# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Mo N2 O7'
_chemical_formula_weight         458.27

_audit_creation_method           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   7.0077(3)
_cell_length_b                   27.0442(16)
_cell_length_c                   9.7840(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.138(4)
_cell_angle_gamma                90.00
_cell_volume                     1812.79(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7355
_cell_measurement_theta_min      3.6875
_cell_measurement_theta_max      32.3829
_cell_oxdiff_length_a            7.0033(4)
_cell_oxdiff_length_b            27.0636(13)
_cell_oxdiff_length_c            9.7817(4)
_cell_oxdiff_angle_alpha         89.921(3)
_cell_oxdiff_angle_beta          102.102(4)
_cell_oxdiff_angle_gamma         90.053(4)
_cell_oxdiff_volume              1812.79(15)
_cell_oxdiff_measurement_reflns_used 7355
_exptl_absorpt_correction_T_min  0.92544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_detector_area_resol_mean 16.3426

_diffrn_reflns_number            22974
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         28.99
_reflns_number_total             4814
_reflns_number_gt                3404
_reflns_threshold_expression     >2σ(I)


_diffrn_orient_matrix_UB_11      0.0044956988
_diffrn_orient_matrix_UB_12      0.0261783467
_diffrn_orient_matrix_UB_13      -0.0027087955
_diffrn_orient_matrix_UB_21      0.0247097109
_diffrn_orient_matrix_UB_22      0.0009000585
_diffrn_orient_matrix_UB_23      0.0741025738
_diffrn_orient_matrix_UB_31      0.1004688714
_diffrn_orient_matrix_UB_32      -0.0013827338
_diffrn_orient_matrix_UB_33      -0.0021212011
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    4.00   56.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979  -45.0000  300.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979   77.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega  -36.00   -2.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979  133.0000  212.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega   49.00  101.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979   45.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   56.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979  -45.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979   77.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00  101.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979   45.0000  330.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega    3.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.4979 -135.0000  325.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega -104.00   -4.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -45.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega  -39.00   -6.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542   45.0000  180.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega  -75.00  -47.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  133.0000  215.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega  -44.00  -17.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542   45.0000  270.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega -101.00  -54.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -45.0000  240.0000 47

;
_diffrn_measurement_method       'ω scans'

