# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_190717zcj4
_database_code_depnum_ccdc_archive 'CCDC 1975884'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;Shandong University
China
;
_audit_update_record             
;
2020-01-13 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2020-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 I N O'
_chemical_formula_sum            'C18 H16 I N O'
_chemical_formula_weight         389.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         ICNO
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8569(3)
_cell_length_b                   9.5546(6)
_cell_length_c                   12.4049(6)
_cell_angle_alpha                96.102(5)
_cell_angle_beta                 104.127(4)
_cell_angle_gamma                93.993(5)
_cell_volume                     779.80(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6860
_cell_measurement_theta_min      5.5400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6316
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.588
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -91.00   1.00    0.10    --  -48.45 -35.00 112.00   26
  2  ω    -79.00 -36.00   1.00    0.10    --  -48.45 -35.00 112.00   43
  3  ω    -25.00   5.00   1.00    0.10    --   48.45 -35.00 112.00   30
  4  ω     44.00 122.00   1.00    0.10    --   48.45  35.00 -91.00   78
  5  ω    -99.00 -73.00   1.00    0.90    --  -86.25 -35.00 112.00   26
  6  ω   -160.00-105.00   1.00    0.90    --  -86.25 -35.00 112.00   55
  7  ω     94.00 151.00   1.00    0.90    --  106.49  35.00 -91.00   57
  8  ω     69.00 118.00   1.00    0.90    --  106.49 -35.00 112.00   49
  9  ω    -41.00  12.00   1.00    0.10    --  -48.45  35.00 -91.00   53
 10  ω     35.00  95.00   1.00    0.10    --   48.45-125.00 -30.00   60
 11  ω    -97.00 -13.00   1.00    0.90    --  -86.25  77.00  60.00   84
 12  ω    -98.00 -21.00   1.00    0.90    --  -86.25  35.00 -91.00   77
 13  ω     35.00 122.00   1.00    0.90    --  106.49 -77.00-180.00   87
 14  ω     76.00 115.00   1.00    0.90    --  106.49 -19.00 -90.00   39
 15  ω     32.00  71.00   1.00    0.90    --  106.49 -19.00 -90.00   39
 16  ω     36.00 117.00   1.00    0.90    --  106.49-125.00 150.00   81
 17  ω     37.00 109.00   1.00    0.90    --  106.49 -99.00 150.00   72
 18  ω    136.00 177.00   1.00    0.90    --  106.49  19.00 -30.00   41
 19  ω    101.00 133.00   1.00    0.90    --  106.49  19.00 -30.00   32
 20  ω     36.00  81.00   1.00    0.90    --  106.49 -38.00 -60.00   45
 21  ω     86.00 112.00   1.00    0.90    --  106.49 -38.00 -60.00   26
 22  ω     41.00 102.00   1.00    0.90    --  106.49 -99.00 -60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1745645000
_diffrn_orient_matrix_UB_12      0.0182316000
_diffrn_orient_matrix_UB_13      0.0567644000
_diffrn_orient_matrix_UB_21      -0.0165510000
_diffrn_orient_matrix_UB_22      -0.1594789000
_diffrn_orient_matrix_UB_23      0.0100312000
_diffrn_orient_matrix_UB_31      0.1531711000
_diffrn_orient_matrix_UB_32      0.0281004000
_diffrn_orient_matrix_UB_33      0.1155333000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2749
_reflns_odcompleteness_completeness 98.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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         0.465
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.076
_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)+(0.0370P)²+0.4458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0811
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.03233(4) 0.84006(3) -0.16485(2) 0.07484(13) Uani 1 1 d . . . . .
O1 O 0.9248(4) 0.6308(4) 0.1931(3) 0.0784(8) Uani 1 1 d . . . . .
N1 N 0.4628(5) 0.1387(4) 0.6281(3) 0.0686(8) Uani 1 1 d . . . . .
C1 C 0.6225(4) 0.5295(3) 0.2358(3) 0.0474(7) Uani 1 1 d . . . . .
