####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 1034019'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 Cl N4, C H4 O'
_chemical_formula_sum            'C25 H21 Cl N4 O'
_chemical_formula_weight         428.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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


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

_cell_length_a                   12.708(3)
_cell_length_b                   18.351(3)
_cell_length_c                   9.0615(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.622(6)
_cell_angle_gamma                90.00
_cell_volume                     2111.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2296
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      21.17

_exptl_crystal_description       Needles
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15832
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.18
_reflns_number_total             4203
_reflns_number_gt                2074
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1212P)²+0.6038P] 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         4203
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2381
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5189(3) 0.9465(2) 0.3458(4) 0.0452(10) Uani 1 1 d . . .
C2 C 0.6090(3) 0.9249(3) 0.4312(5) 0.0581(12) Uani 1 1 d . . .
H2 H 0.6715 0.9510 0.4259 0.070 Uiso 1 1 calc R . .
C3 C 0.6044(4) 0.8663(3) 0.5207(5) 0.0619(12) Uani 1 1 d . . .
H3 H 0.6647 0.8531 0.5763 0.074 Uiso 1 1 calc R . .
C4 C 0.5132(3) 0.8243(2) 0.5341(4) 0.0522(11) Uani 1 1 d . . .
C5 C 0.4237(3) 0.8457(2) 0.4527(4) 0.0482(10) Uani 1 1 d . . .
H5 H 0.3615 0.8197 0.4616 0.058 Uiso 1 1 calc R . .
C6 C 0.4248(3) 0.9055(2) 0.3575(4) 0.0421(9) Uani 1 1 d . . .
C7 C 0.3375(3) 0.9275(2) 0.2659(4) 0.0456(10) Uani 1 1 d . . .
H7 H 0.2744 0.9021 0.2705 0.055 Uiso 1 1 calc R . .
C8 C 0.3427(3) 0.9847(2) 0.1714(4) 0.0425(9) Uani 1 1 d . . .
C9 C 0.4406(3) 1.0223(2) 0.1742(4) 0.0459(10) Uani 1 1 d . . .
C10 C 0.2544(3) 1.0052(2) 0.0585(5) 0.0495(10) Uani 1 1 d . . .
H10 H 0.2568 1.0577 0.0393 0.059 Uiso 1 1 calc R . .
C11 C 0.0936(4) 1.0267(3) 0.2100(5) 0.0629(13) Uani 1 1 d . . .
C12 C 0.1095(5) 1.0938(3) 0.2728(6) 0.0808(16) Uani 1 1 d . . .
H12 H 0.1687 1.1215 0.2538 0.097 Uiso 1 1 calc R . .
C13 C 0.0351(7) 1.1186(3) 0.3643(7) 0.099(2) Uani 1 1 d . . .
H13 H 0.0433 1.1639 0.4096 0.118 Uiso 1 1 calc R . .
C14 C -0.0547(6) 1.0753(4) 0.3905(6) 0.096(2) Uani 1 1 d . . .
H14 H -0.1050 1.0926 0.4531 0.116 Uiso 1 1 calc R . .
C15 C -0.0686(4) 1.0089(3) 0.3254(6) 0.0784(15) Uani 1 1 d . . .
H15 H -0.1275 0.9807 0.3426 0.094 Uiso 1 1 calc R . .
C16 C 0.0070(4) 0.9850(3) 0.2337(5) 0.0660(13) Uani 1 1 d . . .
C17 C 0.0982(3) 0.9241(2) 0.0832(5) 0.0534(11) Uani 1 1 d . . .
C18 C 0.1436(3) 0.8717(2) -0.0197(4) 0.0489(10) Uani 1 1 d . . .
C19 C 0.0976(4) 0.8023(2) -0.0486(5) 0.0601(12) Uani 1 1 d . . .
H19 H 0.0394 0.7869 0.0016 0.072 Uiso 1 1 calc R . .
C20 C 0.1415(4) 0.7579(2) -0.1537(5) 0.0633(12) Uani 1 1 d . . .
H20 H 0.1127 0.7123 -0.1742 0.076 Uiso 1 1 calc R . .
C21 C 0.2264(4) 0.7811(3) -0.2266(5) 0.0630(12) Uani 1 1 d . . .
H21 H 0.2549 0.7509 -0.2968 0.076 Uiso 1 1 calc R . .
C22 C 0.2709(4) 0.8478(3) -0.1988(5) 0.0619(12) Uani 1 1 d . . .
H22 H 0.3294 0.8623 -0.2494 0.074 Uiso 1 1 calc R . .
C23 C 0.2297(3) 0.8931(2) -0.0973(5) 0.0496(10) Uani 1 1 d . . .
C24 C 0.5123(4) 0.7595(2) 0.6351(5) 0.0736(14) Uani 1 1 d . . .
H24A H 0.4490 0.7319 0.6153 0.110 Uiso 1 1 calc R . .
H24B H 0.5150 0.7757 0.7359 0.110 Uiso 1 1 calc R . .
H24C H 0.5724 0.7293 0.6185 0.110 Uiso 1 1 calc R . .
C25 C 0.1879(7) 0.1980(5) 0.7543(13) 0.176(4) Uani 1 1 d . . .
H25A H 0.1220 0.2059 0.7007 0.264 Uiso 1 1 calc R . .
H25B H 0.2292 0.1637 0.7018 0.264 Uiso 1 1 calc R . .
H25C H 0.2254 0.2433 0.7641 0.264 Uiso 1 1 calc R . .
N1 N 0.5244(2) 1.00552(17) 0.2534(4) 0.0463(8) Uani 1 1 d . . .
N2 N 0.1521(3) 0.98603(19) 0.1089(4) 0.0603(10) Uani 1 1 d . . .
N3 N 0.0107(3) 0.9179(2) 0.1508(4) 0.0684(11) Uani 1 1 d . . .
N4 N 0.2673(3) 0.9654(2) -0.0801(4) 0.0633(10) Uani 1 1 d D . .
Cl1 Cl 0.45193(9) 1.09880(6) 0.06175(13) 0.0645(4) Uani 1 1 d . . .
O1 O 0.1695(5) 0.1711(4) 0.8913(8) 0.163(2) Uani 1 1 d . . .
H1A H 0.1076 0.1590 0.8944 0.195 Uiso 1 1 calc R . .
H4A H 0.323(4) 0.979(4) -0.122(9) 0.195 Uiso 1 1 d 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
C1 N1 1.374(5) . ?
C1 C2 1.409(6) . ?
C1 C6 1.421(5) . ?
C2 C3 1.350(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(6) . ?
C4 C24 1.501(6) . ?
C5 C6 1.396(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(5) . ?
C7 C8 1.357(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(5) . ?
C8 C10 1.531(5) . ?
C9 N1 1.294(5) . ?
C9 Cl1 1.745(4) . ?
C10 N2 1.441(5) . ?
C10 N4 1.468(5) . ?
C10 H10 0.9800 . ?
C11 C16 1.365(7) . ?
C11 C12 1.368(7) . ?
C11 N2 1.419(6) . ?
C12 C13 1.363(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.420(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(7) . ?
C15 H15 0.9300 . ?
C16 N3 1.443(6) . ?
C17 N3 1.300(5) . ?
C17 N2 1.342(5) . ?
C17 C18 1.474(6) . ?
C18 C23 1.384(6) . ?
C18 C19 1.421(6) . ?
C19 C20 1.389(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.362(6) . ?
C22 H22 0.9300 . ?
C23 N4 1.416(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O1 1.366(10) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N4 H4A 0.86(6) . ?
O1 H1A 0.8200 . ?

