# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_mo_d8v21734_0m
_database_code_depnum_ccdc_archive 'CCDC 2124079'
loop_
_audit_author_name
_audit_author_address
'Linjuan Jiang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 F3 N'
_chemical_formula_weight         313.31

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'

_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                   7.9625(17)
_cell_length_b                   10.485(2)
_cell_length_c                   10.629(2)
_cell_angle_alpha                110.688(6)
_cell_angle_beta                 108.613(6)
_cell_angle_gamma                90.576(6)
_cell_volume                     779.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7279
_cell_measurement_theta_min      5.451
_cell_measurement_theta_max      54.453

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18061
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.726
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2717
_reflns_number_gt                2203
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0559P)²+0.1576P] 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
_refine_ls_extinction_coef       0.13(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2717
_refine_ls_number_parameters     237
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003

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 0.71789(17) 0.83231(13) 0.46342(15) 0.0591(4) Uani 1 1 d . . . . .
C1 C 0.7185(2) 0.79164(15) 0.32652(18) 0.0577(4) Uani 1 1 d . . . . .
C2 C 0.8788(2) 0.82198(18) 0.3053(2) 0.0708(5) Uani 1 1 d . . . . .
H2 H 0.9806 0.8685 0.3838 0.085 Uiso 1 1 calc R U . . .
C3 C 0.8843(3) 0.7834(2) 0.1706(2) 0.0826(6) Uani 1 1 d . . . . .
H3 H 0.9906 0.8034 0.1581 0.099 Uiso 1 1 calc R U . . .
C4 C 0.7333(3) 0.7143(2) 0.0508(2) 0.0878(6) Uani 1 1 d . . . . .
H4 H 0.7391 0.6895 -0.0406 0.105 Uiso 1 1 calc R U . . .
C5 C 0.5777(3) 0.6832(2) 0.0675(2) 0.0822(6) Uani 1 1 d . . . . .
H5 H 0.4776 0.6371 -0.0129 0.099 Uiso 1 1 calc R U . . .
C6 C 0.5663(2) 0.72013(17) 0.20541(18) 0.0634(4) Uani 1 1 d . . . . .
C7 C 0.4105(2) 0.68939(19) 0.23079(19) 0.0712(5) Uani 1 1 d . . . . .
H7 H 0.3071 0.6421 0.1542 0.085 Uiso 1 1 calc R U . . .
C8 C 0.4115(2) 0.72874(18) 0.36647(19) 0.0658(5) Uani 1 1 d . . . . .
H8 H 0.3092 0.7075 0.3835 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5684(2) 0.80239(15) 0.48297(17) 0.0551(4) Uani 1 1 d . . . . .
C10 C 0.5690(2) 0.84995(16) 0.63225(17) 0.0574(4) Uani 1 1 d . . . . .
C11 C 0.6927(2) 0.95003(18) 0.73794(19) 0.0707(5) Uani 1 1 d . . . . .
H11 H 0.7755 0.9893 0.7124 0.085 Uiso 1 1 calc R U . . .
C12 C 0.7130(3) 1.0061(2) 0.8929(2) 0.0910(6) Uani 1 1 d . . . . .
H12A H 0.6214 0.9584 0.9071 0.136 Uiso 1 1 calc R U . . .
H12B H 0.7022 1.1025 0.9228 0.136 Uiso 1 1 calc R U . . .
H12C H 0.8284 0.9935 0.9483 0.136 Uiso 1 1 calc R U . . .
C13 C 0.42456(19) 0.78227(15) 0.65935(16) 0.0538(4) Uani 1 1 d . . . . .
C14 C 0.2857(3) 0.85061(19) 0.6867(2) 0.0796(6) Uani 1 1 d . . . . .
H14 H 0.2821 0.9398 0.6884 0.096 Uiso 1 1 calc R U . . .
C15 C 0.1520(2) 0.78991(19) 0.7116(2) 0.0778(6) Uani 1 1 d . . . . .
H15 H 0.0587 0.8376 0.7289 0.093 Uiso 1 1 calc R U . . .
C16 C 0.1566(2) 0.65938(17) 0.71106(16) 0.0575(4) Uani 1 1 d . . . . .
C17 C 0.2934(2) 0.58839(17) 0.68257(18) 0.0628(4) Uani 1 1 d . . . . .
H17 H 0.2962 0.4991 0.6807 0.075 Uiso 1 1 calc R U . . .
C18 C 0.4260(2) 0.64994(16) 0.65686(17) 0.0591(4) Uani 1 1 d . . . . .
H18 H 0.5179 0.6014 0.6376 0.071 Uiso 1 1 calc R U . . .
C19 C 0.0176(3) 0.5950(2) 0.7446(2) 0.0785(5) Uani 1 1 d D . . . .
F1 F 0.0700(6) 0.6045(7) 0.8776(4) 0.1150(17) Uani 0.6 1 d D U P A 1
F2 F -0.1349(4) 0.6372(5) 0.7139(7) 0.1171(13) Uani 0.6 1 d D U P A 1
F3 F -0.0188(4) 0.4553(2) 0.6693(4) 0.1118(9) Uani 0.7 1 d D U P A 1
F1' F -0.0458(15) 0.6975(6) 0.8341(12) 0.178(3) Uani 0.4 1 d D U P A 2
F2' F -0.1253(11) 0.5503(14) 0.6469(6) 0.206(4) Uani 0.4 1 d D U P A 2
F3' F 0.0755(15) 0.5299(12) 0.8283(15) 0.142(4) Uani 0.3 1 d D U P A 2


