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

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

data_Compound2g
_database_code_depnum_ccdc_archive 'CCDC 2057955'
loop_
_audit_author_name
_audit_author_address
'Shiqun Xiang'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 F2 N'
_chemical_formula_sum            'C19 H11 F2 N'
_chemical_formula_weight         291.29

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.86350(10)
_cell_length_b                   26.7080(10)
_cell_length_c                   12.5375(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.609(3)
_cell_angle_gamma                90
_cell_volume                     1293.63(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3784
_cell_measurement_theta_min      4.8140
_cell_measurement_theta_max      72.9890

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.892
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6068
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.838
_diffrn_reflns_theta_max         69.919
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.767
_diffrn_reflns_point_group_measured_fraction_full 0.778
_reflns_number_total             1881
_reflns_number_gt                1845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.533
_reflns_Friedel_fraction_max     0.537
_reflns_Friedel_fraction_full    0.555

_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. 
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+3.9800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00124(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 604 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1881
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.3203(9) 0.35994(11) 0.6005(3) 0.0346(8) Uani 1 1 d . . . . .
F2 F 0.1740(9) 0.71193(11) 0.7372(3) 0.0379(9) Uani 1 1 d . . . . .
N1 N 0.5056(11) 0.55380(16) 0.4858(3) 0.0214(9) Uani 1 1 d . . . . .
C1 C 0.6026(13) 0.51781(18) 0.4181(4) 0.0220(11) Uani 1 1 d . . . . .
C2 C 0.5718(13) 0.46386(18) 0.4355(4) 0.0228(11) Uani 1 1 d . . . . .
C3 C 0.4417(14) 0.43855(18) 0.5226(4) 0.0244(11) Uani 1 1 d . . . . .
H3 H 0.350394 0.455530 0.582603 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4535(14) 0.38681(19) 0.5164(4) 0.0264(11) Uani 1 1 d . . . . .
C5 C 0.5820(14) 0.36078(18) 0.4320(4) 0.0282(12) Uani 1 1 d . . . . .
H5 H 0.581245 0.325208 0.431948 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7148(13) 0.38729(19) 0.3456(4) 0.0257(11) Uani 1 1 d . . . . .
H6 H 0.808457 0.370016 0.286267 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7080(12) 0.43897(19) 0.3475(4) 0.0228(11) Uani 1 1 d . . . . .
C8 C 0.8276(14) 0.47621(18) 0.2644(4) 0.0250(12) Uani 1 1 d . . . . .
H8A H 1.077960 0.472530 0.250239 0.030 Uiso 1 1 calc R U . . .
H8B H 0.696363 0.472279 0.196626 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7501(13) 0.52593(19) 0.3166(4) 0.0232(11) Uani 1 1 d . . . . .
C10 C 0.8033(12) 0.5745(2) 0.2809(4) 0.0236(11) Uani 1 1 d . . . . .
H10 H 0.900261 0.581314 0.213144 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7071(13) 0.61231(19) 0.3497(4) 0.0234(11) Uani 1 1 d . . . . .
C12 C 0.7266(13) 0.66836(18) 0.3373(4) 0.0241(11) Uani 1 1 d . . . . .
H12A H 0.584800 0.679908 0.275852 0.029 Uiso 1 1 calc R U . . .
H12B H 0.968556 0.679590 0.327835 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5819(13) 0.68713(18) 0.4413(4) 0.0233(11) Uani 1 1 d . . . . .
C14 C 0.5441(14) 0.7360(2) 0.4787(4) 0.0271(12) Uani 1 1 d . . . . .
H14 H 0.612639 0.763582 0.435922 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4063(15) 0.74399(19) 0.5783(4) 0.0291(13) Uani 1 1 d . . . . .
H15 H 0.376788 0.776969 0.605064 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3123(13) 0.7028(2) 0.6382(4) 0.0277(12) Uani 1 1 d . . . . .
C17 C 0.3406(14) 0.65417(19) 0.6056(4) 0.0237(11) Uani 1 1 d . . . . .
H17 H 0.266194 0.626991 0.648574 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4853(13) 0.64695(19) 0.5055(4) 0.0242(12) Uani 1 1 d . . . . .
C19 C 0.5606(12) 0.60048(18) 0.4487(4) 0.0214(11) 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
F1 C4 1.380(6) . ?
F2 C16 1.378(6) . ?
N1 C1 1.339(7) . ?
N1 C19 1.348(6) . ?
C1 C9 1.416(8) . ?
C1 C2 1.463(7) . ?
C2 C3 1.383(7) . ?
C2 C7 1.395(7) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(7) . ?
C5 C6 1.396(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.517(7) . ?
C8 C9 1.512(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.388(7) . ?
C10 C11 1.381(7) . ?
C10 H10 0.9500 . ?
C11 C19 1.406(7) . ?
C11 C12 1.507(7) . ?
C12 C13 1.510(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.395(7) . ?
C13 C14 1.396(7) . ?
C14 C15 1.379(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(7) . ?
C17 C18 1.393(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.462(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C19 113.5(4) . . ?
N1 C1 C9 125.3(5) . . ?
N1 C1 C2 126.1(5) . . ?
C9 C1 C2 108.6(4) . . ?
C3 C2 C7 122.3(4) . . ?
C3 C2 C1 129.1(5) . . ?
C7 C2 C1 108.6(5) . . ?
C2 C3 C4 115.5(5) . . ?
C2 C3 H3 122.2 . . ?
C4 C3 H3 122.2 . . ?
C5 C4 F1 118.0(4) . . ?
C5 C4 C3 124.4(5) . . ?
F1 C4 C3 117.6(5) . . ?
C4 C5 C6 118.9(5) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 119.1(5) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 119.8(5) . . ?
C6 C7 C8 129.6(5) . . ?
C2 C7 C8 110.6(4) . . ?
C9 C8 C7 102.4(4) . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C10 C9 C1 119.7(5) . . ?
C10 C9 C8 130.5(5) . . ?
C1 C9 C8 109.8(4) . . ?
C11 C10 C9 116.1(5) . . ?
C11 C10 H10 121.9 . . ?
C9 C10 H10 121.9 . . ?
