# Electronic Supplementary Material (ESI) for Analytical Methods.
# 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_891_a
_database_code_depnum_ccdc_archive 'CCDC 1944503'
loop_
_audit_author_name
_audit_author_address
'Suvendu Maity'
;Jadavpur University
India
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N3 S'
_chemical_formula_weight         369.47

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'
S S 0.1246 0.1234 '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                   9.8094(3)
_cell_length_b                   20.7167(7)
_cell_length_c                   9.6437(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.5560(10)
_cell_angle_gamma                90
_cell_volume                     1956.00(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.13

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             950
_exptl_transmission_factor_min   0.745
_exptl_transmission_factor_max   0.854
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18743
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3998
_reflns_number_gt                3001
_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)+(0.0694P)²+0.5994P] 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         3998
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
S1 S 0.27508(7) 0.59645(4) 0.97133(7) 0.0826(3) Uani 1 1 d . . . . .
N3 N 0.57219(17) 0.63064(8) 0.94648(17) 0.0569(4) Uani 1 1 d . . . . .
N2 N 0.63821(18) 0.65106(10) 0.68349(16) 0.0638(5) Uani 1 1 d . . . . .
H2 H 0.561165 0.635994 0.706672 0.077 Uiso 1 1 calc R U . . .
N1 N 0.40675(19) 0.65311(11) 0.5245(2) 0.0743(5) Uani 1 1 d . . . . .
C7 C 0.7394(2) 0.66083(9) 0.7862(2) 0.0526(5) Uani 1 1 d . . . . .
C18 C 0.7319(2) 0.61193(10) 0.46767(19) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.6543(2) 0.66475(10) 0.53844(19) 0.0550(5) Uani 1 1 d . . . . .
H6 H 0.706478 0.704912 0.532817 0.066 Uiso 1 1 calc R U . . .
C12 C 0.7069(2) 0.65022(10) 0.9255(2) 0.0550(5) Uani 1 1 d . . . . .
C5 C 0.5151(2) 0.67527(9) 0.4639(2) 0.0547(5) Uani 1 1 d . . . . .
C13 C 0.5502(2) 0.59212(11) 1.0449(2) 0.0645(6) Uani 1 1 d . . . . .
H13 H 0.623746 0.577464 1.101788 0.077 Uiso 1 1 calc R U . . .
C8 C 0.8716(2) 0.67955(11) 0.7607(2) 0.0640(5) Uani 1 1 d . . . . .
H8 H 0.895279 0.685468 0.669675 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8546(2) 0.62377(12) 0.4097(2) 0.0674(6) Uani 1 1 d . . . . .
H19 H 0.890988 0.665238 0.413049 0.081 Uiso 1 1 calc R U . . .
C14 C 0.4153(2) 0.57048(11) 1.0712(2) 0.0649(6) Uani 1 1 d . . . . .
C15 C 0.3786(3) 0.52762(12) 1.1727(3) 0.0796(7) Uani 1 1 d . . . . .
H15 H 0.440168 0.508847 1.237887 0.096 Uiso 1 1 calc R U . . .
C23 C 0.6790(2) 0.55036(11) 0.4583(3) 0.0701(6) Uani 1 1 d . . . . .
H23 H 0.596622 0.541265 0.496908 0.084 Uiso 1 1 calc R U . . .
C9 C 0.9684(2) 0.68950(12) 0.8695(3) 0.0740(7) Uani 1 1 d . . . . .
H9 H 1.056616 0.701705 0.850745 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5050(3) 0.70493(12) 0.3356(3) 0.0762(7) Uani 1 1 d . . . . .
H4 H 0.582683 0.719842 0.295310 0.091 Uiso 1 1 calc R U . . .
C11 C 0.8055(3) 0.66203(12) 1.0317(2) 0.0713(6) Uani 1 1 d . . . . .
H11 H 0.783607 0.656687 1.123479 0.086 Uiso 1 1 calc R U . . .
C20 C 0.9241(3) 0.57516(16) 0.3468(3) 0.0834(7) Uani 1 1 d . . . . .
H20 H 1.007484 0.583898 0.309972 0.100 Uiso 1 1 calc R U . . .
