# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_70
_database_code_depnum_ccdc_archive 'CCDC 2110093'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_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)
;
loop_
_audit_author_email
vinu@ksu.edu
aakeroy@ksu.edu
_chemical_formula_moiety         'C9 H4 I N O3'
_chemical_formula_sum            'C9 H4 I N O3'
_chemical_formula_weight         301.041
_chemical_oxdiff_formula         'C9 H4 I1 N1 O3'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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

_symmetry_Int_Tables_number      14
_cell_length_a                   4.0639(1)
_cell_length_b                   23.333(1)
_cell_length_c                   10.0221(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.341(3)
_cell_angle_gamma                90
_cell_volume                     948.71(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      33.0180
_cell_measurement_theta_min      2.2070
_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_preparation       ?
_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
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_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_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_reflns_threshold_expression     I>=2u(I)
_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)'
_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_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.0409
_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
_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)
;
_atom_sites_solution_primary     dual
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_
_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_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_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) . . . . ?


_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
_chemical_name_systematic        3-iodo-1-(4-nitrophenyl)prop-2-yn-1-one
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vp-k1-f-3-2
_database_code_depnum_ccdc_archive 'CCDC 2110113'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2020-05-13
_audit_creation_method           
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        1-(4-fluorophenyl)-3-iodoprop-2-yn-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H4 F I O'
_chemical_formula_sum            'C9 H4 F I O'
_chemical_formula_iupac          ?
_chemical_formula_weight         274.02
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   19.4398(5)
_cell_length_b                   19.4398(5)
_cell_length_c                   5.05770(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1911.33(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      6.44
_cell_measurement_theta_max      69.85
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024

_exptl_absorpt_coefficient_mu    26.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.5217.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_T_max  0.18

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            4548
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         70.32
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5

_refine_special_details          'Refined as a 2-component inversion twin.'

_reflns_number_total             1611
_reflns_number_gt                1557
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1014
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.264
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00098(13)
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.04(2)

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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 0.6109(4) 0.2788(4) 0.5966(17) 0.0174(16) Uani d . . . 1 . .
C C2 0.6680(4) 0.2920(5) 0.437(2) 0.0250(19) Uani d . . . 1 . .
H H2 0.7085 0.2651 0.4576 0.03 Uiso calc U . R 1 . .
C C3 0.6663(5) 0.3434(6) 0.249(2) 0.033(2) Uani d . . . 1 . .
H H3 0.7048 0.3524 0.1386 0.039 Uiso calc U . R 1 . .
C C4 0.6066(6) 0.3814(5) 0.228(2) 0.033(2) Uani d . . . 1 . .
C C5 0.5494(5) 0.3708(5) 0.384(2) 0.030(2) Uani d . . . 1 . .
H H5 0.5095 0.3985 0.3632 0.036 Uiso calc U . R 1 . .
C C6 0.5514(5) 0.3191(4) 0.569(2) 0.0238(19) Uani d . . . 1 . .
H H6 0.5126 0.3107 0.6788 0.029 Uiso calc U . R 1 . .
C C7 0.6147(4) 0.2225(4) 0.792(2) 0.0189(16) Uani d . . . 1 . .
O O8 0.6676(3) 0.1885(4) 0.8274(16) 0.0324(15) Uani d . . . 1 . .
C C9 0.5531(4) 0.2079(5) 0.9468(19) 0.0209(17) Uani d . . . 1 . .
C C10 0.5046(5) 0.1968(5) 1.078(2) 0.027(2) Uani d . . . 1 . .
I I11 0.42209(3) 0.17927(3) 1.30967(12) 0.0313(3) Uani d . . . 1 . .
F F12 0.6048(5) 0.4321(3) 0.0456(15) 0.055(2) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 . 1.397(13) ?
C1 C6 . 1.404(12) ?
C1 C7 . 1.476(12) ?
C2 C3 . 1.379(15) ?
C2 H2 . 0.95 ?
C3 C4 . 1.380(16) ?
C3 H3 . 0.95 ?
C4 F12 . 1.351(11) ?
C4 C5 . 1.377(16) ?
C5 C6 . 1.376(14) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O8 . 1.235(11) ?
C7 C9 . 1.460(11) ?
C9 C10 . 1.172(14) ?
C10 I11 . 2.016(10) ?
I11 O8 8_547 2.837(7) ?

