#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229224.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_2229224
loop_
_publ_author_name
'Li, Hongqi'
'Cai, Li'
'Chen, Dongling'
'Li, Jinxing'
'Chen, Yijun'
_publ_section_title
;
 1,2-Bis(2-methoxy-6-formylphenoxy)ethane
;
_journal_coeditor_code           SJ5080
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o306
_journal_paper_doi               10.1107/S1600536810054085
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H18 O6'
_chemical_formula_moiety         'C18 H18 O6'
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32
_chemical_melting_point_gt       391
_chemical_melting_point_lt       393
_chemical_name_common            1,2-Bis(2-methoxy-6-formylphenoxy)ethane
_chemical_name_systematic
;
3,3'-Dimethoxy-2,2'-(ethane-1,2-diyldioxy)dibenzaldehyde
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.817(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.161(3)
_cell_length_b                   30.155(18)
_cell_length_c                   12.934(8)
_cell_measurement_reflns_used    1432
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.00
_cell_measurement_theta_min      2.57
_cell_volume                     1611.4(18)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14774
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.181
_refine_ls_extinction_coef       0.0130(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1519
_reflns_number_total             2815
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5080.cif
_cod_data_source_block           I
_cod_original_cell_volume        1611.6(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229224
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
C C1 0.3389(9) 0.03026(11) 0.5936(2) 0.0647(10) Uani d . 1 . .
H H1A 0.5683 0.0344 0.5956 0.097 Uiso calc R 1 . .
H H1B 0.2895 -0.0008 0.5895 0.097 Uiso calc R 1 . .
H H1C 0.2676 0.0424 0.6556 0.097 Uiso calc R 1 . .
C C2 0.2236(7) 0.09709(10) 0.4969(2) 0.0448(8) Uani d . 1 . .
C C3 0.4057(8) 0.12260(11) 0.5701(2) 0.0554(9) Uani d . 1 . .
H H3 0.5160 0.1092 0.6286 0.066 Uiso calc R 1 . .
C C4 0.4264(8) 0.16785(12) 0.5577(3) 0.0622(10) Uani d . 1 . .
H H4 0.5543 0.1845 0.6071 0.075 Uiso calc R 1 . .
C C5 0.2608(8) 0.18851(11) 0.4733(3) 0.0547(9) Uani d . 1 . .
H H5 0.2717 0.2192 0.4666 0.066 Uiso calc R 1 . .
C C6 0.0754(7) 0.16342(10) 0.3975(2) 0.0453(8) Uani d . 1 . .
C C7 0.0586(7) 0.11786(10) 0.4081(2) 0.0420(8) Uani d . 1 . .
C C8 -0.1070(8) 0.18701(12) 0.3090(3) 0.0612(10) Uani d . 1 . .
H H8 -0.2209 0.1703 0.2564 0.073 Uiso calc R 1 . .
C C9 0.0325(8) 0.06410(9) 0.2724(2) 0.0461(8) Uani d . 1 . .
H H9A -0.1130 0.0407 0.2449 0.055 Uiso calc R 1 . .
H H9B 0.2118 0.0504 0.3156 0.055 Uiso calc R 1 . .
C C10 0.1595(7) 0.08728(10) 0.1841(2) 0.0438(8) Uani d . 1 . .
H H10A 0.2860 0.1129 0.2094 0.053 Uiso calc R 1 . .
H H10B 0.2979 0.0675 0.1501 0.053 Uiso calc R 1 . .
C C11 -0.0342(7) 0.11450(10) 0.0157(2) 0.0440(8) Uani d . 1 . .
C C12 0.1182(8) 0.15543(11) 0.0050(3) 0.0532(9) Uani d . 1 . .
C C13 0.1759(9) 0.16920(13) -0.0933(3) 0.0714(11) Uani d . 1 . .
H H13 0.2742 0.1965 -0.1016 0.086 Uiso calc R 1 . .
C C14 0.0882(11) 0.14262(16) -0.1793(3) 0.0814(13) Uani d . 1 . .
H H14 0.1269 0.1523 -0.2450 0.098 Uiso calc R 1 . .
C C15 -0.0523(10) 0.10304(14) -0.1689(3) 0.0747(12) Uani d . 1 . .
H H15 -0.1064 0.0854 -0.2274 0.090 Uiso calc R 1 . .
