# 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 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_7
_database_code_depnum_ccdc_archive 'CCDC 1416908'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT410_I                   
;
PROBLEM: Short Intra H...H Contact  H12A   ..  H13X    ..       1.60 Ang.  
         Short Intra H...H Contact  H14A   ..  H13X    ..       1.71 Ang.    
RESPONSE: The structure contains disorder of allyl moiety. The short contacts are
between H atom from disordered CH fragment and CH2 of the allyls.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Mo O4'
_chemical_formula_sum            'C16 H14 Mo O4'
_chemical_formula_weight         366.21

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'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.8969(2)
_cell_length_b                   9.4631(3)
_cell_length_c                   9.9920(3)
_cell_angle_alpha                74.851(3)
_cell_angle_beta                 89.546(3)
_cell_angle_gamma                84.8030(19)
_cell_volume                     717.69(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    14028
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.926
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.056
1 1 0 0.137
-1 1 0 0.142
1 -1 0 0.077
0 0 -1 0.105
0 0 1 0.175


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            13930
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         2.112
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3264
_reflns_number_gt                3125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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     
'w=1/[σ²(Fo²)+(0.0249P)²+0.4603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3264
_refine_ls_number_parameters     199
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.121
_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
Mo1 Mo 0.25221(2) 0.73065(2) 0.16345(2) 0.01783(6) Uani 1 1 d . . . . .
O2 O 0.35506(19) 0.83653(17) 0.49637(14) 0.0339(3) Uani 1 1 d . . . . .
C10 C 0.2950(2) 0.7082(2) 0.49603(19) 0.0279(4) Uani 1 1 d . . . . .
C15 C 0.3094(2) 0.8831(2) 0.00115(19) 0.0285(4) Uani 1 1 d . . . . .
C2 C 0.3373(2) 0.51561(19) 0.35205(18) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.1388(3) 0.9017(2) 0.2092(2) 0.0296(4) Uani 1 1 d . . . . .
O3 O 0.3433(2) 0.97542(18) -0.09276(16) 0.0442(4) Uani 1 1 d . . . . .
O4 O 0.0730(2) 1.00202(17) 0.23997(18) 0.0458(4) Uani 1 1 d . . . . .
O1 O 0.1931(2) 0.64873(19) 0.57592(16) 0.0401(3) Uani 1 1 d . . . . .
C4 C 0.5354(2) 0.6278(2) 0.19737(19) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.6089 0.6494 0.1231 0.031 Uiso 1 1 d R U . . .
C6 C 0.2248(3) 0.4073(2) 0.4089(2) 0.0311(4) Uani 1 1 d . . . . .
H6 H 0.1569 0.4144 0.4837 0.037 Uiso 1 1 d R U . . .
C5 C 0.4994(2) 0.7149(2) 0.29094(18) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.5514 0.7985 0.2936 0.030 Uiso 1 1 d R U . . .
C1 C 0.3713(2) 0.6510(2) 0.38332(17) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.4306(3) 0.3797(2) 0.1807(2) 0.0316(4) Uani 1 1 d . . . . .
H9 H 0.4985 0.3693 0.1068 0.038 Uiso 1 1 d R U . . .
C3 C 0.4396(2) 0.5022(2) 0.23614(19) 0.0248(3) Uani 1 1 d . . . . .
C7 C 0.2194(3) 0.2918(2) 0.3517(2) 0.0381(5) Uani 1 1 d . . . . .
H7 H 0.1453 0.2208 0.3883 0.046 Uiso 1 1 d R U . . .
C14 C 0.1274(3) 0.6700(3) -0.0229(2) 0.0384(5) Uani 1 1 d D . . . .
H14A H 0.1251 0.7713 -0.0587 0.046 Uiso 1 1 d R U . A 1
H14B H 0.1829 0.6073 -0.0703 0.046 Uiso 1 1 d R U . C .
C8 C 0.3224(3) 0.2769(2) 0.2386(3) 0.0382(5) Uani 1 1 d . . . . .
H8 H 0.3155 0.1960 0.2030 0.046 Uiso 1 1 d R U . . .
C12 C -0.0348(3) 0.6914(3) 0.1798(3) 0.0410(5) Uani 1 1 d D . . . .
H12A H -0.0448 0.7936 0.1535 0.049 Uiso 1 1 d R U . B 1
H12B H -0.0835 0.6415 0.2617 0.049 Uiso 1 1 d R U . C .
C11 C 0.2801(3) 0.9074(3) 0.5965(2) 0.0442(5) Uani 1 1 d . . . . .
H11A H 0.1608 0.9329 0.5770 0.053 Uiso 1 1 d R U . . .
H11B H 0.3350 0.9949 0.5923 0.053 Uiso 1 1 d R U . . .
H11C H 0.2959 0.8418 0.6876 0.053 Uiso 1 1 d R U . . .
C13 C 0.0520(3) 0.6140(3) 0.0970(3) 0.0288(6) Uani 0.7 1 d D . P C 1
H13 H 0.0569 0.5121 0.1275 0.035 Uiso 0.7 1 d R U P C 1
C13X C -0.0004(7) 0.7199(7) 0.0522(6) 0.0260(12) Uani 0.3 1 d D . P C 2
H13X H -0.0786 0.7900 -0.0029 0.031 Uiso 0.3 1 calc R U P C 2


