#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/72/2207283.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_2207283
loop_
_publ_author_name
'Guo-Wu Rao'
'Wei-Xiao Hu'
_publ_section_title
;
 Diethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
;
_journal_coeditor_code           LH6491
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3664
_journal_page_last               o3665
_journal_paper_doi               10.1107/S1600536805030485
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H12 N4 O4'
_chemical_formula_moiety         'C8 H12 N4 O4'
_chemical_formula_sum            'C8 H12 N4 O4'
_chemical_formula_weight         228.22
_chemical_melting_point          374.5(5)
_chemical_name_systematic
;
Diethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
;
_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                90.00
_cell_angle_beta                 109.090(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4740(10)
_cell_length_b                   13.4510(15)
_cell_length_c                   10.159(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.76
_cell_measurement_theta_min      10.08
_cell_volume                     1094.3(4)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Version 1.05; Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2262
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0895P)²+0.3801P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1165
_reflns_number_total             1954
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6491.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '374-375' was changed to '374.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '374-375' was changed to '374.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207283
_cod_database_fobs_code          2207283
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_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
O1 0.7357(3) 0.61761(18) 0.0420(2) 0.0871(8) Uani d . 1 A . O
O3 0.8615(4) 1.08332(17) 0.3472(2) 0.0915(8) Uani d . 1 . . O
O4 0.7479(3) 1.09764(15) 0.1173(2) 0.0794(7) Uani d D 1 . . O
N1 0.8760(3) 0.80892(16) 0.0889(2) 0.0529(6) Uani d D 1 . . N
N2 0.8244(3) 0.90866(16) 0.0856(2) 0.0546(6) Uani d . 1 . . N
N4 0.9291(3) 0.88550(17) 0.3253(2) 0.0632(7) Uani d D 1 . . N
N5 0.8646(3) 0.78761(17) 0.3128(2) 0.0632(7) Uani d . 1 . . N
C6 0.8434(3) 0.7521(2) 0.1916(2) 0.0533(7) Uani d . 1 A . C
C3 0.8551(3) 0.9437(2) 0.2077(2) 0.0528(7) Uani d . 1 . . C
C2 0.7833(4) 0.6483(2) 0.1585(3) 0.0634(8) Uani d D 1 . . C
C1 0.8210(4) 1.0487(2) 0.2322(3) 0.0643(8) Uani d D 1 . . C
C7 0.7050(6) 1.2015(3) 0.1317(4) 0.1045(14) Uani d D 1 . . C
H7A 0.6170 1.2050 0.1731 0.157 Uiso calc R 1 . . H
H7B 0.8018 1.2366 0.1919 0.157 Uiso calc R 1 . . H
C8 0.6511(8) 1.2459(3) -0.0014(5) 0.147(2) Uani d D 1 . . C
H8A 0.7405 1.2448 -0.0400 0.220 Uiso calc R 1 . . H
H8B 0.6188 1.3135 0.0064 0.220 Uiso calc R 1 . . H
H8C 0.5574 1.2097 -0.0612 0.220 Uiso calc R 1 . . H
O2A 0.8036(5) 0.5971(3) 0.2760(3) 0.0589(10) Uani d PD 0.80 A 1 O
C4A 0.7403(6) 0.4944(3) 0.2632(5) 0.0631(12) Uani d PD 0.80 A 1 C
H4A1 0.7597 0.4626 0.1843 0.095 Uiso calc PR 0.80 A 1 H
H4A2 0.8008 0.4574 0.3463 0.095 Uiso calc PR 0.80 A 1 H
C5A 0.5614(7) 0.4919(6) 0.2445(7) 0.0794(16) Uani d PD 0.80 A 1 C
H5A1 0.5430 0.5176 0.3264 0.119 Uiso calc PR 0.80 A 1 H
H5A2 0.5220 0.4245 0.2294 0.119 Uiso calc PR 0.80 A 1 H
H5A3 0.5019 0.5317 0.1655 0.119 Uiso calc PR 0.80 A 1 H
O2B 0.719(2) 0.6007(12) 0.2393(16) 0.084(6) Uani d PD 0.20 A 2 O
C4B 0.664(6) 0.5014(16) 0.183(3) 0.138(14) Uani d PD 0.20 A 2 C
H4B1 0.5768 0.5055 0.0934 0.166 Uiso calc PR 0.20 A 2 H
H4B2 0.7566 0.4629 0.1733 0.166 Uiso calc PR 0.20 A 2 H
C5B 0.602(6) 0.459(4) 0.288(3) 0.18(3) Uani d PD 0.20 A 2 C
H5B1 0.6896 0.4592 0.3767 0.276 Uiso calc PR 0.20 A 2 H
H5B2 0.5663 0.3918 0.2629 0.276 Uiso calc PR 0.20 A 2 H
H5B3 0.5097 0.4977 0.2942 0.276 Uiso calc PR 0.20 A 2 H
H1 0.847(4) 0.784(2) 0.0069(17) 0.075(9) Uiso d D 1 . . H
H3 0.923(4) 0.911(2) 0.401(2) 0.092(11) Uiso d 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'
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_publ_flag
C1 O4 C7 116.9(3) ?
