# 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_TSAS001b_100K
_database_code_depnum_ccdc_archive 'CCDC 992409'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Nigerloxin dioxane water solvate'
_chemical_name_common            'Nigerloxin dioxane water solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N O5, 0.5(C4 H8 O2), H2 O'
_chemical_formula_sum            'C12 H13 N O7'
_chemical_formula_weight         283.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   28.77(3)
_cell_length_b                   8.771(8)
_cell_length_c                   10.2110(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.17(3)
_cell_angle_gamma                90
_cell_volume                     2448(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1657
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.301
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 45.0467
	          2theta: -19.6352
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 45.0467
	          2theta: -19.6352
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 45.0467
	          2theta: -19.6352
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 45.0467
	          2theta: -19.6352

;
_diffrn_orient_matrix_UB_11      -0.093391
_diffrn_orient_matrix_UB_12      0.036194
_diffrn_orient_matrix_UB_13      -0.024317
_diffrn_orient_matrix_UB_21      0.045289
_diffrn_orient_matrix_UB_22      0.058635
_diffrn_orient_matrix_UB_23      -0.086662
_diffrn_orient_matrix_UB_31      0.098667
_diffrn_orient_matrix_UB_32      -0.067394
_diffrn_orient_matrix_UB_33      0.005964
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  -0.093391
_diffrn_reflns_transf_matrix_12  0.036194
_diffrn_reflns_transf_matrix_13  -0.024317
_diffrn_reflns_transf_matrix_21  0.045289
_diffrn_reflns_transf_matrix_22  0.058635
_diffrn_reflns_transf_matrix_23  -0.086662
_diffrn_reflns_transf_matrix_31  0.098667
_diffrn_reflns_transf_matrix_32  -0.067394
_diffrn_reflns_transf_matrix_33  0.005964

_diffrn_reflns_number            8972
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         25.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2200
_reflns_number_gt                1674
_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       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1168P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2200
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.87006(7) 0.5929(2) 0.54617(19) 0.0218(5) Uani 1 1 d . . . . .
O2 O 0.88354(7) 0.2605(3) 0.6066(2) 0.0282(6) Uani 1 1 d . . . . .
O3 O 0.78210(7) 0.3019(3) 0.1583(2) 0.0260(6) Uani 1 1 d . . . . .
O4 O 0.78241(7) 0.6715(2) 0.1475(2) 0.0251(6) Uani 1 1 d . . . . .
O5 O 0.82611(8) 0.9111(2) 0.3149(2) 0.0261(6) Uani 1 1 d . . . . .
N1 N 0.83076(9) 0.2386(3) 0.3802(3) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.84951(10) 0.4797(3) 0.4597(3) 0.0208(7) Uani 1 1 d . . . . .
C3 C 0.82016(10) 0.4965(3) 0.3288(3) 0.0210(7) Uani 1 1 d . . . . .
C4 C 0.80873(10) 0.6435(3) 0.2666(3) 0.0198(7) Uani 1 1 d . . . . .
C5 C 0.83272(10) 0.7681(3) 0.3611(3) 0.0206(7) Uani 1 1 d . . . . .
C6 C 0.86169(10) 0.7402(3) 0.4950(3) 0.0220(7) Uani 1 1 d . . . . .
C7 C 0.85806(10) 0.3168(4) 0.4988(3) 0.0226(7) Uani 1 1 d . . . . .
C8 C 0.80748(10) 0.3400(3) 0.2731(3) 0.0225(7) Uani 1 1 d . . . . .
C9 C 0.88677(10) 0.8573(4) 0.5933(3) 0.0233(7) Uani 1 1 d . . . . .
H9 H 0.8801 0.9608 0.5667 0.028 Uiso 1 1 calc R U . . .
C10 C 0.91831(10) 0.8295(4) 0.7177(3) 0.0265(7) Uani 1 1 d . . . . .
H10 H 0.9256 0.7261 0.7438 0.032 Uiso 1 1 calc R U . . .
C11 C 0.94289(12) 0.9495(4) 0.8185(3) 0.0338(8) Uani 1 1 d . . . . .
