#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:10:10 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057385.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_7057385
loop_
_publ_author_name
'Gamekkanda, Janaka C.'
'Sinha, Abhijeet S.'
'Desper, John'
'Đaković, Marijana'
'Aakeröy, Christer B.'
_publ_section_title
;
 Competition between hydrogen bonds and halogen bonds: a structural study
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10539
_journal_paper_doi               10.1039/C8NJ00537K
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C10 H10 I2 O2, C12 H10 N2'
_chemical_formula_sum            'C22 H20 I2 N2 O2'
_chemical_formula_weight         598.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                93.5792(12)
_cell_angle_beta                 96.5739(11)
_cell_angle_gamma                107.2327(11)
_cell_formula_units_Z            2
_cell_length_a                   7.8373(7)
_cell_length_b                   11.6273(11)
_cell_length_c                   12.6853(12)
_cell_measurement_reflns_used    7080
_cell_measurement_temperature    228.(2)
_cell_measurement_theta_max      33.11
_cell_measurement_theta_min      2.58
_cell_volume                     1091.15(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      228.(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.0258
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15152
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         33.33
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         7687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0289
_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)+(0.0200P)²+0.6710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                6045
_reflns_number_total             7687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00537k2.cif
_cod_data_source_block           D1A4
_cod_depositor_comments
'Adding full bibliography for 7057378--7057386.cif.'
_cod_database_code               7057385
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.7732(3) 0.1228(2) 0.70196(17) 0.0211(4) Uani d . . 1
C C2 0.9225(3) 0.2441(2) 0.72503(18) 0.0226(4) Uani d . . 1
H H2A 0.9379 0.2826 0.6588 0.027 Uiso calc U R 1
H H2B 0.8872 0.2975 0.7752 0.027 Uiso calc U R 1
C C3 1.1013(3) 0.2280(2) 0.77209(17) 0.0231(4) Uani d . . 1
H H3A 1.0884 0.1962 0.8415 0.028 Uiso calc U R 1
H H3B 1.1943 0.3071 0.7837 0.028 Uiso calc U R 1
C C4 1.1618(3) 0.1418(2) 0.69925(17) 0.0209(4) Uani d . . 1
C C5 1.0121(3) 0.0211(2) 0.67204(18) 0.0233(4) Uani d . . 1
H H5A 1.0478 -0.0295 0.6194 0.028 Uiso calc U R 1
H H5B 0.9973 -0.0211 0.7365 0.028 Uiso calc U R 1
C C6 0.8323(3) 0.0369(2) 0.62753(17) 0.0226(4) Uani d . . 1
H H6A 0.7395 -0.0423 0.6164 0.027 Uiso calc U R 1
H H6B 0.8426 0.0688 0.5581 0.027 Uiso calc U R 1
