# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 1977153'
loop_
_audit_author_name
_audit_author_address
'Partha Roy'
;Jadavpur University
India
;
_audit_update_record             
;
2020-01-13 deposited with the CCDC.	2020-04-13 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         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   29.004(4)
_cell_length_b                   37.698(6)
_cell_length_c                   4.4554(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4871.7(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      27.004

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS
_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  'BRUKER D8 QUEST AREA DETECTOR'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16785
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.772
_diffrn_reflns_theta_max         27.004
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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             2670
_reflns_number_gt                1559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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-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)+(0.0282P)²+9.7713P] 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_abs_structure_details 
;
 Flack x determined using 417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1715
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_restrained_S_all      1.223
_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 0.74401(15) 0.05212(12) 0.6448(12) 0.0668(16) Uani 1 1 d . . . . .
N1 N 0.82008(16) 0.05908(14) 0.3461(11) 0.0474(13) Uani 1 1 d . . . . .
O1 O 0.65066(15) 0.09110(12) 1.2173(15) 0.097(2) Uani 1 1 d . . . . .
C2 C 0.7684(2) 0.15237(15) 1.0032(14) 0.0480(16) Uani 1 1 d . . . . .
C4 C 0.72132(19) 0.09943(16) 0.9641(16) 0.0494(17) Uani 1 1 d . . . . .
C7 C 0.79194(18) 0.10366(15) 0.6808(13) 0.0426(15) Uani 1 1 d . . . . .
C3 C 0.72994(19) 0.13292(16) 1.0813(15) 0.0503(17) Uani 1 1 d . . . . .
H3 H 0.709066 0.142571 1.217143 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7525(2) 0.08468(16) 0.7609(14) 0.0479(17) Uani 1 1 d . . . . .
N2 N 0.92213(19) 0.05104(16) -0.1527(16) 0.0724(19) Uani 1 1 d . . . . .
C11 C 0.8497(2) 0.01044(17) 0.0612(16) 0.0579(19) Uani 1 1 d . . . . .
H11 H 0.824977 -0.003218 0.126356 0.069 Uiso 1 1 calc R U . . .
C8 C 0.7991(2) 0.13714(15) 0.8045(14) 0.0488(16) Uani 1 1 d . . . . .
H8 H 0.825537 0.149663 0.751518 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8540(2) 0.04536(16) 0.1481(13) 0.0430(15) Uani 1 1 d . . . . .
C9 C 0.82550(19) 0.08936(17) 0.4733(13) 0.0466(16) Uani 1 1 d . . . . .
H9 H 0.851830 0.102509 0.430615 0.056 Uiso 1 1 calc R U . . .
C14 C 0.8901(2) 0.06452(17) 0.0298(16) 0.0594(19) Uani 1 1 d . . . . .
H14 H 0.892352 0.088391 0.080371 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9177(2) 0.0169(2) -0.2231(19) 0.068(2) Uani 1 1 d . . . . .
H13 H 0.939767 0.006672 -0.347284 0.082 Uiso 1 1 calc R U . . .
C12 C 0.8827(3) -0.00375(19) -0.1230(16) 0.066(2) Uani 1 1 d . . . . .
H12 H 0.881007 -0.027466 -0.179320 0.079 Uiso 1 1 calc R U . . .
C1 C 0.7770(2) 0.18901(17) 1.1256(17) 0.070(2) Uani 1 1 d . . . . .
H1A H 0.805368 0.198082 1.045253 0.104 Uiso 1 1 calc R U . . .
H1B H 0.752064 0.204359 1.069144 0.104 Uiso 1 1 calc R U . . .
H1C H 0.779072 0.187951 1.340467 0.104 Uiso 1 1 calc R U . . .
C5 C 0.6805(2) 0.07998(19) 1.058(2) 0.080(3) Uani 1 1 d . . . . .
H5 H 0.677271 0.056889 0.987320 0.096 Uiso 1 1 calc R U . . .
H2 H 0.767(2) 0.0480(16) 0.507(17) 0.07(2) 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
O2 C6 1.355(7) . ?
O2 H2 0.92(7) . ?
N1 C9 1.284(7) . ?
N1 C10 1.418(7) . ?
O1 C5 1.195(8) . ?
C2 C3 1.380(7) . ?
C2 C8 1.381(8) . ?
C2 C1 1.506(8) . ?
C4 C3 1.389(8) . ?
C4 C6 1.396(8) . ?
C4 C5 1.454(8) . ?
C7 C8 1.393(7) . ?
C7 C6 1.395(7) . ?
C7 C9 1.447(8) . ?
C3 H3 0.9300 . ?
N2 C13 1.331(8) . ?
N2 C14 1.335(8) . ?
C11 C12 1.368(9) . ?
C11 C10 1.378(8) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C10 C14 1.378(8) . ?
C9 H9 0.9300 . ?
C14 H14 0.9300 . ?
C13 C12 1.355(9) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 H5 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
C6 O2 H2 106(4) . . ?
C9 N1 C10 120.9(5) . . ?
