# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_Pyr-PMDA
_database_code_depnum_ccdc_archive 'CCDC 1546841'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_date             2016-11-17
_audit_creation_method           
'generated by ACTA instruction via SHELXL-2014/7'
_shelx_SHELXL_version_number     2014/7
#-----------------------------------------------------------------------------#


_chemical_formula_moiety         'C16 H10, C10 H2 O6'
_chemical_formula_sum            'C26 H12 O6'
_chemical_formula_weight         420.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.268(6)
_cell_length_b                   9.350(7)
_cell_length_c                   13.757(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.710(11)
_cell_angle_gamma                90
_cell_volume                     933.8(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2326
_cell_measurement_theta_min      2.8059
_cell_measurement_theta_max      27.4623

_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             432
_exptl_special_details           ?

_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9402
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.710747
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       ω
_diffrn_measurement_device       'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC11 with Saturn 724+ CCD'
_diffrn_measurement_device_details 'AFC11 (Right): Eulerian 3 circle'
_diffrn_detector_area_resol_mean 7.111
_diffrn_ambient_temperature      200(2)
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_source_current           24.0000


_diffrn_reflns_number            9337
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994

_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 54.9328
	          2theta: -25.3494
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 54.9328
	          2theta: -25.3494
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 54.9328
	          2theta: -25.3494

;


_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------

_reflns_number_total             2132
_reflns_number_gt                1899
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2132
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035

_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.
;

#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93092(17) 0.12462(14) -0.03571(10) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.86448(19) 0.27342(16) -0.05156(11) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.89686(15) 0.34692(11) 0.03584(8) 0.0468(3) Uani 1 1 d . . . . .
C3 C 0.97700(19) 0.25693(16) 0.10614(12) 0.0412(4) Uani 1 1 d . . . . .
C4 C 0.99853(17) 0.11434(14) 0.06022(10) 0.0316(3) Uani 1 1 d . . . . .
C5 C 0.92940(18) 0.01105(15) -0.10004(10) 0.0342(3) Uani 1 1 d . . . . .
H5A H 0.885(2) 0.0192(16) -0.1668(12) 0.043(4) Uiso 1 1 d . . . . .
O2 O 0.79505(17) 0.32988(13) -0.12134(9) 0.0575(4) Uani 1 1 d . . . . .
O3 O 1.01545(17) 0.29741(13) 0.18643(9) 0.0576(4) Uani 1 1 d . . . . .
C6 C 0.46718(16) 0.07008(13) -0.01115(9) 0.0298(3) Uani 1 1 d . . . . .
C7 C 0.47761(19) 0.17779(14) 0.06200(11) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.4090(2) 0.31447(17) 0.03830(16) 0.0548(5) Uani 1 1 d . . . . .
H8A H 0.417(3) 0.385(2) 0.0904(15) 0.068(6) Uiso 1 1 d . . . . .
C9 C 0.3346(2) 0.34376(18) -0.05265(19) 0.0629(6) Uani 1 1 d . . . . .
H9A H 0.288(3) 0.438(2) -0.0690(15) 0.078(6) Uiso 1 1 d . . . . .
C10 C 0.3242(2) 0.2407(2) -0.12447(15) 0.0557(5) Uani 1 1 d . . . . .
H10A H 0.270(3) 0.258(2) -0.1885(15) 0.067(6) Uiso 1 1 d . . . . .
C11 C 0.39036(18) 0.10186(16) -0.10540(11) 0.0387(3) Uani 1 1 d . . . . .
C12 C 0.5572(2) 0.1418(2) 0.15604(12) 0.0489(4) Uani 1 1 d . . . . .
H12A H 0.568(2) 0.214(2) 0.2053(13) 0.057(5) Uiso 1 1 d . . . . .
C13 C 0.6197(2) 0.0099(2) 0.17658(11) 0.0485(4) Uani 1 1 d . . . . .
H13A H 0.676(3) -0.012(2) 0.2403(14) 0.063(5) Uiso 1 1 d . . . . .




