#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:12:28 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/95/1569564.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_1569564
loop_
_publ_author_name
'Sun, Jiyu'
'Decato, Daniel A.'
'Bryantsev, Vyacheslav S.'
'John, Eric A.'
'Berryman, Orion B.'
_publ_section_title
;
 The interplay between hydrogen and halogen bonding: substituent effects
 and their role in the hydrogen bond enhanced halogen bond.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              8924
_journal_page_last               8935
_journal_paper_doi               10.1039/d3sc02348f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C25 H13 F6 I2 N'
_chemical_formula_sum            'C25 H13 F6 I2 N'
_chemical_formula_weight         695.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.945(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.182(4)
_cell_length_b                   4.5894(10)
_cell_length_c                   29.337(6)
_cell_measurement_reflns_used    9068
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.032
_cell_measurement_theta_min      2.757
_cell_volume                     2341.7(9)
_computing_cell_refinement       'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19640
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.078
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0853 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.7166. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_description       plank
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.377
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0413
_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)+(0.0054P)²+13.3860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3377
_reflns_number_total             4155
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02348f2.cif
_cod_data_source_block           umt_ob229f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569562--1569572.cif.
;
_cod_original_cell_volume        2341.8(9)
_cod_database_code               1569564
_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.
;
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.399
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82942(2) 0.45732(9) 0.29402(2) 0.02518(12) Uani 1 1 d . . . . .
I2 I 0.51525(3) -0.25839(10) 0.27207(2) 0.02606(12) Uani 1 1 d . . . . .
F1 F 1.1256(2) 1.3486(10) 0.42952(14) 0.0444(12) Uani 1 1 d . . . . .
F2 F 1.1238(2) 1.0112(9) 0.47984(14) 0.0428(11) Uani 1 1 d . . . . .
F3 F 1.0490(2) 1.3780(9) 0.47285(14) 0.0386(10) Uani 1 1 d . . . . .
F4 F 0.2264(2) -0.8198(8) 0.35997(16) 0.0437(11) Uani 1 1 d . . . . .
F5 F 0.1711(2) -0.4305(9) 0.32646(13) 0.0379(10) Uani 1 1 d . . . . .
F6 F 0.2445(2) -0.4184(9) 0.39827(13) 0.0359(10) Uani 1 1 d . . . . .
N1 N 0.6584(3) 0.2704(13) 0.36134(18) 0.0230(12) Uani 1 1 d D . . . .
C1 C 0.9117(3) 0.7008(13) 0.3455(2) 0.0203(14) Uani 1 1 d . . . . .
C2 C 0.9802(3) 0.7643(15) 0.3369(2) 0.0245(14) Uani 1 1 d . . . . .
H2 H 0.990525 0.693212 0.308982 0.029 Uiso 1 1 calc R . . . .
C3 C 1.0342(4) 0.9338(15) 0.3694(2) 0.0263(15) Uani 1 1 d . . . . .
H3 H 1.081325 0.984004 0.363471 0.032 Uiso 1 1 calc R . . . .
C4 C 1.0187(3) 1.0286(14) 0.4105(2) 0.0217(14) Uani 1 1 d . . . . .
C5 C 0.9501(3) 0.9634(14) 0.4192(2) 0.0210(14) Uani 1 1 d . . . . .
H5 H 0.940083 1.033847 0.447252 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8947(3) 0.7928(14) 0.3866(2) 0.0217(14) Uani 1 1 d . . . . .
C7 C 0.8250(3) 0.7267(15) 0.3975(2) 0.0227(14) Uani 1 1 d . . . . .
C8 C 0.7699(4) 0.6762(14) 0.4108(2) 0.0238(15) Uani 1 1 d . . . . .
C9 C 0.7035(3) 0.6140(14) 0.4258(2) 0.0210(14) Uani 1 1 d . . . . .
C10 C 0.6486(3) 0.4116(13) 0.4001(2) 0.0195(14) Uani 1 1 d . . . . .
C11 C 0.6929(3) 0.7594(14) 0.4655(2) 0.0219(14) Uani 1 1 d . . . . .
H11 H 0.730701 0.895058 0.482122 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6287(3) 0.7106(14) 0.4811(2) 0.0200(14) Uani 1 1 d . . . . .
C13 C 0.5742(3) 0.5147(13) 0.45539(19) 0.0183(13) Uani 1 1 d . . . . .
H13 H 0.529673 0.480062 0.465250 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5824(3) 0.3648(13) 0.4151(2) 0.0205(14) Uani 1 1 d . . . . .
C15 C 0.5254(3) 0.1638(14) 0.3900(2) 0.0194(14) Uani 1 1 d . . . . .
C16 C 0.4789(3) -0.0082(14) 0.3679(2) 0.0194(14) Uani 1 1 d . . . . .
C17 C 0.4222(3) -0.2111(13) 0.34306(19) 0.0168(13) Uani 1 1 d . . . . .
C18 C 0.4252(3) -0.3488(13) 0.3008(2) 0.0203(14) Uani 1 1 d . . . . .
C19 C 0.3690(3) -0.5468(14) 0.2779(2) 0.0227(14) Uani 1 1 d . . . . .
H19 H 0.371933 -0.638950 0.249484 0.027 Uiso 1 1 calc R . . . .
C20 C 0.3090(4) -0.6109(13) 0.2959(2) 0.0228(15) Uani 1 1 d . . . . .
