# 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
_audit_block_doi                 10.5517/ccdc.csd.cc23spj4
_database_code_depnum_ccdc_archive 'CCDC 1960146'
loop_
_audit_author_name
_audit_author_address
'C. M. Nagaraja'
;IIT Ropar
India
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-04-30 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         ?
_chemical_formula_sum            'C16 H11 Br N O2'
_chemical_formula_weight         329.17

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'
Br Br -0.2901 2.4595 '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                   8.3268(14)
_cell_length_b                   9.2126(13)
_cell_length_c                   9.6765(16)
_cell_angle_alpha                83.964(5)
_cell_angle_beta                 73.197(5)
_cell_angle_gamma                73.333(5)
_cell_volume                     680.55(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(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    1.606
_exptl_crystal_F_000             330
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.020
_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      273(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            12915
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0521
_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       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2770
_reflns_number_gt                2534
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0543P)²+0.4185P] 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         2770
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_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
Br1 Br 0.86502(4) 0.50203(4) 0.87246(3) 0.05713(15) Uani 1 1 d . . . . .
C1 C 0.7002(4) 0.3297(4) 0.3032(3) 0.0487(6) Uani 1 1 d . . . . .
H1A H 0.6806 0.4285 0.2576 0.073 Uiso 1 1 calc R U . . .
H1B H 0.7959 0.2604 0.2404 0.073 Uiso 1 1 calc R U . . .
H1C H 0.5973 0.2952 0.3224 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7756(4) 0.2148(3) 0.5283(3) 0.0429(6) Uani 1 1 d . . . . .
N1 N 0.7408(3) 0.3372(2) 0.4374(2) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.5213(3) 0.3335(3) 0.8149(3) 0.0622(6) Uani 1 1 d . . . . .
C8 C 0.7824(3) 0.6957(3) 0.6366(3) 0.0445(6) Uani 1 1 d . . . . .
H8 H 0.7947 0.7726 0.6846 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7083(3) 0.1240(3) 0.9009(3) 0.0357(5) Uani 1 1 d . . . . .
C4 C 0.7934(3) 0.4342(3) 0.6222(3) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.7766(4) 0.0868(2) 0.5083(3) 0.0678(7) Uani 1 1 d . . . . .
C5 C 0.7495(3) 0.4689(3) 0.4921(2) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.8095(3) 0.5485(3) 0.6937(3) 0.0381(5) Uani 1 1 d . . . . .
C3 C 0.8087(3) 0.2698(3) 0.6591(3) 0.0372(5) Uani 1 1 d . . . . .
C10 C 0.6652(3) 0.2493(3) 0.7961(3) 0.0392(5) Uani 1 1 d . . . . .
C12 C 0.5956(4) 0.1326(3) 1.0399(3) 0.0456(6) Uani 1 1 d . . . . .
H12 H 0.4986 0.2154 1.0646 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7192(3) 0.6146(3) 0.4332(3) 0.0408(5) Uani 1 1 d . . . . .
H6 H 0.6882 0.6366 0.3469 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8513(4) 0.0002(3) 0.8649(3) 0.0449(6) Uani 1 1 d . . . . .
H16 H 0.9276 -0.0064 0.7726 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7703(4) -0.1033(3) 1.1038(3) 0.0548(7) Uani 1 1 d . . . . .
H14 H 0.7923 -0.1796 1.1723 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6276(4) 0.0189(3) 1.1408(3) 0.0528(7) Uani 1 1 d . . . . .
H13 H 0.5527 0.0250 1.2336 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7373(3) 0.7266(3) 0.5087(3) 0.0454(6) Uani 1 1 d . . . . .
H7 H 0.7182 0.8254 0.4715 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8807(4) -0.1144(3) 0.9672(4) 0.0560(8) Uani 1 1 d . . . . .
H15 H 0.9756 -0.1990 0.9429 0.067 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
Br1 C9 1.893(3) . ?
C1 N1 1.446(3) . ?
C2 O1 1.213(3) . ?
C2 N1 1.371(3) . ?
C2 C3 1.533(4) . ?
N1 C5 1.401(3) . ?
O2 C10 1.201(3) . ?
C8 C7 1.374(4) . ?
C8 C9 1.391(4) . ?
C11 C16 1.380(4) . ?
C11 C12 1.395(4) . ?
C11 C10 1.488(3) . ?
C4 C9 1.375(3) . ?
C4 C5 1.392(3) . ?
C4 C3 1.497(3) . ?
