# 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_safin197red
_database_code_depnum_ccdc_archive 'CCDC 881637'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.45

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                   14.0292(9)
_cell_length_b                   5.0669(4)
_cell_length_c                   14.7229(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.433(7)
_cell_angle_gamma                90
_cell_volume                     1032.42(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4358
_cell_measurement_theta_min      2.7989
_cell_measurement_theta_max      25.4585

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '170 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2931
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2931
_reflns_number_gt                2690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;


_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+1.1142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C -0.0108(2) -0.6731(6) -0.1137(2) 0.0247(7) Uani 1 1 d . . . . .
H1 H -0.0513 -0.7992 -0.1489 0.030 Uiso 1 1 calc R U . . .
C2 C 0.0658(2) -0.5693(6) -0.1477(2) 0.0251(7) Uani 1 1 d . . . . .
H2 H 0.0782 -0.6247 -0.2063 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1268(2) -0.3810(6) -0.0973(2) 0.0242(6) Uani 1 1 d . . . . .
H3 H 0.1797 -0.3105 -0.1222 0.029 Uiso 1 1 calc R U . . .
C4 C 0.11006(18) -0.2987(5) -0.0122(2) 0.0211(6) Uani 1 1 d . . . . .
C5 C 0.03077(19) -0.4049(5) 0.0263(2) 0.0208(6) Uani 1 1 d . . . . .
N6 N 0.17151(16) -0.1221(4) 0.04458(17) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.22338(19) 0.0482(5) 0.00993(19) 0.0208(6) Uani 1 1 d . . . . .
H7 H 0.2182 0.0602 -0.0551 0.025 Uiso 1 1 calc R U . . .
C8 C 0.28968(18) 0.2229(5) 0.06776(19) 0.0188(6) Uani 1 1 d . . . . .
C9 C 0.34945(19) 0.3939(5) 0.02696(19) 0.0207(6) Uani 1 1 d . . . . .
H9 H 0.3477 0.3909 -0.0378 0.025 Uiso 1 1 calc R U . . .
C10 C 0.41042(19) 0.5653(5) 0.0807(2) 0.0213(6) Uani 1 1 d . . . . .
H10 H 0.4517 0.6777 0.0530 0.026 Uiso 1 1 calc R U . . .
C11 C 0.41207(18) 0.5753(5) 0.17585(19) 0.0203(6) Uani 1 1 d . . . . .
H11 H 0.4534 0.6972 0.2123 0.024 Uiso 1 1 calc R U . . .
C12 C 0.35388(19) 0.4086(5) 0.21730(19) 0.0202(6) Uani 1 1 d . . . . .
C13 C 0.29328(18) 0.2259(5) 0.16387(19) 0.0206(6) Uani 1 1 d . . . . .
O14 O 0.35101(15) 0.4035(4) 0.31017(14) 0.0279(5) Uani 1 1 d . . . . .
C15 C 0.4035(2) 0.6080(6) 0.3628(2) 0.0304(7) Uani 1 1 d . . . . .
H15A H 0.4726 0.5882 0.3605 0.046 Uiso 1 1 calc R U . . .
H15B H 0.3929 0.5965 0.4268 0.046 Uiso 1 1 calc R U . . .
H15C H 0.3812 0.7799 0.3372 0.046 Uiso 1 1 calc R U . . .
O16 O 0.23981(14) 0.0604(4) 0.20725(14) 0.0268(5) Uani 1 1 d . . . . .
H16 H 0.1872 0.0286 0.1727 0.040 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
C1 C2 1.364(4) . ?
C1 C5 1.416(4) 3_545 ?
C1 H1 0.9500 . ?
C2 C3 1.409(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 N6 1.417(3) . ?
C4 C5 1.434(4) . ?
C5 C1 1.416(4) 3_545 ?
C5 C5 1.434(5) 3_545 ?
N6 C7 1.287(4) . ?
C7 C8 1.454(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(4) . ?
C8 C13 1.408(4) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 O14 1.375(3) . ?
C12 C13 1.407(4) . ?
C13 O16 1.353(3) . ?
O14 C15 1.424(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O16 H16 0.8400 . ?

