#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/44/7014490.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_7014490
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         'C18 H14 N4'
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 108.777(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8270(6)
_cell_length_b                   12.5383(5)
_cell_length_c                   18.6260(8)
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.35
_cell_volume                     2836.2(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8513
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+1.9629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                2643
_reflns_number_total             3261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT00907E.TXT
_cod_data_source_block           3
_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      'C2/c '
_cod_database_code               7014490
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 1.07129(13) 1.33308(12) 0.35813(9) 0.0371(4) Uani 1 1 d . . .
H1 H 1.0737 1.4057 0.3485 0.044 Uiso 1 1 calc R . .
C2 C 1.15938(13) 1.27314(12) 0.40362(9) 0.0359(3) Uani 1 1 d . . .
H2 H 1.2297 1.2981 0.4296 0.043 Uiso 1 1 calc R . .
C3 C 1.12220(12) 1.16961(11) 0.40280(8) 0.0311(3) Uani 1 1 d . . .
H3 H 1.1631 1.1118 0.4282 0.037 Uiso 1 1 calc R . .
C4 C 1.01107(11) 1.16767(11) 0.35647(7) 0.0270(3) Uani 1 1 d . . .
C5 C 0.93571(11) 1.08170(11) 0.33839(7) 0.0269(3) Uani 1 1 d . . .
C6 C 0.82478(12) 1.09209(11) 0.29546(8) 0.0294(3) Uani 1 1 d . . .
C7 C 0.74389(13) 1.01118(13) 0.26715(9) 0.0377(4) Uani 1 1 d . . .
H7 H 0.7535 0.9382 0.2756 0.045 Uiso 1 1 calc R . .
C8 C 0.64952(14) 1.06143(15) 0.22521(10) 0.0468(4) Uani 1 1 d . . .
H8 H 0.5826 1.0293 0.1993 0.056 Uiso 1 1 calc R . .
C9 C 0.67331(13) 1.17181(15) 0.22885(9) 0.0436(4) Uani 1 1 d . . .
H9 H 0.6226 1.2242 0.2052 0.052 Uiso 1 1 calc R . .
C10 C 0.98007(11) 0.97474(11) 0.36725(8) 0.0267(3) Uani 1 1 d . . .
C11 C 0.93786(12) 0.91719(11) 0.41569(8) 0.0302(3) Uani 1 1 d . . .
H11 H 0.8790 0.9446 0.4288 0.036 Uiso 1 1 calc R . .
C12 C 0.98259(12) 0.81978(11) 0.44451(8) 0.0297(3) Uani 1 1 d . . .
H12 H 0.9538 0.7822 0.4769 0.036 Uiso 1 1 calc R . .
C13 C 1.07036(11) 0.77767(10) 0.42530(7) 0.0257(3) Uani 1 1 d . . .
C14 C 1.11267(12) 0.83375(11) 0.37667(8) 0.0305(3) Uani 1 1 d . . .
H14 H 1.1709 0.8057 0.3633 0.037 Uiso 1 1 calc R . .
C15 C 1.06813(12) 0.93113(11) 0.34827(8) 0.0301(3) Uani 1 1 d . . .
H15 H 1.0972 0.9685 0.3159 0.036 Uiso 1 1 calc R . .
C16 C 1.18955(13) 0.61708(12) 0.43400(9) 0.0363(3) Uani 1 1 d . . .
H16 H 1.2182 0.6371 0.3961 0.044 Uiso 1 1 calc R . .
C17 C 1.09603(15) 0.62073(14) 0.51274(11) 0.0499(5) Uani 1 1 d . . .
H17 H 1.0498 0.6405 0.5400 0.060 Uiso 1 1 calc R . .
C18 C 1.15588(14) 0.53062(14) 0.52116(11) 0.0481(4) Uani 1 1 d . . .
H18 H 1.1569 0.4772 0.5560 0.058 Uiso 1 1 calc R . .
N1 N 0.98314(10) 1.27090(9) 0.33047(7) 0.0327(3) Uani 1 1 d . . .
H1A H 0.9196 1.2913 0.3014 0.039 Uiso 1 1 calc R . .
N2 N 0.77693(10) 1.19135(10) 0.27024(7) 0.0356(3) Uani 1 1 d . . .
N3 N 1.11678(10) 0.67765(9) 0.45583(7) 0.0288(3) Uani 1 1 d . . .
N4 N 1.21482(11) 0.52794(10) 0.47198(8) 0.0388(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 109.90(13) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C3 C2 C1 106.89(14) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.49(13) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.11(12) . . ?
N1 C4 C5 123.22(13) . . ?
C3 C4 C5 129.65(13) . . ?
C6 C5 C4 123.90(13) . . ?
C6 C5 C10 119.46(12) . . ?
C4 C5 C10 116.64(12) . . ?
C5 C6 N2 122.07(13) . . ?
C5 C6 C7 129.19(14) . . ?
N2 C6 C7 108.68(13) . . ?
C8 C7 C6 106.80(15) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 C9 106.64(15) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 111.65(15) . . ?
N2 C9 H9 124.2 . . ?
C8 C9 H9 124.2 . . ?
C11 C10 C15 118.35(13) . . ?
C11 C10 C5 121.15(12) . . ?
C15 C10 C5 120.46(12) . . ?
C12 C11 C10 120.65(12) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.31(12) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.64(13) . . ?
C14 C13 N3 120.34(12) . . ?
C12 C13 N3 120.01(12) . . ?
C15 C14 C13 119.88(12) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.17(12) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
N4 C16 N3 112.92(13) . . ?
N4 C16 H16 123.5 . . ?
N3 C16 H16 123.5 . . ?
C18 C17 N3 106.33(14) . . ?
C18 C17 H17 126.8 . . ?
N3 C17 H17 126.8 . . ?
C17 C18 N4 111.18(14) . . ?
C17 C18 H18 124.4 . . ?
N4 C18 H18 124.4 . . ?
C1 N1 C4 108.60(12) . . ?
C1 N1 H1A 125.7 . . ?
C4 N1 H1A 125.7 . . ?
C9 N2 C6 106.24(13) . . ?
C16 N3 C17 105.20(12) . . ?
C16 N3 C13 127.54(12) . . ?
C17 N3 C13 127.25(12) . . ?
C16 N4 C18 104.37(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 1.333(2) . ?
C1 C2 1.394(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.3879(17) . ?
C4 C5 1.4143(19) . ?
C5 C6 1.396(2) . ?
C5 C10 1.4881(19) . ?
C6 N2 1.4003(19) . ?
C6 C7 1.425(2) . ?
C7 C8 1.365(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.327(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3937(19) . ?
C10 C15 1.3988(18) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3906(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.3878(19) . ?
C13 N3 1.4257(17) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N4 1.307(2) . ?
C16 N3 1.3630(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.346(2) . ?
C17 N3 1.3730(19) . ?
C17 H17 0.9300 . ?
C18 N4 1.363(2) . ?
C18 H18 0.9300 . ?
N1 H1A 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652773
2 PubChem 102168041