C10 C11 C19 120.0(5) . . ?
C10 C11 C12 130.4(5) . . ?
C19 C11 C12 109.6(4) . . ?
C11 C12 C13 102.8(4) . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C18 C13 C14 119.7(5) . . ?
C18 C13 C12 110.3(4) . . ?
C14 C13 C12 129.9(5) . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.4(5) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 F2 118.0(5) . . ?
C17 C16 C15 124.8(5) . . ?
F2 C16 C15 117.2(4) . . ?
C16 C17 C18 115.8(5) . . ?
C16 C17 H17 122.1 . . ?
C18 C17 H17 122.1 . . ?
C17 C18 C13 121.8(5) . . ?
C17 C18 C19 129.8(5) . . ?
C13 C18 C19 108.4(4) . . ?
N1 C19 C11 125.4(5) . . ?
N1 C19 C18 125.7(4) . . ?
C11 C19 C18 108.9(4) . . ?

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
C19 N1 C1 C9 0.1(7) . . . . ?
C19 N1 C1 C2 -179.3(5) . . . . ?
N1 C1 C2 C3 -0.2(10) . . . . ?
C9 C1 C2 C3 -179.7(5) . . . . ?
N1 C1 C2 C7 -178.7(5) . . . . ?
C9 C1 C2 C7 1.8(6) . . . . ?
C7 C2 C3 C4 -0.4(7) . . . . ?
C1 C2 C3 C4 -178.7(5) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C2 C3 C4 F1 -178.7(4) . . . . ?
F1 C4 C5 C6 179.4(5) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C5 C6 C7 C2 0.4(8) . . . . ?
C5 C6 C7 C8 -178.7(5) . . . . ?
C3 C2 C7 C6 0.2(8) . . . . ?
C1 C2 C7 C6 178.8(4) . . . . ?
C3 C2 C7 C8 179.5(4) . . . . ?
C1 C2 C7 C8 -1.9(6) . . . . ?
C6 C7 C8 C9 -179.6(5) . . . . ?
C2 C7 C8 C9 1.2(6) . . . . ?
N1 C1 C9 C10 -0.1(8) . . . . ?
C2 C1 C9 C10 179.4(5) . . . . ?
N1 C1 C9 C8 179.5(5) . . . . ?
C2 C1 C9 C8 -1.0(6) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C7 C8 C9 C1 -0.1(5) . . . . ?
C1 C9 C10 C11 0.4(7) . . . . ?
C8 C9 C10 C11 -179.1(5) . . . . ?
C9 C10 C11 C19 -0.8(7) . . . . ?
C9 C10 C11 C12 -179.9(5) . . . . ?
C10 C11 C12 C13 -179.7(5) . . . . ?
C19 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 C18 -0.8(6) . . . . ?
C11 C12 C13 C14 177.6(5) . . . . ?
C18 C13 C14 C15 -1.0(8) . . . . ?
C12 C13 C14 C15 -179.3(5) . . . . ?
C13 C14 C15 C16 0.5(8) . . . . ?
C14 C15 C16 C17 -1.0(8) . . . . ?
C14 C15 C16 F2 -179.7(5) . . . . ?
F2 C16 C17 C18 -179.3(5) . . . . ?
C15 C16 C17 C18 2.0(8) . . . . ?
C16 C17 C18 C13 -2.4(7) . . . . ?
C16 C17 C18 C19 178.2(5) . . . . ?
C14 C13 C18 C17 2.1(8) . . . . ?
C12 C13 C18 C17 -179.3(5) . . . . ?
C14 C13 C18 C19 -178.4(5) . . . . ?
C12 C13 C18 C19 0.2(5) . . . . ?
C1 N1 C19 C11 -0.5(7) . . . . ?
C1 N1 C19 C18 -179.0(5) . . . . ?
C10 C11 C19 N1 0.9(8) . . . . ?
C12 C11 C19 N1 -179.8(5) . . . . ?
C10 C11 C19 C18 179.6(5) . . . . ?
C12 C11 C19 C18 -1.1(6) . . . . ?
C17 C18 C19 N1 -1.3(9) . . . . ?
C13 C18 C19 N1 179.3(5) . . . . ?
C17 C18 C19 C11 -180.0(5) . . . . ?
C13 C18 C19 C11 0.6(5) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_Compound2v
_database_code_depnum_ccdc_archive 'CCDC 2083284'
loop_
_audit_author_name
_audit_author_address
'Shiqun Xiang'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N'
_chemical_formula_sum            'C23 H21 N'
_chemical_formula_weight         311.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   11.0913(14)
_cell_length_b                   16.1163(18)
_cell_length_c                   9.1839(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1259
_cell_measurement_theta_min      4.8030
_cell_measurement_theta_max      71.9870

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.549
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            3709
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.840
_diffrn_reflns_theta_max         64.978
_diffrn_reflns_theta_full        64.978
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             1351
_reflns_number_gt                1043
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1351
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.500000 0.37887(13) 0.750000 0.0208(5) Uani 1 2 d S T P . .
C1 C 0.57900(17) 0.42158(12) 0.83231(17) 0.0218(5) Uani 1 1 d . . . . .
C2 C 0.66156(18) 0.37152(12) 0.92530(17) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.61550(19) 0.30446(12) 1.00382(19) 0.0271(5) Uani 1 1 d . . . . .
H3 H 0.532999 0.289808 0.993246 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6882(2) 0.25895(13) 1.0969(2) 0.0313(5) Uani 1 1 d . . . . .
H4 H 0.655254 0.214188 1.151212 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8094(2) 0.27902(13) 1.1105(2) 0.0332(5) Uani 1 1 d . . . . .
H5 H 0.859747 0.248245 1.174526 0.040 Uiso 1 1 calc R U . . .
C6 C 0.85671(19) 0.34431(14) 1.0301(2) 0.0311(5) Uani 1 1 d . . . . .
H6 H 0.939955 0.357236 1.039016 0.037 Uiso 1 1 calc R U . . .
C7 C 0.78506(17) 0.39137(12) 0.93670(18) 0.0242(5) Uani 1 1 d . . . . .
C8 C 0.83797(19) 0.45995(13) 0.8465(2) 0.0294(5) Uani 1 1 d . . . . .
