#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/14/7211442.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_7211442
loop_
_publ_author_name
'Waidmann, Thomas'
'Fritsch, Nico'
'Tucher, Johannes'
'Rudolf, Marc'
'Glaser, Felix'
'Guldi, Dirk M.'
'Burzlaff, Nicolai'
_publ_section_title
;
 Battlement-shaped 1D coordination polymer based on a
 bis(N-methylimidazole-2-yl)butadiyne ligand
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10157
_journal_paper_doi               10.1039/c3ce41652f
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H10 N4'
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-28T11:59:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.413(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0586(4)
_cell_length_b                   11.6096(4)
_cell_length_c                   12.8621(7)
_cell_measurement_reflns_used    89
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      6
_cell_measurement_wavelength     0.71073
_cell_volume                     1053.08(9)
_computing_cell_refinement       'EVALCCD (Duisenberg, 2003)'
_computing_data_collection       'COLLECT (Bruker-Nonius, 2002)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
 φ- and ω-rotations with 1.60 ° and 192 sec per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_unetI/netI     0.014
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14414
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         6.25
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.4547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1914
_reflns_number_total             2146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41652f.txt
_cod_data_source_block           compound7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7211442
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.18554(17) 0.64825(11) 0.53301(10) 0.0218(3) Uani 1 1 d .
C2 C 0.22584(17) 0.56073(11) 0.48919(10) 0.0218(3) Uani 1 1 d .
C3 C 0.27293(17) 0.46293(11) 0.43701(10) 0.0214(3) Uani 1 1 d .
C4 C 0.31627(17) 0.37864(11) 0.38930(9) 0.0217(3) Uani 1 1 d .
C11 C 0.13725(17) 0.75229(11) 0.58303(9) 0.0192(3) Uani 1 1 d .
C12 C 0.06006(18) 0.87078(11) 0.70561(10) 0.0227(3) Uani 1 1 d .
H12 H 0.0304 0.9023 0.7694 0.027 Uiso 1 1 calc R
C13 C 0.06586(19) 0.92696(11) 0.61323(10) 0.0243(3) Uani 1 1 d .
H13 H 0.0403 1.0049 0.6039 0.029 Uiso 1 1 calc R
C14 C 0.1154(2) 0.66564(12) 0.76171(11) 0.0301(3) Uani 1 1 d .
H14A H -0.0108 0.6437 0.7786 0.045 Uiso 1 1 calc R
H14B H 0.1839 0.6907 0.8237 0.045 Uiso 1 1 calc R
H14C H 0.1789 0.6008 0.7326 0.045 Uiso 1 1 calc R
C21 C 0.36786(17) 0.28038(11) 0.33160(10) 0.0209(3) Uani 1 1 d .
C22 C 0.44779(18) 0.10325(11) 0.29782(10) 0.0256(3) Uani 1 1 d .
H22 H 0.4792 0.0257 0.3037 0.031 Uiso 1 1 calc R
C23 C 0.4393(2) 0.16719(13) 0.20951(11) 0.0301(3) Uani 1 1 d .
H23 H 0.4641 0.139 0.1438 0.036 Uiso 1 1 calc R
C24 C 0.3899(2) 0.14708(12) 0.48572(10) 0.0272(3) Uani 1 1 d .
H24A H 0.3437 0.0698 0.4926 0.041 Uiso 1 1 calc R
H24B H 0.3049 0.1996 0.5177 0.041 Uiso 1 1 calc R
H24C H 0.5135 0.1532 0.5192 0.041 Uiso 1 1 calc R
N11 N 0.11426(16) 0.85349(9) 0.53599(8) 0.0239(3) Uani 1 1 d .
N12 N 0.10631(14) 0.75914(9) 0.68633(8) 0.0198(2) Uani 1 1 d .
N21 N 0.38958(17) 0.27852(10) 0.22980(9) 0.0285(3) Uani 1 1 d .
N22 N 0.40109(14) 0.17538(9) 0.37607(8) 0.0205(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0222(6) 0.0203(6) 0.0230(6) 0.0007(5) 0.0019(5) 0.0009(5)
C2 0.0236(6) 0.0195(6) 0.0223(6) 0.0012(5) 0.0024(5) 0.0010(5)
C3 0.0231(6) 0.0198(6) 0.0214(6) 0.0009(5) 0.0018(5) 0.0013(5)
C4 0.0224(6) 0.0216(6) 0.0212(6) 0.0012(5) 0.0019(5) 0.0016(5)
C11 0.0202(6) 0.0181(6) 0.0195(6) 0.0002(5) 0.0014(4) 0.0007(4)
C12 0.0278(6) 0.0205(6) 0.0199(6) -0.0041(5) 0.0025(5) 0.0024(5)
C13 0.0318(7) 0.0165(6) 0.0248(7) -0.0006(5) 0.0030(5) 0.0045(5)
C14 0.0401(8) 0.0254(7) 0.0247(7) 0.0099(6) 0.0015(6) 0.0008(6)
C21 0.0214(6) 0.0204(6) 0.0211(6) -0.0013(5) 0.0020(5) 0.0024(5)
C22 0.0256(6) 0.0212(6) 0.0302(7) -0.0071(5) 0.0018(5) 0.0038(5)
C23 0.0351(7) 0.0324(7) 0.0230(7) -0.0082(6) 0.0034(5) 0.0085(6)
C24 0.0322(7) 0.0261(7) 0.0236(7) 0.0035(5) 0.0046(5) 0.0017(5)
N11 0.0321(6) 0.0190(5) 0.0208(5) 0.0017(4) 0.0044(4) 0.0046(4)
N12 0.0240(5) 0.0176(5) 0.0178(5) 0.0017(4) 0.0010(4) -0.0005(4)
N21 0.0356(6) 0.0291(6) 0.0211(6) -0.0011(5) 0.0048(5) 0.0082(5)
N22 0.0215(5) 0.0185(5) 0.0216(5) -0.0015(4) 0.0011(4) 0.0008(4)
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 0 '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
C2 C1 C11 179.03(13)
C1 C2 C3 178.43(14)
C4 C3 C2 178.38(14)
C3 C4 C21 179.06(13)
N11 C11 N12 111.86(11)
N11 C11 C1 125.05(11)
N12 C11 C1 123.08(11)
C13 C12 N12 106.35(11)
C12 C13 N11 110.78(11)
N21 C21 N22 112.04(11)
N21 C21 C4 125.02(12)
N22 C21 C4 122.95(11)
C23 C22 N22 106.21(11)
C22 C23 N21 111.11(12)
C11 N11 C13 104.53(10)
C11 N12 C12 106.47(10)
C11 N12 C14 127.15(11)
C12 N12 C14 126.36(11)
C21 N21 C23 104.21(11)
C22 N22 C21 106.43(11)
C22 N22 C24 127.12(11)
C21 N22 C24 126.45(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.2019(18)
C1 C11 1.4169(17)
C2 C3 1.3671(17)
C3 C4 1.2014(18)
C4 C21 1.4168(17)
C11 N11 1.3284(16)
C11 N12 1.3579(16)
C12 C13 1.3576(18)
C12 N12 1.3620(16)
C13 N11 1.3638(16)
C14 N12 1.4550(16)
C21 N21 1.3249(17)
C21 N22 1.3627(16)
C22 C23 1.356(2)
C22 N22 1.3605(16)
C23 N21 1.3673(18)
C24 N22 1.4535(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197344
