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

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

data_lv4826a

_database_code_depnum_ccdc_archive 'CCDC 1058802'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_date             2012-11-06T08:56:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C26 H24 Cl4 N6 Zn'
_chemical_formula_moiety         'C26 H24 N6, Cl4 Zn'
_chemical_formula_weight         627.68

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9759(2)
_cell_length_b                   16.3834(6)
_cell_length_c                   32.0639(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5240.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7073
_cell_measurement_theta_min      3.4531
_cell_measurement_theta_max      30.0948

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.056
0 1 0 0.0774
3 1 1 0.106
-4 3 -1 0.215
-1 -7 -2 0.0769
0 0 1 0.0138
0 0 -1 0.0046

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
      CrysAlisPro, Oxford Diffraction Ltd.,
Analytical numeric absorption correction using a multifaceted crystal
               model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

;
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      -0.0172734
_diffrn_orient_matrix_ub_12      -0.0419244
_diffrn_orient_matrix_ub_13      -0.0012302
_diffrn_orient_matrix_ub_21      0.006924
_diffrn_orient_matrix_ub_22      0.001466
_diffrn_orient_matrix_ub_23      -0.0220184
_diffrn_orient_matrix_ub_31      0.0686171
_diffrn_orient_matrix_ub_32      -0.0106515
_diffrn_orient_matrix_ub_33      0.0018904
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_number            31098
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_full        29
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.954
_reflns_number_total             7278
_reflns_number_gt                5465
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_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)+(0.0275P)²+0.9683P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7278
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Zn1 Zn 0.85089(2) 0.368176(15) 0.886768(8) 0.01271(7) Uani 1 1 d . . .
Cl1 Cl 0.63050(5) 0.40014(3) 0.878110(17) 0.01819(12) Uani 1 1 d . . .
Cl2 Cl 0.94463(5) 0.33317(3) 0.824668(17) 0.01671(12) Uani 1 1 d . . .
Cl3 Cl 0.96031(5) 0.48851(3) 0.903773(18) 0.01816(12) Uani 1 1 d . . .
Cl4 Cl 0.88564(6) 0.26886(4) 0.933353(19) 0.02398(14) Uani 1 1 d . . .
C11 C 0.2222(2) 0.01314(13) 0.70369(7) 0.0189(5) Uani 1 1 d . . .
H11 H 0.1662 -0.0056 0.6817 0.023 Uiso 1 1 calc R . .
N12 N 0.32114(17) 0.06978(11) 0.70027(6) 0.0161(4) Uani 1 1 d . . .
C12 C 0.3487(2) 0.11321(14) 0.66078(7) 0.0222(5) Uani 1 1 d . . .
H12A H 0.3691 0.1706 0.6667 0.033 Uiso 1 1 calc R . .
H12B H 0.2698 0.11 0.6426 0.033 Uiso 1 1 calc R . .
H12C H 0.4255 0.0878 0.6468 0.033 Uiso 1 1 calc R . .
C13 C 0.3821(2) 0.08160(13) 0.73727(7) 0.0158(5) Uani 1 1 d . . .
N13A N 0.31962(16) 0.03156(11) 0.76501(6) 0.0143(4) Uani 1 1 d . . .
C14 C 0.3446(2) 0.01890(14) 0.80722(7) 0.0176(5) Uani 1 1 d . . .
H14 H 0.417 0.0458 0.8207 0.021 Uiso 1 1 calc R . .
C15 C 0.2644(2) -0.03215(14) 0.82873(8) 0.0207(5) Uani 1 1 d . . .
H15 H 0.2803 -0.0404 0.8576 0.025 Uiso 1 1 calc R . .
C16 C 0.1558(2) -0.07413(14) 0.80907(8) 0.0206(5) Uani 1 1 d . . .
H16 H 0.0988 -0.1084 0.8251 0.025 Uiso 1 1 calc R . .
C17 C 0.1341(2) -0.06520(14) 0.76774(7) 0.0190(5) Uani 1 1 d . . .
H17 H 0.0635 -0.0942 0.7545 0.023 Uiso 1 1 calc R . .
C17A C 0.2176(2) -0.01215(13) 0.74436(7) 0.0156(4) Uani 1 1 d . . .
C131 C 0.4856(2) 0.14188(13) 0.74759(7) 0.0149(4) Uani 1 1 d . . .
