# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1025945'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================ 
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 Cl2 N2 O Zn'
_chemical_formula_weight         432.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.050(5)
_cell_length_b                   17.306(5)
_cell_length_c                   14.363(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.430(16)
_cell_angle_gamma                90.00
_cell_volume                     2060.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    19793
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_T_max  0.6870
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19793
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4705
_reflns_number_gt                3748
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0539P)²+1.0309P] 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         4705
_refine_ls_number_parameters     226
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.11248(3) 0.176793(16) 0.37716(2) 0.04115(11) Uani 1 1 d . . .
Cl1 Cl 0.31176(12) 0.19491(5) 0.35999(8) 0.0745(2) Uani 1 1 d . . .
Cl2 Cl -0.12529(10) 0.14951(5) 0.22315(6) 0.0726(3) Uani 1 1 d . . .
O1 O 0.2408(3) 0.01190(12) 0.4752(2) 0.0705(6) Uani 1 1 d . . .
N1 N 0.1555(2) 0.11629(12) 0.51583(16) 0.0422(5) Uani 1 1 d . . .
N2 N 0.0680(2) 0.26300(11) 0.46060(15) 0.0359(4) Uani 1 1 d . . .
C1 C 0.1181(3) 0.15591(15) 0.5786(2) 0.0467(6) Uani 1 1 d . . .
C2 C 0.1221(5) 0.12287(19) 0.6668(2) 0.0666(9) Uani 1 1 d . . .
H2A H 0.0962 0.1519 0.7106 0.080 Uiso 1 1 calc R . .
C3 C 0.1652(5) 0.04531(19) 0.6900(3) 0.0721(10) Uani 1 1 d . . .
H3A H 0.1649 0.0202 0.7487 0.086 Uiso 1 1 calc R . .
C4 C 0.2075(4) 0.00555(17) 0.6298(2) 0.0616(8) Uani 1 1 d . . .
H4A H 0.2398 -0.0470 0.6469 0.074 Uiso 1 1 calc R . .
C5 C 0.2031(3) 0.04294(15) 0.5417(2) 0.0498(6) Uani 1 1 d . . .
C6 C 0.0742(3) 0.23751(15) 0.5458(2) 0.0451(6) Uani 1 1 d . . .
H6A H 0.0510 0.2704 0.5878 0.054 Uiso 1 1 calc R . .
C7 C 0.3159(6) -0.0633(2) 0.5033(4) 0.0969(14) Uani 1 1 d . . .
H7A H 0.3362 -0.0786 0.4466 0.145 Uiso 1 1 calc R . .
H7B H 0.2443 -0.1011 0.5045 0.145 Uiso 1 1 calc R . .
H7C H 0.4184 -0.0613 0.5778 0.145 Uiso 1 1 calc R . .
C8 C 0.0270(3) 0.34262(13) 0.42592(18) 0.0344(5) Uani 1 1 d . . .
C9 C 0.1531(3) 0.39435(13) 0.45933(19) 0.0371(5) Uani 1 1 d . . .
C10 C 0.1125(3) 0.47016(14) 0.4224(2) 0.0452(6) Uani 1 1 d . . .
H10A H 0.1958 0.5069 0.4452 0.054 Uiso 1 1 calc R . .
C11 C -0.0459(4) 0.49322(15) 0.3533(2) 0.0523(6) Uani 1 1 d . . .
H11A H -0.0712 0.5453 0.3281 0.063 Uiso 1 1 calc R . .
C12 C -0.1677(3) 0.44069(16) 0.3207(2) 0.0500(6) Uani 1 1 d . . .
H12A H -0.2767 0.4573 0.2731 0.060 Uiso 1 1 calc R . .
C13 C -0.1357(3) 0.36404(14) 0.3554(2) 0.0399(5) Uani 1 1 d . . .
C14 C 0.3280(3) 0.36896(15) 0.5358(2) 0.0469(5) Uani 1 1 d U . .
H14A H 0.3285 0.3112 0.5363 0.056 Uiso 1 1 calc R . .
C15 C 0.4035(4) 0.3952(2) 0.6560(3) 0.0750(8) Uani 1 1 d U . .
H15A H 0.3370 0.3778 0.6820 0.113 Uiso 1 1 calc R . .
H15B H 0.4108 0.4517 0.6596 0.113 Uiso 1 1 calc R . .
H15C H 0.5119 0.3730 0.7045 0.113 Uiso 1 1 calc R . .
C16 C 0.4276(4) 0.3945(2) 0.4926(3) 0.0829(11) Uani 1 1 d . . .
H16A H 0.5390 0.3766 0.5443 0.124 Uiso 1 1 calc R . .
H16B H 0.4263 0.4510 0.4879 0.124 Uiso 1 1 calc R . .
H16C H 0.3823 0.3724 0.4175 0.124 Uiso 1 1 calc R . .
C17 C -0.2728(3) 0.30822(17) 0.3207(3) 0.0544(7) Uani 1 1 d . . .
H17A H -0.2278 0.2546 0.3367 0.065 Uiso 1 1 calc R . .
C18 C -0.4065(5) 0.3132(2) 0.1960(4) 0.0963(14) Uani 1 1 d . . .
H18A H -0.3620 0.3030 0.1516 0.144 Uiso 1 1 calc R . .
H18B H -0.4540 0.3650 0.1784 0.144 Uiso 1 1 calc R . .
H18C H -0.4898 0.2748 0.1773 0.144 Uiso 1 1 calc R . .
C19 C -0.3385(6) 0.3224(3) 0.3926(5) 0.1098(18) Uani 1 1 d . . .
H19A H -0.2505 0.3180 0.4727 0.165 Uiso 1 1 calc R . .
H19B H -0.4217 0.2840 0.3738 0.165 Uiso 1 1 calc R . .
H19C H -0.3853 0.3743 0.3774 0.165 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.068(2) . ?
Zn1 N2 2.1137(19) . ?
Zn1 Cl1 2.1746(12) . ?
Zn1 Cl2 2.2021(11) . ?
O1 C5 1.324(4) . ?
O1 C7 1.443(4) . ?
N1 C5 1.333(3) . ?
N1 C1 1.344(3) . ?
N2 C6 1.269(3) . ?
N2 C8 1.444(3) . ?
C1 C2 1.369(4) . ?
C1 C6 1.475(4) . ?
C2 C3 1.392(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.348(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.397(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.518(3) . ?
C10 C11 1.376(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12A 0.9500 . ?
C13 C17 1.518(4) . ?
C14 C15 1.511(4) . ?
C14 C16 1.512(4) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.517(5) . ?
C17 C19 1.526(5) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 78.89(8) . . ?
N1 Zn1 Cl1 118.55(7) . . ?
N2 Zn1 Cl1 117.79(6) . . ?
N1 Zn1 Cl2 112.09(7) . . ?
N2 Zn1 Cl2 105.28(6) . . ?
Cl1 Zn1 Cl2 117.57(5) . . ?
C5 O1 C7 118.9(3) . . ?
C5 N1 C1 119.4(2) . . ?
C5 N1 Zn1 126.66(19) . . ?
C1 N1 Zn1 113.71(16) . . ?
C6 N2 C8 120.9(2) . . ?
C6 N2 Zn1 112.99(17) . . ?
C8 N2 Zn1 126.06(14) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C6 114.9(2) . . ?
C2 C1 C6 122.8(3) . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
O1 C5 N1 112.9(2) . . ?
O1 C5 C4 126.1(3) . . ?
N1 C5 C4 121.0(3) . . ?
N2 C6 C1 118.9(2) . . ?
N2 C6 H6A 120.5 . . ?
C1 C6 H6A 120.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 122.7(2) . . ?
C9 C8 N2 117.8(2) . . ?
C13 C8 N2 119.4(2) . . ?
C10 C9 C8 117.5(2) . . ?
C10 C9 C14 121.3(2) . . ?
C8 C9 C14 121.2(2) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C12 C13 C8 116.8(2) . . ?
C12 C13 C17 120.5(2) . . ?
C8 C13 C17 122.7(2) . . ?
C15 C14 C16 111.1(3) . . ?
C15 C14 C9 111.6(2) . . ?
C16 C14 C9 112.5(2) . . ?
C15 C14 H14A 107.1 . . ?
C16 C14 H14A 107.1 . . ?
C9 C14 H14A 107.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 112.6(3) . . ?
C18 C17 C19 110.9(4) . . ?
C13 C17 C19 109.6(3) . . ?
C18 C17 H17A 107.9 . . ?
C13 C17 H17A 107.9 . . ?
C19 C17 H17A 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Zn1 N1 C5 -178.3(2) . . . . ?
Cl1 Zn1 N1 C5 -62.5(2) . . . . ?
Cl2 Zn1 N1 C5 79.6(2) . . . . ?
N2 Zn1 N1 C1 7.01(18) . . . . ?
Cl1 Zn1 N1 C1 122.73(17) . . . . ?
Cl2 Zn1 N1 C1 -95.13(18) . . . . ?
N1 Zn1 N2 C6 -5.41(17) . . . . ?
Cl1 Zn1 N2 C6 -121.97(17) . . . . ?
Cl2 Zn1 N2 C6 104.68(17) . . . . ?
N1 Zn1 N2 C8 177.29(18) . . . . ?
Cl1 Zn1 N2 C8 60.74(18) . . . . ?
Cl2 Zn1 N2 C8 -72.61(17) . . . . ?
C5 N1 C1 C2 -2.1(4) . . . . ?
Zn1 N1 C1 C2 173.0(2) . . . . ?
C5 N1 C1 C6 177.3(2) . . . . ?
Zn1 N1 C1 C6 -7.5(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C6 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 C4 2.5(5) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C7 O1 C5 N1 171.3(3) . . . . ?
C7 O1 C5 C4 -9.7(5) . . . . ?
C1 N1 C5 O1 -178.0(2) . . . . ?
Zn1 N1 C5 O1 7.6(3) . . . . ?
C1 N1 C5 C4 3.0(4) . . . . ?
Zn1 N1 C5 C4 -171.5(2) . . . . ?
C3 C4 C5 O1 180.0(3) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C8 N2 C6 C1 -179.5(2) . . . . ?
Zn1 N2 C6 C1 3.1(3) . . . . ?
N1 C1 C6 N2 3.0(4) . . . . ?
