# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_NLL153
_database_code_depnum_ccdc_archive 'CCDC 1834976'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        NLL153
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O2 S'
_chemical_formula_weight         303.41
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Triclinic
_space_group_IT_number           2
_symmetry_space_group_name_H-M   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                   7.4134(3)
_cell_length_b                   8.4142(3)
_cell_length_c                   12.1239(4)
_cell_angle_alpha                84.720(3)
_cell_angle_beta                 88.990(3)
_cell_angle_gamma                84.549(3)
_cell_volume                     749.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3894
_cell_measurement_theta_min      2.7660
_cell_measurement_theta_max      27.6530

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
 CrysAlisPro 1.171.38.39f (Rigaku Oxford Diffraction, 2015)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            9463
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         27.916
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3035
_reflns_number_gt                2520
_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       'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT V2014/4 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'XCIF, SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0337P)²+0.5106P] 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         3035
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
S1 S 0.06048(6) 0.26297(5) 0.23553(3) 0.01467(12) Uani 1 1 d . . . . .
N1 N 0.16643(18) 0.25006(16) 0.35226(11) 0.0147(3) Uani 1 1 d . . . . .
O1 O -0.12921(16) 0.28097(14) 0.26299(10) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.13511(17) 0.13075(14) 0.17717(10) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.0983(2) 0.3549(2) 0.43793(13) 0.0151(3) Uani 1 1 d . . . . .
H1A H -0.0203 0.3294 0.4651 0.018 Uiso 1 1 calc R U . . .
H1B H 0.0918 0.4671 0.4100 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2411(2) 0.31576(19) 0.52792(13) 0.0130(3) Uani 1 1 d . . . . .
H2 H 0.2385 0.4033 0.5761 0.016 Uiso 1 1 calc R U . . .
C3 C 0.2116(2) 0.15996(19) 0.59567(13) 0.0145(3) Uani 1 1 d . . . . .
H3 H 0.1339 0.0960 0.5648 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2809(2) 0.1017(2) 0.69305(14) 0.0157(4) Uani 1 1 d . . . . .
H4 H 0.2423 0.0038 0.7209 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4120(2) 0.1690(2) 0.76538(14) 0.0173(4) Uani 1 1 d . . . . .
H5A H 0.4964 0.0815 0.7960 0.021 Uiso 1 1 calc R U . . .
H5B H 0.3448 0.2125 0.8269 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5217(2) 0.3000(2) 0.70890(14) 0.0164(4) Uani 1 1 d . . . . .
H6A H 0.4394 0.3903 0.6803 0.020 Uiso 1 1 calc R U . . .
H6B H 0.5989 0.3371 0.7630 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6366(2) 0.2387(2) 0.61561(14) 0.0168(4) Uani 1 1 d . . . . .
H7 H 0.7531 0.1944 0.6340 0.020 Uiso 1 1 calc R U . . .
C8 C 0.5913(2) 0.24042(19) 0.51006(14) 0.0152(3) Uani 1 1 d . . . . .
H8 H 0.6779 0.1930 0.4639 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4169(2) 0.30992(19) 0.45639(13) 0.0135(3) Uani 1 1 d . . . . .
H9 H 0.4336 0.4204 0.4278 0.016 Uiso 1 1 calc R U . . .
C10 C 0.3673(2) 0.2210(2) 0.35738(14) 0.0160(4) Uani 1 1 d . . . . .
H10A H 0.4231 0.2641 0.2895 0.019 Uiso 1 1 calc R U . . .
H10B H 0.4054 0.1073 0.3697 0.019 Uiso 1 1 calc R U . . .
C11 C 0.1116(2) 0.44165(19) 0.15756(13) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.2326(2) 0.4339(2) 0.06909(14) 0.0164(4) Uani 1 1 d . . . . .
H12 H 0.2850 0.3354 0.0497 0.020 Uiso 1 1 calc R U . . .
C13 C 0.2743(2) 0.5754(2) 0.00996(14) 0.0175(4) Uani 1 1 d . . . . .
