#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/23/7122328.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_7122328
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         'C11 H19 N5'
_chemical_formula_sum            'C11 H19 N5'
_chemical_formula_weight         221.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_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_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                94.814(14)
_cell_angle_beta                 103.101(15)
_cell_angle_gamma                96.922(14)
_cell_formula_units_Z            2
_cell_length_a                   6.8335(13)
_cell_length_b                   9.1979(15)
_cell_length_c                   10.0075(17)
_cell_measurement_reflns_used    802
_cell_measurement_temperature    292.55(10)
_cell_measurement_theta_max      24.1110
_cell_measurement_theta_min      4.0740
_cell_volume                     604.13(19)
_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      292.55(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -60.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  120.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -59.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   25.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   42.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   52.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -77.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00   98.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430    0.0000  -30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0651268000
_diffrn_orient_matrix_UB_12      -0.0269174000
_diffrn_orient_matrix_UB_13      0.0552556000
_diffrn_orient_matrix_UB_21      -0.0855843000
_diffrn_orient_matrix_UB_22      -0.0386824000
_diffrn_orient_matrix_UB_23      0.0170626000
_diffrn_orient_matrix_UB_31      0.0055574000
_diffrn_orient_matrix_UB_32      -0.0624060000
_diffrn_orient_matrix_UB_33      -0.0449705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3965
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41540
_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    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0627
_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)+(0.0629P)²+0.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1526
_reflns_number_total             2371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06324a2.cif
_cod_data_source_block           lilh_416_3n3
_cod_depositor_comments
'Adding full bibliography for 7122325--7122329.cif.'
_cod_original_cell_volume        604.14(18)
_cod_database_code               7122328
_reflns_odcompleteness_completeness 99.72
_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, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H9AA(0.4) H9AB(0.4) H9BC(0.6) H9BD(0.6) C10(0.4) H10A(0.4)
 H10B(0.4) C10'(0.6) H10C(0.6) H10D(0.6)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9AA,H9AB), C9(H9BC,H9BD), C10(H10A,H10B), C10'(H10C,H10D)
;
_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, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.4366(3) 0.6960(2) 0.44246(18) 0.0436(5) Uani 1 d . . .
N2 N 0.5793(3) 0.6716(3) 0.3703(2) 0.0603(6) Uani 1 d . . .
N3 N 0.7436(3) 0.6609(2) 0.4602(2) 0.0613(6) Uani 1 d . . .
N4 N 0.7177(3) 0.6774(2) 0.5904(2) 0.0529(6) Uani 1 d . . .
N5 N 0.4448(3) 0.7305(2) 0.68537(18) 0.0516(6) Uani 1 d B . .
C1 C 0.2395(3) 0.7342(2) 0.3708(2) 0.0428(6) Uani 1 d . . .
H1 H 0.1382 0.6997 0.4208 0.051 Uiso 1 calc . . R
C2 C 0.2513(4) 0.9009(3) 0.3745(3) 0.0560(7) Uani 1 d . . .
H2A H 0.3566 0.9385 0.3305 0.067 Uiso 1 calc . . R
H2B H 0.2868 0.9456 0.4697 0.067 Uiso 1 calc . . R
C3 C 0.0487(4) 0.9422(3) 0.3002(3) 0.0659(8) Uani 1 d . . .
H3A H -0.0531 0.9145 0.3506 0.079 Uiso 1 calc . . R
H3B H 0.0618 1.0481 0.2982 0.079 Uiso 1 calc . . R
C4 C -0.0199(5) 0.8656(3) 0.1534(3) 0.0704(8) Uani 1 d . . .
H4A H -0.1524 0.8897 0.1103 0.084 Uiso 1 calc . . R
H4B H 0.0748 0.9007 0.1002 0.084 Uiso 1 calc . . R
C5 C -0.0313(4) 0.7007(3) 0.1525(2) 0.0589(7) Uani 1 d . . .
H5A H -0.0703 0.6543 0.0578 0.071 Uiso 1 calc . . R
H5B H -0.1345 0.6648 0.1989 0.071 Uiso 1 calc . . R
C6 C 0.1725(4) 0.6584(3) 0.2246(2) 0.0537(7) Uani 1 d . . .
H6A H 0.1599 0.5523 0.2259 0.064 Uiso 1 calc . . R
H6B H 0.2738 0.6870 0.1740 0.064 Uiso 1 calc . . R
C7 C 0.5261(3) 0.7005(2) 0.5775(2) 0.0405(5) Uani 1 d . . .
