# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1025096'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Cl4 N2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C30 H16 Cl4 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         546.25
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.336(2)
_cell_length_b                   9.118(3)
_cell_length_c                   17.445(5)
_cell_angle_alpha                103.692(17)
_cell_angle_beta                 93.563(17)
_cell_angle_gamma                107.081(14)
_cell_volume                     1219.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1830
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow

_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.44

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.807

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            9490
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.42
_reflns_number_total             4345
_reflns_number_gt                2787
_reflns_threshold_expression     >2sigma(I)

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.971

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0597P)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    Constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4345
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_refine_diff_density_max         0.269
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.048

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl Uani 0.64611(9) 0.19474(9) 0.48577(3) 1.000 0.0793(3) . .
Cl2 Cl Uani 0.13898(9) 0.41437(8) 0.57372(4) 1.000 0.0817(3) . .
Cl3 Cl Uani 0.41574(7) -0.22116(7) 0.28358(3) 1.000 0.0617(2) . .
Cl4 Cl Uani -0.10999(9) -0.03364(8) 0.37834(4) 1.000 0.0812(3) . .
N1 N Uani 0.7276(2) -0.01960(18) 0.04739(8) 1.000 0.0398(5) . .
N2 N Uani 0.2459(2) -0.30052(19) 0.06930(8) 1.000 0.0437(5) . .
C1 C Uani 0.8054(2) 0.1200(2) 0.10202(10) 1.000 0.0382(6) . .
C2 C Uani 0.9686(3) 0.2112(2) 0.09170(12) 1.000 0.0490(7) . .
C3 C Uani 1.0537(3) 0.3526(3) 0.14399(13) 1.000 0.0569(8) . .
C4 C Uani 0.9803(3) 0.4130(2) 0.21030(13) 1.000 0.0580(8) . .
C5 C Uani 0.8233(3) 0.3310(2) 0.22101(11) 1.000 0.0497(7) . .
C6 C Uani 0.7298(2) 0.1818(2) 0.16832(10) 1.000 0.0375(6) . .
C7 C Uani 0.5647(2) 0.0913(2) 0.17638(9) 1.000 0.0356(6) . .
C8 C Uani 0.4852(2) -0.0562(2) 0.12070(9) 1.000 0.0347(6) . .
C9 C Uani 0.3200(2) -0.1667(2) 0.12267(10) 1.000 0.0376(6) . .
C10 C Uani 0.3291(3) -0.3467(2) 0.00519(10) 1.000 0.0418(7) . .
C11 C Uani 0.2455(3) -0.4910(2) -0.05100(11) 1.000 0.0543(8) . .
C12 C Uani 0.3231(3) -0.5428(3) -0.11457(12) 1.000 0.0611(8) . .
C13 C Uani 0.4820(3) -0.4522(3) -0.12327(11) 1.000 0.0578(8) . .
C14 C Uani 0.5663(3) -0.3093(2) -0.06870(10) 1.000 0.0483(7) . .
C15 C Uani 0.4903(2) -0.2544(2) -0.00308(9) 1.000 0.0380(6) . .
C16 C Uani 0.5735(2) -0.1050(2) 0.05644(9) 1.000 0.0356(6) . .
C17 C Uani 0.4762(2) 0.1587(2) 0.24034(10) 1.000 0.0397(6) . .
C18 C Uani 0.5308(3) 0.1984(2) 0.31729(10) 1.000 0.0437(7) . .
C19 C Uani 0.4393(2) 0.2580(2) 0.38044(10) 1.000 0.0414(6) . .
C20 C Uani 0.3048(3) 0.3138(3) 0.36530(12) 1.000 0.0576(8) . .
C21 C Uani 0.2131(3) 0.3619(3) 0.42317(13) 1.000 0.0616(8) . .
C22 C Uani 0.2550(3) 0.3552(2) 0.49974(12) 1.000 0.0541(8) . .
C23 C Uani 0.3866(3) 0.3041(2) 0.51859(11) 1.000 0.0531(8) . .
C24 C Uani 0.4783(3) 0.2564(2) 0.45921(10) 1.000 0.0468(7) . .
C25 C Uani 0.2135(2) -0.1356(2) 0.18766(10) 1.000 0.0378(6) . .
C26 C Uani 0.0739(3) -0.0882(2) 0.17291(11) 1.000 0.0495(7) . .
C27 C Uani -0.0260(3) -0.0584(2) 0.23085(12) 1.000 0.0545(8) . .
C28 C Uani 0.0121(3) -0.0783(2) 0.30444(12) 1.000 0.0500(7) . .
C29 C Uani 0.1461(3) -0.1292(2) 0.32134(11) 1.000 0.0463(7) . .
C30 C Uani 0.2452(2) -0.1581(2) 0.26223(10) 1.000 0.0398(7) . .
