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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hsd
_database_code_depnum_ccdc_archive 'CCDC 1970675'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-12-08 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+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                   14.3884(13)
_cell_length_b                   26.944(3)
_cell_length_c                   6.9828(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2707.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1420
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_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            21415
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.512
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3356
_reflns_number_gt                1667
_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-2014/7 (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)+(0.1619P)²+1.7095P] 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         3356
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.2411
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   0.767
_refine_ls_restrained_S_all      0.767
_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 0.61775(13) 0.46127(6) 0.0818(3) 0.0368(5) Uani 1 1 d . . . . .
O2 O 0.63323(14) 0.52446(7) -0.1158(3) 0.0418(5) Uani 1 1 d . . . . .
O3 O 0.61756(18) 0.45127(8) 0.6009(3) 0.0550(6) Uani 1 1 d . . . . .
H3 H 0.6248 0.4730 0.6818 0.082 Uiso 1 1 calc R U . . .
N3 N 0.63492(14) 0.54087(7) 0.2032(3) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.62779(17) 0.51065(9) 0.0514(4) 0.0317(6) Uani 1 1 d . . . . .
C4 C 0.6300(2) 0.52451(9) 0.4031(4) 0.0376(6) Uani 1 1 d . . . . .
H4A H 0.5694 0.5327 0.4550 0.045 Uiso 1 1 calc R U . . .
H4B H 0.6765 0.5420 0.4776 0.045 Uiso 1 1 calc R U . . .
C5 C 0.64592(19) 0.46927(9) 0.4207(4) 0.0365(6) Uani 1 1 d . . . . .
H5 H 0.7120 0.4620 0.4017 0.044 Uiso 1 1 calc R U . . .
C6 C 0.58975(18) 0.44295(9) 0.2699(4) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.5239 0.4506 0.2896 0.040 Uiso 1 1 calc R U . . .
C7 C 0.60211(18) 0.38725(9) 0.2708(4) 0.0361(6) Uani 1 1 d . . . . .
C8 C 0.6742(2) 0.36445(10) 0.1715(5) 0.0494(8) Uani 1 1 d . . . . .
H8 H 0.7155 0.3834 0.1000 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6843(3) 0.31332(11) 0.1795(5) 0.0610(9) Uani 1 1 d . . . . .
H9 H 0.7315 0.2981 0.1103 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6255(3) 0.28504(11) 0.2881(5) 0.0599(10) Uani 1 1 d . . . . .
H10 H 0.6334 0.2508 0.2944 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5547(3) 0.30740(12) 0.3877(5) 0.0629(10) Uani 1 1 d . . . . .
H11 H 0.5147 0.2883 0.4619 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5426(2) 0.35845(10) 0.3780(5) 0.0515(8) Uani 1 1 d . . . . .
H12 H 0.4939 0.3733 0.4443 0.062 Uiso 1 1 calc R U . . .
C13 C 0.63695(19) 0.59405(9) 0.1744(4) 0.0360(6) Uani 1 1 d . . . . .
C14 C 0.7169(2) 0.61982(10) 0.2151(5) 0.0503(8) Uani 1 1 d . . . . .
H14 H 0.7701 0.6030 0.2543 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7179(3) 0.67117(11) 0.1972(6) 0.0712(11) Uani 1 1 d . . . . .
H15 H 0.7716 0.6889 0.2253 0.085 Uiso 1 1 calc R U . . .
C16 C 0.6387(3) 0.69572(12) 0.1375(6) 0.0742(12) Uani 1 1 d . . . . .
H16 H 0.6392 0.7301 0.1252 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5598(3) 0.66972(12) 0.0967(6) 0.0692(11) Uani 1 1 d . . . . .
H17 H 0.5070 0.6864 0.0553 0.083 Uiso 1 1 calc R U . . .
C18 C 0.5579(2) 0.61843(11) 0.1165(5) 0.0524(8) Uani 1 1 d . . . . .
H18 H 0.5038 0.6008 0.0908 0.063 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 C2 1.355(3) . ?
O1 C6 1.459(3) . ?
O2 C2 1.228(3) . ?
O3 C5 1.409(3) . ?
O3 H3 0.8200 . ?
N3 C2 1.341(3) . ?
N3 C13 1.447(3) . ?
N3 C4 1.465(3) . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.511(3) . ?
C6 H6 0.9800 . ?
C7 C12 1.377(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 C18 1.374(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C6 120.17(18) . . ?
C5 O3 H3 109.5 . . ?
C2 N3 C13 119.5(2) . . ?
C2 N3 C4 124.5(2) . . ?
C13 N3 C4 115.6(2) . . ?
O2 C2 N3 124.3(2) . . ?
O2 C2 O1 117.0(2) . . ?
N3 C2 O1 118.7(2) . . ?
