# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_wtb_02_150k_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2114142'
loop_
_audit_author_name
_audit_author_address
'wang tianbao'
;sichuan university
China
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2020-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C21 H19 N4'
_chemical_formula_sum            'C21 H19 I N4'
_chemical_formula_weight         454.30
_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      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                   7.887(3)
_cell_length_b                   10.676(5)
_cell_length_c                   11.448(4)
_cell_angle_alpha                80.632(18)
_cell_angle_beta                 89.145(17)
_cell_angle_gamma                86.29(2)
_cell_volume                     949.1(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7691
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.169
_cell_measurement_theta_min      2.423
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1630 before and 0.1159 after correction. The Ratio of minimum to maximum transmission is 0.5119. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1207
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30470
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.423
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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                3173
_reflns_number_total             3565
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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         1.777
_refine_diff_density_min         -1.938
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.030
_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)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_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:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00M), C00L(H00N), C00M(H00O), C00N(H00P), C00O(H00Q), C00P(H00R),
 C00Q(H00S)
2.b Idealised Me refined as rotating group:
 C00C(H00A,H00B,H00C), C00J(H00J,H00K,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I -0.36099(3) 0.77715(2) 0.63471(2) 0.03368(15) Uani 1 1 d . . . . .
N002 N 0.6410(4) 0.5853(3) 0.2558(3) 0.0246(7) Uani 1 1 d . . . . .
N003 N 0.5728(5) 0.7074(3) 0.0891(3) 0.0278(7) Uani 1 1 d . . . . .
N004 N 0.2650(5) 0.6570(4) 0.3096(3) 0.0327(8) Uani 1 1 d . . . . .
N005 N 0.8309(5) 0.8577(4) 0.1785(3) 0.0355(9) Uani 1 1 d . . . . .
C006 C 0.7015(5) 0.5212(4) 0.1663(4) 0.0281(9) Uani 1 1 d . . . . .
C007 C 0.5679(5) 0.6972(4) 0.2077(4) 0.0256(8) Uani 1 1 d . . . . .
C008 C 0.6589(5) 0.5997(4) 0.0601(4) 0.0292(9) Uani 1 1 d . . . . .
C009 C 0.3296(5) 0.7620(4) 0.3354(4) 0.0284(9) Uani 1 1 d . . . . .
C00A C 0.7422(6) 0.9324(4) 0.2434(4) 0.0294(9) Uani 1 1 d . . . . .
C00B C 0.4923(5) 0.7930(4) 0.2771(4) 0.0280(9) Uani 1 1 d . . . . .
C00C C 0.6458(6) 0.5318(4) 0.3813(4) 0.0309(9) Uani 1 1 d . . . . .
H00A H 0.5621 0.4672 0.3981 0.046 Uiso 1 1 calc GR . . . .
H00B H 0.6190 0.5995 0.4283 0.046 Uiso 1 1 calc GR . . . .
H00C H 0.7595 0.4926 0.4018 0.046 Uiso 1 1 calc GR . . . .
C00D C 0.1165(6) 0.6226(5) 0.3595(4) 0.0376(10) Uani 1 1 d . . . . .
H00D H 0.0711 0.5476 0.3418 0.045 Uiso 1 1 calc R . . . .
C00E C 0.5736(6) 0.8968(4) 0.2884(4) 0.0320(10) Uani 1 1 d . . . . .
H00E H 0.5143 0.9551 0.3313 0.038 Uiso 1 1 calc R . . . .
C00F C 0.7028(7) 0.5645(5) -0.0485(4) 0.0387(11) Uani 1 1 d . . . . .
H00F H 0.6729 0.6167 -0.1216 0.046 Uiso 1 1 calc R . . . .
C00G C 0.0271(6) 0.6900(5) 0.4345(4) 0.0377(10) Uani 1 1 d . . . . .
H00G H -0.0786 0.6632 0.4670 0.045 Uiso 1 1 calc R . . . .
C00H C 0.2477(6) 0.8355(4) 0.4133(4) 0.0337(10) Uani 1 1 d . . . . .
H00H H 0.2968 0.9087 0.4319 0.040 Uiso 1 1 calc R . . . .
C00I C 0.7886(7) 0.4041(5) 0.1699(5) 0.0399(11) Uani 1 1 d . . . . .
H00I H 0.8153 0.3499 0.2424 0.048 Uiso 1 1 calc R . . . .
