#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/94/2229485.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_2229485
loop_
_publ_author_name
'Xia, Juan'
'Liu, Xiang'
'Wang, An-Qi'
'Su, Zhong-Xing'
_publ_section_title
;
 2-(2-{2-[2-(Dibromomethyl)phenoxy]ethoxy}benzyloxy)benzaldehyde
;
_journal_coeditor_code           RK2257
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o714
_journal_paper_doi               10.1107/S160053681100643X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H20 Br2 O4'
_chemical_formula_moiety         'C23 H20 Br2 O4'
_chemical_formula_sum            'C23 H20 Br2 O4'
_chemical_formula_weight         520.19
_chemical_name_systematic
;
2-(2-{2-[2-(Dibromomethyl)phenoxy]ethoxy}benzyloxy)benzaldehyde
;
_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                 108.955(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.867(7)
_cell_length_b                   18.070(10)
_cell_length_c                   9.649(5)
_cell_measurement_reflns_used    1808
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.48
_cell_measurement_theta_min      2.25
_cell_volume                     2122(2)
_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    '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'
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15392
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    3.847
_exptl_absorpt_correction_T_max  0.341
_exptl_absorpt_correction_T_min  0.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.753
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0616
_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)+(0.1049P)²+0.4797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.2069
_reflns_number_gt                1905
_reflns_number_total             3944
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2257.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229485
_cod_database_fobs_code          2229485
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
Br Br1 0.56817(7) 0.30130(6) 0.29797(13) 0.1092(5) Uani d . 1 . .
Br Br2 0.37069(9) 0.31794(5) -0.00106(10) 0.0986(5) Uani d . 1 . .
C C1 -0.1269(7) 0.7137(4) -0.1294(8) 0.069(2) Uani d . 1 . .
H H1 -0.1621 0.6777 -0.0919 0.083 Uiso calc R 1 . .
C C2 -0.0059(6) 0.7075(3) -0.0932(6) 0.0509(16) Uani d . 1 . .
C C3 0.0495(7) 0.7556(4) -0.1572(7) 0.0658(19) Uani d . 1 . .
H H3 0.0096 0.7922 -0.2199 0.079 Uiso calc R 1 . .
C C4 0.1583(7) 0.7514(4) -0.1323(8) 0.073(2) Uani d . 1 . .
H H4 0.1932 0.7846 -0.1761 0.088 Uiso calc R 1 . .
C C5 0.2176(6) 0.6962(4) -0.0397(8) 0.070(2) Uani d . 1 . .
H H5 0.2930 0.6929 -0.0213 0.084 Uiso calc R 1 . .
C C6 0.1660(6) 0.6458(4) 0.0260(7) 0.0551(16) Uani d . 1 . .
H H6 0.2062 0.6085 0.0865 0.066 Uiso calc R 1 . .
C C7 0.0548(6) 0.6522(3) -0.0001(6) 0.0511(16) Uani d . 1 . .
C C8 0.0522(5) 0.5531(3) 0.1655(7) 0.0487(15) Uani d . 1 . .
H H8A 0.1057 0.5775 0.2474 0.058 Uiso calc R 1 . .
H H8B 0.0905 0.5182 0.1229 0.058 Uiso calc R 1 . .
C C9 -0.0317(5) 0.5130(3) 0.2169(6) 0.0470(15) Uani d . 1 . .
C C10 -0.1419(6) 0.5287(4) 0.1643(7) 0.0617(18) Uani d . 1 . .
H H10 -0.1676 0.5664 0.0961 0.074 Uiso calc R 1 . .
C C11 -0.2162(6) 0.4878(5) 0.2135(8) 0.070(2) Uani d . 1 . .
H H11 -0.2910 0.4979 0.1766 0.084 Uiso calc R 1 . .
C C12 -0.1791(7) 0.4340(4) 0.3138(8) 0.071(2) Uani d . 1 . .
H H12 -0.2284 0.4073 0.3465 0.085 Uiso calc R 1 . .
C C13 -0.0685(6) 0.4184(4) 0.3684(7) 0.0602(17) Uani d . 1 . .
H H13 -0.0436 0.3811 0.4378 0.072 Uiso calc R 1 . .
C C14 0.0057(5) 0.4576(3) 0.3211(7) 0.0487(16) Uani d . 1 . .
C C15 0.1611(5) 0.3890(3) 0.4722(6) 0.0536(16) Uani d . 1 . .
H H15A 0.1381 0.3412 0.4268 0.064 Uiso calc R 1 . .
H H15B 0.1347 0.3939 0.5552 0.064 Uiso calc R 1 . .
C C16 0.2849(6) 0.3950(4) 0.5223(7) 0.0670(19) Uani d . 1 . .
H H16A 0.3066 0.4437 0.5639 0.080 Uiso calc R 1 . .