C2 C1 C6 N2 -177.6(3) . . . . ?
C6 N2 C8 C9 98.5(3) . . . . ?
Zn1 N2 C8 C9 -84.4(2) . . . . ?
C6 N2 C8 C13 -85.2(3) . . . . ?
Zn1 N2 C8 C13 91.9(2) . . . . ?
C13 C8 C9 C10 1.6(3) . . . . ?
N2 C8 C9 C10 177.8(2) . . . . ?
C13 C8 C9 C14 -180.0(2) . . . . ?
N2 C8 C9 C14 -3.8(3) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C14 C9 C10 C11 -179.9(2) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C11 C12 C13 C17 178.2(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
N2 C8 C13 C12 -177.1(2) . . . . ?
C9 C8 C13 C17 -178.9(2) . . . . ?
N2 C8 C13 C17 5.0(3) . . . . ?
C10 C9 C14 C15 76.2(3) . . . . ?
C8 C9 C14 C15 -102.1(3) . . . . ?
C10 C9 C14 C16 -49.4(4) . . . . ?
C8 C9 C14 C16 132.2(3) . . . . ?
C12 C13 C17 C18 46.8(4) . . . . ?
C8 C13 C17 C18 -135.4(3) . . . . ?
C12 C13 C17 C19 -77.1(4) . . . . ?
C8 C13 C17 C19 100.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1025946'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H48 Cd2 Cl4 N4 O2'
_chemical_formula_weight         959.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P21/c  '

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

_cell_length_a                   10.206(2)
_cell_length_b                   20.164(4)
_cell_length_c                   21.555(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.96(3)
_cell_angle_gamma                90.00
_cell_volume                     4419.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    41065
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5775
_exptl_absorpt_correction_T_max  0.8274
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            41065
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             9952
_reflns_number_gt                7197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0469P)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         9952
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.60067(2) 0.040770(13) 0.067173(12) 0.04057(8) Uani 1 1 d . . .
Cd2 Cd 0.89469(2) 0.063634(13) 0.455789(12) 0.04039(8) Uani 1 1 d . . .
Cl1 Cl 0.35913(9) 0.03926(6) 0.01977(5) 0.0601(3) Uani 1 1 d . . .
Cl2 Cl 0.57088(14) 0.01476(7) 0.17427(5) 0.0798(4) Uani 1 1 d . . .
Cl3 Cl 0.91403(12) 0.18281(6) 0.46756(6) 0.0781(3) Uani 1 1 d . . .
Cl4 Cl 0.86428(9) -0.02674(6) 0.53539(5) 0.0657(3) Uani 1 1 d . . .
O1 O 0.8876(3) -0.02578(14) 0.09577(15) 0.0645(8) Uani 1 1 d . . .
O2 O 0.6237(2) 0.08737(16) 0.51576(12) 0.0620(8) Uani 1 1 d . . .
N1 N 0.8203(3) 0.07576(15) 0.07037(14) 0.0428(7) Uani 1 1 d . . .
N2 N 0.6100(3) 0.15761(14) 0.04772(14) 0.0426(7) Uani 1 1 d . . .
N3 N 0.6720(3) 0.06122(15) 0.42077(13) 0.0407(7) Uani 1 1 d . . .
N4 N 0.8684(3) 0.03436(14) 0.34782(13) 0.0398(7) Uani 1 1 d . . .
C1 C 0.8412(3) 0.13931(18) 0.05550(16) 0.0428(8) Uani 1 1 d . . .
C2 C 0.9662(3) 0.1647(2) 0.05112(19) 0.0527(10) Uani 1 1 d . . .
H2A H 0.9792 0.2090 0.0415 0.063 Uiso 1 1 calc R . .
C3 C 1.0706(4) 0.1215(2) 0.0616(2) 0.0610(11) Uani 1 1 d . . .
H3A H 1.1557 0.1366 0.0579 0.073 Uiso 1 1 calc R . .
C4 C 1.0512(4) 0.0572(2) 0.07730(19) 0.0534(10) Uani 1 1 d . . .
H4A H 1.1219 0.0284 0.0853 0.064 Uiso 1 1 calc R . .
C5 C 0.9221(3) 0.03550(19) 0.08109(17) 0.0458(8) Uani 1 1 d . . .
C6 C 0.7243(3) 0.18187(18) 0.04510(17) 0.0462(8) Uani 1 1 d . . .
H6A H 0.7341 0.2267 0.0366 0.055 Uiso 1 1 calc R . .
C7 C 0.9850(5) -0.0758(2) 0.1045(2) 0.0761(14) Uani 1 1 d . . .
H7A H 0.9446 -0.1168 0.1152 0.114 Uiso 1 1 calc R . .
H7B H 1.0493 -0.0630 0.1375 0.114 Uiso 1 1 calc R . .
H7C H 1.0271 -0.0816 0.0667 0.114 Uiso 1 1 calc R . .
C8 C 0.4956(3) 0.20014(18) 0.0395(2) 0.0505(10) Uani 1 1 d . . .
C9 C 0.4385(4) 0.2132(2) -0.0202(2) 0.0711(13) Uani 1 1 d . . .
C10 C 0.3245(5) 0.2517(3) -0.0246(3) 0.0911(18) Uani 1 1 d . . .
H10A H 0.2850 0.2620 -0.0639 0.109 Uiso 1 1 calc R . .
C11 C 0.2697(4) 0.2742(3) 0.0253(4) 0.098(2) Uani 1 1 d . . .
H11A H 0.1938 0.2998 0.0202 0.118 Uiso 1 1 calc R . .
C12 C 0.3247(4) 0.2598(2) 0.0839(3) 0.0822(17) Uani 1 1 d . . .
H12A H 0.2853 0.2754 0.1184 0.099 Uiso 1 1 calc R . .
C15 C 0.5819(7) 0.2388(4) -0.1055(3) 0.128(3) Uani 1 1 d . . .
H15A H 0.6482 0.2535 -0.0743 0.192 Uiso 1 1 calc R . .
H15B H 0.5294 0.2760 -0.1204 0.192 Uiso 1 1 calc R . .
H15C H 0.6231 0.2193 -0.1395 0.192 Uiso 1 1 calc R . .
C14 C 0.4946(6) 0.1876(3) -0.0776(3) 0.0927(17) Uani 1 1 d . . .
H14A H 0.5506 0.1497 -0.0649 0.111 Uiso 1 1 calc R . .
C13 C 0.4406(3) 0.2216(2) 0.0927(2) 0.0595(11) Uani 1 1 d . . .
C16 C 0.3910(8) 0.1629(4) -0.1271(3) 0.147(3) Uani 1 1 d . . .
H16A H 0.3372 0.1301 -0.1094 0.221 Uiso 1 1 calc R . .
H16B H 0.4334 0.1436 -0.1609 0.221 Uiso 1 1 calc R . .
H16C H 0.3370 0.1993 -0.1424 0.221 Uiso 1 1 calc R . .
C17 C 0.5012(5) 0.2064(2) 0.1574(2) 0.0744(14) Uani 1 1 d . . .
H17A H 0.5666 0.1714 0.1536 0.089 Uiso 1 1 calc R . .
C18 C 0.4009(7) 0.1801(3) 0.1996(3) 0.136(3) Uani 1 1 d . . .
H18A H 0.3575 0.1420 0.1806 0.204 Uiso 1 1 calc R . .
H18B H 0.3371 0.2139 0.2058 0.204 Uiso 1 1 calc R . .
H18C H 0.4449 0.1677 0.2391 0.204 Uiso 1 1 calc R . .
C19 C 0.5733(6) 0.2661(4) 0.1859(3) 0.116(2) Uani 1 1 d . . .
H19A H 0.6352 0.2818 0.1582 0.174 Uiso 1 1 calc R . .
H19B H 0.6191 0.2538 0.2250 0.174 Uiso 1 1 calc R . .
H19C H 0.5112 0.3006 0.1926 0.174 Uiso 1 1 calc R . .
C20 C 0.6405(3) 0.04838(19) 0.36071(18) 0.0447(9) Uani 1 1 d . . .
C21 C 0.5112(3) 0.0477(2) 0.3344(2) 0.0597(11) Uani 1 1 d . . .
H21A H 0.4907 0.0377 0.2925 0.072 Uiso 1 1 calc R . .
C22 C 0.4144(4) 0.0626(2) 0.3734(2) 0.0641(12) Uani 1 1 d . . .
H22A H 0.3267 0.0627 0.3576 0.077 Uiso 1 1 calc R . .
C23 C 0.4451(3) 0.0769(2) 0.4343(2) 0.0548(10) Uani 1 1 d . . .
H23A H 0.3798 0.0873 0.4602 0.066 Uiso 1 1 calc R . .
C24 C 0.5778(3) 0.07575(17) 0.45736(17) 0.0430(8) Uani 1 1 d . . .
C25 C 0.7512(3) 0.03470(19) 0.32310(17) 0.0485(9) Uani 1 1 d . . .
H25A H 0.7349 0.0262 0.2807 0.058 Uiso 1 1 calc R . .
C26 C 0.5350(4) 0.1047(2) 0.5605(2) 0.0702(13) Uani 1 1 d . . .
H26A H 0.5831 0.1113 0.6002 0.105 Uiso 1 1 calc R . .
H26B H 0.4724 0.0696 0.5636 0.105 Uiso 1 1 calc R . .
H26C H 0.4896 0.1448 0.5478 0.105 Uiso 1 1 calc R . .
C27 C 0.9754(3) 0.0236(2) 0.30927(15) 0.0435(9) Uani 1 1 d . . .
C28 C 1.0256(4) -0.0396(2) 0.30398(18) 0.0559(10) Uani 1 1 d . . .
C29 C 1.1338(4) -0.0474(3) 0.2694(2) 0.0744(14) Uani 1 1 d . . .
H29A H 1.1697 -0.0894 0.2652 0.089 Uiso 1 1 calc R . .
C30 C 1.1887(4) 0.0061(3) 0.2414(2) 0.0763(15) Uani 1 1 d . . .
H30A H 1.2604 0.0001 0.2182 0.092 Uiso 1 1 calc R . .
C31 C 1.1378(4) 0.0674(3) 0.2480(2) 0.0726(14) Uani 1 1 d . . .
H31A H 1.1751 0.1029 0.2285 0.087 Uiso 1 1 calc R . .
