# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2475832'
loop_
_audit_author_name
_audit_author_address
'Jian Wang'
;Ning Bo university
China
;
_audit_update_record             
;
2025-07-25 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_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         'C22 H24 N2 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43
_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'
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                   9.1227(3)
_cell_length_b                   9.6393(3)
_cell_length_c                   12.1000(3)
_cell_angle_alpha                103.320(2)
_cell_angle_beta                 93.6970(10)
_cell_angle_gamma                117.1610(10)
_cell_volume                     903.37(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5873
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.83
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.7761.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11338
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.828
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2927
_reflns_number_total             3252
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.057
_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)+(0.0401P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0936
_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:
 C00J(H00K,H00L), C00O(H00Q,H00R)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00H(H00I), C00I(H00J), C00K(H00M), C00L(H00N),
 C00M(H00O), C00N(H00P)
2.c Idealised Me refined as rotating group:
 C00F(H00B,H00C,H00D), C00G(H00F,H00G,H00H), C00P(H00S,H00T,H00U), C00Q(H00V,
 H00W,H00X)
;
_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
O001 O 0.06107(11) 0.60932(11) 0.39269(8) 0.0271(2) Uani 1 1 d . . . . .
O002 O 0.18824(12) 0.40336(11) -0.01163(8) 0.0271(2) Uani 1 1 d . . . . .
N003 N 0.19603(13) 0.21423(12) 0.07107(9) 0.0206(2) Uani 1 1 d . . . . .
N004 N 0.32103(13) 0.63918(13) 0.45063(9) 0.0211(2) Uani 1 1 d . . . . .
C005 C 0.09102(14) 0.25941(14) 0.23467(10) 0.0185(3) Uani 1 1 d . . . . .
C006 C 0.16570(15) 0.33963(14) 0.06654(10) 0.0194(3) Uani 1 1 d . . . . .
C007 C 0.18782(15) 0.60436(14) 0.37013(11) 0.0199(3) Uani 1 1 d . . . . .
C008 C 0.14839(15) 0.16190(14) 0.16853(11) 0.0199(3) Uani 1 1 d . . . . .
C009 C 0.40493(15) 0.59134(14) 0.27809(10) 0.0185(3) Uani 1 1 d . . . . .
C00A C 0.51847(16) 0.58567(15) 0.20898(11) 0.0214(3) Uani 1 1 d . . . . .
H00A H 0.488728 0.558713 0.127218 0.026 Uiso 1 1 calc R . . . .
C00B C 0.22835(15) 0.56546(14) 0.24849(10) 0.0189(3) Uani 1 1 d . . . . .
C00C C 0.45310(15) 0.63571(14) 0.39787(11) 0.0199(3) Uani 1 1 d . . . . .
C00D C 0.09919(15) 0.38495(14) 0.17573(10) 0.0185(3) Uani 1 1 d . . . . .
C00E C 0.02347(15) 0.22042(15) 0.32909(11) 0.0215(3) Uani 1 1 d . . . . .
H00E H -0.015961 0.285577 0.374874 0.026 Uiso 1 1 calc R . . . .
C00F C 0.22632(16) 0.69134(15) 0.19090(11) 0.0234(3) Uani 1 1 d . . . . .
H00B H 0.115038 0.683606 0.184964 0.035 Uiso 1 1 calc GR . . . .
H00C H 0.251499 0.669406 0.113275 0.035 Uiso 1 1 calc GR . . . .
H00D H 0.311136 0.801196 0.237788 0.035 Uiso 1 1 calc GR . . . .
C00G C -0.07721(16) 0.36185(15) 0.13853(11) 0.0233(3) Uani 1 1 d . . . . .
H00F H -0.154058 0.246951 0.096892 0.035 Uiso 1 1 calc GR . . . .
H00G H -0.071415 0.429307 0.087735 0.035 Uiso 1 1 calc GR . . . .
H00H H -0.118332 0.394591 0.207318 0.035 Uiso 1 1 calc GR . . . .
C00H C 0.61020(16) 0.67221(16) 0.45152(11) 0.0241(3) Uani 1 1 d . . . . .
