# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2NA3ENQ
_database_code_depnum_ccdc_archive 'CCDC 1505004'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N2 O2'
_chemical_formula_sum            'C16 H17 N2 O2'
_chemical_formula_weight         269.32

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   14.6578(15)
_cell_length_b                   8.7453(11)
_cell_length_c                   22.209(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.460(7)
_cell_angle_gamma                90
_cell_volume                     2730.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      24.68

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38016
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2409
_reflns_number_gt                1640
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0668P)²+3.6578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2409
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.13155(16) 0.0779(3) 0.05554(10) 0.0689(7) Uani 1 1 d . . . . .
O3 O -0.12700(16) 0.4445(3) -0.11700(10) 0.0670(7) Uani 1 1 d . . . . .
N1 N -0.03739(15) 0.2278(2) 0.07643(10) 0.0377(6) Uani 1 1 d . . . . .
N2 N -0.14143(16) 0.3812(3) 0.00635(11) 0.0457(6) Uani 1 1 d . . . . .
H2 H -0.1890 0.4394 -0.0109 0.055 Uiso 1 1 calc R U . . .
C1 C 0.07550(18) 0.1645(3) 0.01721(13) 0.0411(7) Uani 1 1 d . . . . .
C2 C -0.00665(18) 0.2388(3) 0.02635(12) 0.0364(6) Uani 1 1 d . . . . .
C3 C -0.07199(18) 0.3334(3) -0.01626(12) 0.0378(6) Uani 1 1 d . . . . .
C4 C -0.0672(2) 0.3657(3) -0.07753(12) 0.0416(7) Uani 1 1 d . . . . .
C5 C 0.0275(2) 0.3168(3) -0.14621(14) 0.0551(8) Uani 1 1 d . . . . .
H5 H -0.0158 0.3749 -0.1762 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1048(2) 0.2517(4) -0.15804(16) 0.0638(9) Uani 1 1 d . . . . .
H6 H 0.1137 0.2658 -0.1975 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1727(2) 0.1637(4) -0.11344(16) 0.0609(9) Uani 1 1 d . . . . .
H7 H 0.2247 0.1236 -0.1242 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1637(2) 0.1371(3) -0.05666(14) 0.0497(8) Uani 1 1 d . . . . .
H8 H 0.2079 0.0792 -0.0271 0.060 Uiso 1 1 calc R U . . .
C9 C 0.08515(19) 0.2002(3) -0.04396(13) 0.0403(7) Uani 1 1 d . . . . .
C10 C 0.01688(19) 0.2927(3) -0.08898(12) 0.0401(7) Uani 1 1 d . . . . .
C11 C -0.11869(19) 0.3167(3) 0.06177(12) 0.0394(7) Uani 1 1 d . . . . .
C12 C 0.00802(19) 0.1367(3) 0.13369(12) 0.0418(7) Uani 1 1 d . . . . .
H12A H 0.0324 0.0427 0.1209 0.050 Uiso 1 1 calc R U . . .
H12B H -0.0405 0.1090 0.1537 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0909(2) 0.2185(3) 0.18322(13) 0.0531(8) Uani 1 1 d . . . . .
H13A H 0.1361 0.2568 0.1623 0.064 Uiso 1 1 calc R U . . .
H13B H 0.0653 0.3058 0.2000 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1442(2) 0.1145(4) 0.23847(13) 0.0588(9) Uani 1 1 d . . . . .
H14A H 0.1848 0.1788 0.2707 0.071 Uiso 1 1 calc R U . . .
H14B H 0.0974 0.0685 0.2562 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2031(3) -0.0087(5) 0.22414(18) 0.0819(12) Uani 1 1 d . . . . .
H15A H 0.1636 -0.0773 0.1941 0.123 Uiso 1 1 calc R U . . .
H15B H 0.2335 -0.0636 0.2619 0.123 Uiso 1 1 calc R U . . .
H15C H 0.2505 0.0345 0.2070 0.123 Uiso 1 1 calc R U . . .
C16 C -0.1759(2) 0.3332(4) 0.10318(14) 0.0567(8) Uani 1 1 d . . . . .
H16A H -0.1371 0.3661 0.1436 0.085 Uiso 1 1 calc R U . . .
H16B H -0.2048 0.2369 0.1074 0.085 Uiso 1 1 calc R U . . .
H16C H -0.2246 0.4079 0.0866 0.085 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 C1 1.256(3) . ?
O3 C4 1.255(3) . ?
N1 C2 1.317(3) . ?
N1 C11 1.383(3) . ?
N1 C12 1.488(3) . ?
N2 C11 1.308(3) . ?
N2 C3 1.324(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.433(4) . ?
C1 C9 1.439(4) . ?
C2 C3 1.408(3) . ?
C3 C4 1.411(4) . ?
C4 C10 1.473(4) . ?
C5 C10 1.340(4) . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.325(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.445(4) . ?
C11 C16 1.417(4) . ?
C12 C13 1.563(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.549(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.470(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 C11 103.8(2) . . ?
C2 N1 C12 125.7(2) . . ?
C11 N1 C12 130.5(2) . . ?
C11 N2 C3 101.7(2) . . ?
C11 N2 H2 129.2 . . ?
C3 N2 H2 129.2 . . ?
O2 C1 C2 126.3(3) . . ?
O2 C1 C9 123.4(2) . . ?
C2 C1 C9 110.3(2) . . ?
N1 C2 C3 106.3(2) . . ?
N1 C2 C1 126.1(2) . . ?
C3 C2 C1 127.6(2) . . ?
N2 C3 C2 112.4(2) . . ?
N2 C3 C4 123.8(2) . . ?
C2 C3 C4 123.8(2) . . ?
O3 C4 C3 124.6(3) . . ?
O3 C4 C10 124.8(2) . . ?
C3 C4 C10 110.6(2) . . ?
C10 C5 C6 116.4(3) . . ?
C10 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C5 C6 C7 123.5(3) . . ?
C5 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 116.1(3) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C8 C9 C1 114.7(3) . . ?
C8 C9 C10 122.6(3) . . ?
C1 C9 C10 122.7(2) . . ?
C5 C10 C9 120.1(3) . . ?
C5 C10 C4 115.0(3) . . ?
C9 C10 C4 124.9(2) . . ?
N2 C11 N1 115.9(2) . . ?
N2 C11 C16 121.8(3) . . ?
N1 C11 C16 122.3(2) . . ?
N1 C12 C13 115.2(2) . . ?
N1 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N1 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 113.9(2) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 H14A 108.0 . . ?
C13 C14 H14A 108.0 . . ?
C15 C14 H14B 108.0 . . ?
C13 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C2 C3 -0.5(3) . . . . ?
C12 N1 C2 C3 178.8(2) . . . . ?
C11 N1 C2 C1 -178.7(2) . . . . ?
C12 N1 C2 C1 0.6(4) . . . . ?
O2 C1 C2 N1 -0.5(5) . . . . ?
C9 C1 C2 N1 178.3(2) . . . . ?
O2 C1 C2 C3 -178.3(3) . . . . ?
C9 C1 C2 C3 0.5(4) . . . . ?
C11 N2 C3 C2 0.0(3) . . . . ?
C11 N2 C3 C4 176.3(3) . . . . ?
N1 C2 C3 N2 0.4(3) . . . . ?
C1 C2 C3 N2 178.6(2) . . . . ?
N1 C2 C3 C4 -176.0(2) . . . . ?
C1 C2 C3 C4 2.2(4) . . . . ?
N2 C3 C4 O3 1.0(4) . . . . ?
C2 C3 C4 O3 176.9(3) . . . . ?
N2 C3 C4 C10 -178.3(2) . . . . ?
C2 C3 C4 C10 -2.4(4) . . . . ?
C10 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C1 177.8(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
O2 C1 C9 C8 -2.8(4) . . . . ?
C2 C1 C9 C8 178.4(2) . . . . ?
O2 C1 C9 C10 176.2(3) . . . . ?
C2 C1 C9 C10 -2.6(4) . . . . ?
C6 C5 C10 C9 -0.7(4) . . . . ?
C6 C5 C10 C4 179.5(3) . . . . ?
C8 C9 C10 C5 1.7(4) . . . . ?
C1 C9 C10 C5 -177.2(3) . . . . ?
C8 C9 C10 C4 -178.6(3) . . . . ?
C1 C9 C10 C4 2.5(4) . . . . ?
O3 C4 C10 C5 0.6(4) . . . . ?
C3 C4 C10 C5 179.9(2) . . . . ?
O3 C4 C10 C9 -179.1(3) . . . . ?
C3 C4 C10 C9 0.2(4) . . . . ?
C3 N2 C11 N1 -0.3(3) . . . . ?
C3 N2 C11 C16 -178.3(3) . . . . ?
C2 N1 C11 N2 0.6(3) . . . . ?
C12 N1 C11 N2 -178.7(2) . . . . ?
C2 N1 C11 C16 178.5(3) . . . . ?
C12 N1 C11 C16 -0.8(4) . . . . ?
C2 N1 C12 C13 84.4(3) . . . . ?
C11 N1 C12 C13 -96.4(3) . . . . ?
N1 C12 C13 C14 -173.3(2) . . . . ?
C12 C13 C14 C15 69.5(4) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_mo_2NANQ_0m
_database_code_depnum_ccdc_archive 'CCDC 1505005'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cl N O3'
_chemical_formula_sum            'C12 H8 Cl N O3'
_chemical_formula_weight         249.64