_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 C16 1.936(2) . ?
Mo1 C15 1.9490(19) . ?
Mo1 C13 2.208(2) . ?
Mo1 C1 2.3061(16) . ?
Mo1 C5 2.3117(17) . ?
Mo1 C13X 2.314(5) . ?
Mo1 C12 2.328(2) . ?
Mo1 C14 2.336(2) . ?
Mo1 C4 2.3468(18) . ?
Mo1 C2 2.4313(17) . ?
Mo1 C3 2.4509(18) . ?
O2 C10 1.344(2) . ?
O2 C11 1.439(2) . ?
C10 O1 1.199(2) . ?
C10 C1 1.474(3) . ?
C15 O3 1.151(2) . ?
C2 C6 1.420(3) . ?
C2 C3 1.433(3) . ?
C2 C1 1.444(2) . ?
C16 O4 1.151(3) . ?
C4 C5 1.411(3) . ?
C4 C3 1.433(3) . ?
C4 H4 0.9300 . ?
C6 C7 1.363(3) . ?
C6 H6 0.9300 . ?
C5 C1 1.430(2) . ?
C5 H5 0.9299 . ?
C9 C8 1.364(3) . ?
C9 C3 1.416(3) . ?
C9 H9 0.9299 . ?
C7 C8 1.417(3) . ?
C7 H7 0.9300 . ?
C14 C13 1.336(4) . ?
C14 C13X 1.376(7) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C8 H8 0.9300 . ?
C12 C13X 1.265(6) . ?
C12 C13 1.381(4) . ?
C12 H12A 0.9299 . ?
C12 H12B 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13 0.9300 . ?
C13X H13X 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
C16 Mo1 C15 80.29(8) . . ?
C16 Mo1 C13 106.72(10) . . ?
C15 Mo1 C13 106.84(9) . . ?
C16 Mo1 C1 90.40(7) . . ?
C15 Mo1 C1 131.69(7) . . ?
C13 Mo1 C1 121.17(9) . . ?
C16 Mo1 C5 97.56(7) . . ?
C15 Mo1 C5 97.99(7) . . ?
C13 Mo1 C5 147.61(9) . . ?
C1 Mo1 C5 36.09(6) . . ?
C16 Mo1 C13X 85.54(17) . . ?
C15 Mo1 C13X 88.28(15) . . ?
C1 Mo1 C13X 138.48(15) . . ?
C5 Mo1 C13X 173.38(15) . . ?
C16 Mo1 C12 74.32(9) . . ?
C15 Mo1 C12 114.59(9) . . ?
C13 Mo1 C12 35.34(10) . . ?
C1 Mo1 C12 107.93(8) . . ?
C5 Mo1 C12 143.89(8) . . ?
C13X Mo1 C12 31.63(16) . . ?
C16 Mo1 C14 114.05(8) . . ?
C15 Mo1 C14 75.48(8) . . ?
C13 Mo1 C14 34.05(10) . . ?
C1 Mo1 C14 147.83(8) . . ?
C5 Mo1 C14 145.60(7) . . ?
C13X Mo1 C14 34.42(16) . . ?
C12 Mo1 C14 62.85(8) . . ?
C16 Mo1 C4 131.04(7) . . ?
C15 Mo1 C4 92.23(8) . . ?
C13 Mo1 C4 121.61(9) . . ?
C1 Mo1 C4 59.32(6) . . ?
C5 Mo1 C4 35.25(6) . . ?
C13X Mo1 C4 142.96(16) . . ?
C12 Mo1 C4 147.46(8) . . ?
C14 Mo1 C4 110.48(7) . . ?
C16 Mo1 C2 118.22(7) . . ?
C15 Mo1 C2 150.21(7) . . ?
C13 Mo1 C2 90.64(8) . . ?
C1 Mo1 C2 35.36(6) . . ?
C5 Mo1 C2 58.57(6) . . ?
C13X Mo1 C2 114.81(15) . . ?
C12 Mo1 C2 93.71(8) . . ?
C14 Mo1 C2 112.49(7) . . ?
C4 Mo1 C2 57.98(6) . . ?
C16 Mo1 C3 148.60(7) . . ?
C15 Mo1 C3 119.46(7) . . ?
C13 Mo1 C3 91.32(8) . . ?
C1 Mo1 C3 58.20(6) . . ?
C5 Mo1 C3 57.89(6) . . ?
C13X Mo1 C3 117.04(16) . . ?
C12 Mo1 C3 112.82(8) . . ?
C14 Mo1 C3 95.39(7) . . ?
C4 Mo1 C3 34.67(6) . . ?
C2 Mo1 C3 34.13(6) . . ?
C10 O2 C11 115.20(17) . . ?
O1 C10 O2 124.75(18) . . ?
O1 C10 C1 124.74(19) . . ?
O2 C10 C1 110.52(16) . . ?
O3 C15 Mo1 178.36(17) . . ?
C6 C2 C3 119.65(17) . . ?
C6 C2 C1 133.00(17) . . ?
C3 C2 C1 107.30(15) . . ?
C6 C2 Mo1 122.29(12) . . ?
C3 C2 Mo1 73.68(10) . . ?
C1 C2 Mo1 67.58(9) . . ?
O4 C16 Mo1 178.21(18) . . ?
C5 C4 C3 108.53(16) . . ?
C5 C4 Mo1 71.02(10) . . ?
C3 C4 Mo1 76.64(10) . . ?
C5 C4 H4 125.2 . . ?
C3 C4 H4 126.3 . . ?
Mo1 C4 H4 118.3 . . ?
C7 C6 C2 118.45(19) . . ?
C7 C6 H6 120.7 . . ?
C2 C6 H6 120.9 . . ?
C4 C5 C1 108.28(16) . . ?
C4 C5 Mo1 73.73(10) . . ?
C1 C5 Mo1 71.74(9) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 125.6 . . ?
Mo1 C5 H5 121.4 . . ?
C5 C1 C2 107.81(15) . . ?
C5 C1 C10 126.18(17) . . ?
C2 C1 C10 125.92(16) . . ?
C5 C1 Mo1 72.17(10) . . ?
C2 C1 Mo1 77.06(9) . . ?
C10 C1 Mo1 119.50(12) . . ?
C8 C9 C3 118.87(19) . . ?
C8 C9 H9 120.8 . . ?
C3 C9 H9 120.4 . . ?
C9 C3 C4 132.13(18) . . ?
C9 C3 C2 119.97(17) . . ?
C4 C3 C2 107.89(16) . . ?
C9 C3 Mo1 124.02(13) . . ?
C4 C3 Mo1 68.69(10) . . ?
C2 C3 Mo1 72.18(10) . . ?
C6 C7 C8 122.04(19) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 119.2 . . ?
C13 C14 Mo1 67.70(13) . . ?
C13X C14 Mo1 71.9(2) . . ?
C13 C14 H14A 120.2 . . ?
Mo1 C14 H14A 80.5 . . ?
C13 C14 H14B 119.8 . . ?
C13X C14 H14B 156.6 . . ?
Mo1 C14 H14B 122.9 . . ?
H14A C14 H14B 120.0 . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.4 . . ?
C13X C12 Mo1 73.6(3) . . ?
C13 C12 Mo1 67.58(13) . . ?
C13 C12 H12A 119.8 . . ?
Mo1 C12 H12A 80.7 . . ?
C13X C12 H12B 156.0 . . ?
C13 C12 H12B 120.2 . . ?
Mo1 C12 H12B 122.9 . . ?
H12A C12 H12B 120.0 . . ?
O2 C11 H11A 110.2 . . ?
O2 C11 H11B 109.1 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.2 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C13 C12 127.0(3) . . ?
C14 C13 Mo1 78.25(14) . . ?
C12 C13 Mo1 77.07(14) . . ?
C14 C13 H13 116.7 . . ?
C12 C13 H13 116.3 . . ?
Mo1 C13 H13 119.5 . . ?
C12 C13X C14 134.0(5) . . ?
C12 C13X Mo1 74.8(3) . . ?
C14 C13X Mo1 73.7(2) . . ?
C12 C13X H13X 113.0 . . ?
C14 C13X H13X 113.0 . . ?
Mo1 C13X H13X 134.1 . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.067


####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1416909'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Mo O3'
_chemical_formula_sum            'C16 H14 Mo O3'
_chemical_formula_weight         350.21

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'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.7210(6)
_cell_length_b                   15.6320(12)
_cell_length_c                   23.2461(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2805.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    19844
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.938
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.038
1 0 -1 0.049
0 0 1 0.115
0 0 -1 0.141
0 -1 0 0.026
0 1 0 0.066
1 0 1 0.095