#--------------MOLECULAR GEOMETRY------------------

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.382(2) . ?
C1 C4 1.390(2) . ?
C1 C2 1.485(2) . ?
C2 O2 1.1871(19) . ?
C2 O1 1.395(2) . ?
O1 C3 1.389(2) . ?
C3 O3 1.188(2) . ?
C3 C4 1.487(2) . ?
C4 C5 1.386(2) 3_755 ?
C5 C4 1.386(2) 3_755 ?
C5 H5A 0.961(16) . ?
C6 C11 1.419(2) . ?
C6 C6 1.423(3) 3_655 ?
C6 C7 1.423(2) . ?
C7 C8 1.404(2) . ?
C7 C12 1.432(3) . ?
C8 C9 1.367(3) . ?
C8 H8A 0.97(2) . ?
C9 C10 1.380(3) . ?
C9 H9A 0.97(2) . ?
C10 C11 1.404(2) . ?
C10 H10A 0.96(2) . ?
C11 C13 1.431(2) 3_655 ?
C12 C13 1.340(3) . ?
C12 H12A 0.960(19) . ?
C13 C11 1.431(2) 3_655 ?
C13 H13A 0.970(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C4 123.14(13) . . ?
C5 C1 C2 129.27(14) . . ?
C4 C1 C2 107.58(12) . . ?
O2 C2 O1 121.72(15) . . ?
O2 C2 C1 131.15(15) . . ?
O1 C2 C1 107.13(13) . . ?
C3 O1 C2 110.47(12) . . ?
O3 C3 O1 121.78(15) . . ?
O3 C3 C4 130.97(15) . . ?
O1 C3 C4 107.25(13) . . ?
C5 C4 C1 122.94(12) 3_755 . ?
C5 C4 C3 129.49(14) 3_755 . ?
C1 C4 C3 107.57(13) . . ?
C1 C5 C4 113.92(13) . 3_755 ?
C1 C5 H5A 122.9(9) . . ?
C4 C5 H5A 123.2(9) 3_755 . ?
C11 C6 C6 120.22(15) . 3_655 ?
C11 C6 C7 120.23(14) . . ?
C6 C6 C7 119.54(16) 3_655 . ?
C8 C7 C6 118.25(16) . . ?
C8 C7 C12 123.18(15) . . ?
C6 C7 C12 118.57(14) . . ?
C9 C8 C7 121.03(16) . . ?
C9 C8 H8A 123.0(13) . . ?
C7 C8 H8A 116.0(13) . . ?
C8 C9 C10 121.40(16) . . ?
C8 C9 H9A 120.9(13) . . ?
C10 C9 H9A 117.7(13) . . ?
C9 C10 C11 120.35(18) . . ?
C9 C10 H10A 122.9(12) . . ?
C11 C10 H10A 116.8(12) . . ?
C10 C11 C6 118.73(15) . . ?
C10 C11 C13 122.72(16) . 3_655 ?
C6 C11 C13 118.54(14) . 3_655 ?
C13 C12 C7 121.69(14) . . ?
C13 C12 H12A 119.1(11) . . ?
C7 C12 H12A 119.2(11) . . ?
C12 C13 C11 121.43(15) . 3_655 ?
C12 C13 H13A 120.4(11) . . ?
C11 C13 H13A 118.1(11) 3_655 . ?

