#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/52/7215249.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_7215249
loop_
_publ_author_name
'Viger-Gravel, Jasmine'
'Meyer, Julia E.'
'Korobkov, Ilia'
'Bryce, David L.'
_publ_section_title
;
 Probing halogen bonds with solid-state NMR spectroscopy: observation and
 interpretation of J(77Se,31P) coupling in halogen-bonded
 PSe⋯I motifs
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7285
_journal_paper_doi               10.1039/C4CE00345D
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C24 H15 F4 I2 P Se'
_chemical_formula_weight         743.09
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7022(3)
_cell_length_b                   12.7689(3)
_cell_length_c                   13.9386(3)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.82
_cell_volume                     2392.16(9)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31024
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    4.259
_exptl_absorpt_correction_T_max  0.5313
_exptl_absorpt_correction_T_min  0.3818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0164
_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)+(0.0248P)²+0.8211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0424
_reflns_number_gt                5571
_reflns_number_total             5895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00345d2.cif
_cod_data_source_block           db114
_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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7215248--7215249.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7215249
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
I1 I 0.832493(8) 0.017474(8) 0.038955(8) 0.02932(4) Uani 1 1 d .
I2 I 0.721401(8) -0.244705(8) 0.057601(8) 0.02908(4) Uani 1 1 d .
Se1 Se 0.879919(12) 0.184059(12) 0.232870(12) 0.02547(4) Uani 1 1 d .
P1 P 0.84870(3) 0.33506(3) 0.16898(3) 0.01888(7) Uani 1 1 d .
F1 F 0.88399(9) 0.02883(10) -0.16888(8) 0.0440(3) Uani 1 1 d .
F2 F 0.85993(10) -0.10184(12) -0.32118(8) 0.0532(3) Uani 1 1 d .
F3 F 0.77897(11) -0.29391(13) -0.30962(10) 0.0613(4) Uani 1 1 d .
F4 F 0.72029(10) -0.35413(10) -0.14475(10) 0.0510(3) Uani 1 1 d .
C1 C 0.81247(12) -0.09344(13) -0.07429(12) 0.0265(3) Uani 1 1 d .
C2 C 0.84271(13) -0.06451(15) -0.16011(13) 0.0322(4) Uani 1 1 d .
C3 C 0.83121(13) -0.13172(18) -0.23894(13) 0.0375(4) Uani 1 1 d .
C4 C 0.78991(14) -0.22877(18) -0.23296(14) 0.0408(4) Uani 1 1 d .
C5 C 0.75992(14) -0.25842(15) -0.14791(14) 0.0348(4) Uani 1 1 d .
C6 C 0.77054(12) -0.19219(14) -0.06796(12) 0.0275(3) Uani 1 1 d .
C7 C 0.89386(11) 0.35305(12) 0.05617(11) 0.0235(3) Uani 1 1 d .
C8 C 0.86422(13) 0.44088(14) -0.00101(13) 0.0323(4) Uani 1 1 d .
H8A H 0.8246 0.4931 0.0214 0.039 Uiso 1 1 calc R
C9 C 0.89249(15) 0.45241(18) -0.09079(14) 0.0416(4) Uani 1 1 d .
H9A H 0.8727 0.5127 -0.1297 0.050 Uiso 1 1 calc R
C10 C 0.94953(15) 0.3758(2) -0.12326(15) 0.0462(5) Uani 1 1 d .
H10A H 0.9670 0.3825 -0.1857 0.055 Uiso 1 1 calc R
C11 C 0.98121(15) 0.28986(18) -0.06599(16) 0.0436(5) Uani 1 1 d .
H11A H 1.0219 0.2386 -0.0883 0.052 Uiso 1 1 calc R
C12 C 0.95385(13) 0.27789(14) 0.02446(13) 0.0303(3) Uani 1 1 d .
H12A H 0.9760 0.2188 0.0642 0.036 Uiso 1 1 calc R
C13 C 0.71668(10) 0.36168(11) 0.13645(11) 0.0202(3) Uani 1 1 d .
C14 C 0.66578(12) 0.40086(13) 0.20588(12) 0.0252(3) Uani 1 1 d .