C C16 -0.1190(8) 0.08786(11) -0.0705(2) 0.0526(9) Uani d . 1 . .
C C17 -0.2777(9) 0.04495(12) -0.0610(3) 0.0703(11) Uani d . 1 . .
H H17 -0.3183 0.0360 0.0050 0.084 Uiso calc R 1 . .
C C18 0.3642(9) 0.21970(10) 0.0892(3) 0.0809(12) Uani d . 1 . .
H H18A 0.5724 0.2134 0.0677 0.121 Uiso calc R 1 . .
H H18B 0.3920 0.2335 0.1565 0.121 Uiso calc R 1 . .
H H18C 0.2469 0.2393 0.0398 0.121 Uiso calc R 1 . .
O O1 -0.1379(5) 0.09317(6) 0.33650(14) 0.0448(6) Uani d . 1 . .
O O2 -0.1126(5) 0.10109(6) 0.11105(14) 0.0446(6) Uani d . 1 . .
O O3 0.1872(6) 0.17924(7) 0.09468(19) 0.0640(7) Uani d . 1 . .
O O4 0.1771(5) 0.05236(7) 0.50439(15) 0.0560(6) Uani d . 1 . .
O O5 -0.1154(7) 0.22701(8) 0.30153(19) 0.0849(9) Uani d . 1 . .
O O6 -0.3593(8) 0.02042(9) -0.1333(2) 0.1053(11) Uani 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
O4 C1 H1A . . 109.5 ?
O4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O4 C2 C3 . . 125.0(3) ?
O4 C2 C7 . . 115.8(3) ?
C3 C2 C7 . . 119.1(3) ?
C2 C3 C4 . . 120.7(3) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 120.7(3) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.8(3) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C7 C6 C5 . . 120.0(3) ?
C7 C6 C8 . . 121.8(3) ?
C5 C6 C8 . . 118.2(3) ?
O1 C7 C6 . . 120.2(3) ?
O1 C7 C2 . . 119.9(3) ?
C6 C7 C2 . . 119.7(3) ?
O5 C8 C6 . . 123.2(3) ?
O5 C8 H8 . . 118.4 ?
C6 C8 H8 . . 118.4 ?
O1 C9 C10 . . 113.4(2) ?
O1 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
O1 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
O2 C10 C9 . . 108.3(2) ?
O2 C10 H10A . . 110.0 ?
C9 C10 H10A . . 110.0 ?
O2 C10 H10B . . 110.0 ?
C9 C10 H10B . . 110.0 ?
H10A C10 H10B . . 108.4 ?
O2 C11 C16 . . 119.1(3) ?
O2 C11 C12 . . 120.4(3) ?
C16 C11 C12 . . 120.4(3) ?
O3 C12 C13 . . 125.5(3) ?
O3 C12 C11 . . 115.5(3) ?
C13 C12 C11 . . 119.0(3) ?
C14 C13 C12 . . 120.4(4) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C15 C14 C13 . . 120.7(4) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 120.9(4) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C11 C16 C15 . . 118.6(3) ?
C11 C16 C17 . . 121.3(3) ?
C15 C16 C17 . . 120.1(3) ?
O6 C17 C16 . . 124.3(4) ?
O6 C17 H17 . . 117.8 ?
C16 C17 H17 . . 117.8 ?
O3 C18 H18A . . 109.5 ?
O3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C7 O1 C9 . . 114.8(2) ?
C11 O2 C10 . . 114.8(2) ?
C12 O3 C18 . . 117.6(3) ?
C2 O4 C1 . . 117.4(2) ?
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 O4 . 1.430(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O4 . 1.368(4) ?
C2 C3 . 1.376(4) ?
C2 C7 . 1.413(4) ?
C3 C4 . 1.378(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.396(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.383(4) ?
C6 C8 . 1.479(4) ?
C7 O1 . 1.378(3) ?
C8 O5 . 1.210(4) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.449(3) ?
C9 C10 . 1.489(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.447(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O2 . 1.373(3) ?
C11 C16 . 1.385(4) ?
C11 C12 . 1.402(4) ?
C12 O3 . 1.366(4) ?
C12 C13 . 1.385(4) ?
C13 C14 . 1.384(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.343(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.412(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.464(5) ?
C17 O6 . 1.209(4) ?
C17 H17 . 0.9300 ?
C18 O3 . 1.431(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15643205