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'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   10.1825(5)
_cell_length_b                   6.9858(3)
_cell_length_c                   15.3143(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.202(2)
_cell_angle_gamma                90
_cell_volume                     1084.86(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      28.24

_exptl_crystal_description       PLATE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.346
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31340
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         28.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2734
_reflns_number_gt                2057
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0391P)²+1.1084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2734
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 0.32887(5) 0.17137(10) 0.92781(4) 0.0514(2) Uani 1 1 d . . . . .
O1 O 0.12378(15) 0.1977(3) 1.04514(9) 0.0472(4) Uani 1 1 d . . . . .
O2 O -0.04861(16) 0.3779(3) 0.71679(10) 0.0559(5) Uani 1 1 d . . . . .
O3 O 0.37085(16) 0.5108(3) 0.81799(10) 0.0518(4) Uani 1 1 d . . . . .
N1 N 0.21013(16) 0.3264(3) 0.74909(11) 0.0358(4) Uani 1 1 d . . . . .
H1 H 0.1828 0.2743 0.6999 0.043 Uiso 1 1 calc R U . . .
C1 C 0.08257(19) 0.2419(3) 0.97108(12) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.17130(18) 0.2498(3) 0.89962(13) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.13091(19) 0.3078(3) 0.81776(12) 0.0302(4) Uani 1 1 d . . . . .
C4 C -0.01217(19) 0.3426(3) 0.79310(12) 0.0335(4) Uani 1 1 d . . . . .
C5 C -0.2370(2) 0.3772(3) 0.84107(15) 0.0395(5) Uani 1 1 d . . . . .
H5 H -0.2679 0.4066 0.7836 0.047 Uiso 1 1 calc R U . . .
C6 C -0.3227(2) 0.3761(3) 0.90605(16) 0.0450(6) Uani 1 1 d . . . . .
H6 H -0.4111 0.4063 0.8925 0.054 Uiso 1 1 calc R U . . .
C7 C -0.2772(2) 0.3301(3) 0.99117(16) 0.0446(5) Uani 1 1 d . . . . .
H7 H -0.3354 0.3294 1.0346 0.054 Uiso 1 1 calc R U . . .
C8 C -0.1462(2) 0.2853(3) 1.01242(14) 0.0376(5) Uani 1 1 d . . . . .
H8 H -0.1166 0.2529 1.0698 0.045 Uiso 1 1 calc R U . . .
C9 C -0.05853(18) 0.2887(3) 0.94792(12) 0.0292(4) Uani 1 1 d . . . . .
C10 C -0.10462(18) 0.3344(3) 0.86186(12) 0.0307(4) Uani 1 1 d . . . . .
C11 C 0.3294(2) 0.4220(3) 0.75359(14) 0.0364(5) Uani 1 1 d . . . . .
C12 C 0.4027(2) 0.4022(4) 0.67359(15) 0.0488(6) Uani 1 1 d . . . . .
H12A H 0.4638 0.5063 0.6713 0.073 Uiso 1 1 calc R U . . .
H12B H 0.3413 0.4046 0.6222 0.073 Uiso 1 1 calc R U . . .
H12C H 0.4499 0.2832 0.6760 0.073 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
Cl1 C2 1.713(2) . ?
O1 C1 1.213(2) . ?
O2 C4 1.219(2) . ?
O3 C11 1.208(3) . ?
N1 C11 1.382(3) . ?
N1 C3 1.388(2) . ?
C1 C9 1.485(3) . ?
C1 C2 1.482(3) . ?
C2 C3 1.346(3) . ?
C3 C4 1.491(3) . ?
C4 C10 1.476(3) . ?
C5 C6 1.381(3) . ?
C5 C10 1.390(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.395(3) . ?
C11 C12 1.497(3) . ?

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 N1 C3 125.15(17) . . ?
O1 C1 C9 121.64(18) . . ?
O1 C1 C2 121.16(18) . . ?
C9 C1 C2 117.20(16) . . ?
C3 C2 C1 122.93(18) . . ?
C3 C2 Cl1 122.08(15) . . ?
C1 C2 Cl1 114.95(14) . . ?
C2 C3 N1 125.75(18) . . ?
C2 C3 C4 119.60(17) . . ?
N1 C3 C4 114.47(16) . . ?
O2 C4 C10 122.24(19) . . ?
O2 C4 C3 118.77(18) . . ?
C10 C4 C3 118.99(16) . . ?
C6 C5 C10 119.8(2) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 120.6(2) . . ?
C7 C8 C9 119.8(2) . . ?
C8 C9 C10 119.50(18) . . ?
C8 C9 C1 119.75(18) . . ?
C10 C9 C1 120.75(17) . . ?
C5 C10 C9 120.13(18) . . ?
C5 C10 C4 119.78(18) . . ?
C9 C10 C4 120.07(17) . . ?
O3 C11 N1 121.94(19) . . ?
O3 C11 C12 123.5(2) . . ?
N1 C11 C12 114.55(19) . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_AMPNQ
_database_code_depnum_ccdc_archive 'CCDC 1814961'
loop_
_audit_author_name
_audit_author_address
'SAMIR SHAIKH' 'NATIONAL CHEMICAL LABORATORY PUNE, INDIA'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.	2020-03-17 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         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30

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/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                   20.7144(13)
_cell_length_b                   4.6497(3)
_cell_length_c                   14.7226(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.849(3)
_cell_angle_gamma                90
_cell_volume                     1341.97(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      29.09