C32 C 1.0312(4) 0.0792(2) 0.28315(17) 0.0530(10) Uani 1 1 d . . .
C33 C 0.9611(6) -0.0994(2) 0.3317(2) 0.0845(17) Uani 1 1 d . . .
H33A H 0.9120 -0.0829 0.3657 0.101 Uiso 1 1 calc R . .
C34 C 0.8617(7) -0.1307(3) 0.2840(3) 0.124(3) Uani 1 1 d . . .
H34A H 0.8015 -0.0974 0.2672 0.186 Uiso 1 1 calc R . .
H34B H 0.8140 -0.1647 0.3037 0.186 Uiso 1 1 calc R . .
H34C H 0.9068 -0.1498 0.2511 0.186 Uiso 1 1 calc R . .
C35 C 1.0587(8) -0.1507(3) 0.3598(3) 0.140(3) Uani 1 1 d . . .
H35A H 1.1189 -0.1299 0.3905 0.211 Uiso 1 1 calc R . .
H35B H 1.1068 -0.1692 0.3275 0.211 Uiso 1 1 calc R . .
H35C H 1.0120 -0.1854 0.3790 0.211 Uiso 1 1 calc R . .
C36 C 0.9787(5) 0.1479(3) 0.2908(2) 0.0745(14) Uani 1 1 d . . .
H36A H 0.9161 0.1457 0.3227 0.089 Uiso 1 1 calc R . .
C37 C 1.0875(6) 0.1965(3) 0.3142(3) 0.117(2) Uani 1 1 d . . .
H37A H 1.1327 0.1796 0.3518 0.175 Uiso 1 1 calc R . .
H37B H 1.0492 0.2387 0.3223 0.175 Uiso 1 1 calc R . .
H37C H 1.1486 0.2014 0.2831 0.175 Uiso 1 1 calc R . .
C38 C 0.9022(8) 0.1721(4) 0.2302(3) 0.147(3) Uani 1 1 d . . .
H38A H 0.8355 0.1404 0.2170 0.221 Uiso 1 1 calc R . .
H38B H 0.9617 0.1771 0.1983 0.221 Uiso 1 1 calc R . .
H38C H 0.8618 0.2141 0.2375 0.221 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.345(3) . ?
Cd1 N2 2.396(3) . ?
Cd1 Cl2 2.4119(11) . ?
Cd1 Cl1 2.5333(10) 3_655 ?
Cd1 Cl1 2.5858(12) . ?
Cd1 Cd1 3.7792(11) 3_655 ?
Cd2 N3 2.333(3) . ?
Cd2 N4 2.393(3) . ?
Cd2 Cl3 2.4226(13) . ?
Cd2 Cl4 2.5403(11) . ?
Cd2 Cl4 2.5613(10) 3_756 ?
Cd2 Cd2 3.7591(9) 3_756 ?
Cl1 Cd1 2.5333(10) 3_655 ?
Cl4 Cd2 2.5613(10) 3_756 ?
O1 C5 1.330(4) . ?
O1 C7 1.418(5) . ?
O2 C24 1.326(4) . ?
O2 C26 1.421(4) . ?
N1 C5 1.323(4) . ?
N1 C1 1.342(5) . ?
N2 C6 1.270(4) . ?
N2 C8 1.447(4) . ?
N3 C24 1.328(4) . ?
N3 C20 1.332(5) . ?
N4 C25 1.267(4) . ?
N4 C27 1.444(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.471(5) . ?
C2 C3 1.380(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.359(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(5) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.388(6) . ?
C8 C9 1.393(6) . ?
C9 C10 1.394(7) . ?
C9 C14 1.499(7) . ?
C10 C11 1.335(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.369(8) . ?
C11 H11A 0.9300 . ?
C12 C13 1.410(6) . ?
C12 H12A 0.9300 . ?
C15 C14 1.522(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 C16 1.520(8) . ?
C14 H14A 0.9800 . ?
C13 C17 1.507(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.513(8) . ?
C17 C18 1.523(6) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.391(5) . ?
C20 C25 1.473(5) . ?
C21 C22 1.385(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.354(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.401(5) . ?
C23 H23A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.382(5) . ?
C27 C32 1.398(5) . ?
C28 C29 1.394(5) . ?
C28 C33 1.520(6) . ?
C29 C30 1.378(7) . ?
C29 H29A 0.9300 . ?
C30 C31 1.352(7) . ?
C30 H30A 0.9300 . ?
C31 C32 1.399(5) . ?
C31 H31A 0.9300 . ?
C32 C36 1.499(7) . ?
C33 C35 1.525(8) . ?
C33 C34 1.518(8) . ?
C33 H33A 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.533(7) . ?
C36 C38 1.543(8) . ?
C36 H36A 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N2 69.93(10) . . ?
N1 Cd1 Cl2 103.68(9) . . ?
N2 Cd1 Cl2 113.05(8) . . ?
N1 Cd1 Cl1 89.88(8) . 3_655 ?
N2 Cd1 Cl1 119.03(8) . 3_655 ?
Cl2 Cd1 Cl1 127.69(5) . 3_655 ?
N1 Cd1 Cl1 153.03(8) . . ?
N2 Cd1 Cl1 89.63(7) . . ?
Cl2 Cd1 Cl1 100.42(5) . . ?
Cl1 Cd1 Cl1 84.84(4) 3_655 . ?
N1 Cd1 Cd1 127.47(8) . 3_655 ?
N2 Cd1 Cd1 108.72(7) . 3_655 ?
Cl2 Cd1 Cd1 122.25(4) . 3_655 ?
Cl1 Cd1 Cd1 42.96(2) 3_655 3_655 ?
Cl1 Cd1 Cd1 41.88(3) . 3_655 ?
N3 Cd2 N4 69.89(10) . . ?
N3 Cd2 Cl3 97.06(8) . . ?
N4 Cd2 Cl3 110.34(8) . . ?
N3 Cd2 Cl4 91.78(8) . . ?
N4 Cd2 Cl4 118.03(8) . . ?
Cl3 Cd2 Cl4 130.88(5) . . ?
N3 Cd2 Cl4 157.02(8) . 3_756 ?
N4 Cd2 Cl4 91.52(8) . 3_756 ?
Cl3 Cd2 Cl4 102.20(4) . 3_756 ?
Cl4 Cd2 Cl4 85.07(4) . 3_756 ?
N3 Cd2 Cd2 130.41(7) . 3_756 ?
N4 Cd2 Cd2 109.61(7) . 3_756 ?
Cl3 Cd2 Cd2 125.89(4) . 3_756 ?
Cl4 Cd2 Cd2 42.75(2) . 3_756 ?
Cl4 Cd2 Cd2 42.32(3) 3_756 3_756 ?
Cd1 Cl1 Cd1 95.16(4) 3_655 . ?
Cd2 Cl4 Cd2 94.93(4) . 3_756 ?
C5 O1 C7 119.7(3) . . ?
C24 O2 C26 119.6(3) . . ?
C5 N1 C1 119.3(3) . . ?
C5 N1 Cd1 123.7(2) . . ?
C1 N1 Cd1 116.8(2) . . ?
C6 N2 C8 120.0(3) . . ?
C6 N2 Cd1 115.9(2) . . ?
C8 N2 Cd1 124.1(2) . . ?
C24 N3 C20 119.6(3) . . ?
C24 N3 Cd2 122.6(2) . . ?
C20 N3 Cd2 117.7(2) . . ?
C25 N4 C27 119.5(3) . . ?
C25 N4 Cd2 115.5(2) . . ?
C27 N4 Cd2 124.7(2) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C6 116.7(3) . . ?
C2 C1 C6 120.9(3) . . ?
C3 C2 C1 117.3(4) . . ?
C3 C2 H2A 121.4 . . ?
C1 C2 H2A 121.4 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N1 C5 O1 113.1(3) . . ?
N1 C5 C4 121.9(4) . . ?
O1 C5 C4 125.1(3) . . ?
N2 C6 C1 120.3(3) . . ?
N2 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 122.5(4) . . ?
C13 C8 N2 117.7(4) . . ?
C9 C8 N2 119.6(4) . . ?
C10 C9 C8 116.6(5) . . ?
C10 C9 C14 120.8(5) . . ?
C8 C9 C14 122.6(4) . . ?
C11 C10 C9 122.7(6) . . ?
C11 C10 H10A 118.7 . . ?
C9 C10 H10A 118.7 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 120.8(5) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C14 C15 111.8(5) . . ?
C9 C14 C16 113.6(6) . . ?
C15 C14 C16 109.9(5) . . ?
C9 C14 H14A 107.1 . . ?
C15 C14 H14A 107.1 . . ?
C16 C14 H14A 107.1 . . ?
C8 C13 C12 117.0(5) . . ?
C8 C13 C17 122.5(3) . . ?
C12 C13 C17 120.5(4) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C19 111.1(4) . . ?
C13 C17 C18 112.4(5) . . ?
C19 C17 C18 111.3(5) . . ?
C13 C17 H17A 107.3 . . ?
C19 C17 H17A 107.3 . . ?
C18 C17 H17A 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C21 122.6(3) . . ?
N3 C20 C25 116.1(3) . . ?
C21 C20 C25 121.3(4) . . ?
C22 C21 C20 116.8(4) . . ?
C22 C21 H21A 121.6 . . ?
C20 C21 H21A 121.6 . . ?
C23 C22 C21 121.2(4) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C22 C23 C24 118.4(3) . . ?
C22 C23 H23A 120.8 . . ?
C24 C23 H23A 120.8 . . ?
N3 C24 O2 112.9(3) . . ?
N3 C24 C23 121.3(3) . . ?
O2 C24 C23 125.8(3) . . ?
N4 C25 C20 120.7(3) . . ?
N4 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 122.7(3) . . ?
C28 C27 N4 119.3(3) . . ?
C32 C27 N4 117.7(3) . . ?
C27 C28 C29 117.7(4) . . ?
C27 C28 C33 121.5(3) . . ?
C29 C28 C33 120.8(4) . . ?
C30 C29 C28 121.1(5) . . ?
C30 C29 H29A 119.4 . . ?
C28 C29 H29A 119.4 . . ?
C31 C30 C29 119.7(4) . . ?
C31 C30 H30A 120.2 . . ?
C29 C30 H30A 120.2 . . ?
