#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:54:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180114 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/12/7101215.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_7101215
loop_
_publ_author_name
A.Kraft
A.F.Tominey
G.M.Rosair
D.Andrew
J.Dupre
_publ_section_title
'Unusually weak binding interactions between tetrazole and amidines'
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b604393c
_journal_year                    2006
_chemical_formula_moiety         'C10 H30 N4, 4(C5 H6 N5 O)'
_chemical_formula_sum            'C30 H54 N24 O4'
_chemical_formula_weight         814.97
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.000(12)
_cell_angle_beta                 110.275(12)
_cell_angle_gamma                90.000(11)
_cell_formula_units_Z            2
_cell_length_a                   11.1364(14)
_cell_length_b                   13.482(2)
_cell_length_c                   14.299(2)
_cell_measurement_reflns_used    2725
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      3.23
_cell_volume                     2013.8(5)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.761
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  Xcalibur-2
_diffrn_measurement_method       'φ 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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.1181
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10445
_diffrn_reflns_theta_full        22.32
_diffrn_reflns_theta_max         22.32
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.1043
_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)+(0.0388P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                1513
_reflns_number_total             1959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b604393c.txt
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7101215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.0108(6) 0.9450(4) 0.4971(5) 0.0190(18) Uani 1 1 d .
H1A H 1.1017 0.9333 0.5056 0.023 Uiso 1 1 calc R
H1B H 0.9933 0.9114 0.5526 0.023 Uiso 1 1 calc R
C2 C 0.9274(5) 0.9002(5) 0.3999(5) 0.0177(18) Uani 1 1 d .
H2A H 0.8364 0.9107 0.3917 0.021 Uiso 1 1 calc R
H2B H 0.9440 0.9341 0.3441 0.021 Uiso 1 1 calc R
N3 N 0.9518(4) 0.7927(4) 0.3955(4) 0.0175(15) Uani 1 1 d .
H3A H 0.9265 0.7604 0.4422 0.021 Uiso 1 1 calc R
H3B H 1.0384 0.7826 0.4117 0.021 Uiso 1 1 calc R
C4 C 0.8833(6) 0.7490(5) 0.2955(5) 0.0189(19) Uani 1 1 d .
H4A H 0.8960 0.7924 0.2439 0.023 Uiso 1 1 calc R
H4B H 0.7905 0.7472 0.2843 0.023 Uiso 1 1 calc R
C5 C 0.9275(5) 0.6458(5) 0.2833(5) 0.0169(18) Uani 1 1 d .
H5A H 1.0213 0.6466 0.2988 0.020 Uiso 1 1 calc R
H5B H 0.8869 0.6251 0.2129 0.020 Uiso 1 1 calc R
C6 C 0.8952(6) 0.5700(5) 0.3504(5) 0.0224(19) Uani 1 1 d .
H6A H 0.9403 0.5879 0.4211 0.027 Uiso 1 1 calc R
H6B H 0.8021 0.5716 0.3379 0.027 Uiso 1 1 calc R
N7 N 0.9335(4) 0.4668(4) 0.3320(4) 0.0196(16) Uani 1 1 d .
H7A H 0.8901 0.4494 0.2676 0.029 Uiso 1 1 calc R
H7B H 0.9143 0.4235 0.3735 0.029 Uiso 1 1 calc R
H7C H 1.0191 0.4651 0.3436 0.029 Uiso 1 1 calc R
C11 C 0.6850(7) 0.2843(6) 0.4996(5) 0.0177(18) Uani 1 1 d .
N12 N 0.6175(5) 0.3560(5) 0.4412(4) 0.0223(15) Uani 1 1 d .
N13 N 0.7042(5) 0.4045(4) 0.4114(4) 0.0259(17) Uani 1 1 d .
N14 N 0.8168(5) 0.3611(5) 0.4508(4) 0.0225(15) Uani 1 1 d .
N15 N 0.8073(5) 0.2823(4) 0.5081(4) 0.0200(15) Uani 1 1 d .
N16 N 0.6254(5) 0.2146(4) 0.5417(4) 0.0217(16) Uani 1 1 d .
H16 H 0.5420 0.2198 0.5266 0.026 Uiso 1 1 calc R
C17 C 0.6851(7) 0.1396(6) 0.6038(5) 0.0221(19) Uani 1 1 d .
O17 O 0.8022(4) 0.1267(3) 0.6351(3) 0.0248(13) Uani 1 1 d .
C18 C 0.5987(6) 0.0681(6) 0.6306(5) 0.0211(19) Uani 1 1 d .
C19 C 0.6214(6) -0.0281(6) 0.6262(5) 0.037(2) Uani 1 1 d .
H19B H 0.5688 -0.0754 0.6429 0.045 Uiso 1 1 calc R
H19A H 0.6902 -0.0497 0.6064 0.045 Uiso 1 1 calc R
C20 C 0.4927(6) 0.1083(5) 0.6609(5) 0.033(2) Uani 1 1 d .
