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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032768.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_4032768
loop_
_publ_author_name
'Pan, San-Jiang'
'Ye, Gang'
'Jia, Fei'
'He, Zhenfeng'
'Ke, Hua'
'Yao, Huan'
'Fan, Zhi'
'Jiang, Wei'
_publ_section_title
;
 Regioselective Synthesis of Methylene-Bridged Naphthalene Oligomers and
 Their Host-Guest Chemistry.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9570
_journal_page_last               9575
_journal_paper_doi               10.1021/acs.joc.7b01579
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C56 H72 O6'
_chemical_formula_sum            'C56 H72 O6'
_chemical_formula_weight         841.13
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.262(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.2454(8)
_cell_length_b                   7.4219(3)
_cell_length_c                   18.7073(7)
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      58.77
_cell_measurement_theta_min      2.85
_cell_volume                     2309.51(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10051
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        59.024
_diffrn_reflns_theta_max         59.024
_diffrn_reflns_theta_min         2.848
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0727 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8908. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0855P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2290
_reflns_number_total             3299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01579_si_004.cif
_cod_data_source_block           11n
_cod_depositor_comments
'Adding full bibliography for 4032768--4032770.cif.'
_cod_database_code               4032768
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.44181(9) 0.7545(2) 0.30438(10) 0.0275(5) Uani 1 1 d .
O2 O 0.88604(9) 0.8263(2) 0.35905(9) 0.0223(5) Uani 1 1 d .
O3 O 0.77632(9) 0.3760(2) 0.44103(10) 0.0223(5) Uani 1 1 d .
C1 C 0.52219(14) 0.7646(4) 0.31954(15) 0.0216(6) Uani 1 1 d .
C2 C 0.55312(14) 0.8201(4) 0.26808(15) 0.0228(7) Uani 1 1 d .
H2 H 0.5180 0.8575 0.2168 0.027 Uiso 1 1 calc R
C3 C 0.63775(13) 0.8223(3) 0.29097(14) 0.0187(6) Uani 1 1 d .
C4 C 0.69099(14) 0.7620(3) 0.36697(14) 0.0169(6) Uani 1 1 d .
C5 C 0.65522(14) 0.7073(4) 0.41781(15) 0.0221(6) Uani 1 1 d .
H5 H 0.6888 0.6688 0.4694 0.027 Uiso 1 1 calc R
C6 C 0.57392(14) 0.7084(4) 0.39497(15) 0.0249(7) Uani 1 1 d .
H6 H 0.5521 0.6705 0.4307 0.030 Uiso 1 1 calc R
C7 C 0.67017(14) 0.8828(4) 0.23901(15) 0.0214(6) Uani 1 1 d .
H7 H 0.6351 0.9242 0.1884 0.026 Uiso 1 1 calc R
C8 C 0.75164(14) 0.8834(3) 0.25992(15) 0.0199(6) Uani 1 1 d .
H8 H 0.7726 0.9242 0.2239 0.024 Uiso 1 1 calc R
C9 C 0.80354(13) 0.8238(3) 0.33433(14) 0.0194(6) Uani 1 1 d .
C10 C 0.77619(14) 0.7631(3) 0.38922(14) 0.0157(6) Uani 1 1 d .
C11 C 0.38530(14) 0.7933(4) 0.22627(15) 0.0281(7) Uani 1 1 d .
H11A H 0.3952 0.7142 0.1886 0.034 Uiso 1 1 calc R
H11B H 0.3910 0.9201 0.2129 0.034 Uiso 1 1 calc R
C12 C 0.30217(14) 0.7616(4) 0.22177(16) 0.0284(7) Uani 1 1 d .
H12A H 0.2916 0.8471 0.2571 0.034 Uiso 1 1 calc R
H12B H 0.2987 0.6379 0.2399 0.034 Uiso 1 1 calc R
C13 C 0.23885(15) 0.7857(5) 0.13884(17) 0.0394(8) Uani 1 1 d .
H13A H 0.2442 0.9082 0.1206 0.047 Uiso 1 1 calc R
H13B H 0.2495 0.6984 0.1042 0.047 Uiso 1 1 calc R
C14 C 0.15330(16) 0.7605(5) 0.13031(19) 0.0539(11) Uani 1 1 d .
H14A H 0.1163 0.7709 0.0749 0.081 Uiso 1 1 calc GR
H14B H 0.1405 0.8532 0.1607 0.081 Uiso 1 1 calc GR
H14C H 0.1477 0.6410 0.1498 0.081 Uiso 1 1 calc GR
C15 C 0.91740(14) 0.8427(4) 0.30036(15) 0.0234(6) Uani 1 1 d .
