# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_p21nabs
_database_code_depnum_ccdc_archive 'CCDC 1541806'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N O5 P W'
_chemical_formula_sum            'C27 H18 N O5 P W'
_chemical_formula_weight         651.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   8.2075(16)
_cell_length_b                   18.297(4)
_cell_length_c                   16.182(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.63(3)
_cell_angle_gamma                90.00
_cell_volume                     2402.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    15247
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      29.61

_exptl_crystal_description       rhombus
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    4.914
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.3195
_exptl_absorpt_correction_T_max  0.6470
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -35 1 0.0094
0 35 -1 0.0610
-1 4 16 0.2158
0 5 -28 0.2233
29 0 -21 0.1100
-14 1 13 0.1352
-9 -4 -10 0.1199
4 -1 7 0.1770
4 -5 -10 0.1457

_exptl_absorpt_process_details   numerical

_exptl_special_details           
;
 STOE IPDS 2T software X-RED & X-SHAPE is used
;

_diffrn_ambient_temperature      220(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18474
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         29.23
_reflns_number_total             6473
_reflns_number_gt                4729
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep(Johnson, 1996)'
_computing_publication_material  'X-STEP32, Microsoft Word'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6473
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1694(5) -0.0606(2) 0.7793(3) 0.0336(8) Uani 1 1 d . . .
C2 C 0.1090(5) -0.1031(2) 0.8394(3) 0.0343(9) Uani 1 1 d . . .
H2 H 0.0422 -0.1430 0.8197 0.041 Uiso 1 1 calc R . .
C3 C 0.1375(5) -0.0926(2) 0.9262(3) 0.0322(8) Uani 1 1 d . . .
C4 C 0.2296(5) -0.0331(2) 0.9611(2) 0.0316(8) Uani 1 1 d . . .
H4 H 0.2474 -0.0291 1.0197 0.038 Uiso 1 1 calc R . .
C5 C 0.2968(5) 0.0206(2) 0.9159(2) 0.0306(8) Uani 1 1 d . . .
C6 C 0.3784(5) 0.0864(2) 0.9552(3) 0.0318(8) Uani 1 1 d . . .
C7 C 0.3676(5) 0.1047(3) 1.0377(3) 0.0393(9) Uani 1 1 d . . .
H7 H 0.3112 0.0738 1.0703 0.047 Uiso 1 1 calc R . .
C8 C 0.4403(6) 0.1685(3) 1.0720(3) 0.0441(10) Uani 1 1 d . . .
H8 H 0.4334 0.1815 1.1275 0.053 Uiso 1 1 calc R . .
C9 C 0.5225(6) 0.2124(3) 1.0228(3) 0.0428(10) Uani 1 1 d . . .
H9 H 0.5741 0.2556 1.0447 0.051 Uiso 1 1 calc R . .
C10 C 0.5285(5) 0.1925(3) 0.9417(3) 0.0386(9) Uani 1 1 d . . .
H10 H 0.5841 0.2234 0.9089 0.046 Uiso 1 1 calc R . .
C11 C 0.1255(5) -0.0774(2) 0.6892(3) 0.0338(8) Uani 1 1 d . . .
C12 C 0.2381(5) -0.0674(3) 0.6336(3) 0.0367(9) Uani 1 1 d . . .
H12 H 0.3467 -0.0534 0.6546 0.044 Uiso 1 1 calc R . .
C13 C 0.1947(6) -0.0773(3) 0.5487(3) 0.0399(10) Uani 1 1 d . . .
H13 H 0.2732 -0.0702 0.5127 0.048 Uiso 1 1 calc R . .
C14 C 0.0353(5) -0.0979(2) 0.5164(3) 0.0362(9) Uani 1 1 d . . .
C15 C -0.0786(5) -0.1104(3) 0.5710(3) 0.0429(10) Uani 1 1 d . . .
H15 H -0.1859 -0.1260 0.5498 0.052 Uiso 1 1 calc R . .
C16 C -0.0345(5) -0.1001(3) 0.6554(3) 0.0399(10) Uani 1 1 d . . .
H16 H -0.1127 -0.1083 0.6913 0.048 Uiso 1 1 calc R . .
C17 C 0.0715(5) -0.1456(2) 0.9824(3) 0.0335(9) Uani 1 1 d . . .
C18 C 0.0417(6) -0.2189(3) 0.9600(3) 0.0429(10) Uani 1 1 d . . .
H18 H 0.0633 -0.2353 0.9076 0.051 Uiso 1 1 calc R . .
C19 C -0.0189(7) -0.2676(3) 1.0136(4) 0.0525(13) Uani 1 1 d . . .
H19 H -0.0387 -0.3165 0.9972 0.063 Uiso 1 1 calc R . .
C20 C -0.0502(6) -0.2449(3) 1.0905(3) 0.0509(12) Uani 1 1 d . . .
H20 H -0.0911 -0.2780 1.1267 0.061 Uiso 1 1 calc R . .
C21 C -0.0213(5) -0.1728(3) 1.1145(3) 0.0434(10) Uani 1 1 d . . .
H21 H -0.0425 -0.1571 1.1671 0.052 Uiso 1 1 calc R . .
C22 C 0.0384(5) -0.1240(2) 1.0612(3) 0.0345(9) Uani 1 1 d . . .
H22 H 0.0573 -0.0752 1.0783 0.041 Uiso 1 1 calc R . .
C23 C 0.0908(7) -0.0991(3) 0.3764(3) 0.0571(14) Uani 1 1 d . . .
H23A H 0.0353 -0.1084 0.3202 0.086 Uiso 1 1 calc R . .
H23B H 0.1822 -0.1328 0.3896 0.086 Uiso 1 1 calc R . .
H23C H 0.1320 -0.0493 0.3801 0.086 Uiso 1 1 calc R . .
C24 C 0.6555(6) 0.0403(3) 0.7836(3) 0.0426(10) Uani 1 1 d . . .
C25 C 0.6250(5) 0.1916(3) 0.7541(3) 0.0408(10) Uani 1 1 d . . .
C26 C 0.2865(5) 0.1903(3) 0.7350(3) 0.0383(9) Uani 1 1 d . . .
C27 C 0.4513(5) 0.0888(3) 0.6454(3) 0.0404(10) Uani 1 1 d . . .
N2 N 0.4578(4) 0.13014(19) 0.9058(2) 0.0313(7) Uani 1 1 d . . .
O1 O -0.0214(4) -0.1088(2) 0.43379(19) 0.0470(8) Uani 1 1 d . . .
O2 O 0.7635(5) 0.0008(3) 0.7890(3) 0.0661(11) Uani 1 1 d . . .
O3 O 0.7144(4) 0.2379(2) 0.7442(3) 0.0594(10) Uani 1 1 d . . .
O4 O 0.1956(4) 0.2352(2) 0.7135(3) 0.0610(10) Uani 1 1 d . . .
O5 O 0.4469(5) 0.0738(2) 0.5767(2) 0.0573(10) Uani 1 1 d . . .
P1 P 0.28492(13) 0.01676(6) 0.80862(7) 0.0326(2) Uani 1 1 d . . .
W1 W 0.464588(18) 0.111886(10) 0.765960(10) 0.03237(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(6) . ?
C1 C11 1.481(6) . ?
C1 P1 1.730(4) . ?
C2 C3 1.403(6) . ?
C3 C4 1.395(6) . ?
C3 C17 1.486(6) . ?
C4 C5 1.389(6) . ?
C5 C6 1.475(6) . ?
C5 P1 1.725(4) . ?
C6 N2 1.364(5) . ?
C6 C7 1.393(6) . ?
C7 C8 1.389(7) . ?
C8 C9 1.376(7) . ?
C9 C10 1.370(6) . ?
C10 N2 1.370(6) . ?
C11 C12 1.396(6) . ?
C11 C16 1.408(6) . ?
C12 C13 1.379(6) . ?
C13 C14 1.386(6) . ?
C14 O1 1.362(5) . ?
C14 C15 1.399(6) . ?
C15 C16 1.372(6) . ?
C17 C18 1.400(6) . ?
C17 C22 1.400(6) . ?
C18 C19 1.388(7) . ?
C19 C20 1.373(7) . ?
C20 C21 1.384(7) . ?
C21 C22 1.381(6) . ?
C23 O1 1.413(6) . ?
C24 O2 1.136(6) . ?
C24 W1 2.030(5) . ?
C25 O3 1.147(6) . ?
C25 W1 1.994(4) . ?
C26 O4 1.130(6) . ?
C26 W1 2.056(5) . ?
C27 O5 1.141(5) . ?
C27 W1 1.982(4) . ?
N2 W1 2.296(3) . ?
P1 W1 2.4467(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 120.8(4) . . ?
C2 C1 P1 120.2(3) . . ?
C11 C1 P1 118.8(3) . . ?
C1 C2 C3 126.8(4) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 C17 119.1(4) . . ?
C2 C3 C17 120.1(4) . . ?
C5 C4 C3 124.9(4) . . ?
C4 C5 C6 122.7(4) . . ?
C4 C5 P1 122.4(3) . . ?
C6 C5 P1 114.9(3) . . ?
N2 C6 C7 121.7(4) . . ?
N2 C6 C5 116.9(4) . . ?
C7 C6 C5 121.3(4) . . ?
C8 C7 C6 120.0(4) . . ?
C9 C8 C7 118.6(4) . . ?
C10 C9 C8 119.3(4) . . ?
N2 C10 C9 123.7(4) . . ?
C12 C11 C16 117.2(4) . . ?
C12 C11 C1 121.4(4) . . ?
C16 C11 C1 121.3(4) . . ?
C13 C12 C11 121.9(4) . . ?
C12 C13 C14 120.0(4) . . ?
O1 C14 C13 125.1(4) . . ?
O1 C14 C15 115.7(4) . . ?
C13 C14 C15 119.2(4) . . ?
C16 C15 C14 120.3(4) . . ?
C15 C16 C11 121.3(4) . . ?
C18 C17 C22 117.2(4) . . ?
C18 C17 C3 122.1(4) . . ?
C22 C17 C3 120.7(4) . . ?
C19 C18 C17 121.2(4) . . ?
C20 C19 C18 120.4(5) . . ?
C19 C20 C21 119.7(5) . . ?
C22 C21 C20 120.2(4) . . ?
C21 C22 C17 121.4(4) . . ?
O2 C24 W1 176.2(4) . . ?
O3 C25 W1 177.4(4) . . ?
O4 C26 W1 174.7(4) . . ?
O5 C27 W1 177.9(5) . . ?
C6 N2 C10 116.7(4) . . ?
C6 N2 W1 125.2(3) . . ?
C10 N2 W1 117.9(3) . . ?
C14 O1 C23 117.7(4) . . ?
C5 P1 C1 104.8(2) . . ?
C5 P1 W1 108.02(14) . . ?
C1 P1 W1 146.48(15) . . ?
C27 W1 C25 90.03(19) . . ?
C27 W1 C24 85.87(19) . . ?
C25 W1 C24 88.8(2) . . ?
C27 W1 C26 88.67(19) . . ?
C25 W1 C26 85.49(19) . . ?
C24 W1 C26 172.10(17) . . ?
C27 W1 N2 174.03(15) . . ?
C25 W1 N2 95.88(16) . . ?
C24 W1 N2 95.05(16) . . ?
C26 W1 N2 90.97(15) . . ?
C27 W1 P1 100.35(14) . . ?
C25 W1 P1 169.27(13) . . ?
C24 W1 P1 89.22(14) . . ?
C26 W1 P1 97.39(12) . . ?
N2 W1 P1 73.79(9) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        29.23
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.287
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.130
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541818'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 AL70
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 F N O4 P W'
_chemical_formula_sum            'C26 H15 F N O4 P W'
_chemical_formula_weight         639.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 '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                   16.3244(17)
_cell_length_b                   18.5970(12)
_cell_length_c                   7.2964(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2215.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8849
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      29.57

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.331
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.4131
_exptl_absorpt_correction_T_max  0.8415
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 -2 7 0.2230
29 6 -2 0.1600
0 1 14 0.0130
1 -1 -18 0.0320
0 -11 1 0.0110
0 11 -1 0.0300
-1 -2 -25 0.0260

_exptl_absorpt_process_details   'STOE X-RED & X-SHAPE'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            10058
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.249
_diffrn_reflns_theta_max         29.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5235
_reflns_number_gt                3832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.990
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'

_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0054(4)
_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   -0.01(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5235
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3285(6) 0.1001(6) 0.2617(12) 0.033(3) Uani 1 1 d . . . . .
C2 C 0.3817(6) 0.0448(5) 0.2683(16) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.3621 -0.0002 0.2344 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4657(6) 0.0492(5) 0.3226(16) 0.029(2) Uani 1 1 d . . . . .
C4 C 0.5018(6) 0.1140(6) 0.3759(15) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.5561 0.1125 0.4145 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4637(7) 0.1791(6) 0.3758(16) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.4995(7) 0.2471(6) 0.4437(14) 0.033(2) Uani 1 1 d . . . . .
C7 C 0.5756(7) 0.2471(7) 0.5266(17) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.6042 0.2041 0.5388 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6098(7) 0.3099(7) 0.592(2) 0.045(3) Uani 1 1 d . . . . .
H8 H 0.6608 0.3098 0.6482 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5665(8) 0.3724(7) 0.5700(18) 0.041(3) Uani 1 1 d . . . . .
H9 H 0.5879 0.4159 0.6107 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4906(8) 0.3698(6) 0.4873(17) 0.042(3) Uani 1 1 d . . . . .
H10 H 0.4611 0.4124 0.4766 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2421(6) 0.0870(6) 0.2100(14) 0.031(2) Uani 1 1 d . . . . .
C12 C 0.1960(7) 0.1352(7) 0.1070(16) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.2204 0.1775 0.0665 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1148(7) 0.1219(7) 0.0630(16) 0.036(2) Uani 1 1 d . . . . .
H13 H 0.0843 0.1546 -0.0052 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0808(7) 0.0580(7) 0.1247(17) 0.039(2) Uani 1 1 d . . . . .
C15 C 0.1232(7) 0.0093(6) 0.2312(17) 0.040(3) Uani 1 1 d . . . . .
H15 H 0.0985 -0.0325 0.2739 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2029(6) 0.0250(5) 0.271(2) 0.033(3) Uani 1 1 d . . . . .
H16 H 0.2324 -0.0072 0.3433 0.040 Uiso 1 1 calc R U . . .
C17 C 0.5179(6) -0.0173(5) 0.3225(15) 0.028(2) Uani 1 1 d . . . . .
C18 C 0.4841(7) -0.0836(6) 0.3702(15) 0.037(2) Uani 1 1 d . . . . .
H18 H 0.4292 -0.0861 0.4041 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5304(7) -0.1456(6) 0.3678(16) 0.038(2) Uani 1 1 d . . . . .
H19 H 0.5068 -0.1892 0.4012 0.046 Uiso 1 1 calc R U . . .
C20 C 0.6114(7) -0.1431(6) 0.316(2) 0.039(3) Uani 1 1 d . . . . .
H20 H 0.6426 -0.1850 0.3153 0.047 Uiso 1 1 calc R U . . .
C21 C 0.6467(7) -0.0779(6) 0.2655(16) 0.038(3) Uani 1 1 d . . . . .
H21 H 0.7012 -0.0761 0.2288 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5994(6) -0.0153(6) 0.270(2) 0.037(3) Uani 1 1 d . . . . .
H22 H 0.6230 0.0284 0.2376 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3788(7) 0.3200(7) 0.0373(15) 0.037(2) Uani 1 1 d . . . . .
C24 C 0.3276(6) 0.4235(5) 0.277(4) 0.041(3) Uani 1 1 d . . . . .
C25 C 0.2748(7) 0.3285(8) 0.5436(18) 0.045(3) Uani 1 1 d . . . . .
C26 C 0.2180(6) 0.3151(6) 0.1777(17) 0.036(2) Uani 1 1 d . . . . .
O1 O 0.4069(6) 0.3244(5) -0.1054(13) 0.052(2) Uani 1 1 d . . . . .
O2 O 0.3254(5) 0.4842(5) 0.2558(16) 0.053(3) Uani 1 1 d . . . . .
O3 O 0.2427(7) 0.3397(7) 0.6810(15) 0.073(3) Uani 1 1 d . . . . .
O4 O 0.1546(6) 0.3142(5) 0.1134(16) 0.055(3) Uani 1 1 d . . . . .
F1 F 0.0015(4) 0.0447(5) 0.0814(12) 0.057(2) Uani 1 1 d . . . . .
P1 P 0.35929(16) 0.18822(14) 0.3155(6) 0.0320(7) Uani 1 1 d . . . . .
W1 W 0.32820(2) 0.31679(2) 0.29305(8) 0.03262(13) Uani 1 1 d . . . . .
N2 N 0.4566(6) 0.3088(5) 0.4207(14) 0.035(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.347(14) . ?
C1 C11 1.480(14) . ?
C1 P1 1.759(11) . ?
C2 C3 1.430(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(14) . ?
C3 C17 1.500(13) . ?
C4 C5 1.361(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.479(15) . ?
C5 P1 1.769(11) . ?
C6 N2 1.355(14) . ?
C6 C7 1.383(15) . ?
C7 C8 1.379(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(18) . ?
C9 H9 0.9300 . ?
C10 N2 1.352(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(15) . ?
C11 C16 1.393(14) . ?
C12 C13 1.386(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(17) . ?
C13 H13 0.9300 . ?
C14 F1 1.355(12) . ?
C14 C15 1.380(16) . ?
C15 C16 1.365(15) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.384(15) . ?
C17 C18 1.397(14) . ?
C18 C19 1.379(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(15) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O1 1.140(14) . ?
C23 W1 2.042(11) . ?
C24 O2 1.141(13) . ?
C24 W1 1.988(10) . ?
C25 O3 1.150(16) . ?
C25 W1 2.037(12) . ?
C26 O4 1.137(14) . ?
C26 W1 1.986(10) . ?
P1 W1 2.450(3) . ?
W1 N2 2.299(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 119.9(10) . . ?
C2 C1 P1 121.2(8) . . ?
C11 C1 P1 118.8(8) . . ?
C1 C2 C3 125.8(10) . . ?
C1 C2 H2 117.1 . . ?
C3 C2 H2 117.1 . . ?
C4 C3 C2 122.1(9) . . ?
C4 C3 C17 118.1(9) . . ?
C2 C3 C17 119.8(9) . . ?
C5 C4 C3 125.1(10) . . ?
C5 C4 H4 117.5 . . ?
C3 C4 H4 117.5 . . ?
C4 C5 C6 125.5(10) . . ?
C4 C5 P1 121.8(8) . . ?
C6 C5 P1 112.4(8) . . ?
N2 C6 C7 121.3(10) . . ?
N2 C6 C5 118.7(9) . . ?
C7 C6 C5 120.0(10) . . ?
C8 C7 C6 120.9(12) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 118.1(12) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 119.0(12) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 123.7(12) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C12 C11 C16 117.3(10) . . ?
C12 C11 C1 123.2(10) . . ?
C16 C11 C1 119.4(10) . . ?
C13 C12 C11 121.8(11) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 117.4(11) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
F1 C14 C15 119.4(11) . . ?
F1 C14 C13 117.6(11) . . ?
C15 C14 C13 123.0(10) . . ?
C16 C15 C14 117.3(10) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C11 123.0(11) . . ?
C15 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
C22 C17 C18 118.2(9) . . ?
C22 C17 C3 121.6(9) . . ?
C18 C17 C3 120.2(9) . . ?
C19 C18 C17 121.3(10) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.2(11) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.0(10) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.4(10) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C21 121.0(10) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
O1 C23 W1 177.5(11) . . ?
O2 C24 W1 175(2) . . ?
O3 C25 W1 175.2(14) . . ?
O4 C26 W1 179.3(12) . . ?
C1 P1 C5 104.0(5) . . ?
C1 P1 W1 146.6(4) . . ?
C5 P1 W1 108.1(4) . . ?
C26 W1 C24 89.2(5) . . ?
C26 W1 C25 89.7(5) . . ?
C24 W1 C25 86.8(8) . . ?
C26 W1 C23 88.8(5) . . ?
C24 W1 C23 85.4(8) . . ?
C25 W1 C23 172.0(5) . . ?
C26 W1 N2 175.3(4) . . ?
C24 W1 N2 95.3(5) . . ?
C25 W1 N2 91.9(4) . . ?
C23 W1 N2 90.2(4) . . ?
C26 W1 P1 101.6(4) . . ?
C24 W1 P1 168.3(3) . . ?
C25 W1 P1 97.6(4) . . ?
C23 W1 P1 90.3(4) . . ?
N2 W1 P1 73.8(2) . . ?
C10 N2 C6 117.0(10) . . ?
C10 N2 W1 117.7(8) . . ?
C6 N2 W1 125.1(7) . . ?

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
C11 C1 C2 C3 -177.4(10) . . . . ?
P1 C1 C2 C3 2.0(16) . . . . ?
C1 C2 C3 C4 -0.1(18) . . . . ?
C1 C2 C3 C17 -179.8(10) . . . . ?
C2 C3 C4 C5 -2.6(18) . . . . ?
C17 C3 C4 C5 177.1(11) . . . . ?
C3 C4 C5 C6 175.6(11) . . . . ?
C3 C4 C5 P1 3.0(17) . . . . ?
C4 C5 C6 N2 174.6(11) . . . . ?
P1 C5 C6 N2 -12.2(14) . . . . ?
C4 C5 C6 C7 -4.5(18) . . . . ?
P1 C5 C6 C7 168.7(9) . . . . ?
N2 C6 C7 C8 1.2(19) . . . . ?
C5 C6 C7 C8 -179.7(12) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
C8 C9 C10 N2 -2(2) . . . . ?
C2 C1 C11 C12 -144.0(11) . . . . ?
P1 C1 C11 C12 36.5(13) . . . . ?
C2 C1 C11 C16 38.4(15) . . . . ?
P1 C1 C11 C16 -141.1(10) . . . . ?
C16 C11 C12 C13 -1.4(17) . . . . ?
C1 C11 C12 C13 -179.0(10) . . . . ?
C11 C12 C13 C14 -0.4(17) . . . . ?
C12 C13 C14 F1 -179.8(10) . . . . ?
C12 C13 C14 C15 2.2(18) . . . . ?
F1 C14 C15 C16 -180.0(11) . . . . ?
C13 C14 C15 C16 -1.9(19) . . . . ?
C14 C15 C16 C11 0(2) . . . . ?
C12 C11 C16 C15 1.7(19) . . . . ?
C1 C11 C16 C15 179.4(11) . . . . ?
C4 C3 C17 C22 -37.2(17) . . . . ?
C2 C3 C17 C22 142.5(12) . . . . ?
C4 C3 C17 C18 144.9(11) . . . . ?
C2 C3 C17 C18 -35.4(16) . . . . ?
C22 C17 C18 C19 0.8(17) . . . . ?
C3 C17 C18 C19 178.8(11) . . . . ?
C17 C18 C19 C20 -0.6(18) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C19 C20 C21 C22 1(2) . . . . ?
C18 C17 C22 C21 -0.1(19) . . . . ?
C3 C17 C22 C21 -178.1(11) . . . . ?
C20 C21 C22 C17 -1(2) . . . . ?
C2 C1 P1 C5 -1.4(10) . . . . ?
C11 C1 P1 C5 178.1(8) . . . . ?
C2 C1 P1 W1 162.3(7) . . . . ?
C11 C1 P1 W1 -18.3(12) . . . . ?
C4 C5 P1 C1 -0.9(11) . . . . ?
C6 C5 P1 C1 -174.4(8) . . . . ?
C4 C5 P1 W1 -171.6(9) . . . . ?
C6 C5 P1 W1 14.9(9) . . . . ?
C9 C10 N2 C6 2.3(18) . . . . ?
C9 C10 N2 W1 178.8(10) . . . . ?
C7 C6 N2 C10 -2.0(17) . . . . ?
C5 C6 N2 C10 178.9(10) . . . . ?
C7 C6 N2 W1 -178.2(8) . . . . ?
C5 C6 N2 W1 2.7(15) . . . . ?

