Perfluorohalogenated naphthalenes: synthesis, crystal structure, and intermolecular interaction
Ohtsuka, Naoya; Ota, Hino; Sugiura, Satoshi; Kakinuma, Shuya; Sugiyama, Haruki; Suzuki, Toshiyasu; Momiyama, Norie; CrystEngComm 26 (2024) 764–772; doi:10.1039/D3CE01124K

data_7248005
_publ_section_title
;
 Perfluorohalogenated naphthalenes: synthesis, crystal structure, and
 intermolecular interaction
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              764
_journal_page_last               772
_journal_paper_doi               10.1039/D3CE01124K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '1(C10 F6 I2)'
_chemical_formula_sum            'C10 F6 I2'
_chemical_formula_weight         487.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-21
_audit_creation_method
;
FinalCif V95 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-07-02 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.067(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.5510(12)
_cell_length_b                   4.45154(19)
_cell_length_c                   11.3608(4)
_cell_measurement_reflns_used    6133
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.5510
_cell_measurement_theta_min      2.8110
_cell_volume                     2202.51(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -57.00 -32.00   0.25   21.00    --  -11.26 110.00 104.00  100
  2  \w     46.00  87.00   0.25   21.00    --   12.67 179.00  60.00  164
  3  \w     39.00  66.00   0.25   21.00    --   12.67 179.00 120.00  108
  4  \w     39.00  64.00   0.25   21.00    --   12.67 179.00-120.00  100
  5  \w     -1.00  84.00   0.25   21.00    --   12.67  57.00-180.00  340
  6  \w     29.00  55.00   0.25   21.00    --   12.67-110.00   9.00  104
  7  \w    -72.00  17.00   0.25   21.00    --  -11.26 -77.00-180.00  356
  8  \w    -90.00 -54.00   0.25   21.00    --  -11.26-179.00-180.00  144
  9  \w    -60.00 -24.75   0.25   21.00    --  -11.26 115.00 -86.16  141
 10  \w    -27.00  36.00   0.25   21.00    --  -11.26  57.00  30.00  252
 11  \w     -8.00  86.00   0.25   21.00    --   12.67  37.00 -30.00  376
 12  \w    -14.00  12.00   0.25   21.00    --   12.67 -99.00  60.00  104
 13  \w     27.00  52.00   0.25   21.00    --   12.67 -99.00  60.00  100
 14  \w    -59.00  42.00   0.25   21.00    --   12.67 -77.00-120.00  404
 15  \w      6.00  52.00   0.25   21.00    --   12.67 -99.00 120.00  184
 16  \w    -15.00  86.00   0.25   21.00    --   12.67  77.00 -30.00  404
 17  \w     29.00  87.00   0.25   21.00    --   12.67  57.00  90.00  232
 18  \w     21.00  63.00   0.25   21.00    --   12.67  77.00  30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135323500
_diffrn_orient_matrix_UB_12      0.0840252500
_diffrn_orient_matrix_UB_13      -0.0112894000
_diffrn_orient_matrix_UB_21      0.0089859500
_diffrn_orient_matrix_UB_22      0.1308191500
_diffrn_orient_matrix_UB_23      -0.0090099000
_diffrn_orient_matrix_UB_31      0.0011641000
_diffrn_orient_matrix_UB_32      -0.0351431000
_diffrn_orient_matrix_UB_33      -0.0607208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25044
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.806
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.943
_exptl_crystal_description       plate
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         3.123
_refine_diff_density_min         -2.670
_refine_diff_density_rms         0.362
_refine_ls_abs_structure_details
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         5413
_refine_ls_number_restraints     1022
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+184.7630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2158
_refine_ls_wR_factor_ref         0.2243
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4502
_reflns_number_total             5413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01124k2.cif
_cod_data_source_block           36i2f6221024-150
_cod_depositor_comments
'Adding full bibliography for 7248004--7248006.cif.'
