# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_tyr_a
_database_code_depnum_ccdc_archive 'CCDC 1882469'
loop_
_audit_author_name
_audit_author_address
'Li Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2018-12-01 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O6'
_chemical_formula_weight         365.33

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   10.5965(14)
_cell_length_b                   12.9681(17)
_cell_length_c                   13.0204(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.415(2)
_cell_angle_gamma                90.00
_cell_volume                     1716.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4175
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            coloreless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.974
_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  '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            10558
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.14
_reflns_number_total             3409
_reflns_number_gt                2746
_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)+(0.0704P)²+0.4136P] 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         3409
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.02850(14) 0.05230(9) 0.12676(9) 0.0510(4) Uani 1 1 d . . .
H1 H 0.0084 0.0013 0.0884 0.077 Uiso 1 1 calc R . .
O2 O 0.23444(13) 0.23900(8) 0.46315(8) 0.0454(3) Uani 1 1 d . . .
H2 H 0.2475 0.2472 0.5278 0.068 Uiso 1 1 calc R . .
O3 O 0.16632(14) 0.49337(9) -0.03099(9) 0.0530(4) Uani 1 1 d . . .
O4 O 0.17979(15) 0.58271(9) 0.11775(9) 0.0540(4) Uani 1 1 d . . .
H3 H 0.2059 0.6288 0.0857 0.081 Uiso 1 1 calc R . .
O5 O 0.04043(14) 0.12177(9) -0.02659(8) 0.0518(4) Uani 1 1 d . . .
O6 O 0.20115(14) 0.40778(9) 0.46018(9) 0.0522(4) Uani 1 1 d . . .
N1 N 0.29024(14) 0.24361(13) 0.66831(11) 0.0466(4) Uani 1 1 d . . .
C1 C 0.14958(15) 0.40492(11) 0.12490(11) 0.0312(3) Uani 1 1 d . . .
C2 C 0.16650(15) 0.49731(11) 0.06193(11) 0.0353(3) Uani 1 1 d . . .
C3 C 0.16837(14) 0.32066(11) 0.29400(11) 0.0287(3) Uani 1 1 d . . .
C4 C 0.09384(14) 0.22601(11) 0.12841(11) 0.0301(3) Uani 1 1 d . . .
C5 C 0.12406(14) 0.22966(11) 0.23958(11) 0.0297(3) Uani 1 1 d . . .
H4 H 0.1145 0.1709 0.2776 0.036 Uiso 1 1 calc R . .
C6 C 0.10815(15) 0.31307(11) 0.07127(11) 0.0320(3) Uani 1 1 d . . .
H5 H 0.0901 0.3100 -0.0028 0.038 Uiso 1 1 calc R . .
C7 C 0.20403(15) 0.32575(11) 0.41495(11) 0.0324(3) Uani 1 1 d . . .
C8 C 0.17945(14) 0.40838(11) 0.23623(11) 0.0309(3) Uani 1 1 d . . .
H6 H 0.2070 0.4700 0.2720 0.037 Uiso 1 1 calc R . .
C9 C 0.05138(16) 0.12727(11) 0.07193(11) 0.0344(3) Uani 1 1 d . . .
C10 C 0.36434(15) 0.24886(14) 0.88931(12) 0.0392(4) Uani 1 1 d . . .
C11 C 0.37057(17) 0.15799(14) 0.83405(13) 0.0434(4) Uani 1 1 d . . .
H7 H 0.4003 0.0975 0.8714 0.052 Uiso 1 1 calc R . .
C12 C 0.40808(16) 0.25359(14) 1.00798(12) 0.0412(4) Uani 1 1 d . . .
C13 C 0.33248(18) 0.15807(15) 0.72354(14) 0.0479(4) Uani 1 1 d . . .
H8 H 0.3364 0.0971 0.6870 0.057 Uiso 1 1 calc R . .
C14 C 0.31656(19) 0.33608(15) 0.82809(14) 0.0503(4) Uani 1 1 d . . .
H9 H 0.3083 0.3979 0.8618 0.060 Uiso 1 1 calc R . .
C15 C 0.28157(19) 0.33137(16) 0.71821(14) 0.0520(5) Uani 1 1 d . . .
H10 H 0.2514 0.3904 0.6783 0.062 Uiso 1 1 calc R . .
C16 C 0.45150(19) 0.34594(16) 1.05975(15) 0.0532(5) Uani 1 1 d . . .
H11 H 0.4561 0.4044 1.0197 0.064 Uiso 1 1 calc R . .
C17 C 0.40370(19) 0.16728(17) 1.06953(14) 0.0529(5) Uani 1 1 d . . .
H12 H 0.3751 0.1046 1.0364 0.063 Uiso 1 1 calc R . .
C18 C 0.4880(2) 0.3520(2) 1.17054(16) 0.0655(6) Uani 1 1 d . . .
H13 H 0.5166 0.4144 1.2043 0.079 Uiso 1 1 calc R . .
C19 C 0.4822(2) 0.2665(2) 1.23032(15) 0.0685(7) Uani 1 1 d . . .
H14 H 0.5055 0.2709 1.3046 0.082 Uiso 1 1 calc R . .
C20 C 0.4419(2) 0.1740(2) 1.18046(16) 0.0681(6) Uani 1 1 d . . .
H15 H 0.4402 0.1155 1.2213 0.082 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 C9 1.2694(19) . ?
O1 H1 0.8200 . ?
O2 C7 1.2841(18) . ?
O2 H2 0.8200 . ?
