# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_sb302_aks_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2096084'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration R
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33

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   'P 21 21 21'

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

_cell_length_a                   8.9929(8)
_cell_length_b                   9.6220(10)
_cell_length_c                   17.0576(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1476.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5293
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.392

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9967
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2603
_reflns_number_gt                2244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1000P)²+0.3035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_number_reflns         2603
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.866
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.3038(2) 0.41450(18) 0.46440(11) 0.0457(5) Uani 1 1 d . . .
O1 O 0.1546(3) 0.7802(2) 0.57588(12) 0.0761(6) Uani 1 1 d . . .
N1 N 0.1227(2) 0.5665(2) 0.52056(12) 0.0495(5) Uani 1 1 d . . .
O2 O 0.4547(2) 0.2914(2) 0.54353(12) 0.0772(6) Uani 1 1 d . . .
C12 C 0.3709(2) 0.3576(2) 0.39508(13) 0.0454(5) Uani 1 1 d . . .
C1 C 0.1648(2) 0.4944(2) 0.45038(13) 0.0441(5) Uani 1 1 d . . .
H006 H 0.0849 0.4318 0.4337 0.053 Uiso 1 1 calc R . .
C8 C 0.1668(3) 0.7013(2) 0.52066(14) 0.0502(6) Uani 1 1 d . . .
C2 C 0.1834(2) 0.6123(2) 0.39120(13) 0.0460(5) Uani 1 1 d . . .
H008 H 0.2610 0.5886 0.3531 0.055 Uiso 1 1 calc R . .
C11 C 0.3480(3) 0.3702(3) 0.53626(15) 0.0535(6) Uani 1 1 d . . .
C7 C 0.2334(3) 0.7340(2) 0.44154(14) 0.0489(6) Uani 1 1 d . . .
H00A H 0.3413 0.7244 0.4475 0.059 Uiso 1 1 calc R . .
C9 C 0.1157(3) 0.4825(3) 0.59162(16) 0.0620(7) Uani 1 1 d . . .
H00B H 0.0457 0.4068 0.5849 0.074 Uiso 1 1 calc R . .
H00C H 0.0834 0.5389 0.6356 0.074 Uiso 1 1 calc R . .
C17 C 0.2930(3) 0.2646(3) 0.34974(14) 0.0551(6) Uani 1 1 d . . .
H00D H 0.1998 0.2337 0.3657 0.066 Uiso 1 1 calc R . .
C13 C 0.5097(3) 0.4025(3) 0.37197(17) 0.0593(6) Uani 1 1 d . . .
H00E H 0.5625 0.4657 0.4024 0.071 Uiso 1 1 calc R . .
C14 C 0.5690(3) 0.3520(3) 0.30302(19) 0.0717(9) Uani 1 1 d . . .
H00F H 0.6633 0.3804 0.2873 0.086 Uiso 1 1 calc R . .
C15 C 0.4904(4) 0.2603(3) 0.25733(17) 0.0713(8) Uani 1 1 d . . .
H00G H 0.5310 0.2278 0.2107 0.086 Uiso 1 1 calc R . .
C5 C 0.1083(3) 0.8868(3) 0.34113(19) 0.0739(9) Uani 1 1 d . . .
H00H H 0.0985 0.9723 0.3162 0.089 Uiso 1 1 calc R . .
C10 C 0.2689(3) 0.4265(3) 0.60646(15) 0.0622(7) Uani 1 1 d . . .
H00I H 0.3290 0.5001 0.6289 0.075 Uiso 1 1 calc R . .
H00J H 0.2617 0.3531 0.6453 0.075 Uiso 1 1 calc R . .
C16 C 0.3538(4) 0.2172(3) 0.28014(16) 0.0697(8) Uani 1 1 d . . .
H00K H 0.3006 0.1554 0.2489 0.084 Uiso 1 1 calc R . .
C6 C 0.2069(4) 0.8794(3) 0.41084(18) 0.0787(9) Uani 1 1 d . . .
H00L H 0.1635 0.9348 0.4524 0.094 Uiso 1 1 calc R . .
H00M H 0.3021 0.9205 0.3975 0.094 Uiso 1 1 calc R . .
C3 C 0.0363(3) 0.6421(3) 0.34861(17) 0.0682(8) Uani 1 1 d . . .
H00N H 0.0213 0.5734 0.3078 0.082 Uiso 1 1 calc R . .
