# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_150527_ym1
_database_code_depnum_ccdc_archive 'CCDC 1477460'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;
_audit_creation_date             2015-05-29
_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 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.3522(19)
_cell_length_b                   13.823(3)
_cell_length_c                   9.515(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.847(18)
_cell_angle_gamma                90.00
_cell_volume                     1753.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2440
_cell_measurement_theta_min      3.9250
_exptl_absorpt_coefficient_mu    2.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.036
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_av_unetI/netI     0.1291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9853
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   85.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007    0.0000  -60.0000 139

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   22.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8725  -99.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00  -11.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007  -37.0000  120.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0284094000
_diffrn_orient_matrix_UB_12      0.0425952000
_diffrn_orient_matrix_UB_13      0.0097382000
_diffrn_orient_matrix_UB_21      -0.0034440000
_diffrn_orient_matrix_UB_22      -0.0114398000
_diffrn_orient_matrix_UB_23      0.0723618000
_diffrn_orient_matrix_UB_31      0.0447930000
_diffrn_orient_matrix_UB_32      0.0261104000
_diffrn_orient_matrix_UB_33      0.0161519000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1707
_reflns_number_total             3503
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0665
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0769P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.2086
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C15(H15), C3(H3A), C2(H2), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.32819(4) 0.35003(6) 0.24232(7) 0.0724(4) Uani 1 d . . .
O2 O 0.0056(3) 0.3329(3) 0.6585(4) 0.0456(10) Uani 1 d . . .
C9 C -0.0407(4) 0.2484(4) 0.6975(5) 0.0387(13) Uani 1 d . . .
O3 O -0.0529(3) 0.0778(3) 0.6841(4) 0.0516(10) Uani 1 d . . .
H3 H -0.0484 0.0373 0.6219 0.077 Uiso 1 calc . . GR
C6 C 0.1110(4) 0.2470(4) 0.5029(5) 0.0358(12) Uani 1 d . . .
C10 C -0.1180(3) 0.2667(4) 0.7967(5) 0.0343(12) Uani 1 d . . .
C5 C 0.1874(4) 0.2542(5) 0.4060(5) 0.0404(14) Uani 1 d . . .
H5 H 0.2108 0.1987 0.3632 0.048 Uiso 1 calc . . R
C8 C -0.0096(4) 0.1634(4) 0.6428(5) 0.0394(13) Uani 1 d . . .
C1 C 0.0795(4) 0.3328(5) 0.5643(5) 0.0424(14) Uani 1 d . . .
C11 C -0.1461(4) 0.3632(5) 0.8232(5) 0.0466(15) Uani 1 d . . .
H11 H -0.1128 0.4136 0.7805 0.056 Uiso 1 calc . . R
C4 C 0.2264(4) 0.3407(5) 0.3751(6) 0.0522(17) Uani 1 d . . .
C7 C 0.0657(4) 0.1557(4) 0.5400(5) 0.0406(14) Uani 1 d . . .
C15 C -0.1672(4) 0.1936(5) 0.8662(5) 0.0444(14) Uani 1 d . . .
H15 H -0.1494 0.1293 0.8526 0.053 Uiso 1 calc . . R
C13 C -0.2738(4) 0.3102(5) 0.9801(5) 0.0444(15) Uani 1 d . . .
O1 O 0.0895(3) 0.0776(3) 0.4864(4) 0.0545(11) Uani 1 d . . .
N1 N -0.3522(3) 0.3315(4) 1.0643(5) 0.0540(14) Uani 1 d . . .
C3 C 0.1934(4) 0.4247(5) 0.4364(7) 0.0580(17) Uani 1 d . . .
H3A H 0.2211 0.4839 0.4126 0.070 Uiso 1 calc . . R
C17 C -0.3431(6) 0.4909(7) 1.1838(9) 0.101(3) Uani 1 d . . .
