#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/10/7111059.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111059
loop_
_publ_author_name
'Houjou, Hirohiko'
'Lee, Sung-Kil'
'Hishikawa, Yukio'
'Nagawa, Yoshinobu'
'Hiratani, Kazuhisa'
_publ_section_title
;
 Highly selective formation of 2∶2 macrocycles from a novel
 hydroxybenzaldehyde derivative and diamines
;
_journal_issue                   22
_journal_name_full               'Chemical Communications'
_journal_page_first              2197
_journal_paper_doi               10.1039/b005536k
_journal_year                    2000
_chemical_formula_moiety         'C18 H16 O4 '
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 101.431(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7370(3)
_cell_length_b                   13.7793(6)
_cell_length_c                   14.5413(4)
_cell_measurement_reflns_used    9531
_cell_measurement_temperature    193.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1519.50(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9856
_diffrn_measured_fraction_theta_max 0.9856
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3572
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.607
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2595
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.01000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                2463
_reflns_number_total             3427
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b005536ksup1.cif
_cod_data_source_block           al
_cod_original_formula_sum        'C18 H16 O4 '
_cod_database_code               7111059
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
O(1) O 0.6282(1) 0.32091(8) 0.60583(6) 0.0409(3) Uani 1.00 d
O(2) O 0.8019(2) 0.3365(1) 0.87993(8) 0.0884(5) Uani 1.00 d
O(3) O 0.5757(1) 0.34911(6) 0.31088(6) 0.0361(3) Uani 1.00 d
O(4) O 0.6885(2) 0.12047(10) 0.16940(10) 0.0790(5) Uani 1.00 d
C(1) C 0.5787(2) 0.2444(1) 0.65431(9) 0.0387(4) Uani 1.00 d
C(2) C 0.6385(2) 0.2475(1) 0.75210(10) 0.0449(5) Uani 1.00 d
C(3) C 0.5893(2) 0.1723(2) 0.8065(1) 0.0585(6) Uani 1.00 d
C(4) C 0.4887(2) 0.0964(2) 0.7664(1) 0.0641(6) Uani 1.00 d
C(5) C 0.4335(2) 0.0939(1) 0.6705(1) 0.0570(6) Uani 1.00 d
C(6) C 0.4765(2) 0.1674(1) 0.6138(1) 0.0458(5) Uani 1.00 d
C(7) C 0.7514(3) 0.3265(1) 0.7959(1) 0.0581(6) Uani 1.00 d
C(8) C 0.5605(2) 0.3248(1) 0.50708(9) 0.0364(4) Uani 1.00 d
C(9) C 0.6392(2) 0.4096(1) 0.46640(9) 0.0324(4) Uani 1.00 d
C(10) C 0.7725(2) 0.4615(1) 0.5116(1) 0.0419(5) Uani 1.00 d
C(11) C 0.5541(2) 0.4331(1) 0.36704(10) 0.0332(4) Uani 1.00 d
C(12) C 0.5205(2) 0.3561(1) 0.21624(9) 0.0325(4) Uani 1.00 d
C(13) C 0.5580(2) 0.2761(1) 0.16394(10) 0.0378(4) Uani 1.00 d
C(14) C 0.5042(2) 0.2790(1) 0.0663(1) 0.0526(5) Uani 1.00 d
C(15) C 0.4175(3) 0.3577(2) 0.0224(1) 0.0608(6) Uani 1.00 d
C(16) C 0.3815(2) 0.4352(1) 0.0745(1) 0.0540(6) Uani 1.00 d