H H7 0.624(4) 0.171(3) 0.597(3) 0.043(9) Uiso d . . 1
O O7 0.6085(2) 0.13918(17) 0.65397(14) 0.0283(4) Uani d . . 1
C C8 0.7387(3) 0.0699(2) 0.80391(18) 0.0244(4) Uani d . . 1
C C9 0.7353(3) 0.0320(3) 0.8892(2) 0.0312(5) Uani d . . 1
I I10 0.72878(2) -0.02968(2) 1.03349(2) 0.03274(5) Uani d . . 1
H H11 1.396(4) 0.124(3) 0.719(2) 0.036(8) Uiso d . . 1
O O11 1.3160(2) 0.12158(18) 0.75851(14) 0.0307(4) Uani d . . 1
C C12 1.2075(3) 0.1997(2) 0.60132(18) 0.0239(4) Uani d . . 1
C C13 1.2292(3) 0.2489(2) 0.52160(19) 0.0269(5) Uani d . . 1
I I14 1.25438(2) 0.32950(2) 0.38484(2) 0.02702(5) Uani d . . 1
C C15 0.2396(4) 0.5840(3) 0.8204(2) 0.0358(6) Uani d . . 1
H H15 0.165 0.5032 0.8112 0.043 Uiso calc U R 1
C C16 0.3140(4) 0.6291(3) 0.9182(2) 0.0371(6) Uani d . . 1
H H16 0.3847 0.7109 0.9278 0.044 Uiso calc U R 1
C C17 0.2620(4) 0.6480(2) 0.7240(2) 0.0294(5) Uani d . . 1
C C18 0.3288(4) 0.7740(2) 0.7259(2) 0.0313(5) Uani d . . 1
H H18 0.3584 0.8234 0.791 0.038 Uiso calc U R 1
C C19 0.3506(3) 0.8250(2) 0.6308(2) 0.0308(5) Uani d . . 1
H H19 0.3956 0.9097 0.6332 0.037 Uiso calc U R 1
N N20 0.3110(3) 0.7600(2) 0.53529(16) 0.0290(4) Uani d . . 1
C C21 0.2473(4) 0.6399(2) 0.5341(2) 0.0337(6) Uani d . . 1
H H21 0.22 0.5927 0.4679 0.04 Uiso calc U R 1
C C22 0.2196(4) 0.5815(2) 0.6245(2) 0.0327(5) Uani d . . 1
H H22 0.1721 0.4967 0.619 0.039 Uiso calc U R 1
C C23 0.2970(4) 0.5635(2) 1.0144(2) 0.0319(5) Uani d . . 1
C C24 0.3931(4) 0.6215(3) 1.1113(2) 0.0384(6) Uani d . . 1
H H24 0.4663 0.7024 1.1161 0.046 Uiso calc U R 1
C C25 0.3804(4) 0.5595(3) 1.2005(2) 0.0415(7) Uani d . . 1
H H25 0.4462 0.6008 1.2656 0.05 Uiso calc U R 1
N N26 0.2811(4) 0.4452(2) 1.20042(18) 0.0408(6) Uani d . . 1
C C27 0.1861(5) 0.3889(3) 1.1074(2) 0.0448(7) Uani d . . 1
H H27 0.1137 0.3081 1.1055 0.054 Uiso calc U R 1
C C28 0.1892(4) 0.4440(3) 1.0137(2) 0.0421(7) Uani d . . 1
H H28 0.1193 0.4013 0.9502 0.05 Uiso calc U R 1
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
O7 C1 C8 . 107.57(17)
O7 C1 C2 . 110.63(18)
C8 C1 C2 . 109.18(19)
O7 C1 C6 . 110.08(18)
C8 C1 C6 . 110.01(18)
C2 C1 C6 . 109.35(17)
C3 C2 C1 . 111.47(18)
C3 C2 H2A . 109.3
C1 C2 H2A . 109.3
C3 C2 H2B . 109.3
C1 C2 H2B . 109.3
H2A C2 H2B . 108.0
C2 C3 C4 . 112.21(18)
C2 C3 H3A . 109.2
C4 C3 H3A . 109.2
C2 C3 H3B . 109.2
C4 C3 H3B . 109.2
H3A C3 H3B . 107.9
O11 C4 C12 . 111.64(18)
O11 C4 C5 . 109.03(18)
C12 C4 C5 . 110.73(19)
O11 C4 C3 . 106.55(18)
C12 C4 C3 . 108.56(18)
C5 C4 C3 . 110.24(18)
C6 C5 C4 . 112.47(18)
C6 C5 H5A . 109.1
C4 C5 H5A . 109.1
C6 C5 H5B . 109.1
C4 C5 H5B . 109.1
H5A C5 H5B . 107.8
C5 C6 C1 . 112.40(18)
C5 C6 H6A . 109.1
C1 C6 H6A . 109.1
C5 C6 H6B . 109.1
C1 C6 H6B . 109.1
H6A C6 H6B . 107.9
C1 O7 H7 . 110.(2)
C9 C8 C1 . 171.3(2)
C8 C9 I10 . 179.2(2)
C9 I10 O11 2_757 174.73(8)
C4 O11 H11 . 110.(2)
C13 C12 C4 . 173.8(2)
