#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/70/2207085.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_2207085
loop_
_publ_author_name
'Meng, Xiang-Gao'
'Wu, An-Xin'
_publ_section_title
;
 (RS)-2,6-Dimethoxy-4-(2-methoxypropyl)phenol
;
_journal_coeditor_code           WN6371
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3176
_journal_page_last               o3178
_journal_paper_doi               10.1107/S1600536805027790
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H18 O4'
_chemical_formula_moiety         'C12 H18 O4'
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_chemical_name_systematic
;
(RS)-2,6-Dimethoxy-4-(2-methoxypropyl)phenol
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 102.190(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.740(3)
_cell_length_b                   9.405(2)
_cell_length_c                   9.997(2)
_cell_measurement_reflns_used    2536
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.64
_cell_volume                     1262.7(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6654
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0571
_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)+(0.1154P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1641
_reflns_number_gt                1809
_reflns_number_total             2481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6371.cif
_cod_data_source_block           I
_cod_original_cell_volume        1262.8(5)
_cod_original_sg_symbol_Hall     'p -2yc'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2207085
_cod_database_fobs_code          2207085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
loop_
_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_type_symbol
C1 0.6045(4) 0.5670(6) 0.4852(6) 0.0891(15) Uani d . 1 C
H1A 0.5831 0.6425 0.5370 0.134 Uiso calc R 1 H
H1B 0.6266 0.4879 0.5445 0.134 Uiso calc R 1 H
H1C 0.5499 0.5379 0.4137 0.134 Uiso calc R 1 H
C2 0.8242(5) 1.0225(7) 0.0604(8) 0.107(2) Uani d . 1 C
H2A 0.7639 1.0064 -0.0065 0.161 Uiso calc R 1 H
H2B 0.8803 1.0136 0.0179 0.161 Uiso calc R 1 H
H2C 0.8230 1.1163 0.0978 0.161 Uiso calc R 1 H
C3 0.6677(3) 0.7268(4) 0.3394(4) 0.0567(9) Uani d . 1 C
C4 0.7519(3) 0.7675(4) 0.2909(4) 0.0563(9) Uani d . 1 C
C5 0.7455(3) 0.8834(4) 0.2053(4) 0.0575(9) Uani d . 1 C
C6 0.6549(3) 0.9541(5) 0.1646(4) 0.0615(10) Uani d . 1 C
H6 0.6511 1.0320 0.1064 0.074 Uiso calc R 1 H
C7 0.5725(3) 0.9122(5) 0.2075(4) 0.0604(10) Uani d . 1 C
C8 0.5778(3) 0.7984(5) 0.2970(4) 0.0618(10) Uani d . 1 C
H8 0.5217 0.7701 0.3284 0.074 Uiso calc R 1 H
C9 0.4728(3) 0.9858(6) 0.1579(4) 0.0741(12) Uani d . 1 C
H9A 0.4778 1.0476 0.0820 0.089 Uiso calc R 1 H
H9B 0.4229 0.9142 0.1236 0.089 Uiso calc R 1 H
C10 0.4377(3) 1.0722(5) 0.2650(4) 0.0640(10) Uani d . 1 C