H20C H 0.4435 0.0532 0.6743 0.049 Uiso 1 1 calc R
H20A H 0.4363 0.1495 0.6071 0.049 Uiso 1 1 calc R
H20B H 0.5287 0.1485 0.7213 0.049 Uiso 1 1 calc R
C21 C 0.7088(6) -0.1432(6) 0.0781(5) 0.0142(18) Uani 1 1 d .
N22 N 0.6551(5) -0.2311(4) 0.0484(4) 0.0187(15) Uani 1 1 d .
N23 N 0.7426(5) -0.2788(4) 0.0175(4) 0.0238(16) Uani 1 1 d .
N24 N 0.8409(5) -0.2200(5) 0.0303(4) 0.0210(15) Uani 1 1 d .
N25 N 0.8226(5) -0.1318(5) 0.0688(4) 0.0202(15) Uani 1 1 d .
N26 N 0.6465(5) -0.0715(4) 0.1155(4) 0.0199(15) Uani 1 1 d .
H26 H 0.5648 -0.0805 0.1060 0.024 Uiso 1 1 calc R
C27 C 0.7042(7) 0.0110(5) 0.1657(5) 0.0208(19) Uani 1 1 d .
O27 O 0.8201(4) 0.0257(3) 0.1898(3) 0.0250(13) Uani 1 1 d .
C28 C 0.6217(6) 0.0831(5) 0.1954(5) 0.0190(18) Uani 1 1 d .
C29 C 0.4970(6) 0.0896(5) 0.1496(5) 0.0240(19) Uani 1 1 d .
H29B H 0.4552 0.0473 0.0948 0.029 Uiso 1 1 calc R
H29A H 0.4487 0.1367 0.1713 0.029 Uiso 1 1 calc R
C30 C 0.6928(6) 0.1519(6) 0.2785(6) 0.042(2) Uani 1 1 d .
H30C H 0.6326 0.1989 0.2905 0.063 Uiso 1 1 calc R
H30B H 0.7574 0.1884 0.2600 0.063 Uiso 1 1 calc R
H30A H 0.7350 0.1134 0.3391 0.063 Uiso 1 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'
O O 0.0106 0.0060 '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_1
_geom_angle_site_symmetry_3
C2 C1 C1 112.7(7) . 3_776
C2 C1 H1A 109.0 . .
C1 C1 H1A 109.0 3_776 .
C2 C1 H1B 109.0 . .
C1 C1 H1B 109.0 3_776 .
H1A C1 H1B 107.8 . .
N3 C2 C1 111.6(5) . .
N3 C2 H2A 109.3 . .
C1 C2 H2A 109.3 . .
N3 C2 H2B 109.3 . .
C1 C2 H2B 109.3 . .
H2A C2 H2B 108.0 . .
C2 N3 C4 112.8(5) . .
C2 N3 H3A 109.0 . .
C4 N3 H3A 109.0 . .
C2 N3 H3B 109.0 . .
C4 N3 H3B 109.0 . .
H3A N3 H3B 107.8 . .
N3 C4 C5 113.4(5) . .
N3 C4 H4A 108.9 . .
C5 C4 H4A 108.9 . .
N3 C4 H4B 108.9 . .
C5 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C4 C5 C6 112.8(5) . .
C4 C5 H5A 109.0 . .
C6 C5 H5A 109.0 . .
C4 C5 H5B 109.0 . .
C6 C5 H5B 109.0 . .
H5A C5 H5B 107.8 . .
N7 C6 C5 111.5(5) . .
N7 C6 H6A 109.3 . .
C5 C6 H6A 109.3 . .
N7 C6 H6B 109.3 . .
C5 C6 H6B 109.3 . .
H6A C6 H6B 108.0 . .
C6 N7 H7A 109.5 . .
C6 N7 H7B 109.5 . .
H7A N7 H7B 109.5 . .
C6 N7 H7C 109.5 . .
H7A N7 H7C 109.5 . .
H7B N7 H7C 109.5 . .
N15 C11 N12 114.3(6) . .
N15 C11 N16 124.9(7) . .
N12 C11 N16 120.7(6) . .
C11 N12 N13 103.9(5) . .
N14 N13 N12 109.2(5) . .
N13 N14 N15 109.9(5) . .
C11 N15 N14 102.7(5) . .
C17 N16 C11 125.6(6) . .
C17 N16 H16 117.2 . .
C11 N16 H16 117.2 . .
O17 C17 N16 123.9(6) . .
O17 C17 C18 120.4(7) . .
N16 C17 C18 115.6(6) . .
C19 C18 C20 123.4(6) . .
C19 C18 C17 117.7(6) . .
C20 C18 C17 118.8(6) . .
C18 C19 H19B 120.0 . .
C18 C19 H19A 120.0 . .
H19B C19 H19A 120.0 . .
C18 C20 H20C 109.5 . .
C18 C20 H20A 109.5 . .
H20C C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20C C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
N25 C21 N22 114.2(6) . .
N25 C21 N26 125.1(7) . .
N22 C21 N26 120.7(6) . .
C21 N22 N23 103.4(5) . .
N24 N23 N22 109.0(5) . .