_refine_diff_density_max         1.145
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.162
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1541811'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 F3 N2'
_chemical_formula_weight         376.37

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'
F F 0.0171 0.0103 '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                   10.6860(3)
_cell_length_b                   21.8463(5)
_cell_length_c                   7.44370(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.6580(10)
_cell_angle_gamma                90
_cell_volume                     1735.86(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5204
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.933
_exptl_transmission_factor_max   0.995
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
  SADABS - Bruker/Siemens area detector absorption
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16134
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.668
_diffrn_reflns_theta_max         25.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3069
_reflns_number_gt                2510
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'

_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)+(0.0446P)²+1.2440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3069
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.10669(17) 0.23190(8) 0.9264(2) 0.0154(4) Uani 1 1 d . . . . .
C2 C -0.05304(17) 0.28974(8) 0.9489(2) 0.0171(4) Uani 1 1 d . . . . .
H2 H -0.1021 0.3254 0.9257 0.021 Uiso 1 1 calc R U . . .
C3 C 0.07239(17) 0.29524(8) 1.0052(2) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.14046(18) 0.24167(8) 1.0344(2) 0.0167(4) Uani 1 1 d . . . . .
H4 H 0.2267 0.2435 1.0714 0.020 Uiso 1 1 calc R U . . .
C5 C 0.08126(17) 0.18534(8) 1.0088(2) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.15185(17) 0.12735(8) 1.0416(2) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.09130(18) 0.07408(8) 1.0906(2) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.0033 0.0741 1.1036 0.022 Uiso 1 1 calc R U . . .
C8 C 0.15983(18) 0.02084(9) 1.1206(2) 0.0206(4) Uani 1 1 d . . . . .
H8 H 0.1189 -0.0157 1.1541 0.025 Uiso 1 1 calc R U . . .
C9 C 0.28761(19) 0.02117(9) 1.1015(2) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.3354 -0.0151 1.1214 0.028 Uiso 1 1 calc R U . . .
C10 C 0.34509(19) 0.07500(9) 1.0530(3) 0.0262(5) Uani 1 1 d . . . . .
H10 H 0.4331 0.0752 1.0397 0.031 Uiso 1 1 calc R U . . .
C11 C -0.24072(17) 0.22457(9) 0.8674(2) 0.0171(4) Uani 1 1 d . . . . .
C12 C -0.29482(19) 0.16684(9) 0.8503(3) 0.0230(4) Uani 1 1 d . . . . .
H12 H -0.2453 0.1314 0.8746 0.028 Uiso 1 1 calc R U . . .
C13 C -0.41976(19) 0.16047(10) 0.7983(3) 0.0286(5) Uani 1 1 d . . . . .
H13 H -0.4557 0.1208 0.7867 0.034 Uiso 1 1 calc R U . . .
C14 C -0.4928(2) 0.21171(10) 0.7632(3) 0.0291(5) Uani 1 1 d . . . . .
H14 H -0.5792 0.2076 0.7294 0.035 Uiso 1 1 calc R U . . .
C15 C -0.4389(2) 0.26884(10) 0.7778(3) 0.0304(5) Uani 1 1 d . . . . .
H15 H -0.4884 0.3042 0.7521 0.037 Uiso 1 1 calc R U . . .
C16 C -0.31430(18) 0.27544(9) 0.8291(3) 0.0220(4) Uani 1 1 d . . . . .
H16 H -0.2785 0.3152 0.8382 0.026 Uiso 1 1 calc R U . . .
C17 C 0.13071(17) 0.35626(8) 1.0349(2) 0.0157(4) Uani 1 1 d . . . . .
C18 C 0.06206(18) 0.40463(8) 1.1030(2) 0.0176(4) Uani 1 1 d . . . . .
H18 H -0.0234 0.3986 1.1284 0.021 Uiso 1 1 calc R U . . .
C19 C 0.11692(18) 0.46121(8) 1.1339(2) 0.0188(4) Uani 1 1 d . . . . .
H19 H 0.0690 0.4939 1.1793 0.023 Uiso 1 1 calc R U . . .
C20 C 0.24141(18) 0.47020(8) 1.0986(2) 0.0188(4) Uani 1 1 d . . . . .
C21 C 0.31123(18) 0.42258(9) 1.0292(2) 0.0202(4) Uani 1 1 d . . . . .
H21 H 0.3966 0.4288 1.0037 0.024 Uiso 1 1 calc R U . . .
C22 C 0.25588(17) 0.36641(8) 0.9980(2) 0.0181(4) Uani 1 1 d . . . . .
H22 H 0.3037 0.3340 0.9505 0.022 Uiso 1 1 calc R U . . .
C23 C 0.30016(19) 0.53163(9) 1.1275(3) 0.0250(5) Uani 1 1 d . . . . .
N1 N -0.04057(14) 0.18007(7) 0.95704(19) 0.0160(3) Uani 1 1 d . . . . .
N2 N 0.27870(17) 0.12818(8) 1.0237(2) 0.0302(4) Uani 1 1 d . . . . .
F1 F 0.30465(16) 0.56388(6) 0.97511(17) 0.0533(5) Uani 1 1 d . . . . .
F2 F 0.23943(12) 0.56696(5) 1.24115(17) 0.0357(3) Uani 1 1 d . . . . .
F3 F 0.41848(12) 0.52809(6) 1.19346(19) 0.0444(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
C1 N1 1.348(2) . ?
C1 C2 1.394(3) . ?
C1 C11 1.487(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 C17 1.484(2) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(2) . ?
C5 C6 1.489(2) . ?
C6 N2 1.368(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.374(3) . ?
C10 H10 0.9500 . ?
C11 C16 1.383(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.395(3) . ?
C17 C22 1.396(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(3) . ?
C20 C23 1.493(3) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 F2 1.335(2) . ?
C23 F3 1.337(2) . ?
C23 F1 1.338(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.10(17) . . ?
N1 C1 C11 116.71(16) . . ?
C2 C1 C11 121.19(16) . . ?
C3 C2 C1 119.97(17) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 117.67(16) . . ?
C4 C3 C17 121.34(16) . . ?
C2 C3 C17 120.98(16) . . ?
C3 C4 C5 119.45(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.82(16) . . ?
N1 C5 C6 116.77(15) . . ?
C4 C5 C6 120.40(16) . . ?
N2 C6 C7 120.84(17) . . ?
N2 C6 C5 117.99(16) . . ?
C7 C6 C5 121.17(16) . . ?
C8 C7 C6 119.74(18) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 119.79(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.03(18) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 121.92(19) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C16 C11 C12 118.67(18) . . ?
C16 C11 C1 120.32(17) . . ?
C12 C11 C1 121.01(17) . . ?
C13 C12 C11 120.66(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.10(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.26(19) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.86(19) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.44(18) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C22 118.43(17) . . ?
C18 C17 C3 120.69(17) . . ?
C22 C17 C3 120.87(17) . . ?
C19 C18 C17 120.77(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.99(18) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.07(17) . . ?
C19 C20 C23 120.16(17) . . ?
C21 C20 C23 119.72(17) . . ?
C22 C21 C20 119.65(18) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 121.08(18) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
F2 C23 F3 106.25(16) . . ?
F2 C23 F1 105.68(17) . . ?
F3 C23 F1 105.74(17) . . ?
F2 C23 C20 113.42(16) . . ?
F3 C23 C20 112.65(17) . . ?
F1 C23 C20 112.48(16) . . ?
C5 N1 C1 117.97(15) . . ?
C6 N2 C10 118.67(17) . . ?

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
N1 C1 C2 C3 -0.3(3) . . . . ?
C11 C1 C2 C3 179.64(15) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C17 -178.30(16) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C17 C3 C4 C5 178.53(16) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C6 -179.18(15) . . . . ?
N1 C5 C6 N2 154.49(16) . . . . ?
C4 C5 C6 N2 -26.5(2) . . . . ?
N1 C5 C6 C7 -26.1(2) . . . . ?
C4 C5 C6 C7 152.92(17) . . . . ?
N2 C6 C7 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 -179.88(16) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 N2 0.1(3) . . . . ?
N1 C1 C11 C16 -178.46(16) . . . . ?
C2 C1 C11 C16 1.6(3) . . . . ?
N1 C1 C11 C12 1.8(2) . . . . ?
C2 C1 C11 C12 -178.08(17) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C1 C11 C12 C13 178.92(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C1 C11 C16 C15 -178.74(17) . . . . ?
C4 C3 C17 C18 -144.24(17) . . . . ?
C2 C3 C17 C18 35.1(2) . . . . ?
C4 C3 C17 C22 34.8(2) . . . . ?
C2 C3 C17 C22 -145.86(17) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C3 C17 C18 C19 178.80(16) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C18 C19 C20 C23 178.51(16) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C23 C20 C21 C22 -178.21(16) . . . . ?
C20 C21 C22 C17 -0.1(3) . . . . ?
C18 C17 C22 C21 0.6(3) . . . . ?
C3 C17 C22 C21 -178.48(16) . . . . ?
C19 C20 C23 F2 21.5(2) . . . . ?
C21 C20 C23 F2 -161.00(16) . . . . ?
C19 C20 C23 F3 142.23(17) . . . . ?
C21 C20 C23 F3 -40.3(2) . . . . ?
C19 C20 C23 F1 -98.4(2) . . . . ?
C21 C20 C23 F1 79.1(2) . . . . ?
C4 C5 N1 C1 1.0(2) . . . . ?
C6 C5 N1 C1 180.00(14) . . . . ?
C2 C1 N1 C5 -0.8(2) . . . . ?
C11 C1 N1 C5 179.34(14) . . . . ?
C7 C6 N2 C10 0.7(3) . . . . ?
C5 C6 N2 C10 -179.84(16) . . . . ?
C9 C10 N2 C6 -0.6(3) . . . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_wo40abs
_database_code_depnum_ccdc_archive 'CCDC 1541817'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2 O4 S W'
_chemical_formula_sum            'C27 H18 N2 O4 S W'
_chemical_formula_weight         650.34

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p2(1)/c

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

_cell_length_a                   8.4430(17)
_cell_length_b                   16.193(3)
_cell_length_c                   17.514(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.85(3)
_cell_angle_gamma                90.00
_cell_volume                     2391.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    6192
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      25.43

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    4.955
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5792
_exptl_absorpt_correction_T_max  0.7661
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -8 28 0.0743
-6 20 -27 0.0482
-5 -19 -12 0.0292
5 19 27 0.0352
15 -8 -27 0.0410
-25 24 29 0.0592
7 11 3 0.0482

_exptl_absorpt_process_details   'STOE X-RED & X-SHAPE'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      220(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17632
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.1844
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         29.30
_reflns_number_total             6431
_reflns_number_gt                2551
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0244P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6431
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   0.730
_refine_ls_restrained_S_all      0.730
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2584(8) 0.7074(5) 0.0047(4) 0.0403(18) Uani 1 1 d . . .
C2 C -0.3494(8) 0.6767(4) -0.0557(4) 0.044(2) Uani 1 1 d . A .
H2 H -0.4053 0.7139 -0.0883 0.053 Uiso 1 1 calc R . .
C3 C -0.3624(8) 0.5925(4) -0.0707(4) 0.0351(17) Uani 1 1 d . . .
C4 C -0.2751(9) 0.5412(4) -0.0193(4) 0.0378(19) Uani 1 1 d . A .
H4 H -0.2799 0.4835 -0.0253 0.045 Uiso 1 1 calc R . .
C5 C -0.1809(8) 0.5754(4) 0.0408(4) 0.0337(17) Uani 1 1 d . . .
C6 C -0.0922(8) 0.5211(4) 0.0955(4) 0.0339(17) Uani 1 1 d . A .
C7 C -0.1107(9) 0.4370(5) 0.0974(4) 0.046(2) Uani 1 1 d . . .
H7 H -0.1817 0.4107 0.0622 0.056 Uiso 1 1 calc R A .
C8 C -0.0236(9) 0.3908(5) 0.1519(5) 0.055(2) Uani 1 1 d . A .
H8 H -0.0333 0.3330 0.1531 0.066 Uiso 1 1 calc R . .
C9 C 0.0775(9) 0.4312(5) 0.2043(4) 0.047(2) Uani 1 1 d . . .
H9 H 0.1376 0.4015 0.2416 0.056 Uiso 1 1 calc R A .
C10 C 0.0877(9) 0.5155(5) 0.2003(4) 0.047(2) Uani 1 1 d . A .
H10 H 0.1540 0.5429 0.2368 0.057 Uiso 1 1 calc R . .
C11A C -0.235(2) 0.8037(17) 0.0138(11) 0.042(6) Uiso 0.50 1 d P A 1
C11B C -0.277(2) 0.7953(13) 0.0260(10) 0.033(5) Uiso 0.50 1 d P A 2
C12A C -0.3296(19) 0.8364(10) 0.0659(10) 0.037(4) Uiso 0.50 1 d P A 1
H12A H -0.3884 0.8013 0.0965 0.044 Uiso 0.50 1 calc PR A 1
C12B C -0.3419(19) 0.8178(11) 0.0968(10) 0.051(5) Uiso 0.50 1 d P A 2
H12B H -0.3752 0.7766 0.1303 0.061 Uiso 0.50 1 calc PR A 2
C13A C -0.341(2) 0.9211(13) 0.0750(11) 0.045(4) Uiso 0.50 1 d P A 1
H13A H -0.4036 0.9445 0.1122 0.054 Uiso 0.50 1 calc PR A 1
C13B C -0.355(2) 0.8965(13) 0.1153(13) 0.076(6) Uiso 0.50 1 d P A 2
H13B H -0.3968 0.9103 0.1624 0.091 Uiso 0.50 1 calc PR A 2
C14A C -0.257(2) 0.9692(10) 0.0276(11) 0.039(4) Uiso 0.50 1 d P A 1
C14B C -0.310(3) 0.9565(14) 0.0697(13) 0.060(6) Uiso 0.50 1 d P A 2
C15A C -0.1595(18) 0.9337(9) -0.0294(8) 0.036(3) Uiso 0.50 1 d P A 1
H15A H -0.0998 0.9671 -0.0611 0.043 Uiso 0.50 1 calc PR A 1
C15B C -0.242(3) 0.9392(15) -0.0042(14) 0.072(6) Uiso 0.50 1 d P A 2
H15B H -0.2066 0.9807 -0.0367 0.086 Uiso 0.50 1 calc PR A 2
C16A C -0.1575(18) 0.8496(8) -0.0355(8) 0.031(3) Uiso 0.50 1 d P A 1
H16A H -0.1016 0.8242 -0.0742 0.037 Uiso 0.50 1 calc PR A 1
C16B C -0.235(3) 0.8556(14) -0.0214(13) 0.065(6) Uiso 0.50 1 d P A 2
H16B H -0.1992 0.8403 -0.0693 0.079 Uiso 0.50 1 calc PR A 2
C17 C -0.4591(8) 0.5584(5) -0.1358(4) 0.0426(19) Uani 1 1 d . A .
C18 C -0.5309(10) 0.6090(5) -0.1905(5) 0.064(3) Uani 1 1 d . . .
H18 H -0.5158 0.6665 -0.1873 0.077 Uiso 1 1 calc R A .
C19 C -0.6251(11) 0.5764(6) -0.2501(5) 0.076(3) Uani 1 1 d . A .
H19 H -0.6756 0.6123 -0.2858 0.091 Uiso 1 1 calc R . .
C20 C -0.6459(10) 0.4936(6) -0.2581(5) 0.063(3) Uani 1 1 d . . .
H20 H -0.7082 0.4725 -0.2996 0.075 Uiso 1 1 calc R A .
C21 C -0.5745(9) 0.4405(5) -0.2046(5) 0.056(2) Uani 1 1 d . A .
H21 H -0.5877 0.3831 -0.2096 0.067 Uiso 1 1 calc R . .
C22 C -0.4838(9) 0.4728(5) -0.1439(5) 0.054(2) Uani 1 1 d . . .
H22 H -0.4374 0.4367 -0.1071 0.064 Uiso 1 1 calc R A .
C23A C -0.4034(19) 1.1088(11) 0.0899(9) 0.056(4) Uiso 0.50 1 d P A 1
H23A H -0.4115 1.1685 0.0927 0.084 Uiso 0.50 1 calc PR A 1
H23B H -0.3752 1.0868 0.1402 0.084 Uiso 0.50 1 calc PR A 1
H23C H -0.5045 1.0860 0.0715 0.084 Uiso 0.50 1 calc PR A 1
C23B C -0.224(2) 1.0824(11) 0.0489(10) 0.041(5) Uiso 0.50 1 d P A 2
H23D H -0.2017 1.1412 0.0506 0.062 Uiso 0.50 1 calc PR A 2
H23E H -0.2727 1.0682 -0.0006 0.062 Uiso 0.50 1 calc PR A 2
H23F H -0.1254 1.0519 0.0571 0.062 Uiso 0.50 1 calc PR A 2
C24 C 0.1981(10) 0.6980(6) 0.0657(5) 0.056(2) Uani 1 1 d . . .
C25 C 0.1930(10) 0.7094(5) 0.2181(5) 0.061(2) Uani 1 1 d . . .
C26 C -0.1229(10) 0.7149(5) 0.2265(4) 0.050(2) Uani 1 1 d . . .
C27 C 0.0313(10) 0.8184(4) 0.1300(4) 0.045(2) Uani 1 1 d . . .
N1 N -0.1672(7) 0.6570(3) 0.0527(3) 0.0353(14) Uani 1 1 d . A .
N2 N 0.0070(8) 0.5614(3) 0.1465(4) 0.0366(15) Uani 1 1 d . . .
O1 O 0.3040(8) 0.7039(5) 0.0277(4) 0.089(2) Uani 1 1 d . . .
O2 O 0.2997(8) 0.7164(4) 0.2636(4) 0.103(3) Uani 1 1 d . . .
O3 O -0.1989(9) 0.7294(4) 0.2776(4) 0.082(2) Uani 1 1 d . . .
O4 O 0.0422(8) 0.8899(3) 0.1262(3) 0.0585(18) Uani 1 1 d . . .
S1A S -0.2580(8) 1.0822(4) 0.0273(4) 0.0735(19) Uiso 0.50 1 d P A 1
S1B S -0.3344(8) 1.0606(4) 0.1106(4) 0.0953(18) Uiso 0.50 1 d P A 2
W1 W 0.02387(4) 0.69820(2) 0.140920(18) 0.03991(9) Uani 1 1 d . A .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(8) . ?
C1 N1 1.379(8) . ?
C1 C11B 1.48(2) . ?
C1 C11A 1.58(3) . ?
C2 C3 1.392(9) . ?
C3 C4 1.406(9) . ?
C3 C17 1.476(9) . ?
C4 C5 1.402(8) . ?
C5 N1 1.341(8) . ?
C5 C6 1.477(9) . ?
C6 N2 1.361(8) . ?
C6 C7 1.371(9) . ?
C7 C8 1.393(9) . ?
C8 C9 1.386(10) . ?
C9 C10 1.370(10) . ?
C10 N2 1.357(8) . ?
C11A C16A 1.34(3) . ?
C11A C12A 1.35(3) . ?
C11B C16B 1.34(3) . ?
C11B C12B 1.43(3) . ?
C12A C13A 1.38(2) . ?
C12B C13B 1.32(3) . ?
C13A C14A 1.36(3) . ?
C13B C14B 1.32(3) . ?
C14A C15A 1.44(3) . ?
C14A S1A 1.830(18) . ?
C14B C15B 1.47(3) . ?
C14B S1B 1.85(2) . ?
C15A C16A 1.366(19) . ?
C15B C16B 1.39(3) . ?
C17 C18 1.379(9) . ?
C17 C22 1.407(10) . ?
C18 C19 1.385(10) . ?
C19 C20 1.358(12) . ?
C20 C21 1.388(11) . ?
C21 C22 1.382(9) . ?
C23A S1A 1.740(19) . ?
C23B S1B 1.504(19) . ?
C24 O1 1.145(9) . ?
C24 W1 2.022(10) . ?
C25 O2 1.178(8) . ?
C25 W1 1.926(8) . ?
C26 O3 1.151(9) . ?
C26 W1 2.010(10) . ?
C27 O4 1.164(8) . ?
C27 W1 1.958(7) . ?
N1 W1 2.277(5) . ?
N2 W1 2.222(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 122.0(7) . . ?
C2 C1 C11B 118.7(8) . . ?
N1 C1 C11B 118.6(8) . . ?
C2 C1 C11A 119.9(9) . . ?
N1 C1 C11A 117.5(8) . . ?
C11B C1 C11A 16.3(10) . . ?
C1 C2 C3 122.5(7) . . ?
C2 C3 C4 115.1(6) . . ?
C2 C3 C17 123.2(6) . . ?
C4 C3 C17 121.7(6) . . ?
C5 C4 C3 120.5(6) . . ?
N1 C5 C4 123.2(6) . . ?
N1 C5 C6 116.7(5) . . ?
C4 C5 C6 120.1(6) . . ?
N2 C6 C7 121.9(6) . . ?
N2 C6 C5 114.5(6) . . ?
C7 C6 C5 123.5(6) . . ?
C6 C7 C8 119.5(7) . . ?
C9 C8 C7 119.1(7) . . ?
C10 C9 C8 118.3(7) . . ?
N2 C10 C9 123.5(7) . . ?
C16A C11A C12A 123(2) . . ?
C16A C11A C1 123.2(16) . . ?
C12A C11A C1 112.5(18) . . ?
C16B C11B C12B 118(2) . . ?
C16B C11B C1 120.6(18) . . ?
C12B C11B C1 121.0(16) . . ?
C11A C12A C13A 121(2) . . ?
C13B C12B C11B 120(2) . . ?
C14A C13A C12A 117.1(19) . . ?
C12B C13B C14B 122(2) . . ?
C13A C14A C15A 121.7(16) . . ?
C13A C14A S1A 124.7(17) . . ?
C15A C14A S1A 113.6(13) . . ?
C13B C14B C15B 122(2) . . ?
C13B C14B S1B 113.4(17) . . ?
C15B C14B S1B 125(2) . . ?
C16A C15A C14A 117.4(16) . . ?
C16B C15B C14B 113(2) . . ?
C11A C16A C15A 119.8(18) . . ?
C11B C16B C15B 124(2) . . ?
C18 C17 C22 117.3(6) . . ?
C18 C17 C3 121.4(7) . . ?
C22 C17 C3 121.3(6) . . ?
C17 C18 C19 120.9(8) . . ?
C20 C19 C18 121.4(8) . . ?
C19 C20 C21 119.5(7) . . ?
C20 C21 C22 119.4(8) . . ?
C21 C22 C17 121.6(7) . . ?
O1 C24 W1 173.1(8) . . ?
O2 C25 W1 177.9(8) . . ?
O3 C26 W1 174.5(7) . . ?
O4 C27 W1 176.6(7) . . ?
C5 N1 C1 116.6(6) . . ?
C5 N1 W1 116.6(4) . . ?
C1 N1 W1 126.5(5) . . ?
C10 N2 C6 117.6(6) . . ?
C10 N2 W1 123.1(5) . . ?
C6 N2 W1 119.2(4) . . ?
C23A S1A C14A 104.5(9) . . ?
C23B S1B C14B 81.5(11) . . ?
C25 W1 C27 87.0(3) . . ?
C25 W1 C26 85.8(3) . . ?
C27 W1 C26 87.9(3) . . ?
C25 W1 C24 85.4(3) . . ?
C27 W1 C24 84.9(4) . . ?
C26 W1 C24 168.8(3) . . ?
C25 W1 N2 96.3(3) . . ?
C27 W1 N2 176.5(2) . . ?
C26 W1 N2 93.3(3) . . ?
C24 W1 N2 94.4(3) . . ?
C25 W1 N1 168.4(3) . . ?
C27 W1 N1 104.5(2) . . ?
C26 W1 N1 95.9(2) . . ?
C24 W1 N1 94.1(3) . . ?
N2 W1 N1 72.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        29.30
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.222
_refine_diff_density_min         -3.671
_refine_diff_density_rms         0.160
####################################################################### 
# 
# 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_p41212
_database_code_depnum_ccdc_archive 'CCDC 1541814'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 F N2 O4 W, 1/2 (NCCH3)'
_chemical_formula_sum            'C27 H16.50 F N2.50 O4 W'
_chemical_formula_weight         642.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P41212