C2 C 0.2344(5) 0.6791(4) 0.0231(3) 0.0496(7) Uani 1 1 d . . . . .
H2 H 0.1025 0.6498 0.0237 0.060 Uiso 1 1 calc R . . . .
C3 C 0.3987(4) 0.6341(3) 0.0960(2) 0.0434(6) Uani 1 1 d . . . . .
C4 C 0.5938(5) 0.6789(3) 0.0927(3) 0.0470(7) Uani 1 1 d . . . . .
C5 C 0.3994(4) 0.5385(3) 0.1852(3) 0.0468(7) Uani 1 1 d . . . . .
H5A H 0.3305 0.4459 0.1528 0.056 Uiso 1 1 calc R . . . .
H5B H 0.3349 0.5789 0.2411 0.056 Uiso 1 1 calc R . . . .
C6 C 0.6434(4) 0.3794(3) 0.3958(3) 0.0480(7) Uani 1 1 d . . . . .
C7 C 0.7395(5) 0.6152(4) 0.1765(3) 0.0530(7) Uani 1 1 d . . . . .
C8 C 0.7171(5) 0.4634(4) 0.3209(3) 0.0520(7) Uani 1 1 d . . . . .
H8 H 0.8571 0.4736 0.3344 0.062 Uiso 1 1 calc R . . . .
C9 C 0.5214(5) 0.2161(3) 0.5520(3) 0.0523(7) Uani 1 1 d . . . . .
C10 C 0.3805(5) 0.2674(4) 0.4671(3) 0.0518(7) Uani 1 1 d . . . . .
H10 H 0.2434 0.2472 0.4613 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6306(5) 0.7713(4) 0.0196(3) 0.0579(8) Uani 1 1 d . . . . .
H11 H 0.7624 0.8021 0.0199 0.070 Uiso 1 1 calc R . . . .
C12 C 0.4390(5) 0.3468(4) 0.3923(3) 0.0517(7) Uani 1 1 d . . . . .
H12 H 0.3405 0.3799 0.3379 0.062 Uiso 1 1 calc R . . . .
C13 C 0.2746(5) 0.7696(4) -0.0509(3) 0.0520(7) Uani 1 1 d . . . . .
C14 C 0.4698(6) 0.8170(4) -0.0535(3) 0.0606(8) Uani 1 1 d . . . . .
H14 H 0.4911 0.8784 -0.1038 0.073 Uiso 1 1 calc R . . . .
C15 C 0.7257(5) 0.2507(4) 0.5576(3) 0.0609(9) Uani 1 1 d . . . . .
H15 H 0.8246 0.2206 0.6136 0.073 Uiso 1 1 calc R . . . .
C16 C 0.7818(5) 0.3284(4) 0.4814(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 0.9189 0.3481 0.4871 0.072 Uiso 1 1 calc R . . . .
C17 C 0.2543(7) 0.0946(5) 0.6175(4) 0.0780(11) Uani 1 1 d . . . . .
H17A H 0.1785 0.1755 0.6128 0.117 Uiso 1 1 calc GR . . . .
H17B H 0.2415 0.0503 0.6817 0.117 Uiso 1 1 calc GR . . . .
H17C H 0.2031 0.0286 0.5509 0.117 Uiso 1 1 calc GR . . . .
C18 C 0.6088(8) 0.0733(5) 0.7074(4) 0.0814(12) Uani 1 1 d . . . . .
H18A H 0.6465 -0.0096 0.6697 0.122 Uiso 1 1 calc GR . . . .
H18B H 0.5501 0.0470 0.7661 0.122 Uiso 1 1 calc GR . . . .
H18C H 0.7264 0.1390 0.7391 0.122 Uiso 1 1 calc GR . . . .


_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 C13 2.103(3) . ?
O1 C7 1.232(4) . ?
N1 C9 1.375(5) . ?
N1 C17 1.432(6) . ?
N1 C18 1.449(5) . ?
C1 C5 1.517(4) . ?
C1 C7 1.476(5) . ?
C1 C8 1.341(5) . ?
