# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_wangzhh_0228
_database_code_depnum_ccdc_archive 'CCDC 1540954'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_audit_creation_date             2017-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H23 N O6'
_chemical_formula_sum            'C22 H23 N O6'
_chemical_formula_weight         397.41
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.9730(4)
_cell_length_b                   15.1158(5)
_cell_length_c                   25.0975(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4162.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4450
_cell_measurement_theta_min      4.0150
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74094
_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    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11243
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega   41.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -38.0000    0.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0063493000
_diffrn_orient_matrix_UB_12      0.0033236000
_diffrn_orient_matrix_UB_13      -0.0280463000
_diffrn_orient_matrix_UB_21      0.0314827000
_diffrn_orient_matrix_UB_22      0.0407261000
_diffrn_orient_matrix_UB_23      0.0031221000
_diffrn_orient_matrix_UB_31      0.0560488000
_diffrn_orient_matrix_UB_32      -0.0231547000
_diffrn_orient_matrix_UB_33      0.0014228000
_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                2441
_reflns_number_total             4097
_reflns_odcompleteness_completeness 99.58
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.066
_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)+(0.0473P)²+0.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1458
_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 Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.50553(15) 0.20280(10) 0.46364(6) 0.0449(5) Uani 1 d . . .
H1 H 0.4574 0.2051 0.4886 0.067 Uiso 1 calc . . GR
O2 O 0.80943(17) 0.29862(13) 0.47131(7) 0.0655(6) Uani 1 d . . .
O3 O 0.30686(17) 0.16359(14) 0.32788(9) 0.0810(7) Uani 1 d . . .
O4 O 0.45499(16) 0.08635(11) 0.29100(7) 0.0544(5) Uani 1 d . . .
O5 O 0.64889(16) 0.04668(11) 0.39694(8) 0.0599(6) Uani 1 d . . .
O6 O 0.44975(15) 0.02714(10) 0.41289(7) 0.0474(5) Uani 1 d . . .
N1 N 0.65884(16) 0.32329(11) 0.41291(7) 0.0355(5) Uani 1 d . . .
C1 C 0.5456(2) 0.36350(14) 0.39868(8) 0.0336(5) Uani 1 d . . .
C2 C 0.5436(2) 0.45169(16) 0.38395(10) 0.0491(7) Uani 1 d . . .
H2 H 0.6154 0.4843 0.3829 0.059 Uiso 1 calc . . R
C3 C 0.4332(3) 0.49106(17) 0.37077(12) 0.0576(8) Uani 1 d . . .
H3 H 0.4310 0.5505 0.3612 0.069 Uiso 1 calc . . R
C4 C 0.3281(3) 0.44284(17) 0.37185(11) 0.0554(7) Uani 1 d . . .
H4 H 0.2545 0.4695 0.3629 0.066 Uiso 1 calc . . R
C5 C 0.3306(2) 0.35459(16) 0.38611(10) 0.0451(6) Uani 1 d . . .
H5 H 0.2584 0.3224 0.3867 0.054 Uiso 1 calc . . R
C6 C 0.4391(2) 0.31332(14) 0.39961(9) 0.0346(5) Uani 1 d . . .
C7 C 0.4419(2) 0.21663(14) 0.41506(9) 0.0358(5) Uani 1 d . . .
H7 H 0.3578 0.1960 0.4195 0.043 Uiso 1 calc . . R
C8 C 0.5040(2) 0.15999(13) 0.37086(9) 0.0319(5) Uani 1 d . . .
C9 C 0.6120(2) 0.20763(14) 0.34412(9) 0.0366(5) Uani 1 d . . .
H9A H 0.6528 0.1658 0.3208 0.044 Uiso 1 calc . . R
H9B H 0.5798 0.2546 0.3219 0.044 Uiso 1 calc . . R
C10 C 0.7070(2) 0.24755(14) 0.38146(9) 0.0355(5) Uani 1 d . . .