_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 C9 1.3247(19) . ?
N1 C1 1.366(2) . ?
C1 C6 1.412(2) . ?
C1 C2 1.416(2) . ?
C2 C3 1.359(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(2) . ?
C7 C8 1.350(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.484(2) . ?
C10 C11 1.332(2) . ?
C10 C13 1.500(2) . ?
C11 C12 1.492(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.377(2) . ?
C13 C18 1.379(2) . ?
C14 C15 1.376(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(2) . ?
C16 C19 1.489(2) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 F2' 1.218(6) . ?
C19 F3' 1.282(8) . ?
C19 F2 1.279(3) . ?
C19 F1 1.306(4) . ?
C19 F3 1.373(3) . ?
C19 F1' 1.382(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 118.48(14) . . ?
N1 C1 C6 122.68(14) . . ?
N1 C1 C2 118.65(15) . . ?
C6 C1 C2 118.67(16) . . ?
C3 C2 C1 120.31(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.05(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.15(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.73(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C1 117.08(15) . . ?
C7 C6 C5 123.84(17) . . ?
C1 C6 C5 119.08(16) . . ?
C8 C7 C6 119.87(16) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.02(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
N1 C9 C8 121.86(15) . . ?
N1 C9 C10 117.74(14) . . ?
C8 C9 C10 120.40(14) . . ?
C11 C10 C9 121.04(15) . . ?
C11 C10 C13 121.32(15) . . ?
C9 C10 C13 117.64(13) . . ?
C10 C11 C12 127.10(17) . . ?
C10 C11 H11 116.4 . . ?
C12 C11 H11 116.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.02(15) . . ?
C14 C13 C10 120.77(14) . . ?
C18 C13 C10 121.22(14) . . ?
C15 C14 C13 121.48(16) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.86(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.71(15) . . ?
C15 C16 C19 120.41(16) . . ?
C17 C16 C19 119.86(16) . . ?
C16 C17 C18 119.91(15) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 121.00(14) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
F2' C19 F3' 119.2(7) . . ?
F2 C19 F1 109.0(3) . . ?
F2 C19 F3 104.4(3) . . ?
F1 C19 F3 102.7(3) . . ?
F2' C19 F1' 96.0(6) . . ?
F3' C19 F1' 97.6(6) . . ?
F2' C19 C16 115.0(4) . . ?
F3' C19 C16 115.5(5) . . ?
F2 C19 C16 115.3(2) . . ?
F1 C19 C16 112.9(2) . . ?
F3 C19 C16 111.51(18) . . ?
F1' C19 C16 108.9(3) . . ?

