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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1473103'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 N6 O4, C2 H6 O, 2(H2 O)'
_chemical_formula_sum            'C36 H40 N6 O7'
_chemical_formula_weight         668.74

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.1013(3)
_cell_length_b                   12.1013(3)
_cell_length_c                   24.5291(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3592.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    80000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83727
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5270
_reflns_number_gt                4332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] 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_abs_structure_details 
;
 Flack x determined using 1626 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5270
_refine_ls_number_parameters     227
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0999
_refine_ls_wR_factor_ref         0.3351
_refine_ls_wR_factor_gt          0.3109
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.088
_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
N1 N 0.0663(3) 0.3931(3) 0.39321(15) 0.0465(8) Uani 1 1 d . . . . .
C1 C 0.0988(4) 0.4661(4) 0.43800(17) 0.0466(9) Uani 1 1 d . . . . .
H1 H 0.1629 0.5132 0.4271 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0048(6) 0.5374(6) 0.4472(2) 0.0726(18) Uani 1 1 d . . . . .
H2A H -0.0125 0.5569 0.4862 0.087 Uiso 1 1 calc R U . . .
H2B H -0.0006 0.6063 0.4256 0.087 Uiso 1 1 calc R U . . .
C3 C -0.0971(5) 0.4698(8) 0.4294(3) 0.0818(14) Uani 1 1 d . . . . .
H3A H -0.1619 0.5159 0.4200 0.098 Uiso 1 1 calc R U . . .
H3B H -0.1186 0.4158 0.4578 0.098 Uiso 1 1 calc R U . . .
C4 C -0.0487(5) 0.4089(8) 0.3767(3) 0.0818(14) Uani 1 1 d . . . . .
H4A H -0.0863 0.3375 0.3700 0.098 Uiso 1 1 calc R U . . .
H4B H -0.0545 0.4559 0.3438 0.098 Uiso 1 1 calc R U . . .
C5 C 0.1353(3) 0.3312(4) 0.36347(16) 0.0425(9) Uani 1 1 d . . . . .
O1 O 0.1026(3) 0.2775(4) 0.32390(15) 0.0671(12) Uani 1 1 d . . . . .
C6 C 0.2564(3) 0.3296(4) 0.37895(15) 0.0398(8) Uani 1 1 d . . . . .
C7 C 0.3288(3) 0.3977(3) 0.35013(15) 0.0384(7) Uani 1 1 d . . . . .
H7 H 0.3022 0.4469 0.3229 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4414(3) 0.3918(3) 0.36226(15) 0.0367(7) Uani 1 1 d . . . . .
C9 C 0.4792(3) 0.3218(3) 0.40285(16) 0.0375(7) Uani 1 1 d . . . . .
H9 H 0.5562 0.3166 0.4100 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4047(3) 0.2584(3) 0.43349(15) 0.0394(8) Uani 1 1 d . . . . .
C11 C 0.2919(3) 0.2609(4) 0.42067(16) 0.0445(9) Uani 1 1 d . . . . .
H11 H 0.2408 0.2163 0.4402 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5228(3) 0.4618(3) 0.33315(16) 0.0401(8) Uani 1 1 d . . . . .
C13 C 0.5013(4) 0.5702(4) 0.3182(2) 0.0491(10) Uani 1 1 d . . . . .
H13 H 0.4305 0.6014 0.3245 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5827(5) 0.6318(4) 0.2944(2) 0.0574(12) Uani 1 1 d . . . . .
H14 H 0.5656 0.7060 0.2848 0.069 Uiso 1 1 calc R U . . .
N2 N 0.6841(3) 0.5954(4) 0.28368(19) 0.0614(12) Uani 1 1 d D . . . .
C15 C 0.7051(4) 0.4893(5) 0.2964(2) 0.0606(14) Uani 1 1 d . . . . .
H15 H 0.7760 0.4599 0.2882 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6282(4) 0.4214(5) 0.3209(2) 0.0530(11) Uani 1 1 d . . . . .
H16 H 0.6467 0.3471 0.3294 0.064 Uiso 1 1 calc R U . . .
N3 N 0.4502(3) 0.2012(3) 0.47827(15) 0.0446(8) Uani 1 1 d . . . . .
H3 H 0.5197 0.2156 0.4860 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3986(4) 0.1267(4) 0.51061(17) 0.0441(9) Uani 1 1 d . . . . .
O2 O 0.3100(3) 0.0842(3) 0.50062(16) 0.0599(9) Uani 1 1 d . . . . .
O3 O 0.8334(3) 0.7571(3) 0.24735(18) 0.0585(9) Uani 1 1 d D . . . .
H3C H 0.788(4) 0.715(4) 0.2642(19) 0.050 Uiso 1 1 d D U . . .
H3D H 0.810(4) 0.802(4) 0.2214(18) 0.050 Uiso 1 1 d D U . . .
C20 C 0.8839(4) 0.1161(4) 0.2500 0.0472(13) Uani 1 2 d DS T P . .
C19 C 0.9710(7) 0.0290(7) 0.2500 0.181(10) Uani 1 2 d DS T P . .
O4 O 0.8574(11) 0.1733(18) 0.2974(7) 0.189(12) Uani 0.5 1 d D . P . .


_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
N1 C5 1.337(6) . ?
N1 C4 1.462(6) . ?
N1 C1 1.464(6) . ?
C1 C2 1.538(7) . ?
C1 C17 1.539(6) 7_556 ?
C1 H1 1.0000 . ?
C2 C3 1.453(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.599(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O1 1.233(5) . ?
C5 C6 1.514(5) . ?
C6 C11 1.387(6) . ?
C6 C7 1.396(6) . ?
C7 C8 1.397(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(5) . ?
C8 C12 1.482(5) . ?
C9 C10 1.402(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(5) . ?
C10 N3 1.410(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 C16 1.398(6) . ?
C13 C14 1.366(7) . ?
C13 H13 0.9500 . ?
C14 N2 1.331(8) . ?
C14 H14 0.9500 . ?
N2 C15 1.345(7) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N3 C17 1.354(5) . ?
N3 H3 0.8800 . ?
C17 O2 1.215(5) . ?
C17 C1 1.540(6) 7_556 ?
O3 H3C 0.861(19) . ?
O3 H3D 0.88(2) . ?
C20 O4 1.390(10) . ?
C20 O4 1.390(10) 8_665 ?
C20 C19 1.491(13) . ?

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
C5 N1 C4 121.1(4) . . ?
C5 N1 C1 125.4(3) . . ?
C4 N1 C1 112.6(4) . . ?
N1 C1 C2 103.3(4) . . ?
N1 C1 C17 110.7(4) . 7_556 ?
C2 C1 C17 110.8(4) . 7_556 ?
N1 C1 H1 110.6 . . ?
C2 C1 H1 110.6 . . ?
C17 C1 H1 110.6 7_556 . ?
C3 C2 C1 105.5(5) . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C2 C3 C4 102.8(5) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 100.7(5) . . ?
N1 C4 H4A 111.6 . . ?
C3 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
O1 C5 N1 121.6(4) . . ?
O1 C5 C6 120.0(4) . . ?
N1 C5 C6 118.3(4) . . ?
C11 C6 C7 122.2(3) . . ?
C11 C6 C5 119.6(4) . . ?
C7 C6 C5 118.2(4) . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 C12 118.5(3) . . ?
C7 C8 C12 121.1(3) . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 N3 115.8(3) . . ?
C11 C10 N3 124.5(4) . . ?
C6 C11 C10 118.7(4) . . ?
C6 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C16 116.4(4) . . ?
C13 C12 C8 122.9(4) . . ?
C16 C12 C8 120.7(4) . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N2 C14 C13 124.6(5) . . ?
N2 C14 H14 117.7 . . ?
C13 C14 H14 117.7 . . ?
C14 N2 C15 116.5(4) . . ?
N2 C15 C16 122.8(5) . . ?
N2 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 120.1(4) . . ?
C15 C16 H16 120.0 . . ?
C12 C16 H16 120.0 . . ?
C17 N3 C10 127.1(3) . . ?
C17 N3 H3 116.4 . . ?
C10 N3 H3 116.4 . . ?
O2 C17 N3 124.8(4) . . ?
O2 C17 C1 122.7(4) . 7_556 ?
N3 C17 C1 112.4(4) . 7_556 ?
H3C O3 H3D 121(4) . . ?
O4 C20 O4 118(2) . 8_665 ?
O4 C20 C19 121.0(10) . . ?
O4 C20 C19 121.0(10) 8_665 . ?