H H16B 0.3163 0.3586 0.5984 0.080 Uiso calc R 1 . .
C C17 0.3652(5) 0.4407(4) 0.3435(7) 0.0556(17) Uani d . 1 . .
C C18 0.3584(6) 0.5154(4) 0.3772(8) 0.0675(19) Uani d . 1 . .
H H18 0.3226 0.5295 0.4426 0.081 Uiso calc R 1 . .
C C19 0.4055(6) 0.5681(4) 0.3121(9) 0.077(2) Uani d . 1 . .
H H19 0.4046 0.6176 0.3381 0.092 Uiso calc R 1 . .
C C20 0.4531(6) 0.5485(5) 0.2106(9) 0.076(2) Uani d . 1 . .
H H20 0.4825 0.5846 0.1656 0.091 Uiso calc R 1 . .
C C21 0.4579(6) 0.4750(5) 0.1743(8) 0.071(2) Uani d . 1 . .
H H21 0.4906 0.4622 0.1047 0.086 Uiso calc R 1 . .
C C22 0.4145(5) 0.4197(4) 0.2401(7) 0.0536(16) Uani d . 1 . .
C C23 0.4210(6) 0.3400(4) 0.2060(8) 0.0657(19) Uani d . 1 . .
H H23 0.3725 0.3135 0.2490 0.079 Uiso calc R 1 . .
O O1 -0.1819(4) 0.7608(3) -0.2023(5) 0.0824(16) Uani d . 1 . .
O O2 -0.0053(3) 0.6067(2) 0.0578(4) 0.0549(11) Uani d . 1 . .
O O3 0.1171(4) 0.4474(2) 0.3681(4) 0.0560(11) Uani d . 1 . .
O O4 0.3266(4) 0.3834(2) 0.4054(5) 0.0737(14) 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'
Br Br -0.2901 2.4595 '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
O1 C1 C2 . . 124.9(7) ?
O1 C1 H1 . . 117.5 ?
C2 C1 H1 . . 117.5 ?
C3 C2 C7 . . 118.2(7) ?
C3 C2 C1 . . 119.9(6) ?
C7 C2 C1 . . 121.9(6) ?
C4 C3 C2 . . 122.7(7) ?
C4 C3 H3 . . 118.7 ?
C2 C3 H3 . . 118.7 ?
C3 C4 C5 . . 118.6(7) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
C4 C5 C6 . . 121.2(7) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 C5 . . 118.8(6) ?
C7 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
O2 C7 C6 . . 124.6(6) ?
O2 C7 C2 . . 114.9(6) ?
C6 C7 C2 . . 120.5(6) ?
O2 C8 C9 . . 107.8(5) ?
O2 C8 H8A . . 110.1 ?
C9 C8 H8A . . 110.1 ?
O2 C8 H8B . . 110.1 ?
C9 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.5 ?
C10 C9 C14 . . 119.3(6) ?
C10 C9 C8 . . 122.8(6) ?
C14 C9 C8 . . 117.8(5) ?
C9 C10 C11 . . 120.0(7) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.1(7) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C13 . . 120.3(6) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.6(7) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
O3 C14 C13 . . 125.8(6) ?
O3 C14 C9 . . 114.6(5) ?
C13 C14 C9 . . 119.7(6) ?
O3 C15 C16 . . 107.8(5) ?
O3 C15 H15A . . 110.1 ?
C16 C15 H15A . . 110.1 ?
O3 C15 H15B . . 110.1 ?
C16 C15 H15B . . 110.1 ?
H15A C15 H15B . . 108.5 ?
O4 C16 C15 . . 111.6(5) ?
O4 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
O4 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
O4 C17 C18 . . 124.7(6) ?
O4 C17 C22 . . 114.9(6) ?
C18 C17 C22 . . 120.4(6) ?
C19 C18 C17 . . 119.3(7) ?
C19 C18 H18 . . 120.4 ?
C17 C18 H18 . . 120.4 ?
C20 C19 C18 . . 120.8(7) ?
C20 C19 H19 . . 119.6 ?
C18 C19 H19 . . 119.6 ?
C19 C20 C21 . . 120.1(7) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C20 C21 C22 . . 121.1(7) ?
C20 C21 H21 . . 119.5 ?
C22 C21 H21 . . 119.5 ?
C17 C22 C21 . . 118.2(7) ?
C17 C22 C23 . . 119.5(6) ?
C21 C22 C23 . . 122.3(6) ?
C22 C23 Br2 . . 113.9(5) ?
C22 C23 Br1 . . 111.4(5) ?
Br2 C23 Br1 . . 110.4(3) ?
C22 C23 H23 . . 106.9 ?
Br2 C23 H23 . . 106.9 ?
Br1 C23 H23 . . 106.9 ?
C7 O2 C8 . . 118.4(5) ?
