# 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_NK-2
_database_code_depnum_ccdc_archive 'CCDC 1440015'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Br Cl N2 O'
_chemical_formula_sum            'C20 H20 Br Cl N2 O'
_chemical_formula_weight         419.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5960(8)
_cell_length_b                   13.0323(10)
_cell_length_c                   15.0398(11)
_cell_angle_alpha                89.548(2)
_cell_angle_beta                 69.846(2)
_cell_angle_gamma                82.380(2)
_cell_volume                     1930.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4988
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.14

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25436
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         30.00
_reflns_number_total             11212
_reflns_number_gt                7918
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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 > 2sigma(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. 
;

_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)+(0.059P)²+P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11212
_refine_ls_number_parameters     453
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.91068(3) 0.19454(3) 0.84970(2) 0.03397(9) Uani 1 1 d . . .
Cl1 Cl 0.75546(8) 0.48311(6) 0.78056(6) 0.03217(16) Uani 1 1 d . . .
O1 O 0.9968(2) 0.31744(15) 0.66613(14) 0.0249(4) Uani 1 1 d . . .
C2 C 0.9984(3) 0.3920(2) 0.60361(19) 0.0234(5) Uani 1 1 d . . .
N2 N 0.8965(2) 0.41033(19) 0.57393(17) 0.0247(5) Uani 1 1 d . . .
N3 N 1.1073(2) 0.44158(19) 0.56920(17) 0.0237(5) Uani 1 1 d . . .
H3N H 1.102(3) 0.487(3) 0.530(2) 0.024(8) Uiso 1 1 d . . .
C4 C 1.2298(3) 0.4259(2) 0.5952(2) 0.0240(5) Uani 1 1 d . . .
C5 C 1.2324(3) 0.3228(2) 0.6441(2) 0.0250(6) Uani 1 1 d . . .
H5A H 1.2598 0.2649 0.5961 0.030 Uiso 1 1 calc R . .
H5B H 1.2997 0.3184 0.6765 0.030 Uiso 1 1 calc R . .
C6 C 1.0936(3) 0.3138(2) 0.7154(2) 0.0237(5) Uani 1 1 d . . .
H6 H 1.0655 0.3716 0.7646 0.028 Uiso 1 1 calc R . .
C7 C 0.7786(3) 0.3663(2) 0.6252(2) 0.0250(6) Uani 1 1 d . . .
C8 C 0.7032(3) 0.3927(2) 0.7208(2) 0.0263(6) Uani 1 1 d . . .
C9 C 0.5874(3) 0.3498(2) 0.7701(2) 0.0295(6) Uani 1 1 d . . .
H9 H 0.5393 0.3686 0.8351 0.035 Uiso 1 1 calc R . .
C10 C 0.5424(3) 0.2792(2) 0.7234(2) 0.0323(7) Uani 1 1 d . . .
H10 H 0.4648 0.2475 0.7569 0.039 Uiso 1 1 calc R . .
C11 C 0.6110(3) 0.2550(2) 0.6279(2) 0.0324(7) Uani 1 1 d . . .
H11 H 0.5783 0.2084 0.5954 0.039 Uiso 1 1 calc R . .
C12 C 0.7269(3) 0.2982(2) 0.5795(2) 0.0298(6) Uani 1 1 d . . .
H12 H 0.7722 0.2813 0.5139 0.036 Uiso 1 1 calc R . .
C13 C 1.2311(3) 0.5160(2) 0.6599(2) 0.0256(6) Uani 1 1 d . . .
C14 C 1.3374(3) 0.5140(2) 0.6950(2) 0.0297(6) Uani 1 1 d . . .
H14 H 1.4082 0.4570 0.6781 0.036 Uiso 1 1 calc R . .
C15 C 1.3411(3) 0.5936(3) 0.7540(2) 0.0337(7) Uani 1 1 d . . .
H15 H 1.4133 0.5902 0.7782 0.040 Uiso 1 1 calc R . .
C16 C 1.2398(4) 0.6786(3) 0.7780(2) 0.0360(7) Uani 1 1 d . . .
H16 H 1.2422 0.7332 0.8187 0.043 Uiso 1 1 calc R . .
C17 C 1.1355(3) 0.6826(3) 0.7420(2) 0.0350(7) Uani 1 1 d . . .
H17 H 1.0667 0.7410 0.7571 0.042 Uiso 1 1 calc R . .
C18 C 1.1304(3) 0.6016(2) 0.6836(2) 0.0299(6) Uani 1 1 d . . .
H18 H 1.0576 0.6050 0.6600 0.036 Uiso 1 1 calc R . .
