Interactions between haloperfluorobenzenes and fluoranthene in luminescent cocrystals from π–hole···π to σ–hole···π bonds
Li, Li Li; Wang, Hui; Wang, Weizhou; Jin, Wei Jun; CrystEngComm  (2017) –; doi:10.1039/C7CE00950J

data_7228741
_publ_section_title
;
 Interactions between haloperfluorobenzenes and fluoranthene in
 luminescent cocrystals from \p--hole&#x00B7;&#x00B7;&#x00B7;\p to
 \s--hole&#x00B7;&#x00B7;&#x00B7;\p bonds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00950J
_journal_year                    2017
_chemical_formula_moiety         'C6 F4 I2, C16 H10'
_chemical_formula_sum            'C22 H10 F4 I2'
_chemical_formula_weight         604.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-03 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                99.2518(16)
_cell_angle_beta                 90.4052(15)
_cell_angle_gamma                114.420(2)
_cell_formula_units_Z            16
_cell_length_a                   15.2963(3)
_cell_length_b                   18.1009(4)
_cell_length_c                   30.4800(5)
_cell_measurement_reflns_used    66605
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6660
_cell_measurement_theta_min      3.5980
_cell_volume                     7558.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.825
_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    -27.00  25.00   1.00   10.00    --   12.76 -57.00 -30.00   52
  2  \w    -11.00  53.00   1.00   10.00    --   12.76 -99.00  60.00   64
  3  \w    -11.00  29.00   1.00   10.00    --  -11.04 -99.00  90.00   40
  4  \w    -15.00  13.00   1.00   10.00    --   12.76 -37.00  60.00   28
  5  \w    -12.00  71.00   1.00   10.00    --   12.76  37.00 -60.00   83
  6  \w    -21.00  88.00   1.00   10.00    --   12.76  19.00-150.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0256758000
_diffrn_orient_matrix_UB_12      -0.0228290000
_diffrn_orient_matrix_UB_13      -0.0207482000
_diffrn_orient_matrix_UB_21      -0.0240828000
_diffrn_orient_matrix_UB_22      0.0262020000
_diffrn_orient_matrix_UB_23      0.0005532000
_diffrn_orient_matrix_UB_31      0.0370341000
_diffrn_orient_matrix_UB_32      0.0265768000
_diffrn_orient_matrix_UB_33      -0.0113520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            75567
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.937
_diffrn_reflns_theta_min         3.163
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_description       block
_exptl_crystal_F_000             4544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         2.457
_refine_diff_density_min         -3.125
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2017
_refine_ls_number_reflns         36197
_refine_ls_number_restraints     1056
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0144P)^2^+7.1132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                28572
_reflns_number_total             36197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00950j2.cif
_cod_data_source_block           20161228b
_cod_database_code               7228741
_chemical_oxdiff_formula         c1h1f1i1
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq,
Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57)
\\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq,
Uanis(C61) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq,
Uanis(C68) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C71)
\\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C74) \\sim Ueq,
Uanis(C75) \\sim Ueq, Uanis(C76) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C78)
\\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C81) \\sim Ueq,
Uanis(C82) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C84) \\sim Ueq, Uanis(C85)
\\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C88) \\sim Ueq,
Uanis(C89) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92)
\\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C94) \\sim Ueq, Uanis(C95) \\sim Ueq,
Uanis(C96) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq,
Uanis(C103) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C105) \\sim Ueq,
Uanis(C106) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C108) \\sim Ueq,
Uanis(C109) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C111) \\sim Ueq,
Uanis(C112) \\sim Ueq, Uanis(C113) \\sim Ueq, Uanis(C114) \\sim Ueq,
Uanis(C115) \\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C117) \\sim Ueq,
Uanis(C118) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C120) \\sim Ueq,
Uanis(C121) \\sim Ueq, Uanis(C122) \\sim Ueq, Uanis(C123) \\sim Ueq,
Uanis(C124) \\sim Ueq, Uanis(C125) \\sim Ueq, Uanis(C126) \\sim Ueq,
Uanis(C127) \\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C129) \\sim Ueq,
Uanis(C130) \\sim Ueq, Uanis(C131) \\sim Ueq, Uanis(C132) \\sim Ueq,
Uanis(C133) \\sim Ueq, Uanis(C134) \\sim Ueq, Uanis(C135) \\sim Ueq,
Uanis(C136) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C138) \\sim Ueq,
Uanis(C139) \\sim Ueq, Uanis(C140) \\sim Ueq, Uanis(C141) \\sim Ueq,
Uanis(C142) \\sim Ueq, Uanis(C143) \\sim Ueq, Uanis(C144) \\sim Ueq,
Uanis(C145) \\sim Ueq, Uanis(C146) \\sim Ueq, Uanis(C147) \\sim Ueq,
Uanis(C148) \\sim Ueq, Uanis(C149) \\sim Ueq, Uanis(C150) \\sim Ueq,
Uanis(C151) \\sim Ueq, Uanis(C152) \\sim Ueq, Uanis(C153) \\sim Ueq,
Uanis(C154) \\sim Ueq, Uanis(C155) \\sim Ueq, Uanis(C156) \\sim Ueq,
Uanis(C157) \\sim Ueq, Uanis(C158) \\sim Ueq, Uanis(C159) \\sim Ueq,
Uanis(C160) \\sim Ueq, Uanis(C161) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(C163) \\sim Ueq, Uanis(C164) \\sim Ueq, Uanis(C165) \\sim Ueq,
Uanis(C166) \\sim Ueq, Uanis(C167) \\sim Ueq, Uanis(C168) \\sim Ueq,
Uanis(C169) \\sim Ueq, Uanis(C170) \\sim Ueq, Uanis(C171) \\sim Ueq,
Uanis(C172) \\sim Ueq, Uanis(C173) \\sim Ueq, Uanis(C174) \\sim Ueq,
Uanis(C175) \\sim Ueq, Uanis(C176) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C50(H50), C51(H51), C52(H52), C53(H53), C56(H56), C57(H57), C58(H58),
 C60(H60), C61(H61), C62(H62), C66(H66), C67(H67), C68(H68), C69(H69), C72(H72),
  C73(H73), C74(H74), C76(H76), C77(H77), C78(H78), C82(H82), C83(H83),
 C84(H84), C85(H85), C88(H88), C89(H89), C90(H90), C92(H92), C93(H93), C94(H94),
  C98(H98), C99(H99), C100(H100), C101(H101), C104(H104), C105(H105),
 C106(H106), C108(H108), C109(H109), C110(H110), C114(H114), C115(H115),
 C116(H116), C117(H117), C120(H120), C121(H121), C122(H122), C124(H124),
 C125(H125), C126(H126), C130(H130), C131(H131), C132(H132), C133(H133),
 C136(H136), C137(H137), C138(H138), C140(H140), C141(H141), C142(H142),
 C146(H146), C147(H147), C148(H148), C149(H149), C152(H152), C153(H153),
 C154(H154), C156(H156), C157(H157), C158(H158), C162(H162), C163(H163),
 C164(H164), C165(H165), C168(H168), C169(H169), C170(H170), C172(H172),
 C173(H173), C174(H174)
;
_shelx_res_checksum              42580
_shelx_shelxl_version_number     2014/7
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.752