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

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

data_compound1aSI
_database_code_depnum_ccdc_archive 'CCDC 1436144'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Mo N4 O5 S'
_chemical_formula_sum            'C21 H22 Mo N4 O5 S'
_chemical_formula_weight         538.43

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'
S S 0.1246 0.1234 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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                   26.895(4)
_cell_length_b                   8.4616(10)
_cell_length_c                   21.724(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.874(8)
_cell_angle_gamma                90.00
_cell_volume                     4619.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    29280
_cell_measurement_theta_min      6.294
_cell_measurement_theta_max      34.449

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8180
_exptl_absorpt_correction_T_max  0.9335
_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            27898
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.31
_reflns_number_total             5738
_reflns_number_gt                2236
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0626P)²+3.3532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5738
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1808
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.16050(2) 0.76609(6) 0.16852(3) 0.0629(2) Uani 1 1 d . . .
S1 S 0.13388(8) 1.1230(2) 0.23764(10) 0.0881(6) Uani 1 1 d . . .
C1 C 0.0591(2) 0.7885(6) 0.0551(3) 0.0544(14) Uani 1 1 d . . .
N1 N 0.0321(2) 0.8269(6) -0.0077(3) 0.0636(12) Uani 1 1 d . . .
O1 O 0.21175(16) 0.8925(4) 0.1806(2) 0.0781(12) Uani 1 1 d . . .
N2 N -0.0191(2) 0.7565(6) -0.0305(2) 0.0717(14) Uani 1 1 d . . .
O2 O 0.17722(17) 0.6019(5) 0.1366(2) 0.0810(13) Uani 1 1 d . . .
C2 C 0.0269(3) 0.6886(7) 0.0774(3) 0.0665(16) Uani 1 1 d . . .
N3 N 0.0904(2) 0.6443(5) 0.1838(3) 0.0662(13) Uani 1 1 d . . .
O3 O 0.18283(18) 0.6981(5) 0.2612(2) 0.0781(12) Uani 1 1 d . . .
C3 C -0.0219(3) 0.6742(7) 0.0209(3) 0.0684(16) Uani 1 1 d . . .
O4 O 0.10687(17) 0.8444(5) 0.08667(19) 0.0776(12) Uani 1 1 d . . .
N4 N 0.1032(2) 0.5804(6) 0.2469(3) 0.0707(14) Uani 1 1 d . . .
C4 C -0.0728(2) 0.5881(7) 0.0121(3) 0.084(2) Uani 1 1 d . . .
H4A H -0.0958 0.5935 -0.0332 0.126 Uiso 1 1 calc R . .
H4B H -0.0900 0.6363 0.0392 0.126 Uiso 1 1 calc R . .
H4C H -0.0650 0.4796 0.0248 0.126 Uiso 1 1 calc R . .
O5 O 0.12000(15) 0.9602(4) 0.2084(2) 0.0736(12) Uani 1 1 d . . .
C5 C 0.0430(3) 0.6206(6) 0.1416(3) 0.0654(16) Uani 1 1 d . . .
C6 C 0.0028(3) 0.5224(8) 0.1598(3) 0.102(2) Uani 1 1 d . . .
H6A H 0.0205 0.4695 0.2009 0.152 Uiso 1 1 calc R . .
H6B H -0.0130 0.4454 0.1260 0.152 Uiso 1 1 calc R . .
H6C H -0.0244 0.5903 0.1639 0.152 Uiso 1 1 calc R . .
C7 C 0.1514(3) 0.6120(7) 0.2828(3) 0.0732(19) Uani 1 1 d . . .
C8 C 0.1742(3) 0.5545(8) 0.3524(3) 0.0773(19) Uani 1 1 d . . .
C9 C 0.2212(3) 0.6123(10) 0.3927(4) 0.109(3) Uani 1 1 d . . .
H9 H 0.2393 0.6870 0.3773 0.131 Uiso 1 1 calc R . .
C10 C 0.2423(4) 0.5596(15) 0.4570(5) 0.145(4) Uani 1 1 d . . .
H10 H 0.2749 0.5995 0.4844 0.175 Uiso 1 1 calc R . .
C11 C 0.2170(5) 0.4517(16) 0.4816(5) 0.152(5) Uani 1 1 d . . .
H11 H 0.2315 0.4202 0.5254 0.182 Uiso 1 1 calc R . .
C12 C 0.1709(4) 0.3917(10) 0.4413(5) 0.123(3) Uani 1 1 d . . .
H12 H 0.1541 0.3138 0.4571 0.147 Uiso 1 1 calc R . .
C13 C 0.1470(3) 0.4436(9) 0.3756(4) 0.092(2) Uani 1 1 d . . .
H13 H 0.1141 0.4048 0.3486 0.111 Uiso 1 1 calc R . .
C14 C 0.0467(3) 0.9186(7) -0.0538(3) 0.0626(16) Uani 1 1 d . . .
C15 C 0.0101(3) 0.9423(9) -0.1142(4) 0.099(2) Uani 1 1 d . . .
H15 H -0.0240 0.9012 -0.1251 0.119 Uiso 1 1 calc R . .
C16 C 0.0235(4) 1.0265(11) -0.1590(4) 0.125(3) Uani 1 1 d . . .
H16 H -0.0029 1.0465 -0.1996 0.149 Uiso 1 1 calc R . .
C17 C 0.0730(4) 1.0834(9) -0.1481(4) 0.094(2) Uani 1 1 d . . .
H17 H 0.0814 1.1337 -0.1812 0.113 Uiso 1 1 calc R . .
C18 C 0.1097(3) 1.0635(9) -0.0867(4) 0.093(2) Uani 1 1 d . . .
H18 H 0.1435 1.1062 -0.0764 0.111 Uiso 1 1 calc R . .
C19 C 0.0969(3) 0.9784(8) -0.0382(3) 0.089(2) Uani 1 1 d . . .
H19 H 0.1222 0.9634 0.0037 0.107 Uiso 1 1 calc R . .
C20 C 0.1564(4) 1.2294(8) 0.1832(4) 0.141(4) Uani 1 1 d . . .
H20A H 0.1851 1.1731 0.1766 0.211 Uiso 1 1 calc R . .
H20B H 0.1686 1.3317 0.2014 0.211 Uiso 1 1 calc R . .
H20C H 0.1277 1.2416 0.1417 0.211 Uiso 1 1 calc R . .
C21 C 0.1955(3) 1.1040(9) 0.3052(4) 0.117(3) Uani 1 1 d . . .
H21A H 0.1898 1.0467 0.3403 0.175 Uiso 1 1 calc R . .
H21B H 0.2092 1.2072 0.3206 0.175 Uiso 1 1 calc R . .
H21C H 0.2206 1.0480 0.2911 0.175 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 O2 1.684(4) . ?
Mo1 O1 1.690(4) . ?
Mo1 O4 1.963(4) . ?
Mo1 O3 1.970(4) . ?
Mo1 N3 2.273(5) . ?
Mo1 O5 2.304(4) . ?
S1 O5 1.507(4) . ?
S1 C20 1.757(8) . ?
S1 C21 1.787(7) . ?
C1 O4 1.310(6) . ?
C1 N1 1.337(7) . ?
C1 C2 1.414(8) . ?
N1 N2 1.417(7) . ?
N1 C14 1.429(7) . ?
N2 C3 1.341(7) . ?
C2 C5 1.426(8) . ?
C2 C3 1.448(8) . ?
N3 C5 1.294(7) . ?
N3 N4 1.398(6) . ?
O3 C7 1.323(8) . ?
C3 C4 1.501(8) . ?
N4 C7 1.279(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.523(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.497(9) . ?
C8 C9 1.348(9) . ?
C8 C13 1.389(9) . ?
C9 C10 1.382(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.355(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.339(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.411(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.344(8) . ?
C14 C19 1.367(9) . ?
C15 C16 1.354(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O2 Mo1 O1 105.3(2) . . ?
O2 Mo1 O4 97.09(19) . . ?
O1 Mo1 O4 102.87(18) . . ?
O2 Mo1 O3 98.67(19) . . ?
O1 Mo1 O3 95.21(19) . . ?
O4 Mo1 O3 151.90(19) . . ?
O2 Mo1 N3 92.46(18) . . ?
O1 Mo1 N3 159.51(18) . . ?
O4 Mo1 N3 84.58(18) . . ?
O3 Mo1 N3 71.66(19) . . ?
O2 Mo1 O5 167.04(17) . . ?
O1 Mo1 O5 87.63(17) . . ?
O4 Mo1 O5 78.86(16) . . ?
O3 Mo1 O5 80.61(16) . . ?
N3 Mo1 O5 74.97(14) . . ?
O5 S1 C20 106.1(3) . . ?
O5 S1 C21 106.4(3) . . ?
C20 S1 C21 99.1(4) . . ?
O4 C1 N1 121.5(5) . . ?
O4 C1 C2 130.0(6) . . ?
N1 C1 C2 108.6(5) . . ?
C1 N1 N2 111.2(5) . . ?
C1 N1 C14 131.5(5) . . ?
N2 N1 C14 117.3(5) . . ?
C3 N2 N1 105.2(5) . . ?
C1 C2 C5 124.5(6) . . ?
C1 C2 C3 103.9(5) . . ?
C5 C2 C3 131.5(6) . . ?
C5 N3 N4 118.1(5) . . ?
C5 N3 Mo1 128.8(4) . . ?
N4 N3 Mo1 113.0(4) . . ?
C7 O3 Mo1 121.5(4) . . ?
N2 C3 C2 111.1(6) . . ?
N2 C3 C4 117.7(6) . . ?
C2 C3 C4 131.1(6) . . ?
C1 O4 Mo1 128.3(4) . . ?
C7 N4 N3 111.0(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S1 O5 Mo1 137.0(2) . . ?
N3 C5 C2 120.6(6) . . ?
N3 C5 C6 120.9(6) . . ?
C2 C5 C6 118.5(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 O3 122.4(6) . . ?
N4 C7 C8 120.6(7) . . ?
O3 C7 C8 117.1(7) . . ?
C9 C8 C13 120.2(7) . . ?
C9 C8 C7 119.3(8) . . ?
C13 C8 C7 120.5(8) . . ?
C8 C9 C10 119.4(9) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 122.2(11) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 118.4(10) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.7(10) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 117.9(8) . . ?
C8 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C19 120.2(6) . . ?
C15 C14 N1 118.5(6) . . ?
C19 C14 N1 121.3(6) . . ?
C14 C15 C16 119.3(7) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 123.9(8) . . ?
C15 C16 H16 118.0 . . ?
C17 C16 H16 118.0 . . ?
C16 C17 C18 116.9(7) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 H17 121.6 . . ?
C17 C18 C19 120.7(7) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 118.8(6) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C1 N1 N2 -178.1(5) . . . . ?
C2 C1 N1 N2 0.3(6) . . . . ?
O4 C1 N1 C14 4.4(9) . . . . ?
C2 C1 N1 C14 -177.3(5) . . . . ?
C1 N1 N2 C3 0.0(6) . . . . ?
C14 N1 N2 C3 177.9(5) . . . . ?
O4 C1 C2 C5 -3.4(10) . . . . ?
N1 C1 C2 C5 178.4(5) . . . . ?
O4 C1 C2 C3 177.8(5) . . . . ?
N1 C1 C2 C3 -0.4(6) . . . . ?
O2 Mo1 N3 C5 -82.2(5) . . . . ?
O1 Mo1 N3 C5 127.4(6) . . . . ?
O4 Mo1 N3 C5 14.7(5) . . . . ?
O3 Mo1 N3 C5 179.5(5) . . . . ?
O5 Mo1 N3 C5 94.6(5) . . . . ?
O2 Mo1 N3 N4 93.7(4) . . . . ?
O1 Mo1 N3 N4 -56.8(7) . . . . ?
O4 Mo1 N3 N4 -169.4(4) . . . . ?
O3 Mo1 N3 N4 -4.7(3) . . . . ?
O5 Mo1 N3 N4 -89.5(3) . . . . ?
O2 Mo1 O3 C7 -84.0(4) . . . . ?
O1 Mo1 O3 C7 169.7(4) . . . . ?
O4 Mo1 O3 C7 39.5(6) . . . . ?
N3 Mo1 O3 C7 5.8(4) . . . . ?
O5 Mo1 O3 C7 82.9(4) . . . . ?
N1 N2 C3 C2 -0.3(6) . . . . ?
N1 N2 C3 C4 178.6(5) . . . . ?
C1 C2 C3 N2 0.4(7) . . . . ?
C5 C2 C3 N2 -178.2(6) . . . . ?
C1 C2 C3 C4 -178.3(6) . . . . ?
C5 C2 C3 C4 3.1(11) . . . . ?
N1 C1 O4 Mo1 -162.8(4) . . . . ?
C2 C1 O4 Mo1 19.2(9) . . . . ?
O2 Mo1 O4 C1 72.5(5) . . . . ?
O1 Mo1 O4 C1 -180.0(5) . . . . ?
O3 Mo1 O4 C1 -51.2(6) . . . . ?
N3 Mo1 O4 C1 -19.3(5) . . . . ?
O5 Mo1 O4 C1 -95.0(5) . . . . ?
C5 N3 N4 C7 179.4(5) . . . . ?
Mo1 N3 N4 C7 3.0(6) . . . . ?
C20 S1 O5 Mo1 50.9(5) . . . . ?
C21 S1 O5 Mo1 -53.9(5) . . . . ?
O1 Mo1 O5 S1 -4.3(4) . . . . ?
O4 Mo1 O5 S1 -107.9(4) . . . . ?
O3 Mo1 O5 S1 91.4(4) . . . . ?
N3 Mo1 O5 S1 164.8(4) . . . . ?
N4 N3 C5 C2 177.3(5) . . . . ?
Mo1 N3 C5 C2 -7.0(8) . . . . ?
N4 N3 C5 C6 -1.5(8) . . . . ?
Mo1 N3 C5 C6 174.2(4) . . . . ?
C1 C2 C5 N3 -2.1(9) . . . . ?
C3 C2 C5 N3 176.3(6) . . . . ?
C1 C2 C5 C6 176.7(6) . . . . ?
C3 C2 C5 C6 -4.8(10) . . . . ?
N3 N4 C7 O3 1.7(8) . . . . ?
N3 N4 C7 C8 -179.6(5) . . . . ?
Mo1 O3 C7 N4 -6.6(8) . . . . ?
Mo1 O3 C7 C8 174.5(4) . . . . ?
N4 C7 C8 C9 -168.1(6) . . . . ?
O3 C7 C8 C9 10.7(9) . . . . ?
N4 C7 C8 C13 11.3(9) . . . . ?
O3 C7 C8 C13 -169.8(5) . . . . ?
C13 C8 C9 C10 0.4(12) . . . . ?
C7 C8 C9 C10 179.9(7) . . . . ?
C8 C9 C10 C11 -0.5(16) . . . . ?
C9 C10 C11 C12 1.9(18) . . . . ?
C10 C11 C12 C13 -3.2(17) . . . . ?
C9 C8 C13 C12 -1.6(10) . . . . ?
C7 C8 C13 C12 178.9(6) . . . . ?
C11 C12 C13 C8 3.1(13) . . . . ?
C1 N1 C14 C15 -177.9(6) . . . . ?
N2 N1 C14 C15 4.7(8) . . . . ?
C1 N1 C14 C19 3.7(9) . . . . ?
N2 N1 C14 C19 -173.7(5) . . . . ?
C19 C14 C15 C16 -0.4(11) . . . . ?
N1 C14 C15 C16 -178.8(7) . . . . ?
C14 C15 C16 C17 3.5(14) . . . . ?
C15 C16 C17 C18 -5.1(14) . . . . ?
C16 C17 C18 C19 3.7(12) . . . . ?
C15 C14 C19 C18 -0.7(10) . . . . ?
N1 C14 C19 C18 177.7(6) . . . . ?
C17 C18 C19 C14 -1.0(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_compound1b
_database_code_depnum_ccdc_archive 'CCDC 1436145'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Mo N4 O5'
_chemical_formula_sum            'C19 H18 Mo N4 O5'
_chemical_formula_weight         478.31

