# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a7
_database_code_depnum_ccdc_archive 'CCDC 1007368'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 Cl F N4 O, H2 O'
_chemical_formula_sum            'C21 H22 Cl F N4 O2'
_chemical_formula_weight         416.88

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'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   6.7737(3)
_cell_length_b                   9.6448(3)
_cell_length_c                   15.8855(6)
_cell_angle_alpha                97.023(2)
_cell_angle_beta                 97.739(2)
_cell_angle_gamma                107.511(2)
_cell_volume                     966.05(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      4.473
_cell_measurement_theta_max      61.782

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_T_max  0.9165
_exptl_absorpt_process_details   'North et al., 1968'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31230
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         34.60
_reflns_number_total             8055
_reflns_number_gt                5880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0590P)²+0.0588P] 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         8055
_refine_ls_number_parameters     268
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Cl1 Cl 0.03123(5) -0.31808(3) 0.483374(19) 0.02323(8) Uani 1 1 d . . .
F1 F 1.79188(13) 1.44441(9) 1.05156(5) 0.0317(2) Uani 1 1 d . . .
O1W O 0.54380(14) 0.80610(9) 0.72232(6) 0.02060(18) Uani 1 1 d D . .
H1WA H 0.615(2) 0.8817(12) 0.7069(10) 0.031 Uiso 1 1 d D . .
H1WB H 0.633(2) 0.7664(16) 0.7354(10) 0.031 Uiso 1 1 d D . .
O1 O 0.98011(14) 0.89115(10) 0.85728(6) 0.0248(2) Uani 1 1 d . . .
N1 N 0.46979(15) 0.36138(10) 0.72865(6) 0.01517(18) Uani 1 1 d . . .
C1 C 0.09732(19) -0.14798(12) 0.55001(7) 0.0165(2) Uani 1 1 d . . .
N2 N 0.82132(15) 0.62500(10) 0.74665(6) 0.01468(18) Uani 1 1 d . . .
C2 C -0.05419(19) -0.10846(12) 0.58548(7) 0.0165(2) Uani 1 1 d . . .
H2 H -0.1932 -0.1704 0.5728 0.020 Uiso 1 1 calc R . .
N3 N 1.31856(16) 0.91851(10) 0.83991(6) 0.01757(19) Uani 1 1 d . . .
H3 H 1.3920 0.8768 0.8122 0.021 Uiso 1 1 calc R . .
C3 C 0.00299(18) 0.02850(12) 0.64204(7) 0.0143(2) Uani 1 1 d . . .
N4 N -0.15083(16) 0.05915(10) 0.68089(6) 0.01670(18) Uani 1 1 d . . .
C4 C 0.21322(17) 0.12407(11) 0.65766(7) 0.01378(19) Uani 1 1 d . . .
C5 C 0.26560(18) 0.26127(12) 0.71555(7) 0.01410(19) Uani 1 1 d . . .
C6 C 0.53010(18) 0.47511(12) 0.80569(7) 0.0169(2) Uani 1 1 d . . .
H6A H 0.4934 0.4303 0.8553 0.020 Uiso 1 1 calc R . .
H6B H 0.4548 0.5452 0.7983 0.020 Uiso 1 1 calc R . .
C7 C 0.76440(18) 0.55395(13) 0.82046(7) 0.0172(2) Uani 1 1 d . . .
H7A H 0.8055 0.6279 0.8724 0.021 Uiso 1 1 calc R . .
H7B H 0.8392 0.4838 0.8284 0.021 Uiso 1 1 calc R . .
C8 C 1.04585(18) 0.70402(12) 0.76042(7) 0.0167(2) Uani 1 1 d . . .
H8A H 1.0851 0.7257 0.7058 0.020 Uiso 1 1 calc R . .
H8B H 1.1227 0.6414 0.7816 0.020 Uiso 1 1 calc R . .
C9 C 1.10878(18) 0.84789(12) 0.82457(7) 0.0164(2) Uani 1 1 d . . .
C10 C 1.43117(18) 1.05235(12) 0.89589(7) 0.0154(2) Uani 1 1 d . . .
C11 C 1.65002(19) 1.09370(13) 0.90893(8) 0.0192(2) Uani 1 1 d . . .
H11 H 1.7143 1.0320 0.8824 0.023 Uiso 1 1 calc R . .
C12 C 1.7728(2) 1.22590(14) 0.96107(8) 0.0224(2) Uani 1 1 d . . .
H12 H 1.9189 1.2548 0.9690 0.027 Uiso 1 1 calc R . .
C13 C 1.6732(2) 1.31310(13) 1.00065(8) 0.0208(2) Uani 1 1 d . . .
C14 C 1.4586(2) 1.27405(14) 0.99093(8) 0.0222(2) Uani 1 1 d . . .
H14 H 1.3962 1.3350 1.0194 0.027 Uiso 1 1 calc R . .
C15 C 1.3353(2) 1.14242(13) 0.93802(8) 0.0207(2) Uani 1 1 d . . .
H15 H 1.1894 1.1145 0.9308 0.025 Uiso 1 1 calc R . .
C16 C 0.75882(18) 0.51202(12) 0.66864(7) 0.0163(2) Uani 1 1 d . . .
H16A H 0.8357 0.4426 0.6748 0.020 Uiso 1 1 calc R . .
H16B H 0.7939 0.5583 0.6193 0.020 Uiso 1 1 calc R . .
C17 C 0.52497(18) 0.43053(12) 0.65347(7) 0.0162(2) Uani 1 1 d . . .
H17A H 0.4477 0.4989 0.6442 0.019 Uiso 1 1 calc R . .
H17B H 0.4861 0.3552 0.6023 0.019 Uiso 1 1 calc R . .
C18 C 0.11085(19) 0.28426(12) 0.75789(7) 0.0168(2) Uani 1 1 d . . .
H18 H 0.1410 0.3676 0.7998 0.020 Uiso 1 1 calc R . .
C19 C -0.09181(19) 0.18181(12) 0.73754(8) 0.0177(2) Uani 1 1 d . . .
H19 H -0.1933 0.2020 0.7664 0.021 Uiso 1 1 calc R . .
C20 C 0.36442(18) 0.07603(12) 0.62000(7) 0.0164(2) Uani 1 1 d . . .
H20 H 0.5039 0.1369 0.6309 0.020 Uiso 1 1 calc R . .
C21 C 0.30867(19) -0.05818(12) 0.56786(7) 0.0175(2) Uani 1 1 d . . .
H21 H 0.4097 -0.0897 0.5445 0.021 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 C1 1.7373(11) . ?
F1 C13 1.3659(14) . ?
O1W H1WA 0.831(9) . ?
O1W H1WB 0.824(9) . ?
O1 C9 1.2212(14) . ?
N1 C5 1.3994(14) . ?
N1 C6 1.4613(14) . ?
N1 C17 1.4751(14) . ?
C1 C2 1.3619(16) . ?
C1 C21 1.4016(17) . ?
N2 C8 1.4539(15) . ?
N2 C7 1.4670(15) . ?
N2 C16 1.4674(14) . ?
C2 C3 1.4178(15) . ?
C2 H2 0.9300 . ?
N3 C9 1.3514(15) . ?
N3 C10 1.4082(14) . ?
N3 H3 0.8600 . ?
C3 N4 1.3668(14) . ?
C3 C4 1.4135(15) . ?
N4 C19 1.3142(14) . ?
C4 C20 1.4158(15) . ?
C4 C5 1.4334(14) . ?
C5 C18 1.3761(15) . ?
C6 C7 1.5106(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5254(15) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C15 1.3923(16) . ?
C10 C11 1.3931(16) . ?
C11 C12 1.3862(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.3724(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.3693(18) . ?
C14 C15 1.3884(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.5121(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.3969(16) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.3651(15) . ?
C20 H20 0.9300 . ?
C21 H21 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
H1WA O1W H1WB 101.7(14) . . ?
C5 N1 C6 115.86(9) . . ?
C5 N1 C17 114.69(9) . . ?
C6 N1 C17 109.46(9) . . ?
C2 C1 C21 122.24(10) . . ?
C2 C1 Cl1 119.57(9) . . ?
C21 C1 Cl1 118.14(9) . . ?
C8 N2 C7 111.16(9) . . ?
C8 N2 C16 110.26(9) . . ?
C7 N2 C16 109.03(9) . . ?
C1 C2 C3 119.05(11) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C9 N3 C10 127.70(10) . . ?
C9 N3 H3 116.1 . . ?
C10 N3 H3 116.1 . . ?
N4 C3 C4 123.20(10) . . ?
N4 C3 C2 117.10(10) . . ?
C4 C3 C2 119.68(10) . . ?
C19 N4 C3 116.27(10) . . ?
C3 C4 C20 118.64(10) . . ?
C3 C4 C5 118.15(9) . . ?
C20 C4 C5 123.08(10) . . ?
C18 C5 N1 123.56(10) . . ?
C18 C5 C4 117.07(10) . . ?
N1 C5 C4 119.33(9) . . ?
N1 C6 C7 109.38(9) . . ?
N1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 110.34(9) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 112.33(9) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 N3 125.32(11) . . ?
O1 C9 C8 122.35(11) . . ?
N3 C9 C8 112.33(9) . . ?
C15 C10 C11 119.56(11) . . ?
C15 C10 N3 123.53(11) . . ?
C11 C10 N3 116.90(10) . . ?
C12 C11 C10 120.61(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 118.31(12) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
F1 C13 C14 118.38(11) . . ?
F1 C13 C12 119.05(11) . . ?
C14 C13 C12 122.57(11) . . ?
C13 C14 C15 119.20(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 119.71(12) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
N2 C16 C17 110.50(9) . . ?
N2 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N2 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 C16 109.92(9) . . ?
N1 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N1 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C5 C18 C19 119.65(10) . . ?
C5 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
N4 C19 C18 125.34(10) . . ?
N4 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
C21 C20 C4 121.05(11) . . ?
C21 C20 H20 119.5 . . ?
C4 C20 H20 119.5 . . ?
C20 C21 C1 119.22(10) . . ?
C20 C21 H21 120.4 . . ?
C1 C21 H21 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C3 0.39(17) . . . . ?
Cl1 C1 C2 C3 177.92(8) . . . . ?
C1 C2 C3 N4 -175.53(10) . . . . ?
C1 C2 C3 C4 2.71(16) . . . . ?
C4 C3 N4 C19 -2.68(16) . . . . ?
C2 C3 N4 C19 175.50(10) . . . . ?
N4 C3 C4 C20 174.47(11) . . . . ?
C2 C3 C4 C20 -3.66(16) . . . . ?
N4 C3 C4 C5 -1.55(16) . . . . ?
C2 C3 C4 C5 -179.68(10) . . . . ?
C6 N1 C5 C18 15.36(16) . . . . ?
C17 N1 C5 C18 -113.71(12) . . . . ?
C6 N1 C5 C4 -162.16(10) . . . . ?
C17 N1 C5 C4 68.76(13) . . . . ?
C3 C4 C5 C18 5.67(16) . . . . ?
C20 C4 C5 C18 -170.15(11) . . . . ?
C3 C4 C5 N1 -176.64(10) . . . . ?
C20 C4 C5 N1 7.53(16) . . . . ?
C5 N1 C6 C7 168.66(9) . . . . ?
C17 N1 C6 C7 -59.77(12) . . . . ?
C8 N2 C7 C6 178.85(9) . . . . ?
C16 N2 C7 C6 -59.39(12) . . . . ?
N1 C6 C7 N2 60.67(12) . . . . ?
C7 N2 C8 C9 -74.76(12) . . . . ?
C16 N2 C8 C9 164.21(9) . . . . ?
C10 N3 C9 O1 0.7(2) . . . . ?
C10 N3 C9 C8 -179.21(10) . . . . ?
N2 C8 C9 O1 -2.33(17) . . . . ?
N2 C8 C9 N3 177.60(10) . . . . ?
C9 N3 C10 C15 -7.51(19) . . . . ?
C9 N3 C10 C11 172.16(11) . . . . ?
C15 C10 C11 C12 -2.21(18) . . . . ?
N3 C10 C11 C12 178.11(11) . . . . ?
C10 C11 C12 C13 1.27(19) . . . . ?
C11 C12 C13 F1 -179.35(11) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
F1 C13 C14 C15 178.69(11) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C10 0.07(19) . . . . ?
C11 C10 C15 C14 1.52(18) . . . . ?
N3 C10 C15 C14 -178.83(11) . . . . ?
C8 N2 C16 C17 -179.41(9) . . . . ?
C7 N2 C16 C17 58.29(12) . . . . ?
C5 N1 C17 C16 -168.90(9) . . . . ?
C6 N1 C17 C16 58.91(12) . . . . ?
N2 C16 C17 N1 -58.46(12) . . . . ?
N1 C5 C18 C19 176.73(11) . . . . ?
C4 C5 C18 C19 -5.70(17) . . . . ?
C3 N4 C19 C18 2.81(18) . . . . ?
C5 C18 C19 N4 1.48(19) . . . . ?
C3 C4 C20 C21 1.58(17) . . . . ?
C5 C4 C20 C21 177.39(10) . . . . ?
C4 C20 C21 C1 1.45(17) . . . . ?
C2 C1 C21 C20 -2.49(18) . . . . ?
Cl1 C1 C21 C20 179.94(9) . . . . ?

