#------------------------------------------------------------------------------
#$Date: 2020-04-10 07:18:06 +0300 (Fri, 10 Apr 2020) $
#$Revision: 250584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557777.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_1557777
loop_
_publ_author_name
'Li, Baixue'
'Qin, Anjun'
'Tang, Ben Zhong'
_publ_section_title
;
 Metal-free polycycloaddition of aldehyde-activated internal diynes and
 diazides toward post-functionalizable poly(formyl-1,2,3-triazole)s
;
_journal_name_full               'Polymer Chemistry'
_journal_paper_doi               10.1039/D0PY00193G
_journal_year                    2020
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2019-10-12 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                110.846(5)
_cell_angle_beta                 92.668(5)
_cell_angle_gamma                107.055(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1045(15)
_cell_length_b                   9.4078(14)
_cell_length_c                   9.9658(17)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.79
_cell_volume                     751.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10178
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0679
_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/[\s^2^(Fo^2^)+(0.0569P)^2^+1.2596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1939
_reflns_number_gt                1860
_reflns_number_total             2573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0py00193g2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1557777
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.5831(5) 0.5921(5) 0.1790(4) 0.0675(12) Uani 1 1 d . . .
N3 N 0.7036(4) 0.7291(3) 0.6315(3) 0.0537(8) Uani 1 1 d . . .
C7 C 0.7788(4) 0.3512(4) 0.5541(3) 0.0386(7) Uani 1 1 d . . .
N4 N 0.7488(3) 0.6226(3) 0.6697(3) 0.0439(7) Uani 1 1 d . . .
N2 N 0.6659(3) 0.6676(3) 0.4892(3) 0.0504(8) Uani 1 1 d . . .
C17 C 0.7401(3) 0.4909(4) 0.5511(3) 0.0377(7) Uani 1 1 d . . .
C16 C 0.6879(4) 0.5220(4) 0.4364(4) 0.0404(8) Uani 1 1 d . . .
C12 C 0.6712(4) 0.1992(4) 0.4848(4) 0.0515(9) Uani 1 1 d . . .
H12 H 0.5742 0.1862 0.4387 0.062 Uiso 1 1 calc R . .
C8 C 0.9228(4) 0.3691(4) 0.6219(4) 0.0455(8) Uani 1 1 d . . .
H8 H 0.9961 0.4714 0.6691 0.055 Uiso 1 1 calc R . .
C10 C 0.8485(5) 0.0848(5) 0.5512(5) 0.0589(10) Uani 1 1 d . . .
H10 H 0.8715 -0.0053 0.5512 0.071 Uiso 1 1 calc R . .
C11 C 0.7069(5) 0.0657(4) 0.4837(5) 0.0605(11) Uani 1 1 d . . .
H11 H 0.6341 -0.0370 0.4368 0.073 Uiso 1 1 calc R . .
C15 C 0.6648(4) 0.4235(4) 0.2841(4) 0.0513(9) Uani 1 1 d . . .
H15 H 0.6827 0.3259 0.2616 0.062 Uiso 1 1 calc R . .
C2 C 1.0536(5) 0.8575(5) 0.8267(4) 0.0618(11) Uani 1 1 d . . .
H2 H 1.0101 0.8688 0.7464 0.074 Uiso 1 1 calc R . .
C18 C 0.7963(4) 0.6597(4) 0.8229(4) 0.0499(9) Uani 1 1 d . . .
H18A H 0.7709 0.5594 0.8377 0.060 Uiso 1 1 calc R . .
H18B H 0.7359 0.7216 0.8793 0.060 Uiso 1 1 calc R . .
C1 C 0.9660(4) 0.7521(4) 0.8809(4) 0.0492(9) Uani 1 1 d . . .
C6 C 1.0346(5) 0.7355(6) 0.9984(4) 0.0681(11) Uani 1 1 d . . .
H6 H 0.9775 0.6621 1.0348 0.082 Uiso 1 1 calc R . .
N1 N 0.5487(6) 0.6975(5) 0.1746(4) 0.1019(16) Uani 1 1 d . . .
C14 C 0.6210(5) 0.4544(5) 0.1714(4) 0.0581(10) Uani 1 1 d . . .
