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

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

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1051164'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 Cl2 Cu Hg3 N8 O10'
_chemical_formula_weight         1454.93

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'
Cu Cu 0.3201 1.2651 '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

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

_cell_length_a                   8.2953(2)
_cell_length_b                   10.6258(5)
_cell_length_c                   12.4574(4)
_cell_angle_alpha                83.389(6)
_cell_angle_beta                 81.479(3)
_cell_angle_gamma                84.419(4)
_cell_volume                     1075.11(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             681
_exptl_absorpt_coefficient_mu    11.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_T_max  0.45
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_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  'Stoe-ipds II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9831
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3727
_reflns_number_gt                2457
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0514P)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         3727
_refine_ls_number_parameters     273
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8233(17) 0.3154(12) 0.5700(10) 0.042(3) Uani 1 1 d . . .
H1 H 0.8965 0.3484 0.5121 0.050 Uiso 1 1 calc R . .
C3 C 0.6281(18) 0.1690(14) 0.6475(12) 0.050(3) Uani 1 1 d . . .
H3 H 0.5634 0.1036 0.6431 0.060 Uiso 1 1 calc R . .
C4 C 0.6163(19) 0.2223(14) 0.7438(11) 0.053(3) Uani 1 1 d . . .
H4 H 0.5497 0.1863 0.8040 0.063 Uiso 1 1 calc R . .
C6 C 0.8007(19) 0.3670(14) 0.6675(11) 0.051(3) Uani 1 1 d . . .
H6 H 0.8593 0.4353 0.6744 0.061 Uiso 1 1 calc R . .
C8 C 0.7536(15) 0.4092(10) 0.1839(9) 0.035(3) Uani 1 1 d . . .
H8 H 0.7505 0.3452 0.1394 0.042 Uiso 1 1 calc R . .
C9 C 0.6473(14) 0.4069(11) 0.2806(9) 0.033(3) Uani 1 1 d . . .
H9 H 0.5745 0.3440 0.2986 0.040 Uiso 1 1 calc R . .
C10 C 0.8626(14) 0.5880(12) 0.2159(9) 0.034(3) Uani 1 1 d . . .
H10 H 0.9337 0.6514 0.1937 0.041 Uiso 1 1 calc R . .
C11 C 0.7644(16) 0.5927(11) 0.3160(8) 0.038(3) Uani 1 1 d . . .
H11 H 0.7734 0.6563 0.3597 0.045 Uiso 1 1 calc R . .
C12 C 1.3385(18) 0.4329(14) 0.1042(12) 0.053(3) Uani 1 1 d . . .
H12A H 1.3034 0.4103 0.1812 0.064 Uiso 1 1 calc R . .
H12B H 1.4556 0.4401 0.0937 0.064 Uiso 1 1 calc R . .
C13 C 1.2988(16) 0.3312(12) 0.0382(11) 0.045(3) Uani 1 1 d . . .
H13A H 1.3436 0.3498 -0.0378 0.054 Uiso 1 1 calc R . .
H13B H 1.3481 0.2491 0.0648 0.054 Uiso 1 1 calc R . .
C14 C 0.8250(16) 0.0373(12) 0.2676(10) 0.041(3) Uani 1 1 d . . .
C15 C 0.7340(17) 0.2103(11) 0.5570(10) 0.042(3) Uani 1 1 d . . .
C20 C 0.6502(13) 0.5005(11) 0.3516(8) 0.031(2) Uani 1 1 d . . .
C22 C 0.702(2) 0.0349(14) 0.1989(12) 0.057(4) Uani 1 1 d . . .
H22 H 0.5989 0.0772 0.2142 0.068 Uiso 1 1 calc R . .
C23 C 0.743(2) -0.0338(16) 0.1074(12) 0.067(5) Uani 1 1 d . . .
H23 H 0.6636 -0.0323 0.0615 0.081 Uiso 1 1 calc R . .
C25 C 0.995(2) -0.0945(13) 0.1468(12) 0.065(5) Uani 1 1 d . . .
H25 H 1.0966 -0.1383 0.1307 0.078 Uiso 1 1 calc R . .
C26 C 0.968(2) -0.0274(14) 0.2381(12) 0.062(4) Uani 1 1 d . . .
H26 H 1.0525 -0.0275 0.2798 0.075 Uiso 1 1 calc R . .
Cl1 Cl 0.2248(5) 0.2167(4) 0.3814(3) 0.0651(11) Uani 1 1 d . . .
Cu1 Cu 1.0000 0.5000 0.0000 0.0270(4) Uani 1 2 d S . .
Hg1 Hg 0.5000 0.5000 0.5000 0.0379(2) Uani 1 2 d S . .
Hg2 Hg 0.77626(7) 0.12386(5) 0.41239(4) 0.04737(19) Uani 1 1 d . . .
N1 N 0.8614(10) 0.4973(9) 0.1491(7) 0.029(2) Uani 1 1 d . . .
N2 N 0.6931(16) 0.3207(12) 0.7565(9) 0.054(3) Uani 1 1 d . . .
N3 N 1.1149(12) 0.3267(9) 0.0481(7) 0.034(2) Uani 1 1 d D . .
N4 N 0.8828(15) -0.1000(11) 0.0807(9) 0.051(3) Uani 1 1 d . . .
O1 O 1.2543(12) 0.5534(9) 0.0682(7) 0.045(2) Uani 1 1 d . . .
H1A H 1.2750 0.6090 0.1034 0.068 Uiso 1 1 calc R . .
O1P O 0.274(3) 0.3150(16) 0.4290(12) 0.130(7) Uani 1 1 d . . .
O2P O 0.0959(19) 0.2822(19) 0.3210(14) 0.129(6) Uani 1 1 d . . .
O3P O 0.1405(15) 0.1241(13) 0.4523(13) 0.099(5) Uani 1 1 d . . .
O4P O 0.345(2) 0.1719(15) 0.3007(15) 0.133(7) Uani 1 1 d . . .
H1N H 1.104(13) 0.307(10) 0.1276(13) 0.02(3) Uiso 1 1 d D . .
H2N H 1.104(12) 0.256(6) 0.006(7) 0.02(2) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.370(17) . ?
C1 C15 1.435(18) . ?
C1 H1 0.9300 . ?
C3 C4 1.372(19) . ?
C3 C15 1.38(2) . ?
C3 H3 0.9300 . ?
C4 N2 1.313(18) . ?
C4 H4 0.9300 . ?
C6 N2 1.39(2) . ?
C6 H6 0.9300 . ?
C8 N1 1.348(15) . ?
C8 C9 1.383(15) . ?
C8 H8 0.9300 . ?
C9 C20 1.410(16) . ?
C9 H9 0.9300 . ?
C10 N1 1.345(14) . ?
C10 C11 1.388(15) . ?
C10 H10 0.9300 . ?
C11 C20 1.418(17) . ?
C11 H11 0.9300 . ?
C12 O1 1.455(16) . ?
C12 C13 1.519(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.517(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C26 1.34(2) . ?
C14 C22 1.430(19) . ?
C14 Hg2 2.087(12) . ?
C15 Hg2 2.084(11) . ?
C20 Hg1 2.070(9) . ?
C22 C23 1.41(2) . ?
C22 H22 0.9300 . ?
C23 N4 1.32(2) . ?
C23 H23 0.9300 . ?
C25 N4 1.34(2) . ?
C25 C26 1.389(19) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
Cl1 O1P 1.380(13) . ?
Cl1 O4P 1.395(13) . ?
Cl1 O3P 1.410(12) . ?
Cl1 O2P 1.472(15) . ?
Cu1 N1 2.034(8) 2_765 ?
Cu1 N1 2.034(8) . ?
Cu1 N3 2.057(10) 2_765 ?
Cu1 N3 2.057(10) . ?
Hg1 C20 2.070(9) 2_666 ?
N3 H1N 0.9800(11) . ?
N3 H2N 0.9800(10) . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C15 120.0(13) . . ?
C6 C1 H1 120.0 . . ?
C15 C1 H1 120.0 . . ?
C4 C3 C15 121.4(13) . . ?
C4 C3 H3 119.3 . . ?
C15 C3 H3 119.3 . . ?
N2 C4 C3 124.1(14) . . ?
N2 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C1 C6 N2 122.2(13) . . ?
C1 C6 H6 118.9 . . ?
N2 C6 H6 118.9 . . ?
N1 C8 C9 124.9(10) . . ?
N1 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C8 C9 C20 119.5(11) . . ?
C8 C9 H9 120.3 . . ?
C20 C9 H9 120.3 . . ?
N1 C10 C11 124.1(11) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C20 119.9(10) . . ?
C10 C11 H11 120.0 . . ?
C20 C11 H11 120.0 . . ?
O1 C12 C13 108.8(10) . . ?
O1 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 C12 109.9(10) . . ?
N3 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C26 C14 C22 116.1(12) . . ?
C26 C14 Hg2 122.2(10) . . ?
C22 C14 Hg2 121.5(10) . . ?
C3 C15 C1 115.3(11) . . ?
C3 C15 Hg2 124.0(10) . . ?
C1 C15 Hg2 120.6(10) . . ?
C9 C20 C11 115.8(9) . . ?
C9 C20 Hg1 121.7(8) . . ?
C11 C20 Hg1 122.4(8) . . ?
C23 C22 C14 117.4(15) . . ?
C23 C22 H22 121.3 . . ?
C14 C22 H22 121.3 . . ?
N4 C23 C22 126.0(15) . . ?
N4 C23 H23 117.0 . . ?
C22 C23 H23 117.0 . . ?
N4 C25 C26 124.0(17) . . ?
N4 C25 H25 118.0 . . ?
C26 C25 H25 118.0 . . ?
C14 C26 C25 121.9(15) . . ?
C14 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
O1P Cl1 O4P 112.4(12) . . ?
O1P Cl1 O3P 116.5(11) . . ?
O4P Cl1 O3P 116.5(10) . . ?
O1P Cl1 O2P 101.8(13) . . ?
O4P Cl1 O2P 104.5(12) . . ?
O3P Cl1 O2P 102.6(9) . . ?
N1 Cu1 N1 180.0(5) 2_765 . ?
N1 Cu1 N3 89.5(4) 2_765 2_765 ?
N1 Cu1 N3 90.5(4) . 2_765 ?
N1 Cu1 N3 90.5(4) 2_765 . ?
N1 Cu1 N3 89.5(4) . . ?
N3 Cu1 N3 180.0(5) 2_765 . ?
C20 Hg1 C20 180.000(1) 2_666 . ?
C15 Hg2 C14 178.5(5) . . ?
C10 N1 C8 115.7(9) . . ?
C10 N1 Cu1 122.3(8) . . ?
C8 N1 Cu1 121.8(7) . . ?
C4 N2 C6 116.7(11) . . ?
C13 N3 Cu1 112.1(7) . . ?
C13 N3 H1N 93(6) . . ?
Cu1 N3 H1N 113(6) . . ?
C13 N3 H2N 103(6) . . ?
Cu1 N3 H2N 117(6) . . ?
H1N N3 H2N 116(8) . . ?
C23 N4 C25 114.6(13) . . ?
C12 O1 H1A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.256
_refine_diff_density_min         -1.102
_refine_diff_density_rms         0.241
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1051165'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H60 Cl4 Cu4 Hg3 N10 O22'
_chemical_formula_weight         2054.73

