#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:06:59 +0100 (lun 04 de nov de 2019) $
#$Revision: 222437 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/38/4033860.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_4033860
loop_
_publ_author_name
'Yang, Hongwei'
'Huang, Liping'
'Xu, Minxian'
'Tang, Yongxing'
'Wang, Bohan'
'Cheng, Guangbin'
_publ_section_title
;
 Strategy for Extending the Nitrogen Chain: The Bis(1,2,3-triazole)
 Formation Reaction from Tosylhydrazones and N-Amino Azole.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10629
_journal_page_last               10634
_journal_paper_doi               10.1021/acs.joc.9b00801
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C4 H4 N6'
_chemical_formula_sum            'C4 H4 N6'
_chemical_formula_weight         136.13
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0140(18)
_cell_length_b                   17.049(2)
_cell_length_c                   4.9969(5)
_cell_measurement_reflns_used    729
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      3.76
_cell_volume                     1193.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2003
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         628
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0354
_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)+(0.0396P)²+0.3655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                505
_reflns_number_total             628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00801_si_001.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'Fdd2 '
_cod_database_code               4033860
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 -0.01531(15) 0.16142(11) 0.8132(3) 0.0295(5) Uani 1 1 d .
H1 H -0.0342 0.2102 0.8884 0.035 Uiso 1 1 calc R
C2 C -0.04277(16) 0.08988(11) 0.9028(4) 0.0256(5) Uani 1 1 d .
H2 H -0.0836 0.0776 1.0488 0.031 Uiso 1 1 calc R
N1 N 0.00197(15) 0.04029(7) 0.7339(3) 0.0218(4) Uani 1 1 d .
N2 N 0.05480(13) 0.07800(8) 0.5486(3) 0.0297(5) Uani 1 1 d .
N3 N 0.04351(14) 0.15255(9) 0.5989(3) 0.0319(5) Uani 1 1 d .
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
C1 0.0339(12) 0.0213(10) 0.0332(11) -0.0039(8) -0.0029(11) 0.0045(8)
C2 0.0272(12) 0.0266(11) 0.0229(11) -0.0040(8) 0.0027(10) 0.0016(9)
N1 0.0279(9) 0.0154(7) 0.0221(7) 0.0014(7) 0.0016(7) -0.0008(7)
N2 0.0381(10) 0.0207(8) 0.0303(10) 0.0055(7) 0.0107(10) -0.0006(7)
N3 0.0408(11) 0.0216(9) 0.0334(12) 0.0029(8) 0.0060(9) -0.0011(8)
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_3
C2 C1 N3 109.41(18) .
C2 C1 H1 125.3 .
N3 C1 H1 125.3 .
N1 C2 C1 103.03(19) .
N1 C2 H2 128.5 .
C1 C2 H2 128.5 .
N2 N1 C2 112.68(13) .
N2 N1 N1 119.90(17) 2
C2 N1 N1 127.41(18) 2
N3 N2 N1 105.41(17) .
N2 N3 C1 109.47(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.355(3) .
C1 N3 1.360(2) .
C1 H1 0.9500 .
C2 N1 1.349(3) .
C2 H2 0.9500 .
N1 N2 1.349(3) .
N1 N1 1.375(2) 2
N2 N3 1.3052(19) .