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.766


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0320P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4814
_refine_ls_number_parameters     251
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.004
_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
Mo Mo 0.66601(2) 0.869603(7) 0.43687(2) 0.03368(7) Uani 1 1 d . . .
C1 C 1.0381(3) 0.81875(7) 0.2860(2) 0.0324(5) Uani 1 1 d . . .
C2 C 0.8511(3) 0.82728(8) 0.2061(2) 0.0348(5) Uani 1 1 d . . .
C3 C 0.8021(3) 0.81110(8) 0.0661(2) 0.0392(5) Uani 1 1 d . . .
C4 C 0.9436(3) 0.78744(9) 0.0096(3) 0.0465(6) Uani 1 1 d . . .
H4 H 0.9129 0.7767 -0.0827 0.056 Uiso 1 1 calc R . .
C5 C 1.1290(3) 0.77958(9) 0.0883(3) 0.0504(6) Uani 1 1 d . . .
H5 H 1.2224 0.7639 0.0486 0.061 Uiso 1 1 calc R . .
C6 C 1.1757(3) 0.79482(8) 0.2247(3) 0.0424(6) Uani 1 1 d . . .
H6 H 1.3006 0.7892 0.2773 0.051 Uiso 1 1 calc R . .
C7 C 1.0982(3) 0.83520(7) 0.4283(2) 0.0324(5) Uani 1 1 d . . .
H7 H 1.2279 0.8303 0.4725 0.039 Uiso 1 1 calc R . .
C8 C 0.9442(3) 0.89038(8) 0.6939(2) 0.0324(5) Uani 1 1 d . . .
C9 C 0.9936(3) 0.90657(8) 0.8400(2) 0.0325(5) Uani 1 1 d . . .
C10 C 0.8550(3) 0.92849(8) 0.9028(2) 0.0404(6) Uani 1 1 d . . .
H10 H 0.7303 0.9344 0.8503 0.049 Uiso 1 1 calc R . .
C11 C 0.8994(3) 0.94158(9) 1.0416(2) 0.0421(6) Uani 1 1 d . . .
H11 H 0.8051 0.9563 1.0823 0.051 Uiso 1 1 calc R . .
C12 C 1.0832(3) 0.93288(8) 1.1203(2) 0.0333(5) Uani 1 1 d . . .
C13 C 1.2253(3) 0.91162(8) 1.0603(2) 0.0388(5) Uani 1 1 d . . .
H13 H 1.3498 0.9059 1.1136 0.047 Uiso 1 1 calc R . .
C14 C 1.1806(3) 0.89897(9) 0.9212(2) 0.0387(5) Uani 1 1 d . . .
H14 H 1.2765 0.8851 0.8804 0.046 Uiso 1 1 calc R . .
C15 C 0.5657(4) 0.80595(10) -0.1468(3) 0.0560(7) Uani 1 1 d . . .
H15A H 0.6410 0.8244 -0.2006 0.084 Uiso 1 1 calc R . .
H15B H 0.4293 0.8120 -0.1822 0.084 Uiso 1 1 calc R . .
H15C H 0.5922 0.7713 -0.1535 0.084 Uiso 1 1 calc R . .
C16 C 0.7455(4) 0.99390(9) 0.4139(3) 0.0568(7) Uani 1 1 d . . .
H16A H 0.8617 1.0143 0.4360 0.068 Uiso 1 1 calc R . .
H16B H 0.6891 0.9926 0.4962 0.068 Uiso 1 1 calc R . .
C17 C 0.6055(4) 1.01696(10) 0.2998(3) 0.0663(8) Uani 1 1 d . . .
H17A H 0.6620 1.0195 0.2188 0.099 Uiso 1 1 calc R . .
H17B H 0.5730 1.0494 0.3277 0.099 Uiso 1 1 calc R . .
H17C H 0.4894 0.9971 0.2779 0.099 Uiso 1 1 calc R . .
O1 O 0.6015(2) 0.81379(6) 0.48836(18) 0.0504(4) Uani 1 1 d . . .
O2 O 0.45265(19) 0.90278(6) 0.39748(16) 0.0418(4) Uani 1 1 d . . .
O3 O 0.7142(2) 0.85247(6) 0.25671(16) 0.0423(4) Uani 1 1 d . . .
O4 O 0.75992(19) 0.89763(6) 0.62711(15) 0.0376(4) Uani 1 1 d . . .
O5 O 0.8010(2) 0.94440(6) 0.38128(19) 0.0436(4) Uani 1 1 d D . .
O6 O 1.1183(2) 0.94534(6) 1.25974(15) 0.0417(4) Uani 1 1 d . . .
H6A H 1.2229 0.9335 1.2998 0.062 Uiso 1 1 calc R . .
O7 O 0.6174(2) 0.82105(6) -0.00379(17) 0.0499(4) Uani 1 1 d . . .
N1 N 0.9852(2) 0.85627(6) 0.49892(19) 0.0319(4) Uani 1 1 d . . .
N2 N 1.0724(2) 0.86999(7) 0.63559(18) 0.0363(4) Uani 1 1 d . . .
H5A H 0.893(2) 0.9433(9) 0.345(2) 0.048(8) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo O1 1.6831(17) . ?
Mo O2 1.7166(14) . ?
Mo O3 1.9200(16) . ?
Mo O4 1.9891(14) . ?
Mo N1 2.2205(17) . ?
Mo O5 2.3449(17) . ?
C1 C6 1.396(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.438(3) . ?
C2 O3 1.352(2) . ?
C2 C3 1.410(3) . ?
C3 O7 1.357(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.370(3) . ?
C7 N1 1.288(3) . ?
C8 N2 1.285(3) . ?
C8 O4 1.334(2) . ?
C8 C9 1.465(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.375(3) . ?
C12 O6 1.376(2) . ?
C12 C13 1.383(3) . ?
C13 C14 1.374(3) . ?
C15 O7 1.429(3) . ?
C16 O5 1.448(3) . ?
C16 C17 1.462(3) . ?
N1 N2 1.398(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mo O2 105.06(8) . . ?
O1 Mo O3 99.70(8) . . ?
O2 Mo O3 103.48(7) . . ?
O1 Mo O4 96.80(7) . . ?
O2 Mo O4 96.44(6) . . ?
O3 Mo O4 149.71(6) . . ?
O1 Mo N1 95.23(7) . . ?
O2 Mo N1 157.82(7) . . ?
O3 Mo N1 81.38(6) . . ?
O4 Mo N1 71.94(6) . . ?
O1 Mo O5 171.89(7) . . ?
O2 Mo O5 82.63(7) . . ?
O3 Mo O5 80.67(7) . . ?
O4 Mo O5 79.52(6) . . ?
N1 Mo O5 76.78(6) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 118.10(19) . . ?
C2 C1 C7 122.67(19) . . ?
O3 C2 C1 122.21(19) . . ?
O3 C2 C3 117.74(19) . . ?
C1 C2 C3 120.0(2) . . ?
O7 C3 C4 125.2(2) . . ?
O7 C3 C2 116.1(2) . . ?
C4 C3 C2 118.8(2) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C1 120.9(2) . . ?
N1 C7 C1 124.63(19) . . ?
N2 C8 O4 122.72(19) . . ?
N2 C8 C9 121.17(18) . . ?
O4 C8 C9 116.10(18) . . ?
C10 C9 C14 118.13(19) . . ?
C10 C9 C8 121.07(18) . . ?
C14 C9 C8 120.77(19) . . ?
C11 C10 C9 120.91(19) . . ?
C10 C11 C12 120.0(2) . . ?
C11 C12 O6 117.68(19) . . ?
C11 C12 C13 120.4(2) . . ?
O6 C12 C13 121.86(18) . . ?
C14 C13 C12 119.29(19) . . ?
C13 C14 C9 121.2(2) . . ?
O5 C16 C17 113.2(2) . . ?
C2 O3 Mo 137.13(14) . . ?
C8 O4 Mo 119.89(13) . . ?
C16 O5 Mo 127.34(16) . . ?
C3 O7 C15 117.06(19) . . ?
C7 N1 N2 115.84(17) . . ?
C7 N1 Mo 128.53(14) . . ?
N2 N1 Mo 115.52(13) . . ?
C8 N2 N1 109.44(16) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066



_database_code_depnum_ccdc_archive 'CCDC 1019147'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Mo N3 O6'
_chemical_formula_weight         453.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.97920(10)
_cell_length_b                   10.3039(3)
_cell_length_c                   21.3511(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.342(4)
_cell_angle_gamma                90
_cell_volume                     871.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3057
_cell_measurement_theta_min      4.4050
_cell_measurement_theta_max      28.6570

