#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:09:14 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190088 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/69/7226925.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_7226925
loop_
_publ_author_name
'Perera, M. D.'
'Desper, J.'
'Sinha, A. S.'
'Aakeröy, C. B.'
_publ_section_title
;
 Impact and importance of electrostatic potential calculations for
 predicting structural patterns of hydrogen and halogen bonding
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              8631
_journal_paper_doi               10.1039/C6CE02089E
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
;
(C6 F4 I2) (C10 H7 N3)2
;
_chemical_formula_sum            'C26 H14 F4 I2 N6'
_chemical_formula_weight         740.23
_chemical_name_systematic
;
Mp-p1b-Hb7 1,4-diiodotetrafluorobenzene, ([1,2,3]Triazolo[1,5-a]quinoline)2
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                64.954(6)
_cell_angle_beta                 79.728(5)
_cell_angle_gamma                87.328(5)
_cell_formula_units_Z            1
_cell_length_a                   6.6906(14)
_cell_length_b                   9.568(2)
_cell_length_c                   10.618(2)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.87
_cell_measurement_theta_min      2.35
_cell_volume                     605.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15546
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         33.04
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_T_max  0.7074
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.426
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0181
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0464
_reflns_number_gt                3909
_reflns_number_total             4039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce02089e2.cif
_cod_data_source_block           A1XB4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226924--7226932.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7226925
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.83374(18) 0.20754(14) 0.45789(13) 0.0149(2) Uani 1 1 d .
N12 N 0.64021(19) 0.19922(16) 0.52325(14) 0.0198(2) Uani 1 1 d .
N13 N 0.6398(2) 0.26774(17) 0.60781(15) 0.0225(3) Uani 1 1 d .
C14 C 0.8284(2) 0.31859(19) 0.59783(16) 0.0210(3) Uani 1 1 d .
H14 H 0.8660 0.3712 0.6489 0.025 Uiso 1 1 calc R
C15 C 0.9579(2) 0.28138(17) 0.50092(15) 0.0160(2) Uani 1 1 d .
C16 C 1.1678(2) 0.30124(18) 0.44298(16) 0.0195(3) Uani 1 1 d .
H16 H 1.2569 0.3507 0.4730 0.023 Uiso 1 1 calc R
C17 C 1.2386(2) 0.24881(18) 0.34463(16) 0.0198(3) Uani 1 1 d .
H17 H 1.3787 0.2639 0.3037 0.024 Uiso 1 1 calc R
C18 C 1.1081(2) 0.17086(17) 0.30029(15) 0.0166(2) Uani 1 1 d .
C19 C 1.1803(3) 0.11175(19) 0.20101(17) 0.0245(3) Uani 1 1 d .
H19 H 1.3199 0.1259 0.1588 0.029 Uiso 1 1 calc R
C20 C 1.0514(3) 0.0335(2) 0.16414(18) 0.0296(4) Uani 1 1 d .
H20 H 1.1026 -0.0067 0.0973 0.035 Uiso 1 1 calc R
C21 C 0.8473(3) 0.01307(19) 0.22383(19) 0.0284(3) Uani 1 1 d .
H21 H 0.7594 -0.0402 0.1966 0.034 Uiso 1 1 calc R
C22 C 0.7698(3) 0.06907(18) 0.32235(17) 0.0213(3) Uani 1 1 d .
H22 H 0.6300 0.0541 0.3640 0.026 Uiso 1 1 calc R
C23 C 0.9011(2) 0.14777(16) 0.35912(14) 0.0153(2) Uani 1 1 d .
C31 C 0.1359(2) 0.45650(17) 0.90638(15) 0.0155(2) Uani 1 1 d .
I1 I 0.338314(13) 0.382714(10) 0.775792(9) 0.01712(4) Uani 1 1 d .
C32 C -0.0624(2) 0.40148(16) 0.95087(15) 0.0149(2) Uani 1 1 d .
F32 F -0.13019(14) 0.30457(11) 0.90569(10) 0.02075(18) Uani 1 1 d .
C36 C 0.1955(2) 0.55647(16) 0.95678(14) 0.0150(2) Uani 1 1 d .
F36 F 0.38531(13) 0.61559(11) 0.91718(10) 0.01989(17) 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 0.0033 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'
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'
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
N12 N11 C15 111.46(12) . .
N12 N11 C23 124.71(12) . .
C15 N11 C23 123.83(12) . .
N13 N12 N11 106.07(12) . .
N12 N13 C14 110.39(12) . .
N12 N13 I1 137.60(10) . .
C14 N13 I1 111.11(10) . .
N13 C14 C15 108.38(13) . .
N13 C14 H14 125.8 . .