O3 C2 1.2104(18) . ?
O4 C2 1.3103(18) . ?
O4 H3 0.8200 . ?
O5 C9 1.2570(18) . ?
O6 C7 1.2205(18) . ?
N1 C15 1.326(2) . ?
N1 C13 1.329(2) . ?
C1 C6 1.388(2) . ?
C1 C8 1.3942(19) . ?
C1 C2 1.491(2) . ?
C3 C8 1.387(2) . ?
C3 C5 1.388(2) . ?
C3 C7 1.5135(19) . ?
C4 C6 1.384(2) . ?
C4 C5 1.3922(19) . ?
C4 C9 1.4819(19) . ?
C5 H4 0.9300 . ?
C6 H5 0.9300 . ?
C8 H6 0.9300 . ?
C10 C11 1.392(2) . ?
C10 C14 1.394(3) . ?
C10 C12 1.484(2) . ?
C11 C13 1.380(2) . ?
C11 H7 0.9300 . ?
C12 C17 1.385(3) . ?
C12 C16 1.387(3) . ?
C13 H8 0.9300 . ?
C14 C15 1.374(2) . ?
C14 H9 0.9300 . ?
C15 H10 0.9300 . ?
C16 C18 1.386(3) . ?
C16 H11 0.9300 . ?
C17 C20 1.388(3) . ?
C17 H12 0.9300 . ?
C18 C19 1.366(3) . ?
C18 H13 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H14 0.9300 . ?
C20 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C2 O4 H3 109.5 . . ?
C15 N1 C13 120.69(14) . . ?
C6 C1 C8 119.83(13) . . ?
C6 C1 C2 118.88(13) . . ?
C8 C1 C2 121.24(13) . . ?
O3 C2 O4 124.03(14) . . ?
O3 C2 C1 123.32(14) . . ?
O4 C2 C1 112.64(12) . . ?
C8 C3 C5 119.25(13) . . ?
C8 C3 C7 119.60(12) . . ?
C5 C3 C7 121.14(12) . . ?
C6 C4 C5 120.22(13) . . ?
C6 C4 C9 120.15(12) . . ?
C5 C4 C9 119.58(13) . . ?
C3 C5 C4 120.32(13) . . ?
C3 C5 H4 119.8 . . ?
C4 C5 H4 119.8 . . ?
C4 C6 C1 119.79(13) . . ?
C4 C6 H5 120.1 . . ?
C1 C6 H5 120.1 . . ?
O6 C7 O2 124.39(13) . . ?
O6 C7 C3 120.47(13) . . ?
O2 C7 C3 115.13(12) . . ?
C3 C8 C1 120.55(13) . . ?
C3 C8 H6 119.7 . . ?
C1 C8 H6 119.7 . . ?
O5 C9 O1 123.59(13) . . ?
O5 C9 C4 118.88(13) . . ?
O1 C9 C4 117.53(13) . . ?
C11 C10 C14 117.00(15) . . ?
C11 C10 C12 121.79(16) . . ?
C14 C10 C12 121.20(15) . . ?
C13 C11 C10 119.71(17) . . ?
C13 C11 H7 120.1 . . ?
C10 C11 H7 120.1 . . ?
C17 C12 C16 118.50(16) . . ?
C17 C12 C10 121.16(16) . . ?
C16 C12 C10 120.31(16) . . ?
N1 C13 C11 121.29(16) . . ?
N1 C13 H8 119.4 . . ?
C11 C13 H8 119.4 . . ?
C15 C14 C10 120.45(17) . . ?
C15 C14 H9 119.8 . . ?
C10 C14 H9 119.8 . . ?
N1 C15 C14 120.84(18) . . ?
N1 C15 H10 119.6 . . ?
C14 C15 H10 119.6 . . ?
C18 C16 C12 120.7(2) . . ?
C18 C16 H11 119.6 . . ?
C12 C16 H11 119.6 . . ?
C12 C17 C20 120.2(2) . . ?
C12 C17 H12 119.9 . . ?
C20 C17 H12 119.9 . . ?
C19 C18 C16 120.2(2) . . ?
C19 C18 H13 119.9 . . ?
C16 C18 H13 119.9 . . ?
C18 C19 C20 119.84(17) . . ?
C18 C19 H14 120.1 . . ?
C20 C19 H14 120.1 . . ?
C19 C20 C17 120.5(2) . . ?
C19 C20 H15 119.8 . . ?
C17 C20 H15 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.14
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.114
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1882472'
loop_
_audit_author_name
_audit_author_address
'Li Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2019-03-07 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H58 Mo8 N6 O26'
_chemical_formula_weight         2118.70

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'
Mo Mo -1.6832 0.6857 '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'

_cell_length_a                   11.4623(5)
_cell_length_b                   13.4719(6)
_cell_length_c                   13.5825(6)
_cell_angle_alpha                114.442(2)
_cell_angle_beta                 112.183(2)
_cell_angle_gamma                90.361(2)
_cell_volume                     1734.92(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            20691
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.76
_reflns_number_total             6585
_reflns_number_gt                4414
_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)+(0.0719P)²+4.7271P] 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         6585
_refine_ls_number_parameters     478
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.072
_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
Mo1 Mo 0.33869(5) 0.00120(4) -0.01448(5) 0.02060(16) Uani 1 1 d . . .
Mo2 Mo 0.55610(5) 0.04772(5) 0.24182(5) 0.02352(16) Uani 1 1 d . . .
Mo3 Mo 0.70395(5) 0.25774(5) 0.24617(5) 0.02670(17) Uani 1 1 d . . .