N132 N 0.47556(17) 0.17376(11) 0.78608(6) 0.0178(4) Uani 1 1 d . . .
C133 C 0.5633(2) 0.23197(14) 0.79685(8) 0.0203(5) Uani 1 1 d . . .
H133 H 0.5585 0.2542 0.8242 0.024 Uiso 1 1 calc R . .
C134 C 0.6609(2) 0.26132(14) 0.76990(8) 0.0217(5) Uani 1 1 d . . .
H134 H 0.7194 0.304 0.7783 0.026 Uiso 1 1 calc R . .
C135 C 0.6710(2) 0.22728(14) 0.73083(8) 0.0217(5) Uani 1 1 d . . .
H135 H 0.7374 0.246 0.7119 0.026 Uiso 1 1 calc R . .
C136 C 0.5838(2) 0.16565(14) 0.71934(7) 0.0182(5) Uani 1 1 d . . .
H136 H 0.5908 0.1402 0.6928 0.022 Uiso 1 1 calc R . .
C21 C 0.3342(2) 0.43939(13) 1.04036(7) 0.0151(4) Uani 1 1 d . . .
H21 H 0.2875 0.471 1.0605 0.018 Uiso 1 1 calc R . .
N22 N 0.27834(16) 0.39590(11) 1.00877(6) 0.0134(4) Uani 1 1 d . . .
C22 C 0.13211(19) 0.38857(14) 1.00330(7) 0.0173(5) Uani 1 1 d . . .
H22A H 0.1027 0.4252 0.9809 0.026 Uiso 1 1 calc R . .
H22B H 0.0869 0.4035 1.0293 0.026 Uiso 1 1 calc R . .
H22C H 0.1095 0.3321 0.996 0.026 Uiso 1 1 calc R . .
C23 C 0.37359(19) 0.35855(12) 0.98573(7) 0.0123(4) Uani 1 1 d . . .
N23A N 0.49318(17) 0.37874(10) 1.00355(6) 0.0120(4) Uani 1 1 d . . .
C24 C 0.62330(19) 0.35693(13) 0.99180(7) 0.0141(4) Uani 1 1 d . . .
H24 H 0.6387 0.3231 0.9682 0.017 Uiso 1 1 calc R . .
C25 C 0.7262(2) 0.38515(13) 1.01482(7) 0.0181(5) Uani 1 1 d . . .
H25 H 0.815 0.3705 1.0072 0.022 Uiso 1 1 calc R . .
C26 C 0.7059(2) 0.43629(13) 1.05024(7) 0.0182(5) Uani 1 1 d . . .
H26 H 0.7807 0.4546 1.066 0.022 Uiso 1 1 calc R . .
C27 C 0.5805(2) 0.45884(13) 1.06149(7) 0.0158(5) Uani 1 1 d . . .
H27 H 0.5665 0.4937 1.0848 0.019 Uiso 1 1 calc R . .
C27A C 0.4700(2) 0.42931(13) 1.03777(7) 0.0135(4) Uani 1 1 d . . .
C231 C 0.35473(19) 0.30847(13) 0.94854(7) 0.0133(4) Uani 1 1 d . . .
N232 N 0.44818(17) 0.25015(11) 0.94263(6) 0.0153(4) Uani 1 1 d . . .
C233 C 0.4359(2) 0.20417(14) 0.90864(7) 0.0186(5) Uani 1 1 d . . .
H233 H 0.5024 0.1638 0.9037 0.022 Uiso 1 1 calc R . .
C234 C 0.3328(2) 0.21121(14) 0.88005(7) 0.0203(5) Uani 1 1 d . . .
H234 H 0.3278 0.1759 0.8566 0.024 Uiso 1 1 calc R . .
C235 C 0.2372(2) 0.27104(15) 0.88646(7) 0.0209(5) Uani 1 1 d . . .
H235 H 0.1647 0.2775 0.8675 0.025 Uiso 1 1 calc R . .
C236 C 0.2490(2) 0.32137(14) 0.92100(7) 0.0176(5) Uani 1 1 d . . .
H236 H 0.1862 0.3639 0.9258 0.021 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl4 2.2359(6) . ?
Zn1 Cl2 2.2734(6) . ?
Zn1 Cl1 2.2771(5) . ?
Zn1 Cl3 2.3185(6) . ?
C11 N12 1.359(3) . ?
C11 C17A 1.369(3) . ?
C11 H11 0.95 . ?
N12 C13 1.347(3) . ?
N12 C12 1.478(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N13A 1.361(3) . ?
C13 C131 1.467(3) . ?
N13A C14 1.392(3) . ?
N13A C17A 1.410(3) . ?
C14 C15 1.347(3) . ?
C14 H14 0.95 . ?
C15 C16 1.429(3) . ?
C15 H15 0.95 . ?
C16 C17 1.351(3) . ?
C16 H16 0.95 . ?
C17 C17A 1.418(3) . ?
C17 H17 0.95 . ?
C131 N132 1.344(3) . ?
C131 C136 1.390(3) . ?
N132 C133 1.340(3) . ?
C133 C134 1.388(3) . ?
C133 H133 0.95 . ?
C134 C135 1.375(3) . ?
C134 H134 0.95 . ?
C135 C136 1.383(3) . ?
C135 H135 0.95 . ?
C136 H136 0.95 . ?
C21 N22 1.358(3) . ?
C21 C27A 1.367(3) . ?
C21 H21 0.95 . ?
N22 C23 1.350(3) . ?
N22 C22 1.474(2) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 N23A 1.364(3) . ?
C23 C231 1.460(3) . ?
N23A C27A 1.394(3) . ?
N23A C24 1.398(3) . ?
C24 C25 1.346(3) . ?
C24 H24 0.95 . ?
C25 C26 1.426(3) . ?
C25 H25 0.95 . ?
C26 C27 1.353(3) . ?
C26 H26 0.95 . ?
C27 C27A 1.424(3) . ?
C27 H27 0.95 . ?
C231 N232 1.348(3) . ?
C231 C236 1.391(3) . ?
N232 C233 1.331(3) . ?
C233 C234 1.382(3) . ?
C233 H233 0.95 . ?
C234 C235 1.383(3) . ?
C234 H234 0.95 . ?
C235 C236 1.386(3) . ?
C235 H235 0.95 . ?
C236 H236 0.95 . ?