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
N1 C1 C2 119.6(4) . . ?
N1 C1 C6 122.0(4) . . ?
C2 C1 C6 118.5(4) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 123.3(4) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C24 121.4(4) . . ?
C3 C4 C24 121.2(4) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 123.9(4) . . ?
C5 C6 C1 119.6(4) . . ?
C7 C6 C1 116.4(4) . . ?
C8 C7 C6 122.1(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 115.6(3) . . ?
C7 C8 C10 123.8(3) . . ?
C9 C8 C10 120.4(3) . . ?
N1 C9 C8 126.3(4) . . ?
N1 C9 Cl1 115.3(3) . . ?
C8 C9 Cl1 118.4(3) . . ?
N2 C10 N4 106.7(3) . . ?
N2 C10 C8 111.9(3) . . ?
N4 C10 C8 110.0(3) . . ?
N2 C10 H10 109.4 . . ?
N4 C10 H10 109.4 . . ?
C8 C10 H10 109.4 . . ?
C16 C11 C12 123.0(5) . . ?
C16 C11 N2 104.9(4) . . ?
C12 C11 N2 132.1(5) . . ?
C13 C12 C11 117.4(6) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C14 120.0(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 118.0(6) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C11 C16 C15 120.5(5) . . ?
C11 C16 N3 110.5(4) . . ?
C15 C16 N3 129.0(5) . . ?
N3 C17 N2 115.7(4) . . ?
N3 C17 C18 127.6(4) . . ?
N2 C17 C18 116.8(4) . . ?
C23 C18 C19 119.2(4) . . ?
C23 C18 C17 118.5(4) . . ?
C19 C18 C17 122.1(4) . . ?
C20 C19 C18 118.5(4) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.4(5) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.5(4) . . ?
C22 C23 N4 120.6(4) . . ?
C18 C23 N4 118.7(4) . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C9 N1 C1 117.5(3) . . ?
C17 N2 C11 106.2(4) . . ?
C17 N2 C10 127.8(4) . . ?
C11 N2 C10 125.7(4) . . ?
C17 N3 C16 102.7(4) . . ?
C23 N4 C10 120.7(4) . . ?
C23 N4 H4A 120(6) . . ?
C10 N4 H4A 111(6) . . ?
C25 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.1(4) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 C24 179.8(4) . . . . ?
C3 C4 C5 C6 1.9(6) . . . . ?
C24 C4 C5 C6 -179.2(3) . . . . ?
C4 C5 C6 C7 176.5(4) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
N1 C1 C6 C5 179.7(3) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
N1 C1 C6 C7 1.6(5) . . . . ?
C2 C1 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 C8 -177.9(4) . . . . ?
C1 C6 C7 C8 0.1(6) . . . . ?
C6 C7 C8 C9 -2.0(5) . . . . ?
C6 C7 C8 C10 173.0(4) . . . . ?
C7 C8 C9 N1 2.6(6) . . . . ?
C10 C8 C9 N1 -172.6(4) . . . . ?
C7 C8 C9 Cl1 -177.3(3) . . . . ?
C10 C8 C9 Cl1 7.5(5) . . . . ?
C7 C8 C10 N2 30.2(5) . . . . ?
C9 C8 C10 N2 -155.0(3) . . . . ?
C7 C8 C10 N4 -88.2(5) . . . . ?
C9 C8 C10 N4 86.6(4) . . . . ?
C16 C11 C12 C13 0.9(7) . . . . ?
N2 C11 C12 C13 178.1(4) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C12 C11 C16 C15 -0.9(7) . . . . ?
N2 C11 C16 C15 -178.8(4) . . . . ?
C12 C11 C16 N3 178.8(4) . . . . ?
N2 C11 C16 N3 0.9(5) . . . . ?
C14 C15 C16 C11 0.4(7) . . . . ?
C14 C15 C16 N3 -179.2(4) . . . . ?
N3 C17 C18 C23 170.5(4) . . . . ?
N2 C17 C18 C23 -8.3(5) . . . . ?
N3 C17 C18 C19 -5.3(6) . . . . ?
N2 C17 C18 C19 175.9(4) . . . . ?
C23 C18 C19 C20 0.5(6) . . . . ?
C17 C18 C19 C20 176.2(4) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C22 0.2(7) . . . . ?
C20 C21 C22 C23 -0.6(7) . . . . ?
C21 C22 C23 C18 0.9(6) . . . . ?
C21 C22 C23 N4 -172.6(4) . . . . ?
C19 C18 C23 C22 -0.9(6) . . . . ?
C17 C18 C23 C22 -176.7(4) . . . . ?
C19 C18 C23 N4 172.8(4) . . . . ?
C17 C18 C23 N4 -3.1(5) . . . . ?
C8 C9 N1 C1 -1.0(6) . . . . ?
Cl1 C9 N1 C1 178.9(3) . . . . ?
C2 C1 N1 C9 178.3(4) . . . . ?
C6 C1 N1 C9 -1.2(5) . . . . ?
N3 C17 N2 C11 1.1(5) . . . . ?
C18 C17 N2 C11 -179.9(3) . . . . ?
N3 C17 N2 C10 174.9(4) . . . . ?
C18 C17 N2 C10 -6.1(6) . . . . ?
C16 C11 N2 C17 -1.2(4) . . . . ?
C12 C11 N2 C17 -178.8(5) . . . . ?
C16 C11 N2 C10 -175.1(4) . . . . ?
C12 C11 N2 C10 7.2(7) . . . . ?
N4 C10 N2 C17 27.8(5) . . . . ?
C8 C10 N2 C17 -92.5(5) . . . . ?
N4 C10 N2 C11 -159.6(4) . . . . ?
C8 C10 N2 C11 80.1(5) . . . . ?
N2 C17 N3 C16 -0.6(5) . . . . ?
C18 C17 N3 C16 -179.4(4) . . . . ?
C11 C16 N3 C17 -0.2(5) . . . . ?
C15 C16 N3 C17 179.4(5) . . . . ?
C22 C23 N4 C10 -157.3(4) . . . . ?
C18 C23 N4 C10 29.0(6) . . . . ?
N2 C10 N4 C23 -38.5(5) . . . . ?
C8 C10 N4 C23 83.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.18
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_CMQC
_database_code_depnum_ccdc_archive 'CCDC 1034020'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H8 Cl N O2'
_chemical_formula_sum            'C11 H8 Cl N O2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         221.63

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   3.8274(6)
_cell_length_b                   29.579(4)
_cell_length_c                   8.6242(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.352(7)
_cell_angle_gamma                90.00
_cell_volume                     972.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16786
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         27.88
_reflns_number_total             2296
_reflns_number_gt                1583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1146P)²+0.6337P] 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         2296
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.2030
_refine_ls_wR_factor_gt          0.1784
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5195(10) 0.77626(12) -0.5855(5) 0.0567(9) Uani 1 1 d . . .
H1A H 0.2771 0.7727 -0.5678 0.085 Uiso 1 1 calc R . .
H1B H 0.5496 0.8041 -0.6397 0.085 Uiso 1 1 calc R . .
H1C H 0.6604 0.7767 -0.4874 0.085 Uiso 1 1 calc R . .
C2 C 0.6333(8) 0.69767(10) -0.6111(4) 0.0410(7) Uani 1 1 d . . .
C3 C 0.5347(8) 0.68845(10) -0.4660(3) 0.0400(7) Uani 1 1 d . . .
H3 H 0.4516 0.7113 -0.4053 0.048 Uiso 1 1 calc R . .
C4 C 0.5611(8) 0.64394(10) -0.4105(3) 0.0364(7) Uani 1 1 d . . .