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            25638
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         28.788
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3472
_reflns_number_gt                3190
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0456P)²+0.9913P] 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         3472
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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 0.38013(5) 0.6315(2) 0.38888(7) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.26609(5) 0.6111(2) 0.66579(7) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.14328(5) 0.4489(2) 0.48827(8) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.26732(6) 0.9255(3) 0.35734(8) 0.0152(2) Uani 1 1 d . . . . .
N2 N 0.19363(6) 0.8849(2) 0.50260(8) 0.0117(2) Uani 1 1 d . . . . .
C1 C 0.35326(6) 0.6126(3) 0.45112(9) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.28776(6) 0.7775(3) 0.43968(9) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.25787(6) 0.7597(3) 0.51063(9) 0.0115(2) Uani 1 1 d . . . . .
C4 C 0.28945(6) 0.6018(3) 0.59897(9) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.37562(7) 0.2387(3) 0.68631(9) 0.0158(3) Uani 1 1 d . . . . .
H5 H 0.3546 0.2340 0.7349 0.019 Uiso 1 1 calc R U . . .
C6 C 0.43181(7) 0.0658(3) 0.69408(10) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.4487 -0.0594 0.7475 0.022 Uiso 1 1 calc R U . . .
C7 C 0.46344(7) 0.0754(3) 0.62390(10) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.5024 -0.0408 0.6301 0.022 Uiso 1 1 calc R U . . .
C8 C 0.43824(7) 0.2544(3) 0.54470(10) 0.0164(3) Uani 1 1 d . . . . .
H8 H 0.4598 0.2605 0.4967 0.020 Uiso 1 1 calc R U . . .
C9 C 0.38119(6) 0.4250(3) 0.53607(9) 0.0131(3) Uani 1 1 d . . . . .
C10 C 0.35011(6) 0.4191(3) 0.60716(9) 0.0127(3) Uani 1 1 d . . . . .
C11 C 0.20501(7) 1.0931(3) 0.31678(9) 0.0158(3) Uani 1 1 d . . . . .
H11A H 0.2121 1.2332 0.2702 0.019 Uiso 1 1 calc R U . . .
H11B H 0.1957 1.2028 0.3688 0.019 Uiso 1 1 calc R U . . .
C12 C 0.14325(7) 0.9067(3) 0.26647(10) 0.0187(3) Uani 1 1 d . . . . .
H12A H 0.1513 0.8040 0.2122 0.022 Uiso 1 1 calc R U . . .
H12B H 0.1370 0.7613 0.3120 0.022 Uiso 1 1 calc R U . . .
C13 C 0.07894(8) 1.0887(4) 0.22916(13) 0.0324(4) Uani 1 1 d . . . . .
H13A H 0.0710 1.1905 0.2828 0.049 Uiso 1 1 calc R U . . .
H13B H 0.0399 0.9640 0.1981 0.049 Uiso 1 1 calc R U . . .
H13C H 0.0846 1.2288 0.1825 0.049 Uiso 1 1 calc R U . . .
C14 C 0.14018(7) 0.7118(3) 0.49622(9) 0.0138(3) Uani 1 1 d . . . . .
C15 C 0.07464(7) 0.8540(3) 0.49515(10) 0.0174(3) Uani 1 1 d . . . . .
H15A H 0.0411 0.8383 0.4308 0.026 Uiso 1 1 calc R U . . .
H15B H 0.0832 1.0573 0.5123 0.026 Uiso 1 1 calc R U . . .
H15C H 0.0570 0.7588 0.5417 0.026 Uiso 1 1 calc R U . . .
H2N H 0.1877(9) 1.072(4) 0.5080(13) 0.020(4) Uiso 1 1 d . . . . .
H1N H 0.2909(10) 0.891(4) 0.3175(14) 0.025(5) 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 C1 1.2194(16) . ?
O2 C4 1.2293(16) . ?
O3 C14 1.2313(17) . ?
N1 C2 1.3381(16) . ?
N1 C11 1.4601(17) . ?
N1 H1N 0.89(2) . ?
N2 C14 1.3474(17) . ?
N2 C3 1.4219(16) . ?
N2 H2N 0.89(2) . ?
C1 C9 1.4809(18) . ?
C1 C2 1.5196(17) . ?
C2 C3 1.3781(17) . ?
C3 C4 1.4523(17) . ?
C4 C10 1.4890(18) . ?
C5 C6 1.3885(19) . ?
C5 C10 1.3939(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3946(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3950(18) . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5056(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 C11 128.62(11) . . ?
C2 N1 H1N 115.1(13) . . ?
C11 N1 H1N 115.3(12) . . ?
C14 N2 C3 119.17(11) . . ?
C14 N2 H2N 117.3(12) . . ?
C3 N2 H2N 123.1(12) . . ?
O1 C1 C9 121.90(12) . . ?
O1 C1 C2 119.24(12) . . ?
C9 C1 C2 118.82(11) . . ?
N1 C2 C3 129.01(12) . . ?
N1 C2 C1 111.69(11) . . ?
C3 C2 C1 119.30(11) . . ?
C2 C3 N2 123.36(11) . . ?
C2 C3 C4 121.78(11) . . ?
N2 C3 C4 114.83(11) . . ?
O2 C4 C3 121.27(12) . . ?
O2 C4 C10 119.70(12) . . ?
C3 C4 C10 119.01(11) . . ?
C6 C5 C10 119.91(13) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 120.24(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.18(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.63(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.23(12) . . ?
C8 C9 C1 120.02(12) . . ?
C10 C9 C1 119.74(11) . . ?
C5 C10 C9 119.78(12) . . ?
C5 C10 C4 119.54(11) . . ?
C9 C10 C4 120.67(11) . . ?
N1 C11 C12 112.80(11) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.00(13) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N2 122.18(12) . . ?
O3 C14 C15 120.63(12) . . ?
N2 C14 C15 117.15(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C2 C3 -4.8(2) . . . . ?
C11 N1 C2 C1 175.28(12) . . . . ?
O1 C1 C2 N1 0.89(18) . . . . ?
C9 C1 C2 N1 -176.88(11) . . . . ?
O1 C1 C2 C3 -179.06(12) . . . . ?
C9 C1 C2 C3 3.17(18) . . . . ?
N1 C2 C3 N2 5.9(2) . . . . ?
C1 C2 C3 N2 -174.21(11) . . . . ?
N1 C2 C3 C4 -176.08(13) . . . . ?
C1 C2 C3 C4 3.86(19) . . . . ?
C14 N2 C3 C2 112.19(14) . . . . ?
C14 N2 C3 C4 -66.00(15) . . . . ?
C2 C3 C4 O2 172.51(13) . . . . ?
N2 C3 C4 O2 -9.26(18) . . . . ?
C2 C3 C4 C10 -9.19(19) . . . . ?
N2 C3 C4 C10 169.03(11) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C8 -1.1(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C1 -178.95(12) . . . . ?
O1 C1 C9 C8 -2.6(2) . . . . ?
C2 C1 C9 C8 175.10(12) . . . . ?
O1 C1 C9 C10 177.54(13) . . . . ?
C2 C1 C9 C10 -4.75(18) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
C6 C5 C10 C4 179.44(12) . . . . ?
C8 C9 C10 C5 -0.99(19) . . . . ?
C1 C9 C10 C5 178.86(12) . . . . ?
C8 C9 C10 C4 179.60(12) . . . . ?
C1 C9 C10 C4 -0.55(18) . . . . ?
O2 C4 C10 C5 6.38(19) . . . . ?
C3 C4 C10 C5 -171.94(12) . . . . ?
O2 C4 C10 C9 -174.21(12) . . . . ?
C3 C4 C10 C9 7.47(18) . . . . ?
C2 N1 C11 C12 -80.10(17) . . . . ?
N1 C11 C12 C13 177.51(12) . . . . ?
C3 N2 C14 O3 -6.80(19) . . . . ?
C3 N2 C14 C15 175.64(11) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL'
####################################################################### 
# 
# 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_mo_IMENQ_0m
_database_code_depnum_ccdc_archive 'CCDC 1814962'
loop_
_audit_author_name
_audit_author_address
'SAMIR SHAIKH' 'NATIONAL CHEMICAL LABORATORY PUNE, INDIA'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.	2020-03-17 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         '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           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                   8.1220(3)
_cell_length_b                   15.5877(5)
_cell_length_c                   9.2916(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.5190(10)
_cell_angle_gamma                90
_cell_volume                     1138.78(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      36.37