C8 C 0.2307(4) 0.7046(3) 0.6862(2) 0.0538(7) Uani 1 d B . .
H8A H 0.1681 0.6074 0.6406 0.065 Uiso 1 calc . . R
H8B H 0.1581 0.7780 0.6406 0.065 Uiso 1 calc . . R
C9 C 0.2318(5) 0.7168(4) 0.8372(3) 0.0783(9) Uani 1 d . . .
H9AA H 0.2152 0.8159 0.8695 0.094 Uiso 0.40 calc A 1 R
H9AB H 0.1223 0.6482 0.8532 0.094 Uiso 0.40 calc A 1 R
H9BC H 0.1301 0.7757 0.8553 0.094 Uiso 0.60 calc A 2 R
H9BD H 0.2019 0.6197 0.8652 0.094 Uiso 0.60 calc A 2 R
C11 C 0.5730(5) 0.7320(6) 0.8254(3) 0.0815(11) Uani 1 d . . .
H11A H 0.694(6) 0.817(4) 0.838(3) 0.123(14) Uiso 1 d . . .
H11B H 0.629(7) 0.654(5) 0.836(4) 0.16(2) Uiso 1 d . . .
C10 C 0.4267(14) 0.6816(12) 0.9088(9) 0.071(2) Uani 0.40 d B 1 .
H10A H 0.4199 0.5763 0.9141 0.085 Uiso 0.40 calc B 1 R
H10B H 0.4679 0.7326 1.0017 0.085 Uiso 0.40 calc B 1 R
C10' C 0.4324(9) 0.7863(8) 0.9128(6) 0.0777(17) Uani 0.60 d B 2 .
H10C H 0.4661 0.7557 1.0048 0.093 Uiso 0.60 calc B 2 R
H10D H 0.4417 0.8928 0.9205 0.093 Uiso 0.60 calc B 2 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 C1 120.00(17)
C7 N1 N2 107.30(18)
C7 N1 C1 131.86(17)
N3 N2 N1 106.62(19)
N2 N3 N4 111.53(19)
C7 N4 N3 105.58(19)
C7 N5 C8 126.67(19)
C7 N5 C11 118.0(2)
C8 N5 C11 110.6(2)
N1 C1 H1 108.0
N1 C1 C2 109.91(18)
N1 C1 C6 111.22(17)
C2 C1 H1 108.0
C6 C1 H1 108.0
C6 C1 C2 111.61(19)
C1 C2 H2A 109.5
C1 C2 H2B 109.5
C1 C2 C3 110.56(19)
H2A C2 H2B 108.1
C3 C2 H2A 109.5
C3 C2 H2B 109.5
C2 C3 H3A 109.4
C2 C3 H3B 109.4
H3A C3 H3B 108.0
C4 C3 C2 111.3(2)
C4 C3 H3A 109.4
C4 C3 H3B 109.4
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C5 C4 C3 110.7(2)
C5 C4 H4A 109.5
C5 C4 H4B 109.5
C4 C5 H5A 109.4
C4 C5 H5B 109.4
C4 C5 C6 111.2(2)
H5A C5 H5B 108.0
C6 C5 H5A 109.4
C6 C5 H5B 109.4
C1 C6 C5 110.11(18)
C1 C6 H6A 109.6
C1 C6 H6B 109.6
C5 C6 H6A 109.6
C5 C6 H6B 109.6
H6A C6 H6B 108.2
N4 C7 N1 109.0(2)
N4 C7 N5 123.6(2)
N5 C7 N1 127.32(19)
N5 C8 H8A 111.0
N5 C8 H8B 111.0
N5 C8 C9 103.9(2)
H8A C8 H8B 109.0
C9 C8 H8A 111.0
C9 C8 H8B 111.0
C8 C9 H9AA 110.5
C8 C9 H9AB 110.5
C8 C9 H9BC 110.3
C8 C9 H9BD 110.3
H9AA C9 H9AB 108.6
H9AA C9 H9BC 37.9
H9AA C9 H9BD 135.0
H9AB C9 H9BC 73.8
H9AB C9 H9BD 37.5
H9BC C9 H9BD 108.5
C10 C9 C8 106.4(4)
C10 C9 H9AA 110.5
C10 C9 H9AB 110.5
C10 C9 H9BC 138.6
C10 C9 H9BD 75.1
C10' C9 C8 107.3(3)