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19751
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3210
_reflns_number_gt                2529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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)+(0.0230P)²+3.7396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3210
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.32729(3) 0.159739(14) 0.589174(9) 0.01968(8) Uani 1 1 d . . .
O1 O 0.4398(3) 0.28551(14) 0.73627(8) 0.0362(5) Uani 1 1 d . . .
C4 C 0.5930(3) 0.08757(18) 0.59659(12) 0.0255(6) Uani 1 1 d . . .
H4 H 0.6365 0.0593 0.5645 0.031 Uiso 1 1 d R . .
C16 C 0.2946(3) 0.2743(2) 0.55980(12) 0.0286(6) Uani 1 1 d . . .
C3 C 0.4896(3) 0.05019(18) 0.64071(11) 0.0233(6) Uani 1 1 d . . .
C2 C 0.4467(3) 0.11629(17) 0.68153(11) 0.0224(5) Uani 1 1 d . . .
C5 C 0.6187(3) 0.17423(19) 0.61000(12) 0.0274(6) Uani 1 1 d . . .
H5 H 0.6862 0.2123 0.5889 0.033 Uiso 1 1 d R . .
C10 C 0.5157(4) 0.27833(19) 0.69053(12) 0.0283(6) Uani 1 1 d . . .
C7 C 0.2872(3) 0.01425(19) 0.73678(12) 0.0299(6) Uani 1 1 d . . .
H7 H 0.2195 0.0004 0.7685 0.036 Uiso 1 1 d R . .
O2 O 0.3359(3) 0.12859(18) 0.45800(9) 0.0512(7) Uani 1 1 d . . .
C9 C 0.4260(4) -0.03395(18) 0.64932(12) 0.0287(6) Uani 1 1 d . . .
H9 H 0.4508 -0.0771 0.6231 0.034 Uiso 1 1 d R . .
C12 C 0.0600(4) 0.2033(2) 0.62677(14) 0.0347(7) Uani 1 1 d . . .
H12A H 0.0626 0.2398 0.5952 0.042 Uiso 1 1 d R . .
H12B H 0.0515 0.2256 0.6637 0.042 Uiso 1 1 d R . .
C15 C 0.3316(4) 0.1387(2) 0.50722(13) 0.0329(7) Uani 1 1 d . . .
O3 O 0.2785(3) 0.34280(15) 0.54127(10) 0.0429(6) Uani 1 1 d . . .
C6 C 0.3441(3) 0.09686(18) 0.73034(11) 0.0259(6) Uani 1 1 d . . .
H6 H 0.3164 0.1388 0.7572 0.031 Uiso 1 1 d R . .
C13 C 0.0692(4) 0.1153(2) 0.61865(14) 0.0368(7) Uani 1 1 d . . .
H13 H 0.0657 0.0796 0.6507 0.044 Uiso 1 1 d R . .
C8 C 0.3284(4) -0.05024(19) 0.69675(13) 0.0312(6) Uani 1 1 d . . .
H8 H 0.2872 -0.1054 0.7029 0.037 Uiso 1 1 d R . .
C14 C 0.0825(4) 0.0788(2) 0.56455(15) 0.0399(8) Uani 1 1 d . . .
H14A H 0.0854 0.1135 0.5321 0.048 Uiso 1 1 d R . .
H14B H 0.0881 0.0196 0.5607 0.048 Uiso 1 1 d R . .
C1 C 0.5246(3) 0.19486(18) 0.66100(11) 0.0237(5) Uani 1 1 d . . .
C11 C 0.6072(5) 0.3522(2) 0.66339(14) 0.0395(8) Uani 1 1 d . . .
H11A H 0.5600 0.4048 0.6778 0.047 Uiso 1 1 d R . .
H11B H 0.5927 0.3500 0.6224 0.047 Uiso 1 1 d R . .
H11C H 0.7283 0.3492 0.6726 0.047 Uiso 1 1 d 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 C16 1.933(3) . ?
Mo1 C15 1.934(3) . ?
Mo1 C13 2.219(3) . ?
Mo1 C5 2.312(3) . ?
Mo1 C1 2.326(3) . ?
Mo1 C12 2.342(3) . ?
Mo1 C14 2.346(3) . ?
Mo1 C4 2.347(3) . ?
Mo1 C2 2.433(3) . ?
Mo1 C3 2.437(3) . ?
O1 C10 1.219(3) . ?
C4 C5 1.404(4) . ?
C4 C3 1.425(4) . ?
C4 H4 0.9302 . ?
C16 O3 1.161(4) . ?
C3 C9 1.418(4) . ?
C3 C2 1.442(4) . ?
C2 C6 1.417(4) . ?
C2 C1 1.449(4) . ?
C5 C1 1.427(4) . ?
C5 H5 0.9300 . ?
C10 C1 1.476(4) . ?
C10 C11 1.493(4) . ?
C7 C6 1.372(4) . ?
C7 C8 1.408(4) . ?
C7 H7 0.9300 . ?
O2 C15 1.156(4) . ?
C9 C8 1.359(4) . ?
C9 H9 0.9300 . ?
C12 C13 1.391(5) . ?
C12 H12A 0.9299 . ?
C12 H12B 0.9302 . ?
C6 H6 0.9300 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9301 . ?
C8 H8 0.9299 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9598 . ?
C11 H11C 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
C16 Mo1 C15 79.14(13) . . ?
C16 Mo1 C13 106.38(12) . . ?
C15 Mo1 C13 105.46(13) . . ?
C16 Mo1 C5 96.34(11) . . ?
C15 Mo1 C5 101.89(11) . . ?
C13 Mo1 C5 147.11(11) . . ?
C16 Mo1 C1 96.93(11) . . ?
C15 Mo1 C1 137.39(11) . . ?
C13 Mo1 C1 116.13(11) . . ?
C5 Mo1 C1 35.84(9) . . ?
C16 Mo1 C12 75.36(11) . . ?
C15 Mo1 C12 115.61(12) . . ?
C13 Mo1 C12 35.38(12) . . ?
C5 Mo1 C12 138.64(11) . . ?
C1 Mo1 C12 103.93(10) . . ?
C16 Mo1 C14 107.95(12) . . ?
C15 Mo1 C14 71.45(13) . . ?
C13 Mo1 C14 35.18(12) . . ?
C5 Mo1 C14 152.61(11) . . ?
C1 Mo1 C14 146.13(11) . . ?
C12 Mo1 C14 62.48(12) . . ?
C16 Mo1 C4 125.83(11) . . ?
C15 Mo1 C4 88.59(11) . . ?
C13 Mo1 C4 127.70(11) . . ?
C5 Mo1 C4 35.06(10) . . ?
C1 Mo1 C4 59.22(10) . . ?
C12 Mo1 C4 151.92(10) . . ?
C14 Mo1 C4 117.57(11) . . ?
C16 Mo1 C2 128.31(11) . . ?
C15 Mo1 C2 144.62(11) . . ?
C13 Mo1 C2 88.87(10) . . ?
C5 Mo1 C2 58.26(9) . . ?
C1 Mo1 C2 35.35(9) . . ?
C12 Mo1 C2 94.92(10) . . ?
C14 Mo1 C2 111.71(11) . . ?
C4 Mo1 C2 57.99(9) . . ?
C16 Mo1 C3 153.11(11) . . ?
C15 Mo1 C3 110.85(11) . . ?
C13 Mo1 C3 95.15(11) . . ?
C5 Mo1 C3 57.69(10) . . ?
C1 Mo1 C3 58.41(9) . . ?
C12 Mo1 C3 118.30(10) . . ?
C14 Mo1 C3 98.93(11) . . ?
C4 Mo1 C3 34.59(9) . . ?
C2 Mo1 C3 34.43(9) . . ?
C5 C4 C3 108.4(2) . . ?
C5 C4 Mo1 71.11(15) . . ?
C3 C4 Mo1 76.14(15) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
Mo1 C4 H4 119.0 . . ?
O3 C16 Mo1 178.3(3) . . ?
C9 C3 C4 132.5(3) . . ?
C9 C3 C2 119.5(2) . . ?
C4 C3 C2 108.0(2) . . ?
C9 C3 Mo1 122.88(18) . . ?
C4 C3 Mo1 69.27(15) . . ?
C2 C3 Mo1 72.64(15) . . ?
C6 C2 C3 120.1(3) . . ?
C6 C2 C1 132.7(3) . . ?
C3 C2 C1 107.2(2) . . ?
C6 C2 Mo1 123.69(18) . . ?
C3 C2 Mo1 72.93(14) . . ?
C1 C2 Mo1 68.29(14) . . ?
C4 C5 C1 109.3(2) . . ?
C4 C5 Mo1 73.83(16) . . ?
C1 C5 Mo1 72.61(15) . . ?
C4 C5 H5 125.4 . . ?
C1 C5 H5 125.3 . . ?
Mo1 C5 H5 119.8 . . ?
O1 C10 C1 120.6(3) . . ?
O1 C10 C11 121.7(3) . . ?
C1 C10 C11 117.7(3) . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C8 C9 C3 118.7(3) . . ?
C8 C9 H9 120.7 . . ?
C3 C9 H9 120.6 . . ?
C13 C12 Mo1 67.45(17) . . ?
C13 C12 H12A 120.0 . . ?
Mo1 C12 H12A 82.2 . . ?
C13 C12 H12B 120.0 . . ?
Mo1 C12 H12B 121.0 . . ?
H12A C12 H12B 120.0 . . ?
O2 C15 Mo1 178.0(3) . . ?
C7 C6 C2 117.9(3) . . ?
C7 C6 H6 121.1 . . ?
C2 C6 H6 121.0 . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 Mo1 77.42(18) . . ?
C12 C13 Mo1 77.17(18) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.9 . . ?
Mo1 C13 H13 117.5 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.0 . . ?
C13 C14 Mo1 67.39(17) . . ?
C13 C14 H14A 119.9 . . ?
Mo1 C14 H14A 82.2 . . ?
C13 C14 H14B 120.1 . . ?
Mo1 C14 H14B 121.5 . . ?
H14A C14 H14B 120.0 . . ?
C5 C1 C2 107.1(2) . . ?
C5 C1 C10 127.6(3) . . ?
C2 C1 C10 125.2(2) . . ?
C5 C1 Mo1 71.56(15) . . ?
C2 C1 Mo1 76.36(15) . . ?
C10 C1 Mo1 120.80(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.2 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1416910'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Mo O4'
_chemical_formula_sum            'C22 H16 Mo O4'
_chemical_formula_weight         440.29

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'
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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.2290(3)
_cell_length_b                   8.6290(7)
_cell_length_c                   21.3501(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.029(4)
_cell_angle_gamma                90
_cell_volume                     1770.51(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    17808
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.767
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.050
0 0 1 0.054
1 0 0 0.170
-1 0 0 0.182
0 1 0 0.019
0 -1 0 0.022