C3 C2 C8 117.6(5) . . ?
C3 C2 C1 122.0(6) . . ?
C8 C2 C1 120.5(5) . . ?
C3 C4 C6 119.3(5) . . ?
C3 C4 C5 119.8(6) . . ?
C6 C4 C5 120.9(6) . . ?
C8 C7 C6 119.1(6) . . ?
C8 C7 C9 119.3(5) . . ?
C6 C7 C9 121.6(6) . . ?
C2 C3 C4 122.2(6) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
O2 C6 C7 121.1(6) . . ?
O2 C6 C4 119.4(5) . . ?
C7 C6 C4 119.5(6) . . ?
C13 N2 C14 116.4(6) . . ?
C12 C11 C10 118.7(6) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C2 C8 C7 122.3(5) . . ?
C2 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C11 C10 C14 117.5(6) . . ?
C11 C10 N1 117.5(6) . . ?
C14 C10 N1 125.0(6) . . ?
N1 C9 C7 122.1(5) . . ?
N1 C9 H9 119.0 . . ?
C7 C9 H9 119.0 . . ?
N2 C14 C10 124.2(6) . . ?
N2 C14 H14 117.9 . . ?
C10 C14 H14 117.9 . . ?
N2 C13 C12 123.4(7) . . ?
N2 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C13 C12 C11 119.8(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C5 C4 125.7(7) . . ?
O1 C5 H5 117.2 . . ?
C4 C5 H5 117.2 . . ?

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
C8 C2 C3 C4 -0.9(9) . . . . ?
C1 C2 C3 C4 178.6(6) . . . . ?
C6 C4 C3 C2 0.2(10) . . . . ?
C5 C4 C3 C2 179.2(6) . . . . ?
C8 C7 C6 O2 179.6(6) . . . . ?
C9 C7 C6 O2 -0.5(9) . . . . ?
C8 C7 C6 C4 -0.4(9) . . . . ?
C9 C7 C6 C4 179.4(6) . . . . ?
C3 C4 C6 O2 -179.6(6) . . . . ?
C5 C4 C6 O2 1.4(10) . . . . ?
C3 C4 C6 C7 0.5(9) . . . . ?
C5 C4 C6 C7 -178.5(6) . . . . ?
C3 C2 C8 C7 1.0(9) . . . . ?
C1 C2 C8 C7 -178.5(6) . . . . ?
C6 C7 C8 C2 -0.4(9) . . . . ?
C9 C7 C8 C2 179.8(6) . . . . ?
C12 C11 C10 C14 3.5(9) . . . . ?
C12 C11 C10 N1 -178.2(6) . . . . ?
C9 N1 C10 C11 169.1(6) . . . . ?
C9 N1 C10 C14 -12.7(9) . . . . ?
C10 N1 C9 C7 -178.7(5) . . . . ?
C8 C7 C9 N1 -178.1(6) . . . . ?
C6 C7 C9 N1 2.1(9) . . . . ?
C13 N2 C14 C10 0.6(11) . . . . ?
C11 C10 C14 N2 -2.9(10) . . . . ?
N1 C10 C14 N2 178.9(6) . . . . ?
C14 N2 C13 C12 1.0(12) . . . . ?
N2 C13 C12 C11 -0.3(12) . . . . ?
C10 C11 C12 C13 -2.0(10) . . . . ?
C3 C4 C5 O1 5.3(13) . . . . ?
C6 C4 C5 O1 -175.7(8) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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 1977160'
loop_
_audit_author_name
_audit_author_address
'Partha Roy'
;Jadavpur University
India
;
_audit_update_record             
;
2020-01-13 deposited with the CCDC.	2020-04-13 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         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   7.4213(10)
_cell_length_b                   4.2957(5)
_cell_length_c                   19.130(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.660(4)
_cell_angle_gamma                90
_cell_volume                     609.21(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      0.963
_cell_measurement_theta_max      0.987

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS
_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  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8157
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.885
_reflns_number_total             2695
_reflns_number_gt                1805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.756
_reflns_Friedel_fraction_full    0.772

_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-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)+(0.1085P)²+0.1797P] 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_abs_structure_details 
;
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     171
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.2011
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.094
_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 0.0747(6) 1.0611(12) 0.6046(3) 0.0768(14) Uani 1 1 d . . . . .
O2 O 0.3107(4) 0.4612(10) 0.47431(19) 0.0593(11) Uani 1 1 d . . . . .
H2 H 0.371815 0.343779 0.451276 0.089 Uiso 1 1 calc R U . . .
N1 N 0.5900(5) 0.1414(11) 0.4411(2) 0.0476(10) Uani 1 1 d . . . . .
C2 C 0.6119(6) 0.7692(12) 0.6503(3) 0.0453(11) Uani 1 1 d . . . . .
C4 C 0.3325(5) 0.7639(12) 0.5774(2) 0.0455(12) Uani 1 1 d . . . . .
C11 C 0.8455(6) -0.1525(11) 0.4117(2) 0.0422(10) Uani 1 1 d . . . . .
