# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 2054251'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-01
_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            TPAN-Cl
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Cl N'
_chemical_formula_sum            'C21 H14 Cl N'
_chemical_formula_weight         315.78
_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'
Cl Cl 0.1484 0.1585 '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                   9.509(9)
_cell_length_b                   9.570(10)
_cell_length_c                   10.324(10)
_cell_angle_alpha                63.11(2)
_cell_angle_beta                 79.79(2)
_cell_angle_gamma                81.27(3)
_cell_volume                     821.9(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.17
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1294 before and 0.0977 after correction.
The Ratio of minimum to maximum transmission is 0.7443.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             328
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1668
_diffrn_reflns_av_unetI/netI     0.1316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.409
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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                1509
_reflns_number_total             3691
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050
_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     208
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1979
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.030
_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)+(0.0800P)²+0.1728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2388
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
;
_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
Cl Cl 0.93110(14) 0.67559(17) 0.05765(17) 0.0977(6) Uani 1 1 d . . . . .
N1 N 1.4238(4) 1.2822(5) -0.1932(5) 0.0813(13) Uani 1 1 d . . . . .
C1 C 1.5862(4) 0.9848(4) -0.2859(4) 0.0490(10) Uani 1 1 d . . . . .
C2 C 1.4623(4) 1.0208(5) -0.2162(4) 0.0510(10) Uani 1 1 d . . . . .
C3 C 1.6973(4) 1.0975(5) -0.3676(4) 0.0514(10) Uani 1 1 d . . . . .
C4 C 1.6638(5) 1.2504(5) -0.4699(5) 0.0580(11) Uani 1 1 d . . . . .
H4 H 1.5688 1.2850 -0.4859 0.070 Uiso 1 1 calc R . . . .
C5 C 1.7699(5) 1.3511(5) -0.5477(5) 0.0682(13) Uani 1 1 d . . . . .
H5 H 1.7459 1.4529 -0.6158 0.082 Uiso 1 1 calc R . . . .
C6 C 1.9107(5) 1.3026(6) -0.5258(6) 0.0756(14) Uani 1 1 d . . . . .
H6 H 1.9815 1.3715 -0.5780 0.091 Uiso 1 1 calc R . . . .
C7 C 1.9466(5) 1.1515(6) -0.4260(6) 0.0770(14) Uani 1 1 d . . . . .
H7 H 2.0417 1.1183 -0.4096 0.092 Uiso 1 1 calc R . . . .
C8 C 1.8407(4) 1.0494(6) -0.3505(5) 0.0642(12) Uani 1 1 d . . . . .
H8 H 1.8661 0.9461 -0.2867 0.077 Uiso 1 1 calc R . . . .
C9 C 1.6215(4) 0.8264(5) -0.2825(4) 0.0502(10) Uani 1 1 d . . . . .
C10 C 1.6670(4) 0.8137(5) -0.4124(5) 0.0572(11) Uani 1 1 d . . . . .
H10 H 1.6741 0.9044 -0.5003 0.069 Uiso 1 1 calc R . . . .
C11 C 1.7019(4) 0.6697(5) -0.4135(5) 0.0630(12) Uani 1 1 d . . . . .
H11 H 1.7319 0.6633 -0.5016 0.076 Uiso 1 1 calc R . . . .
C12 C 1.6923(5) 0.5351(6) -0.2845(6) 0.0713(14) Uani 1 1 d . . . . .
H12 H 1.7138 0.4374 -0.2853 0.086 Uiso 1 1 calc R . . . .
C13 C 1.6514(5) 0.5445(6) -0.1549(6) 0.0758(14) Uani 1 1 d . . . . .
H13 H 1.6473 0.4532 -0.0674 0.091 Uiso 1 1 calc R . . . .
C14 C 1.6158(5) 0.6901(5) -0.1529(5) 0.0646(12) Uani 1 1 d . . . . .
H14 H 1.5882 0.6958 -0.0642 0.078 Uiso 1 1 calc R . . . .
C15 C 1.3365(4) 0.9271(5) -0.1453(4) 0.0497(10) Uani 1 1 d . . . . .
C16 C 1.2868(4) 0.8433(5) -0.2059(5) 0.0560(11) Uani 1 1 d . . . . .
H16 H 1.3380 0.8396 -0.2900 0.067 Uiso 1 1 calc R . . . .
C17 C 1.1632(4) 0.7652(5) -0.1443(5) 0.0614(12) Uani 1 1 d . . . . .
H17 H 1.1315 0.7103 -0.1869 0.074 Uiso 1 1 calc R . . . .
C18 C 1.0876(4) 0.7695(5) -0.0191(5) 0.0634(12) Uani 1 1 d . . . . .
C19 C 1.1340(5) 0.8510(5) 0.0440(5) 0.0667(13) Uani 1 1 d . . . . .
H19 H 1.0833 0.8529 0.1290 0.080 Uiso 1 1 calc R . . . .
C20 C 1.2568(4) 0.9300(5) -0.0202(5) 0.0617(12) Uani 1 1 d . . . . .
H20 H 1.2867 0.9866 0.0218 0.074 Uiso 1 1 calc R . . . .
C21 C 1.4444(4) 1.1683(6) -0.2060(5) 0.0609(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C18 1.731(5) . ?
N1 C21 1.141(5) . ?
C1 C2 1.351(5) . ?
C1 C3 1.483(5) . ?
C1 C9 1.487(6) . ?
C2 C15 1.480(5) . ?
C2 C21 1.445(6) . ?
C3 C4 1.392(6) . ?
C3 C8 1.387(6) . ?
C4 C5 1.378(6) . ?
C5 C6 1.372(6) . ?
C6 C7 1.377(7) . ?
C7 C8 1.381(6) . ?
C9 C10 1.388(6) . ?
C9 C14 1.383(6) . ?
C10 C11 1.373(6) . ?
C11 C12 1.372(6) . ?
C12 C13 1.365(7) . ?
C13 C14 1.391(6) . ?
C15 C16 1.390(6) . ?
C15 C20 1.387(6) . ?
C16 C17 1.385(5) . ?
C17 C18 1.377(6) . ?
C18 C19 1.375(6) . ?
C19 C20 1.384(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
C2 C1 C3 122.8(4) . . ?
C2 C1 C9 121.7(3) . . ?
C3 C1 C9 115.4(3) . . ?
C1 C2 C15 128.4(4) . . ?
C1 C2 C21 118.6(4) . . ?
C21 C2 C15 113.1(3) . . ?
C4 C3 C1 121.9(4) . . ?
C8 C3 C1 120.2(4) . . ?
C8 C3 C4 117.7(4) . . ?
C5 C4 C3 120.7(4) . . ?
C6 C5 C4 120.6(5) . . ?
C5 C6 C7 119.8(4) . . ?
C6 C7 C8 119.6(5) . . ?
C7 C8 C3 121.5(5) . . ?
C10 C9 C1 119.5(4) . . ?
C14 C9 C1 122.1(4) . . ?
C14 C9 C10 118.3(4) . . ?
C11 C10 C9 121.2(4) . . ?
C12 C11 C10 119.9(4) . . ?
C13 C12 C11 120.1(5) . . ?
C12 C13 C14 120.3(4) . . ?
C9 C14 C13 120.1(4) . . ?
C16 C15 C2 122.2(4) . . ?
C20 C15 C2 120.4(4) . . ?
C20 C15 C16 117.3(4) . . ?
C17 C16 C15 121.7(4) . . ?
C18 C17 C16 119.3(4) . . ?
C17 C18 Cl 120.0(4) . . ?
C19 C18 Cl 119.5(4) . . ?
C19 C18 C17 120.5(4) . . ?
C18 C19 C20 119.4(4) . . ?
C19 C20 C15 121.8(4) . . ?
N1 C21 C2 176.4(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_mo_0117_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2054255'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 I N3'
_chemical_formula_sum            'C25 H24 I N3'
_chemical_formula_weight         493.37
_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                   9.9437(5)
_cell_length_b                   10.8454(5)
_cell_length_c                   11.7215(5)
_cell_angle_alpha                102.807(2)
_cell_angle_beta                 93.095(2)
_cell_angle_gamma                115.385(2)
_cell_volume                     1097.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.474
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0768 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.3877.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         2.300
_diffrn_ambient_temperature      153.35
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                3856
_reflns_number_total             4518
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.824
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.8819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0715
_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:
 C007(H007), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00C,H00G), C00R(H00K,H00L,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,
 H00V,H00W)
;
_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 0.79811(2) 1.03154(2) 0.68281(2) 0.04861(8) Uani 1 1 d . . . . .
N002 N 0.1502(3) -0.1789(2) 0.9099(2) 0.0448(6) Uani 1 1 d . . . . .
N003 N 0.2762(3) 0.4544(3) 0.9465(2) 0.0448(6) Uani 1 1 d . . . . .
C004 C 0.5433(3) 0.5751(3) 0.7739(2) 0.0334(5) Uani 1 1 d . . . . .
N005 N 0.9731(3) 0.3396(3) 0.5312(2) 0.0592(8) Uani 1 1 d . . . . .
C006 C 0.6937(3) 0.8362(3) 0.7233(3) 0.0359(6) Uani 1 1 d . . . . .
C007 C 0.5824(3) 0.2343(3) 0.5873(2) 0.0360(6) Uani 1 1 d . . . . .
H007 H 0.482659 0.167456 0.548934 0.043 Uiso 1 1 calc R . . . .
C008 C 0.6041(3) 0.3233(3) 0.6993(2) 0.0336(5) Uani 1 1 d . . . . .
C009 C 0.2235(3) -0.0653(3) 0.8657(2) 0.0363(6) Uani 1 1 d . . . . .
C00A C 0.4766(3) 0.3175(3) 0.7622(2) 0.0335(5) Uani 1 1 d . . . . .
C00B C 0.5876(3) 0.7030(3) 0.8610(2) 0.0360(6) Uani 1 1 d . . . . .
H00B H 0.565421 0.700879 0.938550 0.043 Uiso 1 1 calc R . . . .
C00C C 0.3834(3) 0.1823(3) 0.7886(2) 0.0333(5) Uani 1 1 d . . . . .
C00D C 0.3739(3) -0.0228(3) 0.8469(2) 0.0380(6) Uani 1 1 d . . . . .
H00D H 0.423624 -0.077283 0.860416 0.046 Uiso 1 1 calc R . . . .
C00E C 0.4497(3) 0.0971(3) 0.8092(2) 0.0363(6) Uani 1 1 d . . . . .
H00E H 0.550764 0.122651 0.796689 0.044 Uiso 1 1 calc R . . . .
C00F C 0.7526(3) 0.4166(3) 0.7545(2) 0.0380(6) Uani 1 1 d . . . . .
H00F H 0.770683 0.478481 0.831249 0.046 Uiso 1 1 calc R . . . .
C00G C 0.3546(3) 0.4414(3) 0.8821(2) 0.0358(6) Uani 1 1 d . . . . .
C00H C 0.1532(3) 0.0146(3) 0.8365(2) 0.0369(6) Uani 1 1 d . . . . .
H00H H 0.049603 -0.014921 0.842378 0.044 Uiso 1 1 calc R . . . .
C00I C 0.6631(3) 0.8328(3) 0.8364(3) 0.0387(6) Uani 1 1 d . . . . .
H00I H 0.693636 0.918518 0.896941 0.046 Uiso 1 1 calc R . . . .
C00J C 0.2304(3) 0.1341(3) 0.7999(2) 0.0365(6) Uani 1 1 d . . . . .
H00J H 0.179073 0.185528 0.781673 0.044 Uiso 1 1 calc R . . . .
C00K C 0.4582(3) 0.4373(3) 0.8013(2) 0.0340(5) Uani 1 1 d . . . . .
C00L C 0.8522(3) 0.3341(3) 0.5858(2) 0.0389(6) Uani 1 1 d . . . . .
C00M C 0.5763(3) 0.5822(3) 0.6608(2) 0.0381(6) Uani 1 1 d . . . . .
H00M H 0.547619 0.496949 0.600159 0.046 Uiso 1 1 calc R . . . .
C00N C 0.7024(3) 0.2408(3) 0.5303(2) 0.0386(6) Uani 1 1 d . . . . .
H00N H 0.683406 0.181165 0.452335 0.046 Uiso 1 1 calc R . . . .
C00O C 0.6502(3) 0.7117(3) 0.6351(3) 0.0394(6) Uani 1 1 d . . . . .
H00O H 0.670893 0.714690 0.557265 0.047 Uiso 1 1 calc R . . . .
C00P C 0.8736(3) 0.4210(3) 0.7003(2) 0.0400(6) Uani 1 1 d . . . . .
H00P H 0.973369 0.484089 0.741095 0.048 Uiso 1 1 calc R . . . .
C00Q C -0.0034(3) -0.2190(3) 0.9297(3) 0.0502(8) Uani 1 1 d . . . . .
H00A H -0.010012 -0.136044 0.977695 0.075 Uiso 1 1 calc GR . . . .
H00C H -0.033476 -0.293006 0.971588 0.075 Uiso 1 1 calc GR . . . .
H00G H -0.070731 -0.255029 0.853206 0.075 Uiso 1 1 calc GR . . . .
C00R C 0.2203(4) -0.2668(3) 0.9292(3) 0.0500(7) Uani 1 1 d . . . . .
H00K H 0.243660 -0.307226 0.854024 0.075 Uiso 1 1 calc GR . . . .
H00L H 0.150930 -0.343611 0.959474 0.075 Uiso 1 1 calc GR . . . .
H00Q H 0.313690 -0.209164 0.987090 0.075 Uiso 1 1 calc GR . . . .
C00S C 0.9507(4) 0.2398(4) 0.4193(3) 0.0627(10) Uani 1 1 d . . . . .
H00R H 0.908981 0.143748 0.429417 0.094 Uiso 1 1 calc GR . . . .
H00S H 1.047689 0.262943 0.391613 0.094 Uiso 1 1 calc GR . . . .
