# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_zd-2-227_auto
_database_code_depnum_ccdc_archive 'CCDC 2160104'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University 
United States of America
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 Cl I O2'
_chemical_formula_sum            'C13 H14 Cl I O2'
_chemical_formula_weight         364.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H14ClIO2
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'
Cl Cl 0.1484 0.1585 '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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9639(3)
_cell_length_b                   11.1228(3)
_cell_length_c                   13.2590(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1321.97(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6156
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.9060
_cell_measurement_theta_min      3.0720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 8 -1 0.0513
-11 -8 1 0.0453
-2 -3 -18 0.0803
10 -9 3 0.0532
-10 6 -8 0.0622
-1 5 18 0.0858
-8 10 8 0.0802
2 12 11 0.0750

_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.097
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
11.0259 7.6064 -1.0567 0.8733 0.4751 0.1078
-11.0259 -7.6064 1.0567 -0.8733 -0.4751 -0.1078
-2.1351 -3.0639 -18.0598 0.0539 -0.6647 0.7451
10.0705 -9.1617 2.9507 -0.0665 0.8468 0.5277
-10.4141 5.9849 -7.8483 -0.0251 -0.9720 -0.2337
-0.8288 4.9208 17.7112 -0.0846 0.4474 -0.8903
-8.3819 9.7193 7.8764 -0.0116 -0.4019 -0.9156
2.0000 12.0000 11.0000 0.5004 0.2670 -0.7978

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.620
_diffrn_reflns_theta_min         2.390
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00   8.00   1.00   12.00    --  -19.12 -77.00 -30.00   50
  2  ω    -48.00  36.00   1.00   12.00    --   19.27 -57.00 -60.00   84
  3  ω    -50.00  89.00   1.00   12.00    --   19.27   0.00 -90.00  139
  4  ω    -42.00   8.00   1.00   12.00    --  -19.12 -77.00-120.00   50
  5  ω      3.00  56.00   1.00   12.00    --   19.27  57.00  90.00   53
  6  ω     39.00  91.00   1.00   12.00    --   19.27 178.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0433870000
_diffrn_orient_matrix_UB_12      0.0496201000
_diffrn_orient_matrix_UB_13      -0.0165327000
_diffrn_orient_matrix_UB_21      0.0584108000
_diffrn_orient_matrix_UB_22      -0.0176347000
_diffrn_orient_matrix_UB_23      0.0328924000
_diffrn_orient_matrix_UB_31      0.0309474000
_diffrn_orient_matrix_UB_32      -0.0360736000
_diffrn_orient_matrix_UB_33      -0.0387988000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                3467
_reflns_number_total             3681
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 1306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.043
_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)+(0.0227P)²+0.5157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0623
_refine_special_details          'Refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
;
_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 0.23722(3) 0.73198(2) 0.61825(2) 0.01886(8) Uani 1 1 d . . . . .
Cl1 Cl 0.76129(14) 0.46441(9) 0.11422(8) 0.0249(2) Uani 1 1 d . . . . .
O1 O 0.2899(4) 0.4654(3) 0.5098(2) 0.0162(7) Uani 1 1 d . . . . .
O2 O 0.2503(4) 0.2834(2) 0.5628(2) 0.0251(7) Uani 1 1 d . . . . .
C1 C 0.2968(5) 0.5619(4) 0.4346(3) 0.0144(9) Uani 1 1 d . . . . .
C2 C 0.3665(6) 0.6654(4) 0.4932(3) 0.0175(10) Uani 1 1 d . . . . .
H2A H 0.384429 0.732667 0.445836 0.021 Uiso 1 1 calc R . . . .
H2B H 0.464729 0.638792 0.518937 0.021 Uiso 1 1 calc R . . . .
C3 C 0.1401(5) 0.5932(4) 0.3958(4) 0.0185(10) Uani 1 1 d . . . . .
H3A H 0.072817 0.598034 0.454887 0.022 Uiso 1 1 calc R . . . .
H3B H 0.144626 0.674542 0.365681 0.022 Uiso 1 1 calc R . . . .
C4 C 0.0692(6) 0.5106(4) 0.3199(4) 0.0215(11) Uani 1 1 d . . . . .
H4A H 0.135544 0.504294 0.260401 0.026 Uiso 1 1 calc R . . . .
H4B H -0.026090 0.546427 0.297114 0.026 Uiso 1 1 calc R . . . .
C5 C 0.0387(6) 0.3842(4) 0.3604(4) 0.0248(11) Uani 1 1 d . . . . .
H5A H -0.029615 0.390326 0.418874 0.030 Uiso 1 1 calc R . . . .
H5B H -0.012615 0.336894 0.307524 0.030 Uiso 1 1 calc R . . . .
C6 C 0.1794(5) 0.3171(4) 0.3929(4) 0.0219(10) Uani 1 1 d . . . . .
H6A H 0.156920 0.229940 0.394057 0.026 Uiso 1 1 calc R . . . .
H6B H 0.257357 0.330288 0.341198 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2414(6) 0.3516(3) 0.4929(3) 0.0187(9) Uani 1 1 d . . . . .
C8 C 0.4116(5) 0.5327(4) 0.3529(3) 0.0117(9) Uani 1 1 d . . . . .
C9 C 0.4108(6) 0.5954(4) 0.2623(3) 0.0173(10) Uani 1 1 d . . . . .
H9 H 0.334204 0.652534 0.249909 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5192(6) 0.5766(4) 0.1895(4) 0.0183(10) Uani 1 1 d . . . . .
H10 H 0.518101 0.620926 0.128240 0.022 Uiso 1 1 calc R . . . .
C11 C 0.6285(5) 0.4925(4) 0.2075(3) 0.0156(10) Uani 1 1 d . . . . .
C12 C 0.6343(5) 0.4293(4) 0.2975(4) 0.0166(10) Uani 1 1 d . . . . .
H12 H 0.711694 0.372675 0.309413 0.020 Uiso 1 1 calc R . . . .
C13 C 0.5261(5) 0.4498(4) 0.3696(4) 0.0165(9) Uani 1 1 d . . . . .
H13 H 0.529543 0.406926 0.431527 0.020 Uiso 1 1 calc R . . . .