_exptl_crystal_description       needle
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.011
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_min  0.79491
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6290
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.315
_diffrn_reflns_theta_max         28.926
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3373
_reflns_number_gt                3308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.1248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3373
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.852(2) 0.2951(6) 0.7221(3) 0.0284(16) Uani 1 1 d . . . . .
C2 C 0.8727(19) 0.1726(7) 0.6920(3) 0.0245(15) Uani 1 1 d . . . . .
C3 C 0.916(2) 0.1652(7) 0.6276(3) 0.0347(19) Uani 1 1 d . . . . .
C4 C 0.942(3) 0.2787(9) 0.5941(4) 0.059(3) Uani 1 1 d . . . . .
H4 H 0.9764 0.2745 0.5507 0.071 Uiso 1 1 calc R U . . .
C5 C 0.920(4) 0.3997(9) 0.6229(4) 0.076(4) Uani 1 1 d . . . . .
H5 H 0.9395 0.4769 0.5992 0.091 Uiso 1 1 calc R U . . .
C6 C 0.870(3) 0.4068(8) 0.6861(4) 0.053(3) Uani 1 1 d . . . . .
H6 H 0.8488 0.4893 0.7052 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8045(18) 0.3050(6) 0.7876(3) 0.0223(14) Uani 1 1 d . . . . .
H7 H 0.7418 0.3869 0.8034 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8227(14) 0.1302(6) 0.9225(3) 0.0143(12) Uani 1 1 d . . . . .
C9 C 0.7578(15) 0.1302(6) 0.9882(3) 0.0147(12) Uani 1 1 d . . . . .
C10 C 0.8337(14) 0.0210(7) 1.0266(3) 0.0145(15) Uani 1 1 d . . . . .
H10 H 0.9432 -0.0517 1.0102 0.017 Uiso 1 1 calc R U . . .
C11 C 0.7512(15) 0.0187(8) 1.0874(3) 0.0163(15) Uani 1 1 d . . . . .
H11 H 0.8005 -0.0559 1.1128 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5959(17) 0.1252(6) 1.1119(3) 0.0179(12) Uani 1 1 d . . . . .
C13 C 0.5275(15) 0.2350(6) 1.0759(3) 0.0170(13) Uani 1 1 d . . . . .
H13 H 0.4256 0.3084 1.0934 0.020 Uiso 1 1 calc R U . . .
C14 C 0.6083(17) 0.2376(6) 1.0145(3) 0.0181(13) Uani 1 1 d . . . . .
H14 H 0.5617 0.3132 0.9898 0.022 Uiso 1 1 calc R U . . .
C15 C 1.006(2) 0.0324(9) 0.5402(3) 0.048(3) Uani 1 1 d . . . . .
H15A H 1.0066 -0.0595 0.5284 0.071 Uiso 1 1 calc R U . . .
H15B H 0.8361 0.0787 0.5124 0.071 Uiso 1 1 calc R U . . .
H15C H 1.2291 0.0699 0.5360 0.071 Uiso 1 1 calc R U . . .
C16 C 0.476(3) 0.7493(8) 0.6118(4) 0.041(2) Uani 1 1 d . . . . .
C17 C 0.339(3) 0.7866(11) 0.6698(4) 0.053(3) Uani 1 1 d . . . . .
H17A H 0.1834 0.8596 0.6617 0.079 Uiso 1 1 calc R U . . .
H17B H 0.5238 0.8124 0.7009 0.079 Uiso 1 1 calc R U . . .
H17C H 0.2181 0.7129 0.6861 0.079 Uiso 1 1 calc R U . . .
N1 N 0.8424(15) 0.2091(5) 0.8265(3) 0.0160(11) Uani 1 1 d . . . . .
N2 N 0.7796(14) 0.2355(5) 0.8880(2) 0.0179(11) Uani 1 1 d . . . . .
N3 N 0.587(2) 0.7187(9) 0.5675(4) 0.060(2) Uani 1 1 d . . . . .
O1 O 0.3873(9) 0.0149(8) 0.80870(18) 0.0220(11) Uani 1 1 d . . . . .
O3 O 0.8431(12) 0.0602(4) 0.72273(19) 0.0172(9) Uani 1 1 d . . . . .
O4 O 0.9121(11) 0.0185(6) 0.89684(17) 0.0151(10) Uani 1 1 d . . . . .
O7 O 0.9270(16) 0.0444(5) 0.6038(2) 0.0375(15) Uani 1 1 d . . . . .
O6 O 0.5100(13) 0.1155(4) 1.1731(2) 0.0231(10) Uani 1 1 d . . . . .
H6A H 0.4145 0.1842 1.1829 0.035 Uiso 1 1 calc R U . . .
O2 O 0.8749(11) -0.1614(4) 0.7995(2) 0.0185(10) Uani 1 1 d . . . . .
Mo Mo 0.95627(10) 0.00136(5) 0.80672(2) 0.01208(11) Uani 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
C1 C6 1.389(10) . ?
C1 C2 1.423(9) . ?
C1 C7 1.432(9) . ?
C2 O3 1.342(8) . ?
C2 C3 1.403(9) . ?
C3 O7 1.347(9) . ?
C3 C4 1.380(11) . ?
C4 C5 1.396(12) . ?
C5 C6 1.384(11) . ?
C7 N1 1.290(8) . ?
C8 N2 1.314(8) . ?
C8 O4 1.337(8) . ?
C8 C9 1.451(9) . ?
C9 C14 1.398(9) . ?
C9 C10 1.408(9) . ?
C10 C11 1.368(8) . ?
C11 C12 1.386(10) . ?
C12 C13 1.381(8) . ?
C12 O6 1.383(7) . ?
C13 C14 1.379(9) . ?
C15 O7 1.429(8) . ?
C16 N3 1.126(11) . ?
C16 C17 1.450(12) . ?
N1 N2 1.386(7) . ?
N1 Mo 2.236(5) . ?
O1 Mo 1.717(4) 1_455 ?
O1 Mo 2.273(3) . ?
O3 Mo 1.907(4) . ?
O4 Mo 1.956(4) . ?
O2 Mo 1.713(4) . ?
Mo O1 1.717(4) 1_655 ?

