#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012782.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012782
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Gaponik, Pavel N.'
'Grigoriev, Yuri V.'
'Ivashkevich, Ludmila S.'
_publ_section_title
;
 Bis(5-phenyltetrazol-2-yl)methane
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o381
_journal_page_last               o383
_journal_paper_doi               10.1107/S0108270102008466
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C15 H12 N8'
_chemical_formula_sum            'C15 H12 N8'
_chemical_formula_weight         304.33
_chemical_name_systematic
;
Bis(5-phenyltetrazol-2-yl)methane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 100.16(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.053(2)
_cell_length_b                   7.409(2)
_cell_length_c                   17.956(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8
_cell_measurement_theta_min      17.5
_cell_volume                     1447.4(6)
_computing_cell_refinement       'R3m Software'
_computing_data_collection       'R3m Software (Nicolet, 1980)'
_computing_data_reduction        'R3m Software'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nicolet R3m four-circle'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4606
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0693P)²+0.0755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.126
_reflns_number_gt                3025
_reflns_number_total             4258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1109.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012782
_cod_database_fobs_code          2012782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.12733(11) 0.45902(17) -0.09593(8) 0.0477(3) Uani d . 1 . . C
H1A 0.1173(12) 0.518(2) -0.1466(8) 0.053(4) Uiso d . 1 . . H
H1B 0.1127(13) 0.542(2) -0.0542(9) 0.057(4) Uiso d . 1 . . H
N1A 0.31064(9) 0.35311(14) -0.01017(5) 0.0437(2) Uani d . 1 . . N
N2A 0.25352(9) 0.39768(14) -0.07944(5) 0.0435(2) Uani d . 1 . . N
N3A 0.32068(10) 0.37400(16) -0.13275(6) 0.0519(3) Uani d . 1 . . N
N4A 0.42708(10) 0.31252(16) -0.09787(6) 0.0516(3) Uani d . 1 . . N
C5A 0.41962(10) 0.30024(15) -0.02336(6) 0.0402(2) Uani d . 1 . . C
C6A 0.52024(10) 0.23768(15) 0.03519(7) 0.0415(2) Uani d . 1 . . C
C7A 0.50769(12) 0.2363(2) 0.11072(7) 0.0512(3) Uani d . 1 . . C
H7A 0.4346(15) 0.278(2) 0.1254(9) 0.062(4) Uiso d . 1 . . H
C8A 0.60299(14) 0.1781(2) 0.16584(8) 0.0595(3) Uani d . 1 . . C
H8A 0.5926(15) 0.185(2) 0.2179(10) 0.065(4) Uiso d . 1 . . H
C9A 0.71158(13) 0.1187(2) 0.14608(9) 0.0584(3) Uani d . 1 . . C
H9A 0.7806(16) 0.070(2) 0.1858(10) 0.076(5) Uiso d . 1 . . H
C10A 0.72538(12) 0.1201(2) 0.07121(9) 0.0565(3) Uani d . 1 . . C
H10A 0.8000(15) 0.081(2) 0.0555(9) 0.071(5) Uiso d . 1 . . H
C11A 0.63074(12) 0.17982(17) 0.01598(8) 0.0491(3) Uani d . 1 . . C
H11A 0.6419(15) 0.184(2) -0.0358(10) 0.067(5) Uiso d . 1 . . H
N1B 0.03684(9) 0.17582(13) -0.14913(5) 0.0428(2) Uani d . 1 . . N
N2B 0.04398(9) 0.30665(13) -0.09793(5) 0.0427(2) Uani d . 1 . . N
N3B -0.02780(11) 0.28286(16) -0.04728(6) 0.0531(3) Uani d . 1 . . N
N4B -0.08581(11) 0.13010(16) -0.06540(6) 0.0531(3) Uani d . 1 . . N
C5B -0.04471(9) 0.06613(16) -0.12719(6) 0.0397(2) Uani d . 1 . . C
C6B -0.08221(9) -0.10783(16) -0.16309(6) 0.0397(2) Uani d . 1 . . C
C7B -0.04800(11) -0.15581(18) -0.23142(7) 0.0458(3) Uani d . 1 . . C
H7B -0.0021(13) -0.075(2) -0.2564(9) 0.059(4) Uiso d . 1 . . H
C8B -0.08235(12) -0.32230(19) -0.26353(7) 0.0528(3) Uani d . 1 . . C
H8B -0.0555(15) -0.356(2) -0.3121(9) 0.066(4) Uiso d . 1 . . H
C9B -0.15069(12) -0.4402(2) -0.22802(8) 0.0538(3) Uani d . 1 . . C
H9B -0.1710(15) -0.556(2) -0.2488(10) 0.075(5) Uiso d . 1 . . H
C10B -0.18588(12) -0.39208(19) -0.16055(8) 0.0522(3) Uani d . 1 . . C
H10B -0.2349(15) -0.471(2) -0.1343(9) 0.070(5) Uiso d . 1 . . H
C11B -0.15178(11) -0.22668(18) -0.12797(7) 0.0458(3) Uani d . 1 . . C
H11B -0.1763(12) -0.1904(19) -0.0810(8) 0.050(4) Uiso d . 1 . . H
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_publ_flag
N2A C1 N2B 110.18(10) yes
N2A C1 H1A 105.8(8) ?