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
C9 N1 C1 C6 0.5(2) . . . . ?
C9 N1 C1 C2 -179.24(14) . . . . ?
N1 C1 C2 C3 -179.85(15) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
N1 C1 C6 C7 -1.0(2) . . . . ?
C2 C1 C6 C7 178.77(15) . . . . ?
N1 C1 C6 C5 179.27(15) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C4 C5 C6 C7 -178.97(19) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C1 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 -179.97(17) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C1 N1 C9 C8 0.7(2) . . . . ?
C1 N1 C9 C10 -178.73(13) . . . . ?
C7 C8 C9 N1 -1.3(3) . . . . ?
C7 C8 C9 C10 178.05(15) . . . . ?
N1 C9 C10 C11 18.7(2) . . . . ?
C8 C9 C10 C11 -160.69(16) . . . . ?
N1 C9 C10 C13 -161.85(13) . . . . ?
C8 C9 C10 C13 18.7(2) . . . . ?
C9 C10 C11 C12 -178.43(17) . . . . ?
C13 C10 C11 C12 2.2(3) . . . . ?
C11 C10 C13 C14 73.0(2) . . . . ?
C9 C10 C13 C14 -106.46(19) . . . . ?
C11 C10 C13 C18 -107.41(19) . . . . ?
C9 C10 C13 C18 73.16(19) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C10 C13 C14 C15 179.94(18) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C14 C15 C16 C19 177.12(18) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C19 C16 C17 C18 -177.52(16) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
C10 C13 C18 C17 179.66(15) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C15 C16 C19 F2' 78.5(9) . . . . ?
C17 C16 C19 F2' -103.1(9) . . . . ?
C15 C16 C19 F3' -136.5(8) . . . . ?
C17 C16 C19 F3' 42.0(8) . . . . ?
C15 C16 C19 F2 28.4(5) . . . . ?
C17 C16 C19 F2 -153.2(4) . . . . ?
C15 C16 C19 F1 -97.8(4) . . . . ?
C17 C16 C19 F1 80.6(4) . . . . ?
C15 C16 C19 F3 147.2(3) . . . . ?
C17 C16 C19 F3 -34.4(3) . . . . ?
C15 C16 C19 F1' -27.9(7) . . . . ?
C17 C16 C19 F1' 150.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566
C8 H8 F3 0.93 2.64 3.499(3) 153.2 2_566

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v21850_0m
_database_code_depnum_ccdc_archive 'CCDC 2124080'
loop_
_audit_author_name
_audit_author_address
'Linjuan Jiang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 Cl N'
_chemical_formula_weight         367.85

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'

_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                   7.8258(2)
_cell_length_b                   9.6147(3)
_cell_length_c                   13.4508(4)
_cell_angle_alpha                89.6410(10)
_cell_angle_beta                 78.9490(10)
_cell_angle_gamma                77.7140(10)
_cell_volume                     969.93(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      5.234
_cell_measurement_theta_max      54.899

