# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1540268'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 O'
_chemical_formula_weight         226.24
_chemical_oxdiff_usercomment     'Farhat sample 340-A'

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      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                   7.6439(7)
_cell_length_b                   11.271(2)
_cell_length_c                   13.576(3)
_cell_angle_alpha                67.807(18)
_cell_angle_beta                 79.669(11)
_cell_angle_gamma                81.247(11)
_cell_volume                     1060.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    5275
_cell_measurement_theta_min      2.9654
_cell_measurement_theta_max      29.0973

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6097
_exptl_crystal_size_mid          0.4764
_exptl_crystal_size_min          0.3236
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9632
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         29.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4904
_reflns_number_gt                4057
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0473P)²+0.2845P] 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         4904
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
H3B H 0.748(2) 0.0495(16) 0.4385(14) 0.034(4) Uiso 1 1 d . . . . .
H3A H 0.192(2) 0.5166(16) 0.0364(14) 0.038(4) Uiso 1 1 d . . . . .
N3 N 0.14866(14) 0.49300(10) 0.10733(8) 0.0204(2) Uani 1 1 d . . . . .
C8 C -0.01450(15) 0.70279(12) 0.07143(10) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.21279(14) 0.37553(11) 0.17531(8) 0.0226(2) Uani 1 1 d . . . . .
O1 O -0.00879(12) 0.54501(9) 0.24673(7) 0.0266(2) Uani 1 1 d . . . . .
N1 N 0.36013(13) 0.44516(10) -0.05620(8) 0.0209(2) Uani 1 1 d . . . . .
C7 C 0.04108(15) 0.57361(12) 0.15057(10) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.40395(15) 0.33116(12) 0.02037(10) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.43624(16) 0.46407(13) -0.15696(10) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.409096 0.542720 -0.210193 0.028 Uiso 1 1 calc R U . . .
C9 C 0.04605(16) 0.74720(13) -0.03765(10) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.127585 0.696058 -0.067742 0.026 Uiso 1 1 calc R U . . .
C12 C -0.13464(16) 0.78472(13) 0.11141(10) 0.0228(3) Uani 1 1 d . . . . .
H12 H -0.176696 0.759395 0.184324 0.027 Uiso 1 1 calc R U . . .
C10 C -0.01725(16) 0.86915(13) -0.10085(10) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.025020 0.897947 -0.173800 0.030 Uiso 1 1 calc R U . . .
C11 C -0.19066(17) 0.90439(13) 0.04120(11) 0.0271(3) Uani 1 1 d . . . . .
H11 H -0.272221 0.957587 0.069100 0.033 Uiso 1 1 calc R U . . .
C6 C 0.32650(16) 0.30642(12) 0.13256(10) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.366419 0.227388 0.180912 0.026 Uiso 1 1 calc R U . . .
N4 N -0.13510(14) 0.94840(11) -0.06410(9) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.55353(16) 0.37276(14) -0.18645(11) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.602519 0.389772 -0.257721 0.030 Uiso 1 1 calc R U . . .
C2 C 0.52127(16) 0.23515(13) -0.00287(11) 0.0235(3) Uani 1 1 d . . . . .
H2 H 0.549000 0.157800 0.051608 0.028 Uiso 1 1 calc R U . . .
C3 C 0.59608(16) 0.25611(14) -0.10789(11) 0.0259(3) Uani 1 1 d . . . . .
H3 H 0.673644 0.192826 -0.125333 0.031 Uiso 1 1 calc R U . . .
O1' O 0.60568(13) 0.03910(10) 0.24548(8) 0.0310(2) Uani 1 1 d . . . . .
N1' N 0.82530(13) 0.11056(10) 0.53620(8) 0.0218(2) Uani 1 1 d . . . . .
N3' N 0.72254(13) 0.07725(10) 0.37267(9) 0.0203(2) Uani 1 1 d . . . . .
C8' C 0.64071(14) -0.13440(12) 0.41078(9) 0.0180(2) Uani 1 1 d . . . . .
C9' C 0.68079(16) -0.18051(13) 0.51529(10) 0.0214(3) Uani 1 1 d . . . . .
H9' H 0.713557 -0.125316 0.543859 0.026 Uiso 1 1 calc R U . . .
C1' C 0.84265(15) 0.23234(12) 0.46676(10) 0.0203(3) Uani 1 1 d . . . . .
N2' N 0.75423(14) 0.20188(11) 0.30923(9) 0.0236(2) Uani 1 1 d . . . . .
N4' N 0.62460(15) -0.39496(11) 0.54099(9) 0.0267(3) Uani 1 1 d . . . . .
C12' C 0.59040(15) -0.22138(13) 0.37353(10) 0.0207(3) Uani 1 1 d . . . . .
H12' H 0.561018 -0.194277 0.304305 0.025 Uiso 1 1 calc R U . . .
C5' C 0.85043(16) 0.08335(13) 0.63760(10) 0.0243(3) Uani 1 1 d . . . . .
H5' H 0.837946 -0.000098 0.686178 0.029 Uiso 1 1 calc R U . . .
C7' C 0.65265(15) 0.00235(12) 0.33447(10) 0.0200(3) Uani 1 1 d . . . . .
C6' C 0.81201(16) 0.26687(13) 0.35497(10) 0.0233(3) Uani 1 1 d . . . . .
H6' H 0.838825 0.349377 0.309812 0.028 Uiso 1 1 calc R U . . .
C2' C 0.88482(16) 0.32790(13) 0.49780(11) 0.0243(3) Uani 1 1 d . . . . .
H2' H 0.895590 0.411060 0.448289 0.029 Uiso 1 1 calc R U . . .
C10' C 0.67121(17) -0.31030(13) 0.57652(10) 0.0249(3) Uani 1 1 d . . . . .
H10' H 0.698855 -0.339967 0.646299 0.030 Uiso 1 1 calc R U . . .
C11' C 0.58446(17) -0.34892(14) 0.44058(11) 0.0257(3) Uani 1 1 d . . . . .
H11' H 0.550586 -0.405977 0.414300 0.031 Uiso 1 1 calc R U . . .
C4' C 0.89404(16) 0.17280(14) 0.67411(11) 0.0257(3) Uani 1 1 d . . . . .
H4' H 0.911998 0.149352 0.745242 0.031 Uiso 1 1 calc R U . . .
C3' C 0.91049(16) 0.29765(14) 0.60310(11) 0.0264(3) Uani 1 1 d . . . . .
H3' H 0.938257 0.359997 0.625711 0.032 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
N3 C7 1.3596(16) . ?
N3 N2 1.3736(15) . ?
C8 C9 1.3865(17) . ?
C8 C12 1.3902(17) . ?
C8 C7 1.4995(18) . ?
N2 C6 1.2859(16) . ?
O1 C7 1.2224(15) . ?
N1 C5 1.3369(16) . ?
N1 C1 1.3523(16) . ?
C1 C2 1.3914(17) . ?
C1 C6 1.4676(17) . ?
C5 C4 1.3875(18) . ?
C9 C10 1.3839(18) . ?
C12 C11 1.3822(19) . ?
C10 N4 1.3375(17) . ?
C11 N4 1.3343(18) . ?
C4 C3 1.3809(19) . ?
C2 C3 1.3819(18) . ?
O1' C7' 1.2216(15) . ?
N1' C5' 1.3356(17) . ?
N1' C1' 1.3504(17) . ?
N3' C7' 1.3544(17) . ?
N3' N2' 1.3742(15) . ?
C8' C12' 1.3870(18) . ?
C8' C9' 1.3882(17) . ?
C8' C7' 1.5033(18) . ?
C9' C10' 1.3887(19) . ?
C1' C2' 1.3924(18) . ?
C1' C6' 1.4707(18) . ?
N2' C6' 1.2876(17) . ?
N4' C10' 1.3352(18) . ?
N4' C11' 1.3375(17) . ?
C12' C11' 1.3834(19) . ?
C5' C4' 1.3829(19) . ?
C2' C3' 1.3821(19) . ?
C4' C3' 1.382(2) . ?

