#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226318.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_2226318
loop_
_publ_author_name
'Yang, Lin-Tao'
'Ye, Jiao'
'Luo, Xian-Fu'
'Hu, Ai-Xi'
_publ_section_title
;
 2-(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yloxy)acetic acid
 monohydrate
;
_journal_coeditor_code           WM2329
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1433
_journal_paper_doi               10.1107/S1600536810018659
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 O4, H2 O'
_chemical_formula_moiety         'C12 H14 O4, H2 O'
_chemical_formula_sum            'C12 H16 O5'
_chemical_formula_weight         240.25
_chemical_melting_point          383.2
_chemical_name_systematic
;
2-(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yloxy)acetic acid monohydrate
;
_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                 121.0000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1692(7)
_cell_length_b                   9.2516(6)
_cell_length_c                   15.3647(11)
_cell_measurement_reflns_used    3163
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.34
_cell_volume                     1239.06(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6151
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0387
_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)+(0.0517P)²+0.3950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2120
_reflns_number_total             2697
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2329.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226318
_cod_database_fobs_code          2226318
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
C C1 0.31319(14) -0.08179(14) 0.92110(10) 0.0262(3) Uani d . 1 . .
C C2 0.20485(15) 0.01702(14) 0.85462(10) 0.0267(3) Uani d . 1 . .
C C3 0.12122(16) 0.10425(15) 0.88122(11) 0.0303(3) Uani d . 1 . .
C C4 0.14753(18) 0.09740(17) 0.97925(12) 0.0368(3) Uani d . 1 . .
H H4 0.0904 0.1559 0.9989 0.044 Uiso calc R 1 . .
C C5 0.25901(18) 0.00335(16) 1.04785(11) 0.0360(3) Uani d . 1 . .
H H5 0.2796 -0.0005 1.1155 0.043 Uiso calc R 1 . .
C C6 0.34170(16) -0.08577(15) 1.01982(10) 0.0304(3) Uani d . 1 . .
H H6 0.4176 -0.1493 1.0682 0.036 Uiso calc R 1 . .
C C7 0.01064(17) 0.19009(17) 0.78777(12) 0.0377(4) Uani d . 1 . .
H H7A 0.0101 0.2934 0.8043 0.045 Uiso calc R 1 . .
H H7B -0.0949 0.1513 0.7562 0.045 Uiso calc R 1 . .
C C8 0.07678(17) 0.16885(15) 0.71767(11) 0.0346(3) Uani d . 1 . .
C C9 -0.0406(2) 0.1410(2) 0.60728(12) 0.0498(4) Uani d . 1 . .
H H9A 0.0119 0.1132 0.5713 0.075 Uiso calc R 1 . .
H H9B -0.1006 0.2290 0.5767 0.075 Uiso calc R 1 . .
H H9C -0.1091 0.0628 0.6022 0.075 Uiso calc R 1 . .
C C10 0.1872(2) 0.28869(18) 0.73154(13) 0.0449(4) Uani d . 1 . .
H H10A 0.2604 0.3030 0.8041 0.067 Uiso calc R 1 . .
H H10B 0.1299 0.3783 0.7021 0.067 Uiso calc R 1 . .
H H10C 0.2427 0.2624 0.6973 0.067 Uiso calc R 1 . .
C C11 0.48288(15) -0.27410(15) 0.94317(10) 0.0288(3) Uani d . 1 . .
H H11A 0.4348 -0.3362 0.9716 0.035 Uiso calc R 1 . .
H H11B 0.5754 -0.2287 1.0002 0.035 Uiso calc R 1 . .
C C12 0.52628(16) -0.36346(15) 0.87960(10) 0.0292(3) Uani d . 1 . .
O O1 0.16890(11) 0.03407(10) 0.75592(7) 0.0308(2) Uani d . 1 . .
O O2 0.37837(11) -0.16642(10) 0.87999(7) 0.0300(2) Uani d . 1 . .
O O3 0.48249(14) -0.34112(12) 0.79128(8) 0.0443(3) Uani d . 1 . .
O O4 0.61833(13) -0.46912(11) 0.93349(8) 0.0387(3) Uani d . 1 . .
H H4A 0.6434 -0.5164 0.8976 0.058 Uiso calc R 1 . .
O O5W 0.28781(13) -0.12943(12) 0.65785(8) 0.0354(3) Uani d . 1 . .
H H5A 0.259(2) -0.079(2) 0.6924(15) 0.053 Uiso d . 1 . .
H H5B 0.349(2) -0.191(2) 0.7004(15) 0.053 Uiso d . 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'
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
O2 C1 C6 . . 127.47(12) ?
O2 C1 C2 . . 115.14(11) ?