H00I H 0.641120 0.702832 0.533444 0.029 Uiso 1 1 calc R . . . .
C00I C 0.72135(16) 0.66211(16) 0.38009(12) 0.0259(3) Uani 1 1 d . . . . .
H00J H 0.829636 0.684604 0.414012 0.031 Uiso 1 1 calc R . . . .
C00J C 0.33177(17) 0.69501(16) 0.57497(11) 0.0253(3) Uani 1 1 d . . . . .
H00K H 0.403301 0.662869 0.615853 0.030 Uiso 1 1 calc R . . . .
H00L H 0.218158 0.641077 0.592851 0.030 Uiso 1 1 calc R . . . .
C00K C 0.67687(16) 0.61996(16) 0.26080(11) 0.0242(3) Uani 1 1 d . . . . .
H00M H 0.754827 0.614384 0.213971 0.029 Uiso 1 1 calc R . . . .
C00L C 0.01389(16) 0.08370(16) 0.35641(11) 0.0251(3) Uani 1 1 d . . . . .
H00N H -0.034630 0.054533 0.420263 0.030 Uiso 1 1 calc R . . . .
C00M C 0.14366(16) 0.02826(15) 0.19598(12) 0.0245(3) Uani 1 1 d . . . . .
H00O H 0.186008 -0.035054 0.151468 0.029 Uiso 1 1 calc R . . . .
C00N C 0.07443(16) -0.00977(16) 0.29132(12) 0.0260(3) Uani 1 1 d . . . . .
H00P H 0.068641 -0.101158 0.312023 0.031 Uiso 1 1 calc R . . . .
C00O C 0.26168(17) 0.14054(16) -0.01762(11) 0.0257(3) Uani 1 1 d . . . . .
H00Q H 0.255652 0.177953 -0.086581 0.031 Uiso 1 1 calc R . . . .
H00R H 0.189820 0.020583 -0.041154 0.031 Uiso 1 1 calc R . . . .
C00P C 0.44129(19) 0.18253(19) 0.02306(13) 0.0341(3) Uani 1 1 d . . . . .
H00S H 0.476823 0.125604 -0.038125 0.051 Uiso 1 1 calc GR . . . .
H00T H 0.448862 0.148686 0.092675 0.051 Uiso 1 1 calc GR . . . .
H00U H 0.514520 0.300490 0.040982 0.051 Uiso 1 1 calc GR . . . .
C00Q C 0.4042(2) 0.87835(18) 0.61884(13) 0.0403(4) Uani 1 1 d . . . . .
H00V H 0.333859 0.910717 0.578437 0.060 Uiso 1 1 calc GR . . . .
H00W H 0.518500 0.932234 0.604219 0.060 Uiso 1 1 calc GR . . . .
H00X H 0.406976 0.910630 0.702236 0.060 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
O001 C007 1.2244(15) . ?
O002 C006 1.2214(15) . ?
N003 C006 1.3692(16) . ?
N003 C008 1.4050(16) . ?
N003 C00O 1.4611(15) . ?
N004 C007 1.3647(16) . ?
N004 C00C 1.4095(15) . ?
N004 C00J 1.4569(16) . ?
C005 C008 1.3980(17) . ?
C005 C00D 1.5168(16) . ?
C005 C00E 1.3796(18) . ?
C006 C00D 1.5440(16) . ?
C007 C00B 1.5448(16) . ?
C008 C00M 1.3856(17) . ?
C009 C00A 1.3847(17) . ?
C009 C00B 1.5176(16) . ?
C009 C00C 1.3918(17) . ?
C00A C00K 1.3936(18) . ?
C00B C00D 1.5747(16) . ?
C00B C00F 1.5383(16) . ?
C00C C00H 1.3833(18) . ?
C00D C00G 1.5411(16) . ?
C00E C00L 1.3975(18) . ?
C00H C00I 1.3960(18) . ?
C00I C00K 1.3846(19) . ?
C00J C00Q 1.516(2) . ?
C00L C00N 1.3858(19) . ?
C00M C00N 1.3935(19) . ?
C00O C00P 1.513(2) . ?

