# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_j
_database_code_depnum_ccdc_archive 'CCDC 1918331'
loop_
_audit_author_name
_audit_author_address
'Jifu Zheng'
;Changchun Institute Of Applied Chemistry, Chinese Academy Of Sciences
China
;
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H120 I4 N12'
_chemical_formula_weight         1421.20

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   8.6068(9)
_cell_length_b                   14.9193(15)
_cell_length_c                   14.6169(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.458(5)
_cell_angle_gamma                90.00
_cell_volume                     1758.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    1.810
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9787
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3589
_reflns_number_gt                2930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0387P)²+0.8310P] 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         3589
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.2454(3) 0.69056(15) 0.33404(18) 0.0389(5) Uani 1 1 d . . .
C2 C 0.4036(4) 0.80387(18) 0.4501(2) 0.0540(7) Uani 1 1 d . . .
H2A H 0.4232 0.7531 0.4941 0.065 Uiso 1 1 calc R . .
H2B H 0.3422 0.8485 0.4719 0.065 Uiso 1 1 calc R . .
C3 C 0.1040(4) 0.69721(18) 0.4531(2) 0.0551(7) Uani 1 1 d . . .
H3A H 0.0809 0.7576 0.4274 0.066 Uiso 1 1 calc R . .
H3B H 0.1744 0.7015 0.5212 0.066 Uiso 1 1 calc R . .
C4 C 0.3766(3) 0.66106(18) 0.2135(2) 0.0501(6) Uani 1 1 d . . .
H4A H 0.4564 0.7031 0.2549 0.060 Uiso 1 1 calc R . .
H4B H 0.3310 0.6872 0.1488 0.060 Uiso 1 1 calc R . .
C5 C 0.1084(4) 0.58407(17) 0.20343(19) 0.0522(6) Uani 1 1 d . . .
H5A H 0.0264 0.5853 0.2351 0.063 Uiso 1 1 calc R . .
H5B H 0.1540 0.5240 0.2100 0.063 Uiso 1 1 calc R . .
C6 C 0.2723(3) 0.83961(18) 0.2704(2) 0.0492(6) Uani 1 1 d . . .
H6A H 0.1992 0.8127 0.2103 0.059 Uiso 1 1 calc R . .
H6B H 0.3763 0.8537 0.2617 0.059 Uiso 1 1 calc R . .
C7 C 0.2263(3) 0.55234(17) 0.42040(19) 0.0496(6) Uani 1 1 d . . .
H7A H 0.2910 0.5299 0.3827 0.060 Uiso 1 1 calc R . .
H7B H 0.1222 0.5199 0.4002 0.060 Uiso 1 1 calc R . .
C8 C 0.4640(5) 0.5756(2) 0.2075(3) 0.0816(10) Uani 1 1 d . . .
H8A H 0.5046 0.5478 0.2707 0.122 Uiso 1 1 calc R . .
H8B H 0.5553 0.5885 0.1863 0.122 Uiso 1 1 calc R . .
H8C H 0.3880 0.5358 0.1618 0.122 Uiso 1 1 calc R . .
C9 C 0.0248(4) 0.6059(2) 0.0960(2) 0.0723(9) Uani 1 1 d . . .
H9A H -0.0153 0.6665 0.0891 0.108 Uiso 1 1 calc R . .
H9B H -0.0664 0.5657 0.0676 0.108 Uiso 1 1 calc R . .
H9C H 0.1034 0.5995 0.0632 0.108 Uiso 1 1 calc R . .
C10 C -0.0578(4) 0.6521(2) 0.4461(3) 0.0722(9) Uani 1 1 d . . .
H10A H -0.1271 0.6465 0.3787 0.108 Uiso 1 1 calc R . .
H10B H -0.1136 0.6875 0.4800 0.108 Uiso 1 1 calc R . .
H10C H -0.0351 0.5936 0.4752 0.108 Uiso 1 1 calc R . .
C11 C 0.3198(4) 0.5347(2) 0.5280(2) 0.0686(8) Uani 1 1 d . . .
H11A H 0.4197 0.5697 0.5495 0.103 Uiso 1 1 calc R . .
H11B H 0.3474 0.4722 0.5376 0.103 Uiso 1 1 calc R . .
H11C H 0.2515 0.5510 0.5651 0.103 Uiso 1 1 calc R . .
C12 C 0.1946(4) 0.92519(19) 0.2899(3) 0.0650(8) Uani 1 1 d . . .
H12A H 0.0905 0.9116 0.2971 0.098 Uiso 1 1 calc R . .
H12B H 0.1766 0.9658 0.2362 0.098 Uiso 1 1 calc R . .
H12C H 0.2674 0.9525 0.3488 0.098 Uiso 1 1 calc R . .
C13 C 0.5687(4) 0.8432(3) 0.4553(3) 0.0790(10) Uani 1 1 d . . .
H13A H 0.6269 0.8008 0.4298 0.118 Uiso 1 1 calc R . .
H13B H 0.6336 0.8565 0.5221 0.118 Uiso 1 1 calc R . .
H13C H 0.5502 0.8973 0.4175 0.118 Uiso 1 1 calc R . .