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            17799
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2731
_reflns_number_gt                2511
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0434P)²+0.8241P] 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         2731
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.05598(12) 0.44033(6) 0.31497(10) 0.0223(2) Uani 1 1 d . . . . .
O2 O 0.48138(12) 0.58158(6) 0.80370(10) 0.0237(2) Uani 1 1 d . . . . .
N1 N 0.20423(12) 0.61814(6) 0.31719(11) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.38322(13) 0.67432(6) 0.51898(11) 0.0168(2) Uani 1 1 d . . . . .
C12 C 0.18179(17) 0.57704(10) 0.05423(14) 0.0245(3) Uani 1 1 d . . . . .
H12A H 0.2731 0.6163 0.0458 0.037 Uiso 1 1 calc R U . . .
H12B H 0.1004 0.5712 -0.0429 0.037 Uiso 1 1 calc R U . . .
H12C H 0.2302 0.5207 0.0876 0.037 Uiso 1 1 calc R U . . .
C11 C 0.09135(15) 0.61242(8) 0.16606(12) 0.0174(2) Uani 1 1 d . . . . .
H11A H 0.0465 0.6702 0.1337 0.021 Uiso 1 1 calc R U . . .
H11B H -0.0065 0.5750 0.1681 0.021 Uiso 1 1 calc R U . . .
C2 C 0.23260(14) 0.55586(7) 0.42550(12) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.15944(15) 0.47047(7) 0.42211(13) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.21892(15) 0.42168(7) 0.56492(13) 0.0153(2) Uani 1 1 d . . . . .
C8 C 0.16011(16) 0.33807(8) 0.57113(14) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.0850 0.3136 0.4859 0.023 Uiso 1 1 calc R U . . .
C7 C 0.21039(17) 0.29016(8) 0.70084(15) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.1723 0.2327 0.7036 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31697(16) 0.32689(8) 0.82666(15) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.3509 0.2944 0.9157 0.025 Uiso 1 1 calc R U . . .
C3 C 0.34194(15) 0.59221(7) 0.54813(13) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.29831(15) 0.68775(8) 0.37871(13) 0.0161(2) Uani 1 1 d . . . . .
C14 C 0.30146(18) 0.76955(8) 0.29735(14) 0.0221(3) Uani 1 1 d . . . . .
H14A H 0.1862 0.7933 0.2669 0.033 Uiso 1 1 calc R U . . .
H14B H 0.3438 0.7588 0.2091 0.033 Uiso 1 1 calc R U . . .
H14C H 0.3765 0.8106 0.3624 0.033 Uiso 1 1 calc R U . . .
C4 C 0.39337(15) 0.54808(7) 0.69154(13) 0.0161(2) Uani 1 1 d . . . . .
C10 C 0.32775(15) 0.45822(7) 0.69171(13) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.37399(15) 0.41058(8) 0.82299(13) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.4447 0.4355 0.9100 0.022 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
O1 C1 1.2241(15) . ?
O2 C4 1.2232(15) . ?
N1 C13 1.3671(15) . ?
N1 C2 1.3755(14) . ?
N1 C11 1.4747(14) . ?
N2 C13 1.3294(15) . ?
N2 C3 1.3674(15) . ?
C12 C11 1.5186(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C3 1.3786(16) . ?
C2 C1 1.4548(16) . ?
C1 C9 1.5004(16) . ?
C9 C8 1.3942(17) . ?
C9 C10 1.4041(16) . ?
C8 C7 1.3894(18) . ?
C8 H8 0.9500 . ?
C7 C6 1.3916(19) . ?
C7 H7 0.9500 . ?
C6 C5 1.3876(17) . ?
C6 H6 0.9500 . ?
C3 C4 1.4643(16) . ?
C13 C14 1.4858(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C10 1.4988(16) . ?
C10 C5 1.3966(16) . ?
C5 H5 0.9500 . ?

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
C13 N1 C2 106.30(9) . . ?
C13 N1 C11 126.51(10) . . ?
C2 N1 C11 127.17(10) . . ?
C13 N2 C3 104.41(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C11 C12 112.43(10) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C3 C2 N1 105.65(10) . . ?
C3 C2 C1 124.67(10) . . ?
N1 C2 C1 129.59(10) . . ?
O1 C1 C2 124.21(11) . . ?
O1 C1 C9 121.86(11) . . ?
C2 C1 C9 113.92(10) . . ?
C8 C9 C10 119.64(11) . . ?
C8 C9 C1 118.21(11) . . ?
C10 C9 C1 122.13(10) . . ?
C7 C8 C9 120.61(12) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C7 C6 119.55(12) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C5 C6 C7 120.49(11) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N2 C3 C2 111.10(10) . . ?
N2 C3 C4 126.29(10) . . ?
C2 C3 C4 122.47(11) . . ?
N2 C13 N1 112.53(10) . . ?
N2 C13 C14 124.27(11) . . ?
N1 C13 C14 123.19(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C4 C3 123.18(11) . . ?
O2 C4 C10 122.01(11) . . ?
C3 C4 C10 114.81(10) . . ?
C5 C10 C9 119.47(11) . . ?
C5 C10 C4 118.69(11) . . ?
C9 C10 C4 121.83(10) . . ?
C6 C5 C10 120.20(12) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?

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
C13 N1 C11 C12 92.45(14) . . . . ?
C2 N1 C11 C12 -89.44(14) . . . . ?
C13 N1 C2 C3 0.66(12) . . . . ?
C11 N1 C2 C3 -177.76(10) . . . . ?
C13 N1 C2 C1 177.28(12) . . . . ?
C11 N1 C2 C1 -1.14(19) . . . . ?
C3 C2 C1 O1 176.25(12) . . . . ?
N1 C2 C1 O1 0.2(2) . . . . ?
C3 C2 C1 C9 -2.35(17) . . . . ?
N1 C2 C1 C9 -178.40(11) . . . . ?
O1 C1 C9 C8 3.38(17) . . . . ?
C2 C1 C9 C8 -177.98(10) . . . . ?
O1 C1 C9 C10 -175.18(11) . . . . ?
C2 C1 C9 C10 3.46(16) . . . . ?
C10 C9 C8 C7 -1.05(18) . . . . ?
C1 C9 C8 C7 -179.65(11) . . . . ?
C9 C8 C7 C6 1.65(18) . . . . ?
C8 C7 C6 C5 -0.44(18) . . . . ?
C13 N2 C3 C2 0.20(13) . . . . ?
C13 N2 C3 C4 -175.53(11) . . . . ?
N1 C2 C3 N2 -0.55(13) . . . . ?
C1 C2 C3 N2 -177.38(10) . . . . ?
N1 C2 C3 C4 175.37(10) . . . . ?
C1 C2 C3 C4 -1.47(18) . . . . ?
C3 N2 C13 N1 0.24(13) . . . . ?
C3 N2 C13 C14 179.14(11) . . . . ?
C2 N1 C13 N2 -0.58(13) . . . . ?
C11 N1 C13 N2 177.85(10) . . . . ?
C2 N1 C13 C14 -179.49(11) . . . . ?
C11 N1 C13 C14 -1.06(18) . . . . ?
N2 C3 C4 O2 0.1(2) . . . . ?
C2 C3 C4 O2 -175.14(12) . . . . ?
N2 C3 C4 C10 179.33(11) . . . . ?
C2 C3 C4 C10 4.06(16) . . . . ?
C8 C9 C10 C5 -0.76(17) . . . . ?
C1 C9 C10 C5 177.78(11) . . . . ?
C8 C9 C10 C4 -179.42(11) . . . . ?
C1 C9 C10 C4 -0.88(17) . . . . ?
O2 C4 C10 C5 -2.33(18) . . . . ?
C3 C4 C10 C5 178.47(10) . . . . ?
O2 C4 C10 C9 176.34(11) . . . . ?
C3 C4 C10 C9 -2.86(16) . . . . ?
C7 C6 C5 C10 -1.38(18) . . . . ?
C9 C10 C5 C6 1.97(18) . . . . ?
C4 C10 C5 C6 -179.33(11) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL'
####################################################################### 
# 
# 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_cu_amenq_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1814958'
loop_
_audit_author_name
_audit_author_address
'SHAIKH SAMIR' 'NATIONAL CHEMICAL LABORATORY, PUNE INDIA'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.	2020-03-17 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         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   37.44(5)
_cell_length_b                   4.665(13)
_cell_length_c                   14.44(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.0(2)
_cell_angle_gamma                90
_cell_volume                     2496(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3357
_cell_measurement_theta_min      4.77
_cell_measurement_theta_max      64.84