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
C5 C1 C2 O2 0.3(3) . . . . ?
C4 C1 C2 O2 -179.20(15) . . . . ?
C5 C1 C2 O1 -179.97(13) . . . . ?
C4 C1 C2 O1 0.55(14) . . . . ?
O2 C2 O1 C3 179.31(14) . . . . ?
C1 C2 O1 C3 -0.47(15) . . . . ?
C2 O1 C3 O3 -179.58(13) . . . . ?
C2 O1 C3 C4 0.22(15) . . . . ?
C5 C1 C4 C5 0.0(2) . . . 3_755 ?
C2 C1 C4 C5 179.50(12) . . . 3_755 ?
C5 C1 C4 C3 -179.93(12) . . . . ?
C2 C1 C4 C3 -0.41(14) . . . . ?
O3 C3 C4 C5 0.0(3) . . . 3_755 ?
O1 C3 C4 C5 -179.78(13) . . . 3_755 ?
O3 C3 C4 C1 179.92(15) . . . . ?
O1 C3 C4 C1 0.13(14) . . . . ?
C4 C1 C5 C4 0.0(2) . . . 3_755 ?
C2 C1 C5 C4 -179.39(12) . . . 3_755 ?
C11 C6 C7 C8 0.45(19) . . . . ?
C6 C6 C7 C8 -178.98(14) 3_655 . . . ?
C11 C6 C7 C12 -179.60(12) . . . . ?
C6 C6 C7 C12 1.0(2) 3_655 . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C12 C7 C8 C9 179.87(14) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C9 C10 C11 C13 178.90(14) . . . 3_655 ?
C6 C6 C11 C10 178.99(14) 3_655 . . . ?
C7 C6 C11 C10 -0.43(19) . . . . ?
C6 C6 C11 C13 0.2(2) 3_655 . . 3_655 ?
C7 C6 C11 C13 -179.23(12) . . . 3_655 ?
C8 C7 C12 C13 179.33(14) . . . . ?
C6 C7 C12 C13 -0.6(2) . . . . ?
C7 C12 C13 C11 -0.2(2) . . . 3_655 ?


####################################################################### 
# 
# 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_Pyr-DMPMDI
_database_code_depnum_ccdc_archive 'CCDC 1546840'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_date             2016-12-16
_audit_creation_method           
'generated by ACTA instruction via SHELXL-2014/7'
_shelx_SHELXL_version_number     2014/7
#-----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H10, C12 H8 N2 O4'
_chemical_formula_sum            'C28 H18 N2 O4'
_chemical_formula_weight         446.44

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                   12.019(6)
_cell_length_b                   20.022(9)
_cell_length_c                   8.703(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.990(5)
_cell_angle_gamma                90
_cell_volume                     2062.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2610
_cell_measurement_theta_min      3.1290
_cell_measurement_theta_max      27.4700

_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             928
_exptl_special_details           ?

_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9536
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.710747
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       ω
_diffrn_measurement_device       'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC11 with Saturn 724+ CCD'
_diffrn_measurement_device_details 'AFC11 (Right): Eulerian 3 circle'
_diffrn_detector_area_resol_mean 7.111
_diffrn_ambient_temperature      200(2)
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_source_current           24.0000


_diffrn_reflns_number            10514
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991

_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 54.9222
	          2theta: -25.3555
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 54.9222
	          2theta: -25.3555
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 54.9222
	          2theta: -25.3555

;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------

_reflns_number_total             2344
_reflns_number_gt                1931
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.3776P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.035

_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.
;


