#------------------------------------------------------------------------------
#$Date: 2019-11-04 17:31:25 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/27/1552736.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_1552736
loop_
_publ_author_name
'Durka, Krzysztof'
'Górski, Bartosz'
'Błocki, Krzysztof'
'Urban, Mateusz'
'Woźniak, Krzysztof'
'Barbasiewicz, Michał'
'Luliński, Sergiusz'
_publ_section_title
;
 Experimental and Theoretical Insights into Molecular and Solid-State
 Properties of Isomeric Bis(salicylaldehydes).
;
_journal_issue                   40
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              8674
_journal_page_last               8689
_journal_paper_doi               10.1021/acs.jpca.9b07360
_journal_volume                  123
_journal_year                    2019
_chemical_formula_moiety         'C12 H8 O4'
_chemical_formula_sum            'C12 H8 O4'
_chemical_formula_weight         216.18
_chemical_melting_point          153
_chemical_name_systematic
;
 1,5-bis(methoxymethoxy)naphthalene-2,6-dicarboxaldehyde 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.91(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5165(18)
_cell_length_b                   3.78120(10)
_cell_length_c                   16.046(3)
_cell_measurement_reflns_used    5636
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8000
_cell_measurement_theta_min      2.9500
_cell_volume                     917.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4391
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9403
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.723
_diffrn_reflns_theta_min         3.583
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.019
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0436
_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)+(0.0624P)²+0.7638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1865
_reflns_number_total             1937
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp9b07360_si_002.cif
_cod_data_source_block           5
_cod_original_cell_volume        917.7(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1552736
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.66063(7) 1.0473(3) 0.74354(6) 0.0220(3) Uani 1 1 d . .
O2 O 0.50840(7) 0.7492(3) 0.67898(7) 0.0197(3) Uani 1 1 d . .
H2 H 0.5523(15) 0.844(7) 0.7180(14) 0.037(6) Uiso 1 1 d . .
C7 C 0.62508(9) 0.8026(4) 0.60376(9) 0.0160(3) Uani 1 1 d . .
C4 C 0.48351(9) 0.5274(4) 0.53750(8) 0.0148(3) Uani 1 1 d . .
C3 C 0.54000(9) 0.6962(4) 0.60831(9) 0.0156(3) Uani 1 1 d . .
C6 C 0.65604(9) 0.7397(4) 0.52822(9) 0.0170(3) Uani 1 1 d . .
H6 H 0.7142 0.8104 0.5258 0.020 Uiso 1 1 calc R U
C5 C 0.39638(9) 0.4205(4) 0.54085(9) 0.0167(3) Uani 1 1 d . .
H5 H 0.3749 0.4607 0.5910 0.020 Uiso 1 1 calc R U
C2 C 0.68152(10) 0.9873(4) 0.67510(9) 0.0183(3) Uani 1 1 d . .
H2A H 0.7378 1.0664 0.6686 0.022 Uiso 1 1 calc R U
O3 O 1.24552(7) 1.0353(3) 0.66854(7) 0.0224(3) Uani 1 1 d . .
O4 O 1.18883(7) 0.7233(3) 0.52284(7) 0.0200(3) Uani 1 1 d . .
H4 H 1.2277(16) 0.822(7) 0.5662(16) 0.047(7) Uiso 1 1 d . .
C9 C 1.04087(9) 0.5207(4) 0.48750(9) 0.0146(3) Uani 1 1 d . .
C11 C 1.10029(9) 0.8038(4) 0.62590(9) 0.0163(3) Uani 1 1 d . .
C13 C 1.01754(9) 0.7565(4) 0.64865(9) 0.0171(3) Uani 1 1 d . .
H13 H 1.0103 0.8362 0.7028 0.020 Uiso 1 1 calc R U
C10 C 1.11149(9) 0.6857(4) 0.54666(9) 0.0160(3) Uani 1 1 d . .
C8 C 0.94849(9) 0.5981(4) 0.59371(9) 0.0167(3) Uani 1 1 d . .
H8 H 0.8936 0.5672 0.6096 0.020 Uiso 1 1 calc R U
C12 C 1.17186(10) 0.9857(4) 0.68376(9) 0.0195(3) Uani 1 1 d . .
H12 H 1.1615 1.0715 0.7363 0.023 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C3 O2 H2 106.6(14) . .