C19 C 1.3552(3) 0.4219(2) 0.5022(2) 0.0269(6) Uani 1 1 d . . .
H19A H 1.3556 0.4910 0.4744 0.032 Uiso 1 1 calc R . .
H19B H 1.4389 0.4063 0.5180 0.032 Uiso 1 1 calc R . .
C20 C 1.3579(3) 0.3435(3) 0.4301(2) 0.0343(7) Uani 1 1 d . . .
H20 H 1.2876 0.3534 0.4039 0.041 Uiso 1 1 calc R . .
C21 C 1.4497(4) 0.2615(3) 0.3999(3) 0.0463(9) Uani 1 1 d . . .
H21A H 1.5217 0.2488 0.4243 0.056 Uiso 1 1 calc R . .
H21B H 1.4443 0.2149 0.3535 0.056 Uiso 1 1 calc R . .
C22 C 1.0914(3) 0.2105(2) 0.7618(2) 0.0296(6) Uani 1 1 d . . .
H22A H 1.1561 0.2042 0.7965 0.035 Uiso 1 1 calc R . .
H22B H 1.1215 0.1542 0.7121 0.035 Uiso 1 1 calc R . .
Br2 Br 0.82100(3) 0.58558(2) 1.08639(2) 0.03282(9) Uani 1 1 d . . .
Cl2 Cl 0.84402(10) 1.04787(8) 1.05987(7) 0.0387(2) Uani 0.85 1 d PD A 1
Cl2' Cl 0.4376(5) 0.9885(4) 1.2842(4) 0.0387(2) Uani 0.15 1 d PD B 2
O23 O 0.7482(2) 0.82517(16) 1.04470(15) 0.0300(5) Uani 1 1 d . . .
C24 C 0.6516(3) 0.8955(2) 1.03111(17) 0.0272(6) Uani 1 1 d D . .
N24 N 0.5768(3) 0.96313(17) 1.09507(15) 0.0263(6) Uani 0.85 1 d PD A 1
N24' N 0.6081(8) 0.9826(4) 1.0794(5) 0.0263(6) Uani 0.15 1 d PD B 2
N25 N 0.6281(3) 0.8877(2) 0.94755(18) 0.0277(5) Uani 1 1 d . A .
H25N H 0.570(4) 0.934(3) 0.942(3) 0.032(9) Uiso 1 1 d . . .
C26 C 0.6769(3) 0.8024(2) 0.8766(2) 0.0252(6) Uani 1 1 d . . .
C27 C 0.7535(3) 0.7150(2) 0.9146(2) 0.0260(6) Uani 1 1 d . A .
H27A H 0.6879 0.6752 0.9600 0.031 Uiso 1 1 calc R . .
H27B H 0.8131 0.6671 0.8617 0.031 Uiso 1 1 calc R . .
C28 C 0.8377(3) 0.7597(2) 0.9634(2) 0.0269(6) Uani 1 1 d . . .
H28 H 0.8980 0.8040 0.9179 0.032 Uiso 1 1 calc R A .
C29 C 0.6110(2) 0.98469(11) 1.17521(13) 0.0339(3) Uani 0.85 1 d PD A 1
C30 C 0.73007(19) 1.02363(9) 1.16924(14) 0.0339(3) Uani 0.85 1 d PD A 1
C31 C 0.7604(2) 1.04401(14) 1.24980(14) 0.0339(3) Uani 0.85 1 d PD A 1
H31A H 0.8422 1.0705 1.2437 0.041 Uiso 0.85 1 calc PR A 1
C32 C 0.6714(3) 1.02570(18) 1.33934(16) 0.0339(3) Uani 0.85 1 d PD A 1
H32A H 0.6917 1.0394 1.3945 0.041 Uiso 0.85 1 calc PR A 1
C33 C 0.5517(3) 0.98683(17) 1.34667(16) 0.0339(3) Uani 0.85 1 d PD A 1
H33A H 0.4902 0.9741 1.4074 0.041 Uiso 0.85 1 calc PR A 1
C34 C 0.5217(2) 0.96657(15) 1.26655(15) 0.0339(3) Uani 0.85 1 d PD A 1
H34A H 0.4397 0.9401 1.2730 0.041 Uiso 0.85 1 calc PR A 1
C29' C 0.6748(5) 1.0046(4) 1.1433(3) 0.0339(3) Uani 0.15 1 d PD B 2
C30' C 0.6056(5) 1.0095(4) 1.2413(4) 0.0339(3) Uani 0.15 1 d PD B 2
C31' C 0.6698(7) 1.0309(6) 1.3040(4) 0.0339(3) Uani 0.15 1 d PD B 2
H31B H 0.6214 1.0339 1.3703 0.041 Uiso 0.15 1 calc PR B 2
C32' C 0.8054(7) 1.0479(8) 1.2697(6) 0.0339(3) Uani 0.15 1 d PD B 2
H32B H 0.8496 1.0625 1.3125 0.041 Uiso 0.15 1 calc PR B 2
C33' C 0.8754(6) 1.0432(8) 1.1721(6) 0.0339(3) Uani 0.15 1 d PD B 2
H33B H 0.9676 1.0547 1.1484 0.041 Uiso 0.15 1 calc PR B 2
C34' C 0.8110(6) 1.0217(6) 1.1092(5) 0.0339(3) Uani 0.15 1 d PD B 2
H34B H 0.8596 1.0187 1.0429 0.041 Uiso 0.15 1 calc PR B 2
C35 C 0.7723(3) 0.8387(2) 0.7823(2) 0.0269(6) Uani 1 1 d . A .