H11A H 0.9338 1.0502 0.7769 0.051 Uiso 1 1 calc R U . . .
H11B H 0.9784 0.9367 0.8438 0.051 Uiso 1 1 calc R U . . .
H11C H 0.9326 0.9405 0.9011 0.051 Uiso 1 1 calc R U . . .
O6 O 0.95123(8) 0.4464(3) 0.4424(2) 0.0388(7) Uani 1 1 d . . . . .
C12 C 0.96438(12) 0.5994(5) 0.4234(4) 0.0408(9) Uani 1 1 d . . . . .
H12A H 0.9583 0.6650 0.4953 0.049 Uiso 1 1 calc R U . . .
H12B H 0.9436 0.6368 0.3325 0.049 Uiso 1 1 calc R U . . .
C13 C 0.98244(13) 0.3889(5) 0.5689(4) 0.0494(11) Uani 1 1 d . . . . .
H13A H 0.9742 0.2808 0.5788 0.059 Uiso 1 1 calc R U . . .
H13B H 0.9771 0.4469 0.6461 0.059 Uiso 1 1 calc R U . . .
O7 O 0.71808(9) 0.4904(3) 0.4342(2) 0.0310(6) Uani 1 1 d . . . . .
H5A H 0.8112(15) 0.912(5) 0.229(4) 0.051(13) Uiso 1 1 d . . . . .
H1N H 0.8309(10) 0.132(4) 0.374(3) 0.015(7) Uiso 1 1 d . . . . .
H7A H 0.7249(13) 0.611(5) 0.450(4) 0.041(10) Uiso 1 1 d . . . . .
H7B H 0.7388(18) 0.405(6) 0.497(5) 0.082(16) Uiso 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
O1 C2 1.338(4) . ?
O1 C6 1.386(4) . ?
O2 C7 1.221(4) . ?
O3 C8 1.218(4) . ?
O4 C4 1.240(3) . ?
O5 C5 1.333(4) . ?
O5 H5A 0.85(4) . ?
N1 C7 1.400(4) . ?
N1 C8 1.407(4) . ?
N1 H1N 0.93(3) . ?
C2 C3 1.349(4) . ?
C2 C7 1.483(4) . ?
C3 C4 1.430(4) . ?
C3 C8 1.487(4) . ?
C4 C5 1.479(4) . ?
C5 C6 1.383(4) . ?
C6 C9 1.460(4) . ?
C9 C10 1.334(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.487(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O6 C13 1.417(4) . ?
O6 C12 1.423(5) . ?
C12 C13 1.511(5) 5_766 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C12 1.511(5) 5_766 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O7 H7A 1.08(4) . ?
O7 H7B 1.04(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 O1 C6 117.0(2) . . ?
C5 O5 H5A 110(3) . . ?
C7 N1 C8 111.5(3) . . ?
C7 N1 H1N 122.1(17) . . ?
C8 N1 H1N 126.3(17) . . ?
O1 C2 C3 125.8(3) . . ?
O1 C2 C7 122.4(3) . . ?
C3 C2 C7 111.8(3) . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 C8 106.4(3) . . ?
C4 C3 C8 131.9(3) . . ?
O4 C4 C3 126.8(3) . . ?
O4 C4 C5 120.8(3) . . ?
C3 C4 C5 112.4(2) . . ?
O5 C5 C6 119.5(3) . . ?
O5 C5 C4 118.6(2) . . ?
C6 C5 C4 122.0(3) . . ?
C5 C6 O1 121.2(3) . . ?
C5 C6 C9 124.9(3) . . ?
O1 C6 C9 113.9(2) . . ?
O2 C7 N1 126.8(3) . . ?
O2 C7 C2 129.4(3) . . ?
N1 C7 C2 103.8(2) . . ?
O3 C8 N1 124.9(3) . . ?
O3 C8 C3 128.5(3) . . ?
N1 C8 C3 106.6(3) . . ?
C10 C9 C6 124.8(3) . . ?
C10 C9 H9 117.6 . . ?
C6 C9 H9 117.6 . . ?
