#------------------------------------------------------------------------------
#$Date: 2021-12-21 01:35:35 +0200 (Tue, 21 Dec 2021) $
#$Revision: 271547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244088.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_7244088
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         'C9 H5 I O'
_chemical_formula_sum            'C9 H5 I O'
_chemical_formula_weight         256.03
_chemical_name_systematic        3-iodo-1-phenylprop-2-yn-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-01
_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                90
_cell_angle_beta                 91.0130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0763(2)
_cell_length_b                   11.2448(2)
_cell_length_c                   7.2619(2)
_cell_measurement_reflns_used    3738
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      69.84
_cell_measurement_theta_min      4.39
_cell_volume                     822.69(3)
_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 0.963
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5730
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         69.83
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    30.056
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0379 after correction.
The Ratio of minimum to maximum transmission is 0.7535.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dioxane'
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+0.6377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                1416
_reflns_number_total             1501
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           vp-k1-us-3-3
_cod_database_code               7244088
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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 0.5660(3) 0.3758(3) 0.3453(4) 0.0171(6) Uani d . . . 1 . .
C C2 0.5151(3) 0.4745(3) 0.2498(5) 0.0200(6) Uani d . . . 1 . .
H H2 0.5736 0.5332 0.2035 0.024 Uiso calc U . R 1 . .
C C3 0.3798(4) 0.4864(3) 0.2232(5) 0.0257(7) Uani d . . . 1 . .
H H3 0.3453 0.5529 0.1574 0.031 Uiso calc U . R 1 . .
C C4 0.2939(3) 0.4015(3) 0.2924(5) 0.0261(7) Uani d . . . 1 . .
H H4 0.2009 0.4097 0.273 0.031 Uiso calc U . R 1 . .
C C5 0.3439(3) 0.3040(3) 0.3903(5) 0.0249(7) Uani d . . . 1 . .
H H5 0.285 0.2466 0.4392 0.03 Uiso calc U . R 1 . .
C C6 0.4791(3) 0.2913(3) 0.4158(4) 0.0211(6) Uani d . . . 1 . .
H H6 0.5133 0.2247 0.4816 0.025 Uiso calc U . R 1 . .
C C7 0.7103(4) 0.3575(3) 0.3713(5) 0.0205(7) Uani d . . . 1 . .
O O8 0.7558(2) 0.2677(2) 0.4436(4) 0.0310(6) Uani d . . . 1 . .
C C9 0.7994(3) 0.4498(3) 0.3072(5) 0.0254(7) Uani d . . . 1 . .
C C10 0.8770(3) 0.5249(3) 0.2603(5) 0.0259(7) Uani d . . . 1 . .
I I11 1.01141(2) 0.64268(2) 0.17832(3) 0.02469(12) 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'
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 . . 119.6(3) ?
C6 C1 C7 . . 118.8(3) ?
C2 C1 C7 . . 121.6(3) ?
C3 C2 C1 . . 119.9(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 119.8(3) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
O8 C7 C9 . . 119.8(3) ?
O8 C7 C1 . . 122.0(3) ?
C9 C7 C1 . . 118.2(3) ?
C10 C9 C7 . . 177.1(4) ?
C9 C10 I11 . . 177.1(3) ?
C10 I11 O8 . 2_755 167.24(12) ?
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 . 1.395(5) ?
C1 C2 . 1.402(5) ?
C1 C7 . 1.477(5) ?
C2 C3 . 1.380(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.389(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.395(5) ?
C4 H4 . 0.95 ?
C5 C6 . 1.379(5) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O8 . 1.224(4) ?
C7 C9 . 1.454(5) ?
C9 C10 . 1.205(6) ?
C10 I11 . 1.993(4) ?
I11 O8 2_755 2.887(3) ?