C10' C9 H9AA 74.6
C10' C9 H9AB 137.5
C10' C9 H9BC 110.3
C10' C9 H9BD 110.3
C10' C9 C10 38.5(4)
N5 C11 H11A 107(2)
N5 C11 H11B 113(3)
N5 C11 C10 104.3(4)
N5 C11 C10' 100.5(3)
H11A C11 H11B 105(4)
C10 C11 H11A 135(2)
C10 C11 H11B 91(3)
C10 C11 C10' 36.7(4)
C10' C11 H11A 106(2)
C10' C11 H11B 124(3)
C9 C10 C11 105.7(5)
C9 C10 H10A 110.6
C9 C10 H10B 110.6
C11 C10 H10A 110.6
C11 C10 H10B 110.6
H10A C10 H10B 108.7
C9 C10' C11 103.8(4)
C9 C10' H10C 111.0
C9 C10' H10D 111.0
C11 C10' H10C 111.0
C11 C10' H10D 111.0
H10C C10' H10D 109.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.367(3)
N1 C1 1.473(3)
N1 C7 1.346(3)
N2 N3 1.290(3)
N3 N4 1.353(3)
N4 C7 1.330(3)
N5 C7 1.346(3)
N5 C8 1.456(3)
N5 C11 1.472(3)
C1 H1 0.9800
C1 C2 1.522(3)
C1 C6 1.512(3)
C2 H2A 0.9700
C2 H2B 0.9700
C2 C3 1.524(3)
C3 H3A 0.9700
C3 H3B 0.9700
C3 C4 1.520(3)
C4 H4A 0.9700
C4 H4B 0.9700
C4 C5 1.509(4)
C5 H5A 0.9700
C5 H5B 0.9700
C5 C6 1.528(3)
C6 H6A 0.9700
C6 H6B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.504(3)
C9 H9AA 0.9700
C9 H9AB 0.9700
C9 H9BC 0.9700
C9 H9BD 0.9700
C9 C10 1.450(8)
C9 C10' 1.448(6)
C11 H11A 1.05(4)
C11 H11B 0.86(4)
C11 C10 1.497(10)
C11 C10' 1.537(7)
C10 H10A 0.9700
C10 H10B 0.9700
C10' H10C 0.9700
C10' H10D 0.9700
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 -0.1(3)
N1 C1 C2 C3 179.8(2)
N1 C1 C6 C5 -179.6(2)
N2 N1 C1 C2 -90.6(2)
N2 N1 C1 C6 33.6(3)
N2 N1 C7 N4 -1.0(3)
N2 N1 C7 N5 175.9(2)
N2 N3 N4 C7 -0.5(3)
N3 N4 C7 N1 0.9(3)
N3 N4 C7 N5 -176.1(2)
N5 C8 C9 C10 -25.3(5)
N5 C8 C9 C10' 15.1(4)
N5 C11 C10 C9 -24.5(7)
N5 C11 C10' C9 36.8(6)
C1 N1 N2 N3 171.36(19)
C1 N1 C7 N4 -170.1(2)
C1 N1 C7 N5 6.7(4)
C1 C2 C3 C4 -55.3(3)
C2 C1 C6 C5 -56.4(3)
C2 C3 C4 C5 56.1(3)
C3 C4 C5 C6 -56.9(3)
C4 C5 C6 C1 57.0(3)
C6 C1 C2 C3 55.9(3)
C7 N1 N2 N3 0.7(3)
C7 N1 C1 C2 77.5(3)
C7 N1 C1 C6 -158.4(2)
C7 N5 C8 C9 164.6(2)
C7 N5 C11 C10 -148.6(5)
C7 N5 C11 C10' 174.0(3)
C8 N5 C7 N1 27.9(4)
C8 N5 C7 N4 -155.7(2)
C8 N5 C11 C10 8.7(6)
C8 N5 C11 C10' -28.7(5)
C8 C9 C10 C11 31.2(7)
C8 C9 C10' C11 -32.7(5)
C11 N5 C7 N1 -178.9(3)
C11 N5 C7 N4 -2.5(4)
C11 N5 C8 C9 9.7(3)
C10 C9 C10' C11 62.0(7)
C10 C11 C10' C9 -63.0(7)
C10' C9 C10 C11 -66.2(8)
C10' C11 C10 C9 63.9(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102011721