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0200(5)
_cell_length_b                   14.2120(6)
_cell_length_c                   14.6203(7)
_cell_angle_alpha                104.840(3)
_cell_angle_beta                 97.235(3)
_cell_angle_gamma                93.608(5)
_cell_volume                     1590.12(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             982
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    8.771
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1492
_exptl_absorpt_correction_T_max  0.3025
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  stoe-ipds
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18726
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  0.1139
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             5572
_reflns_number_gt                3726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    Sir-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'diamond 3'
_computing_publication_material  'diamond 3'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+6.6680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     390
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      12.039
_refine_ls_shift/su_max          0.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3437(14) 0.0966(8) 0.2404(8) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.3980(16) 0.0438(10) 0.3031(9) 0.052(3) Uani 1 1 d . . . . .
H2 H 0.4820 0.0724 0.3545 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3302(16) -0.0514(9) 0.2913(9) 0.050(3) Uani 1 1 d . . . . .
H3 H 0.3696 -0.0849 0.3353 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1541(15) -0.0456(8) 0.1582(9) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.0672 -0.0755 0.1089 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2169(16) 0.0484(9) 0.1638(9) 0.045(3) Uani 1 1 d . . . . .
H5 H 0.1766 0.0795 0.1180 0.054 Uiso 1 1 calc R U . . .
C6 C 0.684(3) 0.4218(12) 0.3631(10) 0.086(6) Uani 1 1 d . . . . .
H6 H 0.6926 0.3915 0.4126 0.104 Uiso 1 1 calc R U . . .
C7 C 0.772(2) 0.5101(12) 0.3760(11) 0.079(5) Uani 1 1 d . . . . .
H7 H 0.8432 0.5376 0.4335 0.095 Uiso 1 1 calc R U . . .
C8 C 0.5699(17) 0.4267(9) 0.2085(10) 0.054(4) Uani 1 1 d . . . . .
H8 H 0.4989 0.4008 0.1508 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6641(16) 0.5153(9) 0.2252(9) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.6599 0.5462 0.1762 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5818(15) 0.3763(9) 0.2785(9) 0.043(3) Uani 1 1 d . . . . .
C12 C 0.759(3) 0.1791(15) 0.0793(13) 0.104(7) Uani 1 1 d . . . . .
H12 H 0.7230 0.1961 0.0232 0.125 Uiso 1 1 calc R U . . .
C13 C 0.7506(19) 0.0783(14) 0.1851(11) 0.068(4) Uani 1 1 d . . . . .
H13 H 0.7071 0.0233 0.2009 0.081 Uiso 1 1 calc R U . . .
C14 C 0.870(2) 0.1423(18) 0.2480(15) 0.094(6) Uani 1 1 d . . . . .
H14 H 0.9080 0.1282 0.3053 0.112 Uiso 1 1 calc R U . . .
C16 C 0.881(3) 0.2385(15) 0.1480(13) 0.094(6) Uani 1 1 d . . . . .
H16 H 0.9292 0.2933 0.1337 0.112 Uiso 1 1 calc R U . . .
C17B C 1.021(3) 0.5511(16) 0.157(2) 0.066(7) Uani 0.6 1 d D . P A 1
H17A H 0.9439 0.5442 0.0985 0.080 Uiso 0.6 1 calc R U P A 1
H17B H 0.9872 0.4996 0.1856 0.080 Uiso 0.6 1 calc R U P A 1
C18B C 1.153(5) 0.529(3) 0.115(3) 0.060(5) Uiso 0.4 1 d D . P A 2
H18A H 1.1898 0.4638 0.1033 0.072 Uiso 0.4 1 calc R U P A 2
H18B H 1.0599 0.5282 0.0654 0.072 Uiso 0.4 1 calc R U P A 2
C19B C 1.245(3) 0.6075(16) 0.0736(16) 0.060(5) Uiso 0.6 1 d D . P A 1
H19A H 1.3360 0.5836 0.0390 0.072 Uiso 0.6 1 calc R U P A 1
H19B H 1.1485 0.6118 0.0282 0.072 Uiso 0.6 1 calc R U P A 1
C20 C 0.818(2) 0.8548(11) 0.4816(12) 0.075(5) Uani 1 1 d . . . . .
H20A H 0.9342 0.8712 0.5122 0.091 Uiso 1 1 calc R U . . .
H20B H 0.7456 0.8772 0.5296 0.091 Uiso 1 1 calc R U . . .
C21 C 0.7864(19) 0.9056(11) 0.4052(13) 0.072(5) Uani 1 1 d . . . . .
H21A H 0.7697 0.9731 0.4343 0.086 Uiso 1 1 calc R U . . .
H21B H 0.6828 0.8752 0.3635 0.086 Uiso 1 1 calc R U . . .
C22 C 0.9277(18) 0.9042(9) 0.3449(10) 0.052(3) Uani 1 1 d . . . . .
H22A H 0.8941 0.9341 0.2937 0.063 Uiso 1 1 calc R U . . .
H22B H 1.0276 0.9428 0.3844 0.063 Uiso 1 1 calc R U . . .
C33 C 0.691(2) 0.0942(12) 0.0949(11) 0.064(4) Uani 1 1 d . . . . .
Cl1 Cl 0.7157(5) 0.7565(3) 0.0397(3) 0.0614(9) Uani 1 1 d . . . . .
Cl2 Cl 0.3151(4) 0.7504(3) 0.4587(2) 0.0587(9) Uani 1 1 d . . . . .
Cu1 Cu 0.88394(17) 0.68920(9) 0.32599(10) 0.0365(3) Uani 1 1 d . . . . .
Cu2 Cu 1.11477(18) 0.76759(10) 0.21245(10) 0.0401(3) Uani 1 1 d D . . . .
Hg1 Hg 0.45203(7) 0.23850(3) 0.25883(4) 0.04912(17) Uani 1 1 d . . . . .
Hg2 Hg 0.5000 0.0000 0.0000 0.0710(3) Uani 1 2 d S . P . .
N1 N 0.2094(12) -0.0965(7) 0.2185(7) 0.041(2) Uani 1 1 d . . . . .
N2 N 0.7613(13) 0.5593(7) 0.3083(7) 0.044(2) Uani 1 1 d . . . . .
N3 N 0.937(2) 0.2253(11) 0.2327(10) 0.080(4) Uani 1 1 d . . . . .
N4B N 1.249(3) 0.7005(18) 0.1116(18) 0.050(4) Uiso 0.4 1 d D . P A 2
H4BA H 1.1854 0.6971 0.0496 0.060 Uiso 0.4 1 calc R U P A 2
H4BB H 1.3527 0.7421 0.1179 0.060 Uiso 0.4 1 calc R U P A 2
N5 N 0.7844(17) 0.7475(9) 0.4430(9) 0.067(3) Uani 1 1 d . . . . .
H5A H 0.6630 0.7308 0.4289 0.080 Uiso 1 1 calc R U . . .
H5B H 0.8269 0.7173 0.4925 0.080 Uiso 1 1 calc R U . . .
O1 O 1.0136(10) 0.6456(5) 0.2225(6) 0.0420(19) Uani 1 1 d D . . . .
O2 O 0.9675(10) 0.8093(5) 0.3055(6) 0.0420(19) Uani 1 1 d . . . . .
O1W O 1.156(2) 0.3519(11) 0.3888(9) 0.133(6) Uani 1 1 d D U . . .
O3 O 0.1650(12) 0.6862(10) 0.4493(8) 0.086(4) Uani 1 1 d . . . . .
O4 O 0.274(2) 0.8516(10) 0.4974(11) 0.116(5) Uani 1 1 d . . . . .
O5 O 0.4504(14) 0.7320(10) 0.5241(9) 0.086(4) Uani 1 1 d . . . . .
O6 O 0.3693(13) 0.7438(9) 0.3689(7) 0.072(3) Uani 1 1 d . . . . .
O7 O 0.8925(14) 0.7660(12) 0.0664(10) 0.106(5) Uani 1 1 d . . . . .
O8 O 0.6484(18) 0.6637(11) 0.0373(12) 0.116(5) Uani 1 1 d . . . . .
O9 O 0.647(3) 0.8238(16) 0.1026(16) 0.184(10) Uani 1 1 d . . . . .
O10 O 0.678(2) 0.7719(16) -0.0525(12) 0.158(8) Uani 1 1 d . . . . .
H1WA H 1.226(3) 0.3135(17) 0.404(2) 0.13(2) Uiso 1 1 d D U . . .
H1WB H 1.105(4) 0.334(3) 0.3310(11) 0.09(6) Uiso 1 1 d D . . . .
C19A C 1.296(4) 0.600(2) 0.110(3) 0.060(5) Uiso 0.4 1 d D . P A 2
H19C H 1.3831 0.6052 0.1641 0.072 Uiso 0.4 1 calc R U P A 2
H19D H 1.3433 0.5741 0.0524 0.072 Uiso 0.4 1 calc R U P A 2
C17A C 1.092(5) 0.555(2) 0.211(3) 0.066(7) Uani 0.4 1 d D . P A 2
H17C H 1.0119 0.5034 0.2151 0.080 Uiso 0.4 1 calc R U P A 2
H17D H 1.1872 0.5631 0.2612 0.080 Uiso 0.4 1 calc R U P A 2
N4A N 1.300(2) 0.7041(13) 0.1444(12) 0.050(4) Uiso 0.6 1 d D . P A 1