C14 O3 C15 . . 117.5(5) ?
C17 O4 C16 . . 121.6(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
Br1 C23 . 1.941(7) ?
Br2 C23 . 1.931(7) ?
C1 O1 . 1.182(8) ?
C1 C2 . 1.485(10) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.389(9) ?
C2 C7 . 1.400(8) ?
C3 C4 . 1.344(10) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(10) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.395(9) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.376(9) ?
C6 H6 . 0.9300 ?
C7 O2 . 1.366(7) ?
C8 O2 . 1.437(7) ?
C8 C9 . 1.510(8) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.372(9) ?
C9 C14 . 1.390(8) ?
C10 C11 . 1.408(9) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.344(10) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.377(10) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(8) ?
C13 H13 . 0.9300 ?
C14 O3 . 1.368(7) ?
C15 O3 . 1.441(7) ?
C15 C16 . 1.510(9) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 O4 . 1.414(7) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 O4 . 1.367(7) ?
C17 C18 . 1.397(9) ?
C17 C22 . 1.397(9) ?
C18 C19 . 1.385(10) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.361(11) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.379(11) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.394(9) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.486(9) ?
C23 H23 . 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
C1 H1 O2 . 0.93 2.42 2.753(9) 101
C10 H10 O2 . 0.93 2.35 2.710(8) 102
C23 H23 O4 . 0.98 2.19 2.700(8) 111
C5 H5 Br1 2_655 0.93 3.03 3.529(7) 116
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
O1 C1 C2 C3 . . . . -6.0(10) ?
O1 C1 C2 C7 . . . . 176.8(6) ?
C7 C2 C3 C4 . . . . -0.6(10) ?
C1 C2 C3 C4 . . . . -178.0(6) ?
C2 C3 C4 C5 . . . . 0.6(10) ?
C3 C4 C5 C6 . . . . 0.3(10) ?
C4 C5 C6 C7 . . . . -1.1(10) ?
C5 C6 C7 O2 . . . . -179.8(5) ?
C5 C6 C7 C2 . . . . 1.1(9) ?
C3 C2 C7 O2 . . . . -179.5(5) ?
C1 C2 C7 O2 . . . . -2.2(8) ?
C3 C2 C7 C6 . . . . -0.3(9) ?
C1 C2 C7 C6 . . . . 177.0(6) ?
O2 C8 C9 C10 . . . . 0.0(8) ?
O2 C8 C9 C14 . . . . 179.3(5) ?
C14 C9 C10 C11 . . . . -1.3(9) ?
C8 C9 C10 C11 . . . . 178.0(5) ?
C9 C10 C11 C12 . . . . 1.0(10) ?
C10 C11 C12 C13 . . . . -0.4(10) ?
C11 C12 C13 C14 . . . . 0.0(10) ?
C12 C13 C14 O3 . . . . 179.5(6) ?
C12 C13 C14 C9 . . . . -0.3(9) ?
C10 C9 C14 O3 . . . . -178.8(5) ?
C8 C9 C14 O3 . . . . 1.8(7) ?
C10 C9 C14 C13 . . . . 1.0(9) ?
C8 C9 C14 C13 . . . . -178.4(5) ?
O3 C15 C16 O4 . . . . -63.5(7) ?
O4 C17 C18 C19 . . . . 176.8(6) ?
C22 C17 C18 C19 . . . . -3.0(10) ?
C17 C18 C19 C20 . . . . 3.4(11) ?
C18 C19 C20 C21 . . . . -1.9(11) ?
C19 C20 C21 C22 . . . . 0.0(11) ?
O4 C17 C22 C21 . . . . -178.7(6) ?
C18 C17 C22 C21 . . . . 1.1(9) ?
O4 C17 C22 C23 . . . . 0.1(9) ?
C18 C17 C22 C23 . . . . 179.9(6) ?
C20 C21 C22 C17 . . . . 0.4(10) ?
C20 C21 C22 C23 . . . . -178.3(7) ?
C17 C22 C23 Br2 . . . . 130.6(5) ?
C21 C22 C23 Br2 . . . . -50.7(8) ?
C17 C22 C23 Br1 . . . . -103.8(6) ?
C21 C22 C23 Br1 . . . . 75.0(7) ?
C6 C7 O2 C8 . . . . 6.8(8) ?
C2 C7 O2 C8 . . . . -174.1(5) ?
C9 C8 O2 C7 . . . . 177.1(4) ?
C13 C14 O3 C15 . . . . 2.5(8) ?
C9 C14 O3 C15 . . . . -177.8(5) ?
C16 C15 O3 C14 . . . . -172.6(5) ?
C18 C17 O4 C16 . . . . -6.4(10) ?
C22 C17 O4 C16 . . . . 173.5(5) ?
C15 C16 O4 C17 . . . . 105.9(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656549
2 PubChem 139080739