Mo4 Mo 0.48198(5) 0.20705(4) -0.01248(5) 0.02460(16) Uani 1 1 d . . .
O1 O 0.3530(4) 0.0652(4) -0.1153(4) 0.0245(10) Uani 1 1 d . . .
O2 O 0.4140(4) -0.0652(4) 0.0930(4) 0.0252(10) Uani 1 1 d . . .
O3 O 0.5259(4) 0.1030(3) 0.0930(4) 0.0245(10) Uani 1 1 d . . .
O4 O 0.6531(4) 0.2754(4) 0.1019(4) 0.0308(11) Uani 1 1 d . . .
O5 O 0.2224(4) -0.1181(4) -0.1282(4) 0.0293(11) Uani 1 1 d . . .
O6 O 0.7098(4) 0.1519(4) 0.3079(4) 0.0301(11) Uani 1 1 d . . .
O7 O 0.2545(4) 0.0849(4) 0.0512(4) 0.0312(11) Uani 1 1 d . . .
O8 O 0.3951(5) 0.2824(4) 0.0587(4) 0.0371(12) Uani 1 1 d . . .
O9 O 0.6029(5) -0.0227(4) 0.3251(4) 0.0394(13) Uani 1 1 d . . .
O10 O 0.4721(5) 0.2502(4) -0.1156(5) 0.0439(14) Uani 1 1 d . . .
O11 O 0.4635(4) 0.1308(4) 0.2959(4) 0.0338(11) Uani 1 1 d . . .
O12 O 0.8554(5) 0.3361(4) 0.3287(4) 0.0405(13) Uani 1 1 d . . .
O13 O 0.6107(5) 0.3369(4) 0.3042(4) 0.0389(12) Uani 1 1 d . . .
N1 N 0.1312(6) 0.2176(5) -0.4723(6) 0.0413(15) Uani 1 1 d . . .
H1A H 0.1679 0.2478 -0.5005 0.050 Uiso 1 1 calc R . .
N2 N 0.2216(6) 0.3327(5) -0.5564(6) 0.0404(15) Uani 1 1 d . . .
C1 C 0.3117(6) 0.4884(6) -0.6101(6) 0.0293(15) Uani 1 1 d . . .
C2 C 0.3642(6) 0.5734(6) -0.6336(6) 0.0298(15) Uani 1 1 d . . .
C3 C -0.1727(9) -0.0153(7) -0.2333(8) 0.053(2) Uani 1 1 d . . .
H2 H -0.2131 -0.0452 -0.2011 0.063 Uiso 1 1 calc R . .
C4 C -0.0520(6) 0.0758(6) -0.3287(6) 0.0334(16) Uani 1 1 d . . .
C5 C 0.0122(6) 0.1241(6) -0.3796(6) 0.0321(16) Uani 1 1 d . . .
C6 C 0.2014(8) 0.1962(7) -0.3836(8) 0.048(2) Uani 1 1 d . . .
H3 H 0.2904 0.2127 -0.3531 0.058 Uiso 1 1 calc R . .
C7 C 0.3538(8) 0.3874(6) -0.6321(7) 0.0427(19) Uani 1 1 d . . .
H4 H 0.4133 0.3705 -0.6650 0.051 Uiso 1 1 calc R . .
C8 C 0.2220(7) 0.5067(6) -0.5616(6) 0.0346(16) Uani 1 1 d . . .
H5 H 0.1897 0.5720 -0.5465 0.042 Uiso 1 1 calc R . .
C9 C 0.4096(7) 0.5440(7) -0.7214(7) 0.0406(18) Uani 1 1 d . . .
H6 H 0.4083 0.4696 -0.7665 0.049 Uiso 1 1 calc R . .
C10 C 0.4601(8) 0.7353(7) -0.6754(7) 0.045(2) Uani 1 1 d . . .
H7 H 0.4902 0.7890 -0.6908 0.054 Uiso 1 1 calc R . .
C11 C 0.3064(8) 0.3134(7) -0.6045(8) 0.049(2) Uani 1 1 d . . .
H8 H 0.3348 0.2463 -0.6203 0.059 Uiso 1 1 calc R . .
C12 C 0.0049(8) 0.1928(8) -0.5177(8) 0.051(2) Uani 1 1 d . . .
H9 H -0.0432 0.2076 -0.5809 0.061 Uiso 1 1 calc R . .
C13 C -0.0436(9) 0.0073(10) -0.1892(10) 0.079(4) Uani 1 1 d . . .
H10 H 0.0052 -0.0075 -0.1263 0.095 Uiso 1 1 calc R . .
C14 C 0.3693(7) 0.6860(6) -0.5661(6) 0.0347(16) Uani 1 1 d . . .
H11 H 0.3390 0.7072 -0.5071 0.042 Uiso 1 1 calc R . .
C15 C 0.1813(7) 0.4282(7) -0.5361(7) 0.0431(19) Uani 1 1 d . . .
H12 H 0.1221 0.4427 -0.5027 0.052 Uiso 1 1 calc R . .
C16 C 0.4570(8) 0.6253(7) -0.7421(7) 0.051(2) Uani 1 1 d . . .
H13 H 0.4867 0.6050 -0.8014 0.061 Uiso 1 1 calc R . .
C17 C 1.2682(10) 0.4476(9) -0.0989(10) 0.070(3) Uani 1 1 d . . .
H14 H 1.3575 0.4610 -0.0641 0.084 Uiso 1 1 calc R . .