_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 C2 2.155(5) . ?
Cl1 C11 1.745(5) . ?
O1 C1 1.467(5) . ?
O1 C7 1.357(5) . ?
O2 C7 1.201(5) . ?
C1 C2 1.522(6) . ?
C1 C3 1.536(6) . ?
C1 C8 1.528(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.504(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.488(6) . ?
C8 C9 1.390(6) . ?
C8 C13 1.397(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(6) . ?
C11 C12 1.385(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 H13 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
C7 O1 C1 125.7(3) . . ?
O1 C1 C2 102.9(3) . . ?
O1 C1 C3 110.8(4) . . ?
O1 C1 C8 110.8(3) . . ?
C2 C1 C3 112.0(4) . . ?
C2 C1 C8 104.3(4) . . ?
C8 C1 C3 115.3(4) . . ?
I1 C2 H2A 108.4 . . ?
I1 C2 H2B 108.4 . . ?
C1 C2 I1 115.6(3) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C1 C3 H3A 107.8 . . ?
C1 C3 H3B 107.8 . . ?
H3A C3 H3B 107.1 . . ?
C4 C3 C1 118.2(4) . . ?
C4 C3 H3A 107.8 . . ?
C4 C3 H3B 107.8 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.7(4) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.6(4) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 C5 115.7(4) . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
O1 C7 C6 120.5(3) . . ?
O2 C7 O1 116.1(4) . . ?
O2 C7 C6 123.4(4) . . ?
C9 C8 C1 120.2(4) . . ?
C9 C8 C13 118.1(4) . . ?
C13 C8 C1 121.5(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.7(4) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 Cl1 118.9(4) . . ?
C10 C11 C12 121.5(4) . . ?
C12 C11 Cl1 119.6(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.1(4) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.0(4) . . ?
C12 C13 H13 119.5 . . ?

_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.478