H13 H 0.3527 0.5706 -0.0506 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2011(2) 0.7241(2) 0.03963(13) 0.0152(3) Uani 1 1 d . . . . .
C15 C 0.0780(2) 0.7288(2) 0.12748(14) 0.0157(4) Uani 1 1 d . . . . .
H15 H 0.0263 0.8273 0.1474 0.019 Uiso 1 1 calc R U . . .
C16 C 0.0314(2) 0.5890(2) 0.18581(13) 0.0153(4) Uani 1 1 d . . . . .
H16 H -0.0529 0.5935 0.2434 0.018 Uiso 1 1 calc R U . . .
C17 C 0.2560(2) 0.8766(2) -0.02151(15) 0.0206(4) Uani 1 1 d . . . . .
H17A H 0.2877 0.9479 0.0309 0.031 Uiso 1 1 calc R U . . .
H17B H 0.1567 0.9270 -0.0657 0.031 Uiso 1 1 calc R U . . .
H17C H 0.3583 0.8519 -0.0686 0.031 Uiso 1 1 calc R U . . .


_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
S1 O2 1.4348(13) . ?
S1 O1 1.4366(13) . ?
S1 N1 1.6206(14) . ?
S1 C11 1.7696(16) . ?
N1 C1 1.476(2) . ?
N1 C10 1.487(2) . ?
C1 C2 1.526(2) . ?
C2 C3 1.514(2) . ?
C2 C9 1.552(2) . ?
C3 C4 1.329(2) . ?
C4 C5 1.504(2) . ?
C5 C6 1.535(2) . ?
C6 C7 1.504(2) . ?
C7 C8 1.327(2) . ?
C8 C9 1.501(2) . ?
C9 C10 1.539(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.391(2) . ?
C14 C17 1.508(2) . ?
C15 C16 1.385(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
O2 S1 O1 120.58(7) . . ?
O2 S1 N1 106.71(7) . . ?
O1 S1 N1 105.90(7) . . ?
O2 S1 C11 107.66(8) . . ?
O1 S1 C11 107.31(7) . . ?
N1 S1 C11 108.16(7) . . ?
C1 N1 C10 110.21(13) . . ?
C1 N1 S1 118.88(11) . . ?
C10 N1 S1 121.39(11) . . ?
N1 C1 C2 102.30(12) . . ?
C3 C2 C1 110.96(13) . . ?
C3 C2 C9 114.43(13) . . ?
C1 C2 C9 100.55(12) . . ?
C4 C3 C2 129.15(15) . . ?
C3 C4 C5 130.21(15) . . ?
C4 C5 C6 116.05(14) . . ?
C7 C6 C5 111.32(14) . . ?
C8 C7 C6 127.63(16) . . ?
C7 C8 C9 127.68(16) . . ?
C8 C9 C10 112.98(13) . . ?
C8 C9 C2 118.46(13) . . ?
C10 C9 C2 103.34(13) . . ?
N1 C10 C9 103.77(13) . . ?
C12 C11 C16 120.46(15) . . ?
C12 C11 S1 119.68(13) . . ?
C16 C11 S1 119.86(13) . . ?
C11 C12 C13 119.07(16) . . ?
C12 C13 C14 121.30(16) . . ?
C15 C14 C13 118.56(15) . . ?
C15 C14 C17 120.89(15) . . ?
C13 C14 C17 120.55(15) . . ?
C16 C15 C14 121.00(16) . . ?
C15 C16 C11 119.53(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
O2 S1 N1 C1 -170.13(12) . . . . ?
O1 S1 N1 C1 -40.49(13) . . . . ?
C11 S1 N1 C1 74.28(13) . . . . ?
O2 S1 N1 C10 46.85(14) . . . . ?
O1 S1 N1 C10 176.49(12) . . . . ?
C11 S1 N1 C10 -68.73(14) . . . . ?
C10 N1 C1 C2 -28.79(16) . . . . ?
S1 N1 C1 C2 -175.61(11) . . . . ?
N1 C1 C2 C3 -79.01(15) . . . . ?