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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                   9.4209(8)
_cell_length_b                   10.7591(10)
_cell_length_c                   19.0075(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.017(5)
_cell_angle_gamma                90.00
_cell_volume                     1923.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    29888
_cell_measurement_theta_min      4.352
_cell_measurement_theta_max      56.419

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8126
_exptl_absorpt_correction_T_max  0.9313
_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            28606
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4790
_reflns_number_gt                4067
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+1.0728P] 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         4790
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.317965(15) 0.671244(15) 0.206736(8) 0.02825(6) Uani 1 1 d . . .
N1 N 0.73358(15) 0.53801(15) 0.19790(8) 0.0291(3) Uani 1 1 d . . .
O1 O 0.27534(16) 0.77532(16) 0.14245(8) 0.0457(4) Uani 1 1 d . . .
C1 C 0.60984(18) 0.57083(17) 0.22555(9) 0.0272(4) Uani 1 1 d . . .
O2 O 0.25602(16) 0.53264(15) 0.17587(8) 0.0443(4) Uani 1 1 d . . .
N2 N 0.81679(16) 0.47001(15) 0.24604(8) 0.0313(3) Uani 1 1 d . . .
C2 C 0.60741(18) 0.52011(17) 0.29290(9) 0.0278(4) Uani 1 1 d . . .
N3 N 0.37848(15) 0.59444(15) 0.31480(8) 0.0300(3) Uani 1 1 d . . .
O3 O 0.52020(13) 0.64542(12) 0.19111(7) 0.0321(3) Uani 1 1 d . . .
C3 C 0.74246(19) 0.46005(17) 0.30269(10) 0.0295(4) Uani 1 1 d . . .
N4 N 0.27176(16) 0.60868(17) 0.36281(8) 0.0347(4) Uani 1 1 d . . .
O4 O 0.16293(13) 0.71331(14) 0.26859(7) 0.0355(3) Uani 1 1 d . . .
C4 C 0.8098(2) 0.3965(2) 0.36593(11) 0.0398(5) Uani 1 1 d . . .
H4C H 0.9001 0.3629 0.3545 0.060 Uiso 1 1 calc R . .
H4B H 0.7492 0.3305 0.3803 0.060 Uiso 1 1 calc R . .
H4A H 0.8233 0.4553 0.4037 0.060 Uiso 1 1 calc R . .
O5 O 0.41868(18) 0.84110(15) 0.27057(10) 0.0459(4) Uani 1 1 d . . .
H5WB H 0.489(3) 0.875(3) 0.2628(14) 0.056(8) Uiso 1 1 d . . .
H5WA H 0.366(3) 0.890(3) 0.2864(16) 0.066(9) Uiso 1 1 d . . .
C5 C 0.49223(19) 0.53542(18) 0.33878(10) 0.0300(4) Uani 1 1 d . . .
C6 C 0.5018(2) 0.4855(2) 0.41208(11) 0.0483(6) Uani 1 1 d . . .
H6C H 0.5736 0.5302 0.4395 0.072 Uiso 1 1 calc R . .
H6B H 0.5263 0.3990 0.4111 0.072 Uiso 1 1 calc R . .
H6A H 0.4118 0.4954 0.4329 0.072 Uiso 1 1 calc R . .
C7 C 0.16482(19) 0.66823(18) 0.33436(10) 0.0309(4) Uani 1 1 d . . .
C8 C 0.03733(19) 0.68925(17) 0.37464(10) 0.0307(4) Uani 1 1 d . . .
C9 C 0.0388(2) 0.6581(2) 0.44548(11) 0.0423(5) Uani 1 1 d . . .
H9 H 0.1207 0.6247 0.4675 0.051 Uiso 1 1 calc R . .
C10 C -0.0804(3) 0.6761(2) 0.48368(12) 0.0504(6) Uani 1 1 d . . .
H10 H -0.0781 0.6562 0.5313 0.060 Uiso 1 1 calc R . .
C11 C -0.2027(2) 0.7237(2) 0.45091(13) 0.0473(5) Uani 1 1 d . . .
H11 H -0.2832 0.7349 0.4765 0.057 Uiso 1 1 calc R . .
C12 C -0.2062(2) 0.7547(2) 0.38052(13) 0.0427(5) Uani 1 1 d . . .
H12 H -0.2891 0.7864 0.3587 0.051 Uiso 1 1 calc R . .
C13 C -0.0860(2) 0.73869(19) 0.34210(11) 0.0361(4) Uani 1 1 d . . .
H13 H -0.0880 0.7610 0.2948 0.043 Uiso 1 1 calc R . .
C14 C 0.78317(19) 0.56885(18) 0.13033(10) 0.0309(4) Uani 1 1 d . . .
C15 C 0.9221(2) 0.6073(2) 0.12608(12) 0.0420(5) Uani 1 1 d . . .
H15 H 0.9819 0.6126 0.1665 0.050 Uiso 1 1 calc R . .
C16 C 0.9713(3) 0.6380(3) 0.06110(14) 0.0547(6) Uani 1 1 d . . .
H16 H 1.0652 0.6630 0.0576 0.066 Uiso 1 1 calc R . .
C17 C 0.8821(3) 0.6318(3) 0.00144(14) 0.0586(7) Uani 1 1 d . . .
H17 H 0.9155 0.6533 -0.0421 0.070 Uiso 1 1 calc R . .
C18 C 0.7440(3) 0.5939(2) 0.00629(12) 0.0522(6) Uani 1 1 d . . .
H18 H 0.6840 0.5903 -0.0341 0.063 Uiso 1 1 calc R . .
C19 C 0.6928(2) 0.5608(2) 0.07098(11) 0.0404(5) Uani 1 1 d . . .
H19 H 0.5996 0.5337 0.0742 0.048 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 O1 1.6901(14) . ?
Mo1 O2 1.6948(15) . ?
Mo1 O3 1.9634(12) . ?
Mo1 O4 1.9751(13) . ?
Mo1 N3 2.2590(15) . ?
Mo1 O5 2.3645(17) . ?
N1 C1 1.351(2) . ?
N1 N2 1.383(2) . ?
N1 C14 1.429(2) . ?
C1 O3 1.314(2) . ?
C1 C2 1.393(2) . ?
N2 C3 1.319(2) . ?
C2 C3 1.430(2) . ?
C2 C5 1.437(3) . ?
N3 C5 1.307(2) . ?
N3 N4 1.401(2) . ?
C3 C4 1.495(3) . ?
N4 C7 1.289(2) . ?
O4 C7 1.340(2) . ?
C4 H4C 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4A 0.9600 . ?
O5 H5WB 0.78(3) . ?
O5 H5WA 0.80(3) . ?
C5 C6 1.491(3) . ?
C6 H6C 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6A 0.9600 . ?
C7 C8 1.475(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 C19 1.380(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 H19 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
O1 Mo1 O2 105.56(8) . . ?
O1 Mo1 O3 100.36(6) . . ?
O2 Mo1 O3 98.18(7) . . ?
O1 Mo1 O4 97.10(7) . . ?
O2 Mo1 O4 98.96(7) . . ?
O3 Mo1 O4 151.21(6) . . ?
O1 Mo1 N3 159.83(7) . . ?
O2 Mo1 N3 93.37(7) . . ?
O3 Mo1 N3 83.42(5) . . ?
O4 Mo1 N3 72.65(6) . . ?
O1 Mo1 O5 86.14(8) . . ?
O2 Mo1 O5 168.30(7) . . ?
O3 Mo1 O5 79.67(6) . . ?
O4 Mo1 O5 78.86(6) . . ?
N3 Mo1 O5 74.98(6) . . ?
C1 N1 N2 110.59(15) . . ?
C1 N1 C14 128.24(15) . . ?
N2 N1 C14 121.13(14) . . ?
O3 C1 N1 120.72(16) . . ?
O3 C1 C2 130.98(16) . . ?
N1 C1 C2 108.15(15) . . ?
C3 N2 N1 106.04(14) . . ?
C1 C2 C3 103.83(16) . . ?
C1 C2 C5 124.21(16) . . ?
C3 C2 C5 131.91(17) . . ?
C5 N3 N4 115.42(15) . . ?
C5 N3 Mo1 131.14(13) . . ?
N4 N3 Mo1 113.38(11) . . ?
C1 O3 Mo1 127.89(11) . . ?
N2 C3 C2 111.34(16) . . ?
N2 C3 C4 118.19(17) . . ?
C2 C3 C4 130.40(18) . . ?
C7 N4 N3 110.67(15) . . ?
C7 O4 Mo1 119.90(12) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
Mo1 O5 H5WB 126(2) . . ?
Mo1 O5 H5WA 118(2) . . ?
H5WB O5 H5WA 109(3) . . ?
N3 C5 C2 118.40(16) . . ?
N3 C5 C6 120.60(17) . . ?
C2 C5 C6 121.00(17) . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
N4 C7 O4 122.89(17) . . ?
N4 C7 C8 119.89(17) . . ?
O4 C7 C8 117.22(16) . . ?
C9 C8 C13 119.27(18) . . ?
C9 C8 C7 119.98(18) . . ?
C13 C8 C7 120.74(18) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C15 C14 C19 121.18(19) . . ?
C15 C14 N1 118.60(17) . . ?
C19 C14 N1 120.22(17) . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 118.6(2) . . ?
C14 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 O3 173.85(16) . . . . ?
C14 N1 C1 O3 -3.8(3) . . . . ?
N2 N1 C1 C2 -2.1(2) . . . . ?
C14 N1 C1 C2 -179.74(17) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
C14 N1 N2 C3 178.69(16) . . . . ?
O3 C1 C2 C3 -173.03(19) . . . . ?
N1 C1 C2 C3 2.4(2) . . . . ?
O3 C1 C2 C5 4.5(3) . . . . ?
N1 C1 C2 C5 179.90(17) . . . . ?
O1 Mo1 N3 C5 -116.5(2) . . . . ?
O2 Mo1 N3 C5 83.56(18) . . . . ?
O3 Mo1 N3 C5 -14.30(17) . . . . ?
O4 Mo1 N3 C5 -178.10(18) . . . . ?
O5 Mo1 N3 C5 -95.32(18) . . . . ?
O1 Mo1 N3 N4 66.7(2) . . . . ?
O2 Mo1 N3 N4 -93.29(13) . . . . ?
O3 Mo1 N3 N4 168.86(13) . . . . ?
O4 Mo1 N3 N4 5.05(12) . . . . ?
O5 Mo1 N3 N4 87.83(13) . . . . ?
N1 C1 O3 Mo1 162.31(13) . . . . ?
C2 C1 O3 Mo1 -22.8(3) . . . . ?
O1 Mo1 O3 C1 -178.77(16) . . . . ?
O2 Mo1 O3 C1 -71.21(16) . . . . ?
O4 Mo1 O3 C1 54.8(2) . . . . ?
N3 Mo1 O3 C1 21.26(15) . . . . ?
O5 Mo1 O3 C1 97.14(16) . . . . ?
N1 N2 C3 C2 0.7(2) . . . . ?
N1 N2 C3 C4 -176.55(16) . . . . ?
C1 C2 C3 N2 -1.9(2) . . . . ?
C5 C2 C3 N2 -179.17(19) . . . . ?
C1 C2 C3 C4 174.9(2) . . . . ?
C5 C2 C3 C4 -2.3(4) . . . . ?
C5 N3 N4 C7 179.73(17) . . . . ?
Mo1 N3 N4 C7 -2.9(2) . . . . ?
O1 Mo1 O4 C7 -168.69(15) . . . . ?
O2 Mo1 O4 C7 84.26(15) . . . . ?
O3 Mo1 O4 C7 -41.6(2) . . . . ?
N3 Mo1 O4 C7 -6.49(13) . . . . ?
O5 Mo1 O4 C7 -84.07(15) . . . . ?
N4 N3 C5 C2 -178.51(16) . . . . ?
Mo1 N3 C5 C2 4.7(3) . . . . ?
N4 N3 C5 C6 1.4(3) . . . . ?
Mo1 N3 C5 C6 -175.42(16) . . . . ?
C1 C2 C5 N3 4.2(3) . . . . ?
C3 C2 C5 N3 -179.08(19) . . . . ?
C1 C2 C5 C6 -175.7(2) . . . . ?
C3 C2 C5 C6 1.0(3) . . . . ?
N3 N4 C7 O4 -2.6(3) . . . . ?
N3 N4 C7 C8 177.46(16) . . . . ?
Mo1 O4 C7 N4 7.9(3) . . . . ?
Mo1 O4 C7 C8 -172.17(12) . . . . ?
N4 C7 C8 C9 7.6(3) . . . . ?
O4 C7 C8 C9 -172.40(18) . . . . ?
N4 C7 C8 C13 -171.52(19) . . . . ?
O4 C7 C8 C13 8.5(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 -179.3(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
C7 C8 C13 C12 178.28(18) . . . . ?
C1 N1 C14 C15 135.2(2) . . . . ?
N2 N1 C14 C15 -42.2(3) . . . . ?
C1 N1 C14 C19 -44.4(3) . . . . ?
N2 N1 C14 C19 138.21(19) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
N1 C14 C15 C16 -179.7(2) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C15 C14 C19 C18 -0.8(3) . . . . ?
N1 C14 C19 C18 178.75(19) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5WB N2 0.78(3) 2.11(3) 2.884(2) 174(3) 2_655
O5 H5WA O2 0.80(3) 2.07(3) 2.858(2) 174(3) 2

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_compound3a
_database_code_depnum_ccdc_archive 'CCDC 1436146'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Mo N6 O5'
_chemical_formula_sum            'C21 H22 Mo N6 O5'
_chemical_formula_weight         534.39

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   7.7039(12)
_cell_length_b                   9.7133(15)
_cell_length_c                   15.248(2)
_cell_angle_alpha                85.657(7)
_cell_angle_beta                 83.289(7)
_cell_angle_gamma                71.113(7)
_cell_volume                     1071.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    56879
_cell_measurement_theta_min      4.436
_cell_measurement_theta_max      59.260

