#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056451.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_7056451
loop_
_publ_author_name
'Madhu, Suresh'
'Rashmi, E.'
'Gonnade, Rajesh G.'
'Sanjayan, G. J.'
_publ_section_title
;
 Exploring Gem-Dimethyl Effect in the Formation of Imine-Based Macrocycles
 and Cages
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              8721
_journal_page_last               8724
_journal_paper_doi               10.1039/C7NJ02069D
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C40 H44 N4'
_chemical_formula_sum            'C40 H44 N4'
_chemical_formula_weight         580.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-26 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8258(2)
_cell_length_b                   6.0141(2)
_cell_length_c                   30.3167(8)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.32
_cell_volume                     1599.20(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            26842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.692
_diffrn_reflns_theta_min         1.352
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker. 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0505
_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)+(0.0496P)²+0.8375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3732
_reflns_number_total             4114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02069d2.cif
_cod_data_source_block           3
_cod_database_code               7056451
#BEGIN Tags that were not found in dictionaries:
_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   0.978
_shelx_estimated_absorpt_t_max   0.987
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 1.07555(11) 0.60708(18) 0.11698(3) 0.0173(2) Uani 1 1 d . .
N2 N 0.65709(11) 1.07180(18) 0.08872(3) 0.0169(2) Uani 1 1 d . .
C1 C 1.13629(14) 0.7605(2) 0.02821(4) 0.0182(3) Uani 1 1 d . .
H1 H 1.0826 0.8658 0.0439 0.022 Uiso 1 1 calc R U
C2 C 1.16129(14) 0.5452(2) 0.04511(4) 0.0169(2) Uani 1 1 d . .
C3 C 1.23607(16) 0.3923(2) 0.02090(4) 0.0232(3) Uani 1 1 d . .
H3 H 1.2512 0.2449 0.0318 0.028 Uiso 1 1 calc R U
C4 C 1.11587(14) 0.4734(2) 0.08821(4) 0.0182(2) Uani 1 1 d . .
H4 H 1.1169 0.3189 0.0947 0.022 Uiso 1 1 calc R U
C5 C 1.04730(14) 0.5214(2) 0.16107(4) 0.0166(2) Uani 1 1 d . .
C6 C 1.18079(14) 0.6104(2) 0.19329(4) 0.0218(3) Uani 1 1 d . .
H6B H 1.2766 0.5462 0.1857 0.033 Uiso 1 1 calc R U
H6C H 1.1655 0.5690 0.2237 0.033 Uiso 1 1 calc R U
H6A H 1.1852 0.7727 0.1909 0.033 Uiso 1 1 calc R U
C7 C 1.03939(16) 0.2669(2) 0.16448(4) 0.0223(3) Uani 1 1 d . .
H7A H 0.9597 0.2104 0.1422 0.033 Uiso 1 1 calc R U
H7B H 1.0156 0.2251 0.1942 0.033 Uiso 1 1 calc R U
H7C H 1.1379 0.2028 0.1592 0.033 Uiso 1 1 calc R U
C8 C 0.89849(13) 0.6229(2) 0.17386(4) 0.0162(2) Uani 1 1 d . .
C9 C 0.85102(15) 0.5705(2) 0.21506(4) 0.0207(3) Uani 1 1 d . .
H9 H 0.9112 0.4747 0.2348 0.025 Uiso 1 1 calc R U
C10 C 0.71642(15) 0.6578(2) 0.22722(4) 0.0229(3) Uani 1 1 d . .
H10 H 0.6842 0.6195 0.2551 0.027 Uiso 1 1 calc R U
C11 C 0.62843(15) 0.8005(2) 0.19908(4) 0.0212(3) Uani 1 1 d . .
H11 H 0.5359 0.8581 0.2077 0.025 Uiso 1 1 calc R U
C12 C 0.67472(13) 0.8602(2) 0.15814(4) 0.0163(2) Uani 1 1 d . .
C13 C 0.80938(13) 0.7674(2) 0.14589(4) 0.0157(2) Uani 1 1 d . .