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
C7 N3 N2 118.54(10) . . ?
C9 C8 C12 117.71(12) . . ?
C9 C8 C7 125.24(11) . . ?
C12 C8 C7 117.04(11) . . ?
C6 N2 N3 116.94(10) . . ?
C5 N1 C1 117.33(11) . . ?
O1 C7 N3 123.55(12) . . ?
O1 C7 C8 121.24(11) . . ?
N3 C7 C8 115.21(10) . . ?
N1 C1 C2 122.42(11) . . ?
N1 C1 C6 119.50(11) . . ?
C2 C1 C6 118.08(11) . . ?
N1 C5 C4 123.57(12) . . ?
C10 C9 C8 118.68(11) . . ?
C11 C12 C8 119.01(12) . . ?
N4 C10 C9 124.42(12) . . ?
N4 C11 C12 124.14(12) . . ?
N2 C6 C1 130.91(12) . . ?
C11 N4 C10 116.02(11) . . ?
C3 C4 C5 118.69(12) . . ?
C3 C2 C1 119.20(12) . . ?
C4 C3 C2 118.77(12) . . ?
C5' N1' C1' 117.62(12) . . ?
C7' N3' N2' 120.85(11) . . ?
C12' C8' C9' 117.62(12) . . ?
C12' C8' C7' 117.83(11) . . ?
C9' C8' C7' 124.52(11) . . ?
C8' C9' C10' 119.01(12) . . ?
N1' C1' C2' 122.25(12) . . ?
N1' C1' C6' 119.27(12) . . ?
C2' C1' C6' 118.47(12) . . ?
C6' N2' N3' 115.89(11) . . ?
C10' N4' C11' 116.56(12) . . ?
C11' C12' C8' 119.21(12) . . ?
N1' C5' C4' 123.42(13) . . ?
O1' C7' N3' 124.38(12) . . ?
O1' C7' C8' 121.53(12) . . ?
N3' C7' C8' 114.07(11) . . ?
N2' C6' C1' 130.73(12) . . ?
C3' C2' C1' 119.19(13) . . ?
N4' C10' C9' 123.78(12) . . ?
N4' C11' C12' 123.81(13) . . ?
C3' C4' C5' 118.88(12) . . ?
C2' C3' C4' 118.63(13) . . ?

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
C7 N3 N2 C6 -174.03(11) . . . . ?
N2 N3 C7 O1 -3.53(18) . . . . ?
N2 N3 C7 C8 176.58(10) . . . . ?
C9 C8 C7 O1 174.80(12) . . . . ?
C12 C8 C7 O1 -4.33(18) . . . . ?
C9 C8 C7 N3 -5.31(18) . . . . ?
C12 C8 C7 N3 175.56(11) . . . . ?
C5 N1 C1 C2 -0.86(18) . . . . ?
C5 N1 C1 C6 178.95(11) . . . . ?
C1 N1 C5 C4 1.25(19) . . . . ?
C12 C8 C9 C10 -0.76(18) . . . . ?
C7 C8 C9 C10 -179.89(11) . . . . ?
C9 C8 C12 C11 1.32(18) . . . . ?
C7 C8 C12 C11 -179.49(11) . . . . ?
C8 C9 C10 N4 -0.4(2) . . . . ?
C8 C12 C11 N4 -0.8(2) . . . . ?
N3 N2 C6 C1 0.4(2) . . . . ?
N1 C1 C6 N2 2.4(2) . . . . ?
C2 C1 C6 N2 -177.81(13) . . . . ?
C12 C11 N4 C10 -0.3(2) . . . . ?
C9 C10 N4 C11 0.9(2) . . . . ?
N1 C5 C4 C3 -0.6(2) . . . . ?
N1 C1 C2 C3 -0.15(19) . . . . ?
C6 C1 C2 C3 -179.97(11) . . . . ?
C5 C4 C3 C2 -0.46(19) . . . . ?
C1 C2 C3 C4 0.81(19) . . . . ?
C12' C8' C9' C10' 0.87(16) . . . . ?
C7' C8' C9' C10' -177.49(10) . . . . ?
C5' N1' C1' C2' -0.11(17) . . . . ?
C5' N1' C1' C6' -178.62(10) . . . . ?
C7' N3' N2' C6' 176.48(11) . . . . ?
C9' C8' C12' C11' -0.79(16) . . . . ?
C7' C8' C12' C11' 177.68(10) . . . . ?
C1' N1' C5' C4' -0.45(18) . . . . ?
N2' N3' C7' O1' -3.41(18) . . . . ?
N2' N3' C7' C8' 175.15(9) . . . . ?
C12' C8' C7' O1' 5.98(16) . . . . ?
C9' C8' C7' O1' -175.67(11) . . . . ?
C12' C8' C7' N3' -172.62(10) . . . . ?
C9' C8' C7' N3' 5.73(16) . . . . ?
N3' N2' C6' C1' -3.33(19) . . . . ?
N1' C1' C6' N2' 6.7(2) . . . . ?
C2' C1' C6' N2' -171.88(12) . . . . ?
N1' C1' C2' C3' 0.19(18) . . . . ?
C6' C1' C2' C3' 178.71(11) . . . . ?
C11' N4' C10' C9' -0.47(19) . . . . ?
C8' C9' C10' N4' -0.25(19) . . . . ?
C10' N4' C11' C12' 0.56(19) . . . . ?
C8' C12' C11' N4' 0.07(19) . . . . ?
N1' C5' C4' C3' 0.92(19) . . . . ?
C1' C2' C3' C4' 0.27(18) . . . . ?
C5' C4' C3' C2' -0.79(18) . . . . ?

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
N3 H3A N1 0.910(17) 1.936(16) 2.6804(15) 137.8(15) .
C6 H6 O1' 0.93 2.57 3.4219(17) 152.5 .
C2 H2 O1' 0.93 2.55 3.3741(18) 148.6 .
C6' H6' O1 0.93 2.44 3.3119(18) 156.3 1_655
C2' H2' O1 0.93 2.61 3.4027(18) 143.8 1_655
C10' H10' N2 0.93 2.50 3.4176(18) 168.8 2_656
C11' H11' N4' 0.93 2.61 3.4153(19) 145.8 2_646

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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 1540271'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Hg N7 O, C2 H6 O'
_chemical_formula_sum            'C14 H15 Hg N7 O2'
_chemical_formula_weight         513.92

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'
Hg Hg -4.2923 7.6849 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_cell_setting           monoclinic

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

_cell_length_a                   8.2360(2)
_cell_length_b                   14.4820(3)
_cell_length_c                   14.0530(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.015(2)
_cell_angle_gamma                90.00
_cell_volume                     1663.61(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120.0
_cell_measurement_reflns_used    4305
_cell_measurement_theta_min      4.3975
_cell_measurement_theta_max      70.4245