H4AA H 1.3469 0.7484 0.1114 0.060 Uiso 0.6 1 calc R U P A 1
H4AB H 1.3890 0.6954 0.1919 0.060 Uiso 0.6 1 calc R U P A 1
C18A C 1.199(3) 0.543(2) 0.1353(19) 0.060(5) Uiso 0.6 1 d D . P A 1
H18C H 1.2101 0.4751 0.1028 0.072 Uiso 0.6 1 calc R U P A 1
H18D H 1.2765 0.5602 0.1948 0.072 Uiso 0.6 1 calc R U P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(18) . ?
C1 C5 1.410(16) . ?
C1 Hg1 2.083(10) . ?
C2 C3 1.385(16) . ?
C2 H2 0.9300 . ?
C3 N1 1.340(15) . ?
C3 H3 0.9300 . ?
C4 N1 1.330(15) . ?
C4 C5 1.376(16) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.36(2) . ?
C6 C10 1.373(19) . ?
C6 H6 0.9300 . ?
C7 N2 1.346(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(16) . ?
C8 C10 1.390(17) . ?
C8 H8 0.9300 . ?
C9 N2 1.336(15) . ?
C9 H9 0.9300 . ?
C10 Hg1 2.093(11) . ?
C12 C33 1.38(3) . ?
C12 C16 1.38(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.35(3) . ?
C13 C33 1.42(2) . ?
C13 H13 0.9300 . ?
C14 N3 1.35(3) . ?
C14 H14 0.9300 . ?
C16 N3 1.33(2) . ?
C16 H16 0.9300 . ?
C17B O1 1.445(18) . ?
C17B C18A 1.51(2) . ?
C17B H17A 0.9700 . ?
C17B H17B 0.9700 . ?
C18B C19A 1.50(2) . ?
C18B C17A 1.50(2) . ?
C18B H18A 0.9700 . ?
C18B H18B 0.9700 . ?
C19B N4A 1.49(2) . ?
C19B C18A 1.51(2) . ?
C19B H19A 0.9700 . ?
C19B H19B 0.9700 . ?
C20 N5 1.478(19) . ?
C20 C21 1.48(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.52(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O2 1.398(14) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C33 Hg2 2.078(17) . ?
Cl1 O9 1.343(16) . ?
Cl1 O8 1.383(13) . ?
Cl1 O7 1.411(11) . ?
Cl1 O10 1.419(14) . ?
Cl2 O6 1.417(11) . ?
Cl2 O3 1.435(11) . ?
Cl2 O5 1.436(10) . ?
Cl2 O4 1.479(13) . ?
Cu1 O2 1.902(7) . ?
Cu1 O1 1.937(8) . ?
Cu1 N2 1.977(9) . ?
Cu1 N5 1.988(11) . ?
Cu1 Cu2 2.9809(19) . ?
Cu2 O1 1.915(7) . ?
Cu2 O2 1.918(8) . ?
Cu2 N1 2.006(9) 1_665 ?
Cu2 N4B 2.014(17) . ?
Cu2 N4A 2.021(14) . ?
Hg2 C33 2.078(17) 2_655 ?
N1 Cu2 2.006(9) 1_445 ?
N4B C19A 1.49(3) . ?
N4B H4BA 0.9700 . ?
N4B H4BB 0.9700 . ?
N5 H5A 0.9700 . ?
N5 H5B 0.9700 . ?
O1 C17A 1.45(2) . ?
O1W H1WA 0.8585(7) . ?
O1W H1WB 0.8585(7) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
N4A H4AA 0.9700 . ?
N4A H4AB 0.9700 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 116.3(10) . . ?
C2 C1 Hg1 120.2(8) . . ?
C5 C1 Hg1 123.4(8) . . ?
C1 C2 C3 121.3(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
N1 C3 C2 122.0(11) . . ?
N1 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
N1 C4 C5 124.3(11) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C4 C5 C1 118.8(11) . . ?
C4 C5 H5 120.6 . . ?
C1 C5 H5 120.6 . . ?
C7 C6 C10 121.4(13) . . ?
C7 C6 H6 119.3 . . ?
C10 C6 H6 119.3 . . ?
N2 C7 C6 122.3(13) . . ?
N2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C9 C8 C10 119.4(11) . . ?
C9 C8 H8 120.3 . . ?
C10 C8 H8 120.3 . . ?
N2 C9 C8 123.4(11) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C6 C10 C8 116.5(11) . . ?
C6 C10 Hg1 120.8(9) . . ?
C8 C10 Hg1 122.7(8) . . ?
C33 C12 C16 119.0(17) . . ?
C33 C12 H12 120.5 . . ?
C16 C12 H12 120.5 . . ?
C14 C13 C33 120.7(18) . . ?
C14 C13 H13 119.7 . . ?
C33 C13 H13 119.7 . . ?
N3 C14 C13 124.0(17) . . ?
N3 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N3 C16 C12 126.4(19) . . ?
N3 C16 H16 116.8 . . ?
C12 C16 H16 116.8 . . ?
O1 C17B C18A 109.0(18) . . ?
O1 C17B H17A 109.9 . . ?
C18A C17B H17A 109.9 . . ?
O1 C17B H17B 109.9 . . ?
C18A C17B H17B 109.9 . . ?
H17A C17B H17B 108.3 . . ?
C19A C18B C17A 112(3) . . ?
C19A C18B H18A 109.3 . . ?
C17A C18B H18A 109.3 . . ?
C19A C18B H18B 109.3 . . ?
C17A C18B H18B 109.3 . . ?
H18A C18B H18B 108.0 . . ?
N4A C19B C18A 103.2(19) . . ?
N4A C19B H19A 111.1 . . ?
C18A C19B H19A 111.1 . . ?
N4A C19B H19B 111.1 . . ?
C18A C19B H19B 111.1 . . ?
H19A C19B H19B 109.1 . . ?
N5 C20 C21 111.5(14) . . ?
N5 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N5 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 114.2(13) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
O2 C22 C21 112.2(11) . . ?
O2 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
O2 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C12 C33 C13 115.4(16) . . ?
C12 C33 Hg2 123.3(13) . . ?
C13 C33 Hg2 121.1(13) . . ?
O9 Cl1 O8 109.8(15) . . ?
O9 Cl1 O7 109.7(12) . . ?
O8 Cl1 O7 110.1(9) . . ?
O9 Cl1 O10 109.0(15) . . ?
O8 Cl1 O10 109.1(10) . . ?
O7 Cl1 O10 109.2(10) . . ?
O6 Cl2 O3 111.4(7) . . ?
O6 Cl2 O5 109.6(7) . . ?
O3 Cl2 O5 112.2(6) . . ?
O6 Cl2 O4 108.2(9) . . ?
O3 Cl2 O4 107.5(9) . . ?
O5 Cl2 O4 107.8(8) . . ?
O2 Cu1 O1 77.7(3) . . ?
O2 Cu1 N2 162.9(4) . . ?
O1 Cu1 N2 94.7(4) . . ?
O2 Cu1 N5 96.7(4) . . ?
O1 Cu1 N5 170.8(4) . . ?
N2 Cu1 N5 92.6(5) . . ?
O2 Cu1 Cu2 38.9(2) . . ?
O1 Cu1 Cu2 39.0(2) . . ?
N2 Cu1 Cu2 133.1(3) . . ?
N5 Cu1 Cu2 134.3(3) . . ?
O1 Cu2 O2 77.8(3) . . ?
O1 Cu2 N1 172.3(4) . 1_665 ?
O2 Cu2 N1 94.8(4) . 1_665 ?
O1 Cu2 N4B 92.4(8) . . ?
O2 Cu2 N4B 170.0(8) . . ?
N1 Cu2 N4B 95.1(8) 1_665 . ?
O1 Cu2 N4A 93.1(6) . . ?
O2 Cu2 N4A 162.7(6) . . ?
N1 Cu2 N4A 93.5(6) 1_665 . ?
O1 Cu2 Cu1 39.6(2) . . ?
O2 Cu2 Cu1 38.5(2) . . ?
N1 Cu2 Cu1 132.8(3) 1_665 . ?
N4B Cu2 Cu1 131.8(8) . . ?
N4A Cu2 Cu1 129.6(5) . . ?
C1 Hg1 C10 174.9(5) . . ?
C33 Hg2 C33 180.0 . 2_655 ?
C4 N1 C3 117.3(10) . . ?
C4 N1 Cu2 124.5(8) . 1_445 ?
C3 N1 Cu2 118.1(8) . 1_445 ?
C9 N2 C7 116.9(10) . . ?
C9 N2 Cu1 119.8(8) . . ?
C7 N2 Cu1 123.3(9) . . ?
C16 N3 C14 114.5(17) . . ?
C19A N4B Cu2 119(2) . . ?
C19A N4B H4BA 107.7 . . ?
Cu2 N4B H4BA 107.7 . . ?
C19A N4B H4BB 107.7 . . ?
Cu2 N4B H4BB 107.7 . . ?
H4BA N4B H4BB 107.1 . . ?
C20 N5 Cu1 116.0(9) . . ?
C20 N5 H5A 108.3 . . ?
Cu1 N5 H5A 108.3 . . ?
C20 N5 H5B 108.3 . . ?
Cu1 N5 H5B 108.3 . . ?
H5A N5 H5B 107.4 . . ?
C17B O1 Cu2 125.5(13) . . ?
C17A O1 Cu2 126.1(17) . . ?
C17B O1 Cu1 132.6(12) . . ?
C17A O1 Cu1 120.9(15) . . ?
Cu2 O1 Cu1 101.4(4) . . ?
C22 O2 Cu1 129.3(8) . . ?
C22 O2 Cu2 128.1(7) . . ?
Cu1 O2 Cu2 102.6(4) . . ?
H1WA O1W H1WB 115.25(14) . . ?
N4B C19A C18B 115(3) . . ?
N4B C19A H19C 108.5 . . ?
C18B C19A H19C 108.5 . . ?
N4B C19A H19D 108.5 . . ?
C18B C19A H19D 108.5 . . ?
H19C C19A H19D 107.5 . . ?
O1 C17A C18B 110(3) . . ?
O1 C17A H17C 109.8 . . ?
C18B C17A H17C 109.8 . . ?
O1 C17A H17D 109.8 . . ?
C18B C17A H17D 109.8 . . ?
H17C C17A H17D 108.2 . . ?
C19B N4A Cu2 114.9(14) . . ?
C19B N4A H4AA 108.5 . . ?
Cu2 N4A H4AA 108.5 . . ?
C19B N4A H4AB 108.5 . . ?
Cu2 N4A H4AB 108.5 . . ?
H4AA N4A H4AB 107.5 . . ?
C17B C18A C19B 112(2) . . ?
C17B C18A H18C 109.2 . . ?
C19B C18A H18C 109.2 . . ?
C17B C18A H18D 109.2 . . ?
C19B C18A H18D 109.2 . . ?
H18C C18A H18D 107.9 . . ?

