# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1949821'
loop_
_audit_author_name
_audit_author_address
'Sunil Varughese'
;CSIR, NIIST
India
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   20.236(12)
_cell_length_b                   5.793(3)
_cell_length_c                   14.906(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Colorless
_exptl_crystal_colour            Block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Section A 1995, 51, 33-38
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14846
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.395
_diffrn_reflns_theta_max         27.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3851
_reflns_number_gt                3281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    0.956

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0597P)²] 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 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   2.3(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3851
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
O17 O -0.05929(11) 1.3034(3) 0.23439(16) 0.0646(6) Uani 1 1 d . . . . .
N1 N -0.01443(10) 0.9841(4) 0.08225(15) 0.0472(5) Uani 1 1 d . . . . .
C2 C 0.03880(12) 1.0222(4) 0.1466(2) 0.0481(6) Uani 1 1 d . . . . .
H2 H 0.0479 1.1846 0.1602 0.058 Uiso 1 1 calc R U . . .
C3 C -0.02758(12) 0.9352(4) 0.17900(18) 0.0450(6) Uani 1 1 d . . . . .
H3 H -0.0293 0.7716 0.1956 0.054 Uiso 1 1 calc R U . . .
C4 C -0.04376(12) 1.1878(4) 0.03934(17) 0.0465(6) Uani 1 1 d . . . . .
H4 H -0.0393 1.3197 0.0801 0.056 Uiso 1 1 calc R U . . .
C5 C -0.11636(14) 1.1538(6) 0.0183(2) 0.0657(8) Uani 1 1 d . . . . .
H5A H -0.1406 1.1271 0.0734 0.079 Uiso 1 1 calc R U . . .
H5B H -0.1218 1.0196 -0.0199 0.079 Uiso 1 1 calc R U . . .
C6 C -0.14366(16) 1.3670(7) -0.0289(2) 0.0782(10) Uani 1 1 d . . . . .
H6A H -0.1896 1.3408 -0.0442 0.094 Uiso 1 1 calc R U . . .
H6B H -0.1417 1.4976 0.0117 0.094 Uiso 1 1 calc R U . . .
C7 C -0.10536(18) 1.4240(7) -0.1136(2) 0.0840(11) Uani 1 1 d . . . . .
H7A H -0.1119 1.3023 -0.1574 0.101 Uiso 1 1 calc R U . . .
H7B H -0.1220 1.5667 -0.1390 0.101 Uiso 1 1 calc R U . . .
C8 C -0.03244(16) 1.4492(6) -0.0942(3) 0.0742(9) Uani 1 1 d . . . . .
H8A H -0.0254 1.5853 -0.0576 0.089 Uiso 1 1 calc R U . . .
H8B H -0.0088 1.4703 -0.1502 0.089 Uiso 1 1 calc R U . . .
C9 C -0.00507(15) 1.2384(5) -0.0457(2) 0.0595(7) Uani 1 1 d . . . . .
H9A H -0.0071 1.1055 -0.0852 0.071 Uiso 1 1 calc R U . . .
H9B H 0.0409 1.2650 -0.0305 0.071 Uiso 1 1 calc R U . . .
C10 C 0.09837(11) 0.8703(4) 0.14363(18) 0.0453(6) Uani 1 1 d . . . . .
C11 C 0.09758(13) 0.6607(5) 0.09894(19) 0.0531(7) Uani 1 1 d . . . . .
H11 H 0.0591 0.6120 0.0707 0.064 Uiso 1 1 calc R U . . .
C12 C 0.15279(14) 0.5243(5) 0.0958(2) 0.0606(7) Uani 1 1 d . . . . .
H12 H 0.1516 0.3846 0.0652 0.073 Uiso 1 1 calc R U . . .
C13 C 0.21035(13) 0.5931(6) 0.1380(2) 0.0672(8) Uani 1 1 d . . . . .
H13 H 0.2476 0.4994 0.1360 0.081 Uiso 1 1 calc R U . . .
