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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/23/1542336.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_1542336
loop_
_publ_author_name
'Lewis, J. E. M.'
'Bordoli, R. J.'
'Denis, M.'
'Fletcher, C. J.'
'Galli, M.'
'Neal, E. A.'
'Rochette, E. M.'
'Goldup, S. M.'
_publ_section_title
;
 High yielding synthesis of 2,2′-bipyridine macrocycles, versatile
 intermediates in the synthesis of rotaxanes
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3154
_journal_paper_doi               10.1039/C6SC00011H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C60 H60 N4 O8'
_chemical_formula_weight         965.12
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.5350(10)
_cell_angle_beta                 110.1260(10)
_cell_angle_gamma                109.435(2)
_cell_formula_units_Z            1
_cell_length_a                   9.688(2)
_cell_length_b                   11.374(2)
_cell_length_c                   13.628(3)
_cell_measurement_reflns_used    3861
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.3
_cell_volume                     1252.4(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24806
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.630
_diffrn_reflns_theta_min         2.311
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0515
_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)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4291
_reflns_number_total             5778
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc00011h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1542335--1542337.cif.'
_cod_database_code               1542336
_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.
;
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.41975(12) 0.65134(10) 0.02071(9) 0.0285(3) Uani 1 1 d . .
O2 O 1.30881(13) 1.11041(11) 0.55034(10) 0.0433(3) Uani 1 1 d . .
O3 O 1.11326(12) 1.20215(11) 0.26617(9) 0.0351(3) Uani 1 1 d . .
O4 O -0.21642(13) 0.52660(11) 0.30158(10) 0.0355(3) Uani 1 1 d . .
N2 N 0.23596(13) 0.62435(12) 0.09521(10) 0.0246(3) Uani 1 1 d . .
N1 N -0.03385(14) 0.54469(12) 0.22568(10) 0.0263(3) Uani 1 1 d . .
C21 C 0.65186(17) 0.91799(14) 0.03048(13) 0.0277(3) Uani 1 1 d . .
C7 C -0.3041(2) 0.36844(17) 0.38261(15) 0.0358(4) Uani 1 1 d . .
H7A H -0.2665 0.4353 0.4531 0.043 Uiso 1 1 calc R U
H7B H -0.4126 0.3555 0.3350 0.043 Uiso 1 1 calc R U
C18 C 0.95929(17) 1.10977(15) 0.19272(13) 0.0305(3) Uani 1 1 d . .
C4 C -0.17162(17) 0.68618(15) 0.21543(13) 0.0301(3) Uani 1 1 d . .
H4 H -0.2464 0.7103 0.2314 0.036 Uiso 1 1 calc R U
C17 C 1.15929(18) 1.22045(16) 0.38095(13) 0.0341(4) Uani 1 1 d . .
H17A H 1.1402 1.1363 0.3932 0.041 Uiso 1 1 calc R U
H17B H 1.0957 1.2575 0.4062 0.041 Uiso 1 1 calc R U
C19 C 0.92317(18) 1.08127(16) 0.08099(14) 0.0343(4) Uani 1 1 d . .
H19 H 1.0010 1.1261 0.0595 0.041 Uiso 1 1 calc R U
C22 C 0.69009(17) 0.94888(15) 0.14276(13) 0.0298(3) Uani 1 1 d . .
H22 H 0.6122 0.9043 0.1643 0.036 Uiso 1 1 calc R U
C8 C -0.31113(19) 0.24001(16) 0.40146(14) 0.0328(4) Uani 1 1 d . .
C26 C 0.33959(16) 0.58671(14) 0.07289(12) 0.0250(3) Uani 1 1 d . .
C28 C 0.29422(17) 0.41805(14) 0.15327(13) 0.0278(3) Uani 1 1 d . .
H28 H 0.3130 0.3485 0.1723 0.033 Uiso 1 1 calc R U
C16 C 1.33736(18) 1.31358(15) 0.44368(14) 0.0329(4) Uani 1 1 d . .