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 C5 120.7(3) . 3_545 ?
C2 C1 H1 119.7 . . ?
C5 C1 H1 119.7 3_545 . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 N6 123.4(2) . . ?
C3 C4 C5 120.4(3) . . ?
N6 C4 C5 116.1(2) . . ?
C1 C5 C4 122.4(3) 3_545 . ?
C1 C5 C5 119.2(3) 3_545 3_545 ?
C4 C5 C5 118.4(3) . 3_545 ?
C7 N6 C4 121.2(2) . . ?
N6 C7 C8 121.7(3) . . ?
N6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C13 119.8(3) . . ?
C9 C8 C7 119.6(3) . . ?
C13 C8 C7 120.6(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O14 C12 C11 124.4(2) . . ?
O14 C12 C13 115.5(2) . . ?
C11 C12 C13 120.1(2) . . ?
O16 C13 C12 118.3(2) . . ?
O16 C13 C8 122.5(2) . . ?
C12 C13 C8 119.2(2) . . ?
C12 O14 C15 115.5(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 O16 H16 109.5 . . ?

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
C5 C1 C2 C3 -0.3(4) 3_545 . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 N6 176.2(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C1 179.8(3) . . . 3_545 ?
N6 C4 C5 C1 3.8(4) . . . 3_545 ?
C3 C4 C5 C5 -0.8(5) . . . 3_545 ?
N6 C4 C5 C5 -176.8(3) . . . 3_545 ?
C3 C4 N6 C7 27.2(4) . . . . ?
C5 C4 N6 C7 -156.9(3) . . . . ?
C4 N6 C7 C8 -177.4(2) . . . . ?
N6 C7 C8 C9 175.9(2) . . . . ?
N6 C7 C8 C13 -5.3(4) . . . . ?
C13 C8 C9 C10 -0.7(4) . . . . ?
C7 C8 C9 C10 178.1(2) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 O14 179.7(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
O14 C12 C13 O16 -1.3(4) . . . . ?
C11 C12 C13 O16 177.9(2) . . . . ?
O14 C12 C13 C8 178.2(2) . . . . ?
C11 C12 C13 C8 -2.7(4) . . . . ?
C9 C8 C13 O16 -177.9(2) . . . . ?
C7 C8 C13 O16 3.3(4) . . . . ?
C9 C8 C13 C12 2.7(4) . . . . ?
C7 C8 C13 C12 -176.1(2) . . . . ?
C11 C12 O14 C15 7.9(4) . . . . ?
C13 C12 O14 C15 -173.0(2) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_safin197yel
_database_code_depnum_ccdc_archive 'CCDC 881638'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.46

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   'P 21/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                   6.7362(6)
_cell_length_b                   24.2039(15)
_cell_length_c                   6.8686(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.293(9)
_cell_angle_gamma                90.00
_cell_volume                     1036.17(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3241
_cell_measurement_theta_min      2.5194
_cell_measurement_theta_max      25.7756

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_min  0.96948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '132 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7641
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.83
_reflns_number_total             1954
_reflns_number_gt                1608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0475P)²+0.3181P] 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         1954
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.9200(3) 1.01230(6) 1.2285(2) 0.0234(4) Uani 1 1 d . . .
H1 H 0.9623 1.0343 1.3521 0.028 Uiso 1 1 calc R . .
C2 C 0.7510(3) 0.97675(7) 1.1836(2) 0.0258(4) Uani 1 1 d . . .
H2 H 0.6783 0.9740 1.2777 0.031 Uiso 1 1 calc R . .
C3 C 0.6829(3) 0.94423(6) 1.0008(2) 0.0240(4) Uani 1 1 d . . .
H3 H 0.5646 0.9199 0.9717 0.029 Uiso 1 1 calc R . .
C4 C 0.7870(2) 0.94763(6) 0.8644(2) 0.0210(3) Uani 1 1 d . . .
C5 C 0.9673(2) 0.98348(6) 0.9079(2) 0.0204(3) Uani 1 1 d . . .
N6 N 0.7297(2) 0.91433(5) 0.6819(2) 0.0233(3) Uani 1 1 d . . .
C7 C 0.5323(2) 0.90724(6) 0.5613(2) 0.0225(3) Uani 1 1 d . . .
H7 H 0.4238 0.9248 0.5958 0.027 Uiso 1 1 calc R . .
C8 C 0.4702(2) 0.87325(6) 0.3740(2) 0.0211(3) Uani 1 1 d . . .
C9 C 0.2540(2) 0.87040(6) 0.2367(3) 0.0248(4) Uani 1 1 d . . .
H9 H 0.1480 0.8896 0.2701 0.030 Uiso 1 1 calc R . .
C10 C 0.1952(3) 0.84026(7) 0.0552(3) 0.0260(4) Uani 1 1 d . . .
H10 H 0.0485 0.8385 -0.0364 0.031 Uiso 1 1 calc R . .
C11 C 0.3502(3) 0.81189(6) 0.0032(2) 0.0240(4) Uani 1 1 d . . .
H11 H 0.3081 0.7909 -0.1230 0.029 Uiso 1 1 calc R . .
C12 C 0.5637(2) 0.81445(6) 0.1353(2) 0.0216(4) Uani 1 1 d . . .
C13 C 0.6265(2) 0.84487(6) 0.3230(2) 0.0207(3) Uani 1 1 d . . .
O14 O 0.72913(17) 0.79033(5) 0.09830(17) 0.0277(3) Uani 1 1 d . . .
C15 C 0.6786(3) 0.76148(7) -0.0961(3) 0.0303(4) Uani 1 1 d . . .
H15A H 0.5787 0.7313 -0.1043 0.046 Uiso 1 1 calc R . .
H15B H 0.8103 0.7463 -0.1037 0.046 Uiso 1 1 calc R . .
H15C H 0.6120 0.7870 -0.2135 0.046 Uiso 1 1 calc R . .
O16 O 0.83740(17) 0.84656(5) 0.44538(18) 0.0283(3) Uani 1 1 d . . .
H16 H 0.8565 0.8671 0.5496 0.042 Uiso 1 1 calc R . .


