Achieving a series of solid-state [2 + 2] cycloaddition reactions involving 1,2-bis(2-pyridyl)ethylene within halogen-bonded co-crystals
Andren, Max; Bosch, Eric; Krueger, Herman R.; Groeneman, Ryan H.; CrystEngComm 26 (2024) 1349–1352; doi:10.1039/D4CE00097H

data_7248176
_publ_section_title
;
 Achieving a series of solid-state [2 + 2] cycloaddition reactions
 involving 1,2-bis(2-pyridyl)ethylene within halogen-bonded co-crystals
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1349
_journal_page_last               1352
_journal_paper_doi               10.1039/D4CE00097H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C12 H10 N2, 2(C6 Cl5 I)'
_chemical_formula_sum            'C24 H10 Cl10 I2 N2'
_chemical_formula_weight         934.695
_chemical_name_systematic
'(E)-1,2-bis(2-pyridyl)ethene and pentachloroiodobenzene cocrystal'
_chemical_properties_physical    Photo-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_Int_Tables_number      13
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-14 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.3117(4)
_cell_length_b                   3.9776(1)
_cell_length_c                   26.9681(5)
_cell_measurement_reflns_used    4330
_cell_measurement_temperature    299.63(10)
_cell_measurement_theta_max      76.9020
_cell_measurement_theta_min      3.1690
_cell_volume                     1486.21(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.63(10)
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9782
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9782
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15312
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9782
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.52
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    25.075
_exptl_absorpt_correction_T_max  0.505
_exptl_absorpt_correction_T_min  0.135
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_description       needle
_exptl_crystal_F_000             897.753
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.8042
_refine_diff_density_min         -0.7669
_refine_diff_density_rms         0.1802
_refine_ls_d_res_high            0.7840
_refine_ls_d_res_low             13.8551
_refine_ls_goodness_of_fit_ref   1.0324
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0324
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+10.8768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              4
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                2555
_reflns_number_total             3138
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00097h2.cif
_cod_data_source_block           CC22BPEC6Cl5I
_cod_depositor_comments          'Adding full bibliography for 7248176.cif.'
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               7248176
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'