C2 C3 1.387(5) . ?
C2 C13 1.387(5) . ?
C3 C4 1.388(4) . ?
C3 C5 1.507(4) . ?
C4 C7 1.471(5) . ?
C4 C11 1.384(5) . ?
C6 C8 1.447(5) . ?
C6 C12 1.403(4) . ?
C6 C16 1.396(5) . ?
C9 C10 1.400(5) . ?
C9 C15 1.400(5) . ?
C10 C12 1.374(5) . ?
C11 C14 1.375(6) . ?
C13 C14 1.392(5) . ?
C15 C16 1.370(6) . ?

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
C9 N1 C17 121.3(3) . . ?
C9 N1 C18 121.1(4) . . ?
C17 N1 C18 116.3(4) . . ?
C7 C1 C5 108.3(3) . . ?
C8 C1 C5 131.1(3) . . ?
C8 C1 C7 120.5(3) . . ?
C13 C2 C3 117.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 C5 128.6(3) . . ?
C4 C3 C5 111.3(3) . . ?
C3 C4 C7 109.5(3) . . ?
C11 C4 C3 121.6(3) . . ?
C11 C4 C7 128.9(3) . . ?
C3 C5 C1 103.5(2) . . ?
C12 C6 C8 125.1(3) . . ?
C16 C6 C8 119.3(3) . . ?
C16 C6 C12 115.5(3) . . ?
O1 C7 C1 126.8(3) . . ?
O1 C7 C4 125.9(3) . . ?
C4 C7 C1 107.3(3) . . ?
C1 C8 C6 132.4(3) . . ?
N1 C9 C10 121.9(3) . . ?
N1 C9 C15 121.4(3) . . ?
C15 C9 C10 116.7(3) . . ?
C12 C10 C9 121.9(3) . . ?
C14 C11 C4 119.2(3) . . ?
C10 C12 C6 121.8(3) . . ?
C2 C13 I1 119.3(2) . . ?
C2 C13 C14 123.0(3) . . ?
C14 C13 I1 117.8(3) . . ?
C11 C14 C13 118.8(3) . . ?
C16 C15 C9 120.8(3) . . ?
C15 C16 C6 123.3(3) . . ?

_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 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.562
####################################################################### 
# 
# 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_190717zcj3
_database_code_depnum_ccdc_archive 'CCDC 1975885'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;Shandong University
China
;
_audit_update_record             
;
2020-01-13 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2020-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H20 I N O'
_chemical_formula_sum            'C28 H20 I N O'
_chemical_formula_weight         513.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         ICNO
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1130(2)
_cell_length_b                   7.7595(3)
_cell_length_c                   20.7174(5)
_cell_angle_alpha                98.092(2)
_cell_angle_beta                 98.334(2)
_cell_angle_gamma                95.893(3)
_cell_volume                     1111.25(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6522
_cell_measurement_temperature    293(3)
_cell_measurement_theta_max      75.6990
_cell_measurement_theta_min      4.3200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9412
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.369
_diffrn_ambient_temperature      293(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -10.00   1.00    0.10    --  -48.45  96.00 176.00   68
  2  ω     -7.00  22.00   1.00    0.10    --  -48.45  96.00 176.00   29
  3  ω     -7.00  72.00   1.00    0.10    --   48.45 -96.00  66.00   79
  4  ω    -80.00 -54.00   1.00    1.10    --  -86.25  96.00 176.00   26
  5  ω     39.00 105.00   1.00    1.10    --  106.49 -96.00  66.00   66
  6  ω    105.00 150.00   1.00    1.10    --  106.49  96.00 176.00   45
  7  ω    -62.00  24.00   1.00    0.10    --  -48.45  57.00  30.00   86
  8  ω    -10.00  61.00   1.00    0.10    --   48.45 -38.00 150.00   71