H10 H 0.7314 0.2014 0.4067 0.043 Uiso 1 calc . . R
C11 C 0.8191(2) 0.27451(15) 0.35053(10) 0.0417(6) Uani 1 d . . .
C12 C 0.8162(3) 0.3432(2) 0.31417(11) 0.0661(8) Uani 1 d . . .
H12 H 0.7444 0.3748 0.3092 0.079 Uiso 1 calc . . R
C13 C 0.9186(3) 0.3654(3) 0.28517(14) 0.0949(12) Uani 1 d . . .
H13 H 0.9154 0.4115 0.2607 0.114 Uiso 1 calc . . R
C14 C 1.0245(3) 0.3196(3) 0.29249(17) 0.0940(13) Uani 1 d . . .
H14 H 1.0937 0.3347 0.2731 0.113 Uiso 1 calc . . R
C15 C 1.0289(3) 0.2518(2) 0.3281(2) 0.0894(13) Uani 1 d . . .
H15 H 1.1009 0.2203 0.3327 0.107 Uiso 1 calc . . R
C16 C 0.9269(2) 0.22968(18) 0.35744(14) 0.0637(9) Uani 1 d . . .
H16 H 0.9312 0.1839 0.3821 0.076 Uiso 1 calc . . R
C17 C 0.7158(3) 0.33942(18) 0.45983(10) 0.0504(7) Uani 1 d . . .
C18 C 0.6616(3) 0.4072(2) 0.49676(12) 0.0861(11) Uani 1 d . . .
H18A H 0.6774 0.4654 0.4831 0.129 Uiso 1 calc . . GR
H18B H 0.6977 0.4013 0.5314 0.129 Uiso 1 calc . . GR
H18C H 0.5752 0.3980 0.4993 0.129 Uiso 1 calc . . GR
C19 C 0.4095(2) 0.13886(15) 0.32834(10) 0.0400(6) Uani 1 d . . .
C20 C 0.3721(3) 0.06156(19) 0.24861(11) 0.0727(9) Uani 1 d . . .
H20A H 0.4137 0.0241 0.2236 0.109 Uiso 1 calc . . GR
H20B H 0.3439 0.1138 0.2307 0.109 Uiso 1 calc . . GR
H20C H 0.3038 0.0304 0.2634 0.109 Uiso 1 calc . . GR
C21 C 0.5455(2) 0.07241(15) 0.39492(10) 0.0408(6) Uani 1 d . . .
C22 C 0.4756(3) -0.05865(16) 0.43642(12) 0.0640(8) Uani 1 d . . .
H22A H 0.5019 -0.0988 0.4091 0.096 Uiso 1 calc . . GR
H22B H 0.4033 -0.0813 0.4530 0.096 Uiso 1 calc . . GR
H22C H 0.5387 -0.0525 0.4626 0.096 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 H1 0.8200 . ?
O1 C7 1.421(3) . ?
O2 C17 1.232(3) . ?
O3 C19 1.186(3) . ?
O4 C19 1.326(3) . ?
O4 C20 1.449(3) . ?
O5 C21 1.200(3) . ?
O6 C21 1.333(3) . ?
O6 C22 1.453(3) . ?
N1 C1 1.428(3) . ?
N1 C10 1.487(3) . ?
N1 C17 1.355(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.512(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.558(3) . ?
C8 C9 1.540(3) . ?
C8 C19 1.522(3) . ?
C8 C21 1.525(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.526(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.511(3) . ?
C11 C12 1.382(4) . ?
C11 C16 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.360(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C7 O1 H1 109.5 . . ?
C19 O4 C20 115.9(2) . . ?
C21 O6 C22 116.21(19) . . ?
C1 N1 C10 120.24(17) . . ?
C17 N1 C1 122.8(2) . . ?
C17 N1 C10 115.84(19) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 C6 121.0(2) . . ?
