#------------------------------------------------------------------------------
#$Date: 2021-12-21 01:35:35 +0200 (Tue, 21 Dec 2021) $
#$Revision: 271547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244086.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_7244086
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 H4 I N O3'
_chemical_formula_sum            'C9 H4 I N O3'
_chemical_formula_weight         301.041
_chemical_name_systematic        3-iodo-1-(4-nitrophenyl)prop-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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.341(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0639(1)
_cell_length_b                   23.333(1)
_cell_length_c                   10.0221(4)
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      33.0180
_cell_measurement_theta_min      2.2070
_cell_volume                     948.71(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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  'olex2.refine 1.3-ac4 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.8529
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  85.00   0.50   16.33    --   12.33  77.00   0.00  190
  2  ω     20.00  46.00   0.50   16.33    --   12.33  38.00 -60.00   52
  3  ω    -62.00   2.00   0.50   16.33    --   12.33 -19.00  60.00  128
  4  ω    -62.00   3.00   0.50   16.33    --  -12.49 -57.00   0.00  130
  5  ω     28.00  68.00   0.50   16.33    --   12.33-140.00 -35.00   80
  6  ω     16.00  41.00   0.50   16.33    --   12.33-130.00 138.00   50
  7  ω     42.00  80.00   0.50   16.33    --   12.33-178.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159223000
_diffrn_orient_matrix_UB_12      0.0302165000
_diffrn_orient_matrix_UB_13      -0.0035206000
_diffrn_orient_matrix_UB_21      0.1037820000
_diffrn_orient_matrix_UB_22      -0.0030073000
_diffrn_orient_matrix_UB_23      -0.0540973000
_diffrn_orient_matrix_UB_31      -0.1397690000
_diffrn_orient_matrix_UB_32      0.0012298000
_diffrn_orient_matrix_UB_33      -0.0457269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.8529
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11750
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.8529
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.58
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       plate
_exptl_crystal_F_000             566.714
_exptl_crystal_recrystallization_method 'crystallized from dioxane'
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.069
_refine_diff_density_max         1.8023
_refine_diff_density_min         -1.3657
_refine_diff_density_rms         0.1425
_refine_ls_d_res_high            0.6424
_refine_ls_d_res_low             9.1954
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0409
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0347P)²+1.4396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -5
_reflns_limit_k_max              35
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2656
_reflns_number_total             3206
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce01583d2.cif
_cod_data_source_block           exp_70
_cod_database_code               7244086
_chemical_oxdiff_formula         'C9 H4 I1 N1 O3'
_reflns_odcompleteness_completeness 99.89
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3), C2(H2)
;
_olex2_date_sample_data_collection 2021-01-15
_olex2_date_sample_submission    2021-01-15
_olex2_exptl_crystal_mounting_method 'mounted ona MiTeGen loop'
_olex2_submission_original_sample_id VP-K1-4N-3-1
_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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.635
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
I10 I 0.71950(5) 0.076548(9) 0.61036(2) 0.04142(9) Uani 1.000000 .
O11 O 0.1917(6) 0.25934(11) 0.3532(2) 0.0481(6) Uani 1.000000 .
O14 O 1.1349(7) 0.44950(11) 0.7969(3) 0.0525(6) Uani 1.000000 .
N12 N 0.9398(7) 0.45453(11) 0.7007(3) 0.0388(6) Uani 1.000000 .
O13 O 0.8572(8) 0.50091(11) 0.6541(3) 0.0655(8) Uani 1.000000 .
C5 C 0.8605(7) 0.35036(13) 0.6980(3) 0.0314(5) Uani 1.000000 .
H5 H 0.9874(7) 0.34783(13) 0.7781(3) 0.0377(6) Uiso 1.000000 R
C4 C 0.7987(7) 0.40226(12) 0.6380(3) 0.0311(5) Uani 1.000000 .
C1 C 0.5354(6) 0.30637(11) 0.5173(3) 0.0275(5) Uani 1.000000 .
C6 C 0.7285(7) 0.30160(12) 0.6362(3) 0.0301(5) Uani 1.000000 .
H6 H 0.7690(7) 0.26574(12) 0.6742(3) 0.0361(6) Uiso 1.000000 R
C8 C 0.4839(7) 0.19902(13) 0.5024(3) 0.0344(6) Uani 1.000000 .
C3 C 0.6098(8) 0.40827(13) 0.5181(3) 0.0356(6) Uani 1.000000 .
H3 H 0.5743(8) 0.44416(13) 0.4795(3) 0.0428(7) Uiso 1.000000 R
C9 C 0.5686(7) 0.15287(13) 0.5422(3) 0.0345(6) Uani 1.000000 .
C2 C 0.4776(7) 0.35989(13) 0.4584(3) 0.0342(6) Uani 1.000000 .
H2 H 0.3495(7) 0.36277(13) 0.3787(3) 0.0410(7) Uiso 1.000000 R
C7 C 0.3878(7) 0.25489(13) 0.4501(3) 0.0337(6) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13 N12 O14 122.8(3) . . ?
C4 N12 O14 118.5(3) . . ?
C4 N12 O13 118.7(3) . . ?
C4 C5 H5 120.90(16) . . ?
C6 C5 H5 120.90(16) . . ?
C6 C5 C4 118.2(2) . . ?
C5 C4 N12 119.2(3) . . ?
C3 C4 N12 117.7(3) . . ?
C3 C4 C5 123.0(3) . . ?
C2 C1 C6 120.4(2) . . ?
C7 C1 C6 121.0(2) . . ?
C7 C1 C2 118.6(2) . . ?
C1 C6 C5 120.0(3) . . ?
H6 C6 C5 119.99(16) . . ?
H6 C6 C1 119.99(16) . . ?
C7 C8 C9 178.0(3) . . ?
H3 C3 C4 120.84(17) . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3 120.84(17) . . ?
C8 C9 I10 178.7(3) . . ?
C3 C2 C1 120.0(2) . . ?
H2 C2 C1 120.00(15) . . ?
H2 C2 C3 120.00(17) . . ?
C1 C7 O11 121.2(3) . . ?
C8 C7 O11 120.8(3) . . ?
C8 C7 C1 118.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I10 C9 1.991(3) . ?
O11 C7 1.224(4) . ?
O14 N12 1.218(4) . ?
N12 O13 1.218(4) . ?
N12 C4 1.473(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(4) . ?
C5 C6 1.388(4) . ?
C4 C3 1.395(4) . ?
C1 C6 1.393(3) . ?
C1 C2 1.395(4) . ?
C1 C7 1.486(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.192(4) . ?
C8 C7 1.450(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.372(4) . ?
C2 H2 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C7 C1 C6 172.6(3) . . . . ?
O11 C7 C1 C2 -7.7(4) . . . . ?
O14 N12 C4 C5 7.4(3) . . . . ?
O14 N12 C4 C3 -171.9(3) . . . . ?
N12 C4 C5 C6 -179.2(3) . . . . ?
N12 C4 C3 C2 179.8(3) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C5 C6 C1 C2 1.0(3) . . . . ?
C5 C6 C1 C7 -179.2(3) . . . . ?
C4 C3 C2 C1 -0.4(4) . . . . ?
