# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_bh379
_database_code_depnum_ccdc_archive 'CCDC 1973001'
loop_
_audit_author_name
_audit_author_address
'Jeremy Forte'
;Institut Parisien de Chimie Moleculaire, Plateforme Diffraction X, Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 I N O3'
_chemical_formula_sum            'C14 H18 I N O3'
_chemical_formula_weight         375.19
_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                   5.75860(10)
_cell_length_b                   9.11070(10)
_cell_length_c                   14.1698(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8360(10)
_cell_angle_gamma                90
_cell_volume                     740.770(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    200
_cell_measurement_theta_max      66.03
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   0.428
_shelx_estimated_absorpt_T_min   0.117
_exptl_absorpt_coefficient_mu    17.024
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1157 before and 0.0762 after correction.
The Ratio of minimum to maximum transmission is 0.5461.
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    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16820
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.406
_diffrn_reflns_theta_max         66.406
_diffrn_reflns_theta_min         3.130
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   micro-focus
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2507
_reflns_number_total             2572
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         0.293
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1102 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(3)
_refine_ls_extinction_coef       0.00122(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0165
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0066P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0372
_refine_ls_wR_factor_ref         0.0373
_refine_special_details          ?

_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
I1 I 0.49486(4) 0.08566(5) 0.99059(2) 0.03901(11) Uani 1 1 d . . . . .
O1 O 0.2134(5) 0.1734(3) 0.61997(19) 0.0340(7) Uani 1 1 d . . . . .
H1 H 0.159(8) 0.169(5) 0.570(3) 0.029(11) Uiso 1 1 d . . . . .
O2 O 0.9523(5) 0.6426(3) 0.57214(15) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.8812(5) 0.6524(3) 0.72713(15) 0.0265(5) Uani 1 1 d . . . . .
N1 N 0.7820(6) 0.4515(3) 0.64179(18) 0.0234(6) Uani 1 1 d . . . . .
C1 C 0.5940(7) 0.2131(4) 0.8759(2) 0.0267(8) Uani 1 1 d . . . . .
C2 C 0.8002(7) 0.2902(4) 0.8842(2) 0.0278(8) Uani 1 1 d . . . . .
H2 H 0.897812 0.287699 0.941683 0.033 Uiso 1 1 calc R . . . .
C3 C 0.8642(7) 0.3717(4) 0.8075(3) 0.0260(8) Uani 1 1 d . . . . .
H3 H 1.006419 0.425131 0.812418 0.031 Uiso 1 1 calc R . . . .
C4 C 0.7202(7) 0.3751(3) 0.7240(2) 0.0205(7) Uani 1 1 d . . . . .
C5 C 0.5141(6) 0.2940(4) 0.7159(2) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.4495(7) 0.2130(4) 0.7929(2) 0.0250(7) Uani 1 1 d . . . . .
H6 H 0.308344 0.158557 0.788445 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3827(7) 0.2856(4) 0.6193(2) 0.0246(7) Uani 1 1 d . . . . .
H7 H 0.304189 0.381626 0.603985 0.029 Uiso 1 1 calc R . . . .
C8 C 0.5656(7) 0.2566(4) 0.5496(2) 0.0264(8) Uani 1 1 d . . . . .
H8A H 0.656589 0.167910 0.569296 0.032 Uiso 1 1 calc R . . . .
H8B H 0.487748 0.238666 0.485645 0.032 Uiso 1 1 calc R . . . .
C9 C 0.7278(7) 0.3875(4) 0.5467(2) 0.0240(8) Uani 1 1 d . . . . .
H9A H 0.874324 0.356323 0.520744 0.029 Uiso 1 1 calc R . . . .
H9B H 0.653904 0.463162 0.503900 0.029 Uiso 1 1 calc R . . . .
C10 C 0.8807(5) 0.5897(6) 0.64290(17) 0.0215(6) Uani 1 1 d . . . . .
C11 C 0.9899(7) 0.7995(4) 0.7447(2) 0.0262(8) Uani 1 1 d . . . . .
C12 C 0.9482(9) 0.8239(5) 0.8477(3) 0.0400(11) Uani 1 1 d . . . . .
H12A H 1.012935 0.919184 0.868503 0.060 Uiso 1 1 calc R . . . .
H12B H 0.780371 0.822662 0.854661 0.060 Uiso 1 1 calc R . . . .
H12C H 1.024404 0.745810 0.886431 0.060 Uiso 1 1 calc R . . . .
C13 C 1.2466(7) 0.7908(5) 0.7309(3) 0.0376(9) Uani 1 1 d . . . . .
H13A H 1.318125 0.887414 0.742429 0.056 Uiso 1 1 calc R . . . .
H13B H 1.321349 0.719384 0.775427 0.056 Uiso 1 1 calc R . . . .
H13C H 1.267031 0.759800 0.665880 0.056 Uiso 1 1 calc R . . . .
C14 C 0.8631(8) 0.9144(4) 0.6826(3) 0.0336(9) Uani 1 1 d . . . . .
H14A H 0.936419 1.010316 0.694965 0.050 Uiso 1 1 calc R . . . .
H14B H 0.871110 0.888337 0.615884 0.050 Uiso 1 1 calc R . . . .
H14C H 0.699625 0.918836 0.696891 0.050 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 C1 2.115(3) . ?
O1 C7 1.413(4) . ?
O2 C10 1.215(4) . ?
O3 C10 1.323(4) . ?
O3 C11 1.491(4) . ?
N1 C4 1.427(4) . ?
N1 C9 1.477(4) . ?
N1 C10 1.382(6) . ?
C1 C2 1.376(6) . ?
C1 C6 1.382(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.388(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.394(5) . ?
C5 C7 1.509(4) . ?
C7 C8 1.527(5) . ?
C8 C9 1.518(5) . ?
C11 C12 1.515(5) . ?
C11 C13 1.510(6) . ?
C11 C14 1.515(5) . ?

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
C10 O3 C11 120.5(3) . . ?
C4 N1 C9 120.3(3) . . ?
C10 N1 C4 124.5(2) . . ?
C10 N1 C9 115.2(2) . . ?
C2 C1 I1 120.1(2) . . ?
C2 C1 C6 121.8(3) . . ?
C6 C1 I1 118.1(3) . . ?
C1 C2 C3 119.3(3) . . ?
C4 C3 C2 120.0(4) . . ?
C3 C4 N1 122.4(3) . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 N1 117.4(3) . . ?
C4 C5 C7 117.4(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C7 122.5(3) . . ?
C1 C6 C5 119.0(3) . . ?
O1 C7 C5 108.9(3) . . ?
O1 C7 C8 113.1(3) . . ?
C5 C7 C8 105.9(3) . . ?
C9 C8 C7 109.9(3) . . ?
N1 C9 C8 111.6(3) . . ?
O2 C10 O3 126.8(4) . . ?
O2 C10 N1 121.3(3) . . ?
O3 C10 N1 111.9(3) . . ?
O3 C11 C12 101.2(3) . . ?
O3 C11 C13 109.4(3) . . ?
O3 C11 C14 110.4(3) . . ?
C13 C11 C12 111.6(3) . . ?
C13 C11 C14 113.0(3) . . ?
C14 C11 C12 110.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
