# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_11
_database_code_depnum_ccdc_archive 'CCDC 2062350'
loop_
_audit_author_name
_audit_author_address
'Yali Liu'
;Shihezi University
China
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_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         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_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'
N N 0.0061 0.0033 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.6464(2)
_cell_length_b                   30.7588(9)
_cell_length_c                   5.8780(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6901
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16722
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.720
_diffrn_reflns_theta_min         2.745
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2646
_reflns_number_total             2872
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.098
_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)+(0.0319P)²+0.3048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
C2 C -0.3287(3) -0.17870(7) -0.3064(4) 0.0302(5) Uani 1 1 d . . . . .
H2 H -0.275846 -0.165431 -0.435101 0.036 Uiso 1 1 calc R . . . .
C1 C -0.3315(3) -0.22423(7) -0.2879(4) 0.0256(5) Uani 1 1 d . . . . .
C3 C -0.4020(3) -0.15311(7) -0.1390(4) 0.0326(5) Uani 1 1 d . . . . .
H3 H -0.400906 -0.122367 -0.154220 0.039 Uiso 1 1 calc R . . . .
C4 C -0.4776(3) -0.17207(7) 0.0517(4) 0.0309(5) Uani 1 1 d . . . . .
H4 H -0.526060 -0.154140 0.167255 0.037 Uiso 1 1 calc R . . . .
C5 C -0.4830(3) -0.21685(7) 0.0750(4) 0.0281(5) Uani 1 1 d . . . . .
H5 H -0.534949 -0.229740 0.205419 0.034 Uiso 1 1 calc R . . . .
C6 C -0.4112(3) -0.24269(6) -0.0954(4) 0.0237(4) Uani 1 1 d . . . . .
C7 C -0.4843(3) -0.31550(7) 0.0771(4) 0.0269(5) Uani 1 1 d . . . . .
H7 H -0.538056 -0.306945 0.215736 0.032 Uiso 1 1 calc R . . . .
C8 C -0.4597(3) -0.35748(7) 0.0041(4) 0.0285(5) Uani 1 1 d . . . . .
H8 H -0.492443 -0.382965 0.084845 0.034 Uiso 1 1 calc R . . . .
C9 C -0.3773(3) -0.35642(7) -0.2117(4) 0.0265(5) Uani 1 1 d . . . . .
C10 C -0.3506(3) -0.31260(7) -0.2633(4) 0.0243(5) Uani 1 1 d . . . . .
C11 C -0.2683(3) -0.29067(7) -0.4444(4) 0.0264(5) Uani 1 1 d . . . . .
H11 H -0.218469 -0.307853 -0.562015 0.032 Uiso 1 1 calc R . . . .
C12 C -0.3313(3) -0.39227(7) -0.3597(4) 0.0278(5) Uani 1 1 d . . . . .
C13 C -0.3036(3) -0.42093(8) -0.4838(4) 0.0300(5) Uani 1 1 d . . . . .
C14 C -0.2766(3) -0.45792(7) -0.6340(4) 0.0275(5) Uani 1 1 d . . . . .
C15 C -0.3313(3) -0.49955(7) -0.5677(4) 0.0283(5) Uani 1 1 d . . . . .
H15 H -0.386019 -0.503635 -0.424136 0.034 Uiso 1 1 calc R . . . .
C16 C -0.3058(3) -0.53456(7) -0.7103(4) 0.0284(5) Uani 1 1 d . . . . .
H16 H -0.343587 -0.562565 -0.662943 0.034 Uiso 1 1 calc R . . . .
C17 C -0.2260(3) -0.52993(7) -0.9225(4) 0.0276(5) Uani 1 1 d . . . . .
C18 C -0.1717(3) -0.48862(7) -0.9879(4) 0.0296(5) Uani 1 1 d . . . . .
H18 H -0.116315 -0.484699 -1.131097 0.036 Uiso 1 1 calc R . . . .
C19 C -0.1974(3) -0.45304(7) -0.8462(4) 0.0303(5) Uani 1 1 d . . . . .
H19 H -0.160673 -0.425017 -0.894578 0.036 Uiso 1 1 calc R . . . .
C20 C -0.2026(3) -0.56880(7) -1.0763(5) 0.0339(5) Uani 1 1 d . . . . .
H20A H -0.097001 -0.584723 -1.031749 0.051 Uiso 1 1 calc GR . . . .
H20B H -0.191030 -0.558956 -1.234191 0.051 Uiso 1 1 calc GR . . . .
H20C H -0.304513 -0.587939 -1.062933 0.051 Uiso 1 1 calc GR . . . .
N1 N -0.4176(2) -0.28815(5) -0.0850(3) 0.0230(4) Uani 1 1 d . . . . .
N2 N -0.2553(2) -0.24857(6) -0.4625(3) 0.0280(4) 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
C2 H2 0.9500 . ?
C2 C1 1.405(3) . ?
C2 C3 1.379(3) . ?
C1 C6 1.405(3) . ?
C1 N2 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 N1 1.400(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(3) . ?
C7 N1 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.417(3) . ?
C9 C10 1.396(3) . ?
C9 C12 1.448(3) . ?
C10 C11 1.409(3) . ?
C10 N1 1.388(3) . ?
C11 H11 0.9500 . ?
C11 N2 1.303(3) . ?
C12 C13 1.164(3) . ?
C13 C14 1.455(3) . ?
C14 C15 1.402(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(3) . ?
C17 C18 1.391(3) . ?
C17 C20 1.510(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C6 C1 C2 118.2(2) . . ?
N2 C1 C2 118.1(2) . . ?