C(17) C 0.4321(2) 0.4360(1) 0.1712(1) 0.0404(4) Uani 1.00 d
C(18) C 0.6565(2) 0.1933(1) 0.2097(1) 0.0518(5) Uani 1.00 d
H(1) H 0.630(2) 0.178(1) 0.872(1) 0.0623 Uiso 1.00 calc
H(2) H 0.456(2) 0.0456(10) 0.8037(10) 0.0380 Uiso 1.00 calc
H(3) H 0.365(2) 0.039(1) 0.6408(9) 0.0380 Uiso 1.00 calc
H(4) H 0.432(2) 0.164(1) 0.547(1) 0.0623 Uiso 1.00 calc
H(5) H 0.790(2) 0.376(1) 0.7532(10) 0.0380 Uiso 1.00 calc
H(6) H 0.589(2) 0.265(1) 0.4778(9) 0.0380 Uiso 1.00 calc
H(7) H 0.427(2) 0.330(1) 0.496(1) 0.0623 Uiso 1.00 calc
H(8) H 0.826(2) 0.446(1) 0.576(1) 0.0623 Uiso 1.00 calc
H(9) H 0.819(2) 0.514(1) 0.483(1) 0.0623 Uiso 1.00 calc
H(10) H 0.424(2) 0.4455(10) 0.3617(9) 0.0380 Uiso 1.00 calc
H(11) H 0.611(2) 0.493(1) 0.345(1) 0.0623 Uiso 1.00 calc
H(12) H 0.532(2) 0.223(1) 0.0354(9) 0.0380 Uiso 1.00 calc
H(13) H 0.383(2) 0.357(1) -0.047(1) 0.0623 Uiso 1.00 calc
H(14) H 0.319(2) 0.493(1) 0.0466(9) 0.0380 Uiso 1.00 calc
H(15) H 0.409(2) 0.492(1) 0.206(1) 0.0623 Uiso 1.00 calc
H(16) H 0.704(2) 0.197(1) 0.279(1) 0.0623 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) C(8) 117.6(1) 1_555 1_555 yes
C(11) O(3) C(12) 117.8(1) 1_555 1_555 yes
O(1) C(1) C(2) 115.4(1) 1_555 1_555 yes
O(1) C(1) C(6) 124.6(1) 1_555 1_555 yes
C(2) C(1) C(6) 120.0(1) 1_555 1_555 yes
C(1) C(2) C(3) 118.5(2) 1_555 1_555 yes
C(1) C(2) C(7) 120.8(1) 1_555 1_555 yes
C(3) C(2) C(7) 120.7(2) 1_555 1_555 yes
C(2) C(3) C(4) 121.4(2) 1_555 1_555 yes
C(3) C(4) C(5) 119.3(2) 1_555 1_555 yes
C(4) C(5) C(6) 121.4(2) 1_555 1_555 yes
C(1) C(6) C(5) 119.4(2) 1_555 1_555 yes
O(2) C(7) C(2) 124.6(2) 1_555 1_555 yes
O(1) C(8) C(9) 109.3(1) 1_555 1_555 yes
C(8) C(9) C(10) 124.6(1) 1_555 1_555 yes
C(8) C(9) C(11) 114.5(1) 1_555 1_555 yes
C(10) C(9) C(11) 120.9(1) 1_555 1_555 yes
O(3) C(11) C(9) 107.0(1) 1_555 1_555 yes
O(3) C(12) C(13) 115.8(1) 1_555 1_555 yes
O(3) C(12) C(17) 124.0(1) 1_555 1_555 yes
C(13) C(12) C(17) 120.2(1) 1_555 1_555 yes
C(12) C(13) C(14) 118.5(2) 1_555 1_555 yes
C(12) C(13) C(18) 120.9(1) 1_555 1_555 yes
C(14) C(13) C(18) 120.6(2) 1_555 1_555 yes
C(13) C(14) C(15) 121.1(2) 1_555 1_555 yes
C(14) C(15) C(16) 119.7(2) 1_555 1_555 yes
C(15) C(16) C(17) 121.5(2) 1_555 1_555 yes
C(12) C(17) C(16) 119.1(2) 1_555 1_555 yes
O(4) C(18) C(13) 124.4(2) 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.364(2) yes
O(1) C(8) 1.429(2) yes
O(2) C(7) 1.215(2) yes
O(3) C(11) 1.446(2) yes
O(3) C(12) 1.361(2) yes
O(4) C(18) 1.213(2) yes
C(1) C(2) 1.406(2) yes
C(1) C(6) 1.384(2) yes
C(2) C(3) 1.401(2) yes
C(2) C(7) 1.461(2) yes
C(3) C(4) 1.363(3) yes
C(4) C(5) 1.376(3) yes
C(5) C(6) 1.387(2) yes
C(8) C(9) 1.494(2) yes
C(9) C(10) 1.318(2) yes
C(9) C(11) 1.500(2) yes
C(12) C(13) 1.402(2) yes
C(12) C(17) 1.390(2) yes
C(13) C(14) 1.398(2) yes
C(13) C(18) 1.457(2) yes
C(14) C(15) 1.367(3) yes
C(15) C(16) 1.369(3) yes
