# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2012ncs0208a
_database_code_depnum_ccdc_archive 'CCDC 1491434'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 Cl N2 O'
_chemical_formula_sum            'C22 H19 Cl N2 O'
_chemical_formula_weight         362.84

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   18.6683(5)
_cell_length_b                   10.1255(2)
_cell_length_c                   18.9205(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.979(7)
_cell_angle_gamma                90.00
_cell_volume                     3567.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19404
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Left): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24168
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8114
_reflns_number_gt                6553
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 OMIT command was used to remove the following 3 reflections from all 
 refinement calculations -3 5 11, -9 11 6, -6 3 1
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+1.8474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8114
_refine_ls_number_parameters     475
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.00819(8) 0.41948(15) 0.18025(8) 0.0162(3) Uani 1 1 d . . .
C2 C 0.90224(8) 0.29475(14) 0.18121(8) 0.0151(3) Uani 1 1 d . . .
H2 H 0.8912 0.2936 0.2322 0.018 Uiso 1 1 calc R . .
C3 C 0.96649(8) 0.20030(15) 0.17205(8) 0.0161(3) Uani 1 1 d . . .
H3 H 0.9665 0.1282 0.2082 0.019 Uiso 1 1 calc R . .
C4 C 0.89548(7) 0.54344(14) 0.17206(8) 0.0138(3) Uani 1 1 d . . .
C5 C 0.89653(8) 0.63933(15) 0.11923(8) 0.0156(3) Uani 1 1 d . . .
C6 C 0.85803(8) 0.75614(15) 0.12379(8) 0.0189(3) Uani 1 1 d . . .
H6 H 0.8594 0.8209 0.0876 0.023 Uiso 1 1 calc R . .
C7 C 0.81769(8) 0.77767(15) 0.18138(9) 0.0198(3) Uani 1 1 d . . .
H7 H 0.7915 0.8576 0.1848 0.024 Uiso 1 1 calc R . .
C8 C 0.81543(8) 0.68259(15) 0.23425(8) 0.0187(3) Uani 1 1 d . . .
H8 H 0.7874 0.6972 0.2736 0.022 Uiso 1 1 calc R . .
C9 C 0.85420(7) 0.56631(15) 0.22948(8) 0.0155(3) Uani 1 1 d . . .
H9 H 0.8526 0.5017 0.2657 0.019 Uiso 1 1 calc R . .
C10 C 0.83404(8) 0.26426(14) 0.13661(8) 0.0150(3) Uani 1 1 d . . .
C11 C 0.81551(8) 0.32664(15) 0.07254(8) 0.0172(3) Uani 1 1 d . . .
H11 H 0.8471 0.3899 0.0545 0.021 Uiso 1 1 calc R . .
C12 C 0.75101(8) 0.29688(16) 0.03473(9) 0.0210(3) Uani 1 1 d . . .
H12 H 0.7385 0.3408 -0.0088 0.025 Uiso 1 1 calc R . .
C13 C 0.70488(8) 0.20384(17) 0.05992(9) 0.0238(4) Uani 1 1 d . . .
H13 H 0.6608 0.1842 0.0340 0.029 Uiso 1 1 calc R . .
C14 C 0.72333(9) 0.13947(18) 0.12315(9) 0.0271(4) Uani 1 1 d . . .
H14 H 0.6921 0.0748 0.1405 0.033 Uiso 1 1 calc R . .
C15 C 0.78745(9) 0.16963(16) 0.16116(9) 0.0215(3) Uani 1 1 d . . .
H15 H 0.7998 0.1252 0.2045 0.026 Uiso 1 1 calc R . .
C16 C 0.97015(8) 0.14010(15) 0.09805(8) 0.0170(3) Uani 1 1 d . . .
H16A H 0.9248 0.0929 0.0847 0.020 Uiso 1 1 calc R . .
H16B H 0.9757 0.2115 0.0631 0.020 Uiso 1 1 calc R . .
