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

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

data_chenjq_0306
_audit_block_doi                 10.5517/ccdc.csd.cc1nl02b
_database_code_depnum_ccdc_archive 'CCDC 1536641'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H21 Br N2 O3 S'
_chemical_formula_sum            'C22 H21 Br N2 O3 S'
_chemical_formula_weight         473.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Br S'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.7286(5)
_cell_length_b                   15.8258(9)
_cell_length_c                   19.8430(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2113.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    932
_cell_measurement_temperature    291.17(10)
_cell_measurement_theta_max      22.4120
_cell_measurement_theta_min      3.8770
_exptl_absorpt_coefficient_mu    2.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5292
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.17(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_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   24.00   54.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492   38.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   46.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000  -90.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0602106000
_diffrn_orient_matrix_UB_12      0.0265687000
_diffrn_orient_matrix_UB_13      -0.0202919000
_diffrn_orient_matrix_UB_21      -0.0797406000
_diffrn_orient_matrix_UB_22      0.0050290000
_diffrn_orient_matrix_UB_23      -0.0230147000
_diffrn_orient_matrix_UB_31      -0.0335515000
_diffrn_orient_matrix_UB_32      0.0357568000
_diffrn_orient_matrix_UB_33      0.0183310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2363
_reflns_number_total             3622
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0246P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0912
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C14(H14a,H14b)
2.e Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C22(H22a,H22b,H22c)
;
_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 0.24436(12) 0.61791(4) 0.13701(3) 0.1038(3) Uani 1 d . . .
S1 S 0.5063(2) 0.54883(7) -0.18539(5) 0.0521(3) Uani 1 d . . .
O1 O -0.2461(6) 0.2610(2) 0.12154(16) 0.0868(11) Uani 1 d . . .
O2 O 0.7154(5) 0.56465(19) -0.18655(15) 0.0663(9) Uani 1 d . . .
O3 O 0.4244(5) 0.47510(18) -0.21610(15) 0.0665(11) Uani 1 d . . .
N1 N 0.4443(6) 0.5405(2) -0.10453(17) 0.0499(10) Uani 1 d . . .
N2 N -0.1007(6) 0.3873(3) 0.09596(18) 0.0597(11) Uani 1 d . . .
C1 C 0.5105(7) 0.5917(2) -0.0515(2) 0.0455(11) Uani 1 d . . .
C2 C 0.6776(7) 0.6427(3) -0.0469(2) 0.0524(12) Uani 1 d . . .
H2 H 0.7643 0.6489 -0.0830 0.063 Uiso 1 calc . . R
C3 C 0.7101(8) 0.6840(3) 0.0132(2) 0.0650(14) Uani 1 d . . .
H3 H 0.8205 0.7188 0.0177 0.078 Uiso 1 calc . . R
C4 C 0.5808(8) 0.6743(3) 0.0672(2) 0.0650(15) Uani 1 d . . .
H4 H 0.6068 0.7024 0.1074 0.078 Uiso 1 calc . . R
C5 C 0.4153(8) 0.6240(3) 0.0623(2) 0.0563(13) Uani 1 d . . .
C6 C 0.3756(7) 0.5804(3) 0.0027(2) 0.0470(11) Uani 1 d . . .
C7 C 0.2215(8) 0.5233(3) -0.0198(2) 0.0471(11) Uani 1 d . . .
C8 C 0.2665(9) 0.5024(3) -0.0837(2) 0.0528(12) Uani 1 d . . .
H8 H 0.1895 0.4672 -0.1106 0.063 Uiso 1 calc . . R
C9 C 0.0420(7) 0.4905(3) 0.0161(2) 0.0587(14) Uani 1 d . . .
H9A H -0.0501 0.4684 -0.0171 0.070 Uiso 1 calc . . R
H9B H -0.0229 0.5372 0.0387 0.070 Uiso 1 calc . . R
C10 C 0.0846(8) 0.4208(3) 0.0683(2) 0.0560(13) Uani 1 d . . .
