# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/ccz1zkj
_database_code_depnum_ccdc_archive 'CCDC 895638'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_publcif_datablock.id            {06113c2d-cce7-4dc2-b45d-bdae7bfd85d8}

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-3-[(Phenylamino)methylene]chroman-2,4-dione  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

loop_
_symmetry_equiv_pos_as_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                   16.539(3)
_cell_length_b                   6.2596(12)
_cell_length_c                   11.472(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1187.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4605
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       lath

_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;


_exptl_special_details           ?
_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            6335
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 128
	           Slice: -110.0000 - 18.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0613
	          2theta: -20.1098
scan:
	Number of images: 89
	           Slice: -65.0000 - 24.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -15.0000
	             Phi: 0.0000
	             XTD: 45.0613
	          2theta: -20.1098
scan:
	Number of images: 44
	           Slice: -94.0000 - -50.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 15.0000
	             Phi: 180.0000
	             XTD: 45.0613
	          2theta: -20.1098

;
_diffrn_orient_matrix_UB_11      0.150566
_diffrn_orient_matrix_UB_12      -0.046382
_diffrn_orient_matrix_UB_13      0.026101
_diffrn_orient_matrix_UB_21      0.028554
_diffrn_orient_matrix_UB_22      0.078194
_diffrn_orient_matrix_UB_23      -0.025764
_diffrn_orient_matrix_UB_31      -0.003680
_diffrn_orient_matrix_UB_32      0.020119
_diffrn_orient_matrix_UB_33      0.056981
_diffrn_orient_matrix_type       d*Trek
_diffrn_reflns_transf_matrix_11  0.150566
_diffrn_reflns_transf_matrix_12  -0.046382
_diffrn_reflns_transf_matrix_13  0.026101
_diffrn_reflns_transf_matrix_21  0.028554
_diffrn_reflns_transf_matrix_22  0.078194
_diffrn_reflns_transf_matrix_23  -0.025764
_diffrn_reflns_transf_matrix_31  -0.003680
_diffrn_reflns_transf_matrix_32  0.020119
_diffrn_reflns_transf_matrix_33  0.056981

_reflns_number_total             2573
_reflns_number_gt                1943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;
_computing_molecular_graphics    'PLATON (Spek,2003)'
_computing_publication_material  
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;


