#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:47:46 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179394 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/91/4329114.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_4329114
loop_
_publ_author_name
'Guo-Hong Tao'
'Damon A. Parrish'
'Jean'ne M. Shreeve'
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       damon.parrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_publ_section_title
;
 Nitrogen-Rich 5-(1-Methylhydrazinyl)tetrazole and its Copper and Silver
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5305
_journal_page_last               5312
_journal_paper_doi               10.1021/ic300242e
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C2 H6 N6'
_chemical_formula_sum            'C2 H6 N6'
_chemical_formula_weight         114.13
_chemical_name_systematic
; 
 5-(1-methylhydrazinyl)-1H-tetrazole 
;
_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_date             2009-02-11
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.397(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8713(18)
_cell_length_b                   12.770(6)
_cell_length_c                   9.974(5)
_cell_measurement_temperature    93(2)
_cell_volume                     492.2(4)
_computing_cell_refinement       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_reduction
;
Bruker SAINT v7.34A (Bruker, 2005), Bruker XPREP v2005/2 (Bruker, 2004)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4942
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2004/1 (Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         1219
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0399
_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)+(0.0532P)²+0.2183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                1081
_reflns_number_total             1219
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic300242e_si_002_2.cif
_cod_data_source_block           shrv48
_cod_original_cell_volume        492.3(4)
_cod_database_code               4329114
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 0.2665(3) 0.78679(9) 0.73467(12) 0.0124(3) Uani 1 1 d .
C2 C -0.0010(3) 0.92041(10) 0.86789(12) 0.0153(3) Uani 1 1 d .
H2A H -0.0673 0.8647 0.9289 0.023 Uiso 1 1 calc R
H2B H -0.1926 0.9702 0.8542 0.023 Uiso 1 1 calc R
H2C H 0.2034 0.9570 0.9070 0.023 Uiso 1 1 calc R
N1 N 0.3784(3) 0.74424(8) 0.62188(10) 0.0130(2) Uani 1 1 d .
H1 H 0.3509 0.7708 0.5405 0.016 Uiso 1 1 calc R
N2 N 0.5417(3) 0.65293(8) 0.65564(11) 0.0152(3) Uani 1 1 d .
N3 N 0.5281(3) 0.64255(8) 0.78368(11) 0.0149(3) Uani 1 1 d .
N4 N 0.3598(3) 0.72487(8) 0.83859(10) 0.0127(2) Uani 1 1 d .
N5 N 0.0781(3) 0.87503(9) 0.73987(11) 0.0201(3) Uani 1 1 d .
N6 N 0.0634(3) 0.93734(8) 0.62217(11) 0.0173(3) Uani 1 1 d D
H6A H 0.161(4) 1.0006(11) 0.6462(16) 0.021 Uiso 1 1 d D
H6B H -0.170(4) 0.9486(13) 0.5981(17) 0.021 Uiso 1 1 d 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 0.0138(5) 0.0140(5) 0.0093(5) -0.0014(4) 0.0004(4) -0.0027(4)
C2 0.0184(6) 0.0162(6) 0.0116(6) -0.0020(4) 0.0028(4) 0.0020(4)
N1 0.0172(5) 0.0130(5) 0.0087(5) -0.0003(3) 0.0006(4) 0.0001(4)
N2 0.0189(5) 0.0132(5) 0.0136(5) -0.0003(4) 0.0006(4) 0.0010(4)
N3 0.0181(5) 0.0137(5) 0.0128(5) -0.0007(4) 0.0012(4) 0.0006(4)
N4 0.0153(5) 0.0126(5) 0.0101(5) 0.0001(4) 0.0010(4) 0.0000(4)
N5 0.0342(6) 0.0176(5) 0.0086(5) 0.0018(4) 0.0030(4) 0.0097(5)
N6 0.0262(6) 0.0145(5) 0.0110(5) 0.0031(4) 0.0000(4) 0.0013(4)
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
N4 C1 N1 108.93(11)
N4 C1 N5 126.02(11)
N1 C1 N5 124.99(11)
N5 C2 H2A 109.5
N5 C2 H2B 109.5
H2A C2 H2B 109.5
N5 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C1 N1 N2 107.92(10)
C1 N1 H1 126.0
N2 N1 H1 126.0
N3 N2 N1 106.76(10)
N2 N3 N4 111.48(10)
C1 N4 N3 104.91(10)
C1 N5 N6 115.72(10)
C1 N5 C2 120.77(10)
N6 N5 C2 120.31(10)
N5 N6 H6A 106.4(10)
N5 N6 H6B 106.8(11)
H6A N6 H6B 108.0(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N4 1.3363(16)
C1 N1 1.3440(16)
C1 N5 1.3450(16)
C2 N5 1.4514(16)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
N1 N2 1.3592(15)
N1 H1 0.8800
N2 N3 1.2881(16)
N3 N4 1.3683(15)
N5 N6 1.4167(15)
N6 H6A 0.917(13)
N6 H6B 0.934(14)
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 N4 0.88 2.02 2.8496(19) 157.3 4_575
N6 H6A N3 0.917(13) 2.264(14) 3.1739(19) 171.4(14) 2_656
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
N4 C1 N1 N2 0.79(13)
N5 C1 N1 N2 -176.53(11)
C1 N1 N2 N3 -0.39(13)
N1 N2 N3 N4 -0.14(13)
N1 C1 N4 N3 -0.84(13)
N5 C1 N4 N3 176.44(12)
N2 N3 N4 C1 0.61(13)
N4 C1 N5 N6 169.19(11)
N1 C1 N5 N6 -13.96(18)
N4 C1 N5 C2 9.4(2)
N1 C1 N5 C2 -173.78(11)
