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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_zp01

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Cl2 Hg N3 O3'
_chemical_formula_weight         634.90

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.9298(4)
_cell_length_b                   11.1960(5)
_cell_length_c                   12.2592(5)
_cell_angle_alpha                90.6200(10)
_cell_angle_beta                 92.7180(10)
_cell_angle_gamma                105.5080(10)
_cell_volume                     1311.42(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    6.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.614
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6733
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4593
_reflns_number_gt                4299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_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)+(0.0385P)²+3.3213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg -0.191744(18) 0.181994(17) 0.275372(15) 0.04142(8) Uani 1 1 d . . .
Cl1 Cl -0.07467(16) 0.38397(13) 0.21707(13) 0.0638(4) Uani 1 1 d . . .
N1 N -0.1347(4) 0.0297(3) 0.1724(3) 0.0352(8) Uani 1 1 d . . .
O1 O -0.1125(4) 0.2571(4) 0.4919(3) 0.0595(10) Uani 1 1 d . . .
C1 C -0.1891(5) -0.0430(4) 0.0793(3) 0.0354(9) Uani 1 1 d . . .
Cl2 Cl -0.42535(13) 0.08638(14) 0.32347(12) 0.0592(3) Uani 1 1 d . . .
N2 N 0.0002(4) -0.0957(3) 0.1435(3) 0.0361(8) Uani 1 1 d . . .
H2B H 0.0678 -0.1299 0.1522 0.043 Uiso 1 1 calc R . .
C2 C -0.3043(5) -0.0454(5) 0.0099(4) 0.0485(12) Uani 1 1 d . . .
H2A H -0.3611 0.0071 0.0211 0.058 Uiso 1 1 calc R . .
O2 O -0.3329(5) 0.4331(4) 0.5981(4) 0.0724(13) Uani 1 1 d . . .
N3 N 0.0035(3) 0.1174(3) 0.3688(3) 0.0302(7) Uani 1 1 d . . .
C3 C -0.3300(6) -0.1297(6) -0.0765(4) 0.0581(15) Uani 1 1 d . . .
H3A H -0.4056 -0.1332 -0.1254 0.070 Uiso 1 1 calc R . .
O3 O -0.4566(4) 0.5410(4) 0.7615(3) 0.0626(10) Uani 1 1 d . . .
C4 C -0.2476(7) -0.2084(6) -0.0925(4) 0.0612(16) Uani 1 1 d . . .
H4A H -0.2710 -0.2649 -0.1510 0.073 Uiso 1 1 calc R . .
C5 C -0.1328(6) -0.2073(5) -0.0263(4) 0.0526(13) Uani 1 1 d . . .
H5A H -0.0768 -0.2601 -0.0391 0.063 Uiso 1 1 calc R . .
C6 C -0.1042(5) -0.1225(4) 0.0615(3) 0.0368(10) Uani 1 1 d . . .
C7 C -0.0243(4) -0.0056(4) 0.2076(3) 0.0316(9) Uani 1 1 d . . .
C8 C 0.0571(4) 0.0441(4) 0.3089(3) 0.0306(8) Uani 1 1 d . . .
C9 C 0.1824(5) 0.0145(4) 0.3402(4) 0.0390(10) Uani 1 1 d . . .
H9A H 0.2186 -0.0354 0.2952 0.047 Uiso 1 1 calc R . .
C10 C 0.2500(5) 0.0599(5) 0.4375(4) 0.0407(10) Uani 1 1 d . . .
H10A H 0.3322 0.0402 0.4597 0.049 Uiso 1 1 calc R . .
C11 C 0.1953(5) 0.1365(4) 0.5043(3) 0.0358(9) Uani 1 1 d . . .
C12 C 0.2602(6) 0.1862(5) 0.6069(4) 0.0479(12) Uani 1 1 d . . .
H12A H 0.3424 0.1690 0.6327 0.057 Uiso 1 1 calc R . .
C13 C 0.2008(7) 0.2587(5) 0.6661(4) 0.0572(14) Uani 1 1 d . . .
H13A H 0.2443 0.2913 0.7328 0.069 Uiso 1 1 calc R . .
C14 C 0.0762(7) 0.2870(5) 0.6317(4) 0.0551(14) Uani 1 1 d . . .
H14A H 0.0385 0.3372 0.6751 0.066 Uiso 1 1 calc R . .
C15 C 0.0105(5) 0.2398(4) 0.5330(4) 0.0415(10) Uani 1 1 d . . .
