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

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

#=============================================================================
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_audit_creation_date             '10 January 2014'
#=============================================================================

#=============================================================================
# GENERAL AND CHEMICAL DATA
#=============================================================================


_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Cl Mo N2 O2'
_chemical_formula_sum            'C15 H13 Cl Mo N2 O2'
_chemical_formula_weight         384.66

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0476(7)
_cell_length_b                   11.4511(10)
_cell_length_c                   16.8556(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1553.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.14

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

#=============================================================================
# EXPERIMENTAL DATA
#=============================================================================

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30905
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4143
_reflns_number_gt                3864
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0215P)²+0.2428P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_number_reflns         4143
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0446
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 1.03889(2) 0.888836(14) 0.358562(9) 0.01654(5) Uani 1 1 d . . .
Cl1 Cl 1.19021(7) 0.71614(5) 0.30889(3) 0.02635(12) Uani 1 1 d . . .
O1 O 1.0802(2) 0.78740(13) 0.52901(9) 0.0362(4) Uani 1 1 d . . .
O2 O 1.3830(2) 0.99297(15) 0.40546(9) 0.0335(4) Uani 1 1 d . . .
N1 N 1.0445(2) 0.93963(15) 0.23097(9) 0.0228(3) Uani 1 1 d . . .
N2 N 0.8226(2) 0.78298(15) 0.31820(10) 0.0221(4) Uani 1 1 d . . .
C1 C 0.9990(2) 1.09623(17) 0.37372(12) 0.0223(5) Uani 1 1 d . . .
H1 H 1.0681 1.1211 0.3313 0.027 Uiso 1 1 calc R . .
C2 C 0.8530(2) 1.02757(17) 0.36672(13) 0.0215(4) Uani 1 1 d . . .
H2 H 0.7843 1.0195 0.3212 0.026 Uiso 1 1 calc R . .
C3 C 0.8306(3) 0.97324(18) 0.44210(12) 0.0215(4) Uani 1 1 d . . .
H3 H 0.7700 0.9037 0.4523 0.026 Uiso 1 1 calc R . .
C4 C 0.9190(2) 1.04493(17) 0.50134(12) 0.0198(4) Uani 1 1 d . . .
C5 C 0.9156(3) 1.04692(18) 0.58319(13) 0.0241(5) Uani 1 1 d . . .
H5 H 0.8472 0.9943 0.6120 0.029 Uiso 1 1 calc R . .
C6 C 1.0158(3) 1.12861(18) 0.62275(12) 0.0289(5) Uani 1 1 d . . .
H6 H 1.0130 1.1324 0.6790 0.035 Uiso 1 1 calc R . .
C7 C 1.1186(3) 1.20370(19) 0.58138(14) 0.0320(5) Uani 1 1 d . . .
H7 H 1.1854 1.2581 0.6095 0.038 Uiso 1 1 calc R . .
C8 C 1.1254(3) 1.20045(18) 0.49801(13) 0.0281(5) Uani 1 1 d . . .
H8 H 1.1976 1.2509 0.4696 0.034 Uiso 1 1 calc R . .
C9 C 1.0245(3) 1.12213(17) 0.45852(11) 0.0219(4) Uani 1 1 d . . .
C10 C 1.0494(3) 0.96614(17) 0.16585(12) 0.0222(4) Uani 1 1 d . . .
C11 C 1.0580(3) 1.0000(2) 0.08284(12) 0.0296(5) Uani 1 1 d . . .
H11A H 1.1692 1.0303 0.0710 0.044 Uiso 1 1 calc R . .
H11B H 0.9751 1.0606 0.0721 0.044 Uiso 1 1 calc R . .
H11C H 1.0357 0.9318 0.0493 0.044 Uiso 1 1 calc R . .
C12 C 0.7225(3) 0.7225(2) 0.29420(12) 0.0211(4) Uani 1 1 d . . .
C13 C 0.5970(3) 0.64339(18) 0.26418(14) 0.0303(5) Uani 1 1 d . . .
H13A H 0.5895 0.6512 0.2064 0.045 Uiso 1 1 calc R . .
H13B H 0.4893 0.6625 0.2881 0.045 Uiso 1 1 calc R . .
H13C H 0.6271 0.5629 0.2778 0.045 Uiso 1 1 calc R . .
C14 C 1.0600(3) 0.82359(17) 0.46607(12) 0.0224(4) Uani 1 1 d . . .
C15 C 1.2539(3) 0.95742(19) 0.38746(11) 0.0227(5) Uani 1 1 d . . .