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 N003 C008 111.12(10) . . ?
C006 N003 C00O 123.80(11) . . ?
C008 N003 C00O 125.02(10) . . ?
C007 N004 C00C 111.22(10) . . ?
C007 N004 C00J 123.26(10) . . ?
C00C N004 C00J 124.98(10) . . ?
C008 C005 C00D 108.94(10) . . ?
C00E C005 C008 119.52(11) . . ?
C00E C005 C00D 131.13(11) . . ?
O002 C006 N003 124.89(11) . . ?
O002 C006 C00D 126.56(11) . . ?
N003 C006 C00D 108.55(10) . . ?
O001 C007 N004 124.79(11) . . ?
O001 C007 C00B 126.67(11) . . ?
N004 C007 C00B 108.50(10) . . ?
C005 C008 N003 109.72(10) . . ?
C00M C008 N003 127.90(11) . . ?
C00M C008 C005 122.22(12) . . ?
C00A C009 C00B 131.52(11) . . ?
C00A C009 C00C 119.32(11) . . ?
C00C C009 C00B 109.07(10) . . ?
C009 C00A C00K 119.21(12) . . ?
C007 C00B C00D 110.39(10) . . ?
C009 C00B C007 101.52(9) . . ?
C009 C00B C00D 112.67(9) . . ?
C009 C00B C00F 111.46(10) . . ?
C00F C00B C007 107.69(10) . . ?
C00F C00B C00D 112.46(10) . . ?
C009 C00C N004 109.63(11) . . ?
C00H C00C N004 127.77(11) . . ?
C00H C00C C009 122.59(11) . . ?
C005 C00D C006 101.56(9) . . ?
C005 C00D C00B 113.33(10) . . ?
C005 C00D C00G 111.19(10) . . ?
C006 C00D C00B 108.49(9) . . ?
C00G C00D C006 109.04(10) . . ?
C00G C00D C00B 112.55(9) . . ?
C005 C00E C00L 119.05(12) . . ?
C00C C00H C00I 117.14(12) . . ?
C00K C00I C00H 121.30(12) . . ?
N004 C00J C00Q 112.00(11) . . ?
C00I C00K C00A 120.42(12) . . ?
C00N C00L C00E 120.68(12) . . ?
C008 C00M C00N 117.49(12) . . ?
C00L C00N C00M 121.00(12) . . ?
N003 C00O C00P 112.92(11) . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 2475839'
loop_
_audit_author_name
_audit_author_address
'Jian Wang'
;Ning Bo university
China
;
_audit_update_record             
;
2025-07-25 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-07-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_chemical_formula_moiety         'C20 H16 F4 N2 O2'
_chemical_formula_sum            'C20 H16 F4 N2 O2'
_chemical_formula_weight         392.356
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07326 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03233 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.4607(2)
_cell_length_b                   8.2686(2)
_cell_length_c                   14.3732(4)
_cell_angle_alpha                79.310(1)
_cell_angle_beta                 87.117(1)
_cell_angle_gamma                86.788(1)
_cell_volume                     869.20(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.13
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0624 after correction.
The Ratio of minimum to maximum transmission is 0.7763.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             405.712
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.031
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.9958
_diffrn_reflns_Laue_measured_fraction_max 0.9953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25634
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9953
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.31
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2757
_reflns_number_total             3154
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.2818
_refine_diff_density_min         -0.1995
_refine_diff_density_rms         0.0425
_refine_ls_d_res_high            0.8297
_refine_ls_d_res_low             14.1121
_refine_ls_goodness_of_fit_ref   0.9499
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      0.9499
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0950
_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:
 C00G(H00G), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00K(H00a,H00b,H00c), C00L(H00d,H00e,H00f), C00N(H00h,H00i,H00j), C00S(H00k,
 H00l,H00m)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F2 F 0.85310(14) 0.63816(12) -0.00649(6) 0.0388(3) Uani 1.000000 .
F002 F 0.95399(13) 0.85735(12) 0.23172(6) 0.0373(2) Uani 1.000000 .