N3 C4 C5 111.5(2) . . ?
N3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O3 C5 C6 107.9(2) . . ?
O3 C5 C4 111.6(2) . . ?
C6 C5 C4 109.0(2) . . ?
O3 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
O1 C6 C5 108.8(2) . . ?
O1 C6 C7 107.89(19) . . ?
C5 C6 C7 113.7(2) . . ?
O1 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C12 C7 C8 119.1(3) . . ?
C12 C7 C6 119.2(2) . . ?
C8 C7 C6 121.6(2) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C18 120.8(3) . . ?
C14 C13 N3 119.2(2) . . ?
C18 C13 N3 119.8(2) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.3(3) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?

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 N3 C2 O2 8.6(4) . . . . ?
C4 N3 C2 O2 -179.0(3) . . . . ?
C13 N3 C2 O1 -174.3(2) . . . . ?
C4 N3 C2 O1 -1.8(4) . . . . ?
C6 O1 C2 O2 -166.0(2) . . . . ?
C6 O1 C2 N3 16.7(3) . . . . ?
C2 N3 C4 C5 17.8(4) . . . . ?
C13 N3 C4 C5 -169.5(2) . . . . ?
N3 C4 C5 O3 -164.4(2) . . . . ?
N3 C4 C5 C6 -45.4(3) . . . . ?
C2 O1 C6 C5 -45.7(3) . . . . ?
C2 O1 C6 C7 -169.4(2) . . . . ?
O3 C5 C6 O1 179.7(2) . . . . ?
C4 C5 C6 O1 58.4(3) . . . . ?
O3 C5 C6 C7 -60.1(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
O1 C6 C7 C12 -147.6(3) . . . . ?
C5 C6 C7 C12 91.6(3) . . . . ?
O1 C6 C7 C8 34.7(3) . . . . ?
C5 C6 C7 C8 -86.0(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
C6 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C8 C7 C12 C11 0.4(5) . . . . ?
C6 C7 C12 C11 -177.3(3) . . . . ?
C10 C11 C12 C7 -0.9(5) . . . . ?
C2 N3 C13 C14 -112.8(3) . . . . ?
C4 N3 C13 C14 74.1(3) . . . . ?
C2 N3 C13 C18 70.6(3) . . . . ?
C4 N3 C13 C18 -102.5(3) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
N3 C13 C14 C15 -176.7(3) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C14 C13 C18 C17 0.9(5) . . . . ?
N3 C13 C18 C17 177.5(3) . . . . ?
C16 C17 C18 C13 -1.2(5) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_SKD_HB_466_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1970676'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-12-08 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.3130(10)
_cell_length_b                   9.4042(12)
_cell_length_c                   9.8866(13)
_cell_angle_alpha                97.320(7)
_cell_angle_beta                 95.213(7)
_cell_angle_gamma                94.533(7)
_cell_volume                     668.77(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6750
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_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            22687
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.088
_diffrn_reflns_theta_max         29.925
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3653
_reflns_number_gt                2689
_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-2014/7 (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)+(0.1000P)²+0.2022P] 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         3653
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.780
_refine_ls_restrained_S_all      0.780
_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
C1 C 0.20077(17) 0.65687(13) 0.43528(12) 0.0349(3) Uani 1 1 d . . . . .
C11 C 0.47077(18) 0.64713(13) 0.88230(13) 0.0352(3) Uani 1 1 d . . . . .
C3 C 0.35076(17) 0.79242(12) 0.63297(12) 0.0312(3) Uani 1 1 d . . . . .
H3A H 0.2668 0.8255 0.6982 0.037 Uiso 1 1 calc R U . . .
H3B H 0.4671 0.8518 0.6525 0.037 Uiso 1 1 calc R U . . .
C2 C 0.37755(17) 0.63341(12) 0.63429(13) 0.0340(3) Uani 1 1 d . . . . .
H2 H 0.5048 0.6166 0.6181 0.041 Uiso 1 1 calc R U . . .
C4 C 0.23366(16) 0.92091(13) 0.43833(13) 0.0322(3) Uani 1 1 d . . . . .
C10 C 0.33133(18) 0.57576(13) 0.76574(13) 0.0360(3) Uani 1 1 d . . . . .
H10 H 0.3399 0.4715 0.7548 0.043 Uiso 1 1 calc R U . . .
C9 C 0.19018(19) 0.92301(17) 0.29850(15) 0.0446(3) Uani 1 1 d . . . . .
H9 H 0.1873 0.8392 0.2369 0.054 Uiso 1 1 calc R U . . .
C5 C 0.24240(18) 1.04820(14) 0.52824(14) 0.0391(3) Uani 1 1 d . . . . .