C6 C1 N1 119.58(19) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 120.9(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 121.0(2) . . ?
O1 C7 C6 111.84(18) . . ?
O1 C7 H7 108.5 . . ?
O1 C7 C8 108.36(16) . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 110.93(18) . . ?
C8 C7 H7 108.5 . . ?
C9 C8 C7 112.94(17) . . ?
C19 C8 C7 108.43(18) . . ?
C19 C8 C9 108.48(18) . . ?
C19 C8 C21 107.40(17) . . ?
C21 C8 C7 109.02(18) . . ?
C21 C8 C9 110.40(18) . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 C8 116.27(18) . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
N1 C10 C9 112.82(17) . . ?
N1 C10 H10 107.6 . . ?
N1 C10 C11 110.74(17) . . ?
C9 C10 H10 107.6 . . ?
C11 C10 C9 110.33(18) . . ?
C11 C10 H10 107.6 . . ?
C12 C11 C10 121.5(2) . . ?
C16 C11 C10 120.2(2) . . ?
C16 C11 C12 118.2(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.7(3) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O2 C17 N1 119.8(2) . . ?
O2 C17 C18 121.8(2) . . ?
N1 C17 C18 118.4(2) . . ?
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 . . ?
O3 C19 O4 122.6(2) . . ?
O3 C19 C8 126.0(2) . . ?
O4 C19 C8 111.4(2) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 O6 124.4(2) . . ?
O5 C21 C8 125.5(2) . . ?
O6 C21 C8 110.13(19) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
O6 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
O1 C7 C8 C9 -86.2(2) . . . . ?
O1 C7 C8 C19 153.57(17) . . . . ?
O1 C7 C8 C21 36.9(2) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
N1 C1 C6 C7 -0.5(3) . . . . ?
N1 C10 C11 C12 -58.1(3) . . . . ?
N1 C10 C11 C16 123.0(2) . . . . ?
C1 N1 C10 C9 -13.4(3) . . . . ?
C1 N1 C10 C11 110.8(2) . . . . ?
C1 N1 C17 O2 175.5(2) . . . . ?
C1 N1 C17 C18 -4.2(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C6 C7 O1 50.3(3) . . . . ?
C1 C6 C7 C8 -70.8(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C5 C6 C7 O1 -129.6(2) . . . . ?
C5 C6 C7 C8 109.3(2) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C7 C8 C9 37.0(2) . . . . ?
C6 C7 C8 C19 -83.3(2) . . . . ?
C6 C7 C8 C21 160.07(19) . . . . ?
C7 C8 C9 C10 50.2(2) . . . . ?
C7 C8 C19 O3 2.3(3) . . . . ?
C7 C8 C19 O4 -176.39(18) . . . . ?
C7 C8 C21 O5 -118.9(3) . . . . ?
C7 C8 C21 O6 62.1(2) . . . . ?
C8 C9 C10 N1 -67.5(2) . . . . ?
C8 C9 C10 C11 168.05(18) . . . . ?
C9 C8 C19 O3 -120.7(3) . . . . ?
C9 C8 C19 O4 60.6(2) . . . . ?
C9 C8 C21 O5 5.7(3) . . . . ?
C9 C8 C21 O6 -173.33(18) . . . . ?
C9 C10 C11 C12 67.5(3) . . . . ?
C9 C10 C11 C16 -111.4(3) . . . . ?
C10 N1 C1 C2 -118.4(2) . . . . ?
C10 N1 C1 C6 61.3(3) . . . . ?
C10 N1 C17 O2 7.6(3) . . . . ?
C10 N1 C17 C18 -172.1(2) . . . . ?
C10 C11 C12 C13 -178.2(3) . . . . ?
C10 C11 C16 C15 177.8(2) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C11 C16 C15 -1.1(4) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C15 C16 C11 1.1(5) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C17 N1 C1 C2 74.2(3) . . . . ?
C17 N1 C1 C6 -106.1(3) . . . . ?
