# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ia358
_database_code_depnum_ccdc_archive 'CCDC 1895105'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3-ethoxy-2-(phenylmethoxy)benzaldehyde
_chemical_name_common            2-(benzyloxy)-3-ethoxybenzaldehyde
_chemical_melting_point          352
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3768(15)
_cell_length_b                   4.5578(5)
_cell_length_c                   19.4729(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.697(5)
_cell_angle_gamma                90
_cell_volume                     1345.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2176
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.85

_exptl_crystal_description       rods
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12325
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3329
_reflns_number_gt                1762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).

A reflection with large difference between its observed and calculated intensity
was omitted. This is due to obstruction by the beam stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+0.2803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.47072(13) 0.7622(5) 0.31500(12) 0.0822(7) Uani 1 1 d . . . . .
O2 O 0.72410(9) 0.5486(3) 0.31645(7) 0.0398(4) Uani 1 1 d . . . . .
O3 O 0.81147(9) 0.1530(3) 0.40507(8) 0.0431(4) Uani 1 1 d . . . . .
C1 C 0.54682(16) 0.6971(6) 0.31654(14) 0.0569(7) Uani 1 1 d . . . . .
H1 H 0.577619 0.784421 0.283384 0.068 Uiso 1 1 calc R U . . .
C2 C 0.74413(17) 0.3640(5) 0.26052(12) 0.0496(6) Uani 1 1 d . . . . .
H2A H 0.690802 0.256134 0.238458 0.060 Uiso 1 1 calc R U . . .
H2B H 0.790519 0.219886 0.278628 0.060 Uiso 1 1 calc R U . . .
C3 C 0.85515(15) -0.0836(5) 0.44551(12) 0.0475(6) Uani 1 1 d . . . . .
H3A H 0.816769 -0.259318 0.441359 0.057 Uiso 1 1 calc R U . . .
H3B H 0.869063 -0.027197 0.495245 0.057 Uiso 1 1 calc R U . . .
C4 C 0.93798(17) -0.1475(7) 0.41792(14) 0.0646(8) Uani 1 1 d . . . . .
H4A H 0.923359 -0.202572 0.368675 0.097 Uiso 1 1 calc R U . . .
H4B H 0.969445 -0.309389 0.444390 0.097 Uiso 1 1 calc R U . . .
H4C H 0.975527 0.027542 0.422563 0.097 Uiso 1 1 calc R U . . .
C11 C 0.59506(14) 0.4877(5) 0.36752(12) 0.0449(6) Uani 1 1 d . . . . .
C12 C 0.68156(14) 0.4123(5) 0.36401(10) 0.0370(5) Uani 1 1 d . . . . .
C13 C 0.72668(14) 0.2109(5) 0.41183(11) 0.0377(5) Uani 1 1 d . . . . .
C14 C 0.68461(15) 0.0983(5) 0.46334(12) 0.0471(6) Uani 1 1 d . . . . .
H14 H 0.714949 -0.035652 0.496347 0.057 Uiso 1 1 calc R U . . .
C15 C 0.59945(17) 0.1774(6) 0.46748(13) 0.0569(7) Uani 1 1 d . . . . .
H15 H 0.571580 0.098999 0.503427 0.068 Uiso 1 1 calc R U . . .
C16 C 0.55429(16) 0.3696(6) 0.41987(14) 0.0556(7) Uani 1 1 d . . . . .
H16 H 0.495193 0.421813 0.422730 0.067 Uiso 1 1 calc R U . . .
C21 C 0.77549(14) 0.5636(5) 0.20901(10) 0.0394(5) Uani 1 1 d . . . . .
C22 C 0.71480(17) 0.7017(5) 0.15976(12) 0.0502(6) Uani 1 1 d . . . . .
H22 H 0.653947 0.661079 0.158468 0.060 Uiso 1 1 calc R U . . .
C23 C 0.7383(3) 0.8946(6) 0.11266(14) 0.0695(8) Uani 1 1 d . . . . .
H23 H 0.694473 0.987497 0.079570 0.083 Uiso 1 1 calc R U . . .
C24 C 0.8236(3) 0.9515(7) 0.11355(15) 0.0766(9) Uani 1 1 d . . . . .
H24 H 0.839725 1.087104 0.080829 0.092 Uiso 1 1 calc R U . . .
C25 C 0.8884(2) 0.8209(8) 0.16004(19) 0.0770(10) Uani 1 1 d . . . . .
H25 H 0.948821 0.861665 0.159296 0.092 Uiso 1 1 calc R U . . .
C26 C 0.86335(18) 0.6214(7) 0.20985(14) 0.0631(8) Uani 1 1 d . . . . .
H26 H 0.907054 0.529601 0.243253 0.076 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.203(3) . ?
O2 C12 1.369(2) . ?
O2 C2 1.450(3) . ?
O3 C13 1.358(2) . ?
O3 C3 1.434(3) . ?
C1 C11 1.483(4) . ?
C1 H1 0.9500 . ?
C2 C21 1.493(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.492(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C12 1.387(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.405(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.373(3) . ?
C21 C26 1.374(3) . ?
C22 C23 1.363(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.334(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.365(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.429(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C12 O2 C2 115.55(16) . . ?
C13 O3 C3 117.49(17) . . ?
O1 C1 C11 123.4(3) . . ?
O1 C1 H1 118.3 . . ?
C11 C1 H1 118.3 . . ?
O2 C2 C21 106.54(18) . . ?
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 . . ?
O3 C3 C4 107.4(2) . . ?
O3 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
O3 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 C1 120.2(2) . . ?
C16 C11 C1 120.2(2) . . ?
O2 C12 C11 119.5(2) . . ?
O2 C12 C13 120.39(19) . . ?
C11 C12 C13 120.0(2) . . ?
O3 C13 C14 125.0(2) . . ?
O3 C13 C12 115.96(18) . . ?
C14 C13 C12 119.0(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C21 C26 118.2(2) . . ?
C22 C21 C2 119.3(2) . . ?
C26 C21 C2 122.5(2) . . ?
C23 C22 C21 122.7(3) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 122.0(3) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C24 C25 C26 118.5(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 119.4(3) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?

