#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/23/7122329.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_7122329
loop_
_publ_author_name
'Li, Lian-Hua'
'Niu, Zhi-Jie'
'Li, Ying-Xiu'
'Liang, Yong-Min'
_publ_section_title
;
 Transition-metal-free multinitrogenation of amides by C-C bond cleavage:
 a new approach to tetrazoles.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11148
_journal_page_last               11151
_journal_paper_doi               10.1039/c8cc06324a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C13 H15 N5'
_chemical_formula_sum            'C13 H15 N5'
_chemical_formula_weight         241.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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             2018-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.656(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0745(8)
_cell_length_b                   9.2802(7)
_cell_length_c                   11.0512(6)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      4.0460
_cell_volume                     1229.98(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000    0.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0111350000
_diffrn_orient_matrix_UB_12      -0.0577031000
_diffrn_orient_matrix_UB_13      0.0389164000
_diffrn_orient_matrix_UB_21      -0.0045885000
_diffrn_orient_matrix_UB_22      0.0496403000
_diffrn_orient_matrix_UB_23      0.0479534000
_diffrn_orient_matrix_UB_31      -0.0579006000
_diffrn_orient_matrix_UB_32      0.0071860000
_diffrn_orient_matrix_UB_33      -0.0189690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4342
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0459
_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/[σ²(Fo²)+(0.0350P)²+0.3021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1913
_reflns_number_total             2421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06324a2.cif
_cod_data_source_block           lilh_0507
_cod_depositor_comments
'Adding full bibliography for 7122325--7122329.cif.'
_cod_database_code               7122329
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C7(H7), C5(H5), C2(H2), C4(H4), C3(H3)
;
_olex2_date_sample_data_collection 2018-05-07
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_posn
N1 N 0.36379(11) 0.12040(15) 0.58560(12) 0.0294(3) Uani 1 d .
N2 N 0.31608(12) 0.17591(17) 0.47613(13) 0.0380(4) Uani 1 d .
N4 N 0.49568(12) 0.22288(17) 0.49611(13) 0.0363(4) Uani 1 d .
C9 C 0.47464(13) 0.15044(18) 0.59557(14) 0.0281(4) Uani 1 d .
N5 N 0.55163(11) 0.11796(16) 0.68803(13) 0.0319(3) Uani 1 d .
C1 C 0.02015(13) -0.1184(2) 0.65655(16) 0.0342(4) Uani 1 d .
H1 H 0.0058 -0.1212 0.5721 0.041 Uiso 1 calc R
N3 N 0.39559(13) 0.23551(18) 0.42640(13) 0.0416(4) Uani 1 d .
C10 C 0.54366(13) 0.00922(19) 0.78339(15) 0.0310(4) Uani 1 d .
H10A H 0.5073 -0.0776 0.7499 0.037 Uiso 1 calc R
H10B H 0.5029 0.0462 0.8474 0.037 Uiso 1 calc R
C6 C 0.11956(13) -0.05734(18) 0.71027(15) 0.0293(4) Uani 1 d .
C8 C 0.29629(13) 0.05951(18) 0.66831(15) 0.0298(4) Uani 1 d .
H8 H 0.3215 0.0607 0.7511 0.036 Uiso 1 calc R
C7 C 0.19834(13) 0.00078(19) 0.63177(15) 0.0311(4) Uani 1 d .
H7 H 0.1775 -0.0040 0.5482 0.037 Uiso 1 calc R
C5 C 0.13859(14) -0.0556(2) 0.83746(16) 0.0349(4) Uani 1 d .
H5 H 0.2037 -0.0145 0.8757 0.042 Uiso 1 calc R
C2 C -0.05726(14) -0.1746(2) 0.72609(17) 0.0398(5) Uani 1 d .
H2 H -0.1234 -0.2136 0.6885 0.048 Uiso 1 calc R
C12 C 0.72443(15) 0.1203(2) 0.80654(18) 0.0421(5) Uani 1 d .
H12A H 0.7156 0.1911 0.8693 0.051 Uiso 1 calc R
H12B H 0.8033 0.1043 0.8025 0.051 Uiso 1 calc R
C11 C 0.66546(14) -0.0195(2) 0.83080(17) 0.0384(5) Uani 1 d .
H11A H 0.6735 -0.0414 0.9172 0.046 Uiso 1 calc R
H11B H 0.6949 -0.0991 0.7875 0.046 Uiso 1 calc R
C13 C 0.66635(13) 0.1684(2) 0.68431(17) 0.0374(4) Uani 1 d .
H13A H 0.6690 0.2724 0.6759 0.045 Uiso 1 calc R
H13B H 0.6997 0.1241 0.6177 0.045 Uiso 1 calc R
C4 C 0.06215(14) -0.1139(2) 0.90669(17) 0.0406(5) Uani 1 d .
H4 H 0.0767 -0.1136 0.9912 0.049 Uiso 1 calc R
C3 C -0.03630(15) -0.1730(2) 0.85137(17) 0.0420(5) Uani 1 d .