C6 N1 N2 113.9(2) yes
C6 N1 H1 116(2) ?
N2 N1 H1 112(2) ?
C3 N2 N1 111.5(2) yes
C3 N4 N5 113.1(2) yes
C3 N4 H3 114(2) ?
N5 N4 H3 108(2) ?
C6 N5 N4 111.3(2) yes
N5 C6 N1 121.2(2) yes
N5 C6 C2 120.0(2) ?
N1 C6 C2 118.9(2) ?
N2 C3 N4 121.3(2) yes
N2 C3 C1 121.9(2) ?
N4 C3 C1 116.7(2) ?
O1 C2 O2B 112.5(8) ?
O1 C2 O2A 127.5(3) ?
O1 C2 C6 122.0(3) ?
O2B C2 C6 120.4(8) ?
O2A C2 C6 110.3(3) ?
O3 C1 O4 125.2(3) ?
O3 C1 C3 121.7(3) ?
O4 C1 C3 113.1(2) ?
C8 C7 O4 108.8(3) ?
C8 C7 H7A 109.9 ?
O4 C7 H7A 109.9 ?
C8 C7 H7B 109.9 ?
O4 C7 H7B 109.9 ?
H7A C7 H7B 108.3 ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C2 O2A C4A 117.9(3) ?
C5A C4A O2A 111.4(4) ?
C5A C4A H4A1 109.3 ?
O2A C4A H4A1 109.3 ?
C5A C4A H4A2 109.3 ?
O2A C4A H4A2 109.3 ?
H4A1 C4A H4A2 108.0 ?
C2 O2B C4B 110.5(15) ?
C5B C4B O2B 103(2) ?
C5B C4B H4B1 111.3 ?
O2B C4B H4B1 111.3 ?
C5B C4B H4B2 111.3 ?
O2B C4B H4B2 111.3 ?
H4B1 C4B H4B2 109.2 ?
C4B C5B H5B1 109.5 ?
C4B C5B H5B2 109.5 ?
H5B1 C5B H5B2 109.5 ?
C4B C5B H5B3 109.5 ?
H5B1 C5B H5B3 109.5 ?
H5B2 C5B H5B3 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.193(3) ?
O3 C1 1.199(3) ?
O4 C1 1.306(3) ?
O4 C7 1.463(4) ?
N1 C6 1.392(3) yes
N1 N2 1.408(3) yes
N1 H1 0.859(10) ?
N2 C3 1.272(3) yes
N4 C3 1.394(3) yes
N4 N5 1.416(3) yes
N4 H3 0.856(10) ?
N5 C6 1.277(3) yes
C6 C2 1.486(4) ?
C3 C1 1.479(4) ?
C2 O2B 1.292(9) ?
C2 O2A 1.340(4) ?
C7 C8 1.410(5) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
O2A C4A 1.472(5) ?
C4A C5A 1.465(7) ?
C4A H4A1 0.9700 ?
C4A H4A2 0.9700 ?
C5A H5A1 0.9600 ?
C5A H5A2 0.9600 ?
C5A H5A3 0.9600 ?
O2B C4B 1.466(10) ?
C4B C5B 1.453(10) ?
C4B H4B1 0.9700 ?
C4B H4B2 0.9700 ?
C5B H5B1 0.9600 ?
C5B H5B2 0.9600 ?
C5B H5B3 0.9600 ?
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
C6 N1 N2 C3 40.3(3)
C3 N4 N5 C6 41.6(3)
N4 N5 C6 N1 -2.5(4)
N4 N5 C6 C2 177.4(3)
N2 N1 C6 N5 -40.2(4)
N2 N1 C6 C2 140.0(3)
N1 N2 C3 N4 -0.7(3)
N1 N2 C3 C1 176.6(3)
N5 N4 C3 N2 -41.8(4)
N5 N4 C3 C1 140.8(3)
N5 C6 C2 O1 167.3(3)
N1 C6 C2 O1 -12.8(4)
N5 C6 C2 O2B 14.6(11)
N1 C6 C2 O2B -165.6(10)
N5 C6 C2 O2A -17.3(4)
N1 C6 C2 O2A 162.6(3)
C7 O4 C1 O3 -3.2(5)
C7 O4 C1 C3 178.3(3)
N2 C3 C1 O3 -174.4(3)
N4 C3 C1 O3 3.1(4)
N2 C3 C1 O4 4.2(4)
N4 C3 C1 O4 -178.4(2)
C1 O4 C7 C8 171.3(4)
O1 C2 O2A C4A -9.0(6)
O2B C2 O2A C4A 60.0(17)
C6 C2 O2A C4A 175.9(3)
C2 O2A C4A C5A -83.0(6)
O1 C2 O2B C4B 23(3)
O2A C2 O2B C4B -104(3)
C6 C2 O2B C4B 178(2)
C2 O2B C4B C5B 178(3)