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1744
_exptl_crystal_size_mid          0.1119
_exptl_crystal_size_min          0.1115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    16.804
_exptl_absorpt_correction_T_min  0.154
_exptl_absorpt_correction_T_max  0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120.0
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2673
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6695
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.40
_diffrn_reflns_theta_max         70.56
_reflns_number_total             3123
_reflns_number_gt                2825
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    ?
_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)+(0.0271P)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         3123
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0500
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.451660(17) 0.020225(10) 0.823618(9) 0.02121(7) Uani 1 1 d . . .
C1 C 0.5289(5) 0.2354(3) 1.0669(2) 0.0214(7) Uani 1 1 d . . .
N2 N 0.6564(4) 0.1001(2) 1.0133(2) 0.0224(6) Uani 1 1 d . . .
N3 N 0.6577(4) 0.0348(2) 0.9426(2) 0.0204(6) Uani 1 1 d . . .
N4 N 0.6589(4) -0.0945(2) 0.8010(2) 0.0221(6) Uani 1 1 d . . .
N5 N 0.2071(4) -0.0060(3) 0.7590(2) 0.0306(8) Uani 1 1 d . . .
N6 N 0.1003(4) 0.0394(3) 0.7890(2) 0.0298(8) Uani 1 1 d . . .
N7 N 0.9949(5) 0.0814(3) 0.8151(3) 0.0460(10) Uani 1 1 d . . .
O1 O 0.4195(4) 0.1584(2) 0.92459(18) 0.0287(6) Uani 1 1 d . . .
O2 O 0.2474(6) -0.1504(4) 0.6253(3) 0.0680(13) Uani 1 1 d . . .
N1 N 0.5131(4) 0.1230(2) 0.6996(2) 0.0255(7) Uani 1 1 d . . .
C3 C 0.6234(5) 0.1911(3) 0.7155(3) 0.0236(7) Uani 1 1 d . . .
H3 H 0.6940 0.1907 0.7724 0.028 Uiso 1 1 calc R . .
C2 C 0.6365(5) 0.2383(3) 1.1512(3) 0.0235(7) Uani 1 1 d . . .
H2 H 0.7164 0.1930 1.1640 0.028 Uiso 1 1 calc R . .
C5 C 0.4139(5) 0.3045(3) 1.0505(3) 0.0301(9) Uani 1 1 d . . .
H5 H 0.3398 0.3043 0.9950 0.036 Uiso 1 1 calc R . .
C4 C 0.4099(5) 0.1259(3) 0.6177(3) 0.0298(9) Uani 1 1 d . . .
H4 H 0.3327 0.0792 0.6057 0.036 Uiso 1 1 calc R . .
C6 C 0.5321(5) 0.1590(3) 0.9941(2) 0.0225(7) Uani 1 1 d . . .
C7 C 0.7750(5) -0.0235(3) 0.9482(3) 0.0229(7) Uani 1 1 d . . .
C8 C 0.7839(4) -0.0921(3) 0.8732(2) 0.0225(7) Uani 1 1 d . . .
C9 C 0.9164(5) -0.1508(3) 0.8753(3) 0.0286(8) Uani 1 1 d . . .
C10 C 0.9193(5) -0.2155(3) 0.8015(3) 0.0325(9) Uani 1 1 d . . .
C11 C 0.7907(5) -0.2185(3) 0.7288(3) 0.0298(8) Uani 1 1 d . . .
C12 C 0.6627(5) -0.1566(3) 0.7314(3) 0.0253(8) Uani 1 1 d . . .
C13 C 0.8664(8) 0.3436(5) 0.9584(4) 0.0588(15) Uani 1 1 d . . .
H13A H 0.9766 0.3475 0.9409 0.088 Uiso 1 1 calc R . .
H13B H 0.8549 0.2842 0.9888 0.088 Uiso 1 1 calc R . .
C14 C 0.8419(9) 0.4184(5) 1.0276(4) 0.0679(18) Uani 1 1 d . . .
H14A H 0.9209 0.4123 1.0834 0.102 Uiso 1 1 calc R . .
H14B H 0.7336 0.4141 1.0460 0.102 Uiso 1 1 calc R . .
H14C H 0.8552 0.4773 0.9981 0.102 Uiso 1 1 calc R . .
H7 H 0.868(6) -0.020(3) 1.002(3) 0.021(11) Uiso 1 1 d . . .
H9 H 0.999(6) -0.144(4) 0.925(4) 0.027(11) Uiso 1 1 d . . .
H10 H 1.013(7) -0.260(4) 0.803(4) 0.046(15) Uiso 1 1 d . . .
H11 H 0.786(6) -0.261(4) 0.677(4) 0.032(12) Uiso 1 1 d . . .
H12 H 0.575(6) -0.157(3) 0.684(3) 0.020(10) Uiso 1 1 d . . .
H15 H 0.227(10) -0.101(7) 0.662(6) 0.08(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N5 2.140(3) . ?
Hg1 N3 2.242(3) . ?
Hg1 N1 2.393(3) . ?
Hg1 N4 2.431(3) . ?
Hg1 O1 2.486(3) . ?
C1 C5 1.378(6) . ?
C1 C2 1.391(5) . ?
C1 C6 1.510(5) . ?
N2 C6 1.334(5) . ?
N2 N3 1.372(4) . ?
N3 C7 1.279(5) . ?
N4 C12 1.332(5) . ?
N4 C8 1.355(5) . ?
N5 N6 1.213(5) . ?
N6 N7 1.156(6) 1_455 ?
N7 N6 1.156(6) 1_655 ?
O1 C6 1.262(5) . ?
O2 C13 1.415(7) 2_646 ?
O2 H15 0.92(9) . ?
N1 C3 1.342(5) . ?
N1 C4 1.345(5) . ?
C3 C2 1.377(6) 4_565 ?
C3 H3 0.9300 . ?
C2 C3 1.377(6) 4_566 ?
C2 H2 0.9300 . ?
C5 C4 1.384(6) 4_566 ?
C5 H5 0.9300 . ?
C4 C5 1.384(6) 4_565 ?
C4 H4 0.9300 . ?
C7 C8 1.456(5) . ?
C7 H7 1.01(5) . ?
C8 C9 1.381(6) . ?
C9 C10 1.398(6) . ?
C9 H9 0.92(5) . ?
C10 C11 1.380(6) . ?
C10 H10 1.00(6) . ?
C11 C12 1.388(6) . ?
C11 H11 0.95(5) . ?
C12 H12 0.92(5) . ?
C13 O2 1.415(7) 2_656 ?
C13 C14 1.486(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Hg1 N3 157.00(12) . . ?
N5 Hg1 N1 94.19(13) . . ?
N3 Hg1 N1 106.07(11) . . ?
N5 Hg1 N4 117.58(13) . . ?
N3 Hg1 N4 71.50(11) . . ?
N1 Hg1 N4 96.62(11) . . ?
N5 Hg1 O1 102.97(12) . . ?
N3 Hg1 O1 67.79(10) . . ?
N1 Hg1 O1 87.82(10) . . ?
N4 Hg1 O1 138.63(10) . . ?
C5 C1 C2 118.3(4) . . ?
C5 C1 C6 119.2(3) . . ?
C2 C1 C6 122.5(3) . . ?
C6 N2 N3 111.6(3) . . ?
C7 N3 N2 118.9(3) . . ?
C7 N3 Hg1 118.7(2) . . ?
N2 N3 Hg1 122.2(2) . . ?
C12 N4 C8 118.9(3) . . ?
C12 N4 Hg1 129.6(3) . . ?
C8 N4 Hg1 111.4(2) . . ?
N6 N5 Hg1 116.2(3) . . ?
N7 N6 N5 177.7(4) 1_455 . ?
C6 O1 Hg1 109.1(2) . . ?
C13 O2 H15 112(5) 2_646 . ?
C3 N1 C4 117.6(3) . . ?
C3 N1 Hg1 122.4(2) . . ?
C4 N1 Hg1 118.4(3) . . ?
N1 C3 C2 122.9(3) . 4_565 ?
N1 C3 H3 118.6 . . ?
C2 C3 H3 118.6 4_565 . ?
C3 C2 C1 119.2(4) 4_566 . ?
C3 C2 H2 120.4 4_566 . ?
C1 C2 H2 120.4 . . ?
C1 C5 C4 119.2(4) . 4_566 ?
C1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 4_566 . ?
N1 C4 C5 122.8(4) . 4_565 ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 4_565 . ?
O1 C6 N2 128.7(3) . . ?
O1 C6 C1 117.2(3) . . ?
N2 C6 C1 114.1(3) . . ?
N3 C7 C8 120.7(3) . . ?
N3 C7 H7 121(3) . . ?
C8 C7 H7 118(3) . . ?
N4 C8 C9 121.7(4) . . ?
N4 C8 C7 117.3(3) . . ?
C9 C8 C7 121.0(3) . . ?
C8 C9 C10 118.8(4) . . ?
C8 C9 H9 118(3) . . ?
C10 C9 H9 124(3) . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 121(3) . . ?
C9 C10 H10 120(3) . . ?
C10 C11 C12 118.4(4) . . ?
C10 C11 H11 123(3) . . ?
C12 C11 H11 118(3) . . ?
N4 C12 C11 122.8(4) . . ?
N4 C12 H12 117(3) . . ?
C11 C12 H12 120(3) . . ?
O2 C13 C14 111.7(6) 2_656 . ?
O2 C13 H13A 109.3 2_656 . ?
C14 C13 H13A 109.3 . . ?
O2 C13 H13B 109.3 2_656 . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        70.56
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_grat010a
_database_code_depnum_ccdc_archive 'CCDC 1540270'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 Hg N7 O3'
_chemical_formula_weight         531.94