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17707
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3983
_reflns_number_gt                3432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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)+(0.0195P)²+1.6281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3983
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0577
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.821796(16) 0.39652(2) 0.119337(8) 0.01493(6) Uani 1 1 d . . .
O1 O 0.81551(18) -0.0488(2) 0.08795(9) 0.0356(4) Uani 1 1 d . . .
O4 O 0.75356(16) 0.65041(19) 0.20572(8) 0.0280(4) Uani 1 1 d . . .
O3 O 0.50064(15) 0.3702(2) 0.07691(8) 0.0342(4) Uani 1 1 d . . .
O2 O 0.60691(15) -0.02111(19) 0.09999(8) 0.0278(3) Uani 1 1 d . . .
C22 C 0.7805(2) 0.5540(3) 0.17488(10) 0.0206(4) Uani 1 1 d . . .
C21 C 0.6199(2) 0.3771(3) 0.09209(10) 0.0214(4) Uani 1 1 d . . .
C4 C 0.9336(2) 0.3130(3) 0.23448(10) 0.0198(4) Uani 1 1 d . . .
H4 H 1.0012 0.3895 0.2494 0.024 Uiso 1 1 d R . .
C10 C 0.7420(2) 0.0160(3) 0.11344(10) 0.0229(4) Uani 1 1 d . . .
C2 C 0.7233(2) 0.1828(2) 0.21359(10) 0.0191(4) Uani 1 1 d . . .
C12 C 1.0266(2) 0.4526(2) 0.09173(10) 0.0190(4) Uani 1 1 d . . .
C9 C 0.7883(2) 0.3483(3) 0.31184(11) 0.0251(5) Uani 1 1 d . . .
H9 H 0.8497 0.4172 0.3409 0.030 Uiso 1 1 d R . .
C3 C 0.8164(2) 0.2870(2) 0.25804(9) 0.0186(4) Uani 1 1 d . . .
C20 C 1.0086(2) 0.1980(3) 0.03704(11) 0.0279(5) Uani 1 1 d . . .
H20 H 0.9584 0.1244 0.0064 0.033 Uiso 1 1 d R . .
C5 C 0.92493(19) 0.2012(2) 0.18494(10) 0.0186(4) Uani 1 1 d . . .
H5 H 0.9963 0.1712 0.1699 0.022 Uiso 1 1 d R . .
C1 C 0.7856(2) 0.1424(2) 0.16225(10) 0.0189(4) Uani 1 1 d . . .
C6 C 0.6011(2) 0.1412(3) 0.22322(11) 0.0244(5) Uani 1 1 d . . .
H6 H 0.5388 0.0731 0.1942 0.029 Uiso 1 1 d R . .
C14 C 0.8145(2) 0.4086(3) 0.00949(10) 0.0237(5) Uani 1 1 d . . .
H14 H 0.7406 0.3604 -0.0229 0.028 Uiso 1 1 d R . .
C18 C 1.2184(2) 0.2763(3) 0.12559(12) 0.0324(6) Uani 1 1 d . . .
H18 H 1.3083 0.2509 0.1527 0.039 Uiso 1 1 d R . .
C7 C 0.5731(2) 0.2045(3) 0.27789(11) 0.0296(5) Uani 1 1 d . . .
H7 H 0.4909 0.1782 0.2848 0.035 Uiso 1 1 d R . .
C8 C 0.6651(2) 0.3046(3) 0.32133(11) 0.0296(5) Uani 1 1 d . . .
H8 H 0.6445 0.3433 0.3575 0.036 Uiso 1 1 d R . .
C16 C 0.9418(2) 0.5864(3) 0.08583(10) 0.0217(4) Uani 1 1 d . . .
H16 H 0.9658 0.6751 0.1121 0.026 Uiso 1 1 d R . .
C17 C 1.1633(2) 0.4154(3) 0.13446(11) 0.0256(5) Uani 1 1 d . . .
H17 H 1.2140 0.4838 0.1675 0.031 Uiso 1 1 d R . .
C15 C 0.8150(2) 0.5608(3) 0.03342(11) 0.0253(5) Uani 1 1 d . . .
H15 H 0.7435 0.6327 0.0173 0.030 Uiso 1 1 d R . .
C11 C 0.5553(3) -0.1477(3) 0.05436(12) 0.0346(6) Uani 1 1 d . . .
H11A H 0.5818 -0.1329 0.0157 0.041 Uiso 1 1 d R . .
H11B H 0.4557 -0.1513 0.0411 0.041 Uiso 1 1 d R . .
H11C H 0.5937 -0.2433 0.0758 0.041 Uiso 1 1 d R . .
C13 C 0.9478(2) 0.3406(3) 0.04381(10) 0.0198(4) Uani 1 1 d . . .
C19 C 1.1423(3) 0.1698(3) 0.07658(12) 0.0324(5) Uani 1 1 d . . .
H19 H 1.1850 0.0783 0.0708 0.039 Uiso 1 1 d 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 C22 1.942(2) . ?
Mo1 C21 1.951(2) . ?
Mo1 C5 2.214(2) . ?
Mo1 C15 2.300(2) . ?
Mo1 C16 2.303(2) . ?
Mo1 C14 2.323(2) . ?
Mo1 C12 2.4120(19) . ?
Mo1 C13 2.4325(19) . ?
Mo1 C4 2.4381(19) . ?
Mo1 C1 2.453(2) . ?
O1 C10 1.206(3) . ?
O4 C22 1.152(3) . ?
O3 C21 1.152(2) . ?
O2 C10 1.350(3) . ?
O2 C11 1.438(3) . ?
C4 C5 1.412(3) . ?
C4 C3 1.467(3) . ?
C4 H4 0.9300 . ?
C10 C1 1.469(3) . ?
C2 C6 1.382(3) . ?
C2 C3 1.413(3) . ?
C2 C1 1.485(3) . ?
C12 C17 1.420(3) . ?
C12 C16 1.424(3) . ?
C12 C13 1.438(3) . ?
C9 C3 1.381(3) . ?
C9 C8 1.395(3) . ?
C9 H9 0.9300 . ?
C20 C19 1.361(3) . ?
C20 C13 1.408(3) . ?
C20 H20 0.9300 . ?
C5 C1 1.432(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9301 . ?
C14 C15 1.409(3) . ?
C14 C13 1.433(3) . ?
C14 H14 0.9301 . ?
C18 C17 1.366(3) . ?
C18 C19 1.410(4) . ?
C18 H18 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C16 C15 1.410(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C19 H19 0.9301 . ?

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
C22 Mo1 C21 79.23(8) . . ?
C22 Mo1 C5 107.60(8) . . ?
C21 Mo1 C5 110.45(8) . . ?
C22 Mo1 C15 95.86(9) . . ?
C21 Mo1 C15 94.31(8) . . ?
C5 Mo1 C15 148.35(7) . . ?
C22 Mo1 C16 86.69(8) . . ?
C21 Mo1 C16 126.19(8) . . ?
C5 Mo1 C16 123.30(7) . . ?
C15 Mo1 C16 35.68(8) . . ?
C22 Mo1 C14 130.28(9) . . ?
C21 Mo1 C14 92.18(8) . . ?
C5 Mo1 C14 121.07(8) . . ?
C15 Mo1 C14 35.49(8) . . ?
C16 Mo1 C14 59.39(8) . . ?
C22 Mo1 C12 113.41(8) . . ?
C21 Mo1 C12 149.71(8) . . ?
C5 Mo1 C12 92.39(7) . . ?
C15 Mo1 C12 58.21(7) . . ?
C16 Mo1 C12 35.06(7) . . ?
C14 Mo1 C12 58.30(7) . . ?
C22 Mo1 C13 144.96(8) . . ?
C21 Mo1 C13 122.14(8) . . ?
C5 Mo1 C13 91.28(7) . . ?
C15 Mo1 C13 58.14(7) . . ?
C16 Mo1 C13 58.38(7) . . ?
C14 Mo1 C13 34.99(7) . . ?
C12 Mo1 C13 34.53(7) . . ?
C22 Mo1 C4 73.51(8) . . ?
C21 Mo1 C4 110.99(7) . . ?
C5 Mo1 C4 34.92(7) . . ?
C15 Mo1 C4 149.52(8) . . ?
C16 Mo1 C4 114.06(7) . . ?
C14 Mo1 C4 150.80(7) . . ?
C12 Mo1 C4 99.15(7) . . ?
C13 Mo1 C4 115.96(7) . . ?
C22 Mo1 C1 107.76(8) . . ?
C21 Mo1 C1 75.81(8) . . ?
C5 Mo1 C1 35.27(7) . . ?
C15 Mo1 C1 151.83(8) . . ?
C16 Mo1 C1 156.45(7) . . ?
C14 Mo1 C1 117.41(8) . . ?
C12 Mo1 C1 121.71(7) . . ?
C13 Mo1 C1 104.61(7) . . ?
C4 Mo1 C1 55.79(7) . . ?
C10 O2 C11 115.83(18) . . ?
O4 C22 Mo1 177.48(18) . . ?
O3 C21 Mo1 177.8(2) . . ?
C5 C4 C3 107.66(18) . . ?
C5 C4 Mo1 63.85(11) . . ?
C3 C4 Mo1 103.59(12) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Mo1 C4 H4 99.9 . . ?
O1 C10 O2 123.0(2) . . ?
O1 C10 C1 125.4(2) . . ?
O2 C10 C1 111.52(18) . . ?
C6 C2 C3 120.07(19) . . ?
C6 C2 C1 133.4(2) . . ?
C3 C2 C1 106.52(17) . . ?
C17 C12 C16 132.6(2) . . ?
C17 C12 C13 119.6(2) . . ?
C16 C12 C13 107.81(18) . . ?
C17 C12 Mo1 122.97(14) . . ?
C16 C12 Mo1 68.29(11) . . ?
C13 C12 Mo1 73.52(11) . . ?
C3 C9 C8 118.2(2) . . ?
C3 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C3 C2 121.17(19) . . ?
C9 C3 C4 130.8(2) . . ?
C2 C3 C4 107.98(17) . . ?
C19 C20 C13 118.6(2) . . ?
C19 C20 H20 120.6 . . ?
C13 C20 H20 120.8 . . ?
C4 C5 C1 107.15(17) . . ?
C4 C5 Mo1 81.23(12) . . ?
C1 C5 Mo1 81.49(12) . . ?
C4 C5 H5 126.5 . . ?
C1 C5 H5 126.4 . . ?
Mo1 C5 H5 104.7 . . ?
C5 C1 C10 121.87(18) . . ?
C5 C1 C2 107.21(17) . . ?
C10 C1 C2 126.53(18) . . ?
C5 C1 Mo1 63.24(11) . . ?
C10 C1 Mo1 116.55(13) . . ?
C2 C1 Mo1 102.93(13) . . ?
C2 C6 C7 118.4(2) . . ?
C2 C6 H6 120.9 . . ?
C7 C6 H6 120.7 . . ?
C15 C14 C13 108.18(19) . . ?
C15 C14 Mo1 71.38(12) . . ?
C13 C14 Mo1 76.68(11) . . ?
C15 C14 H14 126.0 . . ?
C13 C14 H14 125.9 . . ?
Mo1 C14 H14 117.9 . . ?
C17 C18 C19 121.8(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.0 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.8 . . ?
C15 C16 C12 108.08(19) . . ?
C15 C16 Mo1 72.06(12) . . ?
C12 C16 Mo1 76.65(12) . . ?
C15 C16 H16 126.0 . . ?
C12 C16 H16 125.9 . . ?
Mo1 C16 H16 117.2 . . ?
C18 C17 C12 118.2(2) . . ?
C18 C17 H17 120.8 . . ?
C12 C17 H17 121.0 . . ?
C14 C15 C16 108.75(19) . . ?
C14 C15 Mo1 73.13(12) . . ?
C16 C15 Mo1 72.26(12) . . ?
C14 C15 H15 125.7 . . ?
C16 C15 H15 125.6 . . ?
Mo1 C15 H15 120.8 . . ?
O2 C11 H11A 109.6 . . ?
O2 C11 H11B 109.3 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.6 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C20 C13 C14 133.0(2) . . ?
C20 C13 C12 120.04(19) . . ?
C14 C13 C12 106.98(19) . . ?
C20 C13 Mo1 126.48(15) . . ?
C14 C13 Mo1 68.33(11) . . ?
C12 C13 Mo1 71.95(11) . . ?
C20 C19 C18 121.7(2) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1416911'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Mo N O3'
_chemical_formula_sum            'C19 H21 Mo N O3'
_chemical_formula_weight         407.31

