# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1850654'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.0260(4)
_cell_length_b                   7.7415(2)
_cell_length_c                   16.8380(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.290(2)
_cell_angle_gamma                90
_cell_volume                     1428.60(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.44
_cell_measurement_theta_min      5.29
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0860 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.9070.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8217
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.286
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2172
_reflns_number_total             2489
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.5953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C16(H16), C17(H17)
2.b X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.028
;
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 1.02985(9) 0.74812(14) 0.32322(6) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.80888(10) 0.81158(14) 0.18744(6) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.89466(10) 0.55044(15) 0.21691(7) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.86936(11) 0.56884(15) 0.29593(7) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.8056 0.5176 0.3127 0.022 Uiso 1 1 calc R . . . .
C1 C 1.15819(15) 0.1697(2) 0.18997(9) 0.0273(4) Uani 1 1 d . . . . .
H1 H 1.2182 0.0834 0.1853 0.033 Uiso 1 1 calc R . . . .
C2 C 1.18636(14) 0.3418(2) 0.17866(9) 0.0250(4) Uani 1 1 d . . . . .
H2A H 1.2650 0.3731 0.1654 0.030 Uiso 1 1 calc R . . . .
C3 C 1.09937(13) 0.4681(2) 0.18672(8) 0.0205(3) Uani 1 1 d . . . . .
H3 H 1.1187 0.5866 0.1805 0.025 Uiso 1 1 calc R . . . .
C4 C 0.98409(13) 0.42024(19) 0.20396(8) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.94546(13) 0.66785(18) 0.34658(9) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.91655(13) 0.67332(18) 0.43156(9) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.81937(16) 0.5865(2) 0.45840(10) 0.0314(4) Uani 1 1 d . . . . .
H7 H 0.7673 0.5183 0.4222 0.038 Uiso 1 1 calc R . . . .
C8 C 0.79738(16) 0.5982(2) 0.53786(10) 0.0325(4) Uani 1 1 d . . . . .
H8 H 0.7305 0.5378 0.5558 0.039 Uiso 1 1 calc R . . . .
C9 C 0.87222(15) 0.6970(2) 0.59075(9) 0.0267(4) Uani 1 1 d . . . . .
H9 H 0.8569 0.7054 0.6450 0.032 Uiso 1 1 calc R . . . .
C10 C 0.96910(17) 0.7833(3) 0.56456(10) 0.0371(4) Uani 1 1 d . . . . .
H10 H 1.0208 0.8515 0.6009 0.045 Uiso 1 1 calc R . . . .
C11 C 0.99189(16) 0.7712(2) 0.48517(10) 0.0321(4) Uani 1 1 d . . . . .
H11 H 1.0595 0.8305 0.4676 0.038 Uiso 1 1 calc R . . . .
C12 C 0.85980(12) 0.68185(19) 0.16542(9) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.88159(13) 0.6567(2) 0.07969(9) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.82848(16) 0.5182(2) 0.03850(10) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.8362 0.5050 -0.0168 0.038 Uiso 1 1 calc R . . . .
H14B H 0.7841 0.4355 0.0653 0.038 Uiso 1 1 calc R . . . .
C15 C 0.95108(16) 0.7897(2) 0.04435(10) 0.0301(4) Uani 1 1 d . . . . .
H15A H 0.9453 0.7726 -0.0136 0.045 Uiso 1 1 calc GR . . . .
H15B H 1.0367 0.7830 0.0669 0.045 Uiso 1 1 calc GR . . . .
H15C H 0.9182 0.9035 0.0558 0.045 Uiso 1 1 calc GR . . . .
C16 C 0.95446(14) 0.24797(19) 0.21447(9) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.8749 0.2165 0.2258 0.026 Uiso 1 1 calc R . . . .
C17 C 1.04268(15) 0.1225(2) 0.20815(9) 0.0274(4) Uani 1 1 d . . . . .
H17 H 1.0242 0.0043 0.2162 0.033 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 C5 1.2194(18) . ?
O2 C12 1.2276(18) . ?
N1 N2 1.3964(16) . ?
N1 C4 1.4432(18) . ?
N1 C12 1.3643(18) . ?
N2 H2 0.8800 . ?
N2 C5 1.3646(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C17 1.391(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 C16 1.389(2) . ?
C5 C6 1.500(2) . ?
C6 C7 1.382(2) . ?
C6 C11 1.384(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.502(2) . ?
C13 C14 1.373(2) . ?
C13 C15 1.449(2) . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C4 115.24(11) . . ?
C12 N1 N2 117.24(12) . . ?
C12 N1 C4 125.05(12) . . ?
N1 N2 H2 120.7 . . ?
C5 N2 N1 118.65(11) . . ?
C5 N2 H2 120.7 . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C17 120.49(15) . . ?
C17 C1 H1 119.8 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.78(15) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.49(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 N1 120.18(13) . . ?
C3 C4 C16 121.18(14) . . ?
C16 C4 N1 118.50(13) . . ?
O1 C5 N2 121.56(13) . . ?
O1 C5 C6 122.87(13) . . ?
N2 C5 C6 115.57(12) . . ?
C7 C6 C5 123.47(13) . . ?
C7 C6 C11 118.98(14) . . ?
C11 C6 C5 117.55(14) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.45(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.23(16) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.64(15) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.34(16) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.35(16) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O2 C12 N1 121.63(13) . . ?
O2 C12 C13 121.52(13) . . ?
N1 C12 C13 116.79(12) . . ?
C14 C13 C12 118.83(14) . . ?
C14 C13 C15 124.26(15) . . ?
C15 C13 C12 116.75(13) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16 120.5 . . ?
C17 C16 C4 119.08(15) . . ?
C17 C16 H16 120.5 . . ?
C1 C17 H17 120.0 . . ?
C16 C17 C1 119.97(15) . . ?
C16 C17 H17 120.0 . . ?

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 C5 C6 C7 178.31(15) . . . . ?
O1 C5 C6 C11 -1.6(2) . . . . ?
O2 C12 C13 C14 -118.44(16) . . . . ?
O2 C12 C13 C15 57.18(19) . . . . ?
N1 N2 C5 O1 4.5(2) . . . . ?
N1 N2 C5 C6 -176.64(11) . . . . ?
N1 C4 C16 C17 -175.16(12) . . . . ?
N1 C12 C13 C14 58.88(19) . . . . ?
N1 C12 C13 C15 -125.49(14) . . . . ?
N2 N1 C4 C3 -108.01(14) . . . . ?
N2 N1 C4 C16 67.73(16) . . . . ?
N2 N1 C12 O2 0.38(19) . . . . ?
N2 N1 C12 C13 -176.93(11) . . . . ?
N2 C5 C6 C7 -0.5(2) . . . . ?
N2 C5 C6 C11 179.55(14) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C2 C1 C17 C16 0.5(2) . . . . ?
C2 C3 C4 N1 176.56(12) . . . . ?
C2 C3 C4 C16 0.9(2) . . . . ?
C3 C4 C16 C17 0.5(2) . . . . ?
C4 N1 N2 C5 82.67(15) . . . . ?
C4 N1 C12 O2 -160.86(13) . . . . ?
C4 N1 C12 C13 21.82(19) . . . . ?
C4 C16 C17 C1 -1.2(2) . . . . ?
C5 C6 C7 C8 -179.55(15) . . . . ?
C5 C6 C11 C10 179.21(16) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C12 N1 N2 C5 -80.41(16) . . . . ?
C12 N1 C4 C3 53.56(19) . . . . ?
C12 N1 C4 C16 -130.70(15) . . . . ?
C17 C1 C2 C3 1.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 1850657'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2015-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H18 N3 O2'
_chemical_formula_weight         320.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.7749(5)
_cell_length_b                   12.4865(4)
_cell_length_c                   8.8566(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.2110(10)
_cell_angle_gamma                90
_cell_volume                     1631.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9701
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.776
_cell_measurement_theta_min      2.995
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.8181.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20867
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.771
_diffrn_reflns_theta_max         66.771
_diffrn_reflns_theta_min         4.639
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             2867
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.5199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8AA(H8AA), C3(H3), C4(H4), C9AA(H9AA), C1BA(H1BA), C1AA(H1AA), C2AA(H2AA),
 C0BA(H0BA), C5AA(H5AA)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6AA(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.42914(7) 0.14235(8) 1.04319(11) 0.0193(2) Uani 1 1 d . . . . .
C8AA C 0.20446(9) -0.07737(11) 0.44795(14) 0.0249(3) Uani 1 1 d . . . . .
H8AA H 0.2035 -0.1096 0.3507 0.030 Uiso 1 1 calc R . . . .
C3 C 0.22497(8) -0.09186(10) 0.71845(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.2377 -0.1339 0.8065 0.025 Uiso 1 1 calc R . . . .
C4 C 0.18800(9) 0.07909(11) 0.60347(14) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.1762 0.1535 0.6129 0.026 Uiso 1 1 calc R . . . .
C9AA C 0.18625(9) 0.03095(11) 0.46178(15) 0.0252(3) Uani 1 1 d . . . . .
H9AA H 0.1724 0.0726 0.3737 0.030 Uiso 1 1 calc R . . . .
O6 O 0.23820(6) -0.09196(7) 1.07801(10) 0.0229(2) Uani 1 1 d . . . . .
C7 C 0.33311(9) 0.23084(10) 0.85291(14) 0.0222(3) Uani 1 1 d . . . . .
H7A H 0.2762 0.2648 0.8787 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.3267 0.2030 0.7494 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.3822 0.2837 0.8602 0.033 Uiso 1 1 calc GR . . . .
O8 O 0.15600(6) 0.16063(7) 1.07112(10) 0.0248(2) Uani 1 1 d . . . . .
C7AA C 0.04868(9) 0.11935(11) 0.86889(15) 0.0259(3) Uani 1 1 d . . . . .
C2 C 0.14099(8) 0.11762(10) 0.94819(14) 0.0202(3) Uani 1 1 d . . . . .
N3 N 0.20989(7) 0.06629(8) 0.87825(11) 0.0182(2) Uani 1 1 d . . . . .
N4 N 0.29204(7) 0.05777(8) 0.96554(11) 0.0176(2) Uani 1 1 d . . . . .
C5 C 0.35474(8) 0.14113(10) 0.95985(13) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.44639(8) 0.05743(10) 1.14259(13) 0.0193(3) Uani 1 1 d . . . . .
C1BA C 0.22404(9) -0.13872(11) 0.57622(15) 0.0244(3) Uani 1 1 d . . . . .
H1BA H 0.2368 -0.2129 0.5667 0.029 Uiso 1 1 calc R . . . .
C8 C 0.20724(8) 0.01669(10) 0.73109(13) 0.0182(3) Uani 1 1 d . . . . .
C0AA C 0.00977(10) 0.02895(14) 0.81741(18) 0.0344(4) Uani 1 1 d . . . . .
C1AA C 0.52795(9) 0.05814(11) 1.23234(14) 0.0228(3) Uani 1 1 d . . . . .
H1AA H 0.5693 0.1159 1.2249 0.027 Uiso 1 1 calc R . . . .
C2AA C 0.54780(9) -0.02483(12) 1.33101(14) 0.0256(3) Uani 1 1 d . . . . .
H2AA H 0.6029 -0.0236 1.3917 0.031 Uiso 1 1 calc R . . . .
C3AA C 0.29949(8) -0.02680(10) 1.06875(13) 0.0185(3) Uani 1 1 d . . . . .
C4AA C 0.38568(8) -0.02747(10) 1.15771(13) 0.0189(3) Uani 1 1 d . . . . .
C0BA C 0.48814(9) -0.11074(11) 1.34329(14) 0.0261(3) Uani 1 1 d . . . . .
H0BA H 0.5031 -0.1682 1.4105 0.031 Uiso 1 1 calc R . . . .
C5AA C 0.40737(9) -0.11181(11) 1.25747(14) 0.0229(3) Uani 1 1 d . . . . .
H5AA H 0.3664 -0.1698 1.2660 0.027 Uiso 1 1 calc R . . . .