H17A H -0.3772 0.5520 1.1863 0.151 Uiso 1 calc . . GR
H17B H -0.2744 0.5013 1.1625 0.151 Uiso 1 calc . . GR
H17C H -0.3458 0.4598 1.2737 0.151 Uiso 1 calc . . GR
C2 C 0.1195(4) 0.4216(5) 0.5326(6) 0.0564(16) Uani 1 d . . .
H2 H 0.0973 0.4778 0.5749 0.068 Uiso 1 calc . . R
C12 C -0.2219(4) 0.3838(5) 0.9112(5) 0.0488(15) Uani 1 d . . .
H12 H -0.2395 0.4481 0.9257 0.059 Uiso 1 calc . . R
C18 C -0.3994(4) 0.2541(6) 1.1435(6) 0.0611(19) Uani 1 d . . .
H18A H -0.4277 0.2817 1.2265 0.073 Uiso 1 calc . . R
H18B H -0.3484 0.2077 1.1748 0.073 Uiso 1 calc . . R
C14 C -0.2423(4) 0.2160(5) 0.9553(5) 0.0503(15) Uani 1 d . . .
H14 H -0.2734 0.1656 1.0010 0.060 Uiso 1 calc . . R
C16 C -0.3936(5) 0.4272(6) 1.0714(7) 0.078(2) Uani 1 d . . .
H16A H -0.4643 0.4221 1.0893 0.093 Uiso 1 calc . . R
H16B H -0.3883 0.4583 0.9807 0.093 Uiso 1 calc . . R
C19 C -0.4816(5) 0.2015(7) 1.0578(7) 0.093(3) Uani 1 d . . .
H19A H -0.4528 0.1678 0.9813 0.139 Uiso 1 calc . . GR
H19B H -0.5299 0.2475 1.0211 0.139 Uiso 1 calc . . GR
H19C H -0.5139 0.1559 1.1167 0.139 Uiso 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
Br1 C4 1.905(6) . ?
O2 C9 1.381(6) . ?
O2 C1 1.366(6) . ?
C9 C10 1.455(7) . ?
C9 C8 1.358(7) . ?
O3 H3 0.8200 . ?
O3 C8 1.381(6) . ?
C6 C5 1.412(7) . ?
C6 C1 1.397(7) . ?
C6 C7 1.450(7) . ?
C10 C11 1.412(7) . ?
C10 C15 1.391(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.343(8) . ?
C8 C7 1.441(7) . ?
C1 C2 1.377(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(7) . ?
C4 C3 1.382(8) . ?
C7 O1 1.243(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(7) . ?
C13 N1 1.380(7) . ?
C13 C12 1.411(8) . ?
C13 C14 1.393(8) . ?
N1 C18 1.469(8) . ?
N1 C16 1.437(8) . ?
C3 H3A 0.9300 . ?
C3 C2 1.379(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C16 1.517(10) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.520(9) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C9 121.6(4) . . ?
O2 C9 C10 111.6(5) . . ?
C8 C9 O2 118.6(5) . . ?
C8 C9 C10 129.7(6) . . ?
C8 O3 H3 109.5 . . ?
C5 C6 C7 123.0(5) . . ?
C1 C6 C5 117.1(5) . . ?
C1 C6 C7 119.9(5) . . ?
C11 C10 C9 118.9(5) . . ?
C15 C10 C9 123.3(5) . . ?
C15 C10 C11 117.8(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C9 C8 O3 119.4(5) . . ?
C9 C8 C7 124.1(5) . . ?
O3 C8 C7 116.5(5) . . ?
O2 C1 C6 121.2(5) . . ?
O2 C1 C2 116.3(5) . . ?
C2 C1 C6 122.5(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(6) . . ?
C12 C11 H11 119.5 . . ?
C5 C4 Br1 120.2(5) . . ?
C5 C4 C3 121.4(5) . . ?
C3 C4 Br1 118.5(5) . . ?
C8 C7 C6 114.6(5) . . ?
O1 C7 C6 122.5(5) . . ?
O1 C7 C8 122.9(5) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.3(6) . . ?
C14 C15 H15 119.9 . . ?
N1 C13 C12 121.4(6) . . ?
N1 C13 C14 122.8(6) . . ?