H13 H 0.8408 0.8038 0.1178 0.019 Uiso 1 1 calc R U
C14 C 0.57524(13) 1.0178(2) 0.12737(4) 0.0168(2) Uani 1 1 d . .
C15 C 0.43217(15) 0.8906(3) 0.10792(5) 0.0260(3) Uani 1 1 d . .
H15C H 0.3669 0.9893 0.0884 0.039 Uiso 1 1 calc R U
H15B H 0.3761 0.8388 0.1321 0.039 Uiso 1 1 calc R U
H15A H 0.4623 0.7626 0.0909 0.039 Uiso 1 1 calc R U
C16 C 0.52786(17) 1.2216(2) 0.15310(5) 0.0264(3) Uani 1 1 d . .
H16A H 0.6188 1.3064 0.1644 0.040 Uiso 1 1 calc R U
H16C H 0.4745 1.1725 0.1781 0.040 Uiso 1 1 calc R U
H16B H 0.4600 1.3159 0.1333 0.040 Uiso 1 1 calc R U
C17 C 0.66334(14) 1.2711(2) 0.07552(4) 0.0188(3) Uani 1 1 d . .
H17 H 0.6227 1.3852 0.0924 0.023 Uiso 1 1 calc R U
C18 C 0.81040(14) 1.1801(2) 0.01131(4) 0.0185(3) Uani 1 1 d . .
H18 H 0.8277 1.0338 0.0226 0.022 Uiso 1 1 calc R U
C19 C 0.73132(14) 1.3327(2) 0.03490(4) 0.0175(2) Uani 1 1 d . .
C20 C 0.71078(16) 1.5488(2) 0.01894(4) 0.0237(3) Uani 1 1 d . .
H20 H 0.6606 1.6557 0.0352 0.028 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
C4 N1 C5 119.33(11) . .
C17 N2 C14 120.01(10) . .
C18 C1 C2 120.06(11) 3_775 .
C18 C1 H1 120.0 3_775 .
C2 C1 H1 120.0 . .
C3 C2 C1 118.92(11) . .
C3 C2 C4 117.84(11) . .
C1 C2 C4 123.22(11) . .
C2 C3 C20 121.13(12) . 3_775
C2 C3 H3 119.4 . .
C20 C3 H3 119.4 3_775 .
N1 C4 C2 123.37(12) . .
N1 C4 H4 118.3 . .
C2 C4 H4 118.3 . .
N1 C5 C7 114.93(10) . .
N1 C5 C8 108.92(10) . .
C7 C5 C8 109.42(10) . .
N1 C5 C6 104.94(10) . .
C7 C5 C6 109.93(11) . .
C8 C5 C6 108.46(10) . .
C5 C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C6 H6A 109.5 . .
H6B C6 H6A 109.5 . .
H6C C6 H6A 109.5 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 118.65(11) . .
C13 C8 C5 122.29(10) . .
C9 C8 C5 119.06(11) . .
C10 C9 C8 120.25(12) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 120.61(11) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C10 C11 C12 120.47(12) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C11 C12 C13 118.32(11) . .
C11 C12 C14 119.66(11) . .
C13 C12 C14 121.99(10) . .
C8 C13 C12 121.67(11) . .
C8 C13 H13 119.2 . .
C12 C13 H13 119.2 . .
N2 C14 C12 108.67(9) . .
N2 C14 C16 114.32(10) . .
C12 C14 C16 110.71(10) . .
N2 C14 C15 104.96(10) . .
C12 C14 C15 108.40(10) . .
C16 C14 C15 109.49(11) . .
C14 C15 H15C 109.5 . .
C14 C15 H15B 109.5 . .
H15C C15 H15B 109.5 . .
C14 C15 H15A 109.5 . .
H15C C15 H15A 109.5 . .
H15B C15 H15A 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
H16C C16 H16B 109.5 . .
N2 C17 C19 122.48(11) . .
N2 C17 H17 118.8 . .
C19 C17 H17 118.8 . .
C1 C18 C19 120.78(12) 3_775 .
C1 C18 H18 119.6 3_775 .
C19 C18 H18 119.6 . .