C36 C 0.8221(3) 0.7711(2) 0.7021(2) 0.0287(6) Uani 1 1 d . . .
H36 H 0.7970 0.7034 0.7066 0.034 Uiso 1 1 calc R A .
C37 C 0.9071(3) 0.8011(3) 0.6166(2) 0.0344(7) Uani 1 1 d . A .
H37 H 0.9398 0.7543 0.5630 0.041 Uiso 1 1 calc R . .
C38 C 0.9449(4) 0.9000(3) 0.6089(3) 0.0426(8) Uani 1 1 d . . .
H38 H 1.0027 0.9210 0.5500 0.051 Uiso 1 1 calc R A .
C39 C 0.8979(4) 0.9668(3) 0.6869(3) 0.0453(9) Uani 1 1 d . A .
H39 H 0.9242 1.0341 0.6819 0.054 Uiso 1 1 calc R . .
C40 C 0.8123(4) 0.9373(3) 0.7734(3) 0.0375(7) Uani 1 1 d . . .
H40 H 0.7809 0.9844 0.8267 0.045 Uiso 1 1 calc R A .
C41 C 0.5526(3) 0.7648(2) 0.8605(2) 0.0277(6) Uani 1 1 d . A .
H41A H 0.5116 0.8194 0.8286 0.033 Uiso 1 1 calc R . .
H41B H 0.5848 0.7024 0.8173 0.033 Uiso 1 1 calc R . .
C42 C 0.4449(3) 0.7393(3) 0.9498(2) 0.0336(7) Uani 1 1 d . . .
H42 H 0.3946 0.7950 0.9931 0.040 Uiso 1 1 calc R A .
C43 C 0.4149(3) 0.6458(3) 0.9726(2) 0.0372(7) Uani 1 1 d . A .
H43A H 0.4629 0.5880 0.9311 0.045 Uiso 1 1 calc R . .
H43B H 0.3452 0.6360 1.0306 0.045 Uiso 1 1 calc R . .
C44 C 0.9256(3) 0.6804(2) 0.9986(2) 0.0301(6) Uani 1 1 d . A .
H44A H 0.9750 0.7169 1.0308 0.036 Uiso 1 1 calc R . .
H44B H 0.9937 0.6398 0.9436 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C22 1.953(3) . ?
Cl1 C8 1.742(3) . ?
O1 C2 1.345(3) . ?
O1 C6 1.454(3) . ?
C2 N2 1.297(4) . ?
C2 N3 1.341(4) . ?
N2 C7 1.416(4) . ?
N3 C4 1.469(4) . ?
N3 H3N 0.85(3) . ?
C4 C5 1.528(4) . ?
C4 C13 1.536(4) . ?
C4 C19 1.558(4) . ?
C5 C6 1.511(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C22 1.510(4) . ?
C6 H6 1.0000 . ?
C7 C12 1.399(4) . ?
C7 C8 1.403(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.393(4) . ?
C13 C14 1.397(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.486(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.312(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
Br2 C44 1.957(3) . ?
Cl2 C30 1.729(2) . ?
Cl2' C30' 1.730(2) . ?
O23 C24 1.349(3) . ?
O23 C28 1.458(4) . ?
C24 N24 1.278(2) . ?
C24 N24' 1.293(3) . ?
C24 N25 1.370(3) . ?
N24 C29 1.413(2) . ?
N24' C29' 1.426(2) . ?
N25 C26 1.460(4) . ?
N25 H25N 0.83(4) . ?
C26 C27 1.533(4) . ?
C26 C35 1.544(4) . ?
C26 C41 1.558(4) . ?
C27 C28 1.506(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C44 1.514(4) . ?