H2 H Uiso 1.01790 0.17290 0.04820 1.000 0.0590 calc R
H3 H Uiso 1.16080 0.41050 0.13640 1.000 0.0680 calc R
H4 H Uiso 1.04020 0.50960 0.24670 1.000 0.0700 calc R
H5 H Uiso 0.77570 0.37370 0.26410 1.000 0.0600 calc R
H11 H Uiso 0.13790 -0.55190 -0.04550 1.000 0.0650 calc R
H12 H Uiso 0.26810 -0.63950 -0.15190 1.000 0.0730 calc R
H13 H Uiso 0.53280 -0.48830 -0.16670 1.000 0.0690 calc R
H14 H Uiso 0.67340 -0.24920 -0.07530 1.000 0.0580 calc R
H17 H Uiso 0.37490 0.17410 0.22490 1.000 0.0480 calc R
H18 H Uiso 0.63470 0.18780 0.33270 1.000 0.0530 calc R
H20 H Uiso 0.27620 0.31850 0.31380 1.000 0.0690 calc R
H21 H Uiso 0.12410 0.39840 0.41100 1.000 0.0740 calc R
H23 H Uiso 0.41460 0.30110 0.57050 1.000 0.0640 calc R
H26 H Uiso 0.04700 -0.07610 0.12270 1.000 0.0590 calc R
H27 H Uiso -0.11830 -0.02520 0.22010 1.000 0.0650 calc R
H29 H Uiso 0.16990 -0.14400 0.37120 1.000 0.0560 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C24 1.730(3) . . yes
Cl2 C22 1.739(2) . . yes
Cl3 C30 1.7338(19) . . yes
Cl4 C28 1.738(2) . . yes
N1 C1 1.347(2) . . yes
N1 C16 1.333(2) . . yes
N2 C9 1.298(2) . . yes
N2 C10 1.398(3) . . yes
C1 C2 1.418(3) . . no
C1 C6 1.429(2) . . no
C2 C3 1.350(3) . . no
C3 C4 1.414(3) . . no
C4 C5 1.352(3) . . no
C5 C6 1.414(3) . . no
C6 C7 1.417(3) . . no
C7 C8 1.403(2) . . no
C7 C17 1.487(2) . . no
C8 C9 1.456(3) . . no
C8 C16 1.434(2) . . no
C9 C25 1.508(2) . . no
C10 C11 1.394(3) . . no
C10 C15 1.397(3) . . no
C11 C12 1.376(3) . . no
C12 C13 1.379(4) . . no
C13 C14 1.375(3) . . no
C14 C15 1.403(3) . . no
C15 C16 1.449(2) . . no
C17 C18 1.318(2) . . no
C18 C19 1.468(3) . . no
C19 C20 1.396(3) . . no
C19 C24 1.397(2) . . no
C20 C21 1.371(3) . . no
C21 C22 1.380(3) . . no
C22 C23 1.363(3) . . no
C23 C24 1.388(3) . . no
C25 C26 1.385(3) . . no
C25 C30 1.386(2) . . no
C26 C27 1.377(3) . . no
C27 C28 1.369(3) . . no
C28 C29 1.371(3) . . no
C29 C30 1.386(3) . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C17 H17 0.9300 . . no
C18 H18 0.9300 . . no
C20 H20 0.9300 . . no
C21 H21 0.9300 . . no
C23 H23 0.9300 . . no
C26 H26 0.9300 . . no
C27 H27 0.9300 . . no
C29 H29 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 118.17(15) . . . yes
C9 N2 C10 119.02(17) . . . yes
N1 C1 C2 117.97(16) . . . yes
N1 C1 C6 123.21(16) . . . yes
C2 C1 C6 118.80(16) . . . no
C1 C2 C3 121.2(2) . . . no
C2 C3 C4 120.2(2) . . . no
C3 C4 C5 120.3(2) . . . no
C4 C5 C6 121.65(19) . . . no
C1 C6 C5 117.92(17) . . . no
C1 C6 C7 118.03(16) . . . no
C5 C6 C7 124.04(17) . . . no
C6 C7 C8 118.83(15) . . . no
C6 C7 C17 119.40(15) . . . no
C8 C7 C17 121.66(16) . . . no
C7 C8 C9 125.68(15) . . . no
C7 C8 C16 117.94(16) . . . no
C9 C8 C16 116.37(15) . . . no
N2 C9 C8 124.89(16) . . . yes
N2 C9 C25 112.14(16) . . . yes
C8 C9 C25 122.96(15) . . . no
N2 C10 C11 117.4(2) . . . yes
N2 C10 C15 122.23(16) . . . yes
C11 C10 C15 120.37(19) . . . no
C10 C11 C12 119.6(2) . . . no
C11 C12 C13 120.4(2) . . . no
C12 C13 C14 120.9(2) . . . no
C13 C14 C15 119.8(2) . . . no
C10 C15 C14 118.94(16) . . . no
C10 C15 C16 118.90(15) . . . no
C14 C15 C16 122.16(17) . . . no
N1 C16 C8 123.77(15) . . . yes
N1 C16 C15 117.71(15) . . . yes
C8 C16 C15 118.51(16) . . . no
C7 C17 C18 124.85(18) . . . no
C17 C18 C19 124.7(2) . . . no
C18 C19 C20 122.45(17) . . . no
C18 C19 C24 121.54(18) . . . no
C20 C19 C24 115.97(18) . . . no
C19 C20 C21 122.8(2) . . . no
C20 C21 C22 118.9(2) . . . no
Cl2 C22 C21 119.49(19) . . . yes
Cl2 C22 C23 119.37(16) . . . yes
C21 C22 C23 121.2(2) . . . no
C22 C23 C24 119.10(18) . . . no
Cl1 C24 C19 120.19(16) . . . yes
Cl1 C24 C23 117.71(15) . . . yes
C19 C24 C23 122.1(2) . . . no
C9 C25 C26 119.94(16) . . . no
C9 C25 C30 122.65(16) . . . no
C26 C25 C30 117.36(16) . . . no
C25 C26 C27 121.55(18) . . . no
C26 C27 C28 119.3(2) . . . no
Cl4 C28 C27 118.97(19) . . . yes
Cl4 C28 C29 119.57(16) . . . yes
C27 C28 C29 121.4(2) . . . no
C28 C29 C30 118.34(18) . . . no
Cl3 C30 C25 119.49(13) . . . yes
