#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206938.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_2206938
loop_
_publ_author_name
'Guo-Wu Rao'
'Wei-Xiao Hu'
_publ_section_title
;
 3,6-Bis(4-chlorophenyl)-1-isobutyryl-1,4-dihydro-1,2,4,5-tetrazine
;
_journal_coeditor_code           DN6225
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3276
_journal_page_last               o3277
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C18 H16 Cl2 N4 O'
_chemical_formula_sum            'C18 H16 Cl2 N4 O'
_chemical_formula_weight         375.25
_chemical_melting_point          473.0(10)
_chemical_name_systematic
;
3,6-Bis(4-chlorophenyl)-1-isobutyryl-1,4-dihydro-1,2,4,5-tetrazine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   7.268(4)
_cell_length_b                   11.8130(10)
_cell_length_c                   21.282(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      10.77
_cell_measurement_theta_min      10.12
_cell_volume                     1827.2(10)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Version 1.05; Farrugia, 1997) and PLATON (Spek, 2003)'
_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       \w/2\q
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2019
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.9303
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.212
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(17)
_refine_ls_extinction_coef       0.0017(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1658
_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/[\s^2^(Fo^2^)+(0.0447P)^2^+0.4296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                840
_reflns_number_total             1997
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    dn6225.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '472-474' was changed to '473.0(10)'
- 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 '472-474' was changed to '473.0(10)'
- 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_database_code               2206938
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_type_symbol
C16 1.4950(9) -0.0440(5) 0.4576(3) 0.0628(17) Uani d . 1 C
H16 1.4681 -0.0104 0.4165 0.075 Uiso calc R 1 H
C18 1.6985(10) -0.0351(7) 0.4693(4) 0.116(3) Uani d . 1 C
H18A 1.7638 -0.0762 0.4374 0.174 Uiso calc R 1 H
H18B 1.7268 -0.0664 0.5098 0.174 Uiso calc R 1 H
H18C 1.7347 0.0430 0.4682 0.174 Uiso calc R 1 H
C17 1.4311(12) -0.1640(5) 0.4570(3) 0.115(3) Uani d . 1 C
H17A 1.3024 -0.1664 0.4471 0.173 Uiso calc R 1 H
H17B 1.4511 -0.1971 0.4976 0.173 Uiso calc R 1 H
H17C 1.4989 -0.2056 0.4260 0.173 Uiso calc R 1 H
Cl1 0.9862(4) 0.23932(17) 0.13453(7) 0.1189(9) Uani d . 1 Cl
Cl2 0.8599(3) -0.0054(2) 0.78382(9) 0.1269(10) Uani d . 1 Cl
N2 1.1658(7) 0.0636(4) 0.42558(19) 0.0528(13) Uani d . 1 N
N4 1.1253(7) 0.2547(4) 0.44721(19) 0.0535(13) Uani d . 1 N
H4 1.1544 0.3214 0.4345 0.064 Uiso calc R 1 H
O1 1.4435(5) 0.0319(3) 0.56104(16) 0.0576(11) Uani d . 1 O
N5 1.0751(7) 0.2352(4) 0.5094(2) 0.0580(14) Uani d . 1 N
