# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mchugh_furandppsmartall
_database_code_depnum_ccdc_archive 'CCDC 1506131'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N2 O4'
_chemical_formula_weight         448.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   23.385(2)
_cell_length_b                   5.3635(4)
_cell_length_c                   17.4866(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.455(10)
_cell_angle_gamma                90.00
_cell_volume                     2055.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    879
_cell_measurement_theta_min      5.3970
_cell_measurement_theta_max      69.2100


_exptl_crystal_description       needle
_exptl_crystal_colour            'red - purple'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_min  0.62188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3952
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         69.90
_reflns_number_total             1947
_reflns_number_gt                1246
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0557P)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         1947
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06303(8) -0.0256(4) 0.17880(11) 0.0281(5) Uani 1 1 d . . .
O2 O -0.10508(8) -0.6049(4) 0.02455(11) 0.0287(5) Uani 1 1 d . . .
N1 N 0.07179(9) 0.2309(4) 0.07582(13) 0.0234(5) Uani 1 1 d . . .
C1 C -0.00022(11) -0.0696(5) 0.03390(16) 0.0234(6) Uani 1 1 d . . .
C2 C 0.04573(11) 0.0305(5) 0.10618(16) 0.0248(6) Uani 1 1 d . . .
C3 C -0.04432(11) -0.2541(5) 0.00838(15) 0.0235(6) Uani 1 1 d . . .
C4 C -0.05937(11) -0.4348(5) 0.05849(16) 0.0249(6) Uani 1 1 d . . .
C5 C -0.03446(12) -0.4720(5) 0.14071(17) 0.0287(6) Uani 1 1 d . . .
H5 H -0.0025 -0.3783 0.1785 0.034 Uiso 1 1 calc R . .
C6 C -0.06576(12) -0.6787(6) 0.15894(17) 0.0301(7) Uani 1 1 d . . .
H6 H -0.0586 -0.7513 0.2110 0.036 Uiso 1 1 calc R . .
C7 C -0.10754(12) -0.7506(5) 0.08738(17) 0.0301(7) Uani 1 1 d . . .
H7 H -0.1352 -0.8852 0.0814 0.036 Uiso 1 1 calc R . .
C8 C 0.11963(11) 0.3858(6) 0.13114(16) 0.0269(6) Uani 1 1 d . . .
H8A H 0.1191 0.3651 0.1872 0.032 Uiso 1 1 calc R . .
H8B H 0.1104 0.5627 0.1156 0.032 Uiso 1 1 calc R . .
C9 C 0.18308(11) 0.3272(5) 0.13174(15) 0.0236(6) Uani 1 1 d . . .
C10 C 0.19626(12) 0.1176(6) 0.09574(17) 0.0317(7) Uani 1 1 d . . .
H10 H 0.1647 0.0028 0.0688 0.038 Uiso 1 1 calc R . .
C11 C 0.25576(12) 0.0727(6) 0.09867(19) 0.0375(7) Uani 1 1 d . . .
H11 H 0.2643 -0.0712 0.0728 0.045 Uiso 1 1 calc R . .
C12 C 0.30232(13) 0.2347(6) 0.13860(19) 0.0357(7) Uani 1 1 d . . .
H12 H 0.3427 0.2031 0.1404 0.043 Uiso 1 1 calc R . .
C13 C 0.28961(12) 0.4439(6) 0.17602(18) 0.0357(7) Uani 1 1 d . . .
H13 H 0.3216 0.5554 0.2044 0.043 Uiso 1 1 calc R . .
C14 C 0.23026(12) 0.4919(5) 0.17228(17) 0.0299(6) Uani 1 1 d . . .
H14 H 0.2217 0.6373 0.1974 0.036 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0275(9) 0.0321(12) 0.0221(9) 0.0029(9) 0.0056(7) 0.0029(9)
O2 0.0296(10) 0.0266(11) 0.0281(10) 0.0021(9) 0.0080(8) -0.0019(9)
N1 0.0212(10) 0.0260(13) 0.0213(11) -0.0001(10) 0.0051(8) 0.0026(10)
C1 0.0191(11) 0.0279(15) 0.0226(11) -0.0003(12) 0.0064(9) 0.0031(11)
C2 0.0220(12) 0.0266(16) 0.0236(13) 0.0016(12) 0.0051(10) 0.0094(12)
C3 0.0195(12) 0.0260(15) 0.0236(13) 0.0018(13) 0.0057(10) 0.0069(11)
C4 0.0194(12) 0.0249(15) 0.0275(13) -0.0022(12) 0.0045(10) 0.0018(11)
C5 0.0247(13) 0.0328(17) 0.0272(13) 0.0010(13) 0.0074(11) -0.0006(12)
C6 0.0295(13) 0.0334(17) 0.0285(15) 0.0061(13) 0.0115(11) 0.0056(13)
C7 0.0335(14) 0.0254(15) 0.0366(16) 0.0057(14) 0.0187(12) 0.0005(13)
C8 0.0263(13) 0.0298(16) 0.0234(13) -0.0024(12) 0.0073(10) 0.0008(12)
C9 0.0231(12) 0.0248(15) 0.0197(12) 0.0033(12) 0.0034(10) 0.0001(12)
C10 0.0284(14) 0.0278(16) 0.0366(16) -0.0051(14) 0.0086(12) -0.0045(13)
C11 0.0360(16) 0.0291(17) 0.0512(19) -0.0026(16) 0.0201(14) 0.0054(14)
C12 0.0253(13) 0.0368(18) 0.0463(17) 0.0108(16) 0.0140(12) 0.0064(13)
C13 0.0248(13) 0.0404(19) 0.0377(15) 0.0027(15) 0.0058(12) -0.0081(14)
C14 0.0313(14) 0.0268(15) 0.0309(14) -0.0036(14) 0.0100(11) -0.0040(13)

_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
O1 C2 1.228(3) . ?