Cl3 C30 C29 118.50(14) . . . yes
C25 C30 C29 122.01(17) . . . no
C1 C2 H2 119.00 . . . no
C3 C2 H2 119.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C7 C17 H17 118.00 . . . no
C18 C17 H17 118.00 . . . no
C17 C18 H18 118.00 . . . no
C19 C18 H18 118.00 . . . no
C19 C20 H20 119.00 . . . no
C21 C20 H20 119.00 . . . no
C20 C21 H21 121.00 . . . no
C22 C21 H21 121.00 . . . no
C22 C23 H23 120.00 . . . no
C24 C23 H23 120.00 . . . no
C25 C26 H26 119.00 . . . no
C27 C26 H26 119.00 . . . no
C26 C27 H27 120.00 . . . no
C28 C27 H27 120.00 . . . no
C28 C29 H29 121.00 . . . no
C30 C29 H29 121.00 . . . no

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
C16 N1 C1 C2 -179.37(17) . . . . no
C16 N1 C1 C6 -1.0(3) . . . . no
C1 N1 C16 C8 0.5(3) . . . . no
C1 N1 C16 C15 179.47(16) . . . . no
C10 N2 C9 C8 1.3(3) . . . . no
C10 N2 C9 C25 -179.72(16) . . . . no
C9 N2 C10 C11 -179.90(19) . . . . no
C9 N2 C10 C15 0.6(3) . . . . no
N1 C1 C2 C3 179.7(2) . . . . no
C6 C1 C2 C3 1.3(3) . . . . no
N1 C1 C6 C5 -179.08(17) . . . . no
N1 C1 C6 C7 -0.2(3) . . . . no
C2 C1 C6 C5 -0.7(3) . . . . no
C2 C1 C6 C7 178.17(17) . . . . no
C1 C2 C3 C4 -0.4(3) . . . . no
C2 C3 C4 C5 -1.2(4) . . . . no
C3 C4 C5 C6 1.8(3) . . . . no
C4 C5 C6 C1 -0.8(3) . . . . no
C4 C5 C6 C7 -179.60(19) . . . . no
C1 C6 C7 C8 1.9(2) . . . . no
C1 C6 C7 C17 -174.51(16) . . . . no
C5 C6 C7 C8 -179.34(17) . . . . no
C5 C6 C7 C17 4.3(3) . . . . no
C6 C7 C8 C9 176.89(17) . . . . no
C6 C7 C8 C16 -2.3(2) . . . . no
C17 C7 C8 C9 -6.8(3) . . . . no
C17 C7 C8 C16 174.00(16) . . . . no
C6 C7 C17 C18 -61.2(3) . . . . no
C8 C7 C17 C18 122.5(2) . . . . no
C7 C8 C9 N2 177.74(18) . . . . no
C7 C8 C9 C25 -1.2(3) . . . . no
C16 C8 C9 N2 -3.1(3) . . . . no
C16 C8 C9 C25 178.03(16) . . . . no
C7 C8 C16 N1 1.2(3) . . . . no
C7 C8 C16 C15 -177.81(16) . . . . no
C9 C8 C16 N1 -178.11(16) . . . . no
C9 C8 C16 C15 2.9(2) . . . . no
N2 C9 C25 C26 -75.0(2) . . . . no
N2 C9 C25 C30 102.6(2) . . . . no
C8 C9 C25 C26 104.1(2) . . . . no
C8 C9 C25 C30 -78.4(2) . . . . no
N2 C10 C11 C12 -179.1(2) . . . . no
C15 C10 C11 C12 0.4(3) . . . . no
N2 C10 C15 C14 179.45(18) . . . . no
N2 C10 C15 C16 -0.6(3) . . . . no
C11 C10 C15 C14 0.0(3) . . . . no
C11 C10 C15 C16 179.98(18) . . . . no
C10 C11 C12 C13 -0.6(3) . . . . no
C11 C12 C13 C14 0.3(4) . . . . no
C12 C13 C14 C15 0.1(3) . . . . no
C13 C14 C15 C10 -0.3(3) . . . . no
C13 C14 C15 C16 179.77(19) . . . . no
C10 C15 C16 N1 179.65(17) . . . . no
C10 C15 C16 C8 -1.3(2) . . . . no
C14 C15 C16 N1 -0.4(3) . . . . no
C14 C15 C16 C8 178.68(17) . . . . no
C7 C17 C18 C19 -177.03(17) . . . . no
C17 C18 C19 C20 -15.5(3) . . . . no
C17 C18 C19 C24 162.07(19) . . . . no
C18 C19 C20 C21 176.5(2) . . . . no
C24 C19 C20 C21 -1.2(3) . . . . no
C18 C19 C24 Cl1 4.0(3) . . . . no
C18 C19 C24 C23 -176.33(18) . . . . no
C20 C19 C24 Cl1 -178.28(17) . . . . no
C20 C19 C24 C23 1.4(3) . . . . no
C19 C20 C21 C22 0.0(4) . . . . no
C20 C21 C22 Cl2 -179.5(2) . . . . no
C20 C21 C22 C23 1.0(4) . . . . no
Cl2 C22 C23 C24 179.74(15) . . . . no
C21 C22 C23 C24 -0.8(3) . . . . no
C22 C23 C24 Cl1 179.19(15) . . . . no
C22 C23 C24 C19 -0.5(3) . . . . no
C9 C25 C26 C27 -179.85(17) . . . . no
C30 C25 C26 C27 2.5(3) . . . . no
C9 C25 C30 Cl3 1.2(2) . . . . no
C9 C25 C30 C29 -179.92(18) . . . . no
C26 C25 C30 Cl3 178.76(14) . . . . no
C26 C25 C30 C29 -2.3(3) . . . . no
C25 C26 C27 C28 -1.0(3) . . . . no
C26 C27 C28 Cl4 177.73(15) . . . . no
C26 C27 C28 C29 -0.9(3) . . . . no
Cl4 C28 C29 C30 -177.56(15) . . . . no
C27 C28 C29 C30 1.0(3) . . . . no
C28 C29 C30 Cl3 179.55(15) . . . . no
C28 C29 C30 C25 0.6(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl4 3.6188(16) . 1_655 no
Cl3 C18 3.551(2) . . no
Cl3 C8 3.520(2) . . no
Cl3 C17 3.616(2) . . no
Cl4 Cl1 3.6188(16) . 1_455 no
Cl1 H18 2.6500 . . no
Cl1 H29 3.0500 . 2_656 no
Cl2 H21 3.1400 . 2_566 no
Cl2 H5 2.9300 . 2_666 no
Cl3 H13 3.0900 . 2_645 no
N1 H14 2.5200 . . no
C1 C27 3.515(3) . 1_655 no