C18 C -0.1836(7) 0.0510(8) -0.3739(8) 0.048(2) Uani 1 1 d . . .
H15 H -0.2331 0.0643 -0.4377 0.058 Uiso 1 1 calc R . .
C19 C -0.2433(8) 0.0065(9) -0.3261(9) 0.063(3) Uani 1 1 d . . .
H16 H -0.3325 -0.0088 -0.3573 0.075 Uiso 1 1 calc R . .
C20 C 1.1996(8) 0.4028(7) -0.0592(8) 0.053(2) Uani 1 1 d . . .
H17 H 1.2442 0.3853 0.0027 0.063 Uiso 1 1 calc R . .
C21 C 0.4188(8) 0.7665(6) -0.5860(7) 0.0435(19) Uani 1 1 d . . .
H18 H 0.4242 0.8413 -0.5390 0.052 Uiso 1 1 calc R . .
C22 C 1.0678(7) 0.3822(6) -0.1061(7) 0.0383(18) Uani 1 1 d . . .
C23 C -0.0573(7) 0.1459(8) -0.4742(8) 0.056(3) Uani 1 1 d . . .
H19 H -0.1465 0.1285 -0.5085 0.068 Uiso 1 1 calc R . .
C24 C 0.0177(9) 0.0526(10) -0.2366(9) 0.076(4) Uani 1 1 d . . .
H20 H 0.1069 0.0671 -0.2053 0.092 Uiso 1 1 calc R . .
N3 N 1.2027(12) 0.4729(8) -0.1918(9) 0.093(3) Uani 1 1 d . . .
H21 H 1.2440 0.4997 -0.2194 0.112 Uiso 1 1 calc R . .
C25 C 0.9974(8) 0.3349(6) -0.0615(7) 0.046(2) Uani 1 1 d D . .
C26 C 0.8666(14) 0.2485(9) 0.0288(11) 0.076(4) Uani 1 1 d . . .
H22 H 0.8218 0.2213 0.0599 0.091 Uiso 1 1 calc R . .
C27 C 0.8667(9) 0.3179(9) -0.1011(10) 0.067(3) Uani 1 1 d . . .
H23 H 0.8171 0.3351 -0.1619 0.080 Uiso 1 1 calc R . .
C28 C 0.8075(12) 0.2748(10) -0.0504(14) 0.096(5) Uani 1 1 d . . .
H24 H 0.7187 0.2656 -0.0781 0.115 Uiso 1 1 calc R . .
C29 C 1.0732(11) 0.4550(11) -0.2384(11) 0.092(4) Uani 1 1 d . . .
H25 H 1.0287 0.4735 -0.2996 0.111 Uiso 1 1 calc R . .
C30 C 1.0648(11) 0.3014(12) 0.0312(11) 0.104(5) Uani 1 1 d D . .
H26 H 1.1537 0.3089 0.0632 0.125 Uiso 1 1 calc R . .
C31 C 0.9899(18) 0.2579(14) 0.0695(13) 0.131(6) Uani 1 1 d . . .
H27 H 1.0307 0.2343 0.1272 0.157 Uiso 1 1 calc R . .
C32 C 1.0068(10) 0.4101(10) -0.1966(10) 0.082(4) Uani 1 1 d . . .
H28 H 0.9176 0.3981 -0.2307 0.098 Uiso 1 1 calc R . .
C33 C 0.1448(7) 0.1497(6) -0.3356(7) 0.0395(18) Uani 1 1 d . . .
H33 H 0.1959 0.1353 -0.2730 0.047 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
Mo1 O7 1.683(5) . ?
Mo1 O5 1.764(4) . ?
Mo1 O1 1.947(4) . ?
Mo1 O2 1.954(4) . ?
Mo1 O3 2.135(4) . ?
Mo1 O3 2.358(5) 2_655 ?
Mo2 O11 1.686(5) . ?
Mo2 O9 1.704(5) . ?
Mo2 O6 1.900(4) . ?
Mo2 O2 1.998(4) . ?
Mo2 O3 2.341(4) . ?
Mo2 O1 2.359(4) 2_655 ?
Mo3 O13 1.691(5) . ?
Mo3 O12 1.707(5) . ?
Mo3 O6 1.921(4) . ?
Mo3 O4 1.939(4) . ?
Mo3 O5 2.316(5) 2_655 ?
Mo3 O3 2.447(4) . ?
Mo4 O10 1.694(5) . ?
Mo4 O8 1.698(5) . ?
Mo4 O4 1.898(4) . ?
Mo4 O1 1.996(4) . ?
Mo4 O3 2.323(4) . ?
Mo4 O2 2.357(5) 2_655 ?
O1 Mo2 2.359(4) 2_655 ?
O2 Mo4 2.357(5) 2_655 ?
O3 Mo1 2.358(5) 2_655 ?
O5 Mo3 2.316(5) 2_655 ?
N1 C12 1.317(10) . ?
N1 C6 1.319(10) . ?
N1 H1A 0.8600 . ?
N2 C15 1.325(10) . ?
N2 C11 1.335(10) . ?
C1 C8 1.390(10) . ?
C1 C7 1.398(10) . ?
C1 C2 1.488(9) . ?
C2 C9 1.389(10) . ?
C2 C14 1.398(10) . ?
C3 C13 1.347(12) . ?
C3 C19 1.367(12) . ?
C3 H2 0.9300 . ?
C4 C24 1.369(10) . ?
C4 C18 1.374(10) . ?
C4 C5 1.481(9) . ?
C5 C23 1.383(10) . ?