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
C2 C1 C6 . . 119.7(9) ?
C2 C1 C7 . . 118.9(8) ?
C6 C1 C7 . . 121.4(8) ?
C3 C2 C1 . . 120.8(9) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 117.4(9) ?
C2 C3 H3 . . 121.3 ?
C4 C3 H3 . . 121.3 ?
F12 C4 C5 . . 118.6(10) ?
F12 C4 C3 . . 117.7(10) ?
C5 C4 C3 . . 123.7(9) ?
C6 C5 C4 . . 118.5(9) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C1 . . 119.8(9) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
O8 C7 C9 . . 120.0(9) ?
O8 C7 C1 . . 122.4(8) ?
C9 C7 C1 . . 117.6(7) ?
C10 C9 C7 . . 178.0(11) ?
C9 C10 I11 . . 178.6(10) ?
C10 I11 O8 . 8_547 173.3(3) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vp-k1-us-3-3
_database_code_depnum_ccdc_archive 'CCDC 2110111'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_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)
;
_chemical_name_systematic        3-iodo-1-phenylprop-2-yn-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H5 I O'
_chemical_formula_sum            'C9 H5 I O'
_chemical_formula_iupac          ?
_chemical_formula_weight         256.03

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   10.0763(2)
_cell_length_b                   11.2448(2)
_cell_length_c                   7.2619(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.0130(10)
_cell_angle_gamma                90
_cell_volume                     822.69(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3738
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      69.84
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       Chunk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    30.056
_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_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  0.38

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            5730
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_theta_min         4.39
_diffrn_reflns_theta_max         69.83
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             1501
_reflns_number_gt                1416
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0697
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         1501
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.6377P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) ?

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) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vp-k1-3cn-3-2
_database_code_depnum_ccdc_archive 'CCDC 2110114'
loop_
_audit_author_name
_audit_author_address
'Abhijeet S. Sinha'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_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)
;
_chemical_name_systematic        3-(3-iodopropioloyl)benzonitrile
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H4 I N O'
_chemical_formula_sum            'C10 H4 I N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         281.04

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6138(3)
_cell_length_b                   7.8625(4)
_cell_length_c                   11.1133(5)
_cell_angle_alpha                104.330(2)
_cell_angle_beta                 96.117(2)
_cell_angle_gamma                94.399(3)
_cell_volume                     469.84(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5075
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      69.49
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       'Thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264

_exptl_absorpt_coefficient_mu    26.425
_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_absorpt_correction_T_min  0.13
_exptl_absorpt_correction_T_max  0.50

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            6165
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         70.02
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             1643
_reflns_number_gt                1566
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1053
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         1643
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0843P)²+0.0260P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.992
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker MicroStar'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) ?

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) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_er_proc
_database_code_depnum_ccdc_archive 'CCDC 2110098'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        3-iodo-1-(3-nitrophenyl)prop-2-yn-1-one
_chemical_formula_moiety         'C9 H4 I N O3'
_chemical_formula_sum            'C9 H4 I N O3'
_chemical_formula_weight         301.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H3 I N3 O3'
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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8676(9)
_cell_length_b                   11.0423(10)
_cell_length_c                   13.0715(11)
_cell_angle_alpha                82.581(7)
_cell_angle_beta                 74.932(9)
_cell_angle_gamma                77.837(9)
_cell_volume                     932.79(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5320
_cell_measurement_theta_min      2.5640
_shelx_estimated_absorpt_T_max   0.749
_shelx_estimated_absorpt_T_min   0.685
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    2.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -8 -16 0.0425
2 -9 13 0.0441
1 13 11 0.0532
-2 2 -18 0.0307
1 -10 -13 0.0385
-4 -15 -2 0.0592
-6 -10 7 0.0519
-5 0 13 0.0665
0 12 12 0.0575
6 9 -8 0.0477
1 -12 -11 0.0444
-8 -11 -6 0.0437
-9 -4 1 0.0494
-6 7 8 0.0538
9 5 0 0.0589
-3 1 -5 0.0551
4 -2 5 0.0535
2 1 5 0.0561

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.3714 -8.4116 -16.3294 0.4134 -0.1479 0.8985
1.7760 -9.0337 13.3315 -0.9361 0.3304 0.1203
0.5987 13.1049 10.8284 0.0093 -0.0012 -1.0000
-1.9578 2.0045 -17.8158 0.8720 -0.3088 0.3799
1.3793 -9.5609 -13.3434 0.2970 0.1596 0.9415
-4.3976 -14.9913 -1.9771 -0.5975 -0.3266 0.7323
-5.8289 -9.7242 7.3127 -0.8700 -0.4736 0.1375
-4.6263 -0.0279 13.3328 -0.7496 -0.4066 -0.5223
-0.1069 11.9384 11.9964 -0.1090 -0.0572 -0.9924
5.8286 8.9094 -8.1096 0.8762 0.4768 -0.0706
0.9051 -12.0685 -10.8829 0.0714 0.1458 0.9867
-8.0051 -11.2134 -5.9158 -0.3560 -0.7502 0.5572
-9.1966 -4.1467 0.7705 -0.4294 -0.9019 -0.0475
-5.6834 6.5624 8.3801 -0.2867 -0.5991 -0.7476
9.2472 5.0706 0.0058 0.4296 0.9027 -0.0231
-2.9995 0.9981 -5.0016 0.1997 -0.3418 0.0192
3.9991 -1.9974 5.0022 -0.2132 0.4532 0.0597
1.9998 1.0011 5.0006 -0.1476 0.2214 -0.1507