F1 F 0.77316(14) 1.21161(12) -0.04160(8) 0.0470(3) Uani 1.000000 .
F004 F 0.86620(15) 0.82222(13) 0.55961(7) 0.0453(3) Uani 1.000000 .
O005 O 0.39213(15) 0.60584(13) 0.30748(7) 0.0304(3) Uani 1.000000 .
O006 O 0.68748(18) 0.23208(13) 0.28696(8) 0.0377(3) Uani 1.000000 .
N007 N 0.49093(16) 0.84722(15) 0.21893(8) 0.0243(3) Uani 1.000000 .
N008 N 0.71421(17) 0.38158(15) 0.40418(8) 0.0253(3) Uani 1.000000 .
C009 C 0.77397(19) 0.53571(17) 0.41166(10) 0.0230(3) Uani 1.000000 .
C00A C 0.6264(2) 0.60110(17) 0.18098(10) 0.0238(3) Uani 1.000000 .
C00B C 0.6839(2) 0.75089(17) 0.11132(10) 0.0233(3) Uani 1.000000 .
C00C C 0.48756(19) 0.67984(18) 0.24424(10) 0.0231(3) Uani 1.000000 .
C00D C 0.60474(19) 0.89217(18) 0.13885(10) 0.0234(3) Uani 1.000000 .
C00E C 0.7205(2) 0.35955(18) 0.31209(10) 0.0269(3) Uani 1.000000 .
C00F C 0.8527(2) 0.7535(2) 0.48147(11) 0.0306(3) Uani 1.000000 .
C00G C 0.7877(2) 0.59767(19) 0.49393(10) 0.0268(3) Uani 1.000000 .
H00G H 0.7547(2) 0.53724(19) 0.55466(10) 0.0322(4) Uiso 1.000000 R
C00H C 0.82214(19) 0.62118(18) 0.32090(10) 0.0242(3) Uani 1.000000 .
C00I C 0.8933(2) 0.77289(19) 0.31600(11) 0.0276(3) Uani 1.000000 .
C00J C 0.7840(2) 0.77149(19) 0.02732(10) 0.0276(3) Uani 1.000000 .
C00K C 0.5339(2) 0.47975(18) 0.13220(11) 0.0313(4) Uani 1.000000 .
H00a H 0.4442(12) 0.5401(3) 0.0897(7) 0.0470(5) Uiso 1.000000 GR
H00b H 0.6238(3) 0.4240(11) 0.0955(7) 0.0470(5) Uiso 1.000000 GR
H00c H 0.4747(14) 0.3979(9) 0.18027(12) 0.0470(5) Uiso 1.000000 GR
C00L C 0.6623(2) 0.25404(19) 0.48297(11) 0.0293(3) Uani 1.000000 .
H00d H 0.7702(2) 0.1999(10) 0.5132(5) 0.0439(5) Uiso 1.000000 GR
H00e H 0.5872(13) 0.3035(3) 0.5292(4) 0.0439(5) Uiso 1.000000 GR
H00f H 0.5945(14) 0.1726(8) 0.45971(16) 0.0439(5) Uiso 1.000000 GR
C00M C 0.7839(2) 0.51878(18) 0.24738(10) 0.0255(3) Uani 1.000000 .
C00N C 0.3853(2) 0.9625(2) 0.26711(12) 0.0322(4) Uani 1.000000 .
H00h H 0.2994(11) 0.9023(3) 0.3127(6) 0.0483(5) Uiso 1.000000 GR
H00i H 0.4653(3) 1.0200(11) 0.3006(7) 0.0483(5) Uiso 1.000000 GR
H00j H 0.3200(13) 1.0430(9) 0.22047(15) 0.0483(5) Uiso 1.000000 GR
C00O C 0.9072(2) 0.8442(2) 0.39516(12) 0.0317(4) Uani 1.000000 .
H00O H 0.9522(2) 0.9508(2) 0.39024(12) 0.0380(4) Uiso 1.000000 R
C00P C 0.8155(2) 0.9255(2) -0.02575(11) 0.0316(4) Uani 1.000000 .
