# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cd16212
_database_code_depnum_ccdc_archive 'CCDC 1498124'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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                   5.0293(11)
_cell_length_b                   9.305(2)
_cell_length_c                   14.420(3)
_cell_angle_alpha                78.510(5)
_cell_angle_beta                 87.882(5)
_cell_angle_gamma                83.349(4)
_cell_volume                     656.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1141
_cell_measurement_theta_min      4.495
_cell_measurement_theta_max      56.140

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3806
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2432
_reflns_number_gt                1973
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0652P)²+0.1930P] 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
_refine_ls_extinction_coef       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     192
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.3463(3) 0.20769(17) 0.38803(10) 0.0454(4) Uani 1 1 d . . . . .
O2 O 0.3343(3) 0.17501(19) 0.06470(11) 0.0514(5) Uani 1 1 d . . . . .
O3 O 1.1006(3) -0.16492(15) 0.26867(10) 0.0395(4) Uani 1 1 d . . . . .
O4 O 0.2663(4) 0.4342(3) 0.4979(2) 0.0806(7) Uani 1 1 d D . . . .
C1 C 0.2915(4) 0.2237(2) 0.30370(14) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.4227(4) 0.1482(2) 0.23228(14) 0.0331(5) Uani 1 1 d . . . . .
C3 C 0.2845(4) 0.2058(2) 0.14266(15) 0.0356(5) Uani 1 1 d . . . . .
C4 C 0.0614(4) 0.3168(2) 0.16223(14) 0.0347(5) Uani 1 1 d . . . . .
C5 C 0.0667(4) 0.3290(2) 0.25622(15) 0.0360(5) Uani 1 1 d . . . . .
C6 C -0.1197(5) 0.4250(3) 0.29259(17) 0.0461(6) Uani 1 1 d . . . . .
H6 H -0.1180 0.4323 0.3560 0.055 Uiso 1 1 calc R U . . .
C7 C -0.3089(5) 0.5102(3) 0.23166(18) 0.0508(6) Uani 1 1 d . . . . .
H7 H -0.4347 0.5768 0.2542 0.061 Uiso 1 1 calc R U . . .
C8 C -0.3140(5) 0.4978(3) 0.13814(18) 0.0497(6) Uani 1 1 d . . . . .
H8 H -0.4434 0.5562 0.0987 0.060 Uiso 1 1 calc R U . . .
C9 C -0.1294(4) 0.3999(2) 0.10177(16) 0.0425(5) Uani 1 1 d . . . . .
H9 H -0.1343 0.3907 0.0388 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6468(4) 0.0430(2) 0.24519(14) 0.0328(5) Uani 1 1 d . . . . .
C11 C 0.7797(4) -0.0056(2) 0.33347(14) 0.0355(5) Uani 1 1 d . . . . .
H11 H 0.7140 0.0329 0.3857 0.043 Uiso 1 1 calc R U . . .
C12 C 0.9978(4) -0.1056(2) 0.34312(14) 0.0356(5) Uani 1 1 d . . . . .
C13 C 0.9827(4) -0.1213(2) 0.18280(15) 0.0386(5) Uani 1 1 d . . . . .
C14 C 0.7654(4) -0.0224(2) 0.16988(15) 0.0373(5) Uani 1 1 d . . . . .
H14 H 0.6896 0.0045 0.1102 0.045 Uiso 1 1 calc R U . . .
C15 C 1.1565(5) -0.1621(3) 0.42995(16) 0.0490(6) Uani 1 1 d . . . . .
H15A H 1.3143 -0.1121 0.4262 0.074 Uiso 1 1 calc R U . . .
H15B H 1.2072 -0.2661 0.4357 0.074 Uiso 1 1 calc R U . . .
H15C H 1.0507 -0.1445 0.4842 0.074 Uiso 1 1 calc R U . . .
C16 C 1.1258(5) -0.1946(3) 0.11023(17) 0.0525(6) Uani 1 1 d . . . . .
H16A H 1.0301 -0.1667 0.0519 0.079 Uiso 1 1 calc R U . . .
H16B H 1.1371 -0.2997 0.1312 0.079 Uiso 1 1 calc R U . . .
H16C H 1.3029 -0.1649 0.1006 0.079 Uiso 1 1 calc R U . . .
H4A H 0.285(7) 0.369(3) 0.466(2) 0.101(12) Uiso 1 1 d D . . . .
H4B H 0.374(13) 0.474(10) 0.462(4) 0.29(5) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(2) . ?
O2 C3 1.224(2) . ?
O3 C13 1.359(2) . ?
O3 C12 1.361(3) . ?
O4 H4A 0.825(19) . ?
O4 H4B 0.81(2) . ?
C1 C2 1.456(3) . ?
C1 C5 1.497(3) . ?
C2 C10 1.397(3) . ?
C2 C3 1.464(3) . ?
C3 C4 1.493(3) . ?
C4 C9 1.379(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.426(3) . ?
C10 C14 1.427(3) . ?
C11 C12 1.346(3) . ?
C11 H11 0.9300 . ?
C12 C15 1.482(3) . ?
C13 C14 1.338(3) . ?
C13 C16 1.481(3) . ?
C14 H14 0.9300 . ?
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
C13 O3 C12 119.46(16) . . ?
H4A O4 H4B 86(6) . . ?
O1 C1 C2 128.59(19) . . ?
O1 C1 C5 124.31(18) . . ?
C2 C1 C5 107.11(17) . . ?
C10 C2 C1 126.49(18) . . ?
C10 C2 C3 125.47(18) . . ?
C1 C2 C3 108.00(18) . . ?
O2 C3 C2 129.2(2) . . ?
O2 C3 C4 124.10(19) . . ?
C2 C3 C4 106.65(17) . . ?
C9 C4 C5 121.2(2) . . ?
C9 C4 C3 129.3(2) . . ?
C5 C4 C3 109.44(18) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 C1 130.2(2) . . ?
C4 C5 C1 108.79(18) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 117.6(2) . . ?
C4 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C2 C10 C11 123.19(18) . . ?
C2 C10 C14 122.36(19) . . ?
C11 C10 C14 114.44(18) . . ?
C12 C11 C10 121.65(19) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 O3 121.17(18) . . ?
C11 C12 C15 126.8(2) . . ?
O3 C12 C15 112.05(18) . . ?
C14 C13 O3 121.47(19) . . ?
C14 C13 C16 126.7(2) . . ?
O3 C13 C16 111.78(18) . . ?
C13 C14 C10 121.8(2) . . ?
C13 C14 H14 119.1 . . ?
C10 C14 H14 119.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 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
O1 C1 C2 C10 -2.0(4) . . . . ?
C5 C1 C2 C10 178.34(19) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C5 C1 C2 C3 0.4(2) . . . . ?
C10 C2 C3 O2 0.1(4) . . . . ?
C1 C2 C3 O2 178.0(2) . . . . ?
C10 C2 C3 C4 -179.01(19) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
O2 C3 C4 C9 2.1(4) . . . . ?
C2 C3 C4 C9 -178.7(2) . . . . ?
O2 C3 C4 C5 -177.8(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C9 C4 C5 C1 178.97(19) . . . . ?
C3 C4 C5 C1 -1.1(2) . . . . ?
O1 C1 C5 C6 -0.5(4) . . . . ?
C2 C1 C5 C6 179.2(2) . . . . ?
O1 C1 C5 C4 -179.26(19) . . . . ?
C2 C1 C5 C4 0.4(2) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C1 C5 C6 C7 -179.7(2) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C3 C4 C9 C8 -179.0(2) . . . . ?
C7 C8 C9 C4 -0.8(4) . . . . ?
C1 C2 C10 C11 0.2(3) . . . . ?
C3 C2 C10 C11 177.70(18) . . . . ?
C1 C2 C10 C14 -178.38(19) . . . . ?
C3 C2 C10 C14 -0.8(3) . . . . ?
C2 C10 C11 C12 -179.01(19) . . . . ?
C14 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 O3 -0.1(3) . . . . ?
C10 C11 C12 C15 178.5(2) . . . . ?
C13 O3 C12 C11 0.7(3) . . . . ?
C13 O3 C12 C15 -178.09(18) . . . . ?
C12 O3 C13 C14 -0.8(3) . . . . ?
C12 O3 C13 C16 178.57(18) . . . . ?
O3 C13 C14 C10 0.3(3) . . . . ?
C16 C13 C14 C10 -178.9(2) . . . . ?
C2 C10 C14 C13 178.9(2) . . . . ?
C11 C10 C14 C13 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O1 0.825(19) 2.039(19) 2.864(3) 178(4) .
C16 H16A O2 0.96 2.55 3.450(3) 156.2 2_655
C14 H14 O2 0.93 2.27 2.930(3) 127.4 .
C11 H11 O1 0.93 2.32 2.967(3) 126.2 .

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_20160703a_0m
_database_code_depnum_ccdc_archive 'CCDC 1498122'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 N3 O2 S'
_chemical_formula_sum            'C19 H27 N3 O2 S'
_chemical_formula_weight         361.50

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.252(6)
_cell_length_b                   8.626(6)
_cell_length_c                   15.276(10)
_cell_angle_alpha                96.785(14)
_cell_angle_beta                 98.511(13)
_cell_angle_gamma                117.108(13)
_cell_volume                     935.7(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2186
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.65

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            9128
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3655
_reflns_number_gt                2601
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0796P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3655
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
S1 S 0.83785(9) 0.18012(9) 0.43602(4) 0.0619(2) Uani 1 1 d . . .
O1 O 0.8893(2) 0.3348(2) 0.13978(10) 0.0627(5) Uani 1 1 d . . .
O2 O 0.29272(19) 0.0642(2) 0.20506(10) 0.0593(5) Uani 1 1 d . . .
N1 N 0.8455(2) 0.2443(2) 0.27110(10) 0.0384(4) Uani 1 1 d . . .
N2 N 0.5528(2) 0.1177(2) 0.30474(10) 0.0379(4) Uani 1 1 d . . .
N3 N 0.3587(2) 0.29272(19) -0.08801(9) 0.0350(4) Uani 1 1 d . . .
C1 C 0.7749(3) 0.2614(3) 0.18422(12) 0.0388(4) Uani 1 1 d . . .
C2 C 0.7418(3) 0.1815(2) 0.33295(12) 0.0374(4) Uani 1 1 d . . .
C3 C 0.4640(3) 0.1252(3) 0.21993(12) 0.0384(4) Uani 1 1 d . . .
C4 C 0.5779(2) 0.1982(2) 0.15863(12) 0.0342(4) Uani 1 1 d . . .
C5 C 0.4973(2) 0.2197(2) 0.07287(12) 0.0331(4) Uani 1 1 d . . .
C6 C 0.5892(3) 0.2493(3) 0.00124(12) 0.0375(4) Uani 1 1 d . . .
H6 H 0.7000 0.2435 0.0070 0.045 Uiso 1 1 calc R . .
C7 C 0.5229(3) 0.2864(2) -0.07647(12) 0.0368(4) Uani 1 1 d . . .
C8 C 0.2573(2) 0.2551(2) -0.02263(12) 0.0361(4) Uani 1 1 d . . .
C9 C 0.3242(2) 0.2181(2) 0.05493(12) 0.0364(4) Uani 1 1 d . . .
H9 H 0.2520 0.1906 0.0979 0.044 Uiso 1 1 calc R . .
C10 C 1.0480(3) 0.3026(3) 0.29381(14) 0.0468(5) Uani 1 1 d . . .
H10A H 1.0870 0.2816 0.2388 0.056 Uiso 1 1 calc R . .
H10B H 1.0706 0.2314 0.3336 0.056 Uiso 1 1 calc R . .
C11 C 1.1635(3) 0.4953(3) 0.33893(17) 0.0645(7) Uani 1 1 d . . .
H11A H 1.1469 0.5669 0.2986 0.097 Uiso 1 1 calc R . .
H11B H 1.2930 0.5254 0.3539 0.097 Uiso 1 1 calc R . .
H11C H 1.1249 0.5172 0.3932 0.097 Uiso 1 1 calc R . .
C12 C 0.4302(3) 0.0439(3) 0.36759(13) 0.0491(5) Uani 1 1 d . . .
H12A H 0.4810 -0.0131 0.4057 0.059 Uiso 1 1 calc R . .
H12B H 0.3072 -0.0462 0.3328 0.059 Uiso 1 1 calc R . .
C13 C 0.4117(4) 0.1841(4) 0.42625(16) 0.0642(7) Uani 1 1 d . . .
H13A H 0.5323 0.2709 0.4629 0.096 Uiso 1 1 calc R . .
H13B H 0.3289 0.1300 0.4647 0.096 Uiso 1 1 calc R . .
H13C H 0.3619 0.2413 0.3888 0.096 Uiso 1 1 calc R . .
C14 C 0.6322(3) 0.3246(3) -0.14899(13) 0.0503(5) Uani 1 1 d . . .
H14A H 0.6833 0.4485 -0.1511 0.075 Uiso 1 1 calc R . .
H14B H 0.5511 0.2533 -0.2065 0.075 Uiso 1 1 calc R . .
H14C H 0.7320 0.2966 -0.1357 0.075 Uiso 1 1 calc R . .
C15 C 0.0748(3) 0.2573(3) -0.03655(14) 0.0486(5) Uani 1 1 d . . .
H15A H 0.0220 0.2299 0.0152 0.073 Uiso 1 1 calc R . .
H15B H -0.0098 0.1701 -0.0897 0.073 Uiso 1 1 calc R . .
H15C H 0.0952 0.3733 -0.0440 0.073 Uiso 1 1 calc R . .
C16 C 0.2914(3) 0.3411(2) -0.17078(12) 0.0385(4) Uani 1 1 d . . .
H16A H 0.3984 0.4263 -0.1899 0.046 Uiso 1 1 calc R . .
H16B H 0.2185 0.3985 -0.1563 0.046 Uiso 1 1 calc R . .
C17 C 0.1733(3) 0.1823(3) -0.24802(13) 0.0466(5) Uani 1 1 d . . .
H17A H 0.0643 0.0983 -0.2297 0.056 Uiso 1 1 calc R . .
H17B H 0.2450 0.1232 -0.2619 0.056 Uiso 1 1 calc R . .
C18 C 0.1105(3) 0.2361(3) -0.33219(14) 0.0545(6) Uani 1 1 d . . .
H18A H 0.0312 0.1295 -0.3789 0.065 Uiso 1 1 calc R . .
H18B H 0.0354 0.2913 -0.3182 0.065 Uiso 1 1 calc R . .
C19 C 0.2667(4) 0.3621(4) -0.36922(16) 0.0797(8) Uani 1 1 d . . .
H19A H 0.3347 0.4752 -0.3274 0.120 Uiso 1 1 calc R . .
H19B H 0.2161 0.3775 -0.4263 0.120 Uiso 1 1 calc R . .
H19C H 0.3494 0.3143 -0.3777 0.120 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
S1 C2 1.659(2) . ?
O1 C1 1.225(2) . ?
O2 C3 1.235(2) . ?
N1 C2 1.362(3) . ?
N1 C1 1.421(2) . ?
N1 C10 1.479(3) . ?
N2 C2 1.372(3) . ?
N2 C3 1.415(2) . ?
N2 C12 1.481(2) . ?
N3 C7 1.367(3) . ?
N3 C8 1.371(2) . ?
N3 C16 1.486(2) . ?
C1 C4 1.431(3) . ?
C3 C4 1.420(3) . ?
C4 C5 1.451(3) . ?
C5 C6 1.404(3) . ?
C5 C9 1.408(3) . ?
C6 C7 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C14 1.503(3) . ?
C8 C9 1.366(3) . ?
C8 C15 1.499(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.497(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.499(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 C1 124.97(16) . . ?
C2 N1 C10 119.43(15) . . ?
C1 N1 C10 115.59(16) . . ?
C2 N2 C3 124.53(16) . . ?
C2 N2 C12 119.31(15) . . ?
C3 N2 C12 116.07(16) . . ?
C7 N3 C8 119.60(15) . . ?
C7 N3 C16 120.08(15) . . ?
C8 N3 C16 120.32(16) . . ?
O1 C1 N1 116.89(17) . . ?
O1 C1 C4 126.20(17) . . ?
N1 C1 C4 116.85(16) . . ?
N1 C2 N2 116.14(16) . . ?
N1 C2 S1 121.98(15) . . ?
N2 C2 S1 121.87(14) . . ?
O2 C3 N2 116.78(17) . . ?
O2 C3 C4 125.63(17) . . ?
N2 C3 C4 117.57(16) . . ?
C3 C4 C1 119.72(16) . . ?
C3 C4 C5 120.26(17) . . ?
C1 C4 C5 119.88(17) . . ?
C6 C5 C9 114.19(16) . . ?
C6 C5 C4 122.44(17) . . ?
C9 C5 C4 123.34(17) . . ?
C7 C6 C5 122.84(18) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 N3 120.24(17) . . ?
C6 C7 C14 120.26(18) . . ?
N3 C7 C14 119.49(17) . . ?
C9 C8 N3 119.90(17) . . ?
C9 C8 C15 120.57(18) . . ?
N3 C8 C15 119.52(16) . . ?
C8 C9 C5 123.02(18) . . ?
C8 C9 H9 118.5 . . ?
C5 C9 H9 118.5 . . ?
N1 C10 C11 112.78(17) . . ?
N1 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 112.40(18) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
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 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 112.92(15) . . ?
N3 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N3 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 C18 111.76(18) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 114.55(19) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C2 N1 C1 O1 173.70(18) . . . . ?
C10 N1 C1 O1 -5.5(3) . . . . ?
C2 N1 C1 C4 -3.7(3) . . . . ?
C10 N1 C1 C4 177.12(16) . . . . ?
C1 N1 C2 N2 5.5(3) . . . . ?
C10 N1 C2 N2 -175.35(16) . . . . ?
C1 N1 C2 S1 -175.22(14) . . . . ?
C10 N1 C2 S1 3.9(2) . . . . ?
C3 N2 C2 N1 -4.8(3) . . . . ?
C12 N2 C2 N1 178.83(17) . . . . ?
C3 N2 C2 S1 175.91(14) . . . . ?
C12 N2 C2 S1 -0.5(2) . . . . ?
C2 N2 C3 O2 -178.97(18) . . . . ?
C12 N2 C3 O2 -2.5(3) . . . . ?
C2 N2 C3 C4 2.4(3) . . . . ?
C12 N2 C3 C4 178.87(16) . . . . ?
O2 C3 C4 C1 -178.8(2) . . . . ?
N2 C3 C4 C1 -0.4(3) . . . . ?
O2 C3 C4 C5 5.3(3) . . . . ?
N2 C3 C4 C5 -176.25(15) . . . . ?
O1 C1 C4 C3 -176.2(2) . . . . ?
N1 C1 C4 C3 0.9(3) . . . . ?
O1 C1 C4 C5 -0.3(3) . . . . ?
N1 C1 C4 C5 176.83(15) . . . . ?
C3 C4 C5 C6 -164.18(17) . . . . ?
C1 C4 C5 C6 19.9(3) . . . . ?
C3 C4 C5 C9 17.8(3) . . . . ?
C1 C4 C5 C9 -158.11(17) . . . . ?
C9 C5 C6 C7 4.6(3) . . . . ?
C4 C5 C6 C7 -173.66(17) . . . . ?
C5 C6 C7 N3 -1.3(3) . . . . ?
C5 C6 C7 C14 177.34(17) . . . . ?
C8 N3 C7 C6 -2.4(3) . . . . ?
C16 N3 C7 C6 177.23(16) . . . . ?
C8 N3 C7 C14 178.97(17) . . . . ?
C16 N3 C7 C14 -1.4(2) . . . . ?
C7 N3 C8 C9 2.4(3) . . . . ?
C16 N3 C8 C9 -177.25(16) . . . . ?
C7 N3 C8 C15 -178.34(17) . . . . ?
C16 N3 C8 C15 2.0(2) . . . . ?
N3 C8 C9 C5 1.3(3) . . . . ?
C15 C8 C9 C5 -177.96(18) . . . . ?
C6 C5 C9 C8 -4.6(3) . . . . ?
C4 C5 C9 C8 173.62(17) . . . . ?
C2 N1 C10 C11 -89.3(2) . . . . ?
C1 N1 C10 C11 89.9(2) . . . . ?
C2 N2 C12 C13 87.9(2) . . . . ?
C3 N2 C12 C13 -88.7(2) . . . . ?
C7 N3 C16 C17 88.1(2) . . . . ?
C8 N3 C16 C17 -92.2(2) . . . . ?
N3 C16 C17 C18 -178.66(17) . . . . ?
C16 C17 C18 C19 60.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_dm16481_0m
_database_code_depnum_ccdc_archive 'CCDC 1498114'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O'
_chemical_formula_weight         172.18