C28 H28 1.0000 . ?
C29 C30 1.395(2) . ?
C29 C34 1.413(2) . ?
C30 C31 1.392(2) . ?
C31 C32 1.393(2) . ?
C31 H31A 0.9500 . ?
C32 C33 1.396(2) . ?
C32 H32A 0.9500 . ?
C33 C34 1.384(2) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C29' C30' 1.400(2) . ?
C29' C34' 1.404(2) . ?
C30' C31' 1.388(2) . ?
C31' C32' 1.398(3) . ?
C31' H31B 0.9500 . ?
C32' C33' 1.396(3) . ?
C32' H32B 0.9500 . ?
C33' C34' 1.391(3) . ?
C33' H33B 0.9500 . ?
C34' H34B 0.9500 . ?
C35 C40 1.397(4) . ?
C35 C36 1.402(4) . ?
C36 C37 1.379(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.391(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.372(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.390(5) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.501(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.313(5) . ?
C42 H42 0.9500 . ?
C43 H43A 0.9500 . ?
C43 H43B 0.9500 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C6 117.9(2) . . ?
N2 C2 N3 121.3(3) . . ?
N2 C2 O1 118.7(2) . . ?
N3 C2 O1 119.9(2) . . ?
C2 N2 C7 116.5(2) . . ?
C2 N3 C4 126.5(2) . . ?
C2 N3 H3N 115(2) . . ?
C4 N3 H3N 118(2) . . ?
N3 C4 C5 108.0(2) . . ?
N3 C4 C13 110.7(2) . . ?
C5 C4 C13 111.3(2) . . ?
N3 C4 C19 107.8(2) . . ?
C5 C4 C19 110.2(2) . . ?
C13 C4 C19 108.8(2) . . ?
C6 C5 C4 110.1(2) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
O1 C6 C22 106.0(2) . . ?
O1 C6 C5 108.9(2) . . ?
C22 C6 C5 111.3(2) . . ?
O1 C6 H6 110.2 . . ?
C22 C6 H6 110.2 . . ?
C5 C6 H6 110.2 . . ?
C12 C7 C8 116.6(3) . . ?
C12 C7 N2 120.4(3) . . ?
C8 C7 N2 122.8(3) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 Cl1 118.2(2) . . ?
C7 C8 Cl1 119.4(2) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 C4 122.1(3) . . ?
C14 C13 C4 119.6(3) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.5(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C4 113.6(2) . . ?
C20 C19 H19A 108.8 . . ?
C4 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C4 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 125.1(3) . . ?
C21 C20 H20 117.4 . . ?
C19 C20 H20 117.4 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C6 C22 Br1 112.0(2) . . ?
C6 C22 H22A 109.2 . . ?
Br1 C22 H22A 109.2 . . ?
C6 C22 H22B 109.2 . . ?
Br1 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 O23 C28 117.7(2) . . ?
N24 C24 O23 122.6(2) . . ?
N24' C24 O23 122.4(3) . . ?
N24 C24 N25 119.7(2) . . ?
N24' C24 N25 117.5(3) . . ?
O23 C24 N25 117.6(2) . . ?
C24 N24 C29 121.14(18) . . ?
C24 N24' C29' 116.4(3) . . ?
C24 N25 C26 128.1(2) . . ?
C24 N25 H25N 114(3) . . ?
C26 N25 H25N 118(3) . . ?
N25 C26 C27 107.9(2) . . ?
N25 C26 C35 110.2(2) . . ?
C27 C26 C35 110.2(2) . . ?
N25 C26 C41 108.7(2) . . ?
C27 C26 C41 110.3(2) . . ?
C35 C26 C41 109.5(2) . . ?
C28 C27 C26 109.9(2) . . ?
C28 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
C28 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
O23 C28 C27 109.2(2) . . ?
O23 C28 C44 107.7(2) . . ?
C27 C28 C44 114.9(2) . . ?
O23 C28 H28 108.3 . . ?
C27 C28 H28 108.3 . . ?
C44 C28 H28 108.3 . . ?
C30 C29 N24 123.22(17) . . ?
C30 C29 C34 117.45(16) . . ?
N24 C29 C34 119.33(18) . . ?
C31 C30 C29 121.63(17) . . ?
C31 C30 Cl2 118.37(16) . . ?
C29 C30 Cl2 120.00(14) . . ?
C30 C31 C32 120.26(19) . . ?
C30 C31 H31A 119.9 . . ?
C32 C31 H31A 119.9 . . ?
C31 C32 C33 118.89(18) . . ?
C31 C32 H32A 120.6 . . ?