H3 H -0.0881 -0.2113 0.8986 0.050 Uiso 1 calc R
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
N2 N1 C8 120.27(13)
C9 N1 N2 107.58(13)
C9 N1 C8 131.82(14)
N3 N2 N1 106.21(13)
C9 N4 N3 105.52(14)
N4 C9 N1 108.39(14)
N5 C9 N1 127.46(15)
N5 C9 N4 124.14(15)
C9 N5 C10 127.34(14)
C9 N5 C13 118.87(14)
C13 N5 C10 112.31(13)
C6 C1 H1 119.3
C2 C1 H1 119.3
C2 C1 C6 121.42(16)
N2 N3 N4 112.29(14)
N5 C10 H10A 111.2
N5 C10 H10B 111.2
N5 C10 C11 103.01(13)
H10A C10 H10B 109.1
C11 C10 H10A 111.2
C11 C10 H10B 111.2
C1 C6 C7 118.91(15)
C1 C6 C5 117.74(16)
C5 C6 C7 123.34(15)
N1 C8 H8 119.0
C7 C8 N1 122.04(15)
C7 C8 H8 119.0
C6 C7 H7 116.9
C8 C7 C6 126.23(16)
C8 C7 H7 116.9
C6 C5 H5 119.6
C4 C5 C6 120.78(16)
C4 C5 H5 119.6
C1 C2 H2 120.1
C3 C2 C1 119.86(16)
C3 C2 H2 120.1
H12A C12 H12B 109.1
C11 C12 H12A 111.1
C11 C12 H12B 111.1
C13 C12 H12A 111.1
C13 C12 H12B 111.1
C13 C12 C11 103.36(14)
C10 C11 H11A 110.9
C10 C11 H11B 110.9
C12 C11 C10 104.08(14)
C12 C11 H11A 110.9
C12 C11 H11B 110.9
H11A C11 H11B 109.0
N5 C13 C12 102.82(14)
N5 C13 H13A 111.2
N5 C13 H13B 111.2
C12 C13 H13A 111.2
C12 C13 H13B 111.2
H13A C13 H13B 109.1
C5 C4 H4 119.8
C5 C4 C3 120.45(17)
C3 C4 H4 119.8
C2 C3 C4 119.74(17)
C2 C3 H3 120.1
C4 C3 H3 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.3781(18)
N1 C9 1.359(2)
N1 C8 1.411(2)
N2 N3 1.285(2)
N4 C9 1.338(2)
N4 N3 1.361(2)
C9 N5 1.334(2)
N5 C10 1.470(2)
N5 C13 1.467(2)
C1 H1 0.9300
C1 C6 1.396(2)
C1 C2 1.380(2)
C10 H10A 0.9700
C10 H10B 0.9700
C10 C11 1.526(2)
C6 C7 1.463(2)
C6 C5 1.398(2)
C8 H8 0.9300
C8 C7 1.322(2)
C7 H7 0.9300
C5 H5 0.9300
C5 C4 1.376(2)
C2 H2 0.9300
C2 C3 1.378(3)
C12 H12A 0.9700
C12 H12B 0.9700
C12 C11 1.519(3)
C12 C13 1.515(2)
C11 H11A 0.9700
C11 H11B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
C4 H4 0.9300
C4 C3 1.385(3)
C3 H3 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
N1 N2 N3 N4 0.4(2)
N1 C9 N5 C10 18.9(3)
N1 C9 N5 C13 -176.16(16)
N1 C8 C7 C6 -176.19(16)
N2 N1 C9 N4 0.28(18)
N2 N1 C9 N5 179.00(17)
N2 N1 C8 C7 27.5(2)
N4 C9 N5 C10 -162.60(16)
N4 C9 N5 C13 2.4(3)
C9 N1 N2 N3 -0.39(18)
C9 N1 C8 C7 -159.89(17)
C9 N4 N3 N2 -0.2(2)
C9 N5 C10 C11 159.19(17)
C9 N5 C13 C12 176.03(16)
N5 C10 C11 C12 27.45(18)
C1 C6 C7 C8 -178.79(17)
C1 C6 C5 C4 0.8(3)
C1 C2 C3 C4 0.4(3)
N3 N4 C9 N1 -0.07(18)
N3 N4 C9 N5 -178.84(16)
C10 N5 C13 C12 -16.84(19)
C6 C1 C2 C3 -0.9(3)
C6 C5 C4 C3 -1.3(3)
C8 N1 N2 N3 173.87(15)
C8 N1 C9 N4 -173.06(17)
C8 N1 C9 N5 5.7(3)
C7 C6 C5 C4 -178.99(17)
C5 C6 C7 C8 1.0(3)
C5 C4 C3 C2 0.7(3)
C2 C1 C6 C7 -179.91(17)
C2 C1 C6 C5 0.3(3)
C11 C12 C13 N5 33.36(19)
C13 N5 C10 C11 -6.60(19)
C13 C12 C11 C10 -38.21(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189131