_refine_diff_density_max         1.140
_refine_diff_density_min         -1.301
_refine_diff_density_rms         0.185

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1051166'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H32 B2 Cu2 F8 Hg2 N6 O2'
_chemical_formula_weight         1162.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.5149(11)
_cell_length_b                   12.0894(12)
_cell_length_c                   29.347(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.740(8)
_cell_angle_gamma                90
_cell_volume                     3726.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_F_000             2184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    9.413
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  stoe-ipds
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73828
_diffrn_reflns_av_unetI/netI     0.1947
_diffrn_reflns_av_R_equivalents  0.1544
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         33.939
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14636
_reflns_number_gt                2357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREa
_computing_cell_refinement       X-AREa
_computing_data_reduction        X-AREa
_computing_structure_solution    Sir-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00089(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         14636
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2430
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   0.629
_refine_ls_restrained_S_all      0.629
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C0AA C 0.809(2) 0.8858(13) 0.6502(8) 0.125(6) Uani 1 1 d . . . . .
H0AA H 0.8045 0.8896 0.6831 0.150 Uiso 1 1 calc R U . . .
H0AB H 0.8889 0.9198 0.6424 0.150 Uiso 1 1 calc R U . . .
C1A C 0.4495 0.5100 0.6022 0.114(6) Uani 1 1 d . . . . .
H1AA H 0.5080 0.4561 0.6158 0.137 Uiso 1 1 calc R U . . .
H1AB H 0.4607 0.5102 0.5696 0.137 Uiso 1 1 calc R U . . .
C4AA C 0.7461(15) 0.4703(11) 0.6740(5) 0.091(5) Uani 1 1 d . . . . .
H4AA H 0.6993 0.4872 0.6992 0.109 Uiso 1 1 calc R U . . .
C1AA C 0.1475(17) 0.9970(14) 0.6673(6) 0.102(5) Uani 1 1 d . . . . .
H1AC H 0.1086 1.0042 0.6949 0.122 Uiso 1 1 calc R U . . .
C2AA C 0.2667(17) 0.9626(13) 0.5888(6) 0.106(5) Uani 1 1 d . . . . .
H2AA H 0.3111 0.9547 0.5623 0.127 Uiso 1 1 calc R U . . .
C4A C 0.8207(18) 0.3711(13) 0.6742(5) 0.107(5) Uani 1 1 d . . . . .
H4A H 0.8223 0.3254 0.6997 0.128 Uiso 1 1 calc R U . . .
C3AA C 0.3264(16) 0.7855(14) 0.4572(5) 0.106(5) Uani 1 1 d . . . . .
H3AA H 0.2581 0.7994 0.4367 0.127 Uiso 1 1 calc R U . . .
C6 C 0.5158(14) 0.7546(14) 0.5196(4) 0.097(5) Uani 1 1 d . . . . .
H6 H 0.5822 0.7467 0.5415 0.117 Uiso 1 1 calc R U . . .
C7 C 0.3067(14) 0.7744(13) 0.5024(4) 0.096(5) Uani 1 1 d . . . . .
H7 H 0.2234 0.7784 0.5116 0.116 Uiso 1 1 calc R U . . .
C5AA C 0.5463(15) 0.7613(13) 0.4755(4) 0.097(5) Uani 1 1 d . . . . .
H5AA H 0.6307 0.7563 0.4675 0.116 Uiso 1 1 calc R U . . .
C9 C 0.4555(14) 0.8310(12) 0.2722(5) 0.090(4) Uani 1 1 d . . . . .
H9 H 0.3709 0.8436 0.2784 0.108 Uiso 1 1 calc R U . . .
C10 C 0.4910(14) 0.8461(13) 0.2298(4) 0.090(4) Uani 1 1 d . . . . .
H10 H 0.4326 0.8766 0.2086 0.109 Uiso 1 1 calc R U . . .
C11 C 0.6573(18) 0.7648(13) 0.2937(4) 0.103(5) Uani 1 1 d . . . . .
H11 H 0.7149 0.7328 0.3148 0.124 Uiso 1 1 calc R U . . .
C12 C 0.6909(15) 0.7807(15) 0.2473(5) 0.108(5) Uani 1 1 d . . . . .
H12 H 0.7729 0.7636 0.2390 0.129 Uiso 1 1 calc R U . . .
C13 C 0.1879(18) 1.0564(12) 0.5927(6) 0.106(5) Uani 1 1 d . . . . .
H13 H 0.1746 1.1047 0.5683 0.128 Uiso 1 1 calc R U . . .
C14 C 0.1302(15) 1.0753(16) 0.6339(7) 0.109(5) Uani 1 1 d . . . . .
C15 C 0.2257(15) 0.9050(12) 0.6590(5) 0.090(5) Uani 1 1 d . . . . .
H15 H 0.2392 0.8541 0.6825 0.108 Uiso 1 1 calc R U . . .
C17 C 0.3140(16) 0.4744(14) 0.6107(7) 0.105(5) Uani 1 1 d . . . . .
H17A H 0.3017 0.3990 0.6002 0.126 Uiso 1 1 calc R U . . .
H17B H 0.3022 0.4754 0.6433 0.126 Uiso 1 1 calc R U . . .
C18 C 0.2190(17) 0.5443(15) 0.5883(7) 0.115(6) Uani 1 1 d . . . . .
H18A H 0.1364 0.5089 0.5894 0.138 Uiso 1 1 calc R U . . .
H18B H 0.2382 0.5525 0.5565 0.138 Uiso 1 1 calc R U . . .
C20 C 0.8824(14) 0.4113(13) 0.6010(6) 0.099(5) Uani 1 1 d . . . . .
H20 H 0.9288 0.3978 0.5754 0.119 Uiso 1 1 calc R U . . .
C21 C 0.8014(15) 0.5077(13) 0.6021(5) 0.086(4) Uani 1 1 d . . . . .
H21 H 0.7900 0.5505 0.5759 0.104 Uiso 1 1 calc R U . . .
C22 C 0.707(2) 0.9485(15) 0.6298(8) 0.125(7) Uani 1 1 d . . . . .
H22A H 0.7137 0.9461 0.5970 0.150 Uiso 1 1 calc R U . . .
H22B H 0.7179 1.0249 0.6392 0.150 Uiso 1 1 calc R U . . .
C23 C 0.5798(18) 0.9139(13) 0.6403(6) 0.111(6) Uani 1 1 d . . . . .
H23A H 0.5717 0.9210 0.6729 0.133 Uiso 1 1 calc R U . . .
H23B H 0.5199 0.9651 0.6256 0.133 Uiso 1 1 calc R U . . .
C24 C 0.4480(15) 0.7759(11) 0.4418(4) 0.084(4) Uani 1 1 d . . . . .
C25 C 0.5365(17) 0.7981(12) 0.3067(4) 0.089(4) Uani 1 1 d . . . . .
C26 C 0.8918(16) 0.3411(12) 0.6364(5) 0.093(5) Uani 1 1 d . . . . .
N1 N 0.3982(12) 0.7583(10) 0.5342(3) 0.088(3) Uani 1 1 d . . . . .
N2 N 0.8119 0.7653 0.6362 0.091(3) Uani 1 1 d . . . . .
H2A H 0.8765 0.7280 0.6553 0.110 Uiso 1 1 calc R U . . .
H2B H 0.8383 0.7614 0.6050 0.110 Uiso 1 1 calc R U . . .
N3 N 0.2128(11) 0.6601(9) 0.6106(4) 0.084(3) Uani 1 1 d . . . . .
H3A H 0.1881 0.6513 0.6418 0.101 Uiso 1 1 calc R U . . .
H3B H 0.1468 0.7027 0.5944 0.101 Uiso 1 1 calc R U . . .
N4 N 0.6070(12) 0.8195(9) 0.2160(3) 0.081(3) Uani 1 1 d . . . . .
N5 N 0.2812(11) 0.8857(9) 0.6204(4) 0.080(3) Uani 1 1 d . . . . .
N6 N 0.7426(11) 0.5372(10) 0.6393(4) 0.082(3) Uani 1 1 d . . . . .
O1 O 0.5438(8) 0.8087(7) 0.6278(2) 0.070(2) Uani 1 1 d . . . . .
O2 O 0.4814(7) 0.6173(7) 0.6202(2) 0.070(2) Uani 1 1 d . . . . .
Cu1 Cu 0.6476 0.6811 0.6400 0.0705(4) Uani 1 1 d . . . . .
Cu2 Cu 0.37677(15) 0.74654(12) 0.61093(5) 0.0714(4) Uani 1 1 d . . . . .
Hg1 Hg 0.49018(7) 0.78369(5) 0.37360(2) 0.0897(2) Uani 1 1 d . . . . .
Hg2 Hg 0.00470(6) 1.20697(5) 0.63593(2) 0.1012(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C0AA C22 1.42(2) . ?
C0AA N2 1.513(16) . ?
C1A O2 1.435(8) . ?
C1A C17 1.520(16) . ?
C4AA N6 1.300(16) . ?
C4AA C4A 1.43(2) . ?
C1AA C14 1.37(2) . ?
C1AA C15 1.41(2) . ?
C2AA N5 1.317(17) . ?
C2AA C13 1.413(19) . ?
C4A C26 1.41(2) . ?
C3AA C7 1.358(16) . ?
C3AA C24 1.38(2) . ?
C6 N1 1.328(16) . ?
C6 C5AA 1.351(17) . ?
C7 N1 1.322(15) . ?
C5AA C24 1.407(18) . ?
C9 C10 1.328(17) . ?
C9 C25 1.351(18) . ?
C10 N4 1.341(16) . ?
C11 C25 1.40(2) . ?
C11 C12 1.436(18) . ?
C12 N4 1.328(17) . ?
C13 C14 1.40(2) . ?
C14 Hg2 2.070(18) . ?
C15 N5 1.317(16) . ?
C17 C18 1.44(2) . ?
C18 N3 1.548(19) . ?
C20 C26 1.34(2) . ?
C20 C21 1.44(2) . ?
C21 N6 1.327(17) . ?
C22 C23 1.45(2) . ?
C23 O1 1.371(16) . ?
C24 Hg1 2.071(13) . ?
C25 Hg1 2.054(14) . ?
C26 Hg2 2.010(15) 1_645 ?
N1 Cu2 2.280(10) . ?
N2 Cu1 2.01270(16) . ?
N3 Cu2 2.016(12) . ?
N4 Cu1 2.292(10) 4_575 ?
N5 Cu2 1.987(12) . ?
N6 Cu1 2.007(11) . ?
O1 Cu1 1.913(8) . ?
O1 Cu2 1.952(8) . ?
O2 Cu2 1.923(8) . ?
O2 Cu1 1.972(8) . ?
Cu1 N4 2.292(10) 4_576 ?
Cu1 Cu2 3.0381(16) . ?
Hg2 C26 2.010(15) 1_465 ?