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
C12 O2 C2 C21 170.47(17) . . . . ?
C13 O3 C3 C4 167.52(19) . . . . ?
O1 C1 C11 C12 176.9(2) . . . . ?
O1 C1 C11 C16 -4.3(4) . . . . ?
C2 O2 C12 C11 -112.1(2) . . . . ?
C2 O2 C12 C13 71.8(2) . . . . ?
C16 C11 C12 O2 -174.17(19) . . . . ?
C1 C11 C12 O2 4.7(3) . . . . ?
C16 C11 C12 C13 1.9(3) . . . . ?
C1 C11 C12 C13 -179.17(19) . . . . ?
C3 O3 C13 C14 12.6(3) . . . . ?
C3 O3 C13 C12 -170.55(17) . . . . ?
O2 C12 C13 O3 -3.1(3) . . . . ?
C11 C12 C13 O3 -179.18(18) . . . . ?
O2 C12 C13 C14 173.91(18) . . . . ?
C11 C12 C13 C14 -2.2(3) . . . . ?
O3 C13 C14 C15 177.7(2) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C1 C11 C16 C15 -179.4(2) . . . . ?
O2 C2 C21 C22 -84.1(2) . . . . ?
O2 C2 C21 C26 94.2(3) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
C2 C21 C22 C23 177.6(2) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C2 C21 C26 C25 -178.4(2) . . . . ?
C24 C25 C26 C21 0.9(4) . . . . ?

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 2.48 2.809(3) 100 . yes
C2 H2B O3 0.99 2.45 2.990(3) 114 . yes
C2 H2A O1 0.99 2.53 3.414(3) 149 2_645 yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja017_tw
_database_code_depnum_ccdc_archive 'CCDC 1898076'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        5-bromo-2-(phenylmethoxy)benzaldehyde
_chemical_name_common            2-(benzyloxy)-5-bromobenzaldehyde
_chemical_melting_point          343
_chemical_formula_moiety         'C14 H11 Br O2'
_chemical_formula_sum            'C14 H11 Br O2'
_chemical_formula_weight         291.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   7.316(4)
_cell_length_b                   13.239(10)
_cell_length_c                   12.300(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.36(3)
_cell_angle_gamma                90
_cell_volume                     1171.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8261
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.199
_exptl_absorpt_coefficient_mu    3.493
_shelx_estimated_absorpt_T_min   0.414
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.614846
_exptl_absorpt_correction_T_max  0.745687
_exptl_absorpt_process_details   'TWINABS V2008/4 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            2920
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.280
_diffrn_reflns_theta_max         28.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2920
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).