C30 C31 C32 122.4(4) . . ?
C30 C31 H31A 118.8 . . ?
C32 C31 H31A 118.8 . . ?
C27 C32 C31 116.4(4) . . ?
C27 C32 C36 122.3(3) . . ?
C31 C32 C36 121.3(4) . . ?
C35 C33 C34 111.2(6) . . ?
C35 C33 C28 113.8(5) . . ?
C34 C33 C28 110.5(4) . . ?
C35 C33 H33A 107.0 . . ?
C34 C33 H33A 107.0 . . ?
C28 C33 H33A 107.0 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 C37 111.8(5) . . ?
C32 C36 C38 111.0(5) . . ?
C37 C36 C38 112.0(5) . . ?
C32 C36 H36A 107.2 . . ?
C37 C36 H36A 107.2 . . ?
C38 C36 H36A 107.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1025947'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 Cl2 Hg N2 O'
_chemical_formula_weight         567.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3270(19)
_cell_length_b                   16.828(3)
_cell_length_c                   13.927(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.73(3)
_cell_angle_gamma                90.00
_cell_volume                     2178.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4997
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    7.319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.060
_exptl_absorpt_correction_T_max  0.072
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4997
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4997
_reflns_number_gt                3974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.0004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4973
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.827
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.74050(2) 0.170183(10) 0.327521(14) 0.04992(12) Uani 1 1 d . . .
Cl1 Cl 0.7239(2) 0.22398(10) 0.17148(10) 0.0838(5) Uani 1 1 d . . .
Cl2 Cl 0.5750(2) 0.11936(11) 0.42955(16) 0.0938(6) Uani 1 1 d . . .
O1 O 0.8975(4) 0.0010(2) 0.3046(3) 0.0603(10) Uani 1 1 d . . .
N1 N 0.9649(4) 0.1125(2) 0.3803(3) 0.0410(8) Uani 1 1 d . . .
N2 N 0.8989(4) 0.2680(2) 0.4167(3) 0.0415(8) Uani 1 1 d . . .
C1 C 1.0576(6) 0.1574(3) 0.4353(4) 0.0463(11) Uani 1 1 d . . .
C2 C 1.1892(6) 0.1280(3) 0.4748(4) 0.0589(14) Uani 1 1 d . . .
H2A H 1.2529 0.1600 0.5123 0.071 Uiso 1 1 calc R . .
C3 C 1.2217(6) 0.0498(3) 0.4564(4) 0.0603(14) Uani 1 1 d . . .
H3A H 1.3083 0.0283 0.4822 0.072 Uiso 1 1 calc R . .
C4 C 1.1279(6) 0.0039(3) 0.4008(4) 0.0530(12) Uani 1 1 d . . .
H4A H 1.1489 -0.0490 0.3887 0.064 Uiso 1 1 calc R . .
C5 C 0.9987(5) 0.0381(3) 0.3621(3) 0.0445(10) Uani 1 1 d . . .
C6 C 1.0172(5) 0.2410(3) 0.4498(3) 0.0462(10) Uani 1 1 d . . .
H6A H 1.0817 0.2744 0.4846 0.055 Uiso 1 1 calc R . .
C7 C 0.9246(7) -0.0777(3) 0.2717(6) 0.0774(19) Uani 1 1 d . . .
H7A H 0.8427 -0.0962 0.2316 0.116 Uiso 1 1 calc R . .
H7B H 0.9415 -0.1125 0.3262 0.116 Uiso 1 1 calc R . .
H7C H 1.0077 -0.0773 0.2354 0.116 Uiso 1 1 calc R . .
C8 C 0.8715(5) 0.3526(3) 0.4223(3) 0.0422(10) Uani 1 1 d . . .
C9 C 0.7739(6) 0.3790(3) 0.4855(4) 0.0536(11) Uani 1 1 d . . .
C10 C 0.7474(7) 0.4613(3) 0.4861(5) 0.0694(16) Uani 1 1 d . . .
H10A H 0.6831 0.4816 0.5275 0.083 Uiso 1 1 calc R . .
C11 C 0.8134(8) 0.5118(3) 0.4278(5) 0.0702(17) Uani 1 1 d . . .
H11A H 0.7958 0.5661 0.4311 0.084 Uiso 1 1 calc R . .
C12 C 0.9049(7) 0.4837(3) 0.3647(4) 0.0628(14) Uani 1 1 d . . .
H12A H 0.9472 0.5191 0.3242 0.075 Uiso 1 1 calc R . .
C13 C 0.9370(6) 0.4022(3) 0.3592(3) 0.0482(11) Uani 1 1 d . . .
C14 C 0.7008(9) 0.3234(3) 0.5507(6) 0.077(2) Uani 1 1 d . . .
H14A H 0.7228 0.2691 0.5313 0.093 Uiso 1 1 calc R . .
C15 C 0.5446(15) 0.3315(6) 0.5435(19) 0.219(12) Uani 1 1 d . . .
H15A H 0.5074 0.3236 0.4778 0.329 Uiso 1 1 calc R . .
H15B H 0.5192 0.3837 0.5641 0.329 Uiso 1 1 calc R . .
H15C H 0.5043 0.2924 0.5837 0.329 Uiso 1 1 calc R . .
C16 C 0.766(2) 0.3345(8) 0.6568(9) 0.196(11) Uani 1 1 d . . .
H16A H 0.7203 0.2987 0.6983 0.294 Uiso 1 1 calc R . .
H16B H 0.7517 0.3882 0.6769 0.294 Uiso 1 1 calc R . .
H16C H 0.8677 0.3233 0.6605 0.294 Uiso 1 1 calc R . .
C17 C 1.0306(7) 0.3714(3) 0.2842(4) 0.0600(13) Uani 1 1 d . . .
H17A H 1.0125 0.3141 0.2783 0.072 Uiso 1 1 calc R . .
C18 C 1.1900(8) 0.3815(6) 0.3153(6) 0.099(2) Uani 1 1 d . . .
H18A H 1.2110 0.3583 0.3778 0.148 Uiso 1 1 calc R . .
H18B H 1.2133 0.4371 0.3180 0.148 Uiso 1 1 calc R . .
H18C H 1.2461 0.3556 0.2697 0.148 Uiso 1 1 calc R . .
C19 C 0.9917(10) 0.4076(6) 0.1856(5) 0.105(3) Uani 1 1 d . . .
H19A H 0.8911 0.3995 0.1677 0.158 Uiso 1 1 calc R . .
H19B H 1.0473 0.3826 0.1390 0.158 Uiso 1 1 calc R . .
H19C H 1.0120 0.4635 0.1877 0.158 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 Cl2 2.3440(17) . ?
Hg1 Cl1 2.3475(15) . ?
Hg1 N1 2.368(4) . ?
Hg1 N2 2.477(4) . ?
O1 C5 1.341(6) . ?
O1 C7 1.431(6) . ?
N1 C5 1.320(6) . ?
N1 C1 1.341(6) . ?
N2 C6 1.246(6) . ?
N2 C8 1.449(5) . ?
C1 C2 1.394(7) . ?
C1 C6 1.474(6) . ?
C2 C3 1.378(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.361(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.402(7) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.390(7) . ?
C8 C9 1.391(7) . ?
C9 C10 1.407(7) . ?
C9 C14 1.505(8) . ?
C10 C11 1.358(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.360(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.407(7) . ?
C12 H12A 0.9300 . ?
C13 C17 1.508(8) . ?
C14 C15 1.459(16) . ?
C14 C16 1.563(17) . ?
C14 H14A 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.519(8) . ?
C17 C18 1.524(10) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
Cl2 Hg1 Cl1 134.86(8) . . ?
Cl2 Hg1 N1 105.75(11) . . ?
Cl1 Hg1 N1 115.76(11) . . ?
Cl2 Hg1 N2 109.52(10) . . ?
Cl1 Hg1 N2 101.47(10) . . ?
N1 Hg1 N2 69.00(12) . . ?
C5 O1 C7 119.2(4) . . ?
C5 N1 C1 119.4(4) . . ?
C5 N1 Hg1 123.2(3) . . ?
C1 N1 Hg1 117.3(3) . . ?
C6 N2 C8 119.6(4) . . ?
C6 N2 Hg1 114.6(3) . . ?
C8 N2 Hg1 125.4(3) . . ?
N1 C1 C2 122.0(5) . . ?
N1 C1 C6 117.2(4) . . ?
C2 C1 C6 120.8(5) . . ?
C3 C2 C1 117.8(5) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
N1 C5 O1 112.8(4) . . ?
N1 C5 C4 121.8(4) . . ?
O1 C5 C4 125.3(4) . . ?
N2 C6 C1 121.7(4) . . ?
N2 C6 H6A 119.1 . . ?
C1 C6 H6A 119.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 123.5(5) . . ?
C13 C8 N2 117.9(4) . . ?
C9 C8 N2 118.4(4) . . ?
C8 C9 C10 116.3(5) . . ?
C8 C9 C14 122.4(5) . . ?
C10 C9 C14 121.3(5) . . ?
C11 C10 C9 121.6(6) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C8 C13 C12 116.4(5) . . ?
C8 C13 C17 122.7(4) . . ?
C12 C13 C17 120.7(5) . . ?
C15 C14 C9 113.6(9) . . ?
C15 C14 C16 111.4(13) . . ?
C9 C14 C16 109.6(7) . . ?
C15 C14 H14A 107.3 . . ?
C9 C14 H14A 107.3 . . ?
C16 C14 H14A 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C19 112.3(6) . . ?
C13 C17 C18 111.8(5) . . ?
C19 C17 C18 111.5(6) . . ?
C13 C17 H17A 106.9 . . ?
C19 C17 H17A 106.9 . . ?
C18 C17 H17A 106.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.145
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1025948'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 N2 O Zn'
_chemical_formula_weight         362.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   8.0251(8)
_cell_length_b                   9.2087(9)
_cell_length_c                   10.4640(10)
_cell_angle_alpha                95.054(8)
_cell_angle_beta                 93.455(8)
_cell_angle_gamma                92.379(8)
_cell_volume                     768.04(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5537
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      29.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_T_max  0.6893
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5537
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.1348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.35
_reflns_number_total             3495
_reflns_number_gt                1841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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         3495
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.2146
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.72663(11) 0.63332(8) 0.17876(8) 0.0431(3) Uani 1 1 d . . .
