#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513405.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_1513405
loop_
_publ_author_name
'Palysaeva, Nadezhda V.'
'Kumpan, Katerina P.'
'Struchkova, Marina I.'
'Dalinger, Igor L.'
'Kormanov, Aleksandr V.'
'Aleksandrova, Nataly S.'
'Chernyshev, Victor M.'
'Pyreu, Dmitrii F.'
'Suponitsky, Kyrill Yu'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 A Direct Approach to a
 6-Hetarylamino[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine Library.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              406
_journal_page_last               409
_journal_paper_doi               10.1021/ol403308h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C5 H3 N11 O2'
_chemical_formula_sum            'C5 H3 N11 O2'
_chemical_formula_weight         249.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.461(3)
_cell_length_b                   8.7866(12)
_cell_length_c                   11.3296(16)
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.56
_cell_volume                     1852.7(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12079
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0522
_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)+(0.0415P)²+3.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2207
_reflns_number_total             2693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol403308h_si_003.cif
_cod_data_source_block           sh198
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/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        1852.7(4)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1513405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
O1 O -0.15451(16) 0.3883(4) 0.6949(3) 0.0263(7) Uani 1 1 d .
O2 O -0.10003(17) 0.5614(4) 0.8233(3) 0.0338(8) Uani 1 1 d .
N1 N 0.07289(18) -0.2331(4) 0.3944(3) 0.0176(7) Uani 1 1 d .
N2 N 0.0395(2) -0.2999(4) 0.4741(3) 0.0204(7) Uani 1 1 d .
N3 N 0.03825(17) -0.0547(3) 0.5027(3) 0.0129(6) Uani 1 1 d .
N4 N 0.02841(16) 0.0891(3) 0.5408(3) 0.0133(6) Uani 1 1 d .
N5 N 0.09036(16) 0.1652(4) 0.3913(3) 0.0144(6) Uani 1 1 d .
N6 N 0.09759(17) 0.0269(4) 0.3569(3) 0.0134(6) Uani 1 1 d .
N7 N 0.05368(16) 0.3423(3) 0.5055(3) 0.0121(6) Uani 1 1 d .
H7 H 0.0475 0.4204 0.4521 0.015 Uiso 1 1 d R
N8 N 0.02770(16) 0.3900(3) 0.6004(3) 0.0109(6) Uani 1 1 d .
N9 N -0.04141(16) 0.3722(4) 0.6011(3) 0.0140(6) Uani 1 1 d .
N10 N 0.02256(16) 0.5222(4) 0.7599(3) 0.0133(6) Uani 1 1 d .
N11 N -0.10253(18) 0.4689(4) 0.7424(3) 0.0185(7) Uani 1 1 d .
C1 C 0.0710(2) -0.0860(4) 0.4127(3) 0.0144(7) Uani 1 1 d .
C2 C 0.0187(2) -0.1903(5) 0.5366(4) 0.0179(8) Uani 1 1 d .
H2A H -0.0062 -0.2056 0.5963 0.022 Uiso 1 1 calc R
C3 C 0.05549(18) 0.1887(4) 0.4822(3) 0.0128(7) Uani 1 1 d .
C4 C 0.0646(2) 0.4809(4) 0.6940(3) 0.0122(7) Uani 1 1 d .
H4A H 0.1134 0.5101 0.7095 0.015 Uiso 1 1 calc R
C5 C -0.03968(19) 0.4543(4) 0.6994(3) 0.0130(7) Uani 1 1 d .
O1' O 0.44201(16) 0.3825(4) 0.7435(3) 0.0274(7) Uani 1 1 d .
O2' O 0.38792(17) 0.5579(4) 0.8174(3) 0.0334(8) Uani 1 1 d .
N1' N 0.21538(19) -0.2313(4) 0.2147(3) 0.0194(7) Uani 1 1 d .
N2' N 0.2487(2) -0.2976(4) 0.3277(3) 0.0206(7) Uani 1 1 d .
N3' N 0.24942(16) -0.0527(3) 0.3579(3) 0.0122(6) Uani 1 1 d .
N4' N 0.25958(17) 0.0913(3) 0.4037(3) 0.0135(6) Uani 1 1 d .
N5' N 0.19708(16) 0.1660(4) 0.1926(3) 0.0140(6) Uani 1 1 d .
N6' N 0.18986(17) 0.0280(4) 0.1515(3) 0.0134(6) Uani 1 1 d .
N7' N 0.23380(16) 0.3450(4) 0.3431(3) 0.0122(6) Uani 1 1 d .
H7' H 0.2478 0.4127 0.2952 0.015 Uiso 1 1 d R
N8' N 0.25971(16) 0.3920(3) 0.4643(3) 0.0117(6) Uani 1 1 d .