C5 C6 1.385(3) . ?
C3 C10 1.543(3) . ?
C12 C13 1.377(4) . ?
C6 C7 1.390(4) . ?
C16 C15 1.388(4) . ?
C14 C15 1.370(4) . ?
C14 C13 1.371(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
O1 C2 N1 125.3(3) . . ?
O1 C2 C3 126.7(3) . . ?
N1 C2 C3 108.0(2) . . ?
C2 N1 C5 111.1(2) . . ?
C2 N1 C1 123.9(2) . . ?
C5 N1 C1 125.0(2) . . ?
C7 C8 C9 119.3(2) . . ?
C16 C11 C12 119.5(2) . . ?
C16 C11 C10 122.8(2) . . ?
C12 C11 C10 117.7(2) . . ?
C9 C4 C5 118.8(2) . . ?
C9 C4 C3 132.2(2) . . ?
C5 C4 C3 109.0(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 N1 128.2(2) . . ?
C4 C5 N1 109.5(2) . . ?
C4 C9 C8 120.5(2) . . ?
C4 C9 Br1 118.74(19) . . ?
C8 C9 Br1 120.8(2) . . ?
C4 C3 C2 102.30(19) . . ?
C4 C3 C10 111.0(2) . . ?
C2 C3 C10 109.2(2) . . ?
O2 C10 C11 121.6(2) . . ?
O2 C10 C3 119.3(2) . . ?
C11 C10 C3 119.1(2) . . ?
C13 C12 C11 120.2(3) . . ?
C5 C6 C7 117.1(2) . . ?
C11 C16 C15 119.6(3) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C13 C12 119.7(3) . . ?
C8 C7 C6 122.0(2) . . ?
C14 C15 C16 120.2(3) . . ?

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
O1 C2 N1 C5 179.8(3) . . . . ?
C3 C2 N1 C5 0.9(3) . . . . ?
O1 C2 N1 C1 -0.1(5) . . . . ?
C3 C2 N1 C1 -179.0(2) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C6 177.3(2) . . . . ?
C9 C4 C5 N1 179.7(2) . . . . ?
C3 C4 C5 N1 -2.1(3) . . . . ?
C2 N1 C5 C6 -178.6(2) . . . . ?
C1 N1 C5 C6 1.3(4) . . . . ?
C2 N1 C5 C4 0.8(3) . . . . ?
C1 N1 C5 C4 -179.3(2) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C3 C4 C9 C8 -177.7(2) . . . . ?
C5 C4 C9 Br1 178.84(17) . . . . ?
C3 C4 C9 Br1 1.3(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C8 C9 Br1 -178.12(19) . . . . ?
C9 C4 C3 C2 -179.7(3) . . . . ?
C5 C4 C3 C2 2.5(3) . . . . ?
C9 C4 C3 C10 63.9(3) . . . . ?
C5 C4 C3 C10 -113.8(2) . . . . ?
O1 C2 C3 C4 179.1(3) . . . . ?
N1 C2 C3 C4 -2.0(3) . . . . ?
O1 C2 C3 C10 -63.3(4) . . . . ?
N1 C2 C3 C10 115.6(2) . . . . ?
C16 C11 C10 O2 160.1(3) . . . . ?
C12 C11 C10 O2 -18.5(4) . . . . ?
C16 C11 C10 C3 -19.2(4) . . . . ?
C12 C11 C10 C3 162.2(2) . . . . ?
C4 C3 C10 O2 38.4(4) . . . . ?
C2 C3 C10 O2 -73.6(3) . . . . ?
C4 C3 C10 C11 -142.4(2) . . . . ?
C2 C3 C10 C11 105.6(3) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C13 179.1(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
N1 C5 C6 C7 -179.7(2) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C10 C11 C16 C15 -178.2(3) . . . . ?
C15 C14 C13 C12 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C11 C16 C15 C14 -1.3(5) . . . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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 1960147'
loop_
_audit_author_name
_audit_author_address
'C. M. Nagaraja'
;IIT Ropar
India
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-04-30 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         ?
_chemical_formula_sum            'C17 H14 N O3'
_chemical_formula_weight         280.29

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                   11.1312(4)
_cell_length_b                   8.2115(4)
_cell_length_c                   16.7219(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.1920(10)
_cell_angle_gamma                90
_cell_volume                     1443.50(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(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    1.290
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_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      273(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            14276
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2941
_reflns_number_gt                2496
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0954P)²+0.4481P] 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         2941
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O2 O 0.95508(15) 0.09757(18) 0.61773(10) 0.0628(4) Uani 1 1 d . . . . .