C6 C1 C2 . . 117.38(12) ?
O1 C2 C3 . . 113.96(12) ?
O1 C2 C1 . . 123.09(12) ?
C3 C2 C1 . . 122.93(13) ?
C2 C3 C4 . . 119.42(13) ?
C2 C3 C7 . . 107.23(12) ?
C4 C3 C7 . . 133.33(13) ?
C5 C4 C3 . . 118.58(13) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C4 C5 C6 . . 121.54(13) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C1 C6 C5 . . 120.07(13) ?
C1 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C3 C7 C8 . . 102.50(11) ?
C3 C7 H7A . . 111.3 ?
C8 C7 H7A . . 111.3 ?
C3 C7 H7B . . 111.3 ?
C8 C7 H7B . . 111.3 ?
H7A C7 H7B . . 109.2 ?
O1 C8 C9 . . 105.86(12) ?
O1 C8 C10 . . 106.75(12) ?
C9 C8 C10 . . 112.51(14) ?
O1 C8 C7 . . 104.03(11) ?
C9 C8 C7 . . 115.32(13) ?
C10 C8 C7 . . 111.45(13) ?
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 ?
O2 C11 C12 . . 107.97(11) ?
O2 C11 H11A . . 110.1 ?
C12 C11 H11A . . 110.1 ?
O2 C11 H11B . . 110.1 ?
C12 C11 H11B . . 110.1 ?
H11A C11 H11B . . 108.4 ?
O3 C12 O4 . . 124.54(13) ?
O3 C12 C11 . . 124.88(13) ?
O4 C12 C11 . . 110.58(11) ?
C2 O1 C8 . . 106.73(10) ?
C1 O2 C11 . . 117.15(10) ?
C12 O4 H4A . . 109.5 ?
H5A O5W H5B . . 103.8(18) ?
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
C1 O2 . 1.3720(16) ?
C1 C6 . 1.3903(19) ?
C1 C2 . 1.3906(18) ?
C2 O1 . 1.3738(16) ?
C2 C3 . 1.3781(19) ?
C3 C4 . 1.389(2) ?
C3 C7 . 1.514(2) ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.548(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 O1 . 1.4868(16) ?
C8 C9 . 1.511(2) ?
C8 C10 . 1.513(2) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 O2 . 1.4147(16) ?
C11 C12 . 1.509(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 O3 . 1.2082(17) ?
C12 O4 . 1.3111(16) ?
O4 H4A . 0.8400 ?
O5W H5A . 0.86(2) ?
O5W H5B . 0.85(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
O5W H5A O1 . 0.86(2) 1.95(2) 2.8104(15) 173.0(19)
O5W H5B O3 . 0.85(2) 1.94(2) 2.7888(15) 176.5(19)
O4 H4A O5W 2_646 0.84 1.71 2.5416(15) 170.5
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
O2 C1 C2 O1 . . . . -2.53(19) ?
C6 C1 C2 O1 . . . . 178.40(12) ?
O2 C1 C2 C3 . . . . 175.87(12) ?
C6 C1 C2 C3 . . . . -3.2(2) ?
O1 C2 C3 C4 . . . . -179.74(12) ?
C1 C2 C3 C4 . . . . 1.7(2) ?
O1 C2 C3 C7 . . . . 1.47(16) ?
C1 C2 C3 C7 . . . . -177.06(13) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C7 C3 C4 C5 . . . . 179.06(15) ?
C3 C4 C5 C6 . . . . -1.5(2) ?
O2 C1 C6 C5 . . . . -176.62(13) ?
C2 C1 C6 C5 . . . . 2.3(2) ?
C4 C5 C6 C1 . . . . -0.1(2) ?
C2 C3 C7 C8 . . . . -15.13(15) ?
C4 C3 C7 C8 . . . . 166.32(16) ?
C3 C7 C8 O1 . . . . 22.35(15) ?
C3 C7 C8 C9 . . . . 137.81(14) ?
C3 C7 C8 C10 . . . . -92.32(14) ?
O2 C11 C12 O3 . . . . 2.6(2) ?
O2 C11 C12 O4 . . . . -177.34(11) ?
C3 C2 O1 C8 . . . . 13.73(15) ?
C1 C2 O1 C8 . . . . -167.74(12) ?
C9 C8 O1 C2 . . . . -144.32(13) ?
C10 C8 O1 C2 . . . . 95.60(13) ?
C7 C8 O1 C2 . . . . -22.37(14) ?
C6 C1 O2 C11 . . . . 2.41(19) ?
C2 C1 O2 C11 . . . . -176.54(11) ?
C12 C11 O2 C1 . . . . 173.93(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000976
