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#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010139.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_2010139
loop_
_publ_author_name
'Ueng, C.-H.'
'Wang, Y.'
'Yeh, M.-Y.'
_publ_section_title
;
 Two heterocyclic 1,2,4,5-tetrazines
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1781
_journal_page_last               1784
_journal_paper_doi               10.1107/S0108270194002192
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C16 H14 Br2 N4 O2'
_chemical_formula_sum            'C16 H14 Br2 N4 O2'
_chemical_formula_weight         454
_chemical_name_systematic
3,6-dibromo-1,4-dihydro-1,4-di(p-methoxyphenyl)-1,2,4,5-tetrazine
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   18.975(3)
_cell_length_b                   10.327(2)
_cell_length_c                   8.569(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.83
_cell_measurement_theta_min      10.57
_cell_volume                     1679.1(7)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.008
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1587
_diffrn_reflns_theta_max         24.9
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.80
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   '\y scans'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.80
_exptl_crystal_density_meas      1.79(3)
_exptl_crystal_density_method    'flotation in CHCl~3~/CHBr~3~'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.520
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.28
_refine_ls_number_parameters     137
_refine_ls_number_reflns         875
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.135
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'from counting statistics'
_refine_ls_wR_factor_obs         0.028
_reflns_number_observed          875
_reflns_number_total             1474
_reflns_observed_criterion       I>2.0\s(I)
_cod_data_source_file            al1011.cif
_cod_data_source_block           al1011_structure_2_of_2
_cod_original_cell_volume        1679.2
_cod_database_code               2010139
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Br .43730(4) 0.20775(8) .07844(8)
N(1) .4331(3) 0.1087(5) -0.2289(6)
N(2) .5418(3) 0.1553(6) -0.1225(6)
C(1) .4763(4) 0.1506(7) -0.1111(7)
C(2) .3576(4) 0.1137(7) -0.2185(8)
C(3) .3184(4) 0.2056(8) -0.2935(8)
C(4) .2466(4) 0.2061(9) -0.2715(9)
C(5) .2125(4) 0.1172(8) -.1817(8)
C(6) .2522(5) 0.0235(9) -0.1085(9)
C(7) .3250(4) 0.0222(9) -0.1280(9)
C(8) .1031(6) 0.0310(10) -0.092(2)
O .1409(3) 0.1279(5) -0.1723(6)
H(3) .340(3) 0.278(5) -0.366(6)
H(4) .221(3) 0.258(6) -0.313(7)
H(6) .234(4) -0.034(7) -0.050(8)
H(7) .346(3) -0.041(6) -0.082(8)
H(8A) .051(3) 0.051(6) -0.114(7)
H(8B) .122(4) 0.027(7) -0.005(7)
H(8C) .107(4) -0.051(6) -0.127(9)
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
N(2a) N(1) C(1) 110.3(5) yes
N(2a) N(1) C(2) 111.9(5) yes
C(1) N(1) C(2) 122.7(5) yes
N(1a) N(2) C(1) 112.7(5) yes
Br C(1) N(1) 120.0(5) yes
Br C(1) N(2) 116.6(5) yes
N(1) C(1) N(2) 123.4(6) yes
N(1) C(2) C(3) 122.6(6) yes
N(1) C(2) C(7) 117.4(7) yes
C(3) C(2) C(7) 120.0(7) no
C(2) C(3) C(4) 118.5(7) no
C(2) C(3) H(3) 124(3) no
C(4) C(3) H(3) 117(3) no
C(3) C(4) C(5) 123.1(8) no
C(3) C(4) H(4) 122(4) no
C(5) C(4) H(4) 114(4) no
C(4) C(5) C(6) 118.1(7) no
C(4) C(5) O 116.9(7) yes
C(6) C(5) O 125.0(7) yes
C(5) C(6) C(7) 119.7(8) no
C(5) C(6) H(6) 122(5) no
C(7) C(6) H(6) 118(5) no
C(2) C(7) C(6) 120.6(8) no
C(2) C(7) H(7) 124(4) no
C(6) C(7) H(7) 114(4) no
O C(8) H(8A) 104(4) no
O C(8) H(8B) 104(5) no
O C(8) H(8C) 117(5) no
H(8A) C(8) H(8B) 127(6) no
H(8A) C(8) H(8C) 102(6) no
H(8B) C(8) H(8C) 102(7) no
C(5) O C(8) 118.4(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C(1) 1.880(7) yes
N(1) N(2a) 1.443(8) yes
N(1) C(1) 1.370(9) yes
N(1) C(2) 1.436(9) yes
N(2) C(1) 1.247(9) yes
C(2) C(3) 1.366(11) no
C(2) C(7) 1.369(11) no
C(3) C(4) 1.375(11) no
C(3) H(3) 1.05(6) no
C(4) C(5) 1.362(12) no
C(4) H(4) 0.80(5) no
C(5) C(6) 1.377(12) no
C(5) O 1.366(9) yes
C(6) C(7) 1.393(13) no
C(6) H(6) 0.86(7) no
C(7) H(7) 0.86(6) no
C(8) O 1.410(10) yes
C(8) H(8A) 1.03(6) no
C(8) H(8B) 0.82(6) no
C(8) H(8C) 0.90(7) no
H(8A) H(8C) 1.50(9) no
H(8B) H(8C) 1.34(10) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057350