N2 C1 C6 123.76(19) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.33(18) . . ?
C5 C6 N1 121.7(2) . . ?
N1 C6 C1 117.0(2) . . ?
C8 C7 H7 126.0 . . ?
N1 C7 H7 126.0 . . ?
N1 C7 C8 108.0(2) . . ?
C7 C8 H8 125.7 . . ?
C7 C8 C9 108.6(2) . . ?
C9 C8 H8 125.7 . . ?
C8 C9 C12 128.9(2) . . ?
C10 C9 C8 106.4(2) . . ?
C10 C9 C12 124.7(2) . . ?
C9 C10 C11 133.8(2) . . ?
N1 C10 C9 107.75(19) . . ?
N1 C10 C11 118.43(18) . . ?
C10 C11 H11 117.6 . . ?
N2 C11 C10 124.9(2) . . ?
N2 C11 H11 117.6 . . ?
C13 C12 C9 176.2(2) . . ?
C12 C13 C14 177.1(2) . . ?
C15 C14 C13 120.2(2) . . ?
C19 C14 C13 121.3(2) . . ?
C19 C14 C15 118.4(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.7(2) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 120.4(2) . . ?
C18 C17 C16 118.1(2) . . ?
C18 C17 C20 121.5(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C6 131.05(19) . . ?
C7 N1 C10 109.26(16) . . ?
C10 N1 C6 119.68(19) . . ?
C11 N2 C1 116.14(19) . . ?

_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_11_d
_database_code_depnum_ccdc_archive 'CCDC 2017290'
loop_
_audit_author_name
_audit_author_address
'Yali Liu'
;Shihezi University
China
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 I N2'
_chemical_formula_sum            'C11 H7 I N2'
_chemical_formula_weight         294.09
_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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.3693(5)
_cell_length_b                   4.2733(2)
_cell_length_c                   16.9207(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     966.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      4.73
_shelx_estimated_absorpt_T_max   0.640
_shelx_estimated_absorpt_T_min   0.576
_exptl_absorpt_coefficient_mu    3.269
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16465
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.744
_diffrn_reflns_theta_min         4.729
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2018
_reflns_number_total             2045
_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       'Bruker APEX3'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0114
_refine_ls_R_factor_gt           0.0111
_refine_ls_restrained_S_all      1.027
_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)+(0.0153P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0280
_refine_ls_wR_factor_ref         0.0281
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.56(2)
 0.44(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.54549(2) 0.17967(3) 0.70403(2) 0.02647(6) Uani 1 1 d . . . . .
N1 N 0.49752(16) 0.8533(5) 0.47216(14) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.68749(16) 0.6141(5) 0.50858(13) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.67801(19) 0.8138(5) 0.44350(16) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.7597(2) 0.8958(7) 0.39583(17) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.824443 0.815497 0.406834 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7447(2) 1.0945(7) 0.33284(18) 0.0283(6) Uani 1 1 d . . . . .
H3 H 0.799538 1.147781 0.299753 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6503(2) 1.2188(7) 0.31682(17) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.641296 1.357986 0.273618 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5700(2) 1.1389(6) 0.36394(17) 0.0247(5) Uani 1 1 d . . . . .
H5 H 0.505934 1.224573 0.353062 0.030 Uiso 1 1 calc R . . . .
C6 C 0.58189(19) 0.9336(6) 0.42740(15) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.5105(2) 0.6672(6) 0.53153(17) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.453363 0.610817 0.561755 0.028 Uiso 1 1 calc R . . . .
C8 C 0.60421(18) 0.5415(6) 0.55455(15) 0.0201(5) Uani 1 1 d . . . . .
C9 C 0.6371(2) 0.3533(5) 0.61567(16) 0.0228(5) Uani 1 1 d . . . . .
C10 C 0.7405(2) 0.3096(6) 0.60676(17) 0.0266(6) Uani 1 1 d . . . . .
H10 H 0.782660 0.190387 0.640483 0.032 Uiso 1 1 calc R . . . .
C11 C 0.76988(19) 0.4714(7) 0.54011(17) 0.0222(5) Uani 1 1 d . . . . .
H11 H 0.835970 0.481813 0.519647 0.027 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 C9 2.070(3) . ?
N1 C6 1.401(3) . ?
N1 C7 1.293(4) . ?
N2 C1 1.399(3) . ?
N2 C8 1.393(3) . ?
N2 C11 1.368(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.410(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.418(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.404(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(4) . ?
C11 H11 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 N1 C6 117.6(2) . . ?
C8 N2 C1 120.2(2) . . ?
C11 N2 C1 130.7(2) . . ?
C11 N2 C8 109.1(2) . . ?
N2 C1 C2 122.3(2) . . ?
N2 C1 C6 117.1(2) . . ?
C2 C1 C6 120.5(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C1 122.7(2) . . ?
C5 C6 N1 118.6(2) . . ?
C5 C6 C1 118.7(2) . . ?
N1 C7 H7 117.8 . . ?
N1 C7 C8 124.4(3) . . ?
C8 C7 H7 117.8 . . ?
N2 C8 C7 117.9(2) . . ?
C9 C8 N2 107.1(2) . . ?
C9 C8 C7 135.0(2) . . ?
C8 C9 I1 124.1(2) . . ?
C8 C9 C10 108.1(2) . . ?
C10 C9 I1 127.8(2) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.5(2) . . ?
C11 C10 H10 126.2 . . ?
N2 C11 C10 108.3(2) . . ?
N2 C11 H11 125.9 . . ?
C10 C11 H11 125.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.56(2)
2 0.44(2)