H10 H 0.1659 0.4439 0.1049 0.067 Uiso 1 calc . . R
C11 C 0.1870(8) 0.3434(3) 0.0387(2) 0.0702(15) Uani 1 d . . .
H11A H 0.1790 0.3438 -0.0101 0.084 Uiso 1 calc . . R
H11B H 0.3257 0.3415 0.0519 0.084 Uiso 1 calc . . R
C12 C 0.0750(8) 0.2695(3) 0.0674(2) 0.0584(13) Uani 1 d . . .
C13 C -0.1095(9) 0.3018(3) 0.0980(2) 0.0587(14) Uani 1 d . . .
C14 C 0.1222(9) 0.1896(3) 0.0663(3) 0.0841(18) Uani 1 d . . .
H14A H 0.0375 0.1498 0.0854 0.101 Uiso 1 calc . . R
H14B H 0.2406 0.1723 0.0463 0.101 Uiso 1 calc . . R
C15 C -0.2487(10) 0.4414(3) 0.1263(2) 0.0884(17) Uani 1 d . . .
H15A H -0.3227 0.4695 0.0916 0.133 Uiso 1 calc . . GR
H15B H -0.1844 0.4826 0.1543 0.133 Uiso 1 calc . . GR
H15C H -0.3373 0.4079 0.1532 0.133 Uiso 1 calc . . GR
C16 C 0.3804(7) 0.6380(3) -0.21512(19) 0.0431(11) Uani 1 d . . .
C17 C 0.4760(8) 0.7128(3) -0.2220(2) 0.0587(13) Uani 1 d . . .
H17 H 0.6094 0.7168 -0.2102 0.070 Uiso 1 calc . . R
C18 C 0.3788(8) 0.7824(3) -0.2462(2) 0.0669(16) Uani 1 d . . .
H18 H 0.4471 0.8332 -0.2509 0.080 Uiso 1 calc . . R
C19 C 0.1811(7) 0.7783(3) -0.2636(2) 0.0511(13) Uani 1 d . . .
C20 C 0.0845(8) 0.7020(3) -0.2559(2) 0.0670(15) Uani 1 d . . .
H20 H -0.0493 0.6981 -0.2672 0.080 Uiso 1 calc . . R
C21 C 0.1818(7) 0.6314(3) -0.2320(2) 0.0612(14) Uani 1 d . . .
H21 H 0.1150 0.5803 -0.2273 0.073 Uiso 1 calc . . R
C22 C 0.0719(8) 0.8536(3) -0.2917(2) 0.0790(17) Uani 1 d . . .
H22A H 0.1051 0.8605 -0.3384 0.119 Uiso 1 calc . . GR
H22B H 0.1097 0.9035 -0.2672 0.119 Uiso 1 calc . . GR
H22C H -0.0687 0.8449 -0.2873 0.119 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 C5 1.879(5) . ?
S1 O2 1.429(3) . ?
S1 O3 1.427(3) . ?
S1 N1 1.663(3) . ?
S1 C16 1.748(5) . ?
O1 C13 1.216(6) . ?
N1 C1 1.401(5) . ?
N1 C8 1.402(6) . ?
N2 C10 1.461(6) . ?
N2 C13 1.356(6) . ?
N2 C15 1.444(6) . ?
C1 C2 1.388(6) . ?
C1 C6 1.418(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(6) . ?
C5 C6 1.395(6) . ?
C6 C7 1.445(6) . ?
C7 C8 1.346(5) . ?
C7 C9 1.495(6) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.541(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.523(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(6) . ?
C12 C13 1.473(7) . ?
C12 C14 1.305(6) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.354(6) . ?
C16 C21 1.381(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(6) . ?
C19 C20 1.380(6) . ?
C19 C22 1.508(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O2 S1 N1 106.0(2) . . ?
O2 S1 C16 109.3(2) . . ?
O3 S1 O2 121.1(2) . . ?
O3 S1 N1 104.51(19) . . ?
O3 S1 C16 109.2(2) . . ?
N1 S1 C16 105.52(19) . . ?
C1 N1 S1 126.9(3) . . ?