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   14.4728(11)
_cell_length_b                   14.4895(12)
_cell_length_c                   16.2609(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3410.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      33.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2032
_exptl_absorpt_coefficient_mu    9.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3637
_exptl_absorpt_correction_T_max  0.7133
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            47154
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         33.19
_reflns_number_total             6516
_reflns_number_gt                5017
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0167P)²+2.2961P] 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         6516
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0410
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.852636(5) 0.532111(6) 0.435125(4) 0.01210(3) Uani 1 1 d . . .
N1 N 0.77912(13) 0.43032(13) 0.53535(11) 0.0129(4) Uani 1 1 d . . .
N2 N 0.92238(13) 0.54956(12) 0.55811(11) 0.0117(3) Uani 1 1 d . . .
N3 N 0.99475(13) 0.60971(13) 0.57148(11) 0.0131(3) Uani 1 1 d . . .
N4 N 1.22715(13) 0.86179(13) 0.54356(11) 0.0137(4) Uani 1 1 d . . .
N5 N 0.85962(15) 0.52915(15) 0.30550(12) 0.0213(4) Uani 1 1 d . . .
N6 N 0.82915(16) 0.46363(16) 0.26876(12) 0.0208(4) Uani 1 1 d . . .
N7 N 0.8029(2) 0.40485(19) 0.22748(13) 0.0351(6) Uani 1 1 d . . .
O1 O 0.95872(12) 0.67374(12) 0.44450(10) 0.0197(4) Uani 1 1 d . . .
C1 C 0.82122(16) 0.43390(16) 0.60958(13) 0.0131(4) Uani 1 1 d . . .
C2 C 0.79408(16) 0.37875(17) 0.67504(14) 0.0167(5) Uani 1 1 d . . .
H2A H 0.8243 0.3833 0.7268 0.020 Uiso 1 1 calc R . .
C3 C 0.72211(17) 0.31692(18) 0.66360(15) 0.0203(5) Uani 1 1 d . . .
H3A H 0.7026 0.2778 0.7071 0.024 Uiso 1 1 calc R . .
C4 C 0.67915(18) 0.31332(18) 0.58741(15) 0.0204(5) Uani 1 1 d . . .
H4A H 0.6298 0.2714 0.5779 0.024 Uiso 1 1 calc R . .
C5 C 0.70920(16) 0.37176(17) 0.52532(14) 0.0166(5) Uani 1 1 d . . .
H5A H 0.6787 0.3699 0.4736 0.020 Uiso 1 1 calc R . .
C6 C 0.89716(16) 0.49962(16) 0.61907(13) 0.0138(4) Uani 1 1 d . . .
H6A H 0.9278 0.5053 0.6705 0.017 Uiso 1 1 calc R . .
C7 C 1.00602(15) 0.66874(15) 0.50935(13) 0.0119(4) Uani 1 1 d . . .
C8 C 1.08324(15) 0.73593(15) 0.52284(13) 0.0118(4) Uani 1 1 d . . .
C9 C 1.10414(16) 0.80057(16) 0.46267(14) 0.0156(4) Uani 1 1 d . . .
H9A H 1.0693 0.8029 0.4132 0.019 Uiso 1 1 calc R . .
C10 C 1.17622(17) 0.86163(17) 0.47538(14) 0.0162(4) Uani 1 1 d . . .
H10A H 1.1900 0.9054 0.4336 0.019 Uiso 1 1 calc R . .
C11 C 1.20745(16) 0.79923(16) 0.60200(13) 0.0147(4) Uani 1 1 d . . .
H11A H 1.2437 0.7986 0.6507 0.018 Uiso 1 1 calc R . .
C12 C 1.13669(15) 0.73575(16) 0.59420(13) 0.0141(4) Uani 1 1 d . . .
H12A H 1.1246 0.6926 0.6369 0.017 Uiso 1 1 calc R . .
O2 O 0.91386(13) 0.78622(14) 0.31825(11) 0.0238(4) Uani 1 1 d . . .
H2B H 0.922(2) 0.755(2) 0.359(2) 0.041(10) Uiso 1 1 d . . .
C13 C 0.9792(2) 0.7596(2) 0.25684(15) 0.0298(6) Uani 1 1 d . . .
H13A H 0.9690 0.7961 0.2069 0.045 Uiso 1 1 calc R . .
H13B H 0.9714 0.6939 0.2442 0.045 Uiso 1 1 calc R . .
H13C H 1.0420 0.7705 0.2772 0.045 Uiso 1 1 calc R . .
O3 O 0.61959(17) 0.47597(17) 0.33398(14) 0.0379(5) Uani 1 1 d . . .
H3B H 0.612(3) 0.414(4) 0.327(3) 0.095(17) Uiso 1 1 d . . .
C14 C 0.5373(2) 0.5069(2) 0.37177(19) 0.0326(7) Uani 1 1 d . . .
H14A H 0.5265 0.4715 0.4222 0.049 Uiso 1 1 calc R . .
H14B H 0.4853 0.4982 0.3340 0.049 Uiso 1 1 calc R . .
H14C H 0.5432 0.5726 0.3854 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N5 2.111(2) . ?
Hg1 N2 2.2544(18) . ?
Hg1 N4 2.4045(19) 4_466 ?
Hg1 N1 2.4420(18) . ?
Hg1 O1 2.5674(17) . ?
N1 C5 1.331(3) . ?
N1 C1 1.353(3) . ?
N2 C6 1.280(3) . ?
N2 N3 1.380(3) . ?
N3 C7 1.334(3) . ?
N4 C10 1.331(3) . ?
N4 C11 1.344(3) . ?
N4 Hg1 2.4045(19) 4_566 ?
N5 N6 1.205(3) . ?
N6 N7 1.149(3) . ?
O1 C7 1.259(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.462(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.388(3) . ?
C7 C8 1.498(3) . ?
C8 C9 1.388(3) . ?
C8 C12 1.395(3) . ?
C9 C10 1.383(3) . ?
C11 C12 1.382(3) . ?
O2 C13 1.428(3) . ?
O3 C14 1.413(4) . ?

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
N5 Hg1 N2 150.08(7) . . ?
N5 Hg1 N4 101.13(7) . 4_466 ?
N2 Hg1 N4 97.97(6) . 4_466 ?
N5 Hg1 N1 132.46(7) . . ?
N2 Hg1 N1 70.78(6) . . ?
N4 Hg1 N1 87.76(6) 4_466 . ?
N5 Hg1 O1 92.69(7) . . ?
N2 Hg1 O1 65.79(6) . . ?
N4 Hg1 O1 86.10(6) 4_466 . ?
N1 Hg1 O1 134.72(6) . . ?
C5 N1 C1 118.44(19) . . ?
C5 N1 Hg1 129.39(15) . . ?
C1 N1 Hg1 112.09(14) . . ?
C6 N2 N3 116.83(18) . . ?
C6 N2 Hg1 119.72(15) . . ?
N3 N2 Hg1 123.40(13) . . ?
C7 N3 N2 112.24(17) . . ?
C10 N4 C11 118.0(2) . . ?
C10 N4 Hg1 122.63(15) . 4_566 ?
C11 N4 Hg1 119.32(15) . 4_566 ?
N6 N5 Hg1 119.57(17) . . ?
N7 N6 N5 173.9(3) . . ?
C7 O1 Hg1 109.20(14) . . ?
N1 C1 C2 122.3(2) . . ?
N1 C1 C6 117.23(19) . . ?
C2 C1 C6 120.4(2) . . ?
C3 C2 C1 118.8(2) . . ?
C2 C3 C4 118.7(2) . . ?
C3 C4 C5 119.1(2) . . ?
N1 C5 C4 122.6(2) . . ?
N2 C6 C1 120.0(2) . . ?
O1 C7 N3 127.2(2) . . ?
O1 C7 C8 119.39(19) . . ?
N3 C7 C8 113.39(18) . . ?
C9 C8 C12 117.8(2) . . ?
C9 C8 C7 119.86(19) . . ?
C12 C8 C7 122.30(19) . . ?
C10 C9 C8 119.4(2) . . ?
N4 C10 C9 122.9(2) . . ?
N4 C11 C12 122.8(2) . . ?
C11 C12 C8 119.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        33.19
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.359
_refine_diff_density_min         -1.991
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1540272'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Hg N7 O1.50'
_chemical_formula_weight         504.91