N1 C1 C2 C9 42.44(14) . . . . ?
C1 C2 C3 C4 -164.92(17) . . . . ?
C9 C2 C3 C4 82.2(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 -17.9(3) . . . . ?
C4 C5 C6 C7 -60.71(19) . . . . ?
C5 C6 C7 C8 89.6(2) . . . . ?
C6 C7 C8 C9 2.7(3) . . . . ?
C7 C8 C9 C10 -149.81(17) . . . . ?
C7 C8 C9 C2 -28.8(2) . . . . ?
C3 C2 C9 C8 -48.3(2) . . . . ?
C1 C2 C9 C8 -167.26(14) . . . . ?
C3 C2 C9 C10 77.50(16) . . . . ?
C1 C2 C9 C10 -41.46(15) . . . . ?
C1 N1 C10 C9 2.48(16) . . . . ?
S1 N1 C10 C9 148.34(11) . . . . ?
C8 C9 C10 N1 153.66(13) . . . . ?
C2 C9 C10 N1 24.43(15) . . . . ?
O2 S1 C11 C12 -10.52(15) . . . . ?
O1 S1 C11 C12 -141.71(13) . . . . ?
N1 S1 C11 C12 104.45(14) . . . . ?
O2 S1 C11 C16 170.00(13) . . . . ?
O1 S1 C11 C16 38.81(15) . . . . ?
N1 S1 C11 C16 -75.04(14) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
S1 C11 C12 C13 -178.70(13) . . . . ?
C11 C12 C13 C14 1.8(2) . . . . ?
C12 C13 C14 C15 -2.7(2) . . . . ?
C12 C13 C14 C17 176.58(15) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C17 C14 C15 C16 -178.13(15) . . . . ?
C14 C15 C16 C11 1.3(2) . . . . ?
C12 C11 C16 C15 -2.3(2) . . . . ?
S1 C11 C16 C15 177.18(12) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_mo_HFP1255_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1834977'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        HFP1255
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_space_group_IT_number           2
_symmetry_space_group_name_H-M   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                   6.2605(4)
_cell_length_b                   9.8392(6)
_cell_length_c                   12.7844(7)
_cell_angle_alpha                67.7938(14)
_cell_angle_beta                 88.4599(15)
_cell_angle_gamma                84.1325(16)
_cell_volume                     725.21(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7220
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      33.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            12624
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         33.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5107
_reflns_number_gt                4499
_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 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0510P)²+0.2024P] 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         5107
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.12595(9) 0.40313(7) 0.37510(5) 0.01776(12) Uani 1 1 d . . . . .
O2 O 0.33878(9) 0.58579(6) 0.33799(5) 0.01635(12) Uani 1 1 d . . . . .
O3 O 0.41852(10) 0.67509(7) 0.04343(5) 0.02175(13) Uani 1 1 d . . . . .
O4 O 0.08683(9) 0.63801(7) 0.11334(5) 0.01761(12) Uani 1 1 d . . . . .
C1 C 0.36495(11) 0.45953(8) 0.21307(6) 0.01078(12) Uani 1 1 d . . . . .
C2 C 0.61081(11) 0.43298(8) 0.22673(7) 0.01379(13) Uani 1 1 d . . . . .
H2A H 0.6761 0.4397 0.1538 0.017 Uiso 1 1 calc R U . . .
H2B H 0.6639 0.5102 0.2484 0.017 Uiso 1 1 calc R U . . .
C3 C 0.67801(11) 0.28129(8) 0.31688(6) 0.01399(13) Uani 1 1 d . . . . .
H3A H 0.6163 0.2761 0.3903 0.017 Uiso 1 1 calc R U . . .
H3B H 0.8364 0.2674 0.3253 0.017 Uiso 1 1 calc R U . . .
C4 C 0.60272(11) 0.15719(8) 0.28661(6) 0.01181(13) Uani 1 1 d . . . . .
H4 H 0.6647 0.1636 0.2122 0.014 Uiso 1 1 calc R U . . .