C6AA C 0.00317(11) 0.22560(14) 0.8668(2) 0.0456(4) Uani 1 1 d . . . . .
H6AA H -0.0599 0.2176 0.8278 0.068 Uiso 1 1 calc GR . . . .
H6AB H 0.0350 0.2746 0.8015 0.068 Uiso 1 1 calc GR . . . .
H6AC H 0.0044 0.2546 0.9697 0.068 Uiso 1 1 calc GR . . . .
H0AA H 0.0422(14) -0.0396(17) 0.828(2) 0.055 Uiso 1 1 d R . . . .
H0AB H -0.0549(13) 0.0283(14) 0.786(2) 0.041(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.2894(16) . ?
N1 C6 1.3926(16) . ?
C8AA H8AA 0.9500 . ?
C8AA C9AA 1.386(2) . ?
C8AA C1BA 1.3872(19) . ?
C3 H3 0.9500 . ?
C3 C1BA 1.3883(18) . ?
C3 C8 1.3862(19) . ?
C4 H4 0.9500 . ?
C4 C9AA 1.3904(18) . ?
C4 C8 1.3890(17) . ?
C9AA H9AA 0.9500 . ?
O6 C3AA 1.2235(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C5 1.4900(18) . ?
O8 C2 1.2231(15) . ?
C7AA C2 1.4990(18) . ?
C7AA C0AA 1.335(2) . ?
C7AA C6AA 1.487(2) . ?
C2 N3 1.3789(16) . ?
N3 N4 1.4061(14) . ?
N3 C8 1.4416(15) . ?
N4 C5 1.3962(16) . ?
N4 C3AA 1.3970(16) . ?
C6 C1AA 1.4059(18) . ?
C6 C4AA 1.3999(18) . ?
C1BA H1BA 0.9500 . ?
C0AA H0AA 0.98(2) . ?
C0AA H0AB 0.981(19) . ?
C1AA H1AA 0.9500 . ?
C1AA C2AA 1.3763(19) . ?
C2AA H2AA 0.9500 . ?
C2AA C0BA 1.397(2) . ?
C3AA C4AA 1.4595(17) . ?
C4AA C5AA 1.4002(18) . ?
C0BA H0BA 0.9500 . ?
C0BA C5AA 1.3786(19) . ?
C5AA H5AA 0.9500 . ?
C6AA H6AA 0.9800 . ?
C6AA H6AB 0.9800 . ?
C6AA H6AC 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
C5 N1 C6 118.22(11) . . ?
C9AA C8AA H8AA 120.0 . . ?
C9AA C8AA C1BA 119.95(12) . . ?
C1BA C8AA H8AA 120.0 . . ?
C1BA C3 H3 120.2 . . ?
C8 C3 H3 120.2 . . ?
C8 C3 C1BA 119.54(12) . . ?
C9AA C4 H4 120.5 . . ?
C8 C4 H4 120.5 . . ?
C8 C4 C9AA 118.98(12) . . ?
C8AA C9AA C4 120.52(12) . . ?
C8AA C9AA H9AA 119.7 . . ?
C4 C9AA H9AA 119.7 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
C0AA C7AA C2 120.72(13) . . ?
C0AA C7AA C6AA 124.35(14) . . ?
C6AA C7AA C2 114.68(12) . . ?
O8 C2 C7AA 121.71(11) . . ?
O8 C2 N3 120.16(11) . . ?
N3 C2 C7AA 118.13(11) . . ?
C2 N3 N4 115.11(10) . . ?
C2 N3 C8 128.50(10) . . ?
N4 N3 C8 116.33(9) . . ?
C5 N4 N3 118.54(10) . . ?
C5 N4 C3AA 123.99(10) . . ?
C3AA N4 N3 116.80(10) . . ?
N1 C5 C7 120.04(11) . . ?
N1 C5 N4 122.29(11) . . ?
N4 C5 C7 117.66(11) . . ?
N1 C6 C1AA 118.25(12) . . ?
N1 C6 C4AA 122.79(11) . . ?
C4AA C6 C1AA 118.96(12) . . ?
C8AA C1BA C3 120.09(13) . . ?
C8AA C1BA H1BA 120.0 . . ?
C3 C1BA H1BA 120.0 . . ?
C3 C8 C4 120.92(12) . . ?
C3 C8 N3 119.83(11) . . ?
C4 C8 N3 119.25(11) . . ?
C7AA C0AA H0AA 120.4(12) . . ?
C7AA C0AA H0AB 119.9(10) . . ?
H0AA C0AA H0AB 118.8(16) . . ?
C6 C1AA H1AA 120.0 . . ?
C2AA C1AA C6 119.98(13) . . ?
C2AA C1AA H1AA 120.0 . . ?
C1AA C2AA H2AA 119.5 . . ?
C1AA C2AA C0BA 120.97(12) . . ?
C0BA C2AA H2AA 119.5 . . ?
O6 C3AA N4 121.00(11) . . ?
O6 C3AA C4AA 125.92(11) . . ?
N4 C3AA C4AA 113.08(10) . . ?
C6 C4AA C3AA 119.23(11) . . ?
C6 C4AA C5AA 120.31(12) . . ?
C5AA C4AA C3AA 120.45(12) . . ?
C2AA C0BA H0BA 120.2 . . ?
C5AA C0BA C2AA 119.68(12) . . ?
C5AA C0BA H0BA 120.2 . . ?
C4AA C5AA H5AA 120.0 . . ?
C0BA C5AA C4AA 120.07(12) . . ?
C0BA C5AA H5AA 120.0 . . ?
C7AA C6AA H6AA 109.5 . . ?
C7AA C6AA H6AB 109.5 . . ?
C7AA C6AA H6AC 109.5 . . ?
H6AA C6AA H6AB 109.5 . . ?
H6AA C6AA H6AC 109.5 . . ?
H6AB C6AA H6AC 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
N1 C6 C1AA C2AA -179.45(11) . . . . ?
N1 C6 C4AA C3AA -1.43(17) . . . . ?
N1 C6 C4AA C5AA 178.79(11) . . . . ?
C9AA C8AA C1BA C3 0.3(2) . . . . ?
C9AA C4 C8 C3 0.35(19) . . . . ?
C9AA C4 C8 N3 179.50(11) . . . . ?
O6 C3AA C4AA C6 -175.04(11) . . . . ?
O6 C3AA C4AA C5AA 4.74(19) . . . . ?
O8 C2 N3 N4 6.86(17) . . . . ?
O8 C2 N3 C8 -176.11(12) . . . . ?
C7AA C2 N3 N4 -173.52(10) . . . . ?
C7AA C2 N3 C8 3.51(19) . . . . ?
C2 N3 N4 C5 -88.20(13) . . . . ?
C2 N3 N4 C3AA 82.83(13) . . . . ?
C2 N3 C8 C3 -118.96(14) . . . . ?
C2 N3 C8 C4 61.88(17) . . . . ?
N3 N4 C5 N1 175.78(10) . . . . ?
N3 N4 C5 C7 -4.12(15) . . . . ?
N3 N4 C3AA O6 2.43(16) . . . . ?
N3 N4 C3AA C4AA -178.14(9) . . . . ?
N4 N3 C8 C3 58.04(15) . . . . ?
N4 N3 C8 C4 -121.11(12) . . . . ?
N4 C3AA C4AA C6 5.57(16) . . . . ?
N4 C3AA C4AA C5AA -174.66(11) . . . . ?
C5 N1 C6 C1AA 179.33(11) . . . . ?
C5 N1 C6 C4AA -1.36(17) . . . . ?
C5 N4 C3AA O6 172.92(11) . . . . ?
C5 N4 C3AA C4AA -7.66(16) . . . . ?
C6 N1 C5 C7 179.44(10) . . . . ?
C6 N1 C5 N4 -0.46(17) . . . . ?
C6 C1AA C2AA C0BA 0.31(19) . . . . ?
C6 C4AA C5AA C0BA 1.07(18) . . . . ?
C1BA C8AA C9AA C4 0.4(2) . . . . ?
C1BA C3 C8 C4 0.39(19) . . . . ?
C1BA C3 C8 N3 -178.75(11) . . . . ?
C8 C3 C1BA C8AA -0.73(19) . . . . ?
C8 C4 C9AA C8AA -0.76(19) . . . . ?
C8 N3 N4 C5 94.39(12) . . . . ?
C8 N3 N4 C3AA -94.58(12) . . . . ?
C0AA C7AA C2 O8 -128.95(15) . . . . ?
C0AA C7AA C2 N3 51.44(18) . . . . ?
C1AA C6 C4AA C3AA 177.87(10) . . . . ?
C1AA C6 C4AA C5AA -1.91(17) . . . . ?
C1AA C2AA C0BA C5AA -1.17(19) . . . . ?
C2AA C0BA C5AA C4AA 0.48(19) . . . . ?
C3AA N4 C5 N1 5.45(18) . . . . ?
C3AA N4 C5 C7 -174.45(11) . . . . ?
C3AA C4AA C5AA C0BA -178.71(11) . . . . ?
C4AA C6 C1AA C2AA 1.22(18) . . . . ?
C6AA C7AA C2 O8 45.59(18) . . . . ?
C6AA C7AA C2 N3 -134.02(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-22
_olex2_date_sample_submission    2015-04-21
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1850656'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2015-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.4606(3)
_cell_length_b                   12.6354(4)
_cell_length_c                   12.7086(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.2690(10)
_cell_angle_gamma                90
_cell_volume                     1465.54(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.579
_cell_measurement_theta_min      5.027
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.8773.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.642
_diffrn_reflns_theta_max         66.642
_diffrn_reflns_theta_min         5.026
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2429
_reflns_number_total             2582
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.5082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C13(H13), C14(H14)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.09148(9) -0.02579(7) 0.86460(7) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.18087(9) 0.25705(7) 0.98089(7) 0.0256(2) Uani 1 1 d . . . . .
O3 O -0.01066(10) 0.31255(7) 0.74437(7) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.06975(10) 0.14613(7) 0.80388(8) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.21869(10) 0.17010(8) 0.83485(8) 0.0179(2) Uani 1 1 d . . . . .
C1 C -0.22196(14) 0.01084(12) 0.86594(11) 0.0295(3) Uani 1 1 d . . . . .
H1A H -0.1890 -0.0616 0.8865 0.044 Uiso 1 1 calc GR . . . .
H1B H -0.3287 0.0115 0.8367 0.044 Uiso 1 1 calc GR . . . .
H1C H -0.1942 0.0567 0.9303 0.044 Uiso 1 1 calc GR . . . .
C2 C -0.15023(12) 0.05121(9) 0.77918(9) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.01583(12) 0.04778(9) 0.82340(9) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.29651(12) 0.15316(9) 0.75281(9) 0.0168(2) Uani 1 1 d . . . . .
C5 C 0.31475(12) 0.05044(9) 0.71980(9) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.2812 -0.0079 0.7538 0.024 Uiso 1 1 calc R . . . .
C6 C 0.38256(13) 0.03374(10) 0.63657(10) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.3935 -0.0362 0.6123 0.026 Uiso 1 1 calc R . . . .
C7 C 0.43435(12) 0.11923(10) 0.58880(9) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.4809 0.1076 0.5320 0.025 Uiso 1 1 calc R . . . .
C8 C -0.19059(14) -0.02132(11) 0.67889(11) 0.0292(3) Uani 1 1 d . . . . .
H8A H -0.1474 0.0065 0.6224 0.044 Uiso 1 1 calc GR . . . .
H8B H -0.2974 -0.0242 0.6506 0.044 Uiso 1 1 calc GR . . . .
H8C H -0.1528 -0.0927 0.6996 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.26606(13) 0.22750(9) 0.93016(9) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.42866(13) 0.24517(10) 0.96920(9) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.47879(15) 0.34418(11) 0.98442(10) 0.0272(3) Uani 1 1 d . . . . .
H11A H 0.5804 0.3569 1.0147 0.033 Uiso 1 1 calc R . . . .