H8A H 0.812773 0.452103 0.744027 0.035 Uiso 1 1 calc R U . . .
H8B H 0.926957 0.455609 0.849938 0.035 Uiso 1 1 calc R U . . .
C9 C 0.80133(19) 0.54724(13) 0.8952(2) 0.0285(5) Uani 1 1 d . . . . .
H9A H 0.851306 0.563555 0.979840 0.034 Uiso 1 1 calc R U . . .
H9B H 0.818190 0.586791 0.815318 0.034 Uiso 1 1 calc R U . . .
C10 C 0.66811(18) 0.55376(12) 0.93719(19) 0.0238(5) Uani 1 1 d . . . . .
H10A H 0.657829 0.531508 1.036892 0.029 Uiso 1 1 calc R U . . .
H10B H 0.645205 0.613116 0.939345 0.029 Uiso 1 1 calc R U . . .
C11 C 0.58308(17) 0.50849(12) 0.83660(17) 0.0226(5) Uani 1 1 d . . . . .
C12 C 0.500000 0.55070(16) 0.750000 0.0213(6) Uani 1 2 d S T P . .
H12 H 0.500000 0.609646 0.749999 0.026 Uiso 1 2 calc R U P . .


_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
N1 C1 1.346(2) 4_656 ?
N1 C1 1.346(2) . ?
C1 C11 1.402(3) . ?
C1 C2 1.490(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.411(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.501(3) . ?
C8 C9 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.508(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.394(2) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 118.5(2) 4_656 . ?
N1 C1 C11 123.20(17) . . ?
N1 C1 C2 116.42(17) . . ?
C11 C1 C2 120.35(16) . . ?
C3 C2 C7 119.51(18) . . ?
C3 C2 C1 119.37(18) . . ?
C7 C2 C1 121.11(17) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.73(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.62(19) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 118.42(18) . . ?
C6 C7 C8 121.17(18) . . ?
C2 C7 C8 120.38(17) . . ?
C7 C8 C9 114.31(16) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 113.13(16) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.60(16) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C1 116.75(18) . . ?
C12 C11 C10 121.77(18) . . ?
C1 C11 C10 121.38(17) . . ?
C11 C12 C11 121.6(2) . 4_656 ?
C11 C12 H12 119.2 . . ?
C11 C12 H12 119.2 4_656 . ?

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
C1 N1 C1 C11 0.01(12) 4_656 . . . ?
C1 N1 C1 C2 177.92(16) 4_656 . . . ?
N1 C1 C2 C3 -43.9(2) . . . . ?
C11 C1 C2 C3 134.05(18) . . . . ?
N1 C1 C2 C7 136.88(16) . . . . ?
C11 C1 C2 C7 -45.2(2) . . . . ?
C7 C2 C3 C4 2.4(3) . . . . ?
C1 C2 C3 C4 -176.83(16) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C6 C7 C8 -177.91(18) . . . . ?
C3 C2 C7 C6 -1.8(3) . . . . ?
C1 C2 C7 C6 177.37(16) . . . . ?
C3 C2 C7 C8 176.34(16) . . . . ?
C1 C2 C7 C8 -4.5(3) . . . . ?
C6 C7 C8 C9 -109.3(2) . . . . ?
C2 C7 C8 C9 72.5(2) . . . . ?
C7 C8 C9 C10 -41.5(2) . . . . ?
C8 C9 C10 C11 -42.0(2) . . . . ?
N1 C1 C11 C12 0.0(2) . . . . ?
C2 C1 C11 C12 -177.85(13) . . . . ?
N1 C1 C11 C10 176.29(14) . . . . ?
C2 C1 C11 C10 -1.5(3) . . . . ?
C9 C10 C11 C12 -113.54(18) . . . . ?
C9 C10 C11 C1 70.3(2) . . . . ?
C1 C11 C12 C11 0.01(10) . . . 4_656 ?
C10 C11 C12 C11 -176.29(18) . . . 4_656 ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_Compound2k
_database_code_depnum_ccdc_archive 'CCDC 2059281'
loop_
_audit_author_name
_audit_author_address
'Shiqun Xiang'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl2 N'
_chemical_formula_sum            'C19 H11 Cl2 N'
_chemical_formula_weight         324.19

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1916(3)
_cell_length_b                   8.2658(4)
_cell_length_c                   13.5299(5)
_cell_angle_alpha                87.021(4)
_cell_angle_beta                 75.797(4)
_cell_angle_gamma                68.795(5)
_cell_volume                     726.29(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      5.7070
_cell_measurement_theta_max      72.3740

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.957
_shelx_estimated_absorpt_T_min   0.450
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            13120
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.746
_diffrn_reflns_theta_max         69.975
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2737
_reflns_number_gt                2419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+0.1697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2737
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.81474(10) 0.28931(7) -0.08412(4) 0.0517(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57006(8) 0.98796(6) 0.86648(4) 0.0432(2) Uani 1 1 d . . . . .
N1 N 0.7457(2) 0.5737(2) 0.40144(12) 0.0289(4) Uani 1 1 d . . . . .
C1 C 0.7877(3) 0.4295(2) 0.34523(15) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.7947(3) 0.4227(2) 0.23645(15) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.7585(3) 0.5540(3) 0.16729(16) 0.0360(4) Uani 1 1 d . . . . .
H3 H 0.729662 0.670610 0.187593 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7651(3) 0.5125(3) 0.06846(17) 0.0412(5) Uani 1 1 d . . . . .
H4 H 0.739640 0.600493 0.020191 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8097(3) 0.3397(3) 0.04031(16) 0.0387(5) Uani 1 1 d . . . . .
C6 C 0.8486(3) 0.2071(3) 0.10735(15) 0.0343(4) Uani 1 1 d . . . . .
H6 H 0.880351 0.090391 0.086171 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8400(3) 0.2494(2) 0.20672(15) 0.0302(4) Uani 1 1 d . . . . .
C8 C 0.8672(3) 0.1344(2) 0.29603(15) 0.0322(4) Uani 1 1 d . . . . .
H8A H 1.008217 0.046502 0.283408 0.039 Uiso 1 1 calc R U . . .