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.809
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_process_details   SADABS,BRUKER'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            10094
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.771
_diffrn_reflns_theta_max         66.728
_diffrn_reflns_theta_full        66.728
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2137
_reflns_number_gt                1318
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1148P)²+1.0269P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2137
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.015
_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 0.31860(7) 0.4293(7) 0.58873(18) 0.0778(9) Uani 1 1 d . . . . .
O2 O 0.37561(6) 0.4233(6) 0.27685(16) 0.0675(8) Uani 1 1 d . . . . .
O3 O 0.44182(6) 0.2974(5) 0.4248(2) 0.0722(9) Uani 1 1 d . . . . .
N1 N 0.37680(8) 0.7372(6) 0.5882(2) 0.0553(8) Uani 1 1 d . . . . .
N2 N 0.41291(7) 0.7180(6) 0.41849(18) 0.0431(7) Uani 1 1 d . . . . .
C1 C 0.33188(9) 0.4189(7) 0.5180(2) 0.0496(8) Uani 1 1 d . . . . .
C2 C 0.36542(8) 0.5921(6) 0.5105(2) 0.0432(8) Uani 1 1 d . . . . .
C3 C 0.37966(8) 0.5852(6) 0.4294(2) 0.0414(7) Uani 1 1 d . . . . .
C4 C 0.36322(8) 0.4186(7) 0.3500(2) 0.0451(8) Uani 1 1 d . . . . .
C5 C 0.31659(9) 0.0613(7) 0.2849(3) 0.0553(9) Uani 1 1 d . . . . .
H5 H 0.3267 0.0593 0.2295 0.066 Uiso 1 1 calc R U . . .
C6 C 0.28726(9) -0.1085(8) 0.2933(3) 0.0624(10) Uani 1 1 d . . . . .
H6 H 0.2776 -0.2246 0.2436 0.075 Uiso 1 1 calc R U . . .
C7 C 0.27224(9) -0.1083(8) 0.3734(3) 0.0653(11) Uani 1 1 d . . . . .
H7 H 0.2523 -0.2230 0.3787 0.078 Uiso 1 1 calc R U . . .
C8 C 0.28658(9) 0.0618(8) 0.4464(3) 0.0599(10) Uani 1 1 d . . . . .
H8 H 0.2763 0.0612 0.5014 0.072 Uiso 1 1 calc R U . . .
C9 C 0.31623(8) 0.2353(7) 0.4399(2) 0.0462(8) Uani 1 1 d . . . . .
C10 C 0.33127(8) 0.2361(7) 0.3583(2) 0.0452(8) Uani 1 1 d . . . . .
C11 C 0.40746(10) 0.9278(8) 0.6115(3) 0.0623(10) Uani 1 1 d . . . . .
H11A H 0.4019 1.0655 0.6577 0.075 Uiso 1 1 calc R U . . .
H11B H 0.4114 1.0335 0.5559 0.075 Uiso 1 1 calc R U . . .
C12 C 0.44137(11) 0.7727(11) 0.6488(3) 0.0876(14) Uani 1 1 d . . . . .
H12A H 0.4377 0.6685 0.7040 0.131 Uiso 1 1 calc R U . . .
H12B H 0.4606 0.9085 0.6638 0.131 Uiso 1 1 calc R U . . .
H12C H 0.4476 0.6414 0.6023 0.131 Uiso 1 1 calc R U . . .
C13 C 0.44198(8) 0.5565(6) 0.4109(2) 0.0477(8) Uani 1 1 d . . . . .
C14 C 0.47465(9) 0.7046(8) 0.3868(3) 0.0671(11) Uani 1 1 d . . . . .
H14A H 0.4921 0.7231 0.4419 0.101 Uiso 1 1 calc R U . . .
H14B H 0.4681 0.8915 0.3621 0.101 Uiso 1 1 calc R U . . .
H14C H 0.4848 0.5947 0.3406 0.101 Uiso 1 1 calc R U . . .
H1N H 0.3652(10) 0.672(8) 0.635(3) 0.067(11) Uiso 1 1 d . . . . .
H2N H 0.4132(9) 0.897(8) 0.413(2) 0.053(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 C1 1.198(5) . ?
O2 C4 1.212(5) . ?
O3 C13 1.225(5) . ?
N1 C2 1.328(5) . ?
N1 C11 1.454(5) . ?
N1 H1N 0.91(4) . ?
N2 C13 1.340(4) . ?
N2 C3 1.419(4) . ?
N2 H2N 0.84(4) . ?
C1 C9 1.471(6) . ?
C1 C2 1.509(5) . ?
C2 C3 1.353(5) . ?
C3 C4 1.449(5) . ?
C4 C10 1.486(5) . ?
C5 C6 1.373(5) . ?
C5 C10 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(6) . ?
C11 C12 1.495(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.488(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 C11 131.0(3) . . ?
C2 N1 H1N 109(2) . . ?
C11 N1 H1N 118(2) . . ?
C13 N2 C3 119.9(3) . . ?
C13 N2 H2N 122(2) . . ?
C3 N2 H2N 118(2) . . ?
O1 C1 C9 120.6(3) . . ?
O1 C1 C2 119.2(4) . . ?
C9 C1 C2 120.2(3) . . ?
N1 C2 C3 128.6(3) . . ?
N1 C2 C1 112.6(3) . . ?
C3 C2 C1 118.7(3) . . ?
C2 C3 N2 122.9(3) . . ?
C2 C3 C4 121.5(3) . . ?
N2 C3 C4 115.4(3) . . ?
O2 C4 C3 120.5(3) . . ?
O2 C4 C10 119.3(3) . . ?
C3 C4 C10 120.1(3) . . ?
C6 C5 C10 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 C1 119.2(3) . . ?
C8 C9 C1 121.6(4) . . ?
C9 C10 C5 119.1(3) . . ?
C9 C10 C4 120.0(3) . . ?
C5 C10 C4 120.9(4) . . ?
N1 C11 C12 113.0(4) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 N2 121.2(3) . . ?
O3 C13 C14 121.3(3) . . ?
N2 C13 C14 117.5(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C2 C3 -0.7(6) . . . . ?
C11 N1 C2 C1 -180.0(3) . . . . ?
O1 C1 C2 N1 1.2(4) . . . . ?
C9 C1 C2 N1 -177.5(3) . . . . ?
O1 C1 C2 C3 -178.2(3) . . . . ?
C9 C1 C2 C3 3.1(4) . . . . ?
N1 C2 C3 N2 6.9(5) . . . . ?
C1 C2 C3 N2 -173.8(3) . . . . ?
N1 C2 C3 C4 -178.6(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C13 N2 C3 C2 108.9(4) . . . . ?
C13 N2 C3 C4 -65.9(4) . . . . ?
C2 C3 C4 O2 177.3(3) . . . . ?
N2 C3 C4 O2 -7.9(4) . . . . ?
C2 C3 C4 C10 -3.7(4) . . . . ?
N2 C3 C4 C10 171.2(3) . . . . ?
C10 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C7 C8 C9 C1 -180.0(3) . . . . ?
O1 C1 C9 C10 177.6(3) . . . . ?
C2 C1 C9 C10 -3.7(4) . . . . ?
O1 C1 C9 C8 -2.2(5) . . . . ?
C2 C1 C9 C8 176.5(3) . . . . ?
C8 C9 C10 C5 -0.6(5) . . . . ?
C1 C9 C10 C5 179.6(3) . . . . ?
C8 C9 C10 C4 -179.5(3) . . . . ?
C1 C9 C10 C4 0.7(4) . . . . ?
C6 C5 C10 C9 0.5(5) . . . . ?
C6 C5 C10 C4 179.4(3) . . . . ?
O2 C4 C10 C9 -178.0(3) . . . . ?
C3 C4 C10 C9 3.0(4) . . . . ?
O2 C4 C10 C5 3.1(5) . . . . ?
C3 C4 C10 C5 -175.9(3) . . . . ?
C2 N1 C11 C12 -86.5(5) . . . . ?
C3 N2 C13 O3 -9.2(5) . . . . ?
C3 N2 C13 C14 171.9(3) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL'
####################################################################### 
# 
# 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_mo_amnq_0m
_database_code_depnum_ccdc_archive 'CCDC 1897000'
loop_
_audit_author_name
_audit_author_address
'Vedavati G. Puranik'
;National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2019-02-13 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            naphthoquinones
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O3'
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_weight         244.25

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   Pbca

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

_cell_length_a                   7.8552(6)
_cell_length_b                   13.2661(11)
_cell_length_c                   21.1966(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2208.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      28.00