Cl1 Cl 0.4995(3) 0.7502(2) 0.2190(2) 0.0587(6) Uani 1 1 d . . .
Cl2 Cl 0.9602(3) 0.7508(2) 0.2650(2) 0.0594(6) Uani 1 1 d . . .
O1 O 0.6811(8) 0.4200(5) 0.3928(5) 0.0575(15) Uani 1 1 d . . .
N1 N 0.7380(8) 0.4131(6) 0.1890(6) 0.0459(15) Uani 1 1 d . . .
N2 N 0.7577(8) 0.5668(6) -0.0164(6) 0.0412(14) Uani 1 1 d . . .
C1 C 0.7814(10) 0.3419(7) 0.0755(7) 0.0446(18) Uani 1 1 d . . .
C2 C 0.8136(11) 0.1957(8) 0.0650(9) 0.059(2) Uani 1 1 d . . .
H2A H 0.8436 0.1494 -0.0123 0.071 Uiso 1 1 calc R . .
C3 C 0.8001(12) 0.1191(8) 0.1731(9) 0.063(2) Uani 1 1 d . . .
H3A H 0.8230 0.0207 0.1693 0.076 Uiso 1 1 calc R . .
C4 C 0.7529(12) 0.1891(8) 0.2847(9) 0.061(2) Uani 1 1 d . . .
H4A H 0.7399 0.1381 0.3566 0.073 Uiso 1 1 calc R . .
C5 C 0.7248(10) 0.3358(8) 0.2899(8) 0.051(2) Uani 1 1 d . . .
C6 C 0.7870(9) 0.4311(7) -0.0305(7) 0.0413(17) Uani 1 1 d . . .
H6A H 0.8124 0.3893 -0.1108 0.050 Uiso 1 1 calc R . .
C7 C 0.6482(13) 0.3498(10) 0.5079(8) 0.069(3) Uani 1 1 d . . .
H7A H 0.6185 0.4216 0.5738 0.103 Uiso 1 1 calc R . .
H7B H 0.7466 0.3033 0.5372 0.103 Uiso 1 1 calc R . .
H7C H 0.5579 0.2780 0.4891 0.103 Uiso 1 1 calc R . .
C8 C 0.7591(10) 0.6566(7) -0.1210(7) 0.0426(18) Uani 1 1 d . . .
C9 C 0.8214(11) 0.6144(8) -0.2383(7) 0.050(2) Uani 1 1 d . . .
H9A H 0.8678 0.5238 -0.2517 0.061 Uiso 1 1 calc R . .
C10 C 0.8146(11) 0.7066(8) -0.3355(8) 0.053(2) Uani 1 1 d . . .
H10A H 0.8551 0.6759 -0.4144 0.063 Uiso 1 1 calc R . .
C11 C 0.7493(10) 0.8436(8) -0.3192(7) 0.0461(19) Uani 1 1 d . . .
C12 C 0.6887(11) 0.8840(8) -0.2013(8) 0.057(2) Uani 1 1 d . . .
H12A H 0.6435 0.9750 -0.1876 0.069 Uiso 1 1 calc R . .
C13 C 0.6931(11) 0.7934(7) -0.1033(8) 0.051(2) Uani 1 1 d . . .
H13A H 0.6515 0.8240 -0.0248 0.061 Uiso 1 1 calc R . .
C14 C 0.7475(13) 0.9451(9) -0.4243(9) 0.067(3) Uani 1 1 d . . .
H14A H 0.7941 0.8985 -0.4988 0.100 Uiso 1 1 calc R . .
H14B H 0.8126 1.0329 -0.3952 0.100 Uiso 1 1 calc R . .
H14C H 0.6345 0.9688 -0.4460 0.100 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.046(5) . ?
Zn1 N2 2.112(6) . ?
Zn1 Cl1 2.199(2) . ?
Zn1 Cl2 2.226(2) . ?
O1 C5 1.343(9) . ?
O1 C7 1.449(9) . ?
N1 C5 1.332(9) . ?
N1 C1 1.376(9) . ?
N2 C6 1.279(9) . ?
N2 C8 1.429(9) . ?
C1 C2 1.377(10) . ?
C1 C6 1.439(10) . ?
C2 C3 1.392(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(10) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.383(10) . ?
C8 C13 1.388(10) . ?
C9 C10 1.382(11) . ?
C9 H9A 0.9300 . ?
C10 C11 1.387(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(11) . ?
C11 C14 1.505(11) . ?
C12 C13 1.378(11) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 80.4(2) . . ?
N1 Zn1 Cl1 122.06(19) . . ?
N2 Zn1 Cl1 116.14(18) . . ?
N1 Zn1 Cl2 111.08(19) . . ?
N2 Zn1 Cl2 109.13(17) . . ?
Cl1 Zn1 Cl2 113.47(8) . . ?
C5 O1 C7 117.8(6) . . ?
C5 N1 C1 118.0(6) . . ?
C5 N1 Zn1 129.4(5) . . ?
C1 N1 Zn1 112.2(5) . . ?
C6 N2 C8 122.1(6) . . ?
C6 N2 Zn1 110.4(5) . . ?
C8 N2 Zn1 127.4(4) . . ?
C2 C1 N1 121.9(7) . . ?
C2 C1 C6 123.2(7) . . ?
N1 C1 C6 114.9(6) . . ?
C1 C2 C3 118.3(8) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 119.4(8) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N1 C5 O1 111.0(6) . . ?
N1 C5 C4 122.7(8) . . ?
O1 C5 C4 126.4(7) . . ?
N2 C6 C1 121.2(7) . . ?
N2 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.6(7) . . ?
C9 C8 N2 123.7(6) . . ?
C13 C8 N2 117.7(6) . . ?
C8 C9 C10 120.0(7) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C9 122.0(7) . . ?
C11 C10 H10A 119.0 . . ?
C9 C10 H10A 119.0 . . ?
C10 C11 C12 117.0(7) . . ?
C10 C11 C14 121.6(7) . . ?
C12 C11 C14 121.3(7) . . ?
C13 C12 C11 121.9(7) . . ?
C13 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C12 C13 C8 120.4(7) . . ?
C12 C13 H13A 119.8 . . ?
C8 C13 H13A 119.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.829
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1025949'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cd Cl2 N2 O'
_chemical_formula_weight         409.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   8.0765(5)
_cell_length_b                   9.3574(5)
_cell_length_c                   10.5442(5)
_cell_angle_alpha                94.409(4)
_cell_angle_beta                 93.636(4)
_cell_angle_gamma                92.850(4)
_cell_volume                     791.73(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3661
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      29.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    1.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_T_max  0.7291
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7044
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         29.25
_reflns_number_total             3661
_reflns_number_gt                3117
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)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     SHELXL
_refine_ls_extinction_coef       0.0320(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.71949(3) 0.13849(2) 0.68671(2) 0.04276(12) Uani 1 1 d . . .
Cl1 Cl 0.48491(11) 0.27368(9) 0.72553(9) 0.0587(2) Uani 1 1 d . . .
Cl2 Cl 0.97595(11) 0.26105(9) 0.77280(10) 0.0610(3) Uani 1 1 d . . .
O1 O 0.6801(3) -0.0955(3) 0.8859(2) 0.0634(7) Uani 1 1 d . . .
N1 N 0.7368(3) -0.1006(2) 0.6828(2) 0.0421(6) Uani 1 1 d . . .
N2 N 0.7558(3) 0.0563(2) 0.4767(2) 0.0401(6) Uani 1 1 d . . .
C1 C 0.7811(4) -0.1647(3) 0.5721(3) 0.0456(7) Uani 1 1 d . . .
C3 C 0.8033(5) -0.3855(4) 0.6665(4) 0.0694(11) Uani 1 1 d . . .
H3A H 0.8272 -0.4819 0.6609 0.083 Uiso 1 1 calc R . .
C4 C 0.7566(5) -0.3215(4) 0.7799(4) 0.0631(10) Uani 1 1 d . . .
H4A H 0.7467 -0.3733 0.8511 0.076 Uiso 1 1 calc R . .
C5 C 0.7248(4) -0.1754(3) 0.7840(3) 0.0496(8) Uani 1 1 d . . .
C6 C 0.7868(4) -0.0763(3) 0.4644(3) 0.0438(7) Uani 1 1 d . . .
H6A H 0.8136 -0.1170 0.3855 0.053 Uiso 1 1 calc R . .
C7 C 0.6490(6) -0.1634(4) 1.0004(4) 0.0737(11) Uani 1 1 d . . .
H7A H 0.6142 -0.0936 1.0633 0.111 Uiso 1 1 calc R . .
H7B H 0.7489 -0.2037 1.0323 0.111 Uiso 1 1 calc R . .
H7C H 0.5633 -0.2382 0.9820 0.111 Uiso 1 1 calc R . .
C8 C 0.7580(4) 0.1438(3) 0.3719(3) 0.0385(6) Uani 1 1 d . . .
C9 C 0.8209(4) 0.1033(3) 0.2552(3) 0.0490(8) Uani 1 1 d . . .
H9A H 0.8656 0.0141 0.2420 0.059 Uiso 1 1 calc R . .
C10 C 0.8169(4) 0.1950(3) 0.1596(3) 0.0515(8) Uani 1 1 d . . .
H10A H 0.8575 0.1656 0.0818 0.062 Uiso 1 1 calc R . .
C11 C 0.7542(4) 0.3303(3) 0.1755(3) 0.0459(7) Uani 1 1 d . . .
C12 C 0.6924(5) 0.3681(3) 0.2907(3) 0.0541(9) Uani 1 1 d . . .
H12A H 0.6479 0.4575 0.3036 0.065 Uiso 1 1 calc R . .
C13 C 0.6941(4) 0.2778(3) 0.3878(3) 0.0485(8) Uani 1 1 d . . .
H13A H 0.6519 0.3074 0.4649 0.058 Uiso 1 1 calc R . .
C14 C 0.7543(5) 0.4302(4) 0.0699(3) 0.0623(10) Uani 1 1 d . . .
H14A H 0.7047 0.5175 0.0972 0.093 Uiso 1 1 calc R . .
H14B H 0.6918 0.3851 -0.0042 0.093 Uiso 1 1 calc R . .
H14C H 0.8666 0.4517 0.0495 0.093 Uiso 1 1 calc R . .
