# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2307260'
loop_
_audit_author_name
_audit_author_address
a
;Henan Normal University
China
;
_audit_update_record             
;
2023-11-11 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 I N O7'
_chemical_formula_sum            'C18 H20 I N O7'
_chemical_formula_weight         489.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.68310(10)
_cell_length_b                   6.78090(10)
_cell_length_c                   12.62400(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.7010(10)
_cell_angle_gamma                90
_cell_volume                     967.358(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18370
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.6440
_cell_measurement_theta_min      3.9040
_shelx_estimated_absorpt_T_max   0.197
_shelx_estimated_absorpt_T_min   0.135
_exptl_absorpt_coefficient_mu    13.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction,
2023) 
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    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25397
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.839
_diffrn_reflns_theta_min         3.620
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3727
_reflns_number_total             3749
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.953
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 1652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.045
_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)+(0.0554P)²+0.3860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P), C00R(H00T)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00K(H00D,H00G), C00M(H00L,H00M), C00O(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00I(H00I)
2.d Idealised Me refined as rotating group:
 C00L(H00H,H00J,H00K), C00Q(H00Q,H00R,H00S)
;
_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
I001 I 0.39152(2) 0.81725(6) 0.26418(2) 0.02285(12) Uani 1 1 d . . . . .
O002 O 0.7692(4) 0.9998(6) 0.3292(3) 0.0262(9) Uani 1 1 d . . . . .
O003 O 0.6382(3) 0.5102(5) 0.5173(3) 0.0198(7) Uani 1 1 d . . . . .
O004 O 0.6541(3) 0.5490(5) 0.2428(2) 0.0141(6) Uani 1 1 d . . . . .
O005 O 0.9947(3) 0.1242(6) 0.2641(3) 0.0225(7) Uani 1 1 d . . . . .
O006 O 1.0189(4) 0.3033(9) 0.4179(3) 0.0349(9) Uani 1 1 d . . . . .
N007 N 0.7200(4) 0.7182(6) 0.4126(3) 0.0117(8) Uani 1 1 d . . . . .
O008 O 0.8788(4) 0.5353(7) 0.0672(3) 0.0329(9) Uani 1 1 d . . . . .
C009 C 0.6685(4) 0.6754(7) 0.4975(4) 0.0138(10) Uani 1 1 d . . . . .
O00A O 1.0613(4) 0.5355(9) 0.1816(4) 0.0438(12) Uani 1 1 d . . . . .
C00B C 0.7364(5) 0.9225(8) 0.4019(4) 0.0175(11) Uani 1 1 d . . . . .
C00C C 0.4459(4) 0.3252(11) 0.0602(4) 0.0206(9) Uani 1 1 d . . . . .
H00C H 0.497746 0.215358 0.066511 0.025 Uiso 1 1 calc R . . . .
C00D C 0.3821(4) 0.6134(7) 0.1358(4) 0.0164(9) Uani 1 1 d . . . . .
C00E C 0.2940(5) 0.6434(8) 0.0399(4) 0.0230(11) Uani 1 1 d . . . . .
H00E H 0.242491 0.753551 0.033215 0.028 Uiso 1 1 calc R . . . .
C00F C 0.2822(5) 0.5116(9) -0.0456(4) 0.0261(12) Uani 1 1 d . . . . .
H00F H 0.221769 0.530650 -0.111032 0.031 Uiso 1 1 calc R . . . .
C00G C 0.8602(4) 0.6034(7) 0.3080(4) 0.0150(9) Uani 1 1 d . . . . .
H00A H 0.924314 0.629511 0.374668 0.018 Uiso 1 1 calc R . . . .
H00B H 0.850755 0.722128 0.260907 0.018 Uiso 1 1 calc R . . . .
C00H C 0.9571(5) 0.5021(7) 0.1624(4) 0.0215(10) Uani 1 1 d . . . . .
C00I C 0.3583(5) 0.3510(9) -0.0364(4) 0.0277(13) Uani 1 1 d . . . . .
H00I H 0.350443 0.260457 -0.095282 0.033 Uiso 1 1 calc R . . . .
C00J C 0.9758(4) 0.2819(7) 0.3211(4) 0.0199(11) Uani 1 1 d . . . . .