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'
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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.7229(6)
_cell_length_b                   10.5260(4)
_cell_length_c                   10.5021(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.030(7)
_cell_angle_gamma                90
_cell_volume                     1728.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    17590
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.775
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.086
1 0 0 0.022
0 -1 -1 0.103
0 1 1 0.059
0 1 -1 0.076
0 -1 1 0.069
0 0 -1 0.139


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17479
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3955
_reflns_number_gt                3449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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)+(0.0309P)²+1.8023P] 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         3955
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.853400(11) 0.087956(17) 0.260495(16) 0.01409(7) Uani 1 1 d . . .
O1 O 0.63801(10) 0.17860(15) 0.08458(14) 0.0203(3) Uani 1 1 d . . .
C18 C 0.95586(15) 0.1360(2) 0.3717(2) 0.0252(5) Uani 1 1 d . . .
C9 C 0.80752(15) -0.2237(2) 0.3202(2) 0.0221(5) Uani 1 1 d . . .
H9 H 0.8457 -0.2618 0.3823 0.027 Uiso 1 1 d R . .
C1 C 0.70779(13) 0.0909(2) 0.2764(2) 0.0146(4) Uani 1 1 d . . .
N1 N 0.61271(11) 0.26919(17) 0.27359(17) 0.0173(4) Uani 1 1 d . . .
H1 H 0.6233 0.2694 0.3609 0.021 Uiso 1 1 d R . .
C10 C 0.65013(13) 0.1840(2) 0.2022(2) 0.0157(4) Uani 1 1 d . . .
C19 C 0.85148(14) 0.2668(2) 0.2192(2) 0.0206(4) Uani 1 1 d . . .
C6 C 0.69418(14) -0.1081(2) 0.1241(2) 0.0194(4) Uani 1 1 d . . .
H6 H 0.6586 -0.0709 0.0582 0.023 Uiso 1 1 d R . .
O2 O 1.01555(12) 0.1651(2) 0.4385(2) 0.0407(5) Uani 1 1 d . . .
C7 C 0.71969(15) -0.2313(2) 0.1161(2) 0.0235(5) Uani 1 1 d . . .
H7 H 0.6989 -0.2792 0.0452 0.028 Uiso 1 1 d R . .
C11 C 0.55323(14) 0.3710(2) 0.2220(2) 0.0177(4) Uani 1 1 d . . .
O3 O 0.84498(12) 0.37470(17) 0.19845(18) 0.0319(4) Uani 1 1 d . . .
C2 C 0.72369(13) -0.0371(2) 0.23536(19) 0.0151(4) Uani 1 1 d . . .
C13 C 0.53121(17) 0.4475(3) 0.3367(2) 0.0298(6) Uani 1 1 d . . .
H13A H 0.5072 0.3919 0.3960 0.036 Uiso 1 1 d R . .
H13B H 0.4904 0.5123 0.3091 0.036 Uiso 1 1 d R . .
H13C H 0.5821 0.4863 0.3779 0.036 Uiso 1 1 d R . .
C4 C 0.79836(14) -0.0063(2) 0.43531(19) 0.0170(4) Uani 1 1 d . . .
H4 H 0.8347 -0.0190 0.5100 0.020 Uiso 1 1 d R . .
C5 C 0.75094(13) 0.1058(2) 0.4022(2) 0.0166(4) Uani 1 1 d . . .
H5 H 0.7484 0.1773 0.4537 0.020 Uiso 1 1 d R . .
C8 C 0.77670(16) -0.2891(2) 0.2134(2) 0.0254(5) Uani 1 1 d . . .
H8 H 0.7929 -0.3732 0.2038 0.030 Uiso 1 1 d R . .
C3 C 0.78016(14) -0.0967(2) 0.3345(2) 0.0170(4) Uani 1 1 d . . .
C14 C 0.47176(15) 0.3129(2) 0.1540(2) 0.0245(5) Uani 1 1 d . . .
H14A H 0.4857 0.2640 0.0818 0.029 Uiso 1 1 d R . .
H14B H 0.4327 0.3795 0.1251 0.029 Uiso 1 1 d R . .
H14C H 0.4457 0.2587 0.2123 0.029 Uiso 1 1 d R . .
C12 C 0.59676(17) 0.4567(3) 0.1309(3) 0.0312(6) Uani 1 1 d . . .
H12A H 0.6507 0.4850 0.1724 0.037 Uiso 1 1 d R . .
H12B H 0.5611 0.5289 0.1081 0.037 Uiso 1 1 d R . .
H12C H 0.6059 0.4099 0.0551 0.037 Uiso 1 1 d R . .
C16 C 0.8997(2) -0.0183(3) 0.0993(3) 0.0409(7) Uani 1 1 d . . .
H16 H 0.8752 -0.0965 0.0763 0.049 Uiso 1 1 d R . .
C17 C 0.97044(19) -0.0152(4) 0.1877(3) 0.0472(8) Uani 1 1 d . . .
H17A H 0.9963 0.0616 0.2126 0.057 Uiso 1 1 d R . .
H17B H 0.9920 -0.0909 0.2236 0.057 Uiso 1 1 d R . .
C15 C 0.8636(2) 0.0895(3) 0.0403(2) 0.0349(6) Uani 1 1 d . . .
H15A H 0.8867 0.1690 0.0614 0.042 Uiso 1 1 d R . .
H15B H 0.8161 0.0824 -0.0200 0.042 Uiso 1 1 d 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 C19 1.931(2) . ?
Mo1 C18 1.955(2) . ?
Mo1 C16 2.214(3) . ?
Mo1 C5 2.313(2) . ?
Mo1 C1 2.313(2) . ?
Mo1 C4 2.332(2) . ?
Mo1 C17 2.334(3) . ?
Mo1 C15 2.335(2) . ?
Mo1 C2 2.418(2) . ?
Mo1 C3 2.428(2) . ?
O1 C10 1.231(3) . ?
C18 O2 1.152(3) . ?
C9 C8 1.361(3) . ?
C9 C3 1.418(3) . ?
C9 H9 0.9300 . ?
C1 C5 1.429(3) . ?
C1 C2 1.445(3) . ?
C1 C10 1.497(3) . ?
N1 C10 1.344(3) . ?
N1 C11 1.486(3) . ?
N1 H1 0.9145 . ?
C19 O3 1.159(3) . ?
C6 C7 1.363(3) . ?
C6 C2 1.423(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.423(3) . ?
C7 H7 0.9300 . ?
C11 C13 1.519(3) . ?
C11 C14 1.528(3) . ?
C11 C12 1.528(3) . ?
C2 C3 1.440(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9601 . ?
C13 H13C 0.9599 . ?
C4 C5 1.419(3) . ?