C10 C 0.9353(3) 0.68150(13) 1.0042(3) 0.0795(7) Uani 1 1 d . . . . .
H10 H 1.000128 0.689181 1.076817 0.095 Uiso 1 1 calc R U . . .
C22 C 0.7475(3) 0.50171(13) 0.3919(3) 0.0884(8) Uani 1 1 d . . . . .
H22 H 0.709750 0.460610 0.383701 0.106 Uiso 1 1 calc R U . . .
C17 C 0.1703(3) 0.54928(15) 1.0632(3) 0.0902(8) Uani 1 1 d . . . . .
H17 H 0.076311 0.546842 1.044540 0.108 Uiso 1 1 calc R U . . .
C21 C 0.8716(3) 0.51458(16) 0.3383(3) 0.0885(8) Uani 1 1 d . . . . .
H21 H 0.919202 0.481848 0.296457 0.106 Uiso 1 1 calc R U . . .
C3 C 0.3785(4) 0.71210(13) 0.2685(3) 0.0959(9) Uani 1 1 d . . . . .
H3 H 0.369487 0.732270 0.182266 0.115 Uiso 1 1 calc R U . . .
C2 C 0.2662(3) 0.68945(14) 0.3292(3) 0.0888(8) Uani 1 1 d . . . . .
H2A H 0.179595 0.693481 0.285039 0.107 Uiso 1 1 calc R U . . .
C16 C 0.2382(3) 0.51596(13) 1.1654(3) 0.0893(8) Uani 1 1 d . . . . .
H16 H 0.195992 0.488085 1.225034 0.107 Uiso 1 1 calc R U . . .
C1 C 0.2839(3) 0.66076(16) 0.4560(3) 0.0907(8) Uani 1 1 d . . . . .
H1 H 0.207076 0.645637 0.497624 0.109 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
S1 C17 1.705(3) . ?
S1 C14 1.716(2) . ?
N3 C13 1.269(3) . ?
N3 C12 1.409(3) . ?
N2 C7 1.373(2) . ?
N2 C6 1.445(2) . ?
N2 H2 0.8600 . ?
N1 C5 1.326(3) . ?
N1 C1 1.347(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.417(3) . ?
C18 C23 1.378(3) . ?
C18 C19 1.381(3) . ?
C18 C6 1.519(3) . ?
C6 C5 1.519(3) . ?
C6 H6 0.9800 . ?
C12 C11 1.387(3) . ?
C5 C4 1.379(3) . ?
C13 C14 1.434(3) . ?
C13 H13 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C14 C15 1.385(3) . ?
C15 C16 1.395(4) . ?
C15 H15 0.9300 . ?
C23 C22 1.390(4) . ?
C23 H23 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C4 C3 1.371(4) . ?
C4 H4 0.9300 . ?
C11 C10 1.376(4) . ?
C11 H11 0.9300 . ?
C20 C21 1.357(4) . ?
C20 H20 0.9300 . ?
C10 H10 0.9300 . ?
C22 C21 1.377(4) . ?
C22 H22 0.9300 . ?
C17 C16 1.346(4) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C3 C2 1.363(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.361(4) . ?
C2 H2A 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1 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
C17 S1 C14 90.96(14) . . ?
C13 N3 C12 119.55(18) . . ?
C7 N2 C6 123.49(17) . . ?
C7 N2 H2 118.3 . . ?
C6 N2 H2 118.3 . . ?
C5 N1 C1 117.4(2) . . ?
N2 C7 C8 123.62(19) . . ?
N2 C7 C12 117.78(18) . . ?
C8 C7 C12 118.59(18) . . ?
C23 C18 C19 118.2(2) . . ?
C23 C18 C6 119.96(19) . . ?
C19 C18 C6 121.86(19) . . ?
N2 C6 C5 109.71(16) . . ?
N2 C6 C18 112.42(17) . . ?
C5 C6 C18 110.57(15) . . ?
N2 C6 H6 108.0 . . ?
C5 C6 H6 108.0 . . ?
C18 C6 H6 108.0 . . ?