Refined as a 2-component twin.,Twin
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+0.2957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2920
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.01040(3) 0.47516(2) 0.15594(2) 0.04458(8) Uani 1 1 d . . . . .
O1 O 0.4424(2) 0.64546(11) 0.32510(13) 0.0411(4) Uani 1 1 d . . . . .
O2 O 0.39023(19) 0.35636(9) 0.39137(13) 0.0339(3) Uani 1 1 d . . . . .
C1 C 0.4366(3) 0.55762(15) 0.34930(18) 0.0328(4) Uani 1 1 d . . . . .
H1 H 0.346896 0.537339 0.392018 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3496(3) 0.25284(15) 0.40811(18) 0.0310(4) Uani 1 1 d . . . . .
H2A H 0.456160 0.220489 0.456653 0.037 Uiso 1 1 calc R U . . .
H2B H 0.327177 0.216738 0.336457 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5351(2) 0.37779(14) 0.33973(16) 0.0260(4) Uani 1 1 d . . . . .
C12 C 0.5596(2) 0.47967(14) 0.31687(16) 0.0259(4) Uani 1 1 d . . . . .
C13 C 0.7028(3) 0.50859(14) 0.26240(16) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.719983 0.577700 0.246028 0.033 Uiso 1 1 calc R U . . .
C14 C 0.8187(2) 0.43615(15) 0.23272(16) 0.0283(4) Uani 1 1 d . . . . .
C15 C 0.7967(2) 0.33499(15) 0.25580(17) 0.0287(4) Uani 1 1 d . . . . .
H15 H 0.878795 0.285940 0.235110 0.034 Uiso 1 1 calc R U . . .
C16 C 0.6548(3) 0.30599(14) 0.30899(17) 0.0287(4) Uani 1 1 d . . . . .
H16 H 0.638605 0.236645 0.324726 0.034 Uiso 1 1 calc R U . . .
C21 C 0.1801(2) 0.24712(15) 0.46056(15) 0.0275(4) Uani 1 1 d . . . . .
C22 C 0.1161(3) 0.32843(15) 0.51414(17) 0.0321(4) Uani 1 1 d . . . . .
H22 H 0.176983 0.391923 0.515746 0.038 Uiso 1 1 calc R U . . .
C23 C -0.0368(3) 0.31713(17) 0.56541(18) 0.0368(5) Uani 1 1 d . . . . .
H23 H -0.080127 0.373247 0.601717 0.044 Uiso 1 1 calc R U . . .
C24 C -0.1263(3) 0.22597(17) 0.56435(18) 0.0371(5) Uani 1 1 d . . . . .
H24 H -0.229731 0.218714 0.600667 0.045 Uiso 1 1 calc R U . . .
C25 C -0.0651(3) 0.14485(16) 0.51015(19) 0.0374(5) Uani 1 1 d . . . . .
H25 H -0.127282 0.081723 0.508423 0.045 Uiso 1 1 calc R U . . .
C26 C 0.0870(3) 0.15542(15) 0.45828(18) 0.0328(4) Uani 1 1 d . . . . .
H26 H 0.127983 0.099424 0.420764 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C14 1.8981(19) . ?
O1 C1 1.203(3) . ?
O2 C11 1.360(2) . ?
O2 C2 1.425(2) . ?
C1 C12 1.471(3) . ?
C1 H1 0.9500 . ?
C2 C21 1.499(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 C16 1.390(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.395(2) . ?
C13 C14 1.372(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.387(3) . ?
C21 C26 1.390(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 117.93(13) . . ?
O1 C1 C12 124.09(18) . . ?
O1 C1 H1 118.0 . . ?
C12 C1 H1 118.0 . . ?
O2 C2 C21 108.71(15) . . ?
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 124.49(17) . . ?
O2 C11 C12 115.77(15) . . ?
C16 C11 C12 119.74(17) . . ?
C13 C12 C11 119.79(16) . . ?
C13 C12 C1 119.14(17) . . ?
C11 C12 C1 121.08(17) . . ?
C14 C13 C12 119.28(17) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.44(17) . . ?
C13 C14 Br1 119.29(15) . . ?
C15 C14 Br1 119.26(13) . . ?
C16 C15 C14 119.49(16) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 120.26(18) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C21 C26 118.77(17) . . ?
C22 C21 C2 122.78(18) . . ?
C26 C21 C2 118.41(18) . . ?
C21 C22 C23 120.07(19) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.85(19) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.55(18) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.07(19) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.68(19) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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 -177.06(16) . . . . ?
C2 O2 C11 C16 -4.8(3) . . . . ?
C2 O2 C11 C12 174.77(17) . . . . ?
O2 C11 C12 C13 -178.93(18) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
O2 C11 C12 C1 1.1(3) . . . . ?
C16 C11 C12 C1 -179.38(19) . . . . ?
O1 C1 C12 C13 5.5(3) . . . . ?
O1 C1 C12 C11 -174.5(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C1 C12 C13 C14 179.55(19) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 Br1 178.73(15) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
Br1 C14 C15 C16 -178.34(15) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
O2 C11 C16 C15 179.27(19) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
O2 C2 C21 C22 -18.7(3) . . . . ?
O2 C2 C21 C26 163.46(18) . . . . ?
C26 C21 C22 C23 0.8(3) . . . . ?
C2 C21 C22 C23 -177.08(19) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -1.0(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C22 C21 C26 C25 -1.1(3) . . . . ?
C2 C21 C26 C25 176.9(2) . . . . ?

