Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization
Sinnwell, Michael A.; Blad, Jared N.; Thomas, Logan R.; MacGillivray, Leonard R.; IUCrJ 5 (2018) –; doi:10.1107/S2052252518007583

data_1549602
_publ_section_title
;
 Structural flexibility of halogen bonds showed in a
 single-crystal-to-single-crystal [2+2] photodimerization
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252518007583
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         '1(C28 H4 F16 I4), 2(C12 H10 N2)'
_chemical_formula_sum            'C52 H24 F16 I4 N4'
_chemical_formula_weight         1516.35
_chemical_name_common            (I4F16cb)2(bpe)
_chemical_name_systematic
'rctt-tetrakis-(4-iodo-2,3,5,6-tetrafluorophenyl)cyclobutane, trans-1,2-bis-(4-pyridyl)-ethene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 104.649(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0184(13)
_cell_length_b                   9.7153(10)
_cell_length_c                   19.986(2)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      52.74
_cell_measurement_theta_min      4.617
_cell_volume                     2445.6(4)
_computing_cell_refinement       'apexII (Bruker AXS, 2010)'
_computing_data_collection       'apexII (Bruker AXS, 2010)'
_computing_data_reduction        'apexII (Bruker AXS, 2010)'
_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      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52897
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         2.963
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.8065.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     704
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+2.1900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4016
_reflns_number_total             5012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5014.cif
_cod_data_source_block           mcg164
_cod_database_code               1549602
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.417
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained planarity
 I1A, C1A, C2A, C3A, C4A, C5A, C6A, F1A, F2A, F3A, F4A
 with sigma of 0.1
 I1B, C1B, C2B, C3B, C4B, C5B, C6B, F1B, F2B, F3B, F4B
 with sigma of 0.1
 I2A, C9A, C10A, C11A, C12A, C13A, C14A, F5A, F6A, F7A, F8A
 with sigma of 0.1
 I2B, C9B, C10B, C11B, C12B, C13B, C14B, F8B
 with sigma of 0.1
 N2B, C25B, C26B, C22B, C23B, C24B
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(I1A) = Uanis(I1B)
Uanis(I2A) = Uanis(I2B)
Uanis(N1A) = Uanis(N1B)
Uanis(N2A) = Uanis(N2B)
Uanis(C1A) = Uanis(C1B)
Uanis(C22A) = Uanis(C22B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
4. Rigid body (RIGU) restrains
 I1A, I2A, F1A, F2A, F3A, F4A, F5A, F6A, F7A, F8A, C1A, C2A, C3A, C4A, C5A,
 C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 I1B, I2B, F1B, F2B, F3B, F4B, F5B, F6B, F7B, F8B, C1B, C2B, C3B, C4B, C5B,
 C6B, C7B, C8B, C9B, C10B, C11B, C12B, C13B, C14B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, N2A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A,
 C26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1B, N2B, C15B, C16B, C17B, C18B, C19B, C20B, C21B, C22B, C23B, C24B, C25B,
 C26B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{I1A, I2A, F1A, F2A, F3A, F4A, F5A, F6A, F7A, F8A, C1A, C2A, C3A, C4A, C5A,
C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A} sigma for 1-2: 0.02, 1-3: 0.04
as
{I1B, I2B, F1B, F2B, F3B, F4B, F5B, F6B, F7B, F8B, C1B, C2B, C3B, C4B, C5B,
C6B, C7B, C8B, C9B, C10B, C11B, C12B, C13B, C14B}
{N1A, N2A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A,
C26A} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1B, N2B, C15B, C16B, C17B, C18B, C19B, C20B, C21B, C22B, C23B, C24B, C25B,
C26B}
6. Others
 Sof(I1B)=Sof(I2B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=
 Sof(F7B)=Sof(F8B)=Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=
 Sof(C13B)=Sof(C14B)=1-FVAR(1)
 Sof(I1A)=Sof(I2A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=
 Sof(F7A)=Sof(F8A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(C12A)=
 Sof(C13A)=Sof(C14A)=FVAR(1)
 Sof(N1B)=Sof(N2B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(C18B)=
 Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21B)=
 Sof(C22B)=Sof(C23B)=Sof(H23B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25B)=
 Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(N1A)=Sof(N2A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=
 Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=
 Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=
 Sof(C26A)=Sof(H26A)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C7A(H7A), C8A(H8A), C7B(H7B), C8B(H8B)
7.b Aromatic/amide H refined with riding coordinates:
 C15A(H15A), C16A(H16A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A), C15B(H15B), C16B(H16B),
 C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B), C23B(H23B), C24B(H24B),
 C25B(H25B), C26B(H26B)
;
_shelx_res_checksum              48380
_shelx_hkl_checksum              85985
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'