C16 C 0.0704(4) 0.1637(4) 0.4667(3) 0.0326(9) Uani 1 1 d . . .
C17 C -0.2054(11) 0.2978(9) 0.5598(6) 0.109(4) Uani 1 1 d . . .
H17A H -0.2979 0.2410 0.5482 0.131 Uiso 1 1 calc R . .
H17B H -0.1751 0.2914 0.6354 0.131 Uiso 1 1 calc R . .
C18 C -0.2162(12) 0.4123(10) 0.5450(8) 0.133(5) Uani 1 1 d . . .
H18A H -0.2266 0.4260 0.4674 0.160 Uiso 1 1 calc R . .
H18B H -0.1311 0.4713 0.5736 0.160 Uiso 1 1 calc R . .
C19 C -0.3172(7) 0.5604(6) 0.6090(5) 0.0615(15) Uani 1 1 d . . .
H19A H -0.3030 0.5983 0.5382 0.074 Uiso 1 1 calc R . .
H19B H -0.2359 0.5979 0.6569 0.074 Uiso 1 1 calc R . .
C20 C -0.4439(7) 0.5823(5) 0.6550(5) 0.0598(15) Uani 1 1 d . . .
H20A H -0.4381 0.6701 0.6542 0.072 Uiso 1 1 calc R . .
H20B H -0.5260 0.5387 0.6104 0.072 Uiso 1 1 calc R . .
C21 C -0.5732(8) 0.5608(7) 0.8096(8) 0.096(3) Uani 1 1 d . . .
H21A H -0.5775 0.5300 0.8824 0.144 Uiso 1 1 calc R . .
H21B H -0.6564 0.5182 0.7673 0.144 Uiso 1 1 calc R . .
H21C H -0.5661 0.6480 0.8121 0.144 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.315(4) . ?
Hg1 Cl1 2.3841(14) . ?
Hg1 Cl2 2.3853(13) . ?
Hg1 N3 2.480(3) . ?
N1 C7 1.317(5) . ?
N1 C1 1.394(6) . ?
O1 C15 1.361(6) . ?
O1 C17 1.428(7) . ?
C1 C2 1.386(7) . ?
C1 C6 1.402(7) . ?
N2 C7 1.351(5) . ?
N2 C6 1.379(6) . ?
C2 C3 1.379(8) . ?
O2 C19 1.396(7) . ?
O2 C18 1.427(8) . ?
N3 C8 1.325(5) . ?
N3 C16 1.370(5) . ?
C3 C4 1.372(9) . ?
O3 C20 1.390(7) . ?
O3 C21 1.391(8) . ?
C4 C5 1.365(8) . ?
C5 C6 1.396(7) . ?
C7 C8 1.468(6) . ?
C8 C9 1.408(6) . ?
C9 C10 1.364(6) . ?
C10 C11 1.406(7) . ?
C11 C16 1.412(6) . ?
C11 C12 1.422(6) . ?
C12 C13 1.348(8) . ?
C13 C14 1.405(9) . ?
C14 C15 1.376(7) . ?
C15 C16 1.430(6) . ?
C17 C18 1.329(11) . ?
C19 C20 1.480(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 Cl1 111.26(10) . . ?
N1 Hg1 Cl2 103.47(10) . . ?
Cl1 Hg1 Cl2 133.82(5) . . ?
N1 Hg1 N3 69.88(12) . . ?
Cl1 Hg1 N3 101.51(9) . . ?
Cl2 Hg1 N3 118.81(9) . . ?
C7 N1 C1 106.2(4) . . ?
C7 N1 Hg1 116.6(3) . . ?
C1 N1 Hg1 137.1(3) . . ?
C15 O1 C17 121.6(5) . . ?
C2 C1 N1 130.9(5) . . ?
C2 C1 C6 121.2(4) . . ?
N1 C1 C6 107.8(4) . . ?
C7 N2 C6 106.8(4) . . ?
C3 C2 C1 116.5(5) . . ?
C19 O2 C18 109.4(6) . . ?
C8 N3 C16 118.8(4) . . ?
C8 N3 Hg1 114.4(3) . . ?
C16 N3 Hg1 126.1(3) . . ?
C4 C3 C2 122.0(5) . . ?
C20 O3 C21 112.9(6) . . ?
C5 C4 C3 122.9(5) . . ?
C4 C5 C6 116.2(5) . . ?
N2 C6 C5 132.3(5) . . ?
N2 C6 C1 106.5(4) . . ?
C5 C6 C1 121.2(4) . . ?
N1 C7 N2 112.7(4) . . ?
N1 C7 C8 122.7(4) . . ?
N2 C7 C8 124.5(4) . . ?
N3 C8 C9 122.7(4) . . ?
N3 C8 C7 115.2(4) . . ?
C9 C8 C7 122.1(4) . . ?
C10 C9 C8 119.1(4) . . ?
C9 C10 C11 119.9(4) . . ?
C10 C11 C16 117.7(4) . . ?
C10 C11 C12 122.7(4) . . ?
C16 C11 C12 119.5(4) . . ?
C13 C12 C11 119.1(5) . . ?
C12 C13 C14 123.0(5) . . ?
C15 C14 C13 119.4(5) . . ?
O1 C15 C14 125.2(5) . . ?
O1 C15 C16 115.1(4) . . ?
C14 C15 C16 119.7(5) . . ?
N3 C16 C11 121.7(4) . . ?
N3 C16 C15 118.9(4) . . ?
C11 C16 C15 119.4(4) . . ?
C18 C17 O1 116.5(7) . . ?
C17 C18 O2 111.5(7) . . ?
O2 C19 C20 109.6(5) . . ?
O3 C20 C19 110.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.062
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.090



# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 1.000 295 76 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 971509'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_zp02

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N3 O3'
_chemical_formula_weight         363.42

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n'

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

_cell_length_a                   15.625(4)
_cell_length_b                   9.194(2)
_cell_length_c                   27.403(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3936.7(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      25.38

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9900
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18862
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3586
_reflns_number_gt                2487
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_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)+(0.1908P)²+0.9728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2867
_refine_ls_wR_factor_gt          0.2647
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66048(14) -0.0986(2) 0.05880(8) 0.0557(6) Uani 1 1 d . . .
N1 N 0.45084(16) 0.1319(3) 0.15355(9) 0.0475(6) Uani 1 1 d . . .
C1 C 0.39496(18) 0.1719(3) 0.19061(12) 0.0483(8) Uani 1 1 d . . .
O2 O 0.63949(17) -0.3706(3) 0.10550(9) 0.0702(7) Uani 1 1 d . . .
N2 N 0.36873(17) 0.3088(3) 0.12279(11) 0.0589(8) Uani 1 1 d . . .
H2B H 0.3474 0.3715 0.1029 0.071 Uiso 1 1 calc R . .
C2 C 0.3863(2) 0.1233(4) 0.23802(12) 0.0570(8) Uani 1 1 d . . .
H2A H 0.4203 0.0490 0.2505 0.068 Uiso 1 1 calc R . .
N3 N 0.54098(15) 0.1092(3) 0.06572(9) 0.0444(6) Uani 1 1 d . . .
O3 O 0.5140(2) -0.3436(3) 0.18014(16) 0.1022(11) Uani 1 1 d . . .
C3 C 0.3244(2) 0.1914(4) 0.26605(14) 0.0641(10) Uani 1 1 d . . .
H3A H 0.3166 0.1625 0.2983 0.077 Uiso 1 1 calc R . .
C4 C 0.2732(2) 0.3029(5) 0.24685(15) 0.0719(11) Uani 1 1 d . . .
H4A H 0.2325 0.3468 0.2667 0.086 Uiso 1 1 calc R . .
C5 C 0.2816(2) 0.3481(4) 0.20013(16) 0.0715(11) Uani 1 1 d . . .
H5A H 0.2466 0.4211 0.1877 0.086 Uiso 1 1 calc R . .
C6 C 0.3445(2) 0.2821(4) 0.17063(13) 0.0570(9) Uani 1 1 d . . .
C7 C 0.43172(18) 0.2166(3) 0.11448(11) 0.0470(7) Uani 1 1 d . . .
C8 C 0.4803(2) 0.2079(3) 0.06813(11) 0.0484(8) Uani 1 1 d . . .
C9 C 0.4594(3) 0.3038(4) 0.02989(13) 0.0632(9) Uani 1 1 d . . .
H9A H 0.4156 0.3715 0.0334 0.076 Uiso 1 1 calc R . .
C10 C 0.5050(3) 0.2950(4) -0.01244(14) 0.0703(11) Uani 1 1 d . . .
H10A H 0.4927 0.3576 -0.0381 0.084 Uiso 1 1 calc R . .
C11 C 0.5711(2) 0.1906(4) -0.01733(12) 0.0583(9) Uani 1 1 d . . .
C12 C 0.6210(3) 0.1766(5) -0.05998(13) 0.0775(12) Uani 1 1 d . . .
H12A H 0.6111 0.2376 -0.0865 0.093 Uiso 1 1 calc R . .
C13 C 0.6831(3) 0.0748(5) -0.06228(15) 0.0819(14) Uani 1 1 d . . .
H13A H 0.7166 0.0682 -0.0902 0.098 Uiso 1 1 calc R . .
C14 C 0.6980(2) -0.0210(4) -0.02366(13) 0.0672(10) Uani 1 1 d . . .
H14A H 0.7401 -0.0920 -0.0266 0.081 Uiso 1 1 calc R . .
C15 C 0.6508(2) -0.0111(4) 0.01889(11) 0.0527(8) Uani 1 1 d . . .
C16 C 0.5863(2) 0.0974(3) 0.02282(10) 0.0494(8) Uani 1 1 d . . .
C17 C 0.7216(2) -0.2146(4) 0.05575(14) 0.0678(10) Uani 1 1 d . . .
H17A H 0.7786 -0.1751 0.0512 0.081 Uiso 1 1 calc R . .
H17B H 0.7084 -0.2767 0.0281 0.081 Uiso 1 1 calc R . .
C18 C 0.7182(2) -0.3004(4) 0.10172(13) 0.0655(10) Uani 1 1 d . . .
H18A H 0.7640 -0.3718 0.1019 0.079 Uiso 1 1 calc R . .
H18B H 0.7263 -0.2363 0.1295 0.079 Uiso 1 1 calc R . .
C19 C 0.6309(3) -0.4600(5) 0.14833(17) 0.0842(13) Uani 1 1 d . . .
H19A H 0.6551 -0.5553 0.1420 0.101 Uiso 1 1 calc R . .
H19B H 0.6624 -0.4165 0.1751 0.101 Uiso 1 1 calc R . .
C20 C 0.5432(3) -0.4750(5) 0.16169(18) 0.0838(12) Uani 1 1 d . . .
H20A H 0.5096 -0.5024 0.1334 0.101 Uiso 1 1 calc R . .
H20B H 0.5371 -0.5505 0.1862 0.101 Uiso 1 1 calc R . .
C21 C 0.4260(4) -0.3415(8) 0.1955(3) 0.129(2) Uani 1 1 d . . .
H21A H 0.4114 -0.2459 0.2069 0.193 Uiso 1 1 calc R . .
H21B H 0.4178 -0.4105 0.2213 0.193 Uiso 1 1 calc R . .
H21C H 0.3899 -0.3667 0.1684 0.193 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
O1 C15 1.366(4) . ?
O1 C17 1.434(4) . ?
N1 C7 1.357(4) . ?
N1 C1 1.389(4) . ?
C1 C2 1.380(5) . ?
C1 C6 1.396(5) . ?
O2 C18 1.393(5) . ?
O2 C19 1.439(5) . ?
N2 C7 1.319(4) . ?
N2 C6 1.386(4) . ?
C2 C3 1.385(5) . ?
N3 C8 1.314(4) . ?
N3 C16 1.376(4) . ?
O3 C20 1.387(6) . ?
O3 C21 1.438(6) . ?
C3 C4 1.403(6) . ?
C4 C5 1.352(6) . ?
C5 C6 1.409(5) . ?
C7 C8 1.482(4) . ?
C8 C9 1.408(5) . ?
C9 C10 1.363(6) . ?
C10 C11 1.417(6) . ?
C11 C12 1.410(5) . ?
C11 C16 1.414(5) . ?
C12 C13 1.350(7) . ?
C13 C14 1.396(6) . ?
C14 C15 1.383(4) . ?
C15 C16 1.422(5) . ?
C17 C18 1.487(6) . ?
C19 C20 1.426(7) . ?