C33 C32 H32A 120.6 . . ?
C34 C33 C32 120.81(19) . . ?
C34 C33 H33A 119.6 . . ?
C32 C33 H33A 119.6 . . ?
C33 C34 C29 120.96(19) . . ?
C33 C34 H34A 119.5 . . ?
C29 C34 H34A 119.5 . . ?
C30' C29' C34' 118.71(19) . . ?
C30' C29' N24' 120.6(2) . . ?
C34' C29' N24' 120.7(2) . . ?
C31' C30' C29' 121.0(2) . . ?
C31' C30' Cl2' 119.9(2) . . ?
C29' C30' Cl2' 119.2(2) . . ?
C30' C31' C32' 120.1(2) . . ?
C30' C31' H31B 120.0 . . ?
C32' C31' H31B 120.0 . . ?
C33' C32' C31' 119.4(2) . . ?
C33' C32' H32B 120.3 . . ?
C31' C32' H32B 120.3 . . ?
C34' C33' C32' 120.5(2) . . ?
C34' C33' H33B 119.7 . . ?
C32' C33' H33B 119.7 . . ?
C33' C34' C29' 120.3(2) . . ?
C33' C34' H34B 119.8 . . ?
C29' C34' H34B 119.8 . . ?
C40 C35 C36 117.9(3) . . ?
C40 C35 C26 122.4(3) . . ?
C36 C35 C26 119.6(3) . . ?
C37 C36 C35 121.1(3) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C36 C37 C38 120.1(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C39 C38 C37 119.5(3) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C40 120.9(3) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C39 C40 C35 120.5(3) . . ?
C39 C40 H40 119.8 . . ?
C35 C40 H40 119.8 . . ?
C42 C41 C26 114.1(2) . . ?
C42 C41 H41A 108.7 . . ?
C26 C41 H41A 108.7 . . ?
C42 C41 H41B 108.7 . . ?
C26 C41 H41B 108.7 . . ?
H41A C41 H41B 107.6 . . ?
C43 C42 C41 125.0(3) . . ?
C43 C42 H42 117.5 . . ?
C41 C42 H42 117.5 . . ?
C42 C43 H43A 120.0 . . ?
C42 C43 H43B 120.0 . . ?
H43A C43 H43B 120.0 . . ?
C28 C44 Br2 112.8(2) . . ?
C28 C44 H44A 109.0 . . ?
Br2 C44 H44A 109.0 . . ?
C28 C44 H44B 109.0 . . ?
Br2 C44 H44B 109.0 . . ?
H44A C44 H44B 107.8 . . ?

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
C6 O1 C2 N2 -165.8(2) . . . . ?
C6 O1 C2 N3 18.0(4) . . . . ?
N3 C2 N2 C7 -170.4(3) . . . . ?
O1 C2 N2 C7 13.5(4) . . . . ?
N2 C2 N3 C4 -178.4(3) . . . . ?
O1 C2 N3 C4 -2.3(4) . . . . ?
C2 N3 C4 C5 17.0(4) . . . . ?
C2 N3 C4 C13 -105.1(3) . . . . ?
C2 N3 C4 C19 136.0(3) . . . . ?
N3 C4 C5 C6 -45.0(3) . . . . ?
C13 C4 C5 C6 76.7(3) . . . . ?
C19 C4 C5 C6 -162.5(2) . . . . ?
C2 O1 C6 C22 -167.1(2) . . . . ?
C2 O1 C6 C5 -47.2(3) . . . . ?
C4 C5 C6 O1 60.9(3) . . . . ?
C4 C5 C6 C22 177.4(2) . . . . ?
C2 N2 C7 C12 -121.3(3) . . . . ?
C2 N2 C7 C8 62.9(4) . . . . ?
C12 C7 C8 C9 3.6(4) . . . . ?
N2 C7 C8 C9 179.5(3) . . . . ?
C12 C7 C8 Cl1 -176.1(2) . . . . ?
N2 C7 C8 Cl1 -0.3(4) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
Cl1 C8 C9 C10 178.8(2) . . . . ?
C8 C9 C10 C11 -2.0(5) . . . . ?
C9 C10 C11 C12 2.2(5) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C8 C7 C12 C11 -3.4(4) . . . . ?
N2 C7 C12 C11 -179.4(3) . . . . ?
N3 C4 C13 C18 -3.3(4) . . . . ?
C5 C4 C13 C18 -123.4(3) . . . . ?
C19 C4 C13 C18 115.0(3) . . . . ?
N3 C4 C13 C14 177.9(2) . . . . ?
C5 C4 C13 C14 57.8(3) . . . . ?
