#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150734.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_7150734
loop_
_publ_author_name
'Wei, Siping'
'Liu, Bo'
'Zhao, Dongbing'
'Wang, Zhen'
'Wu, Jie'
'Lan, Jingbo'
'You, Jingsong'
_publ_section_title
;
 Pyrido[1,2-c][1,2,4]triazol-3-ylidene: reactivity and its application
 in organocatalysis and organometallic catalysis
;
_journal_issue                   20
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4241
_journal_page_last               4247
_journal_paper_doi               10.1039/b910073c
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C7 H9 N3'
_chemical_formula_weight         135.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.329(3)
_cell_length_b                   9.235(2)
_cell_length_c                   14.718(4)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      9.29
_cell_measurement_theta_min      4.60
_cell_volume                     722.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega/2-Theta
_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  0.0048
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1408
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        4.234
_diffrn_standards_interval_count 120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.2079
_refine_ls_R_factor_gt           0.0612
_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)+(0.0671P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                471
_reflns_number_total             1288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b910073c.txt
_cod_data_source_block           CCDC_725113
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        723.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150734
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4832(5) 1.0456(3) 0.12446(18) 0.0583(9) Uani 1 d . . .
N2 N 0.2306(5) 0.8796(3) 0.04803(19) 0.0627(9) Uani 1 d . . .
HN2 H 0.3267 0.8858 0.0034 0.075 Uiso 1 calc R . .
N3 N 0.0260(5) 0.7887(3) 0.04327(19) 0.0602(9) Uani 1 d . . .
C1 C 0.2786(7) 0.9603(4) 0.1256(2) 0.0536(10) Uani 1 d . . .
C2 C 0.1265(7) 0.9545(4) 0.1989(3) 0.0669(11) Uani 1 d . . .
H2 H -0.0128 0.8937 0.1979 0.080 Uiso 1 calc R . .
C3 C 0.1873(7) 1.0402(4) 0.2720(3) 0.0760(12) Uani 1 d . . .
H3 H 0.0869 1.0390 0.3215 0.091 Uiso 1 calc R . .
C4 C 0.3964(8) 1.1293(4) 0.2739(3) 0.0751(13) Uani 1 d . . .
H4 H 0.4400 1.1887 0.3235 0.090 Uiso 1 calc R . .
C5 C 0.5353(7) 1.1253(4) 0.1987(3) 0.0677(12) Uani 1 d . . .
H5 H 0.6784 1.1830 0.1996 0.081 Uiso 1 calc R . .
C6 C -0.0351(7) 0.7284(4) -0.0311(2) 0.0656(11) Uani 1 d . . .
H6 H 0.0568 0.7480 -0.0814 0.079 Uiso 1 calc R . .
C7 C -0.2503(6) 0.6268(4) -0.0410(2) 0.0727(12) Uani 1 d . . .
H7A H -0.3370 0.6257 0.0143 0.109 Uiso 1 calc R . .
H7B H -0.1897 0.5313 -0.0531 0.109 Uiso 1 calc R . .
H7C H -0.3635 0.6575 -0.0905 0.109 Uiso 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
N1 0.049(2) 0.0577(16) 0.069(2) -0.0053(17) 0.0097(16) -0.0062(18)
N2 0.057(2) 0.0640(18) 0.069(2) -0.0052(17) 0.0190(17) -0.0062(17)
N3 0.055(2) 0.0527(18) 0.073(2) 0.0011(16) 0.0062(16) -0.0096(17)
C1 0.061(3) 0.0440(18) 0.056(2) 0.004(2) -0.002(2) 0.003(2)
C2 0.071(3) 0.068(2) 0.064(2) -0.001(2) 0.014(2) -0.011(2)
C3 0.088(3) 0.081(3) 0.060(2) -0.002(2) 0.018(2) 0.003(3)
C4 0.090(4) 0.070(3) 0.064(3) -0.001(2) -0.003(3) -0.002(3)
C5 0.066(3) 0.069(2) 0.069(3) -0.002(2) 0.004(2) -0.008(2)
C6 0.074(3) 0.054(2) 0.069(2) 0.005(2) 0.007(2) -0.005(2)
C7 0.074(3) 0.062(2) 0.082(3) 0.000(2) 0.000(2) -0.004(2)
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
C5 N1 C1 116.2(3) . . ?
C1 N2 N3 118.7(3) . . ?
C1 N2 HN2 120.7 . . ?
N3 N2 HN2 120.7 . . ?
C6 N3 N2 118.6(3) . . ?
N1 C1 N2 114.6(3) . . ?
N1 C1 C2 122.9(3) . . ?
N2 C1 C2 122.4(4) . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 116.2(4) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
N1 C5 C4 125.6(4) . . ?
N1 C5 H5 117.2 . . ?
C4 C5 H5 117.2 . . ?
N3 C6 C7 121.7(4) . . ?
N3 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
N1 C5 1.333(4) . ?
N1 C1 1.346(4) . ?
N2 C1 1.374(4) . ?
N2 N3 1.374(3) . ?
N2 HN2 0.8600 . ?
N3 C6 1.253(4) . ?
C1 C2 1.390(5) . ?
C2 C3 1.359(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.482(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 HN2 N1 0.86 2.28 3.119(4) 164.8 3_675
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25944206
2 PubChem 44470448