H16A H 1.3535 1.3978 0.4319 0.040 Uiso 1 1 calc R U
H16B H 1.3980 1.2777 0.4138 0.040 Uiso 1 1 calc R U
C1 C 0.04365(16) 0.60662(14) 0.17127(12) 0.0248(3) Uani 1 1 d . .
C24 C 0.48733(17) 0.81819(15) -0.05992(13) 0.0282(3) Uani 1 1 d . .
H24A H 0.5029 0.7536 -0.1069 0.034 Uiso 1 1 calc R U
H24B H 0.4398 0.8636 -0.1054 0.034 Uiso 1 1 calc R U
C11 C -0.32096(19) 0.00090(16) 0.43132(14) 0.0351(4) Uani 1 1 d . .
C23 C 0.84048(18) 1.04385(15) 0.22369(13) 0.0315(3) Uani 1 1 d . .
H23 H 0.8620 1.0635 0.2982 0.038 Uiso 1 1 calc R U
C25 C 0.36723(17) 0.74522(15) -0.01994(13) 0.0277(3) Uani 1 1 d . .
H25A H 0.3660 0.8069 0.0389 0.033 Uiso 1 1 calc R U
H25B H 0.2585 0.6995 -0.0804 0.033 Uiso 1 1 calc R U
C13 C -0.44916(19) 0.12203(16) 0.33988(13) 0.0332(4) Uani 1 1 d . .
H13 H -0.5400 0.1228 0.2870 0.040 Uiso 1 1 calc R U
C27 C 0.37604(17) 0.48450(15) 0.10127(13) 0.0280(3) Uani 1 1 d . .
H27 H 0.4523 0.4627 0.0855 0.034 Uiso 1 1 calc R U
C30 C 0.15776(15) 0.55893(14) 0.14747(12) 0.0245(3) Uani 1 1 d . .
C29 C 0.18249(16) 0.45519(15) 0.17760(13) 0.0270(3) Uani 1 1 d . .
H29 H 0.1264 0.4114 0.2130 0.032 Uiso 1 1 calc R U
C14 C 1.45291(18) 1.23282(15) 0.60292(14) 0.0354(4) Uani 1 1 d . .
H14A H 1.5348 1.2252 0.5799 0.042 Uiso 1 1 calc R U
H14B H 1.4972 1.2556 0.6829 0.042 Uiso 1 1 calc R U
C20 C 0.77295(19) 0.98717(16) 0.00196(14) 0.0335(4) Uani 1 1 d . .
H20 H 0.7511 0.9689 -0.0726 0.040 Uiso 1 1 calc R U
C5 C -0.13699(17) 0.58554(15) 0.24586(13) 0.0286(3) Uani 1 1 d . .
C6 C -0.19123(19) 0.41715(15) 0.32969(14) 0.0302(3) Uani 1 1 d . .
H6A H -0.0788 0.4456 0.3813 0.036 Uiso 1 1 calc R U
H6B H -0.2182 0.3477 0.2638 0.036 Uiso 1 1 calc R U
C9 C -0.1777(2) 0.23590(17) 0.48106(14) 0.0379(4) Uani 1 1 d . .
H9 H -0.0845 0.3141 0.5253 0.046 Uiso 1 1 calc R U
C2 C 0.01855(17) 0.70877(15) 0.13764(13) 0.0291(3) Uani 1 1 d . .
H2 H 0.0737 0.7495 0.1005 0.035 Uiso 1 1 calc R U
C3 C -0.09141(18) 0.74886(16) 0.16092(14) 0.0324(3) Uani 1 1 d . .
H3 H -0.1102 0.8174 0.1397 0.039 Uiso 1 1 calc R U
C12 C -0.45706(19) 0.00268(16) 0.35419(13) 0.0337(4) Uani 1 1 d . .
H12 H -0.5522 -0.0748 0.3127 0.040 Uiso 1 1 calc R U
C10 C -0.1811(2) 0.11839(17) 0.49567(15) 0.0408(4) Uani 1 1 d . .