C17 C 1.03248(8) 0.04498(15) 0.09609(8) 0.0156(3) Uani 1 1 d . . .
C18 C 1.02646(8) -0.08272(15) 0.12250(8) 0.0196(3) Uani 1 1 d . . .
H18 H 0.9832 -0.1087 0.1421 0.024 Uiso 1 1 calc R . .
C19 C 1.08237(9) -0.17267(16) 0.12071(8) 0.0217(3) Uani 1 1 d . . .
H19 H 1.0768 -0.2600 0.1378 0.026 Uiso 1 1 calc R . .
C20 C 1.14628(9) -0.13431(16) 0.09383(8) 0.0230(3) Uani 1 1 d . . .
H20 H 1.1847 -0.1955 0.0924 0.028 Uiso 1 1 calc R . .
C21 C 1.15415(9) -0.00682(18) 0.06907(9) 0.0263(4) Uani 1 1 d . . .
H21 H 1.1983 0.0201 0.0515 0.032 Uiso 1 1 calc R . .
C22 C 1.09722(9) 0.08205(16) 0.06988(8) 0.0219(3) Uani 1 1 d . . .
H22 H 1.1027 0.1691 0.0523 0.026 Uiso 1 1 calc R . .
Cl1 Cl 0.94513(2) 0.61111(4) 0.045725(19) 0.01950(9) Uani 1 1 d . . .
N1 N 0.93379(6) 0.42354(12) 0.16584(6) 0.0138(2) Uani 1 1 d . . .
N2 N 1.02607(7) 0.29054(13) 0.18976(7) 0.0199(3) Uani 1 1 d D . .
O1 O 1.04797(5) 0.51486(10) 0.18473(6) 0.0193(2) Uani 1 1 d . . .
H2A H 1.0711(3) 0.2643(17) 0.1914(9) 0.023 Uiso 1 1 d D . .
C31 C 0.50547(8) 0.18307(15) 0.17992(8) 0.0155(3) Uani 1 1 d . . .
C32 C 0.40402(8) 0.31334(14) 0.19595(8) 0.0142(3) Uani 1 1 d . . .
H32 H 0.3999 0.3116 0.2484 0.017 Uiso 1 1 calc R . .
C33 C 0.46773(8) 0.40427(15) 0.17998(8) 0.0156(3) Uani 1 1 d . . .
H33 H 0.4732 0.4761 0.2162 0.019 Uiso 1 1 calc R . .
C34 C 0.39073(7) 0.06667(14) 0.18309(8) 0.0135(3) Uani 1 1 d . . .
C35 C 0.38607(7) -0.02976(15) 0.13039(8) 0.0156(3) Uani 1 1 d . . .
C36 C 0.34751(8) -0.14552(15) 0.13890(8) 0.0186(3) Uani 1 1 d . . .
H36 H 0.3456 -0.2114 0.1030 0.022 Uiso 1 1 calc R . .
C37 C 0.31194(8) -0.16424(15) 0.19994(8) 0.0186(3) Uani 1 1 d . . .
H37 H 0.2858 -0.2434 0.2061 0.022 Uiso 1 1 calc R . .
C38 C 0.31431(7) -0.06760(15) 0.25215(8) 0.0165(3) Uani 1 1 d . . .
H38 H 0.2889 -0.0796 0.2935 0.020 Uiso 1 1 calc R . .
C39 C 0.35388(7) 0.04658(15) 0.24369(8) 0.0148(3) Uani 1 1 d . . .
H39 H 0.3559 0.1120 0.2798 0.018 Uiso 1 1 calc R . .
C40 C 0.33204(8) 0.35188(14) 0.16051(8) 0.0143(3) Uani 1 1 d . . .
C41 C 0.30448(8) 0.29475(15) 0.09734(8) 0.0166(3) Uani 1 1 d . . .