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 2.42 2.747(3) 100 . yes
C15 H15 O1 0.95 2.46 3.408(3) 173 2_645 yes
C22 H22 O2 0.95 2.42 2.744(3) 100 . yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/MeOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ia354
_database_code_depnum_ccdc_archive 'CCDC 1898075'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        5-chloro-2-(phenylmethoxy)benzaldehyde
_chemical_name_common            2-(benzyloxy)-5-chlorobenzaldehyde
_chemical_melting_point          342
_chemical_formula_moiety         'C14 H11 Cl O2'
_chemical_formula_sum            'C14 H11 Cl O2'
_chemical_formula_weight         246.68

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   4.9219(2)
_cell_length_b                   16.3089(6)
_cell_length_c                   14.7245(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.171(2)
_cell_angle_gamma                90
_cell_volume                     1166.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9688
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.31

_exptl_crystal_description       blocks
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.312
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9274
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24526
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.877
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2917
_reflns_number_gt                2378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.3701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ia376
_database_code_depnum_ccdc_archive 'CCDC 1898081'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4-(phenylmethoxybenzaldehyde
_chemical_name_common            4-(benzyloxy)benzaldehyde
_chemical_melting_point          373
_chemical_formula_moiety         'C14 H12 O2'
_chemical_formula_sum            'C14 H12 O2'
_chemical_formula_weight         212.24

