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

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

data_l0431a
_database_code_depnum_ccdc_archive 'CCDC 1056137'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 Mo N O4 P'
_chemical_formula_sum            'C26 H16 Mo N O4 P'
_chemical_formula_weight         533.31

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.8048(5)
_cell_length_b                   18.8955(5)
_cell_length_c                   7.3079(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2182.45(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    22962
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25398
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.680
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5011
_reflns_number_gt                4776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       Apex2
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, SADABS-2012/1'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+0.1819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5011
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0184
_refine_ls_R_factor_gt           0.0169
_refine_ls_wR_factor_ref         0.0444
_refine_ls_wR_factor_gt          0.0439
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_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 0.32736(2) 0.18459(2) 0.51511(3) 0.01664(6) Uani 1 1 d . . . . .
P1 P 0.35378(4) 0.31325(3) 0.48148(8) 0.01577(13) Uani 1 1 d . . . . .
O1 O 0.14803(13) 0.18573(10) 0.6949(3) 0.0349(5) Uani 1 1 d . . . . .
O2 O 0.33310(12) 0.02070(9) 0.5753(3) 0.0365(5) Uani 1 1 d . . . . .
O3 O 0.24345(13) 0.14906(13) 0.1285(3) 0.0408(5) Uani 1 1 d . . . . .
O4 O 0.40680(12) 0.18256(10) 0.9148(3) 0.0316(5) Uani 1 1 d . . . . .
N1 N 0.45867(12) 0.19429(9) 0.3808(3) 0.0169(4) Uani 1 1 d . . . . .
C1 C 0.32247(12) 0.39865(11) 0.5375(4) 0.0162(5) Uani 1 1 d . . . . .
C2 C 0.37997(13) 0.45445(10) 0.5284(4) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.3594 0.4998 0.5622 0.021 Uiso 1 1 calc R U . . .
C3 C 0.46460(14) 0.45060(11) 0.4747(3) 0.0164(5) Uani 1 1 d . . . . .
C4 C 0.50103(14) 0.38673(11) 0.4184(3) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.5584 0.3875 0.3795 0.020 Uiso 1 1 calc R U . . .
C5 C 0.45861(15) 0.32213(11) 0.4158(3) 0.0160(5) Uani 1 1 d . . . . .
C6 C 0.49977(13) 0.25663(12) 0.3509(3) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.57691(15) 0.25819(13) 0.2593(4) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.6039 0.3023 0.2369 0.028 Uiso 1 1 calc R U . . .
C8 C 0.61489(16) 0.19615(14) 0.2003(4) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.6677 0.1971 0.1384 0.031 Uiso 1 1 calc R U . . .
C9 C 0.57396(17) 0.13300(14) 0.2337(4) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.5983 0.0893 0.1967 0.028 Uiso 1 1 calc R U . . .
C10 C 0.49666(15) 0.13472(13) 0.3225(3) 0.0217(5) Uani 1 1 d . . . . .
H10 H 0.4686 0.0910 0.3436 0.026 Uiso 1 1 calc R U . . .
C11 C 0.23362(14) 0.41323(12) 0.5922(3) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.18656(15) 0.36513(13) 0.6967(3) 0.0211(5) Uani 1 1 d . . . . .
H12 H 0.2116 0.3218 0.7340 0.025 Uiso 1 1 calc R U . . .
C13 C 0.10368(16) 0.38018(15) 0.7465(4) 0.0259(6) Uani 1 1 d . . . . .
H13 H 0.0724 0.3470 0.8171 0.031 Uiso 1 1 calc R U . . .
C14 C 0.06631(16) 0.44325(15) 0.6940(4) 0.0283(6) Uani 1 1 d . . . . .
H14 H 0.0097 0.4535 0.7290 0.034 Uiso 1 1 calc R U . . .
C15 C 0.11210(16) 0.49147(14) 0.5896(4) 0.0265(5) Uani 1 1 d . . . . .
H15 H 0.0868 0.5349 0.5536 0.032 Uiso 1 1 calc R U . . .
C16 C 0.19445(14) 0.47642(12) 0.5380(4) 0.0213(5) Uani 1 1 d . . . . .
H16 H 0.2248 0.5093 0.4649 0.026 Uiso 1 1 calc R U . . .
C17 C 0.51752(14) 0.51575(11) 0.4771(3) 0.0165(5) Uani 1 1 d . . . . .
C18 C 0.60285(13) 0.51317(11) 0.5280(4) 0.0192(4) Uani 1 1 d . . . . .
H18 H 0.6276 0.4691 0.5604 0.023 Uiso 1 1 calc R U . . .
C19 C 0.65169(13) 0.57408(12) 0.5317(4) 0.0217(5) Uani 1 1 d . . . . .
H19 H 0.7094 0.5716 0.5675 0.026 Uiso 1 1 calc R U . . .
C20 C 0.61664(15) 0.63863(12) 0.4834(3) 0.0216(5) Uani 1 1 d . . . . .
H20 H 0.6501 0.6804 0.4873 0.026 Uiso 1 1 calc R U . . .
C21 C 0.53223(15) 0.64219(12) 0.4291(3) 0.0209(5) Uani 1 1 d . . . . .
H21 H 0.5083 0.6862 0.3932 0.025 Uiso 1 1 calc R U . . .
C22 C 0.48320(15) 0.58127(12) 0.4276(3) 0.0185(5) Uani 1 1 d . . . . .
H22 H 0.4254 0.5841 0.3923 0.022 Uiso 1 1 calc R U . . .
C23 C 0.21391(17) 0.18532(12) 0.6271(4) 0.0234(5) Uani 1 1 d . . . . .
C24 C 0.33148(14) 0.08063(13) 0.5480(4) 0.0242(6) Uani 1 1 d . . . . .
C25 C 0.27460(16) 0.16528(13) 0.2627(4) 0.0244(5) Uani 1 1 d . . . . .
C26 C 0.37884(16) 0.18701(12) 0.7706(4) 0.0219(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.
;

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 C23 1.971(3) . ?
Mo1 C24 1.980(2) . ?
Mo1 C26 2.037(3) . ?
Mo1 C25 2.057(3) . ?
Mo1 N1 2.303(2) . ?
Mo1 P1 2.4790(5) . ?
P1 C5 1.733(2) . ?
P1 C1 1.737(2) . ?
O1 C23 1.153(3) . ?
O2 C24 1.150(3) . ?
O3 C25 1.139(3) . ?
O4 C26 1.146(3) . ?
N1 C10 1.345(3) . ?
N1 C6 1.363(3) . ?
C1 C2 1.394(3) . ?
C1 C11 1.486(3) . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(3) . ?
C3 C17 1.488(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.476(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.399(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C23 Mo1 C24 89.23(9) . . ?
C23 Mo1 C26 89.01(11) . . ?
C24 Mo1 C26 84.15(10) . . ?
C23 Mo1 C25 90.28(11) . . ?
C24 Mo1 C25 86.91(10) . . ?
C26 Mo1 C25 171.04(10) . . ?
C23 Mo1 N1 174.97(8) . . ?
C24 Mo1 N1 95.79(8) . . ?
C26 Mo1 N1 91.66(9) . . ?
C25 Mo1 N1 89.83(9) . . ?
C23 Mo1 P1 100.81(7) . . ?
C24 Mo1 P1 168.35(7) . . ?
C26 Mo1 P1 90.09(6) . . ?
C25 Mo1 P1 98.82(7) . . ?
N1 Mo1 P1 74.21(5) . . ?