H10 0.4291 1.0092 0.3397 0.077 Uiso calc R 1 H
C11 0.5079(4) 1.1886(5) 0.3224(6) 0.0885(14) Uani d . 1 C
H11A 0.5254 1.2417 0.2489 0.133 Uiso calc R 1 H
H11B 0.5669 1.1485 0.3783 0.133 Uiso calc R 1 H
H11C 0.4766 1.2507 0.3769 0.133 Uiso calc R 1 H
C12 0.2791(4) 1.1581(10) 0.2848(6) 0.106(2) Uani d . 1 C
H12A 0.2581 1.0713 0.3206 0.159 Uiso calc R 1 H
H12B 0.2220 1.2083 0.2350 0.159 Uiso calc R 1 H
H12C 0.3133 1.2163 0.3589 0.159 Uiso calc R 1 H
C13 0.0655(4) 0.1060(8) 0.9756(8) 0.1043(19) Uani d . 1 C
H13A 0.0276 0.1819 1.0037 0.156 Uiso calc R 1 H
H13B 0.0755 0.0324 1.0437 0.156 Uiso calc R 1 H
H13C 0.0300 0.0679 0.8900 0.156 Uiso calc R 1 H
C14 0.3877(4) 0.4636(7) 0.6184(6) 0.0979(18) Uani d . 1 C
H14A 0.3470 0.4237 0.5371 0.147 Uiso calc R 1 H
H14B 0.4567 0.4514 0.6159 0.147 Uiso calc R 1 H
H14C 0.3733 0.5631 0.6231 0.147 Uiso calc R 1 H
C15 0.1611(3) 0.2431(5) 0.8537(4) 0.0631(10) Uani d . 1 C
C16 0.2586(3) 0.2793(4) 0.8426(4) 0.0550(9) Uani d . 1 C
C17 0.2706(3) 0.3661(5) 0.7367(4) 0.0635(10) Uani d . 1 C
C18 0.1891(4) 0.4235(5) 0.6469(5) 0.0837(14) Uani d . 1 C
H18 0.1995 0.4826 0.5766 0.100 Uiso calc R 1 H
C19 0.0936(3) 0.3948(5) 0.6597(5) 0.0730(12) Uani d . 1 C
C20 0.0797(3) 0.3014(6) 0.7632(5) 0.0798(13) Uani d . 1 C
H20 0.0155 0.2780 0.7717 0.096 Uiso calc R 1 H
C21 0.0041(4) 0.4538(5) 0.5613(6) 0.0873(15) Uani d . 1 C
H21A -0.0415 0.4939 0.6132 0.105 Uiso calc R 1 H
H21B 0.0255 0.5300 0.5090 0.105 Uiso calc R 1 H
C22 -0.0501(4) 0.3442(6) 0.4642(6) 0.0849(14) Uani d . 1 C
H22 -0.0698 0.2654 0.5170 0.102 Uiso calc R 1 H
C23 0.0156(6) 0.2853(9) 0.3679(7) 0.125(3) Uani d . 1 C
H23A -0.0244 0.2278 0.2979 0.188 Uiso calc R 1 H
H23B 0.0684 0.2286 0.4199 0.188 Uiso calc R 1 H
H23C 0.0434 0.3631 0.3263 0.188 Uiso calc R 1 H
C24 -0.2195(6) 0.3201(9) 0.3515(14) 0.177(5) Uani d . 1 C
H24A -0.1962 0.2309 0.3235 0.266 Uiso calc R 1 H
H24B -0.2668 0.3606 0.2768 0.266 Uiso calc R 1 H
H24C -0.2506 0.3049 0.4277 0.266 Uiso calc R 1 H
O1 0.6832(2) 0.6152(4) 0.4274(4) 0.0855(10) Uani d . 1 O
O2 0.8411(2) 0.7024(4) 0.3321(4) 0.0844(10) Uani d . 1 O
H2 0.8335 0.6277 0.3709 0.127 Uiso calc R 1 H
O3 0.8320(2) 0.9199(4) 0.1675(4) 0.0853(10) Uani d . 1 O
O4 0.3421(2) 1.1273(4) 0.1988(3) 0.0772(9) Uani d . 1 O
O5 0.1574(2) 0.1577(4) 0.9601(3) 0.0859(10) Uani d . 1 O
O6 0.33905(18) 0.2330(3) 0.9336(3) 0.0658(8) Uani d . 1 O
H6A 0.3219 0.2050 1.0028 0.099 Uiso calc R 1 H
O7 0.3678(2) 0.3950(4) 0.7325(4) 0.0867(11) Uani d . 1 O
O8 -0.1376(3) 0.4144(4) 0.3907(4) 0.1023(13) Uani d . 1 O
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 0.0000 '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 0.0000 '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
_geom_angle_publ_flag
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 ?