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.5088(5)
_cell_length_b                   12.9889(6)
_cell_length_c                   7.2608(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1085.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            off-white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19779
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.364
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2698
_reflns_number_gt                2581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.1324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1155 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2698
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.81084(10) 0.92174(9) 0.4508(2) 0.0499(3) Uani 1 1 d . . . . .
O2 O 0.63665(9) 0.45545(8) 0.46188(17) 0.0351(3) Uani 1 1 d . . . . .
C1 C 0.73385(14) 0.87609(12) 0.5283(2) 0.0366(3) Uani 1 1 d . . . . .
H1 H 0.683842 0.915339 0.605181 0.044 Uiso 1 1 calc R U . . .
C2 C 0.53982(12) 0.41118(11) 0.5564(2) 0.0307(3) Uani 1 1 d . . . . .
H2A H 0.466725 0.442683 0.511732 0.037 Uiso 1 1 calc R U . . .
H2B H 0.546465 0.424734 0.690125 0.037 Uiso 1 1 calc R U . . .
C11 C 0.65585(12) 0.55785(10) 0.4861(2) 0.0284(3) Uani 1 1 d . . . . .
C12 C 0.58165(12) 0.62323(11) 0.5821(2) 0.0309(3) Uani 1 1 d . . . . .
H12 H 0.512705 0.597536 0.637437 0.037 Uiso 1 1 calc R U . . .
C13 C 0.61041(13) 0.72668(12) 0.5953(2) 0.0318(3) Uani 1 1 d . . . . .
H13 H 0.560573 0.771972 0.660995 0.038 Uiso 1 1 calc R U . . .
C14 C 0.71048(12) 0.76520(10) 0.5145(2) 0.0284(3) Uani 1 1 d . . . . .
C15 C 0.78471(12) 0.69866(11) 0.4198(2) 0.0309(3) Uani 1 1 d . . . . .
H15 H 0.853959 0.724351 0.365386 0.037 Uiso 1 1 calc R U . . .
C16 C 0.75751(13) 0.59610(11) 0.4053(2) 0.0316(3) Uani 1 1 d . . . . .
H16 H 0.807838 0.550923 0.340330 0.038 Uiso 1 1 calc R U . . .
C21 C 0.53760(12) 0.29706(10) 0.52212(19) 0.0269(3) Uani 1 1 d . . . . .
C22 C 0.62829(12) 0.24426(11) 0.4382(2) 0.0310(3) Uani 1 1 d . . . . .
H22 H 0.695453 0.280671 0.398962 0.037 Uiso 1 1 calc R U . . .
C23 C 0.62131(14) 0.13865(12) 0.4115(2) 0.0376(4) Uani 1 1 d . . . . .
H23 H 0.683447 0.103097 0.353410 0.045 Uiso 1 1 calc R U . . .
C24 C 0.52372(15) 0.08485(12) 0.4695(3) 0.0402(4) Uani 1 1 d . . . . .
H24 H 0.518799 0.012617 0.450541 0.048 Uiso 1 1 calc R U . . .
C25 C 0.43379(15) 0.13668(12) 0.5548(3) 0.0400(4) Uani 1 1 d . . . . .
H25 H 0.367306 0.099935 0.595960 0.048 Uiso 1 1 calc R U . . .
C26 C 0.44051(13) 0.24225(12) 0.5804(2) 0.0344(3) Uani 1 1 d . . . . .
H26 H 0.378151 0.277546 0.638446 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.206(2) . ?
O2 C11 1.3597(16) . ?
O2 C2 1.4294(17) . ?
C1 C14 1.4686(19) . ?
C1 H1 0.9500 . ?
C2 C21 1.5031(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 C12 1.3916(19) . ?
C11 C16 1.400(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C15 C16 1.372(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.389(2) . ?
C21 C26 1.391(2) . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 117.28(11) . . ?
O1 C1 C14 125.80(16) . . ?
O1 C1 H1 117.1 . . ?
C14 C1 H1 117.1 . . ?
O2 C2 C21 109.30(11) . . ?
O2 C2 H2A 109.8 . . ?
C21 C2 H2A 109.8 . . ?
O2 C2 H2B 109.8 . . ?
C21 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
O2 C11 C12 124.18(12) . . ?
O2 C11 C16 115.41(12) . . ?
C12 C11 C16 120.41(13) . . ?
C13 C12 C11 118.64(13) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 121.24(13) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.56(12) . . ?
C13 C14 C1 118.50(13) . . ?
C15 C14 C1 121.92(13) . . ?
C16 C15 C14 119.93(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.21(13) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C21 C26 118.96(13) . . ?
C22 C21 C2 123.12(12) . . ?
C26 C21 C2 117.90(13) . . ?
C23 C22 C21 120.38(13) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.13(14) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.80(14) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.04(14) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.68(14) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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 -176.45(12) . . . . ?
C2 O2 C11 C12 -6.2(2) . . . . ?
C2 O2 C11 C16 174.25(14) . . . . ?
O2 C11 C12 C13 -179.29(14) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C1 177.97(15) . . . . ?
O1 C1 C14 C13 -172.56(17) . . . . ?
O1 C1 C14 C15 6.2(3) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C1 C14 C15 C16 -177.91(15) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
O2 C11 C16 C15 179.35(15) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
O2 C2 C21 C22 10.15(19) . . . . ?
O2 C2 C21 C26 -170.93(14) . . . . ?
C26 C21 C22 C23 0.7(2) . . . . ?
C2 C21 C22 C23 179.59(14) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C22 C21 C26 C25 -0.3(2) . . . . ?
C2 C21 C26 C25 -179.25(15) . . . . ?