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00   3.00   0.50    5.10    --   12.33  -9.00 115.00  110
  2  ω     -6.00  85.00   0.50    5.10    --   12.33   9.00 -70.00  182
  3  ω     33.00  60.00   0.50    5.10    --  -12.49  57.00-120.00   54
  4  ω     16.00  53.00   0.50    5.10    --  -12.49   9.00 -70.00   74
  5  ω    -24.00  11.00   0.50    5.10    --  -12.49  57.00-120.00   70
  6  ω    -74.00   3.00   0.50    5.10    --  -12.49 -57.00 -60.00  154
  7  ω    -73.00  -3.00   0.50    5.10    --  -12.49 -57.00-180.00  140
  8  ω    -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3414
_reflns_number_total             3815
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         1.485
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.106
_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)+(0.0267P)²+9.4850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I -0.11978(16) 0.13871(6) 1.38847(8) 0.01854(19) Uani 0.75 1 d D U P A 4
I2A I 0.38556(16) 0.68749(9) 0.87122(8) 0.0201(2) Uani 0.75 1 d D U P B 1
O1A O 0.1949(19) -0.1040(7) 1.0378(7) 0.0199(19) Uani 0.813(10) 1 d D U P A 4
O2A O 0.5438(10) -0.0197(7) 0.6647(5) 0.0270(16) Uani 0.813(10) 1 d D U P A 3
O4A O 0.684(3) 0.3974(10) 0.5420(10) 0.0236(14) Uani 0.665(12) 1 d D U P B 1
O3A O 0.6858(10) 0.1434(6) 0.6207(5) 0.0303(16) Uani 0.813(10) 1 d D U P A 3
O5A O 1.0469(14) 0.4160(10) 0.1818(7) 0.0301(17) Uani 0.665(12) 1 d D U P B 1
N2A N 1.0752(15) 0.5203(10) 0.1808(7) 0.0222(14) Uani 0.665(12) 1 d D U P B 1
C6A C 0.4666(14) 0.1294(8) 0.7877(6) 0.0167(12) Uani 0.813(10) 1 d D U P A 3
C5A C 0.374(3) 0.0485(9) 0.8668(7) 0.018(3) Uani 0.813(10) 1 d D U P A 3
H5A H 0.3766 -0.0345 0.8540 0.021 Uiso 0.813(10) 1 calc R . P A 3
N1A N 0.5731(11) 0.0809(8) 0.6837(5) 0.0198(13) Uani 0.813(10) 1 d D U P A 3
C14A C 0.880(4) 0.5262(11) 0.3679(8) 0.017(3) Uani 0.665(12) 1 d D U P B 1
H14A H 0.8781 0.4404 0.3681 0.021 Uiso 0.665(12) 1 calc R . P B 1
C13 C 0.7838(11) 0.5884(6) 0.4595(5) 0.0215(11) Uani 1 1 d D . . . .
C4 C 0.2788(10) 0.0934(6) 0.9651(5) 0.0162(10) Uani 1 1 d D U . . .
C3A C 0.186(2) 0.0039(8) 1.0520(6) 0.0134(17) Uani 0.813(10) 1 d D U P A 4
C1A C 0.0147(15) 0.0886(8) 1.2430(6) 0.0195(16) Uani 0.813(10) 1 d D U P A 4
C9A C 0.2702(18) 0.2160(7) 0.9829(8) 0.018(2) Uani 0.813(10) 1 d D U P A 3
H9A H 0.2019 0.2462 1.0503 0.022 Uiso 0.813(10) 1 calc R . P A 3
O6A O 1.1834(15) 0.5783(10) 0.1052(7) 0.0403(19) Uani 0.665(12) 1 d D U P B 1
C2A C 0.098(2) 0.0508(7) 1.1556(6) 0.018(2) Uani 0.813(10) 1 d D U P A 4
C11A C 0.599(2) 0.5604(11) 0.6513(8) 0.0215(11) Uani 0.665(12) 1 d D U P B 1
C15A C 0.979(2) 0.5886(10) 0.2770(8) 0.0187(13) Uani 0.665(12) 1 d D U P B 1
C10A C 0.518(3) 0.6193(12) 0.7283(8) 0.024(2) Uani 0.665(12) 1 d D U P B 1
C12A C 0.684(4) 0.5044(12) 0.5504(9) 0.0178(12) Uani 0.665(12) 1 d D U P B 1
C7A C 0.4650(13) 0.2508(8) 0.8026(7) 0.0175(16) Uani 0.813(10) 1 d D U P A 3
H7A H 0.5317 0.3035 0.7473 0.021 Uiso 0.813(10) 1 calc R . P A 3
C8A C 0.3623(14) 0.2935(7) 0.9014(8) 0.0191(17) Uani 0.813(10) 1 d D U P A 3
H8A H 0.3552 0.3776 0.9132 0.023 Uiso 0.813(10) 1 calc R . P A 3