C00K C 0.7045(6) 1.0218(8) 0.4979(5) 0.0283(13) Uani 1 1 d . . . . .
H00D H 0.775422 1.081960 0.547311 0.034 Uiso 1 1 calc R . . . .
H00G H 0.644707 1.126235 0.472091 0.034 Uiso 1 1 calc R . . . .
C00L C 1.0753(5) -0.0217(9) 0.3259(5) 0.0320(13) Uani 1 1 d . . . . .
H00H H 1.076916 -0.137219 0.279717 0.048 Uiso 1 1 calc GR . . . .
H00J H 1.048487 -0.061268 0.390336 0.048 Uiso 1 1 calc GR . . . .
H00K H 1.154890 0.034893 0.349523 0.048 Uiso 1 1 calc GR . . . .
C00M C 0.6551(5) 0.8620(7) 0.5567(4) 0.0220(12) Uani 1 1 d . . . . .
H00L H 0.699872 0.854271 0.634514 0.026 Uiso 1 1 calc R . . . .
H00M H 0.570748 0.887420 0.553279 0.026 Uiso 1 1 calc R . . . .
C00N C 0.4602(4) 0.4545(7) 0.1478(4) 0.0150(9) Uani 1 1 d . . . . .
C00O C 0.5578(4) 0.4217(7) 0.2487(4) 0.0154(9) Uani 1 1 d . . . . .
H00N H 0.530135 0.452625 0.314764 0.019 Uiso 1 1 calc R . . . .
H00O H 0.583688 0.282262 0.253016 0.019 Uiso 1 1 calc R . . . .
C00P C 0.8942(4) 0.4255(8) 0.2460(4) 0.0155(9) Uani 1 1 d . . . . .
H00P H 0.820534 0.354619 0.206745 0.019 Uiso 1 1 calc R . . . .
C00Q C 0.9212(9) 0.6286(13) -0.0189(6) 0.057(2) Uani 1 1 d . . . . .
H00Q H 0.861610 0.614806 -0.088765 0.085 Uiso 1 1 calc GR . . . .
H00R H 0.994959 0.565142 -0.024137 0.085 Uiso 1 1 calc GR . . . .
H00S H 0.935825 0.768796 -0.001945 0.085 Uiso 1 1 calc GR . . . .
C00R C 0.7452(4) 0.5629(7) 0.3400(4) 0.0112(9) Uani 1 1 d . . . . .
H00T H 0.752275 0.433631 0.379309 0.013 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
I001 C00D 2.112(5) . ?
O002 C00B 1.201(7) . ?
O003 C009 1.219(6) . ?
O004 C00O 1.435(6) . ?
O004 C00R 1.409(5) . ?
O005 C00J 1.338(6) . ?
O005 C00L 1.449(7) . ?
O006 C00J 1.206(6) . ?
N007 C009 1.386(6) . ?
N007 C00B 1.410(5) . ?
N007 C00R 1.474(6) . ?
O008 C00H 1.331(7) . ?
O008 C00Q 1.450(8) . ?
C009 C00M 1.499(6) . ?
O00A C00H 1.202(7) . ?
C00B C00K 1.514(7) . ?
C00C H00C 0.9500 . ?
C00C C00I 1.391(7) . ?
C00C C00N 1.388(7) . ?
C00D C00E 1.390(7) . ?
C00D C00N 1.396(7) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.380(7) . ?
C00F H00F 0.9500 . ?
C00F C00I 1.392(8) . ?
C00G H00A 0.9900 . ?
C00G H00B 0.9900 . ?
C00G C00P 1.544(7) . ?
C00G C00R 1.523(6) . ?
C00H C00P 1.522(7) . ?
C00I H00I 0.9500 . ?
C00J C00P 1.516(7) . ?
C00K H00D 0.9900 . ?
C00K H00G 0.9900 . ?
C00K C00M 1.508(7) . ?
C00L H00H 0.9800 . ?
C00L H00J 0.9800 . ?
C00L H00K 0.9800 . ?
C00M H00L 0.9900 . ?
C00M H00M 0.9900 . ?
C00N C00O 1.495(6) . ?
C00O H00N 0.9900 . ?
C00O H00O 0.9900 . ?
C00P H00P 1.0000 . ?
C00Q H00Q 0.9800 . ?