O3 C2 H2A 109.5 ?
O3 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O3 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
O1 C3 C8 125.4(3) ?
O1 C3 C4 114.1(3) ?
C8 C3 C4 120.5(3) ?
O2 C4 C5 118.7(3) ?
O2 C4 C3 122.2(3) ?
C5 C4 C3 118.9(3) ?
O3 C5 C4 115.3(3) ?
O3 C5 C6 125.1(3) ?
C4 C5 C6 119.6(3) ?
C7 C6 C5 121.7(4) ?
C7 C6 H6 119.2 ?
C5 C6 H6 119.2 ?
C6 C7 C8 119.7(4) ?
C6 C7 C9 121.4(4) ?
C8 C7 C9 118.9(4) ?
C7 C8 C3 119.5(3) ?
C7 C8 H8 120.2 ?
C3 C8 H8 120.2 ?
C10 C9 C7 114.6(3) ?
C10 C9 H9A 108.6 ?
C7 C9 H9A 108.6 ?
C10 C9 H9B 108.6 ?
C7 C9 H9B 108.6 ?
H9A C9 H9B 107.6 ?
O4 C10 C11 111.5(4) yes
O4 C10 C9 105.4(3) yes
C11 C10 C9 113.1(4) yes
O4 C10 H10 108.9 ?
C11 C10 H10 108.9 ?
C9 C10 H10 108.9 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O4 C12 H12A 109.5 ?
O4 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O4 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
O5 C13 H13A 109.5 ?
O5 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O5 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O7 C14 H14A 109.5 ?
O7 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O7 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O5 C15 C20 126.1(3) ?
O5 C15 C16 113.8(3) ?
C20 C15 C16 120.0(4) ?
O6 C16 C17 119.9(3) ?
O6 C16 C15 121.8(3) ?
C17 C16 C15 118.4(3) ?
O7 C17 C16 114.6(3) ?
O7 C17 C18 124.0(4) ?
C16 C17 C18 121.2(4) ?
C19 C18 C17 121.3(4) ?
C19 C18 H18 119.4 ?
C17 C18 H18 119.4 ?
C18 C19 C20 118.4(4) ?
C18 C19 C21 122.1(5) ?
C20 C19 C21 119.5(5) ?
C15 C20 C19 120.6(4) ?
C15 C20 H20 119.7 ?
C19 C20 H20 119.7 ?
C22 C21 C19 113.2(4) ?
C22 C21 H21A 108.9 ?
C19 C21 H21A 108.9 ?
C22 C21 H21B 108.9 ?
C19 C21 H21B 108.9 ?
H21A C21 H21B 107.8 ?
O8 C22 C21 105.3(4) yes
O8 C22 C23 112.4(5) yes
C21 C22 C23 111.8(5) yes
O8 C22 H22 109.1 ?
C21 C22 H22 109.1 ?
C23 C22 H22 109.1 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
O8 C24 H24A 109.5 ?
O8 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
O8 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C3 O1 C1 119.1(4) ?
C4 O2 H2 109.5 ?
C5 O3 C2 116.5(4) ?
C12 O4 C10 115.0(4) ?
C15 O5 C13 119.0(4) ?
C16 O6 H6A 109.5 ?
C17 O7 C14 118.7(4) ?
C24 O8 C22 112.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.405(6) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 O3 1.428(7) ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 O1 1.357(5) ?
C3 C8 1.392(5) ?
C3 C4 1.399(5) ?
C4 O2 1.355(5) ?
C4 C5 1.377(5) ?
C5 O3 1.364(5) ?
C5 C6 1.394(6) ?
C6 C7 1.352(6) ?
C6 H6 0.9300 ?
C7 C8 1.387(6) ?
C7 C9 1.521(6) ?
C8 H8 0.9300 ?
