#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516749.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_1516749
loop_
_publ_author_name
'Tominey, Alan F.'
'Docherty, Paul H.'
'Rosair, Georgina M.'
'Quenardelle, Romain'
'Kraft, Arno'
_publ_section_title
;
 Unusually weak binding interactions in tetrazole-amidine complexes.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1279
_journal_page_last               1282
_journal_paper_doi               10.1021/ol053072+
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C2 H7 N2, C H O2'
_chemical_formula_sum            'C3 H8 N2 O2'
_chemical_formula_weight         104.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 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            4
_cell_length_a                   6.4456(9)
_cell_length_b                   6.4456(9)
_cell_length_c                   12.530(3)
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.513
_cell_measurement_theta_min      3.552
_cell_volume                     520.57(16)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker Nonius X8 Apex 2'
_diffrn_measurement_method       'ω and 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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     42
_refine_ls_number_reflns         511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0335
_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)+(0.0438P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                409
_reflns_number_total             511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol053072%2Bsi20060220_024519.cif
_cod_data_source_block           x80157(4)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        520.55(17)
_cod_original_sg_symbol_H-M      P4(3)2(1)2
_cod_database_code               1516749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
O1 O 0.74145(12) 0.49687(14) -0.00622(6) 0.0251(3) Uani 1 1 d .
N1 N 0.18161(18) 0.43334(17) 1.00463(9) 0.0224(3) Uani 1 1 d .
H1 H 0.281(2) 0.534(3) 1.0049(10) 0.027 Uiso 1 1 d .
H2 H 0.055(2) 0.457(2) 1.0014(14) 0.027 Uiso 1 1 d .
C1 C 0.23744(18) 0.23744(18) 1.0000 0.0192(4) Uani 1 2 d S
C2 C 0.07376(18) 0.07376(18) 1.0000 0.0217(4) Uani 1 2 d S
H2A H 0.0796 -0.0023 1.0658 0.033 Uiso 0.50 1 calc PR
H2B H 0.0965 -0.0192 0.9413 0.033 Uiso 0.50 1 calc PR
H2C H -0.0602 0.1375 0.9929 0.033 Uiso 0.50 1 calc PR
C3 C 0.6788(2) 0.6788(2) 0.0000 0.0273(4) Uani 1 2 d S
H3 H 0.791(3) 0.791(3) 0.0000 0.033 Uiso 1 2 d S
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
O1 0.0165(5) 0.0180(5) 0.0407(6) -0.0012(5) 0.0002(4) 0.0005(3)
N1 0.0140(5) 0.0158(5) 0.0373(6) 0.0002(6) 0.0006(6) 0.0000(4)
C1 0.0168(5) 0.0168(5) 0.0241(9) -0.0002(6) 0.0002(6) -0.0020(7)
C2 0.0183(5) 0.0183(5) 0.0286(9) 0.0000(6) 0.0000(6) -0.0049(7)
C3 0.0183(6) 0.0183(6) 0.0454(11) -0.0003(8) 0.0003(8) -0.0038(7)
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
C1 N1 H1 119.3(10) . .
C1 N1 H2 116.4(12) . .
H1 N1 H2 124.0(16) . .
N1 C1 N1 121.88(15) 7_557 .
N1 C1 C2 119.06(8) 7_557 .
N1 C1 C2 119.06(8) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O1 C3 O1 128.12(18) . 7
O1 C3 H3 115.94(9) . .
O1 C3 H3 115.94(9) 7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.2426(12) .
N1 C1 1.3143(14) .
N1 H1 0.913(15) .
N1 H2 0.831(15) .
C1 N1 1.3143(14) 7_557
C1 C2 1.492(2) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 O1 1.2427(12) 7
C3 H3 1.02(2) .
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
N1 H1 O1 0.913(15) 1.928(15) 2.8414(16) 178.6(15) 7_556
N1 H2 O1 0.831(15) 2.040(15) 2.8697(15) 176.6(16) 1_456