C11 C12 N3 124.24(19) . . ?
C11 C12 C7 119.0(2) . . ?
N3 C12 C7 116.67(17) . . ?
N1 C5 C4 122.3(2) . . ?
N1 C5 C6 117.59(18) . . ?
C4 C5 C6 120.1(2) . . ?
N3 C13 C14 122.0(2) . . ?
N3 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C15 C14 C13 127.5(2) . . ?
C15 C14 S1 111.26(19) . . ?
C13 C14 S1 121.26(17) . . ?
C14 C15 C16 112.0(3) . . ?
C14 C15 H15 124.0 . . ?
C16 C15 H15 124.0 . . ?
C18 C23 C22 120.7(2) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C16 C17 S1 112.8(2) . . ?
C16 C17 H17 123.6 . . ?
S1 C17 H17 123.6 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C17 C16 C15 112.9(3) . . ?
C17 C16 H16 123.5 . . ?
C15 C16 H16 123.5 . . ?
N1 C1 C2 123.5(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_SDL_a
_database_code_depnum_ccdc_archive 'CCDC 1944513'
loop_
_audit_author_name
_audit_author_address
'sunanda dey'
;Jadavpur University
India
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 N3 O'
_chemical_formula_sum            'C29 H23 N3 O'
_chemical_formula_weight         429.50

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                   22.180(3)
_cell_length_b                   5.9098(7)
_cell_length_c                   16.938(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.383(4)
_cell_angle_gamma                90
_cell_volume                     2213.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3486
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.45

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   0.792
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24841
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3882
_reflns_number_gt                2264
_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)+(0.0368P)²+1.7081P] 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         3882
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1556
_refine_ls_R_factor_gt           0.0913
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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 0.72300(12) 0.5964(5) 0.77624(17) 0.0600(8) Uani 1 1 d . . . . .
H1 H 0.724972 0.492161 0.744601 0.090 Uiso 1 1 calc R U . . .
N1 N 0.69482(13) 0.3583(5) 0.65118(18) 0.0420(8) Uani 1 1 d . . . . .
N003 N 0.79100(13) 0.0800(6) 0.69153(19) 0.0508(9) Uani 1 1 d . . . . .
H003 H 0.788544 0.212570 0.711984 0.061 Uiso 1 1 calc R U . . .
C25 C 0.84274(15) -0.0129(7) 0.8177(2) 0.0411(10) Uani 1 1 d . . . . .
C1 C 0.64854(17) 0.4881(7) 0.6387(2) 0.0440(10) Uani 1 1 d . . . . .
H1A H 0.621759 0.459264 0.594900 0.053 Uiso 1 1 calc R U . . .
C2 C 0.63610(15) 0.6761(7) 0.6892(2) 0.0396(10) Uani 1 1 d . . . . .
C19 C 0.89158(16) -0.1022(7) 0.6916(2) 0.0380(9) Uani 1 1 d . . . . .
C13 C 0.75521(16) 0.0337(7) 0.6231(2) 0.0405(10) Uani 1 1 d . . . . .
C11 C 0.58469(16) 0.8214(7) 0.6708(2) 0.0439(10) Uani 1 1 d . . . . .
C12 C 0.70646(16) 0.1766(7) 0.5997(2) 0.0431(10) Uani 1 1 d . . . . .
C3 C 0.67572(17) 0.7271(7) 0.7543(2) 0.0452(11) Uani 1 1 d . . . . .
C18 C 0.83209(16) -0.0793(7) 0.7307(2) 0.0429(10) Uani 1 1 d . . . . .
H18 H 0.812327 -0.227703 0.728509 0.051 Uiso 1 1 calc R U . . .
C6 C 0.57849(17) 1.0197(7) 0.7162(2) 0.0466(11) Uani 1 1 d . . . . .
N2 N 0.82019(17) 0.1857(7) 0.8389(2) 0.0712(12) Uani 1 1 d . . . . .
C14 C 0.76612(17) -0.1521(7) 0.5759(2) 0.0490(11) Uani 1 1 d . . . . .
H14 H 0.797853 -0.249466 0.591089 0.059 Uiso 1 1 calc R U . . .