H15A H 0.9057 0.9637 0.2760 0.028 Uiso 1 1 calc R
H15B H 0.8931 0.7510 0.2589 0.028 Uiso 1 1 calc R
C16 C 1.00723(13) 0.8139(4) 0.34225(15) 0.0246(7) Uani 1 1 d .
H16A H 1.0172 0.6989 0.3716 0.029 Uiso 1 1 calc R
H16B H 1.0305 0.9120 0.3809 0.029 Uiso 1 1 calc R
C17 C 1.05034(14) 0.8089(4) 0.28808(16) 0.0266(7) Uani 1 1 d .
H17A H 1.0383 0.9203 0.2562 0.032 Uiso 1 1 calc R
H17B H 1.0309 0.7049 0.2520 0.032 Uiso 1 1 calc R
C18 C 1.14077(14) 0.7928(4) 0.33560(17) 0.0356(8) Uani 1 1 d .
H18A H 1.1676 0.7818 0.2999 0.053 Uiso 1 1 calc GR
H18B H 1.1523 0.6859 0.3692 0.053 Uiso 1 1 calc GR
H18C H 1.1606 0.9004 0.3683 0.053 Uiso 1 1 calc GR
C19 C 0.83631(13) 0.7171(3) 0.47170(14) 0.0175(6) Uani 1 1 d .
H19A H 0.8064 0.6905 0.5043 0.021 Uiso 1 1 calc R
H19B H 0.8703 0.8241 0.4944 0.021 Uiso 1 1 calc R
C20 C 0.89087(13) 0.5574(3) 0.47658(14) 0.0171(6) Uani 1 1 d .
C21 C 0.97622(13) 0.5771(3) 0.50066(14) 0.0167(6) Uani 1 1 d .
C22 C 0.98340(13) 0.2573(3) 0.47254(13) 0.0156(6) Uani 1 1 d .
H22 H 1.0130 0.1556 0.4684 0.019 Uiso 1 1 calc R
C23 C 0.90288(14) 0.2402(3) 0.45244(14) 0.0165(6) Uani 1 1 d .
H23 H 0.8774 0.1271 0.4350 0.020 Uiso 1 1 calc R
C24 C 0.85742(13) 0.3877(3) 0.45733(14) 0.0171(6) Uani 1 1 d .
C25 C 0.73944(14) 0.2023(4) 0.42136(15) 0.0212(6) Uani 1 1 d .
H25A H 0.7713 0.1125 0.4611 0.025 Uiso 1 1 calc R
H25B H 0.7366 0.1634 0.3696 0.025 Uiso 1 1 calc R
C26 C 0.65542(14) 0.2167(4) 0.41897(15) 0.0228(7) Uani 1 1 d .
H26A H 0.6285 0.3238 0.3876 0.027 Uiso 1 1 calc R
H26B H 0.6241 0.1092 0.3920 0.027 Uiso 1 1 calc R
C27 C 0.65390(15) 0.2316(4) 0.49922(16) 0.0323(8) Uani 1 1 d .
H27A H 0.6839 0.1290 0.5320 0.039 Uiso 1 1 calc R
H27B H 0.6816 0.3439 0.5248 0.039 Uiso 1 1 calc R
C28 C 0.56931(17) 0.2327(5) 0.4956(2) 0.0472(9) Uani 1 1 d .
H28A H 0.5395 0.3351 0.4640 0.071 Uiso 1 1 calc GR
H28B H 0.5718 0.2432 0.5488 0.071 Uiso 1 1 calc GR
H28C H 0.5420 0.1203 0.4717 0.071 Uiso 1 1 calc GR
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
C1 O1 C11 117.37(19) . .
C9 O2 C15 117.82(18) . .
C24 O3 C25 117.38(19) . .
O1 C1 C6 114.3(2) . .
C2 C1 O1 125.8(2) . .
C2 C1 C6 119.9(2) . .
C1 C2 H2 119.9 . .
C1 C2 C3 120.2(2) . .
C3 C2 H2 119.9 . .
C2 C3 C4 120.5(2) . .
C7 C3 C2 120.6(2) . .
C7 C3 C4 118.9(2) . .
C3 C4 C10 120.1(2) . .
C5 C4 C3 116.5(2) . .
C5 C4 C10 123.4(2) . .
C4 C5 H5 119.0 . .
C6 C5 C4 122.0(2) . .
C6 C5 H5 119.0 . .
C1 C6 H6 119.6 . .
C5 C6 C1 120.9(2) . .
C5 C6 H6 119.6 . .
C3 C7 H7 119.4 . .
C8 C7 C3 121.3(2) . .
C8 C7 H7 119.4 . .
C7 C8 H8 120.2 . .
C7 C8 C9 119.7(2) . .