C1 C10 3.458(3) . 2_655 no
C1 C15 3.578(3) . 2_655 no
C2 C10 3.579(3) . 2_655 no
C3 C14 3.595(4) . 2_755 no
C3 C11 3.572(4) . 2_655 no
C4 C12 3.572(4) . 2_655 no
C4 C11 3.584(3) . 2_655 no
C5 C18 3.157(3) . . no
C5 C13 3.551(4) . 2_655 no
C5 C12 3.386(3) . 2_655 no
C6 C14 3.546(3) . 2_655 no
C7 C14 3.385(3) . 2_655 no
C8 Cl3 3.520(2) . . no
C10 C2 3.579(3) . 2_655 no
C10 C1 3.458(3) . 2_655 no
C11 C3 3.572(4) . 2_655 no
C11 C4 3.584(3) . 2_655 no
C12 C5 3.386(3) . 2_655 no
C12 C4 3.572(4) . 2_655 no
C13 C5 3.551(4) . 2_655 no
C14 C6 3.546(3) . 2_655 no
C14 C3 3.595(4) . 2_755 no
C14 C7 3.385(3) . 2_655 no
C15 C1 3.578(3) . 2_655 no
C16 C16 3.451(3) . 2_655 no
C17 C30 3.089(3) . . no
C17 Cl3 3.616(2) . . no
C17 C25 2.823(3) . . no
C17 C26 3.394(3) . . no
C18 C5 3.157(3) . . no
C18 C25 3.557(3) . . no
C18 Cl3 3.551(2) . . no
C18 C30 3.294(3) . . no
C19 C29 3.521(3) . . no
C20 C28 3.552(3) . . no
C22 C24 3.460(3) . 2_666 no
C24 C22 3.460(3) . 2_666 no
C25 C17 2.823(3) . . no
C25 C18 3.557(3) . . no
C26 C17 3.394(3) . . no
C27 C1 3.515(3) . 1_455 no
C28 C20 3.552(3) . . no
C29 C19 3.521(3) . . no
C30 C17 3.089(3) . . no
C30 C18 3.294(3) . . no
C1 H27 2.8300 . 1_655 no
C2 H14 2.9400 . 2_755 no
C2 H26 3.0400 . 1_655 no
C3 H14 2.9300 . 2_755 no
C5 H18 2.8900 . . no
C6 H27 2.8400 . 1_655 no
C6 H18 3.0100 . . no
C9 H17 3.0800 . . no
C13 H3 2.9200 . 2_755 no
C14 H3 2.9100 . 2_755 no
C17 H20 2.7100 . . no
C17 H5 2.6200 . . no
C18 H5 2.5700 . . no
C20 H17 2.6600 . . no
C25 H17 2.6500 . . no
C26 H17 2.8300 . . no
C27 H12 2.8500 . 2_545 no
C29 H4 3.0700 . 1_445 no
C30 H4 2.9500 . 1_445 no
H2 H14 2.4400 . 2_755 no
H3 C13 2.9200 . 2_755 no
H3 C14 2.9100 . 2_755 no
H3 H13 2.4300 . 2_755 no
H3 H14 2.4200 . 2_755 no
H4 C29 3.0700 . 1_665 no
H4 C30 2.9500 . 1_665 no
H5 C17 2.6200 . . no
H5 C18 2.5700 . . no
H5 H18 2.3800 . . no
H5 Cl2 2.9300 . 2_666 no
H12 C27 2.8500 . 2_545 no
H13 Cl3 3.0900 . 2_645 no
H13 H3 2.4300 . 2_755 no
H14 N1 2.5200 . . no
H14 C2 2.9400 . 2_755 no
H14 C3 2.9300 . 2_755 no
H14 H2 2.4400 . 2_755 no
H14 H3 2.4200 . 2_755 no
H17 C9 3.0800 . . no
H17 C20 2.6600 . . no
H17 C25 2.6500 . . no
H17 C26 2.8300 . . no
H17 H20 2.1500 . . no
H18 Cl1 2.6500 . . no
H18 C5 2.8900 . . no
H18 C6 3.0100 . . no
H18 H5 2.3800 . . no
H20 C17 2.7100 . . no
H20 H17 2.1500 . . no
H21 Cl2 3.1400 . 2_566 no
H26 C2 3.0400 . 1_455 no
H27 C1 2.8300 . 1_455 no
H27 C6 2.8400 . 1_455 no
H29 Cl1 3.0500 . 2_656 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C18 H18 Cl1 0.9300 2.6500 3.046(2) 106.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1058218'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 Cl N3 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C30 H20 Cl N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         489.94
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.823(3)
_cell_length_b                   10.668(2)
_cell_length_c                   11.585(3)
_cell_angle_alpha                95.708(3)
_cell_angle_beta                 105.487(5)
_cell_angle_gamma                94.881(3)
_cell_volume                     1156.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1665
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow

_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.969

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            7875
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3911
_reflns_number_gt                3176
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.923
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0692P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl Uani 0.26351(6) 0.94901(5) 0.49766(4) 1.000 0.0404(2) . .
O1 O Uani -0.67564(14) 0.27257(12) 0.27964(11) 1.000 0.0355(4) . .
O2 O Uani -0.59145(15) 0.22738(13) 0.46033(12) 1.000 0.0398(5) . .
N1 N Uani 0.03301(17) 0.78076(15) 0.96569(13) 1.000 0.0274(5) . .
N2 N Uani 0.28272(15) 0.49237(13) 1.02505(12) 1.000 0.0216(4) . .