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
O1W H1WA N4 0.831(9) 2.080(10) 2.8965(13) 167.5(16) 1_665
O1W H1WB N2 0.824(9) 2.137(9) 2.9461(13) 167.3(15) .
N3 H3 O1W 0.86 2.03 2.8740(13) 165.1 1_655

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a8
_database_code_depnum_ccdc_archive 'CCDC 1007369'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 Cl N4 O'
_chemical_formula_sum            'C22 H23 Cl N4 O'
_chemical_formula_weight         394.89

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   Pbca
_symmetry_space_group_name_Hall  -P2ac2ab

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

_cell_length_a                   18.2066(10)
_cell_length_b                   11.0845(6)
_cell_length_c                   19.4301(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3921.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      4.474
_cell_measurement_theta_max      54.994

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8999
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_process_details   'North et al., 1968'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45033
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4490
_reflns_number_gt                3547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0436P)²+1.7934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4490
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.24997(2) -0.08534(3) 0.434734(19) 0.02764(11) Uani 1 1 d . . .
O1 O 0.19670(6) 0.79697(9) 0.82188(5) 0.0271(3) Uani 1 1 d . . .
N1 N 0.14185(6) 0.28792(10) 0.69225(6) 0.0179(2) Uani 1 1 d . . .
C1 C 0.21180(8) -0.01130(13) 0.50516(7) 0.0203(3) Uani 1 1 d . . .
N2 N 0.13701(6) 0.53995(10) 0.72414(6) 0.0174(2) Uani 1 1 d . . .
C2 C 0.16862(8) -0.07374(12) 0.54997(8) 0.0202(3) Uani 1 1 d . . .
H2 H 0.1569(9) -0.1582(15) 0.5429(8) 0.022(4) Uiso 1 1 d . . .
N3 N 0.09170(7) 0.68563(11) 0.82838(6) 0.0192(3) Uani 1 1 d . . .
H3N H 0.0698(10) 0.6258(16) 0.8079(9) 0.027(5) Uiso 1 1 d . . .
C3 C 0.14097(7) -0.01519(12) 0.60927(7) 0.0187(3) Uani 1 1 d . . .
N4 N 0.10218(7) -0.08466(11) 0.65514(6) 0.0222(3) Uani 1 1 d . . .
C4 C 0.15604(7) 0.10930(12) 0.61966(7) 0.0172(3) Uani 1 1 d . . .
C5 C 0.12819(7) 0.16523(12) 0.68072(7) 0.0178(3) Uani 1 1 d . . .
C6 C 0.10482(8) 0.37465(13) 0.64646(8) 0.0193(3) Uani 1 1 d . . .
H6B H 0.0531(9) 0.3818(14) 0.6599(8) 0.020(4) Uiso 1 1 d . . .
H6A H 0.1070(9) 0.3482(14) 0.5987(9) 0.021(4) Uiso 1 1 d . . .
C7 C 0.14079(8) 0.49735(13) 0.65292(7) 0.0193(3) Uani 1 1 d . . .
H7B H 0.1154(8) 0.5549(14) 0.6228(8) 0.015(4) Uiso 1 1 d . . .
H7A H 0.1937(9) 0.4917(14) 0.6371(8) 0.024(4) Uiso 1 1 d . . .
C8 C 0.17170(8) 0.65856(13) 0.73041(8) 0.0206(3) Uani 1 1 d . . .
H8B H 0.1529(9) 0.7112(15) 0.6935(8) 0.023(4) Uiso 1 1 d . . .
H8A H 0.2266(9) 0.6527(14) 0.7265(8) 0.023(4) Uiso 1 1 d . . .
C9 C 0.15589(8) 0.72063(12) 0.79827(7) 0.0189(3) Uani 1 1 d . . .
C10 C 0.06555(7) 0.72009(12) 0.89382(7) 0.0180(3) Uani 1 1 d . . .
C11 C 0.08274(8) 0.83098(13) 0.92371(7) 0.0189(3) Uani 1 1 d . . .
H11 H 0.1134(9) 0.8846(15) 0.9006(8) 0.020(4) Uiso 1 1 d . . .
C12 C 0.05218(8) 0.86089(13) 0.98708(8) 0.0216(3) Uani 1 1 d . . .
H12 H 0.0632(9) 0.9390(15) 1.0077(8) 0.025(4) Uiso 1 1 d . . .
C13 C 0.00444(8) 0.78402(14) 1.02171(7) 0.0223(3) Uani 1 1 d . . .
C14 C -0.01181(8) 0.67344(13) 0.99073(8) 0.0222(3) Uani 1 1 d . . .
H14 H -0.0461(9) 0.6178(15) 1.0132(8) 0.026(4) Uiso 1 1 d . . .
C15 C 0.01856(8) 0.64156(13) 0.92815(8) 0.0201(3) Uani 1 1 d . . .
H15 H 0.0071(9) 0.5658(15) 0.9065(8) 0.021(4) Uiso 1 1 d . . .
C16 C 0.17488(8) 0.45212(12) 0.76835(8) 0.0195(3) Uani 1 1 d . . .
H16B H 0.2268(9) 0.4436(14) 0.7537(9) 0.024(4) Uiso 1 1 d . . .
H16A H 0.1722(9) 0.4783(14) 0.8171(8) 0.020(4) Uiso 1 1 d . . .
C17 C 0.13814(8) 0.32994(13) 0.76332(7) 0.0197(3) Uani 1 1 d . . .
H17B H 0.1640(8) 0.2735(14) 0.7930(8) 0.019(4) Uiso 1 1 d . . .
H17A H 0.0856(10) 0.3366(15) 0.7802(8) 0.025(4) Uiso 1 1 d . . .
C18 C 0.09287(8) 0.09230(13) 0.72761(8) 0.0218(3) Uani 1 1 d . . .
H18 H 0.0741(10) 0.1217(15) 0.7717(9) 0.029(4) Uiso 1 1 d . . .
C19 C 0.08138(8) -0.03032(14) 0.71223(8) 0.0238(3) Uani 1 1 d . . .
H19 H 0.0554(10) -0.0822(15) 0.7457(9) 0.028(4) Uiso 1 1 d . . .
C20 C 0.20102(8) 0.16981(13) 0.57115(8) 0.0198(3) Uani 1 1 d . . .