C18A C 0.797(2) 0.7120(9) 0.4565(10) 0.0206(17) Uani 0.665(12) 1 d D U P B 1
H18A H 0.7358 0.7557 0.5184 0.025 Uiso 0.665(12) 1 calc R . P B 1
C17A C 0.8996(19) 0.7748(10) 0.3647(11) 0.021(2) Uani 0.665(12) 1 d D U P B 1
H17A H 0.9056 0.8598 0.3655 0.025 Uiso 0.665(12) 1 calc R . P B 1
C16A C 0.9913(17) 0.7151(10) 0.2734(10) 0.018(2) Uani 0.665(12) 1 d D U P B 1
H16A H 1.0600 0.7571 0.2107 0.021 Uiso 0.665(12) 1 calc R . P B 1
I2B I 0.3542(8) 0.6379(7) 0.8975(4) 0.0213(8) Uani 0.14 1 d D U P B 1
C10B C 0.506(7) 0.596(3) 0.7454(14) 0.024(2) Uani 0.335(12) 1 d D U P B 2
C11B C 0.580(5) 0.585(2) 0.6509(13) 0.0216(12) Uani 0.335(12) 1 d D U P B 2
C12B C 0.684(8) 0.514(2) 0.5581(17) 0.0179(13) Uani 0.335(12) 1 d D U P B 2
O4B O 0.672(6) 0.4071(19) 0.558(2) 0.0237(16) Uani 0.335(12) 1 d D U P B 2
C14B C 0.867(9) 0.539(3) 0.3618(18) 0.0178(12) Uani 0.335(12) 1 d D U P B 2
H14B H 0.8579 0.4581 0.3489 0.021 Uiso 0.335(12) 1 calc R . P B 2
C18B C 0.766(5) 0.7091(16) 0.4826(19) 0.0206(17) Uani 0.335(12) 1 d D U P B 2
H18B H 0.6934 0.7377 0.5500 0.025 Uiso 0.335(12) 1 calc R . P B 2
C17B C 0.861(4) 0.7862(17) 0.401(2) 0.022(4) Uani 0.335(12) 1 d D U P B 2
H17B H 0.8569 0.8700 0.4126 0.026 Uiso 0.335(12) 1 calc R . P B 2
C15B C 0.965(4) 0.6202(18) 0.2839(14) 0.0187(14) Uani 0.335(12) 1 d D U P B 2
C16B C 0.963(4) 0.7422(19) 0.303(2) 0.028(6) Uani 0.335(12) 1 d D U P B 2
H16B H 1.0302 0.7952 0.2480 0.033 Uiso 0.335(12) 1 calc R . P B 2
N2B N 1.073(3) 0.5645(19) 0.1825(13) 0.0223(14) Uani 0.335(12) 1 d D U P B 2
O5B O 1.043(3) 0.4656(19) 0.1657(14) 0.0297(18) Uani 0.335(12) 1 d D U P B 2
O6B O 1.191(3) 0.6303(18) 0.1224(14) 0.039(2) Uani 0.335(12) 1 d D U P B 2
I1C I -0.1131(7) 0.1754(3) 1.3795(3) 0.01854(19) Uani 0.22 1 d D U P A 3
C1B C 0.031(7) 0.129(3) 1.2340(14) 0.0196(16) Uani 0.187(10) 1 d D U P A 3
C2B C 0.084(11) 0.076(4) 1.153(2) 0.0197(17) Uani 0.187(10) 1 d D U P A 3
C3B C 0.198(12) 0.010(3) 1.061(2) 0.022(5) Uani 0.187(10) 1 d D U P A 3
O1B O 0.172(10) -0.094(3) 1.054(3) 0.026(9) Uani 0.187(10) 1 d D U P A 3
C5B C 0.371(14) 0.033(4) 0.873(3) 0.023(15) Uani 0.187(10) 1 d D U P A 4
H5B H 0.3682 -0.0530 0.8738 0.028 Uiso 0.187(10) 1 calc R . P A 4
C9B C 0.288(9) 0.219(2) 0.958(3) 0.024(11) Uani 0.187(10) 1 d D U P A 4
H9B H 0.2246 0.2653 1.0189 0.028 Uiso 0.187(10) 1 calc R . P A 4
C6B C 0.467(6) 0.093(3) 0.7793(18) 0.0168(13) Uani 0.187(10) 1 d D U P A 4
C8B C 0.388(7) 0.279(3) 0.866(3) 0.028(10) Uani 0.187(10) 1 d D U P A 4
H8B H 0.3923 0.3643 0.8653 0.033 Uiso 0.187(10) 1 calc R . P A 4
N1B N 0.561(5) 0.023(3) 0.6829(18) 0.026(7) Uani 0.187(10) 1 d D U P A 4
C7B C 0.483(5) 0.217(3) 0.775(2) 0.015(6) Uani 0.187(10) 1 d D U P A 4
H7B H 0.5546 0.2574 0.7129 0.017 Uiso 0.187(10) 1 calc R . P A 4
O2B O 0.547(4) -0.090(2) 0.689(2) 0.029(6) Uani 0.187(10) 1 d D U P A 4
O3B O 0.657(6) 0.078(3) 0.604(2) 0.046(9) Uani 0.187(10) 1 d D U P A 4
I2C I 0.3937(15) 0.6437(8) 0.8610(7) 0.0198(12) Uani 0.1 1 d D U P B 2
I1B I -0.068(4) 0.201(2) 1.3594(15) 0.01854(19) Uani 0.02 1 d D . P A 65
I1D I -0.107(6) 0.250(3) 1.342(3) 0.01854(19) Uani 0.01 1 d D . P A 7
I2D I 0.378(7) 0.572(5) 0.906(3) 0.0213(8) Uani 0.01 1 d D . P B 5