  9  ω   -151.00-125.00   1.00    1.10    --  -86.25 -96.00  66.00   26
 10  ω    -97.00 -71.00   1.00    1.10    --  -86.25  19.00  30.00   26
 11  ω    -68.00 -13.00   1.00    1.10    --  -86.25  19.00  30.00   55
 12  ω   -122.00 -88.00   1.00    1.10    --  -86.25 -96.00  66.00   34
 13  ω     33.00 119.00   1.00    1.10    --  106.49 -19.00  30.00   86
 14  ω     35.00  66.00   1.00    1.10    --  106.49-125.00 -90.00   31
 15  ω     80.00 115.00   1.00    1.10    --  106.49 -57.00-150.00   35
 16  ω     92.00 118.00   1.00    1.10    --  106.49 -38.00  30.00   26
 17  ω     34.00  88.00   1.00    1.10    --  106.49 -38.00  30.00   54
 18  ω     79.00 117.00   1.00    1.10    --  106.49-125.00 -90.00   38
 19  ω     93.00 130.00   1.00    1.10    --  106.49  38.00-150.00   37
 20  ω    135.00 177.00   1.00    1.10    --  106.49  38.00-150.00   42
 21  ω     35.00  77.00   1.00    1.10    --  106.49 -57.00-150.00   42
 22  ω     42.00 111.00   1.00    1.10    --  106.49-125.00-150.00   69
 23  ω     95.00 177.00   1.00    1.10    --  106.49 125.00 120.00   82
 24  ω     34.00 120.00   1.00    1.10    --  106.49 -38.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0762535000
_diffrn_orient_matrix_UB_12      -0.1578718000
_diffrn_orient_matrix_UB_13      -0.0369389000
_diffrn_orient_matrix_UB_21      -0.0004259000
_diffrn_orient_matrix_UB_22      -0.0933180000
_diffrn_orient_matrix_UB_23      0.0608873000
_diffrn_orient_matrix_UB_31      -0.2070487000
_diffrn_orient_matrix_UB_32      -0.0850136000
_diffrn_orient_matrix_UB_33      -0.0268579000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3455
_reflns_number_total             3888
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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         0.841
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.079
_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)+(0.0770P)²+1.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1414
_refine_special_details          
;
 ?
;
_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:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_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 -0.02507(5) 0.99340(5) 0.29276(2) 0.07741(19) Uani 1 1 d . . . . .
O1 O 0.7762(5) 0.7388(5) 0.49421(17) 0.0580(8) Uani 1 1 d . . . . .
N1 N 0.3050(6) 0.4446(5) 0.82557(17) 0.0523(9) Uani 1 1 d . . . . .
C1 C 0.2884(6) 0.7875(5) 0.45397(19) 0.0438(8) Uani 1 1 d . . . . .
C2 C 0.4744(6) 0.8016(5) 0.4398(2) 0.0434(8) Uani 1 1 d . . . . .
C3 C 0.2791(6) 0.7136(6) 0.5173(2) 0.0469(9) Uani 1 1 d . . . . .
H3A H 0.2001 0.6007 0.5090 0.056 Uiso 1 1 calc R . . . .
H3B H 0.2284 0.7930 0.5490 0.056 Uiso 1 1 calc R . . . .
C4 C 0.4857(6) 0.6950(5) 0.54199(19) 0.0434(8) Uani 1 1 d . . . . .
C5 C 0.4926(6) 0.6021(5) 0.65514(19) 0.0453(9) Uani 1 1 d . . . . .
C6 C 0.1731(6) 0.5401(6) 0.85649(19) 0.0497(10) Uani 1 1 d . . . . .
C7 C 0.5703(6) 0.6509(5) 0.5981(2) 0.0454(9) Uani 1 1 d . . . . .
H7 H 0.7022 0.6515 0.6013 0.054 Uiso 1 1 calc R . . . .
C8 C 0.3692(6) 0.4993(6) 0.7687(2) 0.0482(9) Uani 1 1 d . . . . .
C9 C 0.6038(6) 0.7441(5) 0.4919(2) 0.0440(9) Uani 1 1 d . . . . .
C10 C 0.1876(7) 0.9049(6) 0.3568(2) 0.0488(9) Uani 1 1 d . . . . .