C14 1.0869(8) 0.1838(5) 0.3401(3) 0.0455(15) Uani d . 1 C
N1 1.2212(7) 0.0637(4) 0.49067(19) 0.0497(13) Uani d . 1 N
C3 1.1268(8) 0.1641(5) 0.4067(2) 0.0472(15) Uani d . 1 C
C11 1.0220(10) 0.2165(6) 0.2134(3) 0.0657(19) Uani d . 1 C
C9 0.9997(10) 0.2792(5) 0.3189(3) 0.0678(19) Uani d . 1 C
H9 0.9618 0.3338 0.3476 0.081 Uiso calc R 1 H
C15 1.3881(10) 0.0197(5) 0.5069(3) 0.0512(16) Uani d . 1 C
C6 1.1253(8) 0.1387(5) 0.5305(3) 0.0511(16) Uani d . 1 C
C5 1.0356(9) 0.1805(6) 0.6398(3) 0.0697(19) Uani d . 1 C
H5 1.0572 0.2567 0.6316 0.084 Uiso calc R 1 H
C12 1.1059(10) 0.1198(6) 0.2333(3) 0.070(2) Uani d . 1 C
H12 1.1399 0.0648 0.2043 0.084 Uiso calc R 1 H
C7 0.9748(10) 0.1477(7) 0.6989(3) 0.081(2) Uani d . 1 C
H7 0.9581 0.2011 0.7305 0.097 Uiso calc R 1 H
C8 0.9404(10) 0.0372(8) 0.7097(3) 0.081(2) Uani d . 1 C
C13 1.1407(10) 0.1033(5) 0.2967(3) 0.071(2) Uani d . 1 C
H13 1.2005 0.0380 0.3101 0.086 Uiso calc R 1 H
C2 1.0312(10) -0.0096(6) 0.6061(3) 0.075(2) Uani d . 1 C
H2 1.0536 -0.0638 0.5753 0.090 Uiso calc R 1 H
C4 1.0640(9) 0.1021(5) 0.5934(3) 0.0557(16) Uani d . 1 C
C1 0.9648(10) -0.0434(6) 0.6647(3) 0.086(2) Uani d . 1 C
H1 0.9377 -0.1189 0.6727 0.103 Uiso calc R 1 H
C10 0.9675(11) 0.2954(5) 0.2559(3) 0.080(2) Uani d . 1 C
H10 0.9081 0.3607 0.2424 0.095 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C16 0.065(5) 0.060(4) 0.063(4) 0.015(4) -0.007(4) -0.007(3)
C18 0.065(6) 0.136(7) 0.148(7) 0.024(5) 0.007(5) -0.053(7)
C17 0.144(9) 0.077(5) 0.126(6) 0.007(6) -0.008(6) -0.049(5)
Cl1 0.180(2) 0.1185(17) 0.0581(9) 0.012(2) -0.0217(15) 0.0090(11)
Cl2 0.1070(17) 0.202(3) 0.0716(12) 0.0083(19) 0.0134(13) 0.0428(15)
N2 0.063(3) 0.052(3) 0.044(3) 0.007(3) -0.010(3) -0.007(2)
N4 0.068(3) 0.042(3) 0.050(3) -0.006(3) 0.006(3) -0.006(3)
O1 0.065(3) 0.049(2) 0.059(2) -0.001(2) -0.013(2) -0.001(2)
N5 0.064(4) 0.057(3) 0.052(3) 0.008(3) 0.000(3) -0.003(3)
C14 0.041(4) 0.043(3) 0.052(3) -0.001(3) 0.001(3) 0.001(3)
N1 0.052(3) 0.053(3) 0.044(3) 0.005(3) -0.004(3) -0.002(3)
C3 0.030(3) 0.055(4) 0.056(4) 0.002(4) -0.004(3) -0.006(3)
C11 0.072(5) 0.075(5) 0.050(3) 0.002(5) -0.006(4) 0.002(4)
C9 0.090(5) 0.057(4) 0.057(4) 0.024(5) -0.005(4) -0.006(3)
C15 0.065(5) 0.038(3) 0.051(4) 0.000(4) -0.001(4) 0.001(3)
C6 0.044(4) 0.059(4) 0.050(3) 0.003(4) -0.006(4) -0.003(3)
C5 0.068(5) 0.083(5) 0.058(4) 0.017(4) 0.003(4) -0.001(4)
C12 0.090(5) 0.068(5) 0.053(4) 0.008(5) -0.007(4) -0.009(3)
C7 0.075(5) 0.109(6) 0.060(4) 0.021(5) 0.006(4) -0.004(4)
C8 0.059(5) 0.122(6) 0.062(4) 0.000(5) 0.002(4) 0.026(5)
C13 0.089(5) 0.063(4) 0.062(4) 0.017(5) -0.012(4) -0.009(4)
C2 0.088(5) 0.082(5) 0.054(4) 0.000(5) -0.001(4) 0.007(4)
C4 0.055(4) 0.060(4) 0.052(4) 0.009(4) -0.006(3) 0.001(4)
C1 0.095(6) 0.089(5) 0.074(5) -0.014(5) -0.010(5) 0.012(5)
C10 0.107(6) 0.060(4) 0.072(4) 0.029(5) -0.017(5) 0.004(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'
Cl Cl 0.1484 0.1585 '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
C17 C16 C18 112.0(7)
C17 C16 C15 108.6(5)
C18 C16 C15 110.9(6)
C17 C16 H16 108.4