C9 C8 H8 120.2 . .
O2 C9 C8 121.9(2) . .
O2 C9 C10 115.5(2) . .
C10 C9 C8 122.5(2) . .
C4 C10 C19 122.5(2) . .
C9 C10 C4 117.6(2) . .
C9 C10 C19 119.7(2) . .
O1 C11 H11A 110.0 . .
O1 C11 H11B 110.0 . .
O1 C11 C12 108.3(2) . .
H11A C11 H11B 108.4 . .
C12 C11 H11A 110.0 . .
C12 C11 H11B 110.0 . .
C11 C12 H12A 109.3 . .
C11 C12 H12B 109.3 . .
C11 C12 C13 111.5(2) . .
H12A C12 H12B 108.0 . .
C13 C12 H12A 109.3 . .
C13 C12 H12B 109.3 . .
C12 C13 H13A 108.7 . .
C12 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C14 C13 C12 114.3(2) . .
C14 C13 H13A 108.7 . .
C14 C13 H13B 108.7 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O2 C15 H15A 110.5 . .
O2 C15 H15B 110.5 . .
O2 C15 C16 106.2(2) . .
H15A C15 H15B 108.7 . .
C16 C15 H15A 110.5 . .
C16 C15 H15B 110.5 . .
C15 C16 H16A 108.8 . .
C15 C16 H16B 108.8 . .
C15 C16 C17 114.0(2) . .
H16A C16 H16B 107.7 . .
C17 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
C16 C17 H17A 109.6 . .
C16 C17 H17B 109.6 . .
C16 C17 C18 110.3(2) . .
H17A C17 H17B 108.1 . .
C18 C17 H17A 109.6 . .
C18 C17 H17B 109.6 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C10 C19 H19A 108.6 . .
C10 C19 H19B 108.6 . .
C10 C19 C20 114.6(2) . .
H19A C19 H19B 107.6 . .
C20 C19 H19A 108.6 . .
C20 C19 H19B 108.6 . .
C21 C20 C19 122.3(2) . .
C24 C20 C19 119.0(2) . .
C24 C20 C21 118.7(2) . .
C20 C21 C21 119.7(3) . 3_766
C22 C21 C20 122.6(2) 3_766 .
C22 C21 C21 117.8(3) 3_766 3_766
C21 C22 H22 119.2 3_766 .
C23 C22 C21 121.6(2) . 3_766
C23 C22 H22 119.2 . .
C22 C23 H23 119.7 . .
C22 C23 C24 120.6(2) . .
C24 C23 H23 119.7 . .
O3 C24 C23 123.0(2) . .
C20 C24 O3 115.6(2) . .
C20 C24 C23 121.3(2) . .
O3 C25 H25A 110.1 . .
O3 C25 H25B 110.1 . .
O3 C25 C26 107.8(2) . .
H25A C25 H25B 108.5 . .
C26 C25 H25A 110.1 . .
C26 C25 H25B 110.1 . .
C25 C26 H26A 108.8 . .
C25 C26 H26B 108.8 . .
H26A C26 H26B 107.7 . .
C27 C26 C25 113.9(2) . .
C27 C26 H26A 108.8 . .
C27 C26 H26B 108.8 . .
C26 C27 H27A 109.0 . .
C26 C27 H27B 109.0 . .
H27A C27 H27B 107.8 . .
C28 C27 C26 112.8(2) . .
C28 C27 H27A 109.0 . .
C28 C27 H27B 109.0 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.376(3) .
O1 C11 1.429(3) .
O2 C9 1.381(3) .
O2 C15 1.437(3) .
O3 C24 1.385(3) .
O3 C25 1.431(3) .
C1 C2 1.365(4) .
C1 C6 1.400(4) .
C2 H2 0.9500 .
C2 C3 1.423(3) .
C3 C4 1.425(3) .
C3 C7 1.403(3) .
C4 C5 1.416(3) .
C4 C10 1.435(3) .
C5 H5 0.9500 .
C5 C6 1.365(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C7 C8 1.373(3) .
C8 H8 0.9500 .
C8 C9 1.395(3) .
C9 C10 1.388(3) .
C10 C19 1.520(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.503(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.517(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.514(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.514(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.517(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.524(3) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.526(3) .
C20 C21 1.440(3) .
C20 C24 1.381(4) .
C21 C21 1.442(5) 3_766
C21 C22 1.415(3) 3_766
C22 C21 1.415(3) 3_766
C22 H22 0.9500 .
C22 C23 1.364(3) .
C23 H23 0.9500 .
C23 C24 1.399(3) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C25 C26 1.519(3) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C26 C27 1.517(4) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C27 C28 1.517(3) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095343