#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 0.04147(10) 0.2500 0.0414(5) Uani 1 2 d S T P . .
H1A H 0.5000 -0.0077(12) 0.2500 0.048(6) Uiso 1 2 d S . P . .
C2 C 0.54713(11) 0.07575(7) 0.13931(16) 0.0380(3) Uani 1 1 d . . . . .
H2A H 0.5804(13) 0.0524(9) 0.0607(18) 0.048(4) Uiso 1 1 d . . . . .
C3 C 0.54861(9) 0.14556(6) 0.13656(14) 0.0295(3) Uani 1 1 d . . . . .
C4 C 0.59747(11) 0.18309(8) 0.02437(16) 0.0363(3) Uani 1 1 d . . . . .
H4A H 0.6307(12) 0.1581(9) -0.0554(18) 0.048(4) Uiso 1 1 d . . . . .
C5 C 0.59749(11) 0.25042(7) 0.02490(15) 0.0353(3) Uani 1 1 d . . . . .
H5A H 0.6307(13) 0.2758(8) -0.0522(18) 0.049(4) Uiso 1 1 d . . . . .
C6 C 0.54869(9) 0.28772(6) 0.13707(13) 0.0278(3) Uani 1 1 d . . . . .
C7 C 0.54744(10) 0.35757(7) 0.13899(15) 0.0339(3) Uani 1 1 d . . . . .
H7A H 0.5807(13) 0.3820(8) 0.0620(18) 0.048(4) Uiso 1 1 d . . . . .
C8 C 0.5000 0.39160(10) 0.2500 0.0376(4) Uani 1 2 d S T P . .
H8A H 0.5000 0.4386(11) 0.2500 0.039(5) Uiso 1 2 d S . P . .
C9 C 0.5000 0.18102(8) 0.2500 0.0246(3) Uani 1 2 d S T P . .
C10 C 0.5000 0.25226(8) 0.2500 0.0236(3) Uani 1 2 d S T P . .
N1 N 0.22511(9) 0.08401(5) 0.03553(12) 0.0320(3) Uani 1 1 d . . . . .
C11 C 0.20557(16) 0.01249(7) 0.0429(2) 0.0465(4) Uani 1 1 d . . . . .
H11A H 0.1999(19) -0.0071(11) -0.059(3) 0.090(7) Uiso 1 1 d . . . . .
H11B H 0.2635(18) -0.0090(11) 0.121(3) 0.079(6) Uiso 1 1 d . . . . .
H11C H 0.127(2) 0.0056(13) 0.075(3) 0.113(8) Uiso 1 1 d . . . . .
C12 C 0.18600(10) 0.13005(6) 0.13354(14) 0.0302(3) Uani 1 1 d . . . . .
O1 O 0.13921(8) 0.11633(5) 0.24130(11) 0.0431(3) Uani 1 1 d . . . . .
C13 C 0.21422(9) 0.19710(6) 0.07640(13) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.27093(9) 0.18768(6) -0.04798(13) 0.0250(3) Uani 1 1 d . . . . .
C15 C 0.27859(10) 0.11448(6) -0.07535(14) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.32065(8) 0.08593(5) -0.17340(11) 0.0404(3) Uani 1 1 d . . . . .
C16 C 0.19098(10) 0.26005(6) 0.12866(14) 0.0264(3) Uani 1 1 d . . . . .
H16A H 0.1507(11) 0.2668(7) 0.2147(16) 0.030(3) Uiso 1 1 d . . . . .