_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 1.366(2) . ?
C1 C5 1.415(2) 3_777 ?
C1 H1 0.9500 . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(2) . ?
C3 H3 0.9500 . ?
C4 N6 1.415(2) . ?
C4 C5 1.429(2) . ?
C5 C1 1.415(2) 3_777 ?
C5 C5 1.418(3) 3_777 ?
N6 C7 1.2837(19) . ?
C7 C8 1.449(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(2) . ?
C8 C13 1.408(2) . ?
C9 C10 1.367(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 O14 1.3643(19) . ?
C12 C13 1.404(2) . ?
C13 O16 1.3494(18) . ?
O14 C15 1.4286(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O16 H16 0.8400 . ?

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 C5 120.43(14) . 3_777 ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 3_777 . ?
C1 C2 C3 121.11(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 120.01(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 N6 122.23(14) . . ?
C3 C4 C5 120.57(14) . . ?
N6 C4 C5 117.13(14) . . ?
C1 C5 C5 119.14(17) 3_777 3_777 ?
C1 C5 C4 122.13(14) 3_777 . ?
C5 C5 C4 118.72(18) 3_777 . ?
C7 N6 C4 121.03(13) . . ?
N6 C7 C8 121.87(14) . . ?
N6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C13 119.45(14) . . ?
C9 C8 C7 120.03(14) . . ?
C13 C8 C7 120.46(13) . . ?
C10 C9 C8 120.42(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.44(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.05(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O14 C12 C11 125.40(14) . . ?
O14 C12 C13 114.39(13) . . ?
C11 C12 C13 120.19(14) . . ?
O16 C13 C12 117.84(13) . . ?
O16 C13 C8 122.71(13) . . ?
C12 C13 C8 119.43(14) . . ?
C12 O14 C15 117.46(12) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 O16 H16 109.5 . . ?

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
C5 C1 C2 C3 -0.9(2) 3_777 . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 N6 177.68(14) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C1 179.45(14) . . . 3_777 ?
N6 C4 C5 C1 2.6(2) . . . 3_777 ?
C3 C4 C5 C5 -1.7(2) . . . 3_777 ?
N6 C4 C5 C5 -178.53(16) . . . 3_777 ?
C3 C4 N6 C7 44.7(2) . . . . ?
C5 C4 N6 C7 -138.50(15) . . . . ?
C4 N6 C7 C8 -179.90(13) . . . . ?
N6 C7 C8 C9 -174.49(14) . . . . ?
N6 C7 C8 C13 2.6(2) . . . . ?
C13 C8 C9 C10 0.2(2) . . . . ?
C7 C8 C9 C10 177.29(14) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 O14 -177.62(15) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
O14 C12 C13 O16 -0.7(2) . . . . ?
C11 C12 C13 O16 -179.25(14) . . . . ?
O14 C12 C13 C8 177.73(13) . . . . ?
C11 C12 C13 C8 -0.8(2) . . . . ?
C9 C8 C13 O16 178.74(14) . . . . ?
C7 C8 C13 O16 1.6(2) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C7 C8 C13 C12 -176.77(14) . . . . ?
C11 C12 O14 C15 2.1(2) . . . . ?
C13 C12 O14 C15 -176.32(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