_refine_diff_density_max         0.847
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.119

_shelxl_version_number           2014/6

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1473104'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N6 O4, 2(C H4 O)'
_chemical_formula_sum            'C24 H30 N6 O6'
_chemical_formula_weight         498.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.1558(2)
_cell_length_b                   12.8129(3)
_cell_length_c                   22.6191(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2363.68(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3265
_cell_measurement_theta_min      3.9050
_cell_measurement_theta_max      62.5680

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.853
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            5130
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.909
_diffrn_reflns_theta_max         62.522
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.767
_reflns_number_total             3281
_reflns_number_gt                3238
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_max     0.703
_reflns_Friedel_fraction_full    0.616

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0546P)²+1.3073P] 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_abs_structure_details 
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3281
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.2051(4) 0.1691(2) 0.15229(12) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.1913(4) 0.2070(3) 0.20802(13) 0.0243(7) Uani 1 1 d . . . . .
O1 O 0.1300(3) 0.29164(18) 0.22088(10) 0.0293(5) Uani 1 1 d . . . . .
C2 C 0.2604(4) 0.1326(3) 0.25459(14) 0.0265(7) Uani 1 1 d . . . . .
H2 H 0.3512 0.0894 0.2378 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1228(5) 0.0627(3) 0.27941(15) 0.0327(8) Uani 1 1 d . . . . .
H3A H 0.0363 0.0508 0.2495 0.039 Uiso 1 1 calc R U . . .
H3B H 0.1666 -0.0055 0.2925 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0575(5) 0.1245(3) 0.33106(16) 0.0381(9) Uani 1 1 d . . . . .
H4A H 0.0012 0.0783 0.3597 0.046 Uiso 1 1 calc R U . . .
H4B H -0.0203 0.1788 0.3176 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2095(5) 0.1734(3) 0.35852(15) 0.0338(8) Uani 1 1 d . . . . .
H5A H 0.1828 0.2402 0.3784 0.041 Uiso 1 1 calc R U . . .
H5B H 0.2613 0.1257 0.3874 0.041 Uiso 1 1 calc R U . . .
N2 N 0.3164(4) 0.1904(2) 0.30693(11) 0.0277(6) Uani 1 1 d . . . . .
C6 C 0.4385(5) 0.2600(3) 0.30736(14) 0.0290(8) Uani 1 1 d . . . . .
O2 O 0.4766(3) 0.3086(2) 0.35263(11) 0.0410(7) Uani 1 1 d . . . . .
C7 C 0.5308(4) 0.2761(3) 0.25065(14) 0.0264(7) Uani 1 1 d . . . . .
C8 C 0.6624(5) 0.2119(3) 0.23773(15) 0.0324(8) Uani 1 1 d . . . . .
H8 H 0.6917 0.1591 0.2653 0.039 Uiso 1 1 calc R U . . .
N3 N 0.7504(4) 0.2213(2) 0.18794(13) 0.0342(7) Uani 1 1 d . . . . .
C9 C 0.7028(4) 0.2944(3) 0.14944(14) 0.0282(7) Uani 1 1 d . . . . .
H9 H 0.7643 0.3016 0.1140 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5690(4) 0.3610(2) 0.15759(14) 0.0230(7) Uani 1 1 d . . . . .
C11 C 0.4858(4) 0.3551(3) 0.21110(14) 0.0244(7) Uani 1 1 d . . . . .
H11 H 0.4010 0.4031 0.2205 0.029 Uiso 1 1 calc R U . . .
N1A N 0.5220(4) 0.4211(2) 0.10861(12) 0.0237(6) Uani 1 1 d . . . . .
C1A C 0.3963(4) 0.4915(2) 0.10545(14) 0.0234(7) Uani 1 1 d . . . . .
O1A O 0.3304(3) 0.53142(18) 0.14833(10) 0.0315(6) Uani 1 1 d . . . . .
C2A C 0.3460(4) 0.5153(3) 0.04111(14) 0.0241(7) Uani 1 1 d . . . . .
H2A H 0.3689 0.4540 0.0150 0.029 Uiso 1 1 calc R U . . .
C3A C 0.4323(4) 0.6134(3) 0.01737(15) 0.0307(8) Uani 1 1 d . . . . .
H3A1 H 0.5423 0.6216 0.0353 0.037 Uiso 1 1 calc R U . . .
H3A2 H 0.4438 0.6104 -0.0262 0.037 Uiso 1 1 calc R U . . .
C4A C 0.3185(5) 0.7026(3) 0.03588(16) 0.0343(8) Uani 1 1 d . . . . .
H4A1 H 0.3346 0.7210 0.0780 0.041 Uiso 1 1 calc R U . . .
H4A2 H 0.3373 0.7655 0.0113 0.041 Uiso 1 1 calc R U . . .
C5A C 0.1485(5) 0.6580(2) 0.02543(15) 0.0282(7) Uani 1 1 d . . . . .
H5A1 H 0.0675 0.6890 0.0529 0.034 Uiso 1 1 calc R U . . .
H5A2 H 0.1122 0.6701 -0.0158 0.034 Uiso 1 1 calc R U . . .
N2A N 0.1713(4) 0.5453(2) 0.03731(12) 0.0240(6) Uani 1 1 d . . . . .
C6A C 0.0428(4) 0.4792(3) 0.03202(14) 0.0249(7) Uani 1 1 d . . . . .
O2A O -0.0964(3) 0.5103(2) 0.02138(12) 0.0352(6) Uani 1 1 d . . . . .
C7A C 0.0798(4) 0.3649(3) 0.04029(14) 0.0236(7) Uani 1 1 d . . . . .
C8A C 0.0692(4) 0.2983(3) -0.00763(14) 0.0274(7) Uani 1 1 d . . . . .
H8A H 0.0362 0.3260 -0.0447 0.033 Uiso 1 1 calc R U . . .
N3A N 0.1037(4) 0.1961(2) -0.00392(12) 0.0270(6) Uani 1 1 d . . . . .
C9A C 0.1470(4) 0.1574(2) 0.04857(14) 0.0254(7) Uani 1 1 d . . . . .
H9A H 0.1731 0.0853 0.0514 0.030 Uiso 1 1 calc R U . . .
C10A C 0.1558(4) 0.2188(2) 0.09973(13) 0.0227(7) Uani 1 1 d . . . . .
C11A C 0.1221(4) 0.3249(2) 0.09525(14) 0.0238(7) Uani 1 1 d . . . . .
H11A H 0.1279 0.3690 0.1290 0.029 Uiso 1 1 calc R U . . .
H1AN H 0.560(5) 0.398(3) 0.0751(19) 0.029 Uiso 1 1 d . U . . .
H1N H 0.239(5) 0.108(3) 0.1478(17) 0.029 Uiso 1 1 d . U . . .
O3 O -0.1648(5) 0.0642(3) 0.10479(16) 0.0639(9) Uani 1 1 d . . . . .
H3 H -0.1300 0.0990 0.1336 0.096 Uiso 1 1 calc R U . . .
C12 C -0.2856(7) -0.0018(4) 0.1234(2) 0.0632(13) Uani 1 1 d . . . . .
H12A H -0.2493 -0.0386 0.1591 0.095 Uiso 1 1 calc R U . . .
H12B H -0.3096 -0.0527 0.0922 0.095 Uiso 1 1 calc R U . . .
H12C H -0.3848 0.0384 0.1323 0.095 Uiso 1 1 calc R U . . .
O4 O 0.2812(3) -0.04459(19) 0.14836(14) 0.0424(7) Uani 1 1 d . . . . .
H4 H 0.3640 -0.0836 0.1481 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1370(5) -0.1066(3) 0.1516(2) 0.0471(10) Uani 1 1 d . . . . .
H13A H 0.1260 -0.1353 0.1916 0.071 Uiso 1 1 calc R U . . .
H13B H 0.1444 -0.1638 0.1230 0.071 Uiso 1 1 calc R U . . .
H13C H 0.0412 -0.0633 0.1425 0.071 Uiso 1 1 calc R U . . .