C5 P1 C1 104.34(10) . . ?
C5 P1 Mo1 106.47(7) . . ?
C1 P1 Mo1 147.12(8) . . ?
C10 N1 C6 117.4(2) . . ?
C10 N1 Mo1 118.08(16) . . ?
C6 N1 Mo1 124.51(14) . . ?
C2 C1 C11 119.27(19) . . ?
C2 C1 P1 120.39(16) . . ?
C11 C1 P1 120.32(16) . . ?
C1 C2 C3 126.79(19) . . ?
C1 C2 H2 116.6 . . ?
C3 C2 H2 116.6 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 C17 119.48(19) . . ?
C4 C3 C17 119.06(19) . . ?
C5 C4 C3 124.2(2) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 P1 122.76(17) . . ?
C6 C5 P1 115.40(16) . . ?
N1 C6 C7 120.9(2) . . ?
N1 C6 C5 117.6(2) . . ?
C7 C6 C5 121.5(2) . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N1 C10 C9 124.2(2) . . ?
N1 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 C1 121.9(2) . . ?
C16 C11 C1 119.9(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C22 C17 C18 118.23(19) . . ?
C22 C17 C3 120.7(2) . . ?
C18 C17 C3 121.05(19) . . ?
C19 C18 C17 120.86(19) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
O1 C23 Mo1 179.1(3) . . ?
O2 C24 Mo1 176.9(2) . . ?
O3 C25 Mo1 174.1(2) . . ?
O4 C26 Mo1 174.4(2) . . ?

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
C5 P1 C1 C2 -1.9(3) . . . . ?
Mo1 P1 C1 C2 157.22(15) . . . . ?
C5 P1 C1 C11 176.87(19) . . . . ?
Mo1 P1 C1 C11 -24.0(3) . . . . ?
C11 C1 C2 C3 -178.0(2) . . . . ?
P1 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C17 -178.7(2) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C17 C3 C4 C5 178.0(2) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C3 C4 C5 P1 0.5(3) . . . . ?
C1 P1 C5 C4 1.4(2) . . . . ?
Mo1 P1 C5 C4 -167.02(18) . . . . ?
C1 P1 C5 C6 -176.85(18) . . . . ?
Mo1 P1 C5 C6 14.77(19) . . . . ?
C10 N1 C6 C7 1.6(3) . . . . ?
Mo1 N1 C6 C7 -176.26(17) . . . . ?
C10 N1 C6 C5 -179.6(2) . . . . ?
Mo1 N1 C6 C5 2.5(3) . . . . ?
C4 C5 C6 N1 169.5(2) . . . . ?
P1 C5 C6 N1 -12.2(3) . . . . ?
C4 C5 C6 C7 -11.7(4) . . . . ?
P1 C5 C6 C7 166.53(19) . . . . ?
N1 C6 C7 C8 -1.7(4) . . . . ?
C5 C6 C7 C8 179.6(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C6 N1 C10 C9 -0.4(4) . . . . ?
Mo1 N1 C10 C9 177.6(2) . . . . ?
C8 C9 C10 N1 -0.8(4) . . . . ?
C2 C1 C11 C12 -144.7(3) . . . . ?
P1 C1 C11 C12 36.4(3) . . . . ?
C2 C1 C11 C16 35.7(3) . . . . ?
P1 C1 C11 C16 -143.1(2) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
C1 C11 C12 C13 179.8(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C12 C11 C16 C15 1.3(4) . . . . ?
C1 C11 C16 C15 -179.1(2) . . . . ?
C2 C3 C17 C22 -37.2(3) . . . . ?
C4 C3 C17 C22 142.8(2) . . . . ?
C2 C3 C17 C18 143.1(2) . . . . ?
C4 C3 C17 C18 -36.9(3) . . . . ?
C22 C17 C18 C19 0.9(4) . . . . ?
C3 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C20 C21 C22 C17 -1.0(3) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C3 C17 C22 C21 -179.9(2) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_l0131a
_database_code_depnum_ccdc_archive 'CCDC 1056138'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 N O4 P W'
_chemical_formula_sum            'C26 H16 N O4 P W'
_chemical_formula_weight         621.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.7856(4)
_cell_length_b                   18.8326(5)
_cell_length_c                   7.2886(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2166.78(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    5.440
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.1719
_exptl_absorpt_correction_T_max  0.3461
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42028
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4970
_reflns_number_gt                4846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_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       Apex2
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A, Sadabs'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0151P)²+0.8667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00074(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4970
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0114
_refine_ls_R_factor_gt           0.0108
_refine_ls_wR_factor_ref         0.0278
_refine_ls_wR_factor_gt          0.0275
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_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_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
W1 W 0.17303(2) 0.31502(2) 0.69244(2) 0.01684(4) Uani 1 1 d . . . . .
P1 P 0.14552(4) 0.18670(3) 0.66098(9) 0.01600(17) Uani 1 1 d . . . . .
O1 O 0.09311(15) 0.31858(11) 1.0925(3) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.16677(14) 0.47977(12) 0.7491(3) 0.0358(6) Uani 1 1 d . . . . .
O3 O 0.25672(15) 0.34959(16) 0.3052(3) 0.0412(6) Uani 1 1 d . . . . .
O4 O 0.35310(16) 0.31247(12) 0.8721(4) 0.0337(6) Uani 1 1 d . . . . .
N1 N 0.04218(15) 0.30591(12) 0.5585(3) 0.0180(5) Uani 1 1 d . . . . .
C1 C 0.17776(14) 0.10172(14) 0.7152(6) 0.0181(7) Uani 1 1 d . . . . .
C2 C 0.12000(14) 0.04523(12) 0.7072(5) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.1406 -0.0002 0.7420 0.021 Uiso 1 1 calc R U . . .
C3 C 0.03519(16) 0.04902(13) 0.6532(3) 0.0173(6) Uani 1 1 d . . . . .
C4 C -0.00138(16) 0.11285(14) 0.5970(4) 0.0174(5) Uani 1 1 d . . . . .
H4 H -0.0588 0.1120 0.5578 0.021 Uiso 1 1 calc R U . . .
C5 C 0.04095(17) 0.17782(13) 0.5946(4) 0.0163(5) Uani 1 1 d . . . . .
C6 C 0.00044(15) 0.24384(15) 0.5295(4) 0.0182(5) Uani 1 1 d . . . . .
C7 C -0.07727(17) 0.24272(15) 0.4381(4) 0.0237(6) Uani 1 1 d . . . . .
H7 H -0.1049 0.1987 0.4163 0.028 Uiso 1 1 calc R U . . .
C8 C -0.1143(2) 0.30495(17) 0.3793(5) 0.0262(6) Uani 1 1 d . . . . .
H8 H -0.1675 0.3044 0.3184 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0725(2) 0.36818(17) 0.4107(4) 0.0240(6) Uani 1 1 d . . . . .
H9 H -0.0963 0.4120 0.3720 0.029 Uiso 1 1 calc R U . . .
C10 C 0.00473(17) 0.36621(15) 0.4997(4) 0.0218(6) Uani 1 1 d . . . . .
H10 H 0.0332 0.4099 0.5207 0.026 Uiso 1 1 calc R U . . .
C11 C 0.26679(16) 0.08663(14) 0.7705(4) 0.0184(5) Uani 1 1 d . . . . .
C12 C 0.31361(18) 0.13456(16) 0.8756(4) 0.0212(6) Uani 1 1 d . . . . .
H12 H 0.2884 0.1778 0.9148 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3972(2) 0.11931(19) 0.9234(4) 0.0267(7) Uani 1 1 d . . . . .