C9 C10 1.502(6) yes
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 O4 1.437(5) yes
C10 C11 1.491(7) yes
C10 H10 0.9800 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 O4 1.373(6) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 O5 1.391(6) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 O7 1.388(6) ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 O5 1.343(5) ?
C15 C20 1.394(6) ?
C15 C16 1.408(5) ?
C16 O6 1.347(4) ?
C16 C17 1.374(6) ?
C17 O7 1.372(5) ?
C17 C18 1.388(6) ?
C18 C19 1.372(7) ?
C18 H18 0.9300 ?
C19 C20 1.402(7) ?
C19 C21 1.509(7) ?
C20 H20 0.9300 ?
C21 C22 1.501(8) yes
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 O8 1.431(6) yes
C22 C23 1.555(10) yes
C22 H22 0.9800 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
C24 O8 1.421(8) ?
C24 H24A 0.9600 ?
C24 H24B 0.9600 ?
C24 H24C 0.9600 ?
O2 H2 0.8200 ?
O6 H6A 0.8200 ?
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
_geom_hbond_publ_flag
O2 H2 O1 . 0.82 2.26 2.676(4) 112 yes
O2 H2 O8 1_655 0.82 2.05 2.774(5) 148 yes
O6 H6A O5 . 0.82 2.25 2.661(4) 111 yes
O6 H6A O4 1_546 0.82 2.05 2.823(4) 156 yes
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
O1 C3 C4 O2 -1.7(6)
C8 C3 C4 O2 178.5(4)
O1 C3 C4 C5 -177.4(4)
C8 C3 C4 C5 2.8(6)
O2 C4 C5 O3 1.3(6)
C3 C4 C5 O3 177.2(4)
O2 C4 C5 C6 -178.3(4)
C3 C4 C5 C6 -2.5(6)
O3 C5 C6 C7 -179.3(4)
C4 C5 C6 C7 0.3(6)
C5 C6 C7 C8 1.6(6)
C5 C6 C7 C9 -177.3(4)
C6 C7 C8 C3 -1.2(6)
C9 C7 C8 C3 177.7(4)
O1 C3 C8 C7 179.3(4)
C4 C3 C8 C7 -1.0(6)
C6 C7 C9 C10 -110.2(5)
C8 C7 C9 C10 70.9(6)
C7 C9 C10 O4 -178.0(4)
C7 C9 C10 C11 59.9(6)
O5 C15 C16 O6 -1.2(6)
C20 C15 C16 O6 175.4(4)
O5 C15 C16 C17 179.9(4)
C20 C15 C16 C17 -3.5(7)
O6 C16 C17 O7 1.6(6)
C15 C16 C17 O7 -179.4(4)
O6 C16 C17 C18 -175.5(4)
C15 C16 C17 C18 3.5(7)
O7 C17 C18 C19 -177.4(5)
C16 C17 C18 C19 -0.5(8)
C17 C18 C19 C20 -2.3(8)
C17 C18 C19 C21 -178.7(5)
O5 C15 C20 C19 176.9(5)
C16 C15 C20 C19 0.8(8)
C18 C19 C20 C15 2.1(8)
C21 C19 C20 C15 178.7(5)
C18 C19 C21 C22 106.4(6)
C20 C19 C21 C22 -70.1(7)
C19 C21 C22 O8 173.7(5)
C19 C21 C22 C23 -64.0(6)
C8 C3 O1 C1 -1.7(7)
C4 C3 O1 C1 178.5(4)
C4 C5 O3 C2 169.2(5)
C6 C5 O3 C2 -11.2(7)
C11 C10 O4 C12 -82.5(6)
C9 C10 O4 C12 154.3(6)
C20 C15 O5 C13 8.5(8)
C16 C15 O5 C13 -175.2(5)
C16 C17 O7 C14 170.4(5)
C18 C17 O7 C14 -12.5(8)
C21 C22 O8 C24 -148.7(8)
C23 C22 O8 C24 89.3(8)