H00P H 0.8859(2) 0.9381(2) -0.08335(11) 0.0379(4) Uiso 1.000000 R
C00Q C 0.6330(2) 1.04989(18) 0.09012(12) 0.0293(3) Uani 1.000000 .
H00Q H 0.5819(2) 1.14508(18) 0.11140(12) 0.0351(4) Uiso 1.000000 R
C00R C 0.7404(2) 1.05955(19) 0.00850(12) 0.0324(4) Uani 1.000000 .
C00S C 0.9542(2) 0.4725(2) 0.19179(12) 0.0356(4) Uani 1.000000 .
H00k H 0.9246(4) 0.3971(13) 0.1503(7) 0.0533(6) Uiso 1.000000 GR
H00l H 1.0025(10) 0.5723(3) 0.1534(7) 0.0533(6) Uiso 1.000000 GR
H00m H 1.0441(7) 0.4185(14) 0.23620(12) 0.0533(6) Uiso 1.000000 GR


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
F2 C00J 1.3517(18) . ?
F002 C00I 1.3515(17) . ?
F1 C00R 1.3564(17) . ?
F004 C00F 1.3598(18) . ?
O005 C00C 1.2186(18) . ?
O006 C00E 1.2170(19) . ?
N007 C00C 1.3655(19) . ?
N007 C00D 1.4008(18) . ?
N007 C00N 1.4547(18) . ?
N008 C009 1.3978(19) . ?
N008 C00E 1.3674(19) . ?
N008 C00L 1.4502(18) . ?
C009 C00G 1.384(2) . ?
C009 C00H 1.403(2) . ?
C00A C00B 1.5089(19) . ?
C00A C00C 1.541(2) . ?
C00A C00K 1.537(2) . ?
C00A C00M 1.593(2) . ?
C00B C00D 1.393(2) . ?
C00B C00J 1.375(2) . ?
C00D C00Q 1.383(2) . ?
C00E C00M 1.547(2) . ?
C00F C00G 1.380(2) . ?
C00F C00O 1.380(2) . ?
C00G H00G 0.9500 . ?
C00H C00I 1.378(2) . ?
C00H C00M 1.518(2) . ?
C00I C00O 1.386(2) . ?
C00J C00P 1.384(2) . ?
C00K H00a 0.9800 . ?
C00K H00b 0.9800 . ?
C00K H00c 0.9800 . ?
C00L H00d 0.9800 . ?
C00L H00e 0.9800 . ?
C00L H00f 0.9800 . ?
C00M C00S 1.535(2) . ?
C00N H00h 0.9800 . ?
C00N H00i 0.9800 . ?
C00N H00j 0.9800 . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00R 1.375(2) . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.379(2) . ?
C00S H00k 0.9800 . ?
C00S H00l 0.9800 . ?
C00S H00m 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
C00D N007 C00C 110.93(12) . . ?
C00N N007 C00C 124.21(12) . . ?
C00N N007 C00D 124.82(12) . . ?
C00E N008 C009 111.51(12) . . ?
C00L N008 C009 125.56(12) . . ?
C00L N008 C00E 122.81(13) . . ?
C00G C009 N008 126.95(13) . . ?
C00H C009 N008 109.11(12) . . ?
C00H C009 C00G 123.93(14) . . ?
C00C C00A C00B 101.04(11) . . ?
C00K C00A C00B 111.87(12) . . ?
C00K C00A C00C 109.52(12) . . ?
C00M C00A C00B 112.56(12) . . ?
C00M C00A C00C 106.73(11) . . ?
C00M C00A C00K 114.13(12) . . ?
C00D C00B C00A 109.35(12) . . ?
C00J C00B C00A 133.31(13) . . ?
C00J C00B C00D 117.17(13) . . ?
N007 C00C O005 125.35(14) . . ?
C00A C00C O005 125.94(13) . . ?
C00A C00C N007 108.70(11) . . ?
C00B C00D N007 109.48(12) . . ?
C00Q C00D N007 127.05(14) . . ?
C00Q C00D C00B 123.42(14) . . ?
N008 C00E O006 124.60(14) . . ?
C00M C00E O006 126.42(13) . . ?