H8B H 0.767014 0.074624 0.310826 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8278(3) 0.2609(2) 0.38199(15) 0.0296(4) Uani 1 1 d . . . . .
C10 C 0.8241(3) 0.2351(2) 0.48438(15) 0.0315(4) Uani 1 1 d . . . . .
H10 H 0.848723 0.123373 0.511994 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7825(3) 0.3809(2) 0.54453(15) 0.0290(4) Uani 1 1 d . . . . .
C12 C 0.7690(3) 0.3990(2) 0.65648(15) 0.0320(4) Uani 1 1 d . . . . .
H12A H 0.902192 0.332332 0.672834 0.038 Uiso 1 1 calc R U . . .
H12B H 0.661319 0.359402 0.698769 0.038 Uiso 1 1 calc R U . . .
C13 C 0.7133(3) 0.5919(2) 0.67230(15) 0.0295(4) Uani 1 1 d . . . . .
C14 C 0.6740(3) 0.6876(2) 0.76147(15) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.681572 0.632675 0.824576 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6233(3) 0.8658(3) 0.75538(15) 0.0323(4) Uani 1 1 d . . . . .
C16 C 0.6150(3) 0.9498(2) 0.66381(16) 0.0333(4) Uani 1 1 d . . . . .
H16 H 0.580542 1.072105 0.662295 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6577(3) 0.8528(2) 0.57439(15) 0.0313(4) Uani 1 1 d . . . . .
H17 H 0.655504 0.907363 0.510932 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7037(3) 0.6742(2) 0.57974(14) 0.0277(4) Uani 1 1 d . . . . .
C19 C 0.7458(3) 0.5432(2) 0.49998(15) 0.0281(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.744(2) . ?
Cl2 C15 1.739(2) . ?
N1 C19 1.344(2) . ?
N1 C1 1.346(2) . ?
C1 C9 1.407(3) . ?
C1 C2 1.464(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.406(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.505(3) . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.386(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C19 1.403(3) . ?
C11 C12 1.506(3) . ?
C12 C13 1.510(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(3) . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.467(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
C19 N1 C1 113.26(16) . . ?
N1 C1 C9 125.54(18) . . ?
N1 C1 C2 125.67(17) . . ?
C9 C1 C2 108.78(16) . . ?
C3 C2 C7 120.85(18) . . ?
C3 C2 C1 130.85(17) . . ?
C7 C2 C1 108.25(17) . . ?
C4 C3 C2 119.04(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 122.56(19) . . ?
C6 C5 Cl1 118.54(16) . . ?
C4 C5 Cl1 118.90(17) . . ?
C5 C6 C7 117.97(18) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C2 120.23(19) . . ?
C6 C7 C8 129.47(17) . . ?
C2 C7 C8 110.27(16) . . ?
C7 C8 C9 102.91(15) . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C1 119.42(18) . . ?
C10 C9 C8 130.81(18) . . ?
C1 C9 C8 109.76(17) . . ?
C9 C10 C11 116.60(18) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
C10 C11 C19 119.36(18) . . ?
C10 C11 C12 130.38(18) . . ?
C19 C11 C12 110.26(16) . . ?
C11 C12 C13 102.62(15) . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C18 120.47(17) . . ?
C14 C13 C12 129.34(18) . . ?
C18 C13 C12 110.19(16) . . ?
C15 C14 C13 117.85(19) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 122.54(18) . . ?
C14 C15 Cl2 118.50(16) . . ?
C16 C15 Cl2 118.96(15) . . ?
C15 C16 C17 119.30(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 118.81(18) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C13 121.00(18) . . ?
C17 C18 C19 130.42(18) . . ?
C13 C18 C19 108.58(16) . . ?
N1 C19 C11 125.81(17) . . ?
N1 C19 C18 125.87(17) . . ?
C11 C19 C18 108.32(17) . . ?

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
C19 N1 C1 C9 0.3(2) . . . . ?
C19 N1 C1 C2 178.82(16) . . . . ?
N1 C1 C2 C3 -1.3(3) . . . . ?
C9 C1 C2 C3 177.37(19) . . . . ?
N1 C1 C2 C7 -178.97(16) . . . . ?
C9 C1 C2 C7 -0.2(2) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -176.60(19) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 Cl1 179.30(16) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
Cl1 C5 C6 C7 -178.72(14) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C5 C6 C7 C8 177.45(18) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 177.73(15) . . . . ?
C3 C2 C7 C8 -178.60(16) . . . . ?
C1 C2 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 -176.95(17) . . . . ?
C2 C7 C8 C9 1.28(19) . . . . ?
N1 C1 C9 C10 0.4(3) . . . . ?
C2 C1 C9 C10 -178.30(16) . . . . ?
N1 C1 C9 C8 179.81(16) . . . . ?
C2 C1 C9 C8 1.1(2) . . . . ?
C7 C8 C9 C10 177.87(18) . . . . ?
C7 C8 C9 C1 -1.43(19) . . . . ?
C1 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 179.99(17) . . . . ?
C9 C10 C11 C19 0.4(3) . . . . ?
C9 C10 C11 C12 -179.34(18) . . . . ?
C10 C11 C12 C13 -178.45(18) . . . . ?
C19 C11 C12 C13 1.75(19) . . . . ?
C11 C12 C13 C14 177.91(18) . . . . ?
C11 C12 C13 C18 -2.05(19) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C15 -179.26(17) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C13 C14 C15 Cl2 179.12(13) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
Cl2 C15 C16 C17 179.91(14) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 C13 -1.9(3) . . . . ?
C16 C17 C18 C19 177.18(17) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
C12 C13 C18 C17 -179.11(16) . . . . ?
C14 C13 C18 C19 -178.34(15) . . . . ?
C12 C13 C18 C19 1.6(2) . . . . ?
C1 N1 C19 C11 -0.7(3) . . . . ?
C1 N1 C19 C18 -179.48(15) . . . . ?
C10 C11 C19 N1 0.3(3) . . . . ?
C12 C11 C19 N1 -179.85(16) . . . . ?
C10 C11 C19 C18 179.30(15) . . . . ?
C12 C11 C19 C18 -0.9(2) . . . . ?
