A family of powerful halogen-bond donors: A structural and theoretical analysis of triply activated 3-iodo-1-phenylprop-2-yn-1-ones
Panikkattu, Vinu V.; Sinha, Abhijeet Shekhar; Aakeröy, Christer; CrystEngComm  (2022) –; doi:10.1039/D1CE01583D

data_7244090
_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 H4 I N O3'
_chemical_formula_sum            'C9 H4 I N O3'
_chemical_formula_weight         301.03
_chemical_name_systematic        3-iodo-1-(3-nitrophenyl)prop-2-yn-1-one
_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             2021-03-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                82.581(7)
_cell_angle_beta                 74.932(9)
_cell_angle_gamma                77.837(9)
_cell_formula_units_Z            4
_cell_length_a                   6.8676(9)
_cell_length_b                   11.0423(10)
_cell_length_c                   13.0715(11)
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5320
_cell_measurement_theta_min      2.5640
_cell_volume                     932.79(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.85a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.85a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.85a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -52.00   3.00   0.50    5.10    --   12.33  -9.00 115.00  110
  2  \w     -6.00  85.00   0.50    5.10    --   12.33   9.00 -70.00  182
  3  \w     33.00  60.00   0.50    5.10    --  -12.49  57.00-120.00   54
  4  \w     16.00  53.00   0.50    5.10    --  -12.49   9.00 -70.00   74
  5  \w    -24.00  11.00   0.50    5.10    --  -12.49  57.00-120.00   70
  6  \w    -74.00   3.00   0.50    5.10    --  -12.49 -57.00 -60.00  154
  7  \w    -73.00  -3.00   0.50    5.10    --  -12.49 -57.00-180.00  140
  8  \w    -82.00   0.00   0.50    5.10    --  -12.49 -77.00  90.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0252730000
_diffrn_orient_matrix_UB_12      0.0386931000
_diffrn_orient_matrix_UB_13      -0.0473683000
_diffrn_orient_matrix_UB_21      0.1025272000
_diffrn_orient_matrix_UB_22      -0.0089550000
_diffrn_orient_matrix_UB_23      0.0050573000
_diffrn_orient_matrix_UB_31      0.0263615000
_diffrn_orient_matrix_UB_32      -0.0526060000
_diffrn_orient_matrix_UB_33      -0.0301379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10762
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.410
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.85a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    2.144
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.485
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     478
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0539
_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/[\s^2^(Fo^2^)+(0.0267P)^2^+9.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3414
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           er_proc
_cod_original_cell_volume        932.79(18)
_cod_database_code               7244090
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C7 H3 I N3 O3'
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.685
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 I2A-C10A \\sim I2B-C10B
 with sigma of 0.02
 O4A-C12A \\sim O4B-C12B
 with sigma of 0.02
 O5A-N2A \\sim O5B-N2B
 with sigma of 0.02
 N2A-O6A \\sim N2B-O6B
 with sigma of 0.02
 N2A-C15A \\sim N2B-C15B
 with sigma of 0.02
 C14A-C13 \\sim C14B-C13
 with sigma of 0.02
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.02
 C13-C12A \\sim C13-C12B
 with sigma of 0.02
 C13-C18A \\sim C13-C18B
 with sigma of 0.02
 C11A-C10A \\sim C11B-C10B
 with sigma of 0.02
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.02
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C18A-C17A \\sim C18B-C17B
 with sigma of 0.02
 C17A-C16A \\sim C17B-C16B
 with sigma of 0.02
 I2A-C11A \\sim I2B-C11B
 with sigma of 0.04
 O4A-C13 \\sim O4B-C13
 with sigma of 0.04
 O4A-C11A \\sim O4B-C11B
 with sigma of 0.04
 O5A-O6A \\sim O5B-O6B
 with sigma of 0.04
 O5A-C15A \\sim O5B-C15B
 with sigma of 0.04
 N2A-C14A \\sim N2B-C14B
 with sigma of 0.04
 N2A-C16A \\sim N2B-C16B
 with sigma of 0.04
 C14A-C16A \\sim C14B-C16B
 with sigma of 0.04
 C13-C11A \\sim C13-C11B
 with sigma of 0.04
 C13-C15A \\sim C13-C15B
 with sigma of 0.04
 C13-C17A \\sim C13-C17B
 with sigma of 0.04
 O6A-C15A \\sim O6B-C15B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C10A-C12A \\sim C10B-C12B