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                   7.1417(9)
_cell_length_b                   7.8540(10)
_cell_length_c                   8.9569(11)
_cell_angle_alpha                72.724(2)
_cell_angle_beta                 74.137(2)
_cell_angle_gamma                68.176(2)
_cell_volume                     437.76(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    1970
_cell_measurement_theta_min      5.726
_cell_measurement_theta_max      55.239

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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            3198
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1713
_reflns_number_gt                1527
_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-2013 (Sheldrick, 2013)'
_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)+(0.0411P)²+0.1113P] 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
_refine_ls_extinction_coef       0.061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1713
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
N1 N 0.21128(17) 0.79026(15) 1.42609(13) 0.0384(3) Uani 1 1 d . . . . .
N2 N 0.13693(15) 1.39524(14) 1.19951(11) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.31811(11) 0.95156(10) 0.72083(9) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.31786(15) 0.80867(14) 0.85270(13) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.27761(15) 0.83857(15) 1.00062(13) 0.0224(2) Uani 1 1 d . . . . .
H2 H 0.2778 0.7363 1.0899 0.027 Uiso 1 1 calc R U . . .
C3 C 0.23465(14) 1.02261(14) 1.02458(12) 0.0214(2) Uani 1 1 d . . . . .
C4 C 0.22788(15) 1.16905(14) 0.88364(13) 0.0221(2) Uani 1 1 d . . . . .
H4 H 0.1947 1.2950 0.8924 0.027 Uiso 1 1 calc R U . . .
C5 C 0.26775(15) 1.13134(14) 0.73874(13) 0.0225(2) Uani 1 1 d . . . . .
C6 C 0.26370(18) 1.26850(16) 0.58348(13) 0.0290(3) Uani 1 1 d . . . . .
H6A H 0.2344 1.3943 0.6003 0.044 Uiso 1 1 calc R U . . .
H6B H 0.1567 1.2689 0.5342 0.044 Uiso 1 1 calc R U . . .
H6C H 0.3973 1.2328 0.5135 0.044 Uiso 1 1 calc R U . . .
C7 C 0.36758(17) 0.62590(15) 0.80983(14) 0.0273(3) Uani 1 1 d . . . . .
H7A H 0.5127 0.5844 0.7603 0.041 Uiso 1 1 calc R U . . .
H7B H 0.2821 0.6408 0.7349 0.041 Uiso 1 1 calc R U . . .
H7C H 0.3408 0.5320 0.9060 0.041 Uiso 1 1 calc R U . . .
C8 C 0.19974(16) 1.05835(15) 1.17488(13) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.20516(17) 0.91154(16) 1.31507(13) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.16358(16) 1.24356(16) 1.19187(12) 0.0245(3) Uani 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
N1 C9 1.1525(15) . ?
N2 C10 1.1545(14) . ?
O1 C1 1.3666(12) . ?
O1 C5 1.3690(13) . ?
C1 C2 1.3490(15) . ?
C1 C7 1.4859(14) . ?
C2 C3 1.4311(15) . ?
C2 H2 0.9500 . ?
C3 C8 1.3936(15) . ?
C3 C4 1.4311(14) . ?
C4 C5 1.3479(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4846(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.4271(15) . ?
C8 C9 1.4287(15) . ?

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
C1 O1 C5 119.45(8) . . ?
C2 C1 O1 121.71(9) . . ?
C2 C1 C7 126.64(10) . . ?
O1 C1 C7 111.64(9) . . ?
C1 C2 C3 120.73(10) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C8 C3 C2 122.56(10) . . ?
C8 C3 C4 121.88(10) . . ?
C2 C3 C4 115.56(9) . . ?
C5 C4 C3 121.14(10) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 O1 121.27(9) . . ?
C4 C5 C6 126.99(10) . . ?
O1 C5 C6 111.74(9) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 C10 120.34(10) . . ?
C3 C8 C9 121.50(10) . . ?
C10 C8 C9 118.13(10) . . ?
N1 C9 C8 178.50(12) . . ?
N2 C10 C8 177.41(11) . . ?

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
C5 O1 C1 C2 -2.84(14) . . . . ?
C5 O1 C1 C7 177.58(8) . . . . ?
O1 C1 C2 C3 -0.40(16) . . . . ?
C7 C1 C2 C3 179.11(9) . . . . ?
C1 C2 C3 C8 -177.58(9) . . . . ?
C1 C2 C3 C4 2.97(14) . . . . ?
C8 C3 C4 C5 178.09(9) . . . . ?
C2 C3 C4 C5 -2.45(15) . . . . ?
C3 C4 C5 O1 -0.65(16) . . . . ?
C3 C4 C5 C6 179.12(10) . . . . ?
C1 O1 C5 C4 3.37(14) . . . . ?
C1 O1 C5 C6 -176.42(8) . . . . ?
C2 C3 C8 C10 178.13(9) . . . . ?
C4 C3 C8 C10 -2.46(15) . . . . ?
C2 C3 C8 C9 0.07(16) . . . . ?
C4 C3 C8 C9 179.49(9) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_20150723a_0m
_database_code_depnum_ccdc_archive 'CCDC 1498117'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N3'
_chemical_formula_weight         227.31

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6023(8)
_cell_length_b                   9.0012(10)
_cell_length_c                   9.9056(11)
_cell_angle_alpha                79.040(2)
_cell_angle_beta                 84.018(2)
_cell_angle_gamma                80.824(2)
_cell_volume                     655.05(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7290
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.43

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            9125
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2417
_reflns_number_gt                2231
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0666P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2417
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
N1 N 0.10928(11) 0.19813(9) 0.26928(8) 0.0198(2) Uani 1 1 d . . .
N2 N -0.52233(12) 0.07398(10) 0.65687(9) 0.0278(2) Uani 1 1 d . . .
N3 N -0.16902(13) 0.31647(11) 0.83373(9) 0.0295(2) Uani 1 1 d . . .
C1 C 0.32618(14) 0.32469(13) 0.36067(11) 0.0264(2) Uani 1 1 d . . .
H1A H 0.3326 0.3742 0.4374 0.040 Uiso 1 1 calc R . .
H1B H 0.3340 0.3972 0.2764 0.040 Uiso 1 1 calc R . .
H1C H 0.4233 0.2424 0.3593 0.040 Uiso 1 1 calc R . .
C2 C 0.15234(13) 0.26266(11) 0.37457(10) 0.0211(2) Uani 1 1 d . . .
C3 C 0.03823(13) 0.26791(10) 0.49050(10) 0.0211(2) Uani 1 1 d . . .
H3 H 0.0681 0.3138 0.5599 0.025 Uiso 1 1 calc R . .
C4 C -0.12355(13) 0.20565(10) 0.50782(10) 0.0191(2) Uani 1 1 d . . .
C5 C -0.16180(13) 0.14095(10) 0.39699(10) 0.0190(2) Uani 1 1 d . . .
H5 H -0.2668 0.0984 0.4036 0.023 Uiso 1 1 calc R . .
C6 C -0.04897(13) 0.13900(11) 0.28029(10) 0.0196(2) Uani 1 1 d . . .
C7 C -0.09788(14) 0.07386(12) 0.16307(10) 0.0240(2) Uani 1 1 d . . .
H7A H -0.2134 0.0414 0.1852 0.036 Uiso 1 1 calc R . .
H7B H -0.0106 -0.0121 0.1478 0.036 Uiso 1 1 calc R . .
H7C H -0.1009 0.1506 0.0811 0.036 Uiso 1 1 calc R . .
C8 C -0.24087(13) 0.20542(11) 0.62878(10) 0.0201(2) Uani 1 1 d . . .
C9 C -0.39684(13) 0.13440(11) 0.64473(9) 0.0207(2) Uani 1 1 d . . .
C10 C -0.20223(13) 0.26759(11) 0.74137(10) 0.0220(2) Uani 1 1 d . . .
C11 C 0.23132(13) 0.19478(11) 0.14249(10) 0.0229(2) Uani 1 1 d . . .
H11A H 0.2210 0.1048 0.1050 0.027 Uiso 1 1 calc R . .
H11B H 0.3535 0.1864 0.1664 0.027 Uiso 1 1 calc R . .
C12 C 0.19199(13) 0.33611(11) 0.03233(10) 0.0217(2) Uani 1 1 d . . .
H12A H 0.2065 0.4263 0.0679 0.026 Uiso 1 1 calc R . .
H12B H 0.0692 0.3466 0.0093 0.026 Uiso 1 1 calc R . .
C13 C 0.31704(15) 0.32476(13) -0.09698(11) 0.0306(3) Uani 1 1 d . . .
H13A H 0.4397 0.3124 -0.0731 0.037 Uiso 1 1 calc R . .
H13B H 0.3014 0.2348 -0.1325 0.037 Uiso 1 1 calc R . .
C14 C 0.28325(16) 0.46499(14) -0.20886(12) 0.0351(3) Uani 1 1 d . . .
H14A H 0.1622 0.4773 -0.2333 0.053 Uiso 1 1 calc R . .
H14B H 0.3636 0.4522 -0.2886 0.053 Uiso 1 1 calc R . .
H14C H 0.3026 0.5539 -0.1753 0.053 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
N1 C2 1.3764(13) . ?
N1 C6 1.3774(13) . ?
N1 C11 1.4838(12) . ?
N2 C9 1.1563(13) . ?
N3 C10 1.1536(13) . ?
C1 C2 1.4985(13) . ?
C2 C3 1.3688(14) . ?
C3 C4 1.4126(14) . ?
C4 C5 1.4116(14) . ?
C4 C8 1.4171(14) . ?
C5 C6 1.3669(14) . ?
C6 C7 1.4996(13) . ?
C8 C10 1.4147(13) . ?
C8 C9 1.4156(14) . ?
C11 C12 1.5223(14) . ?
C12 C13 1.5231(14) . ?
C13 C14 1.5203(16) . ?

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 C6 120.03(8) . . ?
C2 N1 C11 120.16(8) . . ?
C6 N1 C11 119.80(8) . . ?
C3 C2 N1 120.08(9) . . ?
C3 C2 C1 120.93(9) . . ?
N1 C2 C1 118.99(9) . . ?
C2 C3 C4 121.91(9) . . ?
C5 C4 C3 115.85(9) . . ?
C5 C4 C8 121.28(9) . . ?
C3 C4 C8 122.87(9) . . ?
C6 C5 C4 121.90(9) . . ?
C5 C6 N1 120.19(9) . . ?
C5 C6 C7 120.11(9) . . ?
N1 C6 C7 119.70(8) . . ?
C10 C8 C9 117.27(8) . . ?
C10 C8 C4 121.70(9) . . ?
C9 C8 C4 120.93(8) . . ?
N2 C9 C8 178.68(10) . . ?
N3 C10 C8 179.03(11) . . ?
N1 C11 C12 112.94(8) . . ?
C11 C12 C13 110.83(8) . . ?
C14 C13 C12 112.35(9) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_20150806b_0m
_database_code_depnum_ccdc_archive 'CCDC 1498118'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 N3'
_chemical_formula_sum            'C18 H25 N3'
_chemical_formula_weight         283.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'

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

_cell_length_a                   9.3267(14)
_cell_length_b                   14.003(2)
_cell_length_c                   14.7925(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.492(7)
_cell_angle_gamma                90.00
_cell_volume                     1664.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8777
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.48