C1 N1 C8 107.4(3) . . ?
C8 N1 S1 122.2(3) . . ?
C13 N2 C10 114.2(4) . . ?
C13 N2 C15 123.3(5) . . ?
C15 N2 C10 122.0(4) . . ?
N1 C1 C6 107.1(4) . . ?
C2 C1 N1 130.1(4) . . ?
C2 C1 C6 122.8(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.5(5) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 Br1 118.1(4) . . ?
C4 C5 C6 120.2(5) . . ?
C6 C5 Br1 121.7(4) . . ?
C1 C6 C7 107.7(4) . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 C7 135.1(4) . . ?
C6 C7 C9 130.6(4) . . ?
C8 C7 C6 106.4(4) . . ?
C8 C7 C9 123.0(4) . . ?
N1 C8 H8 124.3 . . ?
C7 C8 N1 111.3(4) . . ?
C7 C8 H8 124.3 . . ?
C7 C9 H9A 108.6 . . ?
C7 C9 H9B 108.6 . . ?
C7 C9 C10 114.8(4) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N2 C10 C9 110.7(4) . . ?
N2 C10 H10 109.5 . . ?
N2 C10 C11 103.9(4) . . ?
C9 C10 H10 109.5 . . ?
C11 C10 C9 113.6(4) . . ?
C11 C10 H10 109.5 . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 C10 104.6(4) . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C13 C12 C11 108.0(4) . . ?
C14 C12 C11 128.7(5) . . ?
C14 C12 C13 123.3(5) . . ?
O1 C13 N2 125.0(5) . . ?
O1 C13 C12 127.7(5) . . ?
N2 C13 C12 107.3(5) . . ?
C12 C14 H14A 120.0 . . ?
C12 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 120.6(4) . . ?
C17 C16 C21 120.1(5) . . ?
C21 C16 S1 119.3(4) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 118.0(5) . . ?
C18 C19 C22 121.8(5) . . ?
C20 C19 C22 120.2(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.6 . . ?
C20 C21 C16 118.8(5) . . ?
C20 C21 H21 120.6 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C5 C6 C1 177.8(3) . . . . ?
Br1 C5 C6 C7 -1.6(7) . . . . ?
S1 N1 C1 C2 -21.0(7) . . . . ?
S1 N1 C1 C6 161.6(3) . . . . ?
S1 N1 C8 C7 -162.7(3) . . . . ?
S1 C16 C17 C18 179.1(4) . . . . ?
S1 C16 C21 C20 -179.5(3) . . . . ?
O2 S1 N1 C1 42.4(4) . . . . ?
O2 S1 N1 C8 -161.8(3) . . . . ?
O2 S1 C16 C17 -13.2(4) . . . . ?
O2 S1 C16 C21 166.3(4) . . . . ?
O3 S1 N1 C1 171.4(4) . . . . ?
O3 S1 N1 C8 -32.8(4) . . . . ?
O3 S1 C16 C17 -147.8(4) . . . . ?
O3 S1 C16 C21 31.8(4) . . . . ?
N1 S1 C16 C17 100.4(4) . . . . ?
N1 S1 C16 C21 -80.0(4) . . . . ?
N1 C1 C2 C3 -177.5(4) . . . . ?
N1 C1 C6 C5 178.4(4) . . . . ?
N1 C1 C6 C7 -2.1(5) . . . . ?
N2 C10 C11 C12 -13.9(5) . . . . ?
C1 N1 C8 C7 -2.8(5) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C1 C6 C7 C8 0.4(5) . . . . ?
C1 C6 C7 C9 -179.3(4) . . . . ?
C2 C1 C6 C5 0.7(6) . . . . ?
C2 C1 C6 C7 -179.7(4) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 Br1 -177.9(4) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 179.6(5) . . . . ?
C5 C6 C7 C8 179.8(5) . . . . ?
C5 C6 C7 C9 0.1(8) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C6 C7 C8 N1 1.5(5) . . . . ?
C6 C7 C9 C10 -76.1(6) . . . . ?
C7 C9 C10 N2 -174.7(4) . . . . ?