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'

_cell_length_a                   11.8880(10)
_cell_length_b                   11.8880(10)
_cell_length_c                   32.757(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4629.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1010
_cell_measurement_theta_min      2.533
_cell_measurement_theta_max      30.495

_exptl_crystal_description       prism
_exptl_crystal_colour            dark
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2488
_exptl_absorpt_coefficient_mu    5.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'sadabs bruker-axs'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      143(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-AXS SMART CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            76012
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         30.57
_reflns_number_total             7093
_reflns_number_gt                4534
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep (Johnson, 1996)'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0166P)²+30.1141P] 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   0.007(17)
_refine_ls_number_reflns         7093
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1302(5) 0.8901(5) -0.00620(19) 0.0152(12) Uani 1 1 d . . .
C2 C 0.0612(5) 0.8966(5) -0.04046(19) 0.0154(12) Uani 1 1 d . . .
H2 H 0.0748 0.9530 -0.0604 0.019 Uiso 1 1 calc R . .
C3 C -0.0279(5) 0.8212(6) -0.04597(19) 0.0159(12) Uani 1 1 d . . .
C4 C -0.0452(5) 0.7446(7) -0.01450(18) 0.0176(11) Uani 1 1 d . . .
H4 H -0.1074 0.6946 -0.0156 0.021 Uiso 1 1 calc R . .
C5 C 0.0285(5) 0.7409(6) 0.01878(18) 0.0161(11) Uani 1 1 d . . .
C6 C 0.0099(6) 0.6604(5) 0.0529(2) 0.0182(13) Uani 1 1 d . . .
C7 C -0.0890(6) 0.5985(6) 0.0573(2) 0.0223(14) Uani 1 1 d . . .
H7 H -0.1469 0.6040 0.0374 0.027 Uiso 1 1 calc R . .
C8 C -0.1020(7) 0.5290(7) 0.0908(2) 0.0267(16) Uani 1 1 d . . .
H8 H -0.1699 0.4882 0.0948 0.032 Uiso 1 1 calc R . .
C9 C -0.0150(7) 0.5201(6) 0.11819(19) 0.0271(15) Uani 1 1 d . . .
H9 H -0.0217 0.4728 0.1414 0.033 Uiso 1 1 calc R . .
C10 C 0.0824(6) 0.5809(6) 0.11156(19) 0.0223(13) Uani 1 1 d . . .
H10 H 0.1427 0.5731 0.1304 0.027 Uiso 1 1 calc R . .
C11 C 0.2166(5) 0.9811(5) -0.0004(2) 0.0166(12) Uani 1 1 d . . .
C12 C 0.2132(6) 1.0464(6) 0.0349(2) 0.0200(14) Uani 1 1 d . . .
H12 H 0.1600 1.0296 0.0557 0.024 Uiso 1 1 calc R . .
C13 C 0.2868(6) 1.1357(6) 0.0399(2) 0.0223(15) Uani 1 1 d . . .
H13 H 0.2838 1.1802 0.0639 0.027 Uiso 1 1 calc R . .
C14 C 0.3651(6) 1.1601(6) 0.0096(2) 0.0257(16) Uani 1 1 d . . .
H14 H 0.4158 1.2212 0.0129 0.031 Uiso 1 1 calc R . .
C15 C 0.3689(6) 1.0948(6) -0.0254(2) 0.0254(16) Uani 1 1 d . . .
H15 H 0.4233 1.1105 -0.0459 0.030 Uiso 1 1 calc R . .
C16 C 0.2941(6) 1.0072(6) -0.0308(2) 0.0229(14) Uani 1 1 d . . .
H16 H 0.2955 0.9647 -0.0554 0.027 Uiso 1 1 calc R . .
C17 C -0.1024(6) 0.8227(6) -0.0829(2) 0.0171(13) Uani 1 1 d . . .
C18 C -0.1051(7) 0.9161(7) -0.1083(2) 0.0312(18) Uani 1 1 d . . .
H18 H -0.0586 0.9790 -0.1023 0.037 Uiso 1 1 calc R . .
C19 C -0.1751(8) 0.9192(8) -0.1425(3) 0.039(2) Uani 1 1 d . . .
H19 H -0.1781 0.9839 -0.1595 0.047 Uiso 1 1 calc R . .
C20 C -0.2395(7) 0.8264(7) -0.1509(2) 0.0286(16) Uani 1 1 d . . .
C21 C -0.2392(6) 0.7325(5) -0.12644(17) 0.0215(13) Uani 1 1 d . . .
H21 H -0.2848 0.6693 -0.1328 0.026 Uiso 1 1 calc R . .
C22 C -0.1710(5) 0.7324(6) -0.09244(19) 0.0158(13) Uani 1 1 d . . .
H22 H -0.1711 0.6685 -0.0750 0.019 Uiso 1 1 calc R . .
C23 C 0.3093(7) 0.6377(7) 0.0267(3) 0.0308(18) Uani 1 1 d . . .
C24 C 0.3545(7) 0.6803(6) 0.1061(2) 0.0281(16) Uani 1 1 d . . .
C25 C 0.2179(6) 0.8556(6) 0.1148(2) 0.0221(15) Uani 1 1 d . . .
C26 C 0.3840(6) 0.8412(6) 0.0514(2) 0.0233(15) Uani 1 1 d . . .
F1 F -0.3088(4) 0.8313(4) -0.18384(14) 0.0408(12) Uani 1 1 d . . .
N1 N 0.1181(5) 0.8103(5) 0.02258(16) 0.0154(11) Uani 1 1 d . . .
N2 N 0.0953(5) 0.6503(5) 0.07975(17) 0.0195(11) Uani 1 1 d . . .
O5 O 0.4647(4) 0.8892(5) 0.04156(16) 0.0292(12) Uani 1 1 d . . .
O6 O 0.3538(5) 0.5736(6) 0.0059(2) 0.0478(18) Uani 1 1 d . . .
O7 O 0.4197(5) 0.6402(5) 0.12932(17) 0.0355(14) Uani 1 1 d . . .
O8 O 0.2046(5) 0.9101(5) 0.14386(16) 0.0304(12) Uani 1 1 d . . .
W2 W 0.25239(2) 0.75104(2) 0.067891(6) 0.01762(5) Uani 1 1 d . . .
C1L C 0.5868(19) 0.563(2) 0.0538(6) 0.054(6) Uani 0.50 1 d P . .
H1L1 H 0.6352 0.5780 0.0774 0.082 Uiso 0.50 1 calc PR . .
H1L2 H 0.5815 0.4821 0.0492 0.082 Uiso 0.50 1 calc PR . .
H1L3 H 0.5116 0.5940 0.0589 0.082 Uiso 0.50 1 calc PR . .
C2L C 0.6332(14) 0.6154(14) 0.0188(5) 0.028(3) Uani 0.50 1 d P . .
N1L N 0.6636(9) 0.6636(9) 0.0000 0.076(5) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(8) . ?
C1 C2 1.392(8) . ?
C1 C11 1.504(8) . ?
C2 C3 1.399(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(9) . ?
C3 C17 1.499(9) . ?
C4 C5 1.399(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.353(8) . ?
C5 C6 1.488(9) . ?
C6 N2 1.348(8) . ?
C6 C7 1.394(10) . ?
C7 C8 1.382(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(11) . ?
C9 H9 0.9500 . ?
C10 N2 1.338(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(9) . ?
C11 C16 1.393(10) . ?
C12 C13 1.385(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.384(9) . ?
C17 C18 1.388(10) . ?
C18 C19 1.396(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(11) . ?
C19 H19 0.9500 . ?
C20 F1 1.358(8) . ?
C20 C21 1.375(9) . ?
C21 C22 1.377(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O6 1.150(10) . ?
C23 W2 2.024(9) . ?
C24 O7 1.185(9) . ?
C24 W2 1.937(8) . ?
C25 O8 1.161(9) . ?
C25 W2 2.019(8) . ?
C26 O5 1.163(9) . ?
C26 W2 1.971(8) . ?
N1 W2 2.291(5) . ?
N2 W2 2.253(6) . ?
C1L C2L 1.41(2) . ?
C1L H1L1 0.9800 . ?
C1L H1L2 0.9800 . ?
C1L H1L3 0.9800 . ?
C2L N1L 0.915(16) . ?
C2L C2L 1.27(3) 6 ?
N1L C2L 0.915(16) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(6) . . ?
N1 C1 C11 119.4(6) . . ?
C2 C1 C11 117.7(6) . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 115.8(6) . . ?
C4 C3 C17 121.2(6) . . ?
C2 C3 C17 122.9(6) . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 123.1(6) . . ?
N1 C5 C6 116.1(5) . . ?
C4 C5 C6 120.9(6) . . ?
N2 C6 C7 121.4(6) . . ?
N2 C6 C5 115.8(6) . . ?
C7 C6 C5 122.8(6) . . ?
C8 C7 C6 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 118.7(7) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.2(6) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 122.8(6) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C12 C11 C16 119.3(6) . . ?
C12 C11 C1 119.1(6) . . ?
C16 C11 C1 121.4(6) . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.7(6) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.5(7) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.1(7) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C17 C18 118.1(6) . . ?
C22 C17 C3 121.4(6) . . ?
C18 C17 C3 120.5(6) . . ?
C17 C18 C19 121.1(7) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.3(7) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
F1 C20 C19 117.7(7) . . ?
F1 C20 C21 119.9(7) . . ?
C19 C20 C21 122.3(7) . . ?
C20 C21 C22 118.3(6) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C17 121.9(6) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
O6 C23 W2 171.6(7) . . ?
O7 C24 W2 177.5(7) . . ?
O8 C25 W2 174.0(6) . . ?
O5 C26 W2 176.5(6) . . ?
C1 N1 C5 116.7(5) . . ?
C1 N1 W2 126.6(4) . . ?
C5 N1 W2 114.9(4) . . ?
C10 N2 C6 118.5(6) . . ?
C10 N2 W2 123.9(5) . . ?
C6 N2 W2 117.7(4) . . ?
C24 W2 C26 85.2(3) . . ?
C24 W2 C25 84.4(3) . . ?
C26 W2 C25 92.0(3) . . ?
C24 W2 C23 86.1(3) . . ?
C26 W2 C23 85.1(3) . . ?
C25 W2 C23 170.3(3) . . ?
C24 W2 N2 100.2(3) . . ?
C26 W2 N2 173.8(2) . . ?
C25 W2 N2 91.6(2) . . ?
C23 W2 N2 92.2(3) . . ?
C24 W2 N1 171.7(3) . . ?
C26 W2 N1 102.1(2) . . ?
C25 W2 N1 99.4(2) . . ?
C23 W2 N1 90.3(3) . . ?
N2 W2 N1 72.4(2) . . ?
C2L C1L H1L1 109.5 . . ?
C2L C1L H1L2 109.5 . . ?
H1L1 C1L H1L2 109.5 . . ?
C2L C1L H1L3 109.5 . . ?
H1L1 C1L H1L3 109.5 . . ?
H1L2 C1L H1L3 109.5 . . ?
N1L C2L C2L 46.3(14) . 6 ?
N1L C2L C1L 167(2) . . ?
C2L C2L C1L 142.7(12) 6 . ?
C2L N1L C2L 87(3) 6 . ?

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
N1 C1 C2 C3 2.1(10) . . . . ?
C11 C1 C2 C3 -174.0(6) . . . . ?
C1 C2 C3 C4 2.9(10) . . . . ?
C1 C2 C3 C17 -178.2(6) . . . . ?
C2 C3 C4 C5 -4.2(10) . . . . ?
C17 C3 C4 C5 176.9(6) . . . . ?
C3 C4 C5 N1 0.6(11) . . . . ?
C3 C4 C5 C6 179.2(6) . . . . ?
N1 C5 C6 N2 -12.3(9) . . . . ?
C4 C5 C6 N2 169.1(6) . . . . ?
N1 C5 C6 C7 167.9(7) . . . . ?
C4 C5 C6 C7 -10.8(11) . . . . ?
N2 C6 C7 C8 2.9(11) . . . . ?
C5 C6 C7 C8 -177.2(7) . . . . ?
C6 C7 C8 C9 -2.2(12) . . . . ?
C7 C8 C9 C10 0.2(12) . . . . ?
C8 C9 C10 N2 1.3(12) . . . . ?
N1 C1 C11 C12 -55.6(9) . . . . ?
C2 C1 C11 C12 120.6(7) . . . . ?
N1 C1 C11 C16 129.6(7) . . . . ?
C2 C1 C11 C16 -54.2(9) . . . . ?
C16 C11 C12 C13 -0.7(10) . . . . ?
C1 C11 C12 C13 -175.6(6) . . . . ?
C11 C12 C13 C14 -0.3(11) . . . . ?
C12 C13 C14 C15 0.1(11) . . . . ?
C13 C14 C15 C16 1.3(12) . . . . ?
C14 C15 C16 C11 -2.3(11) . . . . ?
C12 C11 C16 C15 2.0(11) . . . . ?
C1 C11 C16 C15 176.8(6) . . . . ?
C4 C3 C17 C22 -17.1(10) . . . . ?
C2 C3 C17 C22 164.1(6) . . . . ?
C4 C3 C17 C18 162.2(7) . . . . ?
C2 C3 C17 C18 -16.6(10) . . . . ?
C22 C17 C18 C19 0.1(12) . . . . ?
C3 C17 C18 C19 -179.2(8) . . . . ?
C17 C18 C19 C20 -1.4(14) . . . . ?
C18 C19 C20 F1 178.8(8) . . . . ?
C18 C19 C20 C21 1.5(14) . . . . ?
F1 C20 C21 C22 -177.5(6) . . . . ?
C19 C20 C21 C22 -0.3(12) . . . . ?
C20 C21 C22 C17 -1.1(10) . . . . ?
C18 C17 C22 C21 1.2(10) . . . . ?
C3 C17 C22 C21 -179.5(6) . . . . ?
C2 C1 N1 C5 -5.7(9) . . . . ?
C11 C1 N1 C5 170.3(6) . . . . ?
C2 C1 N1 W2 158.3(5) . . . . ?
C11 C1 N1 W2 -25.7(8) . . . . ?
C4 C5 N1 C1 4.3(10) . . . . ?
C6 C5 N1 C1 -174.3(6) . . . . ?
C4 C5 N1 W2 -161.5(5) . . . . ?
C6 C5 N1 W2 19.9(7) . . . . ?
C9 C10 N2 C6 -0.6(11) . . . . ?
C9 C10 N2 W2 179.9(5) . . . . ?
C7 C6 N2 C10 -1.5(10) . . . . ?
C5 C6 N2 C10 178.6(6) . . . . ?
C7 C6 N2 W2 178.0(5) . . . . ?
C5 C6 N2 W2 -1.9(8) . . . . ?
O7 C24 W2 C26 14(16) . . . . ?
O7 C24 W2 C25 -78(16) . . . . ?
O7 C24 W2 C23 100(16) . . . . ?
O7 C24 W2 N2 -169(16) . . . . ?
O7 C24 W2 N1 165(15) . . . . ?
O5 C26 W2 C24 50(10) . . . . ?
O5 C26 W2 C25 134(10) . . . . ?
O5 C26 W2 C23 -36(10) . . . . ?
O5 C26 W2 N2 -101(10) . . . . ?
O5 C26 W2 N1 -126(10) . . . . ?
O8 C25 W2 C24 -2(6) . . . . ?
O8 C25 W2 C26 -87(6) . . . . ?
O8 C25 W2 C23 -15(7) . . . . ?
O8 C25 W2 N2 98(6) . . . . ?
O8 C25 W2 N1 170(6) . . . . ?
O6 C23 W2 C24 -29(5) . . . . ?
O6 C23 W2 C26 56(5) . . . . ?
O6 C23 W2 C25 -17(6) . . . . ?
O6 C23 W2 N2 -129(5) . . . . ?
O6 C23 W2 N1 158(5) . . . . ?
C10 N2 W2 C24 12.2(6) . . . . ?
C6 N2 W2 C24 -167.3(5) . . . . ?
C10 N2 W2 C26 162(2) . . . . ?
C6 N2 W2 C26 -17(3) . . . . ?
C10 N2 W2 C25 -72.3(6) . . . . ?
C6 N2 W2 C25 108.2(5) . . . . ?
C10 N2 W2 C23 98.7(6) . . . . ?
C6 N2 W2 C23 -80.8(5) . . . . ?
C10 N2 W2 N1 -171.7(6) . . . . ?
C6 N2 W2 N1 8.9(5) . . . . ?
C1 N1 W2 C24 -152.2(17) . . . . ?
C5 N1 W2 C24 12(2) . . . . ?
C1 N1 W2 C26 -2.3(6) . . . . ?
C5 N1 W2 C26 161.9(5) . . . . ?
C1 N1 W2 C25 91.7(6) . . . . ?
C5 N1 W2 C25 -104.0(5) . . . . ?
C1 N1 W2 C23 -87.4(6) . . . . ?
C5 N1 W2 C23 76.9(5) . . . . ?
C1 N1 W2 N2 -179.6(6) . . . . ?
C5 N1 W2 N2 -15.3(4) . . . . ?
C1L C2L N1L C2L -137(10) . . . 6 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.397
_refine_diff_density_min         -2.131
_refine_diff_density_rms         0.162
####################################################################### 
# 
# 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_al65
_database_code_depnum_ccdc_archive 'CCDC 1541816'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2 O5 W'
_chemical_formula_sum            'C27 H18 N2 O5 V0 W'
_chemical_formula_weight         634.28

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'p 21/c'
_symmetry_space_group_name_Hall  '-P 2YBC'

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

_cell_length_a                   8.3701(5)
_cell_length_b                   16.0053(7)
_cell_length_c                   17.5299(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.967(5)
_cell_angle_gamma                90.00
_cell_volume                     2345.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    20172
_cell_measurement_theta_min      6.56
_cell_measurement_theta_max      59.13

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    4.967
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.1665
_exptl_absorpt_correction_T_max  0.5853
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
21 17 -8 0.0442
8 -7 28 0.1558
19 -22 28 0.1125
10 -4 -3 0.0704
-19 16 -10 0.1122
-8 -13 14 0.1351
-28 7 9 0.0759
-13 -3 -1 0.0546
-23 28 -13 0.1266
8 -13 -15 0.2216

_exptl_absorpt_process_details   numerical

_exptl_special_details           
;
 STOE IPDS 2T software X-RED & X-SHAPE absorption correction
;