H00T H 0.880314 0.244733 0.360802 0.094 Uiso 1 1 calc GR . . . .
C00T C 1.1262(4) 0.4268(4) 0.5939(3) 0.0590(9) Uani 1 1 d . . . . .
H00U H 1.143208 0.525128 0.622984 0.088 Uiso 1 1 calc GR . . . .
H00V H 1.196943 0.422285 0.540042 0.088 Uiso 1 1 calc GR . . . .
H00W H 1.142123 0.391979 0.661260 0.088 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
I001 C006 2.098(3) . ?
N002 C009 1.368(4) . ?
N002 C00Q 1.445(4) . ?
N002 C00R 1.448(4) . ?
N003 C00G 1.144(4) . ?
C004 C00B 1.399(4) . ?
C004 C00K 1.487(4) . ?
C004 C00M 1.394(4) . ?
N005 C00L 1.377(4) . ?
N005 C00S 1.440(4) . ?
N005 C00T 1.445(4) . ?
C006 C00I 1.382(4) . ?
C006 C00O 1.383(4) . ?
C007 C008 1.389(4) . ?
C007 C00N 1.382(4) . ?
C008 C00A 1.486(4) . ?
C008 C00F 1.396(4) . ?
C009 C00D 1.409(4) . ?
C009 C00H 1.408(4) . ?
C00A C00C 1.474(4) . ?
C00A C00K 1.371(4) . ?
C00B C00I 1.387(4) . ?
C00C C00E 1.397(4) . ?
C00C C00J 1.406(4) . ?
C00D C00E 1.381(4) . ?
C00F C00P 1.379(4) . ?
C00G C00K 1.445(4) . ?
C00H C00J 1.371(4) . ?
C00L C00N 1.406(4) . ?
C00L C00P 1.404(4) . ?
C00M C00O 1.389(4) . ?

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
C009 N002 C00Q 120.1(2) . . ?
C009 N002 C00R 120.8(2) . . ?
C00Q N002 C00R 118.9(2) . . ?
C00B C004 C00K 120.5(2) . . ?
C00M C004 C00B 117.7(2) . . ?
C00M C004 C00K 121.7(2) . . ?
C00L N005 C00S 120.7(3) . . ?
C00L N005 C00T 120.8(3) . . ?
C00S N005 C00T 117.5(3) . . ?
C00I C006 I001 119.8(2) . . ?
C00I C006 C00O 120.5(3) . . ?
C00O C006 I001 119.6(2) . . ?
C00N C007 C008 121.6(3) . . ?
C007 C008 C00A 122.4(2) . . ?
C007 C008 C00F 117.5(2) . . ?
C00F C008 C00A 120.1(2) . . ?
N002 C009 C00D 121.3(3) . . ?
N002 C009 C00H 122.0(2) . . ?
C00H C009 C00D 116.7(2) . . ?
C00C C00A C008 116.4(2) . . ?
C00K C00A C008 120.1(2) . . ?
C00K C00A C00C 123.2(2) . . ?
C00I C00B C004 121.4(3) . . ?
C00E C00C C00A 119.3(2) . . ?
C00E C00C C00J 116.4(2) . . ?
C00J C00C C00A 124.2(2) . . ?
C00E C00D C009 120.7(3) . . ?
C00D C00E C00C 122.4(2) . . ?
C00P C00F C008 121.5(3) . . ?
N003 C00G C00K 175.2(3) . . ?
C00J C00H C009 121.7(2) . . ?
C006 C00I C00B 119.4(3) . . ?
C00H C00J C00C 121.7(3) . . ?
C00A C00K C004 126.2(2) . . ?
C00A C00K C00G 120.8(2) . . ?
C00G C00K C004 112.9(2) . . ?
N005 C00L C00N 121.8(3) . . ?
N005 C00L C00P 121.2(3) . . ?
C00P C00L C00N 117.1(3) . . ?
C00O C00M C004 121.2(3) . . ?
C007 C00N C00L 121.0(3) . . ?
C006 C00O C00M 119.7(3) . . ?
C00F C00P C00L 121.2(3) . . ?

_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_mo_0610_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2054250'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping' 'zhejiang normal university'
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_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            TPAN-F
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 F N'
_chemical_formula_sum            'C21 H14 F N'
_chemical_formula_weight         299.33
_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'
F F 0.0171 0.0103 '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                   8.4617(8)
_cell_length_b                   9.9195(9)
_cell_length_c                   10.0112(10)
_cell_angle_alpha                106.884(5)
_cell_angle_beta                 104.687(5)
_cell_angle_gamma                91.445(5)
_cell_volume                     773.36(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                1873
_reflns_number_total             3176
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.194
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.032
_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)+(0.0445P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_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
F001 F 0.78301(17) 0.80296(14) 0.16399(15) 0.0373(4) Uani 1 1 d . . . . .
N002 N 0.0955(3) 0.3756(2) 0.1373(2) 0.0356(5) Uani 1 1 d . . . . .
C003 C 0.4667(3) 0.2500(2) 0.2688(2) 0.0235(5) Uani 1 1 d . . . . .
C004 C 0.4093(3) 0.3586(2) 0.2203(2) 0.0245(5) Uani 1 1 d . . . . .
C005 C 0.3582(3) 0.1213(2) 0.2492(3) 0.0248(5) Uani 1 1 d . . . . .
C006 C 0.6928(3) 0.6949(2) 0.1792(2) 0.0274(6) Uani 1 1 d . . . . .
C007 C 0.2335(3) 0.3629(2) 0.1717(3) 0.0272(6) Uani 1 1 d . . . . .
C008 C 0.6428(3) 0.2516(2) 0.3426(2) 0.0240(5) Uani 1 1 d . . . . .
C009 C 0.6521(3) 0.4534(2) 0.1622(2) 0.0267(6) Uani 1 1 d . . . . .
H009 H 0.685175 0.360528 0.139878 0.032 Uiso 1 1 calc R . . . .
C00A C 0.5534(3) 0.7244(2) 0.2232(2) 0.0281(6) Uani 1 1 d . . . . .
H00A H 0.520256 0.817318 0.242853 0.034 Uiso 1 1 calc R . . . .
C00B C 0.5110(3) 0.4775(2) 0.2092(2) 0.0236(5) Uani 1 1 d . . . . .
C00C C 0.4624(3) 0.6144(2) 0.2380(2) 0.0268(6) Uani 1 1 d . . . . .
H00C H 0.365185 0.632169 0.268248 0.032 Uiso 1 1 calc R . . . .
C00D C 0.3577(3) 0.0720(3) 0.3663(3) 0.0294(6) Uani 1 1 d . . . . .
H00D H 0.423781 0.123524 0.460630 0.035 Uiso 1 1 calc R . . . .
C00E C 0.7276(3) 0.1364(2) 0.2938(3) 0.0296(6) Uani 1 1 d . . . . .
H00E H 0.670759 0.056373 0.215723 0.035 Uiso 1 1 calc R . . . .
C00F C 0.7452(3) 0.5620(2) 0.1473(3) 0.0275(6) Uani 1 1 d . . . . .
H00F H 0.842059 0.545441 0.116184 0.033 Uiso 1 1 calc R . . . .
C00G C 0.7279(3) 0.3659(2) 0.4610(3) 0.0283(6) Uani 1 1 d . . . . .
H00G H 0.672303 0.444976 0.496134 0.034 Uiso 1 1 calc R . . . .
C00H C 0.2614(3) 0.0429(2) 0.1118(3) 0.0309(6) Uani 1 1 d . . . . .
H00H H 0.259337 0.075313 0.030976 0.037 Uiso 1 1 calc R . . . .
C00I C 0.8927(3) 0.3649(3) 0.5276(3) 0.0327(6) Uani 1 1 d . . . . .
H00I H 0.948597 0.441839 0.609696 0.039 Uiso 1 1 calc R . . . .
C00J C 0.2622(3) -0.0507(3) 0.3466(3) 0.0343(6) Uani 1 1 d . . . . .
H00J H 0.260888 -0.081824 0.427581 0.041 Uiso 1 1 calc R . . . .
C00K C 0.1680(3) -0.0822(3) 0.0920(3) 0.0364(7) Uani 1 1 d . . . . .
H00K H 0.103965 -0.135745 -0.002398 0.044 Uiso 1 1 calc R . . . .
C00L C 0.1681(3) -0.1287(3) 0.2093(3) 0.0364(7) Uani 1 1 d . . . . .
H00L H 0.103919 -0.213931 0.195820 0.044 Uiso 1 1 calc R . . . .
C00M C 0.8928(3) 0.1375(3) 0.3577(3) 0.0356(6) Uani 1 1 d . . . . .
H00M H 0.949669 0.059822 0.321461 0.043 Uiso 1 1 calc R . . . .
C00N C 0.9759(3) 0.2518(3) 0.4746(3) 0.0364(6) Uani 1 1 d . . . . .
H00N H 1.089652 0.252529 0.518352 0.044 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
F001 C006 1.366(3) . ?
N002 C007 1.152(3) . ?
C003 C004 1.358(3) . ?
C003 C005 1.488(3) . ?
C003 C008 1.483(3) . ?
C004 C007 1.449(3) . ?
C004 C00B 1.489(3) . ?
C005 C00D 1.396(3) . ?
C005 C00H 1.394(3) . ?
C006 C00A 1.370(3) . ?
C006 C00F 1.376(3) . ?
C008 C00E 1.397(3) . ?
C008 C00G 1.398(3) . ?
C009 C00B 1.393(3) . ?
C009 C00F 1.383(3) . ?
C00A C00C 1.384(3) . ?
C00B C00C 1.398(3) . ?
C00D C00J 1.380(3) . ?
C00E C00M 1.380(3) . ?
C00G C00I 1.386(3) . ?
C00H C00K 1.390(3) . ?
C00I C00N 1.385(4) . ?
C00J C00L 1.385(4) . ?
C00K C00L 1.380(4) . ?
C00M C00N 1.386(3) . ?

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
C004 C003 C005 122.3(2) . . ?
C004 C003 C008 121.7(2) . . ?
C008 C003 C005 115.93(19) . . ?
C003 C004 C007 119.2(2) . . ?
C003 C004 C00B 126.1(2) . . ?
C007 C004 C00B 114.6(2) . . ?
C00D C005 C003 120.9(2) . . ?
C00H C005 C003 120.6(2) . . ?
C00H C005 C00D 118.5(2) . . ?
F001 C006 C00A 118.2(2) . . ?
F001 C006 C00F 118.3(2) . . ?
C00A C006 C00F 123.5(2) . . ?
N002 C007 C004 175.6(2) . . ?
C00E C008 C003 119.8(2) . . ?
C00E C008 C00G 118.4(2) . . ?
C00G C008 C003 121.8(2) . . ?
C00F C009 C00B 121.3(2) . . ?
C006 C00A C00C 117.8(2) . . ?
C009 C00B C004 120.6(2) . . ?
C009 C00B C00C 118.3(2) . . ?
C00C C00B C004 120.9(2) . . ?
C00A C00C C00B 121.2(2) . . ?
C00J C00D C005 120.7(2) . . ?
C00M C00E C008 120.8(2) . . ?
C006 C00F C009 117.7(2) . . ?
C00I C00G C008 120.6(2) . . ?
C00K C00H C005 120.6(2) . . ?
C00N C00I C00G 120.1(2) . . ?
C00D C00J C00L 120.3(2) . . ?
C00L C00K C00H 120.0(2) . . ?
C00K C00L C00J 119.8(2) . . ?
C00E C00M C00N 120.2(2) . . ?
C00I C00N C00M 119.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_0623_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2054258'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-06-23
_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         'C25 H24 F N3'
_chemical_formula_sum            'C25 H24 F N3'
_chemical_formula_weight         385.47
_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'
F F 0.0171 0.0103 '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      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                   10.6861(5)
_cell_length_b                   21.3893(10)
_cell_length_c                   10.0313(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.138(2)
_cell_angle_gamma                90
_cell_volume                     2075.67(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0666 after correction.
The Ratio of minimum to maximum transmission is 0.9127.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.105
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                2666
_reflns_number_total             4255
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.185
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.047
_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)+(0.0522P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1259
_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:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00D,H00E,H00G), C00R(H00I,H00K,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,
 H00V,H00W)
;
_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
F001 F -0.10921(13) 0.64366(6) 0.44867(15) 0.0475(4) Uani 1 1 d . . . . .
N002 N 0.26837(18) 0.90304(8) 0.3956(2) 0.0380(5) Uani 1 1 d . . . . .
N003 N 0.91399(18) 0.92500(8) 0.5743(2) 0.0414(5) Uani 1 1 d . . . . .
N004 N 0.5464(2) 0.50955(8) 0.3436(2) 0.0432(5) Uani 1 1 d . . . . .
C005 C 0.45343(19) 0.76293(9) 0.4516(2) 0.0251(4) Uani 1 1 d . . . . .
C006 C 0.3001(2) 0.85115(10) 0.4181(2) 0.0290(5) Uani 1 1 d . . . . .
C007 C 0.3280(2) 0.78499(9) 0.4364(2) 0.0267(4) Uani 1 1 d . . . . .
C008 C 0.3986(2) 0.60081(9) 0.2854(2) 0.0282(5) Uani 1 1 d . . . . .
H008 H 0.329567 0.579346 0.204678 0.034 Uiso 1 1 calc R . . . .
C009 C 0.4742(2) 0.69597(8) 0.4290(2) 0.0254(4) Uani 1 1 d . . . . .
C00A C 0.6028(2) 0.85418(9) 0.5850(2) 0.0305(5) Uani 1 1 d . . . . .
H00A H 0.545161 0.860683 0.634329 0.037 Uiso 1 1 calc R . . . .
C00B C 0.0748(2) 0.75757(9) 0.3344(2) 0.0297(5) Uani 1 1 d . . . . .
H00B H 0.056086 0.789884 0.263499 0.036 Uiso 1 1 calc R . . . .