#--------------MOLECULAR GEOMETRY------------------

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3817(18) 2_655 ?
C1 C2 1.3818(18) . ?
C2 C3 1.398(2) . ?
C3 C9 1.4213(15) . ?
C3 C4 1.4358(19) . ?
C4 C5 1.348(2) . ?
C5 C6 1.4329(18) . ?
C6 C7 1.3988(19) . ?
C6 C10 1.4184(14) . ?
C7 C8 1.3834(17) . ?
C8 C7 1.3834(17) 2_655 ?
C9 C3 1.4213(15) 2_655 ?
C9 C10 1.426(2) . ?
C10 C6 1.4184(14) 2_655 ?
N1 C15 1.3899(17) . ?
N1 C12 1.3919(16) . ?
N1 C11 1.4543(18) . ?
C12 O1 1.2058(16) . ?
C12 C13 1.4911(17) . ?
C13 C16 1.3846(17) . ?
C13 C14 1.3885(17) . ?
C14 C16 1.3819(17) 7 ?
C14 C15 1.4902(17) . ?
C15 O2 1.2084(15) . ?
C16 C14 1.3819(17) 7 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 120.44(18) 2_655 . ?
C1 C2 C3 121.09(14) . . ?
C2 C3 C9 118.66(12) . . ?
C2 C3 C4 122.87(12) . . ?
C9 C3 C4 118.48(12) . . ?
C5 C4 C3 121.39(12) . . ?
C4 C5 C6 121.58(12) . . ?
C7 C6 C10 119.05(12) . . ?
C7 C6 C5 122.39(12) . . ?
C10 C6 C5 118.56(12) . . ?
C8 C7 C6 120.49(13) . . ?
C7 C8 C7 120.98(18) . 2_655 ?
C3 C9 C3 120.06(16) 2_655 . ?
C3 C9 C10 119.97(8) 2_655 . ?
C3 C9 C10 119.97(8) . . ?
C6 C10 C6 119.93(15) . 2_655 ?
C6 C10 C9 120.04(8) . . ?
C6 C10 C9 120.03(8) 2_655 . ?
C15 N1 C12 112.38(10) . . ?
C15 N1 C11 124.11(12) . . ?
C12 N1 C11 123.41(12) . . ?
O1 C12 N1 125.33(12) . . ?
O1 C12 C13 128.92(12) . . ?
N1 C12 C13 105.75(10) . . ?
C16 C13 C14 122.28(11) . . ?
C16 C13 C12 129.75(12) . . ?
C14 C13 C12 107.96(11) . . ?
C16 C14 C13 122.94(11) 7 . ?
C16 C14 C15 128.95(11) 7 . ?
C13 C14 C15 108.10(11) . . ?
O2 C15 N1 125.67(12) . . ?
O2 C15 C14 128.55(12) . . ?
N1 C15 C14 105.78(10) . . ?
C14 C16 C13 114.77(11) 7 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 0.14(8) 2_655 . . . ?
C1 C2 C3 C9 -0.28(16) . . . . ?
C1 C2 C3 C4 179.51(10) . . . . ?
C2 C3 C4 C5 179.98(12) . . . . ?
C9 C3 C4 C5 -0.22(17) . . . . ?
C3 C4 C5 C6 -0.10(19) . . . . ?
C4 C5 C6 C7 -179.69(12) . . . . ?
C4 C5 C6 C10 0.31(17) . . . . ?
C10 C6 C7 C8 0.38(15) . . . . ?
C5 C6 C7 C8 -179.62(10) . . . . ?
C6 C7 C8 C7 -0.19(8) . . . 2_655 ?
C2 C3 C9 C3 0.13(8) . . . 2_655 ?
C4 C3 C9 C3 -179.67(11) . . . 2_655 ?
C2 C3 C9 C10 -179.87(8) . . . . ?
C4 C3 C9 C10 0.34(11) . . . . ?
C7 C6 C10 C6 -0.19(8) . . . 2_655 ?
C5 C6 C10 C6 179.81(11) . . . 2_655 ?
C7 C6 C10 C9 179.81(8) . . . . ?
C5 C6 C10 C9 -0.19(11) . . . . ?
C3 C9 C10 C6 179.87(7) 2_655 . . . ?
C3 C9 C10 C6 -0.13(7) . . . . ?
C3 C9 C10 C6 -0.13(7) 2_655 . . 2_655 ?
C3 C9 C10 C6 179.87(7) . . . 2_655 ?
C15 N1 C12 O1 -178.15(11) . . . . ?
C11 N1 C12 O1 5.5(2) . . . . ?
C15 N1 C12 C13 1.89(13) . . . . ?
C11 N1 C12 C13 -174.50(12) . . . . ?
O1 C12 C13 C16 -2.3(2) . . . . ?
N1 C12 C13 C16 177.64(11) . . . . ?
O1 C12 C13 C14 178.29(12) . . . . ?
N1 C12 C13 C14 -1.75(12) . . . . ?
C16 C13 C14 C16 0.33(19) . . . 7 ?
C12 C13 C14 C16 179.78(10) . . . 7 ?
C16 C13 C14 C15 -178.45(10) . . . . ?
C12 C13 C14 C15 1.01(12) . . . . ?
C12 N1 C15 O2 179.46(11) . . . . ?
C11 N1 C15 O2 -4.2(2) . . . . ?
C12 N1 C15 C14 -1.29(13) . . . . ?
C11 N1 C15 C14 175.07(12) . . . . ?
C16 C14 C15 O2 0.6(2) 7 . . . ?
C13 C14 C15 O2 179.32(12) . . . . ?
C16 C14 C15 N1 -178.57(11) 7 . . . ?
C13 C14 C15 N1 0.11(12) . . . . ?
C14 C13 C16 C14 -0.31(18) . . . 7 ?
C12 C13 C16 C14 -179.63(11) . . . 7 ?

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
C11 H11B O2 0.98(2) 2.37(2) 3.272(2) 152.1(17) 6_556