H14A H 0.7010 0.4171 0.2698 0.030 Uiso 1 1 calc R
C15 C 0.56354(12) 0.41624(14) 0.18187(14) 0.0310(3) Uani 1 1 d .
H15A H 0.5288 0.4433 0.2292 0.037 Uiso 1 1 calc R
C16 C 0.51245(12) 0.39213(14) 0.08894(14) 0.0320(4) Uani 1 1 d .
H16A H 0.4428 0.4041 0.0721 0.038 Uiso 1 1 calc R
C17 C 0.56225(13) 0.35068(15) 0.02036(13) 0.0322(4) Uani 1 1 d .
H17A H 0.5264 0.3327 -0.0429 0.039 Uiso 1 1 calc R
C18 C 0.66429(12) 0.33525(13) 0.04364(11) 0.0262(3) Uani 1 1 d .
H18A H 0.6984 0.3068 -0.0035 0.031 Uiso 1 1 calc R
C19 C 0.90484(11) 0.43663(12) 0.25247(11) 0.0222(3) Uani 1 1 d .
C20 C 0.86317(12) 0.53615(13) 0.25182(13) 0.0267(3) Uani 1 1 d .
H20A H 0.8037 0.5522 0.2067 0.032 Uiso 1 1 calc R
C21 C 0.90854(14) 0.61199(14) 0.31702(14) 0.0345(4) Uani 1 1 d .
H21A H 0.8793 0.6794 0.3175 0.041 Uiso 1 1 calc R
C22 C 0.99582(15) 0.58944(16) 0.38080(15) 0.0404(4) Uani 1 1 d .
H22A H 1.0269 0.6415 0.4252 0.049 Uiso 1 1 calc R
C23 C 1.03860(15) 0.49152(18) 0.38070(16) 0.0437(5) Uani 1 1 d .
H23A H 1.0995 0.4768 0.4242 0.052 Uiso 1 1 calc R
C24 C 0.99294(13) 0.41466(14) 0.31726(14) 0.0331(4) Uani 1 1 d .
H24A H 1.0219 0.3470 0.3181 0.040 Uiso 1 1 calc R
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C19 P1 C13 107.79(7)
C19 P1 C7 107.02(7)
C13 P1 C7 104.60(7)
C19 P1 Se1 110.71(5)
C13 P1 Se1 112.59(5)
C7 P1 Se1 113.72(5)
C2 C1 C6 119.33(15)
C2 C1 I1 116.79(13)
C6 C1 I1 123.88(12)
F1 C2 C3 117.87(16)
F1 C2 C1 121.23(16)
C3 C2 C1 120.89(17)
F2 C3 C4 120.22(18)
F2 C3 C2 119.88(19)
C4 C3 C2 119.90(17)
F3 C4 C5 120.6(2)
F3 C4 C3 119.74(18)
C5 C4 C3 119.67(17)
F4 C5 C4 117.90(17)
F4 C5 C6 120.66(17)
C4 C5 C6 121.44(18)
C5 C6 C1 118.77(16)
C5 C6 I2 118.34(13)
C1 C6 I2 122.88(12)
C8 C7 C12 119.96(15)
C8 C7 P1 119.26(12)
C12 C7 P1 120.72(13)
C9 C8 C7 120.07(17)
C8 C9 C10 119.66(19)
C11 C10 C9 120.59(17)
C10 C11 C12 120.18(19)
C7 C12 C11 119.48(18)
C18 C13 C14 119.69(14)
C18 C13 P1 119.78(11)
C14 C13 P1 120.34(12)
C15 C14 C13 120.11(15)
C14 C15 C16 119.83(15)
C17 C16 C15 120.32(15)
C16 C17 C18 120.22(16)
C13 C18 C17 119.79(15)
C24 C19 C20 119.49(15)
C24 C19 P1 118.69(12)
C20 C19 P1 121.80(12)
C21 C20 C19 120.07(16)
C22 C21 C20 119.95(17)
C21 C22 C23 120.33(17)
C24 C23 C22 120.18(18)