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
Cl4 Zn1 Cl2 109.74(2) . . ?
Cl4 Zn1 Cl1 113.49(2) . . ?
Cl2 Zn1 Cl1 110.39(2) . . ?
Cl4 Zn1 Cl3 112.87(2) . . ?
Cl2 Zn1 Cl3 103.11(2) . . ?
Cl1 Zn1 Cl3 106.72(2) . . ?
N12 C11 C17A 107.94(19) . . ?
N12 C11 H11 126 . . ?
C17A C11 H11 126 . . ?
C13 N12 C11 110.80(19) . . ?
C13 N12 C12 126.94(19) . . ?
C11 N12 C12 122.20(19) . . ?
N12 C12 H12A 109.5 . . ?
N12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N12 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N12 C13 N13A 106.38(18) . . ?
N12 C13 C131 127.8(2) . . ?
N13A C13 C131 125.5(2) . . ?
C13 N13A C14 130.05(19) . . ?
C13 N13A C17A 109.25(18) . . ?
C14 N13A C17A 120.69(18) . . ?
C15 C14 N13A 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
N13A C14 H14 120.5 . . ?
C14 C15 C16 121.5(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C17A 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C17A C17 H17 120.3 . . ?
C11 C17A N13A 105.63(19) . . ?
C11 C17A C17 135.1(2) . . ?
N13A C17A C17 119.1(2) . . ?
N132 C131 C136 122.9(2) . . ?
N132 C131 C13 114.60(19) . . ?
C136 C131 C13 122.5(2) . . ?
C133 N132 C131 117.7(2) . . ?
N132 C133 C134 123.0(2) . . ?
N132 C133 H133 118.5 . . ?
C134 C133 H133 118.5 . . ?
C135 C134 C133 118.6(2) . . ?
C135 C134 H134 120.7 . . ?
C133 C134 H134 120.7 . . ?
C134 C135 C136 119.5(2) . . ?
C134 C135 H135 120.2 . . ?
C136 C135 H135 120.2 . . ?
C135 C136 C131 118.3(2) . . ?
C135 C136 H136 120.9 . . ?
C131 C136 H136 120.9 . . ?
N22 C21 C27A 107.34(19) . . ?
N22 C21 H21 126.3 . . ?
C27A C21 H21 126.3 . . ?
C23 N22 C21 110.93(17) . . ?
C23 N22 C22 126.45(19) . . ?
C21 N22 C22 122.52(17) . . ?
N22 C22 H22A 109.5 . . ?
N22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N22 C23 N23A 106.04(18) . . ?
N22 C23 C231 127.67(18) . . ?
N23A C23 C231 126.27(18) . . ?
C23 N23A C27A 109.19(17) . . ?
C23 N23A C24 129.60(18) . . ?
C27A N23A C24 121.21(17) . . ?
C25 C24 N23A 118.2(2) . . ?
C25 C24 H24 120.9 . . ?
N23A C24 H24 120.9 . . ?
C24 C25 C26 122.0(2) . . ?
C24 C25 H25 119 . . ?
C26 C25 H25 119 . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C27A 118.7(2) . . ?
C26 C27 H27 120.6 . . ?
C27A C27 H27 120.6 . . ?
C21 C27A N23A 106.49(18) . . ?
C21 C27A C27 133.9(2) . . ?
N23A C27A C27 119.57(18) . . ?
N232 C231 C236 122.8(2) . . ?
N232 C231 C23 115.09(18) . . ?
C236 C231 C23 122.05(19) . . ?
C233 N232 C231 116.91(19) . . ?
N232 C233 C234 124.4(2) . . ?
N232 C233 H233 117.8 . . ?
C234 C233 H233 117.8 . . ?
C233 C234 C235 118.3(2) . . ?
C233 C234 H234 120.9 . . ?
C235 C234 H234 120.9 . . ?
C234 C235 C236 118.8(2) . . ?
C234 C235 H235 120.6 . . ?
C236 C235 H235 120.6 . . ?
C235 C236 C231 118.8(2) . . ?
C235 C236 H236 120.6 . . ?
C231 C236 H236 120.6 . . ?
#===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_lv4826
_database_code_depnum_ccdc_archive 'CCDC 1058803'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_date             2015-03-31T14:44:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C13 H12 Cl3 N3 Zn'
_chemical_formula_moiety         'C13 H12 Cl3 N3 Zn'
_chemical_formula_weight         381.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.9572(9)
_cell_length_b                   7.6276(2)
_cell_length_c                   14.5488(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.203(4)
_cell_angle_gamma                90
_cell_volume                     3082.36(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22254
_cell_measurement_theta_min      3.8771
_cell_measurement_theta_max      41.0203

