Crystallographic, spectroscopic, and computational characterization of a diiodonaphthoquinone diarylethene photochrome: halogen bonding and photocrystallography
Myers, Shea D.; Marr, Zoe Y.; Sency, Jade A.; Mitchell, Travis B.; Benedict, Jason B.; Patel, Dinesh G.; CrystEngComm 26 (2024) 2510–2517; doi:10.1039/D4CE00112E

data_7248510
_publ_section_title
;
 Crystallographic, spectroscopic, and computational characterization of a
 diiodonaphthoquinone diarylethene photochrome: halogen bonding and
 photocrystallography
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2510
_journal_page_last               2517
_journal_paper_doi               10.1039/D4CE00112E
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H12 I2 O2 S2'
_chemical_formula_sum            'C20 H12 I2 O2 S2'
_chemical_formula_weight         602.22
_chemical_name_systematic
'of 2,3-bis(5-iodo-2-methylthiophen-3-yl)naphthalene-1,4-dione'
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-30 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.134(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.911(4)
_cell_length_b                   7.520(3)
_cell_length_c                   12.479(5)
_cell_measurement_reflns_used    1032
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.21
_cell_measurement_theta_min      3.21
_cell_volume                     994.7(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7591
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.800
_diffrn_reflns_theta_min         1.921
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.383
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.7631.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_description       Cut
_exptl_crystal_F_000             572
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate, Hexanes'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0512P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.688
_reflns_Friedel_fraction_max     0.647
_reflns_number_gt                1856
_reflns_number_total             3542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00112e2.cif
_cod_data_source_block           p21
_cod_depositor_comments
'Adding full bibliography for 7248510--7248511.cif.'
_cod_database_code               7248510
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.345
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.63352
 0.36648
2. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C17)
3. Others
 Sof(S1A)=Sof(S2A)=1-FVAR(1)
 Sof(S1)=Sof(S2)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C9(H9), C8(H8), C10(H10), C15(H15)
4.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              95760
_olex2_submission_special_instructions 'No special instructions were received'