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8684
_exptl_absorpt_correction_T_max  0.9197
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            56274
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         30.17
_reflns_number_total             6305
_reflns_number_gt                5857
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.6042P] 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         6305
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
Mo1 Mo 0.820899(18) 0.099422(14) 0.803354(8) 0.01563(5) Uani 1 1 d . . .
O1 O 0.79106(17) 0.01992(13) 0.90495(8) 0.0230(2) Uani 1 1 d . . .
N1 N 1.20578(19) -0.17453(15) 0.62302(9) 0.0187(3) Uani 1 1 d . . .
C1 C 1.1066(2) -0.05006(17) 0.66442(11) 0.0175(3) Uani 1 1 d . . .
O2 O 0.65476(17) 0.08099(14) 0.74577(8) 0.0231(2) Uani 1 1 d . . .
N2 N 1.2767(2) -0.14294(16) 0.53889(9) 0.0210(3) Uani 1 1 d . . .
C2 C 1.1091(2) 0.06716(18) 0.60573(10) 0.0178(3) Uani 1 1 d . . .
O3 O 1.03269(16) -0.05165(12) 0.74651(8) 0.0197(2) Uani 1 1 d . . .
N3 N 0.90455(19) 0.24822(14) 0.69677(9) 0.0172(3) Uani 1 1 d . . .
C3 C 1.2202(2) 0.00006(19) 0.52903(11) 0.0199(3) Uani 1 1 d . . .
O4 O 0.69122(16) 0.30231(12) 0.83756(8) 0.0179(2) Uani 1 1 d . . .
N4 N 0.81403(19) 0.39625(15) 0.71029(9) 0.0186(3) Uani 1 1 d . . .
C4 C 1.2810(3) 0.0659(2) 0.44408(12) 0.0261(4) Uani 1 1 d . . .
H4A H 1.3460 -0.0099 0.4041 0.039 Uiso 1 1 calc R . .
H4B H 1.3609 0.1193 0.4553 0.039 Uiso 1 1 calc R . .
H4C H 1.1751 0.1306 0.4182 0.039 Uiso 1 1 calc R . .
O5 O 1.05469(16) 0.15327(13) 0.85931(8) 0.0199(2) Uani 1 1 d . . .
C5 C 1.0119(2) 0.21746(18) 0.62291(10) 0.0178(3) Uani 1 1 d . . .
N5 N 0.3624(2) 0.69688(16) 0.91991(11) 0.0255(3) Uani 1 1 d . . .
N6 N 1.15366(19) 0.24701(15) 0.96782(9) 0.0193(3) Uani 1 1 d . . .
C6 C 1.0286(3) 0.33477(19) 0.55592(11) 0.0238(3) Uani 1 1 d . . .
H6A H 0.9572 0.3364 0.5081 0.036 Uiso 1 1 calc R . .
H6B H 1.1556 0.3157 0.5336 0.036 Uiso 1 1 calc R . .
H6C H 0.9839 0.4273 0.5831 0.036 Uiso 1 1 calc R . .
C7 C 0.7071(2) 0.41223(17) 0.78302(11) 0.0171(3) Uani 1 1 d . . .
C8 C 0.5921(2) 0.55808(17) 0.81129(11) 0.0179(3) Uani 1 1 d . . .
C9 C 0.5934(2) 0.68487(19) 0.76220(12) 0.0220(3) Uani 1 1 d . . .
H9 H 0.671(3) 0.678(2) 0.7071(15) 0.026(6) Uiso 1 1 d . . .
C10 C 0.4773(3) 0.81655(19) 0.79342(13) 0.0255(4) Uani 1 1 d . . .
H10 H 0.472(3) 0.902(3) 0.7596(16) 0.035(6) Uiso 1 1 d . . .
C11 C 0.3642(3) 0.81740(19) 0.87158(13) 0.0262(4) Uani 1 1 d . . .
H11 H 0.282(3) 0.902(3) 0.8936(16) 0.030(6) Uiso 1 1 d . . .
C12 C 0.4758(2) 0.57039(18) 0.88924(12) 0.0215(3) Uani 1 1 d . . .
H12 H 0.477(3) 0.484(2) 0.9242(15) 0.024(5) Uiso 1 1 d . . .
C13 C 1.2400(2) -0.32286(18) 0.65224(11) 0.0192(3) Uani 1 1 d . . .
C14 C 1.3863(2) -0.42847(19) 0.60839(12) 0.0228(3) Uani 1 1 d . . .
H14 H 1.468(3) -0.397(3) 0.5612(16) 0.033(6) Uiso 1 1 d . . .
C15 C 1.4207(3) -0.5741(2) 0.63459(12) 0.0253(4) Uani 1 1 d . . .
H15 H 1.519(3) -0.645(3) 0.6059(16) 0.034(6) Uiso 1 1 d . . .
C16 C 1.3126(3) -0.6152(2) 0.70396(13) 0.0264(4) Uani 1 1 d . . .
H16 H 1.339(3) -0.712(3) 0.7198(16) 0.030(6) Uiso 1 1 d . . .
C17 C 1.1676(3) -0.5089(2) 0.74736(12) 0.0245(3) Uani 1 1 d . . .
H17 H 1.097(3) -0.535(3) 0.7929(16) 0.029(6) Uiso 1 1 d . . .
C18 C 1.1294(2) -0.36284(19) 0.72122(12) 0.0219(3) Uani 1 1 d . . .
H18 H 1.032(3) -0.294(2) 0.7490(15) 0.025(5) Uiso 1 1 d . . .
C19 C 1.0248(2) 0.21747(18) 0.93039(11) 0.0189(3) Uani 1 1 d . . .
H19 H 0.907(3) 0.251(2) 0.9620(14) 0.020(5) Uiso 1 1 d . . .
C20 C 1.3462(2) 0.1965(2) 0.93247(13) 0.0281(4) Uani 1 1 d . . .
H20A H 1.4164 0.1266 0.9735 0.042 Uiso 1 1 calc R . .
H20B H 1.3925 0.2776 0.9234 0.042 Uiso 1 1 calc R . .
H20C H 1.3568 0.1519 0.8772 0.042 Uiso 1 1 calc R . .
C21 C 1.1119(3) 0.3191(2) 1.05142(12) 0.0253(3) Uani 1 1 d . . .
H21A H 0.9836 0.3385 1.0711 0.038 Uiso 1 1 calc R . .
H21B H 1.1393 0.4092 1.0437 0.038 Uiso 1 1 calc R . .
H21C H 1.1852 0.2573 1.0947 0.038 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 O2 1.6959(13) . ?
Mo1 O1 1.7028(12) . ?
Mo1 O3 1.9694(12) . ?
Mo1 O4 1.9782(12) . ?
Mo1 N3 2.2689(14) . ?
Mo1 O5 2.2983(12) . ?
N1 C1 1.360(2) . ?
N1 N2 1.3869(19) . ?
N1 C13 1.424(2) . ?
C1 O3 1.3144(19) . ?
C1 C2 1.398(2) . ?
N2 C3 1.317(2) . ?
C2 C3 1.430(2) . ?
C2 C5 1.437(2) . ?
N3 C5 1.309(2) . ?
N3 N4 1.3994(19) . ?
C3 C4 1.494(2) . ?
O4 C7 1.3314(19) . ?
N4 C7 1.289(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O5 C19 1.252(2) . ?
C5 C6 1.499(2) . ?
N5 C12 1.337(2) . ?
N5 C11 1.338(2) . ?
N6 C19 1.317(2) . ?
N6 C21 1.454(2) . ?
N6 C20 1.454(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.473(2) . ?
C8 C12 1.390(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.97(2) . ?
C10 C11 1.391(3) . ?
C10 H10 0.94(3) . ?
C11 H11 0.92(2) . ?
C12 H12 0.96(2) . ?
C13 C18 1.388(2) . ?
C13 C14 1.396(2) . ?
C14 C15 1.388(3) . ?
C14 H14 0.99(2) . ?
C15 C16 1.385(3) . ?
C15 H15 0.93(2) . ?
C16 C17 1.391(3) . ?
C16 H16 0.91(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.90(2) . ?
C18 H18 0.91(2) . ?
C19 H19 0.94(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O2 Mo1 O1 105.51(6) . . ?
O2 Mo1 O3 98.26(6) . . ?
O1 Mo1 O3 101.80(5) . . ?
O2 Mo1 O4 96.92(6) . . ?