C00J C 0.5129(7) 0.8182(5) 0.0053(4) 0.0420(11) Uani 1 1 d . . . . .
H00J H 0.4013 0.8500 0.0307 0.063 Uiso 1 1 calc GR . . . .
H00K H 0.5035 0.7944 -0.0734 0.063 Uiso 1 1 calc GR . . . .
H00L H 0.5935 0.8847 0.0021 0.063 Uiso 1 1 calc GR . . . .
C00K C 0.8046(6) 1.0418(4) 0.2737(4) 0.0339(10) Uani 1 1 d . . . . .
H00M H 0.7369 1.0946 0.3179 0.041 Uiso 1 1 calc R . . . .
C00L C 0.9664(6) 1.0717(5) 0.2383(5) 0.0382(11) Uani 1 1 d . . . . .
H00N H 1.0138 1.1441 0.2602 0.046 Uiso 1 1 calc R . . . .
C00M C 1.0592(6) 0.9964(5) 0.1710(4) 0.0391(11) Uani 1 1 d . . . . .
H00O H 1.1704 1.0162 0.1444 0.047 Uiso 1 1 calc R . . . .
C00N C 0.0943(6) 0.7986(5) 0.4619(4) 0.0374(11) Uani 1 1 d . . . . .
H00P H 0.0350 0.8471 0.5139 0.045 Uiso 1 1 calc R . . . .
C00O C 0.9854(6) 0.8903(5) 0.1430(4) 0.0386(11) Uani 1 1 d . . . . .
H00Q H 1.0489 0.8383 0.0960 0.046 Uiso 1 1 calc R . . . .
C00P C 0.7923(7) 0.4492(5) -0.0431(5) 0.0459(13) Uani 1 1 d . . . . .
H00R H 0.8268 0.4221 -0.1153 0.055 Uiso 1 1 calc R . . . .
C00Q C 0.8347(7) 0.3705(5) 0.0616(5) 0.0462(12) Uani 1 1 d . . . . .
H00S H 0.8968 0.2917 0.0593 0.055 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
N002 C006 1.384(5) . ?
N002 C007 1.330(5) . ?
N002 C00C 1.457(5) . ?
N003 C007 1.344(5) . ?
N003 C008 1.381(6) . ?
N003 C00J 1.454(6) . ?
N004 C009 1.339(6) . ?
N004 C00D 1.342(6) . ?
N005 C00A 1.335(6) . ?
N005 C00O 1.329(6) . ?
C006 C008 1.392(6) . ?
C006 C00I 1.382(6) . ?
C007 C00B 1.484(6) . ?
C008 C00F 1.389(6) . ?
C009 C00B 1.469(6) . ?
C009 C00H 1.404(6) . ?
C00A C00E 1.469(6) . ?
C00A C00K 1.392(6) . ?
C00B C00E 1.341(6) . ?
C00C H00A 0.9800 . ?
C00C H00B 0.9800 . ?
C00C H00C 0.9800 . ?
C00D H00D 0.9500 . ?
C00D C00G 1.367(7) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00P 1.372(8) . ?
C00G H00G 0.9500 . ?
C00G C00N 1.388(7) . ?
C00H H00H 0.9500 . ?
C00H C00N 1.378(7) . ?
C00I H00I 0.9500 . ?
C00I C00Q 1.382(7) . ?
C00J H00J 0.9800 . ?
C00J H00K 0.9800 . ?
C00J H00L 0.9800 . ?
C00K H00M 0.9500 . ?
C00K C00L 1.375(7) . ?
C00L H00N 0.9500 . ?
C00L C00M 1.372(7) . ?
C00M H00O 0.9500 . ?
C00M C00O 1.391(7) . ?
C00N H00P 0.9500 . ?
C00O H00Q 0.9500 . ?
C00P H00R 0.9500 . ?
C00P C00Q 1.379(8) . ?
C00Q H00S 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
C006 N002 C00C 124.3(3) . . ?
C007 N002 C006 109.0(3) . . ?
C007 N002 C00C 126.5(3) . . ?
C007 N003 C008 108.5(3) . . ?
C007 N003 C00J 125.7(4) . . ?
C008 N003 C00J 125.5(4) . . ?
C009 N004 C00D 118.3(4) . . ?
C00O N005 C00A 117.6(4) . . ?
N002 C006 C008 106.5(4) . . ?
C00I C006 N002 131.4(4) . . ?