H11B H 0.4129 0.4020 0.9649 0.033 Uiso 1 1 calc R . . . .
C12 C 0.52135(14) 0.14869(11) 0.99656(11) 0.0304(3) Uani 1 1 d . . . . .
H12A H 0.6247 0.1693 1.0211 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.5064 0.1037 0.9318 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.4940 0.1095 1.0548 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.34746(12) 0.23889(9) 0.70528(9) 0.0189(3) Uani 1 1 d . . . . .
H13 H 0.3341 0.3089 0.7282 0.023 Uiso 1 1 calc R . . . .
C14 C 0.41828(13) 0.22139(10) 0.62379(9) 0.0205(3) Uani 1 1 d . . . . .
H14 H 0.4557 0.2795 0.5921 0.025 Uiso 1 1 calc R . . . .
C15 C -0.03766(13) 0.22246(9) 0.76269(9) 0.0199(3) Uani 1 1 d . . . . .
C16 C -0.18321(13) 0.16825(10) 0.74920(11) 0.0243(3) Uani 1 1 d . . . . .
H16A H -0.2435 0.1747 0.6729 0.029 Uiso 1 1 calc R . . . .
H16B H -0.2373 0.2007 0.7979 0.029 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 C3 1.2054(14) . ?
O2 C9 1.2158(14) . ?
O3 C15 1.2028(15) . ?
N1 N2 1.3928(13) . ?
N1 C3 1.3902(15) . ?
N1 C15 1.3987(15) . ?
N2 C4 1.4419(14) . ?
N2 C9 1.3813(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5267(16) . ?
C2 C3 1.5235(15) . ?
C2 C8 1.5342(16) . ?
C2 C16 1.5385(17) . ?
C4 C5 1.3887(16) . ?
C4 C13 1.3870(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3901(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3900(17) . ?
C7 H7 0.9500 . ?
C7 C14 1.3866(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5034(16) . ?
C10 C11 1.3339(18) . ?
C10 C12 1.4884(18) . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.3914(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.5068(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
N2 N1 C15 122.48(9) . . ?
C3 N1 N2 122.37(9) . . ?
C3 N1 C15 114.74(9) . . ?
N1 N2 C4 115.76(9) . . ?
C9 N2 N1 115.62(9) . . ?
C9 N2 C4 127.04(9) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 C8 109.86(10) . . ?
C1 C2 C16 113.60(10) . . ?
C3 C2 C1 109.60(9) . . ?
C3 C2 C8 107.24(9) . . ?
C3 C2 C16 103.94(9) . . ?
C8 C2 C16 112.25(10) . . ?
O1 C3 N1 124.27(10) . . ?
O1 C3 C2 128.23(10) . . ?
N1 C3 C2 107.45(9) . . ?
C5 C4 N2 119.01(10) . . ?
C13 C4 N2 120.08(10) . . ?
C13 C4 C5 120.88(10) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.39(11) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.05(11) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.9 . . ?
C14 C7 C6 120.15(11) . . ?
C14 C7 H7 119.9 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 121.26(11) . . ?
O2 C9 C10 122.88(10) . . ?
N2 C9 C10 115.78(10) . . ?
C11 C10 C9 118.74(11) . . ?
C11 C10 C12 124.70(12) . . ?
C12 C10 C9 116.37(10) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13 120.3 . . ?
C4 C13 C14 119.39(11) . . ?
C14 C13 H13 120.3 . . ?
C7 C14 C13 120.11(11) . . ?
C7 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O3 C15 N1 123.68(11) . . ?
O3 C15 C16 129.97(11) . . ?
N1 C15 C16 106.34(10) . . ?
C2 C16 H16A 110.4 . . ?
C2 C16 H16B 110.4 . . ?
C15 C16 C2 106.80(9) . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?

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
O2 C9 C10 C11 -60.20(17) . . . . ?
O2 C9 C10 C12 115.04(13) . . . . ?
O3 C15 C16 C2 176.79(12) . . . . ?
N1 N2 C4 C5 -67.42(13) . . . . ?
N1 N2 C4 C13 110.32(12) . . . . ?
N1 N2 C9 O2 -2.01(16) . . . . ?
N1 N2 C9 C10 174.74(9) . . . . ?
N1 C15 C16 C2 -3.73(13) . . . . ?
N2 N1 C3 O1 -2.70(17) . . . . ?
N2 N1 C3 C2 179.70(9) . . . . ?
N2 N1 C15 O3 4.74(17) . . . . ?
N2 N1 C15 C16 -174.78(10) . . . . ?
N2 C4 C5 C6 176.51(10) . . . . ?
N2 C4 C13 C14 -177.98(10) . . . . ?
N2 C9 C10 C11 123.11(12) . . . . ?
N2 C9 C10 C12 -61.64(14) . . . . ?
C1 C2 C3 O1 52.26(16) . . . . ?
C1 C2 C3 N1 -130.26(10) . . . . ?
C1 C2 C16 C15 126.41(11) . . . . ?
C3 N1 N2 C4 93.38(12) . . . . ?
C3 N1 N2 C9 -99.90(12) . . . . ?
C3 N1 C15 O3 177.57(11) . . . . ?
C3 N1 C15 C16 -1.95(13) . . . . ?
C3 C2 C16 C15 7.36(12) . . . . ?
C4 N2 C9 O2 162.97(11) . . . . ?
C4 N2 C9 C10 -20.29(16) . . . . ?
C4 C5 C6 C7 1.43(17) . . . . ?
C4 C13 C14 C7 1.57(17) . . . . ?
C5 C4 C13 C14 -0.28(17) . . . . ?
C5 C6 C7 C14 -0.15(17) . . . . ?
C6 C7 C14 C13 -1.37(17) . . . . ?
C8 C2 C3 O1 -66.95(15) . . . . ?
C8 C2 C3 N1 110.53(11) . . . . ?
C8 C2 C16 C15 -108.20(11) . . . . ?
C9 N2 C4 C5 127.62(12) . . . . ?
C9 N2 C4 C13 -54.64(16) . . . . ?
C13 C4 C5 C6 -1.22(17) . . . . ?
C15 N1 N2 C4 -94.33(12) . . . . ?
C15 N1 N2 C9 72.39(13) . . . . ?
C15 N1 C3 O1 -175.54(11) . . . . ?
C15 N1 C3 C2 6.86(13) . . . . ?
C16 C2 C3 O1 174.01(11) . . . . ?
C16 C2 C3 N1 -8.51(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1850659'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2015-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H15 Cl3 N2 O3'
_chemical_formula_sum            'C19 H15 Cl3 N2 O3'
_chemical_formula_weight         425.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.0186(3)
_cell_length_b                   14.7308(5)
_cell_length_c                   16.1335(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.803(2)
_cell_angle_gamma                90
_cell_volume                     1904.75(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      4.06
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.395
_exptl_absorpt_coefficient_mu    4.556
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.6918.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19972
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.665
_diffrn_reflns_theta_min         4.065
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             3364
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.8582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.19395(7) -0.10286(4) 0.20898(3) 0.03558(17) Uani 1 1 d . . . . .
Cl2 Cl 0.05701(7) 0.06544(4) 0.14552(4) 0.04254(18) Uani 1 1 d . . . . .
Cl3 Cl 0.23738(8) -0.05300(4) 0.03868(4) 0.04296(18) Uani 1 1 d . . . . .
O1 O 0.3177(2) 0.22845(11) 0.19818(10) 0.0366(4) Uani 1 1 d . . . . .
O2 O -0.0534(2) 0.27651(11) 0.07712(11) 0.0389(4) Uani 1 1 d . . . . .
O3 O 0.4535(2) 0.42155(12) 0.08019(11) 0.0387(4) Uani 1 1 d . . . . .
N1 N 0.2975(2) 0.24813(12) 0.05920(12) 0.0321(4) Uani 1 1 d . . . . .
N2 N 0.2179(2) 0.33032(12) 0.07194(12) 0.0313(4) Uani 1 1 d . . . . .
C1 C 0.2294(3) -0.00985(15) 0.14173(14) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.3921(3) 0.03583(15) 0.16784(14) 0.0304(5) Uani 1 1 d . . . . .
H2A H 0.4812 -0.0107 0.1686 0.037 Uiso 1 1 calc R . . . .
H2B H 0.3819 0.0579 0.2254 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4490(3) 0.11550(15) 0.11460(14) 0.0298(5) Uani 1 1 d . . . . .
H3 H 0.4413 0.0986 0.0546 0.036 Uiso 1 1 calc R . . . .
C4 C 0.3477(3) 0.20046(15) 0.12938(14) 0.0303(5) Uani 1 1 d . . . . .
C5 C 0.3044(3) 0.41257(15) 0.08329(14) 0.0323(5) Uani 1 1 d . . . . .
C6 C 0.1711(3) 0.48051(15) 0.09766(13) 0.0319(5) Uani 1 1 d . . . . .
C7 C 0.1846(3) 0.57308(16) 0.10913(15) 0.0370(5) Uani 1 1 d . . . . .
H7 H 0.2897 0.6028 0.1083 0.044 Uiso 1 1 calc R . . . .
C8 C 0.0383(4) 0.62129(17) 0.12189(15) 0.0411(6) Uani 1 1 d . . . . .
H8 H 0.0433 0.6851 0.1301 0.049 Uiso 1 1 calc R . . . .
C9 C 0.0442(3) 0.33825(16) 0.08188(14) 0.0328(5) Uani 1 1 d . . . . .
C10 C 0.0178(3) 0.43657(16) 0.09788(14) 0.0327(5) Uani 1 1 d . . . . .
C11 C -0.1145(3) 0.57737(17) 0.12272(15) 0.0405(6) Uani 1 1 d . . . . .
H11 H -0.2124 0.6118 0.1317 0.049 Uiso 1 1 calc R . . . .
C12 C -0.1281(3) 0.48367(17) 0.11062(14) 0.0368(5) Uani 1 1 d . . . . .
H12 H -0.2330 0.4537 0.1111 0.044 Uiso 1 1 calc R . . . .
C13 C 0.3277(3) 0.22631(15) -0.02640(14) 0.0307(5) Uani 1 1 d . . . . .
C14 C 0.2107(3) 0.17687(16) -0.07195(15) 0.0360(5) Uani 1 1 d . . . . .
H14 H 0.1144 0.1536 -0.0465 0.043 Uiso 1 1 calc R . . . .
C15 C 0.2360(3) 0.16164(18) -0.15576(16) 0.0405(6) Uani 1 1 d . . . . .
H15 H 0.1574 0.1269 -0.1876 0.049 Uiso 1 1 calc R . . . .
C16 C 0.3755(3) 0.19690(17) -0.19297(15) 0.0385(5) Uani 1 1 d . . . . .
H16 H 0.3905 0.1877 -0.2505 0.046 Uiso 1 1 calc R . . . .
C17 C 0.4927(3) 0.24542(16) -0.14655(16) 0.0375(5) Uani 1 1 d . . . . .
H17 H 0.5889 0.2686 -0.1721 0.045 Uiso 1 1 calc R . . . .
C18 C 0.4703(3) 0.26044(16) -0.06270(15) 0.0349(5) Uani 1 1 d . . . . .
H18 H 0.5508 0.2935 -0.0305 0.042 Uiso 1 1 calc R . . . .
C19 C 0.6311(3) 0.13864(17) 0.13992(15) 0.0369(5) Uani 1 1 d . . . . .
H19A H 0.6714 0.1873 0.1043 0.055 Uiso 1 1 calc GR . . . .
H19B H 0.7010 0.0847 0.1337 0.055 Uiso 1 1 calc GR . . . .
H19C H 0.6366 0.1587 0.1979 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.776(2) . ?
Cl2 C1 1.775(2) . ?
Cl3 C1 1.783(2) . ?
O1 C4 1.215(3) . ?
O2 C9 1.201(3) . ?
O3 C5 1.206(3) . ?
N1 N2 1.387(3) . ?
N1 C4 1.382(3) . ?
N1 C13 1.446(3) . ?