C2 C 0.8145(5) -0.3086(3) 0.5623(4) 0.0608(10) Uani 1 1 d . . .
H2A H 0.8444 -0.3524 0.4856 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.246(2) . ?
Cd1 N2 2.329(2) . ?
Cd1 Cl1 2.3695(8) . ?
Cd1 Cl2 2.4073(9) . ?
O1 C5 1.340(4) . ?
O1 C7 1.437(4) . ?
N1 C5 1.327(4) . ?
N1 C1 1.348(4) . ?
N2 C6 1.276(4) . ?
N2 C8 1.425(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.458(5) . ?
C3 C2 1.364(5) . ?
C3 C4 1.379(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.401(4) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.383(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.373(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.370(5) . ?
C11 C14 1.508(5) . ?
C12 C13 1.376(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C2 H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N2 73.01(9) . . ?
N1 Cd1 Cl1 127.86(7) . . ?
N2 Cd1 Cl1 117.64(6) . . ?
N1 Cd1 Cl2 110.95(7) . . ?
N2 Cd1 Cl2 107.65(7) . . ?
Cl1 Cd1 Cl2 112.61(3) . . ?
C5 O1 C7 119.1(3) . . ?
C5 N1 C1 120.0(3) . . ?
C5 N1 Cd1 124.2(2) . . ?
C1 N1 Cd1 115.3(2) . . ?
C6 N2 C8 121.7(2) . . ?
C6 N2 Cd1 113.0(2) . . ?
C8 N2 Cd1 125.10(17) . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C6 116.7(2) . . ?
C2 C1 C6 122.5(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 117.6(4) . . ?
C3 C4 H4A 121.2 . . ?
C5 C4 H4A 121.2 . . ?
N1 C5 O1 112.4(3) . . ?
N1 C5 C4 121.8(3) . . ?
O1 C5 C4 125.8(3) . . ?
N2 C6 C1 120.9(3) . . ?
N2 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 N2 117.6(3) . . ?
C9 C8 N2 124.4(3) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10A 119.0 . . ?
C11 C10 H10A 119.0 . . ?
C12 C11 C10 117.1(3) . . ?
C12 C11 C14 121.9(3) . . ?
C10 C11 C14 121.0(3) . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12A 119.0 . . ?
C13 C12 H12A 119.0 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13A 119.6 . . ?
C8 C13 H13A 119.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1025950'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 Hg N2 O'
_chemical_formula_weight         497.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_HALL  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9723(5)
_cell_length_b                   9.3550(5)
_cell_length_c                   10.6022(10)
_cell_angle_alpha                94.084(6)
_cell_angle_beta                 93.391(6)
_cell_angle_gamma                93.839(5)
_cell_volume                     785.32(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5115
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      25.98

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    10.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.242
_exptl_absorpt_correction_T_max  0.363
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5115
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.98
_reflns_number_total             3086
_reflns_number_gt                2671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.0413P] 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         3063
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.70745(4) 0.63637(3) 0.18989(3) 0.04690(17) Uani 1 1 d . . .
Cl1 Cl 0.9767(3) 0.7599(2) 0.2717(3) 0.0630(7) Uani 1 1 d . . .
Cl2 Cl 0.4826(3) 0.7824(2) 0.2281(3) 0.0585(6) Uani 1 1 d . . .
O1 O 0.6767(9) 0.4017(7) 0.3846(7) 0.0583(17) Uani 1 1 d . . .
C1 C 0.7830(10) 0.3338(8) 0.0731(9) 0.042(2) Uani 1 1 d . . .
C2 C 0.8173(12) 0.1918(9) 0.0639(11) 0.054(2) Uani 1 1 d . . .
H2A H 0.8490 0.1490 -0.0121 0.065 Uiso 1 1 calc R . .
C3 C 0.8044(13) 0.1145(9) 0.1673(13) 0.066(3) Uani 1 1 d . . .
H3A H 0.8276 0.0182 0.1621 0.079 Uiso 1 1 calc R . .
C4 C 0.7573(13) 0.1780(9) 0.2792(12) 0.062(3) Uani 1 1 d . . .
H4A H 0.7481 0.1253 0.3499 0.074 Uiso 1 1 calc R . .
C5 C 0.7228(11) 0.3254(9) 0.2857(10) 0.046(2) Uani 1 1 d . . .
C7 C 0.6452(15) 0.3344(12) 0.5001(11) 0.071(3) Uani 1 1 d . . .
H7A H 0.5581 0.2584 0.4832 0.107 Uiso 1 1 calc R . .
H7B H 0.6101 0.4045 0.5619 0.107 Uiso 1 1 calc R . .
H7C H 0.7464 0.2958 0.5322 0.107 Uiso 1 1 calc R . .
C6 C 0.7909(10) 0.4235(8) -0.0349(9) 0.043(2) Uani 1 1 d . . .
H6 H 0.8240 0.3843 -0.1118 0.052 Uiso 1 1 calc R . .
C8 C 0.7561(9) 0.6409(7) -0.1300(9) 0.0372(18) Uani 1 1 d . . .
C9 C 0.6970(11) 0.7776(8) -0.1097(8) 0.0423(19) Uani 1 1 d . . .
H9A H 0.6581 0.8076 -0.0318 0.051 Uiso 1 1 calc R . .
C10 C 0.6979(12) 0.8682(9) -0.2092(9) 0.049(2) Uani 1 1 d . . .
H10A H 0.6572 0.9587 -0.1967 0.059 Uiso 1 1 calc R . .
C11 C 0.7570(11) 0.8282(9) -0.3251(10) 0.048(2) Uani 1 1 d . . .
C12 C 0.8185(12) 0.6901(9) -0.3449(10) 0.051(2) Uani 1 1 d . . .
H12A H 0.8585 0.6603 -0.4224 0.061 Uiso 1 1 calc R . .
C13 C 0.8179(11) 0.5995(9) -0.2453(10) 0.049(2) Uani 1 1 d . . .
H13A H 0.8599 0.5095 -0.2569 0.058 Uiso 1 1 calc R . .
C14 C 0.7611(14) 0.9255(10) -0.4320(10) 0.059(3) Uani 1 1 d . . .
H14A H 0.7163 1.0149 -0.4059 0.088 Uiso 1 1 calc R . .
H14B H 0.6945 0.8805 -0.5042 0.088 Uiso 1 1 calc R . .
H14C H 0.8753 0.9433 -0.4540 0.088 Uiso 1 1 calc R . .
N1 N 0.7360(8) 0.3970(7) 0.1820(8) 0.0475(19) Uani 1 1 d . . .
N2 N 0.7530(8) 0.5546(6) -0.0253(7) 0.0409(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.262(6) . ?
Hg1 Cl2 2.362(2) . ?
Hg1 N2 2.410(8) . ?
Hg1 Cl1 2.450(2) . ?
O1 C5 1.310(12) . ?
O1 C7 1.444(11) . ?
C1 N1 1.343(12) . ?
C1 C2 1.372(11) . ?
C1 C6 1.469(13) . ?
C2 C3 1.361(15) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.421(12) . ?
C4 H4A 0.9300 . ?
C5 N1 1.334(11) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 N2 1.282(9) . ?
C6 H6 0.9300 . ?
C8 C13 1.384(13) . ?
C8 C9 1.400(10) . ?
C8 N2 1.419(11) . ?
C9 C10 1.400(12) . ?
C9 H9A 0.9300 . ?
C10 C11 1.378(14) . ?
C10 H10A 0.9300 . ?
C11 C12 1.419(12) . ?
C11 C14 1.503(12) . ?
C12 C13 1.399(13) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 Cl2 134.32(18) . . ?
N1 Hg1 N2 71.6(3) . . ?
Cl2 Hg1 N2 118.90(16) . . ?
N1 Hg1 Cl1 108.11(18) . . ?
Cl2 Hg1 Cl1 110.80(8) . . ?
N2 Hg1 Cl1 104.66(16) . . ?
C5 O1 C7 120.2(8) . . ?
N1 C1 C2 121.1(9) . . ?
N1 C1 C6 116.5(7) . . ?
C2 C1 C6 122.3(9) . . ?
C3 C2 C1 119.1(10) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.3(9) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.2(9) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
O1 C5 N1 114.6(7) . . ?
O1 C5 C4 126.8(9) . . ?
N1 C5 C4 118.6(10) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 C1 121.3(9) . . ?
N2 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C13 C8 C9 120.0(7) . . ?
C13 C8 N2 124.3(7) . . ?
C9 C8 N2 115.7(8) . . ?
C10 C9 C8 118.4(8) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C11 C10 C9 122.4(8) . . ?
C11 C10 H10A 118.8 . . ?
C9 C10 H10A 118.8 . . ?
C10 C11 C12 119.0(8) . . ?
C10 C11 C14 122.8(8) . . ?
C12 C11 C14 118.2(10) . . ?
C13 C12 C11 118.7(9) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C8 C13 C12 121.6(8) . . ?
C8 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 C1 121.7(7) . . ?
C5 N1 Hg1 120.6(7) . . ?
C1 N1 Hg1 117.5(5) . . ?
C6 N2 C8 121.7(8) . . ?
C6 N2 Hg1 112.1(6) . . ?
C8 N2 Hg1 125.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.807
_refine_diff_density_min         -2.296
_refine_diff_density_rms         0.229
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1025951'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================ 
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cd Cl2 N2 O2'
_chemical_formula_weight         425.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   ' P 21/c'
_symmetry_space_group_name_HALL  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0890(16)
_cell_length_b                   26.743(5)
_cell_length_c                   7.8060(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.11(3)
_cell_angle_gamma                90.00
_cell_volume                     1553.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3567
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3567
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3567
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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         3549
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.77213(5) 0.126428(12) 0.65005(5) 0.01714(15) Uani 1 1 d . . .
Cl1 Cl 0.6249(2) 0.12326(5) 0.31431(19) 0.0297(3) Uani 1 1 d . . .
Cl2 Cl 0.57577(19) 0.12523(4) 0.81884(19) 0.0233(3) Uani 1 1 d . . .
O1 O 0.7559(6) 0.00662(14) 0.5944(6) 0.0300(10) Uani 1 1 d . . .
O2 O 0.8070(5) 0.21963(13) 0.6345(5) 0.0207(8) Uani 1 1 d . . .