C23 C24 C19 119.96(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.0986(16)
I2 C6 2.1034(16)
Se1 P1 2.1320(4)
P1 C19 1.8111(15)
P1 C13 1.8095(15)
P1 C7 1.8129(15)
F1 C2 1.335(2)
F2 C3 1.338(2)
F3 C4 1.339(2)
F4 C5 1.342(2)
C1 C2 1.390(2)
C1 C6 1.396(2)
C2 C3 1.379(3)
C3 C4 1.372(3)
C4 C5 1.381(3)
C5 C6 1.384(2)
C7 C8 1.390(2)
C7 C12 1.390(2)
C8 C9 1.388(2)
C9 C10 1.382(3)
C10 C11 1.376(3)
C11 C12 1.392(3)
C13 C18 1.393(2)
C13 C14 1.391(2)
C14 C15 1.389(2)
C15 C16 1.382(3)
C16 C17 1.383(3)
C17 C18 1.386(2)
C19 C24 1.388(2)
C19 C20 1.392(2)
C20 C21 1.389(2)
C21 C22 1.375(3)
C22 C23 1.381(3)
C23 C24 1.386(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
C6 C1 C2 F1 -179.38(15)
I1 C1 C2 F1 1.1(2)
C6 C1 C2 C3 0.4(3)
I1 C1 C2 C3 -179.10(14)
F1 C2 C3 F2 -0.9(3)
C1 C2 C3 F2 179.32(16)
F1 C2 C3 C4 179.46(17)
C1 C2 C3 C4 -0.3(3)
F2 C3 C4 F3 0.4(3)
C2 C3 C4 F3 -179.91(18)
F2 C3 C4 C5 -179.54(17)
C2 C3 C4 C5 0.1(3)
F3 C4 C5 F4 0.3(3)
C3 C4 C5 F4 -179.70(18)
F3 C4 C5 C6 -179.95(18)
C3 C4 C5 C6 0.0(3)
F4 C5 C6 C1 179.77(16)
C4 C5 C6 C1 0.1(3)
F4 C5 C6 I2 -0.8(2)
C4 C5 C6 I2 179.54(15)
C2 C1 C6 C5 -0.3(2)
I1 C1 C6 C5 179.21(13)
C2 C1 C6 I2 -179.73(12)
I1 C1 C6 I2 -0.2(2)
C19 P1 C7 C8 -68.02(15)
C13 P1 C7 C8 46.17(15)
Se1 P1 C7 C8 169.40(12)
C19 P1 C7 C12 114.86(14)
C13 P1 C7 C12 -130.95(13)
Se1 P1 C7 C12 -7.72(15)
C12 C7 C8 C9 1.5(3)
P1 C7 C8 C9 -175.60(14)
C7 C8 C9 C10 0.5(3)
C8 C9 C10 C11 -2.1(3)
C9 C10 C11 C12 1.7(3)
C8 C7 C12 C11 -2.0(3)
P1 C7 C12 C11 175.14(14)
C10 C11 C12 C7 0.4(3)
C19 P1 C13 C18 147.37(12)
C7 P1 C13 C18 33.72(14)
Se1 P1 C13 C18 -90.24(12)
C19 P1 C13 C14 -37.60(14)
C7 P1 C13 C14 -151.25(13)
Se1 P1 C13 C14 84.79(13)
C18 C13 C14 C15 -1.8(2)
P1 C13 C14 C15 -176.79(13)
C13 C14 C15 C16 0.3(3)
C14 C15 C16 C17 1.4(3)
C15 C16 C17 C18 -1.5(3)
C14 C13 C18 C17 1.6(2)
P1 C13 C18 C17 176.70(13)
C16 C17 C18 C13 0.0(3)
C13 P1 C19 C24 154.63(13)
C7 P1 C19 C24 -93.35(14)
Se1 P1 C19 C24 31.09(14)
C13 P1 C19 C20 -26.74(15)
C7 P1 C19 C20 85.28(14)
Se1 P1 C19 C20 -150.29(12)
C24 C19 C20 C21 -1.3(2)
P1 C19 C20 C21 -179.96(13)
C19 C20 C21 C22 1.4(3)
C20 C21 C22 C23 -0.2(3)
C21 C22 C23 C24 -1.0(3)
C22 C23 C24 C19 1.1(3)
C20 C19 C24 C23 0.1(3)
P1 C19 C24 C23 178.76(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198418