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'
Hg Hg -4.2923 7.6849 '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                   8.1973(2)
_cell_length_b                   14.0633(3)
_cell_length_c                   14.2839(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.485(2)
_cell_angle_gamma                90
_cell_volume                     1636.13(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5619
_cell_measurement_theta_min      3.1112
_cell_measurement_theta_max      73.8407

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.050
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    17.049
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10707
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.426
_diffrn_reflns_theta_max         74.006
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3271
_reflns_number_gt                2877
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0192P)²+0.8964P] 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_number_reflns         3271
_refine_ls_number_parameters     235
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0436
_refine_ls_wR_factor_gt          0.0417
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.061
_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
Hg Hg 0.53995(2) -0.02007(2) 0.17168(2) 0.01903(5) Uani 1 1 d . . . . .
O1 O 0.5541(3) -0.16894(18) 0.07761(17) 0.0293(6) Uani 1 1 d . . . . .
N1 N 0.3383(3) 0.1035(2) 0.19337(19) 0.0197(5) Uani 1 1 d . . . . .
N2 N 0.3361(3) -0.03035(19) 0.05469(18) 0.0184(5) Uani 1 1 d . . . . .
N3 N 0.3331(3) -0.0990(2) -0.01371(18) 0.0190(5) Uani 1 1 d . . . . .
N4 N 0.4646(4) -0.3855(2) -0.19919(19) 0.0230(6) Uani 1 1 d . . . . .
N5 N 0.7825(4) 0.0078(2) 0.2375(2) 0.0302(7) Uani 1 1 d . . . . .
N6 N 0.8938(4) -0.0340(2) 0.2061(2) 0.0290(7) Uani 1 1 d . . . . .
N7 N 1.0048(4) -0.0712(3) 0.1796(3) 0.0433(9) Uani 1 1 d . . . . .
C1 C 0.2164(4) 0.1040(2) 0.1218(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.0876(4) 0.1686(3) 0.1179(3) 0.0283(8) Uani 1 1 d . . . . .
H2 H 0.0033 0.1682 0.0664 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0845(5) 0.2338(3) 0.1905(3) 0.0328(9) Uani 1 1 d . . . . .
H3 H -0.0020 0.2789 0.1895 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2100(4) 0.2323(3) 0.2649(3) 0.0267(7) Uani 1 1 d . . . . .
H4 H 0.2099 0.2756 0.3160 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3341(4) 0.1666(2) 0.2629(2) 0.0236(7) Uani 1 1 d . . . . .
H5 H 0.4205 0.1662 0.3132 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2226(4) 0.0323(2) 0.0481(2) 0.0202(7) Uani 1 1 d . . . . .
H6 H 0.1416 0.0324 -0.0050 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4486(4) -0.1649(2) 0.0074(2) 0.0198(6) Uani 1 1 d . . . . .
C8 C 0.4492(4) -0.2423(2) -0.0651(2) 0.0193(6) Uani 1 1 d . . . . .
C9 C 0.3474(4) -0.2407(2) -0.1504(2) 0.0219(7) Uani 1 1 d . . . . .
H9 H 0.2708 -0.1905 -0.1639 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3593(4) -0.3128(2) -0.2149(2) 0.0230(7) Uani 1 1 d . . . . .
H10 H 0.2900 -0.3108 -0.2729 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5598(5) -0.3882(3) -0.1167(3) 0.0306(8) Uani 1 1 d . . . . .
H11 H 0.6335 -0.4400 -0.1044 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5554(5) -0.3185(3) -0.0484(2) 0.0285(8) Uani 1 1 d . . . . .
H12 H 0.6247 -0.3229 0.0094 0.034 Uiso 1 1 calc R U . . .
C23 C 0.9342(19) 0.1051(7) 0.4710(8) 0.068(4) Uani 0.5 1 d D U P A 1
H23A H 0.8791 0.1521 0.5072 0.101 Uiso 0.5 1 calc R U P A 1
H23B H 1.0352 0.1327 0.4520 0.101 Uiso 0.5 1 calc R U P A 1
H23C H 0.8611 0.0869 0.4148 0.101 Uiso 0.5 1 calc R U P A 1
C24 C 0.9765(15) 0.0173(7) 0.5321(8) 0.052(3) Uani 0.5 1 d D U P A 1
H24A H 1.0473 0.0372 0.5894 0.062 Uiso 0.5 1 calc R U P A 1
H24B H 0.8737 -0.0085 0.5524 0.062 Uiso 0.5 1 calc R U P A 1
C25 C 1.0632(14) -0.0624(7) 0.4845(8) 0.052(3) Uani 0.5 1 d D U P A 1
H25A H 1.1642 -0.0359 0.4626 0.063 Uiso 0.5 1 calc R U P A 1
H25B H 0.9909 -0.0831 0.4280 0.063 Uiso 0.5 1 calc R U P A 1
C26 C 1.1107(11) -0.1500(7) 0.5446(7) 0.048(2) Uani 0.5 1 d D U P A 1
H26A H 1.0167 -0.1704 0.5777 0.057 Uiso 0.5 1 calc R U P A 1
H26B H 1.1395 -0.2029 0.5039 0.057 Uiso 0.5 1 calc R U P A 1
O27 O 1.2503(8) -0.1273(5) 0.6131(5) 0.0523(18) Uani 0.5 1 d D U P A 1
H27 H 1.2265 -0.0810 0.6462 0.078 Uiso 0.5 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
Hg N5 2.137(3) . ?
Hg N2 2.230(3) . ?
Hg N4 2.410(3) 4_556 ?
Hg N1 2.442(3) . ?
Hg O1 2.498(2) . ?
O1 C7 1.249(4) . ?
N1 C5 1.335(5) . ?
N1 C1 1.346(4) . ?
N2 C6 1.278(4) . ?
N2 N3 1.372(4) . ?
N3 C7 1.335(4) . ?
N4 C11 1.339(4) . ?
N4 C10 1.339(4) . ?
N4 Hg 2.410(3) 4 ?
N5 N6 1.213(5) . ?
N6 N7 1.150(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.462(4) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.504(4) . ?
C8 C12 1.384(5) . ?
C8 C9 1.396(5) . ?
C9 C10 1.382(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C23 C24 1.529(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.526(5) . ?
C24 C23 1.873(18) 3_756 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.527(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 O27 1.455(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O27 H27 0.8400 . ?