C(16) C(17) 1.383(2) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) C(14) 3.369(2) 4_555
O(1) C(13) 3.528(2) 4_555
O(2) C(8) 3.301(2) 4_555
O(2) C(6) 3.401(2) 4_555
O(2) C(16) 3.567(3) 3_666
O(2) O(3) 3.589(2) 4_555
O(3) C(7) 3.462(2) 4_454
O(3) C(4) 3.466(2) 4_554
O(3) C(2) 3.578(2) 4_454
O(4) C(11) 3.366(2) 2_645
O(4) C(10) 3.483(2) 2_645
O(4) C(4) 3.491(3) 3_656
O(4) C(1) 3.591(2) 4_554
C(2) C(12) 3.414(2) 4_555
C(5) C(13) 3.398(2) 4_455
C(5) C(12) 3.460(2) 4_455
C(6) C(13) 3.544(2) 4_455
C(6) C(16) 3.585(2) 4_555
C(9) C(9) 3.554(3) 3_666
C(16) C(16) 3.581(3) 3_665
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
O(1) C(1) C(2) C(3) 178.6(1) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(2) C(7) -2.3(2) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(6) C(5) -179.5(1) 1_555 1_555 1_555 1_555 yes
O(1) C(8) C(9) C(10) 11.0(2) 1_555 1_555 1_555 1_555 yes
O(1) C(8) C(9) C(11) -169.0(1) 1_555 1_555 1_555 1_555 yes
O(2) C(7) C(2) C(1) 176.6(2) 1_555 1_555 1_555 1_555 yes
O(2) C(7) C(2) C(3) -4.3(3) 1_555 1_555 1_555 1_555 yes
O(3) C(11) C(9) C(8) -60.9(2) 1_555 1_555 1_555 1_555 yes
O(3) C(11) C(9) C(10) 119.1(1) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(13) C(14) 179.8(1) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(13) C(18) -2.4(2) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(17) C(16) -179.8(1) 1_555 1_555 1_555 1_555 yes
O(4) C(18) C(13) C(12) 177.5(2) 1_555 1_555 1_555 1_555 yes
O(4) C(18) C(13) C(14) -4.8(3) 1_555 1_555 1_555 1_555 yes
C(1) O(1) C(8) C(9) -176.2(1) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 1.3(2) 1_555 1_555 1_555 1_555 yes
C(1) C(6) C(5) C(4) 0.7(3) 1_555 1_555 1_555 1_555 yes
C(2) C(1) O(1) C(8) -175.6(1) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(6) C(5) 0.2(2) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) -0.3(3) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(6) -1.2(2) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(6) -0.7(3) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(2) C(7) -177.9(2) 1_555 1_555 1_555 1_555 yes
C(6) C(1) O(1) C(8) 4.2(2) 1_555 1_555 1_555 1_555 yes
C(6) C(1) C(2) C(7) 177.9(1) 1_555 1_555 1_555 1_555 yes
C(9) C(11) O(3) C(12) -175.0(1) 1_555 1_555 1_555 1_555 yes
C(11) O(3) C(12) C(13) 174.6(1) 1_555 1_555 1_555 1_555 yes
C(11) O(3) C(12) C(17) -5.5(2) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(14) C(15) 0.2(2) 1_555 1_555 1_555 1_555 yes
C(12) C(17) C(16) C(15) -0.3(2) 1_555 1_555 1_555 1_555 yes
C(13) C(12) C(17) C(16) 0.1(2) 1_555 1_555 1_555 1_555 yes
C(13) C(14) C(15) C(16) -0.3(3) 1_555 1_555 1_555 1_555 yes
C(14) C(13) C(12) C(17) -0.1(2) 1_555 1_555 1_555 1_555 yes
C(14) C(15) C(16) C(17) 0.4(3) 1_555 1_555 1_555 1_555 yes
C(15) C(14) C(13) C(18) -177.6(2) 1_555 1_555 1_555 1_555 yes
C(17) C(12) C(13) C(18) 177.7(1) 1_555 1_555 1_555 1_555 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11277866
