#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:09:14 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190088 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/69/7226931.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_7226931
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 H5 N3) (C6 F3 I3)
;
_chemical_formula_sum            'C12 H5 F3 I3 N3'
_chemical_formula_weight         628.89
_chemical_name_systematic
;
Mp-p1b-H29 [1,2,3]Triazolo[1,5-a]pyridine, 1,3,5-F3-2,4,6-I3-benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90.00
_cell_angle_beta                 90.6496(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3698(6)
_cell_length_b                   13.7351(9)
_cell_length_c                   12.2408(8)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.97
_cell_measurement_theta_min      2.63
_cell_volume                     1575.23(18)
_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 0.989
_diffrn_measured_fraction_theta_max 0.889
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16602
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.07
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    5.979
_exptl_absorpt_correction_T_max  0.2506
_exptl_absorpt_correction_T_min  0.1984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.055
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_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+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                4468
_reflns_number_total             4882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce02089e2.cif
_cod_data_source_block           A2XB3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               7226931
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.7063(3) 0.4510(2) 0.5158(2) 0.0161(5) Uani 1 1 d .
N12 N 0.6027(3) 0.3918(2) 0.4775(2) 0.0197(6) Uani 1 1 d .
N13 N 0.6098(3) 0.3122(2) 0.5387(2) 0.0194(6) Uani 1 1 d .
C14 C 0.7144(4) 0.3200(3) 0.6130(3) 0.0182(6) Uani 1 1 d .
H14 H 0.7396 0.2719 0.6656 0.022 Uiso 1 1 calc R
C15 C 0.7800(3) 0.4092(3) 0.6012(3) 0.0164(6) Uani 1 1 d .
C16 C 0.8907(4) 0.4629(3) 0.6519(3) 0.0305(9) Uani 1 1 d .
H16 H 0.9450 0.4356 0.7103 0.037 Uiso 1 1 calc R
C17 C 0.9177(4) 0.5531(3) 0.6161(4) 0.0408(11) Uani 1 1 d .
H17 H 0.9918 0.5901 0.6497 0.049 Uiso 1 1 calc R
C18 C 0.8373(5) 0.5942(3) 0.5287(4) 0.0396(11) Uani 1 1 d .
H18 H 0.8576 0.6586 0.5053 0.047 Uiso 1 1 calc R
C19 C 0.7324(4) 0.5435(3) 0.4782(3) 0.0274(8) Uani 1 1 d .
H19 H 0.6789 0.5706 0.4192 0.033 Uiso 1 1 calc R
C21 C 0.2733(3) 0.0365(2) 0.5128(2) 0.0126(6) Uani 1 1 d .
I1 I 0.41127(2) 0.155983(14) 0.524210(16) 0.01425(5) Uani 1 1 d .
C22 C 0.1958(3) 0.0192(2) 0.4175(2) 0.0134(6) Uani 1 1 d .
F22 F 0.2013(2) 0.08568(14) 0.33780(15) 0.0205(4) Uani 1 1 d .
C23 C 0.1134(3) -0.0635(2) 0.4006(2) 0.0125(6) Uani 1 1 d .
I2 I 0.01770(2) -0.090464(16) 0.249081(16) 0.01673(6) Uani 1 1 d .
C24 C 0.1047(3) -0.1277(2) 0.4872(3) 0.0138(6) Uani 1 1 d .
F24 F 0.0223(2) -0.20687(14) 0.47562(16) 0.0203(4) Uani 1 1 d .
C25 C 0.1773(3) -0.1141(2) 0.5851(2) 0.0128(6) Uani 1 1 d .
I3 I 0.16236(3) -0.212620(16) 0.712892(17) 0.02079(6) Uani 1 1 d .
C26 C 0.2614(3) -0.0319(2) 0.5947(2) 0.0128(6) Uani 1 1 d .
F26 F 0.3356(2) -0.01753(15) 0.68798(15) 0.0182(4) 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_3
N12 N11 C15 111.5(3) .
N12 N11 C19 124.9(3) .
C15 N11 C19 123.5(3) .
N13 N12 N11 105.6(3) .
N12 N13 C14 110.6(3) .
N12 N13 I1 123.9(2) .
C14 N13 I1 125.3(2) .
N13 C14 C15 108.9(3) .
N13 C14 H14 125.5 .
C15 C14 H14 125.5 .
N11 C15 C14 103.3(3) .
N11 C15 C16 118.5(3) .