H20 H 0.2146(8) 0.2514(15) 0.5787(8) 0.018(4) Uiso 1 1 d . . .
C21 C 0.22866(8) 0.11146(13) 0.51486(8) 0.0211(3) Uani 1 1 d . . .
H21 H 0.2604(9) 0.1522(15) 0.4818(9) 0.026(4) Uiso 1 1 d . . .
C22 C -0.02786(10) 0.81663(17) 1.09028(9) 0.0309(4) Uani 1 1 d . . .
H22B H 0.0002(10) 0.7779(17) 1.1281(10) 0.041(5) Uiso 1 1 d . . .
H22A H -0.0767(13) 0.794(2) 1.0928(11) 0.057(6) Uiso 1 1 d . . .
H22C H -0.0266(11) 0.9019(19) 1.0995(10) 0.046(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7404(14) . ?
O1 C9 1.2160(17) . ?
N1 C5 1.4006(18) . ?
N1 C17 1.4589(18) . ?
N1 C6 1.4732(18) . ?
C1 C2 1.362(2) . ?
C1 C21 1.408(2) . ?
N2 C8 1.4636(18) . ?
N2 C7 1.4638(18) . ?
N2 C16 1.4702(18) . ?
C2 C3 1.415(2) . ?
C2 H2 0.969(16) . ?
N3 C9 1.3633(18) . ?
N3 C10 1.4103(18) . ?
N3 H3N 0.870(18) . ?
C3 N4 1.3734(18) . ?
C3 C4 1.4213(19) . ?
N4 C19 1.318(2) . ?
C4 C20 1.417(2) . ?
C4 C5 1.4314(19) . ?
C5 C18 1.377(2) . ?
C6 C7 1.515(2) . ?
C6 H6B 0.980(17) . ?
C6 H6A 0.973(16) . ?
C7 H7B 0.980(15) . ?
C7 H7A 1.012(17) . ?
C8 C9 1.515(2) . ?
C8 H8B 0.986(17) . ?
C8 H8A 1.005(17) . ?
C10 C15 1.391(2) . ?
C10 C11 1.3950(19) . ?
C11 C12 1.391(2) . ?
C11 H11 0.931(17) . ?
C12 C13 1.391(2) . ?
C12 H12 0.975(17) . ?
C13 C14 1.397(2) . ?
C13 C22 1.501(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.980(17) . ?
C15 H15 0.962(16) . ?
C16 C17 1.514(2) . ?
C16 H16B 0.993(17) . ?
C16 H16A 0.992(16) . ?
C17 H17B 0.973(16) . ?
C17 H17A 1.013(17) . ?
C18 C19 1.407(2) . ?
C18 H18 0.978(18) . ?
C19 H19 0.990(18) . ?
C20 C21 1.367(2) . ?
C20 H20 0.949(16) . ?
C21 H21 0.976(18) . ?
C22 H22B 0.99(2) . ?
C22 H22A 0.92(2) . ?
C22 H22C 0.96(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
C5 N1 C17 116.95(11) . . ?
C5 N1 C6 117.11(11) . . ?
C17 N1 C6 110.01(11) . . ?
C2 C1 C21 122.10(13) . . ?
C2 C1 Cl1 119.57(11) . . ?
C21 C1 Cl1 118.30(11) . . ?
C8 N2 C7 110.38(11) . . ?
C8 N2 C16 110.11(11) . . ?
C7 N2 C16 108.47(11) . . ?
C1 C2 C3 119.52(13) . . ?
C1 C2 H2 121.8(10) . . ?
C3 C2 H2 118.7(10) . . ?
C9 N3 C10 126.81(12) . . ?
C9 N3 H3N 114.5(11) . . ?
C10 N3 H3N 117.6(11) . . ?
N4 C3 C2 117.01(12) . . ?
N4 C3 C4 123.46(13) . . ?
C2 C3 C4 119.50(13) . . ?
C19 N4 C3 115.96(12) . . ?
C20 C4 C3 118.46(13) . . ?
C20 C4 C5 123.42(12) . . ?
C3 C4 C5 118.03(12) . . ?
C18 C5 N1 123.16(13) . . ?
C18 C5 C4 117.35(13) . . ?
N1 C5 C4 119.36(12) . . ?
N1 C6 C7 109.75(11) . . ?
N1 C6 H6B 109.3(9) . . ?
C7 C6 H6B 108.7(9) . . ?
N1 C6 H6A 111.1(9) . . ?
C7 C6 H6A 109.4(9) . . ?
H6B C6 H6A 108.5(13) . . ?
N2 C7 C6 110.35(12) . . ?
N2 C7 H7B 109.4(9) . . ?
C6 C7 H7B 109.3(9) . . ?
N2 C7 H7A 110.6(9) . . ?
C6 C7 H7A 109.3(9) . . ?
H7B C7 H7A 107.9(13) . . ?
N2 C8 C9 113.48(12) . . ?
N2 C8 H8B 108.8(10) . . ?
C9 C8 H8B 107.3(9) . . ?
N2 C8 H8A 111.4(9) . . ?
C9 C8 H8A 106.5(9) . . ?
H8B C8 H8A 109.2(13) . . ?
O1 C9 N3 124.05(13) . . ?
O1 C9 C8 121.89(13) . . ?
N3 C9 C8 114.03(12) . . ?
C15 C10 C11 119.32(13) . . ?
C15 C10 N3 118.07(13) . . ?
C11 C10 N3 122.56(13) . . ?
C12 C11 C10 119.26(13) . . ?
C12 C11 H11 121.0(10) . . ?
C10 C11 H11 119.7(10) . . ?
C13 C12 C11 122.15(14) . . ?
C13 C12 H12 118.3(10) . . ?
C11 C12 H12 119.5(10) . . ?
C12 C13 C14 117.47(13) . . ?
C12 C13 C22 121.80(14) . . ?
C14 C13 C22 120.72(14) . . ?
C15 C14 C13 121.24(14) . . ?
C15 C14 H14 119.1(10) . . ?
C13 C14 H14 119.6(10) . . ?
C14 C15 C10 120.55(13) . . ?
C14 C15 H15 121.4(10) . . ?
C10 C15 H15 118.0(10) . . ?
N2 C16 C17 110.34(12) . . ?
N2 C16 H16B 110.0(10) . . ?
C17 C16 H16B 108.5(9) . . ?
N2 C16 H16A 109.9(9) . . ?
C17 C16 H16A 107.6(9) . . ?
H16B C16 H16A 110.5(13) . . ?
N1 C17 C16 109.05(12) . . ?
N1 C17 H17B 109.5(9) . . ?
C16 C17 H17B 108.9(9) . . ?
N1 C17 H17A 111.9(9) . . ?
C16 C17 H17A 109.3(9) . . ?
H17B C17 H17A 108.2(13) . . ?
C5 C18 C19 119.72(14) . . ?
C5 C18 H18 123.2(10) . . ?
C19 C18 H18 117.1(10) . . ?
N4 C19 C18 125.27(14) . . ?
N4 C19 H19 115.2(10) . . ?
C18 C19 H19 119.5(10) . . ?
C21 C20 C4 121.39(13) . . ?
C21 C20 H20 118.7(9) . . ?
C4 C20 H20 119.9(9) . . ?
C20 C21 C1 118.98(14) . . ?
C20 C21 H21 121.7(10) . . ?
C1 C21 H21 119.3(10) . . ?
C13 C22 H22B 110.6(11) . . ?
C13 C22 H22A 111.1(14) . . ?
H22B C22 H22A 109.9(17) . . ?
C13 C22 H22C 113.1(12) . . ?
H22B C22 H22C 106.0(16) . . ?
H22A C22 H22C 105.9(18) . . ?