_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.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.3253P] 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_abs_structure_details 
;
 Flack x determined using 717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.043
_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
O1 O 0.64528(19) 0.6678(5) 0.2763(3) 0.0221(7) Uani 1 1 d . . . . .
O2 O 0.5739(2) 0.9437(5) 0.2159(3) 0.0242(8) Uani 1 1 d . . . . .
O4 O 0.61309(19) 0.8356(5) 0.6204(3) 0.0268(8) Uani 1 1 d . . . . .
N3 N 0.5068(2) 1.2145(6) 0.3718(3) 0.0186(8) Uani 1 1 d . . . . .
H3 H 0.5100 1.1785 0.2978 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5999(2) 0.8479(7) 0.3010(4) 0.0208(10) Uani 1 1 d . . . . .
C3 C 0.5880(3) 0.9072(8) 0.4207(4) 0.0181(10) Uani 1 1 d . . . . .
C4 C 0.6211(3) 0.7848(8) 0.5168(4) 0.0207(10) Uani 1 1 d . . . . .
C4A C 0.6665(2) 0.5907(7) 0.4826(4) 0.0179(10) Uani 1 1 d . . . . .
C5 C 0.7004(3) 0.4527(8) 0.5650(4) 0.0225(10) Uani 1 1 d . . . . .
H5 H 0.6943 0.4833 0.6456 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7425(3) 0.2729(8) 0.5313(4) 0.0232(10) Uani 1 1 d . . . . .
H6 H 0.7647 0.1797 0.5882 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7522(3) 0.2289(7) 0.4121(4) 0.0219(10) Uani 1 1 d . . . . .
H7 H 0.7811 0.1052 0.3885 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7200(3) 0.3635(7) 0.3292(4) 0.0197(10) Uani 1 1 d . . . . .
H8 H 0.7271 0.3348 0.2485 0.024 Uiso 1 1 calc R U . . .
C8A C 0.6771(3) 0.5417(7) 0.3658(4) 0.0176(10) Uani 1 1 d . . . . .
C31 C 0.5426(3) 1.0870(8) 0.4469(4) 0.0208(10) Uani 1 1 d . . . . .
H31 H 0.5368 1.1217 0.5271 0.025 Uiso 1 1 calc R U . . .
C311 C 0.4634(3) 1.4052(7) 0.3983(4) 0.0174(10) Uani 1 1 d . . . . .
C312 C 0.4428(3) 1.5379(8) 0.3055(4) 0.0192(10) Uani 1 1 d . . . . .
H312 H 0.4564 1.4980 0.2281 0.023 Uiso 1 1 calc R U . . .
C313 C 0.4023(3) 1.7282(8) 0.3262(4) 0.0217(10) Uani 1 1 d . . . . .
H313 H 0.3884 1.8193 0.2631 0.026 Uiso 1 1 calc R U . . .
C314 C 0.3823(3) 1.7849(7) 0.4401(4) 0.0208(10) Uani 1 1 d . . . . .
H314 H 0.3551 1.9157 0.4549 0.025 Uiso 1 1 calc R U . . .
C315 C 0.4020(3) 1.6513(8) 0.5310(4) 0.0199(10) Uani 1 1 d . . . . .
H315 H 0.3883 1.6912 0.6085 0.024 Uiso 1 1 calc R U . . .
C316 C 0.4416(3) 1.4589(7) 0.5113(4) 0.0202(10) Uani 1 1 d . . . . .
H316 H 0.4534 1.3654 0.5742 0.024 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 C2 1.384(5) . ?
O1 C8A 1.397(5) . ?
O2 C2 1.223(5) . ?
O4 C4 1.238(6) . ?
N3 C31 1.315(6) . ?
N3 C311 1.426(5) . ?
N3 H3 0.8800 . ?
C2 C3 1.436(6) . ?
C3 C31 1.386(6) . ?
C3 C4 1.449(7) . ?
C4 C4A 1.482(6) . ?
C4A C8A 1.386(6) . ?
C4A C5 1.397(6) . ?
C5 C6 1.379(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(7) . ?
C7 H7 0.9500 . ?
C8 C8A 1.387(6) . ?
C8 H8 0.9500 . ?
C31 H31 0.9500 . ?
C311 C316 1.387(6) . ?
C311 C312 1.393(6) . ?
C312 C313 1.386(7) . ?
C312 H312 0.9500 . ?
C313 C314 1.394(7) . ?
C313 H313 0.9500 . ?
C314 C315 1.376(7) . ?
C314 H314 0.9500 . ?
C315 C316 1.389(7) . ?
C315 H315 0.9500 . ?
C316 H316 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
C2 O1 C8A 120.9(4) . . ?
C31 N3 C311 126.5(4) . . ?
C31 N3 H3 116.8 . . ?
C311 N3 H3 116.8 . . ?
O2 C2 O1 115.2(4) . . ?
O2 C2 C3 126.0(4) . . ?
O1 C2 C3 118.7(4) . . ?
C31 C3 C2 119.5(4) . . ?
C31 C3 C4 117.9(4) . . ?
C2 C3 C4 122.6(4) . . ?
O4 C4 C3 123.7(4) . . ?
O4 C4 C4A 121.2(4) . . ?
C3 C4 C4A 115.1(4) . . ?
C8A C4A C5 117.8(4) . . ?
C8A C4A C4 120.0(4) . . ?
C5 C4A C4 122.1(4) . . ?
C6 C5 C4A 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 119.4(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 118.7(5) . . ?
C7 C8 H8 120.6 . . ?
C8A C8 H8 120.6 . . ?
C4A C8A C8 122.3(4) . . ?
C4A C8A O1 122.5(4) . . ?
C8 C8A O1 115.1(4) . . ?
N3 C31 C3 126.4(5) . . ?
N3 C31 H31 116.8 . . ?
C3 C31 H31 116.8 . . ?
C316 C311 C312 120.4(4) . . ?
C316 C311 N3 122.2(4) . . ?
C312 C311 N3 117.3(4) . . ?
C313 C312 C311 120.0(4) . . ?
C313 C312 H312 120.0 . . ?
C311 C312 H312 120.0 . . ?
C312 C313 C314 119.6(4) . . ?
C312 C313 H313 120.2 . . ?
C314 C313 H313 120.2 . . ?
C315 C314 C313 120.0(4) . . ?
C315 C314 H314 120.0 . . ?
C313 C314 H314 120.0 . . ?
C314 C315 C316 120.9(4) . . ?
C314 C315 H315 119.5 . . ?
C316 C315 H315 119.5 . . ?
C311 C316 C315 119.0(4) . . ?
C311 C316 H316 120.5 . . ?
C315 C316 H316 120.5 . . ?