C00I C006 C008 122.1(4) . . ?
N002 C007 N003 109.3(3) . . ?
N002 C007 C00B 124.0(4) . . ?
N003 C007 C00B 126.7(4) . . ?
N003 C008 C006 106.7(4) . . ?
N003 C008 C00F 131.7(4) . . ?
C00F C008 C006 121.6(4) . . ?
N004 C009 C00B 114.9(4) . . ?
N004 C009 C00H 122.1(4) . . ?
C00H C009 C00B 123.1(4) . . ?
N005 C00A C00E 119.3(4) . . ?
N005 C00A C00K 122.8(4) . . ?
C00K C00A C00E 117.9(4) . . ?
C009 C00B C007 115.3(4) . . ?
C00E C00B C007 121.0(4) . . ?
C00E C00B C009 123.6(4) . . ?
N002 C00C H00A 109.5 . . ?
N002 C00C H00B 109.5 . . ?
N002 C00C H00C 109.5 . . ?
H00A C00C H00B 109.5 . . ?
H00A C00C H00C 109.5 . . ?
H00B C00C H00C 109.5 . . ?
N004 C00D H00D 118.3 . . ?
N004 C00D C00G 123.4(4) . . ?
C00G C00D H00D 118.3 . . ?
C00A C00E H00E 115.7 . . ?
C00B C00E C00A 128.7(4) . . ?
C00B C00E H00E 115.7 . . ?
C008 C00F H00F 122.3 . . ?
C00P C00F C008 115.4(5) . . ?
C00P C00F H00F 122.3 . . ?
C00D C00G H00G 120.8 . . ?
C00D C00G C00N 118.5(4) . . ?
C00N C00G H00G 120.8 . . ?
C009 C00H H00H 120.9 . . ?
C00N C00H C009 118.2(4) . . ?
C00N C00H H00H 120.9 . . ?
C006 C00I H00I 122.0 . . ?
C00Q C00I C006 116.1(5) . . ?
C00Q C00I H00I 122.0 . . ?
N003 C00J H00J 109.5 . . ?
N003 C00J H00K 109.5 . . ?
N003 C00J H00L 109.5 . . ?
H00J C00J H00K 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00A C00K H00M 120.8 . . ?
C00L C00K C00A 118.4(4) . . ?
C00L C00K H00M 120.8 . . ?
C00K C00L H00N 120.2 . . ?
C00M C00L C00K 119.6(4) . . ?
C00M C00L H00N 120.2 . . ?
C00L C00M H00O 121.0 . . ?
C00L C00M C00O 118.0(5) . . ?
C00O C00M H00O 121.0 . . ?
C00G C00N H00P 120.2 . . ?
C00H C00N C00G 119.6(4) . . ?
C00H C00N H00P 120.2 . . ?
N005 C00O C00M 123.5(4) . . ?
N005 C00O H00Q 118.2 . . ?
C00M C00O H00Q 118.2 . . ?
C00F C00P H00R 118.2 . . ?
C00F C00P C00Q 123.5(4) . . ?
C00Q C00P H00R 118.2 . . ?
C00I C00Q H00S 119.4 . . ?
C00P C00Q C00I 121.3(5) . . ?
C00P C00Q H00S 119.4 . . ?