C14 C13 C12 115.8(5) . . ?
C13 N1 C18 120.0(6) . . ?
C13 N1 C16 121.8(5) . . ?
C16 N1 C18 118.1(5) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 C4 120.5(6) . . ?
C2 C3 H3A 119.8 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
C1 C2 C3 118.1(6) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C11 C12 C13 121.8(6) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
N1 C18 H18A 109.0 . . ?
N1 C18 H18B 109.0 . . ?
N1 C18 C19 112.9(5) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C15 C14 C13 123.3(6) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N1 C16 C17 114.2(6) . . ?
N1 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 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
Br1 C4 C3 C2 179.7(5) . . . . ?
O2 C9 C10 C11 9.3(6) . . . . ?
O2 C9 C10 C15 -171.6(4) . . . . ?
O2 C9 C8 O3 177.9(4) . . . . ?
O2 C9 C8 C7 -3.5(7) . . . . ?
O2 C1 C2 C3 -179.1(5) . . . . ?
C9 O2 C1 C6 0.3(7) . . . . ?
C9 O2 C1 C2 179.4(4) . . . . ?
C9 C10 C11 C12 177.0(5) . . . . ?
C9 C10 C15 C14 -177.7(4) . . . . ?
C9 C8 C7 C6 3.1(7) . . . . ?
C9 C8 C7 O1 -176.4(5) . . . . ?
O3 C8 C7 C6 -178.3(4) . . . . ?
O3 C8 C7 O1 2.2(7) . . . . ?
C6 C5 C4 Br1 -179.2(3) . . . . ?
C6 C5 C4 C3 -0.1(9) . . . . ?
C6 C1 C2 C3 0.0(9) . . . . ?
C10 C9 C8 O3 -1.3(8) . . . . ?
C10 C9 C8 C7 177.3(5) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C10 C15 C14 C13 0.6(8) . . . . ?
C5 C6 C1 O2 179.5(4) . . . . ?
C5 C6 C1 C2 0.4(8) . . . . ?
C5 C6 C7 C8 178.9(4) . . . . ?
C5 C6 C7 O1 -1.6(8) . . . . ?
C5 C4 C3 C2 0.6(9) . . . . ?
C8 C9 C10 C11 -171.4(5) . . . . ?
C8 C9 C10 C15 7.7(8) . . . . ?
C1 O2 C9 C10 -179.0(4) . . . . ?
C1 O2 C9 C8 1.7(7) . . . . ?
C1 C6 C5 C4 -0.4(7) . . . . ?
C1 C6 C7 C8 -1.0(7) . . . . ?
C1 C6 C7 O1 178.5(5) . . . . ?
C11 C10 C15 C14 1.4(7) . . . . ?
C4 C3 C2 C1 -0.6(9) . . . . ?
C7 C6 C5 C4 179.7(5) . . . . ?
C7 C6 C1 O2 -0.6(7) . . . . ?
C7 C6 C1 C2 -179.7(5) . . . . ?
C15 C10 C11 C12 -2.1(7) . . . . ?
C13 N1 C18 C19 -85.7(7) . . . . ?
C13 N1 C16 C17 -89.5(7) . . . . ?
N1 C13 C12 C11 -177.6(5) . . . . ?
N1 C13 C14 C15 176.8(5) . . . . ?
C12 C13 N1 C18 -175.1(5) . . . . ?
C12 C13 N1 C16 8.4(8) . . . . ?
C12 C13 C14 C15 -1.8(8) . . . . ?
C18 N1 C16 C17 93.9(7) . . . . ?
C14 C13 N1 C18 6.3(8) . . . . ?
C14 C13 N1 C16 -170.2(5) . . . . ?
C14 C13 C12 C11 1.1(7) . . . . ?