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
C6 C1 C2 118.4(6) . . ?
C6 C1 C7 120.0(6) . . ?
C2 C1 C7 121.6(6) . . ?
O3 C2 C3 117.2(6) . . ?
O3 C2 C1 122.2(6) . . ?
C3 C2 C1 120.6(6) . . ?
O7 C3 C4 125.6(7) . . ?
O7 C3 C2 115.5(6) . . ?
C4 C3 C2 118.9(7) . . ?
C3 C4 C5 121.2(8) . . ?
C6 C5 C4 119.8(8) . . ?
C5 C6 C1 121.0(7) . . ?
N1 C7 C1 123.7(6) . . ?
N2 C8 O4 120.5(6) . . ?
N2 C8 C9 121.1(6) . . ?
O4 C8 C9 118.3(5) . . ?
C14 C9 C10 118.3(6) . . ?
C14 C9 C8 120.6(6) . . ?
C10 C9 C8 121.1(5) . . ?
C11 C10 C9 120.6(7) . . ?
C10 C11 C12 120.0(7) . . ?
C13 C12 O6 122.1(6) . . ?
C13 C12 C11 120.7(6) . . ?
O6 C12 C11 117.2(5) . . ?
C14 C13 C12 119.6(6) . . ?
C13 C14 C9 120.8(6) . . ?
N3 C16 C17 178.5(11) . . ?
C7 N1 N2 116.0(6) . . ?
C7 N1 Mo 128.7(5) . . ?
N2 N1 Mo 115.1(4) . . ?
C8 N2 N1 110.1(5) . . ?
Mo O1 Mo 171.5(5) 1_455 . ?
C2 O3 Mo 135.3(4) . . ?
C8 O4 Mo 122.1(4) . . ?
C3 O7 C15 117.1(6) . . ?
O2 Mo O1 105.2(3) . 1_655 ?
O2 Mo O3 101.58(19) . . ?
O1 Mo O3 98.3(2) 1_655 . ?
O2 Mo O4 98.2(2) . . ?
O1 Mo O4 98.60(18) 1_655 . ?
O3 Mo O4 149.48(19) . . ?
O2 Mo N1 156.14(19) . . ?
O1 Mo N1 97.9(3) 1_655 . ?
O3 Mo N1 80.74(18) . . ?
O4 Mo N1 71.9(2) . . ?
O2 Mo O1 83.2(3) . . ?
O1 Mo O1 171.5(5) 1_655 . ?
O3 Mo O1 81.34(18) . . ?
O4 Mo O1 78.19(16) . . ?
N1 Mo O1 73.6(3) . . ?

_refine_diff_density_max         1.315
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.088

_database_code_depnum_ccdc_archive 'CCDC 1019148'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Mo N2 O7'
_chemical_formula_weight         458.27

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'
O O 0.0106 0.0060 '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'
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   'P 1 21/c 1'

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                   6.6695(9)
_cell_length_b                   18.7911(19)
_cell_length_c                   14.411(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.799(14)
_cell_angle_gamma                90.00
_cell_volume                     1793.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3498
_cell_measurement_theta_min      4.1436
_cell_measurement_theta_max      30.4002
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_min  0.33416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_detector_area_resol_mean 16.3426

_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14235
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4298
_reflns_number_gt                2544
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4298
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
C1 C -0.0555(8) 0.4300(3) 0.6176(4) 0.0218(12) Uani 1 1 d . . .
C2 C 0.1233(9) 0.4621(3) 0.6579(4) 0.0263(14) Uani 1 1 d . . .
C3 C 0.1422(8) 0.5361(3) 0.6584(4) 0.0225(13) Uani 1 1 d . . .
H3 H 0.2645 0.5575 0.6853 0.027 Uiso 1 1 calc R . .
C4 C -0.0136(9) 0.5780(3) 0.6203(4) 0.0271(13) Uani 1 1 d . . .
C5 C -0.1933(9) 0.5481(3) 0.5803(4) 0.0312(14) Uani 1 1 d . . .
H5 H -0.3006 0.5775 0.5534 0.037 Uiso 1 1 calc R . .
C6 C -0.2145(9) 0.4755(3) 0.5798(4) 0.0271(13) Uani 1 1 d . . .
H6 H -0.3389 0.4552 0.5536 0.033 Uiso 1 1 calc R . .
C7 C -0.0839(9) 0.3546(3) 0.6122(4) 0.0252(13) Uani 1 1 d . . .
H7 H -0.2128 0.3371 0.5874 0.030 Uiso 1 1 calc R . .
C8 C 0.1523(9) 0.1968(3) 0.6559(4) 0.0229(13) Uani 1 1 d . . .
C9 C 0.1388(9) 0.1195(3) 0.6517(4) 0.0253(13) Uani 1 1 d . . .
C10 C 0.2998(9) 0.0768(3) 0.6844(4) 0.0271(13) Uani 1 1 d . . .
H10 H 0.4231 0.0984 0.7096 0.032 Uiso 1 1 calc R . .
C11 C 0.2867(10) 0.0030(3) 0.6815(4) 0.0306(14) Uani 1 1 d . . .
H11 H 0.3996 -0.0255 0.7041 0.037 Uiso 1 1 calc R . .
C12 C 0.1061(9) -0.0282(3) 0.6448(4) 0.0224(12) Uani 1 1 d . . .
C13 C -0.0576(9) 0.0129(3) 0.6109(4) 0.0273(13) Uani 1 1 d . . .
H13 H -0.1809 -0.0090 0.5862 0.033 Uiso 1 1 calc R . .
C14 C -0.0405(9) 0.0864(3) 0.6131(4) 0.0291(14) Uani 1 1 d . . .
H14 H -0.1518 0.1147 0.5880 0.035 Uiso 1 1 calc R . .
C15 C 0.1798(10) 0.6847(3) 0.6503(5) 0.0431(18) Uani 1 1 d . . .
H15A H 0.2087 0.6763 0.7177 0.065 Uiso 1 1 calc R . .
H15B H 0.1683 0.7359 0.6384 0.065 Uiso 1 1 calc R . .
H15C H 0.2896 0.6651 0.6185 0.065 Uiso 1 1 calc R . .
C16 C 0.3292(9) 0.2850(3) 0.9117(4) 0.0319(14) Uani 1 1 d . . .
H16B H 0.4046 0.2422 0.8958 0.038 Uiso 1 1 calc R . .
H16A H 0.2179 0.2693 0.9466 0.038 Uiso 1 1 calc R . .
C17 C 0.4681(10) 0.3330(3) 0.9726(4) 0.0419(17) Uani 1 1 d . . .
H17A H 0.5842 0.3455 0.9402 0.063 Uiso 1 1 calc R . .
H17B H 0.5151 0.3084 1.0311 0.063 Uiso 1 1 calc R . .
H17C H 0.3955 0.3764 0.9864 0.063 Uiso 1 1 calc R . .
O1 O 0.4346(6) 0.33392(17) 0.5753(3) 0.0258(9) Uani 1 1 d . . .
O2 O 0.6092(6) 0.33091(17) 0.7557(2) 0.0245(9) Uani 1 1 d . . .
O3 O 0.2799(6) 0.42302(18) 0.6996(3) 0.0267(9) Uani 1 1 d . . .
O4 O 0.3320(6) 0.22469(18) 0.6903(3) 0.0256(9) Uani 1 1 d . . .
O5 O 0.2455(7) 0.3198(2) 0.8268(3) 0.0333(10) Uani 1 1 d D . .
O6 O 0.0821(6) -0.10067(17) 0.6428(3) 0.0280(9) Uani 1 1 d . . .
H6A H 0.1905 -0.1202 0.6651 0.042 Uiso 1 1 calc R . .
O7 O -0.0050(6) 0.65067(19) 0.6160(3) 0.0367(11) Uani 1 1 d . . .
N1 N 0.0557(7) 0.3087(2) 0.6392(3) 0.0219(10) Uani 1 1 d . . .
N2 N -0.0009(7) 0.2367(2) 0.6296(3) 0.0254(11) Uani 1 1 d . . .
Mo Mo 0.37890(7) 0.32812(2) 0.68571(3) 0.02275(16) Uani 1 1 d . . .
H5A H 0.147(6) 0.344(3) 0.833(5) 0.06(2) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.399(8) . ?
C1 C6 1.420(7) . ?
C1 C7 1.431(7) . ?
C2 O3 1.357(6) . ?
C2 C3 1.397(7) . ?
C3 C4 1.366(7) . ?
C4 O7 1.368(6) . ?
C4 C5 1.386(8) . ?
C5 C6 1.371(7) . ?
C7 N1 1.294(7) . ?
C8 N2 1.287(7) . ?
C8 O4 1.347(6) . ?
C8 C9 1.458(7) . ?
C9 C10 1.378(8) . ?
C9 C14 1.403(8) . ?
C10 C11 1.390(7) . ?
C11 C12 1.387(8) . ?
C12 O6 1.370(6) . ?
C12 C13 1.379(7) . ?
C13 C14 1.385(7) . ?
C15 O7 1.424(7) . ?
C16 O5 1.440(7) . ?
C16 C17 1.500(8) . ?
O1 Mo 1.679(4) . ?
O2 Mo 1.735(4) . ?
O3 Mo 1.920(3) . ?
O4 Mo 1.971(3) . ?
O5 Mo 2.319(4) . ?
N1 N2 1.407(5) . ?
N1 Mo 2.211(5) . ?