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
C22 C0AA N2 115.0(15) . . ?
O2 C1A C17 113.6(8) . . ?
N6 C4AA C4A 121.3(13) . . ?
C14 C1AA C15 118.8(16) . . ?
N5 C2AA C13 123.9(15) . . ?
C26 C4A C4AA 121.4(13) . . ?
C7 C3AA C24 120.0(14) . . ?
N1 C6 C5AA 125.0(13) . . ?
N1 C7 C3AA 124.3(14) . . ?
C6 C5AA C24 118.8(14) . . ?
C10 C9 C25 123.1(14) . . ?
C9 C10 N4 123.4(13) . . ?
C25 C11 C12 119.1(15) . . ?
N4 C12 C11 121.1(15) . . ?
C14 C13 C2AA 118.8(14) . . ?
C1AA C14 C13 117.2(16) . . ?
C1AA C14 Hg2 125.2(12) . . ?
C13 C14 Hg2 117.0(13) . . ?
N5 C15 C1AA 124.9(15) . . ?
C18 C17 C1A 113.2(13) . . ?
C17 C18 N3 112.3(14) . . ?
C26 C20 C21 121.0(15) . . ?
N6 C21 C20 122.2(14) . . ?
C0AA C22 C23 116.4(17) . . ?
O1 C23 C22 117.3(14) . . ?
C3AA C24 C5AA 116.0(12) . . ?
C3AA C24 Hg1 123.9(10) . . ?
C5AA C24 Hg1 120.1(11) . . ?
C9 C25 C11 115.3(13) . . ?
C9 C25 Hg1 124.9(12) . . ?
C11 C25 Hg1 119.7(11) . . ?
C20 C26 C4A 115.0(14) . . ?
C20 C26 Hg2 121.8(12) . 1_645 ?
C4A C26 Hg2 123.2(10) . 1_645 ?
C7 N1 C6 115.9(11) . . ?
C7 N1 Cu2 127.1(10) . . ?
C6 N1 Cu2 116.9(8) . . ?
C0AA N2 Cu1 116.4(8) . . ?
C18 N3 Cu2 114.7(9) . . ?
C12 N4 C10 117.4(12) . . ?
C12 N4 Cu1 121.5(10) . 4_575 ?
C10 N4 Cu1 120.6(8) . 4_575 ?
C15 N5 C2AA 116.1(13) . . ?
C15 N5 Cu2 121.2(9) . . ?
C2AA N5 Cu2 122.7(10) . . ?
C4AA N6 C21 118.7(12) . . ?
C4AA N6 Cu1 121.8(9) . . ?
C21 N6 Cu1 119.6(9) . . ?
C23 O1 Cu1 123.4(9) . . ?
C23 O1 Cu2 131.2(9) . . ?
Cu1 O1 Cu2 103.6(4) . . ?
C1A O2 Cu2 124.1(5) . . ?
C1A O2 Cu1 130.6(5) . . ?
Cu2 O2 Cu1 102.5(4) . . ?
O1 Cu1 O2 76.7(3) . . ?
O1 Cu1 N6 167.6(4) . . ?
O2 Cu1 N6 95.3(4) . . ?
O1 Cu1 N2 93.8(2) . . ?
O2 Cu1 N2 158.8(2) . . ?
N6 Cu1 N2 90.5(3) . . ?
O1 Cu1 N4 93.0(3) . 4_576 ?
O2 Cu1 N4 94.7(4) . 4_576 ?
N6 Cu1 N4 97.1(4) . 4_576 ?
N2 Cu1 N4 104.8(3) . 4_576 ?
O1 Cu1 Cu2 38.7(2) . . ?
O2 Cu1 Cu2 38.2(2) . . ?
N6 Cu1 Cu2 133.1(4) . . ?
N2 Cu1 Cu2 130.43(3) . . ?
N4 Cu1 Cu2 93.3(3) 4_576 . ?
O2 Cu2 O1 77.0(3) . . ?
O2 Cu2 N5 163.4(4) . . ?
O1 Cu2 N5 95.4(4) . . ?
O2 Cu2 N3 93.6(4) . . ?
O1 Cu2 N3 163.7(4) . . ?
N5 Cu2 N3 90.1(5) . . ?
O2 Cu2 N1 96.2(4) . . ?
O1 Cu2 N1 95.5(4) . . ?
N5 Cu2 N1 99.2(4) . . ?
N3 Cu2 N1 98.7(5) . . ?
O2 Cu2 Cu1 39.3(2) . . ?
O1 Cu2 Cu1 37.7(2) . . ?
N5 Cu2 Cu1 130.9(3) . . ?
N3 Cu2 Cu1 131.0(3) . . ?
N1 Cu2 Cu1 99.1(3) . . ?
C25 Hg1 C24 177.3(6) . . ?
C26 Hg2 C14 176.3(7) 1_465 . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.160

_shelxl_version_number           2013-4
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.007 -0.014 0.000 245.4 43.9
2 0.000 0.839 0.250 195.1 46.4
3 0.015 0.086 0.500 245.4 42.8
4 0.000 0.646 0.750 195.3 46.9
5 0.370 0.507 0.486 13.3 0.4
6 0.370 -0.007 0.986 13.2 -0.3
7 0.452 0.590 0.245 12.4 1.0
8 0.452 0.910 0.745 12.3 0.8
9 0.547 0.089 0.255 13.0 0.6
10 0.547 0.410 0.755 12.8 0.5
11 0.629 1.007 0.014 12.9 -0.7
12 0.629 0.493 0.514 12.8 -0.7
_platon_squeeze_details          
; ?
;

####################################################################### 
# 
# 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_exp_2648
_database_code_depnum_ccdc_archive 'CCDC 1051167'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_audit_creation_date             2015-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H18 Hg N2 O2'
_chemical_formula_sum            'C22 H18 Hg N2 O2'
_chemical_formula_weight         542.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 N2 O4 Hg1'
_chemical_oxdiff_usercomment     Py2Hg(OHPh)
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.6075(13)
_cell_length_b                   8.1508(12)
_cell_length_c                   15.9817(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.662(7)
_cell_angle_gamma                90.00
_cell_volume                     1896.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3030
_cell_measurement_theta_min      2.5310
_exptl_absorpt_coefficient_mu    8.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.1534
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8800
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   34.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0127   77.0000  150.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   16.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0127  -99.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   46.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  -19.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   66.00   90.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  178.0000  -30.0000 24
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0117841000
_diffrn_orient_matrix_UB_12      0.0433135000
_diffrn_orient_matrix_UB_13      0.0361122000
_diffrn_orient_matrix_UB_21      0.0141802000
_diffrn_orient_matrix_UB_22      0.0745065000
_diffrn_orient_matrix_UB_23      -0.0178133000
_diffrn_orient_matrix_UB_31      -0.0451167000
_diffrn_orient_matrix_UB_32      0.0122083000
_diffrn_orient_matrix_UB_33      -0.0189466000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2195
_reflns_number_total             3833
_reflns_odcompleteness_completeness 98.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.863
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1134
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2), O1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C12(H12), C19(H19), C9(H9), C8(H8), C3(H3), C18(H18), C15(H15),
 C16(H16), C7(H7), C2(H2A), C13(H13), C10(H10), C4(H4), C5(H5), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Hg1 Hg 0.21305(3) 0.48027(6) 0.73231(2) 0.05003(19) Uani 1 d . . .
O2 O 1.0345(4) 0.4679(9) 0.8333(4) 0.045(2) Uani 1 d . . .
H2 H 1.0426 0.4066 0.8739 0.068 Uiso 1 d . . R
C17 C 0.7574(6) 0.4983(12) 0.7473(5) 0.033(2) Uani 1 d . . .
O1 O 0.3830(4) 0.5332(9) 0.6197(4) 0.051(2) Uani 1 d . . .
H1 H 0.3751 0.6005 0.5816 0.076 Uiso 1 d . . R
C21 C 0.9183(6) 0.5699(15) 0.7378(6) 0.046(3) Uani 1 d . . .
H21 H 0.9626 0.6275 0.7113 0.055 Uiso 1 calc . . R
N2 N 0.3353(6) 0.7537(12) 0.9901(5) 0.050(3) Uani 1 d . . .
C1 C 0.1610(7) 0.3691(15) 0.6224(5) 0.044(3) Uani 1 d . . .
N1 N 0.0852(6) 0.2009(13) 0.4780(4) 0.052(3) Uani 1 d . . .
C12 C 0.5396(7) 0.6255(16) 0.6161(6) 0.054(3) Uani 1 d . . .
H12 H 0.5229 0.6998 0.5734 0.064 Uiso 1 calc . . R
C19 C 0.8772(6) 0.3922(14) 0.8454(6) 0.040(3) Uani 1 d . . .
H19 H 0.8937 0.3229 0.8903 0.048 Uiso 1 calc . . R
C9 C 0.2477(7) 0.7725(14) 0.9595(5) 0.041(3) Uani 1 d . . .
H9 H 0.2092 0.8405 0.9876 0.050 Uiso 1 calc . . R
C8 C 0.3861(8) 0.6544(18) 0.9488(7) 0.068(4) Uani 1 d . . .
H8 H 0.4473 0.6407 0.9687 0.081 Uiso 1 calc . . R
C3 C 0.1748(7) 0.2002(15) 0.5009(5) 0.047(3) Uani 1 d . . .
H3 H 0.2135 0.1419 0.4683 0.056 Uiso 1 calc . . R
C20 C 0.9430(6) 0.4743(13) 0.8079(5) 0.032(2) Uani 1 d . . .
C18 C 0.7844(6) 0.4101(14) 0.8175(6) 0.042(3) Uani 1 d . . .
H18 H 0.7401 0.3606 0.8476 0.050 Uiso 1 calc . . R
C6 C 0.2629(7) 0.5900(15) 0.8435(6) 0.042(3) Uani 1 d . . .
C14 C 0.6580(6) 0.5124(13) 0.7121(5) 0.032(3) Uani 1 d . . .
C15 C 0.5914(7) 0.4117(16) 0.7426(6) 0.052(3) Uani 1 d . . .
H15 H 0.6082 0.3391 0.7861 0.062 Uiso 1 calc . . R
C16 C 0.5009(6) 0.4168(15) 0.7096(6) 0.049(3) Uani 1 d . . .
H16 H 0.4580 0.3455 0.7296 0.059 Uiso 1 calc . . R
C7 C 0.3543(7) 0.5692(16) 0.8778(7) 0.064(4) Uani 1 d . . .
H7 H 0.3932 0.4978 0.8523 0.077 Uiso 1 calc . . R
C2 C 0.2133(6) 0.2835(14) 0.5719(6) 0.048(3) Uani 1 d . . .
H2A H 0.2766 0.2798 0.5845 0.058 Uiso 1 calc . . R
C13 C 0.6310(6) 0.6137(15) 0.6483(6) 0.055(3) Uani 1 d . . .
H13 H 0.6748 0.6782 0.6249 0.066 Uiso 1 calc . . R
C11 C 0.4745(7) 0.5276(14) 0.6474(6) 0.039(3) Uani 1 d . . .
C10 C 0.2134(7) 0.6936(15) 0.8875(6) 0.047(3) Uani 1 d . . .
H10 H 0.1526 0.7129 0.8682 0.056 Uiso 1 calc . . R
C4 C 0.0353(8) 0.278(2) 0.5275(7) 0.091(6) Uani 1 d . . .
H4 H -0.0279 0.2758 0.5145 0.109 Uiso 1 calc . . R
C5 C 0.0677(7) 0.3625(19) 0.5984(7) 0.083(5) Uani 1 d . . .
H5 H 0.0265 0.4160 0.6304 0.099 Uiso 1 calc . . R
C22 C 0.8260(6) 0.5787(14) 0.7075(6) 0.038(3) Uani 1 d . . .
H22 H 0.8098 0.6400 0.6595 0.046 Uiso 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 O2 27.784(6) 4_666 ?
Hg1 O1 3.212(7) . ?
Hg1 C1 2.065(9) . ?
Hg1 C6 2.069(9) . ?
O2 H2 0.8200 . ?
O2 C20 1.366(9) . ?
C17 C18 1.363(12) . ?
C17 C14 1.519(11) . ?
C17 C22 1.393(13) . ?
O1 H1 0.8205 . ?
O1 C11 1.373(10) . ?
C21 H21 0.9300 . ?
C21 C20 1.388(12) . ?
C21 C22 1.397(11) . ?
N2 C9 1.341(10) . ?
N2 C8 1.312(14) . ?
C1 C2 1.350(14) . ?
C1 C5 1.388(12) . ?
N1 C3 1.329(11) . ?
N1 C4 1.281(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(11) . ?
C12 C11 1.367(14) . ?
C19 H19 0.9300 . ?
C19 C20 1.351(13) . ?
C19 C18 1.399(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(12) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(12) . ?
C18 H18 0.9300 . ?
C6 C7 1.411(12) . ?
C6 C10 1.346(14) . ?
C14 C15 1.391(14) . ?
C14 C13 1.345(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(11) . ?
C16 H16 0.9300 . ?
C16 C11 1.376(13) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.378(14) . ?
C5 H5 0.9300 . ?
C22 H22 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
O1 Hg1 O2 56.58(10) . 4_666 ?
C1 Hg1 O2 120.8(3) . 4_666 ?
C1 Hg1 O1 80.2(3) . . ?
C1 Hg1 C6 178.9(4) . . ?
C6 Hg1 O2 60.0(3) . 4_666 ?
C6 Hg1 O1 100.9(3) . . ?
C20 O2 H2 109.5 . . ?
C18 C17 C14 123.3(9) . . ?
C18 C17 C22 117.0(8) . . ?
C22 C17 C14 119.7(8) . . ?
Hg1 O1 H1 115.9 . . ?
C11 O1 Hg1 126.2(5) . . ?
C11 O1 H1 109.6 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.3(9) . . ?
C22 C21 H21 120.4 . . ?
C8 N2 C9 116.8(8) . . ?
C2 C1 Hg1 123.3(7) . . ?
C2 C1 C5 113.9(9) . . ?
C5 C1 Hg1 122.5(8) . . ?
C4 N1 C3 115.4(9) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(9) . . ?
C20 C19 H19 119.6 . . ?
C20 C19 C18 120.8(9) . . ?
C18 C19 H19 119.6 . . ?
N2 C9 H9 119.3 . . ?
N2 C9 C10 121.5(10) . . ?
C10 C9 H9 119.3 . . ?
N2 C8 H8 118.1 . . ?
N2 C8 C7 123.9(10) . . ?
C7 C8 H8 118.1 . . ?
N1 C3 H3 118.6 . . ?
N1 C3 C2 122.9(9) . . ?
C2 C3 H3 118.6 . . ?
O2 C20 C21 116.5(9) . . ?
C19 C20 O2 124.3(8) . . ?
C19 C20 C21 119.2(8) . . ?
C17 C18 C19 121.6(10) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C7 C6 Hg1 122.5(8) . . ?
C10 C6 Hg1 123.6(7) . . ?
C10 C6 C7 113.8(9) . . ?
C15 C14 C17 120.0(8) . . ?
C13 C14 C17 122.7(9) . . ?
C13 C14 C15 117.2(8) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.5(9) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 C15 119.9(10) . . ?
C11 C16 H16 120.0 . . ?
C8 C7 C6 120.3(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C1 C2 C3 121.7(9) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.4(10) . . ?
C14 C13 H13 118.8 . . ?
O1 C11 C16 117.6(10) . . ?
C12 C11 O1 123.4(9) . . ?
C12 C11 C16 119.0(9) . . ?
C9 C10 H10 118.1 . . ?
C6 C10 C9 123.8(9) . . ?
C6 C10 H10 118.1 . . ?
N1 C4 H4 117.3 . . ?
N1 C4 C5 125.3(11) . . ?
C5 C4 H4 117.3 . . ?
C1 C5 H5 119.6 . . ?
C4 C5 C1 120.7(11) . . ?
C4 C5 H5 119.6 . . ?
C17 C22 C21 121.8(9) . . ?
C17 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.94 2.741(10) 166.0 4_666
O1 H1 N2 0.82 1.94 2.749(11) 170.3 4_575