C14 C 0.21230(14) 0.7995(6) 0.1827(2) 0.0655(8) Uani 1 1 d . . . . .
H14 H 0.2510 0.8460 0.2110 0.079 Uiso 1 1 calc R U . . .
C15 C 0.15656(13) 0.9398(5) 0.1858(2) 0.0559(7) Uani 1 1 d . . . . .
H15 H 0.1581 1.0801 0.2161 0.067 Uiso 1 1 calc R U . . .
C16 C -0.06864(12) 1.0934(4) 0.23506(18) 0.0460(5) Uani 1 1 d . . . . .
C18 C -0.12112(11) 0.9917(4) 0.29364(17) 0.0419(5) Uani 1 1 d . . . . .
C19 C -0.14135(13) 1.1157(5) 0.36862(18) 0.0511(6) Uani 1 1 d . . . . .
H19 H -0.1212 1.2560 0.3819 0.061 Uiso 1 1 calc R U . . .
C20 C -0.19071(14) 1.0337(5) 0.4235(2) 0.0608(7) Uani 1 1 d . . . . .
H20 H -0.2031 1.1169 0.4741 0.073 Uiso 1 1 calc R U . . .
C21 C -0.22169(15) 0.8295(6) 0.4036(2) 0.0650(8) Uani 1 1 d . . . . .
H21 H -0.2558 0.7763 0.4399 0.078 Uiso 1 1 calc R U . . .
C22 C -0.20231(16) 0.7027(5) 0.3297(2) 0.0641(8) Uani 1 1 d . . . . .
H22 H -0.2233 0.5642 0.3161 0.077 Uiso 1 1 calc R U . . .
C23 C -0.15142(14) 0.7829(5) 0.27573(18) 0.0533(6) Uani 1 1 d . . . . .
H23 H -0.1375 0.6953 0.2270 0.064 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
O17 C16 1.231(3) . ?
N1 C2 1.459(3) . ?
N1 C4 1.468(3) . ?
N1 C3 1.494(4) . ?
C2 C10 1.493(4) . ?
C2 C3 1.514(3) . ?
C3 C16 1.493(3) . ?
C4 C5 1.515(4) . ?
C4 C9 1.518(4) . ?
C5 C6 1.525(5) . ?
C6 C7 1.518(5) . ?
C7 C8 1.510(5) . ?
C8 C9 1.524(4) . ?
C10 C11 1.385(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.369(5) . ?
C14 C15 1.391(4) . ?
C16 C18 1.496(3) . ?
C18 C23 1.382(3) . ?
C18 C19 1.390(4) . ?
C19 C20 1.375(4) . ?
C20 C21 1.372(4) . ?
C21 C22 1.381(5) . ?
C22 C23 1.387(4) . ?

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 N1 C4 117.60(19) . . ?
C2 N1 C3 61.67(17) . . ?
C4 N1 C3 120.1(2) . . ?
N1 C2 C10 119.2(2) . . ?
N1 C2 C3 60.28(17) . . ?
C10 C2 C3 122.0(2) . . ?
C16 C3 N1 121.6(2) . . ?
C16 C3 C2 117.9(2) . . ?
N1 C3 C2 58.04(16) . . ?
N1 C4 C5 112.2(2) . . ?
N1 C4 C9 108.1(2) . . ?
C5 C4 C9 110.6(2) . . ?
C4 C5 C6 110.0(3) . . ?
C7 C6 C5 112.0(3) . . ?
C8 C7 C6 111.2(3) . . ?
C7 C8 C9 111.6(3) . . ?
C4 C9 C8 111.3(2) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C2 121.4(2) . . ?
C15 C10 C2 119.9(2) . . ?
C12 C11 C10 120.8(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 119.8(3) . . ?
C13 C14 C15 120.2(3) . . ?
C14 C15 C10 120.1(3) . . ?
O17 C16 C3 121.1(2) . . ?
O17 C16 C18 120.2(2) . . ?