H13 H 0.4288 0.1526 0.9936 0.032 Uiso 1 1 calc R U . . .
C14 C 0.43437(18) 0.05633(18) 0.8697(4) 0.0285(7) Uani 1 1 d . . . . .
H14 H 0.4911 0.0459 0.9042 0.034 Uiso 1 1 calc R U . . .
C15 C 0.38842(19) 0.00837(16) 0.7650(4) 0.0263(6) Uani 1 1 d . . . . .
H15 H 0.4138 -0.0351 0.7283 0.032 Uiso 1 1 calc R U . . .
C16 C 0.30557(17) 0.02330(14) 0.7134(6) 0.0230(6) Uani 1 1 d . . . . .
H16 H 0.2751 -0.0094 0.6393 0.028 Uiso 1 1 calc R U . . .
C17 C -0.01774(16) -0.01645(13) 0.6554(3) 0.0177(6) Uani 1 1 d . . . . .
C18 C -0.10312(15) -0.01362(12) 0.7075(5) 0.0198(5) Uani 1 1 d . . . . .
H18 H -0.1278 0.0305 0.7412 0.024 Uiso 1 1 calc R U . . .
C19 C -0.15182(16) -0.07486(14) 0.7101(6) 0.0231(6) Uani 1 1 d . . . . .
H19 H -0.2097 -0.0724 0.7453 0.028 Uiso 1 1 calc R U . . .
C20 C -0.11673(17) -0.13963(14) 0.6618(4) 0.0223(7) Uani 1 1 d . . . . .
H20 H -0.1503 -0.1815 0.6650 0.027 Uiso 1 1 calc R U . . .
C21 C -0.03225(18) -0.14314(14) 0.6087(4) 0.0209(5) Uani 1 1 d . . . . .
H21 H -0.0082 -0.1874 0.5743 0.025 Uiso 1 1 calc R U . . .
C22 C 0.01691(17) -0.08219(14) 0.6058(4) 0.0198(5) Uani 1 1 d . . . . .
H22 H 0.0747 -0.0850 0.5699 0.024 Uiso 1 1 calc R U . . .
C23 C 0.12165(18) 0.31393(13) 0.9481(4) 0.0205(6) Uani 1 1 d . . . . .
C24 C 0.16920(16) 0.41910(15) 0.7231(5) 0.0251(9) Uani 1 1 d . . . . .
C25 C 0.22521(18) 0.33370(17) 0.4413(4) 0.0245(6) Uani 1 1 d . . . . .
C26 C 0.2867(2) 0.31346(14) 0.8043(4) 0.0222(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
W1 C26 1.971(3) . ?
W1 C24 1.974(3) . ?
W1 C23 2.032(3) . ?
W1 C25 2.038(3) . ?
W1 N1 2.291(2) . ?
W1 P1 2.4660(6) . ?
P1 C1 1.725(3) . ?
P1 C5 1.728(3) . ?
O1 C23 1.148(4) . ?
O2 C24 1.159(4) . ?
O3 C25 1.149(4) . ?
O4 C26 1.160(4) . ?
N1 C10 1.350(4) . ?
N1 C6 1.358(3) . ?
C1 C2 1.402(3) . ?
C1 C11 1.489(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 C17 1.490(3) . ?
C4 C5 1.394(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.476(4) . ?
C6 C7 1.396(4) . ?
C7 C8 1.378(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.396(4) . ?
C11 C16 1.404(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.401(4) . ?
C17 C18 1.401(4) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C26 W1 C24 89.76(11) . . ?
C26 W1 C23 89.08(12) . . ?
C24 W1 C23 83.91(13) . . ?
C26 W1 C25 90.34(12) . . ?
C24 W1 C25 86.71(14) . . ?
C23 W1 C25 170.61(11) . . ?
C26 W1 N1 174.78(9) . . ?
C24 W1 N1 95.46(10) . . ?
C23 W1 N1 91.73(10) . . ?
C25 W1 N1 89.70(10) . . ?
C26 W1 P1 100.61(8) . . ?
C24 W1 P1 168.06(7) . . ?
C23 W1 P1 90.29(7) . . ?
C25 W1 P1 99.02(9) . . ?
N1 W1 P1 74.23(6) . . ?
C1 P1 C5 104.84(12) . . ?
C1 P1 W1 146.71(10) . . ?
C5 P1 W1 106.80(9) . . ?
C10 N1 C6 117.5(2) . . ?
C10 N1 W1 117.85(18) . . ?
C6 N1 W1 124.62(17) . . ?
C2 C1 C11 118.7(2) . . ?
C2 C1 P1 120.17(18) . . ?
C11 C1 P1 121.15(19) . . ?
C3 C2 C1 126.6(2) . . ?
C3 C2 H2 116.7 . . ?
C1 C2 H2 116.7 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 C17 119.0(2) . . ?
C2 C3 C17 119.5(2) . . ?
C5 C4 C3 124.2(2) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 P1 122.6(2) . . ?
C6 C5 P1 114.97(19) . . ?
N1 C6 C7 120.9(2) . . ?
N1 C6 C5 117.7(2) . . ?
C7 C6 C5 121.4(2) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 118.7(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N1 C10 C9 123.9(3) . . ?
N1 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C1 121.7(3) . . ?
C16 C11 C1 119.6(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C17 C18 118.6(2) . . ?
C22 C17 C3 120.7(2) . . ?
C18 C17 C3 120.7(2) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
O1 C23 W1 175.0(2) . . ?
O2 C24 W1 177.1(3) . . ?
O3 C25 W1 174.4(3) . . ?
O4 C26 W1 179.2(3) . . ?

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
C5 P1 C1 C2 -2.9(4) . . . . ?
W1 P1 C1 C2 158.6(2) . . . . ?
C5 P1 C1 C11 176.9(3) . . . . ?
W1 P1 C1 C11 -21.6(5) . . . . ?
C11 C1 C2 C3 -178.0(3) . . . . ?
P1 C1 C2 C3 1.8(6) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C1 C2 C3 C17 -179.1(3) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C17 C3 C4 C5 177.9(2) . . . . ?
C3 C4 C5 C6 178.4(2) . . . . ?
C3 C4 C5 P1 0.4(4) . . . . ?
C1 P1 C5 C4 1.9(3) . . . . ?
W1 P1 C5 C4 -167.6(2) . . . . ?
C1 P1 C5 C6 -176.3(2) . . . . ?
W1 P1 C5 C6 14.2(2) . . . . ?
C10 N1 C6 C7 1.5(4) . . . . ?
W1 N1 C6 C7 -176.6(2) . . . . ?
C10 N1 C6 C5 -179.7(2) . . . . ?
W1 N1 C6 C5 2.2(3) . . . . ?
C4 C5 C6 N1 170.2(2) . . . . ?
P1 C5 C6 N1 -11.6(3) . . . . ?
C4 C5 C6 C7 -11.0(4) . . . . ?
P1 C5 C6 C7 167.1(2) . . . . ?
N1 C6 C7 C8 -1.6(4) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C6 N1 C10 C9 -0.7(4) . . . . ?
W1 N1 C10 C9 177.5(2) . . . . ?
C8 C9 C10 N1 -0.1(5) . . . . ?
C2 C1 C11 C12 -144.2(3) . . . . ?
P1 C1 C11 C12 36.0(4) . . . . ?
C2 C1 C11 C16 36.9(5) . . . . ?
P1 C1 C11 C16 -142.9(3) . . . . ?