C19 C4 C13 C14 -63.7(3) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C4 C13 C14 C15 -179.5(3) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C4 C13 C18 C17 -179.4(3) . . . . ?
C16 C17 C18 C13 -0.7(5) . . . . ?
N3 C4 C19 C20 -54.5(3) . . . . ?
C5 C4 C19 C20 63.1(3) . . . . ?
C13 C4 C19 C20 -174.7(3) . . . . ?
C4 C19 C20 C21 -115.3(4) . . . . ?
O1 C6 C22 Br1 -58.9(3) . . . . ?
C5 C6 C22 Br1 -177.2(2) . . . . ?
C28 O23 C24 N24 -173.0(3) . . . . ?
C28 O23 C24 N24' -149.4(5) . . . . ?
C28 O23 C24 N25 11.7(4) . . . . ?
O23 C24 N24 C29 15.2(4) . . . . ?
N25 C24 N24 C29 -169.7(2) . . . . ?
O23 C24 N24' C29' 4.6(8) . . . . ?
N25 C24 N24' C29' -156.5(4) . . . . ?
N24 C24 N25 C26 -163.6(3) . . . . ?
N24' C24 N25 C26 173.9(5) . . . . ?
O23 C24 N25 C26 11.8(5) . . . . ?
C24 N25 C26 C27 4.3(4) . . . . ?
C24 N25 C26 C35 -116.0(3) . . . . ?
C24 N25 C26 C41 124.0(3) . . . . ?
N25 C26 C27 C28 -40.4(3) . . . . ?
C35 C26 C27 C28 79.9(3) . . . . ?
C41 C26 C27 C28 -159.0(2) . . . . ?
C24 O23 C28 C27 -48.5(3) . . . . ?
C24 O23 C28 C44 -173.8(2) . . . . ?
C26 C27 C28 O23 62.8(3) . . . . ?
C26 C27 C28 C44 -176.2(2) . . . . ?
C24 N24 C29 C30 61.8(2) . . . . ?
C24 N24 C29 C34 -118.3(2) . . . . ?
C24 N24' C29' C30' -113.3(6) . . . . ?
C24 N24' C29' C34' 66.7(6) . . . . ?
N25 C26 C35 C40 5.5(4) . . . . ?
C27 C26 C35 C40 -113.4(3) . . . . ?
C41 C26 C35 C40 125.1(3) . . . . ?
N25 C26 C35 C36 -174.9(3) . . . . ?
C27 C26 C35 C36 66.2(3) . . . . ?
C41 C26 C35 C36 -55.3(3) . . . . ?
C40 C35 C36 C37 -0.6(5) . . . . ?
C26 C35 C36 C37 179.8(3) . . . . ?
C35 C36 C37 C38 0.0(5) . . . . ?
C36 C37 C38 C39 0.5(6) . . . . ?
C37 C38 C39 C40 -0.5(6) . . . . ?
C38 C39 C40 C35 -0.1(6) . . . . ?
C36 C35 C40 C39 0.7(5) . . . . ?
C26 C35 C40 C39 -179.7(3) . . . . ?
N25 C26 C41 C42 -52.8(3) . . . . ?
C27 C26 C41 C42 65.3(3) . . . . ?
C35 C26 C41 C42 -173.2(3) . . . . ?
C26 C41 C42 C43 -111.5(4) . . . . ?
O23 C28 C44 Br2 64.6(3) . . . . ?
C27 C28 C44 Br2 -57.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_NK3
_database_code_depnum_ccdc_archive 'CCDC 1440016'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Cl N2 O'
_chemical_formula_sum            'C20 H19 Cl N2 O'
_chemical_formula_weight         338.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.684(2)
_cell_length_b                   11.847(4)
_cell_length_c                   22.594(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1789.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    925
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      18.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17046
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.1550
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.08
_reflns_number_total             3541
_reflns_number_gt                1680
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT, (Bruker, 2001)'
_computing_data_reduction        'SAINT, (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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 > 2sigma(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. 
;

_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)+(0.052P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1784
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.93944(16) 0.71471(10) 0.74244(5) 0.0671(3) Uani 1 1 d . . .
O1 O 0.0129(3) 0.6423(2) 0.57730(11) 0.0449(7) Uani 1 1 d . . .
N1 N 0.6142(4) 0.6341(2) 0.55308(11) 0.0278(7) Uani 1 1 d . . .
H1N H 0.7473 0.6178 0.5505 0.033 Uiso 1 1 d R . .
N2 N 0.6736(4) 0.7321(2) 0.63849(12) 0.0351(8) Uani 1 1 d . . .
