# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_np230_0m
_database_code_depnum_ccdc_archive 'CCDC 1400488'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 Mo N4 O5'
_chemical_formula_sum            'C17 H18 Mo N4 O5'
_chemical_formula_weight         456.03

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

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

_cell_length_a                   9.2570(15)
_cell_length_b                   9.9830(16)
_cell_length_c                   10.7891(17)
_cell_angle_alpha                114.336(2)
_cell_angle_beta                 90.211(2)
_cell_angle_gamma                91.610(2)
_cell_volume                     908.0(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.66
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             567
_exptl_absorpt_coefficient_mu    1.46
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9264
_exptl_absorpt_correction_T_max  0.9466
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4263
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2914
_reflns_number_gt                2825
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0634P)²+0.8518P] 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         2914
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.81561(3) 0.39259(3) 0.65587(3) 0.02498(14) Uani 1 1 d . . .
O1 O 0.9644(3) 0.3051(3) 0.4649(3) 0.0363(6) Uani 1 1 d . . .
O5 O 0.8640(3) 0.5618(3) 0.6611(3) 0.0367(6) Uani 1 1 d . . .
O4 O 0.7118(3) 0.4250(3) 0.7924(3) 0.0438(7) Uani 1 1 d . . .
O3 O 0.9910(3) 0.3619(3) 0.7380(3) 0.0343(6) Uani 1 1 d . . .
O2 O 0.6652(3) 0.3426(3) 0.5183(3) 0.0367(6) Uani 1 1 d . . .
O6 O 0.3524(3) 0.3537(3) 0.6845(3) 0.0526(8) Uani 1 1 d . . .
N3 N 0.8555(3) -0.0762(3) 0.5654(3) 0.0299(6) Uani 1 1 d . . .
C1 C 0.9776(3) 0.1294(4) 0.7522(3) 0.0268(7) Uani 1 1 d . . .
N2 N 0.7548(3) -0.0843(3) 0.4702(3) 0.0301(7) Uani 1 1 d . . .
N4 N 0.3076(3) 0.5906(3) 0.8147(3) 0.0350(7) Uani 1 1 d . . .
N1 N 0.8029(3) 0.1479(3) 0.5841(3) 0.0249(6) Uani 1 1 d . . .
C13 C 0.4788(4) 0.2604(5) 0.3553(4) 0.0391(9) Uani 1 1 d . . .
H13 H 0.4582 0.3575 0.3744 0.047 Uiso 1 1 calc R . .
C6 C 1.0243(3) 0.2761(4) 0.8027(4) 0.0283(7) Uani 1 1 d . . .
C2 C 1.0233(4) 0.0430(4) 0.8198(4) 0.0359(8) Uani 1 1 d . . .
H2 H 0.9918 -0.0549 0.7884 0.043 Uiso 1 1 calc R . .
C7 C 0.8813(3) 0.0667(3) 0.6342(3) 0.0245(7) Uani 1 1 d . . .
C5 C 1.1125(4) 0.3360(4) 0.9174(4) 0.0348(8) Uani 1 1 d . . .
H5 H 1.1417 0.4347 0.9516 0.042 Uiso 1 1 calc R . .
C8 C 0.7229(3) 0.0490(3) 0.4810(3) 0.0262(7) Uani 1 1 d . . .
C9 C 0.6169(4) 0.0831(4) 0.4003(4) 0.0294(7) Uani 1 1 d . . .
C12 C 0.4008(4) 0.1478(5) 0.2568(5) 0.0465(10) Uani 1 1 d . . .
H12 H 0.3274 0.1696 0.2096 0.056 Uiso 1 1 calc R . .
C14 C 0.5892(4) 0.2291(4) 0.4269(4) 0.0298(7) Uani 1 1 d . . .
C16 C 0.4144(5) 0.6057(5) 0.9171(5) 0.0507(11) Uani 1 1 d . . .
H16A H 0.4132 0.7034 0.9879 0.076 Uiso 1 1 calc R . .
H16B H 0.5082 0.5882 0.8770 0.076 Uiso 1 1 calc R . .
H16C H 0.3929 0.5356 0.9548 0.076 Uiso 1 1 calc R . .
C3 C 1.1141(5) 0.1027(4) 0.9318(4) 0.0421(9) Uani 1 1 d . . .
H3 H 1.1463 0.0443 0.9740 0.051 Uiso 1 1 calc R . .
C10 C 0.5357(4) -0.0301(4) 0.2983(4) 0.0418(9) Uani 1 1 d . . .
H10 H 0.5538 -0.1278 0.2791 0.050 Uiso 1 1 calc R . .
C4 C 1.1576(4) 0.2488(4) 0.9816(4) 0.0396(9) Uani 1 1 d . . .
H4 H 1.2174 0.2892 1.0584 0.048 Uiso 1 1 calc R . .
C15 C 0.2876(4) 0.4661(5) 0.7069(4) 0.0413(9) Uani 1 1 d . . .
C11 C 0.4291(5) 0.0031(5) 0.2263(5) 0.0487(11) Uani 1 1 d . . .
H11 H 0.3767 -0.0720 0.1576 0.058 Uiso 1 1 calc R . .
C17 C 0.2184(5) 0.7169(5) 0.8391(6) 0.0595(12) Uani 1 1 d . . .
H17A H 0.2488 0.7969 0.9227 0.089 Uiso 1 1 calc R . .
H17B H 0.1190 0.6906 0.8453 0.089 Uiso 1 1 calc R . .
H17C H 0.2287 0.7465 0.7654 0.089 Uiso 1 1 calc R . .
H20A H 1.020(5) 0.231(6) 0.454(5) 0.055(14) Uiso 1 1 d . . .
H20B H 1.013(6) 0.337(6) 0.420(6) 0.061(16) Uiso 1 1 d . . .
H25 H 0.215(6) 0.475(5) 0.646(5) 0.058(14) Uiso 1 1 d . . .
H27 H 0.714(5) -0.161(5) 0.428(5) 0.043(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 O4 1.683(3) . ?
Mo1 O5 1.714(2) . ?
Mo1 O2 1.931(2) . ?
Mo1 O3 1.938(2) . ?
Mo1 N1 2.237(3) . ?
Mo1 O1 2.348(3) . ?
O3 C6 1.350(4) . ?
O2 C14 1.334(4) . ?
O6 C15 1.222(6) . ?
N3 C7 1.323(4) . ?
N3 N2 1.360(4) . ?
C1 C6 1.390(5) . ?
C1 C2 1.411(5) . ?
C1 C7 1.453(5) . ?
N2 C8 1.329(4) . ?
N4 C15 1.314(5) . ?
N4 C16 1.437(5) . ?
N4 C17 1.459(5) . ?
N1 C8 1.344(4) . ?
N1 C7 1.366(4) . ?
C13 C12 1.370(6) . ?
C13 C14 1.397(5) . ?
C6 C5 1.383(5) . ?
C2 C3 1.376(6) . ?
C5 C4 1.388(5) . ?
C8 C9 1.447(5) . ?
C9 C14 1.396(5) . ?
C9 C10 1.405(5) . ?
C12 C11 1.377(6) . ?
C3 C4 1.378(6) . ?
C10 C11 1.383(6) . ?