N9' N 0.32882(17) 0.3715(4) 0.5353(3) 0.0144(6) Uani 1 1 d .
N10' N 0.26637(16) 0.5245(4) 0.6295(3) 0.0134(6) Uani 1 1 d .
N11' N 0.39071(19) 0.4661(4) 0.7386(3) 0.0192(7) Uani 1 1 d .
C1' C 0.2167(2) -0.0837(4) 0.2346(3) 0.0142(7) Uani 1 1 d .
C2' C 0.2691(2) -0.1876(4) 0.4111(4) 0.0181(8) Uani 1 1 d .
H2'A H 0.2939 -0.2027 0.4958 0.022 Uiso 1 1 calc R
C3' C 0.23240(18) 0.1905(4) 0.3184(3) 0.0120(7) Uani 1 1 d .
C4' C 0.22338(19) 0.4851(4) 0.5208(3) 0.0117(7) Uani 1 1 d .
H4'A H 0.1749 0.5167 0.4874 0.014 Uiso 1 1 calc R
C5' C 0.3276(2) 0.4536(4) 0.6321(4) 0.0144(7) Uani 1 1 d .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 N1 N2 105.9(3)
C2 N2 N1 108.3(3)
C2 N3 N4 130.9(3)
C2 N3 C1 105.4(3)
N4 N3 C1 123.8(3)
C3 N4 N3 110.3(3)
N6 N5 C3 118.5(3)
N5 N6 C1 117.1(3)
C3 N7 N8 118.8(3)
C3 N7 H7 128.7
N8 N7 H7 106.5
C4 N8 N9 111.2(3)
C4 N8 N7 124.0(3)
N9 N8 N7 124.0(3)
C5 N9 N8 99.3(3)
C4 N10 C5 101.9(3)
O2 N11 O1 124.4(4)
O2 N11 C5 117.5(3)
O1 N11 C5 118.1(3)
N1 C1 N6 127.9(3)
N1 C1 N3 110.8(3)
N6 C1 N3 121.3(3)
N2 C2 N3 109.7(3)
N2 C2 H2A 125.2
N3 C2 H2A 125.2
N4 C3 N7 121.7(3)
N4 C3 N5 129.1(3)
N7 C3 N5 109.2(3)
N10 C4 N8 109.5(3)
N10 C4 H4A 125.2
N8 C4 H4A 125.2
N9 C5 N10 118.0(3)
N9 C5 N11 121.1(3)
N10 C5 N11 120.9(3)
C1' N1' N2' 106.0(3)
C2' N2' N1' 108.3(3)
C2' N3' N4' 131.6(3)
C2' N3' C1' 105.5(3)
N4' N3' C1' 122.7(3)
C3' N4' N3' 111.1(3)
N6' N5' C3' 118.6(3)
N5' N6' C1' 116.8(3)
N8' N7' C3' 118.4(3)
N8' N7' H7' 108.3
C3' N7' H7' 121.2
C4' N8' N9' 111.2(3)
C4' N8' N7' 124.1(3)
N9' N8' N7' 123.9(3)
C5' N9' N8' 99.5(3)
C4' N10' C5' 102.6(3)
O2' N11' O1' 125.0(4)
O2' N11' C5' 116.9(3)
O1' N11' C5' 118.1(3)
N1' C1' N6' 127.6(4)
N1' C1' N3' 110.3(3)
N6' C1' N3' 122.0(3)
N2' C2' N3' 109.8(3)
N2' C2' H2'A 125.1
N3' C2' H2'A 125.1
N4' C3' N7' 122.0(3)
N4' C3' N5' 128.8(3)
N7' C3' N5' 109.3(3)
N10' C4' N8' 108.9(3)
N10' C4' H4'A 125.6
N8' C4' H4'A 125.6
N9' C5' N10' 117.9(3)
N9' C5' N11' 121.1(3)
N10' C5' N11' 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N11 1.224(5)
O2 N11 1.215(5)
N1 C1 1.311(5)
N1 N2 1.388(5)
N2 C2 1.327(5)
N3 C2 1.341(5)
N3 N4 1.366(4)
N3 C1 1.379(5)
N4 C3 1.299(5)
N5 N6 1.296(5)
N5 C3 1.405(5)
N6 C1 1.358(5)
N7 C3 1.377(5)
N7 N8 1.380(4)
N7 H7 0.8999
N8 C4 1.354(5)
N8 N9 1.357(4)
N9 C5 1.319(5)
N10 C4 1.309(5)
N10 C5 1.344(5)
N11 C5 1.449(5)
C2 H2A 0.9500