_diffrn_ambient_temperature      210(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22039
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         29.19
_reflns_number_total             6186
_reflns_number_gt                4837
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep (Johnson, 1996)'
_computing_publication_material  'SHELXL-97, X-STEP32, Microsoft Word'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00273(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6186
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2349(4) 0.20873(18) 0.01059(17) 0.0316(6) Uani 1 1 d . . .
C2 C 0.1421(4) 0.1787(2) -0.05177(17) 0.0337(7) Uani 1 1 d . . .
H2 H 0.0844 0.2166 -0.0835 0.040 Uiso 1 1 calc R . .
C3 C 0.1330(4) 0.0938(2) -0.06798(16) 0.0300(6) Uani 1 1 d . . .
C4 C 0.2205(4) 0.04179(19) -0.01784(16) 0.0314(6) Uani 1 1 d . . .
H4 H 0.2164 -0.0163 -0.0253 0.038 Uiso 1 1 calc R . .
C5 C 0.3139(4) 0.07410(18) 0.04319(15) 0.0281(6) Uani 1 1 d . . .
C6 C 0.4058(4) 0.01923(19) 0.09661(15) 0.0284(6) Uani 1 1 d . . .
C7 C 0.3924(4) -0.0673(2) 0.09506(18) 0.0364(7) Uani 1 1 d . . .
H7 H 0.3238 -0.0932 0.0581 0.044 Uiso 1 1 calc R . .
C8 C 0.4796(5) -0.1152(2) 0.14768(19) 0.0407(8) Uani 1 1 d . . .
H8 H 0.4724 -0.1738 0.1465 0.049 Uiso 1 1 calc R . .
C9 C 0.5773(4) -0.0757(2) 0.20198(18) 0.0380(7) Uani 1 1 d . . .
H9 H 0.6377 -0.1068 0.2387 0.046 Uiso 1 1 calc R . .
C10 C 0.5850(4) 0.0103(2) 0.20158(17) 0.0358(7) Uani 1 1 d . . .
H10 H 0.6512 0.0369 0.2391 0.043 Uiso 1 1 calc R . .
C11 C 0.2259(4) 0.2993(2) 0.02890(18) 0.0359(7) Uani 1 1 d . . .
C12 C 0.1637(5) 0.3240(2) 0.0984(2) 0.0425(8) Uani 1 1 d . . .
H12 H 0.1308 0.2832 0.1329 0.051 Uiso 1 1 calc R . .
C13 C 0.1505(5) 0.4073(3) 0.1166(2) 0.0499(9) Uani 1 1 d . . .
H13 H 0.1091 0.4231 0.1633 0.060 Uiso 1 1 calc R . .
C14 C 0.1976(5) 0.4674(2) 0.0666(2) 0.0495(9) Uani 1 1 d . . .
C15 C 0.2556(6) 0.4456(2) -0.0027(2) 0.0552(11) Uani 1 1 d . . .
H15 H 0.2860 0.4870 -0.0372 0.066 Uiso 1 1 calc R . .
C16 C 0.2687(6) 0.3602(2) -0.0213(2) 0.0480(9) Uani 1 1 d . . .
H16 H 0.3073 0.3448 -0.0688 0.058 Uiso 1 1 calc R . .
C17 C 0.0348(4) 0.0601(2) -0.13414(17) 0.0325(6) Uani 1 1 d . . .
C18 C -0.0470(5) 0.1126(2) -0.1850(2) 0.0480(9) Uani 1 1 d . . .
H18 H -0.0396 0.1707 -0.1781 0.058 Uiso 1 1 calc R . .
C19 C -0.1400(5) 0.0808(3) -0.2463(2) 0.0547(10) Uani 1 1 d . . .
H19 H -0.1958 0.1177 -0.2798 0.066 Uiso 1 1 calc R . .
C20 C -0.1514(5) -0.0033(3) -0.2583(2) 0.0489(9) Uani 1 1 d . . .
H20 H -0.2141 -0.0244 -0.3000 0.059 Uiso 1 1 calc R . .
C21 C -0.0705(5) -0.0565(3) -0.2091(2) 0.0519(10) Uani 1 1 d . . .
H21 H -0.0766 -0.1145 -0.2173 0.062 Uiso 1 1 calc R . .
C22 C 0.0209(5) -0.0254(2) -0.1470(2) 0.0465(9) Uani 1 1 d . . .
H22 H 0.0741 -0.0628 -0.1130 0.056 Uiso 1 1 calc R . .
C23 C 0.2209(8) 0.6132(3) 0.0425(3) 0.0806(17) Uani 1 1 d . . .
H23A H 0.1520 0.6087 -0.0036 0.121 Uiso 1 1 calc R . .
H23B H 0.3318 0.6091 0.0294 0.121 Uiso 1 1 calc R . .
H23C H 0.2032 0.6666 0.0668 0.121 Uiso 1 1 calc R . .
C24 C 0.6984(4) 0.1967(2) 0.0718(2) 0.0390(7) Uani 1 1 d . . .
C25 C 0.6948(5) 0.2048(2) 0.2249(2) 0.0456(9) Uani 1 1 d . . .
C26 C 0.3724(5) 0.2118(2) 0.23265(19) 0.0406(8) Uani 1 1 d . . .
C27 C 0.5319(4) 0.3194(2) 0.13218(17) 0.0346(7) Uani 1 1 d . . .
N1 N 0.3262(3) 0.15782(16) 0.05679(14) 0.0294(5) Uani 1 1 d . . .
N2 N 0.5020(3) 0.05812(16) 0.14975(13) 0.0305(5) Uani 1 1 d . . .
O1 O 0.1857(5) 0.54827(18) 0.09283(18) 0.0680(9) Uani 1 1 d . . .
O2 O 0.8069(4) 0.20294(18) 0.0352(2) 0.0603(8) Uani 1 1 d . . .
O3 O 0.7970(5) 0.20750(18) 0.2718(2) 0.0721(11) Uani 1 1 d . . .
O4 O 0.2989(4) 0.2245(2) 0.28527(16) 0.0634(9) Uani 1 1 d . . .
O5 O 0.5471(3) 0.39009(15) 0.12486(14) 0.0430(6) Uani 1 1 d . . .
W1 W 0.521074(16) 0.196418(7) 0.145853(6) 0.03074(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.356(4) . ?
C1 C2 1.393(4) . ?
C1 C11 1.487(4) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.391(4) . ?
C3 C17 1.487(4) . ?
C4 C5 1.392(4) . ?
C4 H4 0.9400 . ?
C5 N1 1.364(4) . ?
C5 C6 1.472(4) . ?
C6 N2 1.351(4) . ?
C6 C7 1.389(4) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.377(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9400 . ?
C10 N2 1.353(4) . ?
C10 H10 0.9400 . ?
C11 C16 1.374(5) . ?
C11 C12 1.407(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.372(6) . ?
C13 H13 0.9400 . ?
C14 O1 1.379(5) . ?
C14 C15 1.378(6) . ?
C15 C16 1.411(5) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C18 1.381(5) . ?
C17 C22 1.390(5) . ?
C18 C19 1.390(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.366(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.367(6) . ?
C20 H20 0.9400 . ?
C21 C22 1.390(5) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 O1 1.404(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 O2 1.143(5) . ?
C24 W1 2.022(4) . ?
C25 O3 1.156(5) . ?
C25 W1 1.960(4) . ?
C26 O4 1.153(5) . ?
C26 W1 2.030(4) . ?
C27 O5 1.146(4) . ?
C27 W1 1.986(3) . ?
N1 W1 2.284(3) . ?
N2 W1 2.221(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(3) . . ?
N1 C1 C11 119.3(3) . . ?
C2 C1 C11 118.3(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 115.8(3) . . ?
C2 C3 C17 122.4(3) . . ?
C4 C3 C17 121.8(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C6 116.3(3) . . ?
C4 C5 C6 121.4(3) . . ?
N2 C6 C7 121.2(3) . . ?
N2 C6 C5 115.9(3) . . ?
C7 C6 C5 122.9(3) . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 123.1(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C16 C11 C12 118.4(3) . . ?
C16 C11 C1 122.4(3) . . ?
C12 C11 C1 119.1(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O1 C14 C13 114.7(4) . . ?
O1 C14 C15 124.5(4) . . ?
C13 C14 C15 120.8(4) . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 120.9(4) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C22 117.4(3) . . ?
C18 C17 C3 121.2(3) . . ?
C22 C17 C3 121.4(3) . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 121.2(4) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 W1 172.5(3) . . ?
O3 C25 W1 178.2(3) . . ?
O4 C26 W1 173.8(3) . . ?
O5 C27 W1 176.3(3) . . ?
C1 N1 C5 116.8(3) . . ?
C1 N1 W1 127.3(2) . . ?
C5 N1 W1 115.47(19) . . ?
C6 N2 C10 118.0(3) . . ?
C6 N2 W1 118.6(2) . . ?
C10 N2 W1 123.4(2) . . ?
C14 O1 C23 117.7(4) . . ?
C25 W1 C27 88.87(13) . . ?
C25 W1 C24 84.90(17) . . ?
C27 W1 C24 83.15(14) . . ?
C25 W1 C26 85.59(17) . . ?
C27 W1 C26 90.22(13) . . ?
C24 W1 C26 168.51(14) . . ?
C25 W1 N2 95.66(12) . . ?
C27 W1 N2 174.70(10) . . ?
C24 W1 N2 94.48(11) . . ?
C26 W1 N2 92.87(11) . . ?
C25 W1 N1 168.24(12) . . ?
C27 W1 N1 102.78(11) . . ?
C24 W1 N1 94.81(12) . . ?
C26 W1 N1 95.81(12) . . ?
N2 W1 N1 72.63(9) . . ?

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
N1 C1 C2 C3 2.8(5) . . . . ?
C11 C1 C2 C3 -174.0(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C17 180.0(3) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C17 C3 C4 C5 179.0(3) . . . . ?
C3 C4 C5 N1 -0.6(5) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
N1 C5 C6 N2 -4.9(4) . . . . ?
C4 C5 C6 N2 174.8(3) . . . . ?
N1 C5 C6 C7 173.0(3) . . . . ?
C4 C5 C6 C7 -7.2(5) . . . . ?
N2 C6 C7 C8 -0.8(5) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 N2 -0.6(5) . . . . ?
N1 C1 C11 C16 121.9(4) . . . . ?
C2 C1 C11 C16 -61.2(5) . . . . ?
N1 C1 C11 C12 -61.5(4) . . . . ?
C2 C1 C11 C12 115.4(4) . . . . ?
C16 C11 C12 C13 -1.9(6) . . . . ?
C1 C11 C12 C13 -178.6(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 O1 -177.0(4) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
O1 C14 C15 C16 177.0(4) . . . . ?
C13 C14 C15 C16 -1.1(7) . . . . ?
C12 C11 C16 C15 2.0(6) . . . . ?
C1 C11 C16 C15 178.7(4) . . . . ?
C14 C15 C16 C11 -0.6(7) . . . . ?
C2 C3 C17 C18 3.0(5) . . . . ?
C4 C3 C17 C18 -177.7(3) . . . . ?
C2 C3 C17 C22 -176.6(3) . . . . ?
C4 C3 C17 C22 2.7(5) . . . . ?
C22 C17 C18 C19 0.3(6) . . . . ?
C3 C17 C18 C19 -179.3(4) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C19 C20 C21 C22 0.7(7) . . . . ?
C20 C21 C22 C17 -1.3(7) . . . . ?
C18 C17 C22 C21 0.7(6) . . . . ?
C3 C17 C22 C21 -179.7(4) . . . . ?
C2 C1 N1 C5 -5.0(5) . . . . ?
C11 C1 N1 C5 171.7(3) . . . . ?
C2 C1 N1 W1 167.0(2) . . . . ?
C11 C1 N1 W1 -16.3(4) . . . . ?
C4 C5 N1 C1 3.9(4) . . . . ?
C6 C5 N1 C1 -176.3(3) . . . . ?
C4 C5 N1 W1 -169.0(2) . . . . ?
C6 C5 N1 W1 10.7(3) . . . . ?
C7 C6 N2 C10 0.0(4) . . . . ?
C5 C6 N2 C10 178.0(3) . . . . ?
C7 C6 N2 W1 178.3(2) . . . . ?
C5 C6 N2 W1 -3.7(3) . . . . ?
C9 C10 N2 C6 0.8(5) . . . . ?
C9 C10 N2 W1 -177.5(3) . . . . ?
C13 C14 O1 C23 -175.5(4) . . . . ?
C15 C14 O1 C23 6.3(7) . . . . ?
O3 C25 W1 C27 178(100) . . . . ?
O3 C25 W1 C24 -99(14) . . . . ?
O3 C25 W1 C26 88(14) . . . . ?
O3 C25 W1 N2 -5(14) . . . . ?
O3 C25 W1 N1 -9(14) . . . . ?
O5 C27 W1 C25 38(4) . . . . ?
O5 C27 W1 C24 -47(4) . . . . ?
O5 C27 W1 C26 123(4) . . . . ?
O5 C27 W1 N2 -111(4) . . . . ?
O5 C27 W1 N1 -141(4) . . . . ?
O2 C24 W1 C25 -37(3) . . . . ?
O2 C24 W1 C27 52(3) . . . . ?
O2 C24 W1 C26 -3(3) . . . . ?
O2 C24 W1 N2 -133(3) . . . . ?
O2 C24 W1 N1 154(3) . . . . ?
O4 C26 W1 C25 28(3) . . . . ?
O4 C26 W1 C27 -61(3) . . . . ?
O4 C26 W1 C24 -6(4) . . . . ?
O4 C26 W1 N2 124(3) . . . . ?
O4 C26 W1 N1 -164(3) . . . . ?
C6 N2 W1 C25 -172.2(3) . . . . ?
C10 N2 W1 C25 6.1(3) . . . . ?
C6 N2 W1 C27 -23.5(14) . . . . ?
C10 N2 W1 C27 154.7(13) . . . . ?
C6 N2 W1 C24 -86.8(2) . . . . ?
C10 N2 W1 C24 91.4(3) . . . . ?
C6 N2 W1 C26 102.0(2) . . . . ?
C10 N2 W1 C26 -79.7(3) . . . . ?
C6 N2 W1 N1 6.8(2) . . . . ?
C10 N2 W1 N1 -174.9(3) . . . . ?
C1 N1 W1 C25 -176.2(7) . . . . ?
C5 N1 W1 C25 -4.2(8) . . . . ?
C1 N1 W1 C27 -4.1(3) . . . . ?
C5 N1 W1 C27 168.0(2) . . . . ?
C1 N1 W1 C24 -88.1(3) . . . . ?
C5 N1 W1 C24 83.9(2) . . . . ?
C1 N1 W1 C26 87.5(3) . . . . ?
C5 N1 W1 C26 -100.5(2) . . . . ?
C1 N1 W1 N2 178.7(3) . . . . ?
C5 N1 W1 N2 -9.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.106
_chemical_absolute_configuration rmad
####################################################################### 
# 
# 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_al36_p_1
_database_code_depnum_ccdc_archive 'CCDC 1541809'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 B F4 N O S'
_chemical_formula_sum            'C23 H18 B F4 N O S'
_chemical_formula_weight         443.25

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.1048(16)
_cell_length_b                   11.553(2)
_cell_length_c                   12.473(3)
_cell_angle_alpha                64.34(3)
_cell_angle_beta                 81.29(3)
_cell_angle_gamma                77.44(3)
_cell_volume                     1025.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6669
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      29.54

_exptl_crystal_description       neadle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11647
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         29.27
_reflns_number_total             5484
_reflns_number_gt                2875
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5484
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.932
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1387(3) -0.4385(2) 0.6059(2) 0.0377(5) Uani 1 1 d . . .
C2 C 0.2294(3) -0.3577(2) 0.5126(2) 0.0402(6) Uani 1 1 d . . .
H2 H 0.2909 -0.3877 0.4556 0.048 Uiso 1 1 calc R . .
C3 C 0.2335(3) -0.2311(2) 0.4991(2) 0.0372(5) Uani 1 1 d . . .
C4 C 0.1430(3) -0.1943(2) 0.5882(2) 0.0395(6) Uani 1 1 d . . .
H4 H 0.1418 -0.1098 0.5834 0.047 Uiso 1 1 calc R . .
C5 C 0.0572(3) -0.2788(2) 0.6814(2) 0.0383(5) Uani 1 1 d . . .
C6 C -0.0304(3) -0.2565(2) 0.7847(2) 0.0377(5) Uani 1 1 d . . .
C7 C -0.1124(4) -0.3497(3) 0.8764(2) 0.0492(7) Uani 1 1 d . . .
H7 H -0.1210 -0.4282 0.8719 0.059 Uiso 1 1 calc R . .
C8 C -0.1816(4) -0.3251(3) 0.9745(2) 0.0551(7) Uani 1 1 d . . .
H8 H -0.2384 -0.3869 1.0391 0.066 Uiso 1 1 calc R . .
C9 C -0.1669(4) -0.2103(3) 0.9772(2) 0.0520(7) Uani 1 1 d . . .
H9 H -0.2119 -0.1917 1.0440 0.062 Uiso 1 1 calc R . .
C10 C -0.0853(4) -0.1225(3) 0.8808(2) 0.0521(7) Uani 1 1 d . . .
H10 H -0.0775 -0.0427 0.8830 0.062 Uiso 1 1 calc R . .
C11 C 0.1237(3) -0.5716(2) 0.6308(2) 0.0375(5) Uani 1 1 d . . .
C12 C 0.0135(4) -0.6385(2) 0.7239(2) 0.0461(6) Uani 1 1 d . . .
H12 H -0.0534 -0.5970 0.7709 0.055 Uiso 1 1 calc R . .
C13 C 0.0018(4) -0.7648(3) 0.7477(2) 0.0527(7) Uani 1 1 d . . .
H13 H -0.0721 -0.8103 0.8118 0.063 Uiso 1 1 calc R . .
C14 C 0.0972(4) -0.8258(2) 0.6785(2) 0.0502(7) Uani 1 1 d . . .
H14 H 0.0888 -0.9128 0.6953 0.060 Uiso 1 1 calc R . .
C15 C 0.2043(4) -0.7594(2) 0.5853(3) 0.0485(6) Uani 1 1 d . . .
H15 H 0.2692 -0.8009 0.5377 0.058 Uiso 1 1 calc R . .
C16 C 0.2179(3) -0.6333(2) 0.5608(2) 0.0441(6) Uani 1 1 d . . .
H16 H 0.2915 -0.5882 0.4962 0.053 Uiso 1 1 calc R . .
C17 C 0.3289(3) -0.1434(2) 0.3980(2) 0.0372(5) Uani 1 1 d . . .
C18 C 0.3604(3) -0.0275(2) 0.3946(2) 0.0415(6) Uani 1 1 d . . .
H18 H 0.3189 -0.0050 0.4597 0.050 Uiso 1 1 calc R . .
C19 C 0.4507(3) 0.0555(2) 0.2991(2) 0.0403(6) Uani 1 1 d . . .
H19 H 0.4712 0.1332 0.2996 0.048 Uiso 1 1 calc R . .
C20 C 0.5111(3) 0.0244(2) 0.2022(2) 0.0382(5) Uani 1 1 d . . .
C21 C 0.4788(3) -0.0903(2) 0.2044(2) 0.0421(6) Uani 1 1 d . . .
H21 H 0.5185 -0.1120 0.1385 0.050 Uiso 1 1 calc R . .
C22 C 0.3908(3) -0.1728(2) 0.2996(2) 0.0411(6) Uani 1 1 d . . .
H22 H 0.3716 -0.2507 0.2989 0.049 Uiso 1 1 calc R . .
C23 C 0.6287(4) 0.2615(3) 0.0980(3) 0.0537(7) Uani 1 1 d . . .
H23A H 0.6918 0.3205 0.0304 0.080 Uiso 1 1 calc R . .
H23B H 0.6832 0.2366 0.1716 0.080 Uiso 1 1 calc R . .
H23C H 0.5121 0.3055 0.1040 0.080 Uiso 1 1 calc R . .
B1 B 0.4687(4) 0.4629(3) 0.2561(3) 0.0470(7) Uani 1 1 d . . .
N1 N -0.0172(3) -0.14264(19) 0.78531(19) 0.0445(5) Uani 1 1 d . . .
O1 O 0.0519(2) -0.39715(14) 0.68747(14) 0.0387(4) Uani 1 1 d . . .
F1 F 0.4454(3) 0.33634(16) 0.32968(17) 0.0789(6) Uani 1 1 d . . .
F2 F 0.4497(3) 0.53093(17) 0.32664(17) 0.0759(6) Uani 1 1 d . . .
F3 F 0.6319(2) 0.45969(16) 0.20472(15) 0.0614(5) Uani 1 1 d . . .
F4 F 0.3545(3) 0.5155(2) 0.17158(19) 0.1013(8) Uani 1 1 d . . .
S1 S 0.62700(10) 0.11852(7) 0.07588(6) 0.0491(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.348(3) . ?
C1 C2 1.366(3) . ?
C1 C11 1.460(3) . ?
C2 C3 1.406(3) . ?
C3 C4 1.408(3) . ?
C3 C17 1.468(3) . ?
C4 C5 1.362(3) . ?
C5 O1 1.347(3) . ?
C5 C6 1.471(3) . ?
C6 N1 1.346(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.385(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.381(4) . ?
C10 N1 1.328(3) . ?
C11 C16 1.397(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.388(4) . ?
C14 C15 1.380(4) . ?
C15 C16 1.379(3) . ?
C17 C18 1.398(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.397(3) . ?
C20 C21 1.395(3) . ?
C20 S1 1.749(2) . ?
C21 C22 1.373(3) . ?
C23 S1 1.791(3) . ?
B1 F4 1.355(4) . ?
B1 F3 1.380(3) . ?
B1 F1 1.386(3) . ?
B1 F2 1.386(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.8(2) . . ?
O1 C1 C11 113.22(19) . . ?
C2 C1 C11 127.0(2) . . ?
C1 C2 C3 121.3(2) . . ?
C2 C3 C4 116.3(2) . . ?
C2 C3 C17 121.4(2) . . ?
C4 C3 C17 122.3(2) . . ?
C5 C4 C3 120.6(2) . . ?
O1 C5 C4 120.6(2) . . ?
O1 C5 C6 113.4(2) . . ?
C4 C5 C6 126.0(2) . . ?
N1 C6 C7 123.5(2) . . ?
N1 C6 C5 114.8(2) . . ?
C7 C6 C5 121.7(2) . . ?
C8 C7 C6 118.2(3) . . ?
C9 C8 C7 119.0(2) . . ?
C8 C9 C10 118.6(2) . . ?
N1 C10 C9 124.1(3) . . ?
C16 C11 C12 119.0(2) . . ?
C16 C11 C1 120.4(2) . . ?
C12 C11 C1 120.5(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C14 120.4(3) . . ?
C15 C14 C13 119.7(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 120.2(2) . . ?
C18 C17 C22 117.4(2) . . ?
C18 C17 C3 121.9(2) . . ?
C22 C17 C3 120.7(2) . . ?
C19 C18 C17 122.0(2) . . ?
C18 C19 C20 119.7(2) . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 S1 116.27(18) . . ?
C19 C20 S1 125.07(18) . . ?
C22 C21 C20 121.4(2) . . ?
C21 C22 C17 120.9(2) . . ?
F4 B1 F3 110.7(2) . . ?
F4 B1 F1 108.7(3) . . ?
F3 B1 F1 108.6(2) . . ?
F4 B1 F2 112.3(3) . . ?
F3 B1 F2 108.6(3) . . ?
F1 B1 F2 107.8(2) . . ?
C10 N1 C6 116.6(2) . . ?
C5 O1 C1 121.32(18) . . ?
C20 S1 C23 103.93(12) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        29.27
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.285
_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_AL204_a
_database_code_depnum_ccdc_archive 'CCDC 1541815'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 B F5 N O'
_chemical_formula_weight         415.16