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
I1A C1A 1.980(7) . ?
I2A C10A 2.019(10) . ?
O1A C3A 1.216(9) . ?
O2A N1A 1.237(10) . ?
O4A C12A 1.201(10) . ?
O3A N1A 1.225(9) . ?
O5A N2A 1.206(11) . ?
N2A O6A 1.262(11) . ?
N2A C15A 1.481(12) . ?
C6A C5A 1.388(10) . ?
C6A N1A 1.475(10) . ?
C6A C7A 1.376(11) . ?
C5A H5A 0.9500 . ?
C5A C4 1.383(10) . ?
C14A H14A 0.9500 . ?
C14A C13 1.397(12) . ?
C14A C15A 1.382(11) . ?
C13 C12A 1.517(11) . ?
C13 C18A 1.383(11) . ?
C13 C12B 1.519(16) . ?
C13 C14B 1.387(16) . ?
C13 C18B 1.378(16) . ?
C4 C3A 1.507(9) . ?
C4 C9A 1.390(9) . ?
C4 C3B 1.508(19) . ?
C4 C5B 1.392(19) . ?
C4 C9B 1.397(19) . ?
C3A C2A 1.445(10) . ?
C1A C2A 1.220(10) . ?
C1A I1B 1.980(7) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.381(12) . ?
C11A C10A 1.213(12) . ?
C11A C12A 1.456(11) . ?
C15A C16A 1.411(13) . ?
C10A I2B 2.220(11) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.390(13) . ?
C8A H8A 0.9500 . ?
C18A H18A 0.9500 . ?
C18A C17A 1.402(14) . ?
C17A H17A 0.9500 . ?
C17A C16A 1.376(16) . ?
C16A H16A 0.9500 . ?
C10B C11B 1.220(17) . ?
C10B I2C 1.607(15) . ?
C10B I2D 2.06(4) . ?
C11B C12B 1.465(16) . ?
C12B O4B 1.203(15) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.398(16) . ?
C18B H18B 0.9500 . ?
C18B C17B 1.388(19) . ?
C17B H17B 0.9500 . ?
C17B C16B 1.39(2) . ?
C15B C16B 1.395(18) . ?
C15B N2B 1.480(16) . ?
C16B H16B 0.9500 . ?
N2B O5B 1.210(16) . ?
N2B O6B 1.254(16) . ?
I1C C1B 1.979(7) . ?
C1B C2B 1.210(19) . ?
C1B I1D 1.980(7) . ?
C2B C3B 1.45(2) . ?
C3B O1B 1.214(19) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.388(19) . ?
C9B H9B 0.9500 . ?
C9B C8B 1.38(2) . ?
C6B N1B 1.490(19) . ?
C6B C7B 1.38(2) . ?
C8B H8B 0.9500 . ?
C8B C7B 1.39(2) . ?
N1B O2B 1.26(2) . ?
N1B O3B 1.23(2) . ?
C7B H7B 0.9500 . ?