H41 H 0.3313 0.2289 0.0750 0.020 Uiso 1 1 calc R . .
C42 C 0.23790(8) 0.33383(16) 0.06694(8) 0.0186(3) Uani 1 1 d . . .
H42 H 0.2194 0.2942 0.0239 0.022 Uiso 1 1 calc R . .
C43 C 0.19826(8) 0.42981(16) 0.09863(8) 0.0200(3) Uani 1 1 d . . .
H43 H 0.1525 0.4554 0.0779 0.024 Uiso 1 1 calc R . .
C44 C 0.22596(8) 0.48827(16) 0.16090(9) 0.0218(3) Uani 1 1 d . . .
H44 H 0.1993 0.5551 0.1826 0.026 Uiso 1 1 calc R . .
C45 C 0.29228(8) 0.44991(15) 0.19171(8) 0.0183(3) Uani 1 1 d . . .
H45 H 0.3108 0.4907 0.2344 0.022 Uiso 1 1 calc R . .
C46 C 0.46348(8) 0.46417(15) 0.10515(8) 0.0173(3) Uani 1 1 d . . .
H46A H 0.4637 0.3924 0.0696 0.021 Uiso 1 1 calc R . .
H46B H 0.4180 0.5138 0.0970 0.021 Uiso 1 1 calc R . .
C47 C 0.52607(8) 0.55550(15) 0.09616(8) 0.0162(3) Uani 1 1 d . . .
C48 C 0.59104(8) 0.50890(16) 0.07394(8) 0.0184(3) Uani 1 1 d . . .
H48 H 0.5958 0.4182 0.0623 0.022 Uiso 1 1 calc R . .
C49 C 0.64901(8) 0.59355(17) 0.06859(8) 0.0210(3) Uani 1 1 d . . .
H49 H 0.6934 0.5602 0.0545 0.025 Uiso 1 1 calc R . .
C50 C 0.64216(8) 0.72684(16) 0.08387(8) 0.0210(3) Uani 1 1 d . . .
H50 H 0.6815 0.7850 0.0794 0.025 Uiso 1 1 calc R . .
C51 C 0.57789(8) 0.77498(16) 0.10571(8) 0.0199(3) Uani 1 1 d . . .
H51 H 0.5729 0.8662 0.1160 0.024 Uiso 1 1 calc R . .
C52 C 0.52082(8) 0.68944(15) 0.11245(8) 0.0188(3) Uani 1 1 d . . .
H52 H 0.4772 0.7227 0.1285 0.023 Uiso 1 1 calc R . .
Cl31 Cl 0.42652(2) -0.00351(4) 0.051640(19) 0.02081(9) Uani 1 1 d . . .
N31 N 0.43036(6) 0.18419(12) 0.17390(6) 0.0140(2) Uani 1 1 d . . .
N32 N 0.52658(7) 0.31000(13) 0.19054(7) 0.0187(3) Uani 1 1 d D . .
O31 O 0.54341(5) 0.08559(11) 0.17761(6) 0.0198(2) Uani 1 1 d . . .
H32A H 0.5714(3) 0.3342(17) 0.1870(9) 0.024 Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.2175(18) . ?
C1 N2 1.3565(19) . ?
C1 N1 1.3974(18) . ?
C2 N1 1.4683(18) . ?
C2 C10 1.510(2) . ?
C2 C3 1.553(2) . ?
C2 H2 1.0000 . ?
C3 N2 1.4603(19) . ?
C3 C16 1.533(2) . ?
C3 H3 1.0000 . ?
C4 C9 1.394(2) . ?
C4 C5 1.395(2) . ?
C4 N1 1.4181(18) . ?
C5 C6 1.390(2) . ?
C5 Cl1 1.7362(16) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 C15 1.395(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.513(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.389(2) . ?
C17 C18 1.394(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N2 H2A 0.880(2) . ?
C31 O31 1.2175(18) . ?
