#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/61/2226110.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_2226110
loop_
_publ_author_name
'Xie, Songwen'
'Nusbaum, Dannette A.'
'Stein, Holly J.'
'Pink, Maren'
_publ_section_title
;
 4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
;
_journal_coeditor_code           FJ2304
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1443
_journal_paper_doi               10.1107/S1600536810018544
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H20 O3'
_chemical_formula_moiety         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32
_chemical_name_systematic
;
4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.032(2)
_cell_length_b                   7.8423(17)
_cell_length_c                   32.140(8)
_cell_measurement_reflns_used    2804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      15.3
_cell_measurement_theta_min      2.3
_cell_volume                     2780.6(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'diamond 1 1 1'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.44280
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8586
_diffrn_reflns_theta_full        15.28
_diffrn_reflns_theta_max         15.28
_diffrn_reflns_theta_min         0.79
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.9989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0368
_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)+(0.0707P)²+0.0727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1755
_reflns_number_total             2173
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2304.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2780.7(11)
_cod_database_code               2226110
_cod_database_fobs_code          2226110
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O O1 -0.01213(10) 0.06346(16) 0.54893(3) 0.0182(3) Uani d . 1 . .
O O2 0.02685(11) 0.22640(18) 0.49329(4) 0.0209(3) Uani d . 1 . .
H H2O 0.018(2) 0.122(4) 0.4790(8) 0.049(7) Uiso d . 1 . .
O O3 0.19151(12) 0.77788(18) 0.76439(3) 0.0250(4) Uani d . 1 . .
C C1 -0.07178(15) 0.5720(2) 0.60649(5) 0.0173(4) Uani d . 1 . .
H H1A -0.0730 0.6650 0.5857 0.021 Uiso calc R 1 . .
H H1B -0.1403 0.5909 0.6258 0.021 Uiso calc R 1 . .
C C2 -0.09016(14) 0.4018(2) 0.58418(5) 0.0152(4) Uani d . 1 . .
H H2 -0.1031 0.3108 0.6055 0.018 Uiso calc R 1 . .
C C3 0.02669(14) 0.3611(2) 0.55976(5) 0.0141(4) Uani d . 1 . .
H H3 0.0446 0.4592 0.5409 0.017 Uiso calc R 1 . .
C C4 0.13603(14) 0.3370(2) 0.58944(5) 0.0148(4) Uani d . 1 . .
H H4 0.1288 0.2227 0.6030 0.018 Uiso calc R 1 . .
C C5 0.13641(15) 0.4715(2) 0.62290(5) 0.0161(4) Uani d . 1 . .
H H5 0.2066 0.4796 0.6399 0.019 Uiso calc R 1 . .
C C6 0.04532(15) 0.5812(2) 0.63059(5) 0.0152(4) Uani d . 1 . .
C C7 0.05757(14) 0.7208(2) 0.66193(5) 0.0157(4) Uani d . 1 . .
C C8 0.11780(15) 0.6918(2) 0.69955(5) 0.0167(4) Uani d . 1 . .
H H8 0.1500 0.5820 0.7054 0.020 Uiso calc R 1 . .
C C9 0.13098(15) 0.8233(2) 0.72858(5) 0.0181(4) Uani d . 1 . .
C C10 0.08441(15) 0.9845(2) 0.72076(5) 0.0202(4) Uani d . 1 . .
H H10 0.0930 1.0736 0.7406 0.024 Uiso calc R 1 . .
C C11 0.02467(16) 1.0126(3) 0.68315(5) 0.0209(4) Uani d . 1 . .
H H11 -0.0067 1.1228 0.6772 0.025 Uiso calc R 1 . .
C C12 0.01008(15) 0.8828(2) 0.65423(5) 0.0189(4) Uani d . 1 . .
H H12 -0.0324 0.9042 0.6291 0.023 Uiso calc R 1 . .
C C13 -0.20110(15) 0.4090(2) 0.55581(5) 0.0194(4) Uani d . 1 . .
H H13A -0.2153 0.2962 0.5436 0.029 Uiso calc R 1 . .
H H13B -0.1870 0.4920 0.5335 0.029 Uiso calc R 1 . .
H H13C -0.2722 0.4433 0.5721 0.029 Uiso calc R 1 . .
C C14 0.01185(14) 0.2031(2) 0.53354(5) 0.0137(4) Uani d . 1 . .
C C15 0.25486(15) 0.3418(2) 0.56468(5) 0.0183(4) Uani d . 1 . .
H H15A 0.3235 0.3277 0.5837 0.027 Uiso calc R 1 . .
H H15B 0.2618 0.4515 0.5503 0.027 Uiso calc R 1 . .
H H15C 0.2552 0.2492 0.5442 0.027 Uiso calc R 1 . .
C C16 0.19283(18) 0.8987(3) 0.79772(5) 0.0244(5) Uani d . 1 . .
H H16A 0.2328 0.8483 0.8220 0.037 Uiso calc R 1 . .
H H16B 0.1094 0.9297 0.8050 0.037 Uiso calc R 1 . .
H H16C 0.2371 1.0010 0.7890 0.037 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 0.0015 0.0009 '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 0.0056 0.0036 '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 O2 H2O . . 110.1(16) ?
C9 O3 C16 . . 117.34(15) ?
C6 C1 C2 . . 113.35(14) ?
