#------------------------------------------------------------------------------
#$Date: 2021-12-21 01:35:35 +0200 (Tue, 21 Dec 2021) $
#$Revision: 271547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244089.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244089
loop_
_publ_author_name
'Panikkattu, Vinu V.'
'Sinha, Abhijeet Shekhar'
'Aakeröy, Christer'
_publ_section_title
;
 A family of powerful halogen-bond donors: A structural and theoretical
 analysis of triply activated 3-iodo-1-phenylprop-2-yn-1-ones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01583D
_journal_year                    2022
_chemical_formula_moiety         'C10 H4 I N O'
_chemical_formula_sum            'C10 H4 I N O'
_chemical_formula_weight         281.04
_chemical_name_systematic        3-(3-iodopropioloyl)benzonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-01
_audit_creation_method
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                104.330(2)
_cell_angle_beta                 96.117(2)
_cell_angle_gamma                94.399(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6138(3)
_cell_length_b                   7.8625(4)
_cell_length_c                   11.1133(5)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      69.49
_cell_measurement_theta_min      4.14
_cell_volume                     469.84(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker MicroStar'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6165
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         70.02
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    26.425
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_correction_T_min  0.13
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1270 before and 0.0697 after correction.
The Ratio of minimum to maximum transmission is 0.0803.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Thin plate'
_exptl_crystal_F_000             264
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dioxane'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.992
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0392
_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/[σ²(Fo²)+(0.0843P)²+0.0260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                1566
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           vp-k1-3cn-3-2
_cod_database_code               7244089
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4451(8) 0.7302(6) 0.5116(4) 0.0427(9) Uani d . . . 1 . .
C C2 0.3174(8) 0.7145(6) 0.6102(5) 0.0464(9) Uani d . . . 1 . .
H H2 0.1662 0.6445 0.5939 0.056 Uiso calc U . R 1 . .
C C3 0.4123(10) 0.8010(6) 0.7310(5) 0.0470(10) Uani d . . . 1 . .
C C4 0.6323(11) 0.9038(8) 0.7575(5) 0.0555(12) Uani d . . . 1 . .
H H4 0.6927 0.9658 0.8413 0.067 Uiso calc U . R 1 . .
C C5 0.7635(11) 0.9153(9) 0.6605(6) 0.0621(14) Uani d . . . 1 . .
H H5 0.9174 0.9819 0.6774 0.075 Uiso calc U . R 1 . .
C C6 0.6671(9) 0.8280(7) 0.5376(5) 0.0511(10) Uani d . . . 1 . .
H H6 0.7562 0.8363 0.4709 0.061 Uiso calc U . R 1 . .
C C7 0.3366(9) 0.6369(7) 0.3809(5) 0.0515(11) Uani d . . . 1 . .
O O8 0.1383(8) 0.5554(8) 0.3572(4) 0.0808(14) Uani d . . . 1 . .
C C9 0.4774(11) 0.6519(8) 0.2819(5) 0.0534(12) Uani d . . . 1 . .
C C10 0.6009(11) 0.6679(7) 0.2032(5) 0.0519(11) Uani d . . . 1 . .
I I11 0.81612(5) 0.70354(4) 0.07821(2) 0.05255(19) Uani d . . . 1 . .
C C12 0.2776(11) 0.7893(7) 0.8330(5) 0.0555(12) Uani d . . . 1 . .
N N13 0.1710(11) 0.7830(8) 0.9131(5) 0.0740(18) Uani 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 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 C1 C2 . . 119.3(4) ?
C6 C1 C7 . . 122.2(4) ?
C2 C1 C7 . . 118.5(4) ?
C3 C2 C1 . . 119.5(5) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 121.5(5) ?
C2 C3 C12 . . 119.7(5) ?
C4 C3 C12 . . 118.8(5) ?
C3 C4 C5 . . 119.3(5) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 119.3(6) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C1 C6 C5 . . 121.1(5) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
O8 C7 C9 . . 120.8(5) ?
O8 C7 C1 . . 122.4(5) ?
C9 C7 C1 . . 116.8(5) ?
C10 C9 C7 . . 177.6(6) ?
C9 C10 I11 . . 177.3(5) ?
C10 I11 N13 . 1_654 174.1(2) ?
N13 C12 C3 . . 178.8(6) ?
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
C1 C6 . 1.376(7) ?
C1 C2 . 1.397(6) ?
C1 C7 . 1.495(7) ?
C2 C3 . 1.375(8) ?
C2 H2 . 0.95 ?
C3 C4 . 1.384(9) ?
C3 C12 . 1.446(7) ?
C4 C5 . 1.386(9) ?
C4 H4 . 0.95 ?
C5 C6 . 1.397(8) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O8 . 1.210(7) ?
C7 C9 . 1.443(7) ?
C9 C10 . 1.196(9) ?
C10 I11 . 1.992(6) ?
I11 N13 1_654 2.981(5) ?
C12 N13 . 1.133(8) ?
