#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/93/7219303.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_7219303
loop_
_publ_author_name
'Li, chen'
'Ge, Haixia'
'Yin, Bing'
'She, Mengyao'
'Liu, Ping'
'Li, Xiangdong'
'Li, Jianli'
_publ_section_title
;
 Novel 3,6-Unsymmetrically Disubstituted-1,2,4,5-Tetrazines: S-Induced
 One-Pot Synthesis, Properties and Theoretical Study
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10808F
_journal_year                    2015
_chemical_formula_sum            'C14 H11 N5'
_chemical_formula_weight         249.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-11-22 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.214(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.781(4)
_cell_length_b                   8.473(3)
_cell_length_c                   24.554(9)
_cell_measurement_reflns_used    2206
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.96
_cell_volume                     2450.4(15)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7356
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.7598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2019
_reflns_number_total             2992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10808f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 
;
_cod_original_cell_volume        2450.5(15)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7219303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.72910(16) -0.1866(2) 0.26849(7) 0.0637(5) Uani 1 1 d .
H1 H 0.7511 -0.1586 0.2336 0.076 Uiso 1 1 calc R
C2 C 0.65310(15) -0.3086(2) 0.27314(7) 0.0604(4) Uani 1 1 d .
H2 H 0.6255 -0.3618 0.2425 0.072 Uiso 1 1 calc R
C3 C 0.61936(15) -0.3493(2) 0.32410(7) 0.0593(4) Uani 1 1 d .
H3 H 0.5670 -0.4301 0.3289 0.071 Uiso 1 1 calc R
C4 C 0.66414(13) -0.26886(18) 0.36831(6) 0.0530(4) Uani 1 1 d .
H4 H 0.6432 -0.2953 0.4035 0.064 Uiso 1 1 calc R
C5 C 0.74044(12) -0.14859(16) 0.35968(5) 0.0439(3) Uani 1 1 d .
C6 C 0.78881(11) -0.05680(16) 0.40568(5) 0.0428(3) Uani 1 1 d .
C7 C 0.86838(11) 0.10583(16) 0.48645(5) 0.0419(3) Uani 1 1 d .
C8 C 0.91294(11) 0.20022(16) 0.53226(5) 0.0414(3) Uani 1 1 d .
C9 C 0.86335(13) 0.19285(18) 0.58305(6) 0.0515(4) Uani 1 1 d .
H9 H 0.8008 0.1280 0.5882 0.062 Uiso 1 1 calc R
C10 C 0.90654(15) 0.2813(2) 0.62571(6) 0.0579(4) Uani 1 1 d .
H10 H 0.8723 0.2752 0.6594 0.069 Uiso 1 1 calc R
C11 C 0.99943(13) 0.37908(18) 0.61974(6) 0.0511(4) Uani 1 1 d .
C12 C 1.04756(13) 0.38607(19) 0.56907(6) 0.0546(4) Uani 1 1 d .
H12 H 1.1099 0.4512 0.5639 0.066 Uiso 1 1 calc R
C13 C 1.00543(12) 0.29895(18) 0.52600(6) 0.0495(4) Uani 1 1 d .
H13 H 1.0394 0.3064 0.4923 0.059 Uiso 1 1 calc R
C14 C 1.04767(17) 0.4735(2) 0.66660(8) 0.0710(5) Uani 1 1 d .
H14A H 1.1093 0.4164 0.6835 0.106 Uiso 1 1 calc R
H14B H 0.9897 0.4913 0.6928 0.106 Uiso 1 1 calc R
H14C H 1.0748 0.5730 0.6535 0.106 Uiso 1 1 calc R
N1 N 0.77347(12) -0.10581(16) 0.31010(5) 0.0568(4) Uani 1 1 d .
N2 N 0.74324(11) -0.07842(15) 0.45449(5) 0.0501(3) Uani 1 1 d .
N3 N 0.78384(10) 0.00402(15) 0.49597(5) 0.0497(3) Uani 1 1 d .
N4 N 0.91573(11) 0.12501(16) 0.43772(5) 0.0560(4) Uani 1 1 d .