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
N5 Hg N2 157.27(12) . . ?
N5 Hg N4 94.05(11) . 4_556 ?
N2 Hg N4 107.61(10) . 4_556 ?
N5 Hg N1 115.04(11) . . ?
N2 Hg N1 71.38(9) . . ?
N4 Hg N1 93.41(10) 4_556 . ?
N5 Hg O1 107.03(11) . . ?
N2 Hg O1 67.60(9) . . ?
N4 Hg O1 88.92(9) 4_556 . ?
N1 Hg O1 137.56(8) . . ?
C7 O1 Hg 108.9(2) . . ?
C5 N1 C1 118.8(3) . . ?
C5 N1 Hg 130.0(2) . . ?
C1 N1 Hg 111.2(2) . . ?
C6 N2 N3 118.6(3) . . ?
C6 N2 Hg 119.2(2) . . ?
N3 N2 Hg 122.1(2) . . ?
C7 N3 N2 111.8(2) . . ?
C11 N4 C10 118.0(3) . . ?
C11 N4 Hg 118.9(2) . 4 ?
C10 N4 Hg 120.5(2) . 4 ?
N6 N5 Hg 116.7(3) . . ?
N7 N6 N5 176.5(4) . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 C6 117.4(3) . . ?
C2 C1 C6 120.6(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 C1 120.4(3) . . ?
N2 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N3 128.5(3) . . ?
O1 C7 C8 117.7(3) . . ?
N3 C7 C8 113.8(3) . . ?
C12 C8 C9 117.7(3) . . ?
C12 C8 C7 119.5(3) . . ?
C9 C8 C7 122.8(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N4 C10 C9 122.7(3) . . ?
N4 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N4 C11 C12 122.7(3) . . ?
N4 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C8 C12 C11 119.5(3) . . ?
C8 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C23 115.2(11) . . ?
C25 C24 C23 27.4(6) . 3_756 ?
C23 C24 C23 142.5(8) . 3_756 ?
C25 C24 H24A 108.5 . . ?
C23 C24 H24A 108.5 . . ?
C23 C24 H24A 94.9 3_756 . ?
C25 C24 H24B 108.5 . . ?
C23 C24 H24B 108.5 . . ?
C23 C24 H24B 91.1 3_756 . ?
H24A C24 H24B 107.5 . . ?
C24 C25 C26 116.3(9) . . ?
C24 C25 H25A 108.2 . . ?
C26 C25 H25A 108.2 . . ?
C24 C25 H25B 108.2 . . ?
C26 C25 H25B 108.2 . . ?
H25A C25 H25B 107.4 . . ?
O27 C26 C25 109.4(8) . . ?
O27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
O27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C26 O27 H27 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
C6 N2 N3 C7 -173.5(3) . . . . ?
Hg N2 N3 C7 10.1(3) . . . . ?
C5 N1 C1 C2 0.6(5) . . . . ?
Hg N1 C1 C2 -179.4(3) . . . . ?
C5 N1 C1 C6 -178.5(3) . . . . ?
Hg N1 C1 C6 1.5(4) . . . . ?
N1 C1 C2 C3 -0.6(6) . . . . ?
C6 C1 C2 C3 178.4(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
Hg N1 C5 C4 -179.8(3) . . . . ?
C3 C4 C5 N1 -0.9(6) . . . . ?
N3 N2 C6 C1 177.0(3) . . . . ?
Hg N2 C6 C1 -6.5(4) . . . . ?
N1 C1 C6 N2 3.0(5) . . . . ?
C2 C1 C6 N2 -176.0(3) . . . . ?
Hg O1 C7 N3 -6.2(4) . . . . ?
Hg O1 C7 C8 172.9(2) . . . . ?
N2 N3 C7 O1 -1.4(5) . . . . ?
N2 N3 C7 C8 179.5(3) . . . . ?
O1 C7 C8 C12 5.4(5) . . . . ?
N3 C7 C8 C12 -175.5(3) . . . . ?
O1 C7 C8 C9 -174.0(3) . . . . ?
N3 C7 C8 C9 5.2(5) . . . . ?
C12 C8 C9 C10 -1.6(5) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
C11 N4 C10 C9 1.0(5) . . . . ?
Hg N4 C10 C9 -160.8(3) 4 . . . ?
C8 C9 C10 N4 0.4(5) . . . . ?
C10 N4 C11 C12 -1.1(6) . . . . ?
Hg N4 C11 C12 161.0(3) 4 . . . ?
C9 C8 C12 C11 1.5(5) . . . . ?
C7 C8 C12 C11 -177.8(4) . . . . ?
N4 C11 C12 C8 -0.2(6) . . . . ?
C23 C24 C25 C26 178.6(11) . . . . ?
C23 C24 C25 C26 -6.6(10) 3_756 . . . ?
C24 C25 C26 O27 -73.7(11) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1540269'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_date             2012-06-28T12:59:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 36G
;
_chemical_name_common            36G
_chemical_formula_moiety         '2(C12 H9 Hg N7 O), H2 O'
_chemical_formula_sum            'C24 H20 Hg2 N14 O3'
_chemical_formula_weight         953.72

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9694(8)
_cell_length_b                   12.3482(6)
_cell_length_c                   15.9191(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2942.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    555
_cell_measurement_theta_min      3
_cell_measurement_theta_max      20

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    2.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1784
_exptl_special_details           
;
 1 degree / 120 seconds / 30mm
;

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

_exptl_absorpt_coefficient_mu    10.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL2008
_exptl_absorpt_correction_T_min  0.1452
_exptl_absorpt_correction_T_max  0.3025

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

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_number            14438
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             2675
_reflns_number_gt                1325
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'maXus, Zortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0723P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2675
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.273
_refine_diff_density_min         -2.239
_refine_diff_density_rms         0.174

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.1514(8) 0.8310(10) 0.1619(8) 0.084(4) Uani 1 1 d . . .
H1 H 0.0994 0.8432 0.1314 0.101 Uiso 1 1 calc R . .
C2 C 0.1512(11) 0.7504(9) 0.2220(9) 0.086(5) Uani 1 1 d . . .
H2 H 0.0997 0.7104 0.2321 0.103 Uiso 1 1 calc R . .
C3 C 0.2276(12) 0.7302(11) 0.2663(9) 0.093(5) Uani 1 1 d . . .
H3 H 0.2296 0.6751 0.306 0.111 Uiso 1 1 calc R . .
C4 C 0.3008(10) 0.7930(12) 0.2509(9) 0.085(4) Uani 1 1 d . . .
H4 H 0.3531 0.7824 0.2813 0.102 Uiso 1 1 calc R . .
C5 C 0.2965(7) 0.8724(9) 0.1899(8) 0.063(3) Uani 1 1 d . . .
C6 C 0.3749(7) 0.9384(9) 0.1697(7) 0.066(3) Uani 1 1 d . . .
H6 H 0.4262 0.9317 0.2023 0.079 Uiso 1 1 calc R . .
C7 C 0.4374(6) 1.1240(9) 0.0240(7) 0.058(3) Uani 1 1 d . . .
C8 C 0.5161(6) 1.1923(9) 0.0011(7) 0.052(3) Uani 1 1 d . . .
C9 C 0.5988(6) 1.1866(9) 0.0395(7) 0.058(3) Uani 1 1 d . . .
H9 H 0.6091 1.1352 0.0811 0.07 Uiso 1 1 calc R . .
C10 C 0.6647(7) 1.2556(8) 0.0168(7) 0.055(3) Uani 1 1 d . . .
H10 H 0.7199 1.2483 0.043 0.066 Uiso 1 1 calc R . .
C11 C 0.5757(6) 1.3387(10) -0.0795(7) 0.070(3) Uani 1 1 d . . .
H11 H 0.5675 1.3909 -0.1209 0.084 Uiso 1 1 calc R . .
C12 C 0.5056(8) 1.2712(9) -0.0611(8) 0.070(3) Uani 1 1 d . . .
H12 H 0.4517 1.2779 -0.0897 0.084 Uiso 1 1 calc R . .
N6 N 0.1217(8) 0.9998(9) -0.1023(7) 0.078(3) Uani 1 1 d . . .
N7 N 0.0605(7) 1.0423(9) -0.1295(8) 0.097(4) Uani 1 1 d . . .
N1 N 0.2215(6) 0.8911(8) 0.1459(6) 0.069(3) Uani 1 1 d . . .
N2 N 0.3745(5) 1.0043(6) 0.1088(5) 0.050(2) Uani 1 1 d . . .
N3 N 0.4492(5) 1.0636(7) 0.0909(5) 0.054(2) Uani 1 1 d . . .
N4 N 0.6556(5) 1.3337(7) -0.0410(5) 0.053(2) Uani 1 1 d . . .
N5 N 0.1848(9) 0.9520(9) -0.0750(8) 0.102(4) Uani 1 1 d . . .
O1 O 0.3705(4) 1.1327(7) -0.0220(5) 0.082(3) Uani 1 1 d . . .
O2 O 0.6043(14) 1.0159(18) 0.2066(15) 0.142(9) Uani 0.5 1 d P . .
H2O H 0.5549 1.0699 0.1997 0.214 Uiso 0.5 1 d PR . .
H2P H 0.6037 0.9714 0.1516 0.214 Uiso 0.5 1 d PR . .
Hg1 Hg 0.25103(3) 1.01853(4) 0.03201(3) 0.0670(2) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.311(12) . ?
C1 C2 1.380(16) . ?
C1 H1 0.93 . ?
C2 C3 1.367(19) . ?
C2 H2 0.93 . ?
C3 C4 1.36(2) . ?
C3 H3 0.93 . ?
C4 C5 1.382(17) . ?
C4 H4 0.93 . ?
C5 N1 1.343(13) . ?
C5 C6 1.465(13) . ?
C6 N2 1.266(12) . ?
C6 H6 0.93 . ?
C7 O1 1.245(11) . ?
C7 N3 1.311(12) . ?
C7 C8 1.494(13) . ?
C8 C9 1.383(12) . ?
C8 C12 1.398(16) . ?
C9 C10 1.352(14) . ?
C9 H9 0.93 . ?
C10 N4 1.340(12) . ?
C10 H10 0.93 . ?
C11 N4 1.345(11) . ?
C11 C12 1.372(14) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
N6 N7 1.141(13) . ?
N6 N5 1.196(14) . ?
N1 Hg1 2.441(9) . ?
N2 N3 1.367(10) . ?
N2 Hg1 2.222(8) . ?
N4 Hg1 2.321(8) 3_575 ?
N5 Hg1 2.135(11) . ?
O1 Hg1 2.435(7) . ?
O2 H2O 1.0017 . ?
O2 H2P 1.0329 . ?
Hg1 N4 2.321(8) 3_475 ?