H2N H 0.7953 0.6980 0.6318 0.042 Uiso 1 1 d R . .
C2 C 0.5380(5) 0.6838(3) 0.60148(14) 0.0282(9) Uani 1 1 d . . .
C3 C 0.3326(4) 0.6829(3) 0.61378(15) 0.0274(9) Uani 1 1 d . . .
H3 H 0.2834 0.7091 0.6508 0.033 Uiso 1 1 calc R . .
C4 C 0.2017(5) 0.6428(3) 0.57058(16) 0.0330(10) Uani 1 1 d . . .
C5 C 0.2874(5) 0.6049(3) 0.51229(15) 0.0319(10) Uani 1 1 d . . .
H5A H 0.2964 0.6705 0.4853 0.038 Uiso 1 1 calc R . .
H5B H 0.1963 0.5489 0.4941 0.038 Uiso 1 1 calc R . .
C6 C 0.4962(5) 0.5522(3) 0.51958(15) 0.0301(9) Uani 1 1 d . . .
C7 C 0.6321(5) 0.8127(3) 0.68274(16) 0.0372(10) Uani 1 1 d . . .
C8 C 0.7479(5) 0.8140(3) 0.73432(17) 0.0500(12) Uani 1 1 d . . .
C9 C 0.7185(7) 0.8965(4) 0.77883(18) 0.0665(14) Uani 1 1 d . . .
H9 H 0.8003 0.8974 0.8132 0.080 Uiso 1 1 calc R . .
C10 C 0.5703(7) 0.9747(4) 0.77144(19) 0.0680(15) Uani 1 1 d . . .
H10 H 0.5459 1.0289 0.8016 0.082 Uiso 1 1 calc R . .
C11 C 0.4547(6) 0.9756(3) 0.7202(2) 0.0610(14) Uani 1 1 d . . .
H11 H 0.3525 1.0306 0.7153 0.073 Uiso 1 1 calc R . .
C12 C 0.4890(5) 0.8960(3) 0.67619(17) 0.0434(11) Uani 1 1 d . . .
H12 H 0.4124 0.8989 0.6408 0.052 Uiso 1 1 calc R . .
C13 C 0.4939(5) 0.4388(3) 0.55170(16) 0.0352(10) Uani 1 1 d . . .
C14 C 0.6651(6) 0.4038(3) 0.58163(17) 0.0496(12) Uani 1 1 d . . .
H14 H 0.7768 0.4532 0.5839 0.060 Uiso 1 1 calc R . .
C15 C 0.6761(8) 0.3005(4) 0.60766(19) 0.0757(16) Uani 1 1 d . . .
H15 H 0.7948 0.2791 0.6279 0.091 Uiso 1 1 calc R . .
C16 C 0.5181(8) 0.2267(4) 0.6051(2) 0.0836(18) Uani 1 1 d . . .
H16 H 0.5254 0.1556 0.6244 0.100 Uiso 1 1 calc R . .
C17 C 0.3470(7) 0.2574(4) 0.5740(2) 0.0800(17) Uani 1 1 d . . .
H17 H 0.2389 0.2058 0.5701 0.096 Uiso 1 1 calc R . .
C18 C 0.3353(6) 0.3655(3) 0.5481(2) 0.0599(14) Uani 1 1 d . . .
H18 H 0.2168 0.3878 0.5281 0.072 Uiso 1 1 calc R . .
C19 C 0.6023(5) 0.5409(3) 0.45915(15) 0.0335(10) Uani 1 1 d . . .
H19A H 0.6240 0.6173 0.4427 0.040 Uiso 1 1 calc R . .
H19B H 0.7353 0.5061 0.4655 0.040 Uiso 1 1 calc R . .
C20 C 0.4901(5) 0.4720(3) 0.41486(16) 0.0442(11) Uani 1 1 d . . .
H20 H 0.4315 0.4033 0.4278 0.053 Uiso 1 1 calc R . .
C21 C 0.4676(6) 0.5006(4) 0.35948(19) 0.0571(14) Uani 1 1 d . . .
H21A H 0.5244 0.5688 0.3452 0.068 Uiso 1 1 calc R . .
H21B H 0.3944 0.4531 0.3334 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.748(4) . ?
O1 C4 1.271(4) . ?
N1 C2 1.342(4) . ?
N1 C6 1.463(4) . ?
N1 H1N 0.9120 . ?
N2 C2 1.360(4) . ?
N2 C7 1.410(4) . ?
N2 H2N 0.9210 . ?
C2 C3 1.401(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.504(5) . ?
C5 C6 1.538(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C13 1.526(5) . ?
C6 C19 1.544(5) . ?