H00O H -0.0455 0.6345 0.3855 0.082 Uiso 1 1 calc R . .
C4 C 0.0363(4) 0.7841(4) 0.3131(3) 0.0920(11) Uani 1 1 d . . .
H00P H -0.0194 0.7983 0.2679 0.110 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
N2 C11 1.357(3) . ?
N2 C12 1.436(3) . ?
N2 C1 1.487(3) . ?
O1 C8 1.214(3) . ?
N1 C8 1.357(3) . ?
N1 C1 1.434(3) . ?
N1 C9 1.458(3) . ?
O2 C11 1.229(3) . ?
C12 C17 1.375(3) . ?
C12 C13 1.378(3) . ?
C1 C2 1.528(3) . ?
C1 H006 0.9800 . ?
C8 C7 1.510(3) . ?
C2 C7 1.520(3) . ?
C2 C3 1.537(3) . ?
C2 H008 0.9800 . ?
C11 C10 1.494(4) . ?
C7 C6 1.513(4) . ?
C7 H00A 0.9800 . ?
C9 C10 1.501(4) . ?
C9 H00B 0.9700 . ?
C9 H00C 0.9700 . ?
C17 C16 1.385(4) . ?
C17 H00D 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H00E 0.9300 . ?
C14 C15 1.373(5) . ?
C14 H00F 0.9300 . ?
C15 C16 1.354(5) . ?
C15 H00G 0.9300 . ?
C5 C4 1.275(5) . ?
C5 C6 1.485(4) . ?
C5 H00H 0.9300 . ?
C10 H00I 0.9700 . ?
C10 H00J 0.9700 . ?
C16 H00K 0.9300 . ?
C6 H00L 0.9700 . ?
C6 H00M 0.9700 . ?
C3 C4 1.494(5) . ?
C3 H00N 0.9700 . ?
C3 H00O 0.9700 . ?
C4 H00P 0.9300 . ?

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
C11 N2 C12 120.04(18) . . ?
C11 N2 C1 123.64(19) . . ?
C12 N2 C1 114.73(17) . . ?
C8 N1 C1 112.69(19) . . ?
C8 N1 C9 122.8(2) . . ?
C1 N1 C9 115.95(18) . . ?
C17 C12 C13 120.3(2) . . ?
C17 C12 N2 119.8(2) . . ?
C13 C12 N2 119.8(2) . . ?
N1 C1 N2 109.75(17) . . ?
N1 C1 C2 102.80(17) . . ?
N2 C1 C2 113.48(17) . . ?
N1 C1 H006 110.2 . . ?
N2 C1 H006 110.2 . . ?
C2 C1 H006 110.2 . . ?
O1 C8 N1 124.9(2) . . ?
O1 C8 C7 126.8(2) . . ?
N1 C8 C7 108.3(2) . . ?
C7 C2 C1 103.36(17) . . ?
C7 C2 C3 112.2(2) . . ?
C1 C2 C3 110.9(2) . . ?
C7 C2 H008 110.1 . . ?
C1 C2 H008 110.1 . . ?
C3 C2 H008 110.1 . . ?
O2 C11 N2 120.9(2) . . ?
O2 C11 C10 120.9(2) . . ?
N2 C11 C10 118.1(2) . . ?
C8 C7 C6 116.1(2) . . ?
C8 C7 C2 103.15(19) . . ?
C6 C7 C2 118.0(2) . . ?
C8 C7 H00A 106.2 . . ?
C6 C7 H00A 106.2 . . ?
C2 C7 H00A 106.2 . . ?
N1 C9 C10 107.5(2) . . ?
N1 C9 H00B 110.2 . . ?
C10 C9 H00B 110.2 . . ?
N1 C9 H00C 110.2 . . ?
C10 C9 H00C 110.2 . . ?
H00B C9 H00C 108.5 . . ?
C12 C17 C16 119.7(3) . . ?
C12 C17 H00D 120.2 . . ?
C16 C17 H00D 120.2 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H00E 120.5 . . ?
C14 C13 H00E 120.5 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H00F 119.6 . . ?
C13 C14 H00F 119.6 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H00G 120.0 . . ?
C14 C15 H00G 120.0 . . ?
C4 C5 C6 124.5(3) . . ?
C4 C5 H00H 117.8 . . ?
C6 C5 H00H 117.8 . . ?
C11 C10 C9 115.6(2) . . ?
C11 C10 H00I 108.4 . . ?
C9 C10 H00I 108.4 . . ?