N2 C5 1.405(3) . ?
N2 C9 1.412(3) . ?
C1 C2 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.515(3) . ?
C3 C19 1.542(3) . ?
C5 C6 1.488(3) . ?
C6 C7 1.380(3) . ?
C6 C10 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(4) . ?
C8 H8 0.9500 . ?
C8 C11 1.386(4) . ?
C9 C10 1.487(3) . ?
C10 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 C18 1.394(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N2 N1 C13 115.31(18) . . ?
C4 N1 N2 116.48(18) . . ?
C4 N1 C13 128.05(18) . . ?
N1 N2 C5 122.99(18) . . ?
N1 N2 C9 123.32(19) . . ?
C5 N2 C9 113.48(18) . . ?
Cl1 C1 Cl3 107.81(12) . . ?
Cl2 C1 Cl1 108.74(12) . . ?
Cl2 C1 Cl3 107.81(12) . . ?
C2 C1 Cl1 108.99(16) . . ?
C2 C1 Cl2 112.18(16) . . ?
C2 C1 Cl3 111.19(16) . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C1 C2 C3 116.93(19) . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C2 C3 H3 110.0 . . ?
C2 C3 C19 108.48(18) . . ?
C4 C3 C2 111.96(17) . . ?
C4 C3 H3 110.0 . . ?
C4 C3 C19 106.47(18) . . ?
C19 C3 H3 110.0 . . ?
O1 C4 N1 121.0(2) . . ?
O1 C4 C3 123.1(2) . . ?
N1 C4 C3 115.78(19) . . ?
O3 C5 N2 125.1(2) . . ?
O3 C5 C6 130.6(2) . . ?
N2 C5 C6 104.26(19) . . ?
C7 C6 C5 129.2(2) . . ?
C7 C6 C10 121.7(2) . . ?
C10 C6 C5 109.1(2) . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.5(2) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.6 . . ?
C11 C8 C7 120.8(2) . . ?
C11 C8 H8 119.6 . . ?
O2 C9 N2 125.0(2) . . ?
O2 C9 C10 130.8(2) . . ?
N2 C9 C10 104.25(19) . . ?
C6 C10 C9 108.8(2) . . ?
C12 C10 C6 121.3(2) . . ?
C12 C10 C9 129.8(2) . . ?
C8 C11 H11 119.2 . . ?
C8 C11 C12 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C12 C11 117.0(2) . . ?
C10 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C14 C13 N1 119.6(2) . . ?
C14 C13 C18 121.2(2) . . ?
C18 C13 N1 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 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
Cl1 C1 C2 C3 177.27(15) . . . . ?
Cl2 C1 C2 C3 -62.3(2) . . . . ?
Cl3 C1 C2 C3 58.6(2) . . . . ?
O2 C9 C10 C6 179.8(2) . . . . ?
O2 C9 C10 C12 -0.9(4) . . . . ?
O3 C5 C6 C7 1.9(4) . . . . ?
O3 C5 C6 C10 -178.4(2) . . . . ?
N1 N2 C5 O3 2.9(4) . . . . ?
N1 N2 C5 C6 -177.93(19) . . . . ?
N1 N2 C9 O2 -3.2(4) . . . . ?
N1 N2 C9 C10 177.24(19) . . . . ?
N1 C13 C14 C15 175.7(2) . . . . ?
N1 C13 C18 C17 -175.0(2) . . . . ?
N2 N1 C4 O1 2.5(3) . . . . ?
N2 N1 C4 C3 -174.31(18) . . . . ?
N2 N1 C13 C14 -91.5(3) . . . . ?
N2 N1 C13 C18 84.7(3) . . . . ?
N2 C5 C6 C7 -177.2(2) . . . . ?
N2 C5 C6 C10 2.5(2) . . . . ?
N2 C9 C10 C6 -0.7(3) . . . . ?
N2 C9 C10 C12 178.6(2) . . . . ?
C1 C2 C3 C4 74.6(3) . . . . ?
C1 C2 C3 C19 -168.24(19) . . . . ?
C2 C3 C4 O1 47.2(3) . . . . ?
C2 C3 C4 N1 -136.1(2) . . . . ?
C4 N1 N2 C5 86.9(3) . . . . ?
C4 N1 N2 C9 -87.5(3) . . . . ?
C4 N1 C13 C14 93.3(3) . . . . ?
C4 N1 C13 C18 -90.6(3) . . . . ?
C5 N2 C9 O2 -178.0(2) . . . . ?
C5 N2 C9 C10 2.4(3) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C5 C6 C10 C9 -1.2(3) . . . . ?
C5 C6 C10 C12 179.5(2) . . . . ?
C6 C7 C8 C11 -0.2(4) . . . . ?
C6 C10 C12 C11 0.4(3) . . . . ?
C7 C6 C10 C9 178.5(2) . . . . ?
C7 C6 C10 C12 -0.8(4) . . . . ?
C7 C8 C11 C12 -0.2(4) . . . . ?
C8 C11 C12 C10 0.1(4) . . . . ?
C9 N2 C5 O3 177.8(2) . . . . ?
C9 N2 C5 C6 -3.1(3) . . . . ?
C9 C10 C12 C11 -178.8(2) . . . . ?
C10 C6 C7 C8 0.6(3) . . . . ?
C13 N1 N2 C5 -89.0(3) . . . . ?
C13 N1 N2 C9 96.7(2) . . . . ?
C13 N1 C4 O1 177.7(2) . . . . ?
C13 N1 C4 C3 0.9(3) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C14 C13 C18 C17 1.1(3) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C19 C3 C4 O1 -71.2(3) . . . . ?
C19 C3 C4 N1 105.5(2) . . . . ?

_olex2_date_sample_data_collection 'Jan 9, 2015'
_olex2_date_sample_submission    'Jan 8, 2015'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10f-diastereomer
_database_code_depnum_ccdc_archive 'CCDC 1850660'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N3 O2 S'
_chemical_formula_sum            'C25 H23 N3 O2 S'
_chemical_formula_weight         429.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4533(3)
_cell_length_b                   10.2640(4)
_cell_length_c                   11.7955(4)
_cell_angle_alpha                73.208(2)
_cell_angle_beta                 79.209(2)
_cell_angle_gamma                78.894(2)
_cell_volume                     1064.58(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      66.698
_cell_measurement_theta_min      3.954
_shelx_estimated_absorpt_T_max   0.859
_shelx_estimated_absorpt_T_min   0.724
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0893 before and 0.0671 after correction. The Ratio of minimum to maximum transmission is 0.7867. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.767
_diffrn_reflns_theta_max         66.767
_diffrn_reflns_theta_min         3.953
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3282
_reflns_number_total             3743
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.5296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H1AA)=Sof(H1AB)=Sof(S1B)=Sof(C20B)=Sof(C21B)=Sof(H21B)=Sof(C25B)=
 Sof(H25B)=Sof(C22B)=Sof(H22B)=Sof(C24B)=Sof(H24B)=Sof(C23B)=Sof(H23B)=1-FVAR(1)
 Sof(S1A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21A)=Sof(C20A)=Sof(H1BC)=
 Sof(H1BD)=Sof(C25A)=Sof(H25A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1BC,H1BD), C1(H1AA,H1AB)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C5(H5), C22A(H22A), C21A(H21A), C15(H15), C6(H6), C8(H8),
 C14(H14), C13(H13), C25A(H25A), C7(H7), C23A(H23A), C24A(H24A), C21B(H21B),
 C25B(H25B), C22B(H22B), C24B(H24B), C23B(H23B)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1A S 1.12359(6) 0.48066(5) 0.35889(4) 0.02720(18) Uani 0.8919(18) 1 d . . P A
1
O1 O 0.91530(14) 0.21269(12) 0.34551(11) 0.0288(3) Uani 1 1 d . . . . .
O2 O 0.67370(14) 0.23292(13) 0.16391(11) 0.0288(3) Uani 1 1 d . . . . .
N2 N 0.63952(15) 0.31345(14) 0.33010(12) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.74961(15) 0.39510(14) 0.27632(13) 0.0217(3) Uani 1 1 d . . . . .
N3 N 0.46869(16) 0.24353(15) 0.49965(13) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.60685(19) 0.23329(17) 0.26308(15) 0.0213(4) Uani 1 1 d . . . . .
C16 C 0.41985(18) 0.16895(17) 0.43686(15) 0.0223(4) Uani 1 1 d . . . . .
C3 C 0.89146(19) 0.32764(17) 0.28018(15) 0.0214(4) Uani 1 1 d . . . . .
C17 C 0.57634(19) 0.30901(17) 0.44795(15) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.70137(19) 0.53415(17) 0.21188(16) 0.0226(4) Uani 1 1 d . . . . .
C11 C 0.48621(18) 0.15756(17) 0.32328(15) 0.0207(4) Uani 1 1 d . . . . .
C12 C 0.4379(2) 0.07520(17) 0.26665(17) 0.0258(4) Uani 1 1 d . . . . .
H12 H 0.483613 0.067495 0.191393 0.031 Uiso 1 1 calc R . . . .
C2 C 1.01078(18) 0.39795(17) 0.19313(15) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.975142 0.495789 0.161784 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7438(2) 0.64219(18) 0.23951(17) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.801636 0.624626 0.299490 0.032 Uiso 1 1 calc R . . . .
C5 C 0.6108(2) 0.55913(19) 0.12528(16) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.581860 0.486404 0.107687 0.033 Uiso 1 1 calc R . . . .
C22A C 1.0195(3) 0.8922(4) 0.2635(4) 0.0246(7) Uani 0.8919(18) 1 d . . P A 1
H22A H 0.972846 0.959164 0.302192 0.029 Uiso 0.8919(18) 1 calc R . P A 1
C21A C 1.0351(3) 0.7544(4) 0.3268(2) 0.0242(5) Uani 0.8919(18) 1 d . . P A 1
H21A H 0.997515 0.729371 0.407406 0.029 Uiso 0.8919(18) 1 calc R . P A 1
C15 C 0.3020(2) 0.09719(19) 0.49252(17) 0.0287(4) Uani 1 1 d . . . . .
H15 H 0.256102 0.103619 0.568071 0.034 Uiso 1 1 calc R . . . .
C6 C 0.5642(2) 0.6942(2) 0.06540(18) 0.0325(4) Uani 1 1 d . . . . .
H6 H 0.502058 0.712340 0.008415 0.039 Uiso 1 1 calc R . . . .
C20A C 1.1074(3) 0.6530(2) 0.2695(3) 0.0210(4) Uani 0.8919(18) 1 d . . P A 1
C8 C 0.6995(2) 0.77643(19) 0.17721(18) 0.0333(4) Uani 1 1 d . . . . .
H8 H 0.729838 0.849201 0.193695 0.040 Uiso 1 1 calc R . . . .
C18 C 0.6443(2) 0.3789(2) 0.51432(17) 0.0305(4) Uani 1 1 d . . . . .
H18A H 0.744126 0.338003 0.518181 0.046 Uiso 1 1 calc GR . . . .
H18B H 0.592624 0.368689 0.593886 0.046 Uiso 1 1 calc GR . . . .
H18C H 0.639751 0.474881 0.473550 0.046 Uiso 1 1 calc GR . . . .
C1 C 1.1447(2) 0.38164(18) 0.25358(18) 0.0293(4) Uani 1 1 d . . . . .
H1BC H 1.225757 0.407589 0.192315 0.035 Uiso 0.8919(18) 1 calc R . P A 1
H1BD H 1.169364 0.285298 0.294159 0.035 Uiso 0.8919(18) 1 calc R . P A 1
H1AA H 1.202251 0.294609 0.246347 0.035 Uiso 0.1081(18) 1 calc R . P A -1
H1AB H 1.109732 0.370573 0.338064 0.035 Uiso 0.1081(18) 1 calc R . P A -1
C14 C 0.2541(2) 0.01737(19) 0.43564(18) 0.0326(5) Uani 1 1 d . . . . .
H14 H 0.175583 -0.029092 0.472879 0.039 Uiso 1 1 calc R . . . .