C5 C 0.6918(8) 0.60904(10) -0.5023(3) 0.0370(7) Uani 1 1 d . . .
C6 C 0.7846(9) 0.62002(11) -0.6527(3) 0.0429(7) Uani 1 1 d . . .
H6 H 0.8673 0.5976 -0.7154 0.051 Uiso 1 1 calc R . .
C7 C 0.7535(9) 0.66312(11) -0.7060(4) 0.0455(8) Uani 1 1 d . . .
H7 H 0.8118 0.6700 -0.8057 0.055 Uiso 1 1 calc R . .
C8 C 0.4980(8) 0.59462(10) -0.2120(3) 0.0377(7) Uani 1 1 d . . .
C9 C 0.6319(8) 0.55762(10) -0.2908(3) 0.0396(7) Uani 1 1 d . . .
C10 C 0.7259(8) 0.56597(10) -0.4384(3) 0.0386(7) Uani 1 1 d . . .
H10 H 0.8129 0.5426 -0.4958 0.046 Uiso 1 1 calc R . .
C11 C 0.6901(10) 0.51230(11) -0.2206(4) 0.0532(9) Uani 1 1 d . . .
H11 H 0.6361 0.5056 -0.1182 0.064 Uiso 1 1 calc R . .
N1 N 0.4629(7) 0.63550(8) -0.2638(3) 0.0390(6) Uani 1 1 d . . .
O2 O 0.8413(9) 0.48256(9) -0.2792(3) 0.0580(9) Uani 1 1 d . . .
O1 O 0.6255(7) 0.73940(8) -0.6772(3) 0.0538(6) Uani 1 1 d . . .
Cl1 Cl 0.3642(2) 0.58610(3) -0.02577(9) 0.0517(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.428(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.359(4) . ?
C2 C3 1.368(4) . ?
C2 C7 1.413(5) . ?
C3 C4 1.401(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.376(4) . ?
C4 C5 1.420(4) . ?
C5 C10 1.389(4) . ?
C5 C6 1.414(4) . ?
C6 C7 1.357(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.292(4) . ?
C8 C9 1.409(4) . ?
C8 Cl1 1.749(3) . ?
C9 C10 1.378(4) . ?
C9 C11 1.479(4) . ?
C10 H10 0.9300 . ?
C11 O2 1.192(4) . ?
C11 H11 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.6(3) . . ?
O1 C2 C7 114.2(3) . . ?
C3 C2 C7 121.2(3) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C4 C3 117.9(3) . . ?
N1 C4 C5 121.4(3) . . ?
C3 C4 C5 120.7(3) . . ?
C10 C5 C6 123.5(3) . . ?
C10 C5 C4 118.0(3) . . ?
C6 C5 C4 118.4(3) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 126.3(3) . . ?
N1 C8 Cl1 115.0(2) . . ?
C9 C8 Cl1 118.8(2) . . ?
C10 C9 C8 116.4(3) . . ?
C10 C9 C11 119.9(3) . . ?
C8 C9 C11 123.6(3) . . ?
C9 C10 C5 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
O2 C11 C9 123.8(3) . . ?
O2 C11 H11 106.4 . . ?
C9 C11 H11 106.4 . . ?
C8 N1 C4 117.3(3) . . ?
C2 O1 C1 117.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1034021'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 Cl N4 O'
_chemical_formula_sum            'C24 H17 Cl N4 O'
_chemical_formula_weight         412.87

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   13.029(2)
_cell_length_b                   22.884(5)
_cell_length_c                   13.417(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.340(6)
_cell_angle_gamma                90.00
_cell_volume                     3997.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1429
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      18.09

_exptl_crystal_description       Prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33107
_diffrn_reflns_av_R_equivalents  0.1230
_diffrn_reflns_av_sigmaI/netI    0.1575
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.68
_reflns_number_total             8414
_reflns_number_gt                2975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0638P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8414
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2247
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1870
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
C1 C 0.4763(4) 0.0404(2) 0.3507(3) 0.0637(13) Uani 1 1 d . . .
C2 C 0.3789(4) 0.0632(2) 0.3332(3) 0.0726(14) Uani 1 1 d . . .
H2 H 0.3696 0.1025 0.3176 0.087 Uiso 1 1 calc R . .
C3 C 0.2970(4) 0.0267(3) 0.3396(4) 0.0823(16) Uani 1 1 d . . .
H3 H 0.2311 0.0413 0.3270 0.099 Uiso 1 1 calc R . .
C4 C 0.3096(4) -0.0322(3) 0.3646(4) 0.0899(17) Uani 1 1 d . . .
H4 H 0.2524 -0.0561 0.3704 0.108 Uiso 1 1 calc R . .
C5 C 0.4077(4) -0.0552(2) 0.3807(4) 0.0730(15) Uani 1 1 d . . .
H5 H 0.4179 -0.0944 0.3968 0.088 Uiso 1 1 calc R . .
C6 C 0.4883(4) -0.0178(2) 0.3720(3) 0.0644(13) Uani 1 1 d . . .
C7 C 0.6436(3) -0.08206(17) 0.4000(3) 0.0579(13) Uani 1 1 d . . .
H7 H 0.6133 -0.1010 0.4574 0.070 Uiso 1 1 calc R . .
C8 C 0.6324(3) -0.12190(17) 0.3098(4) 0.0503(11) Uani 1 1 d . . .
C9 C 0.6152(3) -0.18237(18) 0.3201(3) 0.0495(11) Uani 1 1 d . . .
C10 C 0.6291(3) -0.20089(18) 0.1549(4) 0.0509(11) Uani 1 1 d . . .
C11 C 0.6303(3) -0.24186(19) 0.0761(4) 0.0591(13) Uani 1 1 d . . .
H11 H 0.6216 -0.2814 0.0890 0.071 Uiso 1 1 calc R . .
C12 C 0.6442(3) -0.2233(2) -0.0181(4) 0.0642(13) Uani 1 1 d . . .
C13 C 0.6421(4) -0.3199(2) -0.0857(4) 0.0911(17) Uani 1 1 d . . .
H13A H 0.7005 -0.3326 -0.0456 0.137 Uiso 1 1 calc R . .
H13B H 0.6412 -0.3395 -0.1489 0.137 Uiso 1 1 calc R . .
H13C H 0.5803 -0.3289 -0.0521 0.137 Uiso 1 1 calc R . .
C14 C 0.6577(3) -0.1633(2) -0.0393(4) 0.0666(13) Uani 1 1 d . . .
H14 H 0.6666 -0.1513 -0.1046 0.080 Uiso 1 1 calc R . .
C15 C 0.6576(3) -0.1232(2) 0.0353(4) 0.0638(13) Uani 1 1 d . . .
H15 H 0.6670 -0.0839 0.0210 0.077 Uiso 1 1 calc R . .
C16 C 0.6433(3) -0.14100(18) 0.1340(4) 0.0526(12) Uani 1 1 d . . .
C17 C 0.6465(3) -0.10265(18) 0.2160(4) 0.0569(12) Uani 1 1 d . . .
H17 H 0.6585 -0.0631 0.2055 0.068 Uiso 1 1 calc R . .
C18 C 0.8055(4) -0.0199(2) 0.3975(3) 0.0568(12) Uani 1 1 d . . .
C19 C 0.9112(4) -0.0180(3) 0.3996(4) 0.0777(15) Uani 1 1 d . . .
H19 H 0.9492 -0.0517 0.4127 0.093 Uiso 1 1 calc R . .
C20 C 0.9595(4) 0.0331(3) 0.3827(4) 0.0873(17) Uani 1 1 d . . .