_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
N1 C1 1.356(4) . ?
N1 C10A 1.407(4) . ?
N1 H1N 0.83(4) . ?
C1 O1 1.229(4) . ?
C1 C2 1.529(5) . ?
C2 N2 1.469(4) . ?
C2 C3 1.542(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.508(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.473(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N2 C6 1.337(5) . ?
C6 O2 1.238(4) . ?
C6 C7 1.502(5) . ?
C7 C8 1.383(5) . ?
C7 C11 1.400(5) . ?
C8 N3 1.340(5) . ?
C8 H8 0.9500 . ?
N3 C9 1.337(4) . ?
C9 C10 1.397(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 N1A 1.403(4) . ?
C11 H11 0.9500 . ?
N1A C1A 1.367(4) . ?
N1A H1AN 0.87(4) . ?
C1A O1A 1.221(4) . ?
C1A C2A 1.543(4) . ?
C2A N2A 1.478(5) . ?
C2A C3A 1.538(5) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.531(5) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.518(5) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A N2A 1.480(4) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
N2A C6A 1.353(4) . ?
C6A O2A 1.227(4) . ?
C6A C7A 1.506(5) . ?
C7A C8A 1.382(5) . ?
C7A C11A 1.388(5) . ?
C8A N3A 1.342(4) . ?
C8A H8A 0.9500 . ?
N3A C9A 1.334(4) . ?
C9A C10A 1.401(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.391(5) . ?
C11A H11A 0.9500 . ?
O3 C12 1.365(6) . ?
O3 H3 0.8400 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O4 C13 1.421(5) . ?
O4 H4 0.8400 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C10A 126.8(3) . . ?
C1 N1 H1N 118(3) . . ?
C10A N1 H1N 115(3) . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C2 122.5(3) . . ?
N1 C1 C2 112.7(3) . . ?
N2 C2 C1 110.8(3) . . ?
N2 C2 C3 103.0(3) . . ?
C1 C2 C3 110.2(3) . . ?
N2 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
C4 C3 C2 103.6(3) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 104.1(3) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N2 C5 C4 102.7(3) . . ?
N2 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
N2 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C6 N2 C2 125.0(3) . . ?
C6 N2 C5 122.3(3) . . ?
C2 N2 C5 112.3(3) . . ?
O2 C6 N2 121.9(3) . . ?
O2 C6 C7 120.8(3) . . ?
N2 C6 C7 117.3(3) . . ?
C8 C7 C11 119.9(3) . . ?
C8 C7 C6 119.2(3) . . ?
C11 C7 C6 120.9(3) . . ?
N3 C8 C7 122.7(3) . . ?
N3 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C9 N3 C8 117.1(3) . . ?
N3 C9 C10 124.6(3) . . ?
N3 C9 H9 117.7 . . ?
C10 C9 H9 117.7 . . ?
C11 C10 C9 117.6(3) . . ?
C11 C10 N1A 125.7(3) . . ?
C9 C10 N1A 116.4(3) . . ?
C10 C11 C7 117.9(3) . . ?
C10 C11 H11 121.1 . . ?
C7 C11 H11 121.1 . . ?
C1A N1A C10 127.5(3) . . ?
C1A N1A H1AN 116(3) . . ?
C10 N1A H1AN 114(3) . . ?
O1A C1A N1A 124.4(3) . . ?
O1A C1A C2A 123.3(3) . . ?
N1A C1A C2A 112.3(3) . . ?
N2A C2A C3A 102.0(3) . . ?
N2A C2A C1A 111.3(3) . . ?
C3A C2A C1A 111.7(3) . . ?
N2A C2A H2A 110.5 . . ?
C3A C2A H2A 110.5 . . ?
C1A C2A H2A 110.5 . . ?
C4A C3A C2A 103.7(3) . . ?
C4A C3A H3A1 111.0 . . ?
C2A C3A H3A1 111.0 . . ?
C4A C3A H3A2 111.0 . . ?
C2A C3A H3A2 111.0 . . ?
H3A1 C3A H3A2 109.0 . . ?
C5A C4A C3A 103.3(3) . . ?
C5A C4A H4A1 111.1 . . ?
C3A C4A H4A1 111.1 . . ?
C5A C4A H4A2 111.1 . . ?
C3A C4A H4A2 111.1 . . ?
H4A1 C4A H4A2 109.1 . . ?
N2A C5A C4A 103.0(3) . . ?
N2A C5A H5A1 111.2 . . ?
C4A C5A H5A1 111.2 . . ?
N2A C5A H5A2 111.2 . . ?
C4A C5A H5A2 111.2 . . ?
H5A1 C5A H5A2 109.1 . . ?
C6A N2A C2A 126.0(3) . . ?
C6A N2A C5A 119.9(3) . . ?
C2A N2A C5A 112.7(3) . . ?
O2A C6A N2A 122.0(3) . . ?
O2A C6A C7A 121.7(3) . . ?
N2A C6A C7A 116.3(3) . . ?
C8A C7A C11A 119.3(3) . . ?
C8A C7A C6A 119.4(3) . . ?
C11A C7A C6A 121.3(3) . . ?
N3A C8A C7A 122.7(3) . . ?
N3A C8A H8A 118.6 . . ?
C7A C8A H8A 118.6 . . ?
C9A N3A C8A 118.3(3) . . ?
N3A C9A C10A 122.7(3) . . ?
N3A C9A H9A 118.7 . . ?
C10A C9A H9A 118.7 . . ?
C11A C10A C9A 118.6(3) . . ?
C11A C10A N1 124.1(3) . . ?
C9A C10A N1 117.3(3) . . ?
C7A C11A C10A 118.4(3) . . ?
C7A C11A H11A 120.8 . . ?
C10A C11A H11A 120.8 . . ?
C12 O3 H3 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 O4 H4 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A N1 C1 O1 1.1(6) . . . . ?
C10A N1 C1 C2 -179.0(3) . . . . ?
O1 C1 C2 N2 -27.3(5) . . . . ?
N1 C1 C2 N2 152.8(3) . . . . ?
O1 C1 C2 C3 86.0(4) . . . . ?
N1 C1 C2 C3 -93.8(3) . . . . ?
N2 C2 C3 C4 28.6(4) . . . . ?
C1 C2 C3 C4 -89.7(3) . . . . ?
C2 C3 C4 C5 -38.2(4) . . . . ?
C3 C4 C5 N2 32.4(4) . . . . ?
C1 C2 N2 C6 -63.6(4) . . . . ?
C3 C2 N2 C6 178.5(3) . . . . ?
C1 C2 N2 C5 109.2(3) . . . . ?
C3 C2 N2 C5 -8.6(4) . . . . ?
C4 C5 N2 C6 158.5(3) . . . . ?
C4 C5 N2 C2 -14.6(4) . . . . ?
C2 N2 C6 O2 177.7(3) . . . . ?
C5 N2 C6 O2 5.5(5) . . . . ?
C2 N2 C6 C7 -3.3(5) . . . . ?
C5 N2 C6 C7 -175.5(3) . . . . ?
O2 C6 C7 C8 92.2(4) . . . . ?
N2 C6 C7 C8 -86.8(4) . . . . ?
O2 C6 C7 C11 -87.5(4) . . . . ?
N2 C6 C7 C11 93.5(4) . . . . ?
C11 C7 C8 N3 -0.5(5) . . . . ?
C6 C7 C8 N3 179.8(3) . . . . ?
C7 C8 N3 C9 -1.9(5) . . . . ?
C8 N3 C9 C10 0.0(5) . . . . ?
N3 C9 C10 C11 4.1(5) . . . . ?
N3 C9 C10 N1A -170.2(3) . . . . ?
C9 C10 C11 C7 -6.3(5) . . . . ?
N1A C10 C11 C7 167.5(3) . . . . ?
C8 C7 C11 C10 4.7(5) . . . . ?
C6 C7 C11 C10 -175.6(3) . . . . ?
C11 C10 N1A C1A 6.3(5) . . . . ?
C9 C10 N1A C1A -180.0(3) . . . . ?
C10 N1A C1A O1A 18.7(5) . . . . ?
C10 N1A C1A C2A -161.3(3) . . . . ?
O1A C1A C2A N2A -28.2(4) . . . . ?
N1A C1A C2A N2A 151.8(3) . . . . ?
O1A C1A C2A C3A 85.1(4) . . . . ?
N1A C1A C2A C3A -94.9(3) . . . . ?
N2A C2A C3A C4A 31.3(3) . . . . ?
C1A C2A C3A C4A -87.7(3) . . . . ?
C2A C3A C4A C5A -39.8(3) . . . . ?
C3A C4A C5A N2A 31.8(3) . . . . ?
C3A C2A N2A C6A 154.4(3) . . . . ?
C1A C2A N2A C6A -86.3(4) . . . . ?
C3A C2A N2A C5A -11.8(4) . . . . ?
C1A C2A N2A C5A 107.5(3) . . . . ?
C4A C5A N2A C6A -179.7(3) . . . . ?
C4A C5A N2A C2A -12.6(4) . . . . ?
C2A N2A C6A O2A -170.2(3) . . . . ?
C5A N2A C6A O2A -4.9(5) . . . . ?
C2A N2A C6A C7A 10.1(5) . . . . ?
C5A N2A C6A C7A 175.4(3) . . . . ?
O2A C6A C7A C8A 68.7(5) . . . . ?
N2A C6A C7A C8A -111.6(3) . . . . ?
O2A C6A C7A C11A -110.3(4) . . . . ?
N2A C6A C7A C11A 69.4(4) . . . . ?
C11A C7A C8A N3A -2.3(5) . . . . ?
C6A C7A C8A N3A 178.6(3) . . . . ?
C7A C8A N3A C9A 1.2(5) . . . . ?
C8A N3A C9A C10A 0.9(5) . . . . ?
N3A C9A C10A C11A -1.8(5) . . . . ?
N3A C9A C10A N1 -179.2(3) . . . . ?
C1 N1 C10A C11A 16.7(5) . . . . ?
C1 N1 C10A C9A -166.0(3) . . . . ?
C8A C7A C11A C10A 1.3(5) . . . . ?
C6A C7A C11A C10A -179.6(3) . . . . ?
C9A C10A C11A C7A 0.6(5) . . . . ?
N1 C10A C11A C7A 177.9(3) . . . . ?