C00C C 0.3758(2) 0.66192(9) 0.3136(2) 0.0269(4) Uani 1 1 d . . . . .
H00C H 0.290560 0.681318 0.252560 0.032 Uiso 1 1 calc R . . . .
C00D C 0.2110(2) 0.74646(9) 0.4350(2) 0.0261(5) Uani 1 1 d . . . . .
C00E C -0.0036(2) 0.67712(9) 0.4413(2) 0.0321(5) Uani 1 1 d . . . . .
C00F C 0.6626(2) 0.79656(9) 0.4165(2) 0.0309(5) Uani 1 1 d . . . . .
H00F H 0.646806 0.763007 0.349186 0.037 Uiso 1 1 calc R . . . .
C00G C 0.5225(2) 0.56973(9) 0.3742(2) 0.0297(5) Uani 1 1 d . . . . .
C00H C 0.7138(2) 0.89346(9) 0.6152(2) 0.0317(5) Uani 1 1 d . . . . .
H00H H 0.730451 0.926450 0.684082 0.038 Uiso 1 1 calc R . . . .
C00I C 0.8026(2) 0.88570(9) 0.5464(2) 0.0315(5) Uani 1 1 d . . . . .
C00J C -0.0338(2) 0.72252(9) 0.3355(2) 0.0328(5) Uani 1 1 d . . . . .
H00J H -0.126181 0.729699 0.265381 0.039 Uiso 1 1 calc R . . . .
C00K C 0.57221(19) 0.80499(9) 0.4838(2) 0.0270(5) Uani 1 1 d . . . . .
C00L C 0.5967(2) 0.66494(9) 0.5173(2) 0.0296(5) Uani 1 1 d . . . . .
H00L H 0.666010 0.686875 0.596758 0.036 Uiso 1 1 calc R . . . .
C00M C 0.7736(2) 0.83580(9) 0.4457(2) 0.0332(5) Uani 1 1 d . . . . .
H00M H 0.831647 0.829082 0.396927 0.040 Uiso 1 1 calc R . . . .
C00N C 0.2360(2) 0.69904(9) 0.5390(2) 0.0293(5) Uani 1 1 d . . . . .
H00N H 0.328000 0.690728 0.608521 0.035 Uiso 1 1 calc R . . . .
C00O C 0.6202(2) 0.60352(9) 0.4928(2) 0.0318(5) Uani 1 1 d . . . . .
H00O H 0.703749 0.583774 0.557150 0.038 Uiso 1 1 calc R . . . .
C00P C 0.1284(2) 0.66404(9) 0.5420(2) 0.0320(5) Uani 1 1 d . . . . .
H00P H 0.145634 0.631621 0.612373 0.038 Uiso 1 1 calc R . . . .
C00Q C 0.4511(3) 0.47831(10) 0.2110(3) 0.0513(7) Uani 1 1 d . . . . .
H00D H 0.360427 0.474773 0.212836 0.077 Uiso 1 1 calc GR . . . .
H00E H 0.486193 0.436463 0.205966 0.077 Uiso 1 1 calc GR . . . .
H00G H 0.442330 0.502589 0.124621 0.077 Uiso 1 1 calc GR . . . .
C00R C 0.9610(2) 0.96501(11) 0.7045(3) 0.0509(7) Uani 1 1 d . . . . .
H00I H 0.885845 0.992962 0.697577 0.076 Uiso 1 1 calc GR . . . .
H00K H 1.040241 0.989911 0.710538 0.076 Uiso 1 1 calc GR . . . .
H00Q H 0.988603 0.938984 0.792903 0.076 Uiso 1 1 calc GR . . . .
C00S C 0.6774(3) 0.47938(11) 0.4301(3) 0.0517(7) Uani 1 1 d . . . . .
H00R H 0.751509 0.501695 0.417101 0.078 Uiso 1 1 calc GR . . . .
H00S H 0.674037 0.435983 0.397441 0.078 Uiso 1 1 calc GR . . . .
H00T H 0.695203 0.480036 0.534344 0.078 Uiso 1 1 calc GR . . . .
C00T C 1.0176(2) 0.90655(11) 0.5240(3) 0.0539(7) Uani 1 1 d . . . . .
H00U H 1.062139 0.867724 0.573252 0.081 Uiso 1 1 calc GR . . . .
H00V H 1.087292 0.939597 0.547533 0.081 Uiso 1 1 calc GR . . . .
H00W H 0.973330 0.899873 0.417233 0.081 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
F001 C00E 1.365(2) . ?
N002 C006 1.155(2) . ?
N003 C00I 1.385(3) . ?
N003 C00R 1.461(3) . ?
N003 C00T 1.453(3) . ?
N004 C00G 1.372(2) . ?
N004 C00Q 1.450(3) . ?
N004 C00S 1.447(3) . ?
C005 C007 1.367(3) . ?
C005 C009 1.481(3) . ?
C005 C00K 1.475(3) . ?
C006 C007 1.442(3) . ?
C007 C00D 1.492(3) . ?
C008 C00C 1.381(3) . ?
C008 C00G 1.410(3) . ?
C009 C00C 1.394(3) . ?
C009 C00L 1.398(3) . ?
C00A C00H 1.379(3) . ?
C00A C00K 1.401(3) . ?
C00B C00D 1.395(3) . ?
C00B C00J 1.386(3) . ?
C00D C00N 1.397(3) . ?
C00E C00J 1.372(3) . ?
C00E C00P 1.370(3) . ?
C00F C00K 1.405(3) . ?
C00F C00M 1.379(3) . ?
C00G C00O 1.404(3) . ?
C00H C00I 1.400(3) . ?
C00I C00M 1.411(3) . ?
C00L C00O 1.379(3) . ?
C00N C00P 1.383(3) . ?

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
C00I N003 C00R 118.41(19) . . ?
C00I N003 C00T 118.77(18) . . ?
C00T N003 C00R 116.50(19) . . ?
C00G N004 C00Q 120.83(18) . . ?
C00G N004 C00S 120.57(18) . . ?
C00S N004 C00Q 117.89(18) . . ?
C007 C005 C009 121.34(17) . . ?
C007 C005 C00K 121.70(17) . . ?
C00K C005 C009 116.89(16) . . ?
N002 C006 C007 175.0(2) . . ?
C005 C007 C006 119.51(18) . . ?
C005 C007 C00D 126.02(17) . . ?
C006 C007 C00D 114.47(16) . . ?
C00C C008 C00G 121.12(19) . . ?
C00C C009 C005 121.53(17) . . ?
C00C C009 C00L 116.83(17) . . ?
C00L C009 C005 121.55(17) . . ?
C00H C00A C00K 122.08(19) . . ?
C00J C00B C00D 121.48(19) . . ?
C008 C00C C009 121.90(18) . . ?
C00B C00D C007 121.67(18) . . ?
C00B C00D C00N 118.25(18) . . ?
C00N C00D C007 120.05(17) . . ?
F001 C00E C00J 118.97(18) . . ?
F001 C00E C00P 117.96(19) . . ?
C00P C00E C00J 123.07(19) . . ?
C00M C00F C00K 121.63(19) . . ?
N004 C00G C008 121.00(19) . . ?
N004 C00G C00O 122.03(18) . . ?
C00O C00G C008 116.96(18) . . ?
C00A C00H C00I 121.31(19) . . ?
N003 C00I C00H 122.19(19) . . ?
N003 C00I C00M 120.84(19) . . ?
C00H C00I C00M 116.98(18) . . ?
C00E C00J C00B 117.78(19) . . ?
C00A C00K C005 122.07(18) . . ?
C00A C00K C00F 116.63(18) . . ?
C00F C00K C005 121.29(17) . . ?
C00O C00L C009 122.15(18) . . ?
C00F C00M C00I 121.3(2) . . ?
C00P C00N C00D 120.85(19) . . ?
C00L C00O C00G 121.01(19) . . ?
C00E C00P C00N 118.56(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_0521_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2054256'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-05-21
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 N3'
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.4826(6)
_cell_length_b                   21.4895(11)
_cell_length_c                   9.9353(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.143(2)
_cell_angle_gamma                90
_cell_volume                     2042.31(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.9247.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            54232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             4185
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.031
_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)+(0.0495P)²+0.5614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1056
_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:
 C007(H007), C008(H008), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00D), C00Q(H00H,H00P,H00Q), C00R(H00R,H00S,H00T), C00S(H00U,
 H00V,H00W)
;
_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
N001 N 0.73447(13) 0.89939(6) 0.60562(14) 0.0345(3) Uani 1 1 d . . . . .
N002 N 0.08929(13) 0.92527(6) 0.42867(15) 0.0367(3) Uani 1 1 d . . . . .
N003 N 0.44534(14) 0.50899(6) 0.65557(15) 0.0407(3) Uani 1 1 d . . . . .
C004 C 0.52522(14) 0.69364(6) 0.56856(14) 0.0241(3) Uani 1 1 d . . . . .
C005 C 0.47166(15) 0.56849(6) 0.62441(15) 0.0274(3) Uani 1 1 d . . . . .
C006 C 0.54853(13) 0.75999(6) 0.54691(13) 0.0241(3) Uani 1 1 d . . . . .
C007 C 0.59860(14) 0.59850(6) 0.71110(14) 0.0264(3) Uani 1 1 d . . . . .
H007 H 0.668081 0.576563 0.790236 0.032 Uiso 1 1 calc R U . . .
C008 C 0.40187(14) 0.85163(6) 0.41431(14) 0.0267(3) Uani 1 1 d . . . . .
H008 H 0.460892 0.857106 0.363802 0.032 Uiso 1 1 calc R U . . .
C009 C 0.70452(14) 0.84766(7) 0.58300(14) 0.0270(3) Uani 1 1 d . . . . .
C00A C 0.42944(13) 0.80271(6) 0.51545(14) 0.0243(3) Uani 1 1 d . . . . .
C00B C 0.79717(14) 0.74394(6) 0.56761(14) 0.0243(3) Uani 1 1 d . . . . .
C00C C 1.02521(15) 0.67463(7) 0.57400(15) 0.0302(3) Uani 1 1 d . . . . .
H00C H 1.102610 0.651153 0.575593 0.036 Uiso 1 1 calc R U . . .
C00D C 0.67664(14) 0.78206(6) 0.56308(14) 0.0247(3) Uani 1 1 d . . . . .
C00E C 0.39992(14) 0.66374(6) 0.48215(15) 0.0280(3) Uani 1 1 d . . . . .
H00E H 0.330551 0.686032 0.403659 0.034 Uiso 1 1 calc R U . . .
C00F C 0.62363(14) 0.65898(6) 0.68313(14) 0.0253(3) Uani 1 1 d . . . . .
H00F H 0.710369 0.677726 0.743483 0.030 Uiso 1 1 calc R U . . .
C00G C 0.29178(14) 0.89209(6) 0.38573(15) 0.0282(3) Uani 1 1 d . . . . .
H00G H 0.277398 0.925043 0.317305 0.034 Uiso 1 1 calc R U . . .
C00H C 0.20049(14) 0.88537(6) 0.45618(15) 0.0286(3) Uani 1 1 d . . . . .
C00I C 0.22703(14) 0.83580(7) 0.55670(15) 0.0300(3) Uani 1 1 d . . . . .
H00I H 0.167399 0.829845 0.606340 0.036 Uiso 1 1 calc R U . . .
C00J C 0.77859(15) 0.69671(6) 0.46550(15) 0.0279(3) Uani 1 1 d . . . . .
H00J H 0.687689 0.688028 0.392650 0.034 Uiso 1 1 calc R U . . .
C00K C 0.33764(14) 0.79573(7) 0.58466(15) 0.0280(3) Uani 1 1 d . . . . .
H00K H 0.351978 0.762566 0.652541 0.034 Uiso 1 1 calc R U . . .
C00L C 0.89191(15) 0.66221(7) 0.46935(16) 0.0306(3) Uani 1 1 d . . . . .
H00L H 0.877911 0.629827 0.399639 0.037 Uiso 1 1 calc R U . . .
C00M C 0.93260(14) 0.75601(6) 0.67256(15) 0.0279(3) Uani 1 1 d . . . . .
H00M H 0.947435 0.788466 0.742303 0.033 Uiso 1 1 calc R U . . .
C00N C 1.04504(14) 0.72139(7) 0.67616(15) 0.0300(3) Uani 1 1 d . . . . .
H00N H 1.136135 0.729741 0.748998 0.036 Uiso 1 1 calc R U . . .
C00O C 0.37373(15) 0.60283(7) 0.50720(15) 0.0299(3) Uani 1 1 d . . . . .
H00O H 0.288218 0.583838 0.444271 0.036 Uiso 1 1 calc R U . . .
C00P C 0.04635(17) 0.96605(7) 0.30062(19) 0.0438(4) Uani 1 1 d . . . . .
H00A H 0.123912 0.993693 0.310064 0.066 Uiso 1 1 calc R U . . .
H00B H -0.034056 0.991000 0.294614 0.066 Uiso 1 1 calc R U . . .
H00D H 0.020303 0.940892 0.211025 0.066 Uiso 1 1 calc R U . . .
C00Q C 0.54158(19) 0.47726(8) 0.78686(19) 0.0469(4) Uani 1 1 d . . . . .
H00H H 0.631163 0.470985 0.779622 0.070 Uiso 1 1 calc R U . . .
H00P H 0.502384 0.436830 0.795565 0.070 Uiso 1 1 calc R U . . .
H00Q H 0.556169 0.502560 0.874017 0.070 Uiso 1 1 calc R U . . .
C00R C 0.31348(18) 0.47944(8) 0.5698(2) 0.0467(4) Uani 1 1 d . . . . .
H00R H 0.237997 0.502348 0.581853 0.070 Uiso 1 1 calc R U . . .
H00S H 0.315204 0.436495 0.603685 0.070 Uiso 1 1 calc R U . . .
H00T H 0.297557 0.479373 0.465472 0.070 Uiso 1 1 calc R U . . .