O1 Mo1 O4 96.40(5) . . ?
O3 Mo1 O4 152.17(5) . . ?
O2 Mo1 N3 92.83(6) . . ?
O1 Mo1 N3 159.79(6) . . ?
O3 Mo1 N3 83.49(5) . . ?
O4 Mo1 N3 72.57(5) . . ?
O2 Mo1 O5 169.14(5) . . ?
O1 Mo1 O5 85.18(5) . . ?
O3 Mo1 O5 81.06(5) . . ?
O4 Mo1 O5 79.68(5) . . ?
N3 Mo1 O5 76.32(5) . . ?
C1 N1 N2 110.69(13) . . ?
C1 N1 C13 130.25(14) . . ?
N2 N1 C13 119.05(13) . . ?
O3 C1 N1 122.02(15) . . ?
O3 C1 C2 130.26(15) . . ?
N1 C1 C2 107.67(14) . . ?
C3 N2 N1 105.93(13) . . ?
C1 C2 C3 104.00(14) . . ?
C1 C2 C5 124.89(14) . . ?
C3 C2 C5 131.06(15) . . ?
C1 O3 Mo1 127.36(10) . . ?
C5 N3 N4 115.95(13) . . ?
C5 N3 Mo1 130.45(11) . . ?
N4 N3 Mo1 113.40(10) . . ?
N2 C3 C2 111.70(15) . . ?
N2 C3 C4 117.68(15) . . ?
C2 C3 C4 130.61(16) . . ?
C7 O4 Mo1 119.66(10) . . ?
C7 N4 N3 110.12(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C19 O5 Mo1 120.25(11) . . ?
N3 C5 C2 118.37(14) . . ?
N3 C5 C6 121.29(15) . . ?
C2 C5 C6 120.30(14) . . ?
C12 N5 C11 116.74(16) . . ?
C19 N6 C21 121.10(15) . . ?
C19 N6 C20 121.75(15) . . ?
C21 N6 C20 116.88(14) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 O4 124.01(14) . . ?
N4 C7 C8 120.84(14) . . ?
O4 C7 C8 115.15(14) . . ?
C12 C8 C9 118.48(15) . . ?
C12 C8 C7 119.04(15) . . ?
C9 C8 C7 122.47(15) . . ?
C10 C9 C8 118.09(17) . . ?
C10 C9 H9 122.1(14) . . ?
C8 C9 H9 119.8(14) . . ?
C9 C10 C11 119.13(17) . . ?
C9 C10 H10 119.0(16) . . ?
C11 C10 H10 121.8(15) . . ?
N5 C11 C10 123.55(16) . . ?
N5 C11 H11 114.6(15) . . ?
C10 C11 H11 121.8(15) . . ?
N5 C12 C8 124.00(16) . . ?
N5 C12 H12 117.2(14) . . ?
C8 C12 H12 118.8(13) . . ?
C18 C13 C14 120.41(16) . . ?
C18 C13 N1 121.34(15) . . ?
C14 C13 N1 118.23(15) . . ?
C15 C14 C13 119.40(17) . . ?
C15 C14 H14 121.2(14) . . ?
C13 C14 H14 119.3(14) . . ?
C16 C15 C14 120.74(16) . . ?
C16 C15 H15 119.3(15) . . ?
C14 C15 H15 120.0(15) . . ?
C15 C16 C17 119.33(17) . . ?
C15 C16 H16 118.8(15) . . ?
C17 C16 H16 121.9(16) . . ?
C18 C17 C16 120.74(18) . . ?
C18 C17 H17 119.4(15) . . ?
C16 C17 H17 119.9(15) . . ?
C13 C18 C17 119.37(16) . . ?
C13 C18 H18 120.3(14) . . ?
C17 C18 H18 120.3(14) . . ?
O5 C19 N6 123.45(15) . . ?
O5 C19 H19 123.2(13) . . ?
N6 C19 H19 113.4(13) . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 O3 -176.81(14) . . . . ?
C13 N1 C1 O3 4.8(3) . . . . ?
N2 N1 C1 C2 1.02(18) . . . . ?
C13 N1 C1 C2 -177.40(15) . . . . ?
C1 N1 N2 C3 -0.29(18) . . . . ?
C13 N1 N2 C3 178.33(14) . . . . ?
O3 C1 C2 C3 176.31(16) . . . . ?
N1 C1 C2 C3 -1.27(17) . . . . ?
O3 C1 C2 C5 -5.8(3) . . . . ?
N1 C1 C2 C5 176.60(15) . . . . ?
N1 C1 O3 Mo1 -156.62(12) . . . . ?
C2 C1 O3 Mo1 26.1(2) . . . . ?
O2 Mo1 O3 C1 67.65(14) . . . . ?
O1 Mo1 O3 C1 175.49(13) . . . . ?
O4 Mo1 O3 C1 -54.75(18) . . . . ?
N3 Mo1 O3 C1 -24.28(13) . . . . ?
O5 Mo1 O3 C1 -101.39(14) . . . . ?
O2 Mo1 N3 C5 -81.48(15) . . . . ?
O1 Mo1 N3 C5 123.12(18) . . . . ?
O3 Mo1 N3 C5 16.51(14) . . . . ?
O4 Mo1 N3 C5 -177.85(15) . . . . ?
O5 Mo1 N3 C5 98.86(15) . . . . ?
O2 Mo1 N3 N4 92.96(11) . . . . ?
O1 Mo1 N3 N4 -62.4(2) . . . . ?
O3 Mo1 N3 N4 -169.04(11) . . . . ?
O4 Mo1 N3 N4 -3.41(10) . . . . ?
O5 Mo1 N3 N4 -86.70(10) . . . . ?
N1 N2 C3 C2 -0.56(19) . . . . ?
N1 N2 C3 C4 178.47(14) . . . . ?
C1 C2 C3 N2 1.16(19) . . . . ?
C5 C2 C3 N2 -176.52(16) . . . . ?
C1 C2 C3 C4 -177.72(17) . . . . ?
C5 C2 C3 C4 4.6(3) . . . . ?
O2 Mo1 O4 C7 -86.46(12) . . . . ?
O1 Mo1 O4 C7 167.00(12) . . . . ?
O3 Mo1 O4 C7 36.21(17) . . . . ?
N3 Mo1 O4 C7 4.34(11) . . . . ?
O5 Mo1 O4 C7 83.11(11) . . . . ?
C5 N3 N4 C7 177.27(14) . . . . ?
Mo1 N3 N4 C7 1.97(16) . . . . ?
O2 Mo1 O5 C19 117.2(3) . . . . ?
O1 Mo1 O5 C19 -52.78(12) . . . . ?
O3 Mo1 O5 C19 -155.55(13) . . . . ?
O4 Mo1 O5 C19 44.63(12) . . . . ?
N3 Mo1 O5 C19 119.03(13) . . . . ?
N4 N3 C5 C2 179.67(13) . . . . ?
Mo1 N3 C5 C2 -6.0(2) . . . . ?
N4 N3 C5 C6 -2.5(2) . . . . ?
Mo1 N3 C5 C6 171.80(12) . . . . ?
C1 C2 C5 N3 -3.8(2) . . . . ?
C3 C2 C5 N3 173.41(17) . . . . ?
C1 C2 C5 C6 178.34(16) . . . . ?
C3 C2 C5 C6 -4.4(3) . . . . ?
N3 N4 C7 O4 1.7(2) . . . . ?
N3 N4 C7 C8 -178.35(13) . . . . ?
Mo1 O4 C7 N4 -5.3(2) . . . . ?
Mo1 O4 C7 C8 174.78(10) . . . . ?
N4 C7 C8 C12 178.68(16) . . . . ?
O4 C7 C8 C12 -1.4(2) . . . . ?
N4 C7 C8 C9 -0.5(2) . . . . ?
O4 C7 C8 C9 179.45(15) . . . . ?
C12 C8 C9 C10 -0.5(2) . . . . ?
C7 C8 C9 C10 178.62(15) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C12 N5 C11 C10 -0.7(3) . . . . ?
C9 C10 C11 N5 1.0(3) . . . . ?
C11 N5 C12 C8 -0.3(3) . . . . ?
C9 C8 C12 N5 0.9(3) . . . . ?
C7 C8 C12 N5 -178.32(16) . . . . ?
C1 N1 C13 C18 19.0(3) . . . . ?
N2 N1 C13 C18 -159.28(15) . . . . ?
C1 N1 C13 C14 -162.28(16) . . . . ?
N2 N1 C13 C14 19.4(2) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
N1 C13 C14 C15 -178.94(15) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
N1 C13 C18 C17 179.83(15) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
Mo1 O5 C19 N6 177.48(12) . . . . ?
C21 N6 C19 O5 -178.68(16) . . . . ?
C20 N6 C19 O5 -5.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.17
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1436147'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Mo N4 O6'
_chemical_formula_sum            'C20 H20 Mo N4 O6'
_chemical_formula_weight         508.34