N3 N Uani -0.58510(15) 0.28835(13) 0.37792(13) 1.000 0.0243(4) . .
C1 C Uani 0.3841(2) 0.73553(16) 1.15779(15) 1.000 0.0263(5) . .
C2 C Uani 0.4211(2) 0.84799(17) 1.23524(16) 1.000 0.0313(6) . .
C3 C Uani 0.3263(2) 0.93868(16) 1.22262(16) 1.000 0.0329(6) . .
C4 C Uani 0.1993(2) 0.91867(16) 1.13349(16) 1.000 0.0300(6) . .
C5 C Uani 0.16170(19) 0.80558(15) 1.05376(14) 1.000 0.0238(5) . .
C6 C Uani 0.02131(19) 0.69572(16) 0.85555(14) 1.000 0.0227(5) . .
C7 C Uani 0.08863(18) 0.57650(15) 0.88862(14) 1.000 0.0206(5) . .
C8 C Uani 0.20993(18) 0.58821(15) 0.99130(14) 1.000 0.0198(5) . .
C9 C Uani 0.25511(18) 0.71167(15) 1.06778(14) 1.000 0.0214(5) . .
C10 C Uani 0.03914(18) 0.45888(16) 0.82235(14) 1.000 0.0221(5) . .
C11 C Uani 0.11692(18) 0.35452(15) 0.85568(14) 1.000 0.0219(5) . .
C12 C Uani 0.0804(2) 0.23138(16) 0.78998(15) 1.000 0.0280(5) . .
C13 C Uani 0.1600(2) 0.13526(17) 0.82462(16) 1.000 0.0327(6) . .
C14 C Uani 0.2810(2) 0.15774(17) 0.92490(16) 1.000 0.0335(6) . .
C15 C Uani 0.3198(2) 0.27557(16) 0.98932(16) 1.000 0.0292(6) . .
C16 C Uani 0.23960(19) 0.37705(15) 0.95668(14) 1.000 0.0222(5) . .
C17 C Uani 0.08462(18) 0.76158(14) 0.76743(14) 1.000 0.0204(5) . .
C18 C Uani 0.23117(19) 0.78374(15) 0.78453(15) 1.000 0.0230(5) . .
C19 C Uani 0.28665(19) 0.84413(15) 0.70356(15) 1.000 0.0249(5) . .
C20 C Uani 0.1944(2) 0.87846(14) 0.60208(15) 1.000 0.0246(5) . .
C21 C Uani 0.0490(2) 0.85801(15) 0.58236(15) 1.000 0.0257(5) . .
C22 C Uani -0.00473(19) 0.80192(15) 0.66647(14) 1.000 0.0228(5) . .
C23 C Uani -0.09148(19) 0.43607(17) 0.71897(15) 1.000 0.0267(5) . .
C24 C Uani -0.10580(18) 0.49088(15) 0.61926(14) 1.000 0.0215(5) . .
C25 C Uani -0.23068(18) 0.47708(15) 0.51333(14) 1.000 0.0205(5) . .
C26 C Uani -0.23010(19) 0.55537(16) 0.42333(15) 1.000 0.0249(5) . .
C27 C Uani -0.34503(19) 0.54837(16) 0.32186(15) 1.000 0.0270(5) . .
C28 C Uani -0.46404(19) 0.46178(16) 0.30632(15) 1.000 0.0245(5) . .
C29 C Uani -0.46209(18) 0.38415(14) 0.39528(14) 1.000 0.0203(5) . .
C30 C Uani -0.35041(18) 0.38933(15) 0.49813(14) 1.000 0.0203(5) . .
H1A H Uiso -0.023(2) 0.839(2) 0.959(2) 1.000 0.051(7) . .
H1C H Uiso 0.44680 0.67430 1.16600 1.000 0.0320 calc R
H2 H Uiso 0.50770 0.86260 1.29460 1.000 0.0380 calc R
H3 H Uiso 0.34910 1.01390 1.27520 1.000 0.0400 calc R
H4 H Uiso 0.13770 0.98080 1.12600 1.000 0.0360 calc R
H6 H Uiso -0.08010 0.67060 0.81590 1.000 0.0270 calc R
H12 H Uiso 0.00160 0.21570 0.72270 1.000 0.0340 calc R
H13 H Uiso 0.13390 0.05450 0.78150 1.000 0.0390 calc R
H14 H Uiso 0.33480 0.09200 0.94740 1.000 0.0400 calc R
H15 H Uiso 0.39990 0.28940 1.05550 1.000 0.0350 calc R
H18 H Uiso 0.29270 0.75760 0.85140 1.000 0.0280 calc R
H19 H Uiso 0.38450 0.86130 0.71740 1.000 0.0300 calc R
H21 H Uiso -0.01200 0.88150 0.51370 1.000 0.0310 calc R
H22 H Uiso -0.10260 0.79100 0.65520 1.000 0.0270 calc R
H23 H Uiso -0.16710 0.38050 0.72450 1.000 0.0320 calc R
H24 H Uiso -0.02750 0.54450 0.61590 1.000 0.0260 calc R
H26 H Uiso -0.15080 0.61340 0.43180 1.000 0.0300 calc R
H27 H Uiso -0.34230 0.60210 0.26380 1.000 0.0320 calc R
H28 H Uiso -0.54200 0.45620 0.23880 1.000 0.0290 calc R
H30 H Uiso -0.35460 0.33570 0.55600 1.000 0.0240 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.7388(19) . . yes
O1 N3 1.229(2) . . yes
O2 N3 1.219(2) . . yes
N1 C5 1.382(2) . . yes
N1 C6 1.462(2) . . yes
N2 C8 1.328(2) . . yes
N2 C16 1.363(2) . . yes
N3 C29 1.471(2) . . yes
N1 H1A 0.86(2) . . no
C1 C2 1.384(3) . . no
C1 C9 1.394(3) . . no
C2 C3 1.390(3) . . no
C3 C4 1.375(3) . . no