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            53103
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1949
_reflns_number_gt                1671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL, ORTEP & PLUTON'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0365P)²+2.3868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1949
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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
O1 O 0.31467(17) -0.06412(10) 0.01197(6) 0.0109(3) Uani 1 1 d . . .
O2 O -0.09138(18) 0.04551(11) 0.20314(7) 0.0145(4) Uani 1 1 d . . .
O3 O 0.14769(19) 0.27249(11) 0.13468(7) 0.0170(4) Uani 1 1 d . . .
N1 N 0.4382(2) 0.06614(12) 0.09288(8) 0.0099(4) Uani 1 1 d . . .
H1 H 0.4860 0.0415 0.0586 0.012 Uiso 1 1 calc R . .
N2 N 0.2194(2) 0.13940(12) 0.19647(8) 0.0085(4) Uani 1 1 d . . .
H2 H 0.2602 0.1200 0.2332 0.010 Uiso 1 1 calc R . .
C1 C 0.2197(3) -0.04012(14) 0.05483(9) 0.0081(4) Uani 1 1 d . . .
C2 C 0.2793(3) 0.03560(14) 0.10386(9) 0.0082(4) Uani 1 1 d . . .
C3 C 0.1711(3) 0.06461(14) 0.15164(9) 0.0083(4) Uani 1 1 d . . .
C4 C 0.0034(3) 0.02206(14) 0.15873(9) 0.0084(4) Uani 1 1 d . . .
C5 C -0.2254(3) -0.08874(14) 0.11389(9) 0.0087(4) Uani 1 1 d . . .
H5 H -0.2969 -0.0699 0.1480 0.010 Uiso 1 1 calc R . .
C6 C -0.2864(3) -0.15318(14) 0.06759(10) 0.0100(4) Uani 1 1 d . . .
H6 H -0.3991 -0.1788 0.0704 0.012 Uiso 1 1 calc R . .
C7 C -0.1832(3) -0.18048(15) 0.01698(9) 0.0093(4) Uani 1 1 d . . .
H7 H -0.2259 -0.2240 -0.0149 0.011 Uiso 1 1 calc R . .
C8 C -0.0185(3) -0.14414(14) 0.01319(9) 0.0091(4) Uani 1 1 d . . .
H8 H 0.0519 -0.1626 -0.0214 0.011 Uiso 1 1 calc R . .
C9 C 0.0443(2) -0.08045(14) 0.05997(9) 0.0070(4) Uani 1 1 d . . .
C10 C -0.0595(2) -0.05151(14) 0.11057(9) 0.0082(4) Uani 1 1 d . . .
C11 C 0.5436(3) 0.13454(16) 0.12972(10) 0.0122(5) Uani 1 1 d . . .
H11A H 0.4981 0.2031 0.1265 0.018 Uiso 1 1 calc R . .
H11B H 0.6604 0.1333 0.1135 0.018 Uiso 1 1 calc R . .
H11C H 0.5434 0.1133 0.1740 0.018 Uiso 1 1 calc R . .
C12 C 0.2047(2) 0.23931(15) 0.18440(9) 0.0097(4) Uani 1 1 d . . .
C13 C 0.2703(3) 0.30696(16) 0.23584(10) 0.0153(5) Uani 1 1 d . . .
H13A H 0.3838 0.3316 0.2245 0.023 Uiso 1 1 calc R . .
H13B H 0.2768 0.2691 0.2755 0.023 Uiso 1 1 calc R . .
H13C H 0.1928 0.3643 0.2411 0.023 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
O1 C1 1.218(2) . ?
O2 C4 1.240(2) . ?
O3 C12 1.227(2) . ?
N1 C2 1.333(3) . ?
N1 C11 1.456(3) . ?
N1 H1 0.8800 . ?
N2 C12 1.355(3) . ?
N2 C3 1.425(3) . ?
N2 H2 0.8800 . ?
C1 C9 1.482(3) . ?
C1 C2 1.519(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.441(3) . ?
C4 C10 1.496(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.503(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 C11 128.94(17) . . ?
C2 N1 H1 115.5 . . ?
C11 N1 H1 115.5 . . ?
C12 N2 C3 122.18(17) . . ?
C12 N2 H2 118.9 . . ?
C3 N2 H2 118.9 . . ?
O1 C1 C9 122.00(18) . . ?
O1 C1 C2 119.62(18) . . ?
C9 C1 C2 118.36(17) . . ?
N1 C2 C3 128.44(19) . . ?
N1 C2 C1 111.73(17) . . ?
C3 C2 C1 119.83(17) . . ?
C2 C3 N2 121.35(18) . . ?
C2 C3 C4 122.11(18) . . ?
N2 C3 C4 116.54(17) . . ?
O2 C4 C3 122.00(18) . . ?
O2 C4 C10 118.91(18) . . ?
C3 C4 C10 119.09(17) . . ?
C6 C5 C10 120.36(19) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.27(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.91(19) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.08(19) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.35(18) . . ?
C8 C9 C1 119.73(18) . . ?
C10 C9 C1 119.88(18) . . ?
C5 C10 C9 119.01(18) . . ?
C5 C10 C4 120.32(18) . . ?
C9 C10 C4 120.61(18) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N2 122.97(18) . . ?
O3 C12 C13 122.27(18) . . ?
N2 C12 C13 114.71(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C2 C3 3.2(3) . . . . ?
C11 N1 C2 C1 -177.39(18) . . . . ?
O1 C1 C2 N1 -0.9(3) . . . . ?
C9 C1 C2 N1 -179.21(16) . . . . ?
O1 C1 C2 C3 178.61(18) . . . . ?
C9 C1 C2 C3 0.3(3) . . . . ?
N1 C2 C3 N2 2.8(3) . . . . ?
C1 C2 C3 N2 -176.62(16) . . . . ?
N1 C2 C3 C4 -177.79(19) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C12 N2 C3 C2 82.9(2) . . . . ?
C12 N2 C3 C4 -96.6(2) . . . . ?
C2 C3 C4 O2 177.24(19) . . . . ?
N2 C3 C4 O2 -3.3(3) . . . . ?
C2 C3 C4 C10 -3.7(3) . . . . ?
N2 C3 C4 C10 175.78(16) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C1 -178.70(17) . . . . ?
O1 C1 C9 C8 -3.1(3) . . . . ?
C2 C1 C9 C8 175.24(17) . . . . ?
O1 C1 C9 C10 179.24(18) . . . . ?
C2 C1 C9 C10 -2.5(3) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C6 C5 C10 C4 176.91(17) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C1 C9 C10 C5 178.74(17) . . . . ?
C8 C9 C10 C4 -176.06(17) . . . . ?
C1 C9 C10 C4 1.6(3) . . . . ?
O2 C4 C10 C5 3.4(3) . . . . ?
C3 C4 C10 C5 -175.70(17) . . . . ?
O2 C4 C10 C9 -179.53(18) . . . . ?
C3 C4 C10 C9 1.4(3) . . . . ?
C3 N2 C12 O3 0.7(3) . . . . ?
C3 N2 C12 C13 -177.01(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_cu_impnq_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1814959'
loop_
_audit_author_name
_audit_author_address
'SAMIR SHAIKH' 'NATIONAL CHEMICAL LABORATORY PUNE, INDIA'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.	2020-03-17 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         'C30 H28 N4 O4'
_chemical_formula_sum            'C30 H28 N4 O4'
_chemical_formula_weight         508.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   7.650(3)
_cell_length_b                   11.624(5)
_cell_length_c                   15.228(9)
_cell_angle_alpha                89.143(17)
_cell_angle_beta                 79.65(2)
_cell_angle_gamma                72.548(16)
_cell_volume                     1269.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4365
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      63.89