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
Hg1 O1 C11 C12 -144.8(9) . . . . ?
Hg1 O1 C11 C16 35.4(13) . . . . ?
Hg1 C1 C2 C3 175.5(8) . . . . ?
Hg1 C1 C5 C4 -175.6(12) . . . . ?
Hg1 C6 C7 C8 175.3(10) . . . . ?
Hg1 C6 C10 C9 -177.0(8) . . . . ?
O2 Hg1 O1 C11 -6.3(7) 4_666 . . . ?
O2 Hg1 C1 C2 -5.9(11) 4_666 . . . ?
O2 Hg1 C1 C5 167.6(10) 4_666 . . . ?
O2 Hg1 C6 C7 -1.1(8) 4_666 . . . ?
O2 Hg1 C6 C10 175.4(11) 4_666 . . . ?
C17 C14 C15 C16 -177.5(10) . . . . ?
C17 C14 C13 C12 179.7(10) . . . . ?
O1 Hg1 C1 C2 35.2(10) . . . . ?
O1 Hg1 C1 C5 -151.3(11) . . . . ?
O1 Hg1 C6 C7 -41.7(10) . . . . ?
O1 Hg1 C6 C10 134.8(10) . . . . ?
N2 C9 C10 C6 1.6(17) . . . . ?
N2 C8 C7 C6 2(2) . . . . ?
C1 Hg1 O1 C11 -143.7(8) . . . . ?
C1 Hg1 C6 C7 131(22) . . . . ?
C1 Hg1 C6 C10 -52(22) . . . . ?
N1 C3 C2 C1 0.7(17) . . . . ?
N1 C4 C5 C1 -1(3) . . . . ?
C9 N2 C8 C7 -1(2) . . . . ?
C8 N2 C9 C10 -1.1(16) . . . . ?
C3 N1 C4 C5 3(2) . . . . ?
C20 C21 C22 C17 2.1(16) . . . . ?
C20 C19 C18 C17 6.1(17) . . . . ?
C18 C17 C14 C15 -11.1(16) . . . . ?
C18 C17 C14 C13 172.6(11) . . . . ?
C18 C17 C22 C21 0.0(16) . . . . ?
C18 C19 C20 O2 177.5(9) . . . . ?
C18 C19 C20 C21 -3.8(16) . . . . ?
C6 Hg1 O1 C11 36.1(8) . . . . ?
C6 Hg1 C1 C2 -138(21) . . . . ?
C6 Hg1 C1 C5 36(22) . . . . ?
C14 C17 C18 C19 176.3(9) . . . . ?
C14 C17 C22 C21 179.7(9) . . . . ?
C14 C15 C16 C11 -2.3(18) . . . . ?
C15 C14 C13 C12 3.3(17) . . . . ?
C15 C16 C11 O1 -176.9(9) . . . . ?
C15 C16 C11 C12 3.2(17) . . . . ?
C7 C6 C10 C9 -0.2(17) . . . . ?
C2 C1 C5 C4 -1(2) . . . . ?
C13 C12 C11 O1 179.2(10) . . . . ?
C13 C12 C11 C16 -1.0(17) . . . . ?
C13 C14 C15 C16 -0.9(17) . . . . ?
C11 C12 C13 C14 -2.4(19) . . . . ?
C10 C6 C7 C8 -1.5(17) . . . . ?
C4 N1 C3 C2 -2.9(18) . . . . ?
C5 C1 C2 C3 1.4(17) . . . . ?
C22 C17 C18 C19 -4.0(16) . . . . ?
C22 C17 C14 C15 169.3(10) . . . . ?
C22 C17 C14 C13 -7.1(16) . . . . ?
C22 C21 C20 O2 178.6(9) . . . . ?
C22 C21 C20 C19 -0.1(16) . . . . ?

_olex2_date_sample_data_collection 2014-07-13
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_crystal5
_database_code_depnum_ccdc_archive 'CCDC 1051168'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Hg N2 O3'
_chemical_formula_weight         482.88

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.150(4)
_cell_length_b                   10.919(2)
_cell_length_c                   14.603(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3053.4(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    10.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_T_max  0.4376
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  stoe-ipds
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14934
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.908
_reflns_number_total             5009
_reflns_number_gt                3085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_max     0.859
_reflns_Friedel_fraction_full    0.839