H20 H 1.0309 0.0340 0.3850 0.105 Uiso 1 1 calc R . .
C21 C 0.9066(5) 0.0834(3) 0.3623(4) 0.0791(16) Uani 1 1 d . . .
H21 H 0.9422 0.1180 0.3522 0.095 Uiso 1 1 calc R . .
C22 C 0.8024(4) 0.0832(2) 0.3567(3) 0.0655(13) Uani 1 1 d . . .
H22 H 0.7663 0.1174 0.3418 0.079 Uiso 1 1 calc R . .
C23 C 0.7499(3) 0.0306(2) 0.3737(3) 0.0536(12) Uani 1 1 d . . .
C24 C 0.6407(4) 0.0266(2) 0.3672(3) 0.0611(13) Uani 1 1 d . . .
C25 C 0.6363(3) 0.2261(2) -0.0391(4) 0.0627(13) Uani 1 1 d . . .
C26 C 0.6408(3) 0.1870(2) -0.1164(4) 0.0727(14) Uani 1 1 d . . .
H26 H 0.6330 0.1471 -0.1065 0.087 Uiso 1 1 calc R . .
C27 C 0.6575(4) 0.2100(3) -0.2100(4) 0.0869(17) Uani 1 1 d . . .
H27 H 0.6608 0.1852 -0.2645 0.104 Uiso 1 1 calc R . .
C28 C 0.6696(4) 0.2705(3) -0.2233(5) 0.0888(17) Uani 1 1 d . . .
H28 H 0.6816 0.2853 -0.2863 0.107 Uiso 1 1 calc R . .
C29 C 0.6637(4) 0.3082(2) -0.1433(4) 0.0808(16) Uani 1 1 d . . .
H29 H 0.6712 0.3482 -0.1522 0.097 Uiso 1 1 calc R . .
C30 C 0.6467(3) 0.2857(2) -0.0501(4) 0.0596(12) Uani 1 1 d . . .
C31 C 0.6224(3) 0.27209(19) 0.1068(4) 0.0569(12) Uani 1 1 d . . .
C32 C 0.6081(3) 0.2763(2) 0.2116(4) 0.0550(12) Uani 1 1 d . . .
C33 C 0.6153(3) 0.3292(2) 0.2644(4) 0.0676(14) Uani 1 1 d . . .
H33 H 0.6280 0.3640 0.2313 0.081 Uiso 1 1 calc R . .
C34 C 0.6036(4) 0.3289(2) 0.3646(4) 0.0782(15) Uani 1 1 d . . .
H34 H 0.6066 0.3639 0.4000 0.094 Uiso 1 1 calc R . .
C35 C 1.1188(4) -0.0662(2) 0.1469(4) 0.100(2) Uani 1 1 d . . .
H35A H 1.0809 -0.0754 0.2048 0.150 Uiso 1 1 calc R . .
H35B H 1.1852 -0.0844 0.1525 0.150 Uiso 1 1 calc R . .
H35C H 1.0822 -0.0804 0.0883 0.150 Uiso 1 1 calc R . .
C36 C 0.5871(3) 0.2771(2) 0.4145(4) 0.0777(15) Uani 1 1 d . . .
H36 H 0.5813 0.2775 0.4833 0.093 Uiso 1 1 calc R . .
C37 C 0.5795(3) 0.2259(2) 0.3647(4) 0.0747(15) Uani 1 1 d . . .
H37 H 0.5677 0.1915 0.3993 0.090 Uiso 1 1 calc R . .
C38 C 0.8824(3) 0.10869(18) 0.1201(3) 0.0499(11) Uani 1 1 d . . .
C39 C 0.9854(4) 0.1280(2) 0.1293(3) 0.0670(13) Uani 1 1 d . . .
H39 H 0.9994 0.1678 0.1324 0.080 Uiso 1 1 calc R . .
C40 C 0.5889(3) 0.22452(19) 0.2635(4) 0.0568(12) Uani 1 1 d . . .
C41 C 0.6051(3) 0.16174(17) 0.1086(4) 0.0585(13) Uani 1 1 d . . .
H41 H 0.5491 0.1416 0.0719 0.070 Uiso 1 1 calc R . .
C42 C 1.0641(4) 0.0893(2) 0.1336(4) 0.0753(15) Uani 1 1 d . . .
H42 H 1.1316 0.1027 0.1382 0.090 Uiso 1 1 calc R . .
C43 C 0.7005(3) 0.12403(17) 0.1081(3) 0.0470(11) Uani 1 1 d . . .
C44 C 0.6914(3) 0.06295(19) 0.1037(3) 0.0520(11) Uani 1 1 d . . .
C45 C 0.7969(3) 0.14582(17) 0.1172(3) 0.0527(12) Uani 1 1 d . . .
H45 H 0.8065 0.1860 0.1216 0.063 Uiso 1 1 calc R . .
C46 C 0.8645(4) 0.04772(17) 0.1169(3) 0.0520(12) Uani 1 1 d . . .
C47 C 0.9463(4) 0.0083(2) 0.1235(3) 0.0642(13) Uani 1 1 d . . .
H47 H 0.9342 -0.0318 0.1227 0.077 Uiso 1 1 calc R . .
C48 C 1.0441(4) 0.0292(2) 0.1312(3) 0.0650(13) Uani 1 1 d . . .
N1 N 0.5745(3) 0.06842(15) 0.3485(3) 0.0623(10) Uani 1 1 d . . .
N2 N 0.5960(3) -0.02616(14) 0.3830(3) 0.0591(10) Uani 1 1 d . . .
N3 N 0.7533(3) -0.07017(17) 0.4234(3) 0.0781(12) Uani 1 1 d . . .
H3A H 0.7877 -0.0966 0.4558 0.094 Uiso 1 1 calc R . .
N4 N 0.6140(2) -0.22118(14) 0.2489(3) 0.0539(10) Uani 1 1 d . . .
N5 N 0.5740(3) 0.17285(17) 0.2108(3) 0.0815(13) Uani 1 1 d . . .
H5A H 0.5438 0.1448 0.2407 0.098 Uiso 1 1 calc R . .
N6 N 0.6373(2) 0.31480(15) 0.0433(3) 0.0620(11) Uani 1 1 d . . .
N7 N 0.6208(2) 0.21819(14) 0.0632(3) 0.0587(10) Uani 1 1 d . . .
N8 N 0.7663(3) 0.02541(14) 0.1085(3) 0.0541(9) Uani 1 1 d . . .
O1 O 0.6483(2) -0.25820(15) -0.1011(3) 0.0834(10) Uani 1 1 d . . .
O2 O 1.1310(3) -0.00413(17) 0.1397(3) 0.0911(11) Uani 1 1 d . . .
Cl1 Cl 0.59199(9) -0.21008(5) 0.43836(9) 0.0708(4) Uani 1 1 d . . .
Cl2 Cl 0.56874(9) 0.03234(5) 0.09222(10) 0.0751(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.370(6) . ?
C1 C2 1.384(6) . ?
C1 N1 1.432(5) . ?
C2 C3 1.360(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(6) . ?
C5 H5 0.9300 . ?
C6 N2 1.417(5) . ?
C7 N2 1.436(5) . ?
C7 N3 1.475(5) . ?
C7 C8 1.518(6) . ?
C7 H7 0.9800 . ?
C8 C17 1.353(5) . ?
C8 C9 1.409(5) . ?
C9 N4 1.303(5) . ?
C9 Cl1 1.747(4) . ?
C10 N4 1.367(5) . ?
C10 C16 1.412(5) . ?
C10 C11 1.414(5) . ?
C11 C12 1.352(6) . ?
C11 H11 0.9300 . ?