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            12263
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.99
_reflns_number_total             5351
_reflns_number_gt                4931
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(16)
_refine_ls_number_reflns         5351
_refine_ls_number_parameters     385
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
N1 N -0.08161(15) 0.16106(10) 0.41130(10) 0.0248(3) Uani 1 1 d . . .
N2 N -0.78194(19) 0.02134(13) 0.18117(12) 0.0415(4) Uani 1 1 d . . .
N3 N -0.74743(19) 0.33436(12) 0.23231(12) 0.0386(4) Uani 1 1 d . . .
N4 N 0.93829(16) 0.33199(10) 0.68433(10) 0.0249(3) Uani 1 1 d . . .
N5 N 1.6222(2) 0.47668(14) 0.81920(14) 0.0455(5) Uani 1 1 d . . .
N6 N 1.5816(2) 0.16691(13) 0.76747(15) 0.0441(4) Uani 1 1 d . . .
C1 C -0.0858(2) -0.01590(14) 0.40592(15) 0.0380(5) Uani 1 1 d . . .
H1A H -0.1654 -0.0662 0.3721 0.057 Uiso 1 1 calc R . .
H1B H -0.0303 -0.0243 0.4806 0.057 Uiso 1 1 calc R . .
H1C H -0.0055 -0.0177 0.3836 0.057 Uiso 1 1 calc R . .
C2 C -0.1731(2) 0.07814(12) 0.37717(12) 0.0256(4) Uani 1 1 d . . .
C3 C -0.3431(2) 0.08275(12) 0.31954(12) 0.0257(4) Uani 1 1 d . . .
H3 H -0.4035 0.0263 0.2958 0.031 Uiso 1 1 calc R . .
C4 C -0.4293(2) 0.17003(12) 0.29511(11) 0.0246(4) Uani 1 1 d . . .
C5 C -0.32948(19) 0.25315(12) 0.32884(12) 0.0252(4) Uani 1 1 d . . .
H5 H -0.3805 0.3127 0.3120 0.030 Uiso 1 1 calc R . .
C6 C -0.1598(2) 0.24801(12) 0.38560(12) 0.0249(4) Uani 1 1 d . . .
C7 C -0.0572(2) 0.33788(13) 0.42129(14) 0.0323(4) Uani 1 1 d . . .
H7A H -0.1290 0.3924 0.3928 0.049 Uiso 1 1 calc R . .
H7B H 0.0210 0.3375 0.3973 0.049 Uiso 1 1 calc R . .
H7C H 0.0017 0.3410 0.4965 0.049 Uiso 1 1 calc R . .
C8 C -0.6060(2) 0.17483(13) 0.24241(12) 0.0265(4) Uani 1 1 d . . .
C9 C -0.70402(19) 0.09054(14) 0.20836(12) 0.0297(4) Uani 1 1 d . . .
C10 C -0.68650(19) 0.26210(15) 0.23445(12) 0.0300(4) Uani 1 1 d . . .
C11 C 0.10324(19) 0.15446(12) 0.47279(12) 0.0254(4) Uani 1 1 d . . .
H11A H 0.1348 0.0971 0.5154 0.031 Uiso 1 1 calc R . .
H11B H 0.1469 0.2088 0.5198 0.031 Uiso 1 1 calc R . .
C12 C 0.1820(2) 0.15217(13) 0.40445(12) 0.0307(4) Uani 1 1 d . . .
H12A H 0.1784 0.2155 0.3769 0.037 Uiso 1 1 calc R . .
H12B H 0.1193 0.1094 0.3456 0.037 Uiso 1 1 calc R . .
C13 C 0.3628(2) 0.11823(14) 0.46811(13) 0.0302(4) Uani 1 1 d . . .
H13A H 0.4225 0.1403 0.4341 0.036 Uiso 1 1 calc R . .
H13B H 0.4148 0.1469 0.5373 0.036 Uiso 1 1 calc R . .
C14 C 0.3789(2) 0.01023(15) 0.47964(13) 0.0325(4) Uani 1 1 d . . .
H14A H 0.3205 -0.0188 0.4106 0.039 Uiso 1 1 calc R . .
H14B H 0.3263 -0.0115 0.5182 0.039 Uiso 1 1 calc R . .
C15 C 0.5599(2) -0.02259(15) 0.53666(13) 0.0352(4) Uani 1 1 d . . .
H15A H 0.6145 0.0040 0.5014 0.042 Uiso 1 1 calc R . .
H15B H 0.6155 0.0026 0.6075 0.042 Uiso 1 1 calc R . .
C16 C 0.5804(2) -0.13031(15) 0.54181(14) 0.0364(4) Uani 1 1 d . . .
H16A H 0.5277 -0.1570 0.5783 0.044 Uiso 1 1 calc R . .
H16B H 0.5235 -0.1557 0.4710 0.044 Uiso 1 1 calc R . .
C17 C 0.7609(3) -0.16180(16) 0.59713(18) 0.0472(6) Uani 1 1 d . . .
H17A H 0.8138 -0.1344 0.5611 0.057 Uiso 1 1 calc R . .
H17B H 0.8174 -0.1368 0.6681 0.057 Uiso 1 1 calc R . .
C18 C 0.7827(3) -0.26905(19) 0.6017(2) 0.0621(7) Uani 1 1 d . . .
H18A H 0.7306 -0.2968 0.6372 0.093 Uiso 1 1 calc R . .
H18B H 0.8991 -0.2843 0.6391 0.093 Uiso 1 1 calc R . .
H18C H 0.7321 -0.2941 0.5317 0.093 Uiso 1 1 calc R . .
C19 C 0.9138(2) 0.15589(14) 0.66543(15) 0.0341(4) Uani 1 1 d . . .
H19A H 0.8758 0.1481 0.7144 0.051 Uiso 1 1 calc R . .
H19B H 0.9822 0.1025 0.6707 0.051 Uiso 1 1 calc R . .
H19C H 0.8198 0.1594 0.5955 0.051 Uiso 1 1 calc R . .
C20 C 1.01317(19) 0.24593(12) 0.68995(12) 0.0256(4) Uani 1 1 d . . .
C21 C 1.17736(19) 0.24334(13) 0.71799(12) 0.0256(4) Uani 1 1 d . . .
H21 H 1.2270 0.1846 0.7226 0.031 Uiso 1 1 calc R . .
C22 C 1.2737(2) 0.32732(12) 0.74015(12) 0.0253(4) Uani 1 1 d . . .
C23 C 1.1900(2) 0.41357(13) 0.73084(12) 0.0269(4) Uani 1 1 d . . .
H23 H 1.2477 0.4708 0.7438 0.032 Uiso 1 1 calc R . .
C24 C 1.02645(19) 0.41554(12) 0.70326(11) 0.0254(4) Uani 1 1 d . . .
C25 C 0.9406(2) 0.50824(14) 0.69308(15) 0.0348(4) Uani 1 1 d . . .
H25A H 1.0167 0.5599 0.7067 0.052 Uiso 1 1 calc R . .
H25B H 0.9031 0.5103 0.7427 0.052 Uiso 1 1 calc R . .
H25C H 0.8469 0.5142 0.6233 0.052 Uiso 1 1 calc R . .
C26 C 1.4441(2) 0.32457(13) 0.76975(12) 0.0275(4) Uani 1 1 d . . .
C27 C 1.5417(2) 0.40896(15) 0.79699(13) 0.0322(4) Uani 1 1 d . . .
C28 C 1.5214(2) 0.23770(14) 0.77014(13) 0.0295(4) Uani 1 1 d . . .
C29 C 0.76106(19) 0.33584(13) 0.65600(12) 0.0273(4) Uani 1 1 d . . .
H29A H 0.7455 0.3896 0.6915 0.033 Uiso 1 1 calc R . .
H29B H 0.7341 0.2781 0.6805 0.033 Uiso 1 1 calc R . .
C30 C 0.6420(2) 0.34578(14) 0.53796(12) 0.0301(4) Uani 1 1 d . . .
H30A H 0.6334 0.2850 0.5042 0.036 Uiso 1 1 calc R . .
H30B H 0.6862 0.3922 0.5098 0.036 Uiso 1 1 calc R . .
C31 C 0.4679(2) 0.37757(14) 0.51319(13) 0.0311(4) Uani 1 1 d . . .
H31A H 0.3875 0.3598 0.4415 0.037 Uiso 1 1 calc R . .
H31B H 0.4393 0.3437 0.5591 0.037 Uiso 1 1 calc R . .
C32 C 0.45481(19) 0.48434(14) 0.52625(13) 0.0305(4) Uani 1 1 d . . .
H32A H 0.4846 0.5187 0.4812 0.037 Uiso 1 1 calc R . .
H32B H 0.5330 0.5023 0.5982 0.037 Uiso 1 1 calc R . .
C33 C 0.2795(2) 0.51295(13) 0.49891(13) 0.0303(4) Uani 1 1 d . . .
H33A H 0.2008 0.4862 0.4310 0.036 Uiso 1 1 calc R . .
H33B H 0.2564 0.4849 0.5501 0.036 Uiso 1 1 calc R . .
C34 C 0.2508(2) 0.61911(15) 0.49565(13) 0.0333(4) Uani 1 1 d . . .
H34A H 0.2761 0.6479 0.4457 0.040 Uiso 1 1 calc R . .
H34B H 0.3264 0.6460 0.5642 0.040 Uiso 1 1 calc R . .
C35 C 0.0720(2) 0.64427(15) 0.46482(14) 0.0385(5) Uani 1 1 d . . .
H35A H -0.0036 0.6127 0.3992 0.046 Uiso 1 1 calc R . .
H35B H 0.0502 0.6197 0.5180 0.046 Uiso 1 1 calc R . .
C36 C 0.0363(3) 0.75002(16) 0.45241(16) 0.0507(6) Uani 1 1 d . . .
H36A H 0.1064 0.7816 0.5181 0.076 Uiso 1 1 calc R . .
H36B H -0.0783 0.7607 0.4311 0.076 Uiso 1 1 calc R . .
H36C H 0.0579 0.7751 0.4001 0.076 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
N1 C6 1.370(2) . ?
N1 C2 1.376(2) . ?
N1 C11 1.4889(19) . ?
N2 C9 1.154(2) . ?
N3 C10 1.153(2) . ?
N4 C20 1.374(2) . ?
N4 C24 1.375(2) . ?
N4 C29 1.486(2) . ?
N5 C27 1.149(3) . ?
N6 C28 1.150(2) . ?
C1 C2 1.492(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.369(2) . ?
C3 C4 1.406(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(2) . ?
C4 C8 1.422(2) . ?
C5 C6 1.366(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C10 1.408(3) . ?
C8 C9 1.420(2) . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.531(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.517(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.517(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.512(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.496(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.369(2) . ?
C21 C22 1.414(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.406(2) . ?
C22 C26 1.419(2) . ?
C23 C24 1.365(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.492(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C28 1.413(3) . ?
C26 C27 1.419(3) . ?
C29 C30 1.528(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.537(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.520(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.525(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.507(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.530(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.509(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
C6 N1 C2 120.28(13) . . ?
C6 N1 C11 120.86(13) . . ?
C2 N1 C11 118.81(13) . . ?
C20 N4 C24 120.07(13) . . ?
C20 N4 C29 120.49(14) . . ?
C24 N4 C29 119.43(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 119.69(15) . . ?
C3 C2 C1 120.76(15) . . ?
N1 C2 C1 119.53(14) . . ?
C2 C3 C4 122.14(16) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 115.87(15) . . ?
C3 C4 C8 122.30(15) . . ?
C5 C4 C8 121.80(15) . . ?
C6 C5 C4 121.58(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 N1 120.32(15) . . ?
C5 C6 C7 120.24(15) . . ?
N1 C6 C7 119.44(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C9 118.14(15) . . ?
C10 C8 C4 120.49(15) . . ?
C9 C8 C4 120.91(15) . . ?
N2 C9 C8 179.14(18) . . ?
N3 C10 C8 177.08(16) . . ?
N1 C11 C12 113.28(12) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.51(13) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 113.11(15) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 112.32(15) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 113.75(16) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.13(17) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 113.6(2) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N4 119.84(16) . . ?
C21 C20 C19 120.74(16) . . ?
N4 C20 C19 119.42(14) . . ?
C20 C21 C22 122.00(17) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 115.82(16) . . ?
C23 C22 C26 122.19(16) . . ?
C21 C22 C26 121.98(16) . . ?
C24 C23 C22 121.83(16) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 N4 120.40(16) . . ?
C23 C24 C25 120.58(16) . . ?
N4 C24 C25 119.02(14) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C28 C26 C22 120.94(16) . . ?
C28 C26 C27 117.61(16) . . ?
C22 C26 C27 121.42(16) . . ?
N5 C27 C26 179.2(2) . . ?
N6 C28 C26 178.09(18) . . ?
N4 C29 C30 112.66(14) . . ?
N4 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
N4 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C29 C30 C31 111.49(14) . . ?
C29 C30 H30A 109.3 . . ?
C31 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
C31 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
C32 C31 C30 113.45(15) . . ?
C32 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 C33 111.67(14) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 114.62(15) . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 112.68(16) . . ?
C33 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
C36 C35 C34 113.75(18) . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
C34 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C6 N1 C2 C3 -1.6(2) . . . . ?
C11 N1 C2 C3 -179.27(14) . . . . ?
C6 N1 C2 C1 179.99(15) . . . . ?
C11 N1 C2 C1 2.3(2) . . . . ?
N1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C3 C4 177.14(16) . . . . ?
C2 C3 C4 C5 3.3(2) . . . . ?
C2 C3 C4 C8 -174.94(15) . . . . ?
C3 C4 C5 C6 -2.8(2) . . . . ?
C8 C4 C5 C6 175.51(15) . . . . ?
C4 C5 C6 N1 0.1(2) . . . . ?
C4 C5 C6 C7 -179.33(15) . . . . ?
C2 N1 C6 C5 2.2(2) . . . . ?
C11 N1 C6 C5 179.77(14) . . . . ?
C2 N1 C6 C7 -178.38(14) . . . . ?
C11 N1 C6 C7 -0.8(2) . . . . ?
C3 C4 C8 C10 169.64(15) . . . . ?
C5 C4 C8 C10 -8.5(2) . . . . ?
C3 C4 C8 C9 -2.4(2) . . . . ?
C5 C4 C8 C9 179.43(15) . . . . ?
C10 C8 C9 N2 -172(100) . . . . ?
C4 C8 C9 N2 0(12) . . . . ?
C9 C8 C10 N3 130(4) . . . . ?
C4 C8 C10 N3 -42(4) . . . . ?
C6 N1 C11 C12 -90.01(17) . . . . ?
C2 N1 C11 C12 87.62(17) . . . . ?
N1 C11 C12 C13 -164.48(15) . . . . ?
C11 C12 C13 C14 80.78(18) . . . . ?
C12 C13 C14 C15 176.01(14) . . . . ?
C13 C14 C15 C16 -175.30(14) . . . . ?
C14 C15 C16 C17 179.05(17) . . . . ?
C15 C16 C17 C18 -179.39(18) . . . . ?
C24 N4 C20 C21 2.2(2) . . . . ?
C29 N4 C20 C21 -178.83(15) . . . . ?
C24 N4 C20 C19 -177.85(14) . . . . ?
C29 N4 C20 C19 1.1(2) . . . . ?
N4 C20 C21 C22 -1.0(2) . . . . ?
C19 C20 C21 C22 179.09(15) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C20 C21 C22 C26 179.66(15) . . . . ?
C21 C22 C23 C24 0.7(2) . . . . ?
C26 C22 C23 C24 -179.39(15) . . . . ?
C22 C23 C24 N4 0.5(2) . . . . ?
C22 C23 C24 C25 -179.44(15) . . . . ?
C20 N4 C24 C23 -2.0(2) . . . . ?
C29 N4 C24 C23 179.07(15) . . . . ?
C20 N4 C24 C25 177.93(14) . . . . ?
C29 N4 C24 C25 -1.0(2) . . . . ?
C23 C22 C26 C28 -174.76(16) . . . . ?
C21 C22 C26 C28 5.1(2) . . . . ?
C23 C22 C26 C27 3.4(2) . . . . ?
C21 C22 C26 C27 -176.73(16) . . . . ?
C28 C26 C27 N5 1(15) . . . . ?
C22 C26 C27 N5 -177(100) . . . . ?
C22 C26 C28 N6 67(6) . . . . ?
C27 C26 C28 N6 -112(6) . . . . ?
C20 N4 C29 C30 -90.44(18) . . . . ?
C24 N4 C29 C30 88.50(17) . . . . ?
N4 C29 C30 C31 -164.02(15) . . . . ?
C29 C30 C31 C32 80.38(19) . . . . ?
C30 C31 C32 C33 178.92(14) . . . . ?
C31 C32 C33 C34 -172.00(14) . . . . ?
C32 C33 C34 C35 178.33(14) . . . . ?
C33 C34 C35 C36 -175.31(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_cd16359
_database_code_depnum_ccdc_archive 'CCDC 1498121'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 N3 O3 S'
_chemical_formula_weight         351.46

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/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                   10.9669(13)
_cell_length_b                   14.1993(16)
_cell_length_c                   12.5425(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.925(2)
_cell_angle_gamma                90
_cell_volume                     1756.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2791
_cell_measurement_theta_min      4.612
_cell_measurement_theta_max      52.441