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
O5A N2A O6A 126.3(9) . . ?
O5A N2A C15A 118.2(8) . . ?
O6A N2A C15A 115.5(9) . . ?
C5A C6A N1A 117.7(7) . . ?
C7A C6A C5A 123.1(7) . . ?
C7A C6A N1A 119.2(7) . . ?
C6A C5A H5A 121.2 . . ?
C4 C5A C6A 117.6(8) . . ?
C4 C5A H5A 121.2 . . ?
O2A N1A C6A 118.6(7) . . ?
O3A N1A O2A 123.7(7) . . ?
O3A N1A C6A 117.8(7) . . ?
C13 C14A H14A 119.8 . . ?
C15A C14A H14A 119.8 . . ?
C15A C14A C13 120.5(9) . . ?
C14A C13 C12A 112.6(7) . . ?
C18A C13 C14A 117.6(8) . . ?
C18A C13 C12A 129.8(8) . . ?
C14B C13 C12B 123.1(12) . . ?
C18B C13 C12B 109.4(12) . . ?
C18B C13 C14B 127.4(14) . . ?
C5A C4 C9A 121.1(7) . . ?
C5A C4 C3B 122.2(11) . . ?
C9A C4 C3B 116.4(11) . . ?
C5B C4 C3A 109.9(13) . . ?
C5B C4 C9B 116.0(19) . . ?
C9B C4 C3A 134.1(14) . . ?
O1A C3A C4 122.0(7) . . ?
O1A C3A C2A 121.4(7) . . ?
C2A C3A C4 116.4(6) . . ?
C2A C1A I1A 176.3(7) . . ?
C4 C9A H9A 120.4 . . ?
C8A C9A C4 119.2(8) . . ?
C8A C9A H9A 120.4 . . ?
C1A C2A C3A 176.6(13) . . ?
C10A C11A C12A 172.2(16) . . ?
C14A C15A N2A 118.9(8) . . ?
C14A C15A C16A 122.1(9) . . ?
C16A C15A N2A 119.0(8) . . ?
I2A C10A I2B 16.9(2) . . ?
C11A C10A I2A 169.8(12) . . ?
C11A C10A I2B 153.3(12) . . ?
O4A C12A C13 122.9(9) . . ?
O4A C12A C11A 121.9(10) . . ?
C11A C12A C13 115.1(8) . . ?
C6A C7A H7A 121.2 . . ?
C6A C7A C8A 117.6(7) . . ?
C8A C7A H7A 121.2 . . ?
C9A C8A C7A 121.3(7) . . ?
C9A C8A H8A 119.4 . . ?
C7A C8A H8A 119.4 . . ?
C13 C18A H18A 119.1 . . ?
C13 C18A C17A 121.9(10) . . ?
C17A C18A H18A 119.1 . . ?
C18A C17A H17A 119.5 . . ?
C16A C17A C18A 121.0(9) . . ?
C16A C17A H17A 119.5 . . ?
C15A C16A H16A 121.5 . . ?
C17A C16A C15A 117.0(8) . . ?
C17A C16A H16A 121.5 . . ?
C11B C10B I2C 167(3) . . ?
C10B C11B C12B 154(3) . . ?
C11B C12B C13 115.8(14) . . ?
O4B C12B C13 122.5(17) . . ?
O4B C12B C11B 121.4(18) . . ?
C13 C14B H14B 123.2 . . ?
C13 C14B C15B 113.7(16) . . ?
C15B C14B H14B 123.2 . . ?
C13 C18B H18B 122.2 . . ?
C13 C18B C17B 115.7(16) . . ?
C17B C18B H18B 122.2 . . ?
C18B C17B H17B 119.6 . . ?
C16B C17B C18B 120.7(16) . . ?
C16B C17B H17B 119.6 . . ?
C14B C15B N2B 114.2(13) . . ?
C16B C15B C14B 121.9(15) . . ?
C16B C15B N2B 123.9(15) . . ?
C17B C16B C15B 120.1(15) . . ?
C17B C16B H16B 119.9 . . ?
C15B C16B H16B 119.9 . . ?
O5B N2B C15B 120.2(14) . . ?
O5B N2B O6B 127.3(16) . . ?
O6B N2B C15B 112.5(15) . . ?
C2B C1B I1C 162(3) . . ?
C1B C2B C3B 166(7) . . ?
C2B C3B C4 114(2) . . ?
O1B C3B C4 123(3) . . ?
O1B C3B C2B 119(3) . . ?
C4 C5B H5B 118.8 . . ?
C6B C5B C4 122(2) . . ?
C6B C5B H5B 118.8 . . ?
C4 C9B H9B 119.2 . . ?
C8B C9B C4 122(2) . . ?
C8B C9B H9B 119.2 . . ?
C5B C6B N1B 119.8(18) . . ?
C7B C6B C5B 120.8(18) . . ?
C7B C6B N1B 119.4(19) . . ?
C9B C8B H8B 119.1 . . ?
C9B C8B C7B 122(2) . . ?
C7B C8B H8B 119.1 . . ?
O2B N1B C6B 118.0(19) . . ?
O3B N1B C6B 118(2) . . ?
O3B N1B O2B 124(2) . . ?
C6B C7B C8B 117.2(19) . . ?
C6B C7B H7B 121.4 . . ?
C8B C7B H7B 121.4 . . ?