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24173
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.708
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3791
_reflns_number_gt                3130
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0417P)²+0.2589P] 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
_refine_ls_extinction_coef       0.032(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
Cl1 Cl 0.55372(9) 0.21660(7) 0.97359(4) 0.1033(3) Uani 1 1 d . . . . .
N1 N 0.79917(16) 0.44843(12) 0.39150(9) 0.0467(3) Uani 1 1 d . . . . .
C1 C 0.8999(2) 0.37101(16) 0.30810(11) 0.0501(4) Uani 1 1 d . . . . .
C2 C 0.8822(3) 0.4245(2) 0.21162(12) 0.0660(5) Uani 1 1 d . . . . .
H2 H 0.8012 0.5090 0.2063 0.079 Uiso 1 1 calc R U . . .
C3 C 0.9840(3) 0.3523(3) 0.12641(14) 0.0820(6) Uani 1 1 d . . . . .
H3 H 0.9716 0.3882 0.0632 0.098 Uiso 1 1 calc R U . . .
C4 C 1.1060(3) 0.2258(3) 0.13251(16) 0.0862(7) Uani 1 1 d . . . . .
H4 H 1.1763 0.1792 0.0735 0.103 Uiso 1 1 calc R U . . .
C5 C 1.1236(2) 0.1696(2) 0.22376(15) 0.0749(5) Uani 1 1 d . . . . .
H5 H 1.2043 0.0841 0.2268 0.090 Uiso 1 1 calc R U . . .
C6 C 1.0198(2) 0.24038(17) 0.31424(12) 0.0555(4) Uani 1 1 d . . . . .
C7 C 1.0281(2) 0.18921(17) 0.41149(13) 0.0598(4) Uani 1 1 d . . . . .
H7 H 1.1044 0.1031 0.4192 0.072 Uiso 1 1 calc R U . . .
C8 C 0.9251(2) 0.26523(16) 0.49436(12) 0.0527(4) Uani 1 1 d . . . . .
H8 H 0.9294 0.2309 0.5588 0.063 Uiso 1 1 calc R U . . .
C9 C 0.81082(17) 0.39756(14) 0.48203(10) 0.0423(3) Uani 1 1 d . . . . .
C10 C 0.70041(17) 0.48571(14) 0.57108(10) 0.0409(3) Uani 1 1 d . . . . .
C11 C 0.63016(18) 0.62413(14) 0.55980(10) 0.0437(3) Uani 1 1 d . . . . .
H11 H 0.6615 0.6603 0.4962 0.052 Uiso 1 1 calc R U . . .
C12 C 0.51212(18) 0.72140(14) 0.63564(10) 0.0434(3) Uani 1 1 d . . . . .
H12 H 0.4815 0.6872 0.7000 0.052 Uiso 1 1 calc R U . . .
C13 C 0.44300(19) 0.85719(15) 0.62081(10) 0.0463(3) Uani 1 1 d . . . . .
H13 H 0.4749 0.8901 0.5562 0.056 Uiso 1 1 calc R U . . .
C14 C 0.32220(18) 0.95955(14) 0.69583(10) 0.0435(3) Uani 1 1 d . . . . .
C15 C 0.2346(2) 1.08970(16) 0.66565(12) 0.0556(4) Uani 1 1 d . . . . .
H15 H 0.2537 1.1107 0.5974 0.067 Uiso 1 1 calc R U . . .
C16 C 0.1201(2) 1.18807(19) 0.73512(15) 0.0711(5) Uani 1 1 d . . . . .
H16 H 0.0629 1.2746 0.7135 0.085 Uiso 1 1 calc R U . . .
C17 C 0.0904(2) 1.1584(2) 0.83619(15) 0.0725(5) Uani 1 1 d . . . . .
H17 H 0.0127 1.2246 0.8831 0.087 Uiso 1 1 calc R U . . .
C18 C 0.1759(2) 1.03056(19) 0.86790(13) 0.0666(5) Uani 1 1 d . . . . .
H18 H 0.1559 1.0104 0.9363 0.080 Uiso 1 1 calc R U . . .
C19 C 0.2908(2) 0.93258(16) 0.79886(11) 0.0547(4) Uani 1 1 d . . . . .
H19 H 0.3485 0.8469 0.8213 0.066 Uiso 1 1 calc R U . . .
C20 C 0.66725(17) 0.41783(14) 0.67073(10) 0.0408(3) Uani 1 1 d . . . . .
C21 C 0.70183(19) 0.47535(15) 0.75732(11) 0.0476(3) Uani 1 1 d . . . . .
H21 H 0.7502 0.5561 0.7525 0.057 Uiso 1 1 calc R U . . .
C22 C 0.6658(2) 0.41511(18) 0.85054(11) 0.0572(4) Uani 1 1 d . . . . .
H22 H 0.6887 0.4552 0.9080 0.069 Uiso 1 1 calc R U . . .
C23 C 0.5957(2) 0.29520(18) 0.85695(12) 0.0578(4) Uani 1 1 d . . . . .
C24 C 0.5600(2) 0.23526(18) 0.77306(13) 0.0583(4) Uani 1 1 d . . . . .
H24 H 0.5121 0.1543 0.7785 0.070 Uiso 1 1 calc R U . . .
C25 C 0.5959(2) 0.29656(15) 0.68068(11) 0.0508(4) Uani 1 1 d . . . . .
H25 H 0.5720 0.2560 0.6237 0.061 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
Cl1 C23 1.7417(15) . ?
N1 C9 1.3215(18) . ?
N1 C1 1.3621(18) . ?
C1 C6 1.411(2) . ?
C1 C2 1.414(2) . ?
C2 C3 1.362(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(2) . ?
C7 C8 1.357(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.420(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.4846(18) . ?
C10 C11 1.3470(19) . ?
C10 C20 1.4892(18) . ?
C11 C12 1.4323(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.3321(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.4598(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(2) . ?
C14 C19 1.393(2) . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.3886(19) . ?
C20 C25 1.3911(19) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(2) . ?
C24 C25 1.378(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 118.70(13) . . ?
N1 C1 C6 122.82(14) . . ?
N1 C1 C2 118.14(15) . . ?
C6 C1 C2 119.04(14) . . ?
C3 C2 C1 119.99(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.61(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C1 116.95(14) . . ?
C7 C6 C5 124.09(17) . . ?
C1 C6 C5 118.97(17) . . ?
C8 C7 C6 120.10(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.58(15) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C8 121.83(13) . . ?
N1 C9 C10 117.10(12) . . ?
C8 C9 C10 121.07(12) . . ?
C11 C10 C9 119.52(12) . . ?
C11 C10 C20 121.51(12) . . ?
C9 C10 C20 118.96(11) . . ?
C10 C11 C12 126.73(13) . . ?
C10 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C13 C12 C11 124.83(13) . . ?
C13 C12 H12 117.6 . . ?
C11 C12 H12 117.6 . . ?
C12 C13 C14 126.53(13) . . ?
C12 C13 H13 116.7 . . ?
C14 C13 H13 116.7 . . ?
C15 C14 C19 117.59(13) . . ?
C15 C14 C13 120.18(13) . . ?
C19 C14 C13 122.23(13) . . ?
C16 C15 C14 121.21(15) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.05(16) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.79(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.27(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 121.08(15) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C25 117.72(13) . . ?
C21 C20 C10 121.27(12) . . ?
C25 C20 C10 120.99(12) . . ?
C22 C21 C20 121.36(14) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 119.02(14) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 121.27(14) . . ?
C24 C23 Cl1 119.36(13) . . ?
C22 C23 Cl1 119.37(13) . . ?
C23 C24 C25 119.14(15) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C20 121.48(14) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?