C17 N1 C10 C9 154.8(2) . . . . ?
C17 N1 C10 C11 -81.0(2) . . . . ?
C19 C8 C9 C10 170.45(18) . . . . ?
C19 C8 C21 O5 123.8(3) . . . . ?
C19 C8 C21 O6 -55.2(2) . . . . ?
C20 O4 C19 O3 0.9(4) . . . . ?
C20 O4 C19 C8 179.6(2) . . . . ?
C21 C8 C9 C10 -72.1(2) . . . . ?
C21 C8 C19 O3 119.9(3) . . . . ?
C21 C8 C19 O4 -58.7(2) . . . . ?
C22 O6 C21 O5 0.2(4) . . . . ?
C22 O6 C21 C8 179.3(2) . . . . ?

_olex2_date_sample_data_collection 2017-02-28
_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_luoych_0629
_database_code_depnum_ccdc_archive 'CCDC 1540957'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_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         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 S8 H20 I2'
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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y, z-1/2'

_cell_length_a                   16.8611(8)
_cell_length_b                   7.7647(3)
_cell_length_c                   27.0984(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.764(5)
_cell_angle_gamma                90.00
_cell_volume                     3506.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      22.5120
_cell_measurement_theta_min      3.7950
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91353
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_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  0.0470
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12770
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   19.40   1.0500    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   89.05   1.0500    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  150.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   67.25   1.0500    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 65
;
_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      0.0335850000
_diffrn_orient_matrix_UB_12      -0.0004318000
_diffrn_orient_matrix_UB_13      0.0192753000
_diffrn_orient_matrix_UB_21      -0.0242030000
_diffrn_orient_matrix_UB_22      0.0341524000
_diffrn_orient_matrix_UB_23      0.0168814000
_diffrn_orient_matrix_UB_31      -0.0099228000
_diffrn_orient_matrix_UB_32      -0.0847103000
_diffrn_orient_matrix_UB_33      0.0067069000
_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                3855
_reflns_number_total             6901
_reflns_odcompleteness_completeness 99.65
_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, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.009
_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)+(0.0599P)²+0.9349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1784
_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:
 C7(H7), C10(H10), C27(H27), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C32(H32), C33(H33),
  C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C)
;
_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
O1 O 0.59992(12) 0.6948(2) 0.68653(8) 0.0448(5) Uani 1 d . . .
O2 O 0.74251(15) 0.5201(3) 0.62340(10) 0.0684(8) Uani 1 d . . .
O3 O 0.79681(14) 0.6479(3) 0.69325(9) 0.0625(7) Uani 1 d . . .
O4 O 0.77746(15) 1.0542(3) 0.67178(11) 0.0727(8) Uani 1 d . . .
O5 O 0.78481(14) 0.9592(3) 0.59475(9) 0.0598(7) Uani 1 d . . .
N1 N 0.53231(14) 0.7253(3) 0.64606(10) 0.0408(6) Uani 1 d . . .
C1 C 0.42985(19) 0.5796(4) 0.55959(15) 0.0573(10) Uani 1 d . . .
H1 H 0.4269 0.5207 0.5891 0.069 Uiso 1 calc . . R
C2 C 0.3681(2) 0.5655(5) 0.52035(19) 0.0751(13) Uani 1 d . . .
H2 H 0.3240 0.4966 0.5234 0.090 Uiso 1 calc . . R
C3 C 0.3713(2) 0.6518(6) 0.47713(17) 0.0776(14) Uani 1 d . . .
H3 H 0.3292 0.6426 0.4508 0.093 Uiso 1 calc . . R
C4 C 0.4368(3) 0.7531(5) 0.47225(15) 0.0708(12) Uani 1 d . . .
H4 H 0.4390 0.8119 0.4426 0.085 Uiso 1 calc . . R
C5 C 0.4994(2) 0.7672(4) 0.51179(13) 0.0564(9) Uani 1 d . . .