C4 H4A 0.9500
O1' N11' 1.228(5)
O2' N11' 1.215(5)
N1' C1' 1.315(5)
N1' N2' 1.383(5)
N2' C2' 1.329(5)
N3' C2' 1.333(5)
N3' N4' 1.360(4)
N3' C1' 1.383(5)
N4' C3' 1.294(5)
N5' N6' 1.292(4)
N5' C3' 1.406(5)
N6' C1' 1.355(5)
N7' N8' 1.380(4)
N7' C3' 1.385(5)
N7' H7' 0.8999
N8' C4' 1.358(5)
N8' N9' 1.362(4)
N9' C5' 1.319(5)
N10' C4' 1.316(5)
N10' C5' 1.337(5)
N11' C5' 1.452(5)
C2' H2'A 0.9500
C4' H4'A 0.9500
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
N7 H7 N10 2_564 0.90 2.15 2.923(4) 144
N7' H7' N10' 2_564 0.90 2.09 2.911(4) 152
C2 H2A O1' 3_445 0.95 2.32 3.191(5) 152
C2' H2'A O1 3_545 0.95 2.33 3.194(5) 152
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
C1 N1 N2 C2 0.2(4)
C2 N3 N4 C3 -179.3(4)
C1 N3 N4 C3 -1.4(4)
C3 N5 N6 C1 -0.4(5)
C3 N7 N8 C4 125.4(4)
C3 N7 N8 N9 -65.6(4)
C4 N8 N9 C5 -1.1(4)
N7 N8 N9 C5 -171.3(3)
N2 N1 C1 N6 179.3(4)
N2 N1 C1 N3 0.7(4)
N5 N6 C1 N1 -179.0(4)
N5 N6 C1 N3 -0.5(5)
C2 N3 C1 N1 -1.4(4)
N4 N3 C1 N1 -179.7(3)
C2 N3 C1 N6 179.9(3)
N4 N3 C1 N6 1.6(5)
N1 N2 C2 N3 -1.1(5)
N4 N3 C2 N2 179.7(3)
C1 N3 C2 N2 1.5(4)
N3 N4 C3 N7 -178.8(3)
N3 N4 C3 N5 0.4(5)
N8 N7 C3 N4 5.4(5)
N8 N7 C3 N5 -174.0(3)
N6 N5 C3 N4 0.5(6)
N6 N5 C3 N7 179.8(3)
C5 N10 C4 N8 -1.1(4)
N9 N8 C4 N10 1.5(4)
N7 N8 C4 N10 171.7(3)
N8 N9 C5 N10 0.4(4)
N8 N9 C5 N11 -178.5(3)
C4 N10 C5 N9 0.4(4)
C4 N10 C5 N11 179.4(3)
O2 N11 C5 N9 -170.7(4)
O1 N11 C5 N9 9.0(6)
O2 N11 C5 N10 10.4(6)
O1 N11 C5 N10 -169.9(4)
C1' N1' N2' C2' -0.3(4)
C2' N3' N4' C3' 178.8(4)
C1' N3' N4' C3' 2.5(5)
C3' N5' N6' C1' 0.7(5)
C3' N7' N8' C4' -126.9(4)
C3' N7' N8' N9' 64.2(4)
C4' N8' N9' C5' 1.3(4)
N7' N8' N9' C5' 171.5(3)
N2' N1' C1' N6' -179.4(4)
N2' N1' C1' N3' -0.6(4)
N5' N6' C1' N1' 179.6(4)
N5' N6' C1' N3' 0.9(5)
C2' N3' C1' N1' 1.2(4)
N4' N3' C1' N1' 178.4(3)
C2' N3' C1' N6' -179.9(3)
N4' N3' C1' N6' -2.7(5)
N1' N2' C2' N3' 1.1(5)
N4' N3' C2' N2' -178.2(4)
C1' N3' C2' N2' -1.4(4)
N3' N4' C3' N7' 177.8(3)
N3' N4' C3' N5' -0.9(5)
N8' N7' C3' N4' -5.4(5)
N8' N7' C3' N5' 173.5(3)
N6' N5' C3' N4' -0.7(5)
N6' N5' C3' N7' -179.5(3)
C5' N10' C4' N8' 0.8(4)
N9' N8' C4' N10' -1.4(4)
N7' N8' C4' N10' -171.5(3)
N8' N9' C5' N10' -0.8(4)
N8' N9' C5' N11' 178.9(3)
C4' N10' C5' N9' 0.1(4)
C4' N10' C5' N11' -179.7(3)
O2' N11' C5' N9' 171.5(4)
O1' N11' C5' N9' -9.6(6)
O2' N11' C5' N10' -8.8(6)
O1' N11' C5' N10' 170.1(4)