_cod_original_cell_volume        2202.52(14)
_cod_database_code               7248005
_chemical_oxdiff_formula         C10F6I2
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.949
_oxdiff_exptl_absorpt_empirical_full_min 0.443
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_shelx_estimated_absorpt_t_min   0.761
_shelx_estimated_absorpt_t_max   0.945
_olex2_refinement_description
;
1. Restrained distances
 I12-C2 = I17-C8 = I35A-C26A = I35-C26 = I30-C20 = I30A-C20A = I12A-C2A = I17A-
 C8A
 2.1 with sigma of 0.01
 F18-C7 = F11-C1 = F13-C3 = F14-C4 = F15-C10 = F16-C9
 1.34 with sigma of 0.005
 F29-C19 = F36-C25 = F34-C27 = F33-C28 = F32-C22 = F31-C21
 1.34 with sigma of 0.005
 F14A-C4A = F15A-C10A = F16A-C9A = F18A-C7A = F11A-C1A = F13A-C3A = F34A-C27A =
  F33A-C28A = F32A-C22A = F31A-C21A = F29A-C19A = F36A-C25A
 1.34 with sigma of 0.005
 C19A-I30A \\sim I30A-C21A
 with sigma of 0.02
 C9A-I17A \\sim I17A-C7A
 with sigma of 0.02
 C28-F34 \\sim F34-C26
 with sigma of 0.02
 C21-F32 \\sim F32-C23
 with sigma of 0.02
 C20-F31 \\sim F31-C22
 with sigma of 0.02
 C9-F15 \\sim F15-C5
 with sigma of 0.02
 C5-F14 \\sim F14-C3
 with sigma of 0.02
 C8-F16 \\sim F16-C10
 with sigma of 0.02
 C4-F13 \\sim F13-C2
 with sigma of 0.02
 C24-F29 \\sim F29-C20
 with sigma of 0.02
 C27-F33 \\sim F33-C23
 with sigma of 0.02
 C6A-F11A \\sim F11A-C2A
 with sigma of 0.02
 C1A-I12A \\sim I12A-C3A
 with sigma of 0.02
 C4A-F13A \\sim F13A-C2A
 with sigma of 0.02
 C8A-F16A \\sim F16A-C10A
 with sigma of 0.02
 C24A-F29A \\sim F29A-C20A
 with sigma of 0.02
 C9A-F15A \\sim F15A-C5A
 with sigma of 0.02
 C8A-F18A \\sim F18A-C6A
 with sigma of 0.02
 C27A-I35A \\sim I35A-C25A
 with sigma of 0.02
 C5A-F14A \\sim F14A-C3A
 with sigma of 0.02
 C22A-F31A \\sim F31A-C20A
 with sigma of 0.02
 C21A-F32A \\sim F32A-C23A
 with sigma of 0.02
 C27A-F33A \\sim F33A-C23A
 with sigma of 0.02
 C26A-F36A \\sim F36A-C24A
 with sigma of 0.02
2. Restrained planarity
 I30, F36, F29, C28, C27, C26, C25, C24, C23, C22, C21, C20, C19, F33, F34,
 F32, F31, I35
 with sigma of 0.015
 I35A, I30A, F29A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A,
 F31A, F36A, F33A, F34A, F32A
 with sigma of 0.01
 I12, I17, F18, F16, F15, F11, F13, C7, C8, C9, C10, C5, C6, C1, C2, C3, C4, F14
 with sigma of 0.1
 I12A, I17A, F18A, F16A, F15A, F11A, F13A, C1A, C2A, C3A, C4A, C5A, C6A, C7A,
 C8A, C9A, C10A, F14A
 with sigma of 0.1
3. Rigid bond restraints
 C10A, F15A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F16A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C21A, F31A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F32A, C22A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
I12 \\sim I17A: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006 within 2A
I30 \\sim I30A: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006 within 2A
I17 \\sim I12A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
I35A \\sim I35: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
F13 \\sim F14 \\sim F15 \\sim F16 \\sim F11A \\sim F18 \\sim F18A \\sim F11
\\sim F16A \\sim F15A \\sim F14A \\sim F13A \\sim F36A \\sim F36 \\sim F29A