C00M C00E N008 108.93(12) . . ?
C00G C00F F004 117.93(14) . . ?
C00O C00F F004 117.52(14) . . ?
C00O C00F C00G 124.55(14) . . ?
C00F C00G C009 115.20(14) . . ?
H00G C00G C009 122.40(9) . . ?
H00G C00G C00F 122.40(9) . . ?
C00I C00H C009 116.62(13) . . ?
C00M C00H C009 109.62(12) . . ?
C00M C00H C00I 133.75(13) . . ?
C00H C00I F002 119.94(13) . . ?
C00O C00I F002 117.55(13) . . ?
C00O C00I C00H 122.50(14) . . ?
C00B C00J F2 119.82(13) . . ?
C00P C00J F2 117.88(13) . . ?
C00P C00J C00B 122.29(14) . . ?
H00a C00K C00A 109.5 . . ?
H00b C00K C00A 109.5 . . ?
H00b C00K H00a 109.5 . . ?
H00c C00K C00A 109.5 . . ?
H00c C00K H00a 109.5 . . ?
H00c C00K H00b 109.5 . . ?
H00d C00L N008 109.5 . . ?
H00e C00L N008 109.5 . . ?
H00e C00L H00d 109.5 . . ?
H00f C00L N008 109.5 . . ?
H00f C00L H00d 109.5 . . ?
H00f C00L H00e 109.5 . . ?
C00E C00M C00A 109.94(12) . . ?
C00H C00M C00A 111.97(11) . . ?
C00H C00M C00E 100.65(11) . . ?
C00S C00M C00A 113.22(12) . . ?
C00S C00M C00E 107.56(12) . . ?
C00S C00M C00H 112.64(13) . . ?
H00h C00N N007 109.5 . . ?
H00i C00N N007 109.5 . . ?
H00i C00N H00h 109.5 . . ?
H00j C00N N007 109.5 . . ?
H00j C00N H00h 109.5 . . ?
H00j C00N H00i 109.5 . . ?
C00I C00O C00F 117.08(14) . . ?
H00O C00O C00F 121.46(9) . . ?
H00O C00O C00I 121.46(9) . . ?
H00P C00P C00J 121.46(9) . . ?
C00R C00P C00J 117.08(14) . . ?
C00R C00P H00P 121.46(9) . . ?
H00Q C00Q C00D 122.28(9) . . ?
C00R C00Q C00D 115.44(14) . . ?
C00R C00Q H00Q 122.28(9) . . ?
C00P C00R F1 117.83(14) . . ?
C00Q C00R F1 117.75(15) . . ?
C00Q C00R C00P 124.42(14) . . ?
H00k C00S C00M 109.5 . . ?
H00l C00S C00M 109.5 . . ?
H00l C00S H00k 109.5 . . ?
H00m C00S C00M 109.5 . . ?
H00m C00S H00k 109.5 . . ?
H00m C00S H00l 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C00J C00B C00A -0.5(2) . . . . ?
F2 C00J C00B C00D -175.17(14) . . . . ?
F2 C00J C00P C00R 178.40(15) . . . . ?
F002 C00I C00H C009 175.54(13) . . . . ?
F002 C00I C00H C00M -3.49(19) . . . . ?
F002 C00I C00O C00F -177.02(14) . . . . ?
F1 C00R C00P C00J 178.58(15) . . . . ?
F1 C00R C00Q C00D -179.58(14) . . . . ?
F004 C00F C00G C009 178.86(14) . . . . ?
F004 C00F C00O C00I 179.84(14) . . . . ?
O005 C00C N007 C00D -175.27(15) . . . . ?
O005 C00C N007 C00N 2.78(19) . . . . ?
O005 C00C C00A C00B 173.96(16) . . . . ?
O005 C00C C00A C00K 55.81(16) . . . . ?
O005 C00C C00A C00M -68.21(15) . . . . ?
O006 C00E N008 C009 174.75(16) . . . . ?
O006 C00E N008 C00L -1.6(2) . . . . ?
O006 C00E C00M C00A 68.27(18) . . . . ?
O006 C00E C00M C00H -173.49(18) . . . . ?