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9920
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3252
_reflns_number_gt                2617
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0881P)²+0.5372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     222
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.73062(7) 1.11921(4) 0.44092(5) 0.0549(2) Uani 1 1 d . . . . .
N1 N 0.78398(17) 1.07078(11) 0.26042(15) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.60475(16) 0.99290(11) 0.27189(14) 0.0383(4) Uani 1 1 d . . . . .
N3 N 0.60908(19) 0.78189(12) -0.18773(15) 0.0442(4) Uani 1 1 d . . . . .
O1 O 0.85305(17) 1.03732(12) 0.11968(15) 0.0580(5) Uani 1 1 d . . . . .
O2 O 0.49625(19) 0.87315(12) 0.15097(16) 0.0623(5) Uani 1 1 d . . . . .
O3 O 0.2371(3) 0.79838(19) 0.0292(2) 0.1028(8) Uani 1 1 d D . . . .
H3B H 0.1826 0.8360 -0.0333 0.123 Uiso 1 1 d DR U . . .
H3A H 0.2926 0.8368 0.0772 0.123 Uiso 1 1 d DR U . . .
C1 C 0.7055(2) 1.05827(13) 0.31844(18) 0.0384(5) Uani 1 1 d . . . . .
C2 C 0.7714(2) 1.01838(14) 0.15926(18) 0.0393(5) Uani 1 1 d . . . . .
C3 C 0.66708(19) 0.94913(13) 0.11431(17) 0.0346(4) Uani 1 1 d . . . . .
C4 C 0.5834(2) 0.93406(14) 0.17394(18) 0.0392(5) Uani 1 1 d . . . . .
C5 C 0.6480(2) 0.89282(13) 0.01175(17) 0.0345(4) Uani 1 1 d . . . . .
C6 C 0.7378(2) 0.89364(15) -0.04119(19) 0.0436(5) Uani 1 1 d . . . . .
H6 H 0.8136 0.9326 -0.0092 0.052 Uiso 1 1 calc R U . . .
C7 C 0.7186(2) 0.83965(16) -0.1378(2) 0.0483(5) Uani 1 1 d . . . . .
C8 C 0.5203(2) 0.77600(14) -0.13895(18) 0.0405(5) Uani 1 1 d . . . . .
C9 C 0.5376(2) 0.83081(13) -0.04371(17) 0.0381(5) Uani 1 1 d . . . . .
H9 H 0.4735 0.8270 -0.0141 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8952(2) 1.14126(15) 0.3048(2) 0.0471(5) Uani 1 1 d . . . . .
H10A H 0.8707 1.1921 0.3434 0.056 Uiso 1 1 calc R U . . .
H10B H 0.9061 1.1677 0.2382 0.056 Uiso 1 1 calc R U . . .
C11 C 1.0268(2) 1.09969(19) 0.3904(2) 0.0605(7) Uani 1 1 d . . . . .
H11A H 1.0167 1.0735 0.4566 0.091 Uiso 1 1 calc R U . . .
H11B H 1.0951 1.1479 0.4178 0.091 Uiso 1 1 calc R U . . .
H11C H 1.0533 1.0509 0.3517 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5118(2) 0.97732(16) 0.3271(2) 0.0467(5) Uani 1 1 d . . . . .
H12A H 0.4237 0.9587 0.2664 0.056 Uiso 1 1 calc R U . . .
H12B H 0.5005 1.0360 0.3614 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5618(3) 0.9037(2) 0.4211(2) 0.0668(7) Uani 1 1 d . . . . .
H13A H 0.5763 0.8460 0.3884 0.100 Uiso 1 1 calc R U . . .
H13B H 0.4959 0.8937 0.4510 0.100 Uiso 1 1 calc R U . . .
H13C H 0.6457 0.9240 0.4845 0.100 Uiso 1 1 calc R U . . .
C14 C 0.8174(3) 0.8455(2) -0.1911(3) 0.0781(9) Uani 1 1 d . . . . .
H14A H 0.8461 0.7833 -0.1996 0.117 Uiso 1 1 calc R U . . .
H14B H 0.8948 0.8820 -0.1402 0.117 Uiso 1 1 calc R U . . .
H14C H 0.7745 0.8751 -0.2675 0.117 Uiso 1 1 calc R U . . .
C15 C 0.4048(3) 0.70782(17) -0.1885(2) 0.0560(6) Uani 1 1 d . . . . .
H15A H 0.3515 0.7204 -0.2713 0.084 Uiso 1 1 calc R U . . .
H15B H 0.3492 0.7145 -0.1474 0.084 Uiso 1 1 calc R U . . .
H15C H 0.4396 0.6448 -0.1787 0.084 Uiso 1 1 calc R U . . .
C16 C 0.5843(3) 0.72529(17) -0.2953(2) 0.0567(6) Uani 1 1 d . . . . .
H16A H 0.6225 0.7580 -0.3416 0.068 Uiso 1 1 calc R U . . .
H16B H 0.4874 0.7195 -0.3437 0.068 Uiso 1 1 calc R U . . .
C17 C 0.6456(4) 0.6288(2) -0.2645(3) 0.0774(9) Uani 1 1 d . . . . .
H17A H 0.7413 0.6342 -0.2153 0.116 Uiso 1 1 calc R U . . .
H17B H 0.6305 0.5956 -0.3359 0.116 Uiso 1 1 calc R U . . .
H17C H 0.6043 0.5949 -0.2226 0.116 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 C1 1.678(2) . ?
N1 C1 1.360(3) . ?
N1 C2 1.425(3) . ?
N1 C10 1.485(3) . ?
N2 C1 1.364(3) . ?
N2 C4 1.418(3) . ?
N2 C12 1.479(3) . ?
N3 C7 1.360(3) . ?
N3 C8 1.361(3) . ?
N3 C16 1.490(3) . ?
O1 C2 1.229(2) . ?
O2 C4 1.226(2) . ?
O3 H3B 0.9197 . ?
O3 H3A 0.8429 . ?
C2 C3 1.424(3) . ?
C3 C4 1.431(3) . ?
C3 C5 1.450(3) . ?
C5 C6 1.408(3) . ?
C5 C9 1.410(3) . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C14 1.504(3) . ?
C8 C9 1.367(3) . ?
C8 C15 1.496(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.493(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.489(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.500(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 N1 C2 124.79(16) . . ?
C1 N1 C10 119.69(17) . . ?
C2 N1 C10 115.48(16) . . ?
C1 N2 C4 124.62(17) . . ?
C1 N2 C12 119.80(17) . . ?
C4 N2 C12 115.54(16) . . ?
C7 N3 C8 119.44(17) . . ?
C7 N3 C16 121.13(19) . . ?
C8 N3 C16 119.42(18) . . ?
C4 O2 H3A 149.0 . . ?
H3B O3 H3A 103.3 . . ?
N1 C1 N2 116.35(17) . . ?
N1 C1 S1 122.25(15) . . ?
N2 C1 S1 121.40(16) . . ?
O1 C2 C3 126.31(19) . . ?
O1 C2 N1 116.20(18) . . ?
C3 C2 N1 117.49(18) . . ?
C2 C3 C4 118.94(18) . . ?
C2 C3 C5 120.74(18) . . ?
C4 C3 C5 120.30(17) . . ?
O2 C4 N2 115.84(18) . . ?
O2 C4 C3 126.50(19) . . ?
N2 C4 C3 117.63(17) . . ?
C6 C5 C9 113.52(18) . . ?
C6 C5 C3 123.67(18) . . ?
C9 C5 C3 122.81(18) . . ?
C7 C6 C5 122.9(2) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N3 C7 C6 120.6(2) . . ?
N3 C7 C14 119.5(2) . . ?
C6 C7 C14 120.0(2) . . ?
N3 C8 C9 120.27(18) . . ?
N3 C8 C15 119.68(18) . . ?
C9 C8 C15 120.04(19) . . ?
C8 C9 C5 123.25(19) . . ?
C8 C9 H9 118.4 . . ?
C5 C9 H9 118.4 . . ?
N1 C10 C11 112.37(18) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 112.64(19) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
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 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 112.1(2) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C2 N1 C1 N2 -2.7(3) . . . . ?
C10 N1 C1 N2 179.47(17) . . . . ?
C2 N1 C1 S1 177.14(15) . . . . ?
C10 N1 C1 S1 -0.7(3) . . . . ?
C4 N2 C1 N1 4.5(3) . . . . ?
C12 N2 C1 N1 -177.88(17) . . . . ?
C4 N2 C1 S1 -175.30(15) . . . . ?
C12 N2 C1 S1 2.3(3) . . . . ?
C1 N1 C2 O1 -178.22(19) . . . . ?
C10 N1 C2 O1 -0.3(3) . . . . ?
C1 N1 C2 C3 1.3(3) . . . . ?
C10 N1 C2 C3 179.27(17) . . . . ?
O1 C2 C3 C4 177.9(2) . . . . ?
N1 C2 C3 C4 -1.6(3) . . . . ?
O1 C2 C3 C5 -0.4(3) . . . . ?
N1 C2 C3 C5 -179.88(17) . . . . ?
H3A O2 C4 N2 77.3 . . . . ?
H3A O2 C4 C3 -104.8 . . . . ?
C1 N2 C4 O2 173.3(2) . . . . ?
C12 N2 C4 O2 -4.5(3) . . . . ?
C1 N2 C4 C3 -4.9(3) . . . . ?
C12 N2 C4 C3 177.42(17) . . . . ?
C2 C3 C4 O2 -174.7(2) . . . . ?
C5 C3 C4 O2 3.6(3) . . . . ?
C2 C3 C4 N2 3.2(3) . . . . ?
C5 C3 C4 N2 -178.49(17) . . . . ?
C2 C3 C5 C6 7.8(3) . . . . ?
C4 C3 C5 C6 -170.46(18) . . . . ?
C2 C3 C5 C9 -172.95(18) . . . . ?
C4 C3 C5 C9 8.8(3) . . . . ?
C9 C5 C6 C7 0.4(3) . . . . ?
C3 C5 C6 C7 179.7(2) . . . . ?
C8 N3 C7 C6 -1.8(3) . . . . ?
C16 N3 C7 C6 177.9(2) . . . . ?
C8 N3 C7 C14 179.5(2) . . . . ?
C16 N3 C7 C14 -0.8(3) . . . . ?
C5 C6 C7 N3 0.2(4) . . . . ?
C5 C6 C7 C14 178.9(2) . . . . ?
C7 N3 C8 C9 2.9(3) . . . . ?
C16 N3 C8 C9 -176.82(19) . . . . ?
C7 N3 C8 C15 -175.9(2) . . . . ?
C16 N3 C8 C15 4.4(3) . . . . ?
N3 C8 C9 C5 -2.4(3) . . . . ?
C15 C8 C9 C5 176.45(19) . . . . ?
C6 C5 C9 C8 0.7(3) . . . . ?
C3 C5 C9 C8 -178.62(18) . . . . ?
C1 N1 C10 C11 91.0(2) . . . . ?
C2 N1 C10 C11 -87.0(2) . . . . ?
C1 N2 C12 C13 -89.9(2) . . . . ?
C4 N2 C12 C13 88.0(2) . . . . ?
C7 N3 C16 C17 92.3(3) . . . . ?
C8 N3 C16 C17 -88.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675
O3 H3B O1 0.92 2.05 2.879(3) 149.7 3_675
O3 H3A O2 0.84 2.07 2.783(3) 141.3 .
C6 H6 O1 0.93 2.10 2.757(3) 126.8 .
C9 H9 O2 0.93 2.08 2.739(3) 126.7 .
C15 H15A S1 0.96 2.97 3.761(3) 140.1 3_675
C16 H16A O3 0.97 2.57 3.315(4) 133.3 4_675

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_20150929a_0m
_database_code_depnum_ccdc_archive 'CCDC 1498126'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N2 O2'
_chemical_formula_sum            'C16 H22 N2 O2'
_chemical_formula_weight         274.36

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.932(4)
_cell_length_b                   8.098(5)
_cell_length_c                   12.503(7)
_cell_angle_alpha                100.451(11)
_cell_angle_beta                 99.409(11)
_cell_angle_gamma                99.622(12)
_cell_volume                     763.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4722
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.46

_exptl_crystal_description       Rod
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX area-detector diffractometer'
_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            9304
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2764
_reflns_number_gt                1727
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1289P)²+0.1351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.050(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.3478(2) 0.8052(2) 0.26006(15) 0.0646(6) Uani 1 1 d . . .
O2 O 0.2504(3) 0.9159(3) 0.4076(2) 0.0927(8) Uani 1 1 d . . .
N1 N 0.1648(2) 0.4960(2) 0.67496(16) 0.0526(6) Uani 1 1 d . . .
N2 N 0.3755(3) 0.3940(3) 0.2485(2) 0.0766(7) Uani 1 1 d . . .
C1 C 0.1078(4) 0.7828(4) 0.7421(3) 0.0798(9) Uani 1 1 d . . .
H1A H 0.1068 0.8883 0.7174 0.120 Uiso 1 1 calc R . .
H1B H 0.1874 0.8046 0.8121 0.120 Uiso 1 1 calc R . .
H1C H -0.0074 0.7354 0.7506 0.120 Uiso 1 1 calc R . .
C2 C 0.1646(3) 0.6586(3) 0.6585(2) 0.0545(6) Uani 1 1 d . . .
C3 C 0.2089(3) 0.7050(3) 0.5666(2) 0.0558(6) Uani 1 1 d . . .
H3 H 0.2069 0.8164 0.5581 0.067 Uiso 1 1 calc R . .
C4 C 0.2580(3) 0.5914(3) 0.48331(18) 0.0485(6) Uani 1 1 d . . .
C5 C 0.2590(3) 0.4259(3) 0.50546(19) 0.0520(6) Uani 1 1 d . . .
H5 H 0.2919 0.3449 0.4545 0.062 Uiso 1 1 calc R . .
C6 C 0.2140(3) 0.3810(3) 0.5975(2) 0.0533(6) Uani 1 1 d . . .
C7 C 0.2131(4) 0.2023(3) 0.6145(3) 0.0726(8) Uani 1 1 d . . .
H7A H 0.2581 0.1397 0.5565 0.109 Uiso 1 1 calc R . .
H7B H 0.0958 0.1461 0.6127 0.109 Uiso 1 1 calc R . .
H7C H 0.2848 0.2068 0.6851 0.109 Uiso 1 1 calc R . .
C8 C 0.2999(3) 0.6321(3) 0.3856(2) 0.0517(6) Uani 1 1 d . . .
C9 C 0.3439(3) 0.5035(3) 0.3085(2) 0.0576(7) Uani 1 1 d . . .
C10 C 0.2978(3) 0.7967(3) 0.3569(2) 0.0573(6) Uani 1 1 d . . .
C11 C 0.3571(4) 0.9702(3) 0.2297(3) 0.0746(8) Uani 1 1 d . . .
H11A H 0.4428 1.0572 0.2846 0.089 Uiso 1 1 calc R . .
H11B H 0.2446 1.0035 0.2255 0.089 Uiso 1 1 calc R . .
C12 C 0.4080(5) 0.9522(5) 0.1202(3) 0.0960(11) Uani 1 1 d . . .
H12A H 0.5151 0.9111 0.1241 0.144 Uiso 1 1 calc R . .
H12B H 0.4241 1.0616 0.0998 0.144 Uiso 1 1 calc R . .
H12C H 0.3180 0.8722 0.0656 0.144 Uiso 1 1 calc R . .
C13 C 0.1191(3) 0.4476(3) 0.7751(2) 0.0573(6) Uani 1 1 d . . .
H13A H 0.0628 0.3274 0.7574 0.069 Uiso 1 1 calc R . .
H13B H 0.0360 0.5136 0.7999 0.069 Uiso 1 1 calc R . .
C14 C 0.2759(3) 0.4769(4) 0.8689(2) 0.0707(8) Uani 1 1 d . . .
H14A H 0.3562 0.4061 0.8454 0.085 Uiso 1 1 calc R . .
H14B H 0.3359 0.5958 0.8839 0.085 Uiso 1 1 calc R . .
C15 C 0.2280(4) 0.4360(5) 0.9737(2) 0.0792(9) Uani 1 1 d . . .
H15A H 0.1510 0.5100 0.9981 0.095 Uiso 1 1 calc R . .
H15B H 0.3332 0.4628 1.0308 0.095 Uiso 1 1 calc R . .
C16 C 0.1402(6) 0.2530(5) 0.9638(4) 0.1085(12) Uani 1 1 d . . .
H16A H 0.0314 0.2272 0.9115 0.163 Uiso 1 1 calc R . .
H16B H 0.1188 0.2367 1.0350 0.163 Uiso 1 1 calc R . .
H16C H 0.2142 0.1782 0.9387 0.163 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 C10 1.344(3) . ?
O1 C11 1.448(3) . ?
O2 C10 1.205(3) . ?
N1 C6 1.369(3) . ?
N1 C2 1.369(3) . ?
N1 C13 1.460(3) . ?
N2 C9 1.142(3) . ?
C1 C2 1.494(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.352(4) . ?
C3 C4 1.410(3) . ?
C3 H3 0.9300 . ?
C4 C8 1.398(3) . ?
C4 C5 1.418(3) . ?
C5 C6 1.352(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.415(3) . ?
C8 C10 1.444(3) . ?
C11 C12 1.480(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.517(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.500(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.503(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
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
C10 O1 C11 115.2(2) . . ?
C6 N1 C2 118.9(2) . . ?
C6 N1 C13 120.5(2) . . ?
C2 N1 C13 120.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 121.0(2) . . ?
C3 C2 C1 120.3(2) . . ?
N1 C2 C1 118.7(2) . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C8 C4 C3 124.7(2) . . ?
C8 C4 C5 121.3(2) . . ?
C3 C4 C5 114.0(2) . . ?
C6 C5 C4 122.8(2) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 N1 120.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
N1 C6 C7 119.2(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C9 118.3(2) . . ?
C4 C8 C10 124.1(2) . . ?
C9 C8 C10 117.6(2) . . ?
N2 C9 C8 176.7(2) . . ?
O2 C10 O1 120.5(2) . . ?
O2 C10 C8 126.8(2) . . ?
O1 C10 C8 112.7(2) . . ?
O1 C11 C12 107.1(2) . . ?
O1 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
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 C13 C14 113.0(2) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 113.0(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 114.8(3) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 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
C6 N1 C2 C3 1.2(3) . . . . ?
C13 N1 C2 C3 179.12(19) . . . . ?
C6 N1 C2 C1 178.9(2) . . . . ?
C13 N1 C2 C1 -3.2(3) . . . . ?
N1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -177.9(2) . . . . ?
C2 C3 C4 C8 178.0(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C8 C4 C5 C6 -177.93(19) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 N1 -0.1(4) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C2 N1 C6 C5 -1.1(3) . . . . ?
C13 N1 C6 C5 -178.98(19) . . . . ?
C2 N1 C6 C7 -179.5(2) . . . . ?
C13 N1 C6 C7 2.6(3) . . . . ?
C3 C4 C8 C9 -178.9(2) . . . . ?
C5 C4 C8 C9 -0.1(3) . . . . ?
C3 C4 C8 C10 -0.2(4) . . . . ?
C5 C4 C8 C10 178.6(2) . . . . ?
C4 C8 C9 N2 20(5) . . . . ?
C10 C8 C9 N2 -159(4) . . . . ?
C11 O1 C10 O2 6.2(4) . . . . ?
C11 O1 C10 C8 -176.9(2) . . . . ?
C4 C8 C10 O2 -5.0(4) . . . . ?
C9 C8 C10 O2 173.7(2) . . . . ?
C4 C8 C10 O1 178.26(19) . . . . ?
C9 C8 C10 O1 -3.0(3) . . . . ?
C10 O1 C11 C12 -178.1(2) . . . . ?
C6 N1 C13 C14 87.2(3) . . . . ?
C2 N1 C13 C14 -90.7(3) . . . . ?
N1 C13 C14 C15 176.9(2) . . . . ?
C13 C14 C15 C16 61.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.070
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20160607b_0m
_database_code_depnum_ccdc_archive 'CCDC 1498120'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N3 O2 S, H2 O'
_chemical_formula_sum            'C17 H25 N3 O3 S'
_chemical_formula_weight         351.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.9827(13)
_cell_length_b                   14.2402(17)
_cell_length_c                   12.5749(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.917(8)
_cell_angle_gamma                90.00
_cell_volume                     1768.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9583
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.29