C4 C5 1.402(2) . . no
C5 C9 1.408(2) . . no
C6 C7 1.519(2) . . no
C6 C17 1.526(2) . . no
C7 C10 1.380(2) . . no
C7 C8 1.428(2) . . no
C8 C9 1.475(2) . . no
C10 C23 1.486(2) . . no
C10 C11 1.430(2) . . no
C11 C12 1.417(2) . . no
C11 C16 1.422(2) . . no
C12 C13 1.369(3) . . no
C13 C14 1.407(3) . . no
C14 C15 1.365(3) . . no
C15 C16 1.415(3) . . no
C17 C22 1.393(2) . . no
C17 C18 1.396(3) . . no
C18 C19 1.388(2) . . no
C19 C20 1.382(2) . . no
C20 C21 1.379(3) . . no
C21 C22 1.387(2) . . no
C23 C24 1.326(2) . . no
C24 C25 1.470(2) . . no
C25 C30 1.400(2) . . no
C25 C26 1.400(2) . . no
C26 C27 1.386(3) . . no
C27 C28 1.387(3) . . no
C28 C29 1.382(2) . . no
C29 C30 1.380(2) . . no
C1 H1C 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C6 H6 0.9800 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no
C18 H18 0.9300 . . no
C19 H19 0.9300 . . no
C21 H21 0.9300 . . no
C22 H22 0.9300 . . no
C23 H23 0.9300 . . no
C24 H24 0.9300 . . no
C26 H26 0.9300 . . no
C27 H27 0.9300 . . no
C28 H28 0.9300 . . no
C30 H30 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C6 119.65(16) . . . yes
C8 N2 C16 117.85(14) . . . yes
O1 N3 O2 123.26(15) . . . yes
O1 N3 C29 117.92(14) . . . yes
O2 N3 C29 118.81(14) . . . yes
C5 N1 H1A 117.5(15) . . . no
C6 N1 H1A 116.2(15) . . . no
C2 C1 C9 121.66(17) . . . no
C1 C2 C3 118.73(17) . . . no
C2 C3 C4 120.93(16) . . . no
C3 C4 C5 120.70(17) . . . no
N1 C5 C4 122.17(16) . . . yes
N1 C5 C9 118.90(15) . . . yes
C4 C5 C9 118.85(16) . . . no
N1 C6 C7 109.41(13) . . . yes
C7 C6 C17 112.44(15) . . . no
N1 C6 C17 111.73(14) . . . yes
C6 C7 C10 122.76(15) . . . no
C8 C7 C10 119.16(15) . . . no
C6 C7 C8 118.08(14) . . . no
C7 C8 C9 118.95(15) . . . no
N2 C8 C7 123.62(15) . . . yes
N2 C8 C9 117.38(14) . . . yes
C5 C9 C8 118.88(15) . . . no
C1 C9 C5 119.10(15) . . . no
C1 C9 C8 121.93(15) . . . no
C7 C10 C11 118.26(15) . . . no
C7 C10 C23 122.93(16) . . . no
C11 C10 C23 118.82(15) . . . no
C10 C11 C12 123.02(15) . . . no
C12 C11 C16 118.73(15) . . . no
C10 C11 C16 118.21(14) . . . no
C11 C12 C13 120.65(16) . . . no
C12 C13 C14 120.46(17) . . . no
C13 C14 C15 120.30(17) . . . no
C14 C15 C16 120.83(17) . . . no
C11 C16 C15 119.01(15) . . . no
N2 C16 C11 122.76(15) . . . yes
N2 C16 C15 118.22(15) . . . yes
C18 C17 C22 118.03(15) . . . no
C6 C17 C18 122.04(15) . . . no
C6 C17 C22 119.93(16) . . . no
C17 C18 C19 121.17(16) . . . no
C18 C19 C20 119.05(18) . . . no
Cl1 C20 C21 119.54(13) . . . yes
Cl1 C20 C19 119.19(15) . . . yes
C19 C20 C21 121.28(16) . . . no
C20 C21 C22 118.96(16) . . . no
C17 C22 C21 121.43(17) . . . no
C10 C23 C24 123.37(17) . . . no
C23 C24 C25 127.75(17) . . . no
C26 C25 C30 118.34(15) . . . no
C24 C25 C26 118.55(15) . . . no
C24 C25 C30 123.11(14) . . . no
C25 C26 C27 121.52(17) . . . no
C26 C27 C28 120.43(16) . . . no
C27 C28 C29 117.29(16) . . . no
N3 C29 C28 117.99(15) . . . yes
N3 C29 C30 118.06(14) . . . yes
C28 C29 C30 123.94(16) . . . no
C25 C30 C29 118.48(15) . . . no
C2 C1 H1C 119.00 . . . no
C9 C1 H1C 119.00 . . . no
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
N1 C6 H6 108.00 . . . no
C7 C6 H6 108.00 . . . no
C17 C6 H6 108.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C17 C18 H18 119.00 . . . no
C19 C18 H18 119.00 . . . no
C18 C19 H19 120.00 . . . no
C20 C19 H19 120.00 . . . no
C20 C21 H21 120.00 . . . no
C22 C21 H21 121.00 . . . no
C17 C22 H22 119.00 . . . no
C21 C22 H22 119.00 . . . no
C10 C23 H23 118.00 . . . no
C24 C23 H23 118.00 . . . no
C23 C24 H24 116.00 . . . no