C31 N32 1.355(2) . ?
C31 N31 1.3989(18) . ?
C32 N31 1.4678(18) . ?
C32 C40 1.5109(19) . ?
C32 C33 1.5503(19) . ?
C32 H32 1.0000 . ?
C33 N32 1.4585(19) . ?
C33 C46 1.537(2) . ?
C33 H33 1.0000 . ?
C34 C39 1.392(2) . ?
C34 C35 1.394(2) . ?
C34 N31 1.4183(18) . ?
C35 C36 1.391(2) . ?
C35 Cl31 1.7370(15) . ?
C36 C37 1.385(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.387(2) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.394(2) . ?
C40 C45 1.395(2) . ?
C41 C42 1.390(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.383(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.386(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(2) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.509(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.393(2) . ?
C47 C52 1.396(2) . ?
C48 C49 1.390(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.388(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.384(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.386(2) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
N32 H32A 0.880(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 127.66(13) . . ?
O1 C1 N1 125.68(13) . . ?
N2 C1 N1 106.63(12) . . ?
N1 C2 C10 113.91(12) . . ?
N1 C2 C3 101.62(11) . . ?
C10 C2 C3 116.08(12) . . ?
N1 C2 H2 108.3 . . ?
C10 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
N2 C3 C16 112.15(13) . . ?
N2 C3 C2 99.84(11) . . ?
C16 C3 C2 115.49(12) . . ?
N2 C3 H3 109.6 . . ?
C16 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
C9 C4 C5 118.61(13) . . ?
C9 C4 N1 121.08(13) . . ?
C5 C4 N1 120.28(13) . . ?
C6 C5 C4 121.00(14) . . ?
C6 C5 Cl1 119.40(12) . . ?
C4 C5 Cl1 119.59(11) . . ?
C7 C6 C5 119.66(15) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.15(14) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.89(15) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.69(14) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C11 C10 C15 118.66(14) . . ?
C11 C10 C2 122.95(13) . . ?
C15 C10 C2 118.39(13) . . ?
C10 C11 C12 120.31(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.54(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.66(15) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.88(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.94(15) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C3 111.01(12) . . ?
C17 C16 H16A 109.4 . . ?
C3 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C3 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C22 C17 C18 118.19(14) . . ?
C22 C17 C16 121.76(14) . . ?
C18 C17 C16 120.04(14) . . ?
C19 C18 C17 121.39(15) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 119.59(15) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.01(15) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.96(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.83(15) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C1 N1 C4 120.61(12) . . ?
C1 N1 C2 110.01(11) . . ?
C4 N1 C2 122.16(11) . . ?
C1 N2 C3 113.29(12) . . ?
C1 N2 H2A 121.4(12) . . ?
C3 N2 H2A 121.9(12) . . ?
O31 C31 N32 127.61(13) . . ?
O31 C31 N31 125.87(13) . . ?
N32 C31 N31 106.50(12) . . ?
N31 C32 C40 114.15(12) . . ?
N31 C32 C33 101.36(11) . . ?
C40 C32 C33 115.53(12) . . ?
N31 C32 H32 108.5 . . ?
C40 C32 H32 108.5 . . ?
C33 C32 H32 108.5 . . ?
N32 C33 C46 112.00(12) . . ?
N32 C33 C32 99.52(11) . . ?
C46 C33 C32 114.99(12) . . ?
N32 C33 H33 110.0 . . ?
C46 C33 H33 110.0 . . ?
C32 C33 H33 110.0 . . ?
C39 C34 C35 118.48(13) . . ?
C39 C34 N31 121.02(13) . . ?
C35 C34 N31 120.47(13) . . ?
C36 C35 C34 120.97(14) . . ?
C36 C35 Cl31 119.19(12) . . ?
C34 C35 Cl31 119.81(11) . . ?