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 C1 C2 123.0(13) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.2(12) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 118.4(13) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.5(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.8(11) . . ?
N1 C5 C6 117.4(10) . . ?
C4 C5 C6 120.8(11) . . ?
N2 C6 C5 121.4(10) . . ?
N2 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 N3 129.4(10) . . ?
O1 C7 C8 116.2(10) . . ?
N3 C7 C8 114.4(9) . . ?
C9 C8 C12 116.7(10) . . ?
C9 C8 C7 124.7(10) . . ?
C12 C8 C7 118.6(10) . . ?
C10 C9 C8 120.2(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N4 C10 C9 124.2(10) . . ?
N4 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
N4 C11 C12 123.8(11) . . ?
N4 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C8 119.3(11) . . ?
C11 C12 H12 120.4 . . ?
C8 C12 H12 120.4 . . ?
N7 N6 N5 177.7(14) . . ?
C1 N1 C5 118.1(11) . . ?
C1 N1 Hg1 130.9(9) . . ?
C5 N1 Hg1 110.3(7) . . ?
C6 N2 N3 120.0(9) . . ?
C6 N2 Hg1 118.5(7) . . ?
N3 N2 Hg1 121.5(6) . . ?
C7 N3 N2 111.3(8) . . ?
C10 N4 C11 115.8(9) . . ?
C10 N4 Hg1 117.5(7) . 3_575 ?
C11 N4 Hg1 122.6(7) . 3_575 ?
N6 N5 Hg1 117.8(9) . . ?
C7 O1 Hg1 109.4(7) . . ?
H2O O2 H2P 104.8 . . ?
N5 Hg1 N2 142.6(4) . . ?
N5 Hg1 N4 93.8(4) . 3_475 ?
N2 Hg1 N4 122.7(3) . 3_475 ?
N5 Hg1 O1 106.4(4) . . ?
N2 Hg1 O1 68.2(3) . . ?
N4 Hg1 O1 91.1(3) 3_475 . ?
N5 Hg1 N1 105.1(4) . . ?
N2 Hg1 N1 72.0(3) . . ?
N4 Hg1 N1 110.5(3) 3_475 . ?
O1 Hg1 N1 140.2(3) . . ?




# END of CIF
####################################################################### 
# 
# 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_grat014
_database_code_depnum_ccdc_archive 'CCDC 1540273'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Hg N7 O2'
_chemical_formula_weight         527.94

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.3282(15)
_cell_length_b                   14.3823(17)
_cell_length_c                   11.7472(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.721(7)
_cell_angle_gamma                90
_cell_volume                     1719.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2283
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    8.974
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_T_max  0.8409
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24527
_diffrn_reflns_av_unetI/netI     0.1703
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         33.266
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6560
_reflns_number_gt                3144
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0380P)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_number_reflns         6560
_refine_ls_number_parameters     266
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.014
_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 0.41091(3) 0.01977(2) 0.29342(3) 0.02731(11) Uani 1 1 d . . . . .
N1 N 0.2078(6) -0.0619(5) 0.3316(6) 0.0291(17) Uani 1 1 d . . . . .
N2 N 0.3685(7) 0.0604(4) 0.4659(6) 0.0242(15) Uani 1 1 d . . . . .
N3 N 0.4447(7) 0.1245(4) 0.5347(6) 0.0227(16) Uani 1 1 d . . . . .
N4 N 0.7716(8) 0.3724(4) 0.6756(6) 0.0333(19) Uani 1 1 d . . . . .
N5 N 0.5009(9) -0.0475(5) 0.1657(7) 0.041(2) Uani 1 1 d . . . . .
N6 N 0.5949(10) -0.0952(6) 0.1999(7) 0.0365(18) Uani 1 1 d . . . . .
N7 N 0.6863(10) -0.1421(8) 0.2264(8) 0.070(3) Uani 1 1 d . . . . .
O1 O 0.5514(6) 0.1505(4) 0.3784(5) 0.0350(15) Uani 1 1 d . . . . .
C1 C 0.1880(8) -0.0461(6) 0.4383(9) 0.035(2) Uani 1 1 d . . . . .
C2 C 0.0913(10) -0.0901(7) 0.4844(10) 0.053(3) Uani 1 1 d . . . . .
H2A H 0.0804 -0.0774 0.5615 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0098(9) -0.1527(7) 0.4189(11) 0.055(3) Uani 1 1 d . . . . .
H3A H -0.0596 -0.1822 0.4489 0.066 Uiso 1 1 calc R U . . .
C4 C 0.0316(9) -0.1715(6) 0.3088(10) 0.048(3) Uani 1 1 d . . . . .
H4A H -0.0218 -0.2153 0.2618 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1325(8) -0.1257(6) 0.2673(9) 0.037(3) Uani 1 1 d . . . . .
H5A H 0.1488 -0.1395 0.1919 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2744(8) 0.0227(6) 0.5059(8) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.2596 0.0392 0.5809 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5307(9) 0.1657(5) 0.4792(7) 0.025(2) Uani 1 1 d . . . . .
C8 C 0.6132(8) 0.2381(5) 0.5495(7) 0.026(2) Uani 1 1 d . . . . .
C9 C 0.7058(9) 0.2872(5) 0.5012(7) 0.029(2) Uani 1 1 d . . . . .
H9A H 0.7169 0.2753 0.4239 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7820(9) 0.3537(6) 0.5662(7) 0.033(2) Uani 1 1 d . . . . .
H10A H 0.8443 0.3873 0.5316 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6829(8) 0.3229(5) 0.7228(8) 0.028(2) Uani 1 1 d . . . . .
H11A H 0.6759 0.3344 0.8011 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6021(9) 0.2567(5) 0.6633(7) 0.029(2) Uani 1 1 d . . . . .
H12A H 0.5399 0.2243 0.6995 0.034 Uiso 1 1 calc R U . . .
O2 O -0.1788(13) -0.3031(7) 0.5509(10) 0.049(3) Uani 0.647(11) 1 d D U P A 1
H2 H -0.1398 -0.3483 0.5867 0.074 Uiso 0.647(11) 1 calc R U P A 1
C13 C -0.3541(18) -0.4276(12) 0.2867(16) 0.068(5) Uani 0.647(11) 1 d D U P A 1
H13A H -0.4078 -0.4841 0.2757 0.102 Uiso 0.647(11) 1 calc R U P A 1
H13B H -0.2766 -0.4354 0.2496 0.102 Uiso 0.647(11) 1 calc R U P A 1
H13C H -0.4059 -0.3746 0.2520 0.102 Uiso 0.647(11) 1 calc R U P A 1
C14 C -0.3107(17) -0.4102(9) 0.4147(14) 0.050(3) Uani 0.647(11) 1 d D U P A 1
H14A H -0.3888 -0.3999 0.4516 0.060 Uiso 0.647(11) 1 calc R U P A 1
H14B H -0.2637 -0.4656 0.4507 0.060 Uiso 0.647(11) 1 calc R U P A 1
C15 C -0.2239(17) -0.3287(11) 0.4340(14) 0.046(3) Uani 0.647(11) 1 d D U P A 1
H15A H -0.1462 -0.3407 0.3970 0.056 Uiso 0.647(11) 1 calc R U P A 1
H15B H -0.2711 -0.2749 0.3939 0.056 Uiso 0.647(11) 1 calc R U P A 1
O2' O -0.252(2) -0.2888(12) 0.4950(19) 0.044(4) Uani 0.353(11) 1 d D U P A 2
H2' H -0.3118 -0.2557 0.4578 0.066 Uiso 0.353(11) 1 calc R U P A 2
C13' C -0.426(2) -0.4543(17) 0.431(2) 0.051(5) Uani 0.353(11) 1 d D U P A 2
H13D H -0.4997 -0.4845 0.3820 0.076 Uiso 0.353(11) 1 calc R U P A 2
H13E H -0.4584 -0.4043 0.4755 0.076 Uiso 0.353(11) 1 calc R U P A 2
H13F H -0.3786 -0.5001 0.4846 0.076 Uiso 0.353(11) 1 calc R U P A 2
C14' C -0.333(3) -0.4141(17) 0.357(2) 0.050(4) Uani 0.353(11) 1 d D U P A 2
H14C H -0.2985 -0.4652 0.3141 0.060 Uiso 0.353(11) 1 calc R U P A 2
H14D H -0.3828 -0.3714 0.2993 0.060 Uiso 0.353(11) 1 calc R U P A 2
C15' C -0.223(2) -0.3636(19) 0.424(3) 0.048(3) Uani 0.353(11) 1 d D U P A 2
H15D H -0.1682 -0.4090 0.4744 0.058 Uiso 0.353(11) 1 calc R U P A 2
H15C H -0.1681 -0.3387 0.3696 0.058 Uiso 0.353(11) 1 calc R U P A 2