C9 C10 C11 124.4(3) . . ?
C9 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 O6 C12 109.9(3) . . ?
O6 C12 C13 111.4(3) . 5_766 ?
O6 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 5_766 . ?
O6 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 5_766 . ?
H12A C12 H12B 108.0 . . ?
O6 C13 C12 111.5(3) . 5_766 ?
O6 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 5_766 . ?
O6 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 5_766 . ?
H13A C13 H13B 108.0 . . ?
H7A O7 H7B 124(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C2 C3 -2.2(4) . . . . ?
C6 O1 C2 C7 176.2(3) . . . . ?
O1 C2 C3 C4 1.5(5) . . . . ?
C7 C2 C3 C4 -177.0(3) . . . . ?
O1 C2 C3 C8 178.5(3) . . . . ?
C7 C2 C3 C8 0.0(3) . . . . ?
C2 C3 C4 O4 179.8(3) . . . . ?
C8 C3 C4 O4 3.7(6) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C8 C3 C4 C5 -175.7(3) . . . . ?
O4 C4 C5 O5 -1.1(4) . . . . ?
C3 C4 C5 O5 178.3(3) . . . . ?
O4 C4 C5 C6 179.1(3) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
O5 C5 C6 O1 -179.0(3) . . . . ?
C4 C5 C6 O1 0.8(5) . . . . ?
O5 C5 C6 C9 -0.4(5) . . . . ?
C4 C5 C6 C9 179.4(3) . . . . ?
C2 O1 C6 C5 1.0(4) . . . . ?
C2 O1 C6 C9 -177.7(2) . . . . ?
C8 N1 C7 O2 -177.3(3) . . . . ?
C8 N1 C7 C2 1.2(3) . . . . ?
O1 C2 C7 O2 -0.8(5) . . . . ?
C3 C2 C7 O2 177.7(3) . . . . ?
O1 C2 C7 N1 -179.3(3) . . . . ?
C3 C2 C7 N1 -0.7(3) . . . . ?
C7 N1 C8 O3 178.8(3) . . . . ?
C7 N1 C8 C3 -1.2(3) . . . . ?
C2 C3 C8 O3 -179.3(3) . . . . ?
C4 C3 C8 O3 -2.8(6) . . . . ?
C2 C3 C8 N1 0.7(3) . . . . ?
C4 C3 C8 N1 177.3(3) . . . . ?
C5 C6 C9 C10 -173.4(3) . . . . ?
O1 C6 C9 C10 5.3(4) . . . . ?
C6 C9 C10 C11 -178.6(3) . . . . ?
C13 O6 C12 C13 55.9(4) . . . 5_766 ?
C12 O6 C13 C12 -56.0(5) . . . 5_766 ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_chemical_compound_source        'Aspergillus niger '
####################################################################### 
# 
# 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_SS05062015a_100K
_database_code_depnum_ccdc_archive 'CCDC 1440606'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Nigerloxin monohydrate'
_chemical_name_common            'Nigerloxin monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N O5, H2 O'
_chemical_formula_sum            'C10 H9 N O6'
_chemical_formula_weight         239.18

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'

_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                   11.277(4)
_cell_length_b                   8.788(3)
_cell_length_c                   9.851(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.003(7)
_cell_angle_gamma                90
_cell_volume                     970.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    981
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 44.9434
	          2theta: -19.6782
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 44.9434
	          2theta: -19.6782
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.9434
	          2theta: -19.6782
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 44.9434
	          2theta: -19.6782

;
_diffrn_orient_matrix_UB_11      -0.008058
_diffrn_orient_matrix_UB_12      0.038677
_diffrn_orient_matrix_UB_13      0.079937
_diffrn_orient_matrix_UB_21      -0.006306
_diffrn_orient_matrix_UB_22      0.102019
_diffrn_orient_matrix_UB_23      -0.049997
_diffrn_orient_matrix_UB_31      -0.101910
_diffrn_orient_matrix_UB_32      -0.004444
_diffrn_orient_matrix_UB_33      0.003785
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  -0.008058
_diffrn_reflns_transf_matrix_12  0.038677
_diffrn_reflns_transf_matrix_13  0.079937
_diffrn_reflns_transf_matrix_21  -0.006306
_diffrn_reflns_transf_matrix_22  0.102019
_diffrn_reflns_transf_matrix_23  -0.049997
_diffrn_reflns_transf_matrix_31  -0.101910
_diffrn_reflns_transf_matrix_32  -0.004444
_diffrn_reflns_transf_matrix_33  0.003785
_reflns_shell_number_unique_all  1770

_diffrn_reflns_number            5639
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1710
_reflns_number_gt                1274
_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       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1710
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C2 C 0.74828(17) 0.2210(2) 0.4084(2) 0.0156(4) Uani 1 1 d . . . . .