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
C8 H8 O1A 0.95 2.56 3.463(4) 160.0 4_645
C11 H11 O1A 0.95 2.39 2.954(4) 117.9 .
C4A H4A1 O2 0.99 2.47 3.316(5) 143.3 4_655
C11A H11A O1 0.95 2.30 2.874(4) 118.0 .
N1A H1AN N3A 0.87(4) 2.04(4) 2.882(4) 162(4) 3
N1 H1N O4 0.83(4) 1.99(4) 2.809(4) 168(4) .
O3 H3 N3 0.84 2.22 2.841(5) 131.1 1_455
O4 H4 O2 0.84 1.90 2.727(4) 169.8 4_645
C13 H13C O3 0.98 2.49 3.459(6) 168.4 .

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.046

_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_1-CdCl2
_database_code_depnum_ccdc_archive 'CCDC 1473105'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 Cd Cl2 N6 O4'
_chemical_formula_sum            'C34 H30 Cd Cl2 N6 O4'
_chemical_formula_weight         769.94

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.6335(14)
_cell_length_b                   4.9941(2)
_cell_length_c                   18.5991(12)
_cell_angle_alpha                90
_cell_angle_beta                 123.025(4)
_cell_angle_gamma                90
_cell_volume                     1840.54(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.782
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9361
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         30.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             9361
_reflns_number_gt                8520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_max     0.785
_reflns_Friedel_fraction_full    0.890

_reflns_special_details          
;
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1082P)²+1.7187P] 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 1652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9361
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cd1 Cd 0.0000 -0.34167(8) 0.0000 0.0466(2) Uani 1 2 d S T P . .
Cl1 Cl 0.11507(17) -0.5118(7) 0.07210(19) 0.0975(11) Uani 1 1 d . . . . .
N1 N 0.0040(3) -0.0815(12) 0.1019(3) 0.0388(11) Uani 1 1 d . . . . .
C1 C -0.0504(4) -0.016(2) 0.1024(6) 0.073(3) Uani 1 1 d . . . . .
H1 H -0.0920 -0.1003 0.0622 0.087 Uiso 1 1 calc R U . . .
C2 C -0.0492(3) 0.171(3) 0.1592(5) 0.068(3) Uani 1 1 d . . . . .
H2 H -0.0899 0.2208 0.1543 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0118(2) 0.2824(10) 0.2228(3) 0.0251(9) Uani 1 1 d . . . . .
C4 C 0.0675(3) 0.2060(15) 0.2217(3) 0.0378(15) Uani 1 1 d . . . . .
H4 H 0.1105 0.2777 0.2632 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0619(3) 0.0290(15) 0.1619(4) 0.0385(13) Uani 1 1 d . . . . .
H5 H 0.1016 -0.0170 0.1635 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0165(2) 0.4714(10) 0.2874(3) 0.0231(8) Uani 1 1 d . . . . .
C7 C 0.07299(19) 0.6345(13) 0.3358(3) 0.0225(8) Uani 1 1 d . . . . .
H7 H 0.1088 0.6256 0.3268 0.027 Uiso 1 1 calc R U . . .
C8 C 0.0779(2) 0.8087(10) 0.3968(3) 0.0220(8) Uani 1 1 d . . . . .
C9 C 0.0246(2) 0.8314(10) 0.4091(3) 0.0216(8) Uani 1 1 d . . . . .
H9 H 0.0264 0.9580 0.4484 0.026 Uiso 1 1 calc R U . . .
C10 C -0.03122(18) 0.6633(14) 0.3622(2) 0.0208(7) Uani 1 1 d . . . . .
C11 C -0.0353(2) 0.4864(11) 0.3025(3) 0.0240(8) Uani 1 1 d . . . . .
H11 H -0.0737 0.3736 0.2714 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1413(2) 0.9742(10) 0.4484(3) 0.0234(8) Uani 1 1 d . . . . .
O1 O 0.16494(16) 1.0928(7) 0.4132(2) 0.0296(8) Uani 1 1 d . . . . .
N2 N 0.17186(17) 0.9822(9) 0.5348(3) 0.0220(7) Uani 1 1 d . . . . .
C13 C 0.1644(2) 0.7884(10) 0.5879(3) 0.0210(8) Uani 1 1 d . . . . .
H13 H 0.1551 0.6057 0.5617 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2344(2) 0.7963(11) 0.6736(3) 0.0278(10) Uani 1 1 d . . . . .
H14A H 0.2306 0.7574 0.7230 0.033 Uiso 1 1 calc R U . . .
H14B H 0.2660 0.6667 0.6733 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2573(2) 1.0847(11) 0.6765(3) 0.0293(11) Uani 1 1 d . . . . .
H15A H 0.2340 1.2108 0.6931 0.035 Uiso 1 1 calc R U . . .
H15B H 0.3067 1.1035 0.7168 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2365(2) 1.1297(13) 0.5843(3) 0.0268(10) Uani 1 1 d . . . . .
H16A H 0.2301 1.3226 0.5696 0.032 Uiso 1 1 calc R U . . .
H16B H 0.2704 1.0555 0.5741 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1098(2) 0.8690(9) 0.6054(3) 0.0205(8) Uani 1 1 d . . . . .
O2 O 0.09511(17) 1.1018(6) 0.6072(3) 0.0298(8) Uani 1 1 d . . . . .
N3 N 0.08313(15) 0.6583(12) 0.6209(2) 0.0218(6) Uani 1 1 d . . . . .
H3 H 0.0993 0.5000 0.6206 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.258(5) . ?
Cd1 N1 2.258(5) 2 ?
Cd1 Cl1 2.437(3) 2 ?
Cd1 Cl1 2.437(3) . ?
N1 C5 1.326(8) . ?
N1 C1 1.330(9) . ?
C1 C2 1.397(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(6) . ?
C3 C6 1.484(7) . ?
C4 C5 1.369(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.396(7) . ?
C6 C11 1.399(6) . ?
C7 C8 1.383(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(5) . ?
C8 C12 1.510(6) . ?
C9 C10 1.396(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(7) . ?
C10 N3 1.423(4) 2_556 ?
C11 H11 0.9500 . ?
C12 O1 1.220(6) . ?
C12 N2 1.358(6) . ?
N2 C13 1.460(6) . ?
N2 C16 1.480(6) . ?
C13 C17 1.546(6) . ?
C13 C14 1.552(6) . ?
C13 H13 1.0000 . ?
C14 C15 1.529(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O2 1.219(6) . ?
C17 N3 1.336(7) . ?
N3 C10 1.423(4) 2_556 ?
N3 H3 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N1 109.7(3) . 2 ?
N1 Cd1 Cl1 100.72(15) . 2 ?
N1 Cd1 Cl1 102.43(16) 2 2 ?
N1 Cd1 Cl1 102.43(16) . . ?
N1 Cd1 Cl1 100.72(15) 2 . ?
Cl1 Cd1 Cl1 139.20(19) 2 . ?
C5 N1 C1 116.7(5) . . ?
C5 N1 Cd1 119.9(4) . . ?
C1 N1 Cd1 123.3(5) . . ?
N1 C1 C2 123.2(6) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.8(6) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 115.5(5) . . ?
C4 C3 C6 122.4(4) . . ?
C2 C3 C6 122.1(4) . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 123.4(5) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C11 118.2(4) . . ?
C7 C6 C3 121.1(4) . . ?
C11 C6 C3 120.6(4) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 C12 118.4(4) . . ?
C9 C8 C12 121.4(4) . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 N3 118.4(5) . 2_556 ?
C9 C10 N3 120.4(4) . 2_556 ?
C10 C11 C6 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
O1 C12 N2 121.2(4) . . ?
O1 C12 C8 120.7(4) . . ?
N2 C12 C8 118.1(4) . . ?
C12 N2 C13 126.8(4) . . ?
C12 N2 C16 117.0(4) . . ?
C13 N2 C16 111.9(4) . . ?
N2 C13 C17 113.1(4) . . ?
N2 C13 C14 102.9(3) . . ?
C17 C13 C14 108.8(4) . . ?
N2 C13 H13 110.6 . . ?
C17 C13 H13 110.6 . . ?
C14 C13 H13 110.6 . . ?
C15 C14 C13 102.6(4) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C14 102.1(4) . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
C14 C15 H15B 111.4 . . ?
H15A C15 H15B 109.2 . . ?
N2 C16 C15 102.6(4) . . ?
N2 C16 H16A 111.3 . . ?
C15 C16 H16A 111.3 . . ?
N2 C16 H16B 111.3 . . ?
C15 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
O2 C17 N3 124.7(4) . . ?
O2 C17 C13 122.5(4) . . ?
N3 C17 C13 112.7(4) . . ?
C17 N3 C10 126.8(5) . 2_556 ?
C17 N3 H3 116.6 . . ?
C10 N3 H3 116.6 2_556 . ?