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.728
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            21637
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         65.802
_diffrn_reflns_theta_full        65.802
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4319
_reflns_number_gt                2186
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0669P)²+0.1813P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4319
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.1669(4) 0.1831(2) 0.84708(16) 0.0902(9) Uani 1 1 d . . . . .
O2 O 0.2951(4) -0.0350(2) 1.15561(16) 0.0861(9) Uani 1 1 d . . . . .
O3 O 0.2593(4) 0.7069(2) 0.55239(16) 0.0845(8) Uani 1 1 d . . . . .
O4 O 0.2671(4) 0.3028(2) 0.37859(16) 0.0760(8) Uani 1 1 d . . . . .
N1 N 0.2241(4) -0.0819(3) 0.87055(18) 0.0596(8) Uani 1 1 d . . . . .
N2 N 0.2785(4) -0.1706(3) 0.99797(19) 0.0634(8) Uani 1 1 d . . . . .
N3 N 0.3457(4) 0.6736(2) 0.35186(18) 0.0533(7) Uani 1 1 d . . . . .
N4 N 0.3535(4) 0.5047(3) 0.28241(18) 0.0639(8) Uani 1 1 d . . . . .
C1 C 0.1959(5) 0.1340(3) 0.9167(2) 0.0620(9) Uani 1 1 d . . . . .
C2 C 0.2238(4) 0.0059(3) 0.9295(2) 0.0532(8) Uani 1 1 d . . . . .
C3 C 0.2565(4) -0.0504(3) 1.0067(2) 0.0530(8) Uani 1 1 d . . . . .
C4 C 0.2659(5) 0.0140(3) 1.0857(2) 0.0585(9) Uani 1 1 d . . . . .
C5 C 0.2425(5) 0.2141(3) 1.1494(2) 0.0676(10) Uani 1 1 d . . . . .
H5 H 0.2601 0.1776 1.2032 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2228(5) 0.3348(4) 1.1432(3) 0.0779(12) Uani 1 1 d . . . . .
H6 H 0.2282 0.3795 1.1922 0.093 Uiso 1 1 calc R U . . .
C7 C 0.1949(6) 0.3897(4) 1.0640(3) 0.0828(12) Uani 1 1 d . . . . .
H7 H 0.1829 0.4715 1.0594 0.099 Uiso 1 1 calc R U . . .
C8 C 0.1848(5) 0.3242(3) 0.9918(3) 0.0716(11) Uani 1 1 d . . . . .
H8 H 0.1635 0.3624 0.9390 0.086 Uiso 1 1 calc R U . . .
C9 C 0.2058(4) 0.2019(3) 0.9968(2) 0.0567(9) Uani 1 1 d . . . . .
C10 C 0.2369(4) 0.1457(3) 1.0772(2) 0.0538(8) Uani 1 1 d . . . . .
C11 C 0.2015(5) -0.0668(3) 0.7769(2) 0.0647(10) Uani 1 1 d . . . . .
H11A H 0.1082 0.0096 0.7718 0.078 Uiso 1 1 calc R U . . .
H11B H 0.1575 -0.1308 0.7579 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3812(5) -0.0697(4) 0.7167(2) 0.0717(11) Uani 1 1 d . . . . .
H12A H 0.4716 -0.1484 0.7182 0.086 Uiso 1 1 calc R U . . .
H12B H 0.4301 -0.0099 0.7385 0.086 Uiso 1 1 calc R U . . .
C13 C 0.3552(5) -0.0445(3) 0.6212(2) 0.0719(11) Uani 1 1 d . . . . .
H13A H 0.3114 -0.1054 0.5987 0.108 Uiso 1 1 calc R U . . .
H13B H 0.4722 -0.0454 0.5850 0.108 Uiso 1 1 calc R U . . .
H13C H 0.2657 0.0333 0.6195 0.108 Uiso 1 1 calc R U . . .
C14 C 0.2599(5) -0.1871(3) 0.9151(2) 0.0621(9) Uani 1 1 d . . . . .
C15 C 0.2763(5) -0.3059(3) 0.8737(3) 0.0803(12) Uani 1 1 d . . . . .
H15A H 0.2988 -0.3669 0.9170 0.120 Uiso 1 1 calc R U . . .
H15B H 0.3779 -0.3256 0.8238 0.120 Uiso 1 1 calc R U . . .
H15C H 0.1626 -0.3017 0.8536 0.120 Uiso 1 1 calc R U . . .
C16 C 0.2636(4) 0.6154(3) 0.5124(2) 0.0565(9) Uani 1 1 d . . . . .
C17 C 0.3044(4) 0.5971(3) 0.4172(2) 0.0504(8) Uani 1 1 d . . . . .
C18 C 0.3116(4) 0.4952(3) 0.3719(2) 0.0522(8) Uani 1 1 d . . . . .
C19 C 0.2703(4) 0.3925(3) 0.4181(2) 0.0557(9) Uani 1 1 d . . . . .
C20 C 0.1897(5) 0.3118(3) 0.5667(2) 0.0635(10) Uani 1 1 d . . . . .
H20 H 0.1906 0.2420 0.5373 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1498(5) 0.3213(4) 0.6580(3) 0.0737(11) Uani 1 1 d . . . . .
H21 H 0.1250 0.2576 0.6902 0.088 Uiso 1 1 calc R U . . .
C22 C 0.1462(5) 0.4234(4) 0.7023(3) 0.0762(11) Uani 1 1 d . . . . .
H22 H 0.1198 0.4290 0.7644 0.091 Uiso 1 1 calc R U . . .
C23 C 0.1820(5) 0.5190(3) 0.6544(2) 0.0706(11) Uani 1 1 d . . . . .
H23 H 0.1779 0.5891 0.6844 0.085 Uiso 1 1 calc R U . . .
C24 C 0.2236(4) 0.5102(3) 0.5626(2) 0.0522(8) Uani 1 1 d . . . . .
C25 C 0.2289(4) 0.4055(3) 0.5173(2) 0.0510(8) Uani 1 1 d . . . . .
C26 C 0.3478(4) 0.7979(3) 0.3652(2) 0.0587(9) Uani 1 1 d . . . . .
H26A H 0.4296 0.8179 0.3150 0.070 Uiso 1 1 calc R U . . .
H26B H 0.3976 0.8036 0.4187 0.070 Uiso 1 1 calc R U . . .
C27 C 0.1583(4) 0.8867(3) 0.3741(2) 0.0601(9) Uani 1 1 d . . . . .
H27A H 0.0759 0.8659 0.4236 0.072 Uiso 1 1 calc R U . . .
H27B H 0.1094 0.8821 0.3201 0.072 Uiso 1 1 calc R U . . .
C28 C 0.1602(5) 1.0145(3) 0.3895(2) 0.0690(10) Uani 1 1 d . . . . .
H28A H 0.2090 1.0194 0.4426 0.103 Uiso 1 1 calc R U . . .
H28B H 0.0355 1.0684 0.3962 0.103 Uiso 1 1 calc R U . . .
H28C H 0.2372 1.0367 0.3393 0.103 Uiso 1 1 calc R U . . .
C29 C 0.3725(5) 0.6142(3) 0.2725(2) 0.0647(10) Uani 1 1 d . . . . .
C30 C 0.4164(6) 0.6657(3) 0.1846(2) 0.0975(15) Uani 1 1 d . . . . .
H30A H 0.4557 0.6029 0.1387 0.146 Uiso 1 1 calc R U . . .
H30B H 0.5146 0.7011 0.1853 0.146 Uiso 1 1 calc R U . . .
H30C H 0.3074 0.7265 0.1731 0.146 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
O1 C1 1.220(4) . ?
O2 C4 1.224(4) . ?
O3 C16 1.222(4) . ?
O4 C19 1.221(3) . ?
N1 C2 1.368(4) . ?
N1 C14 1.369(4) . ?
N1 C11 1.470(4) . ?
N2 C14 1.318(4) . ?
N2 C3 1.362(4) . ?
N3 C29 1.353(4) . ?
N3 C17 1.382(4) . ?
N3 C26 1.467(4) . ?
N4 C29 1.327(4) . ?
N4 C18 1.354(4) . ?
C1 C2 1.455(5) . ?
C1 C9 1.488(4) . ?
C2 C3 1.363(4) . ?
C3 C4 1.450(4) . ?
C4 C10 1.487(5) . ?
C5 C6 1.369(5) . ?
C5 C10 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(4) . ?
C11 C12 1.501(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.487(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.433(4) . ?