C4 C3 1.429(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9599 . ?
C12 H12C 0.9601 . ?
C16 C17 1.372(4) . ?
C16 C15 1.385(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9301 . ?
C15 H15A 0.9300 . ?
C15 H15B 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
C19 Mo1 C18 82.80(9) . . ?
C19 Mo1 C16 108.63(11) . . ?
C18 Mo1 C16 105.74(11) . . ?
C19 Mo1 C5 94.00(9) . . ?
C18 Mo1 C5 100.39(9) . . ?
C16 Mo1 C5 147.12(10) . . ?
C19 Mo1 C1 90.62(8) . . ?
C18 Mo1 C1 135.49(9) . . ?
C16 Mo1 C1 117.98(10) . . ?
C5 Mo1 C1 35.98(7) . . ?
C19 Mo1 C4 126.38(9) . . ?
C18 Mo1 C4 89.44(9) . . ?
C16 Mo1 C4 124.45(10) . . ?
C5 Mo1 C4 35.59(7) . . ?
C1 Mo1 C4 59.78(7) . . ?
C19 Mo1 C17 111.97(12) . . ?
C18 Mo1 C17 71.78(11) . . ?
C16 Mo1 C17 35.00(11) . . ?
C5 Mo1 C17 151.08(11) . . ?
C1 Mo1 C17 148.28(10) . . ?
C4 Mo1 C17 115.52(11) . . ?
C19 Mo1 C15 76.83(10) . . ?
C18 Mo1 C15 116.87(11) . . ?
C16 Mo1 C15 35.33(11) . . ?
C5 Mo1 C15 139.63(10) . . ?
C1 Mo1 C15 104.08(9) . . ?
C4 Mo1 C15 148.49(9) . . ?
C17 Mo1 C15 62.60(11) . . ?
C19 Mo1 C2 120.86(8) . . ?
C18 Mo1 C2 147.00(9) . . ?
C16 Mo1 C2 89.00(10) . . ?
C5 Mo1 C2 58.54(7) . . ?
C1 Mo1 C2 35.47(7) . . ?
C4 Mo1 C2 58.39(7) . . ?
C17 Mo1 C2 113.33(10) . . ?
C15 Mo1 C2 92.33(9) . . ?
C19 Mo1 C3 148.79(8) . . ?
C18 Mo1 C3 113.85(9) . . ?
C16 Mo1 C3 92.60(10) . . ?
C5 Mo1 C3 58.21(7) . . ?
C1 Mo1 C3 58.76(7) . . ?
C4 Mo1 C3 34.87(7) . . ?
C17 Mo1 C3 98.60(11) . . ?
C15 Mo1 C3 114.02(9) . . ?
C2 Mo1 C3 34.56(7) . . ?
O2 C18 Mo1 179.0(2) . . ?
C8 C9 C3 118.6(2) . . ?
C8 C9 H9 120.6 . . ?
C3 C9 H9 120.8 . . ?
C5 C1 C2 107.35(18) . . ?
C5 C1 C10 127.78(19) . . ?
C2 C1 C10 124.69(18) . . ?
C5 C1 Mo1 72.00(12) . . ?
C2 C1 Mo1 76.24(12) . . ?
C10 C1 Mo1 121.39(14) . . ?
C10 N1 C11 124.99(18) . . ?
C10 N1 H1 121.1 . . ?
C11 N1 H1 113.9 . . ?
O1 C10 N1 124.1(2) . . ?
O1 C10 C1 120.92(19) . . ?
N1 C10 C1 115.00(18) . . ?
O3 C19 Mo1 175.1(2) . . ?
C7 C6 C2 118.5(2) . . ?
C7 C6 H6 120.8 . . ?
C2 C6 H6 120.7 . . ?
C6 C7 C8 122.0(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
N1 C11 C13 106.29(17) . . ?
N1 C11 C14 110.26(18) . . ?
C13 C11 C14 109.49(19) . . ?
N1 C11 C12 110.33(18) . . ?
C13 C11 C12 109.8(2) . . ?
C14 C11 C12 110.6(2) . . ?
C6 C2 C3 119.2(2) . . ?
C6 C2 C1 133.1(2) . . ?
C3 C2 C1 107.64(18) . . ?
C6 C2 Mo1 125.02(15) . . ?
C3 C2 Mo1 73.09(12) . . ?
C1 C2 Mo1 68.29(11) . . ?
C11 C13 H13A 109.2 . . ?
C11 C13 H13B 109.7 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 C3 108.24(18) . . ?
C5 C4 Mo1 71.48(12) . . ?
C3 C4 Mo1 76.24(12) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Mo1 C4 H4 118.6 . . ?
C4 C5 C1 108.74(19) . . ?
C4 C5 Mo1 72.94(12) . . ?
C1 C5 Mo1 72.02(11) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.5 . . ?
Mo1 C5 H5 121.0 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.2 . . ?
C9 C3 C4 131.9(2) . . ?
C9 C3 C2 120.3(2) . . ?
C4 C3 C2 107.83(19) . . ?
C9 C3 Mo1 124.16(15) . . ?
C4 C3 Mo1 68.88(12) . . ?
C2 C3 Mo1 72.35(12) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C16 C15 123.2(3) . . ?
C17 C16 Mo1 77.25(17) . . ?
C15 C16 Mo1 77.10(16) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.0 . . ?
Mo1 C16 H16 119.1 . . ?
C16 C17 Mo1 67.75(16) . . ?
C16 C17 H17A 120.7 . . ?
Mo1 C17 H17A 80.8 . . ?
C16 C17 H17B 119.3 . . ?
Mo1 C17 H17B 122.1 . . ?
H17A C17 H17B 120.0 . . ?
C16 C15 Mo1 67.58(15) . . ?
C16 C15 H15A 120.0 . . ?
Mo1 C15 H15A 80.5 . . ?
C16 C15 H15B 120.0 . . ?
Mo1 C15 H15B 122.7 . . ?
H15A C15 H15B 120.0 . . ?

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
N1 H1 O1 0.91 2.40 3.295(2) 166.1 4_566

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.311
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1416912'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 O'
_chemical_formula_sum            'C11 H10 O'
_chemical_formula_weight         158.19

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   15.0282(4)
_cell_length_b                   7.5420(2)
_cell_length_c                   14.8454(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.901(2)
_cell_angle_gamma                90
_cell_volume                     1681.69(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    6555
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.079
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.092
-1 0 1 0.085
-1 0 -1 0.090
1 0 1 0.099
1 1 0 0.075
-1 -1 0 0.037
1 -1 0 0.074
-1 1 0 0.089
-1 0 0 0.076
1 0 0 0.107
0 0 -1 0.099
0 0 1 0.093


