#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:51:41 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128957.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_7128957
loop_
_publ_author_name
'Yan, Yong'
'Henfling, Stefan'
'Zhang, Ning-Ning'
'Krautscheid, Harald'
_publ_section_title
;
 Semiconductive coordination polymers with continuous π-π interactions
 and defined crystal structures.
;
_journal_issue                   80
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10407
_journal_page_last               10410
_journal_paper_doi               10.1039/d1cc03333f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C2H8N 1+, C14H5N2O6 1-'
_chemical_formula_sum            'C16 H13 N3 O6'
_chemical_formula_weight         343.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2021-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                71.835(8)
_cell_angle_beta                 78.233(9)
_cell_angle_gamma                71.616(8)
_cell_formula_units_Z            2
_cell_length_a                   6.6813(7)
_cell_length_b                   9.1526(9)
_cell_length_c                   12.8079(13)
_cell_measurement_reflns_used    5681
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      71.03
_cell_measurement_theta_min      5.29
_cell_volume                     701.34(13)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20194
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.983
_diffrn_reflns_theta_min         5.284
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0787P)²+0.0872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             4632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03333f2.cif
_cod_data_source_block           l-hk
_cod_depositor_comments
'Adding full bibliography for 7128957--7128960.cif.'
_cod_database_code               7128957
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.958
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9314(4) 0.2632(3) 0.7281(2) 0.0394(7) Uani 1 1 d . . . . .
O2 O 0.8237(4) 0.0229(3) 0.8836(2) 0.0393(7) Uani 1 1 d . . . . .
O3 O 0.8853(5) -0.2474(3) 0.8325(2) 0.0482(8) Uani 1 1 d . . . . .
N1 N 0.8898(5) 0.0123(3) 0.7773(2) 0.0331(7) Uani 1 1 d . . . . .
C1 C 0.9085(6) -0.1334(4) 0.7571(3) 0.0348(8) Uani 1 1 d . . . . .
C2 C 0.9360(6) 0.1458(4) 0.7004(3) 0.0335(8) Uani 1 1 d . . . . .
C3 C 0.9787(5) 0.1399(4) 0.5835(3) 0.0291(8) Uani 1 1 d . . . . .
C4 C 1.0040(6) 0.2732(4) 0.5003(3) 0.0331(8) Uani 1 1 d . . . . .
H4 H 0.9980 0.3675 0.5185 0.040 Uiso 1 1 calc R U . . .
C5 C 1.0387(6) 0.2712(4) 0.3887(3) 0.0325(8) Uani 1 1 d . . . . .
H5A H 1.0562 0.3641 0.3324 0.039 Uiso 1 1 calc R U . . .
C6 C 1.0473(6) 0.1368(4) 0.3607(3) 0.0318(8) Uani 1 1 d . . . . .
C7 C 1.0174(5) -0.0011(4) 0.4441(3) 0.0288(8) Uani 1 1 d . . . . .
O4 O 0.4227(4) 0.4280(3) 0.8444(2) 0.0432(7) Uani 1 1 d . . . . .
O5 O 0.4207(5) 0.1314(3) 0.8655(2) 0.0433(7) Uani 1 1 d . . . . .
H5 H 0.576(9) 0.084(6) 0.881(4) 0.086(17) Uiso 1 1 d . . . . .
O6 O 0.4408(4) 0.0436(3) 0.6835(2) 0.0404(7) Uani 1 1 d . . . . .
N2 N 0.4386(5) 0.2370(3) 0.7618(2) 0.0346(7) Uani 1 1 d . . . . .
C8 C 0.4478(6) 0.1790(4) 0.6713(3) 0.0347(9) Uani 1 1 d . . . . .
C9 C 0.4412(6) 0.3899(4) 0.7593(3) 0.0339(8) Uani 1 1 d . . . . .
C10 C 0.4688(5) 0.4990(4) 0.6483(3) 0.0326(8) Uani 1 1 d . . . . .