C13 C 0.3225(2) 0.00564(18) 0.32267(18) 0.0308(4) Uani 1 1 d . . . . .
H13 H 0.290020 -0.049128 0.285276 0.037 Uiso 1 1 calc R . . . .
C19 C 1.0500(2) 0.32695(19) 0.09104(17) 0.0313(4) Uani 1 1 d . . . . .
H19A H 1.090377 0.232562 0.121577 0.047 Uiso 1 1 calc GR . . . .
H19B H 1.120133 0.372884 0.030424 0.047 Uiso 1 1 calc GR . . . .
H19C H 0.963894 0.330986 0.057239 0.047 Uiso 1 1 calc GR . . . .
C25A C 1.1644(2) 0.6917(3) 0.1495(3) 0.0238(5) Uani 0.8919(18) 1 d . . P A 1
H25A H 1.214516 0.625147 0.111506 0.029 Uiso 0.8919(18) 1 calc R . P A 1
C7 C 0.6102(2) 0.8018(2) 0.09048(18) 0.0350(5) Uani 1 1 d . . . . .
H7 H 0.580749 0.891939 0.048644 0.042 Uiso 1 1 calc R . . . .
C23A C 1.0735(4) 0.9301(3) 0.1426(3) 0.0258(7) Uani 0.8919(18) 1 d . . P A 1
H23A H 1.060458 1.022099 0.099731 0.031 Uiso 0.8919(18) 1 calc R . P A 1
C24A C 1.1472(3) 0.8298(4) 0.0856(2) 0.0260(5) Uani 0.8919(18) 1 d . . P A 1
H24A H 1.184801 0.855092 0.004981 0.031 Uiso 0.8919(18) 1 calc R . P A 1
S1B S 1.2591(6) 0.4943(6) 0.2162(5) 0.0476(17) Uiso 0.1081(18) 1 d . . P A -1
C20B C 1.163(2) 0.663(2) 0.219(3) 0.016(4) Uiso 0.1081(18) 1 d . . P A 2
C21B C 1.083(3) 0.687(3) 0.314(2) 0.028(6) Uiso 0.1081(18) 1 d . . P A 2
H21B H 1.066426 0.614239 0.380846 0.034 Uiso 0.1081(18) 1 calc R . P A 2
C25B C 1.168(2) 0.768(4) 0.118(2) 0.022(5) Uiso 0.1081(18) 1 d . . P A 2
H25B H 1.214621 0.750244 0.045801 0.026 Uiso 0.1081(18) 1 calc R . P A 2
C22B C 1.023(3) 0.817(4) 0.318(3) 0.035(7) Uiso 0.1081(18) 1 d . . P A 2
H22B H 0.979194 0.833800 0.390709 0.042 Uiso 0.1081(18) 1 calc R . P A 2
C24B C 1.108(3) 0.896(3) 0.120(3) 0.020(6) Uiso 0.1081(18) 1 d . . P A 2
H24B H 1.123463 0.968982 0.053231 0.024 Uiso 0.1081(18) 1 calc R . P A 2
C23B C 1.025(4) 0.917(3) 0.221(3) 0.028(8) Uiso 0.1081(18) 1 d . . P A 2
H23B H 0.971055 1.003063 0.221983 0.033 Uiso 0.1081(18) 1 calc R . P A 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
S1A C20A 1.773(2) . ?
S1A C1 1.782(2) . ?
S1A S1B 1.902(6) . ?
O1 C3 1.214(2) . ?
O2 C10 1.222(2) . ?
N2 N1 1.4034(19) . ?
N2 C10 1.401(2) . ?
N2 C17 1.398(2) . ?
N1 C3 1.388(2) . ?
N1 C4 1.441(2) . ?
N3 C16 1.393(2) . ?
N3 C17 1.286(2) . ?
C10 C11 1.459(2) . ?
C16 C11 1.396(2) . ?
C16 C15 1.406(3) . ?
C3 C2 1.516(2) . ?
C17 C18 1.493(2) . ?
C4 C9 1.388(2) . ?
C4 C5 1.390(3) . ?
C11 C12 1.400(2) . ?
C12 C13 1.376(3) . ?
C2 C1 1.525(2) . ?
C2 C19 1.534(3) . ?
C9 C8 1.386(3) . ?
C5 C6 1.389(3) . ?
C22A C21A 1.389(4) . ?
C22A C23A 1.389(5) . ?
C21A C20A 1.402(4) . ?
C15 C14 1.378(3) . ?
C6 C7 1.386(3) . ?
C20A C25A 1.386(4) . ?
C20A S1B 2.112(7) . ?
C8 C7 1.383(3) . ?
C1 S1B 1.646(6) . ?
C14 C13 1.396(3) . ?
C25A C24A 1.395(3) . ?
C25A S1B 2.042(7) . ?
C23A C24A 1.394(4) . ?
C20B C21B 1.29(3) . ?
C20B C25B 1.36(3) . ?
C21B C22B 1.35(4) . ?
C25B C24B 1.33(4) . ?
C22B C23B 1.30(4) . ?
C24B C23B 1.35(4) . ?

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
C20A S1A C1 103.73(14) . . ?
C20A S1A S1B 70.0(2) . . ?
C1 S1A S1B 52.97(18) . . ?
C10 N2 N1 116.67(14) . . ?
C17 N2 N1 119.31(14) . . ?
C17 N2 C10 123.88(14) . . ?
N2 N1 C4 115.70(13) . . ?
C3 N1 N2 115.93(13) . . ?
C3 N1 C4 127.92(14) . . ?
C17 N3 C16 117.97(15) . . ?
O2 C10 N2 121.17(15) . . ?
O2 C10 C11 125.95(16) . . ?
N2 C10 C11 112.86(14) . . ?
N3 C16 C11 123.04(16) . . ?
N3 C16 C15 118.41(16) . . ?
C11 C16 C15 118.50(17) . . ?
O1 C3 N1 120.10(15) . . ?
O1 C3 C2 122.29(15) . . ?
N1 C3 C2 117.41(14) . . ?
N2 C17 C18 116.80(15) . . ?
N3 C17 N2 122.33(16) . . ?
N3 C17 C18 120.81(16) . . ?
C9 C4 N1 119.05(15) . . ?
C9 C4 C5 120.77(16) . . ?
C5 C4 N1 120.17(15) . . ?
C16 C11 C10 119.33(15) . . ?
C16 C11 C12 120.81(16) . . ?
C12 C11 C10 119.86(16) . . ?
C13 C12 C11 119.81(18) . . ?
C3 C2 C1 110.77(14) . . ?
C3 C2 C19 106.51(14) . . ?
C1 C2 C19 109.60(15) . . ?
C8 C9 C4 119.63(17) . . ?
C6 C5 C4 119.12(17) . . ?
C21A C22A C23A 120.2(3) . . ?
C22A C21A C20A 120.2(2) . . ?
C14 C15 C16 120.32(18) . . ?
C7 C6 C5 120.06(17) . . ?
S1A C20A S1B 57.84(17) . . ?
C21A C20A S1A 116.6(3) . . ?
C21A C20A S1B 163.8(2) . . ?
C25A C20A S1A 124.0(3) . . ?
C25A C20A C21A 119.4(2) . . ?
C25A C20A S1B 67.8(3) . . ?
C7 C8 C9 119.82(18) . . ?
C2 C1 S1A 114.68(13) . . ?
C2 C1 S1B 124.1(2) . . ?
S1B C1 S1A 67.3(2) . . ?
C15 C14 C13 120.61(17) . . ?
C12 C13 C14 119.95(18) . . ?
C20A C25A C24A 120.4(2) . . ?
C20A C25A S1B 73.2(3) . . ?
C24A C25A S1B 160.9(3) . . ?
C8 C7 C6 120.56(17) . . ?
C22A C23A C24A 119.8(2) . . ?
C23A C24A C25A 120.0(2) . . ?
S1A S1B C20A 52.12(17) . . ?
S1A S1B C25A 90.2(2) . . ?
C1 S1B S1A 59.8(2) . . ?
C1 S1B C20A 95.4(3) . . ?
C1 S1B C25A 113.5(3) . . ?
C25A S1B C20A 38.95(14) . . ?
C21B C20B C25B 118(2) . . ?
C20B C21B C22B 121(3) . . ?
C24B C25B C20B 121(2) . . ?
C23B C22B C21B 121(3) . . ?
C25B C24B C23B 119(2) . . ?
C22B C23B C24B 119(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10f-diastereomer_2
_database_code_depnum_ccdc_archive 'CCDC 1850661'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H23 N3 O2 S)'
_chemical_formula_sum            'C50 H46 N6 O4 S2'
_chemical_formula_weight         859.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.6439(3)
_cell_length_b                   12.4156(4)
_cell_length_c                   40.7123(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.515(2)
_cell_angle_gamma                90
_cell_volume                     4349.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6859
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      66.328
_cell_measurement_theta_min      3.724
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    1.538
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1029 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.8083. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            37523
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.766
_diffrn_reflns_theta_max         66.766
_diffrn_reflns_theta_min         3.723
_diffrn_ambient_temperature      109.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5761
_reflns_number_total             7649
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.079
_refine_diff_density_min         -1.057
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         7649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.1048
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1483P)²+13.3561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2902
_refine_ls_wR_factor_ref         0.3073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C017(H017), C01A(H01A)
2.b Secondary CH2 refined with riding coordinates:
 C01D(H01E,H01F), C01E(H01K,H01L)
2.c Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C018(H018), C019(H019),
 C01G(H01N), C01H(H01O), C01I(H01P), C01J(H01J), C01K(H01Q), C01L(H01R),
 C01M(H01M), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C00K(H00D,H00E,H00F), C00V(H00A,H00B,H00C), C01B(H01B,H01C,H01D), C01C(H01G,
 H01H,H01I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S001 S 0.3566(4) 0.3967(3) 0.51986(6) 0.1201(11) Uani 1 1 d . . . . .
S002 S 0.8381(4) 0.9244(3) 0.53389(7) 0.1184(12) Uani 1 1 d . . . . .
O003 O 0.5853(3) 0.2854(2) 0.64979(8) 0.0290(7) Uani 1 1 d . . . . .
O004 O 1.0761(3) 0.9611(3) 0.66196(9) 0.0320(7) Uani 1 1 d . . . . .
O005 O 1.0712(4) 0.7205(3) 0.62603(8) 0.0326(7) Uani 1 1 d . . . . .
O006 O 0.5816(4) 0.5326(3) 0.62233(8) 0.0329(7) Uani 1 1 d . . . . .
N007 N 0.4639(4) 0.4317(3) 0.67003(9) 0.0223(7) Uani 1 1 d . . . . .
N008 N 0.3766(4) 0.4428(3) 0.63929(9) 0.0232(8) Uani 1 1 d . . . . .
N009 N 1.0299(4) 0.7122(3) 0.72625(9) 0.0240(8) Uani 1 1 d . . . . .
N00A N 0.5379(4) 0.5094(3) 0.72179(9) 0.0247(8) Uani 1 1 d . . . . .
N00B N 0.9581(4) 0.8066(3) 0.67706(9) 0.0226(7) Uani 1 1 d . . . . .
N00C N 0.8694(4) 0.8054(3) 0.64629(9) 0.0230(8) Uani 1 1 d . . . . .
C00D C 0.5736(5) 0.3473(3) 0.67286(11) 0.0235(9) Uani 1 1 d . . . . .
C00E C 1.0663(4) 0.8902(3) 0.68274(11) 0.0240(9) Uani 1 1 d . . . . .
C00F C 0.2281(5) 0.3881(4) 0.63526(11) 0.0238(9) Uani 1 1 d . . . . .
C00G C 0.9490(4) 0.7194(3) 0.69818(11) 0.0224(9) Uani 1 1 d . . . . .
C00H C 0.4551(4) 0.5112(3) 0.69397(11) 0.0223(9) Uani 1 1 d . . . . .
C00I C 1.1570(5) 0.8830(4) 0.71457(12) 0.0262(9) Uani 1 1 d . . . . .