H14 H 0.6147 0.3785 0.0790 0.070 Uiso 1 1 calc R . .
C9 C 0.9578(5) 0.2348(5) 0.6193(4) 0.0563(10) Uani 1 1 d . . .
H9 H 1.0552 0.2463 0.6636 0.068 Uiso 1 1 calc R . .
C5 C 1.1871(6) 0.8267(8) 1.0620(5) 0.0917(17) Uani 1 1 d . . .
H5 H 1.2316 0.8158 1.1421 0.110 Uiso 1 1 calc R . .
C3 C 1.2074(6) 0.9475(5) 0.8912(5) 0.0797(14) Uani 1 1 d . . .
H3 H 1.2665 1.0192 0.8541 0.096 Uiso 1 1 calc R . .
C4 C 1.2721(6) 0.9316(7) 1.0088(6) 0.0867(16) Uani 1 1 d . . .
H4 H 1.3749 0.9931 1.0524 0.104 Uiso 1 1 calc R . .
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
C13 0.082(3) 0.060(3) 0.049(2) 0.021(2) -0.016(2) 0.011(2)
N3 0.066(2) 0.0396(16) 0.0576(19) 0.0159(14) 0.0035(15) 0.0251(15)
C7 0.0428(18) 0.0355(17) 0.0424(17) 0.0171(14) 0.0128(14) 0.0166(14)
N4 0.0507(17) 0.0373(15) 0.0445(16) 0.0147(13) 0.0041(13) 0.0174(13)
N2 0.0542(18) 0.0437(17) 0.0553(19) 0.0183(14) 0.0039(14) 0.0210(14)
C17 0.0351(17) 0.0325(17) 0.0425(18) 0.0112(14) 0.0066(14) 0.0109(13)
C16 0.0400(18) 0.0352(17) 0.0447(18) 0.0143(14) 0.0023(14) 0.0130(14)
C12 0.043(2) 0.038(2) 0.068(2) 0.0174(17) 0.0062(17) 0.0108(16)
C8 0.045(2) 0.0403(19) 0.053(2) 0.0195(16) 0.0074(16) 0.0155(15)
C10 0.061(3) 0.049(2) 0.086(3) 0.037(2) 0.030(2) 0.031(2)
C11 0.058(2) 0.0348(19) 0.087(3) 0.0216(19) 0.024(2) 0.0132(17)
C15 0.052(2) 0.047(2) 0.050(2) 0.0135(17) -0.0017(17) 0.0176(17)
C2 0.071(3) 0.048(2) 0.057(2) 0.0134(19) 0.010(2) 0.015(2)
C18 0.061(2) 0.045(2) 0.0401(19) 0.0130(16) 0.0082(16) 0.0167(17)
C1 0.059(2) 0.044(2) 0.0386(18) 0.0077(15) 0.0087(16) 0.0185(17)
C6 0.067(3) 0.083(3) 0.052(2) 0.026(2) 0.006(2) 0.023(2)
N1 0.156(4) 0.070(3) 0.070(3) 0.026(2) -0.028(3) 0.032(3)
C14 0.065(2) 0.059(2) 0.047(2) 0.0165(18) -0.0030(18) 0.021(2)
C9 0.053(2) 0.062(2) 0.069(2) 0.034(2) 0.0123(19) 0.029(2)
C5 0.069(3) 0.141(5) 0.057(3) 0.024(3) 0.006(2) 0.041(3)
C3 0.071(3) 0.056(3) 0.078(3) 0.000(2) 0.021(3) 0.003(2)
C4 0.058(3) 0.094(4) 0.064(3) -0.014(3) 0.006(2) 0.018(3)
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'
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
N1 C13 C14 175.0(4) . . ?
N2 N3 N4 107.3(3) . . ?
C12 C7 C8 119.4(3) . . ?
C12 C7 C17 119.3(3) . . ?
C8 C7 C17 121.2(3) . . ?
N3 N4 C17 111.1(3) . . ?
N3 N4 C18 119.2(3) . . ?
C17 N4 C18 129.7(3) . . ?
N3 N2 C16 108.7(3) . . ?