C25 C24 H24 116.00 . . . no
C25 C26 H26 119.00 . . . no
C27 C26 H26 119.00 . . . no
C26 C27 H27 120.00 . . . no
C28 C27 H27 120.00 . . . no
C27 C28 H28 121.00 . . . no
C29 C28 H28 121.00 . . . no
C25 C30 H30 121.00 . . . no
C29 C30 H30 121.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C5 C4 153.09(17) . . . . no
C6 N1 C5 C9 -30.1(2) . . . . no
C5 N1 C6 C7 47.3(2) . . . . no
C5 N1 C6 C17 -77.86(19) . . . . no
C8 N2 C16 C15 177.63(16) . . . . no
C16 N2 C8 C9 178.38(15) . . . . no
C8 N2 C16 C11 -3.3(3) . . . . no
C16 N2 C8 C7 0.8(3) . . . . no
O2 N3 C29 C30 8.3(2) . . . . no
O1 N3 C29 C28 8.0(2) . . . . no
O1 N3 C29 C30 -170.63(15) . . . . no
O2 N3 C29 C28 -173.08(16) . . . . no
C2 C1 C9 C5 1.4(3) . . . . no
C2 C1 C9 C8 -175.03(17) . . . . no
C9 C1 C2 C3 0.3(3) . . . . no
C1 C2 C3 C4 -1.3(3) . . . . no
C2 C3 C4 C5 0.6(3) . . . . no
C3 C4 C5 C9 1.1(3) . . . . no
C3 C4 C5 N1 177.90(17) . . . . no
C4 C5 C9 C8 174.46(16) . . . . no
C4 C5 C9 C1 -2.1(3) . . . . no
N1 C5 C9 C8 -2.4(2) . . . . no
N1 C5 C9 C1 -178.99(16) . . . . no
N1 C6 C17 C22 -103.31(18) . . . . no
C7 C6 C17 C18 -47.0(2) . . . . no
N1 C6 C17 C18 76.5(2) . . . . no
N1 C6 C7 C10 147.05(17) . . . . no
C17 C6 C7 C8 90.49(18) . . . . no
C7 C6 C17 C22 133.22(16) . . . . no
C17 C6 C7 C10 -88.2(2) . . . . no
N1 C6 C7 C8 -34.3(2) . . . . no
C6 C7 C10 C23 -5.3(3) . . . . no
C8 C7 C10 C11 -3.5(2) . . . . no
C8 C7 C10 C23 176.03(16) . . . . no
C6 C7 C10 C11 175.17(16) . . . . no
C6 C7 C8 C9 6.4(2) . . . . no
C10 C7 C8 N2 2.7(3) . . . . no
C10 C7 C8 C9 -174.89(16) . . . . no
C6 C7 C8 N2 -176.04(16) . . . . no
C7 C8 C9 C1 -169.92(16) . . . . no
C7 C8 C9 C5 13.6(2) . . . . no
N2 C8 C9 C1 12.4(2) . . . . no
N2 C8 C9 C5 -164.11(16) . . . . no
C7 C10 C11 C12 -176.37(17) . . . . no
C7 C10 C11 C16 1.1(2) . . . . no
C7 C10 C23 C24 62.4(3) . . . . no
C11 C10 C23 C24 -118.1(2) . . . . no
C23 C10 C11 C12 4.1(3) . . . . no
C23 C10 C11 C16 -178.41(16) . . . . no
C16 C11 C12 C13 1.4(3) . . . . no
C12 C11 C16 C15 -0.9(3) . . . . no
C10 C11 C16 N2 2.4(3) . . . . no
C10 C11 C12 C13 178.86(17) . . . . no
C12 C11 C16 N2 -180.00(16) . . . . no
C10 C11 C16 C15 -178.56(16) . . . . no
C11 C12 C13 C14 -1.1(3) . . . . no
C12 C13 C14 C15 0.5(3) . . . . no
C13 C14 C15 C16 -0.1(3) . . . . no
C14 C15 C16 N2 179.41(17) . . . . no
C14 C15 C16 C11 0.3(3) . . . . no
C6 C17 C18 C19 -179.80(15) . . . . no
C22 C17 C18 C19 0.0(2) . . . . no
C18 C17 C22 C21 2.5(2) . . . . no
C6 C17 C22 C21 -177.69(15) . . . . no
C17 C18 C19 C20 -2.4(2) . . . . no
C18 C19 C20 Cl1 -177.71(13) . . . . no
C18 C19 C20 C21 2.4(2) . . . . no
C19 C20 C21 C22 0.0(2) . . . . no
Cl1 C20 C21 C22 -179.86(12) . . . . no
C20 C21 C22 C17 -2.5(2) . . . . no
C10 C23 C24 C25 -178.64(16) . . . . no
C23 C24 C25 C30 -7.6(3) . . . . no
C23 C24 C25 C26 172.36(18) . . . . no
C24 C25 C26 C27 -179.21(16) . . . . no
C30 C25 C26 C27 0.8(3) . . . . no
C24 C25 C30 C29 179.94(16) . . . . no
C26 C25 C30 C29 0.0(2) . . . . no
C25 C26 C27 C28 -0.7(3) . . . . no
C26 C27 C28 C29 -0.2(3) . . . . no
C27 C28 C29 N3 -177.64(15) . . . . no
C27 C28 C29 C30 0.9(3) . . . . no
N3 C29 C30 C25 177.72(15) . . . . no
C28 C29 C30 C25 -0.9(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 O2 3.3016(18) . 1_665 no
Cl1 C3 3.397(2) . 1_554 no
Cl1 H3 3.0400 . 1_554 no
O1 C15 3.355(2) . 1_454 no
O1 C6 3.400(3) . 2_466 no
O1 C22 3.406(3) . 2_466 no
O2 Cl1 3.3016(18) . 1_445 no
O2 C26 3.405(3) . 2_466 no
O1 H28 2.4200 . . no
O1 H6 2.5100 . 2_466 no
O1 H22 2.5500 . 2_466 no