C3 C16 C18 118.7(2) . . ?
C23 C18 C19 118.5(2) . . ?
C23 C18 C16 123.1(2) . . ?
C19 C18 C16 118.3(2) . . ?
C20 C19 C18 120.9(3) . . ?
C21 C20 C19 120.1(3) . . ?
C20 C21 C22 120.1(3) . . ?
C21 C22 C23 119.7(3) . . ?
C18 C23 C22 120.7(3) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1949823'
loop_
_audit_author_name
_audit_author_address
'Sunil Varughese'
;CSIR, NIIST
India
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H10.50 N10.50 O10.50'
_chemical_formula_weight         451.79

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.842(4)
_cell_length_b                   9.949(4)
_cell_length_c                   11.468(5)
_cell_angle_alpha                100.231(6)
_cell_angle_beta                 105.032(6)
_cell_angle_gamma                95.125(4)
_cell_volume                     1056.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9516
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4624
_reflns_number_gt                2107
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1318P)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         4624
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.658
_refine_ls_restrained_S_all      0.658
_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 0.4680(2) 0.1396(2) 0.12738(17) 0.0680(6) Uani 1 1 d . . . . .
N2 N 0.2006(2) -0.0870(2) 0.04626(17) 0.0517(5) Uani 1 1 d . . . . .
C7AA C 0.3061(2) -0.2991(3) 0.09645(19) 0.0469(6) Uani 1 1 d . . . . .
C9AA C 0.3244(3) -0.1570(3) 0.0747(2) 0.0497(6) Uani 1 1 d . . . . .
H9AA H 0.395730 -0.138168 0.031683 0.060 Uiso 1 1 calc R U . . .
C2BA C -0.0631(3) -0.2533(3) -0.3252(2) 0.0550(6) Uani 1 1 d . . . . .
H2BA H -0.146774 -0.313738 -0.342034 0.066 Uiso 1 1 calc R U . . .
C4BA C 0.4189(3) -0.3745(3) 0.1070(2) 0.0521(6) Uani 1 1 d . . . . .
H4BA H 0.504328 -0.336266 0.097976 0.062 Uiso 1 1 calc R U . . .
C4AA C -0.0738(2) -0.3065(3) -0.5503(2) 0.0492(6) Uani 1 1 d . . . . .
C1 C 0.1805(3) -0.3584(3) 0.1093(2) 0.0556(6) Uani 1 1 d . . . . .
H1 H 0.103254 -0.309746 0.100911 0.067 Uiso 1 1 calc R U . . .
C6AA C 0.3063(2) -0.0356(2) 0.1669(2) 0.0479(6) Uani 1 1 d . . . . .
C5AA C -0.0002(3) -0.1813(3) -0.2057(2) 0.0577(7) Uani 1 1 d . . . . .
H5AA H -0.043234 -0.192132 -0.144086 0.069 Uiso 1 1 calc R U . . .
C0AA C -0.0050(2) -0.2378(3) -0.4203(2) 0.0468(6) Uani 1 1 d . . . . .
C0BA C 0.3483(2) 0.0742(3) 0.3767(2) 0.0473(6) Uani 1 1 d . . . . .
C3 C 0.4060(3) -0.5059(3) 0.1309(2) 0.0602(7) Uani 1 1 d . . . . .
H3 H 0.482032 -0.556024 0.137482 0.072 Uiso 1 1 calc R U . . .
C4 C 0.4103(3) 0.0946(3) 0.1969(2) 0.0507(6) Uani 1 1 d . . . . .
C5 C 0.4307(2) 0.1544(3) 0.3272(2) 0.0510(6) Uani 1 1 d . . . . .
C6 C 0.2632(3) -0.0487(3) 0.2814(2) 0.0510(6) Uani 1 1 d . . . . .
C3BA C -0.0720(3) -0.2364(3) -0.6441(2) 0.0596(7) Uani 1 1 d . . . . .
H3BA H -0.028765 -0.145113 -0.624403 0.072 Uiso 1 1 calc R U . . .