C5 C 0.67981(12) 0.00932(9) 0.37513(6) 0.01510(14) Uani 1 1 d . . . . .
H5 H 0.6987 0.0077 0.4491 0.018 Uiso 1 1 calc R U . . .
C6 C 0.72500(12) -0.11964(9) 0.36338(7) 0.01724(15) Uani 1 1 d . . . . .
H6 H 0.7723 -0.2005 0.4302 0.021 Uiso 1 1 calc R U . . .
C7 C 0.71166(13) -0.15510(9) 0.25912(8) 0.01951(15) Uani 1 1 d . . . . .
H7A H 0.6687 -0.2564 0.2827 0.023 Uiso 1 1 calc R U . . .
H7B H 0.8577 -0.1561 0.2276 0.023 Uiso 1 1 calc R U . . .
C8 C 0.55825(13) -0.05265(9) 0.16320(7) 0.01829(15) Uani 1 1 d . . . . .
H8A H 0.6147 0.0448 0.1288 0.022 Uiso 1 1 calc R U . . .
H8B H 0.5546 -0.0944 0.1040 0.022 Uiso 1 1 calc R U . . .
C9 C 0.33317(13) -0.03200(9) 0.20293(7) 0.01673(14) Uani 1 1 d . . . . .
H9 H 0.2359 -0.0947 0.1935 0.020 Uiso 1 1 calc R U . . .
C10 C 0.25125(12) 0.06246(8) 0.24966(7) 0.01462(14) Uani 1 1 d . . . . .
H10 H 0.1043 0.0558 0.2695 0.018 Uiso 1 1 calc R U . . .
C11 C 0.35552(11) 0.17805(8) 0.27591(6) 0.01143(12) Uani 1 1 d . . . . .
H11 H 0.2997 0.1742 0.3509 0.014 Uiso 1 1 calc R U . . .
C12 C 0.27762(11) 0.33265(8) 0.18912(6) 0.01127(12) Uani 1 1 d . . . . .
H12A H 0.1187 0.3457 0.1892 0.014 Uiso 1 1 calc R U . . .
H12B H 0.3228 0.3387 0.1128 0.014 Uiso 1 1 calc R U . . .
C13 C 0.26039(11) 0.47567(8) 0.31808(6) 0.01134(12) Uani 1 1 d . . . . .
C14 C 0.24612(15) 0.61662(10) 0.43248(7) 0.02010(16) Uani 1 1 d . . . . .
H14A H 0.2991 0.7062 0.4341 0.030 Uiso 1 1 calc R U . . .
H14B H 0.2872 0.5334 0.5030 0.030 Uiso 1 1 calc R U . . .
H14C H 0.0893 0.6311 0.4244 0.030 Uiso 1 1 calc R U . . .
C15 C 0.29983(12) 0.60335(8) 0.11376(6) 0.01304(13) Uani 1 1 d . . . . .
C16 C 0.00094(15) 0.76741(9) 0.01967(7) 0.02069(16) Uani 1 1 d . . . . .
H16A H -0.1562 0.7771 0.0233 0.031 Uiso 1 1 calc R U . . .
H16B H 0.0450 0.7578 -0.0516 0.031 Uiso 1 1 calc R U . . .
H16C H 0.0557 0.8551 0.0238 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.2024(9) . ?
O2 C13 1.3430(9) . ?
O2 C14 1.4460(9) . ?
O3 C15 1.2043(9) . ?
O4 C15 1.3419(9) . ?
O4 C16 1.4444(10) . ?
C1 C15 1.5273(10) . ?
C1 C13 1.5324(10) . ?
C1 C2 1.5381(10) . ?
C1 C12 1.5456(10) . ?
C2 C3 1.5265(11) . ?
C3 C4 1.5322(10) . ?
C4 C5 1.5072(10) . ?
C4 C11 1.5430(10) . ?
C5 C6 1.3345(11) . ?
C6 C7 1.5063(12) . ?
C7 C8 1.5406(12) . ?
C8 C9 1.5052(12) . ?
C9 C10 1.3377(11) . ?
C10 C11 1.5114(10) . ?