C7 C9 C10 C11 -58.3(6) . . . . ?
C8 N1 C1 C2 -179.6(4) . . . . ?
C8 N1 C1 C6 2.9(5) . . . . ?
C8 C7 C9 C10 104.3(5) . . . . ?
C9 C7 C8 N1 -178.8(4) . . . . ?
C9 C10 C11 C12 -134.2(4) . . . . ?
C10 N2 C13 O1 176.8(4) . . . . ?
C10 N2 C13 C12 -2.7(6) . . . . ?
C10 C11 C12 C13 13.0(5) . . . . ?
C10 C11 C12 C14 -168.1(5) . . . . ?
C11 C12 C13 O1 173.7(5) . . . . ?
C11 C12 C13 N2 -6.9(5) . . . . ?
C13 N2 C10 C9 133.0(4) . . . . ?
C13 N2 C10 C11 10.8(5) . . . . ?
C14 C12 C13 O1 -5.3(9) . . . . ?
C14 C12 C13 N2 174.2(5) . . . . ?
C15 N2 C10 C9 -54.6(6) . . . . ?
C15 N2 C10 C11 -176.9(4) . . . . ?
C15 N2 C13 O1 4.5(8) . . . . ?
C15 N2 C13 C12 -174.9(4) . . . . ?
C16 S1 N1 C1 -73.5(4) . . . . ?
C16 S1 N1 C8 82.3(4) . . . . ?
C16 C17 C18 C19 0.5(8) . . . . ?
C17 C16 C21 C20 0.1(7) . . . . ?
C17 C18 C19 C20 -0.1(8) . . . . ?
C17 C18 C19 C22 -178.7(4) . . . . ?
C18 C19 C20 C21 -0.3(7) . . . . ?
C19 C20 C21 C16 0.3(8) . . . . ?
C21 C16 C17 C18 -0.5(7) . . . . ?
C22 C19 C20 C21 178.3(5) . . . . ?

_olex2_date_sample_data_collection 2017-03-08
_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_chjq_0613_2
_database_code_depnum_ccdc_archive 'CCDC 1559337'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;
_audit_creation_date             2017-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.40
_chemical_absolute_configuration unk
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0741(10)
_cell_length_b                   7.6193(15)
_cell_length_c                   11.4018(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.452(9)
_cell_angle_gamma                90.00
_cell_volume                     875.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    556
_cell_measurement_temperature    294.7(2)
_cell_measurement_theta_max      23.0080
_cell_measurement_theta_min      4.0940
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3472
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      294.7(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00    8.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -30.0000 14

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00  -62.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  -30.0000 17

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   67.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   17.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000    0.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0274233000
_diffrn_orient_matrix_UB_12      -0.0749595000
_diffrn_orient_matrix_UB_13      -0.0279818000
_diffrn_orient_matrix_UB_21      -0.0220527000
_diffrn_orient_matrix_UB_22      -0.0316664000
_diffrn_orient_matrix_UB_23      0.0549738000
_diffrn_orient_matrix_UB_31      -0.0609927000
_diffrn_orient_matrix_UB_32      0.0452588000
_diffrn_orient_matrix_UB_33      -0.0079301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1641
_reflns_number_total             2736
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.047
_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)+(0.0638P)²+0.0372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1792
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O3 O -0.8967(2) -0.7402(6) -0.7257(2) 0.0519(9) Uani 1 d . . .
O2 O -1.0444(3) -0.7613(9) -0.5791(3) 0.0891(17) Uani 1 d . . .
N2 N -0.8240(3) -0.7427(8) -0.5403(3) 0.0483(11) Uani 1 d . . .
O1 O -0.2588(3) -0.7158(9) -0.0630(3) 0.0880(15) Uani 1 d . . .
N1 N -0.4744(4) -0.6547(7) -0.1200(3) 0.0578(14) Uani 1 d . . .
C7 C -0.6250(3) -0.7095(7) -0.4560(3) 0.0371(11) Uani 1 d . . .