H5 H 0.2757 1.0481 0.6213 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6471(2) 0.60186(16) 0.89540(15) 0.0447(3) Uani 1 1 d . . . . .
H16 H 0.6772 0.5254 0.8347 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4283(2) 0.76098(16) 0.97384(15) 0.0472(3) Uani 1 1 d . . . . .
H12 H 0.3108 0.7922 0.9667 0.057 Uiso 1 1 calc R U . . .
C7 C 0.1547(2) 1.17751(19) 0.3422(2) 0.0567(4) Uani 1 1 d . . . . .
H7 H 0.1256 1.2626 0.3101 0.068 Uiso 1 1 calc R U . . .
C8 C 0.1511(2) 1.0518(2) 0.25214(18) 0.0574(4) Uani 1 1 d . . . . .
H8 H 0.1220 1.0535 0.1588 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2017(2) 1.17525(16) 0.47964(19) 0.0506(4) Uani 1 1 d . . . . .
H6 H 0.2063 1.2597 0.5406 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7787(2) 0.6697(2) 0.99815(16) 0.0547(4) Uani 1 1 d . . . . .
H15 H 0.8965 0.6389 1.0058 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7351(2) 0.7824(2) 1.08854(17) 0.0592(4) Uani 1 1 d . . . . .
H14 H 0.8229 0.8275 1.1579 0.071 Uiso 1 1 calc R U . . .
C13 C 0.5607(2) 0.8286(2) 1.07623(18) 0.0606(4) Uani 1 1 d . . . . .
H13 H 0.5316 0.9055 1.1369 0.073 Uiso 1 1 calc R U . . .
O1 O 0.10633(14) 0.62034(11) 0.32724(10) 0.0473(3) Uani 1 1 d . . . . .
O3 O 0.15117(13) 0.60414(11) 0.79491(11) 0.0432(2) Uani 1 1 d . . . . .
O2 O 0.25199(14) 0.56060(9) 0.51881(9) 0.0408(2) Uani 1 1 d . . . . .
N1 N 0.27169(14) 0.79218(10) 0.49192(10) 0.0319(2) Uani 1 1 d . . . . .
H3C H 0.076(3) 0.533(2) 0.750(2) 0.066(6) 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
C1 O1 1.2128(15) . ?
C1 O2 1.3527(16) . ?
C1 N1 1.3650(15) . ?
C11 C12 1.3850(19) . ?
C11 C16 1.3899(19) . ?
C11 C10 1.5164(18) . ?
C3 N1 1.4600(15) . ?
C3 C2 1.5250(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 O2 1.4582(15) . ?
C2 C10 1.5256(18) . ?
C2 H2 0.9800 . ?
C4 C5 1.3906(18) . ?
C4 C9 1.3931(18) . ?
C4 N1 1.4190(15) . ?
C10 O3 1.4125(16) . ?
C10 H10 0.9800 . ?
C9 C8 1.390(2) . ?
C9 H9 0.9300 . ?
C5 C6 1.3869(19) . ?
C5 H5 0.9300 . ?
C16 C15 1.388(2) . ?
C16 H16 0.9300 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9300 . ?
C7 C6 1.374(2) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C15 C14 1.374(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.380(2) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
O3 H3C 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 121.94(11) . . ?
O1 C1 N1 128.33(12) . . ?
O2 C1 N1 109.72(10) . . ?
C12 C11 C16 118.87(13) . . ?
C12 C11 C10 121.24(12) . . ?
C16 C11 C10 119.84(12) . . ?
N1 C3 C2 101.31(9) . . ?
N1 C3 H3A 111.5 . . ?
C2 C3 H3A 111.5 . . ?
N1 C3 H3B 111.5 . . ?
C2 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
O2 C2 C3 103.95(9) . . ?
O2 C2 C10 109.75(10) . . ?
C3 C2 C10 114.26(10) . . ?
O2 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C10 C2 H2 109.6 . . ?
C5 C4 C9 119.48(12) . . ?
C5 C4 N1 118.78(11) . . ?
C9 C4 N1 121.74(12) . . ?
O3 C10 C11 110.10(10) . . ?
O3 C10 C2 110.83(10) . . ?
C11 C10 C2 108.50(10) . . ?
O3 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C2 C10 H10 109.1 . . ?
C8 C9 C4 119.20(15) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C6 C5 C4 120.23(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C15 C16 C11 120.62(14) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C11 C12 C13 120.24(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C6 C7 C8 119.23(14) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 121.22(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C7 C6 C5 120.59(15) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C14 C15 C16 120.03(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 119.85(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C13 C12 120.39(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C10 O3 H3C 107.0(13) . . ?
C1 O2 C2 109.68(9) . . ?
C1 N1 C4 125.20(10) . . ?
C1 N1 C3 110.69(10) . . ?
C4 N1 C3 122.20(9) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060