H5 H 0.5435 0.8357 0.5084 0.068 Uiso 1 calc . . R
C6 C 0.49694(18) 0.6810(4) 0.55574(12) 0.0431(8) Uani 1 d . . .
C7 C 0.56515(17) 0.6802(4) 0.59926(11) 0.0383(7) Uani 1 d . . .
H7 H 0.5840 0.5609 0.6032 0.046 Uiso 1 calc . . R
C8 C 0.63851(17) 0.7898(4) 0.59212(11) 0.0391(7) Uani 1 d . . .
H8A H 0.6653 0.7373 0.5667 0.047 Uiso 1 calc . . R
H8B H 0.6205 0.9034 0.5804 0.047 Uiso 1 calc . . R
C9 C 0.69859(17) 0.8083(4) 0.64041(11) 0.0374(7) Uani 1 d . . .
C10 C 0.65175(18) 0.8404(4) 0.68435(12) 0.0429(8) Uani 1 d . . .
H10 H 0.6877 0.8580 0.7159 0.052 Uiso 1 calc . . R
C11 C 0.59187(17) 0.9863(4) 0.67331(12) 0.0393(7) Uani 1 d . . .
C12 C 0.5947(2) 1.1603(4) 0.68259(13) 0.0501(8) Uani 1 d . . .
H12 H 0.6418 1.2128 0.6977 0.060 Uiso 1 calc . . R
C13 C 0.5251(2) 1.2551(4) 0.66874(14) 0.0584(10) Uani 1 d . . .
H13 H 0.5254 1.3730 0.6748 0.070 Uiso 1 calc . . R
C14 C 0.4554(2) 1.1766(4) 0.64603(15) 0.0595(10) Uani 1 d . . .
H14 H 0.4093 1.2425 0.6374 0.071 Uiso 1 calc . . R
C15 C 0.45282(19) 1.0017(4) 0.63583(13) 0.0491(8) Uani 1 d . . .
H15 H 0.4063 0.9494 0.6198 0.059 Uiso 1 calc . . R
C16 C 0.52151(17) 0.9090(4) 0.65031(11) 0.0386(7) Uani 1 d . . .
C17 C 0.74716(18) 0.6415(4) 0.65039(12) 0.0431(8) Uani 1 d . . .
C18 C 0.8456(3) 0.4964(4) 0.70643(16) 0.0796(13) Uani 1 d . . .
H18A H 0.8868 0.4898 0.6857 0.119 Uiso 1 calc . . GR
H18B H 0.8125 0.3954 0.7016 0.119 Uiso 1 calc . . GR
H18C H 0.8698 0.5036 0.7408 0.119 Uiso 1 calc . . GR
C19 C 0.75741(18) 0.9548(4) 0.63836(14) 0.0454(8) Uani 1 d . . .
C20 C 0.8411(2) 1.0960(5) 0.58913(16) 0.0787(13) Uani 1 d . . .
H20A H 0.8563 1.0900 0.5564 0.118 Uiso 1 calc . . GR
H20B H 0.8879 1.0833 0.6139 0.118 Uiso 1 calc . . GR
H20C H 0.8164 1.2053 0.5933 0.118 Uiso 1 calc . . GR
O6 O 0.23474(12) 0.3770(2) 0.64268(8) 0.0474(6) Uani 1 d . . .
O7 O 0.05586(18) 0.5235(3) 0.68206(10) 0.0882(10) Uani 1 d . . .
O8 O 0.14649(15) 0.4254(3) 0.74306(8) 0.0628(7) Uani 1 d . . .
O9 O 0.13574(15) 0.0172(3) 0.73004(10) 0.0699(8) Uani 1 d . . .
O10 O 0.01393(13) 0.0758(3) 0.68934(9) 0.0562(6) Uani 1 d . . .
N2 N 0.20779(14) 0.3365(3) 0.58976(10) 0.0416(6) Uani 1 d . . .