_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_wtb-1
_database_code_depnum_ccdc_archive 'CCDC 2114144'
loop_
_audit_author_name
_audit_author_address
'wang tianbao'
;sichuan university
China
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C23 H21 N2'
_chemical_formula_sum            'C23 H21 I N2'
_chemical_formula_weight         452.32
_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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.5543(4)
_cell_length_b                   8.6038(2)
_cell_length_c                   14.9273(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.336(3)
_cell_angle_gamma                90
_cell_volume                     2050.41(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    292.2(6)
_cell_measurement_theta_max      71.4600
_cell_measurement_theta_min      4.6030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.363
_diffrn_reflns_theta_min         5.542
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.2(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -16.00   1.00    2.42    --  -34.98 -57.00-180.00   87
  2  ω      1.00  75.00   1.00    2.42    --   34.98 -99.00-150.00   74
  3  ω     23.00  90.00   1.00    2.42    --   34.98-125.00-150.00   67
  4  ω      1.00  75.00   1.00    2.42    --   34.98 -99.00   0.00   74
  5  ω     13.00 106.00   1.00    2.42    --   34.98  38.00-180.00   93
  6  ω    -33.00  53.00   1.00    2.42    --   34.98 -57.00  30.00   86
  7  ω     -3.00 107.00   1.00    2.42    --   34.98  19.00  30.00  110
  8  ω     35.00 133.00   1.00    9.67    --  106.90 -30.00-180.00   98
  9  ω     36.00 113.00   1.00    9.67    --  106.90-111.00-120.00   77
 10  ω     57.00 151.00   1.00    9.67    --  106.90 178.00 -90.00   94
 11  ω     87.00 175.00   1.00    9.67    --  106.90  61.00 120.00   88
 12  ω     37.00 110.00   1.00    9.67    --  106.90 -94.00-120.00   73
 13  ω     39.00 127.00   1.00    9.67    --  106.90 -61.00   0.00   88
 14  ω     87.00 175.00   1.00    9.67    --  106.90  61.00   0.00   88
 15  ω     38.00 136.00   1.00    9.67    --  106.90 -77.00-120.00   98
 16  ω      6.00  82.00   1.00    2.42    --   34.98  77.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790366000
_diffrn_orient_matrix_UB_12      -0.0781801000
_diffrn_orient_matrix_UB_13      0.0152905000
_diffrn_orient_matrix_UB_21      0.0541079000
_diffrn_orient_matrix_UB_22      -0.1336135000
_diffrn_orient_matrix_UB_23      0.0528521000
_diffrn_orient_matrix_UB_31      0.0117456000
_diffrn_orient_matrix_UB_32      0.0898497000
_diffrn_orient_matrix_UB_33      0.0918199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3451
_reflns_number_total             3936
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         1.345
_refine_diff_density_min         -2.032
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.062
_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)+(0.1127P)²+2.1006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1795
_refine_special_details          ?
_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:
 C006(H006), C007(H007), C009(H009), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R)
2.b Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C00J(H00F,H00J,H00K)
;
_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
I001 I 0.69713(2) 0.09213(4) 0.67111(3) 0.04930(19) Uani 1 1 d . . . . .
N002 N 0.3517(3) 0.6257(5) 0.5812(3) 0.0317(8) Uani 1 1 d . . . . .
N003 N 0.3944(3) 0.3883(5) 0.5666(3) 0.0330(9) Uani 1 1 d . . . . .
C004 C 0.2092(3) 0.2893(5) 0.5341(3) 0.0300(9) Uani 1 1 d . . . . .
C005 C 0.2406(3) 0.4360(6) 0.5024(3) 0.0294(9) Uani 1 1 d . . . . .
C006 C 0.1963(3) 0.5307(6) 0.4357(3) 0.0309(9) Uani 1 1 d . . . . .
H006 H 0.2265 0.6121 0.4194 0.037 Uiso 1 1 calc R . . . .
C007 C 0.2070(3) 0.2721(6) 0.6257(4) 0.0390(11) Uani 1 1 d . . . . .
H007 H 0.2290 0.3489 0.6691 0.047 Uiso 1 1 calc R . . . .
C008 C 0.1075(3) 0.5248(5) 0.3850(3) 0.0311(9) Uani 1 1 d . . . . .
C009 C 0.1781(3) 0.1704(6) 0.4705(4) 0.0405(11) Uani 1 1 d . . . . .
H009 H 0.1811 0.1800 0.4094 0.049 Uiso 1 1 calc R . . . .
C00A C 0.4371(3) 0.6241(6) 0.6186(3) 0.0348(10) Uani 1 1 d . . . . .
C00B C 0.2987(3) 0.7600(5) 0.5852(4) 0.0401(12) Uani 1 1 d . . . . .
H00A H 0.3179 0.8096 0.6446 0.060 Uiso 1 1 calc GR . . . .
H00B H 0.2418 0.7263 0.5764 0.060 Uiso 1 1 calc GR . . . .
H00C H 0.3015 0.8322 0.5371 0.060 Uiso 1 1 calc GR . . . .
C00C C 0.3271(3) 0.4815(5) 0.5495(3) 0.0284(9) Uani 1 1 d . . . . .
C00D C 0.1429(4) 0.0389(7) 0.4974(5) 0.0547(15) Uani 1 1 d . . . . .
H00D H 0.1222 -0.0394 0.4545 0.066 Uiso 1 1 calc R . . . .
C00E C 0.0464(3) 0.4462(7) 0.4150(4) 0.0380(11) Uani 1 1 d . . . . .