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            14001
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3481
_reflns_number_gt                3044
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0777P)²+0.6474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3481
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
S1 S -0.21019(5) -0.11923(4) 0.05932(4) 0.0556(2) Uani 1 1 d . . .
O1 O -0.15461(14) 0.12692(11) 0.34905(13) 0.0625(4) Uani 1 1 d . . .
O2 O 0.23329(13) -0.03716(11) 0.38027(13) 0.0588(4) Uani 1 1 d . . .
N1 N -0.16711(13) 0.00703(10) 0.22802(12) 0.0386(3) Uani 1 1 d . . .
N2 N 0.02368(14) -0.07074(9) 0.23958(12) 0.0395(3) Uani 1 1 d . . .
N3 N 0.29660(15) 0.21806(10) 0.68752(13) 0.0448(4) Uani 1 1 d . . .
C1 C -0.09028(17) 0.06606(12) 0.32615(14) 0.0396(4) Uani 1 1 d . . .
C2 C -0.11297(17) -0.05822(11) 0.18164(14) 0.0389(4) Uani 1 1 d . . .
C3 C 0.11214(17) -0.01829(11) 0.34078(14) 0.0392(4) Uani 1 1 d . . .
C4 C 0.05260(16) 0.05084(10) 0.38567(14) 0.0349(3) Uani 1 1 d . . .
C5 C 0.13631(16) 0.10728(11) 0.48842(14) 0.0352(3) Uani 1 1 d . . .
C6 C 0.08088(17) 0.16923(11) 0.54340(14) 0.0383(4) Uani 1 1 d . . .
H6 H -0.0128 0.1730 0.5137 0.046 Uiso 1 1 calc R . .
C7 C 0.15897(18) 0.22411(12) 0.63875(14) 0.0416(4) Uani 1 1 d . . .
C8 C 0.35610(19) 0.16015(13) 0.63770(17) 0.0487(4) Uani 1 1 d . . .
C9 C 0.27871(18) 0.10616(13) 0.54092(16) 0.0441(4) Uani 1 1 d . . .
H9 H 0.3222 0.0673 0.5089 0.053 Uiso 1 1 calc R . .
C10 C -0.31527(17) 0.02256(14) 0.17325(16) 0.0470(4) Uani 1 1 d . . .
H10A H -0.3423 0.0414 0.2339 0.056 Uiso 1 1 calc R . .
H10B H -0.3609 -0.0360 0.1394 0.056 Uiso 1 1 calc R . .
C11 C -0.3592(2) 0.09632(19) 0.0785(2) 0.0683(6) Uani 1 1 d . . .
H11A H -0.3117 0.1538 0.1108 0.102 Uiso 1 1 calc R . .
H11B H -0.4549 0.1067 0.0489 0.102 Uiso 1 1 calc R . .
H11C H -0.3392 0.0757 0.0152 0.102 Uiso 1 1 calc R . .
C12 C 0.09008(19) -0.14121(13) 0.19535(17) 0.0475(4) Uani 1 1 d . . .
H12A H 0.0268 -0.1917 0.1565 0.057 Uiso 1 1 calc R . .
H12B H 0.1672 -0.1679 0.2618 0.057 Uiso 1 1 calc R . .
C13 C 0.1371(2) -0.09923(17) 0.1098(2) 0.0617(5) Uani 1 1 d . . .
H13A H 0.0610 -0.0731 0.0436 0.093 Uiso 1 1 calc R . .
H13B H 0.1782 -0.1472 0.0827 0.093 Uiso 1 1 calc R . .
H13C H 0.2020 -0.0506 0.1486 0.093 Uiso 1 1 calc R . .
C14 C 0.0929(2) 0.29200(15) 0.68824(18) 0.0558(5) Uani 1 1 d . . .
H14A H 0.1229 0.2797 0.7710 0.084 Uiso 1 1 calc R . .
H14B H -0.0036 0.2849 0.6476 0.084 Uiso 1 1 calc R . .
H14C H 0.1171 0.3550 0.6779 0.084 Uiso 1 1 calc R . .
C15 C 0.5080(2) 0.1546(2) 0.6905(2) 0.0787(8) Uani 1 1 d . . .
H15A H 0.5446 0.2166 0.6959 0.118 Uiso 1 1 calc R . .
H15B H 0.5343 0.1163 0.6412 0.118 Uiso 1 1 calc R . .
H15C H 0.5420 0.1275 0.7680 0.118 Uiso 1 1 calc R . .
C16 C 0.3799(2) 0.27483(15) 0.79539(17) 0.0572(5) Uani 1 1 d . . .
H16A H 0.4644 0.2424 0.8415 0.069 Uiso 1 1 calc R . .
H16B H 0.3316 0.2806 0.8439 0.069 Uiso 1 1 calc R . .
C17 C 0.4097(3) 0.37117(17) 0.7639(2) 0.0772(7) Uani 1 1 d . . .
H17A H 0.4570 0.3657 0.7155 0.116 Uiso 1 1 calc R . .
H17B H 0.4649 0.4049 0.8348 0.116 Uiso 1 1 calc R . .
H17C H 0.3264 0.4044 0.7211 0.116 Uiso 1 1 calc R . .
O3 O 0.7072(2) 0.20148(17) 0.4706(2) 0.1032(7) Uani 1 1 d . . .
H3A H 0.7149 0.1586 0.5202 0.155 Uiso 1 1 d R . .
H3B H 0.7343 0.1809 0.4211 0.155 Uiso 1 1 d 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
S1 C2 1.6809(17) . ?
O1 C1 1.229(2) . ?
O2 C3 1.229(2) . ?
N1 C2 1.364(2) . ?
N1 C1 1.425(2) . ?
N1 C10 1.480(2) . ?
N2 C2 1.363(2) . ?
N2 C3 1.428(2) . ?
N2 C12 1.484(2) . ?
N3 C8 1.363(2) . ?
N3 C7 1.363(2) . ?
N3 C16 1.498(2) . ?
C1 C4 1.429(2) . ?
C3 C4 1.428(2) . ?
C4 C5 1.457(2) . ?
C5 C9 1.407(2) . ?
C5 C6 1.412(2) . ?
C6 C7 1.373(2) . ?
C6 H6 0.9300 . ?
C7 C14 1.498(2) . ?
C8 C9 1.375(3) . ?
C8 C15 1.504(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.503(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O3 H3A 0.8503 . ?
O3 H3B 0.8503 . ?

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 C1 124.63(14) . . ?
C2 N1 C10 119.92(14) . . ?
C1 N1 C10 115.42(13) . . ?
C2 N2 C3 124.67(13) . . ?
C2 N2 C12 119.64(14) . . ?
C3 N2 C12 115.66(14) . . ?
C8 N3 C7 119.45(14) . . ?
C8 N3 C16 121.13(16) . . ?
C7 N3 C16 119.41(15) . . ?
O1 C1 N1 115.80(15) . . ?
O1 C1 C4 126.59(16) . . ?
N1 C1 C4 117.58(14) . . ?
N2 C2 N1 116.38(14) . . ?
N2 C2 S1 122.14(12) . . ?
N1 C2 S1 121.48(13) . . ?
O2 C3 C4 126.36(15) . . ?
O2 C3 N2 116.12(14) . . ?
C4 C3 N2 117.52(14) . . ?
C3 C4 C1 119.03(14) . . ?
C3 C4 C5 120.70(15) . . ?
C1 C4 C5 120.24(14) . . ?
C9 C5 C6 113.95(15) . . ?
C9 C5 C4 123.44(15) . . ?
C6 C5 C4 122.60(15) . . ?
C7 C6 C5 123.00(16) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N3 C7 C6 120.23(15) . . ?
N3 C7 C14 119.82(15) . . ?
C6 C7 C14 119.94(16) . . ?
N3 C8 C9 120.67(16) . . ?
N3 C8 C15 119.40(17) . . ?
C9 C8 C15 119.92(18) . . ?
C8 C9 C5 122.64(17) . . ?
C8 C9 H9 118.7 . . ?
C5 C9 H9 118.7 . . ?
N1 C10 C11 112.37(16) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 112.17(16) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
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 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 111.77(18) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H3A O3 H3B 109.6 . . ?

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
C2 N1 C1 O1 173.32(16) . . . . ?
C10 N1 C1 O1 -4.6(2) . . . . ?
C2 N1 C1 C4 -5.0(2) . . . . ?
C10 N1 C1 C4 177.09(14) . . . . ?
C3 N2 C2 N1 -2.5(2) . . . . ?
C12 N2 C2 N1 179.36(14) . . . . ?
C3 N2 C2 S1 177.22(12) . . . . ?
C12 N2 C2 S1 -0.9(2) . . . . ?
C1 N1 C2 N2 4.4(2) . . . . ?
C10 N1 C2 N2 -177.73(14) . . . . ?
C1 N1 C2 S1 -175.30(12) . . . . ?
C10 N1 C2 S1 2.5(2) . . . . ?
C2 N2 C3 O2 -178.24(16) . . . . ?
C12 N2 C3 O2 -0.1(2) . . . . ?
C2 N2 C3 C4 1.3(2) . . . . ?
C12 N2 C3 C4 179.48(14) . . . . ?
O2 C3 C4 C1 177.76(17) . . . . ?
N2 C3 C4 C1 -1.7(2) . . . . ?
O2 C3 C4 C5 -0.3(3) . . . . ?
N2 C3 C4 C5 -179.84(13) . . . . ?
O1 C1 C4 C3 -174.70(18) . . . . ?
N1 C1 C4 C3 3.4(2) . . . . ?
O1 C1 C4 C5 3.4(3) . . . . ?
N1 C1 C4 C5 -178.48(13) . . . . ?
C3 C4 C5 C9 7.7(2) . . . . ?
C1 C4 C5 C9 -170.36(15) . . . . ?
C3 C4 C5 C6 -173.10(14) . . . . ?
C1 C4 C5 C6 8.8(2) . . . . ?
C9 C5 C6 C7 0.6(2) . . . . ?
C4 C5 C6 C7 -178.63(15) . . . . ?
C8 N3 C7 C6 2.9(2) . . . . ?
C16 N3 C7 C6 -176.83(15) . . . . ?
C8 N3 C7 C14 -176.18(17) . . . . ?
C16 N3 C7 C14 4.1(2) . . . . ?
C5 C6 C7 N3 -2.4(2) . . . . ?
C5 C6 C7 C14 176.67(16) . . . . ?
C7 N3 C8 C9 -1.7(3) . . . . ?
C16 N3 C8 C9 177.97(18) . . . . ?
C7 N3 C8 C15 179.1(2) . . . . ?
C16 N3 C8 C15 -1.3(3) . . . . ?
N3 C8 C9 C5 0.0(3) . . . . ?
C15 C8 C9 C5 179.2(2) . . . . ?
C6 C5 C9 C8 0.6(3) . . . . ?
C4 C5 C9 C8 179.80(16) . . . . ?
C2 N1 C10 C11 -89.8(2) . . . . ?
C1 N1 C10 C11 88.3(2) . . . . ?
C2 N2 C12 C13 91.5(2) . . . . ?
C3 N2 C12 C13 -86.80(19) . . . . ?
C8 N3 C16 C17 92.6(2) . . . . ?
C7 N3 C16 C17 -87.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3B O1 0.85 1.97 2.791(3) 163.3 1_655
O3 H3A O2 0.85 2.06 2.890(3) 163.6 3_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_dm16484_0m
_database_code_depnum_ccdc_archive 'CCDC 1498119'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N2 O3 S'
_chemical_formula_weight         306.37

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                   16.414(4)
_cell_length_b                   5.0946(12)
_cell_length_c                   17.538(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.146(4)
_cell_angle_gamma                90
_cell_volume                     1465.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2530
_cell_measurement_theta_min      4.648
_cell_measurement_theta_max      54.594

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5515
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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            9465
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2710
_reflns_number_gt                2105
_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-2013 (Sheldrick, 2013)'
_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)+(0.0532P)²+0.8378P] 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
_refine_ls_extinction_coef       0.0023(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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
S1 S 0.31573(3) 1.21094(11) 0.43943(3) 0.02824(18) Uani 1 1 d . . . . .
N1 N 0.35204(9) 0.8563(3) 0.33455(9) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.21336(9) 0.9237(3) 0.35287(9) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.39721(8) 0.5395(3) 0.25693(9) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.11531(8) 0.6879(3) 0.29083(8) 0.0278(4) Uani 1 1 d . . . . .
O3 O 0.19477(8) -0.0487(3) 0.11159(8) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.29293(12) 0.9867(4) 0.37252(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.33739(12) 0.6456(4) 0.28321(11) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.25303(11) 0.5744(4) 0.26547(10) 0.0194(4) Uani 1 1 d . . . . .
C4 C 0.18900(12) 0.7225(4) 0.30115(10) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.14613(12) 1.0693(4) 0.38804(11) 0.0248(5) Uani 1 1 d . . . . .
H5A H 0.0984 1.0746 0.3518 0.030 Uiso 1 1 calc R U . . .
H5B H 0.1637 1.2523 0.3982 0.030 Uiso 1 1 calc R U . . .
C6 C 0.12135(13) 0.9441(5) 0.46183(12) 0.0341(6) Uani 1 1 d . . . . .
H6A H 0.1075 0.7593 0.4527 0.051 Uiso 1 1 calc R U . . .
H6B H 0.0738 1.0361 0.4809 0.051 Uiso 1 1 calc R U . . .
H6C H 0.1666 0.9556 0.4997 0.051 Uiso 1 1 calc R U . . .
C7 C 0.43878(11) 0.9315(4) 0.34748(12) 0.0266(5) Uani 1 1 d . . . . .
H7A H 0.4421 1.1210 0.3596 0.032 Uiso 1 1 calc R U . . .
H7B H 0.4683 0.9014 0.3001 0.032 Uiso 1 1 calc R U . . .
C8 C 0.47958(13) 0.7762(5) 0.41199(14) 0.0342(5) Uani 1 1 d . . . . .
H8A H 0.4513 0.8090 0.4593 0.051 Uiso 1 1 calc R U . . .
H8B H 0.5367 0.8307 0.4185 0.051 Uiso 1 1 calc R U . . .
H8C H 0.4771 0.5885 0.3998 0.051 Uiso 1 1 calc R U . . .
C9 C 0.23333(11) 0.3650(4) 0.21441(10) 0.0191(4) Uani 1 1 d . . . . .
C10 C 0.29395(12) 0.2087(4) 0.17871(11) 0.0213(4) Uani 1 1 d . . . . .
H10 H 0.3499 0.2443 0.1899 0.026 Uiso 1 1 calc R U . . .
C11 C 0.27380(12) 0.0123(4) 0.12965(11) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.13487(12) 0.0882(4) 0.14521(11) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.15118(12) 0.2878(4) 0.19406(11) 0.0226(4) Uani 1 1 d . . . . .
H13 H 0.1072 0.3795 0.2155 0.027 Uiso 1 1 calc R U . . .
C14 C 0.33114(13) -0.1605(4) 0.08966(12) 0.0271(5) Uani 1 1 d . . . . .
H14A H 0.3211 -0.3438 0.1034 0.041 Uiso 1 1 calc R U . . .
H14B H 0.3873 -0.1133 0.1048 0.041 Uiso 1 1 calc R U . . .
H14C H 0.3229 -0.1386 0.0344 0.041 Uiso 1 1 calc R U . . .
C15 C 0.05262(13) -0.0135(5) 0.12239(13) 0.0334(5) Uani 1 1 d . . . . .
H15A H 0.0439 0.0037 0.0670 0.050 Uiso 1 1 calc R U . . .
H15B H 0.0110 0.0877 0.1483 0.050 Uiso 1 1 calc R U . . .
H15C H 0.0487 -0.1987 0.1368 0.050 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 C1 1.670(2) . ?
N1 C1 1.369(2) . ?
N1 C2 1.416(3) . ?
N1 C7 1.483(2) . ?
N2 C1 1.376(2) . ?
N2 C4 1.417(2) . ?
N2 C5 1.483(2) . ?
O1 C2 1.226(2) . ?
O2 C4 1.229(2) . ?
O3 C12 1.358(2) . ?
O3 C11 1.360(2) . ?
C2 C3 1.454(3) . ?
C3 C9 1.422(3) . ?
C3 C4 1.454(3) . ?
C5 C6 1.512(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.436(3) . ?
C9 C13 1.437(3) . ?
C10 C11 1.352(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.484(3) . ?
C12 C13 1.350(3) . ?
C12 C15 1.487(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
C1 N1 C2 124.79(16) . . ?
C1 N1 C7 119.61(16) . . ?
C2 N1 C7 115.60(16) . . ?
C1 N2 C4 124.86(16) . . ?
C1 N2 C5 119.56(16) . . ?
C4 N2 C5 115.57(15) . . ?
C12 O3 C11 118.76(15) . . ?
N1 C1 N2 116.64(16) . . ?
N1 C1 S1 121.96(14) . . ?
N2 C1 S1 121.40(15) . . ?
O1 C2 N1 117.01(17) . . ?
O1 C2 C3 125.40(18) . . ?
N1 C2 C3 117.59(17) . . ?
C9 C3 C2 120.95(17) . . ?
C9 C3 C4 120.61(17) . . ?
C2 C3 C4 118.45(17) . . ?
O2 C4 N2 116.79(17) . . ?
O2 C4 C3 125.83(18) . . ?
N2 C4 C3 117.38(16) . . ?
N2 C5 C6 111.92(17) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 111.97(17) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C10 123.06(17) . . ?
C3 C9 C13 123.44(18) . . ?
C10 C9 C13 113.50(17) . . ?
C11 C10 C9 122.05(18) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 O3 121.72(18) . . ?
C10 C11 C14 126.53(18) . . ?
O3 C11 C14 111.74(17) . . ?
C13 C12 O3 122.20(18) . . ?
C13 C12 C15 126.13(19) . . ?
O3 C12 C15 111.66(17) . . ?
C12 C13 C9 121.73(18) . . ?
C12 C13 H13 119.1 . . ?
C9 C13 H13 119.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 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
C2 N1 C1 N2 -6.9(3) . . . . ?
C7 N1 C1 N2 174.31(16) . . . . ?
C2 N1 C1 S1 173.06(15) . . . . ?
C7 N1 C1 S1 -5.7(2) . . . . ?
C4 N2 C1 N1 5.0(3) . . . . ?
C5 N2 C1 N1 -176.07(16) . . . . ?
C4 N2 C1 S1 -174.92(14) . . . . ?
C5 N2 C1 S1 4.0(2) . . . . ?
C1 N1 C2 O1 -176.04(18) . . . . ?
C7 N1 C2 O1 2.8(3) . . . . ?
C1 N1 C2 C3 4.5(3) . . . . ?
C7 N1 C2 C3 -176.67(16) . . . . ?
O1 C2 C3 C9 0.6(3) . . . . ?
N1 C2 C3 C9 179.99(16) . . . . ?
O1 C2 C3 C4 -179.41(19) . . . . ?
N1 C2 C3 C4 0.0(3) . . . . ?
C1 N2 C4 O2 178.66(17) . . . . ?
C5 N2 C4 O2 -0.3(3) . . . . ?
C1 N2 C4 C3 -0.9(3) . . . . ?
C5 N2 C4 C3 -179.88(16) . . . . ?
C9 C3 C4 O2 -1.2(3) . . . . ?
C2 C3 C4 O2 178.81(18) . . . . ?
C9 C3 C4 N2 178.41(16) . . . . ?
C2 C3 C4 N2 -1.6(3) . . . . ?
C1 N2 C5 C6 -88.8(2) . . . . ?
C4 N2 C5 C6 90.2(2) . . . . ?
C1 N1 C7 C8 90.5(2) . . . . ?
C2 N1 C7 C8 -88.4(2) . . . . ?
C2 C3 C9 C10 1.3(3) . . . . ?
C4 C3 C9 C10 -178.71(17) . . . . ?
C2 C3 C9 C13 -179.26(17) . . . . ?
C4 C3 C9 C13 0.7(3) . . . . ?
C3 C9 C10 C11 -179.24(18) . . . . ?
C13 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 O3 -0.3(3) . . . . ?
C9 C10 C11 C14 179.95(18) . . . . ?
C12 O3 C11 C10 -1.4(3) . . . . ?
C12 O3 C11 C14 178.38(16) . . . . ?
C11 O3 C12 C13 2.1(3) . . . . ?
C11 O3 C12 C15 -176.84(17) . . . . ?
O3 C12 C13 C9 -1.0(3) . . . . ?
C15 C12 C13 C9 177.77(19) . . . . ?
C3 C9 C13 C12 179.84(18) . . . . ?
C10 C9 C13 C12 -0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15B O2 0.98 2.42 3.359(3) 159.6 2_545
C14 H14C S1 0.98 2.74 3.493(2) 133.8 4_575
C13 H13 O2 0.95 2.05 2.731(2) 126.8 .
C10 H10 O1 0.95 2.04 2.724(2) 127.1 .
C7 H7B O1 0.99 2.56 3.358(2) 138.0 2_655
C6 H6C S1 0.98 3.00 3.504(2) 113.3 .