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'
Mo Mo -1.6832 0.6857 '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)/c
_symmetry_space_group_name_Hall  -P2ybc

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                   7.6247(4)
_cell_length_b                   17.1429(9)
_cell_length_c                   15.4107(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.512(3)
_cell_angle_gamma                90.00
_cell_volume                     2008.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7966
_cell_measurement_theta_min      5.303
_cell_measurement_theta_max      57.636

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_T_max  0.9333
_exptl_absorpt_process_details   SADABS

_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  '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            7803
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         31.15
_reflns_number_total             4749
_reflns_number_gt                3635
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0402P)²+2.1069P] 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         4749
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.59253(4) 0.110385(16) 0.211977(17) 0.02794(11) Uani 1 1 d . . .
O1 O 0.4055(4) 0.08823(18) 0.2563(2) 0.0530(7) Uani 1 1 d . . .
N1 N 0.7834(4) 0.20837(15) 0.45152(16) 0.0285(6) Uani 1 1 d . . .
C1 C 0.7268(4) 0.20433(18) 0.36595(19) 0.0260(7) Uani 1 1 d . . .
N2 N 0.7860(4) 0.28487(15) 0.47954(17) 0.0295(6) Uani 1 1 d . . .
O2 O 0.7352(4) 0.02104(16) 0.2331(2) 0.0572(8) Uani 1 1 d . . .
C2 C 0.6820(4) 0.27939(17) 0.33768(19) 0.0246(7) Uani 1 1 d . . .
O3 O 0.6481(4) 0.01756(17) 0.1543(2) 0.0621(9) Uani 1 1 d . . .
N3 N 0.5483(4) 0.23766(16) 0.20122(16) 0.0284(6) Uani 1 1 d . . .
C3 C 0.7272(4) 0.32771(19) 0.4120(2) 0.0275(7) Uani 1 1 d . . .
O4 O 0.4842(3) 0.13016(13) 0.09195(15) 0.0349(6) Uani 1 1 d . . .
N4 N 0.4564(4) 0.25998(16) 0.12267(17) 0.0331(7) Uani 1 1 d . . .
C4 C 0.7196(6) 0.4140(2) 0.4230(2) 0.0411(9) Uani 1 1 d . . .
H4A H 0.7534 0.4272 0.4825 0.062 Uiso 1 1 calc R . .
H4B H 0.6019 0.4319 0.4078 0.062 Uiso 1 1 calc R . .
H4C H 0.7986 0.4384 0.3858 0.062 Uiso 1 1 calc R . .
O5 O 0.7314(4) 0.13902(14) 0.32306(14) 0.0371(6) Uani 1 1 d . . .
C5 C 0.5977(4) 0.29616(18) 0.2535(2) 0.0252(7) Uani 1 1 d . . .
O6 O 0.8413(3) 0.15756(16) 0.14916(17) 0.0349(6) Uani 1 1 d . . .
H6O H 0.821(6) 0.181(3) 0.115(3) 0.043(14) Uiso 1 1 d . . .
C6 C 0.5632(6) 0.37813(19) 0.2255(2) 0.0395(9) Uani 1 1 d . . .
H6A H 0.5629 0.3816 0.1633 0.059 Uiso 1 1 calc R . .
H6B H 0.6536 0.4114 0.2520 0.059 Uiso 1 1 calc R . .
H6C H 0.4510 0.3944 0.2432 0.059 Uiso 1 1 calc R . .
C7 C 0.4272(4) 0.20139(19) 0.0715(2) 0.0292(7) Uani 1 1 d . . .
C8 C 0.3278(4) 0.2108(2) -0.0137(2) 0.0285(7) Uani 1 1 d . . .
C9 C 0.2635(5) 0.1457(2) -0.0596(2) 0.0368(9) Uani 1 1 d . . .
H9 H 0.282(4) 0.1003(19) -0.040(2) 0.022(9) Uiso 1 1 d . . .
C10 C 0.1690(5) 0.1546(2) -0.1392(2) 0.0416(9) Uani 1 1 d . . .
H10 H 0.115(5) 0.113(2) -0.166(3) 0.045(12) Uiso 1 1 d . . .
C11 C 0.1371(5) 0.2275(3) -0.1737(2) 0.0419(10) Uani 1 1 d . . .
H11 H 0.091(6) 0.236(3) -0.222(3) 0.070(15) Uiso 1 1 d . . .
C12 C 0.2008(5) 0.2926(3) -0.1286(2) 0.0428(9) Uani 1 1 d . . .
H12 H 0.185(6) 0.341(3) -0.146(3) 0.063(14) Uiso 1 1 d . . .
C13 C 0.2957(5) 0.2845(2) -0.0489(2) 0.0383(9) Uani 1 1 d . . .
H13 H 0.343(5) 0.330(2) -0.017(3) 0.046(11) Uiso 1 1 d . . .
C14 C 0.8338(5) 0.14626(19) 0.50943(19) 0.0293(7) Uani 1 1 d . . .
C15 C 0.9714(5) 0.1558(2) 0.5720(2) 0.0363(9) Uani 1 1 d . . .
H15 H 1.027(5) 0.193(2) 0.572(2) 0.022(10) Uiso 1 1 d . . .
C16 C 1.0229(6) 0.0950(3) 0.6261(3) 0.0474(11) Uani 1 1 d . . .
H16 H 1.114(6) 0.102(2) 0.655(3) 0.045(12) Uiso 1 1 d . . .
C17 C 0.9361(7) 0.0249(3) 0.6198(3) 0.0532(12) Uani 1 1 d . . .
H17 H 0.969(6) -0.017(3) 0.649(3) 0.057(13) Uiso 1 1 d . . .
C18 C 0.7975(7) 0.0153(3) 0.5576(3) 0.0513(11) Uani 1 1 d . . .
H18 H 0.740(6) -0.026(3) 0.556(3) 0.049(13) Uiso 1 1 d . . .
C19 C 0.7445(6) 0.0762(2) 0.5021(2) 0.0385(9) Uani 1 1 d . . .
H19 H 0.655(5) 0.069(2) 0.468(3) 0.042(11) Uiso 1 1 d . . .
C20 C 1.0048(6) 0.1171(3) 0.1485(3) 0.0539(11) Uani 1 1 d . . .
H20A H 1.0302 0.0913 0.2034 0.081 Uiso 1 1 calc R . .
H20B H 1.0969 0.1536 0.1392 0.081 Uiso 1 1 calc R . .
H20C H 0.9974 0.0791 0.1026 0.081 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 O1 1.673(3) . ?
Mo1 O3 1.887(3) . ?
Mo1 O2 1.892(3) . ?
Mo1 O4 1.994(2) . ?
Mo1 O5 2.002(2) . ?
Mo1 N3 2.212(3) . ?
Mo1 O6 2.340(3) . ?
N1 C1 1.357(4) . ?
N1 N2 1.380(4) . ?
N1 C14 1.423(4) . ?
C1 O5 1.302(4) . ?
C1 C2 1.393(4) . ?
N2 C3 1.323(4) . ?
O2 O3 1.339(4) . ?
C2 C5 1.432(4) . ?
C2 C3 1.434(4) . ?
N3 C5 1.322(4) . ?
N3 N4 1.403(3) . ?
C3 C4 1.490(5) . ?
O4 C7 1.326(4) . ?
N4 C7 1.285(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.487(4) . ?
O6 C20 1.428(5) . ?
O6 H6O 0.66(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.473(4) . ?
C8 C13 1.388(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.382(5) . ?
C9 H9 0.84(3) . ?
C10 C11 1.373(6) . ?
C10 H10 0.91(4) . ?
C11 C12 1.381(6) . ?
C11 H11 0.81(5) . ?
C12 C13 1.383(5) . ?
C12 H12 0.88(5) . ?
C13 H13 0.98(4) . ?
C14 C15 1.377(5) . ?
C14 C19 1.381(5) . ?
C15 C16 1.374(5) . ?
C15 H15 0.76(3) . ?
C16 C17 1.372(7) . ?
C16 H16 0.81(4) . ?
C17 C18 1.379(6) . ?
C17 H17 0.88(5) . ?
C18 C19 1.390(5) . ?
C18 H18 0.83(4) . ?
C19 H19 0.84(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 Mo1 O3 103.36(15) . . ?