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    Sir-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'diamond 3'
_computing_publication_material  'diamond 3'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5009
_refine_ls_number_parameters     378
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.014
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4358(16) 0.166(3) 0.100(3) 0.048(5) Uani 1 1 d . U . . .
C2 C 0.4388(16) 0.297(3) 0.087(3) 0.045(5) Uani 1 1 d . U . . .
C3 C 0.5003(14) 0.355(2) 0.113(3) 0.041(8) Uani 1 1 d . . . . .
C4 C 0.5559(17) 0.291(3) 0.147(2) 0.051(9) Uani 1 1 d . . . . .
H3B H 0.5953 0.3332 0.1663 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5546(16) 0.165(3) 0.153(2) 0.056(9) Uani 1 1 d . . . . .
H2B H 0.5943 0.1215 0.1705 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4947(17) 0.105(3) 0.134(4) 0.065(12) Uani 1 1 d . . . . .
H1B H 0.4924 0.0212 0.1430 0.078 Uiso 1 1 calc R U . . .
C7 C 0.911(2) 0.226(3) 0.394(3) 0.056(6) Uani 1 1 d . U . . .
H7A H 0.8662 0.2206 0.4194 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7649(15) 0.665(3) 0.384(4) 0.0496(17) Uani 1 1 d . U . . .
C9 C 0.8173(17) 0.598(3) 0.347(3) 0.0497(15) Uani 1 1 d . U . . .
H3A H 0.8131 0.5136 0.3414 0.060 Uiso 1 1 calc R U . . .
C32 C 0.8502(15) 0.210(2) 0.150(2) 0.0425(11) Uani 1 1 d . U . . .
H9B H 0.8766 0.1466 0.1753 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8797(17) 0.660(2) 0.316(2) 0.0497(15) Uani 1 1 d . U . . .
H4A H 0.9165 0.6159 0.2905 0.060 Uiso 1 1 calc R U . . .
C11 C 0.8836(18) 0.788(3) 0.325(2) 0.0496(17) Uani 1 1 d . U . . .
H5A H 0.9231 0.8303 0.3060 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8273(17) 0.850(2) 0.363(4) 0.050(10) Uani 1 1 d . . . . .
C13 C 1.1101(18) 0.896(3) 0.413(2) 0.054(8) Uani 1 1 d . . . . .
H13 H 1.0852 0.9618 0.4374 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7680(16) 0.790(2) 0.390(3) 0.045(5) Uani 1 1 d . U . . .
C15 C 0.6752(16) -0.366(3) 0.161(3) 0.0508(8) Uani 1 1 d . U . . .
H11B H 0.6959 -0.4348 0.1863 0.061 Uiso 1 1 calc R U . . .
C16 C 0.588(2) -0.275(4) 0.086(3) 0.071(13) Uani 1 1 d . . . . .
H10B H 0.5445 -0.2813 0.0572 0.086 Uiso 1 1 calc R U . . .
C17 C 0.7478(18) 0.286(3) 0.075(3) 0.0425(8) Uani 1 1 d . U . . .
H5B H 0.7038 0.2741 0.0496 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7798(18) 0.400(2) 0.071(2) 0.0488(8) Uani 1 1 d . U . . .
H6B H 0.7559 0.4646 0.0441 0.059 Uiso 1 1 calc R U . . .
C19 C 0.8781(19) 0.327(3) 0.145(2) 0.054(10) Uani 1 1 d . . . . .
H8B H 0.9220 0.3410 0.1700 0.065 Uiso 1 1 calc R U . . .
C23 C 1.208(2) 0.829(3) 0.348(3) 0.053(11) Uani 1 1 d . . . . .
H23 H 1.2529 0.8410 0.3263 0.064 Uiso 1 1 calc R U . . .
C24 C 0.7123(18) -0.257(3) 0.163(3) 0.0508(8) Uani 1 1 d . U . . .
H24 H 0.7557 -0.2532 0.1912 0.061 Uiso 1 1 calc R U . . .
C25 C 0.6191(15) -0.164(3) 0.087(3) 0.055(10) Uani 1 1 d . . . . .
H25 H 0.5960 -0.0966 0.0632 0.065 Uiso 1 1 calc R U . . .
C26 C 0.7835(16) 0.186(2) 0.118(3) 0.0425(8) Uani 1 1 d . U . . .
N2 N 0.8446(13) 0.420(2) 0.105(2) 0.0488(8) Uani 1 1 d . U . . .
N3 N 0.6156(15) -0.378(2) 0.126(2) 0.054(7) Uani 1 1 d . . . . .
O1 O 0.7048(12) 0.6040(15) 0.4037(17) 0.053(7) Uani 1 1 d . . . . .
H1 H 0.6851 0.6373 0.4469 0.079 Uiso 1 1 calc R U . . .
O2 O 0.7122(10) 0.8498(15) 0.4277(17) 0.046(5) Uani 1 1 d . U . . .
H2 H 0.7243 0.9181 0.4449 0.068 Uiso 1 1 calc R U . . .
O3 O 0.8295(10) 0.9757(15) 0.376(3) 0.073(7) Uani 1 1 d . . . . .
H3 H 0.8703 0.9979 0.3803 0.110 Uiso 1 1 calc R U . . .
O4 O 0.4998(10) 0.4784(17) 0.0976(17) 0.057(7) Uani 1 1 d . . . . .
H7 H 0.5380 0.5071 0.1112 0.086 Uiso 1 1 calc R U . . .
O6 O 0.3825(11) 0.3536(16) 0.0539(16) 0.045(4) Uani 1 1 d . U . . .
H6 H 0.3667 0.4001 0.0928 0.067 Uiso 1 1 calc R U . . .
C20 C 1.0037(18) 0.138(2) 0.325(3) 0.054(9) Uani 1 1 d . . . . .
H007 H 1.0241 0.0686 0.2987 0.065 Uiso 1 1 calc R U . . .
C21 C 1.0419(17) 0.243(2) 0.327(2) 0.043(5) Uani 1 1 d . U . . .
H009 H 1.0875 0.2435 0.3046 0.052 Uiso 1 1 calc R U . . .
C22 C 1.0133(14) 0.347(2) 0.361(3) 0.043(5) Uani 1 1 d . U . . .
C27 C 0.9440(19) 0.338(3) 0.397(3) 0.062(12) Uani 1 1 d . . . . .
H005 H 0.9220 0.4068 0.4214 0.074 Uiso 1 1 calc R U . . .
C28 C 1.1126(15) 0.689(3) 0.378(3) 0.046(8) Uani 1 1 d . . . . .
C29 C 1.1783(17) 0.712(2) 0.344(2) 0.053(9) Uani 1 1 d . . . . .
H008 H 1.2035 0.6483 0.3175 0.064 Uiso 1 1 calc R U . . .
C30 C 1.077(3) 0.785(4) 0.413(3) 0.079(14) Uani 1 1 d . . . . .
H010 H 1.0317 0.7763 0.4371 0.094 Uiso 1 1 calc R U . . .
N1 N 0.9384(16) 0.1267(19) 0.359(3) 0.056(6) Uani 1 1 d . U . . .
N4 N 1.1725(13) 0.922(2) 0.382(3) 0.052(7) Uani 1 1 d . . . . .
Hg1 Hg 1.06466(6) 0.51552(8) 0.36939(14) 0.0526(3) Uani 1 1 d . . . . .
C31 C 0.6836(15) -0.151(2) 0.122(3) 0.045(7) Uani 1 1 d . . . . .
O5 O 0.3760(12) 0.1053(16) 0.0747(17) 0.049(5) Uani 1 1 d . U . . .
H5 H 0.3512 0.1510 0.0442 0.073 Uiso 1 1 calc R U . . .
Hg2 Hg 0.73793(5) 0.01374(8) 0.11990(13) 0.0488(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O5 1.37(4) . ?
C1 C6 1.40(5) . ?
C1 C2 1.44(5) . ?
C2 O6 1.34(4) . ?
C2 C3 1.39(4) . ?
C3 O4 1.36(3) . ?
C3 C4 1.37(5) . ?
C4 C5 1.38(5) . ?
C4 H3B 0.9300 . ?
C5 C6 1.35(5) . ?
C5 H2B 0.9300 . ?
C6 H1B 0.9300 . ?
C7 N1 1.32(4) . ?
C7 C27 1.38(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.36(5) . ?
C8 O1 1.36(4) . ?
C8 C14 1.37(4) . ?
C9 C10 1.45(4) . ?
C9 H3A 0.9300 . ?
C32 C26 1.38(5) . ?
C32 C19 1.39(4) . ?
C32 H9B 0.9300 . ?
C10 C11 1.41(4) . ?
C10 H4A 0.9300 . ?
C11 C12 1.39(5) . ?
C11 H5A 0.9300 . ?
C12 C14 1.37(5) . ?
C12 O3 1.39(3) . ?
C13 N4 1.31(4) . ?
C13 C30 1.37(5) . ?
C13 H13 0.9300 . ?
C14 O2 1.36(4) . ?
C15 N3 1.25(4) . ?
C15 C24 1.39(4) . ?
C15 H11B 0.9300 . ?
C16 C25 1.35(5) . ?
C16 N3 1.38(5) . ?
C16 H10B 0.9300 . ?
C17 C18 1.39(4) . ?
C17 C26 1.43(5) . ?
C17 H5B 0.9300 . ?
C18 N2 1.36(4) . ?
C18 H6B 0.9300 . ?
C19 N2 1.34(4) . ?
C19 H8B 0.9300 . ?
C23 N4 1.32(4) . ?
C23 C29 1.40(4) . ?
C23 H23 0.9300 . ?
C24 C31 1.41(4) . ?
C24 H24 0.9300 . ?
C25 C31 1.34(4) . ?
C25 H25 0.9300 . ?
C26 Hg2 2.08(2) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?
O4 H7 0.8200 . ?
O6 H6 0.8200 . ?
C20 N1 1.35(4) . ?
C20 C21 1.36(4) . ?
C20 H007 0.9300 . ?
C21 C22 1.35(4) . ?
C21 H009 0.9300 . ?
C22 C27 1.43(5) . ?
C22 Hg1 2.09(2) . ?
C27 H005 0.9300 . ?
C28 C30 1.36(6) . ?
C28 C29 1.37(5) . ?
C28 Hg1 2.11(3) . ?
C29 H008 0.9300 . ?
C30 H010 0.9300 . ?
C31 Hg2 2.08(2) . ?
O5 H5 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C1 C6 122(3) . . ?
O5 C1 C2 119(3) . . ?
C6 C1 C2 119(3) . . ?
O6 C2 C3 125(3) . . ?
O6 C2 C1 118(2) . . ?
C3 C2 C1 117(3) . . ?
O4 C3 C4 125(2) . . ?
O4 C3 C2 114(3) . . ?
C4 C3 C2 121(3) . . ?
C3 C4 C5 121(3) . . ?
C3 C4 H3B 119.3 . . ?
C5 C4 H3B 119.3 . . ?
C6 C5 C4 119(3) . . ?
C6 C5 H2B 120.6 . . ?
C4 C5 H2B 120.6 . . ?
C5 C6 C1 122(3) . . ?
C5 C6 H1B 118.9 . . ?
C1 C6 H1B 118.9 . . ?
N1 C7 C27 124(4) . . ?
N1 C7 H7A 118.1 . . ?
C27 C7 H7A 118.1 . . ?
C9 C8 O1 116(3) . . ?
C9 C8 C14 122(3) . . ?
O1 C8 C14 121(3) . . ?
C8 C9 C10 119(3) . . ?
C8 C9 H3A 120.5 . . ?
C10 C9 H3A 120.5 . . ?
C26 C32 C19 120(3) . . ?
C26 C32 H9B 119.8 . . ?
C19 C32 H9B 119.8 . . ?
C11 C10 C9 119(3) . . ?
C11 C10 H4A 120.7 . . ?
C9 C10 H4A 120.7 . . ?
C12 C11 C10 119(3) . . ?
C12 C11 H5A 120.6 . . ?
C10 C11 H5A 120.6 . . ?
C14 C12 C11 122(2) . . ?
C14 C12 O3 117(3) . . ?
C11 C12 O3 121(3) . . ?
N4 C13 C30 128(4) . . ?
N4 C13 H13 115.8 . . ?
C30 C13 H13 115.8 . . ?
O2 C14 C8 118(3) . . ?
O2 C14 C12 123(2) . . ?
C8 C14 C12 119(3) . . ?
N3 C15 C24 124(3) . . ?
N3 C15 H11B 117.8 . . ?
C24 C15 H11B 117.8 . . ?
C25 C16 N3 124(3) . . ?
C25 C16 H10B 118.2 . . ?
N3 C16 H10B 118.2 . . ?
C18 C17 C26 119(3) . . ?
C18 C17 H5B 120.4 . . ?
C26 C17 H5B 120.4 . . ?
N2 C18 C17 122(3) . . ?
N2 C18 H6B 118.8 . . ?
C17 C18 H6B 118.8 . . ?
N2 C19 C32 123(3) . . ?
N2 C19 H8B 118.5 . . ?
C32 C19 H8B 118.5 . . ?
N4 C23 C29 121(3) . . ?
N4 C23 H23 119.6 . . ?
C29 C23 H23 119.6 . . ?
C15 C24 C31 119(3) . . ?
C15 C24 H24 120.3 . . ?
C31 C24 H24 120.3 . . ?
C16 C25 C31 121(3) . . ?
C16 C25 H25 119.6 . . ?
C31 C25 H25 119.6 . . ?
C32 C26 C17 117(2) . . ?
C32 C26 Hg2 124(2) . . ?
C17 C26 Hg2 119(2) . . ?
C19 N2 C18 118(2) . . ?
C15 N3 C16 116(3) . . ?
C8 O1 H1 109.5 . . ?
C14 O2 H2 109.5 . . ?
C12 O3 H3 109.5 . . ?
C3 O4 H7 109.5 . . ?
C2 O6 H6 109.5 . . ?
N1 C20 C21 124(3) . . ?
N1 C20 H007 117.8 . . ?
C21 C20 H007 117.8 . . ?
C22 C21 C20 120(3) . . ?
C22 C21 H009 120.1 . . ?
C20 C21 H009 120.1 . . ?
C21 C22 C27 117(3) . . ?
C21 C22 Hg1 125(2) . . ?
C27 C22 Hg1 118(2) . . ?
C7 C27 C22 118(3) . . ?
C7 C27 H005 120.9 . . ?
C22 C27 H005 120.9 . . ?
C30 C28 C29 118(3) . . ?
C30 C28 Hg1 120(3) . . ?
C29 C28 Hg1 123(3) . . ?
C28 C29 C23 121(3) . . ?
C28 C29 H008 119.4 . . ?
C23 C29 H008 119.4 . . ?
C28 C30 C13 116(4) . . ?
C28 C30 H010 121.9 . . ?
C13 C30 H010 121.9 . . ?
C7 N1 C20 116(2) . . ?
C13 N4 C23 116(3) . . ?
C22 Hg1 C28 177.7(10) . . ?
C25 C31 C24 116(2) . . ?
C25 C31 Hg2 123(2) . . ?
C24 C31 Hg2 121(2) . . ?
C1 O5 H5 109.5 . . ?
C26 Hg2 C31 174.9(11) . . ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -1.851
_refine_diff_density_rms         0.163