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
C2 C1 C6 117.5(5) . . ?
C2 C1 C7 123.3(5) . . ?
C6 C1 C7 119.2(5) . . ?
O3 C2 C3 118.1(5) . . ?
O3 C2 C1 121.6(5) . . ?
C3 C2 C1 120.2(5) . . ?
C4 C3 C2 120.5(5) . . ?
C3 C4 O7 124.0(5) . . ?
C3 C4 C5 120.8(5) . . ?
O7 C4 C5 115.2(5) . . ?
C6 C5 C4 119.3(6) . . ?
C5 C6 C1 121.7(6) . . ?
N1 C7 C1 123.9(5) . . ?
N2 C8 O4 121.5(5) . . ?
N2 C8 C9 121.7(5) . . ?
O4 C8 C9 116.8(5) . . ?
C10 C9 C14 118.1(5) . . ?
C10 C9 C8 121.6(5) . . ?
C14 C9 C8 120.3(5) . . ?
C9 C10 C11 121.8(6) . . ?
C12 C11 C10 118.9(5) . . ?
O6 C12 C13 117.6(5) . . ?
O6 C12 C11 121.5(5) . . ?
C13 C12 C11 120.9(5) . . ?
C12 C13 C14 119.4(5) . . ?
C13 C14 C9 121.0(5) . . ?
O5 C16 C17 112.0(5) . . ?
C2 O3 Mo 135.4(3) . . ?
C8 O4 Mo 120.6(3) . . ?
C16 O5 Mo 128.7(4) . . ?
C4 O7 C15 118.1(5) . . ?
C7 N1 N2 115.9(5) . . ?
C7 N1 Mo 128.4(4) . . ?
N2 N1 Mo 115.4(3) . . ?
C8 N2 N1 109.6(5) . . ?
O1 Mo O2 105.59(18) . . ?
O1 Mo O3 98.97(16) . . ?
O2 Mo O3 101.70(16) . . ?
O1 Mo O4 98.60(16) . . ?
O2 Mo O4 98.24(15) . . ?
O3 Mo O4 148.70(17) . . ?
O1 Mo N1 92.35(17) . . ?
O2 Mo N1 160.93(17) . . ?
O3 Mo N1 81.39(15) . . ?
O4 Mo N1 72.19(15) . . ?
O1 Mo O5 170.29(17) . . ?
O2 Mo O5 84.11(17) . . ?
O3 Mo O5 78.42(15) . . ?
O4 Mo O5 79.92(15) . . ?
N1 Mo O5 78.04(16) . . ?

