# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_xb2586_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2052806'
loop_
_audit_author_name
_audit_author_address
'zhaoyang wang'
;Northwest University
China
;
_audit_update_record             
;
2020-12-29 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_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         'C11 H10 I N O2'
_chemical_formula_sum            'C11 H10 I N O2'
_chemical_formula_weight         315.10
_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 0.0033 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.149(4)
_cell_length_b                   7.316(3)
_cell_length_c                   15.907(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.238(7)
_cell_angle_gamma                90
_cell_volume                     1139.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.92
_cell_measurement_theta_min      3.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.790
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1618
_diffrn_reflns_av_unetI/netI     0.1537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4743
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.893
_diffrn_reflns_theta_max         24.893
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                910
_reflns_number_total             1982
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.431
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      0.886
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.2047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C4(H4), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00P(H00C,H00D,H00E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 -0.13634(8) 0.62122(15) -0.18731(7) 0.0975(6) Uani 1 1 d . . . . .
O004 O 0.5446(7) 0.6543(8) 0.1389(5) 0.0555(18) Uani 1 1 d . . . . .
O007 O 0.3782(7) 0.4873(9) 0.0510(5) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.3232(10) 1.1066(11) 0.0344(6) 0.061(2) Uani 1 1 d . . . . .
H2 H 0.336123 1.222363 0.041448 0.073 Uiso 1 1 d R . . . .
C1 C 0.2099(10) 1.0296(13) -0.0222(7) 0.045(2) Uani 1 1 d . . . . .
C00D C 0.3623(10) 0.8113(13) 0.0482(7) 0.047(3) Uani 1 1 d . . . . .
C2 C 0.0189(11) 0.7923(15) -0.1132(7) 0.056(3) Uani 1 1 d . . . . .
C00I C 0.2318(11) 0.8344(13) -0.0140(8) 0.055(3) Uani 1 1 d . . . . .
C00J C -0.0020(14) 0.991(2) -0.1197(9) 0.081(4) Uani 1 1 d . . . . .
H00J H -0.083441 1.037303 -0.154495 0.098 Uiso 1 1 calc R . . . .
C4 C 0.4125(11) 0.9827(13) 0.0756(7) 0.052(3) Uani 1 1 d . . . . .
H4 H 0.494967 1.007252 0.116122 0.063 Uiso 1 1 calc R . . . .
C00O C 0.6152(11) 0.4830(13) 0.1710(7) 0.058(3) Uani 1 1 d . . . . .
H00A H 0.632380 0.413217 0.123082 0.070 Uiso 1 1 calc R . . . .
H00B H 0.560200 0.409376 0.199486 0.070 Uiso 1 1 calc R . . . .
C00P C 0.7494(11) 0.5359(15) 0.2354(8) 0.063(3) Uani 1 1 d . . . . .
H00C H 0.730902 0.606906 0.281787 0.095 Uiso 1 1 calc GR . . . .
H00D H 0.803418 0.606800 0.206084 0.095 Uiso 1 1 calc GR . . . .
H00E H 0.798517 0.427363 0.259047 0.095 Uiso 1 1 calc GR . . . .
C00Q C 0.4257(10) 0.6350(13) 0.0792(7) 0.043(2) Uani 1 1 d . . . . .
C00R C 0.0937(13) 1.1042(17) -0.0768(8) 0.064(3) Uani 1 1 d . . . . .
H00R H 0.083059 1.230128 -0.083159 0.077 Uiso 1 1 calc R . . . .
C00S C 0.1307(10) 0.7208(15) -0.0608(7) 0.054(3) Uani 1 1 d . . . . .
H00S H 0.140764 0.594650 -0.055706 0.065 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 C2 2.112(10) . ?
O004 C00O 1.467(11) . ?
O004 C00Q 1.332(12) . ?
O007 C00Q 1.220(11) . ?
N2 H2 0.8600 . ?
N2 C1 1.380(13) . ?
N2 C4 1.327(12) . ?
C1 C00I 1.446(13) . ?
C1 C00R 1.380(15) . ?
C00D C00I 1.439(15) . ?
C00D C4 1.380(13) . ?
C00D C00Q 1.468(12) . ?
C2 C00J 1.467(17) . ?
C2 C00S 1.326(14) . ?
C00I C00S 1.377(14) . ?
C00J H00J 0.9300 . ?
C00J C00R 1.323(17) . ?
C4 H4 0.9300 . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00O C00P 1.524(14) . ?
C00P H00C 0.9600 . ?
C00P H00D 0.9600 . ?
C00P H00E 0.9600 . ?
C00R H00R 0.9300 . ?
C00S H00S 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
C00Q O004 C00O 115.2(8) . . ?
C1 N2 H2 124.0 . . ?
C4 N2 H2 123.2 . . ?
C4 N2 C1 112.8(8) . . ?
N2 C1 C00I 105.2(9) . . ?