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd16209
_database_code_depnum_ccdc_archive 'CCDC 1498125'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

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           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                   8.914(2)
_cell_length_b                   13.304(3)
_cell_length_c                   12.052(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.441(4)
_cell_angle_gamma                90
_cell_volume                     1400.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      5.221
_cell_measurement_theta_max      50.945

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8183
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2750
_reflns_number_gt                1933
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0537P)²+0.1532P] 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         2750
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1067
_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
N1 N 0.15458(16) -0.02924(11) 0.76725(12) 0.0342(4) Uani 1 1 d . . . . .
O1 O 0.33314(16) 0.05065(10) 0.38097(11) 0.0521(4) Uani 1 1 d . . . . .
O2 O -0.04471(16) 0.26577(10) 0.47565(12) 0.0511(4) Uani 1 1 d . . . . .
C1 C 0.2317(2) 0.11326(13) 0.38045(15) 0.0350(4) Uani 1 1 d . . . . .
C2 C 0.1427(2) 0.13559(12) 0.46542(14) 0.0325(4) Uani 1 1 d . . . . .
C3 C 0.0455(2) 0.22044(13) 0.42807(15) 0.0357(4) Uani 1 1 d . . . . .
C4 C 0.0714(2) 0.24859(13) 0.31247(15) 0.0345(4) Uani 1 1 d . . . . .
C5 C 0.18053(19) 0.18448(13) 0.28426(14) 0.0337(4) Uani 1 1 d . . . . .
C6 C 0.2252(2) 0.19199(14) 0.18167(15) 0.0400(5) Uani 1 1 d . . . . .
H6 H 0.2988 0.1491 0.1631 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1568(2) 0.26578(15) 0.10655(16) 0.0453(5) Uani 1 1 d . . . . .
H7 H 0.1844 0.2719 0.0364 0.054 Uiso 1 1 calc R U . . .
C8 C 0.0487(2) 0.33009(15) 0.13472(17) 0.0464(5) Uani 1 1 d . . . . .
H8 H 0.0047 0.3791 0.0834 0.056 Uiso 1 1 calc R U . . .
C9 C 0.0050(2) 0.32245(14) 0.23878(16) 0.0431(5) Uani 1 1 d . . . . .
H9 H -0.0673 0.3660 0.2582 0.052 Uiso 1 1 calc R U . . .
C10 C 0.14610(19) 0.07969(12) 0.56668(14) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.2407(2) -0.00499(12) 0.59538(15) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.3024 -0.0257 0.5459 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2452(2) -0.05780(13) 0.69294(14) 0.0338(4) Uani 1 1 d . . . . .
C13 C 0.0584(2) 0.05154(13) 0.74260(15) 0.0359(4) Uani 1 1 d . . . . .
C14 C 0.0542(2) 0.10434(13) 0.64504(15) 0.0357(4) Uani 1 1 d . . . . .
H14 H -0.0121 0.1588 0.6297 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3473(2) -0.14776(14) 0.71914(17) 0.0473(5) Uani 1 1 d . . . . .
H15A H 0.2862 -0.2077 0.7107 0.071 Uiso 1 1 calc R U . . .
H15B H 0.4039 -0.1432 0.7956 0.071 Uiso 1 1 calc R U . . .
H15C H 0.4173 -0.1499 0.6680 0.071 Uiso 1 1 calc R U . . .
C16 C -0.0427(2) 0.08100(16) 0.82259(18) 0.0550(6) Uani 1 1 d . . . . .
H16A H -0.1005 0.1397 0.7943 0.082 Uiso 1 1 calc R U . . .
H16B H 0.0191 0.0954 0.8956 0.082 Uiso 1 1 calc R U . . .
H16C H -0.1115 0.0268 0.8292 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1706(2) -0.08044(15) 0.87783(15) 0.0438(5) Uani 1 1 d . . . . .
H17A H 0.1967 -0.1505 0.8696 0.053 Uiso 1 1 calc R U . . .
H17B H 0.0737 -0.0780 0.9029 0.053 Uiso 1 1 calc R U . . .
C18 C 0.2933(3) -0.03119(18) 0.96567(17) 0.0606(6) Uani 1 1 d . . . . .
H18A H 0.3897 -0.0350 0.9418 0.091 Uiso 1 1 calc R U . . .
H18B H 0.3010 -0.0653 1.0368 0.091 Uiso 1 1 calc R U . . .
H18C H 0.2671 0.0380 0.9742 0.091 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
N1 C13 1.370(2) . ?
N1 C12 1.373(2) . ?
N1 C17 1.478(2) . ?
O1 C1 1.229(2) . ?
O2 C3 1.234(2) . ?
C1 C2 1.445(2) . ?
C1 C5 1.497(2) . ?
C2 C10 1.424(2) . ?
C2 C3 1.440(2) . ?
C3 C4 1.504(2) . ?
C4 C9 1.377(3) . ?
C4 C5 1.386(2) . ?
C5 C6 1.376(2) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C14 1.406(2) . ?
C10 C11 1.409(2) . ?
C11 C12 1.363(2) . ?
C11 H11 0.9300 . ?
C12 C15 1.499(2) . ?
C13 C14 1.364(2) . ?
C13 C16 1.497(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.512(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C13 N1 C12 119.95(14) . . ?
C13 N1 C17 120.09(15) . . ?
C12 N1 C17 119.76(15) . . ?
O1 C1 C2 130.00(16) . . ?
O1 C1 C5 122.95(16) . . ?
C2 C1 C5 107.04(15) . . ?
C10 C2 C3 125.92(15) . . ?
C10 C2 C1 125.34(16) . . ?
C3 C2 C1 108.69(15) . . ?
O2 C3 C2 130.18(17) . . ?
O2 C3 C4 122.87(17) . . ?
C2 C3 C4 106.94(15) . . ?
C9 C4 C5 120.94(17) . . ?
C9 C4 C3 130.50(17) . . ?
C5 C4 C3 108.56(15) . . ?
C6 C5 C4 121.21(16) . . ?
C6 C5 C1 130.10(17) . . ?
C4 C5 C1 108.69(15) . . ?
C5 C6 C7 117.94(18) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 120.95(18) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.76(18) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.19(18) . . ?
C4 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C14 C10 C11 114.94(16) . . ?
C14 C10 C2 122.50(16) . . ?
C11 C10 C2 122.55(16) . . ?
C12 C11 C10 122.53(16) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 N1 119.95(16) . . ?
C11 C12 C15 120.40(16) . . ?
N1 C12 C15 119.65(15) . . ?
C14 C13 N1 120.01(16) . . ?
C14 C13 C16 120.21(17) . . ?
N1 C13 C16 119.77(16) . . ?
C13 C14 C10 122.60(17) . . ?
C13 C14 H14 118.7 . . ?
C10 C14 H14 118.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 111.00(16) . . ?
N1 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N1 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C1 C2 C10 -6.7(3) . . . . ?
C5 C1 C2 C10 174.40(16) . . . . ?
O1 C1 C2 C3 175.93(19) . . . . ?
C5 C1 C2 C3 -2.96(19) . . . . ?
C10 C2 C3 O2 5.0(3) . . . . ?
C1 C2 C3 O2 -177.63(19) . . . . ?
C10 C2 C3 C4 -174.87(16) . . . . ?
C1 C2 C3 C4 2.47(19) . . . . ?
O2 C3 C4 C9 -1.6(3) . . . . ?
C2 C3 C4 C9 178.35(19) . . . . ?
O2 C3 C4 C5 179.09(17) . . . . ?
C2 C3 C4 C5 -1.00(19) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C6 178.97(16) . . . . ?
C9 C4 C5 C1 179.75(16) . . . . ?
C3 C4 C5 C1 -0.82(19) . . . . ?
O1 C1 C5 C6 3.6(3) . . . . ?
C2 C1 C5 C6 -177.42(18) . . . . ?
O1 C1 C5 C4 -176.64(17) . . . . ?
C2 C1 C5 C4 2.34(19) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C1 C5 C6 C7 179.43(17) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C3 C4 C9 C8 -178.43(18) . . . . ?
C7 C8 C9 C4 -0.5(3) . . . . ?
C3 C2 C10 C14 -1.8(3) . . . . ?
C1 C2 C10 C14 -178.74(16) . . . . ?
C3 C2 C10 C11 177.57(17) . . . . ?
C1 C2 C10 C11 0.7(3) . . . . ?
C14 C10 C11 C12 -1.3(2) . . . . ?
C2 C10 C11 C12 179.23(16) . . . . ?
C10 C11 C12 N1 0.4(3) . . . . ?
C10 C11 C12 C15 179.66(16) . . . . ?
C13 N1 C12 C11 0.8(2) . . . . ?
C17 N1 C12 C11 -174.12(16) . . . . ?
C13 N1 C12 C15 -178.52(16) . . . . ?
C17 N1 C12 C15 6.6(2) . . . . ?
C12 N1 C13 C14 -0.9(2) . . . . ?
C17 N1 C13 C14 174.02(16) . . . . ?
C12 N1 C13 C16 178.64(16) . . . . ?
C17 N1 C13 C16 -6.5(2) . . . . ?
N1 C13 C14 C10 -0.2(3) . . . . ?
C16 C13 C14 C10 -179.69(17) . . . . ?
C11 C10 C14 C13 1.2(3) . . . . ?
C2 C10 C14 C13 -179.31(16) . . . . ?
C13 N1 C17 C18 -87.6(2) . . . . ?
C12 N1 C17 C18 87.2(2) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_20150719a_0m
_database_code_depnum_ccdc_archive 'CCDC 1498115'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N3'
_chemical_formula_sum            'C12 H13 N3'
_chemical_formula_weight         199.25

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9599(7)
_cell_length_b                   7.5636(8)
_cell_length_c                   10.3122(10)
_cell_angle_alpha                98.430(2)
_cell_angle_beta                 92.196(2)
_cell_angle_gamma                103.452(2)
_cell_volume                     520.77(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3892
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.27

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            5014
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2018
_reflns_number_gt                1835
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0739P)²+0.2131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
N1 N 0.29717(15) 0.68168(14) 0.24960(10) 0.0142(3) Uani 1 1 d . . .
N2 N 0.13093(19) 0.03659(17) -0.17885(13) 0.0271(3) Uani 1 1 d . . .
N3 N 0.30408(18) 0.56402(18) -0.33343(12) 0.0256(3) Uani 1 1 d . . .
C1 C 0.1912(2) 0.39267(18) 0.34245(13) 0.0186(3) Uani 1 1 d . . .
H1A H 0.1139 0.2696 0.3124 0.028 Uiso 1 1 calc R . .
H1B H 0.1198 0.4560 0.4038 0.028 Uiso 1 1 calc R . .
H1C H 0.3148 0.3882 0.3848 0.028 Uiso 1 1 calc R . .
C2 C 0.23015(18) 0.49308(17) 0.22732(13) 0.0148(3) Uani 1 1 d . . .
C3 C 0.20118(18) 0.39821(17) 0.10223(13) 0.0149(3) Uani 1 1 d . . .
H3 H 0.1554 0.2707 0.0892 0.018 Uiso 1 1 calc R . .
C4 C 0.23897(17) 0.48865(17) -0.00823(12) 0.0148(3) Uani 1 1 d . . .
C5 C 0.29085(18) 0.68323(18) 0.01902(13) 0.0153(3) Uani 1 1 d . . .
H5 H 0.3052 0.7495 -0.0506 0.018 Uiso 1 1 calc R . .
C6 C 0.32047(18) 0.77664(18) 0.14474(13) 0.0150(3) Uani 1 1 d . . .
C7 C 0.3787(2) 0.98309(18) 0.17073(13) 0.0190(3) Uani 1 1 d . . .
H7A H 0.3710 1.0295 0.0894 0.029 Uiso 1 1 calc R . .
H7B H 0.5119 1.0239 0.2102 0.029 Uiso 1 1 calc R . .
H7C H 0.2905 1.0280 0.2292 0.029 Uiso 1 1 calc R . .
C8 C 0.22298(18) 0.39107(18) -0.13734(13) 0.0163(3) Uani 1 1 d . . .
C9 C 0.17215(19) 0.19611(19) -0.16162(13) 0.0186(3) Uani 1 1 d . . .
C10 C 0.26746(19) 0.48510(19) -0.24610(13) 0.0184(3) Uani 1 1 d . . .
C11 C 0.34475(19) 0.78194(18) 0.38639(13) 0.0179(3) Uani 1 1 d . . .
H11A H 0.4541 0.8884 0.3871 0.021 Uiso 1 1 calc R . .
H11B H 0.3874 0.7021 0.4411 0.021 Uiso 1 1 calc R . .
C12 C 0.1700(2) 0.84556(19) 0.44514(13) 0.0216(3) Uani 1 1 d . . .
H12A H 0.1400 0.9392 0.3998 0.032 Uiso 1 1 calc R . .
H12B H 0.2031 0.8946 0.5366 0.032 Uiso 1 1 calc R . .
H12C H 0.0566 0.7430 0.4360 0.032 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
N1 C2 1.3753(17) . ?
N1 C6 1.3778(16) . ?
N1 C11 1.4861(16) . ?
N2 C9 1.1584(19) . ?
N3 C10 1.1562(19) . ?
C1 C2 1.5010(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3642(19) . ?
C3 C4 1.4150(17) . ?
C3 H3 0.9300 . ?
C4 C8 1.4115(18) . ?
C4 C5 1.4139(18) . ?
C5 C6 1.3659(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4996(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.4158(19) . ?
C8 C10 1.4203(18) . ?
C11 C12 1.5238(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 C6 119.74(11) . . ?
C2 N1 C11 119.92(11) . . ?
C6 N1 C11 120.34(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 120.44(11) . . ?
C3 C2 C1 120.38(11) . . ?
N1 C2 C1 119.18(11) . . ?
C2 C3 C4 121.73(12) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C8 C4 C5 122.19(12) . . ?
C8 C4 C3 122.20(12) . . ?
C5 C4 C3 115.60(12) . . ?
C6 C5 C4 121.87(12) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 N1 120.18(12) . . ?
C5 C6 C7 120.71(11) . . ?
N1 C6 C7 119.12(11) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C9 120.96(12) . . ?
C4 C8 C10 121.05(12) . . ?
C9 C8 C10 117.91(12) . . ?
N2 C9 C8 178.66(14) . . ?
N3 C10 C8 179.02(14) . . ?
N1 C11 C12 113.02(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 . . ?
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 . . ?