O2 C7 1.366(3) . ?
O2 C4 1.372(3) . ?
N1 C3 1.391(3) 5 ?
N1 C2 1.426(3) . ?
N1 C8 1.457(3) . ?
C1 C3 1.386(4) . ?
C1 C1 1.404(5) 5 ?
C1 C2 1.446(3) . ?
C3 N1 1.391(3) 5 ?
C3 C4 1.431(4) . ?
C4 C5 1.364(4) . ?
C5 C6 1.425(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.347(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.375(4) . ?
C9 C14 1.398(4) . ?
C10 C11 1.395(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C4 106.1(2) . . ?
C3 N1 C2 111.2(2) 5 . ?
C3 N1 C8 128.0(2) 5 . ?
C2 N1 C8 120.8(2) . . ?
C3 C1 C1 109.4(3) . 5 ?
C3 C1 C2 142.1(3) . . ?
C1 C1 C2 108.5(3) 5 . ?
O1 C2 N1 122.7(2) . . ?
O1 C2 C1 133.5(3) . . ?
N1 C2 C1 103.8(2) . . ?
C1 C3 N1 107.1(2) . 5 ?
C1 C3 C4 127.0(2) . . ?
N1 C3 C4 126.0(2) 5 . ?
C5 C4 O2 109.9(2) . . ?
C5 C4 C3 129.7(3) . . ?
O2 C4 C3 120.4(2) . . ?
C4 C5 C6 106.6(2) . . ?
C4 C5 H5 126.7 . . ?
C6 C5 H5 126.7 . . ?
C7 C6 C5 106.1(3) . . ?
C7 C6 H6 126.9 . . ?
C5 C6 H6 126.9 . . ?
C6 C7 O2 111.3(3) . . ?
C6 C7 H7 124.4 . . ?
O2 C7 H7 124.4 . . ?
N1 C8 C9 114.2(2) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 C8 122.9(2) . . ?
C14 C9 C8 118.1(3) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?

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
C3 N1 C2 O1 179.6(2) 5 . . . ?
C8 N1 C2 O1 -2.1(4) . . . . ?
C3 N1 C2 C1 0.1(3) 5 . . . ?
C8 N1 C2 C1 178.4(2) . . . . ?
C3 C1 C2 O1 0.5(6) . . . . ?
C1 C1 C2 O1 -179.5(3) 5 . . . ?
C3 C1 C2 N1 180.0(4) . . . . ?
C1 C1 C2 N1 -0.1(3) 5 . . . ?
C1 C1 C3 N1 0.0(4) 5 . . 5 ?
C2 C1 C3 N1 179.9(3) . . . 5 ?
C1 C1 C3 C4 -179.8(3) 5 . . . ?
C2 C1 C3 C4 0.1(6) . . . . ?
C7 O2 C4 C5 -0.7(3) . . . . ?
C7 O2 C4 C3 179.3(2) . . . . ?
C1 C3 C4 C5 -1.0(5) . . . . ?
N1 C3 C4 C5 179.2(3) 5 . . . ?
C1 C3 C4 O2 179.0(3) . . . . ?
N1 C3 C4 O2 -0.8(4) 5 . . . ?
O2 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 O2 0.2(3) . . . . ?
C4 O2 C7 C6 0.3(3) . . . . ?
C3 N1 C8 C9 -79.0(3) 5 . . . ?
C2 N1 C8 C9 103.0(3) . . . . ?
N1 C8 C9 C10 -11.8(4) . . . . ?
N1 C8 C9 C14 169.6(2) . . . . ?