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
O4 Mo1 O5 105.97(13) . . ?
O4 Mo1 O2 98.99(13) . . ?
O5 Mo1 O2 97.49(11) . . ?
O4 Mo1 O3 95.55(13) . . ?
O5 Mo1 O3 97.34(11) . . ?
O2 Mo1 O3 155.49(11) . . ?
O4 Mo1 N1 94.56(12) . . ?
O5 Mo1 N1 159.46(12) . . ?
O2 Mo1 N1 79.64(10) . . ?
O3 Mo1 N1 79.62(10) . . ?
O4 Mo1 O1 169.68(12) . . ?
O5 Mo1 O1 83.90(11) . . ?
O2 Mo1 O1 82.39(11) . . ?
O3 Mo1 O1 79.90(11) . . ?
N1 Mo1 O1 75.56(10) . . ?
C6 O3 Mo1 134.1(2) . . ?
C14 O2 Mo1 142.7(2) . . ?
C7 N3 N2 103.8(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 121.0(3) . . ?
C2 C1 C7 120.5(3) . . ?
C8 N2 N3 111.0(3) . . ?
C15 N4 C16 121.2(4) . . ?
C15 N4 C17 121.7(4) . . ?
C16 N4 C17 117.1(3) . . ?
C8 N1 C7 105.2(3) . . ?
C8 N1 Mo1 128.4(2) . . ?
C7 N1 Mo1 126.3(2) . . ?
C12 C13 C14 120.0(4) . . ?
O3 C6 C5 118.1(3) . . ?
O3 C6 C1 121.2(3) . . ?
C5 C6 C1 120.6(3) . . ?
C3 C2 C1 120.4(3) . . ?
N3 C7 N1 112.0(3) . . ?
N3 C7 C1 123.8(3) . . ?
N1 C7 C1 124.2(3) . . ?
C6 C5 C4 120.0(3) . . ?
N2 C8 N1 107.9(3) . . ?
N2 C8 C9 126.4(3) . . ?
N1 C8 C9 125.7(3) . . ?
C14 C9 C10 119.1(3) . . ?
C14 C9 C8 120.4(3) . . ?
C10 C9 C8 120.4(3) . . ?
C13 C12 C11 121.2(4) . . ?
O2 C14 C9 122.8(3) . . ?
O2 C14 C13 117.5(3) . . ?
C9 C14 C13 119.7(3) . . ?
C2 C3 C4 120.3(4) . . ?
C11 C10 C9 120.3(4) . . ?
C3 C4 C5 120.2(4) . . ?
O6 C15 N4 125.0(4) . . ?
C12 C11 C10 119.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.910
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.152