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
C9 N1 C1 C6 -1.7(2) . . . . ?
C9 N1 C1 C2 178.14(13) . . . . ?
N1 C1 C2 C3 178.25(15) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
N1 C1 C6 C7 2.0(2) . . . . ?
C2 C1 C6 C7 -177.85(14) . . . . ?
N1 C1 C6 C5 -177.83(14) . . . . ?
C2 C1 C6 C5 2.3(2) . . . . ?
C4 C5 C6 C7 179.31(17) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C1 C6 C7 C8 -0.7(2) . . . . ?
C5 C6 C7 C8 179.14(15) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C1 N1 C9 C8 0.1(2) . . . . ?
C1 N1 C9 C10 179.39(12) . . . . ?
C7 C8 C9 N1 1.2(2) . . . . ?
C7 C8 C9 C10 -178.10(13) . . . . ?
N1 C9 C10 C11 -16.42(19) . . . . ?
C8 C9 C10 C11 162.88(13) . . . . ?
N1 C9 C10 C20 162.48(12) . . . . ?
C8 C9 C10 C20 -18.22(19) . . . . ?
C9 C10 C11 C12 175.74(13) . . . . ?
C20 C10 C11 C12 -3.1(2) . . . . ?
C10 C11 C12 C13 -178.75(14) . . . . ?
C11 C12 C13 C14 179.86(13) . . . . ?
C12 C13 C14 C15 -168.13(15) . . . . ?
C12 C13 C14 C19 12.3(2) . . . . ?
C19 C14 C15 C16 -0.4(2) . . . . ?
C13 C14 C15 C16 -179.94(15) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
C13 C14 C19 C18 -179.77(15) . . . . ?
C11 C10 C20 C21 -53.62(19) . . . . ?
C9 C10 C20 C21 127.50(14) . . . . ?
C11 C10 C20 C25 124.63(15) . . . . ?
C9 C10 C20 C25 -54.24(18) . . . . ?
C25 C20 C21 C22 -0.4(2) . . . . ?
C10 C20 C21 C22 177.89(13) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C21 C22 C23 Cl1 178.80(12) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
Cl1 C23 C24 C25 -179.01(12) . . . . ?
C23 C24 C25 C20 -0.1(2) . . . . ?
C21 C20 C25 C24 0.2(2) . . . . ?
C10 C20 C25 C24 -178.11(13) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