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

#=============================================================================
# GEOMETRY
#=============================================================================

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 C15 1.962(2) . ?
Mo1 C14 1.968(2) . ?
Mo1 C2 2.1865(19) . ?
Mo1 N2 2.2276(18) . ?
Mo1 N1 2.2283(16) . ?
Mo1 C3 2.393(2) . ?
Mo1 C1 2.4101(19) . ?
Mo1 Cl1 2.4687(6) . ?
O1 C14 1.150(2) . ?
O2 C15 1.156(3) . ?
N1 C10 1.140(2) . ?
N2 C12 1.137(3) . ?
C1 C2 1.419(3) . ?
C1 C9 1.474(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.426(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.475(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 C9 1.423(3) . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.454(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.448(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C15 Mo1 C14 81.20(8) . . ?
C15 Mo1 C2 107.28(8) . . ?
C14 Mo1 C2 106.09(8) . . ?
C15 Mo1 N2 169.41(8) . . ?
C14 Mo1 N2 98.18(7) . . ?
C2 Mo1 N2 83.10(7) . . ?
C15 Mo1 N1 96.73(7) . . ?
C14 Mo1 N1 170.50(8) . . ?
C2 Mo1 N1 83.39(7) . . ?
N2 Mo1 N1 82.14(6) . . ?
C15 Mo1 C3 108.06(8) . . ?
C14 Mo1 C3 70.85(8) . . ?
C2 Mo1 C3 35.93(8) . . ?
N2 Mo1 C3 81.50(7) . . ?
N1 Mo1 C3 118.47(7) . . ?
C15 Mo1 C1 72.34(8) . . ?
C14 Mo1 C1 106.74(7) . . ?
C2 Mo1 C1 35.54(7) . . ?
N2 Mo1 C1 117.68(6) . . ?
N1 Mo1 C1 81.24(6) . . ?
C3 Mo1 C1 56.38(7) . . ?
C15 Mo1 Cl1 88.27(6) . . ?
C14 Mo1 Cl1 88.02(6) . . ?
C2 Mo1 Cl1 160.20(6) . . ?
N2 Mo1 Cl1 81.14(5) . . ?
N1 Mo1 Cl1 82.63(5) . . ?
C3 Mo1 Cl1 150.30(5) . . ?
C1 Mo1 Cl1 153.00(5) . . ?
C10 N1 Mo1 179.13(19) . . ?
C12 N2 Mo1 173.68(17) . . ?
C2 C1 C9 107.90(17) . . ?
C2 C1 Mo1 63.60(10) . . ?
C9 C1 Mo1 106.41(13) . . ?
C2 C1 H1 126.1 . . ?
C9 C1 H1 126.1 . . ?
Mo1 C1 H1 97.9 . . ?
C1 C2 C3 105.80(18) . . ?
C1 C2 Mo1 80.86(11) . . ?
C3 C2 Mo1 79.95(11) . . ?
C1 C2 H2 127.1 . . ?
C3 C2 H2 127.1 . . ?
Mo1 C2 H2 106.0 . . ?
C2 C3 C4 107.42(18) . . ?
C2 C3 Mo1 64.12(11) . . ?
C4 C3 Mo1 106.58(13) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
Mo1 C3 H3 97.3 . . ?
C5 C4 C9 120.58(18) . . ?
C5 C4 C3 132.56(19) . . ?
C9 C4 C3 106.87(18) . . ?
C4 C5 C6 118.33(19) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C4 120.67(19) . . ?
C8 C9 C1 132.84(19) . . ?
C4 C9 C1 106.49(17) . . ?
N1 C10 C11 179.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 178.8(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 Mo1 176.69(19) . . ?