C37 C36 C35 119.60(14) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 120.22(14) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C39 C38 C37 119.74(14) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C34 120.95(14) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
C41 C40 C45 118.87(13) . . ?
C41 C40 C32 122.51(13) . . ?
C45 C40 C32 118.61(13) . . ?
C42 C41 C40 120.19(14) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C43 C42 C41 120.69(14) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 119.29(14) . . ?
C42 C43 H43 120.4 . . ?
C44 C43 H43 120.4 . . ?
C45 C44 C43 120.48(15) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C40 120.46(14) . . ?
C44 C45 H45 119.8 . . ?
C40 C45 H45 119.8 . . ?
C47 C46 C33 110.77(12) . . ?
C47 C46 H46A 109.5 . . ?
C33 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
C33 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?
C48 C47 C52 118.14(14) . . ?
C48 C47 C46 121.58(14) . . ?
C52 C47 C46 120.25(14) . . ?
C49 C48 C47 120.78(15) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C50 C49 C48 120.07(15) . . ?
C50 C49 H49 120.0 . . ?
C48 C49 H49 120.0 . . ?
C51 C50 C49 119.93(15) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C50 C51 C52 119.68(15) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C47 121.39(15) . . ?
C51 C52 H52 119.3 . . ?
C47 C52 H52 119.3 . . ?
C31 N31 C34 120.78(12) . . ?
C31 N31 C32 109.74(11) . . ?
C34 N31 C32 121.65(12) . . ?
C31 N32 C33 113.07(12) . . ?
C31 N32 H32A 121.4(12) . . ?
C33 N32 H32A 121.3(12) . . ?

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
N1 C2 C3 N2 27.73(13) . . . . ?
C10 C2 C3 N2 151.87(13) . . . . ?
N1 C2 C3 C16 -92.70(14) . . . . ?
C10 C2 C3 C16 31.44(18) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
N1 C4 C5 C6 178.61(13) . . . . ?
C9 C4 C5 Cl1 -177.92(10) . . . . ?
N1 C4 C5 Cl1 -0.04(18) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
Cl1 C5 C6 C7 178.33(11) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
C5 C4 C9 C8 -0.5(2) . . . . ?
N1 C4 C9 C8 -178.38(12) . . . . ?
N1 C2 C10 C11 20.6(2) . . . . ?
C3 C2 C10 C11 -96.93(17) . . . . ?
N1 C2 C10 C15 -159.07(13) . . . . ?
C3 C2 C10 C15 83.41(17) . . . . ?
C15 C10 C11 C12 1.4(2) . . . . ?
C2 C10 C11 C12 -178.27(14) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C2 C10 C15 C14 178.69(15) . . . . ?
N2 C3 C16 C17 69.27(16) . . . . ?
C2 C3 C16 C17 -177.25(12) . . . . ?
C3 C16 C17 C22 -99.05(17) . . . . ?
C3 C16 C17 C18 79.45(17) . . . . ?
C22 C17 C18 C19 -2.2(2) . . . . ?
C16 C17 C18 C19 179.26(14) . . . . ?
C17 C18 C19 C20 1.7(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C18 C17 C22 C21 1.0(2) . . . . ?
C16 C17 C22 C21 179.49(14) . . . . ?
C20 C21 C22 C17 0.8(3) . . . . ?
O1 C1 N1 C4 -15.6(2) . . . . ?
N2 C1 N1 C4 162.87(13) . . . . ?
O1 C1 N1 C2 -166.52(14) . . . . ?
N2 C1 N1 C2 11.98(16) . . . . ?
C9 C4 N1 C1 -104.58(16) . . . . ?
C5 C4 N1 C1 77.60(18) . . . . ?
C9 C4 N1 C2 42.73(19) . . . . ?
C5 C4 N1 C2 -135.09(14) . . . . ?
C10 C2 N1 C1 -151.19(12) . . . . ?
C3 C2 N1 C1 -25.60(14) . . . . ?
