#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:10:02 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240426.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240426
loop_
_publ_author_name
'Hulushe, Siya T.'
'Manyeruke, Meloddy H.'
'Louzada, Marcel'
'Rigin, Sergei'
'Hosten, Eric C.'
'Watkins, Gareth M.'
_publ_section_title
;
 Exploring intermolecular contacts in multi-substituted benzaldehyde
 derivatives: X-ray, Hirshfeld surface and lattice energy analyses
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              16861
_journal_page_last               16874
_journal_paper_doi               10.1039/C9RA10752E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H11 Cl O2'
_chemical_formula_sum            'C14 H11 Cl O2'
_chemical_formula_weight         246.68
_chemical_melting_point          342
_chemical_name_common            2-(benzyloxy)-5-chlorobenzaldehyde
_chemical_name_systematic        5-chloro-2-(phenylmethoxy)benzaldehyde
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.171(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9219(2)
_cell_length_b                   16.3089(6)
_cell_length_c                   14.7245(5)
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.50
_cell_volume                     1166.84(8)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         1.877
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9274
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0398P)²+0.3701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2378
_reflns_number_total             2917
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra10752e2.cif
_cod_data_source_block           ia354
_cod_depositor_comments
'Adding full bibliography for 7240424--7240429.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240426
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.28696(8) 0.07555(2) 0.50325(3) 0.04078(12) Uani 1 1 d . . . . .
O1 O 0.4157(2) 0.25123(7) 0.34328(7) 0.0459(3) Uani 1 1 d . . . . .
O2 O 0.4633(2) 0.35370(6) 0.59046(6) 0.0318(2) Uani 1 1 d . . . . .
C1 C 0.4281(3) 0.28108(9) 0.41874(10) 0.0344(3) Uani 1 1 d . . . . .
H1 H 0.552992 0.325073 0.434861 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5155(3) 0.38663(8) 0.68162(9) 0.0287(3) Uani 1 1 d . . . . .
H2A H 0.582997 0.342818 0.726073 0.034 Uiso 1 1 calc R U . . .
H2B H 0.343461 0.409226 0.698365 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2843(3) 0.28996(7) 0.57458(9) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.2604(3) 0.25321(8) 0.48758(9) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.0815(3) 0.18764(8) 0.46620(9) 0.0284(3) Uani 1 1 d . . . . .
H13 H 0.064100 0.162560 0.407319 0.034 Uiso 1 1 calc R U . . .
C14 C -0.0703(3) 0.15906(8) 0.53016(9) 0.0276(3) Uani 1 1 d . . . . .
C15 C -0.0496(3) 0.19529(8) 0.61609(9) 0.0286(3) Uani 1 1 d . . . . .
H15 H -0.156785 0.175297 0.659586 0.034 Uiso 1 1 calc R U . . .
C16 C 0.1275(3) 0.26064(8) 0.63837(9) 0.0277(3) Uani 1 1 d . . . . .
H16 H 0.142093 0.285547 0.697272 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7279(3) 0.45322(8) 0.68514(9) 0.0266(3) Uani 1 1 d . . . . .
C22 C 0.7883(3) 0.49152(9) 0.60700(9) 0.0324(3) Uani 1 1 d . . . . .
H22 H 0.698484 0.474416 0.548135 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9791(3) 0.55470(9) 0.61387(10) 0.0373(3) Uani 1 1 d . . . . .
H23 H 1.018768 0.580552 0.559676 0.045 Uiso 1 1 calc R U . . .
C24 C 1.1115(3) 0.58028(9) 0.69867(10) 0.0375(3) Uani 1 1 d . . . . .
H24 H 1.242228 0.623541 0.703233 0.045 Uiso 1 1 calc R U . . .
C25 C 1.0521(3) 0.54244(10) 0.77660(10) 0.0438(4) Uani 1 1 d . . . . .
H25 H 1.141575 0.559899 0.835381 0.053 Uiso 1 1 calc R U . . .
C26 C 0.8626(3) 0.47897(10) 0.77001(10) 0.0399(4) Uani 1 1 d . . . . .
H26 H 0.824769 0.452907 0.824332 0.048 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C2 117.61(10) . . ?
O1 C1 C12 123.80(13) . . ?
O1 C1 H1 118.1 . . ?
C12 C1 H1 118.1 . . ?
O2 C2 C21 108.89(10) . . ?
O2 C2 H2A 109.9 . . ?
C21 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C21 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C11 C16 124.11(11) . . ?
O2 C11 C12 116.24(11) . . ?
C16 C11 C12 119.65(11) . . ?
C13 C12 C11 119.60(11) . . ?
C13 C12 C1 118.99(11) . . ?
C11 C12 C1 121.38(12) . . ?
C14 C13 C12 120.02(12) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.83(12) . . ?
C13 C14 Cl1 119.41(10) . . ?
C15 C14 Cl1 119.75(10) . . ?
C16 C15 C14 119.83(12) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 120.07(12) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C21 C26 118.62(12) . . ?
C22 C21 C2 122.59(11) . . ?
C26 C21 C2 118.76(12) . . ?
C21 C22 C23 120.52(13) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.53(13) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.19(13) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.46(14) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.67(13) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.7360(13) . ?
O1 C1 1.2056(17) . ?
O2 C11 1.3584(15) . ?
O2 C2 1.4305(15) . ?
C1 C12 1.4770(18) . ?
C1 H1 0.9500 . ?
C2 C21 1.5026(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 C16 1.3923(17) . ?
C11 C12 1.4021(17) . ?
C12 C13 1.3893(18) . ?
C13 C14 1.3737(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3854(19) . ?
C15 C16 1.3826(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.3826(18) . ?
C21 C26 1.3832(19) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.95 2.45 2.7724(16) 100 . yes
C22 H22 O2 0.95 2.42 2.7472(17) 100 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O2 C2 C21 177.23(11) . . . . ?
C2 O2 C11 C16 7.15(18) . . . . ?
C2 O2 C11 C12 -173.20(11) . . . . ?
O2 C11 C12 C13 180.00(11) . . . . ?
C16 C11 C12 C13 -0.34(19) . . . . ?
O2 C11 C12 C1 1.88(18) . . . . ?
C16 C11 C12 C1 -178.46(12) . . . . ?
O1 C1 C12 C13 1.6(2) . . . . ?
O1 C1 C12 C11 179.70(14) . . . . ?
C11 C12 C13 C14 -0.14(19) . . . . ?
C1 C12 C13 C14 178.03(12) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C12 C13 C14 Cl1 -178.50(10) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
Cl1 C14 C15 C16 178.55(10) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
O2 C11 C16 C15 -179.99(12) . . . . ?
C12 C11 C16 C15 0.38(19) . . . . ?
O2 C2 C21 C22 18.67(18) . . . . ?
O2 C2 C21 C26 -163.33(12) . . . . ?
C26 C21 C22 C23 -0.3(2) . . . . ?
C2 C21 C22 C23 177.69(13) . . . . ?
C21 C22 C23 C24 0.0(2) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C22 C21 C26 C25 0.6(2) . . . . ?
C2 C21 C26 C25 -177.44(15) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