C3 C 0.67569(16) 0.2379(2) 0.2919(2) 0.0165(5) Uani 1 1 d . . . . .
C4 C 0.64762(16) 0.3866(2) 0.2362(2) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.70675(17) 0.5075(2) 0.3198(2) 0.0170(5) Uani 1 1 d . . . . .
C6 C 0.77832(16) 0.4800(2) 0.4386(2) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.76758(17) 0.0560(2) 0.4424(2) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.64005(16) 0.0820(2) 0.2434(2) 0.0165(4) Uani 1 1 d . . . . .
C9 C 0.83639(16) 0.5945(2) 0.5277(2) 0.0179(5) Uani 1 1 d . . . . .
C10 C 0.91204(17) 0.5666(2) 0.6378(2) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.96788(18) 0.6869(2) 0.7294(2) 0.0230(5) Uani 1 1 d . . . . .
H11A H 0.9433 0.7873 0.6932 0.034 Uiso 1 1 calc R U . . .
H11B H 1.0549 0.6781 0.7346 0.034 Uiso 1 1 calc R U . . .
H11C H 0.9423 0.6748 0.8209 0.034 Uiso 1 1 calc R U . . .
N1 N 0.69623(15) -0.0180(2) 0.33941(18) 0.0189(4) Uani 1 1 d . . . . .
O1 O 0.80038(11) 0.33181(14) 0.48448(13) 0.0176(3) Uani 1 1 d . . . . .
O2 O 0.83145(12) -0.00009(16) 0.53447(15) 0.0246(4) Uani 1 1 d . . . . .
O3 O 0.57731(11) 0.04698(16) 0.14136(14) 0.0196(3) Uani 1 1 d . . . . .
O4 O 0.58326(11) 0.41524(15) 0.12971(14) 0.0201(3) Uani 1 1 d . . . . .
O5 O 0.68978(13) 0.65257(15) 0.27801(15) 0.0199(3) Uani 1 1 d . . . . .
O7 O 0.57551(14) 0.76197(19) 0.55359(17) 0.0260(4) Uani 1 1 d . . . . .
H1N H 0.693(2) -0.119(3) 0.335(2) 0.034(7) Uiso 1 1 d . . . . .
H5A H 0.641(3) 0.666(3) 0.196(3) 0.064(9) Uiso 1 1 d . . . . .
H7A H 0.558(2) 0.668(3) 0.553(3) 0.056(9) Uiso 1 1 d . . . . .
H7B H 0.525(2) 0.809(3) 0.500(3) 0.041(8) Uiso 1 1 d . . . . .
H9 H 0.8166(16) 0.697(2) 0.506(2) 0.011(5) Uiso 1 1 d . . . . .
H10 H 0.931(2) 0.453(3) 0.657(2) 0.050(7) Uiso 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
C2 O1 1.328(2) . ?
C2 C3 1.346(3) . ?
C2 C7 1.499(3) . ?
C3 C4 1.440(3) . ?
C3 C8 1.492(3) . ?
C4 O4 1.238(2) . ?
C4 C5 1.462(3) . ?
C5 O5 1.348(2) . ?
C5 C6 1.371(3) . ?
C6 O1 1.392(2) . ?
C6 C9 1.446(3) . ?
C7 O2 1.203(2) . ?
C7 N1 1.389(3) . ?
C8 O3 1.207(2) . ?