C16 C24 1.511(5) . ?
C17 C18 1.361(4) . ?
C18 C19 1.463(4) . ?
C19 C25 1.486(4) . ?
C20 C21 1.369(5) . ?
C20 C25 1.390(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.394(4) . ?
C26 C27 1.491(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.511(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.482(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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 C14 106.1(3) . . ?
C2 N1 C11 126.6(3) . . ?
C14 N1 C11 127.2(3) . . ?
C14 N2 C3 104.6(3) . . ?
C29 N3 C17 106.5(3) . . ?
C29 N3 C26 126.4(3) . . ?
C17 N3 C26 126.9(3) . . ?
C29 N4 C18 104.5(3) . . ?
O1 C1 C2 123.9(3) . . ?
O1 C1 C9 122.1(3) . . ?
C2 C1 C9 114.0(3) . . ?
C3 C2 N1 105.9(3) . . ?
C3 C2 C1 124.7(3) . . ?
N1 C2 C1 129.4(3) . . ?
N2 C3 C2 111.1(3) . . ?
N2 C3 C4 126.6(3) . . ?
C2 C3 C4 122.3(3) . . ?
O2 C4 C3 123.2(3) . . ?
O2 C4 C10 121.2(3) . . ?
C3 C4 C10 115.6(3) . . ?
C6 C5 C10 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C10 C5 H5 119.4 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 C1 119.1(3) . . ?
C10 C9 C1 122.1(3) . . ?
C5 C10 C9 119.2(3) . . ?
C5 C10 C4 119.5(3) . . ?
C9 C10 C4 121.3(3) . . ?
N1 C11 C12 111.6(3) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.7(3) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 N1 112.2(3) . . ?
N2 C14 C15 124.5(3) . . ?
N1 C14 C15 123.3(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 124.8(3) . . ?
O3 C16 C24 120.9(3) . . ?
C17 C16 C24 114.3(3) . . ?
C18 C17 N3 105.0(3) . . ?
C18 C17 C16 125.4(3) . . ?
N3 C17 C16 129.6(3) . . ?
N4 C18 C17 111.8(3) . . ?
N4 C18 C19 126.4(3) . . ?
C17 C18 C19 121.8(3) . . ?
O4 C19 C18 122.8(3) . . ?
O4 C19 C25 121.9(3) . . ?
C18 C19 C25 115.3(3) . . ?
C21 C20 C25 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C25 C20 H20 119.7 . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 C16 118.9(3) . . ?
C25 C24 C16 121.1(3) . . ?
C20 C25 C24 118.7(3) . . ?
C20 C25 C19 119.2(3) . . ?
C24 C25 C19 122.0(3) . . ?
N3 C26 C27 112.2(3) . . ?
N3 C26 H26A 109.2 . . ?
C27 C26 H26A 109.2 . . ?
N3 C26 H26B 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C28 112.1(3) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 C29 N3 112.1(3) . . ?
N4 C29 C30 123.9(3) . . ?
N3 C29 C30 124.0(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C2 C3 -0.9(4) . . . . ?
C11 N1 C2 C3 -177.7(3) . . . . ?
C14 N1 C2 C1 178.9(3) . . . . ?
C11 N1 C2 C1 2.1(6) . . . . ?
O1 C1 C2 C3 179.9(4) . . . . ?
C9 C1 C2 C3 0.0(5) . . . . ?
O1 C1 C2 N1 0.2(6) . . . . ?
C9 C1 C2 N1 -179.8(3) . . . . ?
C14 N2 C3 C2 0.3(4) . . . . ?
C14 N2 C3 C4 -179.5(3) . . . . ?
N1 C2 C3 N2 0.4(4) . . . . ?
C1 C2 C3 N2 -179.4(3) . . . . ?
N1 C2 C3 C4 -179.9(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
N2 C3 C4 O2 -0.3(6) . . . . ?
C2 C3 C4 O2 180.0(3) . . . . ?
N2 C3 C4 C10 179.9(3) . . . . ?
C2 C3 C4 C10 0.2(5) . . . . ?
C10 C5 C6 C7 0.7(6) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C7 C8 C9 -1.2(6) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C7 C8 C9 C1 -179.3(3) . . . . ?
O1 C1 C9 C8 -1.1(5) . . . . ?
C2 C1 C9 C8 178.8(3) . . . . ?
O1 C1 C9 C10 179.2(3) . . . . ?
C2 C1 C9 C10 -0.9(5) . . . . ?
C6 C5 C10 C9 -1.5(5) . . . . ?
C6 C5 C10 C4 177.7(3) . . . . ?
C8 C9 C10 C5 1.0(5) . . . . ?
C1 C9 C10 C5 -179.3(3) . . . . ?
C8 C9 C10 C4 -178.2(3) . . . . ?
C1 C9 C10 C4 1.5(5) . . . . ?
O2 C4 C10 C5 -0.1(5) . . . . ?
C3 C4 C10 C5 179.7(3) . . . . ?
O2 C4 C10 C9 179.1(3) . . . . ?
C3 C4 C10 C9 -1.1(5) . . . . ?
C2 N1 C11 C12 81.8(4) . . . . ?
C14 N1 C11 C12 -94.4(4) . . . . ?
N1 C11 C12 C13 -175.6(3) . . . . ?
C3 N2 C14 N1 -0.9(4) . . . . ?
C3 N2 C14 C15 178.9(3) . . . . ?
C2 N1 C14 N2 1.1(4) . . . . ?
C11 N1 C14 N2 177.9(3) . . . . ?
C2 N1 C14 C15 -178.6(3) . . . . ?
C11 N1 C14 C15 -1.9(5) . . . . ?
C29 N3 C17 C18 0.7(4) . . . . ?
C26 N3 C17 C18 177.0(3) . . . . ?
C29 N3 C17 C16 -179.8(3) . . . . ?
C26 N3 C17 C16 -3.6(5) . . . . ?
O3 C16 C17 C18 179.2(3) . . . . ?
C24 C16 C17 C18 -1.0(5) . . . . ?
O3 C16 C17 N3 -0.1(6) . . . . ?
C24 C16 C17 N3 179.6(3) . . . . ?
C29 N4 C18 C17 0.0(4) . . . . ?
C29 N4 C18 C19 177.7(3) . . . . ?
N3 C17 C18 N4 -0.5(4) . . . . ?
C16 C17 C18 N4 -180.0(3) . . . . ?
N3 C17 C18 C19 -178.2(3) . . . . ?
C16 C17 C18 C19 2.3(5) . . . . ?
N4 C18 C19 O4 -1.1(5) . . . . ?
C17 C18 C19 O4 176.3(3) . . . . ?
N4 C18 C19 C25 179.9(3) . . . . ?
C17 C18 C19 C25 -2.7(4) . . . . ?
C25 C20 C21 C22 0.6(6) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C21 C22 C23 C24 -0.9(6) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C22 C23 C24 C16 -179.5(3) . . . . ?
O3 C16 C24 C23 0.0(5) . . . . ?
C17 C16 C24 C23 -179.7(3) . . . . ?
O3 C16 C24 C25 -179.8(3) . . . . ?
C17 C16 C24 C25 0.4(4) . . . . ?
C21 C20 C25 C24 -1.1(5) . . . . ?
C21 C20 C25 C19 -179.6(3) . . . . ?
C23 C24 C25 C20 0.6(5) . . . . ?
C16 C24 C25 C20 -179.5(3) . . . . ?
C23 C24 C25 C19 179.1(3) . . . . ?
C16 C24 C25 C19 -1.1(5) . . . . ?
O4 C19 C25 C20 1.6(5) . . . . ?
C18 C19 C25 C20 -179.4(3) . . . . ?
O4 C19 C25 C24 -176.9(3) . . . . ?
C18 C19 C25 C24 2.1(4) . . . . ?
C29 N3 C26 C27 92.2(4) . . . . ?
C17 N3 C26 C27 -83.3(4) . . . . ?
N3 C26 C27 C28 179.0(3) . . . . ?
C18 N4 C29 N3 0.4(4) . . . . ?
C18 N4 C29 C30 -179.1(4) . . . . ?
C17 N3 C29 N4 -0.8(4) . . . . ?
C26 N3 C29 N4 -177.0(3) . . . . ?
C17 N3 C29 C30 178.8(3) . . . . ?
C26 N3 C29 C30 2.5(6) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL'