O3 O 0.79361(16) 0.34374(17) 0.67930(10) 0.0719(5) Uani 1 1 d . . . . .
O1 O 0.85268(17) -0.0627(2) 0.47251(10) 0.0696(5) Uani 1 1 d . . . . .
N1 N 0.66240(18) -0.1862(2) 0.46493(10) 0.0606(5) Uani 1 1 d . . . . .
C4 C 0.64812(17) -0.1200(2) 0.59428(11) 0.0468(4) Uani 1 1 d . . . . .
C10 C 0.85777(18) 0.0405(2) 0.64001(12) 0.0463(4) Uani 1 1 d . . . . .
C5 C 0.5868(2) -0.1991(2) 0.51734(12) 0.0555(5) Uani 1 1 d . . . . .
C11 C 0.86468(17) 0.0839(2) 0.72764(11) 0.0461(4) Uani 1 1 d . . . . .
C3 C 0.76540(18) -0.0532(2) 0.58748(11) 0.0451(4) Uani 1 1 d . . . . .
C16 C 0.83521(17) 0.2407(2) 0.74677(13) 0.0517(5) Uani 1 1 d . . . . .
C2 C 0.7692(2) -0.0972(2) 0.50370(12) 0.0524(5) Uani 1 1 d . . . . .
C9 C 0.5899(2) -0.1180(3) 0.65614(14) 0.0589(5) Uani 1 1 d . . . . .
H9 H 0.6286 -0.0666 0.7078 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9039(2) -0.0300(3) 0.79098(13) 0.0592(5) Uani 1 1 d . . . . .
H12 H 0.9218 -0.1353 0.7778 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4709(2) -0.2736(3) 0.50088(17) 0.0743(7) Uani 1 1 d . . . . .
H6 H 0.4315 -0.3253 0.4494 0.089 Uiso 1 1 calc R U . . .
C8 C 0.4729(2) -0.1942(3) 0.63955(18) 0.0759(7) Uani 1 1 d . . . . .
H8 H 0.4334 -0.1945 0.6807 0.091 Uiso 1 1 calc R U . . .
C15 C 0.8485(2) 0.2800(3) 0.83015(15) 0.0671(6) Uani 1 1 d . . . . .
H15 H 0.8288 0.3843 0.8436 0.080 Uiso 1 1 calc R U . . .
C7 C 0.4145(2) -0.2695(4) 0.5629(2) 0.0847(8) Uani 1 1 d . . . . .
H7 H 0.3355 -0.3184 0.5529 0.102 Uiso 1 1 calc R U . . .
C14 C 0.8905(2) 0.1652(4) 0.89239(15) 0.0774(7) Uani 1 1 d . . . . .
H14 H 0.9012 0.1934 0.9482 0.093 Uiso 1 1 calc R U . . .
C13 C 0.9173(3) 0.0087(3) 0.87402(15) 0.0754(7) Uani 1 1 d . . . . .
H13 H 0.9438 -0.0694 0.9165 0.090 Uiso 1 1 calc R U . . .
C1 C 0.6290(3) -0.2493(4) 0.37900(15) 0.0867(9) Uani 1 1 d . . . . .
H1A H 0.5502 -0.3079 0.3651 0.130 Uiso 1 1 calc R U . . .
H1B H 0.6199 -0.1605 0.3401 0.130 Uiso 1 1 calc R U . . .
H1C H 0.6948 -0.3212 0.3751 0.130 Uiso 1 1 calc R U . . .
C17 C 0.7632(3) 0.5064(3) 0.6943(2) 0.0981(10) Uani 1 1 d . . . . .
H17A H 0.7354 0.5650 0.6417 0.147 Uiso 1 1 calc R U . . .
H17B H 0.6965 0.5058 0.7188 0.147 Uiso 1 1 calc R U . . .
H17C H 0.8372 0.5584 0.7324 0.147 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
O2 C10 1.341(2) . ?
O3 C16 1.364(3) . ?
O3 C17 1.420(3) . ?
O1 C2 1.239(3) . ?
N1 C2 1.364(3) . ?
N1 C5 1.404(3) . ?
N1 C1 1.456(3) . ?
C4 C9 1.390(3) . ?
C4 C5 1.402(3) . ?
C4 C3 1.454(3) . ?
C10 C3 1.352(3) . ?
C10 C11 1.485(3) . ?
C5 C6 1.372(3) . ?