C15 C14 H14 125.8 . .
N11 C15 C14 103.69(12) . .
N11 C15 C16 119.44(13) . .
C14 C15 C16 136.87(14) . .
C17 C16 C15 118.78(13) . .
C17 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C16 C17 C18 121.58(13) . .
C16 C17 H17 119.2 . .
C18 C17 H17 119.2 . .
C23 C18 C19 117.57(14) . .
C23 C18 C17 120.07(13) . .
C19 C18 C17 122.34(14) . .
C20 C19 C18 120.67(16) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C21 120.39(15) . .
C19 C20 H20 119.8 . .
C21 C20 H20 119.8 . .
C22 C21 C20 120.86(16) . .
C22 C21 H21 119.6 . .
C20 C21 H21 119.6 . .
C21 C22 C23 118.40(15) . .
C21 C22 H22 120.8 . .
C23 C22 H22 120.8 . .
C22 C23 N11 121.62(13) . .
C22 C23 C18 122.11(13) . .
N11 C23 C18 116.27(12) . .
C32 C31 C36 117.25(12) . .
C32 C31 I1 120.68(10) . .
C36 C31 I1 122.01(10) . .
C31 I1 N13 175.98(5) . .
F32 C32 C31 120.30(12) . .
F32 C32 C36 118.46(12) . 2_567
C31 C32 C36 121.23(12) . 2_567
F36 C36 C32 117.90(12) . 2_567
F36 C36 C31 120.58(12) . .
C32 C36 C31 121.52(13) 2_567 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 N12 1.3442(17) .
N11 C15 1.3644(18) .
N11 C23 1.3946(18) .
N12 N13 1.3164(19) .
N13 C14 1.344(2) .
N13 I1 2.9379(14) .
C14 C15 1.379(2) .
C14 H14 0.9500 .
C15 C16 1.415(2) .
C16 C17 1.346(2) .
C16 H16 0.9500 .
C17 C18 1.430(2) .
C17 H17 0.9500 .
C18 C23 1.400(2) .
C18 C19 1.401(2) .
C19 C20 1.373(3) .
C19 H19 0.9500 .
C20 C21 1.384(3) .
C20 H20 0.9500 .
C21 C22 1.380(2) .
C21 H21 0.9500 .
C22 C23 1.387(2) .
C22 H22 0.9500 .
C31 C32 1.376(2) .
C31 C36 1.3803(19) .
C31 I1 2.0795(13) .
C32 F32 1.3375(15) .
C32 C36 1.3802(18) 2_567
C36 F36 1.3360(16) .
C36 C32 1.3802(18) 2_567
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_4
C15 N11 N12 N13 0.13(17) .
C23 N11 N12 N13 179.73(13) .
N11 N12 N13 C14 -0.22(18) .
N11 N12 N13 I1 167.41(11) .
N12 N13 C14 C15 0.24(19) .
I1 N13 C14 C15 -170.86(10) .
N12 N11 C15 C14 0.02(17) .
C23 N11 C15 C14 -179.59(14) .
N12 N11 C15 C16 -179.88(13) .
C23 N11 C15 C16 0.5(2) .
N13 C14 C15 N11 -0.15(17) .
N13 C14 C15 C16 179.72(18) .
N11 C15 C16 C17 1.2(2) .
C14 C15 C16 C17 -178.69(18) .
C15 C16 C17 C18 -1.5(2) .
C16 C17 C18 C23 0.2(2) .
C16 C17 C18 C19 -178.17(15) .
C23 C18 C19 C20 -0.3(2) .
C17 C18 C19 C20 178.05(15) .
C18 C19 C20 C21 0.6(3) .
C19 C20 C21 C22 -0.7(3) .
C20 C21 C22 C23 0.6(2) .
C21 C22 C23 N11 -179.97(14) .
C21 C22 C23 C18 -0.4(2) .
N12 N11 C23 C22 -1.8(2) .
C15 N11 C23 C22 177.81(14) .
N12 N11 C23 C18 178.67(13) .
C15 N11 C23 C18 -1.8(2) .
C19 C18 C23 C22 0.3(2) .
C17 C18 C23 C22 -178.16(14) .
C19 C18 C23 N11 179.83(13) .
C17 C18 C23 N11 1.4(2) .
C36 C31 C32 F32 179.79(13) .
I1 C31 C32 F32 -2.87(19) .
C36 C31 C32 C36 -0.6(2) 2_567
I1 C31 C32 C36 176.69(11) 2_567
C32 C31 C36 F36 -179.41(13) .
I1 C31 C36 F36 3.29(19) .
C32 C31 C36 C32 0.6(2) 2_567
I1 C31 C36 C32 -176.65(11) 2_567