C00S C -0.01928(17) 0.90669(8) 0.4762(2) 0.0480(4) Uani 1 1 d . . . . .
H00U H -0.063884 0.868364 0.425147 0.072 Uiso 1 1 calc R U . . .
H00V H -0.089443 0.939776 0.452611 0.072 Uiso 1 1 calc R U . . .
H00W H 0.022385 0.899421 0.582933 0.072 Uiso 1 1 calc R U . . .


_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
N001 C009 1.1521(18) . ?
N002 C00H 1.3812(18) . ?
N002 C00P 1.456(2) . ?
N002 C00S 1.455(2) . ?
N003 C005 1.3699(18) . ?
N003 C00Q 1.452(2) . ?
N003 C00R 1.441(2) . ?
C004 C006 1.4771(18) . ?
C004 C00E 1.3974(19) . ?
C004 C00F 1.3978(18) . ?
C005 C007 1.4110(19) . ?
C005 C00O 1.406(2) . ?
C006 C00A 1.4763(18) . ?
C006 C00D 1.3703(18) . ?
C007 H007 0.9500 . ?
C007 C00F 1.3766(19) . ?
C008 H008 0.9500 . ?
C008 C00A 1.4003(18) . ?
C008 C00G 1.3786(19) . ?
C009 C00D 1.4368(19) . ?
C00A C00K 1.4010(18) . ?
C00B C00D 1.4909(18) . ?
C00B C00J 1.3912(19) . ?
C00B C00M 1.3997(19) . ?
C00C H00C 0.9500 . ?
C00C C00L 1.384(2) . ?
C00C C00N 1.382(2) . ?
C00E H00E 0.9500 . ?
C00E C00O 1.381(2) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00H 1.4052(19) . ?
C00H C00I 1.408(2) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.3782(19) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.387(2) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.3818(19) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00P H00A 0.9800 . ?
C00P H00B 0.9800 . ?
C00P H00D 0.9800 . ?
C00Q H00H 0.9800 . ?
C00Q H00P 0.9800 . ?
C00Q H00Q 0.9800 . ?
C00R H00R 0.9800 . ?
C00R H00S 0.9800 . ?
C00R H00T 0.9800 . ?
C00S H00U 0.9800 . ?
C00S H00V 0.9800 . ?
C00S H00W 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
C00H N002 C00P 118.73(13) . . ?
C00H N002 C00S 118.31(13) . . ?
C00S N002 C00P 116.45(13) . . ?
C005 N003 C00Q 120.74(13) . . ?
C005 N003 C00R 120.72(13) . . ?
C00R N003 C00Q 118.06(13) . . ?
C00E C004 C006 121.62(12) . . ?
C00E C004 C00F 116.77(12) . . ?
C00F C004 C006 121.46(12) . . ?
N003 C005 C007 121.03(13) . . ?
N003 C005 C00O 122.06(13) . . ?
C00O C005 C007 116.91(12) . . ?
C00A C006 C004 117.07(11) . . ?
C00D C006 C004 121.97(12) . . ?
C00D C006 C00A 120.86(12) . . ?
C005 C007 H007 119.4 . . ?
C00F C007 C005 121.22(13) . . ?
C00F C007 H007 119.4 . . ?
C00A C008 H008 119.0 . . ?
C00G C008 H008 119.0 . . ?
C00G C008 C00A 122.07(12) . . ?
N001 C009 C00D 175.92(15) . . ?
C008 C00A C006 121.82(12) . . ?
C008 C00A C00K 116.80(12) . . ?
C00K C00A C006 121.38(12) . . ?
C00J C00B C00D 120.97(12) . . ?
C00J C00B C00M 118.38(12) . . ?
C00M C00B C00D 120.63(12) . . ?
C00L C00C H00C 120.2 . . ?
C00N C00C H00C 120.2 . . ?
C00N C00C C00L 119.60(13) . . ?
C006 C00D C009 119.35(12) . . ?
C006 C00D C00B 126.24(12) . . ?
C009 C00D C00B 114.37(11) . . ?
C004 C00E H00E 119.0 . . ?
C00O C00E C004 122.10(13) . . ?
C00O C00E H00E 118.9 . . ?
C004 C00F H00F 119.0 . . ?
C007 C00F C004 121.96(13) . . ?
C007 C00F H00F 119.0 . . ?
C008 C00G H00G 119.5 . . ?
C008 C00G C00H 121.06(13) . . ?
C00H C00G H00G 119.5 . . ?
N002 C00H C00G 121.95(13) . . ?
N002 C00H C00I 121.06(13) . . ?
C00G C00H C00I 116.99(12) . . ?
C00H C00I H00I 119.3 . . ?
C00K C00I C00H 121.44(13) . . ?
C00K C00I H00I 119.3 . . ?
C00B C00J H00J 119.8 . . ?
C00L C00J C00B 120.45(13) . . ?
C00L C00J H00J 119.8 . . ?
C00A C00K H00K 119.2 . . ?
C00I C00K C00A 121.63(13) . . ?
C00I C00K H00K 119.2 . . ?
C00C C00L C00J 120.50(13) . . ?
C00C C00L H00L 119.7 . . ?
C00J C00L H00L 119.7 . . ?
C00B C00M H00M 119.5 . . ?
C00N C00M C00B 120.93(13) . . ?
C00N C00M H00M 119.5 . . ?
C00C C00N H00N 119.9 . . ?
C00M C00N C00C 120.13(13) . . ?
C00M C00N H00N 119.9 . . ?
C005 C00O H00O 119.5 . . ?
C00E C00O C005 121.01(13) . . ?
C00E C00O H00O 119.5 . . ?
N002 C00P H00A 109.5 . . ?
N002 C00P H00B 109.5 . . ?
N002 C00P H00D 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00D 109.5 . . ?
H00B C00P H00D 109.5 . . ?
N003 C00Q H00H 109.5 . . ?
N003 C00Q H00P 109.5 . . ?
N003 C00Q H00Q 109.5 . . ?
H00H C00Q H00P 109.5 . . ?
H00H C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 109.5 . . ?
N003 C00R H00R 109.5 . . ?
N003 C00R H00S 109.5 . . ?
N003 C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 109.5 . . ?
N002 C00S H00U 109.5 . . ?
N002 C00S H00V 109.5 . . ?
N002 C00S H00W 109.5 . . ?
H00U C00S H00V 109.5 . . ?
H00U C00S H00W 109.5 . . ?
H00V C00S H00W 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
N002 C00H C00I C00K 179.92(13) . . . . ?
N003 C005 C007 C00F -177.87(13) . . . . ?
N003 C005 C00O C00E 176.94(14) . . . . ?
C004 C006 C00A C008 -141.40(13) . . . . ?
C004 C006 C00A C00K 37.95(18) . . . . ?
C004 C006 C00D C009 -162.17(12) . . . . ?
C004 C006 C00D C00B 15.5(2) . . . . ?
C004 C00E C00O C005 1.7(2) . . . . ?
C005 C007 C00F C004 0.2(2) . . . . ?
C006 C004 C00E C00O -176.01(13) . . . . ?
C006 C004 C00F C007 175.08(12) . . . . ?
C006 C00A C00K C00I 179.41(13) . . . . ?
C007 C005 C00O C00E -2.0(2) . . . . ?
C008 C00A C00K C00I -1.2(2) . . . . ?
C008 C00G C00H N002 -179.76(13) . . . . ?
C008 C00G C00H C00I 0.1(2) . . . . ?
C00A C006 C00D C009 14.18(19) . . . . ?
C00A C006 C00D C00B -168.12(12) . . . . ?
C00A C008 C00G C00H -0.9(2) . . . . ?
C00B C00J C00L C00C -0.6(2) . . . . ?
C00B C00M C00N C00C 0.9(2) . . . . ?
C00D C006 C00A C008 42.08(19) . . . . ?
C00D C006 C00A C00K -138.56(14) . . . . ?
C00D C00B C00J C00L 178.95(12) . . . . ?
C00D C00B C00M C00N -179.15(12) . . . . ?
C00E C004 C006 C00A 39.66(17) . . . . ?
C00E C004 C006 C00D -143.86(13) . . . . ?
C00E C004 C00F C007 -0.61(19) . . . . ?
C00F C004 C006 C00A -135.81(13) . . . . ?
C00F C004 C006 C00D 40.66(18) . . . . ?
C00F C004 C00E C00O -0.3(2) . . . . ?
C00G C008 C00A C006 -179.25(12) . . . . ?
C00G C008 C00A C00K 1.4(2) . . . . ?
C00G C00H C00I C00K 0.0(2) . . . . ?
C00H C00I C00K C00A 0.5(2) . . . . ?
C00J C00B C00D C006 46.00(19) . . . . ?
C00J C00B C00D C009 -136.20(13) . . . . ?
C00J C00B C00M C00N -0.9(2) . . . . ?
C00L C00C C00N C00M -0.8(2) . . . . ?
C00M C00B C00D C006 -135.74(14) . . . . ?
C00M C00B C00D C009 42.06(17) . . . . ?
C00M C00B C00J C00L 0.66(19) . . . . ?
C00N C00C C00L C00J 0.6(2) . . . . ?
C00O C005 C007 C00F 1.11(19) . . . . ?
C00P N002 C00H C00G 14.2(2) . . . . ?
C00P N002 C00H C00I -165.67(13) . . . . ?
C00Q N003 C005 C007 5.9(2) . . . . ?
C00Q N003 C005 C00O -173.05(14) . . . . ?
C00R N003 C005 C007 177.78(14) . . . . ?
C00R N003 C005 C00O -1.1(2) . . . . ?
C00S N002 C00H C00G 164.93(14) . . . . ?
C00S N002 C00H C00I -15.0(2) . . . . ?

_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_mo_0109_7_0m
_database_code_depnum_ccdc_archive 'CCDC 2054252'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-09
_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            TPAN-Br
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Br N'
_chemical_formula_sum            'C21 H14 Br N'
_chemical_formula_weight         360.24
_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'
Br Br -0.2901 2.4595 '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                   9.4954(9)
_cell_length_b                   9.5538(8)
_cell_length_c                   10.1628(9)
_cell_angle_alpha                63.011(4)
_cell_angle_beta                 81.004(4)
_cell_angle_gamma                80.806(4)
_cell_volume                     807.29(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.544
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0982 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.3152.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14512
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         2.183
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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                2619
_reflns_number_total             3303
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.340
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.045
_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)+(0.0307P)²+0.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_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
Br01 Br -0.07915(4) 0.17470(4) 0.56130(4) 0.04598(14) Uani 1 1 d . . . . .
N002 N 0.4273(3) 0.7815(3) 0.3094(3) 0.0405(7) Uani 1 1 d . . . . .
C003 C 0.6971(3) 0.5954(4) 0.1315(3) 0.0286(7) Uani 1 1 d . . . . .
C004 C 0.3390(3) 0.4272(3) 0.3540(3) 0.0282(6) Uani 1 1 d . . . . .
C005 C 0.4657(3) 0.5194(3) 0.2844(3) 0.0295(7) Uani 1 1 d . . . . .
C006 C 0.6241(3) 0.3231(4) 0.2160(3) 0.0286(7) Uani 1 1 d . . . . .
C007 C 0.2616(3) 0.4321(4) 0.4804(4) 0.0329(7) Uani 1 1 d . . . . .
H007 H 0.293341 0.489425 0.524080 0.039 Uiso 1 1 calc R . . . .
C008 C 0.5884(3) 0.4809(4) 0.2140(3) 0.0289(6) Uani 1 1 d . . . . .
C009 C 0.2890(3) 0.3436(4) 0.2912(3) 0.0309(7) Uani 1 1 d . . . . .
H009 H 0.340577 0.338387 0.205250 0.037 Uiso 1 1 calc R . . . .
C00A C 0.6594(4) 0.7503(4) 0.0295(3) 0.0331(7) Uani 1 1 d . . . . .
H00A H 0.561418 0.785762 0.013507 0.040 Uiso 1 1 calc R . . . .
C00B C 0.4481(3) 0.6681(4) 0.2949(4) 0.0327(7) Uani 1 1 d . . . . .
C00C C 0.6740(3) 0.3132(4) 0.0832(3) 0.0317(7) Uani 1 1 d . . . . .
H00C H 0.684291 0.407037 -0.006441 0.038 Uiso 1 1 calc R . . . .
C00D C 0.1391(3) 0.3547(4) 0.5437(4) 0.0340(7) Uani 1 1 d . . . . .
H00D H 0.088479 0.356826 0.631237 0.041 Uiso 1 1 calc R . . . .
C00E C 0.0916(3) 0.2748(4) 0.4780(4) 0.0330(7) Uani 1 1 d . . . . .
C00F C 0.1658(3) 0.2683(4) 0.3519(3) 0.0326(7) Uani 1 1 d . . . . .
H00F H 0.132287 0.212616 0.307616 0.039 Uiso 1 1 calc R . . . .
C00G C 0.6141(3) 0.1842(4) 0.3463(4) 0.0334(7) Uani 1 1 d . . . . .
H00G H 0.583297 0.188817 0.437883 0.040 Uiso 1 1 calc R . . . .
C00H C 0.6488(4) 0.0395(4) 0.3436(4) 0.0377(8) Uani 1 1 d . . . . .
H00H H 0.641016 -0.054719 0.433328 0.045 Uiso 1 1 calc R . . . .
C00I C 0.7088(4) 0.1672(4) 0.0813(4) 0.0351(7) Uani 1 1 d . . . . .
H00I H 0.742182 0.161392 -0.009394 0.042 Uiso 1 1 calc R . . . .
C00J C 0.6946(3) 0.0304(4) 0.2115(4) 0.0358(7) Uani 1 1 d . . . . .
H00J H 0.716266 -0.069601 0.210287 0.043 Uiso 1 1 calc R . . . .
C00K C 0.7628(4) 0.8529(4) -0.0488(4) 0.0362(8) Uani 1 1 d . . . . .
