#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/14/2211439.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_2211439
loop_
_publ_author_name
'Zhen, Xiao-Li'
'Han, Jian-Rong'
'Wang, Qun-Tao'
'Tian, Xia'
'Liu, Shou-Xin'
_publ_section_title
;
 4-(2,4-Dichlorobenzyloxy)-3-ethoxybenzaldehyde
;
_journal_coeditor_code           HB2214
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5794
_journal_page_last               o5795
_journal_paper_doi               10.1107/S1600536806049671
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H14 Cl2 O3'
_chemical_formula_moiety         'C16 H14 Cl2 O3'
_chemical_formula_sum            'C16 H14 Cl2 O3'
_chemical_formula_weight         325.17
_chemical_name_systematic
;
4-4-(2,4-Dichlorobenzyloxy)-3-ethoxybenzaldehyde
;
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   19.849(3)
_cell_length_b                   19.849(3)
_cell_length_c                   10.340(2)
_cell_measurement_reflns_used    2629
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.30
_cell_volume                     3528.0(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6567
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1601
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0294
_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)+(0.0472P)²+0.7953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                1263
_reflns_number_total             1601
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2214.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               2211439
_cod_database_fobs_code          2211439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
Cl Cl1 0.34754(6) 0.27838(8) 0.36798(11) 0.0759(4) Uani d . 1
Cl Cl2 0.03498(6) 0.11165(5) 0.35177(12) 0.0645(3) Uani d . 1
O O1 0.04996(14) 0.34052(14) 0.3773(2) 0.0490(6) Uani d . 1
O O2 0.08296(14) 0.48186(13) 0.3796(2) 0.0494(6) Uani d . 1
O O3 -0.18716(18) 0.4669(2) 0.3739(4) 0.0851(10) Uani d . 1
C C1 -0.0130(2) 0.35061(18) 0.3790(3) 0.0399(8) Uani d . 1
C C2 0.0054(2) 0.42927(18) 0.3809(3) 0.0395(8) Uani d . 1
C C3 -0.05343(19) 0.4456(2) 0.3825(3) 0.0436(8) Uani d . 1
H H3 -0.0417 0.4972 0.3854 0.052 Uiso calc R 1
C C4 -0.1311(2) 0.3863(2) 0.3798(4) 0.0467(8) Uani d . 1
C C5 -0.1483(2) 0.3095(2) 0.3787(4) 0.0498(8) Uani d . 1
H H5 -0.2000 0.2698 0.3778 0.060 Uiso calc R 1
C C6 -0.0890(2) 0.2909(2) 0.3787(4) 0.0464(8) Uani d . 1
H H6 -0.1007 0.2393 0.3786 0.056 Uiso calc R 1
C C7 0.1066(2) 0.56240(19) 0.3905(4) 0.0518(9) Uani d . 1
H H7A 0.0876 0.5719 0.4709 0.062 Uiso calc R 1
H H7B 0.0856 0.5780 0.3193 0.062 Uiso calc R 1
C C8 0.1932(2) 0.6076(3) 0.3877(4) 0.0680(12) Uani d . 1
H H8A 0.2134 0.5925 0.4595 0.102 Uiso calc R 1
H H8B 0.2106 0.6622 0.3936 0.102 Uiso calc R 1
H H8C 0.2115 0.5973 0.3083 0.102 Uiso calc R 1
C C9 -0.1945(3) 0.4037(3) 0.3779(4) 0.0617(11) Uani d . 1
H H9 -0.2450 0.3617 0.3799 0.074 Uiso calc R 1
C C10 0.0363(2) 0.26315(17) 0.3830(4) 0.0427(8) Uani d . 1
H H10A 0.0044 0.2330 0.3106 0.051 Uiso calc R 1
H H10B 0.0095 0.2382 0.4625 0.051 Uiso calc R 1
C C11 0.11434(19) 0.26784(18) 0.3780(3) 0.0397(7) Uani d . 1
C C12 0.1836(2) 0.3378(2) 0.3905(4) 0.0502(8) Uani d . 1