C14 C15 C16 138.1(4) .
C17 C16 C15 118.7(4) .
C17 C16 H16 120.6 .
C15 C16 H16 120.6 .
C16 C17 C18 120.9(4) .
C16 C17 H17 119.5 .
C18 C17 H17 119.5 .
C19 C18 C17 121.2(4) .
C19 C18 H18 119.4 .
C17 C18 H18 119.4 .
C18 C19 N11 117.1(4) .
C18 C19 H19 121.4 .
N11 C19 H19 121.4 .
C26 C21 C22 116.6(3) .
C26 C21 I1 122.7(2) .
C22 C21 I1 120.5(2) .
C21 I1 N13 177.31(10) .
F22 C22 C23 118.4(3) .
F22 C22 C21 118.2(3) .
C23 C22 C21 123.5(3) .
C24 C23 C22 116.5(3) .
C24 C23 I2 122.7(2) .
C22 C23 I2 120.8(2) .
C23 I2 N12 173.32(11) 2_545
F24 C24 C23 118.5(3) .
F24 C24 C25 118.5(3) .
C23 C24 C25 123.0(3) .
C26 C25 C24 117.3(3) .
C26 C25 I3 120.8(2) .
C24 C25 I3 121.9(2) .
F26 C26 C21 118.1(3) .
F26 C26 C25 118.8(3) .
C21 C26 C25 123.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 N12 1.347(4) .
N11 C15 1.372(4) .
N11 C19 1.374(5) .
N12 N13 1.326(4) .
N13 C14 1.334(4) .
N13 I1 2.845(3) .
C14 C15 1.379(5) .
C14 H14 0.9500 .
C15 C16 1.411(5) .
C16 C17 1.340(7) .
C16 H16 0.9500 .
C17 C18 1.419(7) .
C17 H17 0.9500 .
C18 C19 1.348(6) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C21 C26 1.380(4) .
C21 C22 1.387(4) .
C21 I1 2.093(3) .
C22 F22 1.338(3) .
C22 C23 1.387(4) .
C23 C24 1.381(4) .
C23 I2 2.085(3) .
I2 N12 2.992(3) 2_545
C24 F24 1.341(4) .
C24 C25 1.384(4) .
C25 C26 1.381(4) .
C25 I3 2.075(3) .
C26 F26 1.345(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
C15 N11 N12 N13 0.1(4)
C19 N11 N12 N13 -177.1(3)
N11 N12 N13 C14 -0.2(4)
N11 N12 N13 I1 174.41(19)
N12 N13 C14 C15 0.2(4)
I1 N13 C14 C15 -174.3(2)
N12 N11 C15 C14 0.0(4)
C19 N11 C15 C14 177.3(3)
N12 N11 C15 C16 -178.8(3)
C19 N11 C15 C16 -1.5(5)
N13 C14 C15 N11 -0.1(4)
N13 C14 C15 C16 178.3(4)
N11 C15 C16 C17 1.3(5)
C14 C15 C16 C17 -177.0(4)
C15 C16 C17 C18 -0.2(6)
C16 C17 C18 C19 -0.8(7)
C17 C18 C19 N11 0.6(6)
N12 N11 C19 C18 177.5(3)
C15 N11 C19 C18 0.6(5)
C26 C21 C22 F22 177.9(3)
I1 C21 C22 F22 -6.4(4)
C26 C21 C22 C23 -2.3(5)
I1 C21 C22 C23 173.5(2)
F22 C22 C23 C24 -176.6(3)
C21 C22 C23 C24 3.5(5)
F22 C22 C23 I2 6.3(4)
C21 C22 C23 I2 -173.6(2)
C22 C23 C24 F24 177.8(3)
I2 C23 C24 F24 -5.2(4)
C22 C23 C24 C25 -2.4(5)
I2 C23 C24 C25 174.6(2)
F24 C24 C25 C26 180.0(3)
C23 C24 C25 C26 0.1(5)
F24 C24 C25 I3 0.2(4)
C23 C24 C25 I3 -179.6(2)
C22 C21 C26 F26 179.7(3)
I1 C21 C26 F26 4.1(4)
C22 C21 C26 C25 -0.2(4)
I1 C21 C26 C25 -175.9(2)
C24 C25 C26 F26 -178.7(3)
I3 C25 C26 F26 1.1(4)
C24 C25 C26 C21 1.2(5)
I3 C25 C26 C21 -179.0(2)