_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
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_75_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2110094'
loop_
_audit_author_name
_audit_author_address
'Christer B. Aakeroy'
;Kansas State University
United States of America
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-01-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
vinu@ksu.edu
aakeroy@ksu.edu
_chemical_name_common            ?
_chemical_name_systematic        4-(3-iodoprop-2-ynoyl)benzonitrile
_chemical_formula_moiety         'C10 H4 I N O'
_chemical_formula_sum            'C10 H4 I N O'
_chemical_formula_weight         281.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H4 I1 N1 O1'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   4.06532(16)
_cell_length_b                   24.0246(11)
_cell_length_c                   9.7176(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.002(4)
_cell_angle_gamma                90
_cell_volume                     943.89(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    100.02(19)
_cell_measurement_theta_max      76.3330
_cell_measurement_theta_min      3.6870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    26.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43858
_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_absorpt_special_details   ?
_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    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane'
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_unetI/netI     0.0045
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2731
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.120
_diffrn_reflns_theta_min         3.680
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  24.00   0.50    4.76    --   47.95 -11.00-118.00   58
  2  ω     42.00  71.00   0.50   19.03    --  107.75 -61.00-180.00   58
  3  ω     36.00  70.00   0.50   19.03    --  107.75 -61.00-150.00   68
  4  ω    115.00 178.00   0.50   19.03    --  107.75  15.00-120.00  126
  5  ω    103.00 154.00   0.50   19.03    --  107.75 120.00-133.00  102
  6  ω    101.00 161.00   0.50   19.03    --  107.75  11.00  54.00  120
  7  ω     80.00 105.00   0.50   19.03    --  107.75 -77.00 120.00   50
  8  ω     76.00 106.00   0.50   19.03    --  107.75 -94.00  90.00   60
  9  ω     77.00 113.00   0.50   19.03    --  107.75-127.00 174.20   72
 10  ω     44.00  69.00   0.50   19.03    --  107.75-127.00 174.20   50
 11  ω     42.00  68.00   0.50   19.03    --  107.75 -77.00 120.00   52
 12  ω     35.00  60.00   0.50   19.03    --  107.75 -61.00 150.00   50
 13  ω     -3.00  26.00   0.50    4.76    --   47.95 -19.00 150.00   58
 14  ω    -24.00  23.00   0.50    4.76    --  -47.95  19.00 150.00   94
 15  ω   -105.00 -67.00   0.50   19.03    --  -86.25-148.00-109.00   76
 16  ω   -145.00-120.00   0.50   19.03    --  -86.25-148.00-109.00   50
 17  ω    -17.00  23.00   0.50    4.76    --  -47.95  19.00-120.00   80
 18  ω     95.00 128.00   0.50   19.03    --  107.75-148.00-109.00   66
 19  ω     64.00 112.00   0.50   19.03    --  107.75-125.00-180.00   96
 20  ω     54.00  80.00   0.50   19.03    --  107.75-148.00-109.00   52
;
_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      -0.0425778000
_diffrn_orient_matrix_UB_12      -0.0634728000
_diffrn_orient_matrix_UB_13      0.0124730000
_diffrn_orient_matrix_UB_21      -0.0111442000
_diffrn_orient_matrix_UB_22      -0.0056295000
_diffrn_orient_matrix_UB_23      -0.1585904000
_diffrn_orient_matrix_UB_31      0.3787367000
_diffrn_orient_matrix_UB_32      -0.0072755000
_diffrn_orient_matrix_UB_33      0.0134881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2644
_reflns_number_total             2731
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.532
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.105
_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)+(0.0947P)²+0.7803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5492(18)
 0.4508(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.69037(9) 0.09265(2) 0.59099(3) 0.0422(2) Uani 1 1 d . . . . .
C10 C 0.5129(14) 0.1661(2) 0.5171(6) 0.0411(12) Uani 1 1 d . . . . .
O1 O 0.1064(13) 0.26971(19) 0.3238(5) 0.0564(12) Uani 1 1 d . . . . .
C6 C 0.4005(15) 0.3667(2) 0.4387(5) 0.0430(12) Uani 1 1 d . . . . .
H6 H 0.260063 0.370337 0.357296 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8056(14) 0.3552(2) 0.6874(5) 0.0390(11) Uani 1 1 d . . . . .
H3 H 0.938528 0.351377 0.770687 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5487(18) 0.4134(2) 0.5040(6) 0.0437(14) Uani 1 1 d . . . . .
H5 H 0.515463 0.448442 0.464076 0.052 Uiso 1 1 calc R U . . .
C2 C 0.6679(13) 0.3089(2) 0.6221(5) 0.0388(11) Uani 1 1 d . . . . .
H2 H 0.708829 0.273905 0.660847 0.047 Uiso 1 1 calc R U . . .
C4 C 0.7494(17) 0.4075(2) 0.6309(7) 0.0424(13) Uani 1 1 d . . . . .
C9 C 0.4178(15) 0.2103(2) 0.4762(6) 0.0415(12) Uani 1 1 d . . . . .
C7 C 0.8984(17) 0.4561(3) 0.6958(7) 0.0498(14) Uani 1 1 d . . . . .
N1 N 1.0226(15) 0.4941(2) 0.7490(6) 0.0599(14) Uani 1 1 d . . . . .
C1 C 0.4675(13) 0.3143(2) 0.4982(5) 0.0361(10) Uani 1 1 d . . . . .
C8 C 0.3102(14) 0.2648(3) 0.4240(6) 0.0429(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
I1 C10 2.011(6) . ?
C10 C9 1.182(8) . ?
O1 C8 1.216(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.394(8) . ?
C6 C1 1.402(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.371(8) . ?
C3 C4 1.380(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.413(9) . ?
C2 H2 0.9300 . ?
C2 C1 1.387(7) . ?
C4 C7 1.430(9) . ?
C9 C8 1.455(8) . ?
C7 N1 1.142(9) . ?
C1 C8 1.500(8) . ?