C8 N1 1.394(3) . ?
C9 C10 1.331(3) . ?
C9 H9 0.95(2) . ?
C10 C11 1.487(3) . ?
C10 H10 1.03(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 H1N 0.89(2) . ?
O5 H5A 0.94(3) . ?
O7 H7A 0.85(3) . ?
O7 H7B 0.85(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
O1 C2 C3 126.46(18) . . ?
O1 C2 C7 122.54(17) . . ?
C3 C2 C7 110.98(17) . . ?
C2 C3 C4 120.98(17) . . ?
C2 C3 C8 106.94(17) . . ?
C4 C3 C8 132.08(18) . . ?
O4 C4 C3 126.42(18) . . ?
O4 C4 C5 121.52(18) . . ?
C3 C4 C5 112.05(17) . . ?
O5 C5 C6 118.65(18) . . ?
O5 C5 C4 118.25(18) . . ?
C6 C5 C4 123.10(18) . . ?
C5 C6 O1 120.73(17) . . ?
C5 C6 C9 125.74(18) . . ?
O1 C6 C9 113.53(17) . . ?
O2 C7 N1 127.89(19) . . ?
O2 C7 C2 128.76(19) . . ?
N1 C7 C2 103.33(16) . . ?
O3 C8 N1 126.12(18) . . ?
O3 C8 C3 127.99(18) . . ?
N1 C8 C3 105.88(16) . . ?
C10 C9 C6 125.29(19) . . ?
C10 C9 H9 118.1(12) . . ?
C6 C9 H9 116.5(12) . . ?
C9 C10 C11 124.0(2) . . ?
C9 C10 H10 115.6(14) . . ?
C11 C10 H10 120.4(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 N1 C8 112.80(16) . . ?
C7 N1 H1N 121.6(16) . . ?
C8 N1 H1N 125.4(16) . . ?
C2 O1 C6 116.67(15) . . ?
C5 O5 H5A 115.6(18) . . ?
H7A O7 H7B 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 0.6(3) . . . . ?
C7 C2 C3 C4 -177.76(16) . . . . ?
O1 C2 C3 C8 179.68(17) . . . . ?
C7 C2 C3 C8 1.3(2) . . . . ?
C2 C3 C4 O4 179.23(18) . . . . ?
C8 C3 C4 O4 0.4(3) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C8 C3 C4 C5 -178.57(19) . . . . ?
O4 C4 C5 O5 -0.1(3) . . . . ?
C3 C4 C5 O5 178.88(16) . . . . ?
O4 C4 C5 C6 179.78(17) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
O5 C5 C6 O1 -178.73(16) . . . . ?
C4 C5 C6 O1 1.3(3) . . . . ?
O5 C5 C6 C9 1.8(3) . . . . ?
C4 C5 C6 C9 -178.10(17) . . . . ?
O1 C2 C7 O2 -2.5(3) . . . . ?
C3 C2 C7 O2 175.91(19) . . . . ?
O1 C2 C7 N1 179.09(16) . . . . ?
C3 C2 C7 N1 -2.5(2) . . . . ?
C2 C3 C8 O3 -178.52(18) . . . . ?
C4 C3 C8 O3 0.4(3) . . . . ?
C2 C3 C8 N1 0.3(2) . . . . ?
C4 C3 C8 N1 179.29(19) . . . . ?
C5 C6 C9 C10 -175.23(19) . . . . ?
O1 C6 C9 C10 5.3(3) . . . . ?
C6 C9 C10 C11 -178.36(18) . . . . ?
O2 C7 N1 C8 -175.70(19) . . . . ?
C2 C7 N1 C8 2.7(2) . . . . ?
O3 C8 N1 C7 176.85(18) . . . . ?
C3 C8 N1 C7 -2.0(2) . . . . ?
C3 C2 O1 C6 -0.5(3) . . . . ?
C7 C2 O1 C6 177.66(17) . . . . ?
C5 C6 O1 C2 -0.5(2) . . . . ?
C9 C6 O1 C2 179.05(16) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dioxane and methanol '
_chemical_compound_source        'Aspergillus niger'