N1 N 0.9717(6) 0.05957(15) 0.7576(6) 0.0186(9) Uani 1 1 d . . .
N2 N 1.0541(6) 0.15707(15) 0.8481(6) 0.0178(9) Uani 1 1 d . . .
C1 C 1.1387(7) 0.07100(18) 0.8807(7) 0.0194(11) Uani 1 1 d . . .
C2 C 1.2690(8) 0.0349(2) 0.9641(8) 0.0272(12) Uani 1 1 d . . .
H2A H 1.3828 0.0434 1.0502 0.033 Uiso 1 1 calc R . .
C3 C 1.2211(8) -0.0149(2) 0.9126(10) 0.0316(14) Uani 1 1 d . . .
H3A H 1.3049 -0.0402 0.9635 0.038 Uiso 1 1 calc R . .
C4 C 1.0521(9) -0.02657(19) 0.7882(9) 0.0285(13) Uani 1 1 d . . .
H4A H 1.0203 -0.0596 0.7542 0.034 Uiso 1 1 calc R . .
C5 C 0.9280(8) 0.01186(19) 0.7129(8) 0.0218(11) Uani 1 1 d . . .
C6 C 1.1792(7) 0.12422(19) 0.9195(8) 0.0220(11) Uani 1 1 d . . .
H6A H 1.2950 0.1343 0.9955 0.026 Uiso 1 1 calc R . .
C7 C 0.6932(9) -0.0423(2) 0.5162(10) 0.0377(16) Uani 1 1 d . . .
H7A H 0.5686 -0.0404 0.4344 0.057 Uiso 1 1 calc R . .
H7B H 0.7076 -0.0655 0.6148 0.057 Uiso 1 1 calc R . .
H7C H 0.7621 -0.0535 0.4474 0.057 Uiso 1 1 calc R . .
C8 C 1.0868(7) 0.20884(18) 0.8837(7) 0.0181(10) Uani 1 1 d . . .
C9 C 0.9536(7) 0.24164(18) 0.7673(8) 0.0189(11) Uani 1 1 d . . .
C10 C 0.9754(8) 0.29330(19) 0.7913(9) 0.0261(12) Uani 1 1 d . . .
H10A H 0.8883 0.3151 0.7145 0.031 Uiso 1 1 calc R . .
C11 C 1.1301(9) 0.3114(2) 0.9323(9) 0.0310(14) Uani 1 1 d . . .
H11A H 1.1463 0.3457 0.9478 0.037 Uiso 1 1 calc R . .
C12 C 1.2615(8) 0.2796(2) 1.0510(9) 0.0310(14) Uani 1 1 d . . .
H12A H 1.3628 0.2928 1.1455 0.037 Uiso 1 1 calc R . .
C13 C 1.2411(8) 0.22825(19) 1.0280(8) 0.0229(11) Uani 1 1 d . . .
H13A H 1.3282 0.2068 1.1070 0.028 Uiso 1 1 calc R . .
C14 C 0.6704(8) 0.2521(2) 0.5083(8) 0.0267(13) Uani 1 1 d . . .
H14A H 0.7128 0.2860 0.5264 0.040 Uiso 1 1 calc R . .
H14B H 0.5631 0.2497 0.5325 0.040 Uiso 1 1 calc R . .
H14C H 0.6445 0.2422 0.3821 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.333(4) . ?
Cd1 N2 2.345(4) . ?
Cd1 Cl1 2.4174(16) . ?
Cd1 Cl2 2.4295(16) . ?
Cd1 O2 2.517(3) . ?
O1 C5 1.343(7) . ?
O1 C7 1.449(6) . ?
O2 C9 1.365(6) . ?
O2 C14 1.447(6) . ?
N1 C5 1.333(6) . ?
N1 C1 1.350(7) . ?
N2 C6 1.290(7) . ?
N2 C8 1.416(6) . ?
C1 C2 1.388(7) . ?
C1 C6 1.465(7) . ?
C2 C3 1.402(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(8) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.410(7) . ?
C8 C13 1.411(7) . ?
C9 C10 1.396(7) . ?
C10 C11 1.389(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.392(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.387(8) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N2 70.97(14) . . ?
N1 Cd1 Cl1 109.88(12) . . ?
N2 Cd1 Cl1 131.68(12) . . ?
N1 Cd1 Cl2 107.57(13) . . ?
N2 Cd1 Cl2 108.72(12) . . ?
Cl1 Cd1 Cl2 116.02(6) . . ?
N1 Cd1 O2 134.56(14) . . ?
N2 Cd1 O2 65.62(13) . . ?
Cl1 Cd1 O2 89.95(9) . . ?
Cl2 Cd1 O2 98.56(10) . . ?
C5 O1 C7 118.8(5) . . ?
C9 O2 C14 117.5(4) . . ?
C9 O2 Cd1 118.1(3) . . ?
C14 O2 Cd1 123.9(3) . . ?
C5 N1 C1 119.4(4) . . ?
C5 N1 Cd1 124.4(4) . . ?
C1 N1 Cd1 116.1(3) . . ?
C6 N2 C8 121.8(5) . . ?
C6 N2 Cd1 116.2(3) . . ?
C8 N2 Cd1 122.0(3) . . ?
N1 C1 C2 122.7(5) . . ?
N1 C1 C6 116.6(4) . . ?
C2 C1 C6 120.7(5) . . ?
C1 C2 C3 116.9(5) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
N1 C5 O1 112.1(5) . . ?
N1 C5 C4 121.5(5) . . ?
O1 C5 C4 126.4(5) . . ?
N2 C6 C1 119.9(5) . . ?
N2 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.9(4) . . ?
C9 C8 N2 116.4(4) . . ?
C13 C8 N2 123.7(5) . . ?
O2 C9 C10 123.7(5) . . ?
O2 C9 C8 115.9(4) . . ?
C10 C9 C8 120.3(5) . . ?
C11 C10 C9 118.5(5) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 C12 122.1(5) . . ?
C10 C11 H11A 119.0 . . ?
C12 C11 H11A 119.0 . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C8 119.4(5) . . ?
C12 C13 H13A 120.3 . . ?
C8 C13 H13A 120.3 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.243
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.177
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1025952'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 Hg N2 O2'
_chemical_formula_weight         513.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   8.1151(4)
_cell_length_b                   27.0756(10)
_cell_length_c                   7.9481(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.015(6)
_cell_angle_gamma                90.00
_cell_volume                     1595.20(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5979
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    9.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3293
_exptl_absorpt_correction_T_max  0.3613
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5979
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3660
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0293P)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         3660
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003

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
Hg1 Hg -0.25502(4) -0.123556(10) -0.13943(3) 0.03972(10) Uani 1 1 d . . .
Cl1 Cl -0.1300(3) -0.12306(8) 0.1885(3) 0.0647(6) Uani 1 1 d . . .
Cl2 Cl -0.0824(3) -0.12456(7) -0.3243(3) 0.0510(5) Uani 1 1 d . . .
O1 O -0.2623(8) -0.0048(2) -0.0990(9) 0.0668(17) Uani 1 1 d . . .
O2 O -0.3084(6) -0.22107(17) -0.1206(7) 0.0446(12) Uani 1 1 d . . .
N1 N -0.4725(8) -0.05949(19) -0.2575(8) 0.0368(13) Uani 1 1 d . . .
N2 N -0.5483(7) -0.15751(19) -0.3388(7) 0.0310(12) Uani 1 1 d . . .
C1 C -0.6359(9) -0.0728(3) -0.3757(10) 0.0379(16) Uani 1 1 d . . .
C2 C -0.7707(11) -0.0385(3) -0.4642(12) 0.057(2) Uani 1 1 d . . .
H2A H -0.8842 -0.0482 -0.5488 0.068 Uiso 1 1 calc R . .
C3 C -0.7278(12) 0.0116(3) -0.4202(14) 0.066(3) Uani 1 1 d . . .
H3A H -0.8142 0.0358 -0.4753 0.079 Uiso 1 1 calc R . .
C4 C -0.5630(12) 0.0243(3) -0.2994(12) 0.057(2) Uani 1 1 d . . .
H4A H -0.5341 0.0573 -0.2698 0.069 Uiso 1 1 calc R . .
C5 C -0.4356(10) -0.0123(3) -0.2186(11) 0.0435(18) Uani 1 1 d . . .
C6 C -0.6712(9) -0.1251(3) -0.4110(9) 0.0395(16) Uani 1 1 d . . .
H6A H -0.7867 -0.1354 -0.4885 0.047 Uiso 1 1 calc R . .
C7 C -0.2036(14) 0.0444(3) -0.0303(14) 0.086(3) Uani 1 1 d . . .
H7A H -0.0778 0.0437 0.0506 0.129 Uiso 1 1 calc R . .
H7B H -0.2719 0.0560 0.0360 0.129 Uiso 1 1 calc R . .
H7C H -0.2220 0.0662 -0.1317 0.129 Uiso 1 1 calc R . .
C8 C -0.5831(8) -0.2089(2) -0.3730(9) 0.0306(14) Uani 1 1 d . . .
C9 C -0.4534(9) -0.2417(3) -0.2578(10) 0.0352(15) Uani 1 1 d . . .
C10 C -0.4806(11) -0.2924(3) -0.2831(12) 0.0483(19) Uani 1 1 d . . .
H10A H -0.3970 -0.3144 -0.2034 0.058 Uiso 1 1 calc R . .
C11 C -0.6302(12) -0.3096(3) -0.4250(12) 0.056(2) Uani 1 1 d . . .
H11A H -0.6473 -0.3435 -0.4426 0.068 Uiso 1 1 calc R . .
C12 C -0.7572(11) -0.2776(3) -0.5433(11) 0.055(2) Uani 1 1 d . . .
H12A H -0.8590 -0.2901 -0.6393 0.066 Uiso 1 1 calc R . .
C13 C -0.7333(9) -0.2270(3) -0.5193(10) 0.0415(17) Uani 1 1 d . . .
H13A H -0.8172 -0.2054 -0.6006 0.050 Uiso 1 1 calc R . .
C14 C -0.1704(10) -0.2524(3) 0.0046(11) 0.053(2) Uani 1 1 d . . .
H14A H -0.0777 -0.2324 0.0930 0.079 Uiso 1 1 calc R . .