_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 N5 2.126(8) . ?
Hg1 N2 2.222(7) . ?
Hg1 N4 2.392(6) 4_565 ?
Hg1 O1 2.480(5) . ?
Hg1 N1 2.510(7) . ?
N1 C1 1.323(12) . ?
N1 C5 1.349(10) . ?
N2 C6 1.270(11) . ?
N2 N3 1.381(8) . ?
N3 C7 1.326(11) . ?
N4 C10 1.335(11) . ?
N4 C11 1.350(12) . ?
N4 Hg1 2.392(6) 4_666 ?
N5 N6 1.202(11) . ?
N6 N7 1.159(11) . ?
O1 C7 1.257(10) . ?
C1 C2 1.369(14) . ?
C1 C6 1.472(11) . ?
C2 C3 1.375(12) . ?
C2 H2A 0.9500 . ?
C3 C4 1.376(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(15) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.502(10) . ?
C8 C9 1.385(13) . ?
C8 C12 1.386(12) . ?
C9 C10 1.383(11) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.377(10) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
O2 C15 1.423(15) . ?
O2 H2 0.8400 . ?
C13 C14 1.51(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.470(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O2' C15' 1.424(17) . ?
O2' H2' 0.8400 . ?
C13' C14' 1.51(2) . ?
C13' H13D 0.9800 . ?
C13' H13E 0.9800 . ?
C13' H13F 0.9800 . ?
C14' C15' 1.466(18) . ?
C14' H14C 0.9900 . ?
C14' H14D 0.9900 . ?
C15' H15D 0.9900 . ?
C15' H15C 0.9900 . ?

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
N5 Hg1 N2 160.1(3) . . ?
N5 Hg1 N4 100.3(3) . 4_565 ?
N2 Hg1 N4 99.5(2) . 4_565 ?
N5 Hg1 O1 109.5(3) . . ?
N2 Hg1 O1 68.0(2) . . ?
N4 Hg1 O1 89.7(2) 4_565 . ?
N5 Hg1 N1 113.0(3) . . ?
N2 Hg1 N1 70.2(2) . . ?
N4 Hg1 N1 88.1(2) 4_565 . ?
O1 Hg1 N1 137.1(2) . . ?
C1 N1 C5 118.7(9) . . ?
C1 N1 Hg1 110.9(5) . . ?
C5 N1 Hg1 129.7(7) . . ?
C6 N2 N3 117.7(7) . . ?
C6 N2 Hg1 120.4(6) . . ?
N3 N2 Hg1 121.9(5) . . ?
C7 N3 N2 111.9(7) . . ?
C10 N4 C11 117.3(7) . . ?
C10 N4 Hg1 123.3(6) . 4_666 ?
C11 N4 Hg1 119.2(6) . 4_666 ?
N6 N5 Hg1 116.7(6) . . ?
N7 N6 N5 176.2(10) . . ?
C7 O1 Hg1 109.2(5) . . ?
N1 C1 C2 122.3(8) . . ?
N1 C1 C6 116.7(9) . . ?
C2 C1 C6 121.0(9) . . ?
C1 C2 C3 120.0(11) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 C4 118.2(10) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C3 C4 C5 119.2(8) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 121.4(10) . . ?
N1 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
N2 C6 C1 121.3(8) . . ?
N2 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
O1 C7 N3 128.3(7) . . ?
O1 C7 C8 117.8(8) . . ?
N3 C7 C8 113.9(8) . . ?
C9 C8 C12 118.1(7) . . ?
C9 C8 C7 119.7(8) . . ?
C12 C8 C7 122.1(8) . . ?
C10 C9 C8 119.6(8) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
N4 C10 C9 122.7(9) . . ?
N4 C10 H10A 118.7 . . ?
C9 C10 H10A 118.7 . . ?
N4 C11 C12 123.4(9) . . ?
N4 C11 H11A 118.3 . . ?
C12 C11 H11A 118.3 . . ?
C11 C12 C8 118.8(9) . . ?
C11 C12 H12A 120.6 . . ?
C8 C12 H12A 120.6 . . ?
C15 O2 H2 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C13 110.8(13) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O2 C15 C14 116.6(13) . . ?
O2 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
O2 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C15' O2' H2' 109.5 . . ?
C14' C13' H13D 109.5 . . ?
C14' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C14' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C15' C14' C13' 112.7(17) . . ?
C15' C14' H14C 109.0 . . ?
C13' C14' H14C 109.0 . . ?
C15' C14' H14D 109.0 . . ?
C13' C14' H14D 109.0 . . ?
H14C C14' H14D 107.8 . . ?
O2' C15' C14' 117.8(16) . . ?
O2' C15' H15D 107.9 . . ?
C14' C15' H15D 107.9 . . ?
O2' C15' H15C 107.9 . . ?
C14' C15' H15C 107.9 . . ?
H15D C15' H15C 107.2 . . ?

_refine_diff_density_max         2.501
_refine_diff_density_min         -3.463
_refine_diff_density_rms         0.286