O1 H15 2.9000 . 1_454 no
O1 H3 2.7900 . 1_444 no
O2 H3 2.8700 . 1_444 no
O2 H30 2.4300 . . no
N1 C11 3.224(3) . 2_567 no
N1 C12 3.317(3) . 2_567 no
N1 C16 3.411(3) . 2_567 no
N2 H1C 2.5400 . . no
N2 H28 2.7000 . 1_656 no
C3 Cl1 3.397(2) . 1_556 no
C4 C12 3.425(3) . 2_567 no
C5 C18 3.357(3) . . no
C5 C12 3.372(3) . 2_567 no
C5 C11 3.550(3) . 2_567 no
C6 C24 3.217(2) . . no
C6 O1 3.400(3) . 2_466 no
C8 C18 3.364(3) . . no
C9 C18 3.396(3) . . no
C9 C17 3.550(2) . . no
C11 C5 3.550(3) . 2_567 no
C11 C27 3.580(3) . 2_566 no
C11 N1 3.224(3) . 2_567 no
C12 C5 3.372(3) . 2_567 no
C12 N1 3.317(3) . 2_567 no
C12 C4 3.425(3) . 2_567 no
C15 O1 3.355(2) . 1_656 no
C16 N1 3.411(3) . 2_567 no
C17 C9 3.550(2) . . no
C17 C24 3.341(2) . . no
C18 C9 3.396(3) . . no
C18 C5 3.357(3) . . no
C18 C8 3.364(3) . . no
C19 C29 3.380(3) . 2_566 no
C19 C30 3.456(3) . 2_566 no
C20 C30 3.591(3) . 2_566 no
C22 C24 3.329(2) . . no
C22 O1 3.406(3) . 2_466 no
C24 C22 3.329(2) . . no
C24 C6 3.217(2) . . no
C24 C26 3.532(3) . 2_566 no
C24 C17 3.341(2) . . no
C26 C24 3.532(3) . 2_566 no
C26 O2 3.405(3) . 2_466 no
C27 C11 3.580(3) . 2_566 no
C28 C30 3.600(3) . 2_466 no
C29 C19 3.380(3) . 2_566 no
C29 C30 3.484(3) . 2_466 no
C29 C29 3.555(3) . 2_466 no
C30 C19 3.456(3) . 2_566 no
C30 C28 3.600(3) . 2_466 no
C30 C20 3.591(3) . 2_566 no
C30 C29 3.484(3) . 2_466 no
C1 H23 3.0600 . 2_567 no
C5 H18 2.9800 . . no
C6 H24 2.9700 . . no
C7 H24 3.0300 . . no
C7 H18 2.8100 . . no
C8 H18 2.7500 . . no
C9 H23 2.9900 . 2_567 no
C9 H18 2.7100 . . no
C11 H27 2.9400 . 2_566 no
C12 H23 2.9900 . . no
C16 H27 3.0100 . 2_566 no
C17 H24 2.7200 . . no
C19 H13 3.0000 . 1_565 no
C20 H13 2.8800 . 1_565 no
C21 H13 2.8500 . 1_565 no
C22 H24 2.7300 . . no
C22 H13 2.9300 . 1_565 no
C23 H30 2.8100 . . no
C23 H12 2.5900 . . no
C23 H6 2.6200 . . no
C24 H6 2.7700 . . no
C24 H26 3.0100 . 2_566 no
C26 H24 2.9500 . 2_566 no
C27 H1C 2.8700 . 1_454 no
C28 H1C 2.9800 . 1_454 no
C29 H19 3.0500 . 2_566 no
C30 H23 2.7700 . . no
H1A H4 2.4300 . . no
H1A H4 2.4700 . 2_577 no
H1C N2 2.5400 . . no
H1C C27 2.8700 . 1_656 no
H1C C28 2.9800 . 1_656 no
H1C H27 2.3200 . 1_656 no
H1C H28 2.5500 . 1_656 no
H3 Cl1 3.0400 . 1_556 no
H3 O1 2.7900 . 1_666 no
H3 O2 2.8700 . 1_666 no
H4 H1A 2.4300 . . no
H4 H1A 2.4700 . 2_577 no
H6 C23 2.6200 . . no
H6 C24 2.7700 . . no
H6 H22 2.3400 . . no
H6 O1 2.5100 . 2_466 no
H12 C23 2.5900 . . no
H12 H23 2.5200 . . no
H13 C19 3.0000 . 1_545 no
H13 C20 2.8800 . 1_545 no
H13 C21 2.8500 . 1_545 no
H13 C22 2.9300 . 1_545 no
H15 O1 2.9000 . 1_656 no
H15 H28 2.5400 . 1_656 no
H18 C5 2.9800 . . no
H18 C7 2.8100 . . no
H18 C8 2.7500 . . no
H18 C9 2.7100 . . no
H19 C29 3.0500 . 2_566 no
H21 H21 2.5800 . 2_576 no
H22 H6 2.3400 . . no
H22 O1 2.5500 . 2_466 no
H23 C12 2.9900 . . no
H23 C30 2.7700 . . no
H23 H12 2.5200 . . no
H23 H30 2.2800 . . no
H23 C1 3.0600 . 2_567 no
H23 C9 2.9900 . 2_567 no
H24 C6 2.9700 . . no
H24 C7 3.0300 . . no
H24 C17 2.7200 . . no
H24 C22 2.7300 . . no
H24 H26 2.3700 . . no
H24 C26 2.9500 . 2_566 no
H26 H24 2.3700 . . no
H26 C24 3.0100 . 2_566 no
H27 H1C 2.3200 . 1_454 no
H27 C11 2.9400 . 2_566 no
H27 C16 3.0100 . 2_566 no
H28 O1 2.4200 . . no
H28 N2 2.7000 . 1_454 no
H28 H1C 2.5500 . 1_454 no
H28 H15 2.5400 . 1_454 no
H30 O2 2.4300 . . no
H30 C23 2.8100 . . no
H30 H23 2.2800 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C6 H6 O1 0.9800 2.5100 3.400(3) 150.00 2_466 yes
C22 H22 O1 0.9300 2.5500 3.406(3) 153.00 2_466 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