C11 C10 H00J 108.4 . . ?
C9 C10 H00J 108.4 . . ?
H00I C10 H00J 107.4 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H00K 119.9 . . ?
C17 C16 H00K 119.9 . . ?
C5 C6 C7 114.6(3) . . ?
C5 C6 H00L 108.6 . . ?
C7 C6 H00L 108.6 . . ?
C5 C6 H00M 108.6 . . ?
C7 C6 H00M 108.6 . . ?
H00L C6 H00M 107.6 . . ?
C4 C3 C2 111.2(3) . . ?
C4 C3 H00N 109.4 . . ?
C2 C3 H00N 109.4 . . ?
C4 C3 H00O 109.4 . . ?
C2 C3 H00O 109.4 . . ?
H00N C3 H00O 108.0 . . ?
C5 C4 C3 123.9(3) . . ?
C5 C4 H00P 118.1 . . ?
C3 C4 H00P 118.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_SB-1P_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2096075'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.5567(6)
_cell_length_b                   9.7212(6)
_cell_length_c                   15.0352(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.695(2)
_cell_angle_gamma                90
_cell_volume                     1393.91(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9425
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      23.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   multi-scans
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68044
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.456
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3453
_reflns_number_gt                2375
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²+0.2056P] 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         3453
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.20557(13) 0.32576(14) 0.57558(9) 0.0407(3) Uani 1 1 d . . . . .
O2 O 0.01753(13) 0.19074(15) 0.59235(12) 0.0699(4) Uani 1 1 d . . . . .
N2 N 0.38442(14) 0.24670(15) 0.48250(10) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.58900(16) 0.12771(17) 0.46788(13) 0.0794(5) Uani 1 1 d . . . . .
C8 C 0.33325(15) 0.36243(16) 0.53058(10) 0.0375(3) Uani 1 1 d . . . . .
H5 H 0.312206 0.438490 0.489071 0.045 Uiso 1 1 calc R U . . .
C12 C 0.15006(15) 0.43458(17) 0.62762(11) 0.0392(4) Uani 1 1 d . . . . .
C5 C 0.45917(16) 0.40006(17) 0.59285(11) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.56929(16) 0.31420(18) 0.57443(12) 0.0457(4) Uani 1 1 d . . . . .
C9 C 0.12763(17) 0.20945(18) 0.55734(13) 0.0483(4) Uani 1 1 d . . . . .
C13 C 0.11993(18) 0.56066(19) 0.58774(12) 0.0482(4) Uani 1 1 d . . . . .
H10 H 0.128254 0.571715 0.526872 0.058 Uiso 1 1 calc R U . . .
C7 C 0.52193(18) 0.21685(19) 0.50379(13) 0.0506(4) Uani 1 1 d . . . . .
C17 C 0.13464(18) 0.4171(2) 0.71791(12) 0.0543(5) Uani 1 1 d . . . . .
H14 H 0.153998 0.332750 0.745181 0.065 Uiso 1 1 calc R U . . .
C4 C 0.47744(19) 0.5016(2) 0.65658(12) 0.0535(5) Uani 1 1 d . . . . .
H4 H 0.404839 0.561422 0.668046 0.064 Uiso 1 1 calc R U . . .
C1 C 0.70045(18) 0.3256(2) 0.62001(14) 0.0608(6) Uani 1 1 d . . . . .
H1 H 0.774080 0.267932 0.607047 0.073 Uiso 1 1 calc R U . . .
C10 C 0.18220(19) 0.1050(2) 0.49464(16) 0.0582(5) Uani 1 1 d . . . . .
H6 H 0.103388 0.065034 0.459844 0.070 Uiso 1 1 calc R U . . .
H7 H 0.227729 0.031679 0.529414 0.070 Uiso 1 1 calc R U . . .
C11 C 0.2850(2) 0.1620(2) 0.43140(14) 0.0599(5) Uani 1 1 d . . . . .
H9 H 0.333192 0.087375 0.403340 0.072 Uiso 1 1 calc R U . . .
H8 H 0.235790 0.216224 0.385142 0.072 Uiso 1 1 calc R U . . .
C14 C 0.0776(2) 0.6699(2) 0.63826(15) 0.0641(5) Uani 1 1 d . . . . .
H11 H 0.059848 0.754955 0.611614 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0894(2) 0.5288(3) 0.76733(13) 0.0696(6) Uani 1 1 d . . . . .