_refine_diff_density_max         1.501
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.206

_shelxl_version_number           2014/6

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

data_1-HgCl2
_database_code_depnum_ccdc_archive 'CCDC 1473106'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 Cl2 Hg N6 O4'
_chemical_formula_sum            'C34 H30 Cl2 Hg N6 O4'
_chemical_formula_weight         858.13

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.604(4)
_cell_length_b                   4.9826(8)
_cell_length_c                   18.294(3)
_cell_angle_alpha                90
_cell_angle_beta                 124.204(3)
_cell_angle_gamma                90
_cell_volume                     1779.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.520
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6130
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         30.053
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4675
_reflns_number_gt                4365
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.006(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4675
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Hg1 Hg 0.0000 -0.34209(4) 0.0000 0.02808(14) Uani 1 2 d S T P . .
Cl1 Cl 0.11796(15) -0.4549(6) 0.07569(18) 0.0462(6) Uani 1 1 d . . . . .
N1 N 0.0003(4) -0.0284(15) 0.0990(5) 0.0270(16) Uani 1 1 d . . . . .
C1 C -0.0540(5) 0.034(2) 0.1000(7) 0.041(3) Uani 1 1 d . . . . .
H1 H -0.0959 -0.0564 0.0599 0.049 Uiso 1 1 calc R U . . .
C2 C -0.0535(4) 0.220(2) 0.1551(6) 0.036(3) Uani 1 1 d . . . . .
H2 H -0.0944 0.2606 0.1513 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0076(4) 0.3517(16) 0.2173(5) 0.0200(16) Uani 1 1 d . . . . .
C4 C 0.0641(4) 0.2868(19) 0.2159(6) 0.0243(17) Uani 1 1 d . . . . .
H4 H 0.1067 0.3735 0.2554 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0588(4) 0.0963(15) 0.1573(5) 0.024(2) Uani 1 1 d . . . . .
H5 H 0.0986 0.0525 0.1587 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0132(4) 0.5472(16) 0.2821(5) 0.0162(14) Uani 1 1 d . . . . .
C7 C 0.0699(4) 0.7132(14) 0.3309(5) 0.0173(19) Uani 1 1 d . . . . .
H7 H 0.1054 0.7061 0.3212 0.021 Uiso 1 1 calc R U . . .
C8 C 0.0757(4) 0.8894(16) 0.3937(5) 0.0168(15) Uani 1 1 d . . . . .
C9 C 0.0234(4) 0.9119(15) 0.4071(5) 0.0167(14) Uani 1 1 d . . . . .
H9 H 0.0266 1.0369 0.4485 0.020 Uiso 1 1 calc R U . . .
C10 C -0.0344(3) 0.7446(15) 0.3578(5) 0.0147(14) Uani 1 1 d . . . . .
C11 C -0.0393(4) 0.5654(15) 0.2975(5) 0.0181(15) Uani 1 1 d . . . . .
H11 H -0.0784 0.4522 0.2656 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1397(4) 1.0550(15) 0.4451(5) 0.0167(14) Uani 1 1 d . . . . .
O1 O 0.1628(2) 1.176(2) 0.4094(3) 0.0241(13) Uani 1 1 d . . . . .
N2 N 0.1723(3) 1.0667(13) 0.5355(4) 0.0188(13) Uani 1 1 d . . . . .
C13 C 0.1664(4) 0.8722(15) 0.5905(5) 0.0165(14) Uani 1 1 d . . . . .
H13 H 0.1568 0.6889 0.5638 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2380(4) 0.8817(17) 0.6788(5) 0.0223(17) Uani 1 1 d . . . . .
H14A H 0.2351 0.8445 0.7297 0.027 Uiso 1 1 calc R U . . .
H14B H 0.2697 0.7514 0.6789 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2607(3) 1.170(4) 0.6809(4) 0.0238(16) Uani 1 1 d . . . . .
H15A H 0.2379 1.2969 0.6980 0.029 Uiso 1 1 calc R U . . .
H15B H 0.3110 1.1890 0.7222 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2377(4) 1.2133(14) 0.5857(5) 0.021(2) Uani 1 1 d . . . . .
H16A H 0.2311 1.4064 0.5703 0.025 Uiso 1 1 calc R U . . .
H16B H 0.2712 1.1379 0.5750 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1124(4) 0.9516(17) 0.6090(5) 0.0161(14) Uani 1 1 d . . . . .
O2 O 0.0973(3) 1.184(2) 0.6112(4) 0.0244(15) Uani 1 1 d . . . . .
N3 N 0.0857(3) 0.7388(13) 0.6245(4) 0.0164(13) Uani 1 1 d . . . . .
H3 H 0.1016 0.5800 0.6237 0.020 Uiso 1 1 calc R U . . .


_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 Cl1 2.377(3) . ?
Hg1 Cl1 2.377(3) 2 ?
Hg1 N1 2.388(7) . ?
Hg1 N1 2.388(7) 2 ?
N1 C5 1.332(11) . ?
N1 C1 1.332(13) . ?
C1 C2 1.364(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(12) . ?
C3 C6 1.482(11) . ?
C4 C5 1.384(12) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.389(11) . ?
C6 C11 1.420(11) . ?
C7 C8 1.390(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(11) . ?
C8 C12 1.501(10) . ?
C9 C10 1.409(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(11) . ?
C10 N3 1.419(9) 2_556 ?
C11 H11 0.9500 . ?
C12 O1 1.218(11) . ?
C12 N2 1.379(10) . ?
N2 C13 1.458(10) . ?
N2 C16 1.472(9) . ?
C13 C17 1.543(11) . ?
C13 C14 1.549(10) . ?
C13 H13 1.0000 . ?
C14 C15 1.525(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O2 1.220(13) . ?
C17 N3 1.343(10) . ?
N3 C10 1.419(9) 2_556 ?
N3 H3 0.8800 . ?