C12 C13 I14 . 177.5(2)
C13 I14 N26 1_654 177.81(9)
C16 C15 C17 . 126.2(3)
C16 C15 H15 . 116.9
C17 C15 H15 . 116.9
C15 C16 C23 . 126.2(3)
C15 C16 H16 . 116.9
C23 C16 H16 . 116.9
C22 C17 C18 . 116.9(2)
C22 C17 C15 . 119.3(2)
C18 C17 C15 . 123.7(2)
C19 C18 C17 . 119.2(2)
C19 C18 H18 . 120.4
C17 C18 H18 . 120.4
N20 C19 C18 . 123.5(2)
N20 C19 H19 . 118.3
C18 C19 H19 . 118.3
C21 N20 C19 . 117.0(2)
N20 C21 C22 . 123.5(2)
N20 C21 H21 . 118.2
C22 C21 H21 . 118.2
C21 C22 C17 . 119.9(2)
C21 C22 H22 . 120.1
C17 C22 H22 . 120.1
C24 C23 C28 . 117.1(2)
C24 C23 C16 . 119.4(2)
C28 C23 C16 . 123.5(2)
C25 C24 C23 . 119.4(3)
C25 C24 H24 . 120.3
C23 C24 H24 . 120.3
N26 C25 C24 . 124.1(3)
N26 C25 H25 . 118.0
C24 C25 H25 . 118.0
C25 N26 C27 . 116.9(2)
N26 C27 C28 . 123.2(3)
N26 C27 H27 . 118.4
C28 C27 H27 . 118.4
C27 C28 C23 . 119.4(3)
C27 C28 H28 . 120.3
C23 C28 H28 . 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O7 . 1.433(3)
C1 C8 . 1.485(3)
C1 C2 . 1.528(3)
C1 C6 . 1.536(3)
C2 C3 . 1.527(3)
C2 H2A . 0.98
C2 H2B . 0.98
C3 C4 . 1.533(3)
C3 H3A . 0.98
C3 H3B . 0.98
C4 O11 . 1.437(3)
C4 C12 . 1.479(3)
C4 C5 . 1.529(3)
C5 C6 . 1.524(3)
C5 H5A . 0.98
C5 H5B . 0.98
C6 H6A . 0.98
C6 H6B . 0.98
O7 H7 . 0.84(3)
C8 C9 . 1.194(3)
C9 I10 . 2.007(2)
I10 O11 2_757 2.9273(17)
O11 H11 . 0.84(3)
C12 C13 . 1.197(3)
C13 I14 . 2.024(2)
I14 N26 1_654 2.768(2)
C15 C16 . 1.313(4)
C15 C17 . 1.472(3)
C15 H15 . 0.94
C16 C23 . 1.478(3)
C16 H16 . 0.94
C17 C22 . 1.390(4)
C17 C18 . 1.400(4)
C18 C19 . 1.383(3)
C18 H18 . 0.94
C19 N20 . 1.340(3)
C19 H19 . 0.94
N20 C21 . 1.334(3)
C21 C22 . 1.375(3)
C21 H21 . 0.94
C22 H22 . 0.94
C23 C24 . 1.384(4)
C23 C28 . 1.395(4)
C24 C25 . 1.377(4)
C24 H24 . 0.94
C25 N26 . 1.327(4)
C25 H25 . 0.94
N26 C27 . 1.338(4)
C27 C28 . 1.384(4)
C27 H27 . 0.94
C28 H28 . 0.94
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O7 H7 N20 2_666 0.84(3) 1.95(3) 2.792(3) 172.(3)
O11 H11 O7 1_655 0.84(3) 1.91(3) 2.740(2) 169.(3)
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
O7 C1 C2 C3 -177.70(17)
C8 C1 C2 C3 64.1(2)
C6 C1 C2 C3 -56.3(2)
C1 C2 C3 C4 57.1(2)
C2 C3 C4 O11 -172.21(18)
C2 C3 C4 C12 67.4(2)
C2 C3 C4 C5 -54.0(2)
O11 C4 C5 C6 169.34(17)
C12 C4 C5 C6 -67.4(2)
C3 C4 C5 C6 52.7(2)
C4 C5 C6 C1 -54.7(2)
O7 C1 C6 C5 177.09(18)
C8 C1 C6 C5 -64.5(2)
C2 C1 C6 C5 55.4(2)
C17 C15 C16 C23 -177.5(3)
C16 C15 C17 C22 161.6(3)
C16 C15 C17 C18 -16.7(5)
C22 C17 C18 C19 -0.7(4)
C15 C17 C18 C19 177.7(3)
C17 C18 C19 N20 0.0(4)
C18 C19 N20 C21 0.0(4)
C19 N20 C21 C22 0.6(4)
N20 C21 C22 C17 -1.3(4)
C18 C17 C22 C21 1.3(4)
C15 C17 C22 C21 -177.2(3)
C15 C16 C23 C24 175.9(3)
C15 C16 C23 C28 -3.6(5)
C28 C23 C24 C25 0.9(4)
C16 C23 C24 C25 -178.6(3)
C23 C24 C25 N26 0.4(5)
C24 C25 N26 C27 -1.2(5)
C25 N26 C27 C28 0.7(5)
N26 C27 C28 C23 0.6(5)
C24 C23 C28 C27 -1.4(4)
C16 C23 C28 C27 178.1(3)
