#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/74/1517415.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_1517415
loop_
_publ_author_name
'Gregoliński, Janusz'
'Slepokura, Katarzyna'
'Paćkowski, Tomasz'
'Lisowski, Jerzy'
_publ_section_title
;
 Expansion of a 2 + 2 Macrocycle into a 6 + 6 Macrocycle: Template Effect
 of Cadmium(II).
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4372
_journal_paper_doi               10.1021/ol501602f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C24 H26 N6'
_chemical_formula_sum            'C24 H26 N6'
_chemical_formula_weight         398.51
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                94.02(4)
_cell_angle_beta                 100.02(4)
_cell_angle_gamma                104.01(4)
_cell_formula_units_Z            1
_cell_length_a                   7.468(4)
_cell_length_b                   7.906(3)
_cell_length_c                   8.990(4)
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      3.31
_cell_volume                     503.6(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type
;
Kuma KM4-CCD kappa-geometry diffractometer with a Sapphire2 
CCD camera 
;
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5146
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0414
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1648
_reflns_number_total             2442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol501602f_si_002.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 1517415--1517418.cif.'
_cod_database_code               1517415
#BEGIN Tags that were not found in dictionaries:
_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   0.989
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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
N1 N 0.28740(14) 0.42494(14) 0.56635(12) 0.0160(3) Uani 1 1 d . .
N2 N 0.53087(15) 0.17714(14) 0.79116(12) 0.0169(3) Uani 1 1 d . .
N3 N 0.80435(15) 0.19139(15) 0.57436(12) 0.0174(3) Uani 1 1 d . .
C1 C 0.23327(17) 0.57496(17) 0.57541(15) 0.0161(3) Uani 1 1 d . .
C2 C 0.21173(18) 0.65682(18) 0.71163(15) 0.0180(3) Uani 1 1 d . .
H2 H 0.1722 0.7623 0.7134 0.022 Uiso 1 1 calc R U
C3 C 0.24922(19) 0.58103(18) 0.84405(15) 0.0198(3) Uani 1 1 d . .
H3 H 0.2314 0.6314 0.9377 0.024 Uiso 1 1 calc R U
C4 C 0.31297(18) 0.43096(17) 0.83770(15) 0.0181(3) Uani 1 1 d . .
H4 H 0.3432 0.3783 0.9273 0.022 Uiso 1 1 calc R U
C5 C 0.33217(18) 0.35816(17) 0.69701(14) 0.0162(3) Uani 1 1 d . .
C6 C 0.41409(18) 0.20762(17) 0.68226(15) 0.0168(3) Uani 1 1 d . .
H6 H 0.3789 0.1317 0.5894 0.020 Uiso 1 1 calc R U
C7 C 0.62443(18) 0.04190(17) 0.75715(14) 0.0163(3) Uani 1 1 d . .
H7 H 0.5464 -0.0420 0.6678 0.020 Uiso 1 1 calc R U
C8 C 0.67704(19) -0.05772(18) 0.88931(15) 0.0192(3) Uani 1 1 d . .
H8A H 0.5659 -0.1461 0.9065 0.023 Uiso 1 1 calc R U
H8B H 0.7339 0.0231 0.9840 0.023 Uiso 1 1 calc R U
C9 C 0.8210(2) -0.14597(19) 0.83625(16) 0.0218(3) Uani 1 1 d . .
H9A H 0.7567 -0.2605 0.7751 0.026 Uiso 1 1 calc R U
H9B H 0.9105 -0.1651 0.9245 0.026 Uiso 1 1 calc R U
C10 C 0.92493(19) -0.01629(18) 0.73834(15) 0.0196(3) Uani 1 1 d . .
H10A H 1.0583 0.0336 0.7887 0.023 Uiso 1 1 calc R U
H10B H 0.9205 -0.0766 0.6369 0.023 Uiso 1 1 calc R U
C11 C 0.82062(18) 0.12872(17) 0.72341(14) 0.0165(3) Uani 1 1 d . .
H11 H 0.8866 0.2296 0.8032 0.020 Uiso 1 1 calc R U
C12 C 0.79878(17) 0.35020(18) 0.56972(15) 0.0173(3) Uani 1 1 d . .
H12 H 0.8157 0.4230 0.6624 0.021 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'
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
C5 N1 C1 117.36(12) . .