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
C6 N1 C2 C3 5.07(18) . . . . ?
C11 N1 C2 C3 -174.72(11) . . . . ?
C6 N1 C2 C1 -175.53(10) . . . . ?
C11 N1 C2 C1 4.69(17) . . . . ?
N1 C2 C3 C4 0.20(19) . . . . ?
C1 C2 C3 C4 -179.20(11) . . . . ?
C2 C3 C4 C8 175.42(11) . . . . ?
C2 C3 C4 C5 -5.50(18) . . . . ?
C8 C4 C5 C6 -175.04(11) . . . . ?
C3 C4 C5 C6 5.89(18) . . . . ?
C4 C5 C6 N1 -0.98(19) . . . . ?
C4 C5 C6 C7 178.98(11) . . . . ?
C2 N1 C6 C5 -4.68(18) . . . . ?
C11 N1 C6 C5 175.10(11) . . . . ?
C2 N1 C6 C7 175.37(11) . . . . ?
C11 N1 C6 C7 -4.85(17) . . . . ?
C5 C4 C8 C9 179.54(11) . . . . ?
C3 C4 C8 C9 -1.45(19) . . . . ?
C5 C4 C8 C10 2.88(19) . . . . ?
C3 C4 C8 C10 -178.11(11) . . . . ?
C4 C8 C9 N2 -9(6) . . . . ?
C10 C8 C9 N2 168(6) . . . . ?
C4 C8 C10 N3 -4(8) . . . . ?
C9 C8 C10 N3 179(100) . . . . ?
C2 N1 C11 C12 -91.99(14) . . . . ?
C6 N1 C11 C12 88.23(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1498127'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.34

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   17.031(3)
_cell_length_b                   11.1503(19)
_cell_length_c                   8.1223(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.862(3)
_cell_angle_gamma                90.00
_cell_volume                     1531.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6049
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.15

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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 APEX area-detector diffractometer'
_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            11832
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2985
_reflns_number_gt                2457
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0789P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2985
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.57035(9) 0.70106(18) 0.4179(3) 0.1001(6) Uani 1 1 d . . .
O2 O 0.50081(11) 0.85573(17) 0.4681(3) 0.1105(7) Uani 1 1 d . . .
N1 N 0.50640(10) 0.74960(17) 0.4283(2) 0.0693(5) Uani 1 1 d . . .
N2 N 0.09421(9) 0.62185(15) 0.2002(2) 0.0614(4) Uani 1 1 d . . .
N3 N 0.17631(7) 0.12003(11) 0.15888(15) 0.0394(3) Uani 1 1 d . . .
C1 C 0.36850(9) 0.50785(14) 0.2653(2) 0.0472(4) Uani 1 1 d . . .
H1 H 0.3709 0.4338 0.2135 0.057 Uiso 1 1 calc R . .
C2 C 0.43757(10) 0.56975(15) 0.3114(2) 0.0514(4) Uani 1 1 d . . .
H2 H 0.4860 0.5372 0.2930 0.062 Uiso 1 1 calc R . .
C3 C 0.43405(10) 0.68132(16) 0.3858(2) 0.0509(4) Uani 1 1 d . . .
C4 C 0.36216(11) 0.73115(16) 0.4151(2) 0.0554(4) Uani 1 1 d . . .
H4 H 0.3604 0.8064 0.4639 0.066 Uiso 1 1 calc R . .
C5 C 0.29406(10) 0.66771(15) 0.3711(2) 0.0501(4) Uani 1 1 d . . .
H5 H 0.2461 0.7007 0.3921 0.060 Uiso 1 1 calc R . .
C6 C 0.29418(9) 0.55342(13) 0.29445(18) 0.0408(3) Uani 1 1 d . . .
C7 C 0.21991(9) 0.49212(13) 0.24102(18) 0.0407(3) Uani 1 1 d . . .
C8 C 0.20786(8) 0.36724(13) 0.21277(17) 0.0385(3) Uani 1 1 d . . .
C9 C 0.26313(9) 0.27613(13) 0.26751(19) 0.0431(4) Uani 1 1 d . . .
H9 H 0.3119 0.2984 0.3232 0.052 Uiso 1 1 calc R . .
C10 C 0.24751(9) 0.15695(14) 0.24155(19) 0.0424(4) Uani 1 1 d . . .
C11 C 0.12006(8) 0.20432(14) 0.10429(18) 0.0396(3) Uani 1 1 d . . .
C12 C 0.13515(8) 0.32323(14) 0.13109(18) 0.0411(3) Uani 1 1 d . . .
H12 H 0.0959 0.3782 0.0941 0.049 Uiso 1 1 calc R . .
C13 C 0.30799(11) 0.06418(16) 0.3034(3) 0.0611(5) Uani 1 1 d . . .
H13A H 0.2854 0.0095 0.3760 0.092 Uiso 1 1 calc R . .
H13B H 0.3531 0.1030 0.3627 0.092 Uiso 1 1 calc R . .
H13C H 0.3241 0.0208 0.2110 0.092 Uiso 1 1 calc R . .
C14 C 0.04219(9) 0.16464(16) 0.0140(2) 0.0525(4) Uani 1 1 d . . .
H14A H 0.0107 0.2337 -0.0198 0.079 Uiso 1 1 calc R . .
H14B H 0.0148 0.1160 0.0862 0.079 Uiso 1 1 calc R . .
H14C H 0.0513 0.1189 -0.0820 0.079 Uiso 1 1 calc R . .
C15 C 0.15744(10) -0.00979(14) 0.14152(19) 0.0467(4) Uani 1 1 d . . .
H15A H 0.2057 -0.0540 0.1314 0.056 Uiso 1 1 calc R . .
H15B H 0.1217 -0.0224 0.0408 0.056 Uiso 1 1 calc R . .
C16 C 0.11998(12) -0.05786(16) 0.2868(2) 0.0596(5) Uani 1 1 d . . .
H16A H 0.1562 -0.0492 0.3862 0.089 Uiso 1 1 calc R . .
H16B H 0.1074 -0.1411 0.2690 0.089 Uiso 1 1 calc R . .
H16C H 0.0724 -0.0139 0.2980 0.089 Uiso 1 1 calc R . .
C17 C 0.15085(9) 0.56472(14) 0.21769(19) 0.0438(4) Uani 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 N1 1.228(2) . ?
O2 N1 1.233(3) . ?
N1 C3 1.455(2) . ?
N2 C17 1.151(2) . ?
N3 C10 1.3770(19) . ?
N3 C11 1.3770(19) . ?
N3 C15 1.4858(19) . ?
C1 C2 1.377(2) . ?
C1 C6 1.410(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C4 C5 1.369(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.457(2) . ?
C7 C17 1.422(2) . ?
C7 C8 1.422(2) . ?
C8 C9 1.420(2) . ?
C8 C12 1.421(2) . ?
C9 C10 1.367(2) . ?
C9 H9 0.9300 . ?
C10 C13 1.503(2) . ?
C11 C12 1.363(2) . ?
C11 C14 1.503(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.506(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
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
O1 N1 O2 122.53(17) . . ?
O1 N1 C3 119.09(18) . . ?
O2 N1 C3 118.34(18) . . ?
C10 N3 C11 119.42(13) . . ?
C10 N3 C15 120.36(12) . . ?
C11 N3 C15 120.01(12) . . ?
C2 C1 C6 121.92(15) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 119.22(16) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.17(15) . . ?
C2 C3 N1 119.56(16) . . ?
C4 C3 N1 119.23(16) . . ?
C5 C4 C3 118.97(16) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.24(16) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 116.47(14) . . ?
C1 C6 C7 123.06(14) . . ?
C5 C6 C7 120.36(14) . . ?
C17 C7 C8 115.77(13) . . ?
C17 C7 C6 116.57(13) . . ?
C8 C7 C6 127.64(13) . . ?
C9 C8 C12 114.04(13) . . ?
C9 C8 C7 124.93(13) . . ?
C12 C8 C7 120.97(13) . . ?
C10 C9 C8 122.54(14) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 N3 120.66(14) . . ?
C9 C10 C13 120.30(14) . . ?
N3 C10 C13 119.05(13) . . ?
C12 C11 N3 120.12(13) . . ?
C12 C11 C14 120.19(14) . . ?
N3 C11 C14 119.69(14) . . ?
C11 C12 C8 123.22(14) . . ?
C11 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 112.30(13) . . ?
N3 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N3 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C7 178.72(18) . . ?

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
C6 C1 C2 C3 -1.3(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 N1 -177.34(16) . . . . ?
O1 N1 C3 C2 -9.5(3) . . . . ?
O2 N1 C3 C2 168.0(2) . . . . ?
O1 N1 C3 C4 172.8(2) . . . . ?
O2 N1 C3 C4 -9.7(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
N1 C3 C4 C5 178.40(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C6 C7 177.45(15) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 -176.47(15) . . . . ?
C1 C6 C7 C17 -155.82(15) . . . . ?
C5 C6 C7 C17 20.3(2) . . . . ?
C1 C6 C7 C8 25.7(2) . . . . ?
C5 C6 C7 C8 -158.14(15) . . . . ?
C17 C7 C8 C9 -163.30(14) . . . . ?
C6 C7 C8 C9 15.2(2) . . . . ?
C17 C7 C8 C12 13.6(2) . . . . ?
C6 C7 C8 C12 -167.89(14) . . . . ?
C12 C8 C9 C10 0.7(2) . . . . ?
C7 C8 C9 C10 177.84(15) . . . . ?
C8 C9 C10 N3 0.4(2) . . . . ?
C8 C9 C10 C13 -179.52(15) . . . . ?
C11 N3 C10 C9 -1.0(2) . . . . ?
C15 N3 C10 C9 -175.65(14) . . . . ?
C11 N3 C10 C13 178.90(15) . . . . ?
C15 N3 C10 C13 4.2(2) . . . . ?
C10 N3 C11 C12 0.5(2) . . . . ?
C15 N3 C11 C12 175.14(13) . . . . ?
C10 N3 C11 C14 -179.97(13) . . . . ?
C15 N3 C11 C14 -5.3(2) . . . . ?
N3 C11 C12 C8 0.7(2) . . . . ?
C14 C11 C12 C8 -178.84(14) . . . . ?
C9 C8 C12 C11 -1.3(2) . . . . ?
C7 C8 C12 C11 -178.52(14) . . . . ?
C10 N3 C15 C16 87.36(18) . . . . ?
C11 N3 C15 C16 -87.27(17) . . . . ?
C8 C7 C17 N2 41(8) . . . . ?
C6 C7 C17 N2 -138(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_dm16482_0m
_database_code_depnum_ccdc_archive 'CCDC 1498123'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H35 N3 O2 S'
_chemical_formula_weight         417.60

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/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                   9.2082(16)
_cell_length_b                   12.659(2)
_cell_length_c                   19.962(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.023(3)
_cell_angle_gamma                90
_cell_volume                     2267.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3235
_cell_measurement_theta_min      5.412
_cell_measurement_theta_max      54.947

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6523
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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            11879
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4365
_reflns_number_gt                3292
_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-2013 (Sheldrick, 2013)'
_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)+(0.0523P)²+0.5543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4365
_refine_ls_number_parameters     314
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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 1.25382(4) 0.52769(3) 1.21090(2) 0.02636(14) Uani 1 1 d . . . . .
N1 N 1.04206(14) 0.42458(10) 1.12137(7) 0.0204(3) Uani 1 1 d . . . . .
N2 N 1.04175(14) 0.60729(10) 1.10960(7) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.44373(14) 0.48647(11) 0.87526(7) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.85737(14) 0.32164(9) 1.06121(7) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.85997(14) 0.69372(9) 1.03474(7) 0.0382(3) Uani 1 1 d . . . . .
C1 C 1.10643(16) 0.51950(12) 1.14405(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.90766(17) 0.41247(12) 1.07018(9) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.84140(17) 0.50571(11) 1.03563(8) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.90883(18) 0.60651(12) 1.05664(8) 0.0220(4) Uani 1 1 d . . . . .
C5 C 1.10650(18) 0.71305(12) 1.12978(9) 0.0243(4) Uani 1 1 d . . . . .
H5A H 1.0854 0.7603 1.0892 0.029 Uiso 1 1 calc R U . . .
H5B H 1.2160 0.7066 1.1456 0.029 Uiso 1 1 calc R U . . .
C6 C 1.0433(2) 0.76148(14) 1.18667(10) 0.0331(4) Uani 1 1 d . . . . .
H6A H 0.9359 0.7729 1.1700 0.050 Uiso 1 1 calc R U . . .
H6B H 1.0925 0.8292 1.2005 0.050 Uiso 1 1 calc R U . . .
H6C H 1.0607 0.7136 1.2263 0.050 Uiso 1 1 calc R U . . .
C7 C 1.10817(18) 0.32558(12) 1.15439(9) 0.0271(4) Uani 1 1 d . . . . .
H7A H 1.2178 0.3337 1.1685 0.033 Uiso 1 1 calc R U . . .
H7B H 1.0864 0.2672 1.1206 0.033 Uiso 1 1 calc R U . . .
C8 C 1.0482(2) 0.29732(14) 1.21679(10) 0.0352(5) Uani 1 1 d . . . . .
H8A H 1.0686 0.3552 1.2502 0.053 Uiso 1 1 calc R U . . .
H8B H 1.0967 0.2327 1.2378 0.053 Uiso 1 1 calc R U . . .
H8C H 0.9403 0.2858 1.2027 0.053 Uiso 1 1 calc R U . . .
C9 C 0.70758(17) 0.49918(12) 0.98115(8) 0.0201(4) Uani 1 1 d . . . . .
C10 C 0.63586(17) 0.40202(12) 0.95785(8) 0.0218(4) Uani 1 1 d . . . . .
H10 H 0.6780 0.3382 0.9786 0.026 Uiso 1 1 calc R U . . .
C11 C 0.50868(18) 0.39646(13) 0.90675(9) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.50997(17) 0.58226(13) 0.89424(9) 0.0245(4) Uani 1 1 d . . . . .
C13 C 0.63679(17) 0.58882(12) 0.94549(8) 0.0222(4) Uani 1 1 d . . . . .
H13 H 0.6792 0.6565 0.9577 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4376(2) 0.29102(14) 0.88562(10) 0.0340(4) Uani 1 1 d . . . . .
H14A H 0.3432 0.2860 0.9002 0.051 Uiso 1 1 calc R U . . .
H14B H 0.5046 0.2345 0.9073 0.051 Uiso 1 1 calc R U . . .
H14C H 0.4188 0.2839 0.8355 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4396(2) 0.68089(14) 0.85948(10) 0.0342(4) Uani 1 1 d . . . . .
H15A H 0.4198 0.6717 0.8095 0.051 Uiso 1 1 calc R U . . .
H15B H 0.5074 0.7407 0.8730 0.051 Uiso 1 1 calc R U . . .
H15C H 0.3457 0.6946 0.8733 0.051 Uiso 1 1 calc R U . . .
C16 C 0.30678(18) 0.48030(15) 0.81918(9) 0.0279(4) Uani 1 1 d . . . . .
H16A H 0.2465 0.5449 0.8200 0.033 Uiso 1 1 calc R U . . .
H16B H 0.2465 0.4190 0.8276 0.033 Uiso 1 1 calc R U . . .
C17 C 0.34125(18) 0.46924(14) 0.74851(9) 0.0265(4) Uani 1 1 d . . . . .
H17A H 0.4005 0.4043 0.7473 0.032 Uiso 1 1 calc R U . . .
H17B H 0.4019 0.5303 0.7400 0.032 Uiso 1 1 calc R U . . .
C18 C 0.19963(19) 0.46391(16) 0.69201(9) 0.0337(4) Uani 1 1 d . . . . .
H18A H 0.1393 0.5251 0.6943 0.040 Uiso 0.5 1 d R U P A 1
H18B H 0.1451 0.4071 0.6977 0.040 Uiso 0.5 1 d R U P A 1
H18C H 0.1547 0.5327 0.6866 0.040 Uiso 0.5 1 d R U P B 2
H18D H 0.1321 0.4159 0.7066 0.040 Uiso 0.5 1 d R U P B 2
C19 C 0.2418(7) 0.4608(4) 0.6215(4) 0.0334(10) Uani 0.5 1 d . U P C 1
H19A H 0.3081 0.5212 0.6184 0.040 Uiso 0.5 1 calc R U P C 1
H19B H 0.2984 0.3952 0.6184 0.040 Uiso 0.5 1 calc R U P C 1
C20 C 0.1102(4) 0.4649(3) 0.5616(2) 0.0380(8) Uani 0.5 1 d . U P C 1
H20A H 0.0573 0.5327 0.5630 0.046 Uiso 0.5 1 calc R U P C 1
H20B H 0.0407 0.4072 0.5663 0.046 Uiso 0.5 1 calc R U P C 1
C21 C 0.1511(5) 0.4547(3) 0.4924(2) 0.0397(8) Uani 0.5 1 d . U P C 1
H21A H 0.0585 0.4435 0.4568 0.048 Uiso 0.5 1 calc R U P C 1
H21B H 0.2137 0.3909 0.4933 0.048 Uiso 0.5 1 calc R U P C 1
C22 C 0.2343(5) 0.5489(3) 0.4710(2) 0.0455(9) Uani 0.5 1 d . U P C 1
H22A H 0.3325 0.5559 0.5034 0.055 Uiso 0.5 1 calc R U P C 1
H22B H 0.1770 0.6143 0.4740 0.055 Uiso 0.5 1 calc R U P C 1
C23 C 0.2574(7) 0.5374(5) 0.3977(3) 0.0554(13) Uani 0.5 1 d . U P C 1
H23A H 0.3154 0.4733 0.3946 0.083 Uiso 0.5 1 calc R U P C 1
H23B H 0.3114 0.5991 0.3862 0.083 Uiso 0.5 1 calc R U P C 1
H23C H 0.1604 0.5323 0.3653 0.083 Uiso 0.5 1 calc R U P C 1
C19' C 0.2201(7) 0.4264(4) 0.6213(4) 0.0312(10) Uani 0.5 1 d . U P C 2
H19C H 0.2850 0.3631 0.6276 0.037 Uiso 0.5 1 calc R U P C 2
H19D H 0.1219 0.4058 0.5926 0.037 Uiso 0.5 1 calc R U P C 2
C20' C 0.2892(5) 0.5119(3) 0.58354(19) 0.0329(7) Uani 0.5 1 d . U P C 2
H20C H 0.2267 0.5762 0.5789 0.040 Uiso 0.5 1 calc R U P C 2
H20D H 0.3893 0.5303 0.6112 0.040 Uiso 0.5 1 calc R U P C 2
C21' C 0.3029(5) 0.4756(3) 0.51235(19) 0.0362(7) Uani 0.5 1 d . U P C 2
H21C H 0.3778 0.4182 0.5179 0.043 Uiso 0.5 1 calc R U P C 2
H21D H 0.2061 0.4456 0.4880 0.043 Uiso 0.5 1 calc R U P C 2
C22' C 0.3471(6) 0.5610(3) 0.4680(2) 0.0436(9) Uani 0.5 1 d . U P C 2
H22C H 0.2779 0.6215 0.4655 0.052 Uiso 0.5 1 calc R U P C 2
H22D H 0.4486 0.5862 0.4895 0.052 Uiso 0.5 1 calc R U P C 2
C23' C 0.3446(7) 0.5231(4) 0.3963(3) 0.0499(12) Uani 0.5 1 d . U P C 2
H23D H 0.4142 0.4639 0.3984 0.075 Uiso 0.5 1 calc R U P C 2
H23E H 0.3743 0.5808 0.3696 0.075 Uiso 0.5 1 calc R U P C 2
H23F H 0.2437 0.4997 0.3743 0.075 Uiso 0.5 1 calc R U P C 2