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_crystal6
_database_code_depnum_ccdc_archive 'CCDC 1051169'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Hg2 N4 O3'
_chemical_formula_weight         839.65

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   26.220(5)
_cell_length_b                   9.0815(18)
_cell_length_c                   10.654(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2537.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.198
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    12.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21807
_diffrn_reflns_av_unetI/netI     0.1674
_diffrn_reflns_av_R_equivalents  0.2011
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             4344
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.919

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    Sir-92
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'diamond 3'
_computing_publication_material  'diamond 3'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4344
_refine_ls_number_parameters     313
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.862
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7288(12) 1.286(3) 0.356(3) 0.038(5) Uani 1 1 d . U . . .
C2 C 0.7079(12) 1.173(3) 0.420(3) 0.038(5) Uani 1 1 d . U . . .
H2A H 0.7146 1.1624 0.5049 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6774(13) 1.074(3) 0.362(4) 0.042(6) Uani 1 1 d . U . . .
C4 C 0.6636(13) 1.088(2) 0.234(4) 0.042(6) Uani 1 1 d . U . . .
H4 H 0.6398 1.0257 0.1965 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6880(8) 1.202(3) 0.166(4) 0.028(4) Uani 1 1 d . U . . .
C6 C 0.7194(10) 1.300(3) 0.228(3) 0.028(4) Uani 1 1 d . U . . .
H6 H 0.7346 1.3760 0.1838 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3082(18) 1.119(4) 0.404(4) 0.072(8) Uani 1 1 d . U . . .
H7 H 0.3148 1.0562 0.4710 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2915(18) 1.266(4) 0.424(4) 0.072(8) Uani 1 1 d . U . . .
H8 H 0.2870 1.2965 0.5069 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2888(14) 1.315(3) 0.216(4) 0.051(5) Uani 1 1 d . U . . .
H9 H 0.2817 1.3797 0.1501 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3065(13) 1.170(3) 0.189(4) 0.051(5) Uani 1 1 d . U . . .
H10 H 0.3127 1.1402 0.1066 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3141(13) 1.073(3) 0.287(4) 0.050(5) Uani 1 1 d . U . . .
C12 C 0.3855 0.5869 0.1192 0.048(10) Uani 1 1 d . . . . .
H12 H 0.3741 0.6298 0.0451 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3966(18) 0.584(4) 0.340(4) 0.064(12) Uani 1 1 d . . . . .
H13 H 0.3910 0.6213 0.4201 0.077 Uiso 1 1 calc R U . . .
C14 C 0.4259(17) 0.450(4) 0.319(6) 0.080(16) Uani 1 1 d . . . . .
H14 H 0.4428 0.4090 0.3874 0.096 Uiso 1 1 calc R U . . .
C15 C 0.411(2) 0.452(4) 0.119(5) 0.086(18) Uani 1 1 d . . . . .
H15 H 0.4156 0.4063 0.0415 0.103 Uiso 1 1 calc R U . . .
C16 C 0.4647(17) 0.037(3) 0.060(4) 0.054(9) Uani 1 1 d . . . . .
H16 H 0.4392 0.0723 0.1122 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5136(14) 0.099(3) 0.058(3) 0.040(9) Uani 1 1 d . . . . .
C18 C 0.5509(15) 0.031(4) -0.015(4) 0.057(10) Uani 1 1 d . . . . .
H18 H 0.5845 0.0633 -0.0119 0.068 Uiso 1 1 calc R U . . .
C19 C 0.538(2) -0.084(3) -0.089(4) 0.083(16) Uani 1 1 d . . . . .
H19 H 0.5632 -0.1197 -0.1415 0.099 Uiso 1 1 calc R U . . .
C20 C 0.4558(14) -0.086(3) -0.024(4) 0.048(9) Uani 1 1 d . . . . .
H20 H 0.4231 -0.1246 -0.0297 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5614(11) 0.490(3) 0.222(4) 0.045(10) Uani 1 1 d . . . . .
C22 C 0.6083(14) 0.497(3) 0.274(6) 0.070(13) Uani 1 1 d . . . . .
H22 H 0.6270 0.4102 0.2827 0.084 Uiso 1 1 calc R U . . .
C23 C 0.6295(14) 0.630(5) 0.314(4) 0.063(10) Uani 1 1 d . . . . .
H23 H 0.6620 0.6298 0.3496 0.076 Uiso 1 1 calc R U . . .
C24 C 0.5579(17) 0.753(3) 0.257(6) 0.081(8) Uani 1 1 d . U . . .
H24 H 0.5401 0.8410 0.2498 0.097 Uiso 1 1 calc R U . . .
C25 C 0.5344(18) 0.625(3) 0.218(4) 0.081(8) Uani 1 1 d . U . . .
H25 H 0.5008 0.6276 0.1898 0.097 Uiso 1 1 calc R U . . .
C29 C 0.3776(12) 0.654(3) 0.235(4) 0.049(10) Uani 1 1 d . . . . .
N1 N 0.6048(12) 0.756(3) 0.304(3) 0.057(8) Uani 1 1 d . . . . .
N2 N 0.4953(11) -0.150(3) -0.097(4) 0.061(9) Uani 1 1 d . . . . .
N3 N 0.2823(13) 1.360(3) 0.336(3) 0.061(9) Uani 1 1 d . . . . .
N4 N 0.4297(13) 0.387(3) 0.214(4) 0.069(12) Uani 1 1 d . . . . .
O1 O 0.6546 0.9682 0.4331 0.072(8) Uani 1 1 d . . . . .
H1 H 0.6523 0.8918 0.3925 0.108 Uiso 1 1 calc R U . . .
O2 O 0.6738(9) 1.223(2) 0.044(3) 0.051(6) Uani 1 1 d . . . . .
H2 H 0.6772 1.1462 0.0046 0.076 Uiso 1 1 calc R U . . .
O3 O 0.7581(9) 1.383(2) 0.418(3) 0.050(6) Uani 1 1 d . . . . .
H3 H 0.7865 1.3480 0.4292 0.074 Uiso 1 1 calc R U . . .
Hg1 Hg 0.53097(5) 0.28999(11) 0.1564(17) 0.0490(3) Uani 1 1 d . . . . .
Hg2 Hg 0.34375(5) 0.86129(11) 0.2564(17) 0.0497(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.35(3) . ?
C1 C2 1.35(4) . ?
C1 C6 1.38(4) . ?
C2 C3 1.35(4) . ?
C2 H2A 0.9300 . ?
C3 O1 1.36(3) . ?
C3 C4 1.41(5) . ?
C4 C5 1.42(4) . ?
C4 H4 0.9300 . ?
C5 O2 1.37(4) . ?
C5 C6 1.38(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.32(5) . ?
C7 C8 1.42(4) . ?
C7 H7 0.9300 . ?
C8 N3 1.30(4) . ?
C8 H8 0.9300 . ?
C9 N3 1.35(4) . ?
C9 C10 1.43(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.38(4) . ?
C10 H10 0.9300 . ?
C11 Hg2 2.10(3) . ?
C12 C29 1.39(4) . ?
C12 C15 1.40(3) . ?
C12 H12 0.9300 . ?
C13 C29 1.38(6) . ?
C13 C14 1.46(5) . ?
C13 H13 0.9300 . ?
C14 N4 1.26(5) . ?
C14 H14 0.9300 . ?
C15 N4 1.27(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.40(5) . ?
C16 C20 1.44(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.39(5) . ?
C17 Hg1 2.08(3) . ?
C18 C19 1.36(5) . ?
C18 H18 0.9300 . ?
C19 N2 1.26(6) . ?
C19 H19 0.9300 . ?
C20 N2 1.42(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.35(5) . ?
C21 C25 1.42(4) . ?
C21 Hg1 2.10(3) . ?
C22 C23 1.40(5) . ?
C22 H22 0.9300 . ?
C23 N1 1.32(5) . ?
C23 H23 0.9300 . ?
C24 N1 1.33(5) . ?
C24 C25 1.38(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C29 Hg2 2.09(3) . ?
N4 Hg1 2.87(3) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 C2 119(3) . . ?
O3 C1 C6 122(3) . . ?
C2 C1 C6 119(3) . . ?
C3 C2 C1 121(3) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 O1 118(3) . . ?
C2 C3 C4 122(3) . . ?
O1 C3 C4 119(3) . . ?
C5 C4 C3 116(3) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
O2 C5 C6 122(2) . . ?
O2 C5 C4 118(3) . . ?
C6 C5 C4 120(3) . . ?
C5 C6 C1 121(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C11 C7 C8 118(3) . . ?
C11 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N3 C8 C7 124(4) . . ?
N3 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N3 C9 C10 121(3) . . ?
N3 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C7 C11 C10 120(3) . . ?
C7 C11 Hg2 118(3) . . ?
C10 C11 Hg2 121(2) . . ?
C29 C12 C15 117(3) . . ?
C29 C12 H12 121.4 . . ?
C15 C12 H12 121.3 . . ?
C29 C13 C14 117(4) . . ?
C29 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
N4 C14 C13 124(4) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C12 126(4) . . ?
N4 C15 H15 117.0 . . ?
C12 C15 H15 117.0 . . ?
C17 C16 C20 117(3) . . ?
C17 C16 H16 121.6 . . ?
C20 C16 H16 121.6 . . ?
C18 C17 C16 118(3) . . ?
C18 C17 Hg1 120(3) . . ?
C16 C17 Hg1 122(2) . . ?
C19 C18 C17 119(4) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N2 C19 C18 129(4) . . ?
N2 C19 H19 115.6 . . ?
C18 C19 H19 115.6 . . ?
N2 C20 C16 122(3) . . ?
N2 C20 H20 118.8 . . ?
C16 C20 H20 118.8 . . ?
C22 C21 C25 116(3) . . ?
C22 C21 Hg1 121(2) . . ?
C25 C21 Hg1 123(2) . . ?
C21 C22 C23 122(3) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
N1 C23 C22 122(3) . . ?
N1 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
N1 C24 C25 123(3) . . ?
N1 C24 H24 118.4 . . ?
C25 C24 H24 118.4 . . ?
C24 C25 C21 120(4) . . ?
C24 C25 H25 120.1 . . ?
C21 C25 H25 120.1 . . ?
C13 C29 C12 118(2) . . ?
C13 C29 Hg2 118(3) . . ?
C12 C29 Hg2 124(2) . . ?
C23 N1 C24 118(3) . . ?
C19 N2 C20 114(3) . . ?
C8 N3 C9 118(3) . . ?
C14 N4 C15 118(3) . . ?
C14 N4 Hg1 114(3) . . ?
C15 N4 Hg1 109(3) . . ?
C3 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
C1 O3 H3 109.5 . . ?
C17 Hg1 C21 166.4(12) . . ?
C17 Hg1 N4 99.4(11) . . ?
C21 Hg1 N4 90.7(10) . . ?
C29 Hg2 C11 175.8(14) . . ?

_refine_diff_density_max         0.773
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.194

_shelxl_version_number           2013-4