H00K H 0.735583 0.958061 -0.117910 0.043 Uiso 1 1 calc R . . . .
C00L C 0.8423(3) 0.5451(4) 0.1511(4) 0.0342(7) Uani 1 1 d . . . . .
H00L H 0.870472 0.439179 0.217775 0.041 Uiso 1 1 calc R . . . .
C00M C 0.9449(4) 0.6490(4) 0.0738(4) 0.0394(8) Uani 1 1 d . . . . .
H00M H 1.042991 0.614618 0.089638 0.047 Uiso 1 1 calc R . . . .
C00N C 0.9057(4) 0.8029(4) -0.0266(4) 0.0402(8) Uani 1 1 d . . . . .
H00N H 0.976738 0.873572 -0.079855 0.048 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
Br01 C00E 1.895(3) . ?
N002 C00B 1.141(4) . ?
C003 C008 1.491(4) . ?
C003 C00A 1.396(4) . ?
C003 C00L 1.400(4) . ?
C004 C005 1.493(4) . ?
C004 C007 1.393(4) . ?
C004 C009 1.397(4) . ?
C005 C008 1.359(4) . ?
C005 C00B 1.454(4) . ?
C006 C008 1.483(4) . ?
C006 C00C 1.399(4) . ?
C006 C00G 1.389(4) . ?
C007 C00D 1.387(4) . ?
C009 C00F 1.381(4) . ?
C00A C00K 1.384(4) . ?
C00C C00I 1.389(4) . ?
C00D C00E 1.378(5) . ?
C00E C00F 1.386(4) . ?
C00G C00H 1.381(4) . ?
C00H C00J 1.381(5) . ?
C00I C00J 1.381(5) . ?
C00K C00N 1.383(5) . ?
C00L C00M 1.383(4) . ?
C00M C00N 1.387(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A C003 C008 122.0(3) . . ?
C00A C003 C00L 118.5(3) . . ?
C00L C003 C008 119.4(3) . . ?
C007 C004 C005 119.5(3) . . ?
C007 C004 C009 118.2(3) . . ?
C009 C004 C005 122.1(3) . . ?
C008 C005 C004 127.9(3) . . ?
C008 C005 C00B 119.1(3) . . ?
C00B C005 C004 113.0(3) . . ?
C00C C006 C008 119.1(3) . . ?
C00G C006 C008 122.2(3) . . ?
C00G C006 C00C 118.6(3) . . ?
C00D C007 C004 121.2(3) . . ?
C005 C008 C003 121.5(3) . . ?
C005 C008 C006 122.6(3) . . ?
C006 C008 C003 115.9(2) . . ?
C00F C009 C004 121.1(3) . . ?
C00K C00A C003 120.8(3) . . ?
N002 C00B C005 175.8(3) . . ?
C00I C00C C006 120.6(3) . . ?
C00E C00D C007 119.2(3) . . ?
C00D C00E Br01 119.1(2) . . ?
C00D C00E C00F 121.0(3) . . ?
C00F C00E Br01 119.9(2) . . ?
C009 C00F C00E 119.3(3) . . ?
C00H C00G C006 120.5(3) . . ?
C00G C00H C00J 120.6(3) . . ?
C00J C00I C00C 119.9(3) . . ?
C00I C00J C00H 119.8(3) . . ?
C00N C00K C00A 120.2(3) . . ?
C00M C00L C003 120.3(3) . . ?
C00L C00M C00N 120.6(3) . . ?
C00K C00N C00M 119.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_0514_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2054257'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-05-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 Cl N3'
_chemical_formula_sum            'C25 H24 Cl N3'
_chemical_formula_weight         401.92
_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'
Cl Cl 0.1484 0.1585 '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      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                   11.0058(6)
_cell_length_b                   21.0329(9)
_cell_length_c                   10.2712(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.795(2)
_cell_angle_gamma                90
_cell_volume                     2122.32(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6165
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            43696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3169
_reflns_number_total             4338
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.133
_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)+(0.0744P)²+0.3330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1440
_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:
 C005(H005), C006(H006), C00B(H00B), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00C,H00D), C00R(H00E,H00L,H00N), C00S(H00Q,H00R,H00S), C00T(H00T,
 H00U,H00V)
;
_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
Cl01 Cl -0.11362(6) 0.64507(3) 0.46274(7) 0.04159(19) Uani 1 1 d . . . . .
N002 N 0.2791(2) 0.91108(9) 0.3880(2) 0.0368(5) Uani 1 1 d . . . . .
N003 N 0.5443(2) 0.50832(9) 0.3549(2) 0.0378(5) Uani 1 1 d . . . . .
N004 N 0.9256(2) 0.92589(9) 0.5719(3) 0.0420(5) Uani 1 1 d . . . . .
C005 C 0.3876(2) 0.66696(9) 0.3073(2) 0.0246(4) Uani 1 1 d . . . . .
H005 H 0.307509 0.688143 0.240131 0.030 Uiso 1 1 calc R U . . .
C006 C 0.4081(2) 0.60449(9) 0.2818(2) 0.0260(4) Uani 1 1 d . . . . .
H006 H 0.343411 0.583836 0.196343 0.031 Uiso 1 1 calc R U . . .
C007 C 0.5241(2) 0.57070(9) 0.3808(2) 0.0256(4) Uani 1 1 d . . . . .
C008 C 0.4816(2) 0.70002(9) 0.4297(2) 0.0224(4) Uani 1 1 d . . . . .
C009 C 0.2270(2) 0.75226(9) 0.4291(2) 0.0236(4) Uani 1 1 d . . . . .
C00A C 0.5818(2) 0.81009(9) 0.4812(2) 0.0245(4) Uani 1 1 d . . . . .
C00B C 0.6166(2) 0.60330(10) 0.5054(2) 0.0267(5) Uani 1 1 d . . . . .
H00B H 0.694078 0.581616 0.575824 0.032 Uiso 1 1 calc R U . . .
C00C C 0.3405(2) 0.79149(9) 0.4303(2) 0.0242(4) Uani 1 1 d . . . . .
C00D C 0.3111(2) 0.85869(10) 0.4105(2) 0.0273(5) Uani 1 1 d . . . . .
C00E C 0.4635(2) 0.76861(9) 0.4492(2) 0.0237(4) Uani 1 1 d . . . . .
C00F C 0.7243(2) 0.90092(10) 0.6040(2) 0.0307(5) Uani 1 1 d . . . . .
H00F H 0.741261 0.936560 0.666695 0.037 Uiso 1 1 calc R U . . .
C00G C 0.5964(2) 0.66674(10) 0.5272(2) 0.0260(5) Uani 1 1 d . . . . .
H00G H 0.662331 0.688075 0.610721 0.031 Uiso 1 1 calc R U . . .
C00H C 0.6716(2) 0.79691(10) 0.4227(2) 0.0283(5) Uani 1 1 d . . . . .
H00H H 0.654660 0.761054 0.360680 0.034 Uiso 1 1 calc R U . . .
C00I C 0.6126(2) 0.86295(10) 0.5739(2) 0.0282(5) Uani 1 1 d . . . . .
H00I H 0.554735 0.872889 0.617290 0.034 Uiso 1 1 calc R U . . .
C00J C 0.2546(2) 0.70423(9) 0.5331(2) 0.0263(5) Uani 1 1 d . . . . .
H00J H 0.346317 0.694912 0.599818 0.032 Uiso 1 1 calc R U . . .
C00K C 0.0915(2) 0.76352(10) 0.3306(2) 0.0292(5) Uani 1 1 d . . . . .
H00K H 0.070875 0.795458 0.258272 0.035 Uiso 1 1 calc R U . . .
C00L C 0.0166(2) 0.68367(10) 0.4426(2) 0.0285(5) Uani 1 1 d . . . . .
C00M C 0.7840(2) 0.83425(10) 0.4520(3) 0.0321(5) Uani 1 1 d . . . . .
H00M H 0.842538 0.823766 0.409925 0.039 Uiso 1 1 calc R U . . .
C00N C 0.8129(2) 0.88779(10) 0.5437(3) 0.0315(5) Uani 1 1 d . . . . .
C00O C -0.0141(2) 0.72920(11) 0.3356(2) 0.0314(5) Uani 1 1 d . . . . .
H00O H -0.105800 0.736919 0.266586 0.038 Uiso 1 1 calc R U . . .
C00P C 0.1502(2) 0.67021(10) 0.5399(2) 0.0286(5) Uani 1 1 d . . . . .
H00P H 0.169979 0.637781 0.611001 0.034 Uiso 1 1 calc R U . . .
C00Q C 0.4563(3) 0.47845(11) 0.2170(3) 0.0445(6) Uani 1 1 d . . . . .
H00A H 0.361529 0.481194 0.200602 0.067 Uiso 1 1 calc R U . . .
H00C H 0.481943 0.433698 0.219368 0.067 Uiso 1 1 calc R U . . .
H00D H 0.465755 0.500286 0.137767 0.067 Uiso 1 1 calc R U . . .
C00R C 0.6722(3) 0.47723(12) 0.4470(3) 0.0474(7) Uani 1 1 d . . . . .
H00E H 0.746550 0.498957 0.437502 0.071 Uiso 1 1 calc R U . . .
H00L H 0.668286 0.432756 0.416872 0.071 Uiso 1 1 calc R U . . .
H00N H 0.688027 0.478958 0.548753 0.071 Uiso 1 1 calc R U . . .
C00S C 0.9760(3) 0.96730(13) 0.6999(3) 0.0543(8) Uani 1 1 d . . . . .
H00Q H 0.902702 0.995555 0.693518 0.081 Uiso 1 1 calc R U . . .
H00R H 1.052076 0.992806 0.703768 0.081 Uiso 1 1 calc R U . . .
H00S H 1.007071 0.941311 0.788346 0.081 Uiso 1 1 calc R U . . .
C00T C 1.0273(3) 0.90222(14) 0.5298(4) 0.0624(9) Uani 1 1 d . . . . .
H00T H 1.070011 0.863917 0.586210 0.094 Uiso 1 1 calc R U . . .
H00U H 1.096800 0.934901 0.549247 0.094 Uiso 1 1 calc R U . . .
H00V H 0.983327 0.891913 0.425531 0.094 Uiso 1 1 calc R U . . .


_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
Cl01 C00L 1.739(2) . ?
N002 C00D 1.148(3) . ?
N003 C007 1.377(3) . ?
N003 C00Q 1.450(3) . ?
N003 C00R 1.450(3) . ?
N004 C00N 1.393(3) . ?
N004 C00S 1.462(4) . ?
N004 C00T 1.458(4) . ?
C005 H005 0.9500 . ?
C005 C006 1.378(3) . ?
C005 C008 1.401(3) . ?
C006 H006 0.9500 . ?
C006 C007 1.413(3) . ?
C007 C00B 1.404(3) . ?
C008 C00E 1.482(3) . ?
C008 C00G 1.395(3) . ?
C009 C00C 1.492(3) . ?
C009 C00J 1.400(3) . ?
C009 C00K 1.395(3) . ?
C00A C00E 1.477(3) . ?
C00A C00H 1.395(3) . ?
C00A C00I 1.403(3) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.388(3) . ?
C00C C00D 1.444(3) . ?
C00C C00E 1.366(3) . ?
C00F H00F 0.9500 . ?
C00F C00I 1.379(3) . ?
C00F C00N 1.399(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00M 1.379(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00P 1.382(3) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.388(3) . ?
C00L C00O 1.380(3) . ?
C00L C00P 1.384(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.409(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q H00A 0.9800 . ?
C00Q H00C 0.9800 . ?
C00Q H00D 0.9800 . ?
C00R H00E 0.9800 . ?
C00R H00L 0.9800 . ?
C00R H00N 0.9800 . ?
C00S H00Q 0.9800 . ?
C00S H00R 0.9800 . ?
C00S H00S 0.9800 . ?
C00T H00T 0.9800 . ?
C00T H00U 0.9800 . ?
C00T H00V 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
C007 N003 C00Q 120.42(19) . . ?
C007 N003 C00R 119.9(2) . . ?
C00R N003 C00Q 117.83(19) . . ?
C00N N004 C00S 118.1(2) . . ?
C00N N004 C00T 118.2(2) . . ?
C00T N004 C00S 116.1(2) . . ?
C006 C005 H005 119.2 . . ?
C006 C005 C008 121.69(19) . . ?
C008 C005 H005 119.2 . . ?
C005 C006 H006 119.5 . . ?
C005 C006 C007 121.00(19) . . ?
C007 C006 H006 119.5 . . ?
N003 C007 C006 120.8(2) . . ?
N003 C007 C00B 121.85(19) . . ?
C00B C007 C006 117.32(18) . . ?
C005 C008 C00E 120.91(18) . . ?
C00G C008 C005 117.31(18) . . ?
C00G C008 C00E 121.67(18) . . ?
C00J C009 C00C 119.99(18) . . ?
C00K C009 C00C 121.96(19) . . ?
C00K C009 C00J 117.99(19) . . ?
C00H C00A C00E 120.74(18) . . ?
C00H C00A C00I 116.69(19) . . ?
C00I C00A C00E 122.54(19) . . ?
C007 C00B H00B 119.5 . . ?
C00G C00B C007 120.92(19) . . ?
C00G C00B H00B 119.5 . . ?
C00D C00C C009 114.00(17) . . ?
C00E C00C C009 125.34(18) . . ?
C00E C00C C00D 120.66(19) . . ?
N002 C00D C00C 175.4(2) . . ?
C00A C00E C008 116.49(17) . . ?
C00C C00E C008 120.61(18) . . ?
C00C C00E C00A 122.81(18) . . ?
C00I C00F H00F 119.5 . . ?
C00I C00F C00N 121.0(2) . . ?
C00N C00F H00F 119.5 . . ?
C008 C00G H00G 119.1 . . ?
C00B C00G C008 121.70(19) . . ?
C00B C00G H00G 119.1 . . ?
C00A C00H H00H 118.9 . . ?
C00M C00H C00A 122.1(2) . . ?