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
Cl1 Hg1 Cl1 152.65(15) . 2 ?
Cl1 Hg1 N1 102.1(2) . . ?
Cl1 Hg1 N1 95.7(2) 2 . ?
Cl1 Hg1 N1 95.7(2) . 2 ?
Cl1 Hg1 N1 102.1(2) 2 2 ?
N1 Hg1 N1 98.3(4) . 2 ?
C5 N1 C1 116.9(8) . . ?
C5 N1 Hg1 118.2(6) . . ?
C1 N1 Hg1 124.9(6) . . ?
N1 C1 C2 124.1(9) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.7(9) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 116.0(7) . . ?
C4 C3 C6 120.9(7) . . ?
C2 C3 C6 123.1(8) . . ?
C5 C4 C3 120.3(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 122.8(8) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C11 117.9(7) . . ?
C7 C6 C3 121.7(7) . . ?
C11 C6 C3 120.4(7) . . ?
C6 C7 C8 121.2(7) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 120.8(7) . . ?
C9 C8 C12 121.7(7) . . ?
C7 C8 C12 117.5(7) . . ?
C8 C9 C10 118.3(7) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 N3 118.1(6) . 2_556 ?
C9 C10 N3 120.6(7) . 2_556 ?
C10 C11 C6 120.7(7) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
O1 C12 N2 120.5(7) . . ?
O1 C12 C8 122.1(7) . . ?
N2 C12 C8 117.4(7) . . ?
C12 N2 C13 126.5(6) . . ?
C12 N2 C16 116.8(6) . . ?
C13 N2 C16 111.8(6) . . ?
N2 C13 C17 113.0(6) . . ?
N2 C13 C14 103.2(6) . . ?
C17 C13 C14 108.4(7) . . ?
N2 C13 H13 110.7 . . ?
C17 C13 H13 110.7 . . ?
C14 C13 H13 110.7 . . ?
C15 C14 C13 102.5(6) . . ?
C15 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C14 102.2(8) . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
N2 C16 C15 102.6(7) . . ?
N2 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
N2 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.2 . . ?
O2 C17 N3 124.3(7) . . ?
O2 C17 C13 122.9(7) . . ?
N3 C17 C13 112.8(7) . . ?
C17 N3 C10 126.5(7) . 2_556 ?
C17 N3 H3 116.8 . . ?
C10 N3 H3 116.8 2_556 . ?

_refine_diff_density_max         2.719
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.233

_shelxl_version_number           2014/6

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

data_2-HgCl2
_database_code_depnum_ccdc_archive 'CCDC 1473107'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C66 H66 Cl6 Hg3 N18 O12, 3(C H4 O)'
_chemical_formula_sum            'C69 H78 Cl6 Hg3 N18 O15'
_chemical_formula_weight         2213.96

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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'
'-x, y, -z+1/2'
'-x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.5415(4)
_cell_length_b                   23.0604(13)
_cell_length_c                   35.4200(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8610.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_F_000             4320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.591
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.774
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14589
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.766
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.142
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_point_group_measured_fraction_full 0.846
_reflns_number_total             6830
_reflns_number_gt                6612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.611
_reflns_Friedel_fraction_full    0.752

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0221P)²+595.0108P] 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 2547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(1)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6830
_refine_ls_number_parameters     449
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2076
_refine_ls_wR_factor_gt          0.2068
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.008