C00J C 1.1344(4) 0.7954(4) 0.73520(11) 0.0249(9) Uani 1 1 d . . . . .
C00K C 0.8388(5) 0.6310(3) 0.68710(12) 0.0265(9) Uani 1 1 d . . . . .
H00D H 0.850858 0.571293 0.702885 0.040 Uiso 1 1 calc GR . . . .
H00E H 0.861426 0.605595 0.665276 0.040 Uiso 1 1 calc GR . . . .
H00F H 0.731982 0.658131 0.685875 0.040 Uiso 1 1 calc GR . . . .
C00L C 0.7207(5) 0.8588(3) 0.64477(11) 0.0246(9) Uani 1 1 d . . . . .
C00M C 0.4545(5) 0.4930(4) 0.61546(12) 0.0294(10) Uani 1 1 d . . . . .
C00N C 0.6415(5) 0.4243(3) 0.72815(11) 0.0247(9) Uani 1 1 d . . . . .
C00O C 1.2213(5) 0.7894(4) 0.76623(12) 0.0303(10) Uani 1 1 d . . . . .
H00O H 1.208526 0.730272 0.780517 0.036 Uiso 1 1 calc R . . . .
C00P C 1.2630(5) 0.9647(4) 0.72474(13) 0.0322(11) Uani 1 1 d . . . . .
H00P H 1.276733 1.024521 0.710774 0.039 Uiso 1 1 calc R . . . .
C00Q C 0.7128(5) 0.9672(4) 0.65269(13) 0.0328(11) Uani 1 1 d . . . . .
H00Q H 0.805241 1.007501 0.657968 0.039 Uiso 1 1 calc R . . . .
C00R C 0.0937(5) 0.4472(4) 0.63005(12) 0.0293(10) Uani 1 1 d . . . . .
H00R H 0.098282 0.523373 0.628282 0.035 Uiso 1 1 calc R . . . .
C00S C 0.6614(5) 0.3428(3) 0.70500(11) 0.0244(9) Uani 1 1 d . . . . .
C00T C 0.9441(5) 0.7644(3) 0.62049(12) 0.0265(9) Uani 1 1 d . . . . .
C00U C 0.7309(5) 0.4202(4) 0.75884(12) 0.0311(10) Uani 1 1 d . . . . .
H00U H 0.720782 0.475258 0.774681 0.037 Uiso 1 1 calc R . . . .
C00V C 0.3429(5) 0.6013(4) 0.68597(12) 0.0279(9) Uani 1 1 d . . . . .
H00A H 0.366222 0.636143 0.665413 0.042 Uiso 1 1 calc GR . . . .
H00B H 0.352122 0.654157 0.703933 0.042 Uiso 1 1 calc GR . . . .
H00C H 0.236755 0.572693 0.683316 0.042 Uiso 1 1 calc GR . . . .
C00W C 0.7650(5) 0.2581(4) 0.71285(13) 0.0306(10) Uani 1 1 d . . . . .
H00W H 0.777220 0.202874 0.697151 0.037 Uiso 1 1 calc R . . . .
C00X C 0.5869(5) 0.8002(4) 0.63653(11) 0.0288(10) Uani 1 1 d . . . . .
H00X H 0.593096 0.725949 0.631197 0.035 Uiso 1 1 calc R . . . .
C00Y C 1.3263(5) 0.8714(4) 0.77568(13) 0.0346(11) Uani 1 1 d . . . . .
H00Y H 1.384504 0.868009 0.796668 0.042 Uiso 1 1 calc R . . . .
C00Z C 0.2236(5) 0.2764(4) 0.63812(12) 0.0309(10) Uani 1 1 d . . . . .
H00Z H 0.317077 0.235990 0.641406 0.037 Uiso 1 1 calc R . . . .
C010 C 0.8321(5) 0.3373(4) 0.76595(12) 0.0346(11) Uani 1 1 d . . . . .
H010 H 0.892106 0.335910 0.786756 0.042 Uiso 1 1 calc R . . . .
C011 C 0.4351(5) 0.9579(4) 0.64474(14) 0.0387(12) Uani 1 1 d . . . . .
H011 H 0.336925 0.991995 0.645111 0.046 Uiso 1 1 calc R . . . .
C012 C 0.8499(5) 0.2545(4) 0.74344(13) 0.0338(11) Uani 1 1 d . . . . .
H012 H 0.919152 0.196477 0.749035 0.041 Uiso 1 1 calc R . . . .
C013 C 1.3471(5) 0.9573(4) 0.75512(13) 0.0366(12) Uani 1 1 d . . . . .
H013 H 1.420130 1.011927 0.761981 0.044 Uiso 1 1 calc R . . . .
C014 C 0.4422(5) 0.8507(4) 0.63609(13) 0.0333(11) Uani 1 1 d . . . . .
H014 H 0.349602 0.811496 0.629897 0.040 Uiso 1 1 calc R . . . .
C015 C -0.0492(5) 0.3948(4) 0.62739(12) 0.0328(10) Uani 1 1 d . . . . .
H015 H -0.142465 0.435148 0.623375 0.039 Uiso 1 1 calc R . . . .
C016 C 0.0803(6) 0.2251(4) 0.63609(14) 0.0383(12) Uani 1 1 d . . . . .
H016 H 0.075282 0.149107 0.638482 0.046 Uiso 1 1 calc R . . . .
C017 C 0.8645(6) 0.7780(4) 0.58630(13) 0.0400(12) Uani 1 1 d . . . . .
H017 H 0.752017 0.791710 0.588570 0.048 Uiso 1 1 calc R . . . .
C018 C 0.5692(6) 1.0160(4) 0.65282(14) 0.0402(12) Uani 1 1 d . . . . .
H018 H 0.562931 1.089985 0.658523 0.048 Uiso 1 1 calc R . . . .
C019 C -0.0556(5) 0.2846(4) 0.63056(13) 0.0363(11) Uani 1 1 d . . . . .
H019 H -0.153414 0.249135 0.628962 0.044 Uiso 1 1 calc R . . . .
C01A C 0.3728(6) 0.4971(4) 0.58082(12) 0.0389(12) Uani 1 1 d . . . . .
H01A H 0.261935 0.475353 0.581836 0.047 Uiso 1 1 calc R . . . .
C01B C 0.3757(10) 0.6104(6) 0.56736(17) 0.070(2) Uani 1 1 d . . . . .
H01B H 0.320994 0.658763 0.581364 0.104 Uiso 1 1 calc GR . . . .
H01C H 0.324263 0.611788 0.544832 0.104 Uiso 1 1 calc GR . . . .
H01D H 0.483663 0.634277 0.567145 0.104 Uiso 1 1 calc GR . . . .
C01C C 0.8740(9) 0.6761(7) 0.56656(17) 0.075(2) Uani 1 1 d . . . . .
H01G H 0.982645 0.661971 0.562951 0.112 Uiso 1 1 calc GR . . . .
H01H H 0.812296 0.684261 0.545230 0.112 Uiso 1 1 calc GR . . . .
H01I H 0.833391 0.615800 0.578666 0.112 Uiso 1 1 calc GR . . . .
C01D C 0.4489(12) 0.4158(8) 0.5608(2) 0.093(3) Uani 1 1 d . . . . .
H01E H 0.451063 0.345859 0.572507 0.112 Uiso 1 1 calc R . . . .
H01F H 0.557870 0.438057 0.559216 0.112 Uiso 1 1 calc R . . . .
C01E C 0.9316(11) 0.8810(8) 0.5734(2) 0.091(3) Uani 1 1 d . . . . .
H01K H 1.043641 0.869809 0.571252 0.109 Uiso 1 1 calc R . . . .
H01L H 0.922375 0.939057 0.589721 0.109 Uiso 1 1 calc R . . . .
C01F C 0.6402(15) 0.9533(11) 0.5432(3) 0.114(4) Uani 1 1 d . . . . .
C01G C 0.4522(14) 1.0668(10) 0.5678(3) 0.107(4) Uani 1 1 d . . . . .
H01N H 0.426010 1.126478 0.580793 0.129 Uiso 1 1 calc R . . . .
C01H C 0.3381(14) 0.9972(13) 0.5526(4) 0.125(5) Uani 1 1 d . . . . .
H01O H 0.232413 1.013431 0.555037 0.150 Uiso 1 1 calc R . . . .
C01I C 0.6059(15) 1.0428(11) 0.5628(3) 0.121(4) Uani 1 1 d . . . . .
H01P H 0.687830 1.086787 0.572508 0.145 Uiso 1 1 calc R . . . .
C01J C -0.1483(17) 0.2965(11) 0.5360(3) 0.120(4) Uani 1 1 d . . . . .
H01J H -0.251489 0.273291 0.538207 0.144 Uiso 1 1 calc R . . . .
C01K C 0.3687(16) 0.9066(13) 0.5343(3) 0.126(5) Uani 1 1 d . . . . .
H01Q H 0.286782 0.860563 0.525666 0.151 Uiso 1 1 calc R . . . .
C01L C 0.5156(17) 0.8857(13) 0.5290(3) 0.136(5) Uani 1 1 d . . . . .
H01R H 0.538397 0.825737 0.515821 0.164 Uiso 1 1 calc R . . . .
C01M C -0.0312(16) 0.2254(16) 0.5373(4) 0.157(7) Uani 1 1 d . . . . .
H01M H -0.054060 0.153150 0.542788 0.188 Uiso 1 1 calc R . . . .
C4 C 0.1547(13) 0.3555(14) 0.5278(3) 0.126(5) Uani 1 1 d . . . . .
C5 C -0.1151(15) 0.4072(13) 0.5312(5) 0.187(9) Uani 1 1 d . . . . .
H5 H -0.194023 0.460714 0.529676 0.224 Uiso 1 1 calc R . . . .
C6 C 0.119(3) 0.2482(15) 0.5315(3) 0.175(8) Uani 1 1 d . . . . .
H6 H 0.194265 0.193109 0.530015 0.210 Uiso 1 1 calc R . . . .
C7 C 0.0410(15) 0.4324(13) 0.5289(5) 0.186(9) Uani 1 1 d . . . . .
H7 H 0.069939 0.506055 0.527998 0.223 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
S001 C01D 1.792(8) . ?
S001 C4 1.876(14) . ?
S002 C01E 1.811(8) . ?
S002 C01F 1.822(11) . ?
O003 C00D 1.225(6) . ?
O004 C00E 1.229(5) . ?
O005 C00T 1.228(5) . ?
O006 C00M 1.212(6) . ?
N007 N008 1.405(5) . ?
N007 C00D 1.410(5) . ?
N007 C00H 1.394(6) . ?
N008 C00F 1.447(5) . ?
N008 C00M 1.382(6) . ?
N009 C00G 1.284(6) . ?
N009 C00J 1.398(6) . ?
N00A C00H 1.281(6) . ?
N00A C00N 1.393(6) . ?
N00B N00C 1.405(5) . ?
N00B C00E 1.402(5) . ?
N00B C00G 1.389(6) . ?
N00C C00L 1.443(5) . ?
N00C C00T 1.382(6) . ?
C00D C00S 1.450(6) . ?
C00E C00I 1.451(6) . ?
C00F C00R 1.373(6) . ?
C00F C00Z 1.392(6) . ?
C00G C00K 1.494(6) . ?
C00H C00V 1.496(6) . ?
C00I C00J 1.399(7) . ?
C00I C00P 1.402(6) . ?
C00J C00O 1.408(6) . ?
C00L C00Q 1.387(6) . ?
C00L C00X 1.381(6) . ?
C00M C01A 1.516(7) . ?
C00N C00S 1.405(6) . ?
C00N C00U 1.405(6) . ?
C00O C00Y 1.392(7) . ?
C00P C013 1.376(7) . ?
C00Q C018 1.381(7) . ?
C00R C015 1.391(7) . ?
C00S C00W 1.398(6) . ?
C00T C017 1.502(7) . ?
C00U C010 1.363(7) . ?