C10 C2 N1 C4 58.45(18) . . . . ?
C3 C2 N1 C4 -175.95(12) . . . . ?
O1 C1 N2 C3 -173.04(15) . . . . ?
N1 C1 N2 C3 8.49(17) . . . . ?
C16 C3 N2 C1 99.38(15) . . . . ?
C2 C3 N2 C1 -23.46(16) . . . . ?
N31 C32 C33 N32 -29.60(13) . . . . ?
C40 C32 C33 N32 -153.54(12) . . . . ?
N31 C32 C33 C46 90.22(14) . . . . ?
C40 C32 C33 C46 -33.72(18) . . . . ?
C39 C34 C35 C36 -2.1(2) . . . . ?
N31 C34 C35 C36 179.84(13) . . . . ?
C39 C34 C35 Cl31 175.89(11) . . . . ?
N31 C34 C35 Cl31 -2.18(19) . . . . ?
C34 C35 C36 C37 1.4(2) . . . . ?
Cl31 C35 C36 C37 -176.63(11) . . . . ?
C35 C36 C37 C38 0.5(2) . . . . ?
C36 C37 C38 C39 -1.5(2) . . . . ?
C37 C38 C39 C34 0.8(2) . . . . ?
C35 C34 C39 C38 1.0(2) . . . . ?
N31 C34 C39 C38 179.08(12) . . . . ?
N31 C32 C40 C41 -20.1(2) . . . . ?
C33 C32 C40 C41 96.82(16) . . . . ?
N31 C32 C40 C45 160.92(13) . . . . ?
C33 C32 C40 C45 -82.13(17) . . . . ?
C45 C40 C41 C42 -1.1(2) . . . . ?
C32 C40 C41 C42 180.00(14) . . . . ?
C40 C41 C42 C43 0.2(2) . . . . ?
C41 C42 C43 C44 0.8(2) . . . . ?
C42 C43 C44 C45 -0.8(2) . . . . ?
C43 C44 C45 C40 0.0(2) . . . . ?
C41 C40 C45 C44 1.0(2) . . . . ?
C32 C40 C45 C44 179.98(14) . . . . ?
N32 C33 C46 C47 -69.88(16) . . . . ?
C32 C33 C46 C47 177.46(12) . . . . ?
C33 C46 C47 C48 87.71(17) . . . . ?
C33 C46 C47 C52 -90.10(17) . . . . ?
C52 C47 C48 C49 0.4(2) . . . . ?
C46 C47 C48 C49 -177.49(13) . . . . ?
C47 C48 C49 C50 -1.5(2) . . . . ?
C48 C49 C50 C51 1.2(2) . . . . ?
C49 C50 C51 C52 0.3(2) . . . . ?
C50 C51 C52 C47 -1.4(2) . . . . ?
C48 C47 C52 C51 1.1(2) . . . . ?
C46 C47 C52 C51 178.99(13) . . . . ?
O31 C31 N31 C34 17.0(2) . . . . ?
N32 C31 N31 C34 -161.46(13) . . . . ?
O31 C31 N31 C32 166.58(14) . . . . ?
N32 C31 N31 C32 -11.86(16) . . . . ?
C39 C34 N31 C31 107.19(16) . . . . ?
C35 C34 N31 C31 -74.78(18) . . . . ?
C39 C34 N31 C32 -38.78(19) . . . . ?
C35 C34 N31 C32 139.24(14) . . . . ?
C40 C32 N31 C31 151.63(12) . . . . ?
C33 C32 N31 C31 26.75(14) . . . . ?
C40 C32 N31 C34 -59.09(17) . . . . ?
C33 C32 N31 C34 176.04(12) . . . . ?
O31 C31 N32 C33 171.63(15) . . . . ?
N31 C31 N32 C33 -9.97(17) . . . . ?
C46 C33 N32 C31 -96.39(15) . . . . ?
C32 C33 N32 C31 25.60(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