O006 C00E C00M C00S -55.43(18) . . . . ?
N007 C00C C00A C00B -7.10(12) . . . . ?
N007 C00C C00A C00K -125.26(12) . . . . ?
N007 C00C C00A C00M 110.72(12) . . . . ?
N007 C00D C00B C00A -3.15(13) . . . . ?
N007 C00D C00B C00J 172.73(12) . . . . ?
N007 C00D C00Q C00R -174.60(16) . . . . ?
N008 C009 C00G C00F 179.38(16) . . . . ?
N008 C009 C00H C00I -176.68(12) . . . . ?
N008 C009 C00H C00M 2.57(13) . . . . ?
N008 C00E C00M C00A -114.34(12) . . . . ?
N008 C00E C00M C00H 3.90(13) . . . . ?
N008 C00E C00M C00S 121.96(13) . . . . ?
C009 N008 C00E C00M -2.70(13) . . . . ?
C009 C00G C00F C00O -1.95(17) . . . . ?
C009 C00H C00I C00O -3.98(17) . . . . ?
C009 C00H C00M C00A 112.91(12) . . . . ?
C009 C00H C00M C00E -3.84(13) . . . . ?
C009 C00H C00M C00S -118.12(13) . . . . ?
C00A C00B C00D C00Q 179.12(12) . . . . ?
C00A C00B C00J C00P 178.52(18) . . . . ?
C00A C00C N007 C00D 5.79(13) . . . . ?
C00A C00C N007 C00N -176.17(11) . . . . ?
C00A C00M C00H C00I -68.02(15) . . . . ?
C00B C00A C00M C00E -176.07(12) . . . . ?
C00B C00A C00M C00H 72.93(12) . . . . ?
C00B C00A C00M C00S -55.74(13) . . . . ?
C00B C00D N007 C00C -1.75(14) . . . . ?
C00B C00D N007 C00N -179.78(12) . . . . ?
C00B C00D C00Q C00R 2.72(17) . . . . ?
C00B C00J C00P C00R -0.65(18) . . . . ?
C00C N007 C00D C00Q 175.88(12) . . . . ?
C00C C00A C00B C00D 6.08(12) . . . . ?
C00C C00A C00B C00J -168.88(11) . . . . ?
C00C C00A C00M C00E 73.98(11) . . . . ?
C00C C00A C00M C00H -37.03(12) . . . . ?
C00C C00A C00M C00S -165.70(12) . . . . ?
C00D C00B C00A C00K 122.51(13) . . . . ?
C00D C00B C00A C00M -107.41(12) . . . . ?
C00D C00B C00J C00P 3.86(17) . . . . ?
C00D C00Q C00R C00P 0.83(18) . . . . ?
C00E N008 C009 C00G -179.09(12) . . . . ?
C00E N008 C009 C00H 0.12(13) . . . . ?
C00E C00M C00A C00K -47.15(13) . . . . ?
C00E C00M C00H C00I 175.23(11) . . . . ?
C00F C00G C009 C00H 0.28(17) . . . . ?
C00F C00O C00I C00H 2.51(18) . . . . ?
C00G C009 N008 C00L -2.89(19) . . . . ?
C00G C009 C00H C00I 2.56(17) . . . . ?
C00G C009 C00H C00M -178.19(15) . . . . ?
C00G C00F C00O C00I 0.64(19) . . . . ?
C00H C009 N008 C00L 176.32(12) . . . . ?
C00H C00M C00A C00K -158.16(12) . . . . ?
C00I C00H C00M C00S 60.96(19) . . . . ?
C00J C00B C00A C00K -52.45(19) . . . . ?
C00J C00B C00A C00M 77.63(18) . . . . ?
C00J C00B C00D C00Q -5.00(17) . . . . ?
C00J C00P C00R C00Q -1.83(19) . . . . ?
C00K C00A C00M C00S 73.17(14) . . . . ?
C00L N008 C00E C00M -179.02(15) . . . . ?
C00M C00H C00I C00O 176.99(18) . . . . ?
C00N N007 C00D C00Q -2.16(18) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