C6 C -0.7191(4) -0.7357(8) -0.3652(3) 0.0399(11) Uani 1 d . . .
C16 C -0.9345(4) -0.7490(10) -0.6150(4) 0.0544(15) Uani 1 d . . .
C8 C -0.4886(4) -0.6813(7) -0.4422(3) 0.0400(12) Uani 1 d . . .
C12 C -0.6883(4) -0.7154(8) -0.5652(3) 0.0401(11) Uani 1 d . . .
C17 C -0.9980(4) -0.7425(9) -0.8221(3) 0.0463(12) Uani 1 d . . .
C11 C -0.6155(4) -0.7001(8) -0.6668(4) 0.0474(13) Uani 1 d . . .
H11 H -0.6556 -0.7056 -0.7404 0.057 Uiso 1 calc . . R
C19 C -1.0857(7) -0.5846(9) -0.8142(6) 0.075(2) Uani 1 d . . .
H19A H -1.1330 -0.5871 -0.7415 0.112 Uiso 1 calc . . GR
H19B H -1.1479 -0.5850 -0.8784 0.112 Uiso 1 calc . . GR
H19C H -1.0324 -0.4802 -0.8176 0.112 Uiso 1 calc . . GR
C5 C -0.6718(4) -0.7433(8) -0.2393(3) 0.0428(12) Uani 1 d . . .
H5A H -0.6526 -0.8637 -0.2172 0.051 Uiso 1 calc . . R
H5B H -0.7400 -0.6985 -0.1877 0.051 Uiso 1 calc . . R
C13 C -0.8383(4) -0.7519(9) -0.4180(4) 0.0519(14) Uani 1 d . . .
H13 H -0.9184 -0.7668 -0.3792 0.062 Uiso 1 calc . . R
C9 C -0.4155(4) -0.6686(7) -0.5448(4) 0.0466(13) Uani 1 d . . .
H9 H -0.3238 -0.6550 -0.5410 0.056 Uiso 1 calc . . R
C3 C -0.4431(4) -0.6739(7) -0.3206(4) 0.0407(12) Uani 1 d . . .
C10 C -0.4800(4) -0.6764(7) -0.6537(4) 0.0512(15) Uani 1 d . . .
H10 H -0.4291 -0.6649 -0.7210 0.061 Uiso 1 calc . . R
C4 C -0.5463(4) -0.6311(7) -0.2287(4) 0.0467(13) Uani 1 d . . .
H4 H -0.5711 -0.5073 -0.2363 0.056 Uiso 1 calc . . R
C2 C -0.3268(4) -0.7070(8) -0.2677(4) 0.0496(14) Uani 1 d . . .
C18 C -0.9120(5) -0.7329(14) -0.9293(4) 0.084(2) Uani 1 d . . .
H18A H -0.8533 -0.6342 -0.9227 0.126 Uiso 1 calc . . GR
H18B H -0.9671 -0.7197 -0.9978 0.126 Uiso 1 calc . . GR
H18C H -0.8609 -0.8388 -0.9357 0.126 Uiso 1 calc . . GR
C15 C -0.1965(4) -0.7549(11) -0.3188(4) 0.0695(18) Uani 1 d . . .
H15A H -0.2099 -0.8376 -0.3813 0.104 Uiso 1 calc . . GR
H15B H -0.1412 -0.8065 -0.2592 0.104 Uiso 1 calc . . GR
H15C H -0.1544 -0.6515 -0.3490 0.104 Uiso 1 calc . . GR
C20 C -1.0770(7) -0.9115(10) -0.8186(6) 0.085(2) Uani 1 d . . .
H20A H -1.0173 -1.0097 -0.8198 0.128 Uiso 1 calc . . GR
H20B H -1.1352 -0.9170 -0.8856 0.128 Uiso 1 calc . . GR
H20C H -1.1285 -0.9150 -0.7482 0.128 Uiso 1 calc . . GR
C1 C -0.3451(4) -0.6942(9) -0.1396(4) 0.0583(16) Uani 1 d . . .
