#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208207.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_2208207
loop_
_publ_author_name
'Han, Jian-Rong'
'Zhen, Xiao-Li'
_publ_section_title
;
 3-[6-(5-Formyl-2-methoxyphenoxy)hexyloxy]-4-methoxybenzaldehyde
;
_journal_coeditor_code           WW6460
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o432
_journal_page_last               o433
_journal_paper_doi               10.1107/S1600536805042716
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H26 O6'
_chemical_formula_moiety         'C22 H26 O6'
_chemical_formula_sum            'C22 H26 O6'
_chemical_formula_weight         386.43
_chemical_name_systematic
;
3-[6-(5-Formyl-2-methoxyphenoxy)hexyloxy]-4-methoxybenzaldehyde
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.528(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.867(5)
_cell_length_b                   5.154(2)
_cell_length_c                   18.454(8)
_cell_measurement_reflns_used    1065
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.86
_cell_volume                     1033.2(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4602
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0679
_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)+(0.0386P)²+0.7149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                972
_reflns_number_total             1777
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6460.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208207
_cod_database_fobs_code          2208207
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_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
_atom_site_type_symbol
O1 0.6521(2) 0.4126(5) 0.23676(11) 0.0463(7) Uani d . 1 . . O
O2 0.6772(2) 0.0787(4) 0.13448(11) 0.0391(6) Uani d . 1 . . O
C1 0.7750(3) 0.2393(6) 0.14651(15) 0.0281(8) Uani d . 1 . . C
C2 0.7615(3) 0.4238(7) 0.20241(16) 0.0317(8) Uani d . 1 . . C
C3 0.8533(3) 0.5985(7) 0.21803(17) 0.0391(9) Uani d . 1 . . C
H3 0.8437 0.7196 0.2548 0.047 Uiso calc R 1 . . H
C4 0.9604(3) 0.5952(7) 0.17915(17) 0.0424(9) Uani d . 1 . . C
H4 1.0225 0.7147 0.1896 0.051 Uiso calc R 1 . . H
C5 0.9750(3) 0.4158(7) 0.12524(17) 0.0387(9) Uani d . 1 A . C
C6 0.8821(3) 0.2366(7) 0.10855(16) 0.0337(8) Uani d . 1 . . C
H6 0.8927 0.1156 0.0718 0.040 Uiso calc R 1 . . H
C7 0.6276(4) 0.6089(8) 0.28931(19) 0.0654(13) Uani d . 1 . . C
H7A 0.6827 0.5881 0.3304 0.098 Uiso calc R 1 . . H
H7B 0.5442 0.5934 0.3045 0.098 Uiso calc R 1 . . H
H7C 0.6396 0.7770 0.2682 0.098 Uiso calc R 1 . . H
C8 1.0899(4) 0.4106(12) 0.0854(3) 0.0670(12) Uani d D 1 . . C
H8A 1.1468 0.5502 0.0945 0.100 Uiso d PR 0.854(9) A 1 H
H8B 1.1026 0.2700 0.0501 0.100 Uiso d PR 0.146(9) A 2 H
O3 1.1196(3) 0.2513(10) 0.0430(2) 0.1014(19) Uani d PDU 0.854(9) A 1 O
O3' 1.1744(18) 0.562(4) 0.0906(12) 0.100(11) Uani d PDU 0.146(9) A 2 O
C9 0.6831(3) -0.0940(7) 0.07344(16) 0.0353(9) Uani d . 1 . . C
H9A 0.7521 -0.2118 0.0798 0.042 Uiso calc R 1 . . H
H9B 0.6941 0.0045 0.0293 0.042 Uiso calc R 1 . . H
C10 0.5645(3) -0.2443(7) 0.06856(16) 0.0363(9) Uani d . 1 . . C
H10A 0.4960 -0.1238 0.0652 0.044 Uiso calc R 1 . . H
H10B 0.5560 -0.3458 0.1124 0.044 Uiso calc R 1 . . H
C11 0.5595(3) -0.4246(6) 0.00324(16) 0.0361(9) Uani d . 1 . . C
H11A 0.5694 -0.3229 -0.0404 0.043 Uiso calc R 1 . . H
H11B 0.6277 -0.5458 0.0070 0.043 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C2 O1 C7 . 117.7(3) yes
C1 O2 C9 . 117.0(2) yes
O2 C1 C6 . 125.4(3) yes
O2 C1 C2 . 115.7(3) yes
C6 C1 C2 . 119.0(3) ?