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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                   7.2677(2)
_cell_length_b                   14.2809(3)
_cell_length_c                   17.5498(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.5668(9)
_cell_angle_gamma                90
_cell_volume                     1805.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9360
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.07
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.8312
_exptl_transmission_factor_max   0.9579
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28487
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_full        25.081
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3204
_reflns_number_gt                2532
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'Microsoft Word'
_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)+(0.0435P)²+1.1022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3204
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7876(2) 0.30454(12) 0.19966(10) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.8107(2) 0.39404(12) 0.17609(10) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.860725 0.404520 0.129456 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7629(2) 0.47104(13) 0.21862(10) 0.0167(4) Uani 1 1 d . . . . .
C4 C 0.6911(2) 0.45034(12) 0.28773(10) 0.0173(4) Uani 1 1 d . . . . .
H4 H 0.654782 0.499902 0.318636 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6735(2) 0.36037(13) 0.31026(10) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.6086(2) 0.32868(13) 0.38217(10) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.6090(2) 0.23454(13) 0.40271(11) 0.0193(4) Uani 1 1 d . . . . .
H7 H 0.654542 0.188141 0.371206 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5415(2) 0.21017(14) 0.46996(11) 0.0223(4) Uani 1 1 d . . . . .
H8 H 0.539547 0.146564 0.485693 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4770(3) 0.28012(14) 0.51390(11) 0.0245(4) Uani 1 1 d . . . . .
H9 H 0.427940 0.265239 0.559992 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4847(3) 0.37223(14) 0.48986(11) 0.0236(4) Uani 1 1 d . . . . .
H10 H 0.441980 0.419702 0.521142 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8308(2) 0.21785(12) 0.16137(10) 0.0159(4) Uani 1 1 d . . . . .
C12 C 0.7741(2) 0.13143(13) 0.18672(10) 0.0183(4) Uani 1 1 d . . . . .
H12 H 0.703669 0.128621 0.228587 0.022 Uiso 1 1 calc R U . . .
C13 C 0.8196(3) 0.04976(13) 0.15141(11) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.779796 -0.008958 0.168759 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9235(3) 0.05358(13) 0.09047(11) 0.0229(4) Uani 1 1 d . . . . .
H14 H 0.955333 -0.002538 0.066248 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9809(3) 0.13948(13) 0.06502(11) 0.0223(4) Uani 1 1 d . . . . .
H15 H 1.051766 0.141914 0.023293 0.027 Uiso 1 1 calc R U . . .
C16 C 0.9355(3) 0.22142(13) 0.09997(10) 0.0189(4) Uani 1 1 d . . . . .
H16 H 0.975262 0.280017 0.082397 0.023 Uiso 1 1 calc R U . . .
C17 C 0.7917(2) 0.56736(12) 0.19372(10) 0.0171(4) Uani 1 1 d . . . . .
C18 C 0.7515(2) 0.64465(13) 0.23818(11) 0.0188(4) Uani 1 1 d . . . . .
H18 H 0.697087 0.634590 0.283835 0.023 Uiso 1 1 calc R U . . .
C19 C 0.7894(2) 0.73502(13) 0.21685(11) 0.0190(4) Uani 1 1 d . . . . .
H19 H 0.761533 0.787133 0.246968 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8685(2) 0.74704(13) 0.15084(11) 0.0194(4) Uani 1 1 d . . . . .
C21 C 0.9071(3) 0.67466(13) 0.10403(11) 0.0211(4) Uani 1 1 d . . . . .
H21 H 0.959284 0.686149 0.058055 0.025 Uiso 1 1 calc R U . . .
C22 C 0.8679(2) 0.58469(13) 0.12564(11) 0.0202(4) Uani 1 1 d . . . . .
H22 H 0.892861 0.533606 0.093883 0.024 Uiso 1 1 calc R U . . .
B1 B 0.3030(3) 0.43645(16) 0.12242(14) 0.0267(5) Uani 1 1 d . . . . .
N1 N 0.5492(2) 0.39812(11) 0.42488(9) 0.0213(4) Uani 1 1 d . . . . .
O1 O 0.71945(16) 0.28872(8) 0.26647(7) 0.0165(3) Uani 1 1 d . . . . .
F1 F 0.91180(15) 0.83556(7) 0.13044(6) 0.0275(3) Uani 1 1 d . . . . .
F2 F 0.14725(15) 0.42079(8) 0.06866(6) 0.0279(3) Uani 1 1 d . . . . .
F3 F 0.37841(17) 0.35200(8) 0.15023(7) 0.0349(3) Uani 1 1 d . . . . .
F41 F 0.4425(5) 0.4736(4) 0.0787(3) 0.0329(11) Uani 0.62(2) 1 d . . P A 1
F51 F 0.2756(8) 0.5000(5) 0.1755(4) 0.0416(18) Uani 0.62(2) 1 d . . P A 1
F42 F 0.4075(19) 0.5034(11) 0.1101(13) 0.082(7) Uani 0.38(2) 1 d . . P A 2
F52 F 0.2131(18) 0.4567(14) 0.1942(4) 0.053(4) Uani 0.38(2) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.351(2) . ?
C1 C2 1.361(3) . ?
C1 C11 1.462(2) . ?
C2 C3 1.398(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.413(3) . ?
C3 C17 1.467(3) . ?
C4 C5 1.355(3) . ?
C4 H4 0.9500 . ?
C5 O1 1.348(2) . ?
C5 C6 1.475(3) . ?
C6 N1 1.348(2) . ?
C6 C7 1.392(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.341(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.403(3) . ?
C17 C18 1.405(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9500 . ?
C20 F1 1.362(2) . ?
C20 C21 1.372(3) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
B1 F42 1.258(7) . ?
B1 F51 1.333(4) . ?
B1 F3 1.387(3) . ?
B1 F2 1.393(3) . ?
B1 F41 1.449(4) . ?
B1 F52 1.520(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.68(16) . . ?
O1 C1 C11 112.49(15) . . ?
C2 C1 C11 127.83(16) . . ?
C1 C2 C3 121.81(17) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 116.08(17) . . ?
C2 C3 C17 121.53(16) . . ?
C4 C3 C17 122.37(16) . . ?
C5 C4 C3 120.55(16) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O1 C5 C4 120.90(16) . . ?
O1 C5 C6 112.70(15) . . ?
C4 C5 C6 126.40(16) . . ?
N1 C6 C7 123.81(17) . . ?
N1 C6 C5 114.33(16) . . ?
C7 C6 C5 121.87(16) . . ?
C8 C7 C6 118.43(18) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C9 C8 C7 118.67(18) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 119.11(17) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N1 C10 C9 123.63(18) . . ?
N1 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C12 C11 C16 119.46(17) . . ?
C12 C11 C1 120.89(16) . . ?
C16 C11 C1 119.62(16) . . ?
C13 C12 C11 120.45(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.91(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.95(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.43(17) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 119.80(17) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C22 C17 C18 117.94(17) . . ?
C22 C17 C3 120.47(16) . . ?
C18 C17 C3 121.54(16) . . ?
C19 C18 C17 121.34(17) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 117.84(17) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
F1 C20 C19 118.39(16) . . ?
F1 C20 C21 118.01(17) . . ?
C19 C20 C21 123.60(18) . . ?
C20 C21 C22 118.10(18) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C17 121.14(17) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
F42 B1 F3 120.2(7) . . ?
F51 B1 F3 115.8(4) . . ?
F42 B1 F2 117.4(5) . . ?
F51 B1 F2 113.5(2) . . ?
F3 B1 F2 110.30(17) . . ?
F51 B1 F41 107.4(3) . . ?
F3 B1 F41 103.4(2) . . ?
F2 B1 F41 105.2(2) . . ?
F42 B1 F52 109.4(7) . . ?
F3 B1 F52 93.8(6) . . ?
F2 B1 F52 101.1(5) . . ?
C10 N1 C6 116.33(16) . . ?
C5 O1 C1 120.97(14) . . ?

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
O1 C1 C2 C3 -1.1(3) . . . . ?
C11 C1 C2 C3 179.87(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 C17 178.70(16) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C17 C3 C4 C5 -177.30(16) . . . . ?
C3 C4 C5 O1 -1.7(3) . . . . ?
C3 C4 C5 C6 177.24(16) . . . . ?
O1 C5 C6 N1 -175.57(14) . . . . ?
C4 C5 C6 N1 5.4(3) . . . . ?
O1 C5 C6 C7 4.0(2) . . . . ?
C4 C5 C6 C7 -175.03(17) . . . . ?
N1 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C8 -178.33(16) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 N1 1.2(3) . . . . ?
O1 C1 C11 C12 10.4(2) . . . . ?
C2 C1 C11 C12 -170.43(18) . . . . ?
O1 C1 C11 C16 -167.50(15) . . . . ?
C2 C1 C11 C16 11.6(3) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C1 C11 C12 C13 -178.35(17) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C1 C11 C16 C15 178.23(17) . . . . ?
C2 C3 C17 C22 0.4(3) . . . . ?
C4 C3 C17 C22 178.35(17) . . . . ?
C2 C3 C17 C18 -177.09(16) . . . . ?
C4 C3 C17 C18 0.9(3) . . . . ?
C22 C17 C18 C19 -1.5(3) . . . . ?
C3 C17 C18 C19 176.01(16) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 F1 -178.03(15) . . . . ?
C18 C19 C20 C21 1.9(3) . . . . ?
F1 C20 C21 C22 178.33(16) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C18 C17 C22 C21 1.8(3) . . . . ?
C3 C17 C22 C21 -175.73(17) . . . . ?
C9 C10 N1 C6 -0.1(3) . . . . ?
C7 C6 N1 C10 -1.2(3) . . . . ?
C5 C6 N1 C10 178.44(15) . . . . ?
C4 C5 O1 C1 1.3(2) . . . . ?
C6 C5 O1 C1 -177.79(14) . . . . ?
C2 C1 O1 C5 0.1(2) . . . . ?
C11 C1 O1 C5 179.29(14) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_al176_a
_database_code_depnum_ccdc_archive 'CCDC 1541819'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_audit_creation_date             2014-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014/6

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C27 H15 F3 N2 O4 W)'
_chemical_formula_sum            'C54 H30 F6 N4 O8 W2'
_chemical_formula_weight         1344.52
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.5198(7)
_cell_length_b                   17.2400(9)
_cell_length_c                   19.1014(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.3220(14)
_cell_angle_gamma                90
_cell_volume                     4718.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9507
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.552
_cell_measurement_theta_min      2.877
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.230
_exptl_absorpt_coefficient_mu    4.958
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1383 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.4587.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            78726
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.563
_diffrn_reflns_theta_min         2.254
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13202
_reflns_number_total             14451
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.837
_refine_diff_density_min         -1.492
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         14451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0194
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0118P)²+5.4192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0438
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C29(H29),
  C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43), C45(H45), C46(H46), C48(H48), C49(H49)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.45250(2) 0.88045(2) 0.67596(2) 0.01312(2) Uani 1 1 d . . . . .
F1 F 0.69592(9) 0.34392(7) 0.41520(6) 0.0232(3) Uani 1 1 d . . . . .
F2 F 0.74729(8) 0.30047(7) 0.52037(7) 0.0223(3) Uani 1 1 d . . . . .
F3 F 0.60095(8) 0.29130(7) 0.47676(6) 0.0199(2) Uani 1 1 d . . . . .
O1 O 0.28893(10) 0.84872(9) 0.54716(8) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.30197(10) 0.82355(9) 0.76490(8) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.57220(12) 0.94213(11) 0.81855(9) 0.0331(4) Uani 1 1 d . . . . .
O4 O 0.35317(12) 1.04179(9) 0.67402(9) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.53293(11) 0.76913(9) 0.66150(8) 0.0128(3) Uani 1 1 d . . . . .
N2 N 0.55526(11) 0.90660(10) 0.60457(8) 0.0152(3) Uani 1 1 d . . . . .
C1 C 0.52300(12) 0.69992(11) 0.69349(9) 0.0128(3) Uani 1 1 d . . . . .
C2 C 0.55080(13) 0.63043(11) 0.66628(10) 0.0147(3) Uani 1 1 d . . . . .
H2 H 0.5405 0.5830 0.6891 0.018 Uiso 1 1 calc R . . . .
C3 C 0.59353(13) 0.62940(11) 0.60590(10) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.61155(13) 0.70128(11) 0.57737(10) 0.0152(3) Uani 1 1 d . . . . .
H4 H 0.6449 0.7038 0.5386 0.018 Uiso 1 1 calc R . . . .
C5 C 0.58091(12) 0.76930(11) 0.60545(9) 0.0130(3) Uani 1 1 d . . . . .
C6 C 0.59794(13) 0.84653(11) 0.57683(10) 0.0147(3) Uani 1 1 d . . . . .
C7 C 0.65574(14) 0.85844(12) 0.52611(10) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.6836 0.8156 0.5063 0.022 Uiso 1 1 calc R . . . .
C8 C 0.67208(15) 0.93358(13) 0.50483(11) 0.0230(4) Uani 1 1 d . . . . .
H8 H 0.7106 0.9428 0.4700 0.028 Uiso 1 1 calc R . . . .
C9 C 0.63136(15) 0.99475(13) 0.53523(11) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.6435 1.0467 0.5229 0.028 Uiso 1 1 calc R . . . .
C10 C 0.57257(14) 0.97917(12) 0.58393(11) 0.0200(4) Uani 1 1 d . . . . .
H10 H 0.5433 1.0214 0.6035 0.024 Uiso 1 1 calc R . . . .
C11 C 0.48179(13) 0.69758(11) 0.75958(10) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.52316(13) 0.73841(12) 0.81970(10) 0.0165(4) Uani 1 1 d . . . . .
H12 H 0.5772 0.7690 0.8181 0.020 Uiso 1 1 calc R . . . .
C13 C 0.48506(14) 0.73419(12) 0.88185(10) 0.0186(4) Uani 1 1 d . . . . .
H13 H 0.5132 0.7619 0.9228 0.022 Uiso 1 1 calc R . . . .
C14 C 0.40593(15) 0.68959(12) 0.88435(10) 0.0197(4) Uani 1 1 d . . . . .
H14 H 0.3793 0.6877 0.9266 0.024 Uiso 1 1 calc R . . . .
C15 C 0.36592(14) 0.64789(12) 0.82509(10) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.3120 0.6172 0.8269 0.023 Uiso 1 1 calc R . . . .
C16 C 0.40440(13) 0.65084(11) 0.76305(10) 0.0159(3) Uani 1 1 d . . . . .
H16 H 0.3779 0.6210 0.7230 0.019 Uiso 1 1 calc R . . . .
C17 C 0.61688(12) 0.55540(11) 0.57380(10) 0.0142(3) Uani 1 1 d . . . . .
C18 C 0.64115(13) 0.48995(11) 0.61639(10) 0.0162(4) Uani 1 1 d . . . . .
H18 H 0.6436 0.4934 0.6663 0.019 Uiso 1 1 calc R . . . .
C19 C 0.66160(14) 0.42021(11) 0.58609(10) 0.0165(4) Uani 1 1 d . . . . .
H19 H 0.6784 0.3761 0.6152 0.020 Uiso 1 1 calc R . . . .
C20 C 0.65735(13) 0.41514(11) 0.51274(10) 0.0146(3) Uani 1 1 d . . . . .
C21 C 0.63218(13) 0.47900(11) 0.46980(10) 0.0157(3) Uani 1 1 d . . . . .
H21 H 0.6286 0.4750 0.4198 0.019 Uiso 1 1 calc R . . . .
C22 C 0.61219(13) 0.54907(11) 0.50033(10) 0.0159(3) Uani 1 1 d . . . . .
H22 H 0.5952 0.5929 0.4710 0.019 Uiso 1 1 calc R . . . .
C23 C 0.67612(13) 0.33856(11) 0.48131(10) 0.0155(3) Uani 1 1 d . . . . .
C24 C 0.35196(13) 0.85609(11) 0.59186(10) 0.0148(3) Uani 1 1 d . . . . .
C25 C 0.36010(14) 0.84342(12) 0.73367(10) 0.0168(4) Uani 1 1 d . . . . .
C26 C 0.53358(14) 0.91751(12) 0.76592(11) 0.0200(4) Uani 1 1 d . . . . .
C27 C 0.39082(14) 0.98157(12) 0.67468(10) 0.0189(4) Uani 1 1 d . . . . .
W2 W 0.06901(2) 0.30876(2) 0.14734(2) 0.01391(2) Uani 1 1 d . . . . .
F4 F 0.07293(9) 0.54887(9) 0.70040(7) 0.0326(3) Uani 1 1 d . . . . .
F5 F 0.21763(9) 0.57190(9) 0.70212(7) 0.0317(3) Uani 1 1 d . . . . .
F6 F 0.11458(14) 0.65540(9) 0.65647(8) 0.0476(4) Uani 1 1 d . . . . .
O5 O 0.25121(11) 0.24286(10) 0.09666(9) 0.0277(3) Uani 1 1 d . . . . .
O6 O 0.00779(12) 0.14024(9) 0.18177(8) 0.0259(3) Uani 1 1 d . . . . .
O7 O -0.14176(12) 0.35560(13) 0.15203(11) 0.0451(5) Uani 1 1 d . . . . .
O8 O -0.01525(12) 0.27385(10) -0.01046(8) 0.0272(3) Uani 1 1 d . . . . .
N3 N 0.12463(11) 0.35359(10) 0.25887(8) 0.0148(3) Uani 1 1 d . . . . .
N4 N 0.10454(11) 0.43327(10) 0.13774(8) 0.0158(3) Uani 1 1 d . . . . .
C28 C 0.13380(13) 0.31178(11) 0.32001(10) 0.0156(3) Uani 1 1 d . . . . .
C29 C 0.13421(13) 0.34700(12) 0.38559(10) 0.0162(4) Uani 1 1 d . . . . .
H29 H 0.1366 0.3156 0.4267 0.019 Uiso 1 1 calc R . . . .
C30 C 0.13124(13) 0.42765(11) 0.39202(10) 0.0151(3) Uani 1 1 d . . . . .
C31 C 0.13122(13) 0.47009(11) 0.32971(10) 0.0156(3) Uani 1 1 d . . . . .
H31 H 0.1340 0.5251 0.3317 0.019 Uiso 1 1 calc R . . . .
C32 C 0.12720(12) 0.43256(11) 0.26492(10) 0.0145(3) Uani 1 1 d . . . . .
C33 C 0.12317(13) 0.47645(12) 0.19801(10) 0.0157(3) Uani 1 1 d . . . . .
C34 C 0.13807(14) 0.55624(12) 0.19589(11) 0.0191(4) Uani 1 1 d . . . . .
H34 H 0.1505 0.5852 0.2387 0.023 Uiso 1 1 calc R . . . .
C35 C 0.13461(14) 0.59326(13) 0.13101(11) 0.0208(4) Uani 1 1 d . . . . .
H35 H 0.1444 0.6476 0.1287 0.025 Uiso 1 1 calc R . . . .
C36 C 0.11653(14) 0.54890(13) 0.06949(11) 0.0213(4) Uani 1 1 d . . . . .
H36 H 0.1143 0.5724 0.0243 0.026 Uiso 1 1 calc R . . . .
C37 C 0.10192(14) 0.47037(13) 0.07503(10) 0.0194(4) Uani 1 1 d . . . . .
H37 H 0.0894 0.4407 0.0326 0.023 Uiso 1 1 calc R . . . .
C38 C 0.14706(13) 0.22619(12) 0.31752(10) 0.0162(4) Uani 1 1 d . . . . .
C39 C 0.21772(14) 0.19560(12) 0.28373(10) 0.0184(4) Uani 1 1 d . . . . .
H39 H 0.2542 0.2291 0.2598 0.022 Uiso 1 1 calc R . . . .
C40 C 0.23451(15) 0.11625(13) 0.28521(11) 0.0222(4) Uani 1 1 d . . . . .
H40 H 0.2823 0.0957 0.2620 0.027 Uiso 1 1 calc R . . . .
C41 C 0.18188(15) 0.06693(13) 0.32033(11) 0.0236(4) Uani 1 1 d . . . . .
H41 H 0.1934 0.0127 0.3210 0.028 Uiso 1 1 calc R . . . .
C42 C 0.11230(15) 0.09693(13) 0.35450(11) 0.0219(4) Uani 1 1 d . . . . .
H42 H 0.0764 0.0631 0.3786 0.026 Uiso 1 1 calc R . . . .
C43 C 0.09500(14) 0.17642(12) 0.35352(10) 0.0193(4) Uani 1 1 d . . . . .
H43 H 0.0477 0.1968 0.3774 0.023 Uiso 1 1 calc R . . . .
C44 C 0.12923(13) 0.46644(11) 0.46129(10) 0.0148(3) Uani 1 1 d . . . . .
C45 C 0.15825(14) 0.42696(12) 0.52519(10) 0.0191(4) Uani 1 1 d . . . . .
H45 H 0.1782 0.3745 0.5242 0.023 Uiso 1 1 calc R . . . .
C46 C 0.15818(14) 0.46360(13) 0.58988(10) 0.0200(4) Uani 1 1 d . . . . .
H46 H 0.1778 0.4363 0.6329 0.024 Uiso 1 1 calc R . . . .
C47 C 0.12928(13) 0.54045(12) 0.59133(10) 0.0179(4) Uani 1 1 d . . . . .
C48 C 0.09844(14) 0.58010(12) 0.52861(10) 0.0178(4) Uani 1 1 d . . . . .
H48 H 0.0775 0.6322 0.5298 0.021 Uiso 1 1 calc R . . . .
C49 C 0.09844(13) 0.54286(12) 0.46399(10) 0.0169(4) Uani 1 1 d . . . . .
H49 H 0.0772 0.5699 0.4211 0.020 Uiso 1 1 calc R . . . .
C50 C 0.13321(15) 0.57972(14) 0.66178(11) 0.0231(4) Uani 1 1 d . . . . .
C51 C 0.18883(14) 0.26913(12) 0.11956(10) 0.0193(4) Uani 1 1 d . . . . .
C52 C 0.03316(14) 0.20194(12) 0.16938(10) 0.0192(4) Uani 1 1 d . . . . .
C53 C -0.06493(15) 0.34085(14) 0.15542(12) 0.0247(4) Uani 1 1 d . . . . .
C54 C 0.01623(14) 0.28716(12) 0.04860(10) 0.0186(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 N1 2.2864(16) . ?
W1 N2 2.2243(16) . ?
W1 C24 2.0319(19) . ?
W1 C25 1.975(2) . ?
W1 C26 2.023(2) . ?
W1 C27 1.958(2) . ?
F1 C23 1.343(2) . ?
F2 C23 1.344(2) . ?
F3 C23 1.353(2) . ?
O1 C24 1.153(2) . ?
O2 C25 1.161(2) . ?
O3 C26 1.150(3) . ?
O4 C27 1.172(3) . ?
N1 C1 1.359(2) . ?
N1 C5 1.369(2) . ?
N2 C6 1.358(2) . ?
N2 C10 1.348(3) . ?
C1 C2 1.391(3) . ?
C1 C11 1.483(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.395(3) . ?
C3 C17 1.478(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.475(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.387(3) . ?
C11 C12 1.397(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.391(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.398(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.395(3) . ?
C20 C21 1.386(3) . ?
C20 C23 1.494(3) . ?
C21 C22 1.392(3) . ?
W2 N3 2.2871(16) . ?
W2 N4 2.2221(17) . ?
W2 C51 2.018(2) . ?
W2 C52 1.978(2) . ?
W2 C53 2.052(2) . ?
W2 C54 1.953(2) . ?
F4 C50 1.342(2) . ?
F5 C50 1.345(2) . ?
F6 C50 1.333(3) . ?
O5 C51 1.160(3) . ?
O6 C52 1.162(3) . ?
O7 C53 1.136(3) . ?
O8 C54 1.169(2) . ?
N3 C28 1.360(2) . ?
N3 C32 1.366(3) . ?
N4 C33 1.361(2) . ?
N4 C37 1.353(2) . ?
C28 C29 1.391(3) . ?
C28 C38 1.490(3) . ?
C29 C30 1.397(3) . ?
C30 C31 1.397(3) . ?
C30 C44 1.487(3) . ?
C31 C32 1.389(3) . ?
C32 C33 1.478(3) . ?
C33 C34 1.394(3) . ?
C34 C35 1.388(3) . ?
C35 C36 1.391(3) . ?
C36 C37 1.377(3) . ?
C38 C39 1.401(3) . ?
C38 C43 1.396(3) . ?
C39 C40 1.389(3) . ?
C40 C41 1.387(3) . ?
C41 C42 1.388(3) . ?
C42 C43 1.393(3) . ?
C44 C45 1.402(3) . ?
C44 C49 1.395(3) . ?
C45 C46 1.388(3) . ?
C46 C47 1.391(3) . ?
C47 C48 1.389(3) . ?
C47 C50 1.499(3) . ?
C48 C49 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 W1 N1 71.92(6) . . ?
C24 W1 N1 92.67(6) . . ?
C24 W1 N2 91.41(7) . . ?
C25 W1 N1 101.68(7) . . ?
C25 W1 N2 172.43(7) . . ?
C25 W1 C24 84.75(8) . . ?
C25 W1 C26 88.99(8) . . ?
C26 W1 N1 97.43(7) . . ?
C26 W1 N2 95.79(7) . . ?
C26 W1 C24 169.02(8) . . ?
C27 W1 N1 170.84(7) . . ?
C27 W1 N2 99.36(7) . . ?
C27 W1 C24 84.58(8) . . ?
C27 W1 C25 86.79(8) . . ?
C27 W1 C26 86.07(8) . . ?
C1 N1 W1 126.11(12) . . ?
C1 N1 C5 117.27(16) . . ?
C5 N1 W1 115.29(12) . . ?
C6 N2 W1 118.59(13) . . ?
C10 N2 W1 122.89(14) . . ?
C10 N2 C6 118.38(17) . . ?
N1 C1 C2 121.99(16) . . ?
N1 C1 C11 119.58(16) . . ?
C2 C1 C11 118.43(16) . . ?
C1 C2 C3 120.95(17) . . ?
C2 C3 C17 121.08(17) . . ?
C4 C3 C2 116.62(17) . . ?
C4 C3 C17 122.30(17) . . ?
C5 C4 C3 120.39(17) . . ?
N1 C5 C4 122.30(17) . . ?
N1 C5 C6 115.41(16) . . ?
C4 C5 C6 122.29(16) . . ?
N2 C6 C5 115.41(16) . . ?
N2 C6 C7 121.49(18) . . ?
C7 C6 C5 123.07(18) . . ?
C8 C7 C6 119.38(19) . . ?
C9 C8 C7 118.92(19) . . ?
C8 C9 C10 119.1(2) . . ?
N2 C10 C9 122.7(2) . . ?
C12 C11 C1 120.48(17) . . ?
C16 C11 C1 119.75(16) . . ?
C16 C11 C12 119.67(17) . . ?
C13 C12 C11 119.87(18) . . ?
C14 C13 C12 120.25(18) . . ?
C15 C14 C13 119.88(18) . . ?
C14 C15 C16 120.25(19) . . ?
C15 C16 C11 120.01(18) . . ?
C18 C17 C3 120.45(16) . . ?
C22 C17 C3 120.43(17) . . ?
C22 C17 C18 119.09(17) . . ?
C19 C18 C17 120.40(17) . . ?
C18 C19 C20 119.71(18) . . ?
C19 C20 C23 118.53(17) . . ?
C21 C20 C19 120.60(18) . . ?
C21 C20 C23 120.81(17) . . ?
C20 C21 C22 119.62(17) . . ?
C21 C22 C17 120.57(18) . . ?
F1 C23 F2 107.06(15) . . ?
F1 C23 F3 105.92(15) . . ?
F1 C23 C20 113.44(16) . . ?
F2 C23 F3 106.33(15) . . ?
F2 C23 C20 112.50(15) . . ?
F3 C23 C20 111.11(16) . . ?
O1 C24 W1 172.15(16) . . ?
O2 C25 W1 176.22(17) . . ?
O3 C26 W1 173.44(19) . . ?
O4 C27 W1 179.40(19) . . ?
N4 W2 N3 72.47(6) . . ?
C51 W2 N3 99.78(7) . . ?
C51 W2 N4 94.81(7) . . ?
C51 W2 C53 168.22(8) . . ?
C52 W2 N3 100.47(7) . . ?
C52 W2 N4 171.79(7) . . ?
C52 W2 C51 90.49(8) . . ?
C52 W2 C53 87.12(9) . . ?
C53 W2 N3 91.99(7) . . ?
C53 W2 N4 88.93(8) . . ?
C54 W2 N3 171.13(7) . . ?
C54 W2 N4 99.47(7) . . ?
C54 W2 C51 84.36(8) . . ?
C54 W2 C52 87.27(8) . . ?
C54 W2 C53 84.01(9) . . ?
C28 N3 W2 126.26(13) . . ?
C28 N3 C32 117.24(16) . . ?
C32 N3 W2 114.59(12) . . ?
C33 N4 W2 118.40(13) . . ?
C37 N4 W2 123.78(13) . . ?
C37 N4 C33 117.63(17) . . ?
N3 C28 C29 121.83(18) . . ?
N3 C28 C38 119.50(17) . . ?
C29 C28 C38 118.63(17) . . ?
C28 C29 C30 121.18(18) . . ?
C29 C30 C44 122.08(17) . . ?
C31 C30 C29 116.23(17) . . ?
C31 C30 C44 121.69(18) . . ?
C32 C31 C30 120.61(18) . . ?
N3 C32 C31 122.41(17) . . ?
N3 C32 C33 116.11(16) . . ?
C31 C32 C33 121.46(18) . . ?
N4 C33 C32 115.22(17) . . ?
N4 C33 C34 121.72(18) . . ?
C34 C33 C32 123.06(17) . . ?
C35 C34 C33 119.77(19) . . ?
C34 C35 C36 118.4(2) . . ?
C37 C36 C35 119.07(19) . . ?
N4 C37 C36 123.38(19) . . ?
C39 C38 C28 119.72(18) . . ?
C43 C38 C28 120.66(18) . . ?
C43 C38 C39 119.41(19) . . ?
C40 C39 C38 120.04(19) . . ?
C41 C40 C39 120.3(2) . . ?
C40 C41 C42 119.9(2) . . ?
C41 C42 C43 120.2(2) . . ?
C42 C43 C38 120.03(19) . . ?
C45 C44 C30 120.68(18) . . ?
C49 C44 C30 120.68(17) . . ?
C49 C44 C45 118.64(18) . . ?
C46 C45 C44 120.73(19) . . ?
C45 C46 C47 119.65(19) . . ?
C46 C47 C50 118.69(18) . . ?
C48 C47 C46 120.50(18) . . ?
C48 C47 C50 120.80(19) . . ?
C47 C48 C49 119.46(19) . . ?
C48 C49 C44 120.98(18) . . ?
F4 C50 F5 105.09(17) . . ?
F4 C50 C47 112.39(18) . . ?
F5 C50 C47 111.57(18) . . ?
F6 C50 F4 106.70(19) . . ?
F6 C50 F5 107.25(18) . . ?
F6 C50 C47 113.33(18) . . ?
O5 C51 W2 172.03(17) . . ?
O6 C52 W2 176.82(19) . . ?
O7 C53 W2 172.0(2) . . ?
O8 C54 W2 179.7(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
W1 N1 C1 C2 159.14(14) . . . . ?
W1 N1 C1 C11 -21.1(2) . . . . ?
W1 N1 C5 C4 -161.95(14) . . . . ?
W1 N1 C5 C6 18.06(19) . . . . ?
W1 N2 C6 C5 -8.3(2) . . . . ?
W1 N2 C6 C7 173.34(14) . . . . ?
W1 N2 C10 C9 -174.98(15) . . . . ?
N1 C1 C2 C3 2.4(3) . . . . ?
N1 C1 C11 C12 -59.0(2) . . . . ?
N1 C1 C11 C16 124.67(19) . . . . ?
N1 C5 C6 N2 -6.9(2) . . . . ?
N1 C5 C6 C7 171.46(17) . . . . ?
N2 C6 C7 C8 1.8(3) . . . . ?
C1 N1 C5 C4 5.7(3) . . . . ?
C1 N1 C5 C6 -174.28(16) . . . . ?
C1 C2 C3 C4 3.7(3) . . . . ?
C1 C2 C3 C17 -175.48(17) . . . . ?
C1 C11 C12 C13 -178.45(18) . . . . ?
C1 C11 C16 C15 179.45(18) . . . . ?
C2 C1 C11 C12 120.7(2) . . . . ?
C2 C1 C11 C16 -55.6(2) . . . . ?
C2 C3 C4 C5 -5.0(3) . . . . ?
C2 C3 C17 C18 -31.8(3) . . . . ?
C2 C3 C17 C22 146.14(19) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C3 C4 C5 C6 -179.71(17) . . . . ?
C3 C17 C18 C19 178.97(17) . . . . ?
C3 C17 C22 C21 -178.61(17) . . . . ?
C4 C3 C17 C18 149.05(18) . . . . ?
C4 C3 C17 C22 -33.0(3) . . . . ?
C4 C5 C6 N2 173.14(17) . . . . ?
C4 C5 C6 C7 -8.5(3) . . . . ?
C5 N1 C1 C2 -7.0(3) . . . . ?
C5 N1 C1 C11 172.70(16) . . . . ?
C5 C6 C7 C8 -176.49(18) . . . . ?
C6 N2 C10 C9 0.6(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 N2 1.9(3) . . . . ?
C10 N2 C6 C5 175.96(17) . . . . ?
C10 N2 C6 C7 -2.4(3) . . . . ?
C11 C1 C2 C3 -177.34(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C11 C16 C15 3.1(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -1.9(3) . . . . ?
C16 C11 C12 C13 -2.1(3) . . . . ?
C17 C3 C4 C5 174.21(17) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C17 C22 C21 -0.6(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C18 C19 C20 C23 -177.67(17) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
C19 C20 C23 F1 -162.47(17) . . . . ?
C19 C20 C23 F2 -40.8(2) . . . . ?
C19 C20 C23 F3 78.3(2) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C21 C20 C23 F1 20.4(3) . . . . ?
C21 C20 C23 F2 142.08(18) . . . . ?
C21 C20 C23 F3 -98.8(2) . . . . ?
C22 C17 C18 C19 1.0(3) . . . . ?
C23 C20 C21 C22 177.96(17) . . . . ?
W2 N3 C28 C29 -155.55(14) . . . . ?
W2 N3 C28 C38 26.6(2) . . . . ?
W2 N3 C32 C31 160.06(14) . . . . ?
W2 N3 C32 C33 -18.5(2) . . . . ?
W2 N4 C33 C32 6.2(2) . . . . ?
W2 N4 C33 C34 -174.37(14) . . . . ?
W2 N4 C37 C36 174.45(15) . . . . ?
N3 C28 C29 C30 -4.2(3) . . . . ?
N3 C28 C38 C39 52.2(3) . . . . ?
N3 C28 C38 C43 -133.12(19) . . . . ?
N3 C32 C33 N4 8.6(2) . . . . ?
N3 C32 C33 C34 -170.81(17) . . . . ?
N4 C33 C34 C35 -0.4(3) . . . . ?
C28 N3 C32 C31 -5.2(3) . . . . ?
C28 N3 C32 C33 176.21(16) . . . . ?
C28 C29 C30 C31 -2.2(3) . . . . ?
C28 C29 C30 C44 178.44(17) . . . . ?
C28 C38 C39 C40 175.77(18) . . . . ?
C28 C38 C43 C42 -175.88(18) . . . . ?
C29 C28 C38 C39 -125.7(2) . . . . ?
C29 C28 C38 C43 48.9(3) . . . . ?
C29 C30 C31 C32 4.7(3) . . . . ?
C29 C30 C44 C45 19.5(3) . . . . ?
C29 C30 C44 C49 -160.50(18) . . . . ?
C30 C31 C32 N3 -1.1(3) . . . . ?
C30 C31 C32 C33 177.43(17) . . . . ?
C30 C44 C45 C46 178.70(18) . . . . ?
C30 C44 C49 C48 -178.48(18) . . . . ?
C31 C30 C44 C45 -159.81(18) . . . . ?
C31 C30 C44 C49 20.2(3) . . . . ?
C31 C32 C33 N4 -169.96(17) . . . . ?
C31 C32 C33 C34 10.6(3) . . . . ?
C32 N3 C28 C29 7.8(3) . . . . ?
C32 N3 C28 C38 -170.09(16) . . . . ?
C32 C33 C34 C35 178.97(18) . . . . ?
C33 N4 C37 C36 -0.4(3) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
C34 C35 C36 C37 0.6(3) . . . . ?
C35 C36 C37 N4 -0.3(3) . . . . ?
C37 N4 C33 C32 -178.71(16) . . . . ?
C37 N4 C33 C34 0.7(3) . . . . ?
C38 C28 C29 C30 173.70(17) . . . . ?
C38 C39 C40 C41 -0.3(3) . . . . ?
C39 C38 C43 C42 -1.2(3) . . . . ?
C39 C40 C41 C42 -0.3(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C38 0.6(3) . . . . ?
C43 C38 C39 C40 1.0(3) . . . . ?
C44 C30 C31 C32 -175.94(17) . . . . ?
C44 C45 C46 C47 -0.2(3) . . . . ?
C45 C44 C49 C48 1.5(3) . . . . ?
C45 C46 C47 C48 1.5(3) . . . . ?
C45 C46 C47 C50 -177.73(19) . . . . ?
C46 C47 C48 C49 -1.3(3) . . . . ?
C46 C47 C50 F4 -66.5(2) . . . . ?
C46 C47 C50 F5 51.3(3) . . . . ?
C46 C47 C50 F6 172.45(19) . . . . ?
C47 C48 C49 C44 -0.2(3) . . . . ?
C48 C47 C50 F4 114.2(2) . . . . ?
C48 C47 C50 F5 -128.0(2) . . . . ?
C48 C47 C50 F6 -6.8(3) . . . . ?
C49 C44 C45 C46 -1.3(3) . . . . ?
C50 C47 C48 C49 177.92(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_WO13
_database_code_depnum_ccdc_archive 'CCDC 1542023'
_audit_update_record             
;
2017-04-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 B F4 N O S'
_chemical_formula_weight         443.25