C17 C18 C19 N1 -0.7(3) . . . . ?
C13 C18 C19 N1 178.50(16) . . . . ?
C17 C18 C19 C11 -179.64(18) . . . . ?
C13 C18 C19 C11 -0.5(2) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_Compound2m
_database_code_depnum_ccdc_archive 'CCDC 2088707'
loop_
_audit_author_name
_audit_author_address
'Shiqun Xiang'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   12.6441(2)
_cell_length_b                   17.5664(3)
_cell_length_c                   15.4560(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.037(2)
_cell_angle_gamma                90
_cell_volume                     3135.25(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9366
_cell_measurement_theta_min      3.7420
_cell_measurement_theta_max      76.2100

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.684
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            16507
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.828
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5897
_reflns_number_gt                5102
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.6889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5897
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.03509(9) 0.39234(6) 0.58788(7) 0.0287(2) Uani 1 1 d . . . . .
N2 N 0.59036(9) 0.43343(6) 0.09015(7) 0.0287(2) Uani 1 1 d . . . . .
O1 O -0.26928(8) 0.34546(6) 0.79285(7) 0.0365(2) Uani 1 1 d . . . . .
O2 O 0.36297(8) 0.63277(6) 0.58236(7) 0.0369(2) Uani 1 1 d . . . . .
O3 O 0.25089(9) 0.35907(7) 0.25264(7) 0.0433(3) Uani 1 1 d . . . . .
O4 O 0.89346(8) 0.69504(6) 0.10267(7) 0.0372(2) Uani 1 1 d . . . . .
C1 C 0.10131(10) 0.45425(7) 0.59686(8) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.17965(10) 0.46687(8) 0.54951(8) 0.0283(3) Uani 1 1 d . . . . .
C3 C 0.20329(11) 0.42272(8) 0.48485(9) 0.0325(3) Uani 1 1 d . . . . .
H3 H 0.165786 0.375202 0.463620 0.039 Uiso 1 1 calc R U . . .
C4 C 0.28324(11) 0.45015(9) 0.45228(9) 0.0352(3) Uani 1 1 d . . . . .
H4 H 0.300530 0.420680 0.408151 0.042 Uiso 1 1 calc R U . . .
C5 C 0.33893(11) 0.51977(9) 0.48253(10) 0.0352(3) Uani 1 1 d . . . . .
H5 H 0.393648 0.537072 0.459292 0.042 Uiso 1 1 calc R U . . .
C6 C 0.31438(11) 0.56392(8) 0.54677(9) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.23393(10) 0.53703(8) 0.57981(9) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.19233(11) 0.57493(8) 0.64728(9) 0.0304(3) Uani 1 1 d . . . . .
H8A H 0.153043 0.623731 0.621369 0.036 Uiso 1 1 calc R U . . .
H8B H 0.257078 0.584322 0.709459 0.036 Uiso 1 1 calc R U . . .
C9 C 0.10887(10) 0.51729(7) 0.65528(9) 0.0281(3) Uani 1 1 d . . . . .
C10 C 0.04459(10) 0.51829(7) 0.70978(9) 0.0284(3) Uani 1 1 d . . . . .
H10 H 0.049046 0.559378 0.751092 0.034 Uiso 1 1 calc R U . . .
C11 C -0.02648(10) 0.45592(7) 0.70048(9) 0.0279(3) Uani 1 1 d . . . . .
C12 C -0.10624(11) 0.43889(7) 0.74798(9) 0.0294(3) Uani 1 1 d . . . . .
H12A H -0.169232 0.476968 0.730880 0.035 Uiso 1 1 calc R U . . .
H12B H -0.063714 0.437489 0.817740 0.035 Uiso 1 1 calc R U . . .
C13 C -0.15268(11) 0.36150(7) 0.70907(9) 0.0286(3) Uani 1 1 d . . . . .
C14 C -0.22911(11) 0.31577(8) 0.72994(9) 0.0308(3) Uani 1 1 d . . . . .
C15 C -0.25774(11) 0.24430(8) 0.68768(10) 0.0346(3) Uani 1 1 d . . . . .
H15 H -0.308961 0.212122 0.701858 0.042 Uiso 1 1 calc R U . . .
C16 C -0.21131(12) 0.21993(8) 0.62458(10) 0.0379(3) Uani 1 1 d . . . . .
H16 H -0.231689 0.171133 0.596116 0.045 Uiso 1 1 calc R U . . .
C17 C -0.13602(11) 0.26537(8) 0.60245(10) 0.0343(3) Uani 1 1 d . . . . .
H17 H -0.105463 0.248597 0.558837 0.041 Uiso 1 1 calc R U . . .
C18 C -0.10654(11) 0.33630(8) 0.64605(9) 0.0295(3) Uani 1 1 d . . . . .
C19 C -0.02768(10) 0.39564(7) 0.64026(8) 0.0270(3) Uani 1 1 d . . . . .
C20 C -0.34145(13) 0.29781(9) 0.82065(11) 0.0434(3) Uani 1 1 d . . . . .
H20A H -0.411261 0.284310 0.764763 0.065 Uiso 1 1 calc R U . . .
H20B H -0.363472 0.325022 0.866157 0.065 Uiso 1 1 calc R U . . .
H20C H -0.299151 0.251370 0.850115 0.065 Uiso 1 1 calc R U . . .
C21 C 0.44113(13) 0.66440(9) 0.54684(12) 0.0433(4) Uani 1 1 d . . . . .
H21A H 0.401587 0.670376 0.477973 0.065 Uiso 1 1 calc R U . . .
H21B H 0.507713 0.630373 0.561986 0.065 Uiso 1 1 calc R U . . .
H21C H 0.467856 0.714226 0.576119 0.065 Uiso 1 1 calc R U . . .
C22 C 0.64872(10) 0.49895(7) 0.10306(8) 0.0269(3) Uani 1 1 d . . . . .
C23 C 0.72975(11) 0.51939(8) 0.06070(9) 0.0294(3) Uani 1 1 d . . . . .
C24 C 0.76366(12) 0.47947(8) -0.00160(9) 0.0336(3) Uani 1 1 d . . . . .