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
O7 O 1.012(2) 0.5519(9) 0.8964(8) 0.066(7) Uani 1 1 d D . . . .
H7 H 1.0457 0.5366 0.9155 0.099 Uiso 1 1 calc DR U . . .
C34 C 0.892(3) 0.5798(17) 0.9073(11) 0.101(19) Uani 1 1 d D . . . .
H34A H 0.8253 0.5505 0.9091 0.151 Uiso 1 1 calc R U . . .
H34B H 0.8688 0.6087 0.8882 0.151 Uiso 1 1 calc R U . . .
H34C H 0.9026 0.5990 0.9318 0.151 Uiso 1 1 calc R U . . .
Hg1 Hg 0.63148(10) 0.67771(5) 0.86846(2) 0.0350(3) Uani 1 1 d . . . . .
Hg2 Hg 1.1947(3) 0.56543(16) 1.06190(9) 0.0689(9) Uani 0.5 1 d . . P . .
Cl1 Cl 0.6291(8) 0.7080(5) 0.93101(18) 0.082(4) Uani 1 1 d . . . . .
Cl2 Cl 0.6442(8) 0.6048(3) 0.82277(18) 0.0426(16) Uani 1 1 d . . . . .
Cl3 Cl 1.051(2) 0.5131(10) 1.0256(7) 0.083(6) Uani 0.5 1 d . . P . .
Cl4 Cl 1.301(3) 0.6082(10) 1.1084(5) 0.090(7) Uani 0.5 1 d . . P . .
N1 N 0.869(2) 0.7134(11) 0.8538(6) 0.042(5) Uani 1 1 d . . . . .
C1 C 0.951(2) 0.6986(11) 0.8254(7) 0.029(6) Uani 1 1 d . . . . .
H1 H 0.9220 0.6765 0.8045 0.035 Uiso 1 1 calc R U . . .
C2 C 1.079(2) 0.7166(10) 0.8277(6) 0.022(3) Uani 1 1 d . . . . .
C3 C 1.122(3) 0.7463(9) 0.8581(5) 0.022(3) Uani 1 1 d . . . . .
H3 H 1.2084 0.7576 0.8594 0.026 Uiso 1 1 calc R U . . .
C4 C 1.040(2) 0.7605(13) 0.8874(6) 0.030(6) Uani 1 1 d . . . . .
C5 C 0.910(3) 0.7421(12) 0.8827(7) 0.034(6) Uani 1 1 d . . . . .
H5 H 0.8515 0.7517 0.9020 0.041 Uiso 1 1 calc R U . . .
C6 C 1.175(2) 0.6978(10) 0.7979(6) 0.019(5) Uani 1 1 d . . . . .
O1 O 1.189(2) 0.7280(9) 0.7702(5) 0.042(5) Uani 1 1 d . . . . .
N2 N 1.2373(19) 0.6491(10) 0.8040(5) 0.027(5) Uani 1 1 d . . . . .
C7 C 1.325(3) 0.6267(15) 0.7764(7) 0.049(9) Uani 1 1 d . . . . .
H7A H 1.4109 0.6438 0.7797 0.059 Uiso 1 1 calc R U . . .
H7B H 1.2956 0.6345 0.7504 0.059 Uiso 1 1 calc R U . . .
C8 C 1.326(3) 0.5588(18) 0.7853(9) 0.064(11) Uani 1 1 d . . . . .
H8A H 1.2572 0.5386 0.7715 0.077 Uiso 1 1 calc R U . . .
H8B H 1.4083 0.5410 0.7785 0.077 Uiso 1 1 calc R U . . .
C9 C 1.305(3) 0.5568(11) 0.8251(7) 0.031(4) Uani 1 1 d . . . . .
H9A H 1.3876 0.5568 0.8385 0.037 Uiso 1 1 calc R U . . .
H9B H 1.2590 0.5209 0.8319 0.037 Uiso 1 1 calc R U . . .
C10 C 1.227(3) 0.6105(11) 0.8365(7) 0.031(4) Uani 1 1 d . . . . .
H10 H 1.1362 0.5994 0.8409 0.037 Uiso 1 1 calc R U . . .
C11 C 1.278(3) 0.6419(14) 0.8703(8) 0.043(7) Uani 1 1 d . . . . .
O2 O 1.3646(17) 0.6746(9) 0.8698(4) 0.046(5) Uani 1 1 d . . . . .
N3 N 1.225(2) 0.6246(10) 0.9048(6) 0.032(5) Uani 1 1 d . . . . .
H3A H 1.1668 0.5972 0.9036 0.038 Uiso 1 1 calc DR U . . .
C12 C 1.253(3) 0.6462(17) 0.9419(7) 0.044(9) Uani 1 1 d . . . . .
C13 C 1.220(3) 0.6107(16) 0.9718(8) 0.049(8) Uani 1 1 d . . . . .
H13 H 1.1815 0.5744 0.9661 0.058 Uiso 1 1 calc R U . . .
N4 N 1.238(3) 0.6240(18) 1.0082(7) 0.065(9) Uani 1 1 d . . . . .
C14 C 1.290(3) 0.677(3) 1.0142(8) 0.076(14) Uani 1 1 d . . . . .
H14 H 1.3046 0.6878 1.0398 0.091 Uiso 1 1 calc R U . . .
C15 C 1.324(3) 0.7187(19) 0.9864(8) 0.056(10) Uani 1 1 d . . . . .
C16 C 1.308(3) 0.7003(14) 0.9484(7) 0.037(7) Uani 1 1 d . . . . .
H16 H 1.3340 0.7242 0.9280 0.044 Uiso 1 1 calc R U . . .
C17 C 1.384(3) 0.7733(18) 0.9966(7) 0.052(10) Uani 1 1 d . . . . .
O3 O 1.478(2) 0.7747(12) 1.0154(5) 0.062(7) Uani 1 1 d . . . . .
N5 N 1.337(2) 0.8178(17) 0.9813(6) 0.058(8) Uani 1 1 d . . . . .
C18 C 1.403(4) 0.8768(18) 0.9859(11) 0.077(13) Uani 1 1 d . . . . .
H18A H 1.4788 0.8797 0.9695 0.093 Uiso 1 1 calc R U . . .
H18B H 1.4282 0.8837 1.0124 0.093 Uiso 1 1 calc R U . . .
C19 C 1.298(5) 0.9200(19) 0.9732(14) 0.10(2) Uani 1 1 d . . . . .
H19A H 1.3005 0.9554 0.9891 0.125 Uiso 1 1 calc R U . . .
H19B H 1.3111 0.9314 0.9466 0.125 Uiso 1 1 calc R U . . .
C20 C 1.175(5) 0.890(2) 0.9776(12) 0.103(19) Uani 1 1 d . . . . .
H20A H 1.1419 0.8955 1.0036 0.123 Uiso 1 1 calc R U . . .
H20B H 1.1119 0.9063 0.9596 0.123 Uiso 1 1 calc R U . . .
C21 C 1.197(3) 0.8302(18) 0.9699(8) 0.053(9) Uani 1 1 d . . . . .
H21 H 1.1397 0.8061 0.9859 0.064 Uiso 1 1 calc R U . . .
C22 C 1.179(3) 0.8130(13) 0.9279(7) 0.035(7) Uani 1 1 d . . . . .
O4 O 1.2567(17) 0.8295(9) 0.9040(5) 0.036(4) Uani 1 1 d . . . . .
N6 N 1.073(2) 0.7833(14) 0.9215(6) 0.051(8) Uani 1 1 d . . . . .
H6 H 1.0209 0.7781 0.9406 0.061 Uiso 1 1 calc R U . . .
N7 N 0.580(2) 0.7680(10) 0.8363(7) 0.042(3) Uani 1 1 d . . . . .
C23 C 0.504(3) 0.8064(11) 0.8508(8) 0.042(3) Uani 1 1 d . . . . .
H23 H 0.4561 0.7970 0.8727 0.051 Uiso 1 1 calc R U . . .
C24 C 0.492(3) 0.8592(12) 0.8351(9) 0.042(3) Uani 1 1 d . . . . .
C25 C 0.556(3) 0.8751(12) 0.8025(9) 0.042(3) Uani 1 1 d . . . . .
H25 H 0.5468 0.9125 0.7916 0.051 Uiso 1 1 calc R U . . .
C26 C 0.637(3) 0.8318(10) 0.7861(8) 0.042(3) Uani 1 1 d . . . . .
C27 C 0.634(3) 0.7803(11) 0.8040(8) 0.042(3) Uani 1 1 d . . . . .
H27 H 0.6767 0.7491 0.7917 0.051 Uiso 1 1 calc R U . . .
C28 C 0.414(4) 0.9072(15) 0.8524(11) 0.070(4) Uani 1 1 d . . . . .
O5 O 0.448(3) 0.9366(10) 0.8784(7) 0.070(4) Uani 1 1 d . . . . .
N8 N 0.296(3) 0.9108(11) 0.8376(8) 0.070(4) Uani 1 1 d D . . . .
C29 C 0.202(3) 0.9531(13) 0.8560(10) 0.070(4) Uani 1 1 d D . . . .
H29A H 0.1807 0.9414 0.8821 0.084 Uiso 1 1 calc R U . . .
H29B H 0.2350 0.9932 0.8561 0.084 Uiso 1 1 calc R U . . .
C30 C 0.086(3) 0.9477(12) 0.8299(10) 0.070(4) Uani 1 1 d D . . . .
H30A H 0.0068 0.9507 0.8449 0.084 Uiso 1 1 calc R U . . .
H30B H 0.0864 0.9792 0.8110 0.084 Uiso 1 1 calc R U . . .
C31 C 0.092(3) 0.8890(12) 0.8103(11) 0.070(4) Uani 1 1 d D . . . .
H31A H 0.0566 0.8917 0.7845 0.084 Uiso 1 1 calc R U . . .
H31B H 0.0432 0.8598 0.8247 0.084 Uiso 1 1 calc R U . . .
C32 C 0.234(3) 0.8717(14) 0.8087(10) 0.070(4) Uani 1 1 d D . . . .
H32 H 0.2450 0.8300 0.8156 0.084 Uiso 1 1 calc R U . . .
C33 C 0.711(4) 0.8839(16) 0.7296(11) 0.072(13) Uani 1 1 d . . . . .
O6 O 0.678(3) 0.9348(10) 0.7403(7) 0.088(11) Uani 1 1 d . . . . .
N9 N 0.698(3) 0.8357(13) 0.7499(8) 0.065(9) Uani 1 1 d . . . . .
H9 H 0.7299 0.8036 0.7403 0.078 Uiso 1 1 calc R U . . .
O8 O 0.507(5) 0.471(2) 0.0620(17) 0.10(3) Uani 0.5 1 d D . P . .
H8 H 0.5103 0.4912 0.0818 0.156 Uiso 0.5 1 calc R U P . .
C35 C 0.418(6) 0.497(3) 0.0362(13) 0.046(18) Uani 0.5 1 d D . P . .
H35A H 0.3327 0.4825 0.0419 0.068 Uiso 0.5 1 calc R U P . .
H35B H 0.4412 0.4857 0.0103 0.068 Uiso 0.5 1 calc R U P . .
H35C H 0.4208 0.5388 0.0388 0.068 Uiso 0.5 1 calc R U P . .