 with sigma of 0.04
 C18A-C16A \\sim C18B-C16B
 with sigma of 0.04
 I1A-C1A \\sim I1C-C1B
 with sigma of 0.02
 O1A-C3A \\sim O1B-C3B
 with sigma of 0.02
 O2A-N1A \\sim O2B-N1B
 with sigma of 0.02
 O3A-N1A \\sim O3B-N1B
 with sigma of 0.02
 C6A-C5A \\sim C6B-C5B
 with sigma of 0.02
 C6A-N1A \\sim C6B-N1B
 with sigma of 0.02
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C5A-C4 \\sim C5B-C4
 with sigma of 0.02
 C4-C3A \\sim C4-C3B
 with sigma of 0.02
 C4-C9A \\sim C4-C9B
 with sigma of 0.02
 C3A-C2A \\sim C3B-C2B
 with sigma of 0.02
 C1A-C2A \\sim C1B-C2B
 with sigma of 0.02
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 I1A-C2A \\sim I1C-C2B
 with sigma of 0.04
 O1A-C4 \\sim O1B-C4
 with sigma of 0.04
 O1A-C2A \\sim O1B-C2B
 with sigma of 0.04
 O2A-O3A \\sim O2B-O3B
 with sigma of 0.04
 O2A-C6A \\sim O2B-C6B
 with sigma of 0.04
 O3A-C6A \\sim O3B-C6B
 with sigma of 0.04
 C6A-C4 \\sim C6B-C4
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
 C5A-N1A \\sim C5B-N1B
 with sigma of 0.04
 C5A-C7A \\sim C5B-C7B
 with sigma of 0.04
 N1A-C7A \\sim N1B-C7B
 with sigma of 0.04
 C4-C2A \\sim C4-C2B
 with sigma of 0.04
 C4-C8A \\sim C4-C8B
 with sigma of 0.04
 C3A-C1A \\sim C3B-C1B
 with sigma of 0.04
 C9A-C7A \\sim C9B-C7B
 with sigma of 0.04
 I1A-C1A \\sim I1C-C1B \\sim I1B-C1A \\sim I1D-C1B
 with sigma of 0.002
 I2A-C10A \\sim I2C-C10B \\sim I2B-C10A \\sim I2D-C10B
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
I2A \\sim I2B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C10A \\sim C10B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C18A \\sim C18B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C12A \\sim C12B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
N2A \\sim N2B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
O5A \\sim O5B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
O6B \\sim O6A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C11B \\sim C18B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C12A \\sim C14B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C15B \\sim C15A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C10A \\sim C18B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C1A \\sim C1B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
I2B \\sim I2C: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
I1A \\sim I1C: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C6B \\sim C6A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C2B \\sim C1B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
O4A \\sim O4B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C11A \\sim C11B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(C12A) = Uanis(C14B)
Uanis(C11A) = Uanis(C13)
Uanis(I1C) = Uanis(I1B)
Uanis(I1A) = Uanis(I1C)
Uanis(I1B) = Uanis(I1D)
Uanis(I2B) = Uanis(I2D)
4. Rigid body (RIGU) restrains
 I2A, O4A, O5A, N2A, C14A, O6A, C11A, C15A, C10A, C12A, C18A, C17A, C16A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 I2B, C10B, C11B, C12B, O4B, C14B, C18B, C17B, C15B, C16B, N2B, O5B, O6B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5B, I1A, C1A, C2A, C3A, O1A, C4, C5A, C9A, C3B, C9B, C6A, C8A, C2B, O1B, C6B,
  C8B, N1A, C7A, C1B, N1B, C7B, O2A, O3A, I1C, O2B, O3B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C10B)=Sof(C11B)=Sof(C12B)=Sof(O4B)=Sof(C14B)=Sof(H14B)=Sof(C18B)=
 Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(N2B)=Sof(O5B)=
 Sof(O6B)=1-FVAR(1)
 Sof(O4A)=Sof(O5A)=Sof(N2A)=Sof(C14A)=Sof(H14A)=Sof(O6A)=Sof(C11A)=Sof(C15A)=
 Sof(C10A)=Sof(C12A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=
 Sof(H16A)=FVAR(1)
 Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(O1B)=Sof(C5B)=Sof(H5B)=Sof(C9B)=Sof(H9B)=
 Sof(C6B)=Sof(C8B)=Sof(H8B)=Sof(N1B)=Sof(C7B)=Sof(H7B)=Sof(O2B)=Sof(O3B)=1-
 FVAR(2)
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C6A)=Sof(C5A)=Sof(H5A)=Sof(N1A)=Sof(C3A)=
 Sof(C1A)=Sof(C9A)=Sof(H9A)=Sof(C2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=FVAR(2)
 Fixed Sof: I1A(0.75) I2A(0.75) I2B(0.14) I1C(0.22) I2C(0.1) I1B(0.02)
 I1D(0.01) I2D(0.01)
6.a Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C14A(H14A), C9A(H9A), C7A(H7A), C8A(H8A), C18A(H18A), C17A(H17A),
 C16A(H16A), C14B(H14B), C18B(H18B), C17B(H17B), C16B(H16B), C5B(H5B), C9B(H9B),
  C8B(H8B), C7B(H7B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.612
_oxdiff_exptl_absorpt_empirical_full_min 0.676