C16 C11 C12 C13 -0.4(4) . . . . ?
C1 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C11 -1.5(5) . . . . ?
C12 C11 C16 C15 1.5(5) . . . . ?
C1 C11 C16 C15 -179.6(3) . . . . ?
C4 C3 C17 C22 142.9(2) . . . . ?
C2 C3 C17 C22 -37.0(4) . . . . ?
C4 C3 C17 C18 -37.3(4) . . . . ?
C2 C3 C17 C18 142.8(3) . . . . ?
C22 C17 C18 C19 0.2(5) . . . . ?
C3 C17 C18 C19 -179.6(3) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C18 C17 C22 C21 -0.1(4) . . . . ?
C3 C17 C22 C21 179.7(2) . . . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_l0482a
_database_code_depnum_ccdc_archive 'CCDC 1056139'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 Cr N2 O4'
_chemical_formula_sum            'C26 H16 Cr N2 O4'
_chemical_formula_weight         472.41

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'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.5048(2)
_cell_length_b                   10.4930(3)
_cell_length_c                   12.1845(3)
_cell_angle_alpha                100.514(1)
_cell_angle_beta                 107.177(1)
_cell_angle_gamma                104.629(1)
_cell_volume                     1079.05(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17676
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.567
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19024
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.821
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4942
_reflns_number_gt                4747
_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       Apex2
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, SADABS-2012/1'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+0.7283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4942
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_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
Cr1 Cr 0.34168(2) 0.27708(2) 0.18737(2) 0.01321(6) Uani 1 1 d . . . . .
O1 O 0.39770(15) 0.32451(14) 0.45255(10) 0.0396(3) Uani 1 1 d . . . . .
O2 O 0.11082(11) 0.41870(10) 0.21189(10) 0.0262(2) Uani 1 1 d . . . . .
O3 O 0.19911(12) 0.23263(10) -0.08165(9) 0.0267(2) Uani 1 1 d . . . . .
O4 O 0.08245(12) 0.02517(11) 0.15562(11) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.54912(11) 0.44231(10) 0.21679(9) 0.01309(19) Uani 1 1 d . . . . .
N2 N 0.50710(12) 0.17838(10) 0.17994(9) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.56671(13) 0.57780(12) 0.23800(10) 0.0135(2) Uani 1 1 d . . . . .
C2 C 0.71183(14) 0.67836(12) 0.29691(11) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.7147(18) 0.7709(17) 0.3119(14) 0.020(4) Uiso 1 1 d . . . . .
C3 C 0.84760(14) 0.64363(12) 0.33006(11) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.82937(14) 0.50404(13) 0.29753(11) 0.0158(2) Uani 1 1 d . . . . .
H4 H 0.9163(19) 0.4748(16) 0.3114(14) 0.020(4) Uiso 1 1 d . . . . .
C5 C 0.68127(14) 0.40753(12) 0.24233(11) 0.0141(2) Uani 1 1 d . . . . .
C6 C 0.65569(14) 0.25882(12) 0.20809(11) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.77364(15) 0.20365(13) 0.20389(12) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.8767 0.2623 0.2226 0.024 Uiso 1 1 calc R U . . .
C8 C 0.73909(16) 0.06262(14) 0.17216(13) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.8177 0.0231 0.1683 0.026 Uiso 1 1 calc R U . . .
C9 C 0.58768(16) -0.01990(13) 0.14612(12) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.5612 -0.1169 0.1257 0.026 Uiso 1 1 calc R U . . .
C10 C 0.47577(15) 0.04149(13) 0.15034(12) 0.0192(2) Uani 1 1 d . . . . .
H10 H 0.3720 -0.0156 0.1315 0.023 Uiso 1 1 calc R U . . .
C11 C 0.42766(13) 0.61988(12) 0.19105(11) 0.0137(2) Uani 1 1 d . . . . .
C12 C 0.34115(14) 0.57480(13) 0.06849(11) 0.0165(2) Uani 1 1 d . . . . .
H12 H 0.3702 0.5162 0.0165 0.020 Uiso 1 1 calc R U . . .
C13 C 0.21273(15) 0.61532(14) 0.02230(12) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.1528 0.5828 -0.0609 0.025 Uiso 1 1 calc R U . . .
C14 C 0.17200(15) 0.70341(14) 0.09775(13) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.0842 0.7311 0.0662 0.026 Uiso 1 1 calc R U . . .
C15 C 0.25951(15) 0.75083(13) 0.21913(12) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.2323 0.8120 0.2704 0.024 Uiso 1 1 calc R U . . .
C16 C 0.38705(14) 0.70926(13) 0.26611(11) 0.0171(2) Uani 1 1 d . . . . .
H16 H 0.4465 0.7418 0.3494 0.021 Uiso 1 1 calc R U . . .
C17 C 1.00318(14) 0.74934(13) 0.39425(11) 0.0167(2) Uani 1 1 d . . . . .
C18 C 1.12747(15) 0.71663(15) 0.46436(12) 0.0229(3) Uani 1 1 d . . . . .
H18 H 1.1123 0.6257 0.4709 0.027 Uiso 1 1 calc R U . . .
C19 C 1.27289(16) 0.81602(17) 0.52451(12) 0.0277(3) Uani 1 1 d . . . . .
H19 H 1.3566 0.7925 0.5714 0.033 Uiso 1 1 calc R U . . .
C20 C 1.29647(16) 0.94931(16) 0.51647(13) 0.0288(3) Uani 1 1 d . . . . .
H20 H 1.3958 1.0173 0.5583 0.035 Uiso 1 1 calc R U . . .
C21 C 1.17479(17) 0.98303(14) 0.44725(14) 0.0270(3) Uani 1 1 d . . . . .
H21 H 1.1908 1.0743 0.4415 0.032 Uiso 1 1 calc R U . . .
C22 C 1.02905(15) 0.88379(13) 0.38597(12) 0.0209(3) Uani 1 1 d . . . . .
H22 H 0.9464 0.9077 0.3381 0.025 Uiso 1 1 calc R U . . .
C23 C 0.38882(15) 0.30752(14) 0.35487(12) 0.0214(3) Uani 1 1 d . . . . .
C24 C 0.20443(14) 0.37003(13) 0.20012(11) 0.0174(2) Uani 1 1 d . . . . .
C25 C 0.25940(14) 0.24913(12) 0.01863(12) 0.0176(2) Uani 1 1 d . . . . .
C26 C 0.18461(15) 0.12099(14) 0.16748(12) 0.0212(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cr1 C26 1.8375(13) . ?
Cr1 C24 1.8396(13) . ?
Cr1 C23 1.9021(14) . ?
Cr1 C25 1.9076(13) . ?
Cr1 N2 2.1037(10) . ?
Cr1 N1 2.1566(10) . ?
O1 C23 1.1450(18) . ?
O2 C24 1.1624(16) . ?
O3 C25 1.1447(16) . ?
O4 C26 1.1600(17) . ?
N1 C1 1.3550(15) . ?
N1 C5 1.3601(15) . ?
N2 C10 1.3466(16) . ?
N2 C6 1.3530(15) . ?
C1 C2 1.3910(17) . ?
C1 C11 1.4864(16) . ?
C2 C3 1.3945(17) . ?
C2 H2 0.946(16) . ?
C3 C4 1.3971(17) . ?
C3 C17 1.4834(16) . ?
C4 C5 1.3898(17) . ?
C4 H4 0.933(16) . ?
C5 C6 1.4762(16) . ?
C6 C7 1.3948(17) . ?
C7 C8 1.3848(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3864(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3839(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.3941(17) . ?