C7 C12 1.382(5) . ?
C7 C8 1.399(5) . ?
C8 C9 1.416(5) . ?
C9 C10 1.366(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.373(5) . ?
C13 C14 1.392(5) . ?
C14 C15 1.360(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.410(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.493(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.305(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 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
C2 N1 C6 120.5(3) . . ?
C2 N1 H1N 121.0 . . ?
C6 N1 H1N 110.6 . . ?
C2 N2 C7 126.2(3) . . ?
C2 N2 H2N 107.6 . . ?
C7 N2 H2N 126.0 . . ?
N1 C2 N2 115.6(3) . . ?
N1 C2 C3 122.0(3) . . ?
N2 C2 C3 122.3(3) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
O1 C4 C3 122.7(3) . . ?
O1 C4 C5 118.8(3) . . ?
C3 C4 C5 118.4(3) . . ?
C4 C5 C6 111.9(3) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C13 110.1(3) . . ?
N1 C6 C5 106.0(3) . . ?
C13 C6 C5 113.5(3) . . ?
N1 C6 C19 105.5(3) . . ?
C13 C6 C19 110.4(3) . . ?
C5 C6 C19 110.9(3) . . ?
C12 C7 C8 117.7(3) . . ?
C12 C7 N2 122.9(3) . . ?
C8 C7 N2 119.3(3) . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 Cl1 119.0(3) . . ?
C9 C8 Cl1 119.4(3) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C7 C12 C11 121.5(4) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C18 C13 C14 118.3(3) . . ?
C18 C13 C6 122.4(3) . . ?
C14 C13 C6 119.0(3) . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 120.5(4) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C6 114.1(3) . . ?
C20 C19 H19A 108.7 . . ?
C6 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C6 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 124.0(4) . . ?
C21 C20 H20 118.0 . . ?
C19 C20 H20 118.0 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?

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
C6 N1 C2 N2 161.8(3) . . . . ?
C6 N1 C2 C3 -16.4(5) . . . . ?
C7 N2 C2 N1 162.5(3) . . . . ?
C7 N2 C2 C3 -19.4(5) . . . . ?
N1 C2 C3 C4 -8.9(5) . . . . ?
N2 C2 C3 C4 173.1(3) . . . . ?
C2 C3 C4 O1 -177.7(3) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
O1 C4 C5 C6 -150.4(3) . . . . ?
C3 C4 C5 C6 33.2(4) . . . . ?
C2 N1 C6 C13 -77.2(4) . . . . ?
C2 N1 C6 C5 46.0(4) . . . . ?
C2 N1 C6 C19 163.7(3) . . . . ?
C4 C5 C6 N1 -52.1(4) . . . . ?
C4 C5 C6 C13 68.9(4) . . . . ?
C4 C5 C6 C19 -166.1(3) . . . . ?
C2 N2 C7 C12 -36.1(5) . . . . ?
C2 N2 C7 C8 148.0(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
N2 C7 C8 C9 177.0(3) . . . . ?
C12 C7 C8 Cl1 -176.6(3) . . . . ?
N2 C7 C8 Cl1 -0.5(5) . . . . ?
C7 C8 C9 C10 1.4(6) . . . . ?
Cl1 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 -2.1(7) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C8 C7 C12 C11 -2.7(5) . . . . ?
N2 C7 C12 C11 -178.6(3) . . . . ?
C10 C11 C12 C7 2.1(6) . . . . ?
N1 C6 C13 C18 149.5(3) . . . . ?
C5 C6 C13 C18 30.9(5) . . . . ?
C19 C6 C13 C18 -94.4(4) . . . . ?
N1 C6 C13 C14 -36.1(4) . . . . ?
C5 C6 C13 C14 -154.7(3) . . . . ?
C19 C6 C13 C14 79.9(4) . . . . ?
C18 C13 C14 C15 -1.0(6) . . . . ?
C6 C13 C14 C15 -175.6(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 1.8(7) . . . . ?
C15 C16 C17 C18 -3.1(7) . . . . ?
C14 C13 C18 C17 -0.3(6) . . . . ?
C6 C13 C18 C17 174.1(4) . . . . ?
C16 C17 C18 C13 2.3(7) . . . . ?
N1 C6 C19 C20 -172.3(3) . . . . ?
C13 C6 C19 C20 68.8(4) . . . . ?
C5 C6 C19 C20 -58.0(4) . . . . ?
C6 C19 C20 C21 135.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag

N1 H1N O1 1_655 0.91 1.90 2.722(3) 149 ?
N2 H2N O1 1_655 0.92 2.02 2.861(4) 152 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.08
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.061