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       fragment
_exptl_crystal_colour            pale-brown
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1479
1 0 1 0.1524
-1 0 1 0.1297
-3 0 -1 0.1694
2 0 -1 0.288
0 1 0 0.1393
0 -1 -1 0.158
1 -1 1 0.1604
-3 0 1 0.2112
4 0 -1 0.3433
20 -7 7 0.1981


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,

;
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.633

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      0.0035764
_diffrn_orient_matrix_ub_12      0.0805143
_diffrn_orient_matrix_ub_13      0.0267185
_diffrn_orient_matrix_ub_21      -0.0174169
_diffrn_orient_matrix_ub_22      0.0405564
_diffrn_orient_matrix_ub_23      -0.044981
_diffrn_orient_matrix_ub_31      -0.0183442
_diffrn_orient_matrix_ub_32      -0.0227403
_diffrn_orient_matrix_ub_33      0.0145634
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_number            64497
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.924
_diffrn_reflns_theta_max         40.992
_diffrn_reflns_theta_full        40.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_number_total             10010
_reflns_number_gt                8806
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)

;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+1.2937P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10010
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.38441(2) 0.64386(2) 0.56763(2) 0.01215(2) Uani 1 d . .
Cl1 Cl 0.42472(2) 0.77390(3) 0.72140(2) 0.01999(4) Uani 1 d . .
Cl2 Cl 0.31034(2) 0.55900(2) 0.53630(2) 0.01610(3) Uani 1 d . .
Cl3 Cl 0.38496(2) 0.77964(3) 0.43132(2) 0.01878(3) Uani 1 d . .
C11 C 0.30221(3) 0.11068(10) 0.52267(6) 0.01568(11) Uani 1 d . .
H11 H 0.2796 0.0713 0.5458 0.019 Uiso 1 calc . .
N12 N 0.34869(2) 0.15882(8) 0.58262(5) 0.01436(9) Uani 1 d . .
C12 C 0.36968(3) 0.17885(12) 0.69394(6) 0.01998(13) Uani 1 d . .
H12A H 0.4028 0.1342 0.7247 0.03 Uiso 1 calc . .
H12B H 0.3505 0.1126 0.7206 0.03 Uiso 1 calc . .
H12C H 0.3698 0.3031 0.7111 0.03 Uiso 1 calc . .
C13 C 0.37034(2) 0.20731(9) 0.52457(5) 0.01315(10) Uani 1 d . .
N13A N 0.33761(2) 0.18986(8) 0.42574(5) 0.01264(9) Uani 1 d . .
C14 C 0.34281(3) 0.22284(10) 0.33738(6) 0.01719(12) Uani 1 d . .
H14 H 0.3728 0.2601 0.341 0.021 Uiso 1 calc . .
C15 C 0.30403(3) 0.20058(12) 0.24595(6) 0.02085(13) Uani 1 d . .
H15 H 0.307 0.223 0.1847 0.025 Uiso 1 calc . .
C16 C 0.25869(3) 0.14410(12) 0.23939(6) 0.02195(14) Uani 1 d . .
H16 H 0.2318 0.1322 0.1743 0.026 Uiso 1 calc . .
C17 C 0.25387(3) 0.10736(11) 0.32590(6) 0.01847(12) Uani 1 d . .
H17 H 0.224 0.0673 0.3218 0.022 Uiso 1 calc . .
C17A C 0.29420(2) 0.12982(9) 0.42235(6) 0.01375(10) Uani 1 d . .
C131 C 0.42097(2) 0.26218(9) 0.56058(6) 0.01467(11) Uani 1 d . .
N132 N 0.43158(2) 0.43260(8) 0.58407(5) 0.01347(9) Uani 1 d . .
C133 C 0.47748(3) 0.48396(10) 0.61573(6) 0.01711(12) Uani 1 d . .
H133 H 0.4854 0.6035 0.6337 0.021 Uiso 1 calc . .
C134 C 0.51386(3) 0.36987(11) 0.62334(7) 0.01959(13) Uani 1 d . .
H134 H 0.5458 0.4114 0.6442 0.024 Uiso 1 calc . .
C135 C 0.50287(3) 0.19502(13) 0.59999(10) 0.0300(2) Uani 1 d . .
H135 H 0.5271 0.114 0.6052 0.036 Uiso 1 calc . .
C136 C 0.45555(3) 0.13950(12) 0.56870(10) 0.0296(2) Uani 1 d . .
H136 H 0.4471 0.0197 0.5532 0.036 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Zn1 N132 2.1160(6) . ?
Zn1 Cl2 2.2275(8) . ?
Zn1 Cl3 2.2440(2) . ?
Zn1 Cl1 2.2540(2) . ?
C11 N12 1.3630(10) . ?
C11 C17A 1.3761(10) . ?
C11 H11 0.95 . ?
N12 C13 1.3414(9) . ?
N12 C12 1.4626(10) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N13A 1.3509(9) . ?
C13 C131 1.4769(9) . ?
N13A C14 1.3873(10) . ?
N13A C17A 1.4000(9) . ?
C14 C15 1.3525(12) . ?
C14 H14 0.95 . ?
C15 C16 1.4306(13) . ?
C15 H15 0.95 . ?
C16 C17 1.3605(12) . ?
C16 H16 0.95 . ?
C17 C17A 1.4177(10) . ?
C17 H17 0.95 . ?
C131 N132 1.3473(9) . ?
C131 C136 1.3872(11) . ?
N132 C133 1.3442(9) . ?
C133 C134 1.3885(11) . ?
C133 H133 0.95 . ?
C134 C135 1.3813(13) . ?
C134 H134 0.95 . ?
C135 C136 1.3941(13) . ?
C135 H135 0.95 . ?
C136 H136 0.95 . ?