C12 O1 1.374(5) . ?
C12 C14 1.413(6) . ?
C13 O1 1.429(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.358(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 N3 1.387(5) . ?
C18 C23 1.394(6) . ?
C19 C20 1.352(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.357(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.410(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.425(6) . ?
C24 N1 1.305(5) . ?
C24 N2 1.362(5) . ?
C25 C26 1.372(6) . ?
C25 C30 1.380(6) . ?
C25 N7 1.407(6) . ?
C26 C27 1.387(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.405(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.380(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(6) . ?
C29 H29 0.9300 . ?
C30 N6 1.429(6) . ?
C31 N6 1.317(5) . ?
C31 N7 1.365(5) . ?
C31 C32 1.429(6) . ?
C32 C40 1.402(6) . ?
C32 C33 1.405(6) . ?
C33 C34 1.360(6) . ?
C33 H33 0.9300 . ?
C34 C36 1.382(6) . ?
C34 H34 0.9300 . ?
C35 O2 1.433(6) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.350(6) . ?
C36 H36 0.9300 . ?
C37 C40 1.369(6) . ?
C37 H37 0.9300 . ?
C38 C45 1.401(5) . ?
C38 C39 1.413(5) . ?
C38 C46 1.415(5) . ?
C39 C42 1.354(6) . ?
C39 H39 0.9300 . ?
C40 N5 1.387(5) . ?
C41 N7 1.446(5) . ?
C41 N5 1.467(5) . ?
C41 C43 1.513(5) . ?
C41 H41 0.9800 . ?
C42 C48 1.399(6) . ?
C42 H42 0.9300 . ?
C43 C45 1.352(5) . ?
C43 C44 1.404(5) . ?
C44 N8 1.300(5) . ?
C44 Cl2 1.745(4) . ?
C45 H45 0.9300 . ?
C46 N8 1.378(5) . ?
C46 C47 1.398(5) . ?
C47 C48 1.361(6) . ?
C47 H47 0.9300 . ?
C48 O2 1.366(5) . ?
N3 H3A 0.8600 . ?
N5 H5A 0.8600 . ?

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
C6 C1 C2 119.9(5) . . ?
C6 C1 N1 110.2(4) . . ?
C2 C1 N1 129.9(5) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 117.1(5) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C5 C6 C1 123.1(5) . . ?
C5 C6 N2 132.0(5) . . ?
C1 C6 N2 104.9(4) . . ?
N2 C7 N3 106.2(3) . . ?
N2 C7 C8 112.4(4) . . ?
N3 C7 C8 110.0(3) . . ?
N2 C7 H7 109.4 . . ?
N3 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C17 C8 C9 116.0(4) . . ?
C17 C8 C7 122.3(4) . . ?
C9 C8 C7 121.5(4) . . ?
N4 C9 C8 126.5(4) . . ?
N4 C9 Cl1 114.9(3) . . ?
C8 C9 Cl1 118.6(3) . . ?
N4 C10 C16 122.5(4) . . ?
N4 C10 C11 118.1(4) . . ?
C16 C10 C11 119.3(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 O1 125.8(5) . . ?
C11 C12 C14 121.1(4) . . ?
O1 C12 C14 113.1(5) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C12 C14 H14 119.9 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 123.8(4) . . ?
C15 C16 C10 119.4(4) . . ?
C17 C16 C10 116.8(4) . . ?
C8 C17 C16 121.6(4) . . ?
C8 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 N3 121.4(5) . . ?
C19 C18 C23 119.2(4) . . ?
N3 C18 C23 119.3(4) . . ?
C20 C19 C18 119.7(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 122.0(5) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.0(4) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C18 C23 C22 119.6(4) . . ?
C18 C23 C24 118.0(4) . . ?
C22 C23 C24 122.3(4) . . ?
N1 C24 N2 113.4(4) . . ?
N1 C24 C23 128.0(4) . . ?
N2 C24 C23 118.6(4) . . ?
C26 C25 C30 123.7(5) . . ?
C26 C25 N7 131.8(5) . . ?
C30 C25 N7 104.5(4) . . ?
C25 C26 C27 116.8(5) . . ?
C25 C26 H26 121.6 . . ?
C27 C26 H26 121.6 . . ?
C26 C27 C28 120.7(5) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 119.2(5) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C25 119.1(5) . . ?
C29 C30 N6 130.2(5) . . ?
C25 C30 N6 110.7(4) . . ?
N6 C31 N7 113.2(5) . . ?
N6 C31 C32 128.0(4) . . ?
N7 C31 C32 118.8(4) . . ?
C40 C32 C33 119.2(5) . . ?
C40 C32 C31 117.7(4) . . ?
C33 C32 C31 123.1(4) . . ?
C34 C33 C32 119.1(5) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C33 C34 C36 120.6(5) . . ?
C33 C34 H34 119.7 . . ?
C36 C34 H34 119.7 . . ?
O2 C35 H35A 109.5 . . ?
O2 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O2 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C34 121.0(5) . . ?
C37 C36 H36 119.5 . . ?
C34 C36 H36 119.5 . . ?
C36 C37 C40 120.2(5) . . ?
C36 C37 H37 119.9 . . ?
C40 C37 H37 119.9 . . ?
C45 C38 C39 124.4(4) . . ?
C45 C38 C46 117.8(4) . . ?
C39 C38 C46 117.8(4) . . ?
C42 C39 C38 121.0(4) . . ?
C42 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C37 C40 N5 120.6(4) . . ?
C37 C40 C32 119.8(4) . . ?
N5 C40 C32 119.4(5) . . ?
N7 C41 N5 106.8(3) . . ?
N7 C41 C43 112.2(3) . . ?
N5 C41 C43 111.2(4) . . ?
N7 C41 H41 108.9 . . ?
N5 C41 H41 108.9 . . ?
C43 C41 H41 108.9 . . ?
C39 C42 C48 120.1(5) . . ?
C39 C42 H42 120.0 . . ?
C48 C42 H42 120.0 . . ?
C45 C43 C44 116.6(4) . . ?
C45 C43 C41 123.3(4) . . ?
C44 C43 C41 120.0(4) . . ?
N8 C44 C43 126.4(4) . . ?
N8 C44 Cl2 114.9(3) . . ?
C43 C44 Cl2 118.6(3) . . ?
C43 C45 C38 120.9(4) . . ?
C43 C45 H45 119.5 . . ?
C38 C45 H45 119.5 . . ?
N8 C46 C47 118.0(4) . . ?
N8 C46 C38 121.3(4) . . ?
C47 C46 C38 120.7(4) . . ?
C48 C47 C46 119.1(4) . . ?
C48 C47 H47 120.4 . . ?
C46 C47 H47 120.4 . . ?
C47 C48 O2 125.4(5) . . ?
C47 C48 C42 121.4(5) . . ?
O2 C48 C42 113.2(5) . . ?
C24 N1 C1 104.6(4) . . ?
C24 N2 C6 107.0(4) . . ?
C24 N2 C7 129.1(4) . . ?
C6 N2 C7 123.8(4) . . ?
C18 N3 C7 125.4(4) . . ?
C18 N3 H3A 117.3 . . ?
C7 N3 H3A 117.3 . . ?
C9 N4 C10 116.5(4) . . ?
C40 N5 C41 125.8(4) . . ?
C40 N5 H5A 117.1 . . ?
C41 N5 H5A 117.1 . . ?
C31 N6 C30 104.0(4) . . ?
C31 N7 C25 107.6(4) . . ?
C31 N7 C41 128.8(4) . . ?
C25 N7 C41 123.6(4) . . ?
C44 N8 C46 116.9(3) . . ?