H H12 0.1822 0.3837 0.4000 0.060 Uiso calc R 1
C C13 0.2549(2) 0.3407(2) 0.3891(4) 0.0536(9) Uani d . 1
H H13 0.3008 0.3881 0.3980 0.064 Uiso calc R 1
C C14 0.2576(2) 0.2729(2) 0.3744(3) 0.0527(9) Uani d . 1
C C15 0.1912(2) 0.2029(2) 0.3622(4) 0.0496(8) Uani d . 1
H H15 0.1932 0.1573 0.3526 0.060 Uiso calc R 1
C C16 0.1198(2) 0.2014(2) 0.3646(4) 0.0467(8) 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 0.0000 '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'
Cl Cl 0.1484 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
C1 O1 C10 117.8(3)
C2 O2 C7 118.1(3)
O1 C1 C6 124.4(3)
O1 C1 C2 114.5(3)
C6 C1 C2 121.1(3)
C3 C2 O2 126.5(3)
C3 C2 C1 119.0(3)
O2 C2 C1 114.5(3)
C2 C3 C4 121.2(3)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 119.2(3)
C5 C4 C9 119.4(3)
C3 C4 C9 121.3(4)
C4 C5 C6 120.9(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 118.5(3)
C1 C6 H6 120.7
C5 C6 H6 120.7
O2 C7 C8 107.9(3)
O2 C7 H7A 110.1
C8 C7 H7A 110.1
O2 C7 H7B 110.1
C8 C7 H7B 110.1
H7A C7 H7B 108.4
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 C4 125.7(4)
O3 C9 H9 117.2
C4 C9 H9 117.2
O1 C10 C11 107.3(3)
O1 C10 H10A 110.3
C11 C10 H10A 110.3
O1 C10 H10B 110.3
C11 C10 H10B 110.3
H10A C10 H10B 108.5
C16 C11 C12 116.9(3)
C16 C11 C10 120.9(3)
C12 C11 C10 122.1(3)
C11 C12 C13 121.3(3)
C11 C12 H12 119.4
C13 C12 H12 119.4
C14 C13 C12 119.7(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
C15 C14 C13 121.1(3)
C15 C14 Cl1 120.0(3)
C13 C14 Cl1 118.9(3)
C14 C15 C16 118.1(3)
C14 C15 H15 120.9
C16 C15 H15 120.9
C11 C16 C15 122.8(3)
C11 C16 Cl2 119.1(3)
C15 C16 Cl2 118.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.735(4)
Cl2 C16 1.740(4)
O1 C1 1.360(4)
O1 C10 1.421(4)
O2 C2 1.361(4)
O2 C7 1.428(4)
O3 C9 1.189(5)
C1 C6 1.376(5)
C1 C2 1.415(4)
C2 C3 1.359(4)
C3 C4 1.395(5)
C3 H3 0.9300
C4 C5 1.386(5)
C4 C9 1.463(5)
C5 C6 1.399(5)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.490(5)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9 0.9300
C10 C11 1.505(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C16 1.383(5)
C11 C12 1.388(5)
C12 C13 1.389(5)
C12 H12 0.9300
C13 C14 1.381(5)
C13 H13 0.9300
C14 C15 1.361(5)
C15 C16 1.403(5)
C15 H15 0.9300
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
C5 H5 O3 3_455 0.93 2.52 3.429(5) 167 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
C10 O1 C1 C6 -3.8(5)
C10 O1 C1 C2 176.4(3)
C7 O2 C2 C3 5.0(5)
C7 O2 C2 C1 -175.7(3)
O1 C1 C2 C3 179.9(3)
C6 C1 C2 C3 0.0(5)
O1 C1 C2 O2 0.5(4)
C6 C1 C2 O2 -179.3(3)
O2 C2 C3 C4 178.0(3)
C1 C2 C3 C4 -1.2(5)
C2 C3 C4 C5 1.6(5)
C2 C3 C4 C9 -178.3(3)
C3 C4 C5 C6 -0.7(5)
C9 C4 C5 C6 179.1(3)
O1 C1 C6 C5 -179.0(3)
C2 C1 C6 C5 0.8(5)
C4 C5 C6 C1 -0.5(5)
C2 O2 C7 C8 179.5(3)
C5 C4 C9 O3 -177.1(4)
C3 C4 C9 O3 2.7(7)
C1 O1 C10 C11 179.3(3)
O1 C10 C11 C16 -171.3(3)
O1 C10 C11 C12 10.7(5)
C16 C11 C12 C13 0.2(5)
C10 C11 C12 C13 178.2(4)
C11 C12 C13 C14 0.3(6)
C12 C13 C14 C15 -0.5(6)
C12 C13 C14 Cl1 178.0(3)
C13 C14 C15 C16 0.2(6)
Cl1 C14 C15 C16 -178.3(3)
C12 C11 C16 C15 -0.5(6)
C10 C11 C16 C15 -178.6(4)
C12 C11 C16 Cl2 178.7(3)
C10 C11 C16 Cl2 0.7(5)
C14 C15 C16 C11 0.4(6)
C14 C15 C16 Cl2 -178.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 642645
