#------------------------------------------------------------------------------
#$Date: 2022-06-30 04:58:50 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022626.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022626
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
 Co-operative halogen bonds and nonconventional
 sp-C---H···O hydrogen bonds in 1:1 cocrystals
 formed between diethynylpyridines and N-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
;
2,6-Diethynylpyridine--N-iodosuccinimide (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.6870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4503(8)
_cell_length_b                   12.7805(11)
_cell_length_c                   10.9605(9)
_cell_measurement_reflns_used    4626
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.62
_cell_volume                     1300.84(19)
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_publication_material
;
X-SEED (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15683
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.330
_diffrn_reflns_theta_min         2.473
_exptl_absorpt_coefficient_mu    2.457
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_description       'cut from cube'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.394
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0254
_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/[σ²(Fo²)+(0.0217P)²+1.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                2659
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3030sup1.cif
_cod_data_source_block           26DEP_u008226NIS
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022626
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.47984(2) 0.62904(2) 0.27102(2) 0.01364(6) Uani d 1 . .
O O1 0.5343(2) 0.62403(17) -0.01867(19) 0.0230(5) Uani d 1 . .
N N1 0.6258(3) 0.64370(18) 0.4895(2) 0.0150(5) Uani d 1 . .
C C1 0.9150(4) 0.6114(2) 0.3373(3) 0.0240(7) Uani d 1 . .
O O2 0.1318(2) 0.59239(16) 0.15173(19) 0.0202(4) Uani d 1 . .
N N2 0.3523(2) 0.61269(18) 0.0932(2) 0.0140(5) Uani d 1 . .
C C2 0.8452(3) 0.6124(2) 0.4132(3) 0.0195(6) Uani d 1 . .
C C3 0.7681(3) 0.6209(2) 0.5157(3) 0.0153(6) Uani d 1 . .
C C4 0.8422(3) 0.6107(2) 0.6373(3) 0.0189(6) Uani d 1 . .
H H4 0.941671 0.593203 0.653462 0.023 Uiso calc 1 . .
C C5 0.7698(3) 0.6261(2) 0.7341(3) 0.0191(6) Uani d 1 . .
H H5 0.818836 0.619484 0.817639 0.023 Uiso calc 1 . .
C C6 0.6261(3) 0.6512(2) 0.7085(3) 0.0172(6) Uani d 1 . .
H H6 0.574839 0.663213 0.774008 0.021 Uiso calc 1 . .
C C7 0.5566(3) 0.6588(2) 0.5850(3) 0.0154(6) Uani d 1 . .
C C8 0.4052(4) 0.6891(3) 0.5569(3) 0.0245(7) Uani d 1 . .
C C9 0.2912(4) 0.7176(3) 0.5427(3) 0.0348(9) Uani d 1 . .
C C10 0.4077(3) 0.6126(2) -0.0148(3) 0.0160(6) Uani d 1 . .
C C11 0.2866(3) 0.5959(2) -0.1242(3) 0.0203(6) Uani d 1 . .
H H11A 0.302627 0.531575 -0.170131 0.024 Uiso calc 1 . .
H H11B 0.278095 0.656173 -0.181828 0.024 Uiso calc 1 . .
C C12 0.1517(3) 0.5855(2) -0.0665(3) 0.0187(6) Uani d 1 . .
H H12A 0.081287 0.641080 -0.097690 0.022 Uiso calc 1 . .
H H12B 0.105560 0.516507 -0.086346 0.022 Uiso calc 1 . .
C C13 0.2045(3) 0.5967(2) 0.0719(3) 0.0157(6) Uani d 1 . .
H H1 0.972(3) 0.610(3) 0.276(2) 0.031(10) Uiso d 1 . .
H H9 0.199(2) 0.743(3) 0.532(3) 0.040(11) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C3 . . 118.2(2) ?
C2 C1 H1 . . 179(2) ?
C10 N2 C13 . . 112.7(2) ?
C10 N2 I1 . . 123.44(18) ?
C13 N2 I1 . . 123.83(18) ?
C1 C2 C3 . . 174.2(3) ?
N1 C3 C4 . . 121.8(3) ?
N1 C3 C2 . . 118.3(2) ?
C4 C3 C2 . . 119.9(3) ?
C5 C4 C3 . . 119.3(3) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C6 C5 C4 . . 119.3(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C7 . . 119.0(3) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
N1 C7 C6 . . 122.3(3) ?
N1 C7 C8 . . 118.2(2) ?
C6 C7 C8 . . 119.4(3) ?
C9 C8 C7 . . 174.7(4) ?
C8 C9 H9 . . 178(2) ?
O1 C10 N2 . . 124.3(3) ?
O1 C10 C11 . . 126.6(3) ?
N2 C10 C11 . . 109.2(2) ?
C10 C11 C12 . . 104.5(2) ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11B . . 110.8 ?
C12 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.9 ?
C13 C12 C11 . . 105.1(2) ?
C13 C12 H12A . . 110.7 ?
C11 C12 H12A . . 110.7 ?
C13 C12 H12B . . 110.7 ?
C11 C12 H12B . . 110.7 ?
H12A C12 H12B . . 108.8 ?
O2 C13 N2 . . 125.0(3) ?
O2 C13 C12 . . 126.5(3) ?
N2 C13 C12 . . 108.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 N2 . 2.103(2) ?
O1 C10 . 1.213(3) ?
N1 C7 . 1.347(3) ?
N1 C3 . 1.354(4) ?
C1 C2 . 1.154(4) ?
C1 H1 . 0.936(18) ?
O2 C13 . 1.210(3) ?
N2 C10 . 1.381(3) ?
N2 C13 . 1.387(3) ?
C2 C3 . 1.452(4) ?
C3 C4 . 1.392(4) ?
C4 C5 . 1.380(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.372(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.394(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.459(4) ?
C8 C9 . 1.121(5) ?
C9 H9 . 0.919(18) ?
C10 C11 . 1.512(4) ?
C11 C12 . 1.530(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.514(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 O1 1_556 0.95 2.43 3.283(3) 150.0 yes
C11 H11A I1 3_665 0.99 3.24 4.128(3) 150.0 yes
C12 H12B O2 3_565 0.99 2.62 3.506(3) 148.4 yes

_cod_database_fobs_code 2022626