H24 H 0.733507 0.430289 -0.023722 0.040 Uiso 1 1 calc R U . . .
C25 C 0.84267(12) 0.51365(9) -0.03030(9) 0.0374(3) Uani 1 1 d . . . . .
H25 H 0.866800 0.487386 -0.072880 0.045 Uiso 1 1 calc R U . . .
C26 C 0.88790(11) 0.58616(9) 0.00204(9) 0.0349(3) Uani 1 1 d . . . . .
H26 H 0.941867 0.608591 -0.018725 0.042 Uiso 1 1 calc R U . . .
C27 C 0.85361(11) 0.62510(8) 0.06451(9) 0.0312(3) Uani 1 1 d . . . . .
C28 C 0.77384(10) 0.59138(8) 0.09335(9) 0.0293(3) Uani 1 1 d . . . . .
C29 C 0.72419(11) 0.62233(7) 0.15970(9) 0.0298(3) Uani 1 1 d . . . . .
H29A H 0.681098 0.670217 0.135131 0.036 Uiso 1 1 calc R U . . .
H29B H 0.785669 0.631613 0.223559 0.036 Uiso 1 1 calc R U . . .
C30 C 0.64428(10) 0.55934(7) 0.16150(9) 0.0282(3) Uani 1 1 d . . . . .
C31 C 0.57294(11) 0.55371(7) 0.20947(9) 0.0292(3) Uani 1 1 d . . . . .
H31 H 0.568019 0.593280 0.249560 0.035 Uiso 1 1 calc R U . . .
C32 C 0.50897(10) 0.48708(8) 0.19582(9) 0.0285(3) Uani 1 1 d . . . . .
C33 C 0.42313(11) 0.46257(8) 0.23487(9) 0.0306(3) Uani 1 1 d . . . . .
H33A H 0.355398 0.497085 0.214019 0.037 Uiso 1 1 calc R U . . .
H33B H 0.459131 0.460551 0.304952 0.037 Uiso 1 1 calc R U . . .
C34 C 0.38941(11) 0.38392(8) 0.19242(9) 0.0303(3) Uani 1 1 d . . . . .
C35 C 0.30881(11) 0.33391(8) 0.20023(9) 0.0333(3) Uani 1 1 d . . . . .
C36 C 0.29169(12) 0.26354(8) 0.15444(10) 0.0373(3) Uani 1 1 d . . . . .
H36 H 0.238210 0.228127 0.160309 0.045 Uiso 1 1 calc R U . . .
C37 C 0.35330(12) 0.24531(8) 0.10001(10) 0.0386(3) Uani 1 1 d . . . . .
H37 H 0.341676 0.197054 0.069770 0.046 Uiso 1 1 calc R U . . .
C38 C 0.43069(11) 0.29577(8) 0.08913(10) 0.0340(3) Uani 1 1 d . . . . .
H38 H 0.470886 0.283469 0.050744 0.041 Uiso 1 1 calc R U . . .
C39 C 0.44796(10) 0.36528(8) 0.13621(9) 0.0302(3) Uani 1 1 d . . . . .
C40 C 0.52162(10) 0.42985(7) 0.13708(8) 0.0275(3) Uani 1 1 d . . . . .
C41 C 0.14974(13) 0.31851(9) 0.24472(13) 0.0454(4) Uani 1 1 d . . . . .
H41A H 0.097367 0.313367 0.177723 0.068 Uiso 1 1 calc R U . . .
H41B H 0.110532 0.346424 0.278092 0.068 Uiso 1 1 calc R U . . .
H41C H 0.171757 0.267855 0.272912 0.068 Uiso 1 1 calc R U . . .
C42 C 0.97660(12) 0.73132(9) 0.07586(11) 0.0421(3) Uani 1 1 d . . . . .
H42A H 0.940739 0.743660 0.008181 0.063 Uiso 1 1 calc R U . . .
H42B H 1.042316 0.697001 0.088387 0.063 Uiso 1 1 calc R U . . .
H42C H 1.003815 0.778218 0.112609 0.063 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
N1 C1 1.3448(17) . ?
N1 C19 1.3462(17) . ?
N2 C22 1.3374(17) . ?
N2 C40 1.3413(17) . ?
O1 C14 1.3704(17) . ?
O1 C20 1.4274(17) . ?
O2 C6 1.3666(17) . ?
O2 C21 1.4243(17) . ?
O3 C35 1.3680(17) . ?
O3 C41 1.4251(18) . ?
O4 C27 1.3671(17) . ?
O4 C42 1.4275(17) . ?
C1 C9 1.4074(18) . ?
C1 C2 1.4683(18) . ?
C2 C3 1.3903(19) . ?
C2 C7 1.3956(19) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3936(19) . ?
C7 C8 1.5013(18) . ?
C8 C9 1.5034(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3885(18) . ?
C10 C11 1.3869(19) . ?
C10 H10 0.9500 . ?
C11 C19 1.4059(18) . ?
C11 C12 1.4995(18) . ?
C12 C13 1.5056(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3918(19) . ?
C13 C18 1.3957(19) . ?
C14 C15 1.393(2) . ?
C15 C16 1.395(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3933(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.4703(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C30 1.4092(18) . ?
C22 C23 1.4676(18) . ?
C23 C28 1.3912(19) . ?
C23 C24 1.3925(19) . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3905(19) . ?
C28 C29 1.5052(18) . ?
C29 C30 1.5063(18) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.3849(18) . ?
C31 C32 1.3890(19) . ?
C31 H31 0.9500 . ?
C32 C40 1.4068(18) . ?
C32 C33 1.5037(18) . ?
C33 C34 1.5144(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.3874(19) . ?
C34 C39 1.3905(19) . ?
C35 C36 1.397(2) . ?
C36 C37 1.397(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.380(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.3924(19) . ?
C38 H38 0.9500 . ?
C39 C40 1.4643(18) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C19 113.45(11) . . ?
C22 N2 C40 113.54(11) . . ?
C14 O1 C20 117.22(11) . . ?
C6 O2 C21 117.31(12) . . ?
C35 O3 C41 117.77(12) . . ?
C27 O4 C42 117.49(12) . . ?
N1 C1 C9 125.40(12) . . ?