C11 C12 1.3966(17) . ?
C12 C13 1.3896(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3894(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3865(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3914(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3973(18) . ?
C17 C18 1.3996(18) . ?
C18 C19 1.3892(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3919(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C26 Cr1 C24 86.52(6) . . ?
C26 Cr1 C23 87.12(6) . . ?
C24 Cr1 C23 82.90(6) . . ?
C26 Cr1 C25 88.00(6) . . ?
C24 Cr1 C25 87.90(5) . . ?
C23 Cr1 C25 169.83(5) . . ?
C26 Cr1 N2 95.48(5) . . ?
C24 Cr1 N2 177.21(5) . . ?
C23 Cr1 N2 95.24(5) . . ?
C25 Cr1 N2 94.11(5) . . ?
C26 Cr1 N1 171.36(5) . . ?
C24 Cr1 N1 101.71(5) . . ?
C23 Cr1 N1 91.24(5) . . ?
C25 Cr1 N1 94.87(5) . . ?
N2 Cr1 N1 76.20(4) . . ?
C1 N1 C5 117.07(10) . . ?
C1 N1 Cr1 127.11(8) . . ?
C5 N1 Cr1 114.11(8) . . ?
C10 N2 C6 117.98(11) . . ?
C10 N2 Cr1 124.69(8) . . ?
C6 N2 Cr1 117.33(8) . . ?
N1 C1 C2 122.04(11) . . ?
N1 C1 C11 118.84(10) . . ?
C2 C1 C11 119.04(10) . . ?
C1 C2 C3 121.04(11) . . ?
C1 C2 H2 117.4(10) . . ?
C3 C2 H2 121.6(10) . . ?
C2 C3 C4 116.35(11) . . ?
C2 C3 C17 121.81(11) . . ?
C4 C3 C17 121.83(11) . . ?
C5 C4 C3 120.19(11) . . ?
C5 C4 H4 119.4(10) . . ?
C3 C4 H4 120.4(10) . . ?
N1 C5 C4 122.83(11) . . ?
N1 C5 C6 114.89(10) . . ?
C4 C5 C6 122.28(11) . . ?
N2 C6 C7 121.87(11) . . ?
N2 C6 C5 114.70(10) . . ?
C7 C6 C5 123.43(11) . . ?
C8 C7 C6 119.38(12) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 118.80(12) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 118.85(12) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 123.09(12) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C16 C11 C12 119.44(11) . . ?
C16 C11 C1 121.19(11) . . ?
C12 C11 C1 119.28(11) . . ?
C13 C12 C11 120.26(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.00(12) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.98(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.28(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.03(12) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 118.48(12) . . ?
C22 C17 C3 120.76(11) . . ?
C18 C17 C3 120.76(12) . . ?
C19 C18 C17 120.56(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.34(14) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.73(13) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.28(14) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.61(13) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
O1 C23 Cr1 171.28(12) . . ?
O2 C24 Cr1 173.48(11) . . ?
O3 C25 Cr1 174.56(11) . . ?
O4 C26 Cr1 177.70(12) . . ?

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
C5 N1 C1 C2 -7.84(17) . . . . ?
Cr1 N1 C1 C2 156.29(9) . . . . ?
C5 N1 C1 C11 168.79(10) . . . . ?
Cr1 N1 C1 C11 -27.07(15) . . . . ?
N1 C1 C2 C3 4.21(18) . . . . ?
C11 C1 C2 C3 -172.43(11) . . . . ?
C1 C2 C3 C4 1.94(18) . . . . ?
C1 C2 C3 C17 -179.23(11) . . . . ?
C2 C3 C4 C5 -4.12(17) . . . . ?
C17 C3 C4 C5 177.05(11) . . . . ?
C1 N1 C5 C4 5.60(17) . . . . ?
Cr1 N1 C5 C4 -160.59(9) . . . . ?
C1 N1 C5 C6 -175.03(10) . . . . ?
Cr1 N1 C5 C6 18.79(13) . . . . ?
C3 C4 C5 N1 0.39(18) . . . . ?
C3 C4 C5 C6 -178.94(11) . . . . ?
C10 N2 C6 C7 1.76(18) . . . . ?
Cr1 N2 C6 C7 -178.83(9) . . . . ?
C10 N2 C6 C5 -178.58(11) . . . . ?
Cr1 N2 C6 C5 0.83(14) . . . . ?
N1 C5 C6 N2 -13.22(15) . . . . ?
C4 C5 C6 N2 166.16(11) . . . . ?
N1 C5 C6 C7 166.43(12) . . . . ?
C4 C5 C6 C7 -14.19(19) . . . . ?
N2 C6 C7 C8 -1.2(2) . . . . ?
C5 C6 C7 C8 179.19(12) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
C6 N2 C10 C9 -0.79(19) . . . . ?
Cr1 N2 C10 C9 179.84(10) . . . . ?
C8 C9 C10 N2 -0.8(2) . . . . ?
N1 C1 C11 C16 126.15(12) . . . . ?
C2 C1 C11 C16 -57.11(16) . . . . ?
N1 C1 C11 C12 -57.31(15) . . . . ?
C2 C1 C11 C12 119.43(13) . . . . ?
C16 C11 C12 C13 -1.99(18) . . . . ?
C1 C11 C12 C13 -178.59(11) . . . . ?
C11 C12 C13 C14 1.41(19) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C11 0.19(19) . . . . ?
C12 C11 C16 C15 1.19(18) . . . . ?
C1 C11 C16 C15 177.72(11) . . . . ?
C2 C3 C17 C22 -23.83(18) . . . . ?
C4 C3 C17 C22 154.94(12) . . . . ?
C2 C3 C17 C18 156.27(12) . . . . ?
C4 C3 C17 C18 -24.97(18) . . . . ?
C22 C17 C18 C19 0.2(2) . . . . ?
C3 C17 C18 C19 -179.87(12) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C17 0.6(2) . . . . ?
C18 C17 C22 C21 -0.72(19) . . . . ?
C3 C17 C22 C21 179.37(12) . . . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_l0485a
_database_code_depnum_ccdc_archive 'CCDC 1056140'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 Mo N2 O4'
_chemical_formula_sum            'C26 H16 Mo N2 O4'
_chemical_formula_weight         516.35

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'
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'
O O 0.0106 0.0060 '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                   9.6294(4)
_cell_length_b                   10.4368(4)
_cell_length_c                   12.2967(4)
_cell_angle_alpha                100.380(2)
_cell_angle_beta                 107.819(2)
_cell_angle_gamma                103.596(2)
_cell_volume                     1100.31(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    16795
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.36
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6924
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17388
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_av_R_equivalents  0.0099
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.808
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5031
_reflns_number_gt                4941
_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       Apex2
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, SADABS-2012/1'
_computing_structure_solution    'coordinates from Cr-complex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+0.7084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5031
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0462
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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_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 0.33741(2) 0.27807(2) 0.18633(2) 0.01391(4) Uani 1 1 d . . . . .
O1 O 0.38968(17) 0.32832(16) 0.45994(11) 0.0466(3) Uani 1 1 d . . . . .
O2 O 0.10324(12) 0.43270(11) 0.20994(10) 0.0275(2) Uani 1 1 d . . . . .
O3 O 0.18781(13) 0.23908(11) -0.09152(9) 0.0283(2) Uani 1 1 d . . . . .
O4 O 0.07962(13) 0.01400(12) 0.15347(12) 0.0368(3) Uani 1 1 d . . . . .