C16 N1 C18 C19 91.0(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_150413_ym_1
_database_code_depnum_ccdc_archive 'CCDC 1477461'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;
_audit_creation_date             2015-04-14
_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 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N O5'
_chemical_formula_weight         352.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0399(7)
_cell_length_b                   7.3275(7)
_cell_length_c                   17.4123(17)
_cell_angle_alpha                89.658(8)
_cell_angle_beta                 82.561(8)
_cell_angle_gamma                76.168(8)
_cell_volume                     864.53(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1708
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1660
_cell_measurement_theta_min      3.7450
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.046
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10358
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007  -77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   32.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007  -57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   22.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7944  -99.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   22.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7944  -99.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   -3.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007   37.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7007  178.0000  -30.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0387574000
_diffrn_orient_matrix_UB_12      -0.0388609000
_diffrn_orient_matrix_UB_13      -0.0376055000
_diffrn_orient_matrix_UB_21      0.0769200000
_diffrn_orient_matrix_UB_22      -0.0639853000
_diffrn_orient_matrix_UB_23      0.0156927000
_diffrn_orient_matrix_UB_31      -0.0594852000
_diffrn_orient_matrix_UB_32      -0.0658841000
_diffrn_orient_matrix_UB_33      0.0053267000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2096
_reflns_number_total             3519
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.0164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C12(H12), C13(H13), C16(H16), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.70795(17) 0.66873(17) 0.02772(7) 0.0380(3) Uani 1 d . . .
C2 C 0.7758(2) 0.5284(3) 0.07757(11) 0.0346(5) Uani 1 d . . .
C4 C 0.8001(2) 0.2910(3) -0.02479(11) 0.0386(5) Uani 1 d . . .
O25 O 0.8387(2) 0.12236(19) -0.04607(8) 0.0546(4) Uani 1 d . . .
O26 O 0.8943(2) 0.20528(19) 0.10017(8) 0.0510(4) Uani 1 d . . .
H26 H 0.9470 0.1086 0.0747 0.076 Uiso 1 calc . . GR
C3 C 0.8236(3) 0.3445(3) 0.05203(11) 0.0363(5) Uani 1 d . . .
C5 C 0.7334(2) 0.4453(3) -0.07547(11) 0.0357(5) Uani 1 d . . .
C7 C 0.6581(3) 0.5667(3) -0.19843(12) 0.0449(5) Uani 1 d . . .
C10 C 0.6925(2) 0.6292(3) -0.04709(11) 0.0358(5) Uani 1 d . . .
C11 C 0.7878(3) 0.6039(3) 0.15305(11) 0.0363(5) Uani 1 d . . .
C6 C 0.7146(3) 0.4156(3) -0.15337(12) 0.0446(5) Uani 1 d . . .
H6 H 0.7403 0.2941 -0.1741 0.054 Uiso 1 calc . . R
C8 C 0.6181(3) 0.7511(3) -0.16966(12) 0.0490(5) Uani 1 d . . .
H8 H 0.5808 0.8515 -0.2018 0.059 Uiso 1 calc . . R
C12 C 0.7733(3) 0.7962(3) 0.16439(11) 0.0430(5) Uani 1 d . . .
H12 H 0.7521 0.8757 0.1229 0.052 Uiso 1 calc . . R
N22 N 0.6420(3) 0.5355(4) -0.28032(12) 0.0620(6) Uani 1 d . . .
C13 C 0.7893(3) 0.8710(3) 0.23435(12) 0.0506(6) Uani 1 d . . .
H13 H 0.7821 0.9990 0.2387 0.061 Uiso 1 calc . . R
C16 C 0.8155(3) 0.4922(3) 0.21825(12) 0.0466(5) Uani 1 d . . .
H16 H 0.8265 0.3637 0.2133 0.056 Uiso 1 calc . . R
C9 C 0.6344(3) 0.7830(3) -0.09330(12) 0.0447(5) Uani 1 d . . .
H9 H 0.6071 0.9049 -0.0729 0.054 Uiso 1 calc . . R
C14 C 0.8165(3) 0.7594(3) 0.29994(12) 0.0489(6) Uani 1 d . . .
N17 N 0.8331(3) 0.8324(3) 0.37013(11) 0.0676(6) Uani 1 d . . .
O24 O 0.5862(3) 0.6722(3) -0.31910(10) 0.0926(6) Uani 1 d . . .