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
C8A O1 C2 O2 -178.7(4) . . . . ?
C8A O1 C2 C3 1.9(6) . . . . ?
O2 C2 C3 C31 0.7(7) . . . . ?
O1 C2 C3 C31 -179.9(4) . . . . ?
O2 C2 C3 C4 -179.9(4) . . . . ?
O1 C2 C3 C4 -0.6(6) . . . . ?
C31 C3 C4 O4 -2.3(7) . . . . ?
C2 C3 C4 O4 178.3(4) . . . . ?
C31 C3 C4 C4A 178.0(4) . . . . ?
C2 C3 C4 C4A -1.4(6) . . . . ?
O4 C4 C4A C8A -177.6(4) . . . . ?
C3 C4 C4A C8A 2.1(6) . . . . ?
O4 C4 C4A C5 2.0(7) . . . . ?
C3 C4 C4A C5 -178.4(4) . . . . ?
C8A C4A C5 C6 -0.4(6) . . . . ?
C4 C4A C5 C6 -180.0(4) . . . . ?
C4A C5 C6 C7 0.6(7) . . . . ?
C5 C6 C7 C8 0.0(7) . . . . ?
C6 C7 C8 C8A -0.8(7) . . . . ?
C5 C4A C8A C8 -0.4(6) . . . . ?
C4 C4A C8A C8 179.2(4) . . . . ?
C5 C4A C8A O1 179.5(4) . . . . ?
C4 C4A C8A O1 -0.9(6) . . . . ?
C7 C8 C8A C4A 1.0(7) . . . . ?
C7 C8 C8A O1 -178.9(4) . . . . ?
C2 O1 C8A C4A -1.2(6) . . . . ?
C2 O1 C8A C8 178.8(4) . . . . ?
C311 N3 C31 C3 -176.8(4) . . . . ?
C2 C3 C31 N3 0.8(7) . . . . ?
C4 C3 C31 N3 -178.6(4) . . . . ?
C31 N3 C311 C316 -11.9(7) . . . . ?
C31 N3 C311 C312 168.5(4) . . . . ?
C316 C311 C312 C313 2.0(6) . . . . ?
N3 C311 C312 C313 -178.4(4) . . . . ?
C311 C312 C313 C314 -0.3(7) . . . . ?
C312 C313 C314 C315 -0.6(7) . . . . ?
C313 C314 C315 C316 -0.2(7) . . . . ?
C312 C311 C316 C315 -2.9(6) . . . . ?
N3 C311 C316 C315 177.6(4) . . . . ?
C314 C315 C316 C311 2.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O2 0.88 2.04 2.703(5) 131.3 .
C316 H316 O2 0.95 2.57 3.453(6) 155.4 2_675

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6




####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 932188'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_publcif_datablock.id            {fffe6069-cc8d-46bd-bfd2-5e38eb240432}

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   6.6795(2)
_cell_length_b                   7.3003(3)
_cell_length_c                   24.6020(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.306(7)
_cell_angle_gamma                90.00
_cell_volume                     1196.27(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13855
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b18 (Rigaku, 20112)
;


_exptl_special_details           ?