C12 O1 C13 116.9(4) . . ?
C48 O2 C35 117.8(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
C6 C1 C2 C3 1.1(7) . . . . ?
N1 C1 C2 C3 179.6(5) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C2 C3 C4 C5 -1.9(8) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C1 1.5(7) . . . . ?
C4 C5 C6 N2 -179.9(5) . . . . ?
C2 C1 C6 C5 -2.5(7) . . . . ?
N1 C1 C6 C5 178.7(4) . . . . ?
C2 C1 C6 N2 178.7(4) . . . . ?
N1 C1 C6 N2 -0.2(5) . . . . ?
N2 C7 C8 C17 43.5(6) . . . . ?
N3 C7 C8 C17 -74.6(5) . . . . ?
N2 C7 C8 C9 -142.0(4) . . . . ?
N3 C7 C8 C9 100.0(4) . . . . ?
C17 C8 C9 N4 1.8(6) . . . . ?
C7 C8 C9 N4 -173.1(4) . . . . ?
C17 C8 C9 Cl1 -177.8(3) . . . . ?
C7 C8 C9 Cl1 7.3(5) . . . . ?
N4 C10 C11 C12 179.4(4) . . . . ?
C16 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 O1 179.1(4) . . . . ?
C10 C11 C12 C14 0.0(7) . . . . ?
C11 C12 C14 C15 0.5(7) . . . . ?
O1 C12 C14 C15 -178.7(4) . . . . ?
C12 C14 C15 C16 -0.5(7) . . . . ?
C14 C15 C16 C17 177.3(4) . . . . ?
C14 C15 C16 C10 0.1(6) . . . . ?
N4 C10 C16 C15 -179.5(4) . . . . ?
C11 C10 C16 C15 0.4(6) . . . . ?
N4 C10 C16 C17 3.1(6) . . . . ?
C11 C10 C16 C17 -177.0(4) . . . . ?
C9 C8 C17 C16 0.4(6) . . . . ?
C7 C8 C17 C16 175.2(4) . . . . ?
C15 C16 C17 C8 -179.9(4) . . . . ?
C10 C16 C17 C8 -2.6(6) . . . . ?
N3 C18 C19 C20 -174.0(5) . . . . ?
C23 C18 C19 C20 2.6(7) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
C19 C20 C21 C22 -1.2(8) . . . . ?
C20 C21 C22 C23 0.9(7) . . . . ?
C19 C18 C23 C22 -2.9(6) . . . . ?
N3 C18 C23 C22 173.9(4) . . . . ?
C19 C18 C23 C24 177.0(4) . . . . ?
N3 C18 C23 C24 -6.2(6) . . . . ?
C21 C22 C23 C18 1.1(7) . . . . ?
C21 C22 C23 C24 -178.8(4) . . . . ?
C18 C23 C24 N1 178.2(4) . . . . ?
C22 C23 C24 N1 -1.9(7) . . . . ?
C18 C23 C24 N2 -1.0(6) . . . . ?
C22 C23 C24 N2 178.8(4) . . . . ?
C30 C25 C26 C27 0.5(7) . . . . ?
N7 C25 C26 C27 -179.9(4) . . . . ?
C25 C26 C27 C28 0.3(7) . . . . ?
C26 C27 C28 C29 -0.8(8) . . . . ?
C27 C28 C29 C30 0.5(8) . . . . ?
C28 C29 C30 C25 0.2(7) . . . . ?
C28 C29 C30 N6 -179.8(4) . . . . ?
C26 C25 C30 C29 -0.7(7) . . . . ?
N7 C25 C30 C29 179.6(4) . . . . ?
C26 C25 C30 N6 179.3(4) . . . . ?
N7 C25 C30 N6 -0.4(5) . . . . ?
N6 C31 C32 C40 177.2(4) . . . . ?
N7 C31 C32 C40 -2.5(6) . . . . ?
N6 C31 C32 C33 -4.7(7) . . . . ?
N7 C31 C32 C33 175.6(4) . . . . ?
C40 C32 C33 C34 0.0(6) . . . . ?
C31 C32 C33 C34 -178.1(4) . . . . ?
C32 C33 C34 C36 1.6(7) . . . . ?
C33 C34 C36 C37 -1.9(8) . . . . ?
C34 C36 C37 C40 0.7(7) . . . . ?
C45 C38 C39 C42 178.6(4) . . . . ?
C46 C38 C39 C42 0.8(7) . . . . ?
C36 C37 C40 N5 -175.5(4) . . . . ?
C36 C37 C40 C32 0.9(7) . . . . ?
C33 C32 C40 C37 -1.2(6) . . . . ?
C31 C32 C40 C37 176.9(4) . . . . ?
C33 C32 C40 N5 175.2(4) . . . . ?
C31 C32 C40 N5 -6.7(6) . . . . ?
C38 C39 C42 C48 -1.4(7) . . . . ?
N7 C41 C43 C45 33.5(6) . . . . ?
N5 C41 C43 C45 -85.9(5) . . . . ?
N7 C41 C43 C44 -150.1(4) . . . . ?
N5 C41 C43 C44 90.4(5) . . . . ?
C45 C43 C44 N8 0.9(7) . . . . ?
C41 C43 C44 N8 -175.7(4) . . . . ?
C45 C43 C44 Cl2 179.9(3) . . . . ?
C41 C43 C44 Cl2 3.3(6) . . . . ?
C44 C43 C45 C38 1.1(6) . . . . ?
C41 C43 C45 C38 177.6(4) . . . . ?
C39 C38 C45 C43 179.9(4) . . . . ?
C46 C38 C45 C43 -2.3(6) . . . . ?
C45 C38 C46 N8 1.7(6) . . . . ?
C39 C38 C46 N8 179.6(4) . . . . ?
C45 C38 C46 C47 -177.4(4) . . . . ?
C39 C38 C46 C47 0.5(6) . . . . ?
N8 C46 C47 C48 179.6(4) . . . . ?
C38 C46 C47 C48 -1.3(7) . . . . ?
C46 C47 C48 O2 179.0(4) . . . . ?
C46 C47 C48 C42 0.7(7) . . . . ?
C39 C42 C48 C47 0.7(8) . . . . ?
C39 C42 C48 O2 -177.9(4) . . . . ?
N2 C24 N1 C1 -0.9(5) . . . . ?
C23 C24 N1 C1 179.8(4) . . . . ?
C6 C1 N1 C24 0.6(5) . . . . ?
C2 C1 N1 C24 -178.0(5) . . . . ?
N1 C24 N2 C6 0.8(5) . . . . ?
C23 C24 N2 C6 -179.9(4) . . . . ?
N1 C24 N2 C7 176.3(4) . . . . ?
C23 C24 N2 C7 -4.3(7) . . . . ?
C5 C6 N2 C24 -179.1(5) . . . . ?
C1 C6 N2 C24 -0.3(5) . . . . ?
C5 C6 N2 C7 5.1(8) . . . . ?
C1 C6 N2 C7 -176.2(4) . . . . ?
N3 C7 N2 C24 14.3(6) . . . . ?
C8 C7 N2 C24 -106.0(5) . . . . ?
N3 C7 N2 C6 -170.9(4) . . . . ?
C8 C7 N2 C6 68.9(5) . . . . ?
C19 C18 N3 C7 -163.6(4) . . . . ?
C23 C18 N3 C7 19.7(6) . . . . ?
N2 C7 N3 C18 -21.9(6) . . . . ?
C8 C7 N3 C18 100.0(5) . . . . ?
C8 C9 N4 C10 -1.3(6) . . . . ?
Cl1 C9 N4 C10 178.3(3) . . . . ?