H10 H -0.0901 0.1176 0.5484 0.049 Uiso 1 1 calc R U
C15 C 1.40574(19) 1.33735(16) 0.56842(14) 0.0355(4) Uani 1 1 d . .
H15A H 1.5007 1.4219 0.6062 0.043 Uiso 1 1 calc R U
H15B H 1.3250 1.3436 0.5932 0.043 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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
C26 O1 C25 116.30(10) .
C11 O2 C14 118.38(12) 2_666
C18 O3 C17 117.33(11) .
C5 O4 C6 118.30(11) .
C26 N2 C30 117.79(12) .
C5 N1 C1 116.87(12) .
C22 C21 C20 116.97(14) .
C22 C21 C24 123.42(12) .
C20 C21 C24 119.58(14) .
C8 C7 C6 111.91(12) .
O3 C18 C19 116.57(13) .
O3 C18 C23 124.17(14) .
C19 C18 C23 119.25(14) .
C3 C4 C5 117.54(13) .
O3 C17 C16 107.80(12) .
C20 C19 C18 120.29(14) .
C23 C22 C21 122.13(13) .
C13 C8 C9 117.42(14) .
C13 C8 C7 121.48(14) .
C9 C8 C7 121.10(15) .
N2 C26 O1 118.74(12) .
N2 C26 C27 124.35(13) .
O1 C26 C27 116.90(12) .
C27 C28 C29 119.90(13) .
C17 C16 C15 113.51(12) .
N1 C1 C2 122.73(12) .
N1 C1 C30 116.58(12) .
C2 C1 C30 120.69(13) .
C21 C24 C25 115.28(13) .
O2 C11 C12 125.05(14) 2_666
O2 C11 C10 114.97(14) 2_666
C12 C11 C10 119.97(15) .
C22 C23 C18 119.54(15) .
O1 C25 C24 106.98(11) .
C8 C13 C12 122.42(14) .
C28 C27 C26 117.12(12) .
N2 C30 C29 122.65(12) .
N2 C30 C1 115.29(12) .
C29 C30 C1 122.06(13) .
C30 C29 C28 118.17(13) .
O2 C14 C15 107.34(12) .
C19 C20 C21 121.81(15) .
N1 C5 O4 118.72(13) .
N1 C5 C4 125.05(13) .
O4 C5 C4 116.23(12) .
O4 C6 C7 105.33(11) .
C10 C9 C8 121.40(15) .
C1 C2 C3 118.43(13) .
C4 C3 C2 119.39(13) .
C11 C12 C13 118.88(15) .
C9 C10 C11 119.85(15) .
C14 C15 C16 115.03(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C26 1.3566(16) .
O1 C25 1.4456(16) .
O2 C11 1.3689(18) 2_666
O2 C14 1.4331(18) .
O3 C18 1.3696(18) .
O3 C17 1.424(2) .
O4 C5 1.3649(17) .
O4 C6 1.4382(17) .
N2 C26 1.3162(17) .
N2 C30 1.3508(17) .
N1 C5 1.3197(18) .
N1 C1 1.3535(18) .
C21 C22 1.389(2) .
C21 C20 1.399(2) .
C21 C24 1.510(2) .
C7 C8 1.512(2) .
C7 C6 1.519(2) .
C18 C19 1.387(2) .
C18 C23 1.393(2) .
C4 C3 1.373(2) .
C4 C5 1.389(2) .
C17 C16 1.506(2) .
C19 C20 1.374(2) .
C22 C23 1.385(2) .
C8 C13 1.384(2) .
C8 C9 1.394(2) .
C26 C27 1.4034(19) .
C28 C27 1.3731(19) .
C28 C29 1.4000(19) .
C16 C15 1.529(2) .
C1 C2 1.3874(19) .
C1 C30 1.4843(19) .
C24 C25 1.5161(18) .
C11 O2 1.3689(18) 2_666
C11 C12 1.384(2) .
C11 C10 1.393(2) .
C13 C12 1.387(2) .
C30 C29 1.3841(19) .
C14 C15 1.504(2) .
C9 C10 1.378(2) .
C2 C3 1.3952(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139047953
