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#$Date: 2016-08-07 11:22:01 +0200 (dom 07 de ago de 2016) $
#$Revision: 185522 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/93/7039322.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_7039322
loop_
_publ_author_name
'Chand, Deepak'
'He, Chunlin'
'Hooper, Joseph P.'
'Mitchell, Lauren A.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Mono- and diiodo-1,2,3-triazoles and their mono nitro derivatives.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9684
_journal_page_last               9688
_journal_paper_doi               10.1039/c6dt01731b
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C3 H3 I2 N3'
_chemical_formula_sum            'C3 H3 I2 N3'
_chemical_formula_weight         334.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-09 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4559(8)
_cell_length_b                   4.1982(3)
_cell_length_c                   7.7048(5)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.64
_cell_volume                     370.56(4)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3581
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.186
_exptl_absorpt_coefficient_mu    8.396
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.001
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     41
_refine_ls_number_reflns         838
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0186
_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)+(0.0179P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0452
_refine_ls_wR_factor_ref         0.0453
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                830
_reflns_number_total             838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01731b2.cif
_cod_data_source_block           shrv382
_cod_depositor_comments
'Adding full bibliography for 7039322--7039325.cif.'
_cod_database_code               7039322
_shelx_shelxl_version_number     2014/7
_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   0.135
_shelx_estimated_absorpt_t_max   0.864
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'
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
I1 I 0.82126(2) 0.55476(6) 0.49424(11) 0.02175(13) Uani 1 1 d . . .
C2 C 0.9391(3) 0.3625(12) 0.6689(7) 0.0159(8) Uani 1 1 d . . .
N3 N 0.9016(3) 0.2128(10) 0.8104(5) 0.0189(8) Uani 1 1 d . . .
N4 N 1.0000 0.1251(15) 0.8897(8) 0.0170(11) Uani 1 2 d S T P
C5 C 1.0000 -0.0361(19) 1.0567(12) 0.0261(17) Uani 1 2 d S T P
H5A H 1.0805 -0.0839 1.0909 0.039 Uiso 0.5 1 calc R U P
H5B H 0.9556 -0.2349 1.0476 0.039 Uiso 0.5 1 calc R U P
H5C H 0.9639 0.1019 1.1441 0.039 Uiso 0.5 1 calc R U P
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
I1 0.02029(17) 0.02361(19) 0.0213(2) 0.0028(3) -0.00604(13) 0.00042(7)
C2 0.0128(19) 0.0186(19) 0.016(2) -0.0006(19) -0.0026(17) 0.0007(16)
N3 0.0154(17) 0.0236(19) 0.018(2) -0.0002(17) -0.0013(15) 0.0021(13)
N4 0.016(2) 0.017(2) 0.018(3) 0.000(2) 0.000 0.000
C5 0.030(4) 0.025(4) 0.023(4) 0.007(3) 0.000 0.000
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'
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'
H H 0.0000 0.0000 '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
N3 C2 C2 108.8(2) . 3_755
N3 C2 I1 120.5(3) . .
C2 C2 I1 130.69(13) 3_755 .
C2 N3 N4 103.5(4) . .
N3 N4 N3 115.3(6) 3_755 .
N3 N4 C5 122.3(3) 3_755 .
N3 N4 C5 122.3(3) . .
N4 C5 H5A 109.5 . .
N4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C2 2.070(5) .
C2 N3 1.329(7) .
C2 C2 1.396(8) 3_755
N3 N4 1.334(5) .
N4 N3 1.334(5) 3_755
N4 C5 1.454(11) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
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_4
C2 C2 N3 N4 -0.6(4) 3_755 .
I1 C2 N3 N4 -179.7(4) . .
C2 N3 N4 N3 1.1(7) . 3_755
C2 N3 N4 C5 177.1(6) . .
