#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/52/4505229.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_4505229
loop_
_publ_author_name
'Curtis, Sean M.'
'Le, Nam'
'Fowler, Frank W.'
'Lauher, Joseph W.'
_publ_section_title
;
 A Rational Approach to the Preparation
 ofPolydipyridyldiacetylenes:  An Exercise in Crystal Design
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2313
_journal_paper_doi               10.1021/cg050204x
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C26 H28 N4 O6'
_chemical_formula_weight         492.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.219(6)
_cell_angle_beta                 85.486(4)
_cell_angle_gamma                88.992(5)
_cell_formula_units_Z            1
_cell_length_a                   5.1801(10)
_cell_length_b                   5.2099(10)
_cell_length_c                   23.409(5)
_cell_measurement_temperature    293(2)
_cell_volume                     629.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2897
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         0.87
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_crystal_size_max          .8
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.1564
_refine_ls_R_factor_gt           0.0654
_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)+(0.1425P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.2468
_reflns_number_gt                1225
_reflns_number_total             2275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050204xsi20050508_085012.cif
_cod_data_source_block           4-ox:4-pda
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4505229
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C13 C 0.3801(10) 1.0472(11) 0.7241(2) 0.0656(16) Uani 1 1 d .
N2 N 1.2661(7) 0.6536(7) 0.54699(15) 0.0579(12) Uani 1 1 d .
H2 H 1.3017 0.8074 0.5349 0.069 Uiso 1 1 calc R
C8 C 1.3960(8) 0.4621(10) 0.52345(19) 0.0511(13) Uani 1 1 d .
C9 C 1.0626(9) 0.6160(9) 0.5932(2) 0.0590(14) Uani 1 1 d .
H9A H 1.1402 0.5519 0.6273 0.071 Uiso 1 1 calc R
H9B H 0.9445 0.4870 0.5822 0.071 Uiso 1 1 calc R
C11 C 0.7216(9) 0.8262(9) 0.6590(2) 0.0599(14) Uani 1 1 d .
H11A H 0.6011 0.6923 0.6521 0.072 Uiso 1 1 calc R
H11B H 0.8151 0.7714 0.6916 0.072 Uiso 1 1 calc R
C10 C 0.9119(9) 0.8589(9) 0.6069(2) 0.0574(14) Uani 1 1 d .
H10A H 0.8183 0.9124 0.5742 0.069 Uiso 1 1 calc R
H10B H 1.0318 0.9936 0.6137 0.069 Uiso 1 1 calc R
O1 O 0.2119(7) 1.2381(8) 0.72634(16) 0.0968(15) Uani 1 1 d .
H1 H 0.1107 1.2189 0.7548 0.145 Uiso 1 1 calc R
C4 C 0.6442(11) 0.1355(13) 0.9109(2) 0.094(2) Uani 1 1 d .
H4 H 0.6285 0.0254 0.9430 0.112 Uiso 1 1 calc R
C12 C 0.5729(9) 1.0677(9) 0.6730(2) 0.0615(15) Uani 1 1 d .
H12A H 0.4820 1.1223 0.6399 0.074 Uiso 1 1 calc R
H12B H 0.6949 1.2007 0.6796 0.074 Uiso 1 1 calc R
O3 O 1.3594(6) 0.2330(6) 0.53615(14) 0.0685(11) Uani 1 1 d .
C1 C 0.2737(10) 0.4046(13) 0.9473(2) 0.087(2) Uani 1 1 d .
C5 C 0.4778(10) 0.3432(12) 0.9051(2) 0.0706(16) Uani 1 1 d .
O2 O 0.3744(9) 0.8829(10) 0.7599(2) 0.126(2) Uani 1 1 d .
C6 C 0.5070(12) 0.4901(13) 0.8564(3) 0.095(2) Uani 1 1 d .
H6 H 0.3927 0.6262 0.8506 0.114 Uiso 1 1 calc R
C2 C 0.0988(12) 0.4669(14) 0.9806(2) 0.092(2) Uani 1 1 d .
N1 N 0.8714(10) 0.2456(11) 0.8202(2) 0.0864(16) Uani 1 1 d .
C3 C 0.8380(11) 0.0973(13) 0.8663(3) 0.094(2) Uani 1 1 d .
H3 H 0.9500 -0.0427 0.8698 0.113 Uiso 1 1 calc R
C7 C 0.7061(13) 0.4387(14) 0.8154(3) 0.103(2) Uani 1 1 d .
H7 H 0.7244 0.5456 0.7828 0.124 Uiso 1 1 calc R
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_3
O2 C13 O1 121.3(5) .
O2 C13 C12 125.9(5) .
O1 C13 C12 112.8(5) .
C8 N2 C9 122.4(4) .
O3 C8 N2 124.9(4) .
O3 C8 C8 119.9(5) 2_866
N2 C8 C8 115.1(5) 2_866
N2 C9 C10 112.7(4) .
C12 C11 C10 112.7(4) .
C9 C10 C11 112.5(4) .
C5 C4 C3 117.3(6) .
C11 C12 C13 115.2(4) .
C2 C1 C5 176.3(8) .
C6 C5 C4 118.0(5) .
C6 C5 C1 119.0(6) .
C4 C5 C1 123.0(6) .
C5 C6 C7 120.3(6) .
C1 C2 C2 178.6(10) 2_567
C3 N1 C7 116.7(5) .
N1 C3 C4 124.4(6) .
N1 C7 C6 123.2(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C13 O2 1.179(6) .
C13 O1 1.310(5) .
C13 C12 1.499(7) .
N2 C8 1.305(5) .
N2 C9 1.461(5) .
C8 O3 1.236(5) .
C8 C8 1.524(9) 2_866
C9 C10 1.505(6) .
C11 C12 1.496(6) .
C11 C10 1.512(6) .
C4 C5 1.381(8) .
C4 C3 1.406(8) .
C1 C2 1.195(7) .
C1 C5 1.429(7) .
C5 C6 1.352(8) .
C6 C7 1.381(8) .
C2 C2 1.361(11) 2_567
N1 C3 1.310(7) .
N1 C7 1.317(7) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145762