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6485
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1898
_reflns_number_gt                1415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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)+(0.0420P)²+1.1281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1898
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
O1 O 1.06380(8) 0.32484(16) 0.03451(9) 0.0416(3) Uani 1 1 d . . .
C3 C 0.88951(10) 0.15869(19) 0.06487(10) 0.0285(3) Uani 1 1 d . . .
C7 C 0.91154(10) 0.2125(2) 0.15270(11) 0.0313(4) Uani 1 1 d . . .
H7 H 0.9644 0.2731 0.1655 0.038 Uiso 1 1 d R . .
C2 C 0.93441(10) 0.1830(2) -0.02101(10) 0.0292(3) Uani 1 1 d . . .
C4 C 0.80968(10) 0.0657(2) 0.04662(11) 0.0301(4) Uani 1 1 d . . .
C9 C 0.77457(11) 0.0819(2) 0.20179(12) 0.0380(4) Uani 1 1 d . . .
H9 H 0.7365 0.0566 0.2482 0.046 Uiso 1 1 d R . .
C10 C 0.75228(11) 0.0269(2) 0.11448(12) 0.0348(4) Uani 1 1 d . . .
H10 H 0.6997 -0.0347 0.1022 0.042 Uiso 1 1 d R . .
C6 C 0.88438(11) 0.1082(2) -0.08760(11) 0.0328(4) Uani 1 1 d . . .
H6 H 0.8992 0.1079 -0.1479 0.039 Uiso 1 1 d R . .
C8 C 0.85343(11) 0.1740(2) 0.22041(11) 0.0368(4) Uani 1 1 d . . .
H8 H 0.8670 0.2102 0.2792 0.044 Uiso 1 1 d R . .
C11 C 1.05258(12) 0.3014(2) -0.12486(12) 0.0422(4) Uani 1 1 d . . .
H11A H 1.1077 0.3657 -0.1220 0.051 Uiso 1 1 d R . .
H11B H 1.0091 0.3675 -0.1597 0.051 Uiso 1 1 d R . .
H11C H 1.0617 0.1883 -0.1528 0.051 Uiso 1 1 d R . .
C1 C 1.02017(10) 0.2739(2) -0.03144(11) 0.0322(4) Uani 1 1 d . . .
C5 C 0.80203(10) 0.0259(2) -0.05264(11) 0.0332(4) Uani 1 1 d . . .
H5A H 0.7489 0.0791 -0.0799 0.040 Uiso 1 1 d R . .
H5B H 0.8008 -0.1009 -0.0636 0.040 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2220(19) . ?
C3 C7 1.395(2) . ?
C3 C4 1.408(2) . ?
C3 C2 1.474(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9300 . ?
C2 C6 1.346(2) . ?
C2 C1 1.473(2) . ?
C4 C10 1.379(2) . ?
C4 C5 1.504(2) . ?
C9 C10 1.391(2) . ?
C9 C8 1.394(2) . ?
C9 H9 0.9301 . ?
C10 H10 0.9300 . ?
C6 C5 1.493(2) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C11 C1 1.499(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9701 . ?

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
C7 C3 C4 119.93(15) . . ?
C7 C3 C2 132.16(14) . . ?
C4 C3 C2 107.89(13) . . ?
C8 C7 C3 118.81(15) . . ?
C8 C7 H7 120.6 . . ?
C3 C7 H7 120.5 . . ?
C6 C2 C1 125.98(15) . . ?
C6 C2 C3 108.82(14) . . ?
C1 C2 C3 125.20(14) . . ?
C10 C4 C3 120.98(14) . . ?
C10 C4 C5 130.07(14) . . ?
C3 C4 C5 108.95(14) . . ?
C10 C9 C8 120.68(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.7 . . ?
C4 C10 C9 118.70(15) . . ?
C4 C10 H10 120.7 . . ?
C9 C10 H10 120.6 . . ?
C2 C6 C5 111.61(14) . . ?
C2 C6 H6 124.3 . . ?
C5 C6 H6 124.1 . . ?
C7 C8 C9 120.90(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.4 . . ?
C1 C11 H11A 109.6 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.4 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C1 C2 120.69(15) . . ?
O1 C1 C11 121.02(15) . . ?
C2 C1 C11 118.29(14) . . ?
C6 C5 C4 102.72(12) . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1416913'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Cl Mo N O3, C H4 O'
_chemical_formula_sum            'C22 H20 Cl Mo N O4'
_chemical_formula_weight         493.78

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'
Cl Cl 0.1484 0.1585 '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  '-P 1'

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

_cell_length_a                   7.0020(6)
_cell_length_b                   8.9280(6)
_cell_length_c                   17.3821(7)
_cell_angle_alpha                75.562(5)
_cell_angle_beta                 85.442(6)
_cell_angle_gamma                74.224(6)
_cell_volume                     1012.59(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    19462
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.808
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.072
0 0 -1 0.102
1 0 0 0.063
-1 0 0 0.051
0 1 1 0.046
0 -1 -1 0.027
-1 0 -1 0.065
1 0 1 0.075
-1 -1 -1 0.041