N2B C1 H1A 110.4(8) ?
N2A C1 H1B 108.4(9) ?
N2B C1 H1B 108.0(8) ?
H1A C1 H1B 114.0(12) ?
C5A N1A N2A 101.65(10) yes
N3A N2A N1A 114.11(10) yes
N3A N2A C1 122.51(10) ?
N1A N2A C1 123.32(10) ?
N4A N3A N2A 105.71(10) yes
N3A N4A C5A 106.75(10) yes
N1A C5A N4A 111.77(10) yes
N1A C5A C6A 124.30(10) ?
N4A C5A C6A 123.92(10) ?
C7A C6A C11A 118.86(12) ?
C7A C6A C5A 120.66(11) ?
C11A C6A C5A 120.48(11) ?
C8A C7A C6A 120.51(12) ?
C8A C7A H7A 119.0(10) ?
C6A C7A H7A 120.5(10) ?
C7A C8A C9A 120.16(14) ?
C7A C8A H8A 118.2(10) ?
C9A C8A H8A 121.6(10) ?
C10A C9A C8A 119.88(13) ?
C10A C9A H9A 119.3(9) ?
C8A C9A H9A 120.8(9) ?
C9A C10A C11A 120.14(13) ?
C9A C10A H10A 122.1(10) ?
C11A C10A H10A 117.7(10) ?
C10A C11A C6A 120.43(13) ?
C10A C11A H11A 119.6(10) ?
C6A C11A H11A 119.9(10) ?
C5B N1B N2B 101.67(9) yes
N3B N2B N1B 114.19(10) yes
N3B N2B C1 122.82(10) ?
N1B N2B C1 122.94(10) ?
N4B N3B N2B 105.72(10) yes
N3B N4B C5B 106.53(10) yes
N1B C5B N4B 111.88(11) yes
N1B C5B C6B 124.23(10) ?
N4B C5B C6B 123.83(10) ?
C11B C6B C7B 119.71(11) ?
C11B C6B C5B 119.51(10) ?
C7B C6B C5B 120.78(10) ?
C8B C7B C6B 119.79(12) ?
C8B C7B H7B 119.8(9) ?
C6B C7B H7B 120.4(9) ?
C9B C8B C7B 120.16(12) ?
C9B C8B H8B 121.1(10) ?
C7B C8B H8B 118.7(10) ?
C8B C9B C10B 120.16(13) ?
C8B C9B H9B 120.1(10) ?
C10B C9B H9B 119.7(10) ?
C11B C10B C9B 120.12(12) ?
C11B C10B H10B 117.4(10) ?
C9B C10B H10B 122.5(10) ?
C10B C11B C6B 120.06(12) ?
C10B C11B H11B 121.2(8) ?
C6B C11B H11B 118.7(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2A . 1.4470(16) yes
C1 N2B . 1.4535(16) yes
C1 H1A . 0.997(15) ?
C1 H1B . 1.003(15) ?