C5 C33 1.386(9) . ?
C6 C33 1.375(10) . ?
C6 H3 0.9300 . ?
C7 C11 1.373(10) . ?
C7 H4 0.9300 . ?
C8 C15 1.369(10) . ?
C8 H5 0.9300 . ?
C9 C16 1.392(11) . ?
C9 H6 0.9300 . ?
C10 C16 1.372(12) . ?
C10 C21 1.374(11) . ?
C10 H7 0.9300 . ?
C11 H8 0.9300 . ?
C12 C23 1.371(10) . ?
C12 H9 0.9300 . ?
C13 C24 1.393(11) . ?
C13 H10 0.9300 . ?
C14 C21 1.386(10) . ?
C14 H11 0.9300 . ?
C15 H12 0.9300 . ?
C16 H13 0.9300 . ?
C17 C20 1.363(12) . ?
C17 N3 1.384(13) . ?
C17 H14 0.9300 . ?
C18 C19 1.378(11) . ?
C18 H15 0.9300 . ?
C19 H16 0.9300 . ?
C20 C22 1.373(11) . ?
C20 H17 0.9300 . ?
C21 H18 0.9300 . ?
C22 C32 1.372(12) . ?
C22 C25 1.451(11) . ?
C23 H19 0.9300 . ?
C24 H20 0.9300 . ?
N3 C29 1.350(14) . ?
N3 H21 0.8600 . ?
C25 C27 1.368(12) . ?
C25 C30 1.458(8) . ?
C26 C28 1.229(17) . ?
C26 C31 1.293(19) . ?
C26 H22 0.9300 . ?
C27 C28 1.395(15) . ?
C27 H23 0.9300 . ?
C28 H24 0.9300 . ?
C29 C32 1.368(14) . ?
C29 H25 0.9300 . ?
C30 C31 1.391(16) . ?
C30 H26 0.9300 . ?
C31 H27 0.9300 . ?
C32 H28 0.9300 . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Mo1 O5 103.7(2) . . ?
O7 Mo1 O1 101.2(2) . . ?
O5 Mo1 O1 97.28(19) . . ?
O7 Mo1 O2 101.6(2) . . ?
O5 Mo1 O2 95.45(19) . . ?
O1 Mo1 O2 150.36(18) . . ?
O7 Mo1 O3 99.7(2) . . ?
O5 Mo1 O3 156.5(2) . . ?
O1 Mo1 O3 78.93(16) . . ?
O2 Mo1 O3 78.76(16) . . ?
O7 Mo1 O3 174.58(19) . 2_655 ?
O5 Mo1 O3 81.69(18) . 2_655 ?
O1 Mo1 O3 78.05(16) . 2_655 ?
O2 Mo1 O3 77.47(17) . 2_655 ?
O3 Mo1 O3 74.86(18) . 2_655 ?
O11 Mo2 O9 105.0(2) . . ?
O11 Mo2 O6 101.0(2) . . ?
O9 Mo2 O6 100.7(2) . . ?
O11 Mo2 O2 97.1(2) . . ?
O9 Mo2 O2 101.8(2) . . ?
O6 Mo2 O2 146.17(18) . . ?
O11 Mo2 O3 94.1(2) . . ?
O9 Mo2 O3 160.8(2) . . ?
O6 Mo2 O3 77.35(16) . . ?
O2 Mo2 O3 73.07(15) . . ?
O11 Mo2 O1 163.29(19) . 2_655 ?
O9 Mo2 O1 89.8(2) . 2_655 ?
O6 Mo2 O1 83.37(18) . 2_655 ?
O2 Mo2 O1 71.84(16) . 2_655 ?
O3 Mo2 O1 70.99(15) . 2_655 ?
O13 Mo3 O12 105.2(2) . . ?
O13 Mo3 O6 99.3(2) . . ?
O12 Mo3 O6 102.6(2) . . ?
O13 Mo3 O4 98.6(2) . . ?
O12 Mo3 O4 101.8(2) . . ?
O6 Mo3 O4 144.48(19) . . ?
O13 Mo3 O5 164.2(2) . 2_655 ?
O12 Mo3 O5 90.5(2) . 2_655 ?
O6 Mo3 O5 78.56(18) . 2_655 ?
O4 Mo3 O5 75.86(18) . 2_655 ?
O13 Mo3 O3 94.4(2) . . ?
O12 Mo3 O3 160.4(2) . . ?
O6 Mo3 O3 74.35(16) . . ?
O4 Mo3 O3 73.95(16) . . ?
O5 Mo3 O3 69.94(15) 2_655 . ?
O10 Mo4 O8 105.7(3) . . ?
O10 Mo4 O4 100.9(2) . . ?
O8 Mo4 O4 102.1(2) . . ?
O10 Mo4 O1 100.2(2) . . ?
O8 Mo4 O1 97.7(2) . . ?
O4 Mo4 O1 145.87(19) . . ?
O10 Mo4 O3 160.6(2) . . ?
O8 Mo4 O3 93.4(2) . . ?
O4 Mo4 O3 77.75(17) . . ?
O1 Mo4 O3 73.54(15) . . ?
O10 Mo4 O2 89.7(2) . 2_655 ?
O8 Mo4 O2 162.99(19) . 2_655 ?
O4 Mo4 O2 81.61(18) . 2_655 ?
O1 Mo4 O2 71.92(16) . 2_655 ?
O3 Mo4 O2 70.95(15) . 2_655 ?
Mo1 O1 Mo4 108.5(2) . . ?