C00Q H00R 0.9800 . ?
C00Q H00S 0.9800 . ?
C00R H00T 1.0000 . ?

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
C00R O004 C00O 115.1(3) . . ?
C00J O005 C00L 115.4(4) . . ?
C009 N007 C00B 112.1(4) . . ?
C009 N007 C00R 121.7(4) . . ?
C00B N007 C00R 126.1(5) . . ?
C00H O008 C00Q 117.6(6) . . ?
O003 C009 N007 123.8(4) . . ?
O003 C009 C00M 126.9(4) . . ?
N007 C009 C00M 109.2(4) . . ?
O002 C00B N007 125.4(5) . . ?
O002 C00B C00K 127.6(5) . . ?
N007 C00B C00K 107.0(5) . . ?
C00I C00C H00C 118.9 . . ?
C00N C00C H00C 118.9 . . ?
C00N C00C C00I 122.2(6) . . ?
C00E C00D I001 117.1(4) . . ?
C00E C00D C00N 121.8(4) . . ?
C00N C00D I001 121.1(3) . . ?
C00D C00E H00E 120.3 . . ?
C00F C00E C00D 119.4(5) . . ?
C00F C00E H00E 120.3 . . ?
C00E C00F H00F 119.8 . . ?
C00E C00F C00I 120.4(5) . . ?
C00I C00F H00F 119.8 . . ?
H00A C00G H00B 108.1 . . ?
C00P C00G H00A 109.5 . . ?
C00P C00G H00B 109.5 . . ?
C00R C00G H00A 109.5 . . ?
C00R C00G H00B 109.5 . . ?
C00R C00G C00P 110.5(4) . . ?
O008 C00H C00P 110.0(4) . . ?
O00A C00H O008 125.4(5) . . ?
O00A C00H C00P 124.5(5) . . ?
C00C C00I C00F 118.9(5) . . ?
C00C C00I H00I 120.5 . . ?
C00F C00I H00I 120.5 . . ?
O005 C00J C00P 109.9(4) . . ?
O006 C00J O005 123.8(5) . . ?
O006 C00J C00P 126.2(5) . . ?
C00B C00K H00D 110.5 . . ?
C00B C00K H00G 110.5 . . ?
H00D C00K H00G 108.7 . . ?
C00M C00K C00B 106.1(4) . . ?
C00M C00K H00D 110.5 . . ?
C00M C00K H00G 110.5 . . ?
O005 C00L H00H 109.5 . . ?
O005 C00L H00J 109.5 . . ?
O005 C00L H00K 109.5 . . ?
H00H C00L H00J 109.5 . . ?
H00H C00L H00K 109.5 . . ?
H00J C00L H00K 109.5 . . ?
C009 C00M C00K 105.0(4) . . ?
C009 C00M H00L 110.7 . . ?
C009 C00M H00M 110.7 . . ?
C00K C00M H00L 110.7 . . ?
C00K C00M H00M 110.7 . . ?
H00L C00M H00M 108.8 . . ?
C00C C00N C00D 117.3(4) . . ?
C00C C00N C00O 119.8(5) . . ?
C00D C00N C00O 122.9(4) . . ?
O004 C00O C00N 107.7(4) . . ?
O004 C00O H00N 110.2 . . ?
O004 C00O H00O 110.2 . . ?
C00N C00O H00N 110.2 . . ?
C00N C00O H00O 110.2 . . ?
H00N C00O H00O 108.5 . . ?
C00G C00P H00P 109.1 . . ?
C00H C00P C00G 108.4(4) . . ?
C00H C00P H00P 109.1 . . ?
C00J C00P C00G 112.7(4) . . ?
C00J C00P C00H 108.4(4) . . ?
C00J C00P H00P 109.1 . . ?
O008 C00Q H00Q 109.5 . . ?
O008 C00Q H00R 109.5 . . ?
O008 C00Q H00S 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
H00Q C00Q H00S 109.5 . . ?
H00R C00Q H00S 109.5 . . ?
O004 C00R N007 111.3(4) . . ?
O004 C00R C00G 107.6(4) . . ?
O004 C00R H00T 108.8 . . ?
N007 C00R C00G 111.4(4) . . ?
N007 C00R H00T 108.8 . . ?
C00G C00R H00T 108.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