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
C2 H2A O1 0.99 2.55 3.4988(19) 160 3_465 yes
C2 H2B O1 0.99 2.51 3.343(2) 142 4_645 yes
C22 H22 O2 0.95 2.41 2.7502(17) 101 . yes

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ia355
_database_code_depnum_ccdc_archive 'CCDC 1898078'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3-methoxy-2-(prop-2-ynoxy)benzaldehyde
_chemical_name_common            3-methoxy-2-(prop-2-ynyloxy)benzaldehyde
_chemical_melting_point          326
_chemical_formula_moiety         'C11 H10 O3'
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7110(4)
_cell_length_b                   7.9405(4)
_cell_length_c                   9.1857(5)
_cell_angle_alpha                65.896(2)
_cell_angle_beta                 85.990(2)
_cell_angle_gamma                70.155(2)
_cell_volume                     481.36(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6757
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.607
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.232
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12649
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2396
_reflns_number_gt                1985
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELX program suite (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.0905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2396
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.30876(14) 0.66102(14) 0.86805(12) 0.0635(3) Uani 1 1 d . . . . .
O2 O 0.44565(10) 0.19524(10) 0.75809(9) 0.0399(2) Uani 1 1 d . . . . .
O3 O 0.33828(12) 0.21552(12) 0.47759(10) 0.0487(2) Uani 1 1 d . . . . .
C1 C 0.36116(17) 0.52702(17) 0.82533(15) 0.0475(3) Uani 1 1 d . . . . .
H1 H 0.445104 0.404844 0.896536 0.057 Uiso 1 1 calc R U . . .
C2 C 0.34259(17) 0.06586(15) 0.83383(13) 0.0460(3) Uani 1 1 d . . . . .
H2A H 0.428679 -0.064958 0.904022 0.055 Uiso 1 1 calc R U . . .
H2B H 0.282168 0.050223 0.750829 0.055 Uiso 1 1 calc R U . . .
C3 C 0.20249(18) 0.13918(17) 0.92834(13) 0.0474(3) Uani 1 1 d . . . . .
C4 C 0.0870(2) 0.1982(2) 1.00277(16) 0.0628(4) Uani 1 1 d . . . . .
H4 H -0.006612 0.246118 1.063100 0.075 Uiso 1 1 calc R U . . .
C5 C 0.28170(18) 0.2214(2) 0.33033(15) 0.0532(3) Uani 1 1 d . . . . .
H5A H 0.334493 0.304690 0.241896 0.080 Uiso 1 1 calc R U . . .
H5B H 0.146429 0.275426 0.313610 0.080 Uiso 1 1 calc R U . . .
H5C H 0.325348 0.088286 0.334418 0.080 Uiso 1 1 calc R U . . .
C11 C 0.30266(14) 0.54247(15) 0.67047(13) 0.0376(2) Uani 1 1 d . . . . .
C12 C 0.34390(13) 0.37466(14) 0.64173(12) 0.0347(2) Uani 1 1 d . . . . .
C13 C 0.28909(14) 0.38820(15) 0.49393(12) 0.0387(2) Uani 1 1 d . . . . .
C14 C 0.19336(16) 0.57126(18) 0.37706(14) 0.0480(3) Uani 1 1 d . . . . .
H14 H 0.154153 0.582490 0.276709 0.058 Uiso 1 1 calc R U . . .
C15 C 0.15447(17) 0.73827(17) 0.40584(15) 0.0529(3) Uani 1 1 d . . . . .
H15 H 0.090066 0.863129 0.324201 0.063 Uiso 1 1 calc R U . . .
C16 C 0.20751(15) 0.72602(16) 0.55024(15) 0.0461(3) Uani 1 1 d . . . . .
H16 H 0.179771 0.841526 0.568501 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.2151(14) . ?
O2 C12 1.3792(11) . ?
O2 C2 1.4367(13) . ?
O3 C13 1.3614(13) . ?
O3 C5 1.4279(13) . ?
C1 C11 1.4668(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4541(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.1720(19) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 C12 1.3908(14) . ?
C11 C16 1.3982(15) . ?
C12 C13 1.4013(15) . ?
C13 C14 1.3849(15) . ?
C14 C15 1.3870(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3710(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C12 O2 C2 114.44(8) . . ?
C13 O3 C5 117.76(9) . . ?
O1 C1 C11 123.97(11) . . ?
O1 C1 H1 118.0 . . ?
C11 C1 H1 118.0 . . ?
O2 C2 C3 112.06(9) . . ?
O2 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
O2 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 178.71(13) . . ?
C3 C4 H4 180.0 . . ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C11 C16 119.64(10) . . ?
C12 C11 C1 120.11(9) . . ?
C16 C11 C1 120.24(10) . . ?
O2 C12 C11 119.28(9) . . ?
O2 C12 C13 120.20(9) . . ?
C11 C12 C13 120.47(9) . . ?
O3 C13 C14 125.31(10) . . ?
O3 C13 C12 115.75(9) . . ?
C14 C13 C12 118.94(10) . . ?
C13 C14 C15 120.30(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.05(10) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.59(11) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?