C11 C 0.2984(6) 0.5688(6) 0.6588(2) 0.0495(9) Uani 1 1 d . . . . .
H11 H 0.2078 0.5812 0.6232 0.059 Uiso 1 1 calc R . . . .
C12 C 0.3724(7) 0.9188(6) 0.3421(2) 0.0507(10) Uani 1 1 d . . . . .
H12 H 0.3980 0.9636 0.3045 0.061 Uiso 1 1 calc R . . . .
C13 C 0.5173(7) 0.8660(6) 0.3834(2) 0.0507(10) Uani 1 1 d . . . . .
H13 H 0.6415 0.8731 0.3740 0.061 Uiso 1 1 calc R . . . .
C14 C 0.1412(6) 0.8373(6) 0.4120(2) 0.0493(9) Uani 1 1 d . . . . .
H14 H 0.0160 0.8261 0.4205 0.059 Uiso 1 1 calc R . . . .
C15 C 0.5627(7) 0.5354(7) 0.7666(2) 0.0576(11) Uani 1 1 d . . . . .
H15 H 0.6523 0.5271 0.8031 0.069 Uiso 1 1 calc R . . . .
C16 C 0.6236(7) 0.5837(7) 0.7105(2) 0.0542(10) Uani 1 1 d . . . . .
H16 H 0.7541 0.6045 0.7095 0.065 Uiso 1 1 calc R . . . .
C17 C 0.4032(6) 0.3253(6) 0.8593(2) 0.0474(9) Uani 1 1 d . . . . .
C18 C 0.2379(6) 0.5174(7) 0.7146(2) 0.0521(10) Uani 1 1 d . . . . .
H18 H 0.1076 0.4947 0.7156 0.062 Uiso 1 1 calc R . . . .
C19 C 0.4842(8) 0.1949(7) 0.8241(3) 0.0614(12) Uani 1 1 d . . . . .
H19 H 0.4693 0.1834 0.7783 0.074 Uiso 1 1 calc R . . . .
C20 C 0.4210(8) 0.3367(7) 0.9275(2) 0.0586(11) Uani 1 1 d . . . . .
H20 H 0.3651 0.4219 0.9518 0.070 Uiso 1 1 calc R . . . .
C21 C 0.0329(7) 0.4513(9) 0.8845(2) 0.0648(13) Uani 1 1 d . . . . .
H21 H 0.0203 0.3295 0.8798 0.078 Uiso 1 1 calc R . . . .
C22 C 0.1854(9) 0.7191(7) 0.8605(3) 0.0697(14) Uani 1 1 d . . . . .
H22 H 0.2751 0.7795 0.8406 0.084 Uiso 1 1 calc R . . . .
C23 C 0.5217(10) 0.2212(9) 0.9593(3) 0.0756(15) Uani 1 1 d . . . . .
H23 H 0.5323 0.2289 1.0049 0.091 Uiso 1 1 calc R . . . .
C24 C 0.5865(10) 0.0825(8) 0.8564(3) 0.0797(16) Uani 1 1 d . . . . .
H24 H 0.6429 -0.0028 0.8324 0.096 Uiso 1 1 calc R . . . .
C25 C -0.0856(9) 0.5408(13) 0.9186(3) 0.089(2) Uani 1 1 d . . . . .
H25 H -0.1763 0.4803 0.9381 0.106 Uiso 1 1 calc R . . . .
C26 C -0.0723(11) 0.7176(14) 0.9245(3) 0.101(3) Uani 1 1 d . . . . .
H26 H -0.1527 0.7778 0.9485 0.121 Uiso 1 1 calc R . . . .
C27 C 0.6058(11) 0.0961(9) 0.9247(4) 0.0856(18) Uani 1 1 d . . . . .
H27 H 0.6755 0.0205 0.9466 0.103 Uiso 1 1 calc R . . . .
C28 C 0.0592(13) 0.8096(11) 0.8951(3) 0.100(2) Uani 1 1 d . . . . .