C1AA C 0.1261(3) -0.0931(3) -0.1768(2) 0.0527(6) Uani 1 1 d . . . . .
C7 C -0.1408(2) -0.4422(3) -0.5836(2) 0.0558(6) Uani 1 1 d . . . . .
H7 H -0.145996 -0.491133 -0.522630 0.067 Uiso 1 1 calc R U . . .
C8 C -0.1993(3) -0.5048(3) -0.7056(2) 0.0617(7) Uani 1 1 d . . . . .
H8 H -0.241855 -0.596408 -0.726469 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1671(3) -0.4887(3) 0.1345(3) 0.0643(7) Uani 1 1 d . . . . .
H9 H 0.082087 -0.526836 0.144350 0.077 Uiso 1 1 calc R U . . .
C10 C 0.2799(3) -0.5616(3) 0.1448(2) 0.0613(7) Uani 1 1 d . . . . .
H10 H 0.270910 -0.649591 0.161323 0.074 Uiso 1 1 calc R U . . .
C2AA C 0.1879(3) -0.0825(3) -0.2693(2) 0.0589(7) Uani 1 1 d . . . . .
H2AA H 0.274683 -0.026468 -0.251231 0.071 Uiso 1 1 calc R U . . .
C3AA C -0.1329(3) -0.2994(3) -0.7656(2) 0.0665(8) Uani 1 1 d . . . . .
H3AA H -0.131434 -0.250210 -0.827187 0.080 Uiso 1 1 calc R U . . .
C1BA C 0.3519(3) 0.1129(3) 0.4990(2) 0.0616(7) Uani 1 1 d . . . . .
H1BA H 0.298493 0.058157 0.533678 0.074 Uiso 1 1 calc R U . . .
C8AA C 0.1240(3) -0.1533(3) -0.3891(2) 0.0581(7) Uani 1 1 d . . . . .
H8AA H 0.168660 -0.143909 -0.450075 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4349(3) 0.2326(3) 0.5693(3) 0.0752(9) Uani 1 1 d . . . . .
H11 H 0.435010 0.260790 0.651094 0.090 Uiso 1 1 calc R U . . .
C12 C 0.1903(4) -0.0042(3) -0.0496(2) 0.0614(7) Uani 1 1 d . . . . .
C13 C 0.5153(3) 0.2756(3) 0.3991(3) 0.0683(8) Uani 1 1 d . . . . .
H13 H 0.568937 0.330873 0.365043 0.082 Uiso 1 1 calc R U . . .
C14 C -0.1956(3) -0.4334(3) -0.7966(2) 0.0672(8) Uani 1 1 d . . . . .
H14 H -0.235576 -0.476096 -0.879131 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5183(3) 0.3117(3) 0.5195(3) 0.0784(9) Uani 1 1 d . . . . .
H15 H 0.577083 0.390666 0.569155 0.094 Uiso 1 1 calc R U . . .
H6A H 0.277(2) -0.130(3) 0.311(2) 0.048(7) Uiso 1 1 d . . . . .
H6B H 0.156(3) -0.043(3) 0.271(2) 0.057(7) Uiso 1 1 d . . . . .
H12A H 0.277(3) 0.046(3) -0.048(3) 0.077(9) Uiso 1 1 d . . . . .
H12B H 0.118(3) 0.065(3) -0.031(3) 0.086(10) 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 C4 1.214(3) . ?
N2 C9AA 1.451(3) . ?
N2 C6AA 1.471(3) . ?
N2 C12 1.475(3) . ?
C7AA C1 1.376(3) . ?
C7AA C4BA 1.386(3) . ?
C7AA C9AA 1.482(4) . ?
C9AA C6AA 1.514(3) . ?
C2BA C5AA 1.380(3) . ?
C2BA C0AA 1.382(3) . ?
C4BA C3 1.385(4) . ?
C4AA C3BA 1.385(3) . ?
C4AA C7 1.389(3) . ?