H00E H 0.0609 0.3918 0.4709 0.046 Uiso 1 1 calc R . . . .
C00F C 0.4643(3) 0.4740(7) 0.6093(4) 0.0366(11) Uani 1 1 d . . . . .
C00G C 0.1716(4) 0.1388(8) 0.6522(5) 0.0523(14) Uani 1 1 d . . . . .
H00G H 0.1701 0.1263 0.7137 0.063 Uiso 1 1 calc R . . . .
C00H C 0.0832(3) 0.6089(7) 0.3028(4) 0.0447(13) Uani 1 1 d . . . . .
H00H H 0.1228 0.6667 0.2832 0.054 Uiso 1 1 calc R . . . .
C00I C 0.1384(4) 0.0241(7) 0.5871(5) 0.0585(16) Uani 1 1 d . . . . .
H00I H 0.1131 -0.0630 0.6047 0.070 Uiso 1 1 calc R . . . .
C00J C 0.3971(4) 0.2241(7) 0.5398(5) 0.0495(14) Uani 1 1 d . . . . .
H00F H 0.3792 0.1596 0.5834 0.074 Uiso 1 1 calc GR . . . .
H00J H 0.4533 0.1970 0.5397 0.074 Uiso 1 1 calc GR . . . .
H00K H 0.3606 0.2088 0.4788 0.074 Uiso 1 1 calc GR . . . .
C00K C -0.0590(3) 0.5279(7) 0.2793(4) 0.0473(13) Uani 1 1 d . . . . .
H00L H -0.1143 0.5275 0.2436 0.057 Uiso 1 1 calc R . . . .
C00L C -0.0365(3) 0.4481(7) 0.3622(4) 0.0456(12) Uani 1 1 d . . . . .
H00M H -0.0771 0.3952 0.3830 0.055 Uiso 1 1 calc R . . . .
C00M C 0.5486(3) 0.4329(9) 0.6410(5) 0.0530(15) Uani 1 1 d . . . . .
H00N H 0.5668 0.3321 0.6351 0.064 Uiso 1 1 calc R . . . .
C00N C 0.4933(4) 0.7426(8) 0.6601(4) 0.0539(15) Uani 1 1 d . . . . .
H00O H 0.4755 0.8435 0.6663 0.065 Uiso 1 1 calc R . . . .
C00O C 0.0008(4) 0.6077(9) 0.2498(5) 0.0578(18) Uani 1 1 d . . . . .
H00P H -0.0141 0.6615 0.1938 0.069 Uiso 1 1 calc R . . . .
C00P C 0.5764(4) 0.6997(11) 0.6908(5) 0.067(2) Uani 1 1 d . . . . .
H00Q H 0.6158 0.7740 0.7188 0.080 Uiso 1 1 calc R . . . .
C00Q C 0.6033(4) 0.5477(12) 0.6812(5) 0.070(2) Uani 1 1 d . . . . .
H00R H 0.6599 0.5243 0.7028 0.084 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
N002 C00A 1.375(6) . ?
N002 C00B 1.462(6) . ?
N002 C00C 1.351(6) . ?
N003 C00C 1.342(6) . ?
N003 C00F 1.378(7) . ?
N003 C00J 1.472(7) . ?
C004 C005 1.489(7) . ?
C004 C007 1.386(7) . ?
C004 C009 1.398(7) . ?
C005 C006 1.344(7) . ?
C005 C00C 1.471(6) . ?
C006 H006 0.9300 . ?
C006 C008 1.465(6) . ?
C007 H007 0.9300 . ?
C007 C00G 1.392(9) . ?
C008 C00E 1.387(7) . ?
C008 C00H 1.389(7) . ?
C009 H009 0.9300 . ?
C009 C00D 1.379(9) . ?
C00A C00F 1.387(8) . ?
C00A C00N 1.408(8) . ?
C00B H00A 0.9600 . ?
C00B H00B 0.9600 . ?
C00B H00C 0.9600 . ?
C00D H00D 0.9300 . ?
C00D C00I 1.367(10) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.391(7) . ?
C00F C00M 1.396(7) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.392(10) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.385(8) . ?
C00I H00I 0.9300 . ?
C00J H00F 0.9600 . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00K H00L 0.9300 . ?
C00K C00L 1.378(9) . ?
C00K C00O 1.369(10) . ?
C00L H00M 0.9300 . ?
C00M H00N 0.9300 . ?
