#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:10:02 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240429.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_7240429
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_absolute_configuration unk
_chemical_formula_moiety         'C14 H10 Br2 O2'
_chemical_formula_sum            'C14 H10 Br2 O2'
_chemical_formula_weight         370.04
_chemical_melting_point          340
_chemical_name_common            2-(benzyloxy)-3,5-dibromobenzaldehyde
_chemical_name_systematic        3,5-dibromo-2-(phenylmethoxy)benzaldehyde
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0992(2)
_cell_length_b                   17.1619(7)
_cell_length_c                   18.9382(8)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.46
_cell_volume                     1332.30(10)
_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 1.000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34685
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_min         1.601
_exptl_absorpt_coefficient_mu    6.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7522
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/water'
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.015(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0229P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0458
_refine_ls_wR_factor_ref         0.0472
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3010
_reflns_number_total             3341
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra10752e2.cif
_cod_data_source_block           ja027
_cod_depositor_comments
'Adding full bibliography for 7240424--7240429.cif.'
_cod_database_code               7240429
_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   0.122
_shelx_estimated_absorpt_t_max   0.802
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Br1 Br 0.21621(8) 0.49183(2) 0.72125(2) 0.03534(9) Uani 1 1 d . . . . .
Br2 Br 0.09419(9) 0.80373(2) 0.80839(2) 0.04293(10) Uani 1 1 d . . . . .
O1 O 0.7572(7) 0.79510(13) 0.55816(13) 0.0502(6) Uani 1 1 d . . . . .
O2 O 0.5952(5) 0.56810(11) 0.59846(10) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.7108(8) 0.72806(17) 0.57047(15) 0.0291(6) Uani 1 1 d . . . . .
H1 H 0.797638 0.690204 0.539057 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3650(8) 0.54099(17) 0.54448(16) 0.0290(7) Uani 1 1 d . . . . .
H2A H 0.299296 0.584675 0.513451 0.035 Uiso 1 1 calc R U . . .
H2B H 0.167106 0.519083 0.566911 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4653(6) 0.62141(16) 0.64455(15) 0.0225(6) Uani 1 1 d . . . . .
C12 C 0.2955(7) 0.59839(14) 0.70396(14) 0.0243(6) Uani 1 1 d . . . . .
C13 C 0.1813(7) 0.65216(15) 0.75309(15) 0.0267(6) Uani 1 1 d . . . . .
H13 H 0.064672 0.635802 0.793815 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2436(8) 0.73068(15) 0.74064(15) 0.0283(6) Uani 1 1 d . . . . .
C15 C 0.4087(8) 0.75517(16) 0.68230(16) 0.0297(6) Uani 1 1 d . . . . .
H15 H 0.446795 0.809171 0.674971 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5214(7) 0.70083(17) 0.63337(16) 0.0265(6) Uani 1 1 d . . . . .
C21 C 0.5386(7) 0.47954(17) 0.50267(15) 0.0264(6) Uani 1 1 d . . . . .
C22 C 0.6624(7) 0.49518(19) 0.43667(16) 0.0346(7) Uani 1 1 d . . . . .
H22 H 0.637466 0.545784 0.417062 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8234(9) 0.4379(2) 0.39836(18) 0.0443(9) Uani 1 1 d . . . . .
H23 H 0.909534 0.449524 0.352991 0.053 Uiso 1 1 calc R U . . .
C24 C 0.8579(9) 0.3645(2) 0.42621(19) 0.0440(9) Uani 1 1 d . . . . .
H24 H 0.965842 0.325004 0.399894 0.053 Uiso 1 1 calc R U . . .
C25 C 0.7358(9) 0.34807(18) 0.49238(19) 0.0423(8) Uani 1 1 d . . . . .
H25 H 0.760047 0.297314 0.511707 0.051 Uiso 1 1 calc R U . . .
C26 C 0.5787(8) 0.40517(17) 0.53052(17) 0.0333(7) Uani 1 1 d . . . . .
H26 H 0.496973 0.393648 0.576285 0.040 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C2 113.9(2) . . ?
O1 C1 C16 122.7(3) . . ?
O1 C1 H1 118.6 . . ?
C16 C1 H1 118.6 . . ?
O2 C2 C21 106.6(2) . . ?
O2 C2 H2A 110.4 . . ?
C21 C2 H2A 110.4 . . ?
O2 C2 H2B 110.4 . . ?
C21 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O2 C11 C12 121.5(2) . . ?
O2 C11 C16 119.3(3) . . ?
C12 C11 C16 119.0(3) . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 Br1 120.4(2) . . ?
C13 C12 Br1 118.0(2) . . ?
C12 C13 C14 117.9(3) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 Br2 120.4(2) . . ?
C13 C14 Br2 117.8(2) . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 119.8(3) . . ?
C15 C16 C1 119.5(3) . . ?
C11 C16 C1 120.7(3) . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C2 121.2(3) . . ?
C26 C21 C2 120.1(3) . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C21 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
Br1 C12 1.886(2) . ?
Br2 C14 1.896(3) . ?
O1 C1 1.189(3) . ?
O2 C11 1.372(3) . ?
O2 C2 1.467(3) . ?
C1 C16 1.497(4) . ?
C1 H1 0.9500 . ?
C2 C21 1.498(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 C12 1.381(4) . ?
C11 C16 1.398(4) . ?
C12 C13 1.391(4) . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.362(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C21 C22 1.376(4) . ?
C21 C26 1.391(4) . ?
C22 C23 1.388(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(4) . ?
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 2.52 2.836(3) 100 . yes
C2 H2A O1 0.99 2.48 3.448(4) 167 4_466 yes
C2 H2B O2 0.99 2.56 3.350(4) 137 1_455 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 -176.0(2) . . . . ?
C2 O2 C11 C12 85.6(3) . . . . ?
C2 O2 C11 C16 -98.0(3) . . . . ?
O2 C11 C12 C13 175.9(3) . . . . ?
C16 C11 C12 C13 -0.5(4) . . . . ?
O2 C11 C12 Br1 -3.3(4) . . . . ?
C16 C11 C12 Br1 -179.7(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
Br1 C12 C13 C14 179.2(2) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C12 C13 C14 Br2 -179.0(2) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
Br2 C14 C15 C16 179.1(2) . . . . ?
C14 C15 C16 C11 -0.2(4) . . . . ?
C14 C15 C16 C1 -178.3(3) . . . . ?
O2 C11 C16 C15 -175.9(3) . . . . ?
C12 C11 C16 C15 0.6(4) . . . . ?
O2 C11 C16 C1 2.2(4) . . . . ?
C12 C11 C16 C1 178.6(2) . . . . ?
O1 C1 C16 C15 -3.8(5) . . . . ?
O1 C1 C16 C11 178.1(3) . . . . ?
O2 C2 C21 C22 -103.1(3) . . . . ?
O2 C2 C21 C26 76.5(4) . . . . ?
C26 C21 C22 C23 0.2(5) . . . . ?
C2 C21 C22 C23 179.9(3) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 0.1(6) . . . . ?
C24 C25 C26 C21 0.6(5) . . . . ?
C22 C21 C26 C25 -0.8(5) . . . . ?
C2 C21 C26 C25 179.5(3) . . . . ?
