#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:41:19 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557294.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_1557294
loop_
_publ_author_name
'Schnell, Simon D.'
'Hoff, Lukas V.'
'Panchagnula, Advaita'
'Wurzenberger, Maximilian H. H.'
'Klapötke, Thomas M.'
'Sieber, Simon'
'Linden, Anthony'
'Gademann, Karl'
_publ_section_title
;
 3-Bromotetrazine: labelling of macromolecules via monosubstituted
 bifunctional s-tetrazines
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              3042
_journal_page_last               3047
_journal_paper_doi               10.1039/C9SC06169J
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C2 H Br N4'
_chemical_formula_sum            'C2 H Br N4'
_chemical_formula_weight         160.98
_chemical_melting_point          344
_chemical_name_systematic        3-bromotetrazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7468(5)
_cell_length_b                   5.60166(19)
_cell_length_c                   12.9507(4)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      73.5270
_cell_measurement_theta_min      3.3990
_cell_volume                     924.72(6)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_collection
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.945
_diffrn_reflns_theta_min         6.838
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_exptl_absorpt_coefficient_mu    10.963
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.00063(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0285P)²+0.4717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                904
_reflns_number_total             926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc06169j2.cif
_cod_data_source_block           2
_cod_depositor_comments
;Adding full bibliography for 1557290--1557295.cif.

 Adding full bibliography for 1557290--1557295.cif.
;
_cod_database_code               1557294
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.742
_oxdiff_exptl_absorpt_empirical_full_max 1.469
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_file
;
TITL gd1803_a.res in Pbca
    x.res
    created by SHELXL-2018/1 at 17:51:47 on 06-Mar-2018
REM Old TITL GD1803 in Pbca
REM SHELXT solution in Pbca
REM R1 0.073, Rweak 0.003, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C6 Br
CELL 1.54184 12.7468 5.60166 12.9507 90 90 90
ZERR 8 0.0005 0.00019 0.0004 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N
UNIT 16 8 8 32
TEMP -113
L.S. 10
PLAN  10
BOND $H
CONF
fmap 2
ACTA
WGHT    0.028500    0.471700
EXTI    0.000631
FVAR       3.50941
BR1   3    0.646811    0.323707    0.475037    11.00000    0.03190    0.03146 =
         0.01984    0.00168    0.00010   -0.00041
N2    4    0.584883    0.680903    0.343886    11.00000    0.02205    0.02423 =
         0.03113   -0.00337    0.00169    0.00074
N3    4    0.571151    0.776433    0.250792    11.00000    0.02304    0.02650 =
         0.03775    0.00521   -0.00135    0.00076
N5    4    0.663354    0.451197    0.174696    11.00000    0.02637    0.03157 =
         0.02160   -0.00037    0.00154   -0.00196
N6    4    0.677312    0.354742    0.267156    11.00000    0.02231    0.02437 =
         0.02231   -0.00154   -0.00021    0.00087
C1    1    0.634772    0.472126    0.346045    11.00000    0.01898    0.02126 =
         0.02071    0.00008   -0.00100   -0.00137
C4    1    0.609148    0.654714    0.170686    11.00000    0.02616    0.03367 =
         0.02916    0.00757   -0.00204   -0.00196
AFIX  43
H4    2    0.596353    0.719338    0.104045    11.00000   -1.20000
AFIX   0
HKLF 4




REM  gd1803_a.res in Pbca
REM R1 =  0.0185 for     904 Fo > 4sig(Fo)  and  0.0189 for all     926 data
REM     65 parameters refined using      0 restraints