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
C21 C1 C2 C3 -1.6(2) . . . . ?
Cl1 C1 C2 C3 176.48(10) . . . . ?
C1 C2 C3 N4 -175.45(13) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
C2 C3 N4 C19 175.43(13) . . . . ?
C4 C3 N4 C19 -2.7(2) . . . . ?
N4 C3 C4 C20 175.61(13) . . . . ?
C2 C3 C4 C20 -2.42(19) . . . . ?
N4 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 -179.05(12) . . . . ?
C17 N1 C5 C18 18.37(19) . . . . ?
C6 N1 C5 C18 -115.39(15) . . . . ?
C17 N1 C5 C4 -157.34(12) . . . . ?
C6 N1 C5 C4 68.90(16) . . . . ?
C20 C4 C5 C18 -172.12(13) . . . . ?
C3 C4 C5 C18 4.33(19) . . . . ?
C20 C4 C5 N1 3.8(2) . . . . ?
C3 C4 C5 N1 -179.72(12) . . . . ?
C5 N1 C6 C7 -164.65(12) . . . . ?
C17 N1 C6 C7 58.60(15) . . . . ?
C8 N2 C7 C6 -179.95(12) . . . . ?
C16 N2 C7 C6 59.34(14) . . . . ?
N1 C6 C7 N2 -58.85(15) . . . . ?
C7 N2 C8 C9 167.55(12) . . . . ?
C16 N2 C8 C9 -72.73(15) . . . . ?
C10 N3 C9 O1 -7.4(2) . . . . ?
C10 N3 C9 C8 174.47(13) . . . . ?
N2 C8 C9 O1 155.69(13) . . . . ?
N2 C8 C9 N3 -26.14(18) . . . . ?
C9 N3 C10 C15 -152.96(14) . . . . ?
C9 N3 C10 C11 29.6(2) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
N3 C10 C11 C12 177.09(13) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C12 C13 C22 179.56(14) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C22 C13 C14 C15 -178.91(14) . . . . ?
C13 C14 C15 C10 -0.9(2) . . . . ?
C11 C10 C15 C14 1.0(2) . . . . ?
N3 C10 C15 C14 -176.55(12) . . . . ?
C8 N2 C16 C17 178.70(12) . . . . ?
C7 N2 C16 C17 -60.42(15) . . . . ?
C5 N1 C17 C16 163.94(12) . . . . ?
C6 N1 C17 C16 -59.24(15) . . . . ?
N2 C16 C17 N1 60.72(15) . . . . ?
N1 C5 C18 C19 -179.84(13) . . . . ?
C4 C5 C18 C19 -4.1(2) . . . . ?
C3 N4 C19 C18 3.1(2) . . . . ?
C5 C18 C19 N4 0.3(2) . . . . ?
C3 C4 C20 C21 1.1(2) . . . . ?
C5 C4 C20 C21 177.49(13) . . . . ?
C4 C20 C21 C1 0.1(2) . . . . ?
C2 C1 C21 C20 0.2(2) . . . . ?
Cl1 C1 C21 C20 -177.90(11) . . . . ?

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
N3 H3N N2 0.870(18) 2.248(17) 2.7186(17) 113.8(14) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_a18
_database_code_depnum_ccdc_archive 'CCDC 1007370'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 Cl N4 O'
_chemical_formula_sum            'C22 H23 Cl N4 O'
_chemical_formula_weight         394.89

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.0751(4)
_cell_length_b                   9.2785(4)
_cell_length_c                   14.1227(8)
_cell_angle_alpha                105.382(3)
_cell_angle_beta                 92.801(3)
_cell_angle_gamma                119.213(2)
_cell_volume                     978.02(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      5.171
_cell_measurement_theta_max      57.575