N5 N 0.87519(11) 0.04115(17) 0.39621(5) 0.0565(4) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 124.79(15)
N1 C1 H1 117.6
C2 C1 H1 117.6
C3 C2 C1 118.00(15)
C3 C2 H2 121.0
C1 C2 H2 121.0
C2 C3 C4 118.88(16)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 119.01(14)
C5 C4 H4 120.5
C3 C4 H4 120.5
N1 C5 C4 122.98(14)
N1 C5 C6 116.05(13)
C4 C5 C6 120.97(12)
N2 C6 N5 124.24(13)
N2 C6 C5 117.27(13)
N5 C6 C5 118.49(12)
N4 C7 N3 123.90(13)
N4 C7 C8 117.96(12)
N3 C7 C8 118.13(12)
C13 C8 C9 118.26(13)
C13 C8 C7 120.90(12)
C9 C8 C7 120.85(13)
C10 C9 C8 120.18(14)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 121.74(14)
C9 C10 H10 119.1
C11 C10 H10 119.1
C12 C11 C10 117.56(14)
C12 C11 C14 120.78(16)
C10 C11 C14 121.66(15)
C13 C12 C11 121.50(15)
C13 C12 H12 119.3
C11 C12 H12 119.2
C12 C13 C8 120.76(14)
C12 C13 H13 119.6
C8 C13 H13 119.6
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 N1 C5 116.34(14)
N3 N2 C6 118.34(12)
N2 N3 C7 117.73(12)
N5 N4 C7 118.17(12)
N4 N5 C6 117.57(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.328(2)
C1 C2 1.374(3)
C1 H1 0.9300
C2 C3 1.365(2)
C2 H2 0.9300
C3 C4 1.378(2)
C3 H3 0.9300
C4 C5 1.378(2)
C4 H4 0.9300
C5 N1 1.3360(18)
C5 C6 1.476(2)
C6 N2 1.3363(17)
C6 N5 1.3372(19)
C7 N4 1.3407(17)
C7 N3 1.3419(18)
C7 C8 1.468(2)
C8 C13 1.385(2)
C8 C9 1.3896(19)
C9 C10 1.377(2)
C9 H9 0.9300
C10 C11 1.383(2)
C10 H10 0.9300
C11 C12 1.380(2)
C11 C14 1.503(2)
C12 C13 1.374(2)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N2 N3 1.3165(17)
N4 N5 1.3234(18)
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
N1 C1 C2 C3 0.7(3)
C1 C2 C3 C4 -1.1(2)
C2 C3 C4 C5 0.8(2)
C3 C4 C5 N1 0.0(2)
C3 C4 C5 C6 178.69(13)
N1 C5 C6 N2 168.89(13)
C4 C5 C6 N2 -9.9(2)
N1 C5 C6 N5 -11.56(19)
C4 C5 C6 N5 169.65(13)
N4 C7 C8 C13 -3.77(19)
N3 C7 C8 C13 175.32(12)
N4 C7 C8 C9 176.21(13)
N3 C7 C8 C9 -4.7(2)
C13 C8 C9 C10 -0.4(2)
C7 C8 C9 C10 179.59(13)
C8 C9 C10 C11 -0.1(2)
C9 C10 C11 C12 0.4(2)
C9 C10 C11 C14 -178.94(15)
C10 C11 C12 C13 -0.2(2)
C14 C11 C12 C13 179.12(14)
C11 C12 C13 C8 -0.3(2)
C9 C8 C13 C12 0.6(2)
C7 C8 C13 C12 -179.42(13)
C2 C1 N1 C5 0.0(3)
C4 C5 N1 C1 -0.4(2)
C6 C5 N1 C1 -179.15(13)
N5 C6 N2 N3 1.5(2)
C5 C6 N2 N3 -178.96(12)
C6 N2 N3 C7 0.4(2)
N4 C7 N3 N2 -2.0(2)
C8 C7 N3 N2 179.00(11)
N3 C7 N4 N5 1.5(2)
C8 C7 N4 N5 -179.43(12)
C7 N4 N5 C6 0.4(2)
N2 C6 N5 N4 -2.0(2)
C5 C6 N5 N4 178.54(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199721