\\sim F29 \\sim F34A \\sim F33A \\sim F32A \\sim F31A \\sim F31 \\sim F32 \\sim
F33 \\sim F34: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C6A \\sim C5A \\sim C4A \\sim C3A \\sim C2A \\sim C1A \\sim C7A \\sim C9A \\sim
C10A \\sim C8A \\sim C2 \\sim C4 \\sim C6 \\sim C10 \\sim C8 \\sim C9 \\sim C5
\\sim C3 \\sim C1 \\sim C7 \\sim C26A \\sim C25A \\sim C24A \\sim C19A \\sim
C20A \\sim C21A \\sim C22A \\sim C23A \\sim C28A \\sim C27A \\sim C25 \\sim C24
\\sim C23 \\sim C22 \\sim C21 \\sim C20 \\sim C19 \\sim C26 \\sim C27 \\sim
C28: within 2A with sigma of 0.008 and sigma for terminal atoms of 0.016 within
2A
Uanis(I12) \\sim Ueq, Uanis(I17A) \\sim Ueq, Uanis(I30) \\sim Ueq, Uanis(I30A)
\\sim Ueq, Uanis(I35) \\sim Ueq, Uanis(I17) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(I35A) \\sim Ueq, Uanis(I12A) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F16)
\\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F15A) \\sim Ueq,
Uanis(F16A) \\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F18) \\sim Ueq, Uanis(F18A)
\\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F36) \\sim Ueq, Uanis(F36A) \\sim Ueq,
Uanis(F29) \\sim Ueq, Uanis(F29A) \\sim Ueq, Uanis(F31) \\sim Ueq, Uanis(F32)
\\sim Ueq, Uanis(F31A) \\sim Ueq, Uanis(F33) \\sim Ueq, Uanis(F32A) \\sim Ueq,
Uanis(F33A) \\sim Ueq, Uanis(F34A) \\sim Ueq, Uanis(F34) \\sim Ueq: with sigma
of 0.003 and sigma for terminal atoms of 0.006
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C28) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C4A) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C8A) \\sim Ueq,
Uanis(C9A) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(C7A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C3A) \\sim Ueq,
Uanis(C26A) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C24A) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C21A) \\sim Ueq,
Uanis(C22A) \\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C28A) \\sim Ueq,
Uanis(C27A) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of
0.015 and sigma for terminal atoms of 0.03
5. Others
 Sof(I35A)=Sof(I12A)=Sof(I17A)=Sof(F18A)=Sof(F16A)=Sof(F15A)=Sof(F11A)=
 Sof(F13A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(C7A)=
 Sof(C8A)=Sof(C9A)=Sof(C10A)=Sof(F14A)=Sof(I30A)=Sof(F29A)=Sof(C19A)=Sof(C20A)=
 Sof(C21A)=Sof(C22A)=Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(C26A)=Sof(C27A)=
 Sof(C28A)=Sof(F31A)=Sof(F36A)=Sof(F33A)=Sof(F34A)=Sof(F32A)=1-FVAR(1)
 Sof(I12)=Sof(I30)=Sof(I17)=Sof(F36)=Sof(F18)=Sof(F29)=Sof(C28)=Sof(C27)=
 Sof(C26)=Sof(C25)=Sof(C24)=Sof(C23)=Sof(C22)=Sof(C21)=Sof(C20)=Sof(C19)=
 Sof(F33)=Sof(F34)=Sof(F32)=Sof(F31)=Sof(F16)=Sof(F15)=Sof(F11)=Sof(F13)=
 Sof(C7)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(C5)=Sof(C6)=Sof(C1)=Sof(C2)=Sof(C3)=
 Sof(C4)=Sof(F14)=Sof(I35)=FVAR(1)
6.a Naphthalene refined as free rotating group:
 C28(C27,C26,C25,C24,C23,C22,C21,C20,C19), C7(C8,C9,C10,C5,C6,C1,C2,C3,C4),
 C1A(C2A,C3A,C4A,C5A,C6A,C7A,C8A,C9A,C10A), C19A(C20A,C21A,C22A,C23A,C24A,C25A,
 C26A,C27A,C28A)
;
_shelx_res_checksum              17035