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
N132 Zn1 Cl2 113.484(17) . . ?
N132 Zn1 Cl3 100.209(18) . . ?
Cl2 Zn1 Cl3 111.23(2) . . ?
N132 Zn1 Cl1 99.843(18) . . ?
Cl2 Zn1 Cl1 113.56(3) . . ?
Cl3 Zn1 Cl1 117.20(2) . . ?
N12 C11 C17A 107.15(6) . . ?
N12 C11 H11 126.4 . . ?
C17A C11 H11 126.4 . . ?
C13 N12 C11 110.56(6) . . ?
C13 N12 C12 124.56(6) . . ?
C11 N12 C12 124.34(7) . . ?
N12 C12 H12A 109.5 . . ?
N12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N12 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N12 C13 N13A 107.14(6) . . ?
N12 C13 C131 127.01(7) . . ?
N13A C13 C131 125.81(6) . . ?
C13 N13A C14 128.99(6) . . ?
C13 N13A C17A 109.07(6) . . ?
C14 N13A C17A 121.94(6) . . ?
C15 C14 N13A 118.22(7) . . ?
C15 C14 H14 120.9 . . ?
N13A C14 H14 120.9 . . ?
C14 C15 C16 121.48(7) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 120.36(8) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C17A 118.85(7) . . ?
C16 C17 H17 120.6 . . ?
C17A C17 H17 120.6 . . ?
C11 C17A N13A 106.07(6) . . ?
C11 C17A C17 134.79(7) . . ?
N13A C17A C17 119.11(7) . . ?
N132 C131 C136 122.45(7) . . ?
N132 C131 C13 117.72(6) . . ?
C136 C131 C13 119.83(7) . . ?
C133 N132 C131 118.07(6) . . ?
C133 N132 Zn1 112.90(5) . . ?
C131 N132 Zn1 128.85(5) . . ?
N132 C133 C134 122.83(7) . . ?
N132 C133 H133 118.6 . . ?
C134 C133 H133 118.6 . . ?
C135 C134 C133 118.85(7) . . ?
C135 C134 H134 120.6 . . ?
C133 C134 H134 120.6 . . ?
C134 C135 C136 118.87(8) . . ?
C134 C135 H135 120.6 . . ?
C136 C135 H135 120.6 . . ?
C131 C136 C135 118.89(8) . . ?
C131 C136 H136 120.6 . . ?
C135 C136 H136 120.6 . . ?

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_lv713
_database_code_depnum_ccdc_archive 'CCDC 1058804'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_date             2014-11-11T09:36:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C13 H15 Cl N3 O1.50'
_chemical_formula_moiety         'C13 H12 N3, Cl, 1.5(H2 O)'
_chemical_formula_weight         272.73

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3552(5)
_cell_length_b                   10.0184(6)
_cell_length_c                   18.5955(10)
_cell_angle_alpha                90.392(4)
_cell_angle_beta                 92.574(5)
_cell_angle_gamma                107.298(5)
_cell_volume                     1306.66(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3192
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      29.57

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             572
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0575
0 -1 1 0.0602
0 1 0 0.0574
0 -1 0 0.0649
0 0 1 0.036
0 0 -1 0.0667
-1 0 0 0.2256
1 0 0 0.2363
1 -1 -2 0.2203


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.