C00M C00Q 1.366(11) . ?
C00N H00O 0.9300 . ?
C00N C00P 1.380(10) . ?
C00O H00P 0.9300 . ?
C00P H00Q 0.9300 . ?
C00P C00Q 1.400(13) . ?
C00Q H00R 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
C00A N002 C00B 123.7(4) . . ?
C00C N002 C00A 108.4(4) . . ?
C00C N002 C00B 127.6(4) . . ?
C00C N003 C00F 108.7(4) . . ?
C00C N003 C00J 127.3(4) . . ?
C00F N003 C00J 123.9(4) . . ?
C007 C004 C005 120.5(4) . . ?
C007 C004 C009 119.4(5) . . ?
C009 C004 C005 120.1(4) . . ?
C006 C005 C004 125.5(4) . . ?
C006 C005 C00C 117.7(4) . . ?
C00C C005 C004 116.8(4) . . ?
C005 C006 H006 115.2 . . ?
C005 C006 C008 129.7(4) . . ?
C008 C006 H006 115.2 . . ?
C004 C007 H007 120.3 . . ?
C004 C007 C00G 119.5(5) . . ?
C00G C007 H007 120.3 . . ?
C00E C008 C006 124.6(4) . . ?
C00E C008 C00H 118.3(4) . . ?
C00H C008 C006 117.0(4) . . ?
C004 C009 H009 119.6 . . ?
C00D C009 C004 120.7(5) . . ?
C00D C009 H009 119.6 . . ?
N002 C00A C00F 107.1(4) . . ?
N002 C00A C00N 131.3(6) . . ?
C00F C00A C00N 121.6(5) . . ?
N002 C00B H00A 109.5 . . ?
N002 C00B H00B 109.5 . . ?
N002 C00B H00C 109.5 . . ?
H00A C00B H00B 109.5 . . ?
H00A C00B H00C 109.5 . . ?
H00B C00B H00C 109.5 . . ?
N002 C00C C005 125.3(4) . . ?
N003 C00C N002 108.9(4) . . ?
N003 C00C C005 125.8(4) . . ?
C009 C00D H00D 120.1 . . ?
C00I C00D C009 119.9(6) . . ?
C00I C00D H00D 120.1 . . ?
C008 C00E H00E 119.8 . . ?
C008 C00E C00L 120.4(5) . . ?
C00L C00E H00E 119.8 . . ?
N003 C00F C00A 106.8(4) . . ?
N003 C00F C00M 131.6(6) . . ?
C00A C00F C00M 121.6(6) . . ?
C007 C00G H00G 119.9 . . ?
C00I C00G C007 120.2(6) . . ?
C00I C00G H00G 119.9 . . ?
C008 C00H H00H 119.6 . . ?
C00O C00H C008 120.8(6) . . ?
C00O C00H H00H 119.6 . . ?
C00D C00I C00G 120.3(6) . . ?
C00D C00I H00I 119.8 . . ?
C00G C00I H00I 119.8 . . ?
N003 C00J H00F 109.5 . . ?
N003 C00J H00J 109.5 . . ?
N003 C00J H00K 109.5 . . ?
H00F C00J H00J 109.5 . . ?
H00F C00J H00K 109.5 . . ?
H00J C00J H00K 109.5 . . ?
C00L C00K H00L 120.2 . . ?
C00O C00K H00L 120.2 . . ?
C00O C00K C00L 119.5(5) . . ?
C00E C00L H00M 119.8 . . ?
C00K C00L C00E 120.4(5) . . ?
C00K C00L H00M 119.8 . . ?
C00F C00M H00N 121.5 . . ?
C00Q C00M C00F 116.9(7) . . ?
C00Q C00M H00N 121.5 . . ?
C00A C00N H00O 122.0 . . ?
C00P C00N C00A 115.9(7) . . ?
C00P C00N H00O 122.0 . . ?
C00H C00O H00P 119.8 . . ?
C00K C00O C00H 120.5(6) . . ?
C00K C00O H00P 119.8 . . ?
C00N C00P H00Q 119.0 . . ?
C00N C00P C00Q 122.1(6) . . ?
C00Q C00P H00Q 119.0 . . ?
C00M C00Q C00P 121.9(6) . . ?
C00M C00Q H00R 119.1 . . ?
C00P C00Q H00R 119.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-20
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.210
_oxdiff_exptl_absorpt_empirical_full_min 0.571