O23 O 0.6826(3) 0.3741(3) -0.30575(10) 0.0875(6) Uani 1 d . . .
C15 C 0.8268(3) 0.5667(3) 0.28923(12) 0.0506(6) Uani 1 d . . .
H15 H 0.8416 0.4880 0.3312 0.061 Uiso 1 calc . . R
C18 C 0.8624(5) 0.7109(4) 0.43681(14) 0.0876(9) Uani 1 d . . .
H18A H 0.9260 0.7680 0.4731 0.105 Uiso 1 calc . . R
H18B H 0.9500 0.5909 0.4194 0.105 Uiso 1 calc . . R
C20 C 0.8448(4) 1.0296(4) 0.38026(15) 0.0831(9) Uani 1 d . . .
H20A H 0.8028 1.0684 0.4342 0.100 Uiso 1 calc . . R
H20B H 0.7546 1.1096 0.3495 0.100 Uiso 1 calc . . R
C21 C 1.0486(5) 1.0572(4) 0.3570(2) 0.1126(12) Uani 1 d . . .
H21A H 1.0853 1.0328 0.3023 0.169 Uiso 1 calc . . GR
H21B H 1.1403 0.9722 0.3847 0.169 Uiso 1 calc . . GR
H21C H 1.0507 1.1843 0.3691 0.169 Uiso 1 calc . . GR
C1 C 0.6736(6) 0.6779(6) 0.47762(18) 0.1476(16) Uani 1 d . . .
H1A H 0.6058 0.6287 0.4413 0.221 Uiso 1 calc . . GR
H1B H 0.5919 0.7945 0.4999 0.221 Uiso 1 calc . . GR
H1C H 0.7019 0.5895 0.5179 0.221 Uiso 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
O1 C2 1.379(2) . ?
O1 C10 1.360(2) . ?
C2 C3 1.371(2) . ?
C2 C11 1.449(3) . ?
C4 O25 1.247(2) . ?
C4 C3 1.437(3) . ?
C4 C5 1.456(3) . ?
O26 H26 0.8200 . ?
O26 C3 1.358(2) . ?
C5 C10 1.389(3) . ?
C5 C6 1.403(3) . ?
C7 C6 1.363(3) . ?
C7 C8 1.395(3) . ?
C7 N22 1.469(3) . ?
C10 C9 1.392(3) . ?
C11 C12 1.402(3) . ?
C11 C16 1.402(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.375(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(3) . ?
N22 O24 1.219(3) . ?
N22 O23 1.220(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.407(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.373(3) . ?
C9 H9 0.9300 . ?
C14 N17 1.367(3) . ?
C14 C15 1.409(3) . ?
N17 C18 1.464(3) . ?
N17 C20 1.480(3) . ?
C15 H15 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C1 1.496(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.500(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C2 121.43(14) . . ?
O1 C2 C11 111.74(15) . . ?
C3 C2 O1 119.49(16) . . ?
C3 C2 C11 128.77(19) . . ?
O25 C4 C3 121.26(19) . . ?
O25 C4 C5 123.02(18) . . ?
C3 C4 C5 115.71(16) . . ?
C3 O26 H26 109.5 . . ?
C2 C3 C4 122.29(18) . . ?
O26 C3 C2 120.00(17) . . ?
O26 C3 C4 117.71(16) . . ?
C10 C5 C4 119.41(17) . . ?
C10 C5 C6 118.24(19) . . ?
C6 C5 C4 122.31(18) . . ?
C6 C7 C8 122.14(19) . . ?
C6 C7 N22 119.3(2) . . ?
C8 C7 N22 118.6(2) . . ?
O1 C10 C5 121.52(18) . . ?
O1 C10 C9 116.29(17) . . ?
C5 C10 C9 122.18(18) . . ?
C12 C11 C2 120.87(18) . . ?
C12 C11 C16 116.10(17) . . ?
C16 C11 C2 123.03(17) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.34(19) . . ?
C7 C6 H6 120.3 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.3(2) . . ?