N1 C1 C2 126.06(12) . . ?
C9 C1 C2 108.53(12) . . ?
C3 C2 C7 120.90(13) . . ?
C3 C2 C1 131.32(13) . . ?
C7 C2 C1 107.78(11) . . ?
C4 C3 C2 117.98(13) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.79(13) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 119.97(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O2 C6 C5 125.90(13) . . ?
O2 C6 C7 115.34(12) . . ?
C5 C6 C7 118.76(13) . . ?
C6 C7 C2 120.59(12) . . ?
C6 C7 C8 128.23(13) . . ?
C2 C7 C8 111.17(11) . . ?
C7 C8 C9 102.40(11) . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C10 C9 C1 119.71(12) . . ?
C10 C9 C8 130.19(12) . . ?
C1 C9 C8 110.09(11) . . ?
C11 C10 C9 116.22(12) . . ?
C11 C10 H10 121.9 . . ?
C9 C10 H10 121.9 . . ?
C10 C11 C19 119.70(12) . . ?
C10 C11 C12 130.06(12) . . ?
C19 C11 C12 110.23(11) . . ?
C11 C12 C13 102.44(10) . . ?
C11 C12 H12A 111.3 . . ?
C13 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
C13 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C18 120.37(12) . . ?
C14 C13 C12 128.56(12) . . ?
C18 C13 C12 111.05(11) . . ?
O1 C14 C13 115.95(12) . . ?
O1 C14 C15 125.10(12) . . ?
C13 C14 C15 118.94(13) . . ?
C14 C15 C16 120.08(13) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 121.49(13) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.05(13) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C13 121.05(13) . . ?
C17 C18 C19 131.23(13) . . ?
C13 C18 C19 107.72(11) . . ?
N1 C19 C11 125.50(12) . . ?
N1 C19 C18 125.92(12) . . ?
C11 C19 C18 108.56(11) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C30 125.44(12) . . ?
N2 C22 C23 125.94(12) . . ?
C30 C22 C23 108.61(11) . . ?
C28 C23 C24 121.19(13) . . ?
C28 C23 C22 108.06(11) . . ?
C24 C23 C22 130.75(13) . . ?
C25 C24 C23 117.96(14) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C24 C25 C26 121.49(13) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C27 C26 C25 119.86(13) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
O4 C27 C26 125.31(13) . . ?
O4 C27 C28 115.63(12) . . ?
C26 C27 C28 119.05(13) . . ?
C27 C28 C23 120.45(12) . . ?
C27 C28 C29 128.52(13) . . ?
C23 C28 C29 111.03(11) . . ?
C28 C29 C30 102.49(10) . . ?
C28 C29 H29A 111.3 . . ?
C30 C29 H29A 111.3 . . ?
C28 C29 H29B 111.3 . . ?
C30 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C31 C30 C22 119.61(12) . . ?
C31 C30 C29 130.58(12) . . ?
C22 C30 C29 109.82(11) . . ?
C30 C31 C32 116.41(12) . . ?
C30 C31 H31 121.8 . . ?
C32 C31 H31 121.8 . . ?
C31 C32 C40 119.20(12) . . ?
C31 C32 C33 130.62(12) . . ?
C40 C32 C33 110.17(11) . . ?
C32 C33 C34 102.08(11) . . ?
C32 C33 H33A 111.4 . . ?
C34 C33 H33A 111.4 . . ?
C32 C33 H33B 111.4 . . ?
C34 C33 H33B 111.4 . . ?
H33A C33 H33B 109.2 . . ?
C35 C34 C39 120.14(13) . . ?
C35 C34 C33 128.83(12) . . ?
C39 C34 C33 110.97(12) . . ?
O3 C35 C34 115.88(13) . . ?
O3 C35 C36 125.17(13) . . ?
C34 C35 C36 118.95(13) . . ?
C35 C36 C37 119.92(13) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 121.53(13) . . ?
C38 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
C37 C38 C39 117.87(14) . . ?
C37 C38 H38 121.1 . . ?
C39 C38 H38 121.1 . . ?
C34 C39 C38 121.53(13) . . ?
C34 C39 C40 108.09(12) . . ?
C38 C39 C40 130.37(13) . . ?
N2 C40 C32 125.77(12) . . ?
N2 C40 C39 125.55(12) . . ?
C32 C40 C39 108.68(12) . . ?
O3 C41 H41A 109.5 . . ?
O3 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O3 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O4 C42 H42A 109.5 . . ?
O4 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O4 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C19 N1 C1 C9 0.93(17) . . . . ?
C19 N1 C1 C2 179.41(11) . . . . ?
N1 C1 C2 C3 2.0(2) . . . . ?
C9 C1 C2 C3 -179.35(12) . . . . ?
N1 C1 C2 C7 -178.51(11) . . . . ?
C9 C1 C2 C7 0.18(13) . . . . ?
C7 C2 C3 C4 0.69(18) . . . . ?
C1 C2 C3 C4 -179.83(12) . . . . ?
C2 C3 C4 C5 -0.10(19) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C21 O2 C6 C5 3.68(19) . . . . ?
C21 O2 C6 C7 -176.77(11) . . . . ?
C4 C5 C6 O2 179.68(12) . . . . ?
C4 C5 C6 C7 0.14(19) . . . . ?
O2 C6 C7 C2 -179.14(10) . . . . ?
C5 C6 C7 C2 0.45(18) . . . . ?
O2 C6 C7 C8 1.62(19) . . . . ?
C5 C6 C7 C8 -178.79(12) . . . . ?
C3 C2 C7 C6 -0.88(18) . . . . ?
C1 C2 C7 C6 179.53(11) . . . . ?
C3 C2 C7 C8 178.48(11) . . . . ?
C1 C2 C7 C8 -1.11(13) . . . . ?
C6 C7 C8 C9 -179.18(12) . . . . ?
C2 C7 C8 C9 1.52(13) . . . . ?
N1 C1 C9 C10 0.20(18) . . . . ?
C2 C1 C9 C10 -178.50(10) . . . . ?
N1 C1 C9 C8 179.51(11) . . . . ?
C2 C1 C9 C8 0.81(13) . . . . ?
C7 C8 C9 C10 177.82(12) . . . . ?
