#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/44/7014489.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_7014489
loop_
_publ_author_name
'Pogozhev, Dmitry'
'Baudron, Stéphane A'
'Hosseini, Mir Wais'
_publ_section_title
;
 Dipyrrin based silver [2 + 2] metallamacrocycles.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              437
_journal_page_last               445
_journal_paper_doi               10.1039/c0dt00907e
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C20 H15 N3'
_chemical_formula_sum            'C20 H15 N3'
_chemical_formula_weight         297.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.5270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1131(3)
_cell_length_b                   7.2051(2)
_cell_length_c                   19.4251(5)
_cell_measurement_reflns_used    5119
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.43
_cell_volume                     1498.62(7)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11268
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.6794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                2959
_reflns_number_total             3465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT00907E.TXT
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n '
_cod_database_code               7014489
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41234(14) 0.6284(2) 0.41432(8) 0.0350(3) Uani 1 1 d . . .
H1 H 0.4733 0.5390 0.4159 0.042 Uiso 1 1 calc R . .
C2 C 0.41521(14) 0.7597(2) 0.46793(8) 0.0346(3) Uani 1 1 d . . .
H2 H 0.4770 0.7724 0.5107 0.041 Uiso 1 1 calc R . .
C3 C 0.30897(13) 0.8668(2) 0.44527(7) 0.0298(3) Uani 1 1 d . . .
H3 H 0.2855 0.9650 0.4699 0.036 Uiso 1 1 calc R . .
C4 C 0.24245(12) 0.79888(19) 0.37743(7) 0.0261(3) Uani 1 1 d . . .
C5 C 0.13287(12) 0.86598(18) 0.32946(7) 0.0251(3) Uani 1 1 d . . .
C6 C 0.07811(12) 0.78844(19) 0.26235(7) 0.0250(3) Uani 1 1 d . . .
C7 C -0.03965(13) 0.8320(2) 0.21467(8) 0.0311(3) Uani 1 1 d . . .
H7 H -0.0928 0.9277 0.2198 0.037 Uiso 1 1 calc R . .
C8 C -0.06004(14) 0.7064(2) 0.15978(8) 0.0349(3) Uani 1 1 d . . .
H8 H -0.1299 0.6995 0.1207 0.042 Uiso 1 1 calc R . .
C9 C 0.04567(14) 0.5896(2) 0.17412(8) 0.0337(3) Uani 1 1 d . . .
H9 H 0.0560 0.4920 0.1449 0.040 Uiso 1 1 calc R . .
C10 C 0.06733(12) 1.02866(19) 0.35069(7) 0.0252(3) Uani 1 1 d . . .
C11 C 0.06729(16) 1.1999(2) 0.31770(9) 0.0374(4) Uani 1 1 d . . .
H11 H 0.1135 1.2158 0.2847 0.045 Uiso 1 1 calc R . .
C12 C -0.00090(15) 1.3471(2) 0.33351(9) 0.0354(4) Uani 1 1 d . . .
H12 H 0.0005 1.4609 0.3111 0.043 Uiso 1 1 calc R . .
C13 C -0.07161(12) 1.32731(19) 0.38249(7) 0.0251(3) Uani 1 1 d . . .
C14 C -0.07078(12) 1.15602(19) 0.41569(7) 0.0258(3) Uani 1 1 d . . .
H14 H -0.1173 1.1399 0.4485 0.031 Uiso 1 1 calc R . .
C15 C -0.00152(12) 1.00914(19) 0.40051(7) 0.0257(3) Uani 1 1 d . . .
H15 H -0.0010 0.8963 0.4239 0.031 Uiso 1 1 calc R . .
C16 C -0.14576(12) 1.48515(19) 0.39837(7) 0.0258(3) Uani 1 1 d . . .
C17 C -0.19786(13) 1.6187(2) 0.34703(8) 0.0317(3) Uani 1 1 d . . .