C11 C12 1.372(3) . ?
C11 C16 1.392(3) . ?
C3 C2 1.461(3) . ?
C16 C15 1.391(3) . ?
C9 C8 1.388(3) . ?
C12 C13 1.384(3) . ?
C6 C7 1.379(4) . ?
C8 C7 1.378(4) . ?
C15 C14 1.368(4) . ?
C14 C13 1.376(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
C16 O3 C17 118.3(2) . . ?
C2 N1 C5 110.55(16) . . ?
C2 N1 C1 124.0(2) . . ?
C5 N1 C1 125.3(2) . . ?
C9 C4 C5 118.88(19) . . ?
C9 C4 C3 134.77(18) . . ?
C5 C4 C3 106.35(16) . . ?
O2 C10 C3 122.01(17) . . ?
O2 C10 C11 113.94(16) . . ?
C3 C10 C11 124.01(17) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 N1 128.7(2) . . ?
C4 C5 N1 109.09(17) . . ?
C12 C11 C16 119.48(18) . . ?
C12 C11 C10 119.90(16) . . ?
C16 C11 C10 120.60(17) . . ?
C10 C3 C4 132.40(17) . . ?
C10 C3 C2 120.56(17) . . ?
C4 C3 C2 106.94(16) . . ?
O3 C16 C15 125.50(19) . . ?
O3 C16 C11 115.18(17) . . ?
C15 C16 C11 119.32(19) . . ?
O1 C2 N1 125.42(18) . . ?
O1 C2 C3 127.54(19) . . ?
N1 C2 C3 107.04(17) . . ?
C8 C9 C4 118.9(2) . . ?
C11 C12 C13 121.4(2) . . ?
C5 C6 C7 118.0(2) . . ?
C7 C8 C9 120.9(2) . . ?
C14 C15 C16 120.0(2) . . ?
C8 C7 C6 121.2(2) . . ?
C15 C14 C13 121.3(2) . . ?
C14 C13 C12 118.6(2) . . ?

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
C9 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C6 -178.56(19) . . . . ?
C9 C4 C5 N1 -179.85(16) . . . . ?
C3 C4 C5 N1 1.1(2) . . . . ?
C2 N1 C5 C6 177.8(2) . . . . ?
C1 N1 C5 C6 1.4(4) . . . . ?
C2 N1 C5 C4 -1.9(2) . . . . ?
C1 N1 C5 C4 -178.2(2) . . . . ?
O2 C10 C11 C12 -102.4(2) . . . . ?
C3 C10 C11 C12 75.2(2) . . . . ?
O2 C10 C11 C16 75.8(2) . . . . ?
C3 C10 C11 C16 -106.7(2) . . . . ?
O2 C10 C3 C4 -175.40(17) . . . . ?
C11 C10 C3 C4 7.3(3) . . . . ?
O2 C10 C3 C2 0.5(3) . . . . ?
C11 C10 C3 C2 -176.79(16) . . . . ?
C9 C4 C3 C10 -2.5(4) . . . . ?
C5 C4 C3 C10 176.25(19) . . . . ?
C9 C4 C3 C2 -178.9(2) . . . . ?
C5 C4 C3 C2 -0.09(19) . . . . ?
C17 O3 C16 C15 1.4(3) . . . . ?
C17 O3 C16 C11 -179.3(2) . . . . ?
C12 C11 C16 O3 -178.14(18) . . . . ?
C10 C11 C16 O3 3.7(3) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
C10 C11 C16 C15 -176.89(18) . . . . ?
C5 N1 C2 O1 -178.63(19) . . . . ?
C1 N1 C2 O1 -2.2(3) . . . . ?
C5 N1 C2 C3 1.8(2) . . . . ?
C1 N1 C2 C3 178.2(2) . . . . ?
C10 C3 C2 O1 2.5(3) . . . . ?
C4 C3 C2 O1 179.38(19) . . . . ?
C10 C3 C2 N1 -177.87(16) . . . . ?
C4 C3 C2 N1 -1.0(2) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C3 C4 C9 C8 178.5(2) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 176.8(2) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
N1 C5 C6 C7 -179.8(2) . . . . ?
C4 C9 C8 C7 -0.6(3) . . . . ?
O3 C16 C15 C14 179.5(2) . . . . ?
C11 C16 C15 C14 0.2(3) . . . . ?
C9 C8 C7 C6 0.9(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C16 C15 C14 C13 -1.7(4) . . . . ?
C15 C14 C13 C12 1.6(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041