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_process_details   'North et al., 1968'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            58473
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         29.38
_reflns_number_total             5375
_reflns_number_gt                4420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0503P)²+0.3399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5375
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 -0.73754(4) -0.53367(4) -0.13919(2) 0.02714(10) Uani 1 1 d . . .
O1 O 0.34372(14) 0.61046(13) 0.60594(7) 0.0307(2) Uani 1 1 d . . .
N1 N -0.01010(13) 0.21834(13) 0.14212(7) 0.0178(2) Uani 1 1 d . . .
C1 C -0.56091(15) -0.32291(16) -0.08215(9) 0.0196(2) Uani 1 1 d . . .
N2 N 0.20561(13) 0.41810(13) 0.33723(7) 0.0185(2) Uani 1 1 d . . .
C2 C -0.50623(15) -0.20986(16) -0.13537(9) 0.0186(2) Uani 1 1 d . . .
H2 H -0.560(2) -0.239(2) -0.2046(13) 0.029(4) Uiso 1 1 d . . .
N3 N 0.29757(14) 0.71396(14) 0.48410(8) 0.0196(2) Uani 1 1 d . . .
H3N H 0.269(2) 0.680(2) 0.4230(13) 0.026(4) Uiso 1 1 d . . .
C3 C -0.35700(15) -0.04152(16) -0.09084(9) 0.0178(2) Uani 1 1 d . . .
N4 N -0.30344(14) 0.06474(15) -0.14872(8) 0.0226(2) Uani 1 1 d . . .
C4 C -0.26581(15) 0.00556(15) 0.00754(8) 0.0168(2) Uani 1 1 d . . .
C5 C -0.10814(15) 0.17103(16) 0.04679(9) 0.0179(2) Uani 1 1 d . . .
C6 C 0.17519(16) 0.33982(17) 0.15677(9) 0.0208(2) Uani 1 1 d . . .
H6B H 0.214(2) 0.295(2) 0.0991(12) 0.025(4) Uiso 1 1 d . . .
H6A H 0.202(2) 0.460(2) 0.1626(12) 0.025(4) Uiso 1 1 d . . .
C7 C 0.26650(16) 0.34999(17) 0.25293(9) 0.0213(2) Uani 1 1 d . . .
H7B H 0.391(2) 0.432(2) 0.2635(12) 0.024(4) Uiso 1 1 d . . .
H7A H 0.247(2) 0.231(2) 0.2485(11) 0.021(4) Uiso 1 1 d . . .
C8 C 0.30170(18) 0.44938(18) 0.43351(9) 0.0234(3) Uani 1 1 d . . .
H8B H 0.252(2) 0.346(2) 0.4533(13) 0.034(4) Uiso 1 1 d . . .
H8A H 0.423(2) 0.485(2) 0.4279(12) 0.024(4) Uiso 1 1 d . . .
C9 C 0.31523(16) 0.59929(17) 0.51812(9) 0.0203(2) Uani 1 1 d . . .
C10 C 0.31005(16) 0.87138(16) 0.53914(9) 0.0191(2) Uani 1 1 d . . .
C11 C 0.41117(16) 0.96912(17) 0.63586(9) 0.0227(3) Uani 1 1 d . . .
H11 H 0.477(2) 0.931(2) 0.6666(12) 0.029(4) Uiso 1 1 d . . .
C12 C 0.41924(19) 1.12383(18) 0.68662(10) 0.0293(3) Uani 1 1 d . . .
H12 H 0.491(2) 1.189(2) 0.7507(14) 0.037(5) Uiso 1 1 d . . .
C13 C 0.3283(2) 1.18070(19) 0.64219(12) 0.0318(3) Uani 1 1 d . . .
H13 H 0.331(2) 1.285(3) 0.6747(14) 0.044(5) Uiso 1 1 d . . .
C14 C 0.23013(19) 1.08329(18) 0.54557(11) 0.0287(3) Uani 1 1 d . . .
H14 H 0.164(2) 1.125(2) 0.5145(14) 0.040(5) Uiso 1 1 d . . .
C15 C 0.21921(17) 0.92843(17) 0.49195(9) 0.0220(2) Uani 1 1 d . . .
C16 C 0.02005(16) 0.29926(17) 0.32495(9) 0.0207(2) Uani 1 1 d . . .
H16B H -0.004(2) 0.183(2) 0.3259(12) 0.028(4) Uiso 1 1 d . . .
H16A H -0.021(2) 0.348(2) 0.3825(12) 0.025(4) Uiso 1 1 d . . .
C17 C -0.07724(15) 0.27784(17) 0.22693(9) 0.0193(2) Uani 1 1 d . . .
H17B H -0.0646(18) 0.391(2) 0.2322(11) 0.017(3) Uiso 1 1 d . . .
H17A H -0.199(2) 0.194(2) 0.2191(12) 0.022(4) Uiso 1 1 d . . .
C18 C -0.05524(17) 0.27307(17) -0.01381(10) 0.0238(3) Uani 1 1 d . . .
H18 H 0.050(2) 0.384(2) 0.0062(12) 0.030(4) Uiso 1 1 d . . .
C19 C -0.15792(18) 0.21458(18) -0.10936(10) 0.0257(3) Uani 1 1 d . . .
H19 H -0.119(2) 0.292(2) -0.1519(13) 0.037(5) Uiso 1 1 d . . .
C20 C -0.32857(16) -0.11718(16) 0.05921(9) 0.0191(2) Uani 1 1 d . . .
H20 H -0.266(2) -0.084(2) 0.1251(12) 0.027(4) Uiso 1 1 d . . .
C21 C -0.47483(16) -0.27867(17) 0.01578(9) 0.0208(2) Uani 1 1 d . . .
H21 H -0.514(2) -0.360(2) 0.0516(12) 0.028(4) Uiso 1 1 d . . .
C22 C 0.1133(2) 0.8252(2) 0.38662(11) 0.0291(3) Uani 1 1 d . . .
H22C H 0.061(2) 0.885(2) 0.3661(14) 0.039(5) Uiso 1 1 d . . .
H22B H 0.020(2) 0.704(2) 0.3809(13) 0.037(5) Uiso 1 1 d . . .
H22A H 0.183(2) 0.815(2) 0.3392(14) 0.037(5) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7380(12) . ?
O1 C9 1.2207(15) . ?
N1 C5 1.4090(14) . ?
N1 C6 1.4605(15) . ?
N1 C17 1.4696(15) . ?
C1 C2 1.3631(18) . ?
C1 C21 1.4042(17) . ?
N2 C8 1.4564(15) . ?
N2 C7 1.4588(16) . ?
N2 C16 1.4625(16) . ?
C2 C3 1.4142(17) . ?
C2 H2 0.977(17) . ?
N3 C9 1.3486(16) . ?
N3 C10 1.4065(16) . ?
N3 H3N 0.815(17) . ?
C3 N4 1.3693(16) . ?
C3 C4 1.4210(16) . ?
N4 C19 1.3085(17) . ?
C4 C20 1.4150(17) . ?
C4 C5 1.4278(16) . ?
C5 C18 1.3731(17) . ?
C6 C7 1.5118(17) . ?
C6 H6B 0.978(16) . ?
C6 H6A 0.995(16) . ?
C7 H7B 0.979(16) . ?
C7 H7A 1.013(16) . ?
C8 C9 1.5215(18) . ?
C8 H8B 0.964(18) . ?
C8 H8A 0.995(16) . ?
C10 C11 1.3922(17) . ?
C10 C15 1.4012(18) . ?
C11 C12 1.3879(19) . ?
C11 H11 0.966(17) . ?
C12 C13 1.380(2) . ?
C12 H12 0.938(19) . ?
C13 C14 1.383(2) . ?
C13 H13 0.94(2) . ?
C14 C15 1.3872(19) . ?
C14 H14 1.002(19) . ?
C15 C22 1.5032(19) . ?
C16 C17 1.5161(16) . ?
C16 H16B 0.996(17) . ?
C16 H16A 1.000(16) . ?
C17 H17B 0.985(15) . ?
C17 H17A 0.972(16) . ?
C18 C19 1.4066(17) . ?
C18 H18 0.954(17) . ?
C19 H19 1.001(18) . ?
C20 C21 1.3692(17) . ?
C20 H20 0.954(16) . ?
C21 H21 0.957(17) . ?
C22 H22C 0.976(19) . ?
C22 H22B 1.003(19) . ?
C22 H22A 0.962(19) . ?

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
C5 N1 C6 115.12(10) . . ?
C5 N1 C17 114.39(9) . . ?
C6 N1 C17 110.54(9) . . ?
C2 C1 C21 122.50(11) . . ?
C2 C1 Cl1 119.10(9) . . ?
C21 C1 Cl1 118.33(10) . . ?
C8 N2 C7 112.00(10) . . ?
C8 N2 C16 111.66(10) . . ?
C7 N2 C16 109.72(10) . . ?
C1 C2 C3 119.09(11) . . ?
C1 C2 H2 124.4(10) . . ?
C3 C2 H2 116.5(10) . . ?
C9 N3 C10 128.99(11) . . ?
C9 N3 H3N 112.1(12) . . ?
C10 N3 H3N 118.8(12) . . ?
N4 C3 C2 116.87(10) . . ?
N4 C3 C4 123.48(11) . . ?
C2 C3 C4 119.56(11) . . ?
C19 N4 C3 116.11(11) . . ?
C20 C4 C3 118.87(11) . . ?
C20 C4 C5 123.07(10) . . ?
C3 C4 C5 117.92(11) . . ?
C18 C5 N1 123.09(11) . . ?
C18 C5 C4 117.38(11) . . ?
N1 C5 C4 119.44(10) . . ?
N1 C6 C7 108.93(10) . . ?
N1 C6 H6B 107.7(9) . . ?
C7 C6 H6B 110.6(9) . . ?
N1 C6 H6A 111.6(9) . . ?
C7 C6 H6A 108.1(9) . . ?
H6B C6 H6A 109.9(13) . . ?
N2 C7 C6 109.04(10) . . ?
N2 C7 H7B 107.7(9) . . ?
C6 C7 H7B 109.3(9) . . ?
N2 C7 H7A 111.8(9) . . ?
C6 C7 H7A 110.4(9) . . ?
H7B C7 H7A 108.5(13) . . ?
N2 C8 C9 113.21(10) . . ?
N2 C8 H8B 111.8(11) . . ?
C9 C8 H8B 108.5(11) . . ?
N2 C8 H8A 108.7(9) . . ?
C9 C8 H8A 105.5(9) . . ?
H8B C8 H8A 108.9(14) . . ?
O1 C9 N3 126.29(12) . . ?
O1 C9 C8 121.24(11) . . ?
N3 C9 C8 112.45(10) . . ?
C11 C10 C15 121.03(12) . . ?
C11 C10 N3 121.65(11) . . ?
C15 C10 N3 117.31(11) . . ?
C12 C11 C10 119.22(13) . . ?
C12 C11 H11 120.4(10) . . ?
C10 C11 H11 120.4(10) . . ?
C13 C12 C11 120.65(13) . . ?
C13 C12 H12 121.7(11) . . ?
C11 C12 H12 117.6(11) . . ?
C12 C13 C14 119.44(13) . . ?
C12 C13 H13 122.6(12) . . ?
C14 C13 H13 118.0(12) . . ?
C13 C14 C15 121.79(14) . . ?
C13 C14 H14 118.6(11) . . ?
C15 C14 H14 119.6(11) . . ?
C14 C15 C10 117.85(12) . . ?
C14 C15 C22 121.05(12) . . ?
C10 C15 C22 121.10(12) . . ?
N2 C16 C17 110.38(10) . . ?
N2 C16 H16B 110.1(9) . . ?
C17 C16 H16B 109.7(9) . . ?
N2 C16 H16A 109.1(9) . . ?
C17 C16 H16A 109.7(9) . . ?
H16B C16 H16A 107.8(13) . . ?
N1 C17 C16 110.34(10) . . ?
N1 C17 H17B 111.6(8) . . ?
C16 C17 H17B 107.7(8) . . ?
N1 C17 H17A 110.7(9) . . ?
C16 C17 H17A 108.6(9) . . ?
H17B C17 H17A 107.8(12) . . ?
C5 C18 C19 119.79(12) . . ?
C5 C18 H18 122.5(10) . . ?
C19 C18 H18 117.7(10) . . ?
N4 C19 C18 125.29(12) . . ?
N4 C19 H19 116.0(10) . . ?
C18 C19 H19 118.8(10) . . ?
C21 C20 C4 120.92(11) . . ?
C21 C20 H20 121.1(10) . . ?
C4 C20 H20 118.0(10) . . ?
C20 C21 C1 119.05(12) . . ?
C20 C21 H21 119.5(10) . . ?
C1 C21 H21 121.4(10) . . ?
C15 C22 H22C 109.6(11) . . ?
C15 C22 H22B 111.7(10) . . ?
H22C C22 H22B 109.2(15) . . ?
C15 C22 H22A 111.8(11) . . ?
H22C C22 H22A 106.7(15) . . ?
H22B C22 H22A 107.8(15) . . ?