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19360
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4623
_reflns_number_gt                4062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 > 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)+(0.0228P)²+1.1700P] 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         4623
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.59348(3) -0.19990(2) 0.356300(12) 0.01653(6) Uani 1 1 d . . .
Cl1 Cl 0.54279(10) 0.54522(8) -0.15789(4) 0.03083(15) Uani 1 1 d . . .
O3 O 0.2478(3) -0.0713(2) 0.46548(11) 0.0326(4) Uani 1 1 d . . .
C20 C 0.3768(4) -0.1230(3) 0.42546(15) 0.0238(5) Uani 1 1 d . . .
O1 O 0.8471(2) -0.1248(2) 0.14321(10) 0.0253(4) Uani 1 1 d . . .
N1 N 0.5209(3) 0.0015(2) 0.11700(11) 0.0196(4) Uani 1 1 d . . .
H1 H 0.4087 -0.0027 0.1275 0.024 Uiso 1 1 d R . .
C14 C 0.5416(4) 0.3822(3) -0.07833(14) 0.0236(5) Uani 1 1 d . . .
C8 C 0.9271(4) -0.6667(3) 0.37184(16) 0.0267(5) Uani 1 1 d . . .
H8 H 0.9906 -0.7634 0.4055 0.032 Uiso 1 1 d R . .
C10 C 0.6689(3) -0.1126(3) 0.15894(13) 0.0187(5) Uani 1 1 d . . .
C2 C 0.7454(3) -0.3749(3) 0.26848(13) 0.0185(5) Uani 1 1 d . . .
C6 C 0.9537(4) -0.4414(3) 0.26270(14) 0.0222(5) Uani 1 1 d . . .
H6 H 1.0302 -0.3884 0.2252 0.027 Uiso 1 1 d R . .
C11 C 0.5373(4) 0.1273(3) 0.05035(13) 0.0198(5) Uani 1 1 d . . .
O4 O 0.5238(3) 0.1675(2) 0.30268(13) 0.0387(5) Uani 1 1 d . . .
C21 C 0.5534(4) 0.0303(3) 0.32206(15) 0.0247(5) Uani 1 1 d . . .
C5 C 0.4146(3) -0.2326(3) 0.25777(14) 0.0200(5) Uani 1 1 d . . .
H5 H 0.2977 -0.1567 0.2393 0.024 Uiso 1 1 d R . .
C4 C 0.4297(4) -0.3689(3) 0.32144(14) 0.0217(5) Uani 1 1 d . . .
H4 H 0.3254 -0.3947 0.3538 0.026 Uiso 1 1 d R . .
C1 C 0.6090(3) -0.2306(3) 0.22637(13) 0.0181(5) Uani 1 1 d . . .
C17 C 0.8879(4) -0.1467(3) 0.38287(17) 0.0301(6) Uani 1 1 d . . .
H17A H 0.8020 -0.0509 0.3894 0.036 Uiso 1 1 d R . .
H17B H 0.9900 -0.1455 0.3452 0.036 Uiso 1 1 d R . .
C7 C 1.0393(4) -0.5839(3) 0.31325(16) 0.0261(5) Uani 1 1 d . . .
H7 H 1.1752 -0.6282 0.3092 0.031 Uiso 1 1 d R . .
C12 C 0.7166(4) 0.1447(3) 0.01314(14) 0.0250(5) Uani 1 1 d . . .
H12 H 0.8350 0.0700 0.0309 0.030 Uiso 1 1 d R . .
C3 C 0.6316(3) -0.4599(3) 0.32769(14) 0.0196(5) Uani 1 1 d . . .
C16 C 0.3612(4) 0.2359(3) 0.02066(15) 0.0246(5) Uani 1 1 d . . .
H16 H 0.2411 0.2228 0.0443 0.030 Uiso 1 1 d R . .
C18 C 0.8642(4) -0.2935(3) 0.42963(15) 0.0274(6) Uani 1 1 d . . .
H18 H 0.9507 -0.3889 0.4228 0.033 Uiso 1 1 d R . .
C15 C 0.3622(4) 0.3637(3) -0.04347(15) 0.0269(5) Uani 1 1 d . . .
H15 H 0.2437 0.4364 -0.0628 0.032 Uiso 1 1 d R . .
C9 C 0.7274(4) -0.6071(3) 0.37968(15) 0.0236(5) Uani 1 1 d . . .
H9 H 0.6551 -0.6621 0.4183 0.028 Uiso 1 1 d R . .
C13 C 0.7170(4) 0.2737(3) -0.05092(15) 0.0278(6) Uani 1 1 d . . .
H13 H 0.8364 0.2870 -0.0753 0.033 Uiso 1 1 d R . .
C19 C 0.7121(4) -0.2982(4) 0.48628(15) 0.0304(6) Uani 1 1 d . . .
H19A H 0.6251 -0.2033 0.4935 0.036 Uiso 1 1 d R . .
H19B H 0.6976 -0.3961 0.5169 0.036 Uiso 1 1 d R . .
O2 O 0.0950(3) 0.0553(2) 0.15449(11) 0.0290(4) Uani 1 1 d . . .
H2 H 0.0173 -0.0012 0.1511 0.035 Uiso 1 1 d R . .
C22 C 0.0004(6) 0.1814(5) 0.1889(2) 0.0606(11) Uani 1 1 d . . .
H22A H -0.0289 0.1393 0.2437 0.073 Uiso 1 1 d R . .
H22B H -0.1207 0.2415 0.1616 0.073 Uiso 1 1 d R . .
H22C H 0.0865 0.2501 0.1856 0.073 Uiso 1 1 d 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 C21 1.939(3) . ?
Mo1 C20 1.943(3) . ?
Mo1 C18 2.216(2) . ?
Mo1 C5 2.319(2) . ?
Mo1 C1 2.332(2) . ?
Mo1 C4 2.338(2) . ?
Mo1 C19 2.340(2) . ?
Mo1 C17 2.342(2) . ?
Mo1 C3 2.434(2) . ?
Mo1 C2 2.435(2) . ?
Cl1 C14 1.741(2) . ?
O3 C20 1.160(3) . ?
O1 C10 1.237(3) . ?
N1 C10 1.349(3) . ?
N1 C11 1.420(3) . ?
N1 H1 0.8013 . ?
C14 C13 1.375(4) . ?
C14 C15 1.384(4) . ?
C8 C9 1.363(4) . ?
C8 C7 1.419(4) . ?
C8 H8 0.9300 . ?
C10 C1 1.485(3) . ?
C2 C6 1.423(3) . ?
C2 C3 1.442(3) . ?
C2 C1 1.442(3) . ?
C6 C7 1.364(3) . ?
C6 H6 0.9299 . ?
C11 C16 1.388(3) . ?
C11 C12 1.395(3) . ?
O4 C21 1.151(3) . ?
C5 C4 1.412(3) . ?
C5 C1 1.428(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.423(3) . ?
C4 H4 0.9300 . ?
C17 C18 1.404(4) . ?
C17 H17A 0.9301 . ?
C17 H17B 0.9300 . ?
C7 H7 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C3 C9 1.421(3) . ?
C16 C15 1.383(3) . ?
C16 H16 0.9299 . ?
C18 C19 1.394(4) . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9 0.9299 . ?
C13 H13 0.9300 . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
O2 C22 1.390(4) . ?
O2 H2 0.8502 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9601 . ?
C22 H22C 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
C21 Mo1 C20 78.04(10) . . ?
C21 Mo1 C18 106.59(11) . . ?
C20 Mo1 C18 106.52(10) . . ?
C21 Mo1 C5 98.23(10) . . ?
C20 Mo1 C5 99.81(9) . . ?
C18 Mo1 C5 146.83(9) . . ?
C21 Mo1 C1 93.03(9) . . ?
C20 Mo1 C1 133.53(9) . . ?
C18 Mo1 C1 119.64(9) . . ?
C5 Mo1 C1 35.76(8) . . ?
C21 Mo1 C4 130.81(10) . . ?
C20 Mo1 C4 92.63(10) . . ?
C18 Mo1 C4 122.24(10) . . ?
C5 Mo1 C4 35.30(8) . . ?
C1 Mo1 C4 59.23(8) . . ?
C21 Mo1 C19 111.36(11) . . ?
C20 Mo1 C19 73.37(10) . . ?
C18 Mo1 C19 35.50(9) . . ?
C5 Mo1 C19 146.93(9) . . ?
C1 Mo1 C19 148.39(9) . . ?
C4 Mo1 C19 111.74(9) . . ?
C21 Mo1 C17 73.41(10) . . ?
C20 Mo1 C17 111.88(10) . . ?
C18 Mo1 C17 35.75(10) . . ?
C5 Mo1 C17 144.13(9) . . ?
C1 Mo1 C17 108.73(9) . . ?
C4 Mo1 C17 150.01(9) . . ?
C19 Mo1 C17 62.61(10) . . ?
C21 Mo1 C3 151.19(10) . . ?
C20 Mo1 C3 118.89(9) . . ?
C18 Mo1 C3 91.35(9) . . ?
C5 Mo1 C3 57.82(8) . . ?
C1 Mo1 C3 58.24(8) . . ?
C4 Mo1 C3 34.63(8) . . ?
C19 Mo1 C3 96.41(9) . . ?
C17 Mo1 C3 115.42(9) . . ?
C21 Mo1 C2 121.32(9) . . ?
C20 Mo1 C2 150.63(9) . . ?
C18 Mo1 C2 89.69(9) . . ?
C5 Mo1 C2 58.24(8) . . ?
C1 Mo1 C2 35.13(8) . . ?
C4 Mo1 C2 58.07(8) . . ?
C19 Mo1 C2 113.32(9) . . ?
C17 Mo1 C2 95.67(9) . . ?
C3 Mo1 C2 34.45(8) . . ?
O3 C20 Mo1 177.5(2) . . ?
C10 N1 C11 127.9(2) . . ?
C10 N1 H1 118.7 . . ?
C11 N1 H1 113.3 . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 Cl1 120.2(2) . . ?
C15 C14 Cl1 119.1(2) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.6 . . ?
O1 C10 N1 123.8(2) . . ?
O1 C10 C1 119.7(2) . . ?
N1 C10 C1 116.5(2) . . ?
C6 C2 C3 119.0(2) . . ?
C6 C2 C1 133.8(2) . . ?
C3 C2 C1 107.2(2) . . ?
C6 C2 Mo1 123.67(16) . . ?
C3 C2 Mo1 72.73(13) . . ?
C1 C2 Mo1 68.54(13) . . ?
C7 C6 C2 118.9(2) . . ?
C7 C6 H6 120.6 . . ?
C2 C6 H6 120.5 . . ?
C16 C11 C12 119.3(2) . . ?
C16 C11 N1 116.6(2) . . ?
C12 C11 N1 124.0(2) . . ?
O4 C21 Mo1 177.9(2) . . ?
C4 C5 C1 108.7(2) . . ?
C4 C5 Mo1 73.10(13) . . ?
C1 C5 Mo1 72.65(13) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.6 . . ?
Mo1 C5 H5 120.4 . . ?
C5 C4 C3 108.4(2) . . ?
C5 C4 Mo1 71.60(13) . . ?
C3 C4 Mo1 76.38(14) . . ?
C5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
Mo1 C4 H4 118.1 . . ?
C5 C1 C2 107.6(2) . . ?
C5 C1 C10 128.8(2) . . ?
C2 C1 C10 123.5(2) . . ?
C5 C1 Mo1 71.59(13) . . ?
C2 C1 Mo1 76.33(13) . . ?
C10 C1 Mo1 121.42(15) . . ?
C18 C17 Mo1 67.22(14) . . ?
C18 C17 H17A 120.2 . . ?
Mo1 C17 H17A 82.8 . . ?
C18 C17 H17B 119.8 . . ?
Mo1 C17 H17B 120.9 . . ?
H17A C17 H17B 120.0 . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 118.9 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C9 C3 C4 131.9(2) . . ?
C9 C3 C2 120.1(2) . . ?
C4 C3 C2 108.0(2) . . ?
C9 C3 Mo1 123.21(16) . . ?
C4 C3 Mo1 68.99(13) . . ?
C2 C3 Mo1 72.82(13) . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 Mo1 77.14(15) . . ?
C17 C18 Mo1 77.02(15) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.8 . . ?
Mo1 C18 H18 116.8 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C8 C9 C3 118.9(2) . . ?
C8 C9 H9 120.5 . . ?
C3 C9 H9 120.6 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.9 . . ?
C18 C19 Mo1 67.35(14) . . ?
C18 C19 H19A 119.9 . . ?
Mo1 C19 H19A 82.5 . . ?
C18 C19 H19B 120.1 . . ?
Mo1 C19 H19B 121.0 . . ?
H19A C19 H19B 120.0 . . ?
C22 O2 H2 111.5 . . ?
O2 C22 H22A 109.2 . . ?
O2 C22 H22B 110.0 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.2 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
N1 H1 O2 0.80 2.16 2.936(3) 164.1 .
O2 H2 O1 0.85 1.86 2.714(2) 179.8 1_455

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.082