C5 C 0.62155(19) 1.0645(8) 0.7802(3) 0.0544(12) Uani 1 1 d . . . . .
H5 H 0.617845 1.195955 0.809598 0.065 Uiso 1 1 calc R U . . .
C4 C 0.66779(19) 0.9225(8) 0.7998(2) 0.0525(11) Uani 1 1 d . . . . .
H4 H 0.694502 0.953710 0.843428 0.063 Uiso 1 1 calc R U . . .
C24 C 0.92289(18) -0.3027(7) 0.6976(2) 0.0534(12) Uani 1 1 d . . . . .
H24 H 0.906913 -0.424112 0.724046 0.064 Uiso 1 1 calc R U . . .
C10 C 0.53916(17) 0.7771(8) 0.6094(2) 0.0558(12) Uani 1 1 d . . . . .
H10 H 0.541537 0.647134 0.578874 0.067 Uiso 1 1 calc R U . . .
C20 C 0.91521(19) 0.0732(8) 0.6512(2) 0.0559(12) Uani 1 1 d . . . . .
H20 H 0.894873 0.210844 0.647059 0.067 Uiso 1 1 calc R U . . .
C15 C 0.73093(18) -0.1945(8) 0.5072(2) 0.0593(12) Uani 1 1 d . . . . .
H15 H 0.738745 -0.320489 0.476751 0.071 Uiso 1 1 calc R U . . .
C7 C 0.52983(19) 1.1695(8) 0.6979(3) 0.0593(12) Uani 1 1 d . . . . .
H7 H 0.526896 1.301930 0.727016 0.071 Uiso 1 1 calc R U . . .
C17 C 0.67275(19) 0.1312(9) 0.5293(3) 0.0667(14) Uani 1 1 d . . . . .
H17 H 0.641264 0.227970 0.512550 0.080 Uiso 1 1 calc R U . . .
C9 C 0.49168(19) 0.9230(9) 0.5946(3) 0.0685(14) Uani 1 1 d . . . . .
H9 H 0.461850 0.889105 0.554736 0.082 Uiso 1 1 calc R U . . .
C28 C 0.87216(19) -0.1579(9) 0.8711(3) 0.0667(14) Uani 1 1 d . . . . .
H28 H 0.887641 -0.294298 0.854180 0.080 Uiso 1 1 calc R U . . .
C8 C 0.4874(2) 1.1223(9) 0.6384(3) 0.0697(14) Uani 1 1 d . . . . .
H8 H 0.455488 1.221939 0.626773 0.084 Uiso 1 1 calc R U . . .
C22 C 1.0004(2) -0.1525(11) 0.6241(3) 0.0756(16) Uani 1 1 d . . . . .
H22 H 1.036969 -0.169572 0.601390 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6845(2) -0.0523(9) 0.4836(3) 0.0783(16) Uani 1 1 d . . . . .
H16 H 0.660978 -0.079955 0.436744 0.094 Uiso 1 1 calc R U . . .
C21 C 0.9695(2) 0.0465(10) 0.6164(3) 0.0734(15) Uani 1 1 d . . . . .
H21 H 0.984793 0.164843 0.587751 0.088 Uiso 1 1 calc R U . . .
C23 C 0.9773(2) -0.3267(10) 0.6653(3) 0.0767(16) Uani 1 1 d . . . . .
H23 H 0.998562 -0.461959 0.671496 0.092 Uiso 1 1 calc R U . . .
C30 C 0.8557(3) 0.1016(14) 0.9729(3) 0.097(2) Uani 1 1 d . . . . .
H30 H 0.859589 0.145362 1.025834 0.117 Uiso 1 1 calc R U . . .
C29 C 0.8784(2) -0.0986(13) 0.9501(3) 0.0904(19) Uani 1 1 d . . . . .
H29 H 0.898028 -0.194953 0.987115 0.108 Uiso 1 1 calc R U . . .
C27 C 0.8272(3) 0.2368(11) 0.9174(4) 0.0900(19) Uani 1 1 d . . . . .
H27 H 0.811497 0.373168 0.933920 0.108 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 C3 1.332(4) . ?