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.0880(3)
_cell_length_b                   26.1395(7)
_cell_length_c                   7.7459(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.1370(10)
_cell_angle_gamma                90
_cell_volume                     1980.70(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7670
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.99
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.8344
_exptl_transmission_factor_max   0.9705
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17873
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         25.031
_diffrn_reflns_theta_full        25.031
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3494
_reflns_number_gt                2888
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'Microsoft Word'
_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)+(0.0392P)²+3.7523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3494
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3767(3) 0.45613(10) 0.8039(3) 0.0140(5) Uani 1 1 d . . . . .
C2 C 0.3030(3) 0.41580(9) 0.8431(3) 0.0148(5) Uani 1 1 d . . . . .
H2 H 0.223085 0.422193 0.883897 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3431(3) 0.36521(10) 0.8244(3) 0.0149(6) Uani 1 1 d . . . . .
C4 C 0.4630(3) 0.35826(10) 0.7655(3) 0.0161(6) Uani 1 1 d . . . . .
H4 H 0.493398 0.324605 0.749323 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5359(3) 0.39907(9) 0.7316(3) 0.0151(6) Uani 1 1 d . . . . .
C6 C 0.6657(3) 0.39669(10) 0.6800(3) 0.0160(6) Uani 1 1 d . . . . .
C7 C 0.7406(3) 0.44011(10) 0.6623(4) 0.0183(6) Uani 1 1 d . . . . .
H7 H 0.708425 0.473162 0.682855 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8632(3) 0.43424(10) 0.6143(4) 0.0208(6) Uani 1 1 d . . . . .
H8 H 0.916369 0.463255 0.600320 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9069(3) 0.38559(11) 0.5870(4) 0.0210(6) Uani 1 1 d . . . . .
H9 H 0.990602 0.380392 0.553936 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8255(3) 0.34425(10) 0.6090(4) 0.0202(6) Uani 1 1 d . . . . .
H10 H 0.856596 0.310818 0.591152 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3470(3) 0.51038(9) 0.8149(3) 0.0140(5) Uani 1 1 d . . . . .
C12 C 0.4364(3) 0.54735(10) 0.7768(3) 0.0156(6) Uani 1 1 d . . . . .
H12 H 0.516881 0.536822 0.743668 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4090(3) 0.59895(9) 0.7867(3) 0.0148(5) Uani 1 1 d . . . . .
H13 H 0.470795 0.623524 0.760840 0.018 Uiso 1 1 calc R U . . .
C14 C 0.2915(3) 0.61502(9) 0.8342(3) 0.0137(5) Uani 1 1 d . . . . .
C15 C 0.2009(3) 0.57818(10) 0.8719(3) 0.0168(6) Uani 1 1 d . . . . .
H15 H 0.119872 0.588834 0.903437 0.020 Uiso 1 1 calc R U . . .
C16 C 0.2286(3) 0.52694(10) 0.8633(4) 0.0169(6) Uani 1 1 d . . . . .
H16 H 0.167052 0.502446 0.890290 0.020 Uiso 1 1 calc R U . . .
C17 C 0.2652(3) 0.32115(10) 0.8662(3) 0.0154(6) Uani 1 1 d . . . . .
C18 C 0.3107(3) 0.27091(10) 0.8493(4) 0.0191(6) Uani 1 1 d . . . . .
H18 H 0.394273 0.265653 0.816129 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2363(3) 0.22930(10) 0.8800(4) 0.0217(6) Uani 1 1 d . . . . .
H19 H 0.268981 0.195676 0.868997 0.026 Uiso 1 1 calc R U . . .
C20 C 0.1133(3) 0.23640(10) 0.9272(4) 0.0217(6) Uani 1 1 d . . . . .
H20 H 0.060123 0.207729 0.944538 0.026 Uiso 1 1 calc R U . . .
C21 C 0.0686(3) 0.28552(11) 0.9488(4) 0.0251(7) Uani 1 1 d . . . . .
H21 H -0.014400 0.290470 0.983733 0.030 Uiso 1 1 calc R U . . .
C22 C 0.1439(3) 0.32739(10) 0.9199(4) 0.0208(6) Uani 1 1 d . . . . .
H22 H 0.112605 0.360865 0.936763 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3767(3) 0.71434(10) 0.7784(4) 0.0233(6) Uani 1 1 d . . . . .
H23A H 0.379205 0.703160 0.658524 0.035 Uiso 1 1 calc R U . . .
H23B H 0.465609 0.707862 0.860725 0.035 Uiso 1 1 calc R U . . .
H23C H 0.356285 0.751016 0.776800 0.035 Uiso 1 1 calc R U . . .
B1 B 0.1841(3) 0.41860(12) 0.3153(5) 0.0245(7) Uani 1 1 d . . . . .
N1 N 0.7070(2) 0.34874(8) 0.6536(3) 0.0170(5) Uani 1 1 d . . . . .
O1 O 0.49205(18) 0.44730(6) 0.7498(2) 0.0153(4) Uani 1 1 d . . . . .
F1 F 0.10055(16) 0.37627(6) 0.2960(3) 0.0293(4) Uani 1 1 d . . . . .
F2 F 0.1562(3) 0.44852(7) 0.4520(3) 0.0509(6) Uani 1 1 d . . . . .
F3 F 0.1527(2) 0.44682(6) 0.1582(2) 0.0362(5) Uani 1 1 d . . . . .
F4 F 0.3180(2) 0.40365(10) 0.3576(4) 0.0771(9) Uani 1 1 d . . . . .
S1 S 0.24623(7) 0.67941(2) 0.85055(10) 0.02009(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.349(3) . ?
C1 C2 1.367(4) . ?
C1 C11 1.456(3) . ?
C2 C3 1.401(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(4) . ?
C3 C17 1.474(4) . ?
C4 C5 1.358(4) . ?
C4 H4 0.9500 . ?
C5 O1 1.355(3) . ?
C5 C6 1.460(4) . ?
C6 N1 1.352(3) . ?
C6 C7 1.389(4) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(4) . ?
C9 H9 0.9500 . ?
C10 N1 1.328(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(4) . ?
C11 C16 1.405(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(4) . ?
C14 S1 1.757(2) . ?
C15 C16 1.373(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.395(4) . ?
C17 C18 1.408(4) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 S1 1.799(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
B1 F4 1.368(4) . ?
B1 F1 1.377(4) . ?
B1 F3 1.392(4) . ?
B1 F2 1.399(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.6(2) . . ?
O1 C1 C11 113.0(2) . . ?
C2 C1 C11 127.4(2) . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 116.7(2) . . ?
C2 C3 C17 122.2(2) . . ?
C4 C3 C17 121.2(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
O1 C5 C4 120.3(2) . . ?
O1 C5 C6 113.9(2) . . ?
C4 C5 C6 125.7(2) . . ?
N1 C6 C7 123.2(2) . . ?
N1 C6 C5 114.3(2) . . ?
C7 C6 C5 122.5(2) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N1 C10 C9 123.9(2) . . ?
N1 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C12 C11 C16 118.5(2) . . ?
C12 C11 C1 120.4(2) . . ?
C16 C11 C1 121.1(2) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 S1 124.3(2) . . ?
C15 C14 S1 116.6(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C22 C17 C18 117.8(2) . . ?
C22 C17 C3 121.8(2) . . ?
C18 C17 C3 120.4(2) . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F4 B1 F1 109.8(3) . . ?
F4 B1 F3 111.2(3) . . ?
F1 B1 F3 109.2(3) . . ?
F4 B1 F2 110.3(3) . . ?
F1 B1 F2 107.5(3) . . ?
F3 B1 F2 108.7(2) . . ?
C10 N1 C6 116.9(2) . . ?
C1 O1 C5 121.3(2) . . ?
C14 S1 C23 103.94(13) . . ?

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
O1 C1 C2 C3 -1.5(4) . . . . ?
C11 C1 C2 C3 179.3(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C17 179.9(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C17 C3 C4 C5 -178.3(2) . . . . ?
C3 C4 C5 O1 -1.7(4) . . . . ?
C3 C4 C5 C6 176.3(2) . . . . ?
O1 C5 C6 N1 -177.1(2) . . . . ?
C4 C5 C6 N1 4.8(4) . . . . ?
O1 C5 C6 C7 3.8(4) . . . . ?
C4 C5 C6 C7 -174.3(3) . . . . ?
N1 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 N1 0.6(4) . . . . ?
O1 C1 C11 C12 -1.9(3) . . . . ?
C2 C1 C11 C12 177.3(3) . . . . ?
O1 C1 C11 C16 177.9(2) . . . . ?
C2 C1 C11 C16 -2.9(4) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C1 C11 C12 C13 179.9(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C12 C13 C14 S1 -179.9(2) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
S1 C14 C15 C16 -179.7(2) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
C1 C11 C16 C15 -179.4(2) . . . . ?
C2 C3 C17 C22 2.7(4) . . . . ?
C4 C3 C17 C22 -178.1(3) . . . . ?
C2 C3 C17 C18 -178.6(2) . . . . ?
C4 C3 C17 C18 0.6(4) . . . . ?
C22 C17 C18 C19 1.7(4) . . . . ?
C3 C17 C18 C19 -177.1(3) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 -2.1(4) . . . . ?
C19 C20 C21 C22 1.5(5) . . . . ?
C20 C21 C22 C17 0.8(5) . . . . ?
C18 C17 C22 C21 -2.4(4) . . . . ?
C3 C17 C22 C21 176.4(3) . . . . ?
C9 C10 N1 C6 -0.6(4) . . . . ?
C7 C6 N1 C10 0.1(4) . . . . ?
C5 C6 N1 C10 -179.0(2) . . . . ?
C2 C1 O1 C5 0.7(4) . . . . ?
C11 C1 O1 C5 -180.0(2) . . . . ?
C4 C5 O1 C1 0.9(4) . . . . ?
C6 C5 O1 C1 -177.3(2) . . . . ?
C13 C14 S1 C23 3.9(3) . . . . ?
C15 C14 S1 C23 -175.9(2) . . . . ?

