#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/52/4505230.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_4505230
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                84.790(7)
_cell_angle_beta                 89.247(7)
_cell_angle_gamma                80.962(7)
_cell_formula_units_Z            1
_cell_length_a                   5.215(2)
_cell_length_b                   6.860(3)
_cell_length_c                   18.858(7)
_cell_measurement_temperature    293(2)
_cell_volume                     663.5(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0864
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2974
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0627
_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)+(0.1060P)²+0.0068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                1362
_reflns_number_total             2402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050204xsi20050508_085012.cif
_cod_data_source_block           5-ox:3-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               4505230
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
N2 N 0.1997(7) 1.3123(5) 0.45622(19) 0.0464(10) Uani 1 1 d .
O3 O -0.2350(6) 1.3628(4) 0.47452(16) 0.0567(10) Uani 1 1 d .
O2 O 1.0583(7) 0.5770(4) 0.21968(19) 0.0752(11) Uani 1 1 d .
O1 O 0.9025(6) 0.2967(4) 0.24521(16) 0.0713(11) Uani 1 1 d .
H1 H 1.0252 0.2527 0.2206 0.107 Uiso 1 1 calc R
C9 C 0.2022(8) 1.1303(5) 0.4206(2) 0.0498(12) Uani 1 1 d .
H9A H 0.0617 1.1518 0.3862 0.060 Uiso 1 1 calc R
H9B H 0.1691 1.0250 0.4558 0.060 Uiso 1 1 calc R
C13 C 0.6834(8) 0.5752(5) 0.2948(2) 0.0474(12) Uani 1 1 d .
H13A H 0.6743 0.4865 0.3375 0.057 Uiso 1 1 calc R
H13B H 0.5232 0.5809 0.2686 0.057 Uiso 1 1 calc R
C8 C -0.0179(9) 1.4094(5) 0.4808(2) 0.0419(11) Uani 1 1 d .
C14 C 0.9036(9) 0.4878(6) 0.2503(2) 0.0469(12) Uani 1 1 d .
C12 C 0.6976(8) 0.7814(5) 0.3169(2) 0.0498(12) Uani 1 1 d .
H12A H 0.8440 0.7748 0.3487 0.060 Uiso 1 1 calc R
H12B H 0.7249 0.8690 0.2751 0.060 Uiso 1 1 calc R
C11 C 0.4497(8) 0.8644(5) 0.3540(2) 0.0474(12) Uani 1 1 d .
H11A H 0.3067 0.8778 0.3207 0.057 Uiso 1 1 calc R
H11B H 0.4166 0.7696 0.3931 0.057 Uiso 1 1 calc R
C10 C 0.4527(8) 1.0633(6) 0.3830(2) 0.0509(12) Uani 1 1 d .
H10A H 0.5966 1.0525 0.4159 0.061 Uiso 1 1 calc R
H10B H 0.4781 1.1610 0.3441 0.061 Uiso 1 1 calc R
C1 C 0.7976(9) 0.3228(6) 0.0469(2) 0.0571(13) Uani 1 1 d .
N1 N 0.2901(7) 0.1365(5) 0.16121(19) 0.0562(11) Uani 1 1 d .
C3 C 0.4404(9) 0.2538(6) 0.1271(2) 0.0534(13) Uani 1 1 d .
H3 H 0.4078 0.3883 0.1335 0.064 Uiso 1 1 calc R
C7 C 0.3378(10) -0.0555(6) 0.1516(2) 0.0588(14) Uani 1 1 d .
H7 H 0.2329 -0.1395 0.1745 0.071 Uiso 1 1 calc R
C4 C 0.6436(9) 0.1875(6) 0.0823(2) 0.0501(12) Uani 1 1 d .
C2 C 0.9244(9) 0.4368(6) 0.0170(2) 0.0562(13) Uani 1 1 d .
C5 C 0.6908(10) -0.0132(7) 0.0747(2) 0.0628(14) Uani 1 1 d .
H5 H 0.8267 -0.0654 0.0462 0.075 Uiso 1 1 calc R
C6 C 0.5363(10) -0.1342(7) 0.1092(3) 0.0696(16) Uani 1 1 d .
H6 H 0.5654 -0.2695 0.1041 0.083 Uiso 1 1 calc R
H2 H 0.345(9) 1.356(6) 0.462(2) 0.066(16) Uiso 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'
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(4) .
N2 C9 C10 114.2(3) .
C14 C13 C12 115.8(3) .
O3 C8 N2 124.7(4) .
O3 C8 C8 120.9(5) 2_586
N2 C8 C8 114.4(5) 2_586
O2 C14 O1 122.6(4) .
O2 C14 C13 125.7(4) .
O1 C14 C13 111.6(4) .
C11 C12 C13 110.9(3) .
C10 C11 C12 114.9(3) .
C9 C10 C11 110.9(3) .
C2 C1 C4 179.5(6) .
C3 N1 C7 117.6(4) .
N1 C3 C4 124.0(4) .
N1 C7 C6 122.4(4) .
C5 C4 C3 116.9(4) .
C5 C4 C1 122.1(4) .
C3 C4 C1 121.0(4) .
C1 C2 C2 178.4(7) 2_765
C6 C5 C4 119.5(4) .
C5 C6 C7 119.7(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C8 1.323(5) .
N2 C9 1.468(5) .
O3 C8 1.234(5) .
O2 C14 1.199(4) .
O1 C14 1.324(4) .
C9 C10 1.506(5) .
C13 C14 1.494(5) .
C13 C12 1.524(5) .
C8 C8 1.531(7) 2_586
C12 C11 1.518(5) .
C11 C10 1.517(5) .
C1 C2 1.200(5) .
C1 C4 1.436(6) .
N1 C3 1.329(5) .
N1 C7 1.330(5) .
C3 C4 1.392(6) .
C7 C6 1.372(6) .
C4 C5 1.380(5) .
C2 C2 1.373(9) 2_765
C5 C6 1.364(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145763