N1 N 0.55791(12) 0.44720(11) 0.21816(9) 0.0138(2) Uani 1 1 d . . . . .
N2 N 0.51814(12) 0.17832(11) 0.18039(10) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.57571(14) 0.58325(13) 0.24108(11) 0.0142(2) Uani 1 1 d . . . . .
C2 C 0.71910(15) 0.68149(13) 0.30074(11) 0.0163(2) Uani 1 1 d . . . . .
H2 H 0.7255(19) 0.7754(18) 0.3186(15) 0.022(4) Uiso 1 1 d . . . . .
C3 C 0.85206(14) 0.64312(13) 0.33288(11) 0.0159(2) Uani 1 1 d . . . . .
C4 C 0.83323(15) 0.50312(14) 0.29967(12) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.9163(19) 0.4712(17) 0.3148(14) 0.017(4) Uiso 1 1 d . . . . .
C5 C 0.68722(14) 0.40892(13) 0.24370(11) 0.0151(2) Uani 1 1 d . . . . .
C6 C 0.66318(15) 0.25950(13) 0.20890(11) 0.0161(2) Uani 1 1 d . . . . .
C7 C 0.78091(16) 0.20477(14) 0.20463(13) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.8816 0.2636 0.2234 0.025 Uiso 1 1 calc R U . . .
C8 C 0.74961(17) 0.06380(15) 0.17267(14) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.8283 0.0247 0.1688 0.029 Uiso 1 1 calc R U . . .
C9 C 0.60185(17) -0.01923(14) 0.14650(13) 0.0233(3) Uani 1 1 d . . . . .
H9 H 0.5779 -0.1161 0.1261 0.028 Uiso 1 1 calc R U . . .
C10 C 0.48981(16) 0.04151(14) 0.15058(12) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.3883 -0.0158 0.1315 0.024 Uiso 1 1 calc R U . . .
C11 C 0.43805(14) 0.62701(12) 0.19455(11) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.35165(15) 0.58168(13) 0.07292(12) 0.0175(2) Uani 1 1 d . . . . .
H12 H 0.3806 0.5227 0.0217 0.021 Uiso 1 1 calc R U . . .
C13 C 0.22364(16) 0.62246(15) 0.02654(12) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.1641 0.5899 -0.0560 0.026 Uiso 1 1 calc R U . . .
C14 C 0.18280(16) 0.71076(15) 0.10092(13) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.0954 0.7388 0.0693 0.027 Uiso 1 1 calc R U . . .
C15 C 0.26957(16) 0.75792(14) 0.22119(13) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.2419 0.8189 0.2718 0.026 Uiso 1 1 calc R U . . .
C16 C 0.39706(15) 0.71650(13) 0.26841(12) 0.0183(2) Uani 1 1 d . . . . .
H16 H 0.4562 0.7493 0.3510 0.022 Uiso 1 1 calc R U . . .
C17 C 1.00638(15) 0.74581(14) 0.39674(11) 0.0179(2) Uani 1 1 d . . . . .
C18 C 1.12875(16) 0.70868(16) 0.46401(13) 0.0240(3) Uani 1 1 d . . . . .
H18 H 1.1133 0.6168 0.4687 0.029 Uiso 1 1 calc R U . . .
C19 C 1.27292(17) 0.80540(18) 0.52411(13) 0.0300(3) Uani 1 1 d . . . . .
H19 H 1.3554 0.7791 0.5693 0.036 Uiso 1 1 calc R U . . .
C20 C 1.29688(17) 0.93936(18) 0.51847(14) 0.0315(4) Uani 1 1 d . . . . .
H20 H 1.3952 1.0052 0.5605 0.038 Uiso 1 1 calc R U . . .
C21 C 1.17731(18) 0.97746(16) 0.45145(15) 0.0296(3) Uani 1 1 d . . . . .
H21 H 1.1939 1.0694 0.4470 0.035 Uiso 1 1 calc R U . . .
C22 C 1.03288(16) 0.88137(14) 0.39062(13) 0.0228(3) Uani 1 1 d . . . . .
H22 H 0.9515 0.9082 0.3445 0.027 Uiso 1 1 calc R U . . .
C23 C 0.38430(17) 0.31049(16) 0.36389(13) 0.0245(3) Uani 1 1 d . . . . .
C24 C 0.19205(15) 0.37835(14) 0.19857(12) 0.0184(3) Uani 1 1 d . . . . .
C25 C 0.24875(15) 0.25113(13) 0.00716(12) 0.0189(3) Uani 1 1 d . . . . .
C26 C 0.17519(16) 0.11237(15) 0.16521(14) 0.0227(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 C26 1.9540(14) . ?
Mo1 C24 1.9591(14) . ?
Mo1 C23 2.0357(15) . ?
Mo1 C25 2.0432(14) . ?
Mo1 N2 2.2405(11) . ?
Mo1 N1 2.2929(10) . ?
O1 C23 1.1451(19) . ?
O2 C24 1.1599(17) . ?
O3 C25 1.1433(18) . ?
O4 C26 1.1588(18) . ?
N1 C1 1.3553(16) . ?
N1 C5 1.3596(16) . ?
N2 C10 1.3470(17) . ?
N2 C6 1.3522(16) . ?
C1 C2 1.3926(17) . ?
C1 C11 1.4859(17) . ?
C2 C3 1.3944(18) . ?
C2 H2 0.948(17) . ?
C3 C4 1.3964(18) . ?
C3 C17 1.4857(17) . ?
C4 C5 1.3896(18) . ?
C4 H4 0.917(17) . ?
C5 C6 1.4825(17) . ?
C6 C7 1.3945(18) . ?
C7 C8 1.3858(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3826(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.3929(18) . ?
C11 C12 1.3970(18) . ?
C12 C13 1.3891(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3909(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.397(2) . ?
C17 C18 1.3987(19) . ?
C18 C19 1.392(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C26 Mo1 C24 86.87(6) . . ?
C26 Mo1 C23 86.74(6) . . ?
C24 Mo1 C23 82.15(6) . . ?
C26 Mo1 C25 88.26(6) . . ?
C24 Mo1 C25 87.06(5) . . ?
C23 Mo1 C25 168.34(5) . . ?
C26 Mo1 N2 97.11(5) . . ?
C24 Mo1 N2 175.62(5) . . ?
C23 Mo1 N2 96.20(5) . . ?
C25 Mo1 N2 94.87(5) . . ?
C26 Mo1 N1 169.08(5) . . ?
C24 Mo1 N1 103.64(5) . . ?
C23 Mo1 N1 91.68(5) . . ?
C25 Mo1 N1 95.18(4) . . ?
N2 Mo1 N1 72.30(4) . . ?
C1 N1 C5 117.43(11) . . ?
C1 N1 Mo1 125.56(8) . . ?
C5 N1 Mo1 115.04(8) . . ?
C10 N2 C6 118.32(11) . . ?
C10 N2 Mo1 123.31(9) . . ?
C6 N2 Mo1 118.37(8) . . ?
N1 C1 C2 121.99(11) . . ?
N1 C1 C11 118.20(11) . . ?
C2 C1 C11 119.72(11) . . ?
C1 C2 C3 120.79(12) . . ?
C1 C2 H2 119.1(10) . . ?
C3 C2 H2 120.1(10) . . ?
C2 C3 C4 116.56(12) . . ?
C2 C3 C17 121.88(12) . . ?
C4 C3 C17 121.54(12) . . ?
C5 C4 C3 120.35(12) . . ?
C5 C4 H4 118.6(10) . . ?