I1 I 0.74833(3) 0.810030(15) 0.200233(17) 0.07519(11) Uani 1 1 d . . .
N1 N 0.3033(2) 0.77462(13) 0.35117(15) 0.0424(4) Uani 1 1 d . . .
N2 N 0.2420(2) 0.64791(14) 0.25252(15) 0.0430(5) Uani 1 1 d . . .
N3 N 0.1925(3) 0.64839(13) 0.39923(15) 0.0434(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0366(12) 0.0389(12) 0.0419(12) 0.0021(10) 0.0147(10) 0.0011(9)
C2 0.0550(16) 0.0558(16) 0.0501(15) -0.0038(12) 0.0168(13) -0.0130(12)
C3 0.0639(17) 0.0534(15) 0.0601(17) -0.0073(12) 0.0366(14) -0.0071(12)
C4 0.0556(15) 0.0514(14) 0.0521(15) 0.0045(12) 0.0298(12) 0.0040(12)
C5 0.0607(16) 0.0446(14) 0.0505(15) -0.0071(11) 0.0183(13) -0.0115(12)
C6 0.0501(14) 0.0410(13) 0.0564(15) 0.0086(11) 0.0185(12) -0.0014(11)
C7 0.0557(15) 0.0437(13) 0.0502(14) 0.0073(11) 0.0194(12) -0.0025(11)
C8 0.085(2) 0.069(2) 0.109(3) 0.0083(19) 0.058(2) 0.0236(18)
C9 0.070(2) 0.078(2) 0.0570(18) -0.0029(15) 0.0076(15) -0.0111(17)
C10 0.066(2) 0.072(2) 0.097(2) -0.0019(18) 0.0514(19) -0.0090(16)
C11 0.0644(19) 0.073(2) 0.0624(18) 0.0196(15) 0.0146(15) -0.0039(15)
C12 0.0556(16) 0.0412(15) 0.099(2) 0.0051(14) 0.0280(16) 0.0015(12)
C13 0.0549(18) 0.097(2) 0.073(2) 0.0064(19) 0.0079(16) -0.0249(18)
I1 0.06594(16) 0.07093(17) 0.08360(19) 0.00271(11) 0.01971(12) -0.01606(10)
N1 0.0455(11) 0.0400(10) 0.0426(11) 0.0005(9) 0.0164(9) -0.0051(9)
N2 0.0473(12) 0.0397(11) 0.0465(12) -0.0008(9) 0.0220(9) -0.0036(9)
N3 0.0498(12) 0.0390(10) 0.0469(12) -0.0002(9) 0.0239(9) -0.0042(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(3) . ?
C1 N2 1.342(3) . ?
C1 N3 1.347(3) . ?
C2 N1 1.468(3) . ?
C2 C13 1.514(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N3 1.466(3) . ?
C3 C10 1.518(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.473(3) . ?
C4 C8 1.497(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.472(3) . ?
C5 C9 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.479(3) . ?
C6 C12 1.514(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N3 1.474(3) . ?
C7 C11 1.519(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 120.1(2) . . ?
N1 C1 N3 120.0(2) . . ?
N2 C1 N3 119.9(2) . . ?
N1 C2 C13 112.6(2) . . ?
N1 C2 H2A 109.1 . . ?
C13 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C13 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C3 C10 112.3(2) . . ?
N3 C3 H3A 109.1 . . ?
C10 C3 H3A 109.1 . . ?
N3 C3 H3B 109.1 . . ?
C10 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C8 112.8(2) . . ?
N2 C4 H4A 109.0 . . ?
C8 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C8 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N2 C5 C9 111.9(2) . . ?
N2 C5 H5A 109.2 . . ?
C9 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C9 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C12 111.7(2) . . ?
N1 C6 H6A 109.3 . . ?
C12 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C12 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N3 C7 C11 112.4(2) . . ?
N3 C7 H7A 109.1 . . ?
C11 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C11 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C2 121.0(2) . . ?
C1 N1 C6 120.9(2) . . ?
C2 N1 C6 118.1(2) . . ?
C1 N2 C5 120.7(2) . . ?
C1 N2 C4 120.3(2) . . ?
C5 N2 C4 118.9(2) . . ?
C1 N3 C3 121.0(2) . . ?
C1 N3 C7 120.8(2) . . ?
C3 N3 C7 118.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1918332'
loop_
_audit_author_name
_audit_author_address
'Jifu Zheng'
;Changchun Institute Of Applied Chemistry, Chinese Academy Of Sciences
China
;
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H28 Cl N3 O2'
_chemical_formula_weight         293.83

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.9771(9)
_cell_length_b                   18.0751(17)
_cell_length_c                   8.9806(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.318(2)
_cell_angle_gamma                90.00
_cell_volume                     1569.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4402
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1602
_reflns_number_gt                1358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0586P)²+1.2245P] 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         1602
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61854(13) 0.14548(7) 0.26644(15) 0.0280(3) Uani 1 1 d . . .
N2 N 0.5000 0.03353(10) 0.2500 0.0307(4) Uani 1 2 d S . .
C1 C 0.5000 0.10776(12) 0.2500 0.0247(4) Uani 1 2 d S . .