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
C21 C1 C2 C3 0.15(18) . . . . ?
Cl1 C1 C2 C3 -176.65(9) . . . . ?
C1 C2 C3 N4 177.54(11) . . . . ?
C1 C2 C3 C4 0.90(17) . . . . ?
C2 C3 N4 C19 -174.87(11) . . . . ?
C4 C3 N4 C19 1.63(18) . . . . ?
N4 C3 C4 C20 -177.30(11) . . . . ?
C2 C3 C4 C20 -0.89(17) . . . . ?
N4 C3 C4 C5 -1.41(17) . . . . ?
C2 C3 C4 C5 175.00(11) . . . . ?
C6 N1 C5 C18 -23.94(17) . . . . ?
C17 N1 C5 C18 105.71(14) . . . . ?
C6 N1 C5 C4 152.55(11) . . . . ?
C17 N1 C5 C4 -77.81(14) . . . . ?
C20 C4 C5 C18 175.43(12) . . . . ?
C3 C4 C5 C18 -0.27(17) . . . . ?
C20 C4 C5 N1 -1.25(17) . . . . ?
C3 C4 C5 N1 -176.95(10) . . . . ?
C5 N1 C6 C7 -168.85(10) . . . . ?
C17 N1 C6 C7 59.64(13) . . . . ?
C8 N2 C7 C6 -173.77(11) . . . . ?
C16 N2 C7 C6 61.64(13) . . . . ?
N1 C6 C7 N2 -62.02(13) . . . . ?
C7 N2 C8 C9 149.45(11) . . . . ?
C16 N2 C8 C9 -87.04(13) . . . . ?
C10 N3 C9 O1 1.2(2) . . . . ?
C10 N3 C9 C8 -176.85(12) . . . . ?
N2 C8 C9 O1 157.95(12) . . . . ?
N2 C8 C9 N3 -23.88(16) . . . . ?
C9 N3 C10 C11 27.5(2) . . . . ?
C9 N3 C10 C15 -153.75(13) . . . . ?
C15 C10 C11 C12 1.13(19) . . . . ?
N3 C10 C11 C12 179.79(12) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C13 C14 C15 C22 -179.37(13) . . . . ?
C11 C10 C15 C14 -1.45(19) . . . . ?
N3 C10 C15 C14 179.83(11) . . . . ?
C11 C10 C15 C22 178.54(12) . . . . ?
N3 C10 C15 C22 -0.17(18) . . . . ?
C8 N2 C16 C17 176.65(10) . . . . ?
C7 N2 C16 C17 -58.56(13) . . . . ?
C5 N1 C17 C16 171.47(10) . . . . ?
C6 N1 C17 C16 -56.64(13) . . . . ?
N2 C16 C17 N1 55.69(13) . . . . ?
N1 C5 C18 C19 178.13(12) . . . . ?
C4 C5 C18 C19 1.58(19) . . . . ?
C3 N4 C19 C18 -0.2(2) . . . . ?
C5 C18 C19 N4 -1.4(2) . . . . ?
C3 C4 C20 C21 -0.17(18) . . . . ?
C5 C4 C20 C21 -175.83(11) . . . . ?
C4 C20 C21 C1 1.19(19) . . . . ?
C2 C1 C21 C20 -1.20(19) . . . . ?
Cl1 C1 C21 C20 175.62(10) . . . . ?

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
N3 H3N N2 0.815(17) 2.165(17) 2.6662(15) 119.8(14) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.38
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_a21
_database_code_depnum_ccdc_archive 'CCDC 1036519'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 Cl3 N5 O'
_chemical_formula_sum            'C25 H26 Cl3 N5 O'
_chemical_formula_weight         518.86

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6408(3)
_cell_length_b                   12.9637(3)
_cell_length_c                   19.8442(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1580(10)
_cell_angle_gamma                90.00
_cell_volume                     2455.04(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      4.461
_cell_measurement_theta_max      61.009