H28 H 0.0647 0.9308 0.8983 0.120 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 C10 2.100(5) . ?
O1 C9 1.225(5) . ?
N1 C6 1.422(6) . ?
N1 C8 1.425(5) . ?
N1 C17 1.417(6) . ?
C1 C2 1.393(6) . ?
C1 C3 1.512(6) . ?
C1 C14 1.384(6) . ?
C2 C9 1.463(6) . ?
C2 C13 1.393(6) . ?
C3 C4 1.512(6) . ?
C4 C7 1.335(6) . ?
C4 C9 1.493(6) . ?
C5 C7 1.455(6) . ?
C5 C11 1.394(6) . ?
C5 C16 1.403(6) . ?
C6 C21 1.395(7) . ?
C6 C22 1.373(7) . ?
C8 C15 1.385(7) . ?
C8 C18 1.385(6) . ?
C10 C12 1.389(7) . ?
C10 C14 1.391(6) . ?
C11 C18 1.384(6) . ?
C12 C13 1.377(7) . ?
C15 C16 1.383(7) . ?
C17 C19 1.385(7) . ?
C17 C20 1.391(6) . ?
C19 C24 1.375(8) . ?
C20 C23 1.382(8) . ?
C21 C25 1.359(9) . ?
C22 C28 1.410(9) . ?
C23 C27 1.365(10) . ?
C24 C27 1.390(10) . ?
C25 C26 1.352(13) . ?
C26 C28 1.379(13) . ?

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
C6 N1 C8 118.9(4) . . ?
C17 N1 C6 119.6(3) . . ?
C17 N1 C8 119.9(4) . . ?
C2 C1 C3 111.0(4) . . ?
C14 C1 C2 120.5(4) . . ?
C14 C1 C3 128.5(4) . . ?
C1 C2 C9 110.1(4) . . ?
C1 C2 C13 121.2(4) . . ?
C13 C2 C9 128.7(4) . . ?
C1 C3 C4 103.5(3) . . ?
C7 C4 C3 131.8(4) . . ?
C7 C4 C9 119.8(4) . . ?
C9 C4 C3 108.4(3) . . ?
C11 C5 C7 125.3(4) . . ?
C11 C5 C16 117.2(4) . . ?
C16 C5 C7 117.4(4) . . ?
C21 C6 N1 119.6(5) . . ?
C22 C6 N1 120.7(5) . . ?
C22 C6 C21 119.7(5) . . ?
C4 C7 C5 131.3(4) . . ?
C15 C8 N1 120.9(4) . . ?
C15 C8 C18 118.8(4) . . ?
C18 C8 N1 120.3(4) . . ?
O1 C9 C2 126.7(4) . . ?
O1 C9 C4 126.5(4) . . ?
C2 C9 C4 106.8(3) . . ?
C12 C10 I1 117.5(3) . . ?
C12 C10 C14 122.5(4) . . ?
C14 C10 I1 119.9(3) . . ?
C18 C11 C5 121.2(4) . . ?
C13 C12 C10 119.6(4) . . ?
C12 C13 C2 118.7(4) . . ?
C1 C14 C10 117.5(4) . . ?
C16 C15 C8 120.4(4) . . ?
C15 C16 C5 121.4(4) . . ?
C19 C17 N1 119.9(4) . . ?
C19 C17 C20 119.0(4) . . ?
C20 C17 N1 121.2(4) . . ?
C11 C18 C8 120.8(4) . . ?
C24 C19 C17 120.5(5) . . ?
C23 C20 C17 119.9(5) . . ?
C25 C21 C6 120.7(6) . . ?
C6 C22 C28 118.7(6) . . ?
C27 C23 C20 120.9(5) . . ?
C19 C24 C27 120.1(5) . . ?
C26 C25 C21 120.3(7) . . ?
C25 C26 C28 120.7(6) . . ?
C23 C27 C24 119.5(5) . . ?
C26 C28 C22 119.7(7) . . ?

_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 2.018
_oxdiff_exptl_absorpt_empirical_full_min 0.515