C3 C7 C6 119.99(13) . .
C3 C7 C2 120.44(13) . .
C6 C7 C2 119.54(13) . .
C3 C4 C4 117.83(16) . 3_666
C3 C4 C5 121.22(13) . .
C4 C4 C5 120.94(16) 3_666 .
O2 C3 C7 121.79(13) . .
O2 C3 C4 117.66(12) . .
C7 C3 C4 120.56(13) . .
C5 C6 C7 120.99(13) 3_666 .
C5 C6 H6 119.5 3_666 .
C7 C6 H6 119.5 . .
C6 C5 C4 119.68(13) 3_666 .
C6 C5 H5 120.2 3_666 .
C4 C5 H5 120.2 . .
O1 C2 C7 123.84(14) . .
O1 C2 H2A 118.1 . .
C7 C2 H2A 118.1 . .
C10 O4 H4 108.2(16) . .
C9 C9 C8 121.15(16) 3_766 3_766
C9 C9 C10 117.54(16) 3_766 .
C8 C9 C10 121.31(13) 3_766 .
C10 C11 C13 119.81(13) . .
C10 C11 C12 120.11(14) . .
C13 C11 C12 120.05(13) . .
C8 C13 C11 120.87(13) . .
C8 C13 H13 119.6 . .
C11 C13 H13 119.6 . .
O4 C10 C11 121.70(13) . .
O4 C10 C9 117.35(13) . .
C11 C10 C9 120.95(13) . .
C13 C8 C9 119.69(13) . 3_766
C13 C8 H8 120.2 . .
C9 C8 H8 120.2 3_766 .
O3 C12 C11 123.69(14) . .
O3 C12 H12 118.2 . .
C11 C12 H12 118.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2336(18) .
O2 C3 1.3472(17) .
O2 H2 0.89(2) .
C7 C3 1.398(2) .
C7 C6 1.420(2) .
C7 C2 1.455(2) .
C4 C3 1.422(2) .
C4 C4 1.424(3) 3_666
C4 C5 1.4235(19) .
C6 C5 1.362(2) 3_666
C6 H6 0.9500 .
C5 C6 1.362(2) 3_666
C5 H5 0.9500 .
C2 H2A 0.9500 .
O3 C12 1.2352(19) .
O4 C10 1.3459(17) .
O4 H4 0.89(3) .
C9 C9 1.422(3) 3_766
C9 C8 1.4223(19) 3_766
C9 C10 1.423(2) .
C11 C10 1.395(2) .
C11 C13 1.422(2) .
C11 C12 1.452(2) .
C13 C8 1.365(2) .
C13 H13 0.9500 .
C8 C9 1.4224(19) 3_766
C8 H8 0.9500 .
C12 H12 0.9500 .
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_4
C6 C7 C3 O2 179.61(13) . .
C2 C7 C3 O2 -2.2(2) . .
C6 C7 C3 C4 -0.6(2) . .
C2 C7 C3 C4 177.65(13) . .
C4 C4 C3 O2 179.67(15) 3_666 .
C5 C4 C3 O2 0.5(2) . .
C4 C4 C3 C7 -0.2(2) 3_666 .
C5 C4 C3 C7 -179.40(13) . .
C3 C7 C6 C5 0.7(2) . 3_666
C2 C7 C6 C5 -177.51(13) . 3_666
C3 C4 C5 C6 179.84(13) . 3_666
C4 C4 C5 C6 0.6(2) 3_666 3_666
C3 C7 C2 O1 3.2(2) . .
C6 C7 C2 O1 -178.61(14) . .
C10 C11 C13 C8 -0.3(2) . .
C12 C11 C13 C8 177.50(13) . .
C13 C11 C10 O4 -179.60(13) . .
C12 C11 C10 O4 2.6(2) . .
C13 C11 C10 C9 0.6(2) . .
C12 C11 C10 C9 -177.21(13) . .
C9 C9 C10 O4 179.80(15) 3_766 .
C8 C9 C10 O4 -0.3(2) 3_766 .
C9 C9 C10 C11 -0.4(2) 3_766 .
C8 C9 C10 C11 179.50(13) 3_766 .
C11 C13 C8 C9 -0.2(2) . 3_766
C10 C11 C12 O3 -2.5(2) . .
C13 C11 C12 O3 179.69(14) . .