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
C12 O2 C2 C3 -66.77(11) . . . . ?
O1 C1 C11 C12 -169.14(11) . . . . ?
O1 C1 C11 C16 11.76(18) . . . . ?
C2 O2 C12 C11 109.86(10) . . . . ?
C2 O2 C12 C13 -72.62(12) . . . . ?
C16 C11 C12 O2 176.85(9) . . . . ?
C1 C11 C12 O2 -2.26(15) . . . . ?
C16 C11 C12 C13 -0.67(15) . . . . ?
C1 C11 C12 C13 -179.78(9) . . . . ?
C5 O3 C13 C14 -2.26(16) . . . . ?
C5 O3 C13 C12 178.57(9) . . . . ?
O2 C12 C13 O3 1.76(14) . . . . ?
C11 C12 C13 O3 179.25(9) . . . . ?
O2 C12 C13 C14 -177.46(9) . . . . ?
C11 C12 C13 C14 0.03(15) . . . . ?
O3 C13 C14 C15 -178.45(10) . . . . ?
C12 C13 C14 C15 0.69(17) . . . . ?
C13 C14 C15 C16 -0.78(18) . . . . ?
C14 C15 C16 C11 0.14(18) . . . . ?
C12 C11 C16 C15 0.58(16) . . . . ?
C1 C11 C16 C15 179.69(10) . . . . ?

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 2.47 2.8025(13) 100 . yes
C2 H2B O3 0.99 2.40 2.9889(14) 118 . yes
C4 H4 O1 0.95 2.32 3.1986(19) 154 2_567 yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja027
_database_code_depnum_ccdc_archive 'CCDC 1898074'
loop_
_audit_author_name
_audit_author_address
'Eric Cyriel Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3,5-dibromo-2-(phenylmethoxy)benzaldehyde
_chemical_name_common            2-(benzyloxy)-3,5-dibromobenzaldehyde
_chemical_melting_point          340
_chemical_formula_moiety         'C14 H10 Br2 O2'
_chemical_formula_sum            'C14 H10 Br2 O2'
_chemical_formula_weight         370.04

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

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'

_cell_length_a                   4.0992(2)
_cell_length_b                   17.1619(7)
_cell_length_c                   18.9382(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1332.30(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.12

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    6.074
_shelx_estimated_absorpt_T_min   0.122
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7522
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            34685
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3341
_reflns_number_gt                3010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).

Refined as a 2-component inversion twin.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.015(11)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3341
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0472
_refine_ls_wR_factor_gt          0.0458
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/water'