C3 C4 H4 121.0(10) . . ?
N1 C5 C4 122.49(12) . . ?
N1 C5 C6 115.82(11) . . ?
C4 C5 C6 121.69(11) . . ?
N2 C6 C7 121.59(12) . . ?
N2 C6 C5 115.56(11) . . ?
C7 C6 C5 122.85(12) . . ?
C8 C7 C6 119.38(13) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 118.96(13) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 118.78(13) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 122.95(13) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C16 C11 C12 119.34(12) . . ?
C16 C11 C1 121.60(12) . . ?
C12 C11 C1 119.00(11) . . ?
C13 C12 C11 120.33(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.95(13) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.96(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.40(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.00(13) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 118.48(13) . . ?
C22 C17 C3 120.87(12) . . ?
C18 C17 C3 120.65(13) . . ?
C19 C18 C17 120.43(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.43(15) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.84(14) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.16(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.65(14) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
O1 C23 Mo1 170.39(13) . . ?
O2 C24 Mo1 175.82(12) . . ?
O3 C25 Mo1 173.66(12) . . ?
O4 C26 Mo1 179.50(15) . . ?

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
C5 N1 C1 C2 -7.19(18) . . . . ?
Mo1 N1 C1 C2 155.99(9) . . . . ?
C5 N1 C1 C11 169.31(11) . . . . ?
Mo1 N1 C1 C11 -27.51(15) . . . . ?
N1 C1 C2 C3 4.07(19) . . . . ?
C11 C1 C2 C3 -172.38(11) . . . . ?
C1 C2 C3 C4 1.47(18) . . . . ?
C1 C2 C3 C17 -179.90(12) . . . . ?
C2 C3 C4 C5 -3.62(18) . . . . ?
C17 C3 C4 C5 177.75(12) . . . . ?
C1 N1 C5 C4 4.97(18) . . . . ?
Mo1 N1 C5 C4 -159.97(10) . . . . ?
C1 N1 C5 C6 -175.48(11) . . . . ?
Mo1 N1 C5 C6 19.58(13) . . . . ?
C3 C4 C5 N1 0.44(19) . . . . ?
C3 C4 C5 C6 -179.08(12) . . . . ?
C10 N2 C6 C7 1.88(19) . . . . ?
Mo1 N2 C6 C7 -178.53(10) . . . . ?
C10 N2 C6 C5 -178.55(11) . . . . ?
Mo1 N2 C6 C5 1.04(15) . . . . ?
N1 C5 C6 N2 -13.95(16) . . . . ?
C4 C5 C6 N2 165.60(12) . . . . ?
N1 C5 C6 C7 165.61(12) . . . . ?
C4 C5 C6 C7 -14.8(2) . . . . ?
N2 C6 C7 C8 -1.3(2) . . . . ?
C5 C6 C7 C8 179.18(13) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.4(2) . . . . ?
C6 N2 C10 C9 -0.8(2) . . . . ?
Mo1 N2 C10 C9 179.63(11) . . . . ?
C8 C9 C10 N2 -0.9(2) . . . . ?
N1 C1 C11 C16 126.75(13) . . . . ?
C2 C1 C11 C16 -56.66(17) . . . . ?
N1 C1 C11 C12 -56.00(16) . . . . ?
C2 C1 C11 C12 120.58(14) . . . . ?
C16 C11 C12 C13 -1.76(19) . . . . ?
C1 C11 C12 C13 -179.06(12) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 1.15(19) . . . . ?
C1 C11 C16 C15 178.39(12) . . . . ?
C2 C3 C17 C22 -23.04(19) . . . . ?
C4 C3 C17 C22 155.52(13) . . . . ?
C2 C3 C17 C18 157.24(13) . . . . ?
C4 C3 C17 C18 -24.20(19) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
C3 C17 C18 C19 -179.70(13) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C17 0.3(2) . . . . ?
C18 C17 C22 C21 -0.8(2) . . . . ?
C3 C17 C22 C21 179.43(13) . . . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_l0158a
_database_code_depnum_ccdc_archive 'CCDC 1056141'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 N2 O4 W'
_chemical_formula_sum            'C26 H16 N2 O4 W'
_chemical_formula_weight         604.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.0777(2)
_cell_length_b                   15.6562(4)
_cell_length_c                   18.1170(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.058(1)
_cell_angle_gamma                90
_cell_volume                     2152.22(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    53057
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    5.404
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3575
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60945
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4947
_reflns_number_gt                4638
_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       Apex2
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+1.4021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4947
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0129
_refine_ls_R_factor_gt           0.0114
_refine_ls_wR_factor_ref         0.0268
_refine_ls_wR_factor_gt          0.0265
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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
W1 W 0.61122(2) 0.39280(2) 0.71555(2) 0.02000(2) Uani 1 1 d . . . . .
O1 O 0.85727(19) 0.55363(9) 0.72326(9) 0.0442(3) Uani 1 1 d . . . . .
O2 O 0.94964(16) 0.27997(8) 0.76204(7) 0.0297(3) Uani 1 1 d . . . . .
O3 O 0.46064(18) 0.22837(9) 0.77187(8) 0.0383(3) Uani 1 1 d . . . . .
O4 O 0.6942(2) 0.44927(10) 0.89034(7) 0.0463(4) Uani 1 1 d . . . . .
N1 N 0.36395(17) 0.47184(8) 0.65262(7) 0.0198(3) Uani 1 1 d . . . . .
N2 N 0.52398(17) 0.35874(8) 0.58834(7) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.2834(2) 0.52965(10) 0.68498(9) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.1843(2) 0.59714(10) 0.64187(9) 0.0217(3) Uani 1 1 d . . . . .
H2 H 0.1323 0.6370 0.6669 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1602(2) 0.60706(10) 0.56203(9) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.2285(2) 0.54235(10) 0.52801(9) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.2083 0.5436 0.4732 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3253(2) 0.47626(10) 0.57325(9) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.3925(2) 0.40565(10) 0.53815(9) 0.0205(3) Uani 1 1 d . . . . .
C7 C 0.3180(2) 0.38483(11) 0.45884(9) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.2250 0.4185 0.4250 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3802(2) 0.31489(11) 0.42970(10) 0.0275(3) Uani 1 1 d . . . . .
H8 H 0.3301 0.2994 0.3759 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5168(2) 0.26794(11) 0.48055(10) 0.0267(3) Uani 1 1 d . . . . .
H9 H 0.5633 0.2201 0.4620 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5850(2) 0.29152(10) 0.55882(9) 0.0239(3) Uani 1 1 d . . . . .
H10 H 0.6790 0.2589 0.5933 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2925(2) 0.51550(10) 0.76752(9) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.3353(3) 0.58071(11) 0.82277(10) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.3657 0.6357 0.8092 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3335(3) 0.56536(12) 0.89796(11) 0.0409(5) Uani 1 1 d . . . . .
H13 H 0.3651 0.6098 0.9359 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2866(3) 0.48646(12) 0.91833(10) 0.0331(4) Uani 1 1 d . . . . .
H14 H 0.2861 0.4767 0.9700 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2402(2) 0.42167(11) 0.86314(10) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.2059 0.3675 0.8765 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2440(2) 0.43602(10) 0.78809(9) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.2133 0.3912 0.7504 0.026 Uiso 1 1 calc R U . . .
C17 C 0.0671(2) 0.68116(10) 0.51501(9) 0.0209(3) Uani 1 1 d . . . . .
C18 C -0.0125(2) 0.67559(11) 0.43329(9) 0.0254(3) Uani 1 1 d . . . . .