H14B H -0.1194 -0.2721 -0.0627 0.079 Uiso 1 1 calc R . .
H14C H -0.2217 -0.2736 0.0674 0.079 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.378(5) . ?
Hg1 Cl1 2.3816(19) . ?
Hg1 Cl2 2.4080(18) . ?
Hg1 N2 2.439(5) . ?
O1 C5 1.355(9) . ?
O1 C7 1.444(9) . ?
O2 C9 1.357(8) . ?
O2 C14 1.434(8) . ?
N1 C5 1.320(8) . ?
N1 C1 1.326(8) . ?
N2 C6 1.276(8) . ?
N2 C8 1.424(7) . ?
C1 C2 1.388(10) . ?
C1 C6 1.451(9) . ?
C2 C3 1.408(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.335(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(10) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.388(9) . ?
C8 C9 1.397(9) . ?
C9 C10 1.392(9) . ?
C10 C11 1.360(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(11) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(10) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 Cl1 110.18(15) . . ?
N1 Hg1 Cl2 106.86(14) . . ?
Cl1 Hg1 Cl2 124.98(8) . . ?
N1 Hg1 N2 69.36(18) . . ?
Cl1 Hg1 N2 125.57(13) . . ?
Cl2 Hg1 N2 104.80(13) . . ?
C5 O1 C7 119.5(7) . . ?
C9 O2 C14 119.4(5) . . ?
C5 N1 C1 119.7(6) . . ?
C5 N1 Hg1 123.5(5) . . ?
C1 N1 Hg1 116.7(4) . . ?
C6 N2 C8 121.8(6) . . ?
C6 N2 Hg1 114.3(4) . . ?
C8 N2 Hg1 123.9(4) . . ?
N1 C1 C2 122.2(7) . . ?
N1 C1 C6 117.6(6) . . ?
C2 C1 C6 120.2(7) . . ?
C1 C2 C3 117.0(8) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 H2A 121.5 . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 119.3(8) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 O1 112.4(6) . . ?
N1 C5 C4 121.8(7) . . ?
O1 C5 C4 125.7(7) . . ?
N2 C6 C1 121.8(6) . . ?
N2 C6 H6A 119.1 . . ?
C1 C6 H6A 119.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.7(6) . . ?
C13 C8 N2 123.0(6) . . ?
C9 C8 N2 117.3(6) . . ?
O2 C9 C10 123.8(7) . . ?
O2 C9 C8 116.1(6) . . ?
C10 C9 C8 120.0(7) . . ?
C11 C10 C9 119.5(8) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 121.1(7) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C11 C12 C13 120.1(7) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C8 C13 C12 119.4(7) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.726
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.152
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1026069'
_audit_update_record             
;
2014-09-25 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

#================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 N2 O2 Zn'
_chemical_formula_weight         378.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_HALL  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7220(15)
_cell_length_b                   19.870(4)
_cell_length_c                   10.576(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.50(3)
_cell_angle_gamma                90.00
_cell_volume                     1622.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11877
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11877
_diffrn_reflns_av_R_equivalents  0.1393
_diffrn_reflns_av_sigmaI/netI    0.1288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2859
_reflns_number_gt                2036
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+9.2201P] 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         2845
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2072
_refine_ls_wR_factor_gt          0.1917
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.28870(13) 0.07318(4) 0.32009(9) 0.0311(3) Uani 1 1 d . . .
Cl1 Cl 0.0413(3) 0.11796(11) 0.2318(2) 0.0393(5) Uani 1 1 d . . .
Cl2 Cl 0.5493(3) 0.10417(11) 0.24702(19) 0.0386(5) Uani 1 1 d . . .
O1 O 0.3236(8) 0.2120(3) 0.4827(5) 0.0390(14) Uani 1 1 d . . .
O2 O 0.2666(9) -0.0211(3) 0.1586(5) 0.0463(16) Uani 1 1 d . . .
N1 N 0.2661(9) 0.1007(3) 0.5152(6) 0.0311(15) Uani 1 1 d . . .
N2 N 0.2554(9) -0.0243(3) 0.4079(6) 0.0302(15) Uani 1 1 d . . .
C1 C 0.2205(11) 0.0472(4) 0.5891(7) 0.0318(18) Uani 1 1 d . . .
C2 C 0.1743(12) 0.0550(5) 0.7162(8) 0.038(2) Uani 1 1 d . . .
H2A H 0.1420 0.0183 0.7649 0.046 Uiso 1 1 calc R . .
C3 C 0.1792(13) 0.1204(4) 0.7666(8) 0.042(2) Uani 1 1 d . . .
H3A H 0.1492 0.1271 0.8502 0.050 Uiso 1 1 calc R . .
C4 C 0.2282(12) 0.1761(5) 0.6937(8) 0.040(2) Uani 1 1 d . . .
H4A H 0.2323 0.2193 0.7275 0.049 Uiso 1 1 calc R . .
C5 C 0.2707(11) 0.1636(4) 0.5674(8) 0.0342(18) Uani 1 1 d . . .
C6 C 0.2184(11) -0.0203(4) 0.5263(7) 0.0330(18) Uani 1 1 d . . .
H6A H 0.1909 -0.0588 0.5716 0.040 Uiso 1 1 calc R . .
C7 C 0.3450(14) 0.2806(4) 0.5316(9) 0.047(2) Uani 1 1 d . . .
H7A H 0.3820 0.3097 0.4650 0.071 Uiso 1 1 calc R . .
H7B H 0.4304 0.2807 0.5992 0.071 Uiso 1 1 calc R . .
H7C H 0.2365 0.2964 0.5626 0.071 Uiso 1 1 calc R . .
C8 C 0.2554(11) -0.0888(4) 0.3411(8) 0.0344(19) Uani 1 1 d . . .
C9 C 0.2639(12) -0.0853(4) 0.2092(8) 0.037(2) Uani 1 1 d . . .
C10 C 0.2579(13) -0.1459(5) 0.1357(9) 0.045(2) Uani 1 1 d . . .
H10A H 0.2614 -0.1443 0.0480 0.055 Uiso 1 1 calc R . .
C11 C 0.2467(14) -0.2079(5) 0.1993(10) 0.059(3) Uani 1 1 d . . .
H11A H 0.2368 -0.2471 0.1517 0.071 Uiso 1 1 calc R . .
C12 C 0.2499(14) -0.2128(4) 0.3297(9) 0.053(3) Uani 1 1 d . . .
H12A H 0.2512 -0.2546 0.3693 0.063 Uiso 1 1 calc R . .
C13 C 0.2510(13) -0.1520(4) 0.4022(9) 0.047(2) Uani 1 1 d . . .
H13A H 0.2489 -0.1540 0.4900 0.056 Uiso 1 1 calc R . .
C14 C 0.2574(15) -0.0128(5) 0.0242(8) 0.054(3) Uani 1 1 d . . .
H14A H 0.2614 0.0343 0.0040 0.081 Uiso 1 1 calc R . .
H14B H 0.1510 -0.0317 -0.0085 0.081 Uiso 1 1 calc R . .
H14C H 0.3536 -0.0353 -0.0129 0.081 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.147(6) . ?
Zn1 N2 2.167(7) . ?
Zn1 Cl2 2.260(2) . ?
Zn1 Cl1 2.285(2) . ?
Zn1 O2 2.537(6) . ?
O1 C5 1.383(10) . ?
O1 C7 1.466(9) . ?
O2 C9 1.383(10) . ?
O2 C14 1.431(10) . ?
N1 C5 1.366(10) . ?
N1 C1 1.371(10) . ?
N2 C6 1.294(10) . ?
N2 C8 1.463(10) . ?
C1 C2 1.409(11) . ?
C1 C6 1.496(11) . ?
C2 C3 1.406(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.405(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.406(11) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.400(12) . ?
C8 C13 1.412(12) . ?
C9 C10 1.433(11) . ?
C10 C11 1.408(14) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(14) . ?
C11 H11A 0.9300 . ?
C12 C13 1.432(13) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 78.6(2) . . ?
N1 Zn1 Cl2 110.8(2) . . ?
N2 Zn1 Cl2 120.46(19) . . ?
N1 Zn1 Cl1 101.86(19) . . ?
N2 Zn1 Cl1 114.58(18) . . ?
Cl2 Zn1 Cl1 119.78(8) . . ?
N1 Zn1 O2 146.0(2) . . ?
N2 Zn1 O2 67.8(2) . . ?
Cl2 Zn1 O2 90.91(17) . . ?
Cl1 Zn1 O2 88.37(16) . . ?
C5 O1 C7 116.8(6) . . ?
C9 O2 C14 119.3(7) . . ?
C9 O2 Zn1 115.0(5) . . ?
C14 O2 Zn1 125.7(5) . . ?
C5 N1 C1 118.9(7) . . ?
C5 N1 Zn1 128.3(5) . . ?
C1 N1 Zn1 112.2(5) . . ?
C6 N2 C8 121.6(7) . . ?
C6 N2 Zn1 113.0(5) . . ?
C8 N2 Zn1 125.1(5) . . ?
N1 C1 C2 122.3(7) . . ?
N1 C1 C6 116.2(7) . . ?
C2 C1 C6 121.5(7) . . ?
C3 C2 C1 117.3(8) . . ?
C3 C2 H2A 121.4 . . ?
C1 C2 H2A 121.4 . . ?
C4 C3 C2 121.7(8) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 117.1(8) . . ?
C3 C4 H4A 121.5 . . ?
C5 C4 H4A 121.5 . . ?
N1 C5 O1 112.3(7) . . ?
N1 C5 C4 122.7(8) . . ?
O1 C5 C4 124.9(7) . . ?
N2 C6 C1 119.0(7) . . ?
N2 C6 H6A 120.5 . . ?
C1 C6 H6A 120.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.2(8) . . ?
C9 C8 N2 116.0(7) . . ?
C13 C8 N2 123.8(7) . . ?
O2 C9 C8 115.6(7) . . ?
O2 C9 C10 124.5(8) . . ?
C8 C9 C10 119.8(8) . . ?
C11 C10 C9 118.6(8) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C12 C11 C10 122.6(9) . . ?
C12 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
C11 C12 C13 118.3(8) . . ?
C11 C12 H12A 120.8 . . ?
C13 C12 H12A 120.8 . . ?
C8 C13 C12 120.3(8) . . ?
C8 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.146