_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support MiTeGen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            15473
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2728
_reflns_number_gt                2464
_reflns_threshold_expression     >2sigma(I)

_diffrn_measurement_details      
;
scan:
	Number of images: 212
	           Slice: -32.0000 - 74.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -150.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 181
	           Slice: -68.5000 - 22.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 90.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 184
	           Slice: -69.0000 - 23.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -90.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 144
	           Slice: -82.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -90.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 30
	           Slice: 3.0000 - 18.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -60.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 236
	           Slice: -44.0000 - 74.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 30.0000
	             XTD: 44.9816
	          2theta: -15.9849
scan:
	Number of images: 137
	           Slice: -97.0000 - -28.5000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -36.0000
	             Phi: -90.0000
	             XTD: 44.9816
	          2theta: -15.9849

;
_diffrn_orient_matrix_UB_11      -0.138828
_diffrn_orient_matrix_UB_12      -0.053577
_diffrn_orient_matrix_UB_13      0.017913
_diffrn_orient_matrix_UB_21      0.042864
_diffrn_orient_matrix_UB_22      -0.123928
_diffrn_orient_matrix_UB_23      -0.038465
_diffrn_orient_matrix_UB_31      0.005636
_diffrn_orient_matrix_UB_32      -0.010154
_diffrn_orient_matrix_UB_33      0.038994
_diffrn_orient_matrix_type       d*Trek
_diffrn_reflns_transf_matrix_11  -0.138828
_diffrn_reflns_transf_matrix_12  -0.053577
_diffrn_reflns_transf_matrix_13  0.017913
_diffrn_reflns_transf_matrix_21  0.042864
_diffrn_reflns_transf_matrix_22  -0.123928
_diffrn_reflns_transf_matrix_23  -0.038465
_diffrn_reflns_transf_matrix_31  0.005636
_diffrn_reflns_transf_matrix_32  -0.010154
_diffrn_reflns_transf_matrix_33  0.038994




_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;
_computing_molecular_graphics    'PLATON (Spek,2009)'
_computing_publication_material  
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;