_diffrn_measured_fraction_theta_max 0.993
# start Validation Reply Form
_vrf_PLAT910_2                   
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 15 Report
RESPONSE: The beamstop is fixed and this area can not be smaller.
;
# end Validation Reply Form
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.161
_refine_diff_density_min         -1.689
_refine_diff_density_rms         0.146
_database_code_depnum_ccdc_archive 'CCDC 1019149'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Mo2 N4 O12'
_chemical_formula_sum            'C30 H24 Mo2 N4 O12'
_chemical_formula_weight         824.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic



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

_cell_length_a                   9.2163(3)
_cell_length_b                   9.9981(4)
_cell_length_c                   10.1284(3)
_cell_angle_alpha                63.594(4)
_cell_angle_beta                 65.191(3)
_cell_angle_gamma                89.389(3)
_cell_volume                     740.79(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6832
_cell_measurement_theta_min      4.0776
_cell_measurement_theta_max      29.1482


_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red almost black'
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.023
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_min  0.93683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9618
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3193
_reflns_number_gt                3001
_reflns_threshold_expression     >2σ(I)
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0284P)²+0.2405P] 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         3193
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0515
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O3 O 0.29341(17) 0.63873(16) 0.27436(16) 0.0216(3) Uani 1 1 d . . .
C14 C 0.1432(2) 0.0763(2) 1.0298(2) 0.0197(4) Uani 1 1 d . . .
C13 C 0.0756(3) -0.0259(2) 1.1976(3) 0.0220(4) Uani 1 1 d . . .
C12 C -0.0668(3) -0.0093(2) 1.3079(2) 0.0211(4) Uani 1 1 d . . .
C11 C -0.1393(3) 0.1105(3) 1.2500(3) 0.0287(5) Uani 1 1 d . . .
O5 O 0.43167(19) 0.83935(18) -0.04869(18) 0.0308(4) Uani 1 1 d . . .
C2 C 0.4363(2) 0.6221(2) 0.1733(2) 0.0179(4) Uani 1 1 d . . .
C3 C 0.5094(2) 0.7259(2) 0.0016(2) 0.0219(4) Uani 1 1 d . . .
N1 N 0.31642(19) 0.40370(18) 0.52624(19) 0.0160(3) Uani 1 1 d . . .
C7 C 0.4419(2) 0.3961(2) 0.4096(2) 0.0181(4) Uani 1 1 d . . .
C1 C 0.5094(2) 0.5028(2) 0.2356(2) 0.0184(4) Uani 1 1 d . . .
C6 C 0.6549(3) 0.4852(3) 0.1265(3) 0.0236(4) Uani 1 1 d . . .
C4 C 0.6525(3) 0.7046(3) -0.1031(3) 0.0242(4) Uani 1 1 d . . .
C5 C 0.7244(3) 0.5849(3) -0.0415(3) 0.0266(5) Uani 1 1 d . . .
C15 C 0.5132(3) 0.9524(3) -0.2209(3) 0.0440(7) Uani 1 1 d . . .
H15A H 0.6210 1.0013 -0.2484 0.066 Uiso 1 1 calc R . .
H15B H 0.4478 1.0297 -0.2429 0.066 Uiso 1 1 calc R . .
H15C H 0.5267 0.9035 -0.2892 0.066 Uiso 1 1 calc R . .
Mo Mo 0.160641(19) 0.571853(18) 0.504271(19) 0.01553(6) Uani 1 1 d . . .
O2 O -0.02478(16) 0.62299(15) 0.51106(16) 0.0182(3) Uani 1 1 d . . .
O4 O 0.06348(16) 0.41205(15) 0.73937(16) 0.0191(3) Uani 1 1 d . . .
O6 O -0.1421(2) -0.10995(17) 1.47471(17) 0.0289(4) Uani 1 1 d . . .
H6A H -0.1000 -0.1870 1.4933 0.043 Uiso 1 1 calc R . .
O1 O 0.25474(18) 0.70171(16) 0.52239(18) 0.0253(3) Uani 1 1 d . . .
C8 C 0.1410(2) 0.3016(2) 0.7908(2) 0.0170(4) Uani 1 1 d . . .
N2 N 0.2735(2) 0.28718(18) 0.68668(19) 0.0181(3) Uani 1 1 d . . .
C9 C 0.0700(2) 0.1961(2) 0.9695(2) 0.0177(4) Uani 1 1 d . . .
C10 C -0.0721(3) 0.2122(2) 1.0809(3) 0.0260(5) Uani 1 1 d . . .
H13 H 0.131(3) -0.107(3) 1.229(3) 0.018(5) Uiso 1 1 d . . .
H14 H 0.237(3) 0.073(3) 0.953(3) 0.023(6) Uiso 1 1 d . . .
H6 H 0.699(3) 0.407(3) 0.172(3) 0.020(6) Uiso 1 1 d . . .
H7 H 0.494(3) 0.312(3) 0.447(3) 0.019(6) Uiso 1 1 d . . .
H10 H -0.124(3) 0.294(3) 1.041(3) 0.027(6) Uiso 1 1 d . . .
H5 H 0.818(3) 0.573(3) -0.112(3) 0.031(7) Uiso 1 1 d . . .
H11 H -0.233(3) 0.116(3) 1.321(3) 0.031(7) Uiso 1 1 d . . .
H4 H 0.698(3) 0.767(3) -0.209(3) 0.036(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.351(2) . ?
O3 Mo 1.8995(13) . ?
C14 C13 1.379(3) . ?
C14 C9 1.393(3) . ?
C13 C12 1.389(3) . ?
C12 O6 1.367(2) . ?
C12 C11 1.383(3) . ?
C11 C10 1.388(3) . ?
O5 C3 1.354(3) . ?
O5 C15 1.431(3) . ?
C2 C1 1.395(3) . ?
C2 C3 1.408(3) . ?
C3 C4 1.390(3) . ?
N1 C7 1.292(2) . ?
N1 N2 1.393(2) . ?
N1 Mo 2.1957(15) . ?
C7 C1 1.433(3) . ?
C1 C6 1.405(3) . ?
C6 C5 1.374(3) . ?
C4 C5 1.388(3) . ?
Mo O1 1.6855(15) . ?
Mo O2 1.7608(13) . ?
Mo O4 1.9703(13) . ?
Mo O2 2.4231(14) 2_566 ?
O2 Mo 2.4231(14) 2_566 ?
O4 C8 1.336(2) . ?
C8 N2 1.294(3) . ?
C8 C9 1.463(3) . ?
C9 C10 1.390(3) . ?