C11 C 0.4845(6) 0.4479(4) 0.5530(3) 0.0317(8) Uani 1 1 d . . . . .
C12 C 0.4801(6) 0.6514(4) 0.6376(3) 0.0347(9) Uani 1 1 d . . . . .
H12 H 0.4693 0.6856 0.7019 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5072(6) 0.7550(4) 0.5334(3) 0.0339(9) Uani 1 1 d . . . . .
H13 H 0.5130 0.8597 0.5275 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5258(6) 0.7086(4) 0.4388(3) 0.0316(8) Uani 1 1 d . . . . .
N3 N 0.8852(5) 0.2340(3) 0.9819(3) 0.0384(8) Uani 1 1 d . . . . .
H3A H 1.0039 0.1826 1.0167 0.046 Uiso 1 1 calc R U . . .
H3B H 0.8906 0.1861 0.9285 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6952(7) 0.2169(5) 1.0632(3) 0.0467(10) Uani 1 1 d . . . . .
H15A H 0.5680 0.2603 1.0246 0.070 Uiso 1 1 calc R U . . .
H15B H 0.6820 0.2756 1.1177 0.070 Uiso 1 1 calc R U . . .
H15C H 0.7102 0.1037 1.1011 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8844(7) 0.4012(4) 0.9298(3) 0.0420(10) Uani 1 1 d . . . . .
H16A H 1.0204 0.4059 0.8842 0.063 Uiso 1 1 calc R U . . .
H16B H 0.8635 0.4564 0.9872 0.063 Uiso 1 1 calc R U . . .
H16C H 0.7688 0.4531 0.8830 0.063 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O2 N1 C2 116.9(3) . . ?
O2 N1 C1 116.8(3) . . ?
C2 N1 C1 126.3(3) . . ?
O3 C1 N1 120.7(3) . . ?
O3 C1 C6 123.1(3) . 2_756 ?
N1 C1 C6 116.2(3) . 2_756 ?
O1 C2 N1 121.3(3) . . ?
O1 C2 C3 122.7(3) . . ?
N1 C2 C3 115.9(3) . . ?
C4 C3 C7 119.4(3) . 2_756 ?
C4 C3 C2 120.1(3) . . ?
C7 C3 C2 120.5(3) 2_756 . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 C1 120.3(3) . 2_756 ?
C7 C6 C1 119.6(3) . 2_756 ?
C7 C7 C3 119.8(4) 2_756 2_756 ?
C7 C7 C6 119.4(4) 2_756 . ?
C3 C7 C6 120.8(3) 2_756 . ?
N2 O5 H5 102(3) . . ?
O5 N2 C9 116.4(3) . . ?
O5 N2 C8 116.3(3) . . ?
C9 N2 C8 127.3(3) . . ?
O6 C8 N2 121.6(3) . . ?
O6 C8 C14 122.8(3) . 2_666 ?
N2 C8 C14 115.5(3) . 2_666 ?
O4 C9 N2 121.0(3) . . ?
O4 C9 C10 123.1(3) . . ?
N2 C9 C10 115.9(3) . . ?
C12 C10 C11 119.9(3) . . ?
C12 C10 C9 120.0(3) . . ?
C11 C10 C9 120.1(3) . . ?
C10 C11 C11 119.7(4) . 2_666 ?
C10 C11 C14 121.3(3) . 2_666 ?
C11 C11 C14 119.0(4) 2_666 2_666 ?
C10 C12 C13 120.5(3) . . ?
C10 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C11 119.7(3) . 2_666 ?
C13 C14 C8 120.4(3) . 2_666 ?
C11 C14 C8 119.8(3) 2_666 2_666 ?
C16 N3 C15 112.7(3) . . ?
C16 N3 H3A 109.1 . . ?
C15 N3 H3A 109.1 . . ?
C16 N3 H3B 109.1 . . ?
C15 N3 H3B 109.1 . . ?
H3A N3 H3B 107.8 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O1 C2 1.222(4) . ?
O2 N1 1.368(4) . ?