N2 C1 C00R 132.6(10) . . ?
C00R C1 C00I 122.2(11) . . ?
C00I C00D C00Q 125.2(9) . . ?
C4 C00D C00I 107.9(9) . . ?
C4 C00D C00Q 126.8(9) . . ?
C00J C2 I001 118.3(9) . . ?
C00S C2 I001 120.5(8) . . ?
C00S C2 C00J 121.2(11) . . ?
C00D C00I C1 105.6(9) . . ?
C00S C00I C1 118.2(10) . . ?
C00S C00I C00D 136.2(9) . . ?
C2 C00J H00J 119.6 . . ?
C00R C00J C2 120.8(12) . . ?
C00R C00J H00J 119.6 . . ?
N2 C4 C00D 108.5(9) . . ?
N2 C4 H4 125.8 . . ?
C00D C4 H4 125.8 . . ?
O004 C00O H00A 110.4 . . ?
O004 C00O H00B 110.4 . . ?
O004 C00O C00P 106.6(8) . . ?
H00A C00O H00B 108.6 . . ?
C00P C00O H00A 110.4 . . ?
C00P C00O H00B 110.4 . . ?
C00O C00P H00C 109.5 . . ?
C00O C00P H00D 109.5 . . ?
C00O C00P H00E 109.5 . . ?
H00C C00P H00D 109.5 . . ?
H00C C00P H00E 109.5 . . ?
H00D C00P H00E 109.5 . . ?
O004 C00Q C00D 112.4(9) . . ?
O007 C00Q O004 123.6(9) . . ?
O007 C00Q C00D 123.9(9) . . ?
C1 C00R H00R 121.1 . . ?
C00J C00R C1 117.8(11) . . ?
C00J C00R H00R 121.1 . . ?
C2 C00S C00I 119.7(10) . . ?
C2 C00S H00S 120.2 . . ?
C00I C00S H00S 120.2 . . ?

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
I001 C2 C00J C00R -177.9(9) . . . . ?
I001 C2 C00S C00I 179.0(7) . . . . ?
N2 C1 C00I C00D -1.0(11) . . . . ?
N2 C1 C00I C00S 177.1(9) . . . . ?
N2 C1 C00R C00J -175.8(11) . . . . ?
C1 N2 C4 C00D -0.2(12) . . . . ?
C1 C00I C00S C2 1.6(15) . . . . ?
C00D C00I C00S C2 178.9(11) . . . . ?
C2 C00J C00R C1 -3.5(17) . . . . ?
C00I C1 C00R C00J 2.7(16) . . . . ?
C00I C00D C4 N2 -0.5(12) . . . . ?
C00I C00D C00Q O004 -177.9(9) . . . . ?
C00I C00D C00Q O007 5.1(16) . . . . ?
C00J C2 C00S C00I -2.5(16) . . . . ?
C4 N2 C1 C00I 0.7(12) . . . . ?
C4 N2 C1 C00R 179.5(11) . . . . ?
C4 C00D C00I C1 0.9(11) . . . . ?
C4 C00D C00I C00S -176.7(12) . . . . ?
C4 C00D C00Q O004 -1.1(14) . . . . ?
C4 C00D C00Q O007 -178.1(10) . . . . ?
C00O O004 C00Q O007 -1.5(14) . . . . ?
C00O O004 C00Q C00D -178.5(8) . . . . ?
C00Q O004 C00O C00P 178.1(9) . . . . ?
C00Q C00D C00I C1 178.2(9) . . . . ?
C00Q C00D C00I C00S 0.7(19) . . . . ?
C00Q C00D C4 N2 -177.7(10) . . . . ?
C00R C1 C00I C00D -179.8(9) . . . . ?
C00R C1 C00I C00S -1.8(15) . . . . ?
C00S C2 C00J C00R 3.5(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_h2020102001_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2052807'
loop_
_audit_author_name
_audit_author_address
wangzhaoyang
;Northwest University
China
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-10-25
_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         'C10 H8 I N O2'
_chemical_formula_sum            'C10 H8 I N O2'
_chemical_formula_weight         301.07
_chemical_absolute_configuration ?
_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 0.0033 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      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                   4.3378(3)
_cell_length_b                   10.2121(7)
_cell_length_c                   22.8286(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1011.26(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.617
_shelx_estimated_absorpt_T_min   0.559
_exptl_absorpt_coefficient_mu    3.138
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.5294.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11486
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      180.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1831
_reflns_number_total             1839
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 
;
 Flack x determined using 713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0178
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+0.7744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0435
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C009(H009), C00A(H00A), C00C(H00E), C00E(H00F)
2.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.38987(6) 0.01415(2) 0.65389(2) 0.02704(10) Uani 1 1 d . . . . .
O002 O 0.7538(7) 0.5799(3) 0.57130(13) 0.0288(7) Uani 1 1 d . . . . .
N003 N 0.2032(8) 0.3239(3) 0.69859(13) 0.0220(7) Uani 1 1 d . . . . .