C16 C10 N4 C9 -1.2(6) . . . . ?
C11 C10 N4 C9 178.8(4) . . . . ?
C37 C40 N5 C41 -164.4(4) . . . . ?
C32 C40 N5 C41 19.2(6) . . . . ?
N7 C41 N5 C40 -18.9(6) . . . . ?
C43 C41 N5 C40 103.7(5) . . . . ?
N7 C31 N6 C30 -0.3(5) . . . . ?
C32 C31 N6 C30 180.0(4) . . . . ?
C29 C30 N6 C31 -179.5(4) . . . . ?
C25 C30 N6 C31 0.4(5) . . . . ?
N6 C31 N7 C25 0.1(5) . . . . ?
C32 C31 N7 C25 179.8(4) . . . . ?
N6 C31 N7 C41 -179.1(4) . . . . ?
C32 C31 N7 C41 0.6(6) . . . . ?
C26 C25 N7 C31 -179.5(5) . . . . ?
C30 C25 N7 C31 0.2(4) . . . . ?
C26 C25 N7 C41 -0.2(7) . . . . ?
C30 C25 N7 C41 179.4(4) . . . . ?
N5 C41 N7 C31 9.0(6) . . . . ?
C43 C41 N7 C31 -113.1(5) . . . . ?
N5 C41 N7 C25 -170.1(4) . . . . ?
C43 C41 N7 C25 67.8(5) . . . . ?
C43 C44 N8 C46 -1.5(7) . . . . ?
Cl2 C44 N8 C46 179.5(3) . . . . ?
C47 C46 N8 C44 179.2(4) . . . . ?
C38 C46 N8 C44 0.1(6) . . . . ?
C11 C12 O1 C13 -3.1(7) . . . . ?
C14 C12 O1 C13 176.1(4) . . . . ?
C47 C48 O2 C35 -3.9(7) . . . . ?
C42 C48 O2 C35 174.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 1034022'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 Cl N4, C H4 O'
_chemical_formula_sum            'C24 H19 Cl N4 O'
_chemical_formula_weight         414.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   9.3626(13)
_cell_length_b                   9.5165(16)
_cell_length_c                   12.620(2)
_cell_angle_alpha                85.853(7)
_cell_angle_beta                 86.132(7)
_cell_angle_gamma                80.744(7)
_cell_volume                     1105.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5849
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.45

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18825
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         27.81
_reflns_number_total             5152
_reflns_number_gt                3498
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1869P)²+0.7516P] 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         5152
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.3013
_refine_ls_wR_factor_gt          0.2696
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.2325(4) 0.7270(4) 0.4987(3) 0.0523(8) Uani 1 1 d . . .
C2 C 0.1603(5) 0.8089(6) 0.5808(4) 0.0836(14) Uani 1 1 d . . .
H2 H 0.2123 0.8548 0.6240 0.100 Uiso 1 1 calc R . .
C3 C 0.0121(6) 0.8202(7) 0.5961(4) 0.0984(18) Uani 1 1 d . . .
H3 H -0.0360 0.8763 0.6489 0.118 Uiso 1 1 calc R . .
C4 C -0.0660(5) 0.7503(6) 0.5349(4) 0.0901(15) Uani 1 1 d . . .
H4 H -0.1656 0.7565 0.5487 0.108 Uiso 1 1 calc R . .
C5 C 0.0005(4) 0.6718(5) 0.4541(3) 0.0693(11) Uani 1 1 d . . .
H5 H -0.0543 0.6270 0.4121 0.083 Uiso 1 1 calc R . .
C6 C 0.1521(3) 0.6582(4) 0.4339(3) 0.0480(7) Uani 1 1 d . . .
C7 C 0.2286(3) 0.5799(3) 0.3515(2) 0.0447(7) Uani 1 1 d . . .
H7 H 0.1784 0.5322 0.3082 0.054 Uiso 1 1 calc R . .
C8 C 0.3746(3) 0.5729(3) 0.3343(2) 0.0376(6) Uani 1 1 d . . .
C9 C 0.4428(3) 0.6447(3) 0.4066(2) 0.0409(7) Uani 1 1 d . . .
C10 C 0.4624(3) 0.5000(3) 0.2416(2) 0.0423(7) Uani 1 1 d . . .
H10 H 0.5524 0.4458 0.2680 0.051 Uiso 1 1 calc R . .
C11 C 0.3716(4) 0.2634(3) 0.2316(3) 0.0472(7) Uani 1 1 d . . .
C12 C 0.4309(4) 0.1763(4) 0.3154(3) 0.0570(9) Uani 1 1 d . . .
H12 H 0.4887 0.2083 0.3627 0.068 Uiso 1 1 calc R . .
C13 C 0.3984(5) 0.0372(4) 0.3246(3) 0.0651(10) Uani 1 1 d . . .
H13 H 0.4355 -0.0258 0.3795 0.078 Uiso 1 1 calc R . .
C14 C 0.3122(5) -0.0075(4) 0.2535(3) 0.0678(11) Uani 1 1 d . . .
H14 H 0.2936 -0.1008 0.2614 0.081 Uiso 1 1 calc R . .
C15 C 0.2530(4) 0.0803(4) 0.1714(3) 0.0616(10) Uani 1 1 d . . .
H15 H 0.1955 0.0476 0.1242 0.074 Uiso 1 1 calc R . .
C16 C 0.2814(4) 0.2196(4) 0.1611(3) 0.0522(8) Uani 1 1 d . . .
C17 C 0.3018(4) 0.4352(4) 0.1091(3) 0.0493(8) Uani 1 1 d . . .
C18 C 0.3032(4) 0.5744(4) 0.0529(3) 0.0552(9) Uani 1 1 d . . .
C19 C 0.2133(5) 0.6236(5) -0.0320(4) 0.0720(11) Uani 1 1 d . . .
H19 H 0.1430 0.5713 -0.0488 0.086 Uiso 1 1 calc R . .
C20 C 0.2297(6) 0.7488(5) -0.0896(4) 0.0819(14) Uani 1 1 d . . .
H20 H 0.1717 0.7812 -0.1461 0.098 Uiso 1 1 calc R . .
C21 C 0.3344(6) 0.8264(5) -0.0620(4) 0.0796(13) Uani 1 1 d . . .
H21 H 0.3455 0.9111 -0.1011 0.096 Uiso 1 1 calc R . .
C22 C 0.4202(5) 0.7826(4) 0.0195(3) 0.0648(10) Uani 1 1 d . . .
H22 H 0.4882 0.8374 0.0366 0.078 Uiso 1 1 calc R . .
C23 C 0.4067(4) 0.6537(4) 0.0788(3) 0.0533(8) Uani 1 1 d . . .
C24 C 0.0879(11) 1.2202(17) -0.1633(7) 0.289(10) Uani 1 1 d . . .
H24A H 0.0231 1.2093 -0.1020 0.433 Uiso 1 1 calc R . .
H24B H 0.1081 1.1323 -0.1983 0.433 Uiso 1 1 calc R . .
H24C H 0.0436 1.2947 -0.2115 0.433 Uiso 1 1 calc R . .
N1 N 0.3799(3) 0.7170(3) 0.4841(2) 0.0509(7) Uani 1 1 d . . .
N2 N 0.3833(3) 0.4025(3) 0.1963(2) 0.0501(7) Uani 1 1 d . . .
N3 N 0.2381(3) 0.3299(3) 0.0844(2) 0.0567(7) Uani 1 1 d . . .
N4 N 0.4989(3) 0.6029(3) 0.1586(2) 0.0558(7) Uani 1 1 d . . .