C11 C12 1.5442(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
C13 O2 C14 115.57(6) . . ?
C15 O4 C16 116.06(6) . . ?
C15 C1 C13 106.50(6) . . ?
C15 C1 C2 110.46(6) . . ?
C13 C1 C2 110.92(6) . . ?
C15 C1 C12 107.88(6) . . ?
C13 C1 C12 110.85(6) . . ?
C2 C1 C12 110.13(6) . . ?
C3 C2 C1 110.70(6) . . ?
C2 C3 C4 111.71(6) . . ?
C5 C4 C3 110.06(6) . . ?
C5 C4 C11 111.33(6) . . ?
C3 C4 C11 108.91(6) . . ?
C6 C5 C4 128.59(7) . . ?
C5 C6 C7 129.15(7) . . ?
C6 C7 C8 117.73(7) . . ?
C9 C8 C7 112.91(7) . . ?
C10 C9 C8 128.92(7) . . ?
C9 C10 C11 130.23(7) . . ?
C10 C11 C4 116.43(6) . . ?
C10 C11 C12 109.43(6) . . ?
C4 C11 C12 110.93(6) . . ?
C11 C12 C1 113.39(6) . . ?
O1 C13 O2 123.70(7) . . ?
O1 C13 C1 126.22(7) . . ?
O2 C13 C1 110.07(6) . . ?
O3 C15 O4 123.88(7) . . ?
O3 C15 C1 125.97(7) . . ?
O4 C15 C1 110.12(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
C15 C1 C2 C3 -173.48(6) . . . . ?
C13 C1 C2 C3 68.67(7) . . . . ?
C12 C1 C2 C3 -54.42(8) . . . . ?
C1 C2 C3 C4 60.05(8) . . . . ?
C2 C3 C4 C5 177.70(6) . . . . ?
C2 C3 C4 C11 -60.00(7) . . . . ?
C3 C4 C5 C6 -151.26(8) . . . . ?
C11 C4 C5 C6 87.89(9) . . . . ?
C4 C5 C6 C7 -0.22(14) . . . . ?
C5 C6 C7 C8 -23.77(12) . . . . ?
C6 C7 C8 C9 -53.00(10) . . . . ?
C7 C8 C9 C10 84.05(11) . . . . ?
C8 C9 C10 C11 0.81(14) . . . . ?
C9 C10 C11 C4 -21.45(12) . . . . ?
C9 C10 C11 C12 105.29(9) . . . . ?
C5 C4 C11 C10 -56.69(8) . . . . ?
C3 C4 C11 C10 -178.22(6) . . . . ?
C5 C4 C11 C12 177.31(6) . . . . ?
C3 C4 C11 C12 55.79(7) . . . . ?
C10 C11 C12 C1 176.54(6) . . . . ?
C4 C11 C12 C1 -53.66(8) . . . . ?
C15 C1 C12 C11 172.90(5) . . . . ?
C13 C1 C12 C11 -70.85(7) . . . . ?
C2 C1 C12 C11 52.28(7) . . . . ?
C14 O2 C13 O1 -1.77(11) . . . . ?
C14 O2 C13 C1 177.49(6) . . . . ?
C15 C1 C13 O1 116.02(8) . . . . ?
C2 C1 C13 O1 -123.75(8) . . . . ?
C12 C1 C13 O1 -1.07(10) . . . . ?
C15 C1 C13 O2 -63.22(7) . . . . ?
C2 C1 C13 O2 57.02(8) . . . . ?
C12 C1 C13 O2 179.69(6) . . . . ?
C16 O4 C15 O3 1.87(11) . . . . ?
C16 O4 C15 C1 -176.42(6) . . . . ?
C13 C1 C15 O3 132.19(8) . . . . ?
C2 C1 C15 O3 11.66(10) . . . . ?
C12 C1 C15 O3 -108.76(8) . . . . ?
C13 C1 C15 O4 -49.56(7) . . . . ?
C2 C1 C15 O4 -170.09(6) . . . . ?
C12 C1 C15 O4 69.49(7) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