C00M C00H H00H 118.9 . . ?
C00A C00I H00I 119.0 . . ?
C00F C00I C00A 121.9(2) . . ?
C00F C00I H00I 119.0 . . ?
C009 C00J H00J 119.6 . . ?
C00P C00J C009 120.8(2) . . ?
C00P C00J H00J 119.6 . . ?
C009 C00K H00K 119.2 . . ?
C00O C00K C009 121.6(2) . . ?
C00O C00K H00K 119.2 . . ?
C00O C00L Cl01 119.99(17) . . ?
C00O C00L C00P 121.1(2) . . ?
C00P C00L Cl01 118.84(17) . . ?
C00H C00M H00M 119.6 . . ?
C00H C00M C00N 120.7(2) . . ?
C00N C00M H00M 119.6 . . ?
N004 C00N C00F 121.8(2) . . ?
N004 C00N C00M 120.7(2) . . ?
C00F C00N C00M 117.46(19) . . ?
C00K C00O H00O 120.6 . . ?
C00L C00O C00K 118.8(2) . . ?
C00L C00O H00O 120.6 . . ?
C00J C00P C00L 119.6(2) . . ?
C00J C00P H00P 120.2 . . ?
C00L C00P H00P 120.2 . . ?
N003 C00Q H00A 109.5 . . ?
N003 C00Q H00C 109.5 . . ?
N003 C00Q H00D 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00A C00Q H00D 109.5 . . ?
H00C C00Q H00D 109.5 . . ?
N003 C00R H00E 109.5 . . ?
N003 C00R H00L 109.5 . . ?
N003 C00R H00N 109.5 . . ?
H00E C00R H00L 109.5 . . ?
H00E C00R H00N 109.5 . . ?
H00L C00R H00N 109.5 . . ?
N004 C00S H00Q 109.5 . . ?
N004 C00S H00R 109.5 . . ?
N004 C00S H00S 109.5 . . ?
H00Q C00S H00R 109.5 . . ?
H00Q C00S H00S 109.5 . . ?
H00R C00S H00S 109.5 . . ?
N004 C00T H00T 109.5 . . ?
N004 C00T H00U 109.5 . . ?
N004 C00T H00V 109.5 . . ?
H00T C00T H00U 109.5 . . ?
H00T C00T H00V 109.5 . . ?
H00U C00T H00V 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
Cl01 C00L C00O C00K 173.98(17) . . . . ?
Cl01 C00L C00P C00J -174.63(16) . . . . ?
N003 C007 C00B C00G 178.0(2) . . . . ?
C005 C006 C007 N003 -180.0(2) . . . . ?
C005 C006 C007 C00B 0.1(3) . . . . ?
C005 C008 C00E C00A -129.2(2) . . . . ?
C005 C008 C00E C00C 47.5(3) . . . . ?
C005 C008 C00G C00B -0.6(3) . . . . ?
C006 C005 C008 C00E 174.96(19) . . . . ?
C006 C005 C008 C00G -1.3(3) . . . . ?
C006 C007 C00B C00G -2.0(3) . . . . ?
C007 C00B C00G C008 2.4(3) . . . . ?
C008 C005 C006 C007 1.6(3) . . . . ?
C009 C00C C00E C008 17.2(3) . . . . ?
C009 C00C C00E C00A -166.3(2) . . . . ?
C009 C00J C00P C00L 0.1(3) . . . . ?
C009 C00K C00O C00L 1.1(3) . . . . ?
C00A C00H C00M C00N 0.1(3) . . . . ?
C00C C009 C00J C00P 175.69(19) . . . . ?
C00C C009 C00K C00O -176.3(2) . . . . ?
C00D C00C C00E C008 -163.41(19) . . . . ?
C00D C00C C00E C00A 13.1(3) . . . . ?
C00E C008 C00G C00B -176.90(19) . . . . ?
C00E C00A C00H C00M -179.2(2) . . . . ?
C00E C00A C00I C00F 179.3(2) . . . . ?
C00G C008 C00E C00A 47.0(3) . . . . ?
C00G C008 C00E C00C -136.3(2) . . . . ?
C00H C00A C00E C008 33.2(3) . . . . ?
C00H C00A C00E C00C -143.4(2) . . . . ?
C00H C00A C00I C00F 1.2(3) . . . . ?
C00H C00M C00N N004 -179.3(2) . . . . ?
C00H C00M C00N C00F 0.5(3) . . . . ?
C00I C00A C00E C008 -144.9(2) . . . . ?
C00I C00A C00E C00C 38.5(3) . . . . ?
C00I C00A C00H C00M -1.0(3) . . . . ?
C00I C00F C00N N004 179.5(2) . . . . ?
C00I C00F C00N C00M -0.3(3) . . . . ?
C00J C009 C00C C00D -135.9(2) . . . . ?
C00J C009 C00C C00E 43.5(3) . . . . ?
C00J C009 C00K C00O 1.0(3) . . . . ?
C00K C009 C00C C00D 41.3(3) . . . . ?
C00K C009 C00C C00E -139.3(2) . . . . ?
C00K C009 C00J C00P -1.6(3) . . . . ?
C00N C00F C00I C00A -0.6(3) . . . . ?
C00O C00L C00P C00J 2.1(3) . . . . ?
C00P C00L C00O C00K -2.7(3) . . . . ?
C00Q N003 C007 C006 7.7(3) . . . . ?
C00Q N003 C007 C00B -172.3(2) . . . . ?
C00R N003 C007 C006 171.7(2) . . . . ?
C00R N003 C007 C00B -8.3(3) . . . . ?
C00S N004 C00N C00F 19.4(3) . . . . ?
C00S N004 C00N C00M -160.8(2) . . . . ?
C00T N004 C00N C00F 167.8(2) . . . . ?
C00T N004 C00N C00M -12.4(3) . . . . ?

_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_mo_0117_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2054898'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-10 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            NTPAN-I
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 I N3'
_chemical_formula_sum            'C25 H24 I N3'
_chemical_formula_weight         493.37
_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                   9.2457(5)
_cell_length_b                   10.2690(6)
_cell_length_c                   12.5126(7)
_cell_angle_alpha                79.213(3)
_cell_angle_beta                 71.430(2)
_cell_angle_gamma                73.837(3)
_cell_volume                     1075.28(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8836
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.753
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0736 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.3841.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21031
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_min         2.391
_diffrn_ambient_temperature      152.66
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                3633
_reflns_number_total             4424
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.951
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+1.1246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0775
_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:
 C005(H005), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00P(H00P), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00L(H00C,H00F,H00G), C00Q(H00L,H00M,H00N), C00R(H00O,H00Q,H00R), C00T(H00T,
 H00U,H00V)
;
_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 0.68377(3) 0.15077(2) 1.02503(2) 0.05569(10) Uani 1 1 d . . . . .
N002 N 0.4679(3) 0.9389(3) 0.6955(2) 0.0405(6) Uani 1 1 d . . . . .
N003 N 0.9688(3) 0.1512(3) 0.3739(2) 0.0445(6) Uani 1 1 d . . . . .
N004 N 0.8182(4) 0.6267(3) -0.0253(2) 0.0483(7) Uani 1 1 d . . . . .
C005 C 0.6544(3) 0.3703(3) 0.6990(2) 0.0345(6) Uani 1 1 d . . . . .
H005 H 0.581541 0.445760 0.674314 0.041 Uiso 1 1 calc R . . . .
C006 C 0.7888(3) 0.3074(3) 0.6191(2) 0.0324(6) Uani 1 1 d . . . . .
C007 C 0.7933(3) 0.5103(3) 0.3204(2) 0.0326(6) Uani 1 1 d . . . . .
C008 C 0.5468(3) 0.8306(3) 0.6307(2) 0.0335(6) Uani 1 1 d . . . . .
C009 C 0.7668(3) 0.4678(3) 0.1440(3) 0.0376(7) Uani 1 1 d . . . . .
H009 H 0.741783 0.410993 0.104074 0.045 Uiso 1 1 calc R . . . .
C00A C 0.7589(3) 0.4307(3) 0.2568(2) 0.0349(6) Uani 1 1 d . . . . .
H00A H 0.729183 0.348221 0.292659 0.042 Uiso 1 1 calc R . . . .
C00B C 0.8370(3) 0.6301(3) 0.2629(3) 0.0368(7) Uani 1 1 d . . . . .
H00B H 0.860306 0.687414 0.303522 0.044 Uiso 1 1 calc R . . . .
C00C C 0.8195(3) 0.3515(3) 0.4951(2) 0.0324(6) Uani 1 1 d . . . . .
C00D C 0.5584(3) 0.6830(3) 0.4973(2) 0.0316(6) Uani 1 1 d . . . . .
H00D H 0.512848 0.662509 0.446157 0.038 Uiso 1 1 calc R . . . .
C00E C 0.4805(3) 0.7937(3) 0.5583(2) 0.0322(6) Uani 1 1 d . . . . .
H00E H 0.380734 0.845163 0.550971 0.039 Uiso 1 1 calc R . . . .
C00F C 0.7014(3) 0.6008(3) 0.5084(2) 0.0310(6) Uani 1 1 d . . . . .
C00G C 0.8112(3) 0.5886(3) 0.0866(2) 0.0370(7) Uani 1 1 d . . . . .
C00H C 0.8911(4) 0.1947(3) 0.6584(3) 0.0386(7) Uani 1 1 d . . . . .
H00H H 0.981399 0.148679 0.605571 0.046 Uiso 1 1 calc R . . . .
C00I C 0.8473(4) 0.6682(3) 0.1499(3) 0.0400(7) Uani 1 1 d . . . . .
H00I H 0.879479 0.749710 0.114031 0.048 Uiso 1 1 calc R . . . .
C00J C 0.6259(4) 0.3242(3) 0.8137(3) 0.0388(7) Uani 1 1 d . . . . .
H00J H 0.534159 0.367647 0.866890 0.047 Uiso 1 1 calc R . . . .
C00K C 0.7695(3) 0.6389(3) 0.5787(2) 0.0349(6) Uani 1 1 d . . . . .
H00K H 0.868152 0.585815 0.587021 0.042 Uiso 1 1 calc R . . . .
C00L C 0.8500(4) 0.7561(3) -0.0797(3) 0.0466(8) Uani 1 1 d . . . . .
H00C H 0.761211 0.829721 -0.048161 0.070 Uiso 1 1 calc GR . . . .
H00F H 0.865243 0.760766 -0.161352 0.070 Uiso 1 1 calc GR . . . .
H00G H 0.945182 0.766125 -0.066574 0.070 Uiso 1 1 calc GR . . . .
C00M C 0.7757(3) 0.4802(3) 0.4433(2) 0.0321(6) Uani 1 1 d . . . . .
C00N C 0.9032(3) 0.2418(3) 0.4250(3) 0.0354(6) Uani 1 1 d . . . . .
C00O C 0.7320(4) 0.2147(3) 0.8498(2) 0.0388(7) Uani 1 1 d . . . . .
C00P C 0.6958(4) 0.7527(3) 0.6365(3) 0.0384(7) Uani 1 1 d . . . . .
H00P H 0.747097 0.778790 0.681146 0.046 Uiso 1 1 calc R . . . .
C00Q C 0.5592(4) 1.0140(3) 0.7248(3) 0.0446(8) Uani 1 1 d . . . . .
H00L H 0.609345 0.957542 0.781440 0.067 Uiso 1 1 calc GR . . . .
H00M H 0.489871 1.097695 0.755920 0.067 Uiso 1 1 calc GR . . . .
H00N H 0.639934 1.037589 0.656663 0.067 Uiso 1 1 calc GR . . . .
C00R C 0.3121(4) 1.0127(3) 0.6888(3) 0.0409(7) Uani 1 1 d . . . . .
H00O H 0.319023 1.062496 0.613179 0.061 Uiso 1 1 calc GR . . . .
H00Q H 0.266090 1.077284 0.746037 0.061 Uiso 1 1 calc GR . . . .
H00R H 0.245867 0.948062 0.702741 0.061 Uiso 1 1 calc GR . . . .
C00S C 0.8638(4) 0.1486(3) 0.7728(3) 0.0409(7) Uani 1 1 d . . . . .
H00S H 0.935037 0.072127 0.798119 0.049 Uiso 1 1 calc R . . . .
C00T C 0.7702(5) 0.5481(4) -0.0874(3) 0.0541(9) Uani 1 1 d . . . . .
H00T H 0.826250 0.452192 -0.079222 0.081 Uiso 1 1 calc GR . . . .
H00U H 0.794938 0.583583 -0.167851 0.081 Uiso 1 1 calc GR . . . .
H00V H 0.656879 0.555343 -0.057176 0.081 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
I001 C00O 2.107(3) . ?
N002 C008 1.392(4) . ?
N002 C00Q 1.451(4) . ?
N002 C00R 1.449(4) . ?
N003 C00N 1.142(4) . ?
N004 C00G 1.367(4) . ?
N004 C00L 1.438(4) . ?
N004 C00T 1.452(4) . ?
C005 C006 1.402(4) . ?
C005 C00J 1.387(4) . ?
C006 C00C 1.490(4) . ?
C006 C00H 1.397(4) . ?
C007 C00A 1.397(4) . ?
C007 C00B 1.398(4) . ?
C007 C00M 1.476(4) . ?
C008 C00E 1.397(4) . ?
C008 C00P 1.404(4) . ?
C009 C00A 1.375(4) . ?
C009 C00G 1.409(4) . ?
C00B C00I 1.375(4) . ?
C00C C00M 1.371(4) . ?
C00C C00N 1.445(4) . ?
C00D C00E 1.383(4) . ?
C00D C00F 1.389(4) . ?
C00F C00K 1.393(4) . ?
C00F C00M 1.489(4) . ?
C00G C00I 1.403(4) . ?
C00H C00S 1.386(4) . ?
C00J C00O 1.382(4) . ?
C00K C00P 1.384(4) . ?
C00O C00S 1.382(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N002 C00Q 118.7(3) . . ?