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
C9 C10 I1 177.7(5) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C1 118.7(5) . . ?
C1 C6 H6 120.7 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 C7 121.5(6) . . ?
C5 C4 C7 118.8(5) . . ?
C10 C9 C8 178.2(6) . . ?
N1 C7 C4 178.5(8) . . ?
C6 C1 C8 117.4(5) . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 C8 121.8(5) . . ?
O1 C8 C9 121.5(6) . . ?
O1 C8 C1 121.9(6) . . ?
C9 C8 C1 116.6(5) . . ?

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
C6 C5 C4 C3 2.0(11) . . . . ?
C6 C5 C4 C7 -180.0(6) . . . . ?
C6 C1 C8 O1 -7.2(8) . . . . ?
C6 C1 C8 C9 171.7(5) . . . . ?
C3 C2 C1 C6 -0.6(9) . . . . ?
C3 C2 C1 C8 -179.6(5) . . . . ?
C5 C6 C1 C2 2.2(9) . . . . ?
C5 C6 C1 C8 -178.7(5) . . . . ?
C2 C3 C4 C5 -0.3(10) . . . . ?
C2 C3 C4 C7 -178.3(6) . . . . ?
C2 C1 C8 O1 171.8(6) . . . . ?
C2 C1 C8 C9 -9.3(8) . . . . ?
C4 C3 C2 C1 -0.4(9) . . . . ?
C1 C6 C5 C4 -2.9(10) . . . . ?


_olex2_date_sample_data_collection 2021-01-17
_olex2_date_sample_submission    2021-01-15
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id VP-K1-4CN-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 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.651
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5492(18) 2306 1990 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4508(18) 2324 1990 nmt 1.0000 -0.0003 0.0001 -0.0045 -1.0001 -0.0061
-0.4948 0.0009 -0.9999

_twin_special_details            
;
Component 2 rotated by 179.8873° 
around [0.97 -0.00 -0.24] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