_refine_diff_density_max         1.087
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_AL134
_database_code_depnum_ccdc_archive 'CCDC 1541808'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2 O4 S W'
_chemical_formula_sum            'C27 H18 N2 O4 S W'
_chemical_formula_weight         650.34

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'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.8635(6)
_cell_length_b                   16.7687(9)
_cell_length_c                   18.1335(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.182(6)
_cell_angle_gamma                90
_cell_volume                     2366.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    15288
_cell_measurement_theta_min      4.67
_cell_measurement_theta_max      29.50

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    5.007
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.3524
_exptl_absorpt_correction_T_max  0.4464
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 21 13 0.0909
-1 12 -17 0.1304
1 -11 13 0.0950
17 14 1 0.1197
-29 -21 1 0.0853
1 -3 -3 0.1293

_exptl_absorpt_process_details   'STOE X-RED & X-SHAPE'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            18073
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.673
_diffrn_reflns_theta_max         29.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6352
_reflns_number_gt                4616
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'

_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)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6352
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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
C1 C 0.3780(5) -0.0016(3) 0.1842(2) 0.0339(8) Uani 1 1 d . . . . .
C2 C 0.4264(5) -0.0674(3) 0.1455(2) 0.0360(8) Uani 1 1 d . . . . .
H2 H 0.4977 -0.1057 0.1708 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3705(5) -0.0773(2) 0.0696(2) 0.0341(8) Uani 1 1 d . . . . .
C4 C 0.2751(5) -0.0140(3) 0.0347(2) 0.0355(8) Uani 1 1 d . . . . .
H4 H 0.2401 -0.0158 -0.0165 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2318(5) 0.0512(2) 0.0748(2) 0.0345(8) Uani 1 1 d . . . . .
C6 C 0.1372(5) 0.1205(2) 0.0394(2) 0.0357(8) Uani 1 1 d . . . . .
C7 C 0.1293(6) 0.1376(3) -0.0361(2) 0.0454(10) Uani 1 1 d . . . . .
H7 H 0.1779 0.1030 -0.0673 0.054 Uiso 1 1 calc R U . . .
C8 C 0.0484(7) 0.2064(3) -0.0640(3) 0.0546(13) Uani 1 1 d . . . . .
H8 H 0.0423 0.2188 -0.1143 0.066 Uiso 1 1 calc R U . . .
C9 C -0.0235(7) 0.2569(3) -0.0167(3) 0.0491(11) Uani 1 1 d . . . . .
H9 H -0.0788 0.3035 -0.0344 0.059 Uiso 1 1 calc R U . . .
C10 C -0.0112(6) 0.2360(3) 0.0580(3) 0.0456(10) Uani 1 1 d . . . . .
H10 H -0.0599 0.2698 0.0900 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4514(5) 0.0091(3) 0.2635(2) 0.0346(8) Uani 1 1 d . . . . .
C12 C 0.5418(6) 0.0779(3) 0.2857(2) 0.0427(10) Uani 1 1 d . . . . .
H12 H 0.5485 0.1184 0.2512 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6233(7) 0.0878(4) 0.3590(3) 0.0538(12) Uani 1 1 d . . . . .
H13 H 0.6868 0.1334 0.3732 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6063(8) 0.0271(4) 0.4098(3) 0.0587(14) Uani 1 1 d . . . . .
H14 H 0.6573 0.0328 0.4590 0.070 Uiso 1 1 calc R U . . .
C15 C 0.5161(8) -0.0405(3) 0.3887(2) 0.0556(13) Uani 1 1 d . . . . .
H15 H 0.5061 -0.0801 0.4237 0.067 Uiso 1 1 calc R U . . .
C16 C 0.4394(6) -0.0510(3) 0.3158(2) 0.0435(10) Uani 1 1 d . . . . .
H16 H 0.3801 -0.0978 0.3017 0.052 Uiso 1 1 calc R U . . .
C17 C 0.4150(5) -0.1488(2) 0.0293(2) 0.0357(8) Uani 1 1 d . . . . .
C18 C 0.4570(6) -0.2200(3) 0.0685(2) 0.0421(10) Uani 1 1 d . . . . .
H18 H 0.4549 -0.2215 0.1197 0.051 Uiso 1 1 calc R U . . .
C19 C 0.5012(6) -0.2877(3) 0.0327(2) 0.0444(10) Uani 1 1 d . . . . .
H19 H 0.5285 -0.3341 0.0599 0.053 Uiso 1 1 calc R U . . .
C20 C 0.5055(7) -0.2874(3) -0.0438(2) 0.0461(10) Uani 1 1 d . . . . .
C21 C 0.4628(6) -0.2177(3) -0.0836(2) 0.0457(10) Uani 1 1 d . . . . .
H21 H 0.4657 -0.2166 -0.1347 0.055 Uiso 1 1 calc R U . . .
C22 C 0.4161(6) -0.1498(3) -0.0479(2) 0.0402(9) Uani 1 1 d . . . . .
H22 H 0.3849 -0.1041 -0.0756 0.048 Uiso 1 1 calc R U . . .
C23 C 0.4415(10) -0.3890(4) -0.1675(4) 0.0767(18) Uani 1 1 d . . . . .
H23A H 0.4734 -0.4368 -0.1913 0.115 Uiso 1 1 calc R U . . .
H23B H 0.4494 -0.3443 -0.1998 0.115 Uiso 1 1 calc R U . . .
H23C H 0.3257 -0.3939 -0.1570 0.115 Uiso 1 1 calc R U . . .
C24 C -0.0829(6) 0.0469(3) 0.1864(2) 0.0420(10) Uani 1 1 d . . . . .
C25 C -0.0870(6) 0.2024(3) 0.2365(2) 0.0447(10) Uani 1 1 d . . . . .
C26 C 0.2531(6) 0.2280(3) 0.2401(2) 0.0442(10) Uani 1 1 d . . . . .
C27 C 0.1430(6) 0.0986(3) 0.3106(2) 0.0430(10) Uani 1 1 d . . . . .
N1 N 0.2739(4) 0.0561(2) 0.15037(17) 0.0326(7) Uani 1 1 d . . . . .
N2 N 0.0675(4) 0.1696(2) 0.08605(19) 0.0370(7) Uani 1 1 d . . . . .
O1 O -0.1866(5) -0.0005(2) 0.1776(2) 0.0597(9) Uani 1 1 d . . . . .
O2 O -0.1935(5) 0.2426(2) 0.2554(2) 0.0608(10) Uani 1 1 d . . . . .
O3 O 0.3299(6) 0.2806(2) 0.2669(2) 0.0690(11) Uani 1 1 d . . . . .
O4 O 0.1693(5) 0.0780(2) 0.37140(18) 0.0653(11) Uani 1 1 d . . . . .
S1 S 0.5824(3) -0.37438(11) -0.08289(9) 0.0885(6) Uani 1 1 d . . . . .
W1 W 0.09410(2) 0.13567(2) 0.20601(2) 0.03559(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.356(5) . ?
C1 C2 1.390(6) . ?
C1 C11 1.482(5) . ?
C2 C3 1.394(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(6) . ?
C3 C17 1.473(6) . ?
C4 C5 1.384(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.365(5) . ?
C5 C6 1.476(6) . ?
C6 N2 1.352(5) . ?
C6 C7 1.391(6) . ?
C7 C8 1.379(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.339(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(6) . ?
C11 C16 1.396(6) . ?
C12 C13 1.401(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.400(5) . ?
C17 C18 1.406(6) . ?
C18 C19 1.376(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(7) . ?
C20 S1 1.767(5) . ?
C21 C22 1.386(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 S1 1.777(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O1 1.134(5) . ?
C24 W1 2.034(5) . ?
C25 O2 1.165(6) . ?
C25 W1 1.951(5) . ?
C26 O3 1.139(6) . ?
C26 W1 2.031(5) . ?
C27 O4 1.146(5) . ?
C27 W1 1.980(4) . ?
N1 W1 2.281(3) . ?
N2 W1 2.229(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.0(3) . . ?
N1 C1 C11 118.6(3) . . ?
C2 C1 C11 119.3(4) . . ?
C1 C2 C3 121.4(4) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 115.5(4) . . ?
C2 C3 C17 121.5(4) . . ?
C4 C3 C17 122.9(3) . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 122.2(4) . . ?
N1 C5 C6 115.2(4) . . ?
C4 C5 C6 122.7(4) . . ?
N2 C6 C7 121.6(4) . . ?
N2 C6 C5 115.5(3) . . ?
C7 C6 C5 122.7(4) . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 118.3(5) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 123.0(5) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C12 C11 C16 119.1(4) . . ?
C12 C11 C1 119.8(4) . . ?
C16 C11 C1 121.1(4) . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.9(5) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C22 C17 C18 117.5(4) . . ?
C22 C17 C3 122.8(4) . . ?
C18 C17 C3 119.7(3) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 S1 123.8(3) . . ?
C19 C20 S1 117.1(4) . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C17 121.2(4) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 W1 176.6(4) . . ?
O2 C25 W1 179.1(5) . . ?
O3 C26 W1 170.8(4) . . ?
O4 C27 W1 178.9(4) . . ?
C1 N1 C5 117.1(3) . . ?
C1 N1 W1 126.1(2) . . ?
C5 N1 W1 113.7(3) . . ?
C10 N2 C6 118.4(4) . . ?
C10 N2 W1 123.9(3) . . ?
C6 N2 W1 117.7(3) . . ?
C20 S1 C23 104.7(3) . . ?
C25 W1 C27 87.65(19) . . ?
C25 W1 C26 85.4(2) . . ?
C27 W1 C26 85.47(19) . . ?
C25 W1 C24 87.72(19) . . ?
C27 W1 C24 88.41(19) . . ?
C26 W1 C24 170.95(17) . . ?
C25 W1 N2 99.13(16) . . ?
C27 W1 N2 173.15(15) . . ?
C26 W1 N2 94.03(15) . . ?
C24 W1 N2 92.85(15) . . ?
C25 W1 N1 169.64(16) . . ?
C27 W1 N1 101.06(15) . . ?
C26 W1 N1 100.76(16) . . ?
C24 W1 N1 86.94(15) . . ?
N2 W1 N1 72.30(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
N1 C1 C2 C3 0.2(6) . . . . ?
C11 C1 C2 C3 -175.4(4) . . . . ?
C1 C2 C3 C4 4.8(6) . . . . ?
C1 C2 C3 C17 -177.1(4) . . . . ?
C2 C3 C4 C5 -3.7(6) . . . . ?
C17 C3 C4 C5 178.2(4) . . . . ?
C3 C4 C5 N1 -2.4(6) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
N1 C5 C6 N2 -15.8(5) . . . . ?
C4 C5 C6 N2 164.2(4) . . . . ?
N1 C5 C6 C7 160.0(4) . . . . ?
C4 C5 C6 C7 -20.0(6) . . . . ?
N2 C6 C7 C8 0.0(7) . . . . ?
C5 C6 C7 C8 -175.5(4) . . . . ?
C6 C7 C8 C9 -0.2(7) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C8 C9 C10 N2 0.2(7) . . . . ?
N1 C1 C11 C12 -53.9(5) . . . . ?
C2 C1 C11 C12 121.8(4) . . . . ?
N1 C1 C11 C16 129.7(4) . . . . ?
C2 C1 C11 C16 -54.6(6) . . . . ?
C16 C11 C12 C13 1.0(7) . . . . ?
C1 C11 C12 C13 -175.5(4) . . . . ?
C11 C12 C13 C14 -2.0(7) . . . . ?
C12 C13 C14 C15 1.3(8) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C11 -1.3(8) . . . . ?
C12 C11 C16 C15 0.6(7) . . . . ?
C1 C11 C16 C15 177.1(4) . . . . ?
C2 C3 C17 C22 -156.8(4) . . . . ?
C4 C3 C17 C22 21.1(6) . . . . ?
C2 C3 C17 C18 23.8(6) . . . . ?
C4 C3 C17 C18 -158.3(4) . . . . ?
C22 C17 C18 C19 1.4(7) . . . . ?
C3 C17 C18 C19 -179.2(4) . . . . ?
C17 C18 C19 C20 0.0(7) . . . . ?
C18 C19 C20 C21 -0.6(7) . . . . ?
C18 C19 C20 S1 174.4(4) . . . . ?
C19 C20 C21 C22 -0.3(7) . . . . ?
S1 C20 C21 C22 -174.9(4) . . . . ?
C20 C21 C22 C17 1.7(7) . . . . ?
C18 C17 C22 C21 -2.2(6) . . . . ?
C3 C17 C22 C21 178.4(4) . . . . ?
C2 C1 N1 C5 -6.3(6) . . . . ?
C11 C1 N1 C5 169.3(3) . . . . ?
C2 C1 N1 W1 152.4(3) . . . . ?
C11 C1 N1 W1 -32.0(5) . . . . ?
C4 C5 N1 C1 7.5(6) . . . . ?
C6 C5 N1 C1 -172.5(3) . . . . ?
C4 C5 N1 W1 -153.9(3) . . . . ?
C6 C5 N1 W1 26.2(4) . . . . ?
C9 C10 N2 C6 -0.4(6) . . . . ?
C9 C10 N2 W1 178.7(3) . . . . ?
C7 C6 N2 C10 0.2(6) . . . . ?
C5 C6 N2 C10 176.1(4) . . . . ?
C7 C6 N2 W1 -178.9(3) . . . . ?
C5 C6 N2 W1 -3.1(4) . . . . ?
C21 C20 S1 C23 -46.9(5) . . . . ?
C19 C20 S1 C23 138.3(4) . . . . ?

_refine_diff_density_max         1.373
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_wo21abs
_database_code_depnum_ccdc_archive 'CCDC 1541813'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2 O5 W'
_chemical_formula_sum            'C27 H18 N2 O5 W'
_chemical_formula_weight         634.28

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.1178(16)
_cell_length_b                   16.843(3)
_cell_length_c                   16.736(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.90(3)
_cell_angle_gamma                90.00
_cell_volume                     2288.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    13590
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      29.57

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.3064
_exptl_absorpt_correction_T_max  0.5302
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -11 0.0991
1 -26 26 0.0484
29 -20 -9 0.1320
-16 -5 2 0.2359
-1 -27 -30 0.1088
0 13 9 0.0700
9 -20 -5 0.1254
19 18 -30 0.0845

_exptl_absorpt_process_details   numerical

_exptl_special_details           
;
 STOE IPDS 2T software X-RED & X-SHAPE is used
;

_diffrn_ambient_temperature      220(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11284
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4005
_reflns_number_gt                3231
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep(Johnson, 1996)'
_computing_publication_material  'X-STEP32, Microsoft Word'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0285P)²+19.4889P] 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     SHELXL
_refine_ls_extinction_coef       0.0026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4005
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7648(10) 0.1907(5) 0.5232(5) 0.0283(18) Uani 1 1 d . . .
C2 C 0.8500(11) 0.1457(5) 0.5801(5) 0.034(2) Uani 1 1 d . . .
H2 H 0.9113 0.1720 0.6202 0.041 Uiso 1 1 calc R . .
C3 C 0.8476(11) 0.0634(5) 0.5796(5) 0.0320(19) Uani 1 1 d . . .
C4 C 0.7568(11) 0.0295(5) 0.5164(5) 0.0315(19) Uani 1 1 d . . .
H4 H 0.7502 -0.0261 0.5130 0.038 Uiso 1 1 calc R . .
C5 C 0.6770(10) 0.0744(5) 0.4594(5) 0.0307(19) Uani 1 1 d . . .
C6 C 0.5913(10) 0.0393(5) 0.3899(5) 0.0274(18) Uani 1 1 d . . .
C7 C 0.6055(12) -0.0396(5) 0.3692(5) 0.036(2) Uani 1 1 d . . .
H7 H 0.6709 -0.0738 0.4007 0.044 Uiso 1 1 calc R . .
C8 C 0.5235(12) -0.0686(5) 0.3019(5) 0.037(2) Uani 1 1 d . . .
H8 H 0.5324 -0.1223 0.2873 0.045 Uiso 1 1 calc R . .
C9 C 0.4304(12) -0.0177(6) 0.2577(5) 0.039(2) Uani 1 1 d . . .
H9 H 0.3739 -0.0358 0.2117 0.047 Uiso 1 1 calc R . .
C10 C 0.4189(12) 0.0601(6) 0.2802(5) 0.038(2) Uani 1 1 d . . .
H10 H 0.3544 0.0946 0.2485 0.046 Uiso 1 1 calc R . .
C11 C 0.7773(11) 0.2783(6) 0.5242(6) 0.037(2) Uani 1 1 d . . .
C12 C 0.8620(13) 0.3161(6) 0.4643(7) 0.046(2) Uani 1 1 d . . .
H12 H 0.9075 0.2863 0.4226 0.055 Uiso 1 1 calc R . .
C13 C 0.8803(14) 0.3981(6) 0.4655(7) 0.050(3) Uani 1 1 d . . .
H13 H 0.9417 0.4236 0.4259 0.060 Uiso 1 1 calc R . .
C14 C 0.8087(14) 0.4415(6) 0.5246(7) 0.050(3) Uani 1 1 d . . .
H14 H 0.8153 0.4972 0.5233 0.060 Uiso 1 1 calc R . .
C15 C 0.7267(14) 0.4046(6) 0.5860(6) 0.048(3) Uani 1 1 d . . .
H15 H 0.6815 0.4349 0.6274 0.057 Uiso 1 1 calc R . .
C16 C 0.7116(12) 0.3220(6) 0.5860(6) 0.040(2) Uani 1 1 d . . .
H16 H 0.6570 0.2962 0.6278 0.048 Uiso 1 1 calc R . .
C17 C 0.9346(11) 0.0151(5) 0.6402(5) 0.0312(19) Uani 1 1 d . . .
C18 C 0.9854(12) 0.0469(5) 0.7142(5) 0.035(2) Uani 1 1 d . . .
H18 H 0.9631 0.1006 0.7252 0.042 Uiso 1 1 calc R . .
C19 C 1.0670(13) 0.0018(6) 0.7712(5) 0.040(2) Uani 1 1 d . . .
H19 H 1.1025 0.0251 0.8195 0.048 Uiso 1 1 calc R . .
C20 C 1.0959(12) -0.0773(6) 0.7567(6) 0.040(2) Uani 1 1 d . . .
C21 C 1.0436(12) -0.1106(5) 0.6848(5) 0.036(2) Uani 1 1 d . . .
H21 H 1.0615 -0.1650 0.6755 0.043 Uiso 1 1 calc R . .
C22 C 0.9669(11) -0.0659(5) 0.6276(5) 0.033(2) Uani 1 1 d . . .
H22 H 0.9350 -0.0895 0.5789 0.039 Uiso 1 1 calc R . .
C23 C 1.2396(16) -0.0982(7) 0.8822(7) 0.059(3) Uani 1 1 d . . .
H23A H 1.2913 -0.1410 0.9122 0.089 Uiso 1 1 calc R . .
H23B H 1.1511 -0.0756 0.9131 0.089 Uiso 1 1 calc R . .
H23C H 1.3207 -0.0575 0.8712 0.089 Uiso 1 1 calc R . .
C24 C 0.3111(12) 0.2023(6) 0.4706(6) 0.041(2) Uani 1 1 d . . .
C25 C 0.3003(13) 0.2496(6) 0.3151(6) 0.044(2) Uani 1 1 d . . .
C26 C 0.6313(14) 0.2579(6) 0.2993(7) 0.047(3) Uani 1 1 d . . .
C27 C 0.4717(11) 0.3278(6) 0.4186(5) 0.037(2) Uani 1 1 d . . .
N1 N 0.6730(8) 0.1570(4) 0.4643(4) 0.0312(16) Uani 1 1 d . . .
N2 N 0.4962(9) 0.0903(4) 0.3464(4) 0.0310(16) Uani 1 1 d . . .
O1 O 1.1741(10) -0.1288(4) 0.8081(4) 0.054(2) Uani 1 1 d . . .
O2 O 0.2128(10) 0.2003(5) 0.5196(5) 0.056(2) Uani 1 1 d . . .
O3 O 0.1851(11) 0.2722(5) 0.2740(5) 0.069(2) Uani 1 1 d . . .
O4 O 0.7062(11) 0.2891(5) 0.2502(6) 0.075(3) Uani 1 1 d . . .
O5 O 0.4570(10) 0.3948(4) 0.4360(4) 0.0497(18) Uani 1 1 d . . .
W1 W 0.47833(5) 0.21701(2) 0.38459(2) 0.03039(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.352(11) . ?
C1 C2 1.392(12) . ?
C1 C11 1.478(13) . ?
C2 C3 1.386(13) . ?
C3 C4 1.401(12) . ?
C3 C17 1.472(12) . ?
C4 C5 1.372(12) . ?
C5 N1 1.394(11) . ?
C5 C6 1.470(12) . ?
C6 N2 1.359(11) . ?
C6 C7 1.378(12) . ?
C7 C8 1.388(13) . ?
C8 C9 1.355(13) . ?
C9 C10 1.368(13) . ?
C10 N2 1.362(11) . ?
C11 C12 1.381(14) . ?
C11 C16 1.383(13) . ?
C12 C13 1.389(14) . ?
C13 C14 1.366(15) . ?
C14 C15 1.381(16) . ?
C15 C16 1.398(14) . ?
C17 C22 1.405(12) . ?
C17 C18 1.405(12) . ?
C18 C19 1.380(13) . ?
C19 C20 1.375(13) . ?
C20 O1 1.370(11) . ?
C20 C21 1.389(13) . ?
C21 C22 1.362(12) . ?
C23 O1 1.437(12) . ?
C24 O2 1.153(13) . ?
C24 W1 2.010(11) . ?
C25 O3 1.214(12) . ?
C25 W1 1.920(10) . ?
C26 O4 1.157(13) . ?
C26 W1 2.027(12) . ?
C27 O5 1.171(12) . ?
C27 W1 1.953(10) . ?
N1 W1 2.287(7) . ?
N2 W1 2.234(7) . ?