C008 N002 C00R 118.8(2) . . ?
C00R N002 C00Q 116.7(3) . . ?
C00G N004 C00L 120.7(3) . . ?
C00G N004 C00T 120.9(3) . . ?
C00L N004 C00T 117.7(3) . . ?
C00J C005 C006 121.2(3) . . ?
C005 C006 C00C 122.3(3) . . ?
C00H C006 C005 117.7(3) . . ?
C00H C006 C00C 119.9(3) . . ?
C00A C007 C00B 116.3(3) . . ?
C00A C007 C00M 124.2(3) . . ?
C00B C007 C00M 119.4(3) . . ?
N002 C008 C00E 121.5(3) . . ?
N002 C008 C00P 121.2(3) . . ?
C00E C008 C00P 117.3(3) . . ?
C00A C009 C00G 121.3(3) . . ?
C009 C00A C007 122.1(3) . . ?
C00I C00B C007 122.5(3) . . ?
C00M C00C C006 127.5(3) . . ?
C00M C00C C00N 118.6(3) . . ?
C00N C00C C006 113.8(2) . . ?
C00E C00D C00F 122.0(3) . . ?
C00D C00E C008 120.7(3) . . ?
C00D C00F C00K 117.4(3) . . ?
C00D C00F C00M 119.1(2) . . ?
C00K C00F C00M 123.5(3) . . ?
N004 C00G C009 121.6(3) . . ?
N004 C00G C00I 121.6(3) . . ?
C00I C00G C009 116.8(3) . . ?
C00S C00H C006 121.4(3) . . ?
C00B C00I C00G 121.0(3) . . ?
C00O C00J C005 119.5(3) . . ?
C00P C00K C00F 121.1(3) . . ?
C007 C00M C00F 114.6(2) . . ?
C00C C00M C007 123.3(3) . . ?
C00C C00M C00F 122.1(3) . . ?
N003 C00N C00C 177.0(3) . . ?
C00J C00O I001 117.8(2) . . ?
C00J C00O C00S 120.8(3) . . ?
C00S C00O I001 121.5(2) . . ?
C00K C00P C008 121.3(3) . . ?
C00O C00S C00H 119.4(3) . . ?

_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_1230xzp03_0m
_database_code_depnum_ccdc_archive 'CCDC 2054253'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_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            TPAN-I
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 I N'
_chemical_formula_sum            'C21 H14 I N'
_chemical_formula_weight         407.23
_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      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                   9.6674(4)
_cell_length_b                   9.7329(4)
_cell_length_c                   10.2634(7)
_cell_angle_alpha                63.694(2)
_cell_angle_beta                 81.390(3)
_cell_angle_gamma                80.864(2)
_cell_volume                     851.27(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74.34
_cell_measurement_theta_min      28.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.747
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1564 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.0894.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8529
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.096
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_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                3161
_reflns_number_total             3273
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.304
_refine_diff_density_min         -3.590
_refine_diff_density_rms         0.316
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.1053
_refine_ls_restrained_S_all      1.207
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2529
_refine_ls_wR_factor_ref         0.2556
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C007(H007), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_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 -0.07856(4) 0.17377(4) 0.57456(5) 0.0611(3) Uani 1 1 d . . . . .
C002 C 0.1053(5) 0.2815(6) 0.4777(5) 0.0377(10) Uani 1 1 d . . . . .
C003 C 0.6254(5) 0.3258(6) 0.2143(5) 0.0339(9) Uani 1 1 d . . . . .
C004 C 0.1736(6) 0.2748(6) 0.3520(5) 0.0399(10) Uani 1 1 d . . . . .
H004 H 0.140136 0.220129 0.310615 0.048 Uiso 1 1 calc R . . . .
C005 C 0.3467(6) 0.4314(5) 0.3486(5) 0.0349(9) Uani 1 1 d . . . . .
C006 C 0.5919(5) 0.4813(6) 0.2104(5) 0.0338(9) Uani 1 1 d . . . . .
C007 C 0.6611(6) 0.7435(6) 0.0314(6) 0.0415(11) Uani 1 1 d . . . . .
H007 H 0.566915 0.778217 0.016384 0.050 Uiso 1 1 calc R . . . .
C008 C 0.6989(5) 0.5917(6) 0.1297(5) 0.0350(9) Uani 1 1 d . . . . .
C009 C 0.4698(5) 0.5216(6) 0.2784(5) 0.0331(9) Uani 1 1 d . . . . .
C00A C 0.2756(5) 0.4356(7) 0.4771(6) 0.0417(11) Uani 1 1 d . . . . .
H00A H 0.309862 0.488636 0.519700 0.050 Uiso 1 1 calc R . . . .
N00B N 0.4310(7) 0.7801(8) 0.3003(8) 0.0611(14) Uani 1 1 d . . . . .
C00C C 0.2940(5) 0.3517(6) 0.2879(5) 0.0372(9) Uani 1 1 d . . . . .
H00C H 0.339394 0.349008 0.202414 0.045 Uiso 1 1 calc R . . . .
C00D C 0.6115(6) 0.1921(6) 0.3457(5) 0.0438(11) Uani 1 1 d . . . . .
H00D H 0.580496 0.199951 0.432615 0.053 Uiso 1 1 calc R . . . .
C00E C 0.6752(6) 0.3113(7) 0.0856(5) 0.0414(11) Uani 1 1 d . . . . .
H00E H 0.686275 0.399555 -0.001114 0.050 Uiso 1 1 calc R . . . .
C00F C 0.4525(6) 0.6682(7) 0.2860(7) 0.0439(11) Uani 1 1 d . . . . .
C00G C 0.6446(7) 0.0475(7) 0.3452(7) 0.0551(14) Uani 1 1 d . . . . .
H00G H 0.634469 -0.041110 0.431786 0.066 Uiso 1 1 calc R . . . .
C00H C 0.1555(6) 0.3619(7) 0.5410(6) 0.0431(11) Uani 1 1 d . . . . .
H00H H 0.108806 0.366077 0.625412 0.052 Uiso 1 1 calc R . . . .
C00I C 0.7638(8) 0.8429(7) -0.0439(7) 0.0512(13) Uani 1 1 d . . . . .
H00I H 0.738286 0.943093 -0.110899 0.061 Uiso 1 1 calc R . . . .
C00J C 0.6928(8) 0.0355(7) 0.2152(9) 0.0564(15) Uani 1 1 d . . . . .
H00J H 0.714659 -0.061071 0.215274 0.068 Uiso 1 1 calc R . . . .
C00K C 0.8413(6) 0.5423(7) 0.1506(6) 0.0433(11) Uani 1 1 d . . . . .
H00K H 0.867908 0.440583 0.213430 0.052 Uiso 1 1 calc R . . . .
C00L C 0.7082(8) 0.1687(9) 0.0848(8) 0.0505(15) Uani 1 1 d . . . . .
H00L H 0.740477 0.160962 -0.002019 0.061 Uiso 1 1 calc R . . . .
C00M C 0.9418(7) 0.6417(10) 0.0796(7) 0.0545(14) Uani 1 1 d . . . . .
H00M H 1.035484 0.607790 0.097900 0.065 Uiso 1 1 calc R . . . .
C00N C 0.9060(8) 0.7928(9) -0.0195(8) 0.0574(15) Uani 1 1 d . . . . .
H00N H 0.974856 0.859454 -0.068633 0.069 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
I001 C002 2.094(5) . ?
C002 C004 1.383(7) . ?
C002 C00H 1.392(7) . ?
C003 C006 1.480(7) . ?
C003 C00D 1.406(7) . ?
C003 C00E 1.396(7) . ?
C004 C00C 1.399(8) . ?
C005 C009 1.490(7) . ?
C005 C00A 1.408(7) . ?
C005 C00C 1.377(7) . ?
C006 C008 1.489(7) . ?
C006 C009 1.373(7) . ?
C007 C008 1.398(7) . ?
C007 C00I 1.390(9) . ?
C008 C00K 1.399(7) . ?
C009 C00F 1.445(7) . ?
C00A C00H 1.382(8) . ?
N00B C00F 1.145(9) . ?
C00D C00G 1.394(9) . ?
C00E C00L 1.378(9) . ?
C00G C00J 1.395(11) . ?
C00I C00N 1.404(11) . ?
C00J C00L 1.400(11) . ?
C00K C00M 1.369(9) . ?
C00M C00N 1.391(11) . ?

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
C004 C002 I001 120.5(4) . . ?
C004 C002 C00H 120.8(5) . . ?
C00H C002 I001 118.7(4) . . ?
C00D C003 C006 121.4(4) . . ?
C00E C003 C006 119.4(4) . . ?
C00E C003 C00D 119.2(5) . . ?
C002 C004 C00C 119.0(4) . . ?
C00A C005 C009 118.8(4) . . ?
C00C C005 C009 122.7(4) . . ?
C00C C005 C00A 118.4(5) . . ?
C003 C006 C008 116.3(4) . . ?
C009 C006 C003 122.1(5) . . ?
C009 C006 C008 121.6(5) . . ?
C00I C007 C008 120.2(5) . . ?
C007 C008 C006 121.6(4) . . ?
C007 C008 C00K 118.8(5) . . ?
C00K C008 C006 119.5(4) . . ?
C006 C009 C005 127.8(4) . . ?
C006 C009 C00F 118.9(5) . . ?
C00F C009 C005 113.3(4) . . ?
C00H C00A C005 120.9(5) . . ?
C005 C00C C004 121.5(5) . . ?
C00G C00D C003 119.7(5) . . ?
C00L C00E C003 121.2(5) . . ?
N00B C00F C009 174.9(7) . . ?
C00D C00G C00J 120.2(6) . . ?
C00A C00H C002 119.4(5) . . ?
C007 C00I C00N 120.4(6) . . ?
C00G C00J C00L 120.0(5) . . ?
C00M C00K C008 120.8(6) . . ?
C00E C00L C00J 119.6(6) . . ?
C00K C00M C00N 121.0(7) . . ?
C00M C00N C00I 118.8(6) . . ?


_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_mo_0114_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2054254'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-14
_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         'C25 H24 Br N3'
_chemical_formula_sum            'C25 H24 Br N3'
_chemical_formula_weight         446.38
_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'
Br Br -0.2901 2.4595 '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                   9.8541(6)
_cell_length_b                   10.6234(6)
_cell_length_c                   11.7377(7)
_cell_angle_alpha                102.009(3)
_cell_angle_beta                 94.363(3)
_cell_angle_gamma                114.749(2)
_cell_volume                     1072.89(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.699
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0778 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.3514.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19279
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         2.189
_diffrn_ambient_temperature      150.48
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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                3674
_reflns_number_total             4427
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.338
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.024
_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)+(0.0421P)²+0.3902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0842
_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:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G),
 C00I(H00I), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00E,H00F,H00H), C00R(H00J,H00K,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,
 H00V,H00W)
;
_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
Br01 Br 0.20934(3) -0.02275(2) 0.31310(2) 0.04829(10) Uani 1 1 d . . . . .
N002 N 0.7167(2) 0.54340(19) 0.05145(17) 0.0411(4) Uani 1 1 d . . . . .
N003 N 0.8560(2) 1.1830(2) 0.08846(18) 0.0429(4) Uani 1 1 d . . . . .
N004 N 0.0291(2) 0.6643(2) 0.46828(18) 0.0526(5) Uani 1 1 d . . . . .
C005 C 0.5245(2) 0.6844(2) 0.23985(17) 0.0324(4) Uani 1 1 d . . . . .
C006 C 0.5402(2) 0.5615(2) 0.19964(18) 0.0323(4) Uani 1 1 d . . . . .
C007 C 0.6413(2) 0.5566(2) 0.11771(18) 0.0341(4) Uani 1 1 d . . . . .
C008 C 0.3974(2) 0.6804(2) 0.30155(18) 0.0322(4) Uani 1 1 d . . . . .
C009 C 0.7723(2) 0.8666(2) 0.20315(19) 0.0349(4) Uani 1 1 d . . . . .
H009 H 0.822883 0.812930 0.222929 0.042 Uiso 1 1 calc R . . . .
C00A C 0.3362(2) 0.1603(2) 0.16448(19) 0.0367(5) Uani 1 1 d . . . . .
H00A H 0.305727 0.073452 0.104491 0.044 Uiso 1 1 calc R . . . .
C00B C 0.4202(2) 0.7735(2) 0.41198(18) 0.0341(4) Uani 1 1 d . . . . .
H00B H 0.520655 0.842416 0.449550 0.041 Uiso 1 1 calc R . . . .
C00C C 0.2482(2) 0.5851(2) 0.24715(18) 0.0364(5) Uani 1 1 d . . . . .
H00C H 0.229342 0.521437 0.171380 0.044 Uiso 1 1 calc R . . . .
C00D C 0.5537(2) 0.9099(2) 0.19205(19) 0.0350(4) Uani 1 1 d . . . . .
H00D H 0.453088 0.887202 0.205052 0.042 Uiso 1 1 calc R . . . .
C00E C 0.6192(2) 0.8210(2) 0.21358(18) 0.0323(4) Uani 1 1 d . . . . .
C00F C 0.1493(3) 0.6711(2) 0.41361(19) 0.0376(5) Uani 1 1 d . . . . .
C00G C 0.6312(2) 1.0299(2) 0.15245(19) 0.0366(5) Uani 1 1 d . . . . .
H00G H 0.582258 1.086605 0.137206 0.044 Uiso 1 1 calc R . . . .
C00H C 0.3064(2) 0.1569(2) 0.2772(2) 0.0363(5) Uani 1 1 d . . . . .
C00I C 0.4110(2) 0.2918(2) 0.14015(19) 0.0344(4) Uani 1 1 d . . . . .
H00I H 0.432299 0.294408 0.062848 0.041 Uiso 1 1 calc R . . . .
C00J C 0.7813(2) 1.0693(2) 0.13437(18) 0.0345(4) Uani 1 1 d . . . . .