C7 C8 C9 C1 -1.39(13) . . . . ?
C1 C9 C10 C11 -1.52(17) . . . . ?
C8 C9 C10 C11 179.33(12) . . . . ?
C9 C10 C11 C19 1.68(17) . . . . ?
C9 C10 C11 C12 -179.96(12) . . . . ?
C10 C11 C12 C13 -177.91(12) . . . . ?
C19 C11 C12 C13 0.57(13) . . . . ?
C11 C12 C13 C14 178.24(12) . . . . ?
C11 C12 C13 C18 -0.33(13) . . . . ?
C20 O1 C14 C13 -175.79(12) . . . . ?
C20 O1 C14 C15 3.29(19) . . . . ?
C18 C13 C14 O1 179.78(11) . . . . ?
C12 C13 C14 O1 1.33(18) . . . . ?
C18 C13 C14 C15 0.64(18) . . . . ?
C12 C13 C14 C15 -177.81(12) . . . . ?
O1 C14 C15 C16 -179.91(12) . . . . ?
C13 C14 C15 C16 -0.86(19) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C13 -0.96(19) . . . . ?
C16 C17 C18 C19 177.78(12) . . . . ?
C14 C13 C18 C17 0.28(18) . . . . ?
C12 C13 C18 C17 178.98(11) . . . . ?
C14 C13 C18 C19 -178.72(10) . . . . ?
C12 C13 C18 C19 -0.02(13) . . . . ?
C1 N1 C19 C11 -0.76(17) . . . . ?
C1 N1 C19 C18 -179.12(11) . . . . ?
C10 C11 C19 N1 -0.56(18) . . . . ?
C12 C11 C19 N1 -179.22(11) . . . . ?
C10 C11 C19 C18 178.05(11) . . . . ?
C12 C11 C19 C18 -0.62(13) . . . . ?
C17 C18 C19 N1 0.1(2) . . . . ?
C13 C18 C19 N1 178.99(11) . . . . ?
C17 C18 C19 C11 -178.46(13) . . . . ?
C13 C18 C19 C11 0.40(13) . . . . ?
C40 N2 C22 C30 1.72(17) . . . . ?
C40 N2 C22 C23 -179.70(11) . . . . ?
N2 C22 C23 C28 -178.71(11) . . . . ?
C30 C22 C23 C28 0.06(13) . . . . ?
N2 C22 C23 C24 1.4(2) . . . . ?
C30 C22 C23 C24 -179.85(13) . . . . ?
C28 C23 C24 C25 -0.09(18) . . . . ?
C22 C23 C24 C25 179.82(12) . . . . ?
C23 C24 C25 C26 0.12(19) . . . . ?
C24 C25 C26 C27 0.2(2) . . . . ?
C42 O4 C27 C26 0.37(18) . . . . ?
C42 O4 C27 C28 179.26(11) . . . . ?
C25 C26 C27 O4 178.36(12) . . . . ?
C25 C26 C27 C28 -0.49(19) . . . . ?
O4 C27 C28 C23 -178.43(11) . . . . ?
C26 C27 C28 C23 0.53(18) . . . . ?
O4 C27 C28 C29 1.14(19) . . . . ?
C26 C27 C28 C29 -179.90(12) . . . . ?
C24 C23 C28 C27 -0.24(18) . . . . ?
C22 C23 C28 C27 179.84(11) . . . . ?
C24 C23 C28 C29 -179.88(11) . . . . ?
C22 C23 C28 C29 0.19(14) . . . . ?
C27 C28 C29 C30 -179.96(12) . . . . ?
C23 C28 C29 C30 -0.35(13) . . . . ?
N2 C22 C30 C31 -1.45(19) . . . . ?
C23 C22 C30 C31 179.77(11) . . . . ?
N2 C22 C30 C29 178.49(11) . . . . ?
C23 C22 C30 C29 -0.29(13) . . . . ?
C28 C29 C30 C31 -179.68(12) . . . . ?
C28 C29 C30 C22 0.39(13) . . . . ?
C22 C30 C31 C32 -0.17(17) . . . . ?
C29 C30 C31 C32 179.91(12) . . . . ?
C30 C31 C32 C40 1.25(17) . . . . ?
C30 C31 C32 C33 -179.06(12) . . . . ?
C31 C32 C33 C34 -178.97(12) . . . . ?
C40 C32 C33 C34 0.74(13) . . . . ?
C32 C33 C34 C35 -177.23(12) . . . . ?
C32 C33 C34 C39 0.01(13) . . . . ?
C41 O3 C35 C34 165.59(12) . . . . ?
C41 O3 C35 C36 -13.7(2) . . . . ?
C39 C34 C35 O3 -176.36(11) . . . . ?
C33 C34 C35 O3 0.65(19) . . . . ?
C39 C34 C35 C36 2.93(19) . . . . ?
C33 C34 C35 C36 179.94(12) . . . . ?
O3 C35 C36 C37 177.69(12) . . . . ?
C34 C35 C36 C37 -1.5(2) . . . . ?
C35 C36 C37 C38 -0.7(2) . . . . ?
C36 C37 C38 C39 1.6(2) . . . . ?
C35 C34 C39 C38 -2.13(19) . . . . ?
C33 C34 C39 C38 -179.65(11) . . . . ?
C35 C34 C39 C40 176.79(11) . . . . ?
C33 C34 C39 C40 -0.72(14) . . . . ?
C37 C38 C39 C34 -0.13(19) . . . . ?
C37 C38 C39 C40 -178.79(12) . . . . ?
C22 N2 C40 C32 -0.50(17) . . . . ?
C22 N2 C40 C39 -179.95(11) . . . . ?
C31 C32 C40 N2 -0.98(19) . . . . ?
C33 C32 C40 N2 179.27(11) . . . . ?
C31 C32 C40 C39 178.54(11) . . . . ?
C33 C32 C40 C39 -1.20(14) . . . . ?
C34 C39 C40 N2 -179.28(11) . . . . ?
C38 C39 C40 N2 -0.5(2) . . . . ?
C34 C39 C40 C32 1.19(14) . . . . ?
C38 C39 C40 C32 179.99(12) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037