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
N1 C1 C2 122.1(8) . . ?
N1 C1 C11 117.7(7) . . ?
C2 C1 C11 120.2(8) . . ?
C3 C2 C1 122.3(8) . . ?
C2 C3 C4 114.7(8) . . ?
C2 C3 C17 122.9(8) . . ?
C4 C3 C17 122.4(8) . . ?
C5 C4 C3 122.5(8) . . ?
C4 C5 N1 121.4(8) . . ?
C4 C5 C6 122.7(8) . . ?
N1 C5 C6 115.9(7) . . ?
N2 C6 C7 121.6(8) . . ?
N2 C6 C5 115.3(7) . . ?
C7 C6 C5 123.1(8) . . ?
C6 C7 C8 120.2(8) . . ?
C9 C8 C7 118.5(8) . . ?
C8 C9 C10 119.7(9) . . ?
N2 C10 C9 123.3(9) . . ?
C12 C11 C16 120.0(9) . . ?
C12 C11 C1 119.1(9) . . ?
C16 C11 C1 120.8(9) . . ?
C11 C12 C13 120.2(11) . . ?
C14 C13 C12 119.7(11) . . ?
C13 C14 C15 120.9(10) . . ?
C14 C15 C16 119.5(10) . . ?
C11 C16 C15 119.7(10) . . ?
C22 C17 C18 116.8(8) . . ?
C22 C17 C3 121.4(8) . . ?
C18 C17 C3 121.7(8) . . ?
C19 C18 C17 122.0(8) . . ?
C20 C19 C18 119.5(8) . . ?
O1 C20 C19 125.6(9) . . ?
O1 C20 C21 114.8(8) . . ?
C19 C20 C21 119.6(9) . . ?
C22 C21 C20 121.0(8) . . ?
C21 C22 C17 121.0(8) . . ?
O2 C24 W1 174.6(8) . . ?
O3 C25 W1 177.0(10) . . ?
O4 C26 W1 171.7(9) . . ?
O5 C27 W1 175.1(8) . . ?
C1 N1 C5 116.7(7) . . ?
C1 N1 W1 127.4(6) . . ?
C5 N1 W1 115.0(5) . . ?
C6 N2 C10 116.8(8) . . ?
C6 N2 W1 119.3(5) . . ?
C10 N2 W1 123.9(6) . . ?
C20 O1 C23 118.4(8) . . ?
C25 W1 C27 83.1(4) . . ?
C25 W1 C24 87.6(4) . . ?
C27 W1 C24 83.5(4) . . ?
C25 W1 C26 86.5(4) . . ?
C27 W1 C26 84.3(4) . . ?
C24 W1 C26 167.0(4) . . ?
C25 W1 N2 98.7(4) . . ?
C27 W1 N2 177.8(3) . . ?
C24 W1 N2 97.8(3) . . ?
C26 W1 N2 94.6(3) . . ?
C25 W1 N1 170.3(3) . . ?
C27 W1 N1 105.9(3) . . ?
C24 W1 N1 89.8(3) . . ?
C26 W1 N1 97.8(3) . . ?
N2 W1 N1 72.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.821
_refine_diff_density_min         -1.605
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1541810'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 F N2 O4 W'
_chemical_formula_sum            'C26 H15 F N2 O4 W'
_chemical_formula_weight         622.25

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'
F F 0.0171 0.0103 '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'
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                   7.611(2)
_cell_length_b                   13.016(4)
_cell_length_c                   13.175(4)
_cell_angle_alpha                79.773(6)
_cell_angle_beta                 73.331(6)
_cell_angle_gamma                83.135(6)
_cell_volume                     1227.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      6.531
_cell_measurement_theta_max      60.895

_exptl_crystal_description       platelett
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    4.747
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4872
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS - Bruker/Siemens area detector absorption
;

_exptl_special_details           
;
 Bruker-AXS smart-APEX P4 CCD area detector difractometer is used
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         15071
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        3
_diffrn_reflns_number            15071
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6890
_reflns_number_gt                6419
_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.
;
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.039 0.000 0.000 184 37 ' '
_platon_squeeze_details          
;
The general procedure (based on a preliminary implementation of the technique)
has been described in more detail in: Acta Cryst. (1990), A46, 194 as the 
'BYPASS procedure' P. v.d. Sluis & A.L. Spek) 
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep (Johnson, 1996)'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0235P)²+0.5842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6890
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2348(3) 0.74025(16) 0.55812(15) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.3491(3) 0.72040(16) 0.45930(15) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.4246 0.7730 0.4147 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3546(3) 0.62474(16) 0.42468(14) 0.0132(4) Uani 1 1 d . . . . .
C4 C 0.2485(3) 0.54876(16) 0.49720(15) 0.0138(4) Uani 1 1 d . . . . .
H4 H 0.2511 0.4811 0.4788 0.017 Uiso 1 1 calc R U . . .
C5 C 0.1395(3) 0.57154(15) 0.59572(14) 0.0123(3) Uani 1 1 d . . . . .
C6 C 0.0330(3) 0.49176(16) 0.67715(14) 0.0137(4) Uani 1 1 d . . . . .
C7 C 0.0678(3) 0.38521(17) 0.67380(15) 0.0164(4) Uani 1 1 d . . . . .
H7 H 0.1584 0.3605 0.6154 0.020 Uiso 1 1 calc R U . . .
C8 C -0.0308(3) 0.31482(17) 0.75637(17) 0.0196(4) Uani 1 1 d . . . . .
H8 H -0.0088 0.2416 0.7552 0.023 Uiso 1 1 calc R U . . .
C9 C -0.1616(3) 0.35325(17) 0.84035(16) 0.0183(4) Uani 1 1 d . . . . .
H9 H -0.2301 0.3069 0.8983 0.022 Uiso 1 1 calc R U . . .
C10 C -0.1910(3) 0.45982(17) 0.83849(15) 0.0169(4) Uani 1 1 d . . . . .
H10 H -0.2828 0.4858 0.8957 0.020 Uiso 1 1 calc R U . . .
C11 C 0.2421(3) 0.84169(17) 0.59249(16) 0.0167(4) Uani 1 1 d . . . . .
C12 C 0.2862(3) 0.84438(19) 0.68786(18) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.3024 0.7810 0.7337 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3063(3) 0.9395(2) 0.7158(2) 0.0329(6) Uani 1 1 d . . . . .
H13 H 0.3374 0.9424 0.7801 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2800(4) 1.0289(2) 0.6478(3) 0.0395(7) Uani 1 1 d . . . . .
C15 C 0.2368(4) 1.0298(2) 0.5539(2) 0.0396(7) Uani 1 1 d . . . . .
H15 H 0.2185 1.0939 0.5097 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2204(4) 0.93496(18) 0.52454(19) 0.0266(5) Uani 1 1 d . . . . .
H16 H 0.1945 0.9334 0.4585 0.032 Uiso 1 1 calc R U . . .
C17 C 0.4718(3) 0.60465(16) 0.31814(14) 0.0136(4) Uani 1 1 d . . . . .
C18 C 0.5303(3) 0.68806(17) 0.23606(15) 0.0171(4) Uani 1 1 d . . . . .
H18 H 0.4924 0.7580 0.2487 0.020 Uiso 1 1 calc R U . . .
C19 C 0.6424(3) 0.66953(18) 0.13695(16) 0.0202(4) Uani 1 1 d . . . . .
H19 H 0.6814 0.7267 0.0821 0.024 Uiso 1 1 calc R U . . .
C20 C 0.6981(3) 0.56775(19) 0.11744(16) 0.0206(4) Uani 1 1 d . . . . .
H20 H 0.7754 0.5552 0.0494 0.025 Uiso 1 1 calc R U . . .
C21 C 0.6406(3) 0.48427(18) 0.19740(16) 0.0179(4) Uani 1 1 d . . . . .
H21 H 0.6777 0.4145 0.1840 0.021 Uiso 1 1 calc R U . . .
C22 C 0.5285(3) 0.50289(16) 0.29721(15) 0.0151(4) Uani 1 1 d . . . . .
H22 H 0.4901 0.4455 0.3518 0.018 Uiso 1 1 calc R U . . .
C23 C -0.2628(3) 0.71446(15) 0.63308(15) 0.0140(4) Uani 1 1 d . . . . .
C24 C -0.3840(3) 0.70726(18) 0.85456(16) 0.0189(4) Uani 1 1 d . . . . .
C25 C -0.0238(3) 0.7054(2) 0.87261(17) 0.0224(5) Uani 1 1 d . . . . .
C26 C -0.1630(3) 0.85751(19) 0.73460(17) 0.0205(4) Uani 1 1 d . . . . .
N1 N 0.1238(2) 0.66778(13) 0.62493(12) 0.0130(3) Uani 1 1 d . . . . .
N2 N -0.0950(2) 0.52940(14) 0.75888(12) 0.0134(3) Uani 1 1 d . . . . .
F1 F 0.2977(3) 1.12278(16) 0.67534(19) 0.0639(7) Uani 1 1 d . . . . .
W1 W -0.14083(2) 0.70258(2) 0.75203(2) 0.01332(3) Uani 1 1 d . . . . .
O1 O -0.3303(2) 0.72373(13) 0.56394(12) 0.0206(3) Uani 1 1 d . . . . .
O2 O -0.5303(2) 0.70932(15) 0.91459(13) 0.0275(4) Uani 1 1 d . . . . .
O3 O 0.0351(3) 0.7146(2) 0.94105(14) 0.0415(5) Uani 1 1 d . . . . .
O4 O -0.1810(3) 0.94792(14) 0.72545(15) 0.0305(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
C1 N1 1.359(2) . ?
C1 C2 1.391(3) . ?
C1 C11 1.482(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 C17 1.480(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.357(3) . ?
C5 C6 1.481(2) . ?
C6 N2 1.349(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.355(2) . ?
C10 H10 0.9500 . ?
C11 C16 1.398(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(5) . ?
C14 F1 1.367(3) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.393(3) . ?
C17 C18 1.403(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O1 1.150(2) . ?
C23 W1 2.014(2) . ?
C24 O2 1.167(3) . ?
C24 W1 1.955(2) . ?
C25 O3 1.146(3) . ?
C25 W1 2.039(2) . ?
C26 O4 1.157(3) . ?
C26 W1 1.981(2) . ?
N1 W1 2.2765(18) . ?
N2 W1 2.2291(19) . ?

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
N1 C1 C2 121.80(19) . . ?
N1 C1 C11 119.73(18) . . ?
C2 C1 C11 118.40(17) . . ?
C1 C2 C3 121.11(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 116.31(18) . . ?
C2 C3 C17 121.18(16) . . ?
C4 C3 C17 122.48(19) . . ?
C5 C4 C3 120.39(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 122.66(17) . . ?
N1 C5 C6 115.23(17) . . ?
C4 C5 C6 122.11(18) . . ?
N2 C6 C7 121.68(17) . . ?
N2 C6 C5 115.31(18) . . ?
C7 C6 C5 122.92(18) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 118.84(18) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 123.0(2) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C16 C11 C12 119.8(2) . . ?
C16 C11 C1 119.58(19) . . ?
C12 C11 C1 120.40(19) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 117.9(2) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C15 C14 F1 118.0(3) . . ?
C15 C14 C13 123.8(2) . . ?
F1 C14 C13 118.2(3) . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C22 C17 C18 118.41(18) . . ?
C22 C17 C3 121.00(17) . . ?
C18 C17 C3 120.58(19) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.21(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.88(18) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O1 C23 W1 178.16(17) . . ?
O2 C24 W1 178.84(18) . . ?
O3 C25 W1 174.6(2) . . ?
O4 C26 W1 178.1(2) . . ?
C5 N1 C1 117.34(17) . . ?
C5 N1 W1 114.25(12) . . ?
C1 N1 W1 125.70(14) . . ?
C6 N2 C10 118.05(18) . . ?
C6 N2 W1 117.85(12) . . ?
C10 N2 W1 124.08(15) . . ?
C24 W1 C26 86.82(9) . . ?
C24 W1 C23 89.10(8) . . ?
C26 W1 C23 87.55(8) . . ?
C24 W1 C25 89.62(8) . . ?
C26 W1 C25 87.11(10) . . ?
C23 W1 C25 174.57(9) . . ?
C24 W1 N2 98.08(8) . . ?
C26 W1 N2 174.98(7) . . ?
C23 W1 N2 91.38(7) . . ?
C25 W1 N2 94.02(8) . . ?
C24 W1 N1 168.42(7) . . ?
C26 W1 N1 102.90(8) . . ?
C23 W1 N1 85.08(7) . . ?
C25 W1 N1 97.07(8) . . ?
N2 W1 N1 72.11(6) . . ?

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
N1 C1 C2 C3 -0.1(3) . . . . ?
C11 C1 C2 C3 177.07(18) . . . . ?
C1 C2 C3 C4 -3.9(3) . . . . ?
C1 C2 C3 C17 178.11(17) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
C17 C3 C4 C5 -179.43(17) . . . . ?
C3 C4 C5 N1 2.8(3) . . . . ?
C3 C4 C5 C6 -176.60(17) . . . . ?
N1 C5 C6 N2 13.8(2) . . . . ?
C4 C5 C6 N2 -166.75(17) . . . . ?
N1 C5 C6 C7 -162.82(17) . . . . ?
C4 C5 C6 C7 16.6(3) . . . . ?
N2 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C8 176.29(17) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C9 C10 N2 -1.3(3) . . . . ?
N1 C1 C11 C16 -129.8(2) . . . . ?
C2 C1 C11 C16 53.0(3) . . . . ?
N1 C1 C11 C12 55.8(3) . . . . ?
C2 C1 C11 C12 -121.5(2) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
C1 C11 C12 C13 175.2(2) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C12 C13 C14 F1 179.3(2) . . . . ?
F1 C14 C15 C16 179.3(2) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 2.1(4) . . . . ?
C12 C11 C16 C15 -2.1(4) . . . . ?
C1 C11 C16 C15 -176.6(2) . . . . ?
C2 C3 C17 C22 157.42(18) . . . . ?
C4 C3 C17 C22 -20.5(3) . . . . ?
C2 C3 C17 C18 -21.9(3) . . . . ?
C4 C3 C17 C18 160.22(18) . . . . ?
C22 C17 C18 C19 -0.4(3) . . . . ?
C3 C17 C18 C19 178.92(18) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 0.1(3) . . . . ?
C3 C17 C22 C21 -179.21(17) . . . . ?
C4 C5 N1 C1 -6.8(3) . . . . ?
C6 C5 N1 C1 172.68(16) . . . . ?
C4 C5 N1 W1 155.69(14) . . . . ?
C6 C5 N1 W1 -24.86(19) . . . . ?
C2 C1 N1 C5 5.4(3) . . . . ?
C11 C1 N1 C5 -171.74(17) . . . . ?
C2 C1 N1 W1 -154.82(15) . . . . ?
C11 C1 N1 W1 28.0(2) . . . . ?
C7 C6 N2 C10 -0.3(3) . . . . ?
C5 C6 N2 C10 -177.00(16) . . . . ?
C7 C6 N2 W1 -178.63(13) . . . . ?
C5 C6 N2 W1 4.7(2) . . . . ?
C9 C10 N2 C6 1.1(3) . . . . ?
C9 C10 N2 W1 179.23(14) . . . . ?

_refine_diff_density_max         1.291
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_AL186_a
_database_code_depnum_ccdc_archive 'CCDC 1541812'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2018-06-07 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         ?
_chemical_formula_sum            'C23 H18 N2 S'
_chemical_formula_weight         354.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   19.3924(2)
_cell_length_b                   5.14157(5)
_cell_length_c                   18.1289(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.9167(7)
_cell_angle_gamma                90
_cell_volume                     1780.58(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5420
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      66.85
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.4880
_exptl_transmission_factor_max   0.7528
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.661
_shelx_estimated_absorpt_T_min   0.456
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10917
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         66.877
_diffrn_reflns_theta_full        66.877
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3146
_reflns_number_gt                2518
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'Microsoft Word'
_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)+(0.0729P)²+3.1743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71347(16) 0.6546(6) 0.31874(18) 0.0218(7) Uani 1 1 d . . . . .
C2 C 0.71497(16) 0.5010(7) 0.38190(17) 0.0232(7) Uani 1 1 d . . . . .
H2 H 0.6757 0.3960 0.3867 0.028 Uiso 1 1 calc R U . . .
C3 C 0.77370(15) 0.4994(6) 0.43835(18) 0.0231(7) Uani 1 1 d . . . . .
C4 C 0.82935(17) 0.6572(7) 0.42799(18) 0.0268(8) Uani 1 1 d . . . . .
H4 H 0.8709 0.6601 0.4644 0.032 Uiso 1 1 calc R U . . .
C5 C 0.82410(16) 0.8103(7) 0.36450(19) 0.0270(8) Uani 1 1 d . . . . .
C6 C 0.88070(17) 0.9959(7) 0.35469(19) 0.0297(8) Uani 1 1 d . . . . .
C7 C 0.87689(19) 1.1503(8) 0.2915(2) 0.0392(9) Uani 1 1 d . . . . .
H7 H 0.8382 1.1353 0.2517 0.047 Uiso 1 1 calc R U . . .
C8 C 0.9296(2) 1.3255(9) 0.2870(2) 0.0472(11) Uani 1 1 d . . . . .
H8 H 0.9277 1.4312 0.2437 0.057 Uiso 1 1 calc R U . . .
C9 C 0.98532(19) 1.3472(9) 0.3458(2) 0.0418(10) Uani 1 1 d . . . . .
H9 H 1.0220 1.4687 0.3446 0.050 Uiso 1 1 calc R U . . .
C10 C 0.98487(18) 1.1827(8) 0.4065(2) 0.0381(9) Uani 1 1 d . . . . .
H10 H 1.0227 1.1952 0.4472 0.046 Uiso 1 1 calc R U . . .
C11 C 0.65117(16) 0.6622(6) 0.25760(17) 0.0209(7) Uani 1 1 d . . . . .
C12 C 0.64459(16) 0.8576(6) 0.20300(18) 0.0228(7) Uani 1 1 d . . . . .
H12 H 0.6800 0.9867 0.2055 0.027 Uiso 1 1 calc R U . . .
C13 C 0.58765(15) 0.8662(6) 0.14553(18) 0.0213(7) Uani 1 1 d . . . . .
H13 H 0.5846 0.9994 0.1088 0.026 Uiso 1 1 calc R U . . .
C14 C 0.53469(15) 0.6805(6) 0.14119(17) 0.0179(6) Uani 1 1 d . . . . .
C15 C 0.54037(16) 0.4875(6) 0.19545(17) 0.0212(7) Uani 1 1 d . . . . .
H15 H 0.5047 0.3599 0.1935 0.025 Uiso 1 1 calc R U . . .
C16 C 0.59797(16) 0.4805(6) 0.25247(18) 0.0228(7) Uani 1 1 d . . . . .
H16 H 0.6010 0.3469 0.2891 0.027 Uiso 1 1 calc R U . . .
C17 C 0.77545(16) 0.3376(7) 0.50602(18) 0.0237(7) Uani 1 1 d . . . . .
C18 C 0.83611(17) 0.2028(8) 0.5384(2) 0.0351(9) Uani 1 1 d . . . . .
H18 H 0.8781 0.2260 0.5189 0.042 Uiso 1 1 calc R U . . .
C19 C 0.83554(19) 0.0368(8) 0.5984(2) 0.0369(9) Uani 1 1 d . . . . .
H19 H 0.8769 -0.0552 0.6188 0.044 Uiso 1 1 calc R U . . .
C20 C 0.77539(17) 0.0025(7) 0.62922(19) 0.0304(8) Uani 1 1 d . . . . .
H20 H 0.7753 -0.1116 0.6704 0.036 Uiso 1 1 calc R U . . .
C21 C 0.71526(17) 0.1383(7) 0.59859(19) 0.0260(7) Uani 1 1 d . . . . .
H21 H 0.6738 0.1182 0.6193 0.031 Uiso 1 1 calc R U . . .
C22 C 0.71542(16) 0.3025(7) 0.53827(19) 0.0255(7) Uani 1 1 d . . . . .
H22 H 0.6738 0.3939 0.5182 0.031 Uiso 1 1 calc R U . . .
C23 C 0.41503(17) 0.4175(7) 0.0719(2) 0.0288(8) Uani 1 1 d . . . . .
H23A H 0.3757 0.4108 0.0301 0.043 Uiso 1 1 calc R U . . .
H23B H 0.3972 0.4136 0.1193 0.043 Uiso 1 1 calc R U . . .
H23C H 0.4457 0.2673 0.0694 0.043 Uiso 1 1 calc R U . . .
N1 N 0.76690(13) 0.8105(5) 0.30985(15) 0.0243(6) Uani 1 1 d . . . . .
N2 N 0.93505(14) 1.0086(7) 0.41152(17) 0.0357(8) Uani 1 1 d . . . . .
S1 S 0.46355(4) 0.71124(14) 0.06650(4) 0.0194(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(4) . ?
C1 C2 1.387(5) . ?
C1 C11 1.493(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(5) . ?
C3 C17 1.478(5) . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.354(4) . ?
C5 C6 1.488(5) . ?
C6 N2 1.343(4) . ?
C6 C7 1.385(5) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 N2 1.331(5) . ?
C10 H10 0.9500 . ?
C11 C16 1.383(4) . ?
C11 C12 1.401(5) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 S1 1.766(3) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.401(4) . ?
C17 C18 1.404(5) . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 S1 1.791(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
N1 C1 C2 122.2(3) . . ?
N1 C1 C11 116.0(3) . . ?
C2 C1 C11 121.8(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 C17 122.3(3) . . ?
C2 C3 C17 120.8(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 C6 116.1(3) . . ?
C4 C5 C6 120.9(3) . . ?
N2 C6 C7 122.0(3) . . ?
N2 C6 C5 115.9(3) . . ?
C7 C6 C5 122.1(3) . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 116.7(4) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
N2 C10 C9 124.6(3) . . ?
N2 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
C16 C11 C12 117.4(3) . . ?
C16 C11 C1 122.1(3) . . ?
C12 C11 C1 120.5(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 S1 124.3(2) . . ?
C13 C14 S1 116.9(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C11 C16 C15 121.9(3) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C22 C17 C18 117.3(3) . . ?
C22 C17 C3 121.1(3) . . ?
C18 C17 C3 121.5(3) . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 118.7(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 121.6(3) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C5 117.6(3) . . ?
C10 N2 C6 117.6(3) . . ?
C14 S1 C23 103.33(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
N1 C1 C2 C3 -1.5(5) . . . . ?
C11 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C17 179.6(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C17 C3 C4 C5 -178.2(3) . . . . ?
C3 C4 C5 N1 -1.5(5) . . . . ?
C3 C4 C5 C6 175.4(3) . . . . ?
N1 C5 C6 N2 175.4(3) . . . . ?
C4 C5 C6 N2 -1.7(5) . . . . ?
N1 C5 C6 C7 -3.3(5) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
N2 C6 C7 C8 -1.1(6) . . . . ?
C5 C6 C7 C8 177.5(4) . . . . ?
C6 C7 C8 C9 -0.6(7) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C8 C9 C10 N2 0.0(6) . . . . ?
N1 C1 C11 C16 168.2(3) . . . . ?
C2 C1 C11 C16 -13.6(5) . . . . ?
N1 C1 C11 C12 -12.1(4) . . . . ?
C2 C1 C11 C12 166.0(3) . . . . ?
C16 C11 C12 C13 -1.0(5) . . . . ?
C1 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C12 C13 C14 S1 179.1(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
S1 C14 C15 C16 -179.4(2) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
C1 C11 C16 C15 -179.7(3) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C4 C3 C17 C22 142.8(3) . . . . ?
C2 C3 C17 C22 -36.7(5) . . . . ?
C4 C3 C17 C18 -40.4(5) . . . . ?
C2 C3 C17 C18 140.2(3) . . . . ?
C22 C17 C18 C19 1.8(5) . . . . ?
C3 C17 C18 C19 -175.1(3) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
C18 C17 C22 C21 -1.2(5) . . . . ?
C3 C17 C22 C21 175.7(3) . . . . ?
C2 C1 N1 C5 1.3(5) . . . . ?
C11 C1 N1 C5 179.5(3) . . . . ?
C4 C5 N1 C1 0.1(5) . . . . ?
C6 C5 N1 C1 -176.8(3) . . . . ?
C9 C10 N2 C6 -1.7(6) . . . . ?
C7 C6 N2 C10 2.2(5) . . . . ?
C5 C6 N2 C10 -176.4(3) . . . . ?
C15 C14 S1 C23 -9.2(3) . . . . ?
C13 C14 S1 C23 171.7(2) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.075