_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 > 2sigma(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)+(0.0473P)²+0.4205P] 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         2728
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.96968(10) 0.16970(11) 0.46208(3) 0.01970(18) Uani 1 1 d . . .
C2 C 0.95768(15) 0.26453(15) 0.50834(4) 0.0180(2) Uani 1 1 d . . .
H2 H 1.0803 0.3003 0.5275 0.022 Uiso 1 1 calc R . .
O3 O 0.98085(11) 0.44831(13) 0.60415(3) 0.0289(2) Uani 1 1 d . . .
N3 N 0.63925(12) 0.45520(12) 0.60561(3) 0.01538(19) Uani 1 1 d . . .
H3 H 0.5282 0.4248 0.5862 0.018 Uiso 1 1 calc R . .
C3 C 0.78555(14) 0.31362(14) 0.53004(4) 0.0150(2) Uani 1 1 d . . .
O4 O 0.42775(10) 0.30536(10) 0.51855(3) 0.01618(17) Uani 1 1 d . . .
C4 C 0.59241(14) 0.26473(13) 0.50195(4) 0.0137(2) Uani 1 1 d . . .
C5 C 0.43566(15) 0.09938(14) 0.42032(4) 0.0159(2) Uani 1 1 d . . .
H5 H 0.3063 0.1285 0.4315 0.019 Uiso 1 1 calc R . .
C6 C 0.45339(16) -0.00193(14) 0.37365(4) 0.0184(2) Uani 1 1 d . . .
H6 H 0.3364 -0.0424 0.3527 0.022 Uiso 1 1 calc R . .
C7 C 0.64363(17) -0.04529(15) 0.35709(4) 0.0212(2) Uani 1 1 d . . .
H7 H 0.6547 -0.1160 0.3250 0.025 Uiso 1 1 calc R . .
C8 C 0.81501(17) 0.01319(16) 0.38666(4) 0.0213(2) Uani 1 1 d . . .
H8 H 0.9441 -0.0157 0.3753 0.026 Uiso 1 1 calc R . .
C8A C 0.79424(15) 0.11569(14) 0.43361(4) 0.0167(2) Uani 1 1 d . . .
C311 C 0.61349(15) 0.54109(13) 0.65591(4) 0.0154(2) Uani 1 1 d . . .
C312 C 0.76868(15) 0.62605(14) 0.68775(4) 0.0175(2) Uani 1 1 d . . .
H312 H 0.9014 0.6266 0.6763 0.021 Uiso 1 1 calc R . .
C313 C 0.72697(16) 0.70976(15) 0.73638(4) 0.0199(2) Uani 1 1 d . . .
H313 H 0.8324 0.7677 0.7580 0.024 Uiso 1 1 calc R . .
C314 C 0.53409(17) 0.71032(16) 0.75387(4) 0.0219(2) Uani 1 1 d . . .
H314 H 0.5076 0.7669 0.7874 0.026 Uiso 1 1 calc R . .
C315 C 0.38016(17) 0.62679(16) 0.72164(4) 0.0219(2) Uani 1 1 d . . .
H315 H 0.2475 0.6272 0.7331 0.026 Uiso 1 1 calc R . .
C316 C 0.41876(16) 0.54285(15) 0.67292(4) 0.0182(2) Uani 1 1 d . . .
H316 H 0.3126 0.4865 0.6511 0.022 Uiso 1 1 calc R . .
C4A C 0.60762(15) 0.15983(14) 0.45147(4) 0.0145(2) Uani 1 1 d . . .
C31 C 0.81252(15) 0.41354(14) 0.58339(4) 0.0168(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
O1 C2 1.3395(13) . ?
O1 C8A 1.3770(12) . ?
C2 C3 1.3519(14) . ?
C2 H2 0.9500 . ?
O3 C31 1.2261(13) . ?
N3 C31 1.3512(13) . ?
N3 C311 1.4093(13) . ?
N3 H3 0.8800 . ?
C3 C4 1.4613(13) . ?
C3 C31 1.5005(14) . ?
O4 C4 1.2377(12) . ?
C4 C4A 1.4691(14) . ?
C5 C6 1.3782(14) . ?
C5 C4A 1.4033(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3996(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3773(16) . ?
C7 H7 0.9500 . ?
C8 C8A 1.3919(14) . ?
C8 H8 0.9500 . ?
C8A C4A 1.3904(14) . ?
C311 C316 1.3960(14) . ?
C311 C312 1.3968(14) . ?
C312 C313 1.3901(15) . ?
C312 H312 0.9500 . ?
C313 C314 1.3887(16) . ?
C313 H313 0.9500 . ?
C314 C315 1.3911(15) . ?
C314 H314 0.9500 . ?
C315 C316 1.3875(15) . ?
C315 H315 0.9500 . ?
C316 H316 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
C2 O1 C8A 118.51(8) . . ?