C20 C19 C18 119.26(11) . .
C20 C19 C17 118.37(11) . .
C18 C19 C17 122.33(12) . .
C3 C20 C19 119.78(12) 3_775 .
C3 C20 H20 120.1 3_775 .
C19 C20 H20 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.2658(16) .
N1 C5 1.4794(15) .
N2 C17 1.2665(17) .
N2 C14 1.4794(15) .
C1 C18 1.3820(17) 3_775
C1 C2 1.4011(18) .
C1 H1 0.9500 .
C2 C3 1.3885(17) .
C2 C4 1.4734(16) .
C3 C20 1.3895(17) 3_775
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 C7 1.5361(18) .
C5 C8 1.5368(16) .
C5 C6 1.5404(17) .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C6 H6A 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C13 1.3943(17) .
C8 C9 1.3967(16) .
C9 C10 1.3857(18) .
C9 H9 0.9500 .
C10 C11 1.3855(19) .
C10 H10 0.9500 .
C11 C12 1.3961(16) .
C11 H11 0.9500 .
C12 C13 1.4000(16) .
C12 C14 1.5355(17) .
C13 H13 0.9500 .
C14 C16 1.5357(18) .
C14 C15 1.5368(18) .
C15 H15C 0.9800 .
C15 H15B 0.9800 .
C15 H15A 0.9800 .
C16 H16A 0.9800 .
C16 H16C 0.9800 .
C16 H16B 0.9800 .
C17 C19 1.4760(16) .
C17 H17 0.9500 .
C18 C1 1.3819(17) 3_775
C18 C19 1.3969(17) .
C18 H18 0.9500 .
C19 C20 1.3917(18) .
C20 C3 1.3894(17) 3_775
C20 H20 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
C18 C1 C2 C3 -1.87(18) 3_775 .
C18 C1 C2 C4 176.35(11) 3_775 .
C1 C2 C3 C20 1.6(2) . 3_775
C4 C2 C3 C20 -176.71(12) . 3_775
C5 N1 C4 C2 -173.73(11) . .
C3 C2 C4 N1 165.36(12) . .
C1 C2 C4 N1 -12.88(19) . .
C4 N1 C5 C7 -11.64(16) . .
C4 N1 C5 C8 -134.80(12) . .
C4 N1 C5 C6 109.24(13) . .
N1 C5 C8 C13 1.39(16) . .
C7 C5 C8 C13 -125.00(13) . .
C6 C5 C8 C13 115.08(13) . .
N1 C5 C8 C9 -178.11(11) . .
C7 C5 C8 C9 55.49(15) . .
C6 C5 C8 C9 -64.42(15) . .
C13 C8 C9 C10 1.22(19) . .
C5 C8 C9 C10 -179.26(12) . .
C8 C9 C10 C11 -1.0(2) . .
C9 C10 C11 C12 -0.5(2) . .
C10 C11 C12 C13 1.77(19) . .
C10 C11 C12 C14 179.76(12) . .
C9 C8 C13 C12 0.05(18) . .
C5 C8 C13 C12 -179.45(11) . .
C11 C12 C13 C8 -1.53(18) . .
C14 C12 C13 C8 -179.47(11) . .
C17 N2 C14 C12 -134.39(12) . .
C17 N2 C14 C16 -10.17(17) . .
C17 N2 C14 C15 109.81(13) . .
C11 C12 C14 N2 174.26(11) . .
C13 C12 C14 N2 -7.84(16) . .
C11 C12 C14 C16 47.93(15) . .
C13 C12 C14 C16 -134.17(12) . .
C11 C12 C14 C15 -72.19(14) . .
C13 C12 C14 C15 105.72(13) . .
C14 N2 C17 C19 -174.45(11) . .
C1 C18 C19 C20 -2.11(19) 3_775 .
C1 C18 C19 C17 175.61(11) 3_775 .
N2 C17 C19 C20 169.47(13) . .
N2 C17 C19 C18 -8.3(2) . .
C18 C19 C20 C3 2.4(2) . 3_775
C17 C19 C20 C3 -175.44(12) . 3_775
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139178007