C21 C 0.1253(2) 0.4288(4) 0.49207(14) 0.0575(9) Uani 1 d . . .
H21 H 0.1690 0.4996 0.5029 0.069 Uiso 1 calc . . R
C22 C 0.0993(3) 0.4104(6) 0.44216(15) 0.0743(12) Uani 1 d . . .
H22 H 0.1259 0.4679 0.4194 0.089 Uiso 1 calc . . R
C23 C 0.0346(3) 0.3086(5) 0.42495(14) 0.0725(12) Uani 1 d . . .
H23 H 0.0178 0.2960 0.3908 0.087 Uiso 1 calc . . R
C24 C -0.0050(2) 0.2256(5) 0.45866(14) 0.0667(11) Uani 1 d . . .
H24 H -0.0496 0.1580 0.4475 0.080 Uiso 1 calc . . R
C25 C 0.0216(2) 0.2424(4) 0.50939(12) 0.0508(9) Uani 1 d . . .
H25 H -0.0053 0.1850 0.5320 0.061 Uiso 1 calc . . R
C26 C 0.08732(18) 0.3433(4) 0.52684(11) 0.0390(7) Uani 1 d . . .
C27 C 0.11828(17) 0.3666(4) 0.58206(11) 0.0381(7) Uani 1 d . . .
H27 H 0.1096 0.4874 0.5903 0.046 Uiso 1 calc . . R
C28 C 0.07552(17) 0.2561(4) 0.61660(11) 0.0382(7) Uani 1 d . . .
H28A H 0.0707 0.1394 0.6037 0.046 Uiso 1 calc . . R
H28B H 0.0218 0.3007 0.6165 0.046 Uiso 1 calc . . R
C29 C 0.11968(17) 0.2516(4) 0.67093(11) 0.0379(7) Uani 1 d . . .
C30 C 0.21049(17) 0.2306(4) 0.66963(12) 0.0412(7) Uani 1 d . . .
H30 H 0.2415 0.2207 0.7032 0.049 Uiso 1 calc . . R
C31 C 0.22648(16) 0.0841(4) 0.63631(12) 0.0401(7) Uani 1 d . . .
C32 C 0.23719(18) -0.0911(4) 0.64352(14) 0.0505(9) Uani 1 d . . .
H32 H 0.2385 -0.1398 0.6750 0.061 Uiso 1 calc . . R
C33 C 0.2460(2) -0.1924(4) 0.60256(15) 0.0579(10) Uani 1 d . . .
H33 H 0.2533 -0.3105 0.6066 0.069 Uiso 1 calc . . R
C34 C 0.2441(2) -0.1204(5) 0.55585(15) 0.0605(10) Uani 1 d . . .
H34 H 0.2508 -0.1905 0.5290 0.073 Uiso 1 calc . . R
C35 C 0.23208(19) 0.0559(4) 0.54831(14) 0.0522(9) Uani 1 d . . .
H35 H 0.2300 0.1052 0.5169 0.063 Uiso 1 calc . . R
C36 C 0.22351(17) 0.1531(4) 0.58926(12) 0.0405(7) Uani 1 d . . .
C37 C 0.1031(2) 0.4170(4) 0.69821(12) 0.0470(8) Uani 1 d . . .
C38 C 0.1335(3) 0.5747(4) 0.77301(14) 0.0795(13) Uani 1 d . . .
H38A H 0.1488 0.6770 0.7569 0.119 Uiso 1 calc . . GR
H38B H 0.1654 0.5644 0.8054 0.119 Uiso 1 calc . . GR
H38C H 0.0778 0.5816 0.7766 0.119 Uiso 1 calc . . GR
C39 C 0.09234(19) 0.1024(4) 0.70028(12) 0.0421(7) Uani 1 d . . .
C40 C -0.0181(2) -0.0665(5) 0.71495(14) 0.0683(11) Uani 1 d . . .