Mo1 O1 Mo2 110.44(19) . 2_655 ?
Mo4 O1 Mo2 103.72(18) . 2_655 ?
Mo1 O2 Mo2 108.95(19) . . ?
Mo1 O2 Mo4 110.42(19) . 2_655 ?
Mo2 O2 Mo4 103.73(18) . 2_655 ?
Mo1 O3 Mo4 91.63(15) . . ?
Mo1 O3 Mo2 91.76(15) . . ?
Mo4 O3 Mo2 161.7(2) . . ?
Mo1 O3 Mo1 105.14(18) . 2_655 ?
Mo4 O3 Mo1 98.55(15) . 2_655 ?
Mo2 O3 Mo1 97.93(16) . 2_655 ?
Mo1 O3 Mo3 162.4(2) . . ?
Mo4 O3 Mo3 85.66(13) . . ?
Mo2 O3 Mo3 85.67(13) . . ?
Mo1 O3 Mo3 92.46(15) 2_655 . ?
Mo4 O4 Mo3 115.5(2) . . ?
Mo1 O5 Mo3 115.9(2) . 2_655 ?
Mo2 O6 Mo3 116.9(2) . . ?
C12 N1 C6 120.2(7) . . ?
C12 N1 H1A 119.9 . . ?
C6 N1 H1A 119.9 . . ?
C15 N2 C11 117.3(6) . . ?
C8 C1 C7 116.7(6) . . ?
C8 C1 C2 121.9(6) . . ?
C7 C1 C2 121.4(7) . . ?
C9 C2 C14 118.4(6) . . ?
C9 C2 C1 121.6(7) . . ?
C14 C2 C1 120.0(6) . . ?
C13 C3 C19 118.9(8) . . ?
C13 C3 H2 120.5 . . ?
C19 C3 H2 120.5 . . ?
C24 C4 C18 117.8(7) . . ?
C24 C4 C5 121.2(7) . . ?
C18 C4 C5 121.0(6) . . ?
C23 C5 C33 116.3(7) . . ?
C23 C5 C4 121.7(6) . . ?
C33 C5 C4 122.0(6) . . ?
N1 C6 C33 121.0(7) . . ?
N1 C6 H3 119.5 . . ?
C33 C6 H3 119.5 . . ?
C11 C7 C1 119.3(7) . . ?
C11 C7 H4 120.4 . . ?
C1 C7 H4 120.4 . . ?
C15 C8 C1 119.8(7) . . ?
C15 C8 H5 120.1 . . ?
C1 C8 H5 120.1 . . ?
C2 C9 C16 120.3(8) . . ?
C2 C9 H6 119.8 . . ?
C16 C9 H6 119.8 . . ?
C16 C10 C21 120.4(7) . . ?
C16 C10 H7 119.8 . . ?
C21 C10 H7 119.8 . . ?
N2 C11 C7 123.4(7) . . ?
N2 C11 H8 118.3 . . ?
C7 C11 H8 118.3 . . ?
N1 C12 C23 121.7(7) . . ?
N1 C12 H9 119.2 . . ?
C23 C12 H9 119.2 . . ?
C3 C13 C24 120.9(8) . . ?
C3 C13 H10 119.5 . . ?
C24 C13 H10 119.5 . . ?
C21 C14 C2 120.8(7) . . ?
C21 C14 H11 119.6 . . ?
C2 C14 H11 119.6 . . ?
N2 C15 C8 123.5(7) . . ?
N2 C15 H12 118.2 . . ?
C8 C15 H12 118.2 . . ?
C10 C16 C9 120.2(8) . . ?
C10 C16 H13 119.9 . . ?
C9 C16 H13 119.9 . . ?
C20 C17 N3 118.8(9) . . ?
C20 C17 H14 120.6 . . ?
N3 C17 H14 120.6 . . ?
C4 C18 C19 121.0(8) . . ?
C4 C18 H15 119.5 . . ?
C19 C18 H15 119.5 . . ?
C3 C19 C18 120.6(8) . . ?
C3 C19 H16 119.7 . . ?
C18 C19 H16 119.7 . . ?
C17 C20 C22 123.3(9) . . ?
C17 C20 H17 118.4 . . ?
C22 C20 H17 118.4 . . ?
C10 C21 C14 119.7(7) . . ?
C10 C21 H18 120.1 . . ?
C14 C21 H18 120.1 . . ?
C32 C22 C20 116.0(8) . . ?
C32 C22 C25 122.0(8) . . ?
C20 C22 C25 122.1(7) . . ?
C12 C23 C5 120.3(7) . . ?
C12 C23 H19 119.9 . . ?
C5 C23 H19 119.9 . . ?
C4 C24 C13 120.7(8) . . ?
C4 C24 H20 119.7 . . ?
C13 C24 H20 119.7 . . ?
C29 N3 C17 119.1(9) . . ?
C29 N3 H21 120.4 . . ?
C17 N3 H21 120.4 . . ?
C27 C25 C22 124.3(8) . . ?
C27 C25 C30 115.1(9) . . ?
C22 C25 C30 120.6(8) . . ?
C28 C26 C31 121.0(11) . . ?
C28 C26 H22 119.5 . . ?
C31 C26 H22 119.5 . . ?
C25 C27 C28 120.2(11) . . ?
C25 C27 H23 119.9 . . ?
C28 C27 H23 119.9 . . ?
C26 C28 C27 123.5(12) . . ?
C26 C28 H24 118.2 . . ?
C27 C28 H24 118.2 . . ?
N3 C29 C32 120.7(10) . . ?