C14 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 C11 -179.6(3) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C9 1.0(4) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C8 C9 C14 C13 178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        69.90
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_mchugh_b2t2dpp
_database_code_depnum_ccdc_archive 'CCDC 1506132'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N2 O2 S2'
_chemical_formula_weight         480.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   5.5724(3)
_cell_length_b                   11.3414(7)
_cell_length_c                   17.3547(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.822(5)
_cell_angle_gamma                90.00
_cell_volume                     1089.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1476
_cell_measurement_theta_min      8.1190
_cell_measurement_theta_max      72.3860

_exptl_crystal_description       'flattened needle'
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    2.465
_exptl_absorpt_correction_T_min  0.46588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4332
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         73.21
_reflns_number_total             2123
_reflns_number_gt                1727
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0837P)²+0.5646P] 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         2123
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
S1 S 0.27478(15) -0.37484(7) 0.96426(5) 0.0368(3) Uani 1 1 d . . .
O1 O 0.3237(4) 0.08031(18) 0.88746(11) 0.0306(5) Uani 1 1 d . . .
N1 N 0.0497(4) 0.1740(2) 0.95830(13) 0.0255(5) Uani 1 1 d . . .
C1 C 0.0870(5) -0.0224(2) 0.97710(15) 0.0259(6) Uani 1 1 d . . .
C2 C 0.1766(5) 0.0739(2) 0.93467(16) 0.0258(6) Uani 1 1 d . . .
C3 C 0.1100(5) -0.1434(3) 0.98860(15) 0.0256(6) Uani 1 1 d . . .
C4 C 0.2668(5) -0.2231(2) 0.95346(15) 0.0261(6) Uani 1 1 d . . .
C5 C 0.4336(5) -0.1875(3) 0.90409(17) 0.0322(6) Uani 1 1 d . . .
H5 H 0.4597 -0.1076 0.8908 0.039 Uiso 1 1 calc R . .
C6 C 0.5591(6) -0.2838(3) 0.87618(18) 0.0353(7) Uani 1 1 d . . .
H6 H 0.6779 -0.2751 0.8416 0.042 Uiso 1 1 calc R . .
C7 C 0.4948(6) -0.3890(3) 0.90308(17) 0.0339(7) Uani 1 1 d . . .
H7 H 0.5625 -0.4621 0.8899 0.041 Uiso 1 1 calc R . .
C8 C 0.0944(5) 0.2889(2) 0.92575(16) 0.0279(6) Uani 1 1 d . . .
H8A H 0.2576 0.2884 0.9086 0.033 Uiso 1 1 calc R . .
H8B H 0.0946 0.3488 0.9672 0.033 Uiso 1 1 calc R . .
C9 C -0.0872(5) 0.3260(2) 0.85766(16) 0.0271(6) Uani 1 1 d . . .
C10 C -0.3031(5) 0.2663(3) 0.83864(16) 0.0290(6) Uani 1 1 d . . .
H10 H -0.3377 0.1984 0.8674 0.035 Uiso 1 1 calc R . .
C11 C -0.4703(5) 0.3053(3) 0.77748(16) 0.0325(7) Uani 1 1 d . . .
H11 H -0.6172 0.2635 0.7644 0.039 Uiso 1 1 calc R . .
C12 C -0.4215(6) 0.4050(3) 0.73609(17) 0.0374(7) Uani 1 1 d . . .
H12 H -0.5366 0.4331 0.6955 0.045 Uiso 1 1 calc R . .
C13 C -0.2038(6) 0.4637(3) 0.75407(18) 0.0385(7) Uani 1 1 d . . .
H13 H -0.1687 0.5312 0.7250 0.046 Uiso 1 1 calc R . .
C14 C -0.0372(6) 0.4244(3) 0.81425(17) 0.0332(6) Uani 1 1 d . . .
H14 H 0.1120 0.4647 0.8260 0.040 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0456(5) 0.0196(4) 0.0475(5) -0.0006(3) 0.0147(3) 0.0019(3)
O1 0.0311(11) 0.0242(11) 0.0380(10) 0.0018(8) 0.0097(8) -0.0012(8)
N1 0.0277(12) 0.0191(12) 0.0297(11) 0.0017(9) 0.0034(9) -0.0002(9)
C1 0.0258(13) 0.0212(14) 0.0309(13) -0.0014(11) 0.0042(10) 0.0004(10)
C2 0.0244(13) 0.0195(14) 0.0326(13) 0.0000(10) -0.0003(10) 0.0003(10)
C3 0.0245(13) 0.0238(14) 0.0279(12) 0.0010(11) 0.0009(10) -0.0026(10)
C4 0.0281(14) 0.0154(13) 0.0337(14) -0.0006(10) -0.0011(11) 0.0000(10)
C5 0.0295(15) 0.0261(15) 0.0412(15) -0.0011(12) 0.0052(11) 0.0039(11)
C6 0.0347(16) 0.0323(17) 0.0398(16) 0.0006(13) 0.0081(12) 0.0024(13)
C7 0.0357(16) 0.0282(16) 0.0388(15) -0.0054(12) 0.0082(12) 0.0064(12)
C8 0.0260(14) 0.0190(14) 0.0379(14) 0.0015(11) 0.0011(11) -0.0018(10)
C9 0.0280(14) 0.0202(13) 0.0340(14) -0.0008(11) 0.0069(11) 0.0049(11)
C10 0.0310(15) 0.0238(15) 0.0331(13) 0.0030(11) 0.0070(11) 0.0013(11)
C11 0.0278(14) 0.0348(17) 0.0348(15) -0.0032(12) 0.0033(11) 0.0017(12)
C12 0.0407(17) 0.0390(18) 0.0320(14) 0.0034(13) 0.0023(12) 0.0125(14)
C13 0.054(2) 0.0233(16) 0.0397(15) 0.0065(13) 0.0118(13) 0.0070(13)
C14 0.0382(16) 0.0231(15) 0.0399(15) -0.0010(12) 0.0106(12) -0.0017(12)

_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
S1 C7 1.722(3) . ?