_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 C1 1.6785(16) . ?
N1 C1 1.3708(19) . ?
N1 C2 1.425(2) . ?
N1 C7 1.4816(19) . ?
N2 C1 1.3704(19) . ?
N2 C4 1.426(2) . ?
N2 C5 1.4838(19) . ?
N3 C12 1.372(2) . ?
N3 C11 1.372(2) . ?
N3 C16 1.488(2) . ?
O1 C2 1.2373(19) . ?
O2 C4 1.2344(19) . ?
C2 C3 1.432(2) . ?
C3 C4 1.440(2) . ?
C3 C9 1.451(2) . ?
C5 C6 1.517(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C13 1.418(2) . ?
C9 C10 1.424(2) . ?
C10 C11 1.371(2) . ?
C10 H10 0.9500 . ?
C11 C14 1.504(2) . ?
C12 C13 1.371(2) . ?
C12 C15 1.502(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.521(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.521(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19' 1.541(7) . ?
C18 C19 1.543(8) . ?
C18 H18A 0.9598 . ?
C18 H18B 0.8989 . ?
C18 H18C 0.9592 . ?
C18 H18D 0.9604 . ?
C19 C20 1.498(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.529(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.534(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C19' C20' 1.537(6) . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20' C21' 1.526(5) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C21' C22' 1.510(5) . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22' C23' 1.504(7) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 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
C1 N1 C2 124.91(13) . . ?
C1 N1 C7 119.39(13) . . ?
C2 N1 C7 115.57(12) . . ?
C1 N2 C4 124.74(12) . . ?
C1 N2 C5 119.53(13) . . ?
C4 N2 C5 115.65(12) . . ?
C12 N3 C11 119.13(14) . . ?
C12 N3 C16 120.20(14) . . ?
C11 N3 C16 120.62(14) . . ?
N2 C1 N1 116.00(14) . . ?
N2 C1 S1 122.07(11) . . ?
N1 C1 S1 121.92(12) . . ?
O1 C2 N1 116.11(14) . . ?
O1 C2 C3 126.24(15) . . ?
N1 C2 C3 117.62(13) . . ?
C2 C3 C4 118.76(14) . . ?
C2 C3 C9 120.78(13) . . ?
C4 C3 C9 120.45(13) . . ?
O2 C4 N2 116.10(14) . . ?
O2 C4 C3 126.21(15) . . ?
N2 C4 C3 117.65(13) . . ?
N2 C5 C6 111.67(13) . . ?
N2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 112.10(14) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 113.61(14) . . ?
C13 C9 C3 123.20(14) . . ?
C10 C9 C3 123.19(14) . . ?
C11 C10 C9 122.90(15) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 N3 120.64(15) . . ?
C10 C11 C14 119.93(15) . . ?
N3 C11 C14 119.43(15) . . ?
C13 C12 N3 120.71(15) . . ?
C13 C12 C15 120.03(15) . . ?
N3 C12 C15 119.23(14) . . ?
C12 C13 C9 122.97(15) . . ?
C12 C13 H13 118.5 . . ?
C9 C13 H13 118.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 112.59(13) . . ?
N3 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 C18 111.63(13) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 C19' 115.6(3) . . ?
C17 C18 C19 109.1(3) . . ?
C17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 110.6 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 107.1 . . ?
C17 C18 H18C 108.6 . . ?
C19' C18 H18C 108.4 . . ?
C17 C18 H18D 108.0 . . ?
C19' C18 H18D 107.7 . . ?
H18C C18 H18D 108.5 . . ?
C20 C19 C18 113.7(5) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.7(4) . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 115.5(3) . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21B 108.4 . . ?
C22 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 112.2(4) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20' C19' C18 112.5(4) . . ?
C20' C19' H19C 109.1 . . ?
C18 C19' H19C 109.1 . . ?
C20' C19' H19D 109.1 . . ?
C18 C19' H19D 109.1 . . ?
H19C C19' H19D 107.8 . . ?
C21' C20' C19' 112.0(4) . . ?
C21' C20' H20C 109.2 . . ?
C19' C20' H20C 109.2 . . ?
C21' C20' H20D 109.2 . . ?
C19' C20' H20D 109.2 . . ?
H20C C20' H20D 107.9 . . ?
C22' C21' C20' 114.9(3) . . ?
C22' C21' H21C 108.5 . . ?
C20' C21' H21C 108.5 . . ?
C22' C21' H21D 108.5 . . ?
C20' C21' H21D 108.5 . . ?
H21C C21' H21D 107.5 . . ?
C23' C22' C21' 112.4(4) . . ?
C23' C22' H22C 109.1 . . ?
C21' C22' H22C 109.1 . . ?
C23' C22' H22D 109.1 . . ?
C21' C22' H22D 109.1 . . ?
H22C C22' H22D 107.9 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 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
C4 N2 C1 N1 4.9(2) . . . . ?
C5 N2 C1 N1 -178.61(13) . . . . ?
C4 N2 C1 S1 -174.09(12) . . . . ?
C5 N2 C1 S1 2.4(2) . . . . ?
C2 N1 C1 N2 -6.2(2) . . . . ?
C7 N1 C1 N2 178.05(14) . . . . ?
C2 N1 C1 S1 172.75(12) . . . . ?
C7 N1 C1 S1 -3.0(2) . . . . ?
C1 N1 C2 O1 -172.63(15) . . . . ?
C7 N1 C2 O1 3.2(2) . . . . ?
C1 N1 C2 C3 5.6(2) . . . . ?
C7 N1 C2 C3 -178.56(14) . . . . ?
O1 C2 C3 C4 174.79(17) . . . . ?
N1 C2 C3 C4 -3.2(2) . . . . ?
O1 C2 C3 C9 -4.3(3) . . . . ?
N1 C2 C3 C9 177.70(13) . . . . ?
C1 N2 C4 O2 174.71(15) . . . . ?
C5 N2 C4 O2 -1.9(2) . . . . ?
C1 N2 C4 C3 -3.0(2) . . . . ?
C5 N2 C4 C3 -179.63(14) . . . . ?
C2 C3 C4 O2 -175.41(17) . . . . ?
C9 C3 C4 O2 3.7(3) . . . . ?
C2 C3 C4 N2 2.0(2) . . . . ?
C9 C3 C4 N2 -178.85(13) . . . . ?
C1 N2 C5 C6 -87.64(18) . . . . ?
C4 N2 C5 C6 89.17(17) . . . . ?
C1 N1 C7 C8 87.26(18) . . . . ?
C2 N1 C7 C8 -88.85(17) . . . . ?
C2 C3 C9 C13 179.63(15) . . . . ?
C4 C3 C9 C13 0.5(2) . . . . ?
C2 C3 C9 C10 -1.1(2) . . . . ?
C4 C3 C9 C10 179.77(15) . . . . ?
C13 C9 C10 C11 -1.3(2) . . . . ?
C3 C9 C10 C11 179.41(15) . . . . ?
C9 C10 C11 N3 0.0(2) . . . . ?
C9 C10 C11 C14 -178.98(16) . . . . ?
C12 N3 C11 C10 1.8(2) . . . . ?
C16 N3 C11 C10 179.21(14) . . . . ?
C12 N3 C11 C14 -179.29(15) . . . . ?
C16 N3 C11 C14 -1.8(2) . . . . ?
C11 N3 C12 C13 -2.1(2) . . . . ?
C16 N3 C12 C13 -179.52(14) . . . . ?
C11 N3 C12 C15 179.58(15) . . . . ?
C16 N3 C12 C15 2.1(2) . . . . ?
N3 C12 C13 C9 0.6(2) . . . . ?
C15 C12 C13 C9 178.98(16) . . . . ?
C10 C9 C13 C12 1.0(2) . . . . ?
C3 C9 C13 C12 -179.70(15) . . . . ?
C12 N3 C16 C17 87.96(18) . . . . ?
C11 N3 C16 C17 -89.46(19) . . . . ?
N3 C16 C17 C18 -179.58(15) . . . . ?
C16 C17 C18 C19' -166.0(2) . . . . ?
C16 C17 C18 C19 176.0(3) . . . . ?
C17 C18 C19 C20 -175.0(3) . . . . ?
C19' C18 C19 C20 70.6(14) . . . . ?
C18 C19 C20 C21 -176.3(3) . . . . ?
C19 C20 C21 C22 -69.6(5) . . . . ?
C20 C21 C22 C23 -174.2(4) . . . . ?
C17 C18 C19' C20' -75.2(5) . . . . ?
C19 C18 C19' C20' -2.6(12) . . . . ?
C18 C19' C20' C21' -177.6(4) . . . . ?
C19' C20' C21' C22' 170.8(4) . . . . ?
C20' C21' C22' C23' -174.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15C O1 0.98 2.52 3.455(2) 159.4 3_667
C14 H14A O2 0.98 2.52 3.470(2) 163.5 3_667
C13 H13 O2 0.95 2.05 2.741(2) 128.0 .
C10 H10 O1 0.95 2.06 2.749(2) 127.6 .
C8 H8B S1 0.98 3.01 3.9840(19) 174.7 2_747
C8 H8A S1 0.98 2.98 3.4935(19) 113.7 .
C6 H6C S1 0.98 3.01 3.5110(19) 113.2 .

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd16210
_database_code_depnum_ccdc_archive 'CCDC 1498116'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N3'
_chemical_formula_weight         199.25

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'

_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                   7.084(3)
_cell_length_b                   7.646(3)
_cell_length_c                   10.376(5)
_cell_angle_alpha                98.929(9)
_cell_angle_beta                 91.731(9)
_cell_angle_gamma                103.705(9)
_cell_volume                     538.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    959
_cell_measurement_theta_min      5.562
_cell_measurement_theta_max      54.045

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3546
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3089
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1996
_reflns_number_gt                1569
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0659P)²+0.0598P] 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
_refine_ls_extinction_coef       0.142(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1996
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
N1 N 0.29535(18) 0.18008(16) 0.74875(12) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.1345(3) -0.4597(2) 0.32228(18) 0.0725(6) Uani 1 1 d . . . . .
N3 N 0.3066(3) 0.0588(3) 0.16938(15) 0.0689(5) Uani 1 1 d . . . . .
C1 C 0.2396(2) -0.0123(2) 0.49226(14) 0.0339(4) Uani 1 1 d . . . . .
C2 C 0.2021(2) -0.1000(2) 0.60197(14) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.1566 -0.2264 0.5887 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2298(2) -0.0068(2) 0.72645(14) 0.0354(4) Uani 1 1 d . . . . .
C4 C 0.3191(2) 0.2736(2) 0.64466(15) 0.0361(4) Uani 1 1 d . . . . .
C5 C 0.2910(2) 0.1800(2) 0.52030(15) 0.0373(4) Uani 1 1 d . . . . .
H5 H 0.3062 0.2452 0.4512 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2244(2) -0.1099(2) 0.36361(15) 0.0401(4) Uani 1 1 d . . . . .
C7 C 0.1753(2) -0.3023(3) 0.33943(16) 0.0481(5) Uani 1 1 d . . . . .
C8 C 0.2692(2) -0.0176(3) 0.25614(16) 0.0463(5) Uani 1 1 d . . . . .
C9 C 0.1890(3) -0.1061(2) 0.84019(16) 0.0492(5) Uani 1 1 d . . . . .
H9A H 0.1158 -0.2291 0.8094 0.074 Uiso 1 1 calc R U . . .
H9B H 0.1154 -0.0450 0.9001 0.074 Uiso 1 1 calc R U . . .
H9C H 0.3098 -0.1077 0.8839 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3753(3) 0.4777(2) 0.67017(18) 0.0510(5) Uani 1 1 d . . . . .
H10A H 0.3664 0.5225 0.5893 0.077 Uiso 1 1 calc R U . . .
H10B H 0.5066 0.5195 0.7083 0.077 Uiso 1 1 calc R U . . .
H10C H 0.2890 0.5222 0.7293 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3425(2) 0.2801(2) 0.88470(15) 0.0464(5) Uani 1 1 d . . . . .
H11A H 0.4511 0.3850 0.8852 0.056 Uiso 1 1 calc R U . . .
H11B H 0.3834 0.2010 0.9386 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1734(3) 0.3450(3) 0.94455(17) 0.0587(5) Uani 1 1 d . . . . .
H12A H 0.1438 0.4366 0.8992 0.088 Uiso 1 1 calc R U . . .
H12B H 0.2078 0.3957 1.0351 0.088 Uiso 1 1 calc R U . . .
H12C H 0.0614 0.2437 0.9372 0.088 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
N1 C3 1.374(2) . ?
N1 C4 1.378(2) . ?
N1 C11 1.484(2) . ?
N2 C7 1.153(2) . ?
N3 C8 1.152(2) . ?
C1 C2 1.409(2) . ?
C1 C5 1.410(2) . ?
C1 C6 1.412(2) . ?
C2 C3 1.359(2) . ?
C2 H2 0.9300 . ?
C3 C9 1.499(2) . ?
C4 C5 1.359(2) . ?
C4 C10 1.495(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 C8 1.415(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C3 N1 C4 119.84(13) . . ?
C3 N1 C11 119.86(13) . . ?
C4 N1 C11 120.30(13) . . ?
C2 C1 C5 115.03(13) . . ?
C2 C1 C6 122.50(14) . . ?
C5 C1 C6 122.47(13) . . ?
C3 C2 C1 122.48(14) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 N1 119.94(13) . . ?
C2 C3 C9 120.58(14) . . ?
N1 C3 C9 119.47(13) . . ?
C5 C4 N1 119.90(14) . . ?
C5 C4 C10 120.71(14) . . ?
N1 C4 C10 119.40(14) . . ?
C4 C5 C1 122.40(14) . . ?
C4 C5 H5 118.8 . . ?
C1 C5 H5 118.8 . . ?
C7 C6 C1 120.90(14) . . ?
C7 C6 C8 118.01(14) . . ?
C1 C6 C8 120.99(15) . . ?
N2 C7 C6 178.63(19) . . ?
N3 C8 C6 179.4(2) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.46(13) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
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 . . ?

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
C5 C1 C2 C3 -5.5(2) . . . . ?
C6 C1 C2 C3 175.28(14) . . . . ?
C1 C2 C3 N1 0.5(2) . . . . ?
C1 C2 C3 C9 -179.60(14) . . . . ?
C4 N1 C3 C2 4.8(2) . . . . ?
C11 N1 C3 C2 -174.50(13) . . . . ?
C4 N1 C3 C9 -175.11(14) . . . . ?
C11 N1 C3 C9 5.6(2) . . . . ?
C3 N1 C4 C5 -4.7(2) . . . . ?
C11 N1 C4 C5 174.58(13) . . . . ?
C3 N1 C4 C10 175.18(14) . . . . ?
C11 N1 C4 C10 -5.6(2) . . . . ?
N1 C4 C5 C1 -0.7(2) . . . . ?
C10 C4 C5 C1 179.43(14) . . . . ?
C2 C1 C5 C4 5.6(2) . . . . ?
C6 C1 C5 C4 -175.20(14) . . . . ?
C2 C1 C6 C7 -1.7(2) . . . . ?
C5 C1 C6 C7 179.11(14) . . . . ?
C2 C1 C6 C8 -177.99(14) . . . . ?
C5 C1 C6 C8 2.9(2) . . . . ?
C3 N1 C11 C12 -92.70(18) . . . . ?
C4 N1 C11 C12 88.03(18) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4