;
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      -0.0548427
_diffrn_orient_matrix_ub_12      -0.05788
_diffrn_orient_matrix_ub_13      -0.021578
_diffrn_orient_matrix_ub_21      -0.0211668
_diffrn_orient_matrix_ub_22      -0.0408644
_diffrn_orient_matrix_ub_23      0.0312505
_diffrn_orient_matrix_ub_31      -0.0822683
_diffrn_orient_matrix_ub_32      0.0219489
_diffrn_orient_matrix_ub_33      0.0040329
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_number            11805
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         30.324
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_reflns_number_total             6970
_reflns_number_gt                5342
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Water molecule hydrogen atoms were refined with geometries restrained to ideal 
values.


;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.4851P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6970
_refine_ls_number_parameters     360
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.5276(3) -0.08524(19) 0.20311(10) 0.0212(4) Uani 1 d . .
H11 H 0.4454 -0.1706 0.1832 0.025 Uiso 1 calc . .
N12 N 0.5638(2) -0.05107(15) 0.27460(8) 0.0183(3) Uani 1 d . .
C12 C 0.4694(3) -0.14265(18) 0.33191(10) 0.0232(4) Uani 1 d . .
H12A H 0.5523 -0.1965 0.3504 0.035 Uiso 1 calc . .
H12B H 0.3487 -0.2069 0.3125 0.035 Uiso 1 calc . .
H12C H 0.4441 -0.0856 0.3711 0.035 Uiso 1 calc . .
C13 C 0.6875(2) 0.07812(17) 0.28376(10) 0.0173(3) Uani 1 d . .
N13A N 0.7300(2) 0.12803(15) 0.21698(8) 0.0169(3) Uani 1 d . .
C14 C 0.8563(3) 0.25518(18) 0.19730(10) 0.0205(4) Uani 1 d . .
H14 H 0.9237 0.3227 0.2327 0.025 Uiso 1 calc . .
C15 C 0.8795(3) 0.2793(2) 0.12680(10) 0.0244(4) Uani 1 d . .
H15 H 0.9664 0.3646 0.1126 0.029 Uiso 1 calc . .
C16 C 0.7771(3) 0.1800(2) 0.07243(11) 0.0270(4) Uani 1 d . .
H16 H 0.7936 0.2012 0.023 0.032 Uiso 1 calc . .
C17 C 0.6569(3) 0.0560(2) 0.09144(10) 0.0249(4) Uani 1 d . .
H17 H 0.5897 -0.0106 0.0556 0.03 Uiso 1 calc . .
C17A C 0.6322(3) 0.02662(18) 0.16536(10) 0.0205(4) Uani 1 d . .
C131 C 0.7583(2) 0.15503(18) 0.35157(9) 0.0171(3) Uani 1 d . .
N132 N 0.7621(2) 0.29039(15) 0.35085(8) 0.0182(3) Uani 1 d . .
C133 C 0.8170(3) 0.36447(19) 0.41223(10) 0.0208(4) Uani 1 d . .
H133 H 0.8214 0.4602 0.4128 0.025 Uiso 1 calc . .
C134 C 0.8679(3) 0.30796(19) 0.47534(10) 0.0223(4) Uani 1 d . .
H134 H 0.901 0.363 0.5184 0.027 Uiso 1 calc . .
C135 C 0.8696(3) 0.17054(19) 0.47430(10) 0.0230(4) Uani 1 d . .
H135 H 0.9075 0.1305 0.5164 0.028 Uiso 1 calc . .
C136 C 0.8153(3) 0.09146(18) 0.41098(10) 0.0197(4) Uani 1 d . .
H136 H 0.8171 -0.0029 0.4084 0.024 Uiso 1 calc . .
C21 C 0.3884(3) 0.29291(19) 0.13800(10) 0.0205(4) Uani 1 d . .
H21 H 0.4393 0.3403 0.0959 0.025 Uiso 1 calc . .
N22 N 0.4218(2) 0.34553(15) 0.20680(8) 0.0193(3) Uani 1 d . .
C22 C 0.5519(3) 0.48566(19) 0.22556(11) 0.0251(4) Uani 1 d . .
H22A H 0.4783 0.5523 0.2292 0.038 Uiso 1 calc . .
H22B H 0.6444 0.5153 0.1881 0.038 Uiso 1 calc . .
H22C H 0.6196 0.4826 0.2718 0.038 Uiso 1 calc . .
C23 C 0.3276(3) 0.24979(18) 0.25317(10) 0.0184(4) Uani 1 d . .
N23A N 0.2331(2) 0.13358(15) 0.21347(8) 0.0177(3) Uani 1 d . .