C18 C16 H16 108.4
C15 C16 H16 108.4
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C3 N2 N1 111.2(4)
C3 N4 N5 118.0(4)
C3 N4 H4 121.0
N5 N4 H4 121.0
C6 N5 N4 114.0(5)
C9 C14 C13 118.6(5)
C9 C14 C3 122.7(5)
C13 C14 C3 118.7(5)
C15 N1 C6 121.8(5)
C15 N1 N2 119.5(5)
C6 N1 N2 116.0(5)
N2 C3 N4 121.7(5)
N2 C3 C14 119.5(5)
N4 C3 C14 118.8(5)
C10 C11 C12 120.0(6)
C10 C11 Cl1 119.9(6)
C12 C11 Cl1 120.1(5)
C14 C9 C10 121.0(6)
C14 C9 H9 119.5
C10 C9 H9 119.5
O1 C15 N1 119.0(5)
O1 C15 C16 122.9(6)
N1 C15 C16 118.1(5)
N5 C6 N1 119.4(5)
N5 C6 C4 119.6(6)
N1 C6 C4 120.6(5)
C4 C5 C7 120.8(6)
C4 C5 H5 119.6
C7 C5 H5 119.6
C11 C12 C13 120.1(6)
C11 C12 H12 120.0
C13 C12 H12 120.0
C8 C7 C5 119.0(6)
C8 C7 H7 120.5
C5 C7 H7 120.5
C7 C8 C1 122.1(6)
C7 C8 Cl2 119.5(7)
C1 C8 Cl2 118.4(7)
C14 C13 C12 120.1(6)
C14 C13 H13 119.9
C12 C13 H13 119.9
C4 C2 C1 120.9(6)
C4 C2 H2 119.6
C1 C2 H2 119.6
C2 C4 C5 118.9(6)
C2 C4 C6 121.0(6)
C5 C4 C6 120.0(6)
C8 C1 C2 118.3(7)
C8 C1 H1 120.8
C2 C1 H1 120.8
C11 C10 C9 120.3(6)
C11 C10 H10 119.9
C9 C10 H10 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C16 C17 1.491(8)
C16 C18 1.503(9)
C16 C15 1.508(7)
C16 H16 0.9800
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
Cl1 C11 1.721(6)
Cl2 C8 1.755(6)
N2 C3 1.284(6)
N2 N1 1.443(5)
N4 C3 1.375(6)
N4 N5 1.392(5)
N4 H4 0.8600
O1 C15 1.228(6)
N5 C6 1.278(7)
C14 C9 1.369(7)
C14 C13 1.381(7)
C14 C3 1.466(7)
N1 C15 1.364(7)
N1 C6 1.411(7)
C11 C10 1.358(8)
C11 C12 1.362(8)
C9 C10 1.374(7)
C9 H9 0.9300
C6 C4 1.475(8)
C5 C4 1.369(7)
C5 C7 1.388(8)
C5 H5 0.9300
C12 C13 1.388(7)
C12 H12 0.9300
C7 C8 1.349(9)
C7 H7 0.9300
C8 C1 1.363(9)
C13 H13 0.9300
C2 C4 1.368(8)
C2 C1 1.394(8)
C2 H2 0.9300
C1 H1 0.9300
C10 H10 0.9300
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
N4 H4 O1 3_456 0.86 2.32 2.851(6) 120.7
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
C3 N4 N5 C6 34.2(8)
C3 N2 N1 C15 -123.6(6)
C3 N2 N1 C6 38.0(7)
N1 N2 C3 N4 -5.3(8)
N1 N2 C3 C14 173.4(5)
N5 N4 C3 N2 -31.7(8)
N5 N4 C3 C14 149.7(5)
C9 C14 C3 N2 162.7(6)
C13 C14 C3 N2 -17.9(8)
C9 C14 C3 N4 -18.6(9)
C13 C14 C3 N4 160.8(6)
C13 C14 C9 C10 -0.5(10)
C3 C14 C9 C10 178.9(7)
C6 N1 C15 O1 11.0(8)
N2 N1 C15 O1 171.5(5)
C6 N1 C15 C16 -170.1(5)
N2 N1 C15 C16 -9.6(7)
C17 C16 C15 O1 93.5(7)
C18 C16 C15 O1 -30.0(8)
C17 C16 C15 N1 -85.4(7)
C18 C16 C15 N1 151.2(6)
N4 N5 C6 N1 -0.5(8)
N4 N5 C6 C4 -173.5(5)
C15 N1 C6 N5 125.0(6)
N2 N1 C6 N5 -36.2(8)
C15 N1 C6 C4 -62.2(7)
N2 N1 C6 C4 136.7(5)
C10 C11 C12 C13 -1.9(11)
Cl1 C11 C12 C13 177.7(6)
C4 C5 C7 C8 -1.3(11)
C5 C7 C8 C1 0.5(12)
C5 C7 C8 Cl2 -179.0(5)
C9 C14 C13 C12 -0.2(9)
C3 C14 C13 C12 -179.6(6)
C11 C12 C13 C14 1.4(10)
C1 C2 C4 C5 1.9(10)
C1 C2 C4 C6 -176.9(6)
C7 C5 C4 C2 0.1(10)
C7 C5 C4 C6 178.9(6)
N5 C6 C4 C2 147.1(7)
N1 C6 C4 C2 -25.8(9)
N5 C6 C4 C5 -31.7(9)
N1 C6 C4 C5 155.5(6)
C7 C8 C1 C2 1.4(12)
Cl2 C8 C1 C2 -179.1(5)
C4 C2 C1 C8 -2.7(11)
C12 C11 C10 C9 1.2(12)
Cl1 C11 C10 C9 -178.3(6)
C14 C9 C10 C11 0.0(13)
_cod_database_fobs_code 2206938
_journal_paper_doi 10.1107/S1600536805018519