N3 C29 H25 119.6 . . ?
C32 C29 H25 119.6 . . ?
C31 C30 C25 116.8(12) . . ?
C31 C30 H26 121.6 . . ?
C25 C30 H26 121.6 . . ?
C26 C31 C30 123.3(14) . . ?
C26 C31 H27 118.4 . . ?
C30 C31 H27 118.4 . . ?
C29 C32 C22 122.0(9) . . ?
C29 C32 H28 119.0 . . ?
C22 C32 H28 119.0 . . ?
C6 C33 C5 120.6(7) . . ?
C6 C33 H33 119.7 . . ?
C5 C33 H33 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.76
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.287
_refine_diff_density_min         -1.408
_refine_diff_density_rms         0.276
####################################################################### 
# 
# 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_e_a
_database_code_depnum_ccdc_archive 'CCDC 1882470'
loop_
_audit_author_name
_audit_author_address
'Li Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2018-12-01 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N O8'
_chemical_formula_weight         409.34

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           Triclinic
_symmetry_space_group_name_H-M   'P1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.7875(6)
_cell_length_b                   7.4323(7)
_cell_length_c                   9.6959(8)
_cell_angle_alpha                85.473(5)
_cell_angle_beta                 69.797(4)
_cell_angle_gamma                84.779(5)
_cell_volume                     456.54(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4633
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      25.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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            9641
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.03
_reflns_number_total             3552
_reflns_number_gt                2856
_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)+(0.0620P)²+0.0402P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(11)
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     276
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.8770(3) 0.3711(3) 1.06563(19) 0.0423(5) Uani 1 1 d . . .
O2 O 1.1985(3) 0.2488(3) 0.9718(2) 0.0496(5) Uani 1 1 d . . .
O3 O 0.9664(3) 0.3049(3) 0.3054(2) 0.0483(5) Uani 1 1 d . . .
H3 H 0.9225 0.3156 0.2360 0.072 Uiso 1 1 calc R . .
O4 O 0.6593(3) 0.7442(3) 0.5954(2) 0.0619(7) Uani 1 1 d . . .
H4 H 0.5580 0.8159 0.6008 0.093 Uiso 1 1 calc R . .
O5 O 1.3571(3) -0.0167(3) 0.5743(2) 0.0570(6) Uani 1 1 d . . .
O6 O 1.4103(3) 0.0973(3) 0.7565(3) 0.0642(7) Uani 1 1 d . . .
H6 H 1.3580 0.1777 0.8141 0.096 Uiso 1 1 calc R . .
O7 O 0.4141(3) 0.5757(4) 0.7466(3) 0.0674(7) Uani 1 1 d . . .
O8 O 0.6561(4) 0.4347(4) 0.4221(2) 0.0800(10) Uani 1 1 d . . .
C1 C 0.9965(4) 0.3220(3) 0.8098(3) 0.0279(6) Uani 1 1 d . . .
C2 C 1.0253(4) 0.3124(3) 0.9588(3) 0.0317(6) Uani 1 1 d . . .
C3 C 0.7734(3) 0.4612(3) 0.6742(2) 0.0277(6) Uani 1 1 d . . .
N1 N 1.3897(4) 0.5812(4) 0.2898(4) 0.0602(8) Uani 1 1 d . . .
C4 C 0.8874(4) 0.3585(3) 0.5536(3) 0.0260(5) Uani 1 1 d . . .
C6 C 0.5948(4) 0.5974(4) 0.6743(3) 0.0345(6) Uani 1 1 d . . .
C7 C 1.0899(4) 0.7574(4) 0.1881(3) 0.0343(6) Uani 1 1 d . . .
C8 C 1.1142(4) 0.2219(3) 0.6868(3) 0.0282(6) Uani 1 1 d . . .
C9 C 1.0541(4) 0.2419(3) 0.5630(2) 0.0283(6) Uani 1 1 d . . .
H9 H 1.1293 0.1738 0.4826 0.034 Uiso 1 1 calc R . .
C10 C 1.3057(4) 0.0916(4) 0.6720(3) 0.0385(6) Uani 1 1 d . . .
C11 C 0.8250(4) 0.3703(4) 0.4198(3) 0.0319(6) Uani 1 1 d . . .
C12 C 0.8290(4) 0.4396(3) 0.7987(3) 0.0308(6) Uani 1 1 d . . .
H12 H 0.7514 0.5065 0.8793 0.037 Uiso 1 1 calc R . .
C13 C 0.9250(4) 0.8441(4) 0.1331(3) 0.0392(6) Uani 1 1 d . . .
C14 C 1.2484(6) 0.6995(5) 0.3741(4) 0.0622(10) Uani 1 1 d . . .
H14 H 1.2519 0.7204 0.4665 0.075 Uiso 1 1 calc R . .
C15 C 1.2429(4) 0.6325(4) 0.1053(3) 0.0462(7) Uani 1 1 d . . .
H15 H 1.2447 0.6072 0.0124 0.055 Uiso 1 1 calc R . .
C16 C 1.0982(5) 0.7904(4) 0.3254(3) 0.0483(7) Uani 1 1 d . . .
H16 H 1.0016 0.8742 0.3841 0.058 Uiso 1 1 calc R . .
C17 C 0.9407(6) 0.8357(5) -0.0135(4) 0.0544(8) Uani 1 1 d . . .
H17 H 1.0592 0.7786 -0.0799 0.065 Uiso 1 1 calc R . .