C6 N2 C7 116.68(11) . .
C12 N3 C11 116.80(12) . .
N1 C1 C2 123.07(13) . .
N1 C1 C12 114.92(12) . 2_666
C2 C1 C12 122.01(12) . 2_666
C3 C2 C1 118.68(13) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C4 C3 C2 118.93(13) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 118.76(13) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
N1 C5 C4 123.05(13) . .
N1 C5 C6 114.73(12) . .
C4 C5 C6 122.14(12) . .
N2 C6 C5 121.34(12) . .
N2 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
N2 C7 C8 115.11(11) . .
N2 C7 C11 109.48(11) . .
C8 C7 C11 101.44(11) . .
N2 C7 H7 110.2 . .
C8 C7 H7 110.2 . .
C11 C7 H7 110.2 . .
C7 C8 C9 102.84(11) . .
C7 C8 H8A 111.2 . .
C9 C8 H8A 111.2 . .
C7 C8 H8B 111.2 . .
C9 C8 H8B 111.2 . .
H8A C8 H8B 109.1 . .
C8 C9 C10 105.15(11) . .
C8 C9 H9A 110.7 . .
C10 C9 H9A 110.7 . .
C8 C9 H9B 110.7 . .
C10 C9 H9B 110.7 . .
H9A C9 H9B 108.8 . .
C11 C10 C9 105.74(11) . .
C11 C10 H10A 110.6 . .
C9 C10 H10A 110.6 . .
C11 C10 H10B 110.6 . .
C9 C10 H10B 110.6 . .
H10A C10 H10B 108.7 . .
N3 C11 C10 113.67(11) . .
N3 C11 C7 111.37(11) . .
C10 C11 C7 103.77(11) . .
N3 C11 H11 109.3 . .
C10 C11 H11 109.3 . .
C7 C11 H11 109.3 . .
N3 C12 C1 121.94(13) . 2_666
N3 C12 H12 119.0 . .
C1 C12 H12 119.0 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.3439(17) .
N1 C1 1.3442(17) .
N2 C6 1.2708(17) .
N2 C7 1.4543(17) .
N3 C12 1.2696(17) .
N3 C11 1.4565(17) .
C1 C2 1.3972(19) .
C1 C12 1.4757(19) 2_666
C2 C3 1.3856(19) .
C2 H2 0.9500 .
C3 C4 1.3824(19) .
C3 H3 0.9500 .
C4 C5 1.3974(19) .
C4 H4 0.9500 .
C5 C6 1.4720(19) .
C6 H6 0.9500 .
C7 C8 1.5181(19) .
C7 C11 1.551(2) .
C7 H7 1.0000 .
C8 C9 1.538(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.552(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.5352(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11 1.0000 .
C12 C1 1.4757(19) 2_666
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
C5 N1 C1 C2 -3.78(18) . .
C5 N1 C1 C12 175.12(11) . 2_666
N1 C1 C2 C3 0.53(19) . .
C12 C1 C2 C3 -178.29(12) 2_666 .
C1 C2 C3 C4 2.30(19) . .
C2 C3 C4 C5 -1.82(19) . .
C1 N1 C5 C4 4.31(18) . .
C1 N1 C5 C6 -172.24(11) . .
C3 C4 C5 N1 -1.57(19) . .
C3 C4 C5 C6 174.72(12) . .
C7 N2 C6 C5 -170.94(12) . .
N1 C5 C6 N2 150.16(12) . .
C4 C5 C6 N2 -26.42(19) . .
C6 N2 C7 C8 -149.44(12) . .
C6 N2 C7 C11 97.09(14) . .
N2 C7 C8 C9 -163.46(11) . .
C11 C7 C8 C9 -45.38(13) . .
C7 C8 C9 C10 32.54(14) . .
C8 C9 C10 C11 -6.72(14) . .
C12 N3 C11 C10 -150.12(12) . .
C12 N3 C11 C7 93.10(14) . .
C9 C10 C11 N3 -142.16(11) . .
C9 C10 C11 C7 -21.03(13) . .
N2 C7 C11 N3 -74.05(14) . .
C8 C7 C11 N3 163.88(10) . .
N2 C7 C11 C10 163.28(10) . .
C8 C7 C11 C10 41.22(13) . .
C11 N3 C12 C1 -174.85(11) . 2_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102333680
