11A . . 109.1 ?
C10 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
C11 C12 C15 . . 110.78(13) ?
C11 C12 C13 . . 109.46(12) ?
C15 C12 C13 . . 112.58(13) ?
C11 C12 H12 . . 108.0 ?
C15 C12 H12 . . 108.0 ?
C13 C12 H12 . . 108.0 ?
C14 C13 C12 . . 112.18(13) ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13B . . 109.2 ?
C12 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C9 . . 110.86(13) ?
C13 C14 H14A . . 109.5 ?
C9 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C16 C15 C12 . . 115.32(15) ?
C16 C15 H15A . . 108.4 ?
C12 C15 H15A . . 108.4 ?
C16 C15 H15B . . 108.4 ?
C12 C15 H15B . . 108.4 ?
H15A C15 H15B . . 107.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 . 1.9002(16) ?
O1 C2 . 1.3536(17) ?
O1 C1 . 1.4322(17) ?
O2 C8 . 1.2192(18) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.398(2) ?
C2 C7 . 1.413(2) ?
C3 C4 . 1.380(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.379(2) ?
C6 C7 . 1.390(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.509(2) ?
C8 C9 . 1.512(2) ?
C9 C10 . 1.529(2) ?
C9 C14 . 1.544(2) ?
C9 H9 . 1.0000 ?
C10 C11 . 1.520(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.521(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C15 . 1.524(2) ?
C12 C13 . 1.534(2) ?
C12 H12 . 1.0000 ?
C13 C14 . 1.528(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.518(2) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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
C1 O1 C2 C3 . . . . 5.2(2) ?
C1 O1 C2 C7 . . . . -177.20(13) ?
O1 C2 C3 C4 . . . . 176.77(14) ?
C7 C2 C3 C4 . . . . -0.8(2) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
C3 C4 C5 Br1 . . . . -178.97(11) ?
C4 C5 C6 C7 . . . . 0.7(2) ?
Br1 C5 C6 C7 . . . . 179.06(11) ?
C5 C6 C7 C2 . . . . -0.8(2) ?
C5 C6 C7 C8 . . . . -179.56(14) ?
O1 C2 C7 C6 . . . . -176.87(13) ?
C3 C2 C7 C6 . . . . 0.9(2) ?
O1 C2 C7 C8 . . . . 1.7(2) ?
C3 C2 C7 C8 . . . . 179.47(14) ?
C6 C7 C8 O2 . . . . 18.9(2) ?
C2 C7 C8 O2 . . . . -159.73(16) ?
C6 C7 C8 C9 . . . . -159.20(14) ?
C2 C7 C8 C9 . . . . 22.2(2) ?
O2 C8 C9 C10 . . . . -39.5(2) ?
C7 C8 C9 C10 . . . . 138.54(14) ?
O2 C8 C9 C14 . . . . 81.31(18) ?
C7 C8 C9 C14 . . . . -100.62(16) ?
C8 C9 C10 C11 . . . . -179.57(13) ?
C14 C9 C10 C11 . . . . 58.95(17) ?
C9 C10 C11 C12 . . . . -59.46(17) ?
C10 C11 C12 C15 . . . . -179.67(13) ?
C10 C11 C12 C13 . . . . 55.60(18) ?
C11 C12 C13 C14 . . . . -53.76(18) ?
C15 C12 C13 C14 . . . . -177.44(14) ?
C12 C13 C14 C9 . . . . 56.16(18) ?
C8 C9 C14 C13 . . . . 179.77(13) ?
C10 C9 C14 C13 . . . . -57.84(17) ?
C11 C12 C15 C16 . . . . 172.94(15) ?
C13 C12 C15 C16 . . . . -64.1(2) ?