O1 Mo1 O2 104.06(14) . . ?
O3 Mo1 O2 41.51(12) . . ?
O1 Mo1 O4 96.50(13) . . ?
O3 Mo1 O4 78.36(12) . . ?
O2 Mo1 O4 119.19(12) . . ?
O1 Mo1 O5 96.71(14) . . ?
O3 Mo1 O5 119.11(12) . . ?
O2 Mo1 O5 78.06(12) . . ?
O4 Mo1 O5 154.68(10) . . ?
O1 Mo1 N3 97.16(13) . . ?
O3 Mo1 N3 146.62(12) . . ?
O2 Mo1 N3 153.34(12) . . ?
O4 Mo1 N3 73.33(9) . . ?
O5 Mo1 N3 83.66(9) . . ?
O1 Mo1 O6 172.79(12) . . ?
O3 Mo1 O6 82.95(12) . . ?
O2 Mo1 O6 82.95(12) . . ?
O4 Mo1 O6 81.23(10) . . ?
O5 Mo1 O6 82.97(10) . . ?
N3 Mo1 O6 75.64(10) . . ?
C1 N1 N2 110.4(2) . . ?
C1 N1 C14 128.4(3) . . ?
N2 N1 C14 121.2(2) . . ?
O5 C1 N1 121.2(3) . . ?
O5 C1 C2 130.7(3) . . ?
N1 C1 C2 108.0(3) . . ?
C3 N2 N1 106.6(2) . . ?
O3 O2 Mo1 69.06(18) . . ?
C1 C2 C5 123.4(3) . . ?
C1 C2 C3 104.3(3) . . ?
C5 C2 C3 132.2(3) . . ?
O2 O3 Mo1 69.43(18) . . ?
C5 N3 N4 114.7(3) . . ?
C5 N3 Mo1 131.9(2) . . ?
N4 N3 Mo1 113.35(19) . . ?
N2 C3 C2 110.7(3) . . ?
N2 C3 C4 118.4(3) . . ?
C2 C3 C4 130.9(3) . . ?
C7 O4 Mo1 118.74(19) . . ?
C7 N4 N3 111.5(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 O5 Mo1 127.69(19) . . ?
N3 C5 C2 119.1(3) . . ?
N3 C5 C6 120.4(3) . . ?
C2 C5 C6 120.6(3) . . ?
C20 O6 Mo1 124.9(2) . . ?
C20 O6 H6O 116(4) . . ?
Mo1 O6 H6O 113(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 O4 122.5(3) . . ?
N4 C7 C8 120.9(3) . . ?
O4 C7 C8 116.7(3) . . ?
C13 C8 C9 119.2(3) . . ?
C13 C8 C7 120.7(3) . . ?
C9 C8 C7 120.1(3) . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119(2) . . ?
C8 C9 H9 121(2) . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 118(3) . . ?
C9 C10 H10 121(3) . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 124(4) . . ?
C12 C11 H11 116(4) . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 125(3) . . ?
C13 C12 H12 114(3) . . ?
C12 C13 C8 120.2(4) . . ?
C12 C13 H13 121(2) . . ?
C8 C13 H13 119(2) . . ?
C15 C14 C19 120.3(3) . . ?
C15 C14 N1 120.2(3) . . ?
C19 C14 N1 119.5(3) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120(3) . . ?
C14 C15 H15 120(3) . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 125(3) . . ?
C15 C16 H16 114(3) . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 125(3) . . ?
C18 C17 H17 115(3) . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 120(3) . . ?
C19 C18 H18 119(3) . . ?
C14 C19 C18 119.1(4) . . ?
C14 C19 H19 124(3) . . ?
C18 C19 H19 117(3) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 O5 172.6(3) . . . . ?
C14 N1 C1 O5 -8.0(5) . . . . ?
N2 N1 C1 C2 -3.2(4) . . . . ?
C14 N1 C1 C2 176.2(3) . . . . ?
C1 N1 N2 C3 1.4(4) . . . . ?
C14 N1 N2 C3 -178.0(3) . . . . ?
O1 Mo1 O2 O3 94.4(2) . . . . ?
O4 Mo1 O2 O3 -11.5(2) . . . . ?
O5 Mo1 O2 O3 -171.6(2) . . . . ?
N3 Mo1 O2 O3 -123.9(3) . . . . ?
O6 Mo1 O2 O3 -87.3(2) . . . . ?
O5 C1 C2 C5 12.4(6) . . . . ?
N1 C1 C2 C5 -172.4(3) . . . . ?
O5 C1 C2 C3 -171.8(4) . . . . ?
N1 C1 C2 C3 3.4(4) . . . . ?
O1 Mo1 O3 O2 -96.2(2) . . . . ?
O4 Mo1 O3 O2 169.8(2) . . . . ?
O5 Mo1 O3 O2 9.4(2) . . . . ?
N3 Mo1 O3 O2 137.4(2) . . . . ?
O6 Mo1 O3 O2 87.3(2) . . . . ?
O1 Mo1 N3 C5 94.0(3) . . . . ?
O3 Mo1 N3 C5 -138.1(3) . . . . ?
O2 Mo1 N3 C5 -48.7(5) . . . . ?
O4 Mo1 N3 C5 -171.3(3) . . . . ?
O5 Mo1 N3 C5 -2.0(3) . . . . ?
O6 Mo1 N3 C5 -86.4(3) . . . . ?
O1 Mo1 N3 N4 -88.8(2) . . . . ?
O3 Mo1 N3 N4 39.0(3) . . . . ?
O2 Mo1 N3 N4 128.4(3) . . . . ?
O4 Mo1 N3 N4 5.9(2) . . . . ?
O5 Mo1 N3 N4 175.2(2) . . . . ?
O6 Mo1 N3 N4 90.8(2) . . . . ?
N1 N2 C3 C2 0.8(4) . . . . ?
N1 N2 C3 C4 -178.6(3) . . . . ?
C1 C2 C3 N2 -2.7(4) . . . . ?
C5 C2 C3 N2 172.7(3) . . . . ?
C1 C2 C3 C4 176.7(4) . . . . ?
C5 C2 C3 C4 -8.0(6) . . . . ?
O1 Mo1 O4 C7 88.5(3) . . . . ?
O3 Mo1 O4 C7 -169.1(3) . . . . ?
O2 Mo1 O4 C7 -161.4(2) . . . . ?
O5 Mo1 O4 C7 -32.6(4) . . . . ?
N3 Mo1 O4 C7 -7.0(2) . . . . ?
O6 Mo1 O4 C7 -84.6(2) . . . . ?
C5 N3 N4 C7 173.8(3) . . . . ?
Mo1 N3 N4 C7 -3.9(4) . . . . ?
N1 C1 O5 Mo1 159.4(2) . . . . ?
C2 C1 O5 Mo1 -26.0(5) . . . . ?
O1 Mo1 O5 C1 -79.6(3) . . . . ?
O3 Mo1 O5 C1 171.0(3) . . . . ?
O2 Mo1 O5 C1 177.4(3) . . . . ?
O4 Mo1 O5 C1 41.4(4) . . . . ?
N3 Mo1 O5 C1 16.9(3) . . . . ?
O6 Mo1 O5 C1 93.1(3) . . . . ?
N4 N3 C5 C2 175.9(3) . . . . ?
Mo1 N3 C5 C2 -6.9(5) . . . . ?
N4 N3 C5 C6 -3.1(5) . . . . ?
Mo1 N3 C5 C6 174.1(3) . . . . ?
C1 C2 C5 N3 4.7(5) . . . . ?
C3 C2 C5 N3 -169.9(3) . . . . ?
C1 C2 C5 C6 -176.3(3) . . . . ?
C3 C2 C5 C6 9.1(6) . . . . ?
O1 Mo1 O6 C20 163.1(10) . . . . ?
O3 Mo1 O6 C20 -45.5(3) . . . . ?
O2 Mo1 O6 C20 -3.6(3) . . . . ?
O4 Mo1 O6 C20 -124.7(3) . . . . ?
O5 Mo1 O6 C20 75.2(3) . . . . ?
N3 Mo1 O6 C20 160.4(3) . . . . ?
N3 N4 C7 O4 -2.0(5) . . . . ?
N3 N4 C7 C8 178.2(3) . . . . ?
Mo1 O4 C7 N4 7.9(5) . . . . ?
Mo1 O4 C7 C8 -172.3(2) . . . . ?
N4 C7 C8 C13 13.7(5) . . . . ?
O4 C7 C8 C13 -166.1(3) . . . . ?
N4 C7 C8 C9 -165.6(3) . . . . ?
O4 C7 C8 C9 14.6(5) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C7 C8 C9 C10 179.5(3) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 0.2(6) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
C7 C8 C13 C12 -179.4(3) . . . . ?
C1 N1 C14 C15 142.9(4) . . . . ?
N2 N1 C14 C15 -37.8(5) . . . . ?
C1 N1 C14 C19 -36.7(5) . . . . ?
N2 N1 C14 C19 142.6(3) . . . . ?
C19 C14 C15 C16 1.4(6) . . . . ?
N1 C14 C15 C16 -178.2(4) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C15 C16 C17 C18 0.9(7) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C15 C14 C19 C18 -1.2(6) . . . . ?
N1 C14 C19 C18 178.4(4) . . . . ?
C17 C18 C19 C14 0.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6O N2 0.66(4) 2.17(4) 2.795(4) 158(5) 4_565