C00W C012 1.384(7) . ?
C00X C014 1.397(6) . ?
C00Y C013 1.379(8) . ?
C00Z C016 1.388(7) . ?
C010 C012 1.396(8) . ?
C011 C014 1.380(7) . ?
C011 C018 1.378(7) . ?
C015 C019 1.376(7) . ?
C016 C019 1.388(7) . ?
C017 C01C 1.505(8) . ?
C017 C01E 1.519(10) . ?
C01A C01B 1.512(9) . ?
C01A C01D 1.490(9) . ?
C01F C01I 1.417(17) . ?
C01F C01L 1.441(19) . ?
C01G C01H 1.409(18) . ?
C01G C01I 1.396(15) . ?
C01H C01K 1.39(2) . ?
C01J C01M 1.340(18) . ?
C01J C5 1.422(19) . ?
C01K C01L 1.334(17) . ?
C01M C6 1.37(2) . ?
C4 C6 1.38(2) . ?
C4 C7 1.374(17) . ?
C5 C7 1.397(19) . ?

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
C01D S001 C4 102.3(5) . . ?
C01E S002 C01F 102.9(5) . . ?
N008 N007 C00D 116.4(3) . . ?
C00H N007 N008 119.5(3) . . ?
C00H N007 C00D 123.4(4) . . ?
N007 N008 C00F 116.7(3) . . ?
C00M N008 N007 114.4(3) . . ?
C00M N008 C00F 128.2(4) . . ?
C00G N009 C00J 117.6(4) . . ?
C00H N00A C00N 118.2(4) . . ?
C00E N00B N00C 117.0(3) . . ?
C00G N00B N00C 119.0(3) . . ?
C00G N00B C00E 123.5(4) . . ?
N00B N00C C00L 116.2(3) . . ?
C00T N00C N00B 115.3(3) . . ?
C00T N00C C00L 128.0(4) . . ?
O003 C00D N007 120.5(4) . . ?
O003 C00D C00S 126.4(4) . . ?
N007 C00D C00S 113.1(4) . . ?
O004 C00E N00B 120.4(4) . . ?
O004 C00E C00I 126.3(4) . . ?
N00B C00E C00I 113.3(4) . . ?
C00R C00F N008 119.7(4) . . ?
C00R C00F C00Z 121.0(4) . . ?
C00Z C00F N008 119.3(4) . . ?
N009 C00G N00B 123.1(4) . . ?
N009 C00G C00K 119.6(4) . . ?
N00B C00G C00K 117.2(4) . . ?
N007 C00H C00V 117.1(4) . . ?
N00A C00H N007 122.8(4) . . ?
N00A C00H C00V 120.1(4) . . ?
C00J C00I C00E 119.3(4) . . ?
C00J C00I C00P 120.6(4) . . ?
C00P C00I C00E 120.1(4) . . ?
N009 C00J C00I 122.8(4) . . ?
N009 C00J C00O 118.1(4) . . ?
C00I C00J C00O 119.1(4) . . ?
C00Q C00L N00C 120.0(4) . . ?
C00X C00L N00C 119.3(4) . . ?
C00X C00L C00Q 120.6(4) . . ?
O006 C00M N008 120.9(4) . . ?
O006 C00M C01A 122.1(4) . . ?
N008 C00M C01A 116.9(4) . . ?
N00A C00N C00S 122.7(4) . . ?
N00A C00N C00U 118.8(4) . . ?
C00S C00N C00U 118.5(4) . . ?
C00Y C00O C00J 119.1(5) . . ?
C013 C00P C00I 119.4(5) . . ?
C018 C00Q C00L 119.4(4) . . ?
C00F C00R C015 119.6(4) . . ?
C00N C00S C00D 119.4(4) . . ?
C00W C00S C00D 120.3(4) . . ?
C00W C00S C00N 120.4(4) . . ?
O005 C00T N00C 119.9(4) . . ?
O005 C00T C017 122.8(4) . . ?
N00C C00T C017 117.2(4) . . ?
C010 C00U C00N 120.2(5) . . ?
C012 C00W C00S 120.2(5) . . ?
C00L C00X C014 119.7(4) . . ?
C013 C00Y C00O 121.1(5) . . ?
C016 C00Z C00F 119.0(4) . . ?
C00U C010 C012 121.7(5) . . ?
C018 C011 C014 120.6(4) . . ?
C00W C012 C010 119.0(4) . . ?
C00P C013 C00Y 120.6(4) . . ?
C011 C014 C00X 119.4(4) . . ?
C019 C015 C00R 120.1(4) . . ?
C019 C016 C00Z 120.1(5) . . ?
C00T C017 C01C 110.9(5) . . ?
C00T C017 C01E 105.0(5) . . ?
C01C C017 C01E 118.7(6) . . ?
C011 C018 C00Q 120.3(5) . . ?
C015 C019 C016 120.2(4) . . ?
C01B C01A C00M 110.2(5) . . ?
C01D C01A C00M 107.2(5) . . ?
C01D C01A C01B 114.1(6) . . ?
C01A C01D S001 114.7(6) . . ?
C017 C01E S002 113.9(6) . . ?
C01I C01F S002 121.5(12) . . ?
C01I C01F C01L 119.5(12) . . ?
C01L C01F S002 118.9(11) . . ?
C01I C01G C01H 116.1(13) . . ?
C01K C01H C01G 124.9(13) . . ?
C01G C01I C01F 120.3(14) . . ?
C01M C01J C5 118.7(15) . . ?
C01L C01K C01H 118.5(16) . . ?
C01K C01L C01F 120.7(17) . . ?
C01J C01M C6 125.5(18) . . ?
C6 C4 S001 120.3(12) . . ?
C7 C4 S001 119.7(14) . . ?
C7 C4 C6 120.0(15) . . ?
C7 C5 C01J 115.7(14) . . ?
C01M C6 C4 116.3(16) . . ?
C4 C7 C5 123.0(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1850655'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2015-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H14 N2 O2'
_chemical_formula_sum            'C12 H15 N2 O2'
_chemical_formula_weight         219.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4560(4)
_cell_length_b                   10.7425(5)
_cell_length_c                   11.1944(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.483(2)
_cell_angle_gamma                90
_cell_volume                     1121.60(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.663
_cell_measurement_theta_min      4.742
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8338.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10507
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.658
_diffrn_reflns_theta_min         4.741
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1793
_reflns_number_total             1980
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.3337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1192
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.15961(11) 0.41479(10) 0.58374(10) 0.0334(3) Uani 1 1 d . . . . .
O2 O -0.08352(11) 0.05298(9) 0.61457(8) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.06152(12) 0.21983(10) 0.59381(10) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.17412(13) 0.15496(11) 0.55638(11) 0.0259(3) Uani 1 1 d . . . . .
C0AA C -0.13961(18) 0.24306(15) 0.80608(13) 0.0329(4) Uani 1 1 d . . . . .
H0AA H -0.1786 0.1610 0.8208 0.049 Uiso 1 1 calc GR . . . .
H0AB H -0.1942 0.3076 0.8404 0.049 Uiso 1 1 calc GR . . . .
H0AC H -0.0388 0.2472 0.8444 0.049 Uiso 1 1 calc GR . . . .
C2 C -0.15099(16) 0.26404(13) 0.66887(12) 0.0239(3) Uani 1 1 d . . . . .
C3 C -0.05956(14) 0.16426(12) 0.62321(11) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.28327(15) 0.11428(13) 0.65133(13) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.38042(16) 0.02596(14) 0.62311(15) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.3696 -0.0083 0.5439 0.038 Uiso 1 1 calc R . . . .
C6 C 0.49332(17) -0.01183(15) 0.71132(17) 0.0384(4) Uani 1 1 d . . . . .
H6 H 0.5595 -0.0721 0.6919 0.046 Uiso 1 1 calc R . . . .
C7 C 0.51047(17) 0.03755(15) 0.82754(16) 0.0386(4) Uani 1 1 d . . . . .
H7 H 0.5884 0.0121 0.8873 0.046 Uiso 1 1 calc R . . . .
C8 C 0.06209(15) 0.34974(13) 0.60348(12) 0.0253(3) Uani 1 1 d . . . . .
C9 C -0.07754(16) 0.38588(13) 0.64125(13) 0.0281(3) Uani 1 1 d . . . . .
H9A H -0.1384 0.4319 0.5753 0.034 Uiso 1 1 calc R . . . .
H9B H -0.0603 0.4396 0.7141 0.034 Uiso 1 1 calc R . . . .
C10 C -0.30693(16) 0.25468(15) 0.60625(13) 0.0299(4) Uani 1 1 d . . . . .
H10A H -0.3116 0.2644 0.5186 0.045 Uiso 1 1 calc GR . . . .
H10B H -0.3634 0.3204 0.6367 0.045 Uiso 1 1 calc GR . . . .
H10C H -0.3457 0.1732 0.6233 0.045 Uiso 1 1 calc GR . . . .
C11 C 0.29943(15) 0.16345(14) 0.76752(13) 0.0291(4) Uani 1 1 d . . . . .
H11 H 0.2334 0.2237 0.7873 0.035 Uiso 1 1 calc R . . . .
C12 C 0.41279(16) 0.12409(15) 0.85499(14) 0.0348(4) Uani 1 1 d . . . . .
H12 H 0.4230 0.1573 0.9346 0.042 Uiso 1 1 calc R . . . .
H2 H 0.140(2) 0.0955(18) 0.5059(18) 0.042 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
O1 C8 1.2061(17) . ?
O2 C3 1.2176(16) . ?
N1 N2 1.3935(16) . ?
N1 C3 1.3783(17) . ?
N1 C8 1.3997(18) . ?
N2 C4 1.4229(18) . ?
N2 H2 0.88(2) . ?
C0AA H0AA 0.9800 . ?
C0AA H0AB 0.9800 . ?
C0AA H0AC 0.9800 . ?
C0AA C2 1.5386(18) . ?
C2 C3 1.5177(19) . ?
C2 C9 1.5368(19) . ?
C2 C10 1.528(2) . ?
C4 C5 1.393(2) . ?
C4 C11 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(3) . ?
C7 H7 0.9500 . ?
C7 C12 1.380(2) . ?
C8 C9 1.502(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.393(2) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 121.90(11) . . ?
C3 N1 N2 124.13(11) . . ?
C3 N1 C8 113.96(11) . . ?
N1 N2 C4 115.16(11) . . ?
N1 N2 H2 109.6(12) . . ?
C4 N2 H2 113.8(13) . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C2 C0AA H0AA 109.5 . . ?
C2 C0AA H0AB 109.5 . . ?
C2 C0AA H0AC 109.5 . . ?
C3 C2 C0AA 106.42(11) . . ?
C3 C2 C9 103.44(11) . . ?
C3 C2 C10 111.05(11) . . ?
C9 C2 C0AA 111.47(12) . . ?
C10 C2 C0AA 110.60(12) . . ?
C10 C2 C9 113.44(12) . . ?
O2 C3 N1 123.87(13) . . ?
O2 C3 C2 127.69(13) . . ?
N1 C3 C2 108.43(11) . . ?
C5 C4 N2 117.66(13) . . ?
C11 C4 N2 122.49(13) . . ?
C11 C4 C5 119.78(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.73(15) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.74(15) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.4 . . ?
C12 C7 C6 119.11(14) . . ?
C12 C7 H7 120.4 . . ?
O1 C8 N1 123.84(13) . . ?
O1 C8 C9 129.48(13) . . ?
N1 C8 C9 106.68(11) . . ?
C2 C9 H9A 110.4 . . ?
C2 C9 H9B 110.4 . . ?
C8 C9 C2 106.49(11) . . ?
C8 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 120.1 . . ?
C4 C11 C12 119.74(14) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.90(15) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?

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
O1 C8 C9 C2 -172.87(13) . . . . ?
N1 N2 C4 C5 165.68(12) . . . . ?
N1 N2 C4 C11 -17.39(19) . . . . ?
N1 C8 C9 C2 7.25(14) . . . . ?