H4A H 0.5805 0.6334 0.1589 0.067 Uiso 1 1 calc R . .
Cl1 Cl 0.63067(8) 0.63743(11) 0.39114(7) 0.0594(3) Uani 1 1 d . . .
O1 O 0.2388(5) 1.2613(6) -0.1261(3) 0.1151(16) Uani 1 1 d D . .
H1A H 0.217(8) 1.306(7) -0.070(4) 0.138 Uiso 1 1 d 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
C1 N1 1.369(4) . ?
C1 C6 1.408(5) . ?
C1 C2 1.411(5) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(4) . ?
C7 C8 1.361(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.420(4) . ?
C8 C10 1.527(4) . ?
C9 N1 1.291(4) . ?
C9 Cl1 1.747(3) . ?
C10 N4 1.443(4) . ?
C10 N2 1.446(4) . ?
C10 H10 0.9800 . ?
C11 N2 1.384(4) . ?
C11 C12 1.385(5) . ?
C11 C16 1.395(5) . ?
C12 C13 1.400(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(5) . ?
C15 H15 0.9300 . ?
C16 N3 1.404(5) . ?
C17 N3 1.312(4) . ?
C17 N2 1.370(4) . ?
C17 C18 1.458(5) . ?
C18 C23 1.389(5) . ?
C18 C19 1.413(6) . ?
C19 C20 1.375(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.395(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.349(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.408(5) . ?
C22 H22 0.9300 . ?
C23 N4 1.381(5) . ?
C24 O1 1.632(13) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N4 H4A 0.8600 . ?
O1 H1A 0.85(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 121.7(3) . . ?
N1 C1 C2 118.7(3) . . ?
C6 C1 C2 119.6(3) . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 117.6(3) . . ?
C1 C6 C5 118.8(3) . . ?
C7 C6 C5 123.7(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 115.5(3) . . ?
C7 C8 C10 123.9(3) . . ?
C9 C8 C10 120.5(3) . . ?
N1 C9 C8 126.5(3) . . ?
N1 C9 Cl1 115.3(2) . . ?
C8 C9 Cl1 118.2(2) . . ?
N4 C10 N2 108.5(3) . . ?
N4 C10 C8 111.4(3) . . ?
N2 C10 C8 111.1(2) . . ?
N4 C10 H10 108.6 . . ?
N2 C10 H10 108.6 . . ?
C8 C10 H10 108.6 . . ?
N2 C11 C12 132.1(3) . . ?
N2 C11 C16 104.6(3) . . ?
C12 C11 C16 123.3(3) . . ?
C11 C12 C13 116.0(3) . . ?
C11 C12 H12 122.0 . . ?
C13 C12 H12 122.0 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 122.6(4) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C15 C16 C11 119.3(3) . . ?
C15 C16 N3 129.9(3) . . ?
C11 C16 N3 110.7(3) . . ?
N3 C17 N2 113.3(3) . . ?
N3 C17 C18 128.6(3) . . ?
N2 C17 C18 117.9(3) . . ?
C23 C18 C19 119.9(4) . . ?
C23 C18 C17 117.5(3) . . ?
C19 C18 C17 122.4(4) . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.0(4) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 122.0(4) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 119.9(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
N4 C23 C18 120.0(3) . . ?
N4 C23 C22 120.8(4) . . ?
C18 C23 C22 119.1(4) . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 117.4(3) . . ?
C17 N2 C11 107.2(3) . . ?
C17 N2 C10 124.7(3) . . ?
C11 N2 C10 128.1(3) . . ?
C17 N3 C16 104.1(3) . . ?
C23 N4 C10 121.9(3) . . ?
C23 N4 H4A 119.0 . . ?
C10 N4 H4A 119.0 . . ?
C24 O1 H1A 106(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.8(4) . . . . ?
C6 C1 C2 C3 0.0(7) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C3 C4 C5 -2.6(10) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
N1 C1 C6 C7 -1.1(5) . . . . ?
C2 C1 C6 C7 178.7(4) . . . . ?
N1 C1 C6 C5 179.3(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C4 C5 C6 C7 -179.5(4) . . . . ?
C1 C6 C7 C8 -1.0(5) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C6 C7 C8 C9 2.1(5) . . . . ?
C6 C7 C8 C10 -175.1(3) . . . . ?
C7 C8 C9 N1 -1.5(5) . . . . ?
C10 C8 C9 N1 175.8(3) . . . . ?
C7 C8 C9 Cl1 178.7(2) . . . . ?
C10 C8 C9 Cl1 -4.0(4) . . . . ?
C7 C8 C10 N4 102.5(3) . . . . ?
C9 C8 C10 N4 -74.5(4) . . . . ?
C7 C8 C10 N2 -18.6(4) . . . . ?
C9 C8 C10 N2 164.4(3) . . . . ?
N2 C11 C12 C13 -177.8(3) . . . . ?
C16 C11 C12 C13 1.7(5) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C11 1.9(5) . . . . ?
C14 C15 C16 N3 178.4(4) . . . . ?
N2 C11 C16 C15 176.9(3) . . . . ?
C12 C11 C16 C15 -2.7(5) . . . . ?
N2 C11 C16 N3 -0.3(4) . . . . ?
C12 C11 C16 N3 -179.9(3) . . . . ?
N3 C17 C18 C23 -164.1(3) . . . . ?
N2 C17 C18 C23 11.6(5) . . . . ?
N3 C17 C18 C19 10.0(6) . . . . ?
N2 C17 C18 C19 -174.2(3) . . . . ?
C23 C18 C19 C20 0.9(6) . . . . ?
C17 C18 C19 C20 -173.1(4) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C19 C20 C21 C22 -0.1(7) . . . . ?
C20 C21 C22 C23 0.9(6) . . . . ?
C19 C18 C23 N4 -177.2(3) . . . . ?
C17 C18 C23 N4 -2.9(5) . . . . ?
C19 C18 C23 C22 -0.1(5) . . . . ?
C17 C18 C23 C22 174.2(3) . . . . ?
C21 C22 C23 N4 176.3(3) . . . . ?
C21 C22 C23 C18 -0.8(5) . . . . ?
C8 C9 N1 C1 -0.5(5) . . . . ?
Cl1 C9 N1 C1 179.3(3) . . . . ?
C6 C1 N1 C9 1.8(5) . . . . ?
C2 C1 N1 C9 -178.1(4) . . . . ?
N3 C17 N2 C11 0.0(4) . . . . ?
C18 C17 N2 C11 -176.4(3) . . . . ?
N3 C17 N2 C10 -178.8(3) . . . . ?
C18 C17 N2 C10 4.8(5) . . . . ?
C12 C11 N2 C17 179.7(3) . . . . ?
C16 C11 N2 C17 0.2(3) . . . . ?
C12 C11 N2 C10 -1.5(6) . . . . ?
C16 C11 N2 C10 178.9(3) . . . . ?
N4 C10 N2 C17 -26.7(4) . . . . ?
C8 C10 N2 C17 96.1(3) . . . . ?
N4 C10 N2 C11 154.8(3) . . . . ?
C8 C10 N2 C11 -82.5(4) . . . . ?
N2 C17 N3 C16 -0.1(4) . . . . ?
C18 C17 N3 C16 175.8(3) . . . . ?
C15 C16 N3 C17 -176.5(4) . . . . ?
C11 C16 N3 C17 0.2(4) . . . . ?
C18 C23 N4 C10 -23.0(5) . . . . ?
C22 C23 N4 C10 160.0(3) . . . . ?
N2 C10 N4 C23 35.8(4) . . . . ?
C8 C10 N4 C23 -86.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.81
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.383
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.091