_diffrn_measured_fraction_theta_max 0.732
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.845
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1436148'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Mo N5 O6, C H4 O'
_chemical_formula_sum            'C20 H23 Mo N5 O7'
_chemical_formula_weight         541.37

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc

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                   7.4244(2)
_cell_length_b                   17.9776(6)
_cell_length_c                   16.4764(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.410(2)
_cell_angle_gamma                90.00
_cell_volume                     2195.26(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    46735
_cell_measurement_theta_min      4.531
_cell_measurement_theta_max      47.725

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8632
_exptl_absorpt_correction_T_max  0.9173
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            45667
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4454
_reflns_number_gt                3700
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0584P)²+6.1672P] 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         4454
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.06330(5) 0.209881(19) 0.102372(19) 0.02362(13) Uani 1 1 d . . .
O1 O 0.2672(4) 0.17467(17) 0.08734(18) 0.0339(7) Uani 1 1 d . . .
N1 N 0.2590(4) 0.42221(18) 0.1759(2) 0.0253(7) Uani 1 1 d . . .
O1M O 0.5542(14) 0.3347(4) -0.2129(6) 0.159(3) Uani 1 1 d . . .
H1M H 0.5853 0.2978 -0.1863 0.239 Uiso 1 1 calc R . .
C1M C 0.5034(7) 0.3887(3) -0.1623(4) 0.0479(14) Uani 1 1 d . . .
H1M1 H 0.5333 0.3742 -0.1070 0.072 Uiso 1 1 calc R . .
H1M2 H 0.3755 0.3963 -0.1699 0.072 Uiso 1 1 calc R . .
H1M3 H 0.5652 0.4340 -0.1739 0.072 Uiso 1 1 calc R . .
C1 C 0.1929(5) 0.3663(2) 0.1287(2) 0.0241(8) Uani 1 1 d . . .
N2 N 0.2912(5) 0.48486(18) 0.1296(2) 0.0268(7) Uani 1 1 d . . .
C2 C 0.1821(5) 0.3913(2) 0.0482(2) 0.0242(8) Uani 1 1 d . . .
O2 O 0.0347(5) 0.1871(2) 0.2143(2) 0.0477(9) Uani 1 1 d . . .
O3 O -0.0468(5) 0.1347(2) 0.1624(2) 0.0522(10) Uani 1 1 d . . .
N3 N 0.0668(4) 0.27886(18) -0.00823(19) 0.0243(7) Uani 1 1 d . . .
C3 C 0.2467(5) 0.4664(2) 0.0537(2) 0.0257(8) Uani 1 1 d . . .
O4 O -0.0719(4) 0.15287(17) 0.01400(16) 0.0312(7) Uani 1 1 d . . .
N4 N 0.0028(5) 0.2413(2) -0.0791(2) 0.0281(7) Uani 1 1 d . . .
C4 C 0.2724(6) 0.5229(2) -0.0109(3) 0.0333(10) Uani 1 1 d . . .
H4A H 0.3290 0.5664 0.0130 0.050 Uiso 1 1 calc R . .
H4B H 0.1573 0.5362 -0.0364 0.050 Uiso 1 1 calc R . .
H4C H 0.3475 0.5026 -0.0509 0.050 Uiso 1 1 calc R . .
O5 O 0.1473(4) 0.30319(15) 0.16012(16) 0.0269(6) Uani 1 1 d . . .
C5 C 0.1140(5) 0.3483(2) -0.0198(2) 0.0263(9) Uani 1 1 d . . .
N5 N -0.2073(6) 0.1150(3) -0.2702(2) 0.0451(11) Uani 1 1 d . . .
H5 H -0.2161 0.1335 -0.3184 0.054 Uiso 1 1 calc R . .
O6 O -0.1959(4) 0.2764(2) 0.10685(18) 0.0409(8) Uani 1 1 d . . .
C6 C 0.0954(7) 0.3824(3) -0.1029(2) 0.0350(10) Uani 1 1 d . . .
H6A H 0.2112 0.3836 -0.1259 0.052 Uiso 1 1 calc R . .
H6B H 0.0497 0.4321 -0.0990 0.052 Uiso 1 1 calc R . .
H6C H 0.0134 0.3532 -0.1371 0.052 Uiso 1 1 calc R . .
C7 C -0.0617(5) 0.1776(2) -0.0614(2) 0.0266(9) Uani 1 1 d . . .
C8 C -0.1306(5) 0.1279(2) -0.1276(2) 0.0285(9) Uani 1 1 d . . .
C9 C -0.1790(6) 0.0555(3) -0.1145(3) 0.0344(10) Uani 1 1 d . . .
H9 H -0.163(7) 0.037(3) -0.066(3) 0.039(14) Uiso 1 1 d . . .
C10 C -0.2418(6) 0.0129(3) -0.1809(3) 0.0450(13) Uani 1 1 d . . .
H10 H -0.2744 -0.0365 -0.1741 0.054 Uiso 1 1 calc R . .
C11 C -0.2548(7) 0.0450(4) -0.2563(3) 0.0496(14) Uani 1 1 d . . .
H11 H -0.282(7) 0.019(3) -0.306(3) 0.049(15) Uiso 1 1 d . . .
C12 C -0.1458(6) 0.1552(3) -0.2069(3) 0.0337(10) Uani 1 1 d . . .
H12 H -0.095(7) 0.203(3) -0.218(3) 0.040(14) Uiso 1 1 d . . .
C13 C 0.2873(5) 0.4254(2) 0.2626(2) 0.0239(8) Uani 1 1 d . . .
C14 C 0.2559(6) 0.4918(2) 0.3019(2) 0.0271(9) Uani 1 1 d . . .
H14 H 0.210(6) 0.529(3) 0.273(3) 0.024(11) Uiso 1 1 d . . .
C15 C 0.2870(6) 0.4952(3) 0.3854(3) 0.0317(10) Uani 1 1 d . . .
H15 H 0.271(7) 0.536(3) 0.411(3) 0.040(14) Uiso 1 1 d . . .
C16 C 0.3476(6) 0.4335(3) 0.4295(3) 0.0319(9) Uani 1 1 d . . .
H16 H 0.366(6) 0.437(3) 0.486(3) 0.030(12) Uiso 1 1 d . . .
C17 C 0.3755(6) 0.3675(3) 0.3889(3) 0.0300(9) Uani 1 1 d . . .
H17 H 0.418(6) 0.328(3) 0.416(3) 0.029(12) Uiso 1 1 d . . .
C18 C 0.3473(6) 0.3628(2) 0.3056(3) 0.0276(9) Uani 1 1 d . . .
H18 H 0.365(6) 0.317(3) 0.275(3) 0.025(11) Uiso 1 1 d . . .
C19 C -0.3695(8) 0.2603(4) 0.0733(5) 0.075(2) Uani 1 1 d . . .
H19A H -0.3844 0.2816 0.0199 0.112 Uiso 1 1 calc R . .
H19B H -0.4576 0.2810 0.1072 0.112 Uiso 1 1 calc R . .
H19C H -0.3852 0.2074 0.0699 0.112 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 O1 1.673(3) . ?
Mo1 O3 1.890(3) . ?
Mo1 O2 1.913(3) . ?
Mo1 O4 2.001(3) . ?
Mo1 O5 2.009(3) . ?
Mo1 N3 2.206(3) . ?
Mo1 O6 2.271(3) . ?
N1 C1 1.346(5) . ?
N1 N2 1.389(5) . ?
N1 C13 1.433(5) . ?
O1M C1M 1.348(9) . ?
O1M H1M 0.8200 . ?
C1M H1M1 0.9600 . ?
C1M H1M2 0.9600 . ?
C1M H1M3 0.9600 . ?
C1 O5 1.300(5) . ?
C1 C2 1.400(5) . ?
N2 C3 1.318(5) . ?
C2 C5 1.429(6) . ?
C2 C3 1.432(6) . ?
O2 O3 1.387(5) . ?
N3 C5 1.314(5) . ?
N3 N4 1.407(4) . ?
C3 C4 1.493(6) . ?
O4 C7 1.325(5) . ?
N4 C7 1.281(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.499(5) . ?
N5 C12 1.327(6) . ?
N5 C11 1.330(8) . ?
N5 H5 0.8600 . ?
O6 C19 1.401(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.479(6) . ?
C8 C9 1.370(7) . ?
C8 C12 1.394(6) . ?
C9 C10 1.392(7) . ?
C9 H9 0.87(5) . ?
C10 C11 1.368(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.96(6) . ?
C12 H12 0.96(5) . ?
C13 C14 1.385(6) . ?
C13 C18 1.388(6) . ?
C14 C15 1.383(6) . ?
C14 H14 0.88(4) . ?