C24 C 0.1110(3) 0.00662(18) 0.23554(10) 0.0202(4) Uani 1 d . .
H24 H 0.0883 -0.0101 0.285 0.024 Uiso 1 calc . .
C25 C 0.0266(3) -0.09121(19) 0.18488(10) 0.0221(4) Uani 1 d . .
H25 H -0.0574 -0.1777 0.1992 0.027 Uiso 1 calc . .
C26 C 0.0595(3) -0.06894(19) 0.11019(10) 0.0231(4) Uani 1 d . .
H26 H -0.0023 -0.1402 0.0757 0.028 Uiso 1 calc . .
C27 C 0.1785(3) 0.0534(2) 0.08838(10) 0.0228(4) Uani 1 d . .
H27 H 0.2016 0.0681 0.0388 0.027 Uiso 1 calc . .
C27A C 0.2684(3) 0.15940(19) 0.14061(10) 0.0191(4) Uani 1 d . .
C231 C 0.3283(3) 0.26524(18) 0.33192(10) 0.0187(4) Uani 1 d . .
N232 N 0.3404(2) 0.15346(16) 0.36889(8) 0.0209(3) Uani 1 d . .
C233 C 0.3488(3) 0.1660(2) 0.44048(10) 0.0242(4) Uani 1 d . .
H233 H 0.3572 0.0881 0.4678 0.029 Uiso 1 calc . .
C234 C 0.3460(3) 0.2861(2) 0.47760(11) 0.0276(4) Uani 1 d . .
H234 H 0.3561 0.2911 0.5287 0.033 Uiso 1 calc . .
C235 C 0.3280(3) 0.3977(2) 0.43816(11) 0.0280(4) Uani 1 d . .
H235 H 0.3226 0.4806 0.4619 0.034 Uiso 1 calc . .
C236 C 0.3177(3) 0.3884(2) 0.36379(10) 0.0237(4) Uani 1 d . .
H236 H 0.3039 0.4636 0.3354 0.028 Uiso 1 calc . .
Cl1 Cl -0.11749(7) 0.74087(5) 0.35279(2) 0.02384(11) Uani 1 d . .
Cl2 Cl 0.20361(7) 0.62554(5) 0.10481(3) 0.02777(12) Uani 1 d . .
O1 O 0.7753(3) 0.53791(19) 0.04302(10) 0.0407(4) Uani 1 d . .
O2 O 0.6044(2) 0.74506(16) 0.03535(9) 0.0359(4) Uani 1 d . .
O3 O 0.1037(2) 0.56439(15) 0.26838(8) 0.0294(3) Uani 1 d . .
H1AO H 0.898(3) 0.575(3) 0.0544(15) 0.070(10) Uiso 1 d . .
H1BO H 0.778(4) 0.501(3) 0.0018(11) 0.085(12) Uiso 1 d . .
H2AO H 0.654(4) 0.676(3) 0.0381(16) 0.077(10) Uiso 1 d . .
H2BO H 0.501(3) 0.710(3) 0.0565(14) 0.060(9) Uiso 1 d . .
H3AO H 0.036(3) 0.606(2) 0.2879(11) 0.040(7) Uiso 1 d . .
H3BO H 0.116(4) 0.590(3) 0.2262(10) 0.068(10) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C11 N12 1.365(2) . ?
C11 C17A 1.373(3) . ?
C11 H11 0.95 . ?
N12 C13 1.347(2) . ?
N12 C12 1.470(2) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N13A 1.357(2) . ?
C13 C131 1.464(2) . ?
N13A C14 1.397(2) . ?
N13A C17A 1.400(2) . ?
C14 C15 1.344(3) . ?
C14 H14 0.95 . ?
C15 C16 1.432(3) . ?
C15 H15 0.95 . ?
C16 C17 1.353(3) . ?
C16 H16 0.95 . ?
C17 C17A 1.416(3) . ?
C17 H17 0.95 . ?
C131 N132 1.348(2) . ?
C131 C136 1.389(2) . ?
N132 C133 1.336(2) . ?
C133 C134 1.391(3) . ?
C133 H133 0.95 . ?
C134 C135 1.381(3) . ?
C134 H134 0.95 . ?
C135 C136 1.389(3) . ?
C135 H135 0.95 . ?
C136 H136 0.95 . ?
C21 N22 1.364(2) . ?
C21 C27A 1.369(3) . ?
C21 H21 0.95 . ?
N22 C23 1.347(2) . ?
N22 C22 1.474(2) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 N23A 1.358(2) . ?
C23 C231 1.471(2) . ?
N23A C24 1.398(2) . ?
N23A C27A 1.402(2) . ?
C24 C25 1.344(3) . ?
C24 H24 0.95 . ?
C25 C26 1.428(3) . ?
C25 H25 0.95 . ?
C26 C27 1.354(3) . ?
C26 H26 0.95 . ?
C27 C27A 1.421(3) . ?
C27 H27 0.95 . ?
C231 N232 1.341(2) . ?
C231 C236 1.390(2) . ?
N232 C233 1.333(2) . ?
C233 C234 1.389(3) . ?
C233 H233 0.95 . ?
C234 C235 1.377(3) . ?
C234 H234 0.95 . ?
C235 C236 1.383(3) . ?
C235 H235 0.95 . ?
C236 H236 0.95 . ?
O1 H1AO 0.880(17) . ?
O1 H1BO 0.854(16) . ?
O2 H2AO 0.874(16) . ?
O2 H2BO 0.851(16) . ?
O3 H3AO 0.831(15) . ?
O3 H3BO 0.828(16) . ?