C00K C 0.4562(2) 0.4215(2) 0.22700(18) 0.0326(4) Uani 1 1 d . . . . .
C00L C 0.3007(3) 0.7678(2) 0.46786(19) 0.0365(5) Uani 1 1 d . . . . .
H00L H 0.320648 0.830245 0.544429 0.044 Uiso 1 1 calc R . . . .
C00M C 0.1272(3) 0.5809(2) 0.30047(19) 0.0390(5) Uani 1 1 d . . . . .
H00M H 0.026671 0.515857 0.260041 0.047 Uiso 1 1 calc R . . . .
C00N C 0.8517(2) 0.9870(2) 0.16506(19) 0.0351(4) Uani 1 1 d . . . . .
H00N H 0.955468 1.014737 0.159464 0.042 Uiso 1 1 calc R . . . .
C00O C 0.4226(3) 0.4132(2) 0.33951(19) 0.0367(5) Uani 1 1 d . . . . .
H00O H 0.450669 0.499423 0.399658 0.044 Uiso 1 1 calc R . . . .
C00P C 0.3497(3) 0.2826(2) 0.3653(2) 0.0384(5) Uani 1 1 d . . . . .
H00P H 0.329355 0.279032 0.442659 0.046 Uiso 1 1 calc R . . . .
C00Q C 0.7864(3) 1.2744(3) 0.0675(2) 0.0479(6) Uani 1 1 d . . . . .
H00E H 0.690498 1.216661 0.010812 0.072 Uiso 1 1 calc GR . . . .
H00F H 0.855238 1.350136 0.035153 0.072 Uiso 1 1 calc GR . . . .
H00H H 0.766286 1.318256 0.142297 0.072 Uiso 1 1 calc GR . . . .
C00R C 1.0090(3) 1.2193(3) 0.0687(2) 0.0491(6) Uani 1 1 d . . . . .
H00J H 1.078480 1.257611 0.145106 0.074 Uiso 1 1 calc GR . . . .
H00K H 1.038653 1.292013 0.023960 0.074 Uiso 1 1 calc GR . . . .
H00Q H 1.013773 1.133081 0.023596 0.074 Uiso 1 1 calc GR . . . .
C00S C -0.1258(3) 0.5722(3) 0.4062(2) 0.0554(7) Uani 1 1 d . . . . .
H00R H -0.147407 0.607720 0.339785 0.083 Uiso 1 1 calc GR . . . .
H00S H -0.196222 0.572557 0.460749 0.083 Uiso 1 1 calc GR . . . .
H00T H -0.138497 0.473906 0.376092 0.083 Uiso 1 1 calc GR . . . .
C00T C 0.0508(3) 0.7712(3) 0.5752(2) 0.0654(8) Uani 1 1 d . . . . .
H00U H 0.127750 0.774942 0.635570 0.098 Uiso 1 1 calc GR . . . .
H00V H -0.045407 0.746138 0.604193 0.098 Uiso 1 1 calc GR . . . .
H00W H 0.084744 0.865331 0.558611 0.098 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
Br01 C00H 1.898(2) . ?
N002 C007 1.143(3) . ?
N003 C00J 1.370(3) . ?
N003 C00Q 1.452(3) . ?
N003 C00R 1.441(3) . ?
N004 C00F 1.373(3) . ?
N004 C00S 1.450(3) . ?
N004 C00T 1.440(3) . ?
C005 C006 1.370(3) . ?
C005 C008 1.483(3) . ?
C005 C00E 1.472(3) . ?
C006 C007 1.445(3) . ?
C006 C00K 1.486(3) . ?
C008 C00B 1.395(3) . ?
C008 C00C 1.391(3) . ?
C009 C00E 1.402(3) . ?
C009 C00N 1.379(3) . ?
C00A C00H 1.382(3) . ?
C00A C00I 1.383(3) . ?
C00B C00L 1.377(3) . ?
C00C C00M 1.377(3) . ?
C00D C00E 1.400(3) . ?
C00D C00G 1.382(3) . ?
C00F C00L 1.409(3) . ?
C00F C00M 1.407(3) . ?
C00G C00J 1.405(3) . ?
C00H C00P 1.383(3) . ?
C00I C00K 1.403(3) . ?
C00J C00N 1.406(3) . ?
C00K C00O 1.397(3) . ?
C00O C00P 1.381(3) . ?

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
C00J N003 C00Q 120.32(19) . . ?
C00J N003 C00R 120.3(2) . . ?
C00R N003 C00Q 119.24(19) . . ?
C00F N004 C00S 120.4(2) . . ?
C00F N004 C00T 120.7(2) . . ?
C00T N004 C00S 117.2(2) . . ?
C006 C005 C008 120.23(18) . . ?
C006 C005 C00E 122.77(18) . . ?
C00E C005 C008 116.66(17) . . ?
C005 C006 C007 120.50(18) . . ?
C005 C006 C00K 126.57(18) . . ?
C007 C006 C00K 112.86(17) . . ?
N002 C007 C006 175.6(2) . . ?
C00B C008 C005 122.47(18) . . ?
C00C C008 C005 120.01(18) . . ?
C00C C008 C00B 117.46(19) . . ?
C00N C009 C00E 122.0(2) . . ?
C00H C00A C00I 119.08(19) . . ?
C00L C00B C008 121.6(2) . . ?
C00M C00C C008 121.61(19) . . ?
C00G C00D C00E 121.88(19) . . ?
C009 C00E C005 124.06(19) . . ?
C00D C00E C005 119.30(18) . . ?
C00D C00E C009 116.58(19) . . ?
N004 C00F C00L 121.9(2) . . ?
N004 C00F C00M 121.4(2) . . ?
C00M C00F C00L 116.70(19) . . ?
C00D C00G C00J 121.0(2) . . ?
C00A C00H Br01 119.50(16) . . ?
C00A C00H C00P 121.03(19) . . ?
C00P C00H Br01 119.45(16) . . ?
C00A C00I C00K 121.53(19) . . ?
N003 C00J C00G 121.5(2) . . ?
N003 C00J C00N 121.29(19) . . ?
C00G C00J C00N 117.22(19) . . ?
C00I C00K C006 120.51(18) . . ?
C00O C00K C006 121.94(19) . . ?
C00O C00K C00I 117.52(19) . . ?
C00B C00L C00F 121.25(19) . . ?
C00C C00M C00F 121.3(2) . . ?
C009 C00N C00J 120.95(19) . . ?
C00P C00O C00K 121.5(2) . . ?
C00O C00P C00H 119.4(2) . . ?


_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_mo_0110_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2054237'
loop_
_audit_author_name
_audit_author_address
'Xiong Zuping'
;zhejiang normal university
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_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            TPAN
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N'
_chemical_formula_sum            'C21 H15 N'
_chemical_formula_weight         281.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.8520(18)
_cell_length_b                   9.5451(16)
_cell_length_c                   16.504(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.615(5)
_cell_angle_gamma                90
_cell_volume                     1501.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4380
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0856 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24679
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         2.486
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_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                1956
_reflns_number_total             3069
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.277
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.037
_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)+(0.0487P)²+0.8503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1435
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C006(H006), C008(H008), C009(H009), C00A(H00A), C00B(H00B),
 C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
;
_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
N001 N 0.1352(2) 0.4564(2) 0.59250(12) 0.0480(5) Uani 1 1 d . . . . .
C002 C 0.1694(2) 0.4897(2) 0.53399(14) 0.0385(5) Uani 1 1 d . . . . .
C003 C 0.2001(2) 0.3938(2) 0.39954(14) 0.0392(6) Uani 1 1 d . . . . .
C004 C 0.3307(2) 0.6747(2) 0.37499(14) 0.0387(5) Uani 1 1 d . . . . .
C005 C 0.2308(2) 0.2604(2) 0.43356(14) 0.0412(6) Uani 1 1 d . . . . .
H005 H 0.263859 0.250006 0.492505 0.049 Uiso 1 1 calc R . . . .
C006 C 0.3851(2) 0.8447(3) 0.53133(14) 0.0427(6) Uani 1 1 d . . . . .
H006 H 0.466737 0.820052 0.513863 0.051 Uiso 1 1 calc R . . . .
C007 C 0.2633(2) 0.7656(2) 0.50362(14) 0.0403(6) Uani 1 1 d . . . . .
C008 C 0.1648(2) 0.1572(3) 0.29708(15) 0.0447(6) Uani 1 1 d . . . . .
H008 H 0.152815 0.076798 0.262021 0.054 Uiso 1 1 calc R . . . .
C009 C 0.2706(3) 0.7742(2) 0.31482(14) 0.0441(6) Uani 1 1 d . . . . .
H009 H 0.183811 0.816318 0.316159 0.053 Uiso 1 1 calc R . . . .
C00A C 0.1333(3) 0.2892(3) 0.26242(15) 0.0452(6) Uani 1 1 d . . . . .
H00A H 0.099786 0.298981 0.203462 0.054 Uiso 1 1 calc R . . . .
C00B C 0.1437(3) 0.8048(2) 0.52885(15) 0.0449(6) Uani 1 1 d . . . . .
H00B H 0.059686 0.752155 0.510764 0.054 Uiso 1 1 calc R . . . .
C00C C 0.1503(2) 0.4070(3) 0.31313(15) 0.0437(6) Uani 1 1 d . . . . .
H00C H 0.127994 0.496986 0.288826 0.052 Uiso 1 1 calc R . . . .
C00D C 0.2139(3) 0.1429(3) 0.38298(15) 0.0450(6) Uani 1 1 d . . . . .
H00D H 0.235895 0.052735 0.407090 0.054 Uiso 1 1 calc R . . . .
C00E C 0.3891(3) 0.9581(3) 0.58372(14) 0.0456(6) Uani 1 1 d . . . . .
H00E H 0.473599 1.009565 0.603141 0.055 Uiso 1 1 calc R . . . .
C00F C 0.2148(2) 0.5176(2) 0.45758(14) 0.0423(6) Uani 1 1 d . . . . .
C00G C 0.5257(3) 0.6564(3) 0.31143(15) 0.0465(6) Uani 1 1 d . . . . .
H00G H 0.613999 0.617118 0.310660 0.056 Uiso 1 1 calc R . . . .
C00H C 0.4585(2) 0.6144(3) 0.37172(15) 0.0436(6) Uani 1 1 d . . . . .
H00H H 0.499616 0.544189 0.411093 0.052 Uiso 1 1 calc R . . . .
C00I C 0.3359(3) 0.8122(3) 0.25330(15) 0.0471(6) Uani 1 1 d . . . . .
H00I H 0.292292 0.877672 0.211441 0.057 Uiso 1 1 calc R . . . .
C00J C 0.2644(2) 0.6454(2) 0.44575(14) 0.0426(6) Uani 1 1 d . . . . .
C00K C 0.4642(3) 0.7554(3) 0.25244(15) 0.0476(6) Uani 1 1 d . . . . .
H00K H 0.510394 0.784313 0.211227 0.057 Uiso 1 1 calc R . . . .
C00L C 0.1474(3) 0.9208(3) 0.58043(15) 0.0483(6) Uani 1 1 d . . . . .
H00L H 0.065325 0.947737 0.596786 0.058 Uiso 1 1 calc R . . . .
C00M C 0.2694(3) 0.9968(3) 0.60797(15) 0.0474(6) Uani 1 1 d . . . . .
H00M H 0.271519 1.075553 0.643478 0.057 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
N001 C002 1.145(3) . ?
C002 C00F 1.465(3) . ?
C003 C005 1.394(3) . ?
C003 C00C 1.392(3) . ?
C003 C00F 1.505(3) . ?
C004 C009 1.394(3) . ?
C004 C00H 1.398(3) . ?
C004 C00J 1.501(3) . ?
C005 C00D 1.383(3) . ?
C006 C007 1.393(3) . ?
C006 C00E 1.380(3) . ?
C007 C00B 1.396(3) . ?
C007 C00J 1.494(3) . ?
C008 C00A 1.386(3) . ?
C008 C00D 1.384(3) . ?
C009 C00I 1.381(3) . ?
C00A C00C 1.387(3) . ?
C00B C00L 1.391(3) . ?
C00E C00M 1.387(3) . ?
C00F C00J 1.347(3) . ?
C00G C00H 1.386(3) . ?
C00G C00K 1.382(3) . ?
C00I C00K 1.379(4) . ?
C00L C00M 1.380(4) . ?

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
N001 C002 C00F 174.4(3) . . ?
C005 C003 C00F 119.0(2) . . ?
C00C C003 C005 118.7(2) . . ?
C00C C003 C00F 122.2(2) . . ?
C009 C004 C00H 118.5(2) . . ?
C009 C004 C00J 119.4(2) . . ?
C00H C004 C00J 121.8(2) . . ?
C00D C005 C003 121.1(2) . . ?
C00E C006 C007 121.1(2) . . ?
C006 C007 C00B 118.6(2) . . ?
C006 C007 C00J 118.7(2) . . ?
C00B C007 C00J 122.6(2) . . ?
C00D C008 C00A 119.7(2) . . ?
C00I C009 C004 120.7(2) . . ?
C008 C00A C00C 120.5(2) . . ?
C00L C00B C007 120.2(2) . . ?
C00A C00C C003 120.2(2) . . ?
C005 C00D C008 119.8(2) . . ?
C006 C00E C00M 119.8(2) . . ?
C002 C00F C003 113.8(2) . . ?
C00J C00F C002 119.4(2) . . ?
C00J C00F C003 126.8(2) . . ?
C00K C00G C00H 119.9(2) . . ?
C00G C00H C004 120.5(2) . . ?
C00K C00I C009 120.2(2) . . ?
C007 C00J C004 115.4(2) . . ?
C00F C00J C004 121.8(2) . . ?
C00F C00J C007 122.8(2) . . ?
C00I C00K C00G 120.1(2) . . ?
C00M C00L C00B 120.4(2) . . ?
C00L C00M C00E 119.9(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/PE'