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
C15 O1 C17 117.7(3) . . ?
C7 N1 C1 106.7(2) . . ?
C2 C1 N1 131.6(3) . . ?
C2 C1 C6 123.3(3) . . ?
N1 C1 C6 105.1(3) . . ?
C18 O2 C19 114.0(3) . . ?
C7 N2 C6 104.7(3) . . ?
C1 C2 C3 116.4(3) . . ?
C8 N3 C16 117.9(3) . . ?
C20 O3 C21 115.6(4) . . ?
C2 C3 C4 121.4(4) . . ?
C5 C4 C3 121.6(3) . . ?
C4 C5 C6 118.6(4) . . ?
N2 C6 C1 110.2(3) . . ?
N2 C6 C5 131.0(3) . . ?
C1 C6 C5 118.8(3) . . ?
N2 C7 N1 113.4(3) . . ?
N2 C7 C8 124.4(3) . . ?
N1 C7 C8 122.2(3) . . ?
N3 C8 C9 124.2(3) . . ?
N3 C8 C7 116.7(3) . . ?
C9 C8 C7 119.0(3) . . ?
C10 C9 C8 118.4(4) . . ?
C9 C10 C11 120.1(3) . . ?
C12 C11 C16 119.8(4) . . ?
C12 C11 C10 122.9(4) . . ?
C16 C11 C10 117.3(3) . . ?
C13 C12 C11 119.9(4) . . ?
C12 C13 C14 121.5(4) . . ?
C15 C14 C13 120.5(4) . . ?
O1 C15 C14 125.2(3) . . ?
O1 C15 C16 115.5(3) . . ?
C14 C15 C16 119.2(3) . . ?
N3 C16 C11 122.1(3) . . ?
N3 C16 C15 119.0(3) . . ?
C11 C16 C15 119.0(3) . . ?
O1 C17 C18 108.8(3) . . ?
O2 C18 C17 109.9(3) . . ?
C20 C19 O2 110.7(4) . . ?
O3 C20 C19 109.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 971510'