O1 H1 0.8200 . ?
N1 C1 1.286(4) . ?
N1 C12 1.419(5) . ?
N003 C13 1.381(4) . ?
N003 C18 1.437(4) . ?
N003 H003 0.8600 . ?
C25 N2 1.336(5) . ?
C25 C28 1.374(5) . ?
C25 C18 1.525(5) . ?
C1 C2 1.441(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.390(5) . ?
C2 C11 1.442(5) . ?
C19 C20 1.368(5) . ?
C19 C24 1.374(5) . ?
C19 C18 1.527(5) . ?
C13 C14 1.391(5) . ?
C13 C12 1.405(5) . ?
C11 C6 1.415(5) . ?
C11 C10 1.417(5) . ?
C12 C17 1.385(5) . ?
C3 C4 1.407(5) . ?
C18 H18 0.9800 . ?
C6 C7 1.412(5) . ?
C6 C5 1.413(5) . ?
N2 C27 1.361(6) . ?
C14 C15 1.373(5) . ?
C14 H14 0.9300 . ?
C5 C4 1.347(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C24 C23 1.370(6) . ?
C24 H24 0.9300 . ?
C10 C9 1.369(5) . ?
C10 H10 0.9300 . ?
C20 C21 1.390(6) . ?
C20 H20 0.9300 . ?
C15 C16 1.366(6) . ?
C15 H15 0.9300 . ?
C7 C8 1.354(6) . ?
C7 H7 0.9300 . ?
C17 C16 1.368(6) . ?
C17 H17 0.9300 . ?
C9 C8 1.400(6) . ?
C9 H9 0.9300 . ?
C28 C29 1.380(7) . ?
C28 H28 0.9300 . ?
C8 H8 0.9300 . ?
C22 C21 1.362(7) . ?
C22 C23 1.366(7) . ?
C22 H22 0.9300 . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C30 C27 1.353(8) . ?
C30 C29 1.355(8) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C27 H27 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
C3 O1 H1 109.5 . . ?
C1 N1 C12 122.1(3) . . ?
C13 N003 C18 124.2(3) . . ?
C13 N003 H003 117.9 . . ?
C18 N003 H003 117.9 . . ?
N2 C25 C28 122.7(4) . . ?
N2 C25 C18 116.9(4) . . ?
C28 C25 C18 120.4(4) . . ?
N1 C1 C2 123.3(4) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 C11 118.9(4) . . ?
C1 C2 C11 121.0(4) . . ?
C20 C19 C24 118.7(4) . . ?
C20 C19 C18 121.8(4) . . ?
C24 C19 C18 119.5(4) . . ?
N003 C13 C14 121.7(4) . . ?
N003 C13 C12 119.9(4) . . ?
C14 C13 C12 118.4(4) . . ?
C6 C11 C10 117.3(4) . . ?
C6 C11 C2 118.9(4) . . ?
C10 C11 C2 123.8(4) . . ?
C17 C12 C13 118.7(4) . . ?
C17 C12 N1 124.4(4) . . ?
C13 C12 N1 117.0(3) . . ?
O1 C3 C2 122.2(4) . . ?
O1 C3 C4 116.9(4) . . ?
C2 C3 C4 121.0(4) . . ?
N003 C18 C25 108.9(3) . . ?
N003 C18 C19 113.3(3) . . ?
C25 C18 C19 111.5(3) . . ?
N003 C18 H18 107.6 . . ?
C25 C18 H18 107.6 . . ?
C19 C18 H18 107.6 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 C11 120.3(4) . . ?
C5 C6 C11 119.0(4) . . ?
C25 N2 C27 116.1(5) . . ?
C15 C14 C13 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C23 C24 C19 121.0(4) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C16 C17 C12 121.8(4) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C25 C28 C29 119.2(5) . . ?
C25 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C21 C22 C23 119.6(5) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C23 C24 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C27 C30 C29 118.7(6) . . ?
C27 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C30 C29 C28 119.1(6) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C30 C27 N2 124.1(6) . . ?
C30 C27 H27 117.9 . . ?
N2 C27 H27 117.9 . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041