C14 C -0.5284(6) -0.6187(10) -0.0052(5) 0.078(2) Uani 1 d . . .
H14A H -0.5648 -0.5023 -0.0041 0.117 Uiso 1 calc . . GR
H14B H -0.4592 -0.6278 0.0528 0.117 Uiso 1 calc . . GR
H14C H -0.5970 -0.7021 0.0118 0.117 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
O3 C16 1.323(5) . ?
O3 C17 1.495(4) . ?
O2 C16 1.187(5) . ?
N2 C16 1.397(5) . ?
N2 C12 1.414(5) . ?
N2 C13 1.404(5) . ?
O1 C1 1.239(5) . ?
N1 C4 1.442(5) . ?
N1 C1 1.357(6) . ?
N1 C14 1.448(6) . ?
C7 C6 1.423(5) . ?
C7 C8 1.399(5) . ?
C7 C12 1.395(5) . ?
C6 C5 1.511(5) . ?
C6 C13 1.344(5) . ?
C8 C9 1.391(6) . ?
C8 C3 1.458(6) . ?
C12 C11 1.380(5) . ?
C17 C19 1.496(8) . ?
C17 C18 1.505(6) . ?
C17 C20 1.514(9) . ?
C11 H11 0.9300 . ?
C11 C10 1.384(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.530(6) . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.398(6) . ?
C3 C4 1.517(6) . ?
C3 C2 1.338(5) . ?
C10 H10 0.9300 . ?
C4 H4 0.9800 . ?
C2 C15 1.485(6) . ?
C2 C1 1.477(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C16 O3 C17 120.1(3) . . ?
C16 N2 C12 130.5(3) . . ?
C16 N2 C13 121.1(3) . . ?
C13 N2 C12 108.3(3) . . ?
C4 N1 C14 124.3(4) . . ?
C1 N1 C4 111.3(4) . . ?
C1 N1 C14 124.0(4) . . ?
C8 C7 C6 126.9(3) . . ?
C12 C7 C6 110.0(3) . . ?
C12 C7 C8 123.1(3) . . ?
C7 C6 C5 119.3(3) . . ?
C13 C6 C7 106.6(3) . . ?
C13 C6 C5 134.1(4) . . ?
O3 C16 N2 110.3(4) . . ?
O2 C16 O3 127.5(4) . . ?
O2 C16 N2 122.2(4) . . ?
C7 C8 C3 114.4(3) . . ?
C9 C8 C7 116.3(4) . . ?
C9 C8 C3 129.3(4) . . ?
C7 C12 N2 105.1(3) . . ?
C11 C12 N2 134.6(4) . . ?
C11 C12 C7 120.3(4) . . ?
O3 C17 C19 110.3(4) . . ?
O3 C17 C18 101.7(3) . . ?
O3 C17 C20 110.3(5) . . ?
C19 C17 C18 110.7(6) . . ?
C19 C17 C20 111.8(4) . . ?
C18 C17 C20 111.6(6) . . ?
C12 C11 H11 121.6 . . ?
C12 C11 C10 116.8(4) . . ?
C10 C11 H11 121.6 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C6 C5 C4 107.9(4) . . ?
H5A C5 H5B 108.4 . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
N2 C13 H13 125.0 . . ?
C6 C13 N2 110.0(4) . . ?
C6 C13 H13 125.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C3 C4 117.0(3) . . ?
C2 C3 C8 133.6(4) . . ?
C2 C3 C4 109.4(4) . . ?
C11 C10 C9 123.5(4) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N1 C4 C5 114.0(4) . . ?
N1 C4 C3 103.0(3) . . ?
N1 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C3 C4 C5 113.3(4) . . ?
C3 C4 H4 108.8 . . ?
C3 C2 C15 130.0(4) . . ?
C3 C2 C1 108.5(4) . . ?
C1 C2 C15 121.5(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C1 N1 125.6(5) . . ?
O1 C1 C2 126.6(4) . . ?
N1 C1 C2 107.7(3) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 C12 C11 C10 -178.9(6) . . . . ?
C7 C6 C5 C4 28.8(7) . . . . ?