H17 H -0.1873 1.6103 0.3012 0.038 Uiso 1 1 calc R . .
C18 C -0.26554(14) 1.7642(2) 0.36481(9) 0.0369(4) Uani 1 1 d . . .
H18 H -0.3003 1.8505 0.3295 0.044 Uiso 1 1 calc R . .
C19 C -0.23401(15) 1.6601(2) 0.47814(9) 0.0384(4) Uani 1 1 d . . .
H19 H -0.2455 1.6734 0.5236 0.046 Uiso 1 1 calc R . .
C20 C -0.16609(13) 1.5084(2) 0.46564(8) 0.0318(3) Uani 1 1 d . . .
H20 H -0.1344 1.4228 0.5018 0.038 Uiso 1 1 calc R . .
N1 N 0.30956(11) 0.65032(17) 0.36084(7) 0.0307(3) Uani 1 1 d . . .
H1A H 0.2884 0.5841 0.3227 0.037 Uiso 1 1 calc R . .
N2 N 0.12871(11) 0.63671(17) 0.23472(6) 0.0289(3) Uani 1 1 d . . .
N3 N -0.28402(12) 1.78851(19) 0.42925(8) 0.0395(3) Uani 1 1 d . . .
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
_geom_angle_publ_flag
N1 C1 C2 110.12(13) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C3 C2 C1 107.03(13) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.05(13) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
N1 C4 C5 122.27(12) . . ?
N1 C4 C3 107.64(12) . . ?
C5 C4 C3 129.97(13) . . ?
C6 C5 C4 124.32(12) . . ?
C6 C5 C10 116.59(12) . . ?
C4 C5 C10 119.09(12) . . ?
C5 C6 N2 123.35(12) . . ?
C5 C6 C7 127.88(13) . . ?
N2 C6 C7 108.48(12) . . ?
C8 C7 C6 107.01(13) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 106.56(13) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 111.46(13) . . ?
N2 C9 H9 124.3 . . ?
C8 C9 H9 124.3 . . ?
C11 C10 C15 118.53(12) . . ?
C11 C10 C5 120.59(12) . . ?
C15 C10 C5 120.76(12) . . ?
C12 C11 C10 120.68(13) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.99(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.18(12) . . ?
C14 C13 C16 121.22(12) . . ?
C12 C13 C16 120.61(13) . . ?
C15 C14 C13 120.92(12) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 120.70(13) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C20 C16 C17 116.53(13) . . ?
C20 C16 C13 121.66(13) . . ?
C17 C16 C13 121.81(12) . . ?
C18 C17 C16 119.49(14) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N3 C18 C17 124.29(15) . . ?
N3 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
N3 C19 C20 124.34(15) . . ?
N3 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
C19 C20 C16 119.41(14) . . ?
C19 C20 H20 120.3 . . ?
C16 C20 H20 120.3 . . ?
C1 N1 C4 108.15(12) . . ?
C1 N1 H1A 125.9 . . ?
C4 N1 H1A 125.9 . . ?
C9 N2 C6 106.49(12) . . ?
C18 N3 C19 115.93(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3316(19) . ?
C1 C2 1.401(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.414(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.3909(17) . ?
C4 C5 1.4062(19) . ?
C5 C6 1.3989(19) . ?
C5 C10 1.4951(18) . ?
C6 N2 1.4004(17) . ?
C6 C7 1.4214(19) . ?
C7 C8 1.371(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(2) . ?
C8 H8 0.9300 . ?
C9 N2 1.3309(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(2) . ?
C10 C15 1.3924(18) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3939(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.3914(19) . ?
C13 C16 1.4845(18) . ?
C14 C15 1.3859(18) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C20 1.3945(19) . ?
C16 C17 1.395(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9300 . ?
C18 N3 1.333(2) . ?
C18 H18 0.9300 . ?
C19 N3 1.336(2) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1A 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652772
2 PubChem 101432288