N1A C5A . 1.3271(15) yes
N1A N2A . 1.3333(14) yes
N2A N3A . 1.3223(14) yes
N3A N4A . 1.3127(16) yes
N4A C5A . 1.3579(15) yes
C5A C6A . 1.4645(17) yes
C6A C7A . 1.3873(17) ?
C6A C11A . 1.3939(17) ?
C7A C8A . 1.3812(19) ?
C7A H7A . 0.945(16) ?
C8A C9A . 1.382(2) ?
C8A H8A . 0.964(16) ?
C9A C10A . 1.379(2) ?
C9A H9A . 1.014(19) ?
C10A C11A . 1.3812(19) ?
C10A H10A . 0.961(16) ?
C11A H11A . 0.959(17) ?
N1B C5B . 1.3242(15) yes
N1B N2B . 1.3287(13) yes
N2B N3B . 1.3200(15) yes
N3B N4B . 1.3131(16) yes
N4B C5B . 1.3564(15) yes
C5B C6B . 1.4677(16) yes
C6B C11B . 1.3913(16) ?
C6B C7B . 1.3922(16) ?
C7B C8B . 1.3860(19) ?
C7B H7B . 0.949(15) ?
C8B C9B . 1.382(2) ?
C8B H8B . 1.001(16) ?
C9B C10B . 1.383(2) ?
C9B H9B . 0.946(18) ?
C10B C11B . 1.3813(19) ?
C10B H10B . 0.973(17) ?
C11B H11B . 0.968(14) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1B N3B 3_565 1.003(15) 2.548(15) 3.5324(18) 166.9(12)
C10A H10A CgTz 3_655 0.961(16) 3.116(16) 3.9153(18) 141.6(12)
C9B H9B CgBz 2_444 0.946(18) 2.877(16) 3.6548(18) 140.1(13)
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
C5A N1A N2A N3A 0.36(13)
C5A N1A N2A C1 177.73(10)
N2B C1 N2A N3A 99.30(13)
N2B C1 N2A N1A -77.85(14)
N1A N2A N3A N4A -0.46(14)
C1 N2A N3A N4A -177.85(11)
N2A N3A N4A C5A 0.35(14)
N2A N1A C5A N4A -0.12(13)
N2A N1A C5A C6A 179.37(10)
N3A N4A C5A N1A -0.15(14)
N3A N4A C5A C6A -179.64(11)
N1A C5A C6A C7A -2.31(18)
N4A C5A C6A C7A 177.13(12)
N1A C5A C6A C11A 178.22(11)
N4A C5A C6A C11A -2.35(17)
C11A C6A C7A C8A -0.2(2)
C5A C6A C7A C8A -179.67(12)
C6A C7A C8A C9A -0.7(2)
C7A C8A C9A C10A 0.9(2)
C8A C9A C10A C11A -0.3(2)
C9A C10A C11A C6A -0.6(2)
C7A C6A C11A C10A 0.80(19)
C5A C6A C11A C10A -179.71(12)
C5B N1B N2B N3B -0.21(13)
C5B N1B N2B C1 177.35(10)
N2A C1 N2B N3B 112.74(13)
N2A C1 N2B N1B -64.61(14)
N1B N2B N3B N4B -0.23(14)
C1 N2B N3B N4B -177.79(11)
N2B N3B N4B C5B 0.56(14)
N2B N1B C5B N4B 0.58(13)
N2B N1B C5B C6B -176.81(10)
N3B N4B C5B N1B -0.75(14)
N3B N4B C5B C6B 176.65(10)
N1B C5B C6B C11B 168.85(11)
N4B C5B C6B C11B -8.23(17)
N1B C5B C6B C7B -10.54(17)
N4B C5B C6B C7B 172.38(11)
C11B C6B C7B C8B -0.69(17)
C5B C6B C7B C8B 178.70(11)
C6B C7B C8B C9B 0.21(19)
C7B C8B C9B C10B 0.5(2)
C8B C9B C10B C11B -0.7(2)
C9B C10B C11B C6B 0.18(19)
C7B C6B C11B C10B 0.49(17)
C5B C6B C11B C10B -178.90(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3732892
