#------------------------------------------------------------------------------
#$Date: 2021-10-06 19:16:29 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269786 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158240.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_7158240
loop_
_publ_author_name
'Alvarez, Marie Stacey'
'Houzé, Cedric'
'Groni, Sihem'
'Schöllhorn, Bernd'
'Fave, Claire'
_publ_section_title
;
 Halogen bonding effect on electrochemical anion oxidation in ionic
 liquids.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7587
_journal_page_last               7593
_journal_paper_doi               10.1039/d1ob01031j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         ' C6 H10 I N2, Br '
_chemical_formula_sum            'C6 H10 Br I N2'
_chemical_formula_weight         316.97
_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
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-28 deposited with the CCDC.	2021-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7188(9)
_cell_length_b                   11.8757(9)
_cell_length_c                   13.5901(10)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.87
_cell_volume                     1891.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40914
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.580
_diffrn_reflns_theta_min         2.865
_exptl_absorpt_coefficient_mu    7.548
_exptl_absorpt_correction_T_max  0.6461
_exptl_absorpt_correction_T_min  0.3307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.273
_refine_diff_density_min         -1.793
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0283P)²+5.1578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             2897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01031j2.cif
_cod_data_source_block           2724_GuillotICMMO
_cod_depositor_comments
'Adding full bibliography for 7158240--7158241.cif.'
_cod_database_code               7158240
_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   0.243
_shelx_estimated_absorpt_t_max   0.501
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4998(3) 0.1302(2) 0.5955(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.3362(3) 0.0449(3) 0.5625(2) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.269480 0.000189 0.569735 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3666(3) 0.1052(3) 0.4821(3) 0.0205(6) Uani 1 1 d . . . . .
H3 H 0.325259 0.110618 0.422108 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4182(3) 0.0173(3) 0.7331(2) 0.0200(6) Uani 1 1 d . . . . .
H4A H 0.491446 -0.018571 0.748160 0.030 Uiso 1 1 calc R U . . .
H4B H 0.356698 -0.038070 0.739473 0.030 Uiso 1 1 calc R U . . .
H4C H 0.404986 0.079584 0.779004 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5301(3) 0.2348(3) 0.4376(2) 0.0226(6) Uani 1 1 d . . . . .
H5A H 0.506636 0.220147 0.368821 0.027 Uiso 1 1 calc R U . . .
H5B H 0.613144 0.220898 0.442687 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5052(3) 0.3571(3) 0.4633(3) 0.0269(7) Uani 1 1 d . . . . .
H6A H 0.423194 0.371517 0.456849 0.040 Uiso 1 1 calc R U . . .
H6B H 0.547307 0.406633 0.418493 0.040 Uiso 1 1 calc R U . . .
H6C H 0.529085 0.372010 0.531207 0.040 Uiso 1 1 calc R U . . .
N1 N 0.4205(2) 0.0609(2) 0.63204(19) 0.0162(5) Uani 1 1 d . . . . .
N2 N 0.4690(2) 0.1573(2) 0.50369(19) 0.0178(5) Uani 1 1 d . . . . .
I1 I 0.64033(2) 0.19344(2) 0.67184(2) 0.01633(7) Uani 1 1 d . . . . .
Br1 Br 0.82940(3) 0.32123(2) 0.79043(2) 0.01781(8) Uani 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 0.0031 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2910 2.4595 '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
N1 C1 N2 107.9(3) . . ?
N1 C1 I1 125.9(2) . . ?
N2 C1 I1 126.1(2) . . ?
C3 C2 N1 107.0(3) . . ?
C2 C3 N2 107.1(3) . . ?
N2 C5 C6 111.3(3) . . ?
C1 N1 C2 109.1(3) . . ?
C1 N1 C4 125.2(3) . . ?
C2 N1 C4 125.4(3) . . ?
C1 N2 C3 108.9(3) . . ?
C1 N2 C5 126.0(3) . . ?
C3 N2 C5 124.9(3) . . ?
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
C1 N1 1.337(4) . ?
C1 N2 1.338(4) . ?
C1 I1 2.086(3) . ?
C2 C3 1.354(5) . ?
C2 N1 1.380(4) . ?
C3 N2 1.382(4) . ?
C4 N1 1.467(4) . ?
C5 N2 1.471(4) . ?
C5 C6 1.522(5) . ?
