Co-operative halogen bonds and nonconventional <i>sp</i>-C—H···O hydrogen bonds in 1:1 cocrystals formed between diethynylpyridines and <i>N</i>-halosuccinimides
Bosch, Eric; Bowling, Nathan P.; Acta Crystallographica Section C 78 (2022) –; doi:10.1107/S2053229622006635

data_2022627
_publ_section_title
;
 Co-operative halogen bonds and nonconventional
 <i>sp</i>-C---H&#x00B7;&#x00B7;&#x00B7;O hydrogen bonds in 1:1 cocrystals
 formed between diethynylpyridines and <i>N</i>-halosuccinimides
;
_journal_coeditor_code           EF3030
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622006635
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C4 H4 I N O2, C9 H5 N'
_chemical_formula_moiety         'C4 H4 I N O2, C9 H5 N'
_chemical_formula_sum            'C13 H9 I N2 O2'
_chemical_formula_weight         352.12
_chemical_name_systematic
;
3,5-Diethynylpyridine--<i>N</i>-iodosuccinimide (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
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;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
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;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
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;
X-SEED (Barbour, 2020)
;
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;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
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;
SHELXT2018 (Sheldrick, 2015<i>a</i>)
;
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_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_k_min       -6
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_diffrn_reflns_limit_l_min       -30
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.367
_diffrn_reflns_theta_min         1.730
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
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_refine_diff_density_min         -0.555
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_refine_ls_number_reflns         2931
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0155P)^2^+1.0427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0463
_reflns_number_gt                2463
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           35DEP_u008226NIS
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022627
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_shelx_res_checksum              96407
_cod_database_fobs_code 2022627