H13 H 0.077918 0.518629 0.827931 0.083 Uiso 1 1 calc R U . . .
C2 C 0.7171(2) 0.4252(3) 0.68486(15) 0.0725(7) Uani 1 1 d . . . . .
H2 H 0.803222 0.434328 0.716819 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6077(2) 0.5120(3) 0.70335(15) 0.0710(6) Uani 1 1 d . . . . .
H3 H 0.621503 0.578321 0.747645 0.085 Uiso 1 1 calc R U . . .
C15 C 0.0618(2) 0.6533(3) 0.72683(16) 0.0716(6) Uani 1 1 d . . . . .
H12 H 0.032019 0.726966 0.760277 0.086 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
N1 C9 1.372(2) . ?
N1 C12 1.437(2) . ?
N1 C8 1.4765(19) . ?
O2 C9 1.220(2) . ?
N2 C7 1.364(2) . ?
N2 C8 1.440(2) . ?
N2 C11 1.441(2) . ?
O1 C7 1.224(2) . ?
C8 C5 1.521(2) . ?
C8 H5 0.9800 . ?
C12 C17 1.385(2) . ?
C12 C13 1.386(2) . ?
C5 C4 1.379(3) . ?
C5 C6 1.385(2) . ?
C6 C1 1.394(2) . ?
C6 C7 1.472(3) . ?
C9 C10 1.502(3) . ?
C13 C14 1.381(3) . ?
C13 H10 0.9300 . ?
C17 C16 1.400(3) . ?
C17 H14 0.9300 . ?
C4 C3 1.394(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C10 C11 1.516(3) . ?
C10 H6 0.9700 . ?
C10 H7 0.9700 . ?
C11 H9 0.9700 . ?
C11 H8 0.9700 . ?
C14 C15 1.359(4) . ?
C14 H11 0.9300 . ?
C16 C15 1.373(4) . ?
C16 H13 0.9300 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 H12 0.9300 . ?

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
C9 N1 C12 120.04(13) . . ?
C9 N1 C8 124.15(14) . . ?
C12 N1 C8 114.62(12) . . ?
C7 N2 C8 113.69(15) . . ?
C7 N2 C11 126.56(16) . . ?
C8 N2 C11 118.73(13) . . ?
N2 C8 N1 111.03(13) . . ?
N2 C8 C5 102.48(12) . . ?
N1 C8 C5 114.86(13) . . ?
N2 C8 H5 109.4 . . ?
N1 C8 H5 109.4 . . ?
C5 C8 H5 109.4 . . ?
C17 C12 C13 119.99(16) . . ?
C17 C12 N1 120.62(16) . . ?
C13 C12 N1 119.27(14) . . ?
C4 C5 C6 120.43(16) . . ?
C4 C5 C8 131.27(15) . . ?
C6 C5 C8 108.25(15) . . ?
C5 C6 C1 121.65(19) . . ?
C5 C6 C7 109.23(14) . . ?
C1 C6 C7 129.12(17) . . ?
O2 C9 N1 120.59(17) . . ?
O2 C9 C10 120.92(17) . . ?
N1 C9 C10 118.48(15) . . ?
C14 C13 C12 120.11(18) . . ?
C14 C13 H10 119.9 . . ?
C12 C13 H10 119.9 . . ?
O1 C7 N2 124.8(2) . . ?
O1 C7 C6 128.91(18) . . ?
N2 C7 C6 106.23(14) . . ?
C12 C17 C16 118.7(2) . . ?
C12 C17 H14 120.6 . . ?
C16 C17 H14 120.6 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C2 C1 C6 117.63(19) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C9 C10 C11 114.32(16) . . ?
C9 C10 H6 108.7 . . ?
C11 C10 H6 108.7 . . ?
C9 C10 H7 108.7 . . ?
C11 C10 H7 108.7 . . ?
H6 C10 H7 107.6 . . ?
N2 C11 C10 107.83(16) . . ?
N2 C11 H9 110.1 . . ?
C10 C11 H9 110.1 . . ?
N2 C11 H8 110.1 . . ?
C10 C11 H8 110.1 . . ?
H9 C11 H8 108.5 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H11 119.9 . . ?
C13 C14 H11 119.9 . . ?
C15 C16 C17 120.37(19) . . ?
C15 C16 H13 119.8 . . ?
C17 C16 H13 119.8 . . ?
C1 C2 C3 121.09(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H12 119.7 . . ?
C16 C15 H12 119.7 . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044



