#------------------------------------------------------------------------------
#$Date: 2020-02-12 04:52:34 +0200 (Wed, 12 Feb 2020) $
#$Revision: 248065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239919.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_7239919
loop_
_publ_author_name
'Setter, Caitlin J.'
'Whittaker, Jacob J.'
'Brock, Aidan J.'
'Arachchige, Kasun'
'McMurtrie, John'
'Clegg, Jack Kay'
'Pfrunder, Michael Craig'
_publ_section_title
;
 Straightening Out Halogen Bonds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00176G
_journal_year                    2020
_chemical_formula_moiety         'C6 F4 I2, 2(C17 H10 N2 O2)'
_chemical_formula_sum            'C40 H20 F4 I2 N4 O4'
_chemical_formula_weight         950.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-09 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                71.17(3)
_cell_angle_beta                 87.33(3)
_cell_angle_gamma                82.84(3)
_cell_formula_units_Z            1
_cell_length_a                   3.9340(8)
_cell_length_b                   14.576(3)
_cell_length_c                   16.601(3)
_cell_measurement_reflns_used    12077
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      1.630
_cell_volume                     893.9(3)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12077
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.630
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.624
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.095(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0648P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3116
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00176g2.cif
_cod_data_source_block           pbnpdH14DITFB
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        893.9(4)
_cod_database_code               7239919
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H2-O2
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C6(H6), C13(H13), C7(H7), C12(H12), C3(H3), C4(H4), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
I1 I 1.08271(4) -0.26333(2) 0.46210(2) 0.02177(14) Uani 1 1 d .
F2 F 1.4925(5) -0.37134(12) 0.34010(11) 0.0338(4) Uani 1 1 d .
F1 F 1.1927(6) -0.44953(13) 0.63200(12) 0.0352(5) Uani 1 1 d .
O1 O -0.3314(6) 0.53933(14) 0.04702(13) 0.0266(5) Uani 1 1 d .
O2 O -0.2095(6) 0.35789(14) 0.10062(13) 0.0252(4) Uani 1 1 d D
H2 H -0.298(10) 0.4136(19) 0.068(2) 0.038 Uiso 1 1 d DR
C19 C 1.3306(7) -0.40424(18) 0.48472(18) 0.0201(6) Uani 1 1 d .
N2 N 0.7223(7) -0.06705(19) 0.42787(19) 0.0329(6) Uani 1 1 d .
C15 C 0.4214(7) 0.18195(19) 0.35370(19) 0.0236(6) Uani 1 1 d .
H15 H 0.515821 0.178987 0.406246 0.028 Uiso 1 1 calc R
C18 C 1.4939(7) -0.43386(19) 0.41988(18) 0.0223(6) Uani 1 1 d .
C16 C 0.2732(7) 0.27045(18) 0.29790(18) 0.0225(6) Uani 1 1 d .
H16 H 0.271243 0.328485 0.312357 0.027 Uiso 1 1 calc R
C11 C 0.1288(7) 0.27512(18) 0.22180(17) 0.0210(6) Uani 1 1 d .
C14 C 0.4273(7) 0.09747(18) 0.33008(18) 0.0228(6) Uani 1 1 d .
C17 C 0.5916(8) 0.0054(2) 0.3857(2) 0.0254(6) Uani 1 1 d .
C8 C -0.1643(7) 0.54500(19) 0.10704(17) 0.0202(6) Uani 1 1 d .
C10 C -0.0345(7) 0.36842(18) 0.16200(17) 0.0204(6) Uani 1 1 d .
C20 C 1.3432(8) -0.4729(2) 0.56551(19) 0.0230(5) Uani 1 1 d .
C6 C -0.0051(7) 0.66179(19) 0.18071(18) 0.0233(6) Uani 1 1 d .
H6 H 0.085799 0.607954 0.227100 0.028 Uiso 1 1 calc R
C13 C 0.2807(8) 0.10092(19) 0.25404(19) 0.0260(6) Uani 1 1 d .
H13 H 0.283507 0.043032 0.239308 0.031 Uiso 1 1 calc R
N1 N -0.1177(8) 1.01117(19) 0.11654(19) 0.0364(6) Uani 1 1 d .
C7 C 0.0000(8) 0.7560(2) 0.18286(19) 0.0251(6) Uani 1 1 d .
H7 H 0.091359 0.766984 0.230474 0.030 Uiso 1 1 calc R
C12 C 0.1306(7) 0.18958(19) 0.19991(19) 0.0237(6) Uani 1 1 d .
H12 H 0.029473 0.192312 0.148205 0.028 Uiso 1 1 calc R
C2 C -0.1324(7) 0.83475(19) 0.11337(19) 0.0241(6) Uani 1 1 d .
C3 C -0.2692(8) 0.81920(19) 0.04346(19) 0.0253(6) Uani 1 1 d .
H3 H -0.357664 0.872994 -0.003292 0.030 Uiso 1 1 calc R
C4 C -0.2750(8) 0.72459(19) 0.04284(18) 0.0234(6) Uani 1 1 d .
H4 H -0.369728 0.713403 -0.004299 0.028 Uiso 1 1 calc R
C5 C -0.1413(7) 0.64513(18) 0.11170(17) 0.0211(6) Uani 1 1 d .
C9 C -0.0032(7) 0.45930(18) 0.16890(18) 0.0210(5) Uani 1 1 d .
H9 H 0.123777 0.464663 0.214155 0.025 Uiso 1 1 calc R
C1 C -0.1244(8) 0.9333(2) 0.1154(2) 0.0281(6) 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'
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'
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'
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
C10 O2 H2 110(3) . .
C18 C19 I1 121.6(2) . .
C18 C19 C20 116.6(2) . .
C20 C19 I1 121.7(2) . .