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
N12 C11 C17A 107.32(16) . . ?
N12 C11 H11 126.3 . . ?
C17A C11 H11 126.3 . . ?
C13 N12 C11 110.63(15) . . ?
C13 N12 C12 126.17(15) . . ?
C11 N12 C12 123.11(15) . . ?
N12 C12 H12A 109.5 . . ?
N12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N12 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N12 C13 N13A 106.64(15) . . ?
N12 C13 C131 127.82(16) . . ?
N13A C13 C131 125.49(16) . . ?
C13 N13A C14 129.05(16) . . ?
C13 N13A C17A 109.31(15) . . ?
C14 N13A C17A 121.56(15) . . ?
C15 C14 N13A 118.08(18) . . ?
C15 C14 H14 121 . . ?
N13A C14 H14 121 . . ?
C14 C15 C16 121.91(19) . . ?
C14 C15 H15 119 . . ?
C16 C15 H15 119 . . ?
C17 C16 C15 120.04(18) . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C16 C17 C17A 119.30(18) . . ?
C16 C17 H17 120.4 . . ?
C17A C17 H17 120.4 . . ?
C11 C17A N13A 106.09(16) . . ?
C11 C17A C17 134.85(18) . . ?
N13A C17A C17 119.06(17) . . ?
N132 C131 C136 123.81(16) . . ?
N132 C131 C13 114.33(15) . . ?
C136 C131 C13 121.86(15) . . ?
C133 N132 C131 117.14(16) . . ?
N132 C133 C134 123.07(16) . . ?
N132 C133 H133 118.5 . . ?
C134 C133 H133 118.5 . . ?
C135 C134 C133 118.89(17) . . ?
C135 C134 H134 120.6 . . ?
C133 C134 H134 120.6 . . ?
C134 C135 C136 119.24(18) . . ?
C134 C135 H135 120.4 . . ?
C136 C135 H135 120.4 . . ?
C131 C136 C135 117.73(16) . . ?
C131 C136 H136 121.1 . . ?
C135 C136 H136 121.1 . . ?
N22 C21 C27A 107.51(16) . . ?
N22 C21 H21 126.2 . . ?
C27A C21 H21 126.2 . . ?
C23 N22 C21 110.45(15) . . ?
C23 N22 C22 126.43(16) . . ?
C21 N22 C22 123.05(16) . . ?
N22 C22 H22A 109.5 . . ?
N22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N22 C23 N23A 106.83(15) . . ?
N22 C23 C231 127.22(16) . . ?
N23A C23 C231 125.94(16) . . ?
C23 N23A C24 129.53(15) . . ?
C23 N23A C27A 108.95(15) . . ?
C24 N23A C27A 121.47(15) . . ?
C25 C24 N23A 118.24(17) . . ?
C25 C24 H24 120.9 . . ?
N23A C24 H24 120.9 . . ?
C24 C25 C26 121.92(18) . . ?
C24 C25 H25 119 . . ?
C26 C25 H25 119 . . ?
C27 C26 C25 120.23(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C27A 119.18(17) . . ?
C26 C27 H27 120.4 . . ?
C27A C27 H27 120.4 . . ?
C21 C27A N23A 106.24(16) . . ?
C21 C27A C27 134.78(18) . . ?
N23A C27A C27 118.96(16) . . ?
N232 C231 C236 123.95(17) . . ?
N232 C231 C23 115.07(15) . . ?
C236 C231 C23 120.97(16) . . ?
C233 N232 C231 116.55(16) . . ?
N232 C233 C234 124.01(18) . . ?
N232 C233 H233 118 . . ?
C234 C233 H233 118 . . ?
C235 C234 C233 118.06(18) . . ?
C235 C234 H234 121 . . ?
C233 C234 H234 121 . . ?
C234 C235 C236 119.65(18) . . ?
C234 C235 H235 120.2 . . ?
C236 C235 H235 120.2 . . ?
C235 C236 C231 117.71(18) . . ?
C235 C236 H236 121.1 . . ?
C231 C236 H236 121.1 . . ?
H1AO O1 H1BO 102(2) . . ?
H2AO O2 H2BO 100(2) . . ?
H3AO O3 H3BO 108(2) . . ?

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
O1 H1AO Cl2 0.880(17) 2.308(18) 3.1672(19) 165(3) 1_655
O1 H1BO Cl2 0.854(16) 2.375(17) 3.2234(17) 173(3) 2_665
O2 H2AO O1 0.874(16) 1.856(16) 2.729(2) 176(3) .
O2 H2BO Cl2 0.851(16) 2.324(16) 3.1711(17) 174(3) .
O3 H3AO Cl1 0.831(15) 2.359(15) 3.1841(15) 172(2) .
O3 H3BO Cl2 0.828(16) 2.375(16) 3.1820(16) 165(2) .