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
C2 O3 Mo 139.33(12) . . ?
C13 C14 C9 120.70(19) . . ?
C14 C13 C12 119.75(19) . . ?
O6 C12 C11 117.56(19) . . ?
O6 C12 C13 122.28(18) . . ?
C11 C12 C13 120.15(19) . . ?
C12 C11 C10 120.0(2) . . ?
C3 O5 C15 116.34(17) . . ?
O3 C2 C1 121.25(17) . . ?
O3 C2 C3 118.72(18) . . ?
C1 C2 C3 120.02(18) . . ?
O5 C3 C4 124.96(19) . . ?
O5 C3 C2 116.38(18) . . ?
C4 C3 C2 118.7(2) . . ?
C7 N1 N2 115.01(16) . . ?
C7 N1 Mo 128.73(13) . . ?
N2 N1 Mo 116.25(11) . . ?
N1 C7 C1 125.24(18) . . ?
C2 C1 C6 119.89(19) . . ?
C2 C1 C7 122.21(18) . . ?
C6 C1 C7 117.90(19) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C4 C3 121.4(2) . . ?
C6 C5 C4 120.0(2) . . ?
O1 Mo O2 106.64(7) . . ?
O1 Mo O3 99.31(7) . . ?
O2 Mo O3 102.41(6) . . ?
O1 Mo O4 96.90(6) . . ?
O2 Mo O4 95.61(6) . . ?
O3 Mo O4 151.09(6) . . ?
O1 Mo N1 101.06(6) . . ?
O2 Mo N1 150.90(6) . . ?
O3 Mo N1 81.43(6) . . ?
O4 Mo N1 72.04(6) . . ?
O1 Mo O2 177.62(6) . 2_566 ?
O2 Mo O2 74.47(6) . 2_566 ?
O3 Mo O2 82.42(6) . 2_566 ?
O4 Mo O2 80.86(5) . 2_566 ?
N1 Mo O2 77.54(5) . 2_566 ?
Mo O2 Mo 105.53(6) . 2_566 ?
C8 O4 Mo 120.64(12) . . ?
N2 C8 O4 121.47(17) . . ?
N2 C8 C9 120.91(17) . . ?
O4 C8 C9 117.62(17) . . ?
C8 N2 N1 109.22(15) . . ?
C10 C9 C14 119.15(18) . . ?
C10 C9 C8 120.72(18) . . ?
C14 C9 C8 120.11(18) . . ?
C11 C10 C9 120.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.069
# start Validation Reply Form
_vrf_PLAT910_1b                  
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) .....         13 Report
RESPONSE: The beamstop is fixed and this area can not be smaller.
;
# end Validation Reply Form


_database_code_depnum_ccdc_archive 'CCDC 1019150'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Mo N2 O6'
_chemical_formula_weight         428.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic


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

_cell_length_a                   6.92430(10)
_cell_length_b                   7.5678(2)
_cell_length_c                   15.8992(4)
_cell_angle_alpha                95.560(2)
_cell_angle_beta                 90.676(2)
_cell_angle_gamma                100.214(2)
_cell_volume                     815.73(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17950
_cell_measurement_theta_min      3.8227
_cell_measurement_theta_max      33.0859


_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_min  0.96512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25526
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         29.00
_reflns_number_total             4316
_reflns_number_gt                3928
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'



