#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:00:53 +0100 (vie 05 de feb de 2021) $
#$Revision: 261615 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/15/7241557.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_7241557
loop_
_publ_author_name
'Peloquin, Andrew J.'
'Kobra, Khadijatul'
'McMillen, Colin D.'
'Iacono, Scott T.'
'Pennington, William T.'
_publ_section_title
;
 Isolation of hydrazine oxidation products via halogen bonding: C--I bond
 scission and crystal polymorphism
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              419
_journal_page_last               426
_journal_paper_doi               10.1039/D0CE01568G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C6 F4 I2, 0.5(C4 H12 N4)'
_chemical_formula_sum            'C8 H6 F4 I2 N2'
_chemical_formula_weight         459.95
_chemical_name_common
'bis(1,3-diiodo-2,4,5,6-tetrafluorobenzene) 1,4-dimethylhexahydro-s-tetrazine cocrystal'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                103.485(5)
_cell_angle_beta                 96.047(6)
_cell_angle_gamma                93.183(5)
_cell_formula_units_Z            2
_cell_length_a                   6.3151(9)
_cell_length_b                   8.5815(12)
_cell_length_c                   11.0306(15)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.45
_cell_volume                     576.08(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12764
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    5.486
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.094
_refine_diff_density_max         1.330
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0213
_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)+(0.0112P)²+1.5122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2288
_reflns_number_total             2361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01568g2.cif
_cod_data_source_block           2(13-F4DIB)(14-DMeTetz)
_cod_depositor_comments
'Adding full bibliography for 7241557--7241566.cif.'
_cod_database_code               7241557
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.158
_shelx_estimated_absorpt_t_max   0.627
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.16848(3) 0.39776(2) 0.20376(2) 0.01983(7) Uani 1 1 d . . . . .
I2 I 0.36556(3) 0.86728(2) 0.70772(2) 0.01954(7) Uani 1 1 d . . . . .
F1 F 0.1428(3) 0.5982(2) 0.48054(19) 0.0250(4) Uani 1 1 d . . . . .
F2 F 0.7908(3) 0.9248(2) 0.57638(19) 0.0260(4) Uani 1 1 d . . . . .
F3 F 0.8991(3) 0.7896(3) 0.3465(2) 0.0264(4) Uani 1 1 d . . . . .
F4 F 0.6296(3) 0.5681(2) 0.18130(19) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.3791(5) 0.5764(4) 0.3280(3) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.3295(5) 0.6472(4) 0.4470(3) 0.0191(6) Uani 1 1 d . . . . .
C3 C 0.4624(5) 0.7646(4) 0.5333(3) 0.0175(6) Uani 1 1 d . . . . .
C4 C 0.6552(5) 0.8107(4) 0.4979(3) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.7119(5) 0.7421(4) 0.3803(3) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.5728(5) 0.6278(4) 0.2964(3) 0.0203(6) Uani 1 1 d . . . . .
N1 N -0.1024(4) 0.1435(3) 0.0135(2) 0.0178(5) Uani 1 1 d . . . . .
N2 N -0.1978(5) 0.0063(3) 0.0495(3) 0.0190(5) Uani 1 1 d . . . . .
C7 C -0.2735(6) 0.2350(4) -0.0266(3) 0.0231(7) Uani 1 1 d . . . . .
H7A H -0.211263 0.329275 -0.050185 0.035 Uiso 1 1 calc R U . . .
H7B H -0.359008 0.270129 0.042400 0.035 Uiso 1 1 calc R U . . .
H7C H -0.364864 0.166977 -0.099103 0.035 Uiso 1 1 calc R U . . .
C8 C -0.0310(5) -0.0880(4) 0.0879(3) 0.0191(6) Uani 1 1 d . . . . .
H8A H -0.096882 -0.182382 0.111460 0.023 Uiso 1 1 calc R U . . .
H8B H 0.060355 -0.022111 0.162719 0.023 Uiso 1 1 calc R U . . .
H1N2 H -0.270(7) -0.045(5) -0.012(4) 0.019(10) Uiso 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 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.0(3) . . ?
C6 C1 I1 122.1(2) . . ?
C2 C1 I1 120.8(2) . . ?
F1 C2 C3 118.3(3) . . ?
F1 C2 C1 118.2(3) . . ?
C3 C2 C1 123.5(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 I2 122.8(2) . . ?
C2 C3 I2 119.9(2) . . ?
F2 C4 C3 120.5(3) . . ?
F2 C4 C5 118.4(3) . . ?
C3 C4 C5 121.1(3) . . ?
F3 C5 C6 119.9(3) . . ?
F3 C5 C4 120.4(3) . . ?
C6 C5 C4 119.6(3) . . ?
F4 C6 C5 118.0(3) . . ?
F4 C6 C1 120.5(3) . . ?
C5 C6 C1 121.4(3) . . ?
N2 N1 C7 108.5(3) . . ?
N2 N1 C8 109.7(2) . 2 ?
C7 N1 C8 111.3(3) . 2 ?
N1 N2 C8 109.5(3) . . ?
N1 N2 H1N2 105(3) . . ?
C8 N2 H1N2 110(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 111.6(3) . 2 ?
N2 C8 H8A 109.3 . . ?
N1 C8 H8A 109.3 2 . ?
N2 C8 H8B 109.3 . . ?
N1 C8 H8B 109.3 2 . ?
H8A C8 H8B 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.099(3) . ?
I2 C3 2.090(3) . ?
F1 C2 1.347(4) . ?
F2 C4 1.341(4) . ?
F3 C5 1.347(4) . ?
F4 C6 1.348(4) . ?
C1 C6 1.383(5) . ?
C1 C2 1.388(5) . ?
C2 C3 1.384(4) . ?
C3 C4 1.382(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.378(5) . ?
N1 N2 1.448(4) . ?
N1 C7 1.461(4) . ?
N1 C8 1.477(4) 2 ?
N2 C8 1.451(4) . ?
N2 H1N2 0.80(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A I1 0.98 3.21 4.135(4) 158.0 2_565
C7 H7B I2 0.98 3.24 3.911(4) 126.9 2_566
C7 H7B F4 0.98 2.67 3.353(4) 127.4 1_455
C7 H7C I2 0.98 3.20 4.150(3) 163.4 1_444
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.4(3) . . . . ?
I1 C1 C2 F1 0.0(4) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
I1 C1 C2 C3 179.5(2) . . . . ?
F1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
F1 C2 C3 I2 -2.3(4) . . . . ?
C1 C2 C3 I2 178.1(2) . . . . ?
C2 C3 C4 F2 179.4(3) . . . . ?
I2 C3 C4 F2 0.4(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
I2 C3 C4 C5 -178.6(2) . . . . ?
F2 C4 C5 F3 0.1(5) . . . . ?
C3 C4 C5 F3 179.2(3) . . . . ?
F2 C4 C5 C6 -178.2(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
F3 C5 C6 F4 -0.7(5) . . . . ?
C4 C5 C6 F4 177.5(3) . . . . ?
F3 C5 C6 C1 -179.9(3) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C2 C1 C6 F4 -178.1(3) . . . . ?
I1 C1 C6 F4 2.6(4) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
I1 C1 C6 C5 -178.2(2) . . . . ?
C7 N1 N2 C8 179.1(3) . . . . ?
C8 N1 N2 C8 57.2(3) 2 . . . ?
N1 N2 C8 N1 -58.3(3) . . . 2 ?