C15 C16 1.387(6) . ?
C15 H15 0.85(5) . ?
C16 C17 1.384(6) . ?
C16 H16 0.94(5) . ?
C17 C18 1.379(6) . ?
C17 H17 0.89(5) . ?
C18 H18 0.98(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O1 Mo1 O3 103.31(17) . . ?
O1 Mo1 O2 102.42(16) . . ?
O3 Mo1 O2 42.77(15) . . ?
O1 Mo1 O4 96.76(14) . . ?
O3 Mo1 O4 78.50(14) . . ?
O2 Mo1 O4 120.80(14) . . ?
O1 Mo1 O5 97.35(14) . . ?
O3 Mo1 O5 118.76(14) . . ?
O2 Mo1 O5 76.79(13) . . ?
O4 Mo1 O5 154.19(12) . . ?
O1 Mo1 N3 92.02(14) . . ?
O3 Mo1 N3 149.48(14) . . ?
O2 Mo1 N3 157.55(14) . . ?
O4 Mo1 N3 73.54(12) . . ?
O5 Mo1 N3 84.45(11) . . ?
O1 Mo1 O6 168.61(14) . . ?
O3 Mo1 O6 88.05(16) . . ?
O2 Mo1 O6 86.48(14) . . ?
O4 Mo1 O6 84.49(12) . . ?
O5 Mo1 O6 77.57(12) . . ?
N3 Mo1 O6 77.43(12) . . ?
C1 N1 N2 111.0(3) . . ?
C1 N1 C13 129.2(3) . . ?
N2 N1 C13 119.7(3) . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
O5 C1 N1 121.1(3) . . ?
O5 C1 C2 131.1(4) . . ?
N1 C1 C2 107.8(3) . . ?
C3 N2 N1 105.9(3) . . ?
C1 C2 C5 124.5(4) . . ?
C1 C2 C3 104.1(3) . . ?
C5 C2 C3 131.4(4) . . ?
O3 O2 Mo1 67.74(19) . . ?
O2 O3 Mo1 69.5(2) . . ?
C5 N3 N4 114.6(3) . . ?
C5 N3 Mo1 132.1(3) . . ?
N4 N3 Mo1 113.3(2) . . ?
N2 C3 C2 111.2(3) . . ?
N2 C3 C4 118.0(4) . . ?
C2 C3 C4 130.8(4) . . ?
C7 O4 Mo1 117.1(3) . . ?
C7 N4 N3 110.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 O5 Mo1 128.4(2) . . ?
N3 C5 C2 119.1(4) . . ?
N3 C5 C6 120.7(4) . . ?
C2 C5 C6 120.3(4) . . ?
C12 N5 C11 117.5(5) . . ?
C12 N5 H5 121.2 . . ?
C11 N5 H5 121.2 . . ?
C19 O6 Mo1 129.8(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 O4 123.8(4) . . ?
N4 C7 C8 119.3(4) . . ?
O4 C7 C8 116.9(4) . . ?
C9 C8 C12 118.4(4) . . ?
C9 C8 C7 122.7(4) . . ?
C12 C8 C7 118.9(4) . . ?
C8 C9 C10 118.4(5) . . ?
C8 C9 H9 119(3) . . ?
C10 C9 H9 123(3) . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N5 C11 C10 123.4(5) . . ?
N5 C11 H11 111(3) . . ?
C10 C11 H11 125(3) . . ?
N5 C12 C8 123.3(5) . . ?
N5 C12 H12 117(3) . . ?
C8 C12 H12 119(3) . . ?
C14 C13 C18 121.2(4) . . ?
C14 C13 N1 118.8(4) . . ?
C18 C13 N1 120.0(4) . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 H14 123(3) . . ?
C13 C14 H14 118(3) . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 120(3) . . ?
C16 C15 H15 119(3) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16 121(3) . . ?
C15 C16 H16 120(3) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119(3) . . ?
C16 C17 H17 120(3) . . ?
C17 C18 C13 118.9(4) . . ?
C17 C18 H18 123(3) . . ?
C13 C18 H18 118(3) . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 O5 -177.5(3) . . . . ?
C13 N1 C1 O5 -1.5(6) . . . . ?
N2 N1 C1 C2 0.7(4) . . . . ?
C13 N1 C1 C2 176.8(4) . . . . ?
C1 N1 N2 C3 -0.9(4) . . . . ?
C13 N1 N2 C3 -177.4(3) . . . . ?
O5 C1 C2 C5 -0.4(7) . . . . ?
N1 C1 C2 C5 -178.4(4) . . . . ?
O5 C1 C2 C3 177.7(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
O1 Mo1 O2 O3 -96.3(3) . . . . ?
O4 Mo1 O2 O3 9.5(3) . . . . ?
O5 Mo1 O2 O3 169.0(3) . . . . ?
N3 Mo1 O2 O3 134.9(4) . . . . ?
O6 Mo1 O2 O3 90.9(2) . . . . ?
O1 Mo1 O3 O2 94.0(2) . . . . ?
O4 Mo1 O3 O2 -171.7(3) . . . . ?
O5 Mo1 O3 O2 -12.3(3) . . . . ?
N3 Mo1 O3 O2 -147.8(3) . . . . ?
O6 Mo1 O3 O2 -86.9(2) . . . . ?
O1 Mo1 N3 C5 -94.9(4) . . . . ?
O3 Mo1 N3 C5 144.2(4) . . . . ?
O2 Mo1 N3 C5 35.6(6) . . . . ?
O4 Mo1 N3 C5 168.7(4) . . . . ?
O5 Mo1 N3 C5 2.3(4) . . . . ?
O6 Mo1 N3 C5 80.8(4) . . . . ?
O1 Mo1 N3 N4 86.6(3) . . . . ?
O3 Mo1 N3 N4 -34.3(4) . . . . ?
O2 Mo1 N3 N4 -143.0(4) . . . . ?
O4 Mo1 N3 N4 -9.9(2) . . . . ?
O5 Mo1 N3 N4 -176.2(3) . . . . ?
O6 Mo1 N3 N4 -97.8(3) . . . . ?
N1 N2 C3 C2 0.7(4) . . . . ?
N1 N2 C3 C4 -178.3(3) . . . . ?
C1 C2 C3 N2 -0.2(4) . . . . ?
C5 C2 C3 N2 177.7(4) . . . . ?
C1 C2 C3 C4 178.6(4) . . . . ?
C5 C2 C3 C4 -3.6(7) . . . . ?
O1 Mo1 O4 C7 -79.0(3) . . . . ?
O3 Mo1 O4 C7 178.7(3) . . . . ?
O2 Mo1 O4 C7 172.1(3) . . . . ?
O5 Mo1 O4 C7 43.7(4) . . . . ?
N3 Mo1 O4 C7 11.1(3) . . . . ?
O6 Mo1 O4 C7 89.6(3) . . . . ?
C5 N3 N4 C7 -171.7(4) . . . . ?
Mo1 N3 N4 C7 7.1(4) . . . . ?
N1 C1 O5 Mo1 -175.2(3) . . . . ?
C2 C1 O5 Mo1 7.0(6) . . . . ?
O1 Mo1 O5 C1 85.0(3) . . . . ?
O3 Mo1 O5 C1 -165.4(3) . . . . ?
O2 Mo1 O5 C1 -173.9(4) . . . . ?
O4 Mo1 O5 C1 -37.6(5) . . . . ?
N3 Mo1 O5 C1 -6.4(3) . . . . ?
O6 Mo1 O5 C1 -84.7(3) . . . . ?
N4 N3 C5 C2 -179.5(3) . . . . ?
Mo1 N3 C5 C2 1.9(6) . . . . ?
N4 N3 C5 C6 1.0(5) . . . . ?
Mo1 N3 C5 C6 -177.6(3) . . . . ?
C1 C2 C5 N3 -4.1(6) . . . . ?
C3 C2 C5 N3 178.4(4) . . . . ?
C1 C2 C5 C6 175.4(4) . . . . ?
C3 C2 C5 C6 -2.1(7) . . . . ?
O1 Mo1 O6 C19 111.4(8) . . . . ?
O3 Mo1 O6 C19 -64.1(5) . . . . ?
O2 Mo1 O6 C19 -106.9(5) . . . . ?
O4 Mo1 O6 C19 14.5(5) . . . . ?
O5 Mo1 O6 C19 175.8(5) . . . . ?
N3 Mo1 O6 C19 88.8(5) . . . . ?
N3 N4 C7 O4 2.4(6) . . . . ?
N3 N4 C7 C8 -177.9(3) . . . . ?
Mo1 O4 C7 N4 -12.0(5) . . . . ?
Mo1 O4 C7 C8 168.3(3) . . . . ?
N4 C7 C8 C9 171.0(4) . . . . ?
O4 C7 C8 C9 -9.3(6) . . . . ?
N4 C7 C8 C12 -8.4(6) . . . . ?
O4 C7 C8 C12 171.3(4) . . . . ?
C12 C8 C9 C10 -0.3(6) . . . . ?
C7 C8 C9 C10 -179.7(4) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C12 N5 C11 C10 -0.6(7) . . . . ?
C9 C10 C11 N5 1.2(8) . . . . ?
C11 N5 C12 C8 -0.6(7) . . . . ?
C9 C8 C12 N5 1.0(7) . . . . ?
C7 C8 C12 N5 -179.5(4) . . . . ?
C1 N1 C13 C14 -143.3(4) . . . . ?
N2 N1 C13 C14 32.5(5) . . . . ?
C1 N1 C13 C18 37.5(6) . . . . ?
N2 N1 C13 C18 -146.7(4) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
N1 C13 C14 C15 -178.6(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C16 C17 C18 C13 -1.0(6) . . . . ?
C14 C13 C18 C17 0.1(6) . . . . ?
N1 C13 C18 C17 179.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 O6 0.86 2.05 2.819(6) 149.0 4_565

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.898
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.102