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8242
_exptl_absorpt_correction_T_max  0.8557
_exptl_absorpt_process_details   'North et al., 1968'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36222
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         30.64
_reflns_number_total             7551
_reflns_number_gt                6536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0518P)²+0.6250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7551
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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 1.51243(3) 0.62738(3) 0.057711(19) 0.04084(10) Uani 1 1 d . . .
O1 O 0.98371(9) -0.07676(7) 0.23276(4) 0.02872(19) Uani 1 1 d . . .
N1 N 0.95671(9) 0.36987(7) 0.15411(5) 0.01794(17) Uani 1 1 d . . .
C1 C 1.35392(11) 0.57812(9) 0.07532(6) 0.0223(2) Uani 1 1 d . . .
Cl2 Cl 0.60431(3) -0.22689(2) -0.070401(13) 0.02359(7) Uani 1 1 d . . .
N2 N 0.87107(9) 0.17304(7) 0.19786(4) 0.01759(17) Uani 1 1 d . . .
C2 C 1.23365(11) 0.63015(9) 0.05228(5) 0.0206(2) Uani 1 1 d . . .
H2 H 1.2335(15) 0.6926(11) 0.0261(8) 0.027(4) Uiso 1 1 d . . .
Cl3 Cl 0.57855(3) -0.20247(3) -0.228034(15) 0.03513(9) Uani 1 1 d . . .
N3 N 0.80011(10) -0.04300(7) 0.15197(5) 0.02075(18) Uani 1 1 d . . .
C3 C 1.10359(10) 0.59158(8) 0.06642(5) 0.01716(19) Uani 1 1 d . . .
N4 N 0.71192(9) -0.04516(7) 0.01002(4) 0.01833(17) Uani 1 1 d . . .
C4 C 1.10019(10) 0.49793(8) 0.10353(5) 0.01546(18) Uani 1 1 d . . .
N5 N 0.98752(10) 0.64934(7) 0.04377(5) 0.02117(18) Uani 1 1 d . . .
C5 C 0.96631(10) 0.46119(8) 0.11688(5) 0.01693(18) Uani 1 1 d . . .
C6 C 0.82469(12) 0.35608(9) 0.18163(6) 0.0240(2) Uani 1 1 d . . .
H6B H 0.8051(16) 0.4198(13) 0.2053(8) 0.035(4) Uiso 1 1 d . . .
H6A H 0.7431(16) 0.3413(12) 0.1451(8) 0.029(4) Uiso 1 1 d . . .
C7 C 0.83698(12) 0.26745(9) 0.23185(6) 0.0229(2) Uani 1 1 d . . .
H7B H 0.9093(16) 0.2825(11) 0.2721(8) 0.027(4) Uiso 1 1 d . . .
H7A H 0.7488(16) 0.2583(12) 0.2488(7) 0.025(4) Uiso 1 1 d . . .
C8 C 0.87020(12) 0.08452(9) 0.24317(5) 0.0210(2) Uani 1 1 d . . .
H8B H 0.7782(14) 0.0852(11) 0.2611(7) 0.021(3) Uiso 1 1 d . . .
H8A H 0.9411(15) 0.0889(11) 0.2821(7) 0.023(3) Uiso 1 1 d . . .
C9 C 0.88947(11) -0.01854(8) 0.20857(5) 0.0191(2) Uani 1 1 d . . .
C10 C 0.82391(13) -0.13458(9) 0.11237(5) 0.0217(2) Uani 1 1 d . . .
H10B H 0.9058(16) -0.1696(12) 0.1338(8) 0.031(4) Uiso 1 1 d . . .
H10A H 0.7424(16) -0.1796(12) 0.1121(7) 0.027(4) Uiso 1 1 d . . .
C11 C 0.83709(11) -0.10316(9) 0.03974(5) 0.0195(2) Uani 1 1 d . . .
H11B H 0.8458(14) -0.1634(11) 0.0131(7) 0.021(3) Uiso 1 1 d . . .
H11A H 0.9204(15) -0.0602(11) 0.0403(7) 0.025(3) Uiso 1 1 d . . .
C12 C 0.69308(11) 0.04736(9) 0.04983(5) 0.0208(2) Uani 1 1 d . . .
H12B H 0.6088(16) 0.0852(12) 0.0293(8) 0.030(4) Uiso 1 1 d . . .
H12A H 0.7713(15) 0.0951(11) 0.0530(7) 0.024(3) Uiso 1 1 d . . .
C13 C 0.67727(11) 0.01606(9) 0.12220(6) 0.0217(2) Uani 1 1 d . . .
H13B H 0.5946(15) -0.0274(12) 0.1221(7) 0.027(4) Uiso 1 1 d . . .
H13A H 0.6667(14) 0.0775(11) 0.1482(7) 0.023(3) Uiso 1 1 d . . .
C14 C 0.70202(10) -0.03090(8) -0.06133(5) 0.01883(19) Uani 1 1 d . . .
C15 C 0.65377(10) -0.11263(8) -0.10473(5) 0.01866(19) Uani 1 1 d . . .
C16 C 0.63953(12) -0.10080(10) -0.17524(5) 0.0246(2) Uani 1 1 d . . .
C17 C 0.67154(14) -0.00802(12) -0.20357(6) 0.0344(3) Uani 1 1 d . . .
H17 H 0.6627(17) 0.0005(13) -0.2513(9) 0.042(4) Uiso 1 1 d . . .
C18 C 0.71851(16) 0.07313(12) -0.16126(7) 0.0364(3) Uani 1 1 d . . .
H18 H 0.7436(19) 0.1377(14) -0.1781(9) 0.047(5) Uiso 1 1 d . . .
C19 C 0.73399(13) 0.06220(10) -0.09092(6) 0.0274(2) Uani 1 1 d . . .
H19 H 0.7643(16) 0.1160(12) -0.0640(8) 0.029(4) Uiso 1 1 d . . .
C20 C 1.00568(11) 0.18572(8) 0.17264(5) 0.01836(19) Uani 1 1 d . . .
H20B H 1.0264(14) 0.1222(10) 0.1505(7) 0.017(3) Uiso 1 1 d . . .
H20A H 1.0824(15) 0.2015(11) 0.2109(7) 0.022(3) Uiso 1 1 d . . .
C21 C 0.99464(11) 0.27351(8) 0.12168(5) 0.01781(19) Uani 1 1 d . . .
H21B H 1.0832(14) 0.2821(10) 0.1027(7) 0.019(3) Uiso 1 1 d . . .
H21A H 0.9220(15) 0.2556(11) 0.0820(7) 0.024(3) Uiso 1 1 d . . .
C22 C 0.85158(11) 0.52228(9) 0.09502(6) 0.0215(2) Uani 1 1 d . . .
H22 H 0.7561(16) 0.5017(12) 0.1018(8) 0.028(4) Uiso 1 1 d . . .
C23 C 0.86807(11) 0.61360(9) 0.05889(6) 0.0226(2) Uani 1 1 d . . .
H23 H 0.7858(16) 0.6549(12) 0.0418(8) 0.028(4) Uiso 1 1 d . . .
C24 C 1.22904(10) 0.44919(8) 0.12818(5) 0.01719(18) Uani 1 1 d . . .
H24 H 1.2311(14) 0.3898(11) 0.1566(7) 0.022(3) Uiso 1 1 d . . .
C25 C 1.35433(11) 0.48782(9) 0.11417(5) 0.0204(2) Uani 1 1 d . . .
H25 H 1.4414(15) 0.4551(12) 0.1332(8) 0.028(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7369(11) . ?
O1 C9 1.2255(13) . ?
N1 C5 1.4054(13) . ?
N1 C6 1.4655(13) . ?
N1 C21 1.4748(13) . ?
C1 C2 1.3630(15) . ?
C1 C25 1.4014(15) . ?
Cl2 C15 1.7257(11) . ?
N2 C7 1.4574(14) . ?
N2 C8 1.4585(13) . ?
N2 C20 1.4650(13) . ?
C2 C3 1.4145(14) . ?
C2 H2 0.962(15) . ?
Cl3 C16 1.7337(12) . ?
N3 C9 1.3526(13) . ?
N3 C10 1.4598(14) . ?
N3 C13 1.4626(14) . ?
C3 N5 1.3683(13) . ?
C3 C4 1.4227(14) . ?
N4 C14 1.4176(13) . ?
N4 C12 1.4617(13) . ?
N4 C11 1.4722(13) . ?
C4 C24 1.4175(14) . ?
C4 C5 1.4353(14) . ?
N5 C23 1.3149(14) . ?
C5 C22 1.3794(14) . ?
C6 C7 1.5144(16) . ?
C6 H6B 0.982(17) . ?
C6 H6A 1.010(16) . ?
C7 H7B 1.002(15) . ?
C7 H7A 0.966(15) . ?
C8 C9 1.5256(15) . ?
C8 H8B 1.002(14) . ?
C8 H8A 0.957(14) . ?
C10 C11 1.5203(15) . ?
C10 H10B 0.957(16) . ?
C10 H10A 0.978(15) . ?
C11 H11B 0.953(14) . ?
C11 H11A 0.976(15) . ?
C12 C13 1.5207(16) . ?
C12 H12B 0.987(15) . ?
C12 H12A 0.971(15) . ?
C13 H13B 0.976(15) . ?
C13 H13A 0.962(14) . ?
C14 C19 1.3955(16) . ?
C14 C15 1.4025(15) . ?
C15 C16 1.3947(14) . ?
C16 C17 1.3810(19) . ?
C17 C18 1.382(2) . ?
C17 H17 0.945(18) . ?
C18 C19 1.3899(18) . ?
C18 H18 0.946(18) . ?
C19 H19 0.901(16) . ?
C20 C21 1.5161(14) . ?
C20 H20B 0.968(13) . ?
C20 H20A 1.003(14) . ?
C21 H21B 0.987(14) . ?
C21 H21A 1.004(15) . ?
C22 C23 1.4047(15) . ?
C22 H22 0.985(15) . ?
C23 H23 0.977(15) . ?
C24 C25 1.3720(14) . ?
C24 H24 0.952(14) . ?
C25 H25 0.968(15) . ?