C18 C 0.7465(5) 0.9332(4) 0.2289(4) 0.0547(9) Uani 1 1 d . . .
H18 H 0.7344 0.9410 0.3268 0.066 Uiso 1 1 calc R . .
C19 C 1.3884(5) 0.5479(5) 0.1589(4) 0.0556(8) Uani 1 1 d . . .
H19 H 1.4891 0.4651 0.1023 0.067 Uiso 1 1 calc R . .
C20 C 0.5867(5) 1.0105(6) 0.1805(5) 0.0763(12) Uani 1 1 d . . .
H20 H 0.4682 1.0693 0.2456 0.092 Uiso 1 1 calc R . .
C21 C 0.7777(7) 0.9136(6) -0.0603(5) 0.0738(12) Uani 1 1 d . . .
H21 H 0.7865 0.9072 -0.1577 0.089 Uiso 1 1 calc R . .
C22 C 0.6039(7) 0.9998(6) 0.0383(7) 0.0891(17) Uani 1 1 d . . .
H22 H 0.4963 1.0518 0.0064 0.107 Uiso 1 1 calc R . .
H2 H 1.492(7) 0.533(6) 0.326(5) 0.096(14) 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
O1 C2 1.244(3) . ?
O2 C2 1.270(3) . ?
O3 C11 1.286(3) . ?
O3 H3 0.8200 . ?
O4 C6 1.300(3) . ?
O4 H4 0.8200 . ?
O5 C10 1.228(3) . ?
O6 C10 1.261(3) . ?
O6 H6 0.8200 . ?
O7 C6 1.202(4) . ?
O8 C11 1.195(3) . ?
C1 C12 1.399(3) . ?
C1 C8 1.410(3) . ?
C1 C2 1.519(3) . ?
C3 C12 1.378(3) . ?
C3 C4 1.399(3) . ?
C3 C6 1.507(3) . ?
N1 C19 1.316(5) . ?
N1 C14 1.334(5) . ?
N1 H2 0.91(5) . ?
C4 C9 1.386(3) . ?
C4 C11 1.491(3) . ?
C7 C16 1.394(4) . ?
C7 C15 1.397(4) . ?
C7 C13 1.476(3) . ?
C8 C9 1.389(3) . ?
C8 C10 1.520(3) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C13 C17 1.394(4) . ?
C13 C18 1.394(4) . ?
C14 C16 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C19 1.353(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C21 1.398(5) . ?
C17 H17 0.9300 . ?
C18 C20 1.387(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C22 1.350(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 H3 109.5 . . ?
C6 O4 H4 109.5 . . ?
C10 O6 H6 109.5 . . ?
C12 C1 C8 118.1(2) . . ?
C12 C1 C2 114.8(2) . . ?
C8 C1 C2 127.1(2) . . ?
O1 C2 O2 121.6(2) . . ?
O1 C2 C1 118.2(2) . . ?
O2 C2 C1 120.2(2) . . ?
C12 C3 C4 118.6(2) . . ?
C12 C3 C6 118.0(2) . . ?
C4 C3 C6 123.3(2) . . ?
C19 N1 C14 121.3(3) . . ?
C19 N1 H2 123(3) . . ?
C14 N1 H2 116(3) . . ?
C9 C4 C3 118.73(19) . . ?
C9 C4 C11 120.9(2) . . ?
C3 C4 C11 120.3(2) . . ?
O7 C6 O4 124.1(3) . . ?
O7 C6 C3 123.2(3) . . ?
O4 C6 C3 112.6(2) . . ?
C16 C7 C15 116.6(3) . . ?
C16 C7 C13 122.5(2) . . ?
C15 C7 C13 120.9(3) . . ?
C9 C8 C1 118.2(2) . . ?
C9 C8 C10 114.53(19) . . ?
C1 C8 C10 127.2(2) . . ?
C4 C9 C8 123.1(2) . . ?
C4 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
O5 C10 O6 121.2(2) . . ?
O5 C10 C8 118.2(2) . . ?
O6 C10 C8 120.6(2) . . ?
O8 C11 O3 124.1(2) . . ?
O8 C11 C4 121.6(2) . . ?
O3 C11 C4 114.4(2) . . ?
C3 C12 C1 123.2(2) . . ?
C3 C12 H12 118.4 . . ?
C1 C12 H12 118.4 . . ?
C17 C13 C18 118.5(3) . . ?
C17 C13 C7 121.4(3) . . ?
C18 C13 C7 120.1(3) . . ?
N1 C14 C16 120.4(3) . . ?
N1 C14 H14 119.8 . . ?
C16 C14 H14 119.8 . . ?
C19 C15 C7 120.6(3) . . ?
C19 C15 H15 119.7 . . ?
C7 C15 H15 119.7 . . ?
C14 C16 C7 120.1(3) . . ?
C14 C16 H16 120.0 . . ?
C7 C16 H16 120.0 . . ?
C13 C17 C21 119.8(4) . . ?
C13 C17 H17 120.1 . . ?
C21 C17 H17 120.1 . . ?
C20 C18 C13 121.0(4) . . ?
C20 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
N1 C19 C15 121.0(3) . . ?
N1 C19 H19 119.5 . . ?
C15 C19 H19 119.5 . . ?
C22 C20 C18 119.6(4) . . ?
C22 C20 H20 120.2 . . ?
C18 C20 H20 120.2 . . ?
C22 C21 C17 119.7(4) . . ?
C22 C21 H21 120.1 . . ?
C17 C21 H21 120.1 . . ?
C20 C22 C21 121.4(4) . . ?
C20 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