C4AA C0AA 1.476(3) . ?
C1 C9 1.380(4) . ?
C6AA C6 1.503(3) . ?
C6AA C4 1.506(3) . ?
C5AA C1AA 1.383(3) . ?
C0AA C8AA 1.384(3) . ?
C0BA C1BA 1.376(3) . ?
C0BA C5 1.380(3) . ?
C0BA C6 1.503(3) . ?
C3 C10 1.372(4) . ?
C4 C5 1.460(3) . ?
C5 C13 1.392(3) . ?
C3BA C3AA 1.372(4) . ?
C1AA C2AA 1.367(4) . ?
C1AA C12 1.508(3) . ?
C7 C8 1.372(3) . ?
C8 C14 1.370(4) . ?
C9 C10 1.371(4) . ?
C2AA C8AA 1.381(3) . ?
C3AA C14 1.362(4) . ?
C1BA C11 1.371(4) . ?
C11 C15 1.380(4) . ?
C13 C15 1.356(4) . ?

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
C9AA N2 C6AA 62.39(15) . . ?
C9AA N2 C12 117.3(2) . . ?
C6AA N2 C12 118.8(2) . . ?
C1 C7AA C4BA 118.4(2) . . ?
C1 C7AA C9AA 121.9(2) . . ?
C4BA C7AA C9AA 119.6(2) . . ?
N2 C9AA C7AA 118.9(2) . . ?
N2 C9AA C6AA 59.46(15) . . ?
C7AA C9AA C6AA 120.6(2) . . ?
C5AA C2BA C0AA 121.7(2) . . ?
C3 C4BA C7AA 120.9(2) . . ?
C3BA C4AA C7 117.6(2) . . ?
C3BA C4AA C0AA 120.2(2) . . ?
C7 C4AA C0AA 122.2(2) . . ?
C7AA C1 C9 121.1(2) . . ?
N2 C6AA C6 118.4(2) . . ?
N2 C6AA C4 123.6(2) . . ?
C6 C6AA C4 107.86(19) . . ?
N2 C6AA C9AA 58.15(15) . . ?
C6 C6AA C9AA 123.9(2) . . ?
C4 C6AA C9AA 118.1(2) . . ?
C2BA C5AA C1AA 120.7(2) . . ?
C2BA C0AA C8AA 116.9(2) . . ?
C2BA C0AA C4AA 123.2(2) . . ?
C8AA C0AA C4AA 119.9(2) . . ?
C1BA C0BA C5 119.7(2) . . ?
C1BA C0BA C6 129.2(2) . . ?
C5 C0BA C6 111.1(2) . . ?
C10 C3 C4BA 119.3(3) . . ?
O1 C4 C5 126.8(2) . . ?
O1 C4 C6AA 126.9(2) . . ?
C5 C4 C6AA 106.3(2) . . ?
C0BA C5 C13 120.5(2) . . ?
C0BA C5 C4 110.5(2) . . ?
C13 C5 C4 129.0(2) . . ?
C0BA C6 C6AA 104.2(2) . . ?
C3AA C3BA C4AA 121.1(3) . . ?
C2AA C1AA C5AA 118.0(2) . . ?
C2AA C1AA C12 120.3(2) . . ?
C5AA C1AA C12 121.6(2) . . ?
C8 C7 C4AA 120.8(2) . . ?
C14 C8 C7 120.4(3) . . ?
C10 C9 C1 119.6(3) . . ?
C9 C10 C3 120.7(3) . . ?
C1AA C2AA C8AA 121.3(2) . . ?
C14 C3AA C3BA 120.4(3) . . ?
C11 C1BA C0BA 119.5(3) . . ?
C2AA C8AA C0AA 121.3(2) . . ?
C1BA C11 C15 120.5(3) . . ?
N2 C12 C1AA 111.1(2) . . ?
C15 C13 C5 119.0(3) . . ?
C3AA C14 C8 119.6(3) . . ?
C13 C15 C11 120.7(3) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.071