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
C5 N1 C6 115.10(8) . . ?
C5 N1 C21 116.43(8) . . ?
C6 N1 C21 109.97(8) . . ?
C2 C1 C25 122.26(10) . . ?
C2 C1 Cl1 118.78(9) . . ?
C25 C1 Cl1 118.94(8) . . ?
C7 N2 C8 110.73(8) . . ?
C7 N2 C20 109.43(8) . . ?
C8 N2 C20 112.45(9) . . ?
C1 C2 C3 119.63(10) . . ?
C1 C2 H2 122.3(9) . . ?
C3 C2 H2 118.1(9) . . ?
C9 N3 C10 120.49(9) . . ?
C9 N3 C13 126.62(9) . . ?
C10 N3 C13 112.86(8) . . ?
N5 C3 C2 116.62(9) . . ?
N5 C3 C4 124.00(9) . . ?
C2 C3 C4 119.37(9) . . ?
C14 N4 C12 115.91(9) . . ?
C14 N4 C11 113.70(8) . . ?
C12 N4 C11 111.11(8) . . ?
C24 C4 C3 118.40(9) . . ?
C24 C4 C5 123.74(9) . . ?
C3 C4 C5 117.78(9) . . ?
C23 N5 C3 115.73(9) . . ?
C22 C5 N1 122.63(9) . . ?
C22 C5 C4 116.97(9) . . ?
N1 C5 C4 120.30(9) . . ?
N1 C6 C7 110.29(9) . . ?
N1 C6 H6B 108.1(9) . . ?
C7 C6 H6B 109.1(10) . . ?
N1 C6 H6A 112.6(9) . . ?
C7 C6 H6A 108.0(9) . . ?
H6B C6 H6A 108.7(13) . . ?
N2 C7 C6 109.53(9) . . ?
N2 C7 H7B 110.8(9) . . ?
C6 C7 H7B 110.9(9) . . ?
N2 C7 H7A 109.0(9) . . ?
C6 C7 H7A 109.4(9) . . ?
H7B C7 H7A 107.0(12) . . ?
N2 C8 C9 113.57(8) . . ?
N2 C8 H8B 107.2(8) . . ?
C9 C8 H8B 109.8(8) . . ?
N2 C8 H8A 112.6(9) . . ?
C9 C8 H8A 107.2(9) . . ?
H8B C8 H8A 106.3(11) . . ?
O1 C9 N3 122.03(10) . . ?
O1 C9 C8 119.59(10) . . ?
N3 C9 C8 118.37(9) . . ?
N3 C10 C11 109.46(9) . . ?
N3 C10 H10B 109.2(9) . . ?
C11 C10 H10B 112.0(9) . . ?
N3 C10 H10A 107.5(9) . . ?
C11 C10 H10A 109.2(9) . . ?
H10B C10 H10A 109.3(13) . . ?
N4 C11 C10 110.04(9) . . ?
N4 C11 H11B 109.1(8) . . ?
C10 C11 H11B 109.4(8) . . ?
N4 C11 H11A 109.9(9) . . ?
C10 C11 H11A 108.8(8) . . ?
H11B C11 H11A 109.7(12) . . ?
N4 C12 C13 109.17(9) . . ?
N4 C12 H12B 110.1(9) . . ?
C13 C12 H12B 109.6(9) . . ?
N4 C12 H12A 113.8(9) . . ?
C13 C12 H12A 106.9(8) . . ?
H12B C12 H12A 107.2(12) . . ?
N3 C13 C12 109.70(9) . . ?
N3 C13 H13B 108.3(9) . . ?
C12 C13 H13B 110.1(9) . . ?
N3 C13 H13A 111.0(8) . . ?
C12 C13 H13A 108.5(8) . . ?
H13B C13 H13A 109.3(12) . . ?
C19 C14 C15 117.95(10) . . ?
C19 C14 N4 123.05(10) . . ?
C15 C14 N4 118.97(9) . . ?
C16 C15 C14 120.65(10) . . ?
C16 C15 Cl2 119.80(9) . . ?
C14 C15 Cl2 119.48(8) . . ?
C17 C16 C15 120.54(11) . . ?
C17 C16 Cl3 119.49(9) . . ?
C15 C16 Cl3 119.95(9) . . ?
C16 C17 C18 119.26(11) . . ?
C16 C17 H17 121.0(10) . . ?
C18 C17 H17 119.7(10) . . ?
C17 C18 C19 120.79(12) . . ?
C17 C18 H18 122.5(11) . . ?
C19 C18 H18 116.7(11) . . ?
C18 C19 C14 120.80(12) . . ?
C18 C19 H19 119.7(10) . . ?
C14 C19 H19 119.5(10) . . ?
N2 C20 C21 109.29(8) . . ?
N2 C20 H20B 108.0(8) . . ?
C21 C20 H20B 109.7(8) . . ?
N2 C20 H20A 111.0(8) . . ?
C21 C20 H20A 109.1(8) . . ?
H20B C20 H20A 109.8(11) . . ?
N1 C21 C20 110.06(8) . . ?
N1 C21 H21B 110.7(8) . . ?
C20 C21 H21B 110.9(8) . . ?
N1 C21 H21A 110.5(8) . . ?
C20 C21 H21A 109.0(8) . . ?
H21B C21 H21A 105.7(11) . . ?
C5 C22 C23 120.04(10) . . ?
C5 C22 H22 121.7(9) . . ?
C23 C22 H22 118.2(9) . . ?
N5 C23 C22 125.43(10) . . ?
N5 C23 H23 114.9(9) . . ?
C22 C23 H23 119.6(9) . . ?
C25 C24 C4 121.40(10) . . ?
C25 C24 H24 118.1(8) . . ?
C4 C24 H24 120.5(8) . . ?
C24 C25 C1 118.85(10) . . ?
C24 C25 H25 120.0(9) . . ?
C1 C25 H25 121.0(9) . . ?

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
C25 C1 C2 C3 -1.34(17) . . . . ?
Cl1 C1 C2 C3 -179.65(8) . . . . ?
C1 C2 C3 N5 177.89(10) . . . . ?
C1 C2 C3 C4 -1.09(16) . . . . ?
N5 C3 C4 C24 -175.66(10) . . . . ?
C2 C3 C4 C24 3.24(14) . . . . ?
N5 C3 C4 C5 1.12(15) . . . . ?
C2 C3 C4 C5 -179.97(9) . . . . ?
C2 C3 N5 C23 -178.34(10) . . . . ?
C4 C3 N5 C23 0.58(15) . . . . ?
C6 N1 C5 C22 -13.50(15) . . . . ?
C21 N1 C5 C22 117.34(11) . . . . ?
C6 N1 C5 C4 162.73(10) . . . . ?
C21 N1 C5 C4 -66.43(12) . . . . ?
C24 C4 C5 C22 173.91(10) . . . . ?
C3 C4 C5 C22 -2.69(14) . . . . ?
C24 C4 C5 N1 -2.52(15) . . . . ?
C3 C4 C5 N1 -179.12(9) . . . . ?
C5 N1 C6 C7 -168.72(9) . . . . ?
C21 N1 C6 C7 57.40(12) . . . . ?
C8 N2 C7 C6 -174.49(9) . . . . ?
C20 N2 C7 C6 61.00(11) . . . . ?
N1 C6 C7 N2 -59.34(12) . . . . ?
C7 N2 C8 C9 173.76(9) . . . . ?
C20 N2 C8 C9 -63.47(12) . . . . ?
C10 N3 C9 O1 -7.93(16) . . . . ?
C13 N3 C9 O1 174.31(11) . . . . ?
C10 N3 C9 C8 172.65(9) . . . . ?
C13 N3 C9 C8 -5.12(16) . . . . ?
N2 C8 C9 O1 125.23(11) . . . . ?
N2 C8 C9 N3 -55.33(13) . . . . ?
C9 N3 C10 C11 -121.65(11) . . . . ?
C13 N3 C10 C11 56.40(12) . . . . ?
C14 N4 C11 C10 -167.94(9) . . . . ?
C12 N4 C11 C10 59.14(12) . . . . ?
N3 C10 C11 N4 -55.92(12) . . . . ?
C14 N4 C12 C13 168.65(9) . . . . ?
C11 N4 C12 C13 -59.55(11) . . . . ?
C9 N3 C13 C12 120.47(11) . . . . ?
C10 N3 C13 C12 -57.44(12) . . . . ?
N4 C12 C13 N3 57.52(11) . . . . ?
C12 N4 C14 C19 27.51(15) . . . . ?
C11 N4 C14 C19 -103.07(12) . . . . ?
C12 N4 C14 C15 -150.42(9) . . . . ?
C11 N4 C14 C15 79.00(12) . . . . ?
C19 C14 C15 C16 0.49(15) . . . . ?
N4 C14 C15 C16 178.52(9) . . . . ?
C19 C14 C15 Cl2 -176.62(8) . . . . ?
N4 C14 C15 Cl2 1.41(13) . . . . ?
C14 C15 C16 C17 -0.58(16) . . . . ?
Cl2 C15 C16 C17 176.52(9) . . . . ?
C14 C15 C16 Cl3 -179.55(8) . . . . ?
Cl2 C15 C16 Cl3 -2.44(13) . . . . ?
C15 C16 C17 C18 0.27(19) . . . . ?
Cl3 C16 C17 C18 179.24(11) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 -0.2(2) . . . . ?
C15 C14 C19 C18 -0.10(17) . . . . ?
N4 C14 C19 C18 -178.05(11) . . . . ?
C7 N2 C20 C21 -61.05(11) . . . . ?
C8 N2 C20 C21 175.44(8) . . . . ?
C5 N1 C21 C20 169.33(9) . . . . ?
C6 N1 C21 C20 -57.47(11) . . . . ?
N2 C20 C21 N1 59.21(11) . . . . ?
N1 C5 C22 C23 179.00(10) . . . . ?
C4 C5 C22 C23 2.65(16) . . . . ?
C3 N5 C23 C22 -0.70(17) . . . . ?
C5 C22 C23 N5 -0.98(18) . . . . ?
C3 C4 C24 C25 -3.12(15) . . . . ?
C5 C4 C24 C25 -179.70(10) . . . . ?
C4 C24 C25 C1 0.78(16) . . . . ?
C2 C1 C25 C24 1.52(17) . . . . ?
Cl1 C1 C25 C24 179.82(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.64
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.051