O2 C15 Mo1 176.96(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 Mo1 C1 C2 -169.13(14) . . . . ?
C14 Mo1 C1 C2 -94.40(14) . . . . ?
N2 Mo1 C1 C2 14.60(14) . . . . ?
N1 Mo1 C1 C2 90.88(13) . . . . ?
C3 Mo1 C1 C2 -42.09(13) . . . . ?
Cl1 Mo1 C1 C2 144.87(11) . . . . ?
C15 Mo1 C1 C9 -66.92(13) . . . . ?
C14 Mo1 C1 C9 7.81(15) . . . . ?
C2 Mo1 C1 C9 102.21(18) . . . . ?
N2 Mo1 C1 C9 116.81(13) . . . . ?
N1 Mo1 C1 C9 -166.91(14) . . . . ?
C3 Mo1 C1 C9 60.12(13) . . . . ?
Cl1 Mo1 C1 C9 -112.92(14) . . . . ?
C9 C1 C2 C3 -23.1(2) . . . . ?
Mo1 C1 C2 C3 76.74(13) . . . . ?
C9 C1 C2 Mo1 -99.85(14) . . . . ?
C15 Mo1 C2 C1 10.85(14) . . . . ?
C14 Mo1 C2 C1 96.43(13) . . . . ?
N2 Mo1 C2 C1 -167.01(13) . . . . ?
N1 Mo1 C2 C1 -84.18(12) . . . . ?
C3 Mo1 C2 C1 107.98(18) . . . . ?
Cl1 Mo1 C2 C1 -129.54(15) . . . . ?
C15 Mo1 C2 C3 -97.13(13) . . . . ?
C14 Mo1 C2 C3 -11.55(14) . . . . ?
N2 Mo1 C2 C3 85.01(12) . . . . ?
N1 Mo1 C2 C3 167.85(13) . . . . ?
C1 Mo1 C2 C3 -107.98(18) . . . . ?
Cl1 Mo1 C2 C3 122.48(17) . . . . ?
C1 C2 C3 C4 23.0(2) . . . . ?
Mo1 C2 C3 C4 100.38(14) . . . . ?
C1 C2 C3 Mo1 -77.42(13) . . . . ?
C15 Mo1 C3 C2 94.73(13) . . . . ?
C14 Mo1 C3 C2 168.25(14) . . . . ?
N2 Mo1 C3 C2 -89.96(12) . . . . ?
N1 Mo1 C3 C2 -13.76(14) . . . . ?
C1 Mo1 C3 C2 41.60(12) . . . . ?
Cl1 Mo1 C3 C2 -144.77(11) . . . . ?
C15 Mo1 C3 C4 -6.97(16) . . . . ?
C14 Mo1 C3 C4 66.56(14) . . . . ?
C2 Mo1 C3 C4 -101.70(18) . . . . ?
N2 Mo1 C3 C4 168.34(14) . . . . ?
N1 Mo1 C3 C4 -115.46(14) . . . . ?
C1 Mo1 C3 C4 -60.10(13) . . . . ?
Cl1 Mo1 C3 C4 113.53(13) . . . . ?
C2 C3 C4 C5 166.5(2) . . . . ?
Mo1 C3 C4 C5 -126.1(2) . . . . ?
C2 C3 C4 C9 -14.2(2) . . . . ?
Mo1 C3 C4 C9 53.27(17) . . . . ?
C9 C4 C5 C6 1.4(3) . . . . ?
C3 C4 C5 C6 -179.3(2) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 C4 -1.3(3) . . . . ?
C7 C8 C9 C1 179.5(2) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C3 C4 C9 C8 -179.47(19) . . . . ?
C5 C4 C9 C1 179.38(18) . . . . ?
C3 C4 C9 C1 -0.1(2) . . . . ?
C2 C1 C9 C8 -166.3(2) . . . . ?
Mo1 C1 C9 C8 126.7(2) . . . . ?
C2 C1 C9 C4 14.4(2) . . . . ?
Mo1 C1 C9 C4 -52.55(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.063

#=============================================================================
#   END
#=============================================================================
_database_code_depnum_ccdc_archive 'CCDC 980993'