N2 N1 C3 O2 -3.27(19) . . . . ?
N2 N1 C3 C2 175.56(11) . . . . ?
N2 N1 C8 O1 -2.0(2) . . . . ?
N2 N1 C8 C9 177.91(11) . . . . ?
N2 C4 C5 C6 176.67(13) . . . . ?
N2 C4 C11 C12 -176.83(13) . . . . ?
C0AA C2 C3 O2 70.31(17) . . . . ?
C0AA C2 C3 N1 -108.46(13) . . . . ?
C0AA C2 C9 C8 104.21(13) . . . . ?
C3 N1 N2 C4 -88.39(15) . . . . ?
C3 N1 C8 O1 178.63(12) . . . . ?
C3 N1 C8 C9 -1.48(15) . . . . ?
C3 C2 C9 C8 -9.76(14) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C4 C11 C12 C7 0.6(2) . . . . ?
C5 C4 C11 C12 0.0(2) . . . . ?
C5 C6 C7 C12 0.7(2) . . . . ?
C6 C7 C12 C11 -1.0(2) . . . . ?
C8 N1 N2 C4 92.29(15) . . . . ?
C8 N1 C3 O2 176.11(12) . . . . ?
C8 N1 C3 C2 -5.06(14) . . . . ?
C9 C2 C3 O2 -172.13(13) . . . . ?
C9 C2 C3 N1 9.10(13) . . . . ?
C10 C2 C3 O2 -50.12(18) . . . . ?
C10 C2 C3 N1 131.11(12) . . . . ?
C10 C2 C9 C8 -130.16(12) . . . . ?
C11 C4 C5 C6 -0.3(2) . . . . ?

_olex2_date_sample_data_collection 2015-01-09
_olex2_date_sample_submission    2015-01-08
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1850658'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2022(6)
_cell_length_b                   8.6904(6)
_cell_length_c                   12.6628(10)
_cell_angle_alpha                87.880(3)
_cell_angle_beta                 75.115(4)
_cell_angle_gamma                64.061(3)
_cell_volume                     781.49(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6731
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.493
_cell_measurement_theta_min      3.626
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0971 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.8173.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9220
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.678
_diffrn_reflns_theta_min         3.625
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2400
_reflns_number_total             2666
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C14(H14), C15(H15), C18(H18), C19(H19)
2.b X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.16518(15) 0.81169(14) 0.92848(9) 0.0270(3) Uani 1 1 d . . . . .
O2 O 0.47914(15) 0.67150(13) 0.65063(9) 0.0301(3) Uani 1 1 d . . . . .
O3 O 0.60638(15) 0.95526(14) 0.70691(9) 0.0279(3) Uani 1 1 d . . . . .
N1 N 0.26144(17) 0.93973(15) 0.72285(10) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.34971(17) 0.91539(15) 0.80634(10) 0.0199(3) Uani 1 1 d . . . . .
C1 C -0.0416(2) 1.45793(19) 0.67319(13) 0.0257(4) Uani 1 1 d . . . . .
H1 H -0.1088 1.5729 0.6628 0.031 Uiso 1 1 calc R . . . .
C2 C -0.1012(2) 1.3917(2) 0.76878(14) 0.0265(4) Uani 1 1 d . . . . .
H2 H -0.2076 1.4631 0.8227 0.032 Uiso 1 1 calc R . . . .
C3 C -0.0035(2) 1.22018(19) 0.78447(13) 0.0235(3) Uani 1 1 d . . . . .
H3 H -0.0439 1.1757 0.8483 0.028 Uiso 1 1 calc R . . . .
C4 C 0.1556(2) 1.11580(18) 0.70347(12) 0.0198(3) Uani 1 1 d . . . . .
C5 C 0.3046(2) 0.83463(18) 0.89990(12) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.4623(2) 0.78844(18) 0.95093(12) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.4884(2) 0.70967(19) 1.04603(12) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.3985 0.6796 1.0894 0.027 Uiso 1 1 calc R . . . .
C8 C 0.6530(2) 0.67608(18) 1.07579(12) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.6865(2) 0.5918(2) 1.17897(13) 0.0274(4) Uani 1 1 d . . . . .
H9A H 0.5918 0.5537 1.2093 0.041 Uiso 1 1 calc GR . . . .
H9B H 0.6805 0.6727 1.2312 0.041 Uiso 1 1 calc GR . . . .
H9C H 0.8085 0.4950 1.1624 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.3370(2) 0.79824(19) 0.64638(12) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.2264(2) 0.80759(19) 0.56738(12) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.3368(2) 0.7374(2) 0.45238(13) 0.0308(4) Uani 1 1 d . . . . .
H12A H 0.2551 0.7321 0.4117 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.4346 0.6241 0.4523 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.3918 0.8106 0.4189 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.0408(2) 0.8635(2) 0.60467(14) 0.0297(4) Uani 1 1 d . . . . .
H13A H -0.0283 0.8600 0.5577 0.036 Uiso 1 1 calc R . . . .
H13B H -0.0196 0.9059 0.6776 0.036 Uiso 1 1 calc R . . . .
C14 C 0.1182(2) 1.3524(2) 0.59322(13) 0.0260(4) Uani 1 1 d . . . . .
H14 H 0.1591 1.3968 0.5294 0.031 Uiso 1 1 calc R . . . .
C15 C 0.2172(2) 1.18052(19) 0.60831(12) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.3244 1.1093 0.5547 0.027 Uiso 1 1 calc R . . . .
C16 C 0.5305(2) 0.90876(18) 0.78754(13) 0.0210(3) Uani 1 1 d . . . . .
C17 C 0.5950(2) 0.83458(18) 0.88487(12) 0.0204(3) Uani 1 1 d . . . . .
C18 C 0.7586(2) 0.80369(19) 0.91293(13) 0.0229(3) Uani 1 1 d . . . . .
H18 H 0.8473 0.8352 0.8695 0.027 Uiso 1 1 calc R . . . .
C19 C 0.7851(2) 0.72392(19) 1.00848(13) 0.0236(3) Uani 1 1 d . . . . .
H19 H 0.8944 0.7015 1.0285 0.028 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 C5 1.2084(18) . ?
O2 C10 1.2164(19) . ?
O3 C16 1.2067(19) . ?
N1 N2 1.3891(17) . ?
N1 C4 1.4403(18) . ?
N1 C10 1.3952(19) . ?
N2 C5 1.405(2) . ?
N2 C16 1.4157(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(2) . ?
C1 C14 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 C15 1.382(2) . ?
C5 C6 1.486(2) . ?
C6 C7 1.381(2) . ?
C6 C17 1.391(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.399(2) . ?
C8 C9 1.502(2) . ?
C8 C19 1.403(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.492(2) . ?
C11 C12 1.489(2) . ?
C11 C13 1.333(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.481(2) . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C4 115.65(11) . . ?
N2 N1 C10 114.83(12) . . ?
C10 N1 C4 125.51(12) . . ?
N1 N2 C5 121.80(12) . . ?
N1 N2 C16 121.82(12) . . ?
C5 N2 C16 112.42(12) . . ?
C2 C1 H1 120.1 . . ?
C14 C1 H1 120.1 . . ?
C14 C1 C2 119.87(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.54(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.98(15) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 N1 118.55(13) . . ?
C15 C4 N1 120.36(13) . . ?
C15 C4 C3 121.02(14) . . ?
O1 C5 N2 125.04(14) . . ?
O1 C5 C6 130.12(14) . . ?
N2 C5 C6 104.84(12) . . ?
C7 C6 C5 129.56(14) . . ?
C7 C6 C17 121.60(14) . . ?
C17 C6 C5 108.83(13) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.68(14) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 C9 120.43(14) . . ?
C7 C8 C19 119.01(14) . . ?
C19 C8 C9 120.56(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N1 120.25(14) . . ?
O2 C10 C11 123.19(13) . . ?
N1 C10 C11 116.39(13) . . ?
C12 C11 C10 116.33(14) . . ?
C13 C11 C10 119.06(14) . . ?
C13 C11 C12 124.36(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 120.0 . . ?
C11 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C1 C14 H14 120.0 . . ?
C1 C14 C15 119.99(15) . . ?
C15 C14 H14 120.0 . . ?
C4 C15 C14 119.59(14) . . ?
C4 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
O3 C16 N2 124.22(14) . . ?
O3 C16 C17 130.93(14) . . ?
N2 C16 C17 104.85(12) . . ?
C6 C17 C16 108.64(13) . . ?
C18 C17 C6 120.82(14) . . ?
C18 C17 C16 130.50(14) . . ?
C17 C18 H18 121.2 . . ?
C17 C18 C19 117.55(14) . . ?
C19 C18 H18 121.2 . . ?
C8 C19 H19 118.8 . . ?
C18 C19 C8 122.33(14) . . ?
C18 C19 H19 118.8 . . ?

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 C5 C6 C7 -1.4(3) . . . . ?
O1 C5 C6 C17 177.31(15) . . . . ?
O2 C10 C11 C12 -44.1(2) . . . . ?
O2 C10 C11 C13 130.45(17) . . . . ?
O3 C16 C17 C6 -174.86(15) . . . . ?
O3 C16 C17 C18 2.9(3) . . . . ?
N1 N2 C5 O1 -16.1(2) . . . . ?
N1 N2 C5 C6 164.00(12) . . . . ?
N1 N2 C16 O3 14.9(2) . . . . ?
N1 N2 C16 C17 -164.73(11) . . . . ?
N1 C4 C15 C14 -177.10(13) . . . . ?
N1 C10 C11 C12 140.69(14) . . . . ?
N1 C10 C11 C13 -44.77(19) . . . . ?
N2 N1 C4 C3 -66.11(17) . . . . ?
N2 N1 C4 C15 110.85(15) . . . . ?
N2 N1 C10 O2 -5.9(2) . . . . ?
N2 N1 C10 C11 169.48(12) . . . . ?
N2 C5 C6 C7 178.52(14) . . . . ?
N2 C5 C6 C17 -2.79(15) . . . . ?
N2 C16 C17 C6 4.72(15) . . . . ?
N2 C16 C17 C18 -177.55(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C14 C15 C4 -0.2(2) . . . . ?
C2 C1 C14 C15 0.7(2) . . . . ?
C2 C3 C4 N1 177.03(13) . . . . ?
C2 C3 C4 C15 0.1(2) . . . . ?
C3 C4 C15 C14 -0.2(2) . . . . ?
C4 N1 N2 C5 118.12(14) . . . . ?
C4 N1 N2 C16 -85.97(16) . . . . ?
C4 N1 C10 O2 150.45(14) . . . . ?
C4 N1 C10 C11 -34.18(19) . . . . ?
C5 N2 C16 O3 172.85(13) . . . . ?
C5 N2 C16 C17 -6.76(16) . . . . ?
C5 C6 C7 C8 178.53(13) . . . . ?
C5 C6 C17 C16 -1.22(16) . . . . ?
C5 C6 C17 C18 -179.21(13) . . . . ?
C6 C7 C8 C9 179.57(13) . . . . ?
C6 C7 C8 C19 0.2(2) . . . . ?
C6 C17 C18 C19 0.6(2) . . . . ?
C7 C6 C17 C16 177.60(13) . . . . ?
C7 C6 C17 C18 -0.4(2) . . . . ?
C7 C8 C19 C18 0.0(2) . . . . ?
C9 C8 C19 C18 -179.37(14) . . . . ?
C10 N1 N2 C5 -83.13(16) . . . . ?
C10 N1 N2 C16 72.78(16) . . . . ?
C10 N1 C4 C3 137.73(15) . . . . ?
C10 N1 C4 C15 -45.3(2) . . . . ?
C14 C1 C2 C3 -0.8(2) . . . . ?
C16 N2 C5 O1 -174.05(13) . . . . ?
C16 N2 C5 C6 6.04(15) . . . . ?
C16 C17 C18 C19 -176.92(14) . . . . ?
C17 C6 C7 C8 0.0(2) . . . . ?
C17 C18 C19 C8 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