H18 H -0.0124 0.6226 0.4077 0.030 Uiso 1 1 calc R U . . .
C19 C -0.0912(2) 0.74610(12) 0.38939(10) 0.0302(4) Uani 1 1 d . . . . .
H19 H -0.1434 0.7415 0.3339 0.036 Uiso 1 1 calc R U . . .
C20 C -0.0942(2) 0.82359(12) 0.42592(10) 0.0324(4) Uani 1 1 d . . . . .
H20 H -0.1499 0.8718 0.3957 0.039 Uiso 1 1 calc R U . . .
C21 C -0.0155(2) 0.83028(11) 0.50671(10) 0.0303(4) Uani 1 1 d . . . . .
H21 H -0.0163 0.8834 0.5319 0.036 Uiso 1 1 calc R U . . .
C22 C 0.0646(2) 0.75967(11) 0.55097(10) 0.0259(3) Uani 1 1 d . . . . .
H22 H 0.1183 0.7649 0.6063 0.031 Uiso 1 1 calc R U . . .
C23 C 0.7626(2) 0.49674(12) 0.71389(10) 0.0282(4) Uani 1 1 d . . . . .
C24 C 0.8257(2) 0.32409(11) 0.74594(9) 0.0232(3) Uani 1 1 d . . . . .
C25 C 0.5024(2) 0.28836(11) 0.74568(10) 0.0255(3) Uani 1 1 d . . . . .
C26 C 0.6622(2) 0.42840(12) 0.82570(10) 0.0296(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
W1 C24 1.9511(17) . ?
W1 C26 1.9747(17) . ?
W1 C25 2.0185(18) . ?
W1 C23 2.0421(18) . ?
W1 N2 2.2312(13) . ?
W1 N1 2.2932(13) . ?
O1 C23 1.148(2) . ?
O2 C24 1.168(2) . ?
O3 C25 1.154(2) . ?
O4 C26 1.156(2) . ?
N1 C1 1.360(2) . ?
N1 C5 1.3645(19) . ?
N2 C10 1.348(2) . ?
N2 C6 1.354(2) . ?
C1 C2 1.392(2) . ?
C1 C11 1.488(2) . ?
C2 C3 1.400(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 C17 1.483(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.469(2) . ?
C6 C7 1.393(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.394(2) . ?
C17 C18 1.400(2) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C24 W1 C26 90.76(7) . . ?
C24 W1 C25 84.49(7) . . ?
C26 W1 C25 85.09(7) . . ?
C24 W1 C23 88.01(7) . . ?
C26 W1 C23 82.63(7) . . ?
C25 W1 C23 165.51(7) . . ?
C24 W1 N2 95.46(6) . . ?
C26 W1 N2 173.65(6) . . ?
C25 W1 N2 94.20(6) . . ?
C23 W1 N2 98.85(6) . . ?
C24 W1 N1 167.28(5) . . ?
C26 W1 N1 101.20(6) . . ?
C25 W1 N1 100.70(6) . . ?
C23 W1 N1 89.23(6) . . ?
N2 W1 N1 72.71(5) . . ?
C1 N1 C5 116.77(13) . . ?
C1 N1 W1 127.51(10) . . ?
C5 N1 W1 113.38(10) . . ?
C10 N2 C6 117.81(13) . . ?
C10 N2 W1 124.57(11) . . ?
C6 N2 W1 117.47(10) . . ?
N1 C1 C2 122.10(14) . . ?
N1 C1 C11 117.93(14) . . ?
C2 C1 C11 119.82(14) . . ?
C1 C2 C3 120.86(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 116.12(14) . . ?
C4 C3 C17 120.95(14) . . ?
C2 C3 C17 122.93(14) . . ?
C5 C4 C3 120.69(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C5 C4 122.74(14) . . ?
N1 C5 C6 115.65(13) . . ?
C4 C5 C6 121.61(13) . . ?
N2 C6 C7 121.85(14) . . ?
N2 C6 C5 116.04(13) . . ?
C7 C6 C5 122.00(14) . . ?
C8 C7 C6 119.62(16) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 118.58(15) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 119.17(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 122.94(15) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C12 C11 C16 119.18(14) . . ?
C12 C11 C1 121.96(15) . . ?
C16 C11 C1 118.70(14) . . ?
C13 C12 C11 119.78(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.93(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.64(16) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.86(16) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.59(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C22 C17 C18 118.29(15) . . ?
C22 C17 C3 120.48(14) . . ?
C18 C17 C3 121.16(15) . . ?
C19 C18 C17 120.85(16) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.29(16) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 119.59(16) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.27(17) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.71(15) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O1 C23 W1 171.13(15) . . ?
O2 C24 W1 176.91(14) . . ?
O3 C25 W1 170.65(15) . . ?
O4 C26 W1 179.14(16) . . ?

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
C5 N1 C1 C2 -8.1(2) . . . . ?
W1 N1 C1 C2 153.25(12) . . . . ?
C5 N1 C1 C11 167.42(14) . . . . ?
W1 N1 C1 C11 -31.22(19) . . . . ?
N1 C1 C2 C3 1.5(2) . . . . ?
C11 C1 C2 C3 -173.99(14) . . . . ?
C1 C2 C3 C4 5.0(2) . . . . ?
C1 C2 C3 C17 -175.39(14) . . . . ?
C2 C3 C4 C5 -4.7(2) . . . . ?
C17 C3 C4 C5 175.70(14) . . . . ?
C1 N1 C5 C4 8.5(2) . . . . ?
W1 N1 C5 C4 -155.48(12) . . . . ?
C1 N1 C5 C6 -171.19(13) . . . . ?
W1 N1 C5 C6 24.85(16) . . . . ?
C3 C4 C5 N1 -2.1(2) . . . . ?
C3 C4 C5 C6 177.53(14) . . . . ?
C10 N2 C6 C7 1.6(2) . . . . ?
W1 N2 C6 C7 -174.20(12) . . . . ?
C10 N2 C6 C5 177.74(13) . . . . ?
W1 N2 C6 C5 1.95(17) . . . . ?
N1 C5 C6 N2 -18.4(2) . . . . ?
C4 C5 C6 N2 161.95(14) . . . . ?
N1 C5 C6 C7 157.77(14) . . . . ?
C4 C5 C6 C7 -21.9(2) . . . . ?
N2 C6 C7 C8 -0.6(2) . . . . ?
C5 C6 C7 C8 -176.55(15) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C6 N2 C10 C9 -1.3(2) . . . . ?
W1 N2 C10 C9 174.14(12) . . . . ?
C8 C9 C10 N2 0.1(2) . . . . ?
N1 C1 C11 C12 133.41(17) . . . . ?
C2 C1 C11 C12 -51.0(2) . . . . ?
N1 C1 C11 C16 -51.3(2) . . . . ?
C2 C1 C11 C16 124.32(17) . . . . ?
C16 C11 C12 C13 1.6(3) . . . . ?
C1 C11 C12 C13 176.84(18) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
C1 C11 C16 C15 -176.07(15) . . . . ?
C4 C3 C17 C22 -152.83(15) . . . . ?
C2 C3 C17 C22 27.6(2) . . . . ?
C4 C3 C17 C18 23.9(2) . . . . ?
C2 C3 C17 C18 -155.73(15) . . . . ?
C22 C17 C18 C19 0.1(2) . . . . ?
C3 C17 C18 C19 -176.65(15) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C18 C17 C22 C21 0.2(2) . . . . ?
C3 C17 C22 C21 177.04(15) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051