N23 N24 N25 110.6(5) . .
C21 N25 N24 102.8(5) . .
C27 N26 C21 124.1(6) . .
C27 N26 H26 118.0 . .
C21 N26 H26 118.0 . .
O27 C27 N26 122.5(6) . .
O27 C27 C28 120.2(7) . .
N26 C27 C28 117.2(6) . .
C29 C28 C27 123.2(7) . .
C29 C28 C30 122.0(6) . .
C27 C28 C30 114.8(6) . .
C28 C29 H29B 120.0 . .
C28 C29 H29A 120.0 . .
H29B C29 H29A 120.0 . .
C28 C30 H30C 109.5 . .
C28 C30 H30B 109.5 . .
H30C C30 H30B 109.5 . .
C28 C30 H30A 109.5 . .
H30C C30 H30A 109.5 . .
H30B C30 H30A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.505(9) .
C1 C1 1.509(12) 3_776
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 N3 1.480(7) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
N3 C4 1.489(8) .
N3 H3A 0.9200 .
N3 H3B 0.9200 .
C4 C5 1.505(9) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.528(8) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 N7 1.505(8) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
N7 H7A 0.9100 .
N7 H7B 0.9100 .
N7 H7C 0.9100 .
C11 N15 1.326(7) .
C11 N12 1.328(8) .
C11 N16 1.401(8) .
N12 N13 1.351(7) .
N13 N14 1.320(7) .
N14 N15 1.368(7) .
N16 C17 1.358(8) .
N16 H16 0.8800 .
C17 O17 1.236(7) .
C17 C18 1.503(9) .
C18 C19 1.327(9) .
C18 C20 1.493(8) .
C19 H19B 0.9500 .
C19 H19A 0.9500 .
C20 H20C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 N25 1.328(7) .
C21 N22 1.329(8) .
C21 N26 1.400(8) .
N22 N23 1.363(7) .
N23 N24 1.312(7) .
N24 N25 1.354(7) .
N26 C27 1.359(8) .
N26 H26 0.8800 .
C27 O27 1.231(7) .
C27 C28 1.497(9) .
C28 C29 1.317(8) .
C28 C30 1.499(9) .
C29 H29B 0.9500 .
C29 H29A 0.9500 .
C30 H30C 0.9800 .
C30 H30B 0.9800 .
C30 H30A 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N24 0.92 1.90 2.802(8) 165.0 4_566
N3 H3A N23 0.92 2.63 3.365(7) 136.8 4_566
N3 H3B N15 0.92 1.92 2.749(8) 149.6 3_766
N3 H3B O17 0.92 2.43 3.115(6) 131.1 3_766
N7 H7A O17 0.91 2.08 2.966(7) 165.4 4_565
N7 H7B N14 0.91 1.98 2.852(7) 159.0 .
N7 H7B N13 0.91 2.59 3.245(7) 129.3 .
N7 H7C O27 0.91 2.17 2.975(6) 147.6 2_755
N7 H7C N25 0.91 2.20 2.914(7) 134.4 2_755
N16 H16 N22 0.88 2.18 3.027(7) 160.0 2_655
N26 H26 N12 0.88 2.09 2.933(7) 160.6 2_645
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
_geom_torsion_site_symmetry_1
C1 C1 C2 N3 179.2(6) 3_776
C1 C2 N3 C4 -172.5(5) .
C2 N3 C4 C5 168.1(5) .
N3 C4 C5 C6 66.4(7) .
C4 C5 C6 N7 176.6(5) .
N15 C11 N12 N13 -1.0(8) .
N16 C11 N12 N13 -177.1(6) .
C11 N12 N13 N14 0.6(7) .
N12 N13 N14 N15 0.0(7) .
N12 C11 N15 N14 1.0(8) .
N16 C11 N15 N14 176.8(6) .
N13 N14 N15 C11 -0.6(7) .
N15 C11 N16 C17 5.7(10) .
N12 C11 N16 C17 -178.7(7) .
C11 N16 C17 O17 3.9(10) .
C11 N16 C17 C18 -173.9(6) .
O17 C17 C18 C19 -43.9(10) .
N16 C17 C18 C19 133.9(7) .
O17 C17 C18 C20 135.9(7) .
N16 C17 C18 C20 -46.2(9) .
N25 C21 N22 N23 -0.2(7) .
N26 C21 N22 N23 179.9(5) .
C21 N22 N23 N24 0.5(6) .
N22 N23 N24 N25 -0.6(7) .
N22 C21 N25 N24 -0.2(7) .
N26 C21 N25 N24 179.8(6) .
N23 N24 N25 C21 0.5(7) .
N25 C21 N26 C27 -13.9(10) .
N22 C21 N26 C27 166.1(6) .
C21 N26 C27 O27 -6.3(10) .
C21 N26 C27 C28 176.5(6) .
O27 C27 C28 C29 159.2(6) .
N26 C27 C28 C29 -23.6(9) .
O27 C27 C28 C30 -17.7(9) .
N26 C27 C28 C30 159.6(6) .