C16 C15 H15 120.9 . .
C16 C15 C14 118.3(3) . .
C14 C15 H15 120.9 . .
F2 C18 C19 120.0(2) . .
F2 C18 C20 118.2(3) . 2_846
C20 C18 C19 121.8(3) 2_846 .
C15 C16 H16 119.4 . .
C11 C16 C15 121.2(3) . .
C11 C16 H16 119.4 . .
C16 C11 C10 122.1(2) . .
C16 C11 C12 119.7(3) . .
C12 C11 C10 118.2(3) . .
C15 C14 C17 119.1(3) . .
C13 C14 C15 121.1(3) . .
C13 C14 C17 119.8(3) . .
N2 C17 C14 178.7(3) . .
O1 C8 C5 117.2(2) . .
O1 C8 C9 121.2(2) . .
C9 C8 C5 121.6(3) . .
O2 C10 C11 114.3(2) . .
O2 C10 C9 122.2(3) . .
C9 C10 C11 123.5(3) . .
F1 C20 C19 120.2(3) . .
F1 C20 C18 118.2(3) . 2_846
C18 C20 C19 121.6(3) 2_846 .
C7 C6 H6 119.5 . .
C7 C6 C5 120.9(3) . .
C5 C6 H6 119.5 . .
C14 C13 H13 120.2 . .
C12 C13 C14 119.7(3) . .
C12 C13 H13 120.2 . .
C6 C7 H7 120.6 . .
C6 C7 C2 118.8(3) . .
C2 C7 H7 120.6 . .
C11 C12 H12 120.0 . .
C13 C12 C11 119.9(3) . .
C13 C12 H12 120.0 . .
C7 C2 C1 118.8(3) . .
C3 C2 C7 121.0(3) . .
C3 C2 C1 120.3(3) . .
C2 C3 H3 120.3 . .
C4 C3 C2 119.4(3) . .
C4 C3 H3 120.3 . .
C3 C4 H4 119.9 . .
C3 C4 C5 120.2(3) . .
C5 C4 H4 119.9 . .
C6 C5 C8 123.3(2) . .
C6 C5 C4 119.7(2) . .
C4 C5 C8 116.9(3) . .
C8 C9 H9 120.4 . .
C10 C9 C8 119.3(3) . .
C10 C9 H9 120.4 . .
N1 C1 C2 179.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C19 2.085(3) .
F2 C18 1.343(3) .
F1 C20 1.348(3) .
O1 C8 1.249(4) .
O2 H2 0.855(19) .
O2 C10 1.315(4) .
C19 C18 1.387(4) .
C19 C20 1.389(4) .
N2 C17 1.136(4) .
C15 H15 0.9500 .
C15 C16 1.398(4) .
C15 C14 1.405(4) .
C18 C20 1.379(4) 2_846
C16 H16 0.9500 .
C16 C11 1.387(4) .
C11 C10 1.489(4) .
C11 C12 1.406(4) .
C14 C17 1.452(4) .
C14 C13 1.396(5) .
C8 C5 1.500(4) .
C8 C9 1.432(4) .
C10 C9 1.387(4) .
C6 H6 0.9500 .
C6 C7 1.388(4) .
C6 C5 1.388(4) .
C13 H13 0.9500 .
C13 C12 1.391(4) .
N1 C1 1.145(4) .
C7 H7 0.9500 .
C7 C2 1.404(4) .
C12 H12 0.9500 .
C2 C3 1.395(5) .
C2 C1 1.452(4) .
C3 H3 0.9500 .
C3 C4 1.385(4) .
C4 H4 0.9500 .
C4 C5 1.405(4) .
C9 H9 0.9500 .
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
I1 C19 C18 F2 -0.5(4) .
I1 C19 C18 C20 -179.7(2) 2_846
I1 C19 C20 F1 0.1(4) .
I1 C19 C20 C18 179.7(2) 2_846
O1 C8 C5 C6 170.9(3) .
O1 C8 C5 C4 -7.3(4) .
O1 C8 C9 C10 -0.2(4) .
O2 C10 C9 C8 -0.4(4) .
C15 C16 C11 C10 179.2(3) .
C15 C16 C11 C12 0.0(4) .
C15 C14 C13 C12 1.0(4) .
C18 C19 C20 F1 179.5(3) .
C18 C19 C20 C18 -0.8(5) 2_846
C16 C15 C14 C17 177.7(3) .
C16 C15 C14 C13 -1.7(4) .
C16 C11 C10 O2 -168.9(2) .
C16 C11 C10 C9 12.0(4) .
C16 C11 C12 C13 -0.8(4) .
C11 C10 C9 C8 178.7(2) .
C14 C15 C16 C11 1.3(4) .
C14 C13 C12 C11 0.3(4) .
C17 C14 C13 C12 -178.5(3) .
C10 C11 C12 C13 180.0(2) .
C20 C19 C18 F2 -180.0(3) .
C20 C19 C18 C20 0.8(5) 2_846
C6 C7 C2 C3 0.5(4) .
C6 C7 C2 C1 -179.5(3) .
C7 C6 C5 C8 -178.0(3) .
C7 C6 C5 C4 0.2(4) .
C7 C2 C3 C4 0.1(4) .
C12 C11 C10 O2 10.3(3) .
C12 C11 C10 C9 -168.8(3) .
C2 C3 C4 C5 -0.6(4) .
C3 C4 C5 C8 178.7(2) .
C3 C4 C5 C6 0.4(4) .
C5 C8 C9 C10 179.5(2) .
C5 C6 C7 C2 -0.6(4) .
C9 C8 C5 C6 -8.8(4) .
C9 C8 C5 C4 173.0(3) .
C1 C2 C3 C4 -179.9(3) .