H20 H 0.270885 -0.747792 0.280151 0.027 Uiso 1 1 calc R . . . .
C21 C 0.3044(3) -0.4748(14) 0.3373(2) 0.0223(14) Uani 1 1 d . . . . .
C22 C 0.3601(3) -0.2800(13) 0.3609(2) 0.0193(13) Uani 1 1 d . . . . .
H22 H 0.356734 -0.190961 0.389417 0.023 Uiso 1 1 calc R . . . .
C23 C 1.0789(4) 1.1960(15) 0.4478(2) 0.0270(16) Uani 1 1 d . . . . .
C24 C 0.6189(4) 0.8648(15) 0.5242(2) 0.0268(16) Uani 1 1 d . . . . .
H24A H 0.572665 0.986864 0.514783 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.663917 0.987363 0.538258 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.613589 0.720597 0.547710 0.040 Uiso 1 1 calc GR . . . .
C25 C 0.2373(4) -0.5373(14) 0.3560(2) 0.0242(14) Uani 1 1 d . . . . .
H1A H 0.7034(18) 0.256(15) 0.358(2) 0.03(2) Uiso 1 1 d D . . . .
H1B H 0.631(4) 0.120(11) 0.351(3) 0.05(3) Uiso 1 1 d 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'
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
_geom_angle_publ_flag
C2 C1 I1 118.2(4) . . ?
C2 C1 C6 122.5(6) . . ?
C6 C1 I1 119.3(5) . . ?
C1 C2 C3 119.4(6) . . ?
C4 C3 C2 119.3(6) . . ?
C3 C4 C23 120.1(6) . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 C23 118.7(5) . . ?
C4 C5 C6 120.2(5) . . ?
C1 C6 C5 117.4(5) . . ?
C1 C6 C7 124.4(6) . . ?
C5 C6 C7 118.2(5) . . ?
C8 C7 C6 174.2(6) . . ?
C7 C8 C9 179.0(7) . . ?
C10 C9 C8 119.7(5) . . ?
C11 C9 C8 119.6(6) . . ?
C11 C9 C10 120.7(5) . . ?
N1 C10 C9 120.9(5) . . ?
N1 C10 C14 121.2(6) . . ?
C9 C10 C14 117.8(5) . . ?
C12 C11 C9 121.9(6) . . ?
C11 C12 C24 121.2(6) . . ?
C13 C12 C11 117.4(5) . . ?
C13 C12 C24 121.4(5) . . ?
C12 C13 C14 122.6(5) . . ?
C10 C14 C15 119.6(5) . . ?
C13 C14 C10 119.6(6) . . ?
C13 C14 C15 120.8(5) . . ?
C16 C15 C14 177.9(6) . . ?
C15 C16 C17 177.8(6) . . ?
C18 C17 C16 122.5(5) . . ?
C18 C17 C22 117.8(5) . . ?
C22 C17 C16 119.7(5) . . ?
C17 C18 I2 120.1(4) . . ?
C19 C18 I2 119.2(4) . . ?
C19 C18 C17 120.7(6) . . ?
C20 C19 C18 120.5(6) . . ?
C19 C20 C21 119.8(6) . . ?
C20 C21 C25 119.7(6) . . ?
C22 C21 C20 120.5(6) . . ?
C22 C21 C25 119.9(6) . . ?
C21 C22 C17 120.7(5) . . ?
F1 C23 F2 106.5(5) . . ?
F1 C23 C4 112.9(5) . . ?
F2 C23 C4 110.3(5) . . ?
F3 C23 F1 107.7(5) . . ?
F3 C23 F2 105.7(5) . . ?
F3 C23 C4 113.2(5) . . ?
F4 C25 F5 106.4(5) . . ?
F4 C25 F6 107.3(5) . . ?
F4 C25 C21 112.2(5) . . ?
F5 C25 C21 111.2(5) . . ?
F6 C25 F5 106.0(5) . . ?
F6 C25 C21 113.2(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.111(6) . ?
I2 C18 2.091(6) . ?
F1 C23 1.329(7) . ?
F2 C23 1.350(8) . ?
F3 C23 1.329(7) . ?
F4 C25 1.322(8) . ?
F5 C25 1.354(7) . ?
F6 C25 1.326(7) . ?
N1 C10 1.365(8) . ?
C1 C2 1.372(8) . ?
C1 C6 1.393(8) . ?
C2 C3 1.391(9) . ?
C3 C4 1.387(8) . ?
C4 C5 1.378(8) . ?
C4 C23 1.512(9) . ?
C5 C6 1.407(8) . ?
C6 C7 1.426(8) . ?
C7 C8 1.200(8) . ?
C8 C9 1.429(8) . ?
C9 C10 1.411(8) . ?
C9 C11 1.402(8) . ?
C10 C14 1.413(8) . ?
C11 C12 1.392(8) . ?
C12 C13 1.386(8) . ?
C12 C24 1.506(8) . ?
C13 C14 1.411(8) . ?
C14 C15 1.423(9) . ?
C15 C16 1.199(8) . ?
C16 C17 1.422(8) . ?
C17 C18 1.406(8) . ?
C17 C22 1.411(8) . ?
C18 C19 1.386(9) . ?
C19 C20 1.376(9) . ?
C20 C21 1.390(8) . ?
C21 C22 1.376(8) . ?
C21 C25 1.503(8) . ?
