#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/52/4505231.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_4505231
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            'C28 H32 N4 O6'
_chemical_formula_weight         520.58
_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                94.246(4)
_cell_angle_beta                 90.234(4)
_cell_angle_gamma                100.533(4)
_cell_formula_units_Z            1
_cell_length_a                   5.2263(10)
_cell_length_b                   6.9022(13)
_cell_length_c                   19.145(4)
_cell_measurement_temperature    293(2)
_cell_volume                     677.0(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3136
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.07
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.0629
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2082
_reflns_number_gt                1449
_reflns_number_total             2460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050204xsi20050508_085012.cif
_cod_data_source_block           5-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               4505231
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
O3 O 1.2301(8) 1.3602(6) 0.0233(2) 0.0635(15) Uani 1 1 d .
N2 N 0.7978(9) 1.3103(7) 0.0436(3) 0.0529(16) Uani 1 1 d .
H2 H 0.6550 1.3540 0.0394 0.063 Uiso 1 1 calc R
C8 C 1.0176(12) 1.4115(9) 0.0186(3) 0.0478(17) Uani 1 1 d .
C9 C 0.7947(12) 1.1276(9) 0.0778(3) 0.0555(19) Uani 1 1 d .
H9A H 0.9369 1.1481 0.1118 0.067 Uiso 1 1 calc R
H9B H 0.8239 1.0248 0.0430 0.067 Uiso 1 1 calc R
C10 C 0.5451(12) 1.0588(9) 0.1139(4) 0.0572(19) Uani 1 1 d .
H10A H 0.4004 1.0534 0.0815 0.069 Uiso 1 1 calc R
H10B H 0.5264 1.1529 0.1529 0.069 Uiso 1 1 calc R
C13 C 0.2892(13) 0.5716(10) 0.2023(3) 0.0602(19) Uani 1 1 d .
H13A H 0.2843 0.4813 0.1608 0.072 Uiso 1 1 calc R
H13B H 0.4500 0.5708 0.2277 0.072 Uiso 1 1 calc R
C11 C 0.5359(12) 0.8557(9) 0.1409(3) 0.0565(18) Uani 1 1 d .
H11A H 0.5526 0.7627 0.1014 0.068 Uiso 1 1 calc R
H11B H 0.6851 0.8617 0.1718 0.068 Uiso 1 1 calc R
O1 O 0.0514(12) 0.3095(8) 0.2578(4) 0.110(2) Uani 1 1 d .
H1 H -0.0734 0.2738 0.2826 0.165 Uiso 1 1 calc R
C5 C 0.3624(14) 0.8478(11) 0.4146(4) 0.065(2) Uani 1 1 d .
C12 C 0.2939(12) 0.7774(10) 0.1795(4) 0.0600(19) Uani 1 1 d .
H12A H 0.2808 0.8661 0.2206 0.072 Uiso 1 1 calc R
H12B H 0.1433 0.7756 0.1496 0.072 Uiso 1 1 calc R
O2 O -0.0758(12) 0.5897(9) 0.2740(4) 0.107(2) Uani 1 1 d .
N1 N 0.6683(13) 1.1293(10) 0.3397(3) 0.079(2) Uani 1 1 d .
C2 C 0.0750(15) 0.5717(11) 0.4828(4) 0.072(2) Uani 1 1 d .
C7 C 0.7124(15) 0.9475(13) 0.3379(4) 0.079(2) Uani 1 1 d .
H7 H 0.8485 0.9157 0.3108 0.095 Uiso 1 1 calc R
C14 C 0.0666(15) 0.4960(10) 0.2473(4) 0.061(2) Uani 1 1 d .
C1 C 0.2024(15) 0.6973(11) 0.4519(4) 0.072(2) Uani 1 1 d .
C6 C 0.5670(15) 0.8018(11) 0.3740(4) 0.074(2) Uani 1 1 d .
H6 H 0.6046 0.6749 0.3714 0.088 Uiso 1 1 calc R
C4 C 0.3143(15) 1.0401(11) 0.4169(4) 0.076(2) Uani 1 1 d .
H4 H 0.1797 1.0766 0.4434 0.092 Uiso 1 1 calc R
C3 C 0.4724(18) 1.1754(12) 0.3787(4) 0.086(3) Uani 1 1 d .
H3 H 0.4412 1.3041 0.3801 0.103 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
C8 N2 C9 121.6(5) .
O3 C8 N2 123.2(5) .
O3 C8 C8 122.3(7) 2_785
N2 C8 C8 114.5(7) 2_785
N2 C9 C10 113.2(5) .
C9 C10 C11 111.7(5) .
C14 C13 C12 115.0(6) .
C12 C11 C10 115.1(5) .
C6 C5 C4 118.3(7) .
C6 C5 C1 120.2(7) .
C4 C5 C1 121.4(7) .
C13 C12 C11 113.0(5) .
C7 N1 C3 118.5(7) .
C1 C2 C2 178.8(12) 2_566
N1 C7 C6 123.2(8) .
O2 C14 O1 121.5(7) .
O2 C14 C13 125.8(6) .
O1 C14 C13 112.6(7) .
C2 C1 C5 178.7(10) .
C7 C6 C5 118.9(8) .
C3 C4 C5 118.2(8) .
N1 C3 C4 122.9(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C8 1.230(7) .
N2 C8 1.341(7) .
N2 C9 1.461(7) .
C8 C8 1.498(11) 2_785
C9 C10 1.495(8) .
C10 C11 1.522(8) .
C13 C14 1.491(9) .
C13 C12 1.513(9) .
C11 C12 1.502(8) .
O1 C14 1.305(8) .
C5 C6 1.394(10) .
C5 C4 1.393(11) .
C5 C1 1.444(10) .
O2 C14 1.168(8) .
N1 C7 1.315(10) .
N1 C3 1.341(10) .
C2 C1 1.189(10) .
C2 C2 1.358(14) 2_566
C7 C6 1.377(10) .
C4 C3 1.384(10) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145764