N4 C17 C16 104.0(3) . . ?
N4 C17 C7 125.2(3) . . ?
C16 C17 C7 130.9(3) . . ?
N2 C16 C17 108.9(3) . . ?
N2 C16 C15 124.0(3) . . ?
C17 C16 C15 127.0(3) . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C14 C15 C16 128.1(4) . . ?
C14 C15 H15 116.0 . . ?
C16 C15 H15 116.0 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N4 C18 C1 115.0(3) . . ?
N4 C18 H18A 108.5 . . ?
C1 C18 H18A 108.5 . . ?
N4 C18 H18B 108.5 . . ?
C1 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C2 C1 C6 118.6(4) . . ?
C2 C1 C18 122.8(3) . . ?
C6 C1 C18 118.5(3) . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C15 C14 C13 126.0(4) . . ?
C15 C14 H14 117.0 . . ?
C13 C14 H14 117.0 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
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
C13 N1 1.138(5) . ?
C13 C14 1.413(6) . ?
N3 N2 1.311(4) . ?
N3 N4 1.348(4) . ?
C7 C12 1.376(5) . ?
C7 C8 1.382(4) . ?
C7 C17 1.466(4) . ?
N4 C17 1.353(4) . ?
N4 C18 1.452(4) . ?
N2 C16 1.360(4) . ?
C17 C16 1.373(4) . ?
C16 C15 1.436(5) . ?
C12 C11 1.383(5) . ?
C12 H12 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C10 C11 1.358(5) . ?
C10 C9 1.369(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C15 C14 1.329(5) . ?
C15 H15 0.9300 . ?
C2 C1 1.367(5) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9300 . ?
C18 C1 1.499(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C1 C6 1.380(5) . ?
C6 C5 1.377(6) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C5 C4 1.348(8) . ?
C5 H5 0.9300 . ?
C3 C4 1.362(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
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
N2 N3 N4 C17 0.0(4) . . . . ?
N2 N3 N4 C18 -179.5(3) . . . . ?
N4 N3 N2 C16 -0.4(4) . . . . ?
N3 N4 C17 C16 0.4(4) . . . . ?
C18 N4 C17 C16 179.8(3) . . . . ?
N3 N4 C17 C7 -179.2(3) . . . . ?
C18 N4 C17 C7 0.2(5) . . . . ?
C12 C7 C17 N4 126.5(4) . . . . ?
C8 C7 C17 N4 -55.3(5) . . . . ?
C12 C7 C17 C16 -53.1(5) . . . . ?
C8 C7 C17 C16 125.2(4) . . . . ?
N3 N2 C16 C17 0.7(4) . . . . ?
N3 N2 C16 C15 -177.1(3) . . . . ?
N4 C17 C16 N2 -0.7(4) . . . . ?
C7 C17 C16 N2 179.0(3) . . . . ?
N4 C17 C16 C15 177.0(3) . . . . ?
C7 C17 C16 C15 -3.4(6) . . . . ?
C8 C7 C12 C11 0.3(5) . . . . ?
C17 C7 C12 C11 178.6(3) . . . . ?
C12 C7 C8 C9 0.1(5) . . . . ?
C17 C7 C8 C9 -178.1(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C7 C12 C11 C10 0.0(6) . . . . ?
N2 C16 C15 C14 0.5(6) . . . . ?
C17 C16 C15 C14 -176.8(4) . . . . ?
N3 N4 C18 C1 -88.8(4) . . . . ?
C17 N4 C18 C1 91.8(4) . . . . ?
C3 C2 C1 C6 -1.3(6) . . . . ?
C3 C2 C1 C18 175.7(4) . . . . ?
N4 C18 C1 C2 29.8(5) . . . . ?
N4 C18 C1 C6 -153.2(3) . . . . ?
C2 C1 C6 C5 1.8(6) . . . . ?
C18 C1 C6 C5 -175.3(4) . . . . ?
C16 C15 C14 C13 -1.9(7) . . . . ?
N1 C13 C14 C15 -170(6) . . . . ?
C11 C10 C9 C8 1.2(6) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C1 C6 C5 C4 -1.1(7) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C6 C5 C4 C3 -0.2(8) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?