C6 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
C6 C1 H1B . . 108.9 ?
C2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C13 C2 C1 . . 110.76(14) ?
C13 C2 C3 . . 111.93(13) ?
C1 C2 C3 . . 107.97(13) ?
C13 C2 H2 . . 108.7 ?
C1 C2 H2 . . 108.7 ?
C3 C2 H2 . . 108.7 ?
C14 C3 C2 . . 111.34(13) ?
C14 C3 C4 . . 109.16(14) ?
C2 C3 C4 . . 111.26(13) ?
C14 C3 H3 . . 108.3 ?
C2 C3 H3 . . 108.3 ?
C4 C3 H3 . . 108.3 ?
C5 C4 C15 . . 110.53(14) ?
C5 C4 C3 . . 110.86(14) ?
C15 C4 C3 . . 110.06(13) ?
C5 C4 H4 . . 108.4 ?
C15 C4 H4 . . 108.4 ?
C3 C4 H4 . . 108.4 ?
C6 C5 C4 . . 125.23(15) ?
C6 C5 H5 . . 117.4 ?
C4 C5 H5 . . 117.4 ?
C5 C6 C7 . . 121.65(15) ?
C5 C6 C1 . . 120.98(16) ?
C7 C6 C1 . . 117.32(14) ?
C12 C7 C8 . . 118.65(15) ?
C12 C7 C6 . . 120.89(15) ?
C8 C7 C6 . . 120.46(16) ?
C7 C8 C9 . . 120.42(17) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
O3 C9 C10 . . 124.50(15) ?
O3 C9 C8 . . 114.65(16) ?
C10 C9 C8 . . 120.85(16) ?
C9 C10 C11 . . 118.43(16) ?
C9 C10 H10 . . 120.8 ?
C11 C10 H10 . . 120.8 ?
C12 C11 C10 . . 121.27(18) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C7 . . 120.36(16) ?
C11 C12 H12 . . 119.8 ?
C7 C12 H12 . . 119.8 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O1 C14 O2 . . 123.06(15) ?
O1 C14 C3 . . 122.03(14) ?
O2 C14 C3 . . 114.91(15) ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O3 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
O1 C14 . 1.230(2) ?
O2 C14 . 1.317(2) ?
O2 H2O . 0.94(3) ?
O3 C9 . 1.378(2) ?
O3 C16 . 1.430(2) ?
C1 C6 . 1.508(2) ?
C1 C2 . 1.528(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C13 . 1.527(2) ?
C2 C3 . 1.543(2) ?
C2 H2 . 1.0000 ?
C3 C14 . 1.508(2) ?
C3 C4 . 1.549(2) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.507(2) ?
C4 C15 . 1.534(2) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.346(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.493(2) ?
C7 C12 . 1.396(3) ?
C7 C8 . 1.398(2) ?
C8 C9 . 1.399(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(3) ?
C10 C11 . 1.394(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.388(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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
O2 H2O O1 5_556 0.94(3) 1.71(3) 2.6523(19) 175(2)
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
C6 C1 C2 C13 . . . . -172.40(14) ?
C6 C1 C2 C3 . . . . -49.53(18) ?
C13 C2 C3 C14 . . . . -52.46(19) ?
C1 C2 C3 C14 . . . . -174.62(13) ?
C13 C2 C3 C4 . . . . -174.47(15) ?
C1 C2 C3 C4 . . . . 63.37(17) ?
C14 C3 C4 C5 . . . . -166.45(14) ?
C2 C3 C4 C5 . . . . -43.19(19) ?
C14 C3 C4 C15 . . . . 70.95(17) ?
C2 C3 C4 C15 . . . . -165.78(14) ?
C15 C4 C5 C6 . . . . 132.37(18) ?
C3 C4 C5 C6 . . . . 10.1(2) ?
C4 C5 C6 C7 . . . . -174.49(16) ?
C4 C5 C6 C1 . . . . 3.0(3) ?
C2 C1 C6 C5 . . . . 17.8(2) ?
C2 C1 C6 C7 . . . . -164.57(14) ?
C5 C6 C7 C12 . . . . 140.02(18) ?
C1 C6 C7 C12 . . . . -37.5(2) ?
C5 C6 C7 C8 . . . . -39.5(2) ?
C1 C6 C7 C8 . . . . 142.90(16) ?
C12 C7 C8 C9 . . . . -0.6(2) ?
C6 C7 C8 C9 . . . . 178.94(15) ?
C16 O3 C9 C10 . . . . 8.2(2) ?
C16 O3 C9 C8 . . . . -171.22(15) ?
C7 C8 C9 O3 . . . . 179.71(14) ?
C7 C8 C9 C10 . . . . 0.2(2) ?
O3 C9 C10 C11 . . . . -179.78(16) ?
C8 C9 C10 C11 . . . . -0.4(2) ?
C9 C10 C11 C12 . . . . 0.9(3) ?
C10 C11 C12 C7 . . . . -1.3(3) ?
C8 C7 C12 C11 . . . . 1.2(2) ?
C6 C7 C12 C11 . . . . -178.39(15) ?
C2 C3 C14 O1 . . . . -60.2(2) ?
C4 C3 C14 O1 . . . . 63.06(19) ?
C2 C3 C14 O2 . . . . 120.03(15) ?
C4 C3 C14 O2 . . . . -116.76(15) ?