H003 H 0.118375 0.258325 0.717706 0.026 Uiso 1 1 calc R . . . .
C004 C 0.4881(9) 0.4389(4) 0.63443(16) 0.0207(8) Uani 1 1 d . . . . .
O005 O 0.1818(9) 0.7382(3) 0.70638(14) 0.0414(9) Uani 1 1 d . . . . .
C006 C 0.4076(9) 0.3111(4) 0.65244(16) 0.0205(7) Uani 1 1 d . . . . .
C007 C 0.6899(9) 0.4534(4) 0.58695(16) 0.0227(8) Uani 1 1 d . . . . .
C008 C 0.3221(9) 0.5284(4) 0.67224(16) 0.0230(8) Uani 1 1 d . . . . .
C009 C 0.8049(10) 0.3427(4) 0.55964(17) 0.0254(9) Uani 1 1 d . . . . .
H009 H 0.941290 0.352012 0.527346 0.030 Uiso 1 1 calc R . . . .
C00A C 0.1533(9) 0.4508(4) 0.70989(16) 0.0246(8) Uani 1 1 d . . . . .
H00A H 0.020235 0.482953 0.739661 0.030 Uiso 1 1 calc R . . . .
C00B C 0.9585(12) 0.5988(5) 0.5235(2) 0.0396(12) Uani 1 1 d . . . . .
H00B H 0.865251 0.563665 0.487666 0.059 Uiso 1 1 calc GR . . . .
H00C H 1.152934 0.553177 0.531302 0.059 Uiso 1 1 calc GR . . . .
H00D H 0.998553 0.692574 0.518445 0.059 Uiso 1 1 calc GR . . . .
C00C C 0.3275(12) 0.6688(4) 0.67293(18) 0.0308(10) Uani 1 1 d . . . . .
H00E H 0.455313 0.711204 0.644972 0.037 Uiso 1 1 calc R . . . .
C00D C 0.5230(9) 0.2002(4) 0.62536(17) 0.0214(8) Uani 1 1 d . . . . .
C00E C 0.7236(9) 0.2175(4) 0.57882(17) 0.0237(9) Uani 1 1 d . . . . .
H00F H 0.807257 0.143021 0.559628 0.028 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 2.090(4) . ?
O002 C007 1.369(5) . ?
O002 C00B 1.421(5) . ?
N003 H003 0.8800 . ?
N003 C006 1.383(5) . ?
N003 C00A 1.339(5) . ?
C004 C006 1.412(6) . ?
C004 C007 1.401(5) . ?
C004 C008 1.449(6) . ?
O005 C00C 1.219(5) . ?
C006 C00D 1.384(6) . ?
C007 C009 1.384(6) . ?
C008 C00A 1.379(6) . ?
C008 C00C 1.434(6) . ?
C009 H009 0.9500 . ?
C009 C00E 1.397(6) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9800 . ?
C00B H00C 0.9800 . ?
C00B H00D 0.9800 . ?
C00C H00E 0.9500 . ?
C00D C00E 1.384(6) . ?
C00E H00F 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
C007 O002 C00B 117.1(3) . . ?
C006 N003 H003 125.0 . . ?
C00A N003 H003 125.0 . . ?
C00A N003 C006 110.0(3) . . ?
C006 C004 C008 106.7(4) . . ?
C007 C004 C006 118.5(4) . . ?
C007 C004 C008 134.8(4) . . ?
N003 C006 C004 107.0(3) . . ?
N003 C006 C00D 130.5(4) . . ?
C00D C006 C004 122.5(4) . . ?
O002 C007 C004 115.3(4) . . ?
O002 C007 C009 125.5(3) . . ?
C009 C007 C004 119.2(4) . . ?
C00A C008 C004 105.8(4) . . ?
C00A C008 C00C 125.2(4) . . ?
C00C C008 C004 129.0(4) . . ?
C007 C009 H009 119.5 . . ?
C007 C009 C00E 121.0(4) . . ?
C00E C009 H009 119.5 . . ?
N003 C00A C008 110.5(4) . . ?
N003 C00A H00A 124.8 . . ?
C008 C00A H00A 124.8 . . ?
O002 C00B H00B 109.5 . . ?
O002 C00B H00C 109.5 . . ?
O002 C00B H00D 109.5 . . ?
H00B C00B H00C 109.5 . . ?
H00B C00B H00D 109.5 . . ?
H00C C00B H00D 109.5 . . ?
O005 C00C C008 125.5(4) . . ?
O005 C00C H00E 117.3 . . ?
C008 C00C H00E 117.3 . . ?
C006 C00D I001 120.3(3) . . ?
C006 C00D C00E 117.8(4) . . ?
C00E C00D I001 121.9(3) . . ?
C009 C00E H00F 119.5 . . ?
C00D C00E C009 121.1(4) . . ?
C00D C00E H00F 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