_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
O7 C34 1.472(19) . ?
O7 H7 0.8400 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
Hg1 Cl1 2.323(6) . ?
Hg1 Cl2 2.337(7) . ?
Hg1 N7 2.43(2) . ?
Hg1 N1 2.68(3) . ?
Hg2 Cl4 2.22(3) . ?
Hg2 Cl3 2.32(2) . ?
Hg2 N4 2.38(3) . ?
Cl3 Cl3 1.91(5) 2_567 ?
N1 C5 1.29(3) . ?
N1 C1 1.37(3) . ?
C1 C2 1.42(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.35(3) . ?
C2 C6 1.52(3) . ?
C3 C4 1.39(3) . ?
C3 H3 0.9500 . ?
C4 N6 1.37(3) . ?
C4 C5 1.44(4) . ?
C5 H5 0.9500 . ?
C6 O1 1.21(3) . ?
C6 N2 1.32(3) . ?
N2 C7 1.45(3) . ?
N2 C10 1.46(3) . ?
C7 C8 1.60(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.43(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.54(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.50(4) . ?
C10 H10 1.0000 . ?
C11 O2 1.18(3) . ?
C11 N3 1.41(3) . ?
N3 C12 1.44(3) . ?
N3 H3A 0.8800 . ?
C12 C13 1.38(4) . ?
C12 C16 1.39(5) . ?
C13 N4 1.34(4) . ?
C13 H13 0.9500 . ?
N4 C14 1.36(6) . ?
C14 C15 1.42(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.42(4) . ?
C15 C17 1.46(5) . ?
C16 H16 0.9500 . ?
C17 O3 1.19(4) . ?
C17 N5 1.26(5) . ?
N5 C18 1.54(5) . ?
N5 C21 1.55(3) . ?
C18 C19 1.55(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.48(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.43(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.55(3) . ?
C21 H21 1.0000 . ?
C22 O4 1.24(3) . ?
C22 N6 1.33(4) . ?
N6 H6 0.8800 . ?
N7 C23 1.30(3) . ?
N7 C27 1.31(4) . ?
C23 C24 1.34(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.39(4) . ?
C24 C28 1.51(4) . ?
C25 C26 1.44(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.35(4) . ?
C26 N9 1.44(4) . ?
C27 H27 0.9500 . ?
C28 O5 1.20(5) . ?
C28 N8 1.35(5) . ?
N8 C32 1.52(2) . ?
N8 C29 1.54(2) . ?
C29 C30 1.53(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.52(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.55(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.50(5) 3_656 ?
C32 H32 1.0000 . ?
C33 O6 1.28(4) . ?
C33 N9 1.33(5) . ?
C33 C32 1.50(5) 3_656 ?
N9 H9 0.8800 . ?
O8 C35 1.43(3) . ?
O8 H8 0.8713 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C34 O7 H7 109.5 . . ?
O7 C34 H34A 109.5 . . ?
O7 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O7 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Cl1 Hg1 Cl2 151.3(4) . . ?
Cl1 Hg1 N7 100.7(6) . . ?
Cl2 Hg1 N7 107.7(6) . . ?
Cl1 Hg1 N1 95.9(5) . . ?
Cl2 Hg1 N1 91.9(5) . . ?
N7 Hg1 N1 81.6(8) . . ?
Cl4 Hg2 Cl3 165.7(9) . . ?
Cl4 Hg2 N4 104.1(11) . . ?
Cl3 Hg2 N4 88.7(10) . . ?
Cl3 Cl3 Hg2 133.6(9) 2_567 . ?
C5 N1 C1 120(2) . . ?
C5 N1 Hg1 108.6(18) . . ?
C1 N1 Hg1 130.8(17) . . ?
N1 C1 C2 119(2) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 121(2) . . ?
C3 C2 C6 118(2) . . ?
C1 C2 C6 121(2) . . ?
C2 C3 C4 120(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N6 C4 C3 126(2) . . ?
N6 C4 C5 118(2) . . ?
C3 C4 C5 116(2) . . ?
N1 C5 C4 124(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
O1 C6 N2 124(2) . . ?
O1 C6 C2 118(2) . . ?
N2 C6 C2 117.3(19) . . ?
C6 N2 C7 121(2) . . ?
C6 N2 C10 128(2) . . ?
C7 N2 C10 111(2) . . ?
N2 C7 C8 103(2) . . ?
N2 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
N2 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C7 103(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C8 C9 C10 108(2) . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C11 108(2) . . ?
N2 C10 C9 104(2) . . ?
C11 C10 C9 114(2) . . ?
N2 C10 H10 110.4 . . ?
C11 C10 H10 110.3 . . ?
C9 C10 H10 110.4 . . ?
O2 C11 N3 120(3) . . ?
O2 C11 C10 125(3) . . ?
N3 C11 C10 114(3) . . ?
C11 N3 C12 128(3) . . ?
C11 N3 H3A 116.0 . . ?
C12 N3 H3A 116.0 . . ?
C13 C12 C16 121(3) . . ?
C13 C12 N3 116(3) . . ?
C16 C12 N3 123(3) . . ?
N4 C13 C12 124(3) . . ?
N4 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C13 N4 C14 115(3) . . ?
C13 N4 Hg2 128(3) . . ?
C14 N4 Hg2 118(2) . . ?
N4 C14 C15 127(3) . . ?
N4 C14 H14 116.6 . . ?
C15 C14 H14 116.6 . . ?
C14 C15 C16 115(4) . . ?
C14 C15 C17 121(3) . . ?
C16 C15 C17 123(3) . . ?
C12 C16 C15 118(3) . . ?
C12 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
O3 C17 N5 123(4) . . ?
O3 C17 C15 122(4) . . ?
N5 C17 C15 115(3) . . ?
C17 N5 C18 120(2) . . ?
C17 N5 C21 129(3) . . ?
C18 N5 C21 107(3) . . ?
N5 C18 C19 102(3) . . ?
N5 C18 H18A 111.3 . . ?
C19 C18 H18A 111.3 . . ?
N5 C18 H18B 111.3 . . ?
C19 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
C20 C19 C18 107(4) . . ?
C20 C19 H19A 110.2 . . ?
C18 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C18 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C21 C20 C19 106(3) . . ?
C21 C20 H20A 110.4 . . ?
C19 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
C19 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?
C20 C21 C22 114(3) . . ?
C20 C21 N5 107(3) . . ?
C22 C21 N5 109(2) . . ?
C20 C21 H21 109.1 . . ?
C22 C21 H21 109.1 . . ?
N5 C21 H21 109.1 . . ?
O4 C22 N6 127(2) . . ?
O4 C22 C21 120(3) . . ?
N6 C22 C21 114(3) . . ?
C22 N6 C4 125(2) . . ?
C22 N6 H6 117.7 . . ?
C4 N6 H6 117.7 . . ?
C23 N7 C27 118(3) . . ?
C23 N7 Hg1 122(2) . . ?
C27 N7 Hg1 119.7(19) . . ?
N7 C23 C24 121(3) . . ?
N7 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 123(3) . . ?
C23 C24 C28 123(3) . . ?
C25 C24 C28 114(3) . . ?
C24 C25 C26 116(3) . . ?
C24 C25 H25 121.9 . . ?
C26 C25 H25 121.9 . . ?
C27 C26 C25 114(3) . . ?
C27 C26 N9 119(2) . . ?
C25 C26 N9 126(3) . . ?
N7 C27 C26 128(3) . . ?
N7 C27 H27 116.2 . . ?
C26 C27 H27 116.2 . . ?
O5 C28 N8 123(3) . . ?
O5 C28 C24 124(4) . . ?
N8 C28 C24 113(3) . . ?
C28 N8 C32 129(3) . . ?
C28 N8 C29 118(3) . . ?
C32 N8 C29 112(3) . . ?
C30 C29 N8 102(3) . . ?
C30 C29 H29A 111.4 . . ?
N8 C29 H29A 111.4 . . ?
C30 C29 H29B 111.3 . . ?
N8 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C31 C30 C29 108(3) . . ?
C31 C30 H30A 110.0 . . ?
C29 C30 H30A 110.0 . . ?
C31 C30 H30B 110.1 . . ?
C29 C30 H30B 110.1 . . ?
H30A C30 H30B 108.4 . . ?
C30 C31 C32 107(3) . . ?
C30 C31 H31A 110.3 . . ?
C32 C31 H31A 110.4 . . ?
C30 C31 H31B 110.4 . . ?
C32 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
C33 C32 N8 109(3) 3_656 . ?
C33 C32 C31 111(3) 3_656 . ?
N8 C32 C31 104(2) . . ?
C33 C32 H32 110.8 3_656 . ?
N8 C32 H32 110.8 . . ?
C31 C32 H32 110.7 . . ?
O6 C33 N9 125(3) . . ?
O6 C33 C32 123(3) . 3_656 ?
N9 C33 C32 112(3) . 3_656 ?
C33 N9 C26 125(3) . . ?
C33 N9 H9 117.3 . . ?
C26 N9 H9 117.3 . . ?
C35 O8 H8 112.8 . . ?
O8 C35 H35A 109.9 . . ?
O8 C35 H35B 109.2 . . ?
H35A C35 H35B 109.5 . . ?
O8 C35 H35C 109.3 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

_refine_diff_density_max         1.896
_refine_diff_density_min         -4.761
_refine_diff_density_rms         0.251

_shelxl_version_number           2014/6