C13 C12 H12 118.9 . . ?
O24 N22 C7 118.3(2) . . ?
O24 N22 O23 123.4(2) . . ?
O23 N22 C7 118.3(2) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.76(19) . . ?
C14 C13 H13 119.1 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 122.07(19) . . ?
C15 C16 H16 119.0 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.71(19) . . ?
C8 C9 H9 120.6 . . ?
C13 C14 C15 116.16(18) . . ?
N17 C14 C13 122.3(2) . . ?
N17 C14 C15 121.5(2) . . ?
C14 N17 C18 120.5(2) . . ?
C14 N17 C20 122.1(2) . . ?
C18 N17 C20 117.0(2) . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
N17 C18 H18A 109.0 . . ?
N17 C18 H18B 109.0 . . ?
N17 C18 C1 112.8(3) . . ?
H18A C18 H18B 107.8 . . ?
C1 C18 H18A 109.0 . . ?
C1 C18 H18B 109.0 . . ?
N17 C20 H20A 109.0 . . ?
N17 C20 H20B 109.0 . . ?
N17 C20 C21 112.9(2) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C1 H1A 109.5 . . ?
C18 C1 H1B 109.5 . . ?
C18 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -1.9(3) . . . . ?
O1 C2 C3 O26 178.71(14) . . . . ?
O1 C2 C11 C12 -13.1(2) . . . . ?
O1 C2 C11 C16 167.38(15) . . . . ?
O1 C10 C9 C8 179.43(15) . . . . ?
C2 O1 C10 C5 3.8(2) . . . . ?
C2 O1 C10 C9 -176.00(14) . . . . ?
C2 C11 C12 C13 -178.23(16) . . . . ?
C2 C11 C16 C15 179.88(16) . . . . ?
C4 C5 C10 O1 -1.9(2) . . . . ?
C4 C5 C10 C9 177.88(15) . . . . ?
C4 C5 C6 C7 -177.64(16) . . . . ?
O25 C4 C3 C2 -177.70(16) . . . . ?
O25 C4 C3 O26 1.7(3) . . . . ?
O25 C4 C5 C10 179.63(16) . . . . ?
O25 C4 C5 C6 -2.4(3) . . . . ?
C3 C2 C11 C12 166.20(17) . . . . ?
C3 C2 C11 C16 -13.3(3) . . . . ?
C3 C4 C5 C10 -1.7(2) . . . . ?
C3 C4 C5 C6 176.26(15) . . . . ?
C5 C4 C3 C2 3.6(2) . . . . ?
C5 C4 C3 O26 -177.04(14) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C10 O1 C2 C3 -1.9(2) . . . . ?
C10 O1 C2 C11 177.49(13) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C11 C2 C3 C4 178.87(15) . . . . ?
C11 C2 C3 O26 -0.5(3) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
C11 C16 C15 C14 -1.7(3) . . . . ?
C6 C5 C10 O1 -179.89(14) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C6 C7 N22 O24 178.05(19) . . . . ?
C6 C7 N22 O23 -1.0(3) . . . . ?
C8 C7 C6 C5 0.0(3) . . . . ?
C8 C7 N22 O24 -3.0(3) . . . . ?
C8 C7 N22 O23 177.95(18) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 N17 179.87(18) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
N22 C7 C6 C5 178.87(15) . . . . ?
N22 C7 C8 C9 -179.35(16) . . . . ?
C13 C14 N17 C18 -179.6(2) . . . . ?
C13 C14 N17 C20 -6.6(3) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C14 N17 C18 C1 -83.1(3) . . . . ?
C14 N17 C20 C21 -81.6(3) . . . . ?
N17 C14 C15 C16 -178.22(18) . . . . ?
C15 C14 N17 C18 0.0(3) . . . . ?
C15 C14 N17 C20 173.1(2) . . . . ?
C18 N17 C20 C21 91.7(3) . . . . ?
C20 N17 C18 C1 103.5(3) . . . . ?

_olex2_date_sample_data_collection 2015-04-13
_olex2_submission_special_instructions 'No special instructions were received'