END

WGHT      0.0285      0.4717

REM Highest difference peak  0.324,  deepest hole -0.434,  1-sigma level  0.067
Q1    1   0.6458  0.1610  0.4383  11.00000  0.05    0.32
Q2    1   0.6600  0.3185  0.2474  11.00000  0.05    0.27
Q3    1   0.6075  0.5819  0.3335  11.00000  0.05    0.27
Q4    1   0.6557  0.4988  0.5201  11.00000  0.05    0.25
Q5    1   0.6424  0.4695  0.4484  11.00000  0.05    0.22
Q6    1   0.6543  0.4269  0.3058  11.00000  0.05    0.22
Q7    1   0.6404  0.3402  0.3875  11.00000  0.05    0.22
Q8    1   0.6518  0.1831  0.3300  11.00000  0.05    0.21
Q9    1   0.6424  0.1541  0.5114  11.00000  0.05    0.20
Q10   1   0.6409  0.5647  0.1814  11.00000  0.05    0.20
;
_shelx_res_checksum              50521
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.64681(2) 0.32371(4) 0.47504(2) 0.02773(12) Uani 1 1 d . .
N2 N 0.58488(13) 0.6809(3) 0.34389(14) 0.0258(4) Uani 1 1 d . .
N3 N 0.57115(14) 0.7764(3) 0.25079(15) 0.0291(3) Uani 1 1 d . .
N5 N 0.66335(13) 0.4512(3) 0.17470(12) 0.0265(3) Uani 1 1 d . .
N6 N 0.67731(13) 0.3547(3) 0.26716(12) 0.0230(3) Uani 1 1 d . .
C1 C 0.63477(13) 0.4721(3) 0.34604(14) 0.0203(3) Uani 1 1 d . .
C4 C 0.60915(17) 0.6547(3) 0.17069(16) 0.0297(4) Uani 1 1 d . .
H4 H 0.596353 0.719338 0.104045 0.036 Uiso 1 1 calc R U
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
Br1 0.03190(18) 0.03146(17) 0.01984(15) 0.00168(6) 0.00010(7) -0.00041(7)
N2 0.0220(8) 0.0242(8) 0.0311(9) -0.0034(6) 0.0017(7) 0.0007(5)
N3 0.0230(8) 0.0265(8) 0.0378(8) 0.0052(7) -0.0014(7) 0.0008(6)
N5 0.0264(8) 0.0316(8) 0.0216(7) -0.0004(6) 0.0015(6) -0.0020(6)
N6 0.0223(8) 0.0244(7) 0.0223(7) -0.0015(6) -0.0002(6) 0.0009(6)
C1 0.0190(8) 0.0213(8) 0.0207(8) 0.0001(7) -0.0010(6) -0.0014(6)
C4 0.0262(11) 0.0337(10) 0.0292(10) 0.0076(8) -0.0020(8) -0.0020(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0230
0 0 -1 0.0230
-1 0 0 0.0387
1 0 0 0.0410
1 4 -1 0.1284
5 -3 1 0.0956
-5 -1 0 0.0549
-5 1 0 0.0735
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 N2 C1 115.79(16)
N2 N3 C4 116.86(16)
N6 N5 C4 116.93(16)
N5 N6 C1 115.94(15)
N6 C1 N2 127.78(17)
N6 C1 Br1 115.61(13)
N2 C1 Br1 116.61(14)
N3 C4 N5 126.53(19)
N3 C4 H4 116.7
N5 C4 H4 116.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.8723(19)
N2 N3 1.331(2)
N2 C1 1.332(2)
N3 C4 1.333(3)
N5 N6 1.326(2)
N5 C4 1.334(3)
N6 C1 1.330(2)
C4 H4 0.9500
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 N2 N3 C4 -0.5(2)
C4 N5 N6 C1 0.4(2)
N5 N6 C1 N2 -4.0(3)
N5 N6 C1 Br1 175.90(12)
N3 N2 C1 N6 4.0(3)
N3 N2 C1 Br1 -175.86(13)
N2 N3 C4 N5 -2.9(3)
N6 N5 C4 N3 3.0(3)
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 0.0008 1.0016 -0.0028 0.1188 -0.0088
-0.0001 -0.0008 -1.0016 0.0028 -0.1188 0.0088
-0.9993 -0.0012 -0.0011 0.0312 0.0092 0.1164
0.9993 0.0012 0.0011 -0.0312 -0.0092 -0.1164
0.9696 3.9958 -1.0084 -1.0890 -0.1317 0.1767
5.0190 -2.9899 1.0131 0.6364 0.0753 -0.8040
-4.9892 -1.0047 -0.0036 0.4214 0.0472 0.5108
-5.0041 0.9930 -0.0076 -0.1089 0.0453 0.6530