O3 C1 1.207(4) . ?
N1 C2 1.386(5) . ?
N1 C1 1.399(4) . ?
C1 C6 1.485(5) 2_756 ?
C2 C3 1.480(5) . ?
C3 C4 1.378(5) . ?
C3 C7 1.414(5) 2_756 ?
C4 C5 1.405(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.416(5) . ?
C6 C1 1.485(5) 2_756 ?
C7 C7 1.407(7) 2_756 ?
C7 C3 1.414(5) 2_756 ?
O4 C9 1.216(4) . ?
O5 N2 1.385(4) . ?
O5 H5 1.02(5) . ?
O6 C8 1.215(4) . ?
N2 C9 1.395(4) . ?
N2 C8 1.401(5) . ?
C8 C14 1.478(5) 2_666 ?
C9 C10 1.475(5) . ?
C10 C12 1.383(5) . ?
C10 C11 1.412(5) . ?
C11 C11 1.413(7) 2_666 ?
C11 C14 1.426(5) 2_666 ?
C12 C13 1.390(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9500 . ?
C14 C11 1.426(5) 2_666 ?
C14 C8 1.478(5) 2_666 ?
N3 C16 1.465(4) . ?
N3 C15 1.485(5) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 O3 -6.4(5) . . . . ?
C2 N1 C1 O3 172.1(4) . . . . ?
O2 N1 C1 C6 172.3(3) . . . 2_756 ?
C2 N1 C1 C6 -9.2(5) . . . 2_756 ?
O2 N1 C2 O1 4.7(5) . . . . ?
C1 N1 C2 O1 -173.8(3) . . . . ?
O2 N1 C2 C3 -172.0(3) . . . . ?
C1 N1 C2 C3 9.5(5) . . . . ?
O1 C2 C3 C4 -3.5(5) . . . . ?
N1 C2 C3 C4 173.2(3) . . . . ?
O1 C2 C3 C7 179.9(3) . . . 2_756 ?
N1 C2 C3 C7 -3.4(5) . . . 2_756 ?
C7 C3 C4 C5 -1.5(5) 2_756 . . . ?
C2 C3 C4 C5 -178.2(3) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C4 C5 C6 C1 -177.8(3) . . . 2_756 ?
C5 C6 C7 C7 -1.1(6) . . . 2_756 ?
C1 C6 C7 C7 177.9(4) 2_756 . . 2_756 ?
C5 C6 C7 C3 178.7(3) . . . 2_756 ?
C1 C6 C7 C3 -2.4(5) 2_756 . . 2_756 ?
O5 N2 C8 O6 -0.1(5) . . . . ?
C9 N2 C8 O6 -178.7(3) . . . . ?
O5 N2 C8 C14 -178.0(3) . . . 2_666 ?
C9 N2 C8 C14 3.4(5) . . . 2_666 ?
O5 N2 C9 O4 -1.9(5) . . . . ?
C8 N2 C9 O4 176.7(3) . . . . ?
O5 N2 C9 C10 177.7(3) . . . . ?
C8 N2 C9 C10 -3.7(5) . . . . ?
O4 C9 C10 C12 1.7(5) . . . . ?
N2 C9 C10 C12 -177.9(3) . . . . ?
O4 C9 C10 C11 -178.6(4) . . . . ?
N2 C9 C10 C11 1.8(5) . . . . ?
C12 C10 C11 C11 1.1(6) . . . 2_666 ?
C9 C10 C11 C11 -178.6(4) . . . 2_666 ?
C12 C10 C11 C14 179.8(3) . . . 2_666 ?
C9 C10 C11 C14 0.0(5) . . . 2_666 ?
C11 C10 C12 C13 -0.1(5) . . . . ?
C9 C10 C12 C13 179.7(3) . . . . ?
C10 C12 C13 C14 -0.7(6) . . . . ?
C12 C13 C14 C11 0.5(5) . . . 2_666 ?
C12 C13 C14 C8 179.3(3) . . . 2_666 ?