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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4316
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
Mo Mo 0.570579(17) 0.846012(17) 0.700380(8) 0.01586(5) Uani 1 1 d . . .
C1 C 0.9814(2) 0.8218(2) 0.57257(10) 0.0174(3) Uani 1 1 d . . .
C2 C 0.7932(2) 0.7236(2) 0.54770(10) 0.0182(3) Uani 1 1 d . . .
C3 C 0.7615(3) 0.6319(2) 0.46733(11) 0.0234(3) Uani 1 1 d . . .
C4 C 0.9151(3) 0.6354(2) 0.41196(11) 0.0256(4) Uani 1 1 d . . .
C5 C 1.1015(3) 0.7291(2) 0.43560(11) 0.0241(3) Uani 1 1 d . . .
C6 C 1.1331(2) 0.8223(2) 0.51560(11) 0.0209(3) Uani 1 1 d . . .
C7 C 1.0239(2) 0.9240(2) 0.65404(10) 0.0174(3) Uani 1 1 d . . .
C8 C 0.8216(2) 1.0513(2) 0.83652(10) 0.0173(3) Uani 1 1 d . . .
C9 C 0.8542(2) 1.1460(2) 0.92215(10) 0.0177(3) Uani 1 1 d . . .
C10 C 0.6969(2) 1.1556(2) 0.97487(11) 0.0202(3) Uani 1 1 d . . .
C11 C 0.7266(2) 1.2298(2) 1.05826(11) 0.0204(3) Uani 1 1 d . . .
C12 C 0.9166(2) 1.2959(2) 1.08913(10) 0.0180(3) Uani 1 1 d . . .
C13 C 1.0759(2) 1.2931(2) 1.03624(11) 0.0220(3) Uani 1 1 d . . .
C14 C 1.0442(2) 1.2172(2) 0.95363(11) 0.0218(3) Uani 1 1 d . . .
C15 C 0.6017(3) 0.4270(2) 0.74939(12) 0.0217(3) Uani 1 1 d . . .
C16 C 0.4528(3) 0.3666(2) 0.81339(13) 0.0296(4) Uani 1 1 d . . .
H16A H 0.5145 0.3906 0.8701 0.044 Uiso 1 1 calc R . .
H16B H 0.4031 0.2370 0.8013 0.044 Uiso 1 1 calc R . .
H16C H 0.3438 0.4328 0.8106 0.044 Uiso 1 1 calc R . .
O1 O 0.52153(18) 1.02800(16) 0.65570(8) 0.0243(3) Uani 1 1 d . . .
O2 O 0.34398(16) 0.72704(16) 0.72350(7) 0.0203(2) Uani 1 1 d . . .
O3 O 0.64170(16) 0.71043(16) 0.60127(8) 0.0221(2) Uani 1 1 d . . .
O4 O 0.63810(16) 0.96854(15) 0.81582(7) 0.0192(2) Uani 1 1 d . . .
O5 O 0.68042(17) 0.61797(16) 0.76579(8) 0.0222(2) Uani 1 1 d D . .
O6 O 0.95508(17) 1.36679(17) 1.17154(7) 0.0209(2) Uani 1 1 d . . .
H6A H 0.8540 1.3409 1.1998 0.031 Uiso 1 1 calc R . .
N1 N 0.89491(19) 0.94182(17) 0.71033(8) 0.0164(3) Uani 1 1 d . . .
N2 N 0.96573(19) 1.04483(18) 0.78581(9) 0.0189(3) Uani 1 1 d . . .
H3 H 0.640(3) 0.564(3) 0.4481(15) 0.032(6) Uiso 1 1 d . . .
H4 H 0.898(4) 0.582(3) 0.3582(16) 0.041(7) Uiso 1 1 d . . .
H5 H 1.207(3) 0.734(3) 0.3988(14) 0.024(5) Uiso 1 1 d . . .
H6 H 1.262(3) 0.882(3) 0.5309(14) 0.029(6) Uiso 1 1 d . . .
H7 H 1.151(3) 0.982(2) 0.6640(12) 0.016(5) Uiso 1 1 d . . .
H10 H 0.568(4) 1.111(3) 0.9560(16) 0.037(6) Uiso 1 1 d . . .
H11 H 0.620(4) 1.228(3) 1.0968(16) 0.039(6) Uiso 1 1 d . . .
H13 H 1.206(3) 1.338(3) 1.0620(13) 0.022(5) Uiso 1 1 d . . .
H14 H 1.142(3) 1.209(3) 0.9219(14) 0.031(6) Uiso 1 1 d . . .
H15A H 0.543(3) 0.411(3) 0.6944(14) 0.029(6) Uiso 1 1 d . . .
H15B H 0.700(3) 0.370(3) 0.7514(13) 0.021(5) Uiso 1 1 d . . .
H51 H 0.7941(16) 0.636(3) 0.7811(12) 0.016(5) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo O1 1.6931(13) . ?
Mo O2 1.7275(11) . ?
Mo O3 1.9137(12) . ?
Mo O4 1.9857(11) . ?
Mo N1 2.2329(13) . ?
Mo O5 2.3309(12) . ?
C1 C6 1.395(2) . ?
C1 C2 1.412(2) . ?
C1 C7 1.442(2) . ?
C2 O3 1.3549(19) . ?
C2 C3 1.389(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.386(3) . ?
C5 C6 1.389(2) . ?
C7 N1 1.286(2) . ?
C8 N2 1.295(2) . ?
C8 O4 1.3354(18) . ?
C8 C9 1.471(2) . ?
C9 C10 1.390(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.388(2) . ?
C12 O6 1.3712(19) . ?
C12 C13 1.397(2) . ?
C13 C14 1.381(2) . ?
C15 O5 1.4482(19) . ?
C15 C16 1.501(2) . ?
N1 N2 1.3991(18) . ?

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 Mo O2 105.10(6) . . ?
O1 Mo O3 98.98(6) . . ?
O2 Mo O3 103.42(5) . . ?
O1 Mo O4 97.07(6) . . ?
O2 Mo O4 96.73(5) . . ?
O3 Mo O4 149.88(5) . . ?
O1 Mo N1 95.05(5) . . ?
O2 Mo N1 158.01(6) . . ?
O3 Mo N1 81.59(5) . . ?
O4 Mo N1 71.72(5) . . ?
O1 Mo O5 172.28(5) . . ?
O2 Mo O5 82.12(5) . . ?
O3 Mo O5 81.70(5) . . ?
O4 Mo O5 79.12(5) . . ?
N1 Mo O5 77.40(5) . . ?
C6 C1 C2 118.78(15) . . ?
C6 C1 C7 118.21(14) . . ?
C2 C1 C7 123.00(14) . . ?
O3 C2 C3 118.25(14) . . ?
O3 C2 C1 121.80(14) . . ?
C3 C2 C1 119.92(15) . . ?
C4 C3 C2 119.97(16) . . ?
C5 C4 C3 120.97(16) . . ?
C4 C5 C6 119.18(16) . . ?
C5 C6 C1 121.18(16) . . ?
N1 C7 C1 124.20(14) . . ?
N2 C8 O4 122.56(14) . . ?
N2 C8 C9 121.10(14) . . ?
O4 C8 C9 116.30(14) . . ?
C10 C9 C14 118.98(15) . . ?
C10 C9 C8 120.27(14) . . ?
C14 C9 C8 120.62(15) . . ?
C11 C10 C9 121.05(15) . . ?
C10 C11 C12 119.23(15) . . ?
O6 C12 C11 121.78(14) . . ?
O6 C12 C13 117.72(14) . . ?
C11 C12 C13 120.49(15) . . ?
C14 C13 C12 119.56(15) . . ?
C13 C14 C9 120.63(15) . . ?
O5 C15 C16 111.12(14) . . ?
C2 O3 Mo 136.91(10) . . ?
C8 O4 Mo 120.55(10) . . ?
C15 O5 Mo 125.21(10) . . ?
C7 N1 N2 115.57(13) . . ?
C7 N1 Mo 128.60(11) . . ?
N2 N1 Mo 115.68(9) . . ?
C8 N2 N1 109.11(12) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.083

_database_code_depnum_ccdc_archive 'CCDC 1019151'