H40A H 0.0012 -0.1733 0.7035 0.102 Uiso 1 calc . . GR
H40B H -0.0757 -0.0646 0.7080 0.102 Uiso 1 calc . . GR
H40C H -0.0011 -0.0556 0.7503 0.102 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 N1 1.475(3) . ?
O1 C10 1.436(3) . ?
O2 C17 1.188(3) . ?
O3 C17 1.325(3) . ?
O3 C18 1.449(4) . ?
O4 C19 1.199(4) . ?
O5 C19 1.333(4) . ?
O5 C20 1.448(4) . ?
N1 C7 1.501(4) . ?
N1 C16 1.445(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(5) . ?
C1 C6 1.395(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C6 C7 1.517(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.538(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.535(4) . ?
C9 C10 1.546(4) . ?
C9 C17 1.534(4) . ?
C9 C19 1.516(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.516(4) . ?
C11 C12 1.374(4) . ?
C11 C16 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O6 N2 1.471(3) . ?
O6 C30 1.443(3) . ?
O7 C37 1.184(4) . ?
O8 C37 1.321(4) . ?
O8 C38 1.451(4) . ?
O9 C39 1.202(3) . ?
O10 C39 1.326(4) . ?
O10 C40 1.452(4) . ?
N2 C27 1.510(4) . ?
N2 C36 1.449(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.364(5) . ?
C21 C26 1.386(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(4) . ?
C26 C27 1.519(4) . ?
C27 H27 0.9800 . ?
C27 C28 1.529(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.546(4) . ?
C29 C30 1.545(4) . ?
C29 C37 1.529(4) . ?
C29 C39 1.516(4) . ?
C30 H30 0.9800 . ?
C30 C31 1.502(4) . ?
C31 C32 1.382(4) . ?
C31 C36 1.377(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.387(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.379(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.394(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.368(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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 N1 104.43(19) . . ?
C17 O3 C18 116.4(3) . . ?
C19 O5 C20 115.7(3) . . ?
O1 N1 C7 104.4(2) . . ?
C16 N1 O1 101.1(2) . . ?
C16 N1 C7 111.4(2) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 120.9(4) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 117.8(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 123.8(3) . . ?
N1 C7 C6 108.8(2) . . ?
N1 C7 H7 106.5 . . ?
N1 C7 C8 112.6(2) . . ?
C6 C7 H7 106.5 . . ?
C6 C7 C8 115.4(2) . . ?
C8 C7 H7 106.5 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 C10 108.9(2) . . ?
C17 C9 C8 109.7(2) . . ?
C17 C9 C10 108.8(2) . . ?
C19 C9 C8 112.9(2) . . ?
C19 C9 C10 108.7(2) . . ?
C19 C9 C17 107.8(2) . . ?
O1 C10 C9 106.9(2) . . ?
O1 C10 H10 111.9 . . ?
O1 C10 C11 101.8(2) . . ?
C9 C10 H10 111.9 . . ?
C11 C10 C9 111.8(2) . . ?
C11 C10 H10 111.9 . . ?
C12 C11 C10 134.0(3) . . ?
C12 C11 C16 120.7(3) . . ?
C16 C11 C10 105.3(2) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.9(3) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 121.4 . . ?
C16 C15 C14 117.3(3) . . ?
C16 C15 H15 121.4 . . ?
C11 C16 N1 110.6(2) . . ?
C15 C16 N1 127.4(3) . . ?
C15 C16 C11 121.9(3) . . ?
O2 C17 O3 122.9(3) . . ?
O2 C17 C9 125.3(3) . . ?
O3 C17 C9 111.8(3) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O5 123.9(3) . . ?
O4 C19 C9 124.5(3) . . ?
O5 C19 C9 111.6(3) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C30 O6 N2 104.82(19) . . ?
C37 O8 C38 116.4(3) . . ?
C39 O10 C40 116.3(3) . . ?
O6 