C2 C 0.75684(16) 0.12105(11) 0.3566(2) 0.0386(4) Uani 1 1 d . . .
H2A H 0.7897 0.0790 0.3087 0.046 Uiso 1 1 calc R . .
H2B H 0.7551 0.1081 0.4609 0.046 Uiso 1 1 calc R . .
C3 C 0.84615(18) 0.18894(12) 0.3537(2) 0.0447(5) Uani 1 1 d . . .
H3A H 0.8407 0.2234 0.4348 0.054 Uiso 1 1 calc R . .
H3B H 0.9421 0.1754 0.3638 0.054 Uiso 1 1 calc R . .
C4 C 0.78169(18) 0.22120(10) 0.1960(2) 0.0392(4) Uani 1 1 d . . .
H4A H 0.8107 0.2720 0.1884 0.047 Uiso 1 1 calc R . .
H4B H 0.8052 0.1921 0.1153 0.047 Uiso 1 1 calc R . .
C5 C 0.62853(17) 0.21662(9) 0.1884(2) 0.0326(4) Uani 1 1 d . . .
H5A H 0.5989 0.2576 0.2422 0.039 Uiso 1 1 calc R . .
H5B H 0.5737 0.2159 0.0829 0.039 Uiso 1 1 calc R . .
C6 C 0.3977(2) -0.01329(10) 0.3009(2) 0.0426(5) Uani 1 1 d . . .
H6A H 0.3097 -0.0139 0.2249 0.051 Uiso 1 1 calc R . .
H6B H 0.3835 0.0036 0.3983 0.051 Uiso 1 1 calc R . .
C7 C 0.4664(3) -0.08906(11) 0.3165(2) 0.0599(7) Uani 1 1 d . . .
H7A H 0.5345 -0.0940 0.4139 0.072 Uiso 1 1 calc R . .
H7B H 0.3988 -0.1285 0.3068 0.072 Uiso 1 1 calc R . .
Cl1 Cl 0.0000 0.07754(5) 0.7500 0.0604(3) Uani 1 2 d S . .
O1 O 0.85529(17) 0.05993(10) 0.0309(2) 0.0570(4) Uani 1 1 d . . .
H1W H 0.903(4) 0.0674(16) -0.039(4) 0.096(11) Uiso 1 1 d . . .
H2W H 0.905(4) 0.025(2) 0.095(4) 0.116(13) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0225(7) 0.0285(7) 0.0326(7) 0.0038(5) 0.0057(5) 0.0018(5)
N2 0.0349(10) 0.0252(10) 0.0327(10) 0.000 0.0096(8) 0.000
C1 0.0245(10) 0.0276(11) 0.0223(10) 0.000 0.0062(8) 0.000
C2 0.0222(8) 0.0544(11) 0.0374(9) 0.0086(8) 0.0039(7) 0.0066(7)
C3 0.0241(9) 0.0661(13) 0.0437(10) -0.0087(9) 0.0079(8) -0.0068(8)
C4 0.0338(10) 0.0427(10) 0.0442(10) -0.0041(8) 0.0154(8) -0.0102(7)
C5 0.0312(9) 0.0289(8) 0.0381(9) 0.0026(7) 0.0095(7) -0.0041(6)
C6 0.0575(12) 0.0336(10) 0.0363(9) -0.0013(7) 0.0110(8) -0.0180(8)
C7 0.106(2) 0.0291(10) 0.0407(11) 0.0008(8) 0.0116(12) -0.0125(10)
Cl1 0.0744(6) 0.0674(5) 0.0423(4) 0.000 0.0197(4) 0.000
O1 0.0521(9) 0.0656(11) 0.0580(10) -0.0119(8) 0.0227(8) 0.0043(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3413(17) . ?
N1 C5 1.480(2) . ?
N1 C2 1.484(2) . ?
N2 C1 1.342(3) . ?
N2 C6 1.482(2) . ?
N2 C6 1.482(2) 2_655 ?
C1 N1 1.3413(17) 2_655 ?
C2 C3 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.515(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.522(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.507(5) 2_655 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1 H1W 0.89(4) . ?
O1 H2W 0.91(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
C1 N1 C5 123.40(13) . . ?
C1 N1 C2 125.77(14) . . ?
C5 N1 C2 110.76(13) . . ?
C1 N2 C6 124.83(10) . . ?
C1 N2 C6 124.83(10) . 2_655 ?
C6 N2 C6 110.3(2) . 2_655 ?
N1 C1 N1 118.89(19) . 2_655 ?
N1 C1 N2 120.55(10) . . ?
N1 C1 N2 120.55(10) 2_655 . ?
N1 C2 C3 102.74(14) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 102.16(14) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C3 102.17(14) . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C4 102.21(13) . . ?
N1 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
N1 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
N2 C6 C7 102.34(17) . . ?
N2 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
N2 C6 H6B 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C7 C7 C6 101.84(13) 2_655 . ?
C7 C7 H7A 111.4 2_655 . ?
C6 C7 H7A 111.4 . . ?
C7 C7 H7B 111.4 2_655 . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
H1W O1 H2W 104(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.069