O1 C2 C3 . 124.7(3) yes
O1 C2 C1 . 114.8(3) yes
C3 C2 C1 . 120.5(3) ?
C2 C3 C4 . 120.1(3) ?
C2 C3 H3 . 120.0 ?
C4 C3 H3 . 120.0 ?
C5 C4 C3 . 120.0(3) ?
C5 C4 H4 . 120.0 ?
C3 C4 H4 . 120.0 ?
C4 C5 C6 . 120.6(3) ?
C4 C5 C8 . 119.5(4) ?
C6 C5 C8 . 119.9(4) ?
C1 C6 C5 . 119.9(3) ?
C1 C6 H6 . 120.1 ?
C5 C6 H6 . 120.1 ?
O1 C7 H7A . 109.5 ?
O1 C7 H7B . 109.5 ?
H7A C7 H7B . 109.5 ?
O1 C7 H7C . 109.5 ?
H7A C7 H7C . 109.5 ?
H7B C7 H7C . 109.5 ?
O3 C8 O3' . 106.2(13) ?
O3 C8 C5 . 126.5(5) yes
O3' C8 C5 . 127.3(14) ?
O3 C8 H8A . 116.6 ?
C5 C8 H8A . 116.9 ?
O3' C8 H8B . 114.0 ?
C5 C8 H8B . 118.7 ?
H8A C8 H8B . 124.3 ?
O2 C9 C10 . 108.0(3) yes
O2 C9 H9A . 110.1 ?
C10 C9 H9A . 110.1 ?
O2 C9 H9B . 110.1 ?
C10 C9 H9B . 110.1 ?
H9A C9 H9B . 108.4 ?
C9 C10 C11 . 112.0(3) ?
C9 C10 H10A . 109.2 ?
C11 C10 H10A . 109.2 ?
C9 C10 H10B . 109.2 ?
C11 C10 H10B . 109.2 ?
H10A C10 H10B . 107.9 ?
C11 C11 C10 3_645 112.9(3) ?
C11 C11 H11A 3_645 109.0 ?
C10 C11 H11A . 109.0 ?
C11 C11 H11B 3_645 109.0 ?
C10 C11 H11B . 109.0 ?
H11A C11 H11B . 107.8 ?
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 C2 . 1.363(4) yes
O1 C7 . 1.431(4) yes
O2 C1 . 1.360(4) yes
O2 C9 . 1.438(3) yes
C1 C6 . 1.375(4) ?
C1 C2 . 1.413(4) ?
C2 C3 . 1.369(4) ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.397(4) ?
C5 C8 . 1.466(5) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 O3 . 1.186(5) yes
C8 O3' . 1.206(10) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9869 ?
O3 H8B . 0.2495 ?
O3' H8A . 0.3161 ?
C9 C10 . 1.504(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.522(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C11 3_645 1.510(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
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_4
_geom_torsion
C9 O2 C1 C6 . -5.1(4)
C9 O2 C1 C2 . 174.1(3)
C7 O1 C2 C3 . 4.8(5)
C7 O1 C2 C1 . -174.3(3)
O2 C1 C2 O1 . 0.5(4)
C6 C1 C2 O1 . 179.7(3)
O2 C1 C2 C3 . -178.6(3)
C6 C1 C2 C3 . 0.6(5)
O1 C2 C3 C4 . -179.2(3)
C1 C2 C3 C4 . -0.2(5)
C2 C3 C4 C5 . -0.4(5)
C3 C4 C5 C6 . 0.5(5)
C3 C4 C5 C8 . -178.7(3)
O2 C1 C6 C5 . 178.7(3)
C2 C1 C6 C5 . -0.5(5)
C4 C5 C6 C1 . -0.1(5)
C8 C5 C6 C1 . 179.2(3)
C4 C5 C8 O3 . 171.9(5)
C6 C5 C8 O3 . -7.3(7)
C4 C5 C8 O3' . -5.8(17)
C6 C5 C8 O3' . 175.0(16)
C1 O2 C9 C10 . -177.7(3)
O2 C9 C10 C11 . 177.4(3)
C9 C10 C11 C11 3_645 -179.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134120828