C7 C6 C13 N2 1.9(8) . . . . ?
C7 C8 C9 C10 2.8(8) . . . . ?
C7 C8 C3 C4 -21.5(7) . . . . ?
C7 C8 C3 C2 154.1(6) . . . . ?
C7 C12 C11 C10 -1.0(8) . . . . ?
C6 C7 C8 C9 176.6(6) . . . . ?
C6 C7 C8 C3 -1.9(9) . . . . ?
C6 C7 C12 N2 1.0(6) . . . . ?
C6 C7 C12 C11 -177.4(6) . . . . ?
C6 C5 C4 N1 -167.8(4) . . . . ?
C6 C5 C4 C3 -50.4(6) . . . . ?
C16 O3 C17 C19 63.3(7) . . . . ?
C16 O3 C17 C18 -179.2(6) . . . . ?
C16 O3 C17 C20 -60.7(7) . . . . ?
C16 N2 C12 C7 175.7(6) . . . . ?
C16 N2 C12 C11 -6.2(12) . . . . ?
C16 N2 C13 C6 -177.4(6) . . . . ?
C8 C7 C6 C5 -3.0(10) . . . . ?
C8 C7 C6 C13 178.1(6) . . . . ?
C8 C7 C12 N2 -178.9(6) . . . . ?
C8 C7 C12 C11 2.7(8) . . . . ?
C8 C9 C10 C11 -1.4(9) . . . . ?
C8 C3 C4 N1 173.4(4) . . . . ?
C8 C3 C4 C5 49.8(6) . . . . ?
C8 C3 C2 C15 4.1(12) . . . . ?
C8 C3 C2 C1 -174.1(6) . . . . ?
C12 N2 C16 O3 5.6(10) . . . . ?
C12 N2 C16 O2 -174.6(8) . . . . ?
C12 N2 C13 C6 -1.4(8) . . . . ?
C12 C7 C6 C5 177.1(5) . . . . ?
C12 C7 C6 C13 -1.8(7) . . . . ?
C12 C7 C8 C9 -3.5(8) . . . . ?
C12 C7 C8 C3 178.0(4) . . . . ?
C12 C11 C10 C9 0.5(9) . . . . ?
C17 O3 C16 O2 1.0(11) . . . . ?
C17 O3 C16 N2 -179.3(5) . . . . ?
C5 C6 C13 N2 -176.8(6) . . . . ?
C13 N2 C16 O3 -179.3(5) . . . . ?
C13 N2 C16 O2 0.4(11) . . . . ?
C13 N2 C12 C7 0.2(6) . . . . ?
C13 N2 C12 C11 178.2(7) . . . . ?
C13 C6 C5 C4 -152.6(7) . . . . ?
C9 C8 C3 C4 160.2(5) . . . . ?
C9 C8 C3 C2 -24.2(10) . . . . ?
C3 C8 C9 C10 -179.0(5) . . . . ?
C3 C2 C1 O1 -179.7(6) . . . . ?
C3 C2 C1 N1 0.5(7) . . . . ?
C4 N1 C1 O1 177.5(6) . . . . ?
C4 N1 C1 C2 -2.7(6) . . . . ?
C4 C3 C2 C15 179.9(7) . . . . ?
C4 C3 C2 C1 1.7(6) . . . . ?
C2 C3 C4 N1 -3.2(6) . . . . ?
C2 C3 C4 C5 -126.9(5) . . . . ?
C15 C2 C1 O1 1.9(10) . . . . ?
C15 C2 C1 N1 -177.9(6) . . . . ?
C1 N1 C4 C5 126.7(5) . . . . ?
C1 N1 C4 C3 3.5(6) . . . . ?
C14 N1 C4 C5 -60.7(7) . . . . ?
C14 N1 C4 C3 176.1(5) . . . . ?
C14 N1 C1 O1 4.9(10) . . . . ?
C14 N1 C1 C2 -175.3(5) . . . . ?

_olex2_date_sample_data_collection 2017-06-14
_olex2_submission_special_instructions 'No special instructions were received'