H11 H 0.904623 -0.092458 0.453491 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6752(7) 0.2507(12) 0.4965(3) 0.0424(10) Uani 1 1 d D . . . .
C3 C 0.4368(7) 0.8651(12) 0.6369(3) 0.0445(11) Uani 1 1 d . . . . .
H3 H 0.385214 1.001224 0.668040 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7216(8) 0.8849(14) 0.7131(3) 0.0585(14) Uani 1 1 d . . . . .
H1A H 0.839603 0.793143 0.713739 0.088 Uiso 1 1 calc R U . . .
H1B H 0.732080 1.107355 0.710790 0.088 Uiso 1 1 calc R U . . .
H1C H 0.663049 0.827980 0.754981 0.088 Uiso 1 1 calc R U . . .
C6 C 0.4090(6) 0.5607(12) 0.5305(2) 0.0436(11) Uani 1 1 d . . . . .
C7 C 0.5893(6) 0.4595(11) 0.5431(2) 0.0416(11) Uani 1 1 d . . . . .
C8 C 0.6868(5) 0.5660(11) 0.6025(2) 0.0414(10) Uani 1 1 d . . . . .
H8 H 0.805233 0.499690 0.610569 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1486(7) 0.8817(16) 0.5654(3) 0.0601(15) Uani 1 1 d D . . . .
C10 C 0.6781(7) -0.0590(11) 0.3955(2) 0.0444(11) Uani 1 1 d . . . . .
C12 C 0.9257(8) -0.3345(16) 0.3665(3) 0.0650(16) Uani 1 1 d . . . . .
H12 H 1.043019 -0.399965 0.377560 0.078 Uiso 1 1 calc R U . . .
C14 C 0.6694(9) -0.3340(15) 0.2878(3) 0.0671(17) Uani 1 1 d . . . . .
H14 H 0.610280 -0.395494 0.246170 0.080 Uiso 1 1 calc R U . . .
N2 N 0.5849(8) -0.1465(15) 0.3341(3) 0.0812(18) Uani 1 1 d . . . . .
C13 C 0.8452(9) -0.4309(16) 0.3043(3) 0.0681(17) Uani 1 1 d . . . . .
H13 H 0.906397 -0.557697 0.273982 0.082 Uiso 1 1 calc R U . . .
H9 H 0.773(4) 0.208(13) 0.507(3) 0.043(15) Uiso 1 1 d D . . . .
H5 H 0.092(8) 0.861(16) 0.531(2) 0.07(2) Uiso 1 1 d 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 C5 1.222(7) . ?
O2 C6 1.341(6) . ?
O2 H2 0.8200 . ?
N1 C9 1.297(6) . ?
N1 C10 1.408(7) . ?
C2 C3 1.376(7) . ?
C2 C8 1.397(7) . ?
C2 C1 1.505(7) . ?
C4 C6 1.392(7) . ?
C4 C3 1.414(7) . ?
C4 C5 1.464(7) . ?
C11 C12 1.328(8) . ?
C11 C10 1.329(7) . ?
C11 H11 0.9300 . ?
C9 C7 1.435(7) . ?
C9 H9 0.77(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 C7 1.417(6) . ?
C7 C8 1.395(6) . ?
C8 H8 0.9300 . ?
C5 H5 0.77(3) . ?
C10 N2 1.387(7) . ?
C12 C13 1.369(8) . ?
C12 H12 0.9300 . ?
C14 N2 1.371(8) . ?
C14 C13 1.392(10) . ?
C14 H14 0.9300 . ?
C13 H13 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
C6 O2 H2 109.5 . . ?
C9 N1 C10 120.3(4) . . ?
C3 C2 C8 117.8(4) . . ?
C3 C2 C1 121.4(5) . . ?
C8 C2 C1 120.8(5) . . ?
C6 C4 C3 119.2(4) . . ?
C6 C4 C5 121.4(4) . . ?
C3 C4 C5 119.4(5) . . ?
C12 C11 C10 118.0(5) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N1 C9 C7 121.3(4) . . ?
N1 C9 H9 123(4) . . ?
C7 C9 H9 115(4) . . ?
C2 C3 C4 122.3(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C6 C4 119.6(4) . . ?
O2 C6 C7 120.9(4) . . ?
C4 C6 C7 119.5(4) . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 C9 118.8(4) . . ?
C6 C7 C9 122.0(4) . . ?
C7 C8 C2 122.0(4) . . ?
C7 C8 H8 119.0 . . ?
C2 C8 H8 119.0 . . ?
O1 C5 C4 124.3(5) . . ?
O1 C5 H5 111(5) . . ?
C4 C5 H5 124(5) . . ?
C11 C10 N2 122.7(5) . . ?
C11 C10 N1 119.8(4) . . ?
N2 C10 N1 117.6(5) . . ?
C11 C12 C13 123.6(6) . . ?
C11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
N2 C14 C13 118.8(6) . . ?
N2 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 N2 C10 118.8(6) . . ?
C12 C13 C14 118.2(6) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.168