O1 C2 C3 125.41(9) . . ?
O1 C2 H2 117.3 . . ?
C3 C2 H2 117.3 . . ?
C31 N3 C311 128.32(9) . . ?
C31 N3 H3 115.8 . . ?
C311 N3 H3 115.8 . . ?
C2 C3 C4 119.69(9) . . ?
C2 C3 C31 115.12(9) . . ?
C4 C3 C31 125.18(9) . . ?
O4 C4 C3 124.07(9) . . ?
O4 C4 C4A 121.56(9) . . ?
C3 C4 C4A 114.36(9) . . ?
C6 C5 C4A 120.38(9) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.04(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.86(10) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 118.31(10) . . ?
C7 C8 H8 120.8 . . ?
C8A C8 H8 120.8 . . ?
O1 C8A C4A 121.45(9) . . ?
O1 C8A C8 116.24(9) . . ?
C4A C8A C8 122.31(10) . . ?
C316 C311 C312 119.78(9) . . ?
C316 C311 N3 116.44(9) . . ?
C312 C311 N3 123.75(9) . . ?
C313 C312 C311 119.32(10) . . ?
C313 C312 H312 120.3 . . ?
C311 C312 H312 120.3 . . ?
C314 C313 C312 121.24(10) . . ?
C314 C313 H313 119.4 . . ?
C312 C313 H313 119.4 . . ?
C313 C314 C315 119.03(10) . . ?
C313 C314 H314 120.5 . . ?
C315 C314 H314 120.5 . . ?
C316 C315 C314 120.57(10) . . ?
C316 C315 H315 119.7 . . ?
C314 C315 H315 119.7 . . ?
C315 C316 C311 120.06(10) . . ?
C315 C316 H316 120.0 . . ?
C311 C316 H316 120.0 . . ?
C8A C4A C5 118.10(9) . . ?
C8A C4A C4 120.57(9) . . ?
C5 C4A C4 121.33(9) . . ?
O3 C31 N3 124.85(10) . . ?
O3 C31 C3 120.74(9) . . ?
N3 C31 C3 114.39(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
C8A O1 C2 C3 -0.19(16) . . . . ?
O1 C2 C3 C4 -0.90(16) . . . . ?
O1 C2 C3 C31 177.81(9) . . . . ?
C2 C3 C4 O4 -179.32(10) . . . . ?
C31 C3 C4 O4 2.11(16) . . . . ?
C2 C3 C4 C4A 1.16(14) . . . . ?
C31 C3 C4 C4A -177.41(9) . . . . ?
C4A C5 C6 C7 0.06(15) . . . . ?
C5 C6 C7 C8 -0.48(16) . . . . ?
C6 C7 C8 C8A 0.34(17) . . . . ?
C2 O1 C8A C4A 0.95(15) . . . . ?
C2 O1 C8A C8 -178.27(9) . . . . ?
C7 C8 C8A O1 179.44(9) . . . . ?
C7 C8 C8A C4A 0.22(16) . . . . ?
C31 N3 C311 C316 -170.52(10) . . . . ?
C31 N3 C311 C312 11.18(16) . . . . ?
C316 C311 C312 C313 0.66(15) . . . . ?
N3 C311 C312 C313 178.90(9) . . . . ?
C311 C312 C313 C314 0.06(16) . . . . ?
C312 C313 C314 C315 -0.63(16) . . . . ?
C313 C314 C315 C316 0.49(17) . . . . ?
C314 C315 C316 C311 0.21(16) . . . . ?
C312 C311 C316 C315 -0.79(15) . . . . ?
N3 C311 C316 C315 -179.17(9) . . . . ?
O1 C8A C4A C5 -179.80(9) . . . . ?
C8 C8A C4A C5 -0.63(15) . . . . ?
O1 C8A C4A C4 -0.60(15) . . . . ?
C8 C8A C4A C4 178.58(9) . . . . ?
C6 C5 C4A C8A 0.48(15) . . . . ?
C6 C5 C4A C4 -178.72(9) . . . . ?
O4 C4 C4A C8A -179.98(9) . . . . ?
C3 C4 C4A C8A -0.45(14) . . . . ?
O4 C4 C4A C5 -0.80(15) . . . . ?
C3 C4 C4A C5 178.73(9) . . . . ?
C311 N3 C31 O3 -1.28(18) . . . . ?
C311 N3 C31 C3 177.24(9) . . . . ?
C2 C3 C31 O3 1.09(15) . . . . ?
C4 C3 C31 O3 179.72(10) . . . . ?
C2 C3 C31 N3 -177.50(9) . . . . ?
C4 C3 C31 N3 1.13(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O4 0.88 1.95 2.7064(11) 143 .
C2 H2 O3 0.95 2.31 2.7065(13) 104 .
C312 H312 O3 0.95 2.30 2.8914(13) 120 .
C2 H2 O4 0.95 2.35 3.1452(13) 141 1_655
C5 H5 O1 0.95 2.44 3.3893(13) 174 1_455
C316 H316 O3 0.95 2.44 3.3394(13) 159 1_455

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