S1 C4 1.732(3) . ?
O1 C2 1.228(3) . ?
N1 C3 1.399(3) 3_557 ?
N1 C2 1.423(3) . ?
N1 C8 1.454(3) . ?
C1 C3 1.390(4) . ?
C1 C1 1.419(5) 3_557 ?
C1 C2 1.440(4) . ?
C3 N1 1.399(3) 3_557 ?
C3 C4 1.442(4) . ?
C4 C5 1.396(4) . ?
C5 C6 1.414(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.345(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.521(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.386(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.399(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C4 92.12(15) . . ?
C3 N1 C2 111.6(2) 3_557 . ?
C3 N1 C8 129.1(2) 3_557 . ?
C2 N1 C8 119.3(2) . . ?
C3 C1 C1 109.3(3) . 3_557 ?
C3 C1 C2 142.3(3) . . ?
C1 C1 C2 108.4(3) 3_557 . ?
O1 C2 N1 122.6(2) . . ?
O1 C2 C1 133.3(3) . . ?
N1 C2 C1 104.1(2) . . ?
C1 C3 N1 106.5(2) . 3_557 ?
C1 C3 C4 127.5(3) . . ?
N1 C3 C4 126.0(3) 3_557 . ?
C5 C4 C3 124.0(3) . . ?
C5 C4 S1 110.1(2) . . ?
C3 C4 S1 125.9(2) . . ?
C4 C5 C6 112.3(3) . . ?
C4 C5 H5 123.9 . . ?
C6 C5 H5 123.9 . . ?
C7 C6 C5 113.8(3) . . ?
C7 C6 H6 123.1 . . ?
C5 C6 H6 123.1 . . ?
C6 C7 S1 111.7(2) . . ?
C6 C7 H7 124.2 . . ?
S1 C7 H7 124.2 . . ?
N1 C8 C9 114.9(2) . . ?
N1 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
N1 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C8 121.9(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?

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
C3 N1 C2 O1 179.0(2) 3_557 . . . ?
C8 N1 C2 O1 0.0(4) . . . . ?
C3 N1 C2 C1 -0.4(3) 3_557 . . . ?
C8 N1 C2 C1 -179.4(2) . . . . ?
C3 C1 C2 O1 0.6(6) . . . . ?
C1 C1 C2 O1 -178.9(3) 3_557 . . . ?
C3 C1 C2 N1 180.0(3) . . . . ?
C1 C1 C2 N1 0.4(3) 3_557 . . . ?
C1 C1 C3 N1 -0.1(4) 3_557 . . 3_557 ?
C2 C1 C3 N1 -179.6(3) . . . 3_557 ?
C1 C1 C3 C4 -179.9(3) 3_557 . . . ?
C2 C1 C3 C4 0.6(6) . . . . ?
C1 C3 C4 C5 3.7(4) . . . . ?
N1 C3 C4 C5 -176.2(3) 3_557 . . . ?
C1 C3 C4 S1 -175.2(2) . . . . ?
N1 C3 C4 S1 4.9(4) 3_557 . . . ?
C7 S1 C4 C5 -0.5(2) . . . . ?
C7 S1 C4 C3 178.5(2) . . . . ?
C3 C4 C5 C6 -178.4(3) . . . . ?
S1 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 S1 0.2(3) . . . . ?
C4 S1 C7 C6 0.2(2) . . . . ?
C3 N1 C8 C9 -81.7(3) 3_557 . . . ?
C2 N1 C8 C9 97.1(3) . . . . ?
N1 C8 C9 C10 12.4(4) . . . . ?
N1 C8 C9 C14 -169.0(3) . . . . ?
C14 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 1.8(5) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C9 -0.5(5) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C8 C9 C14 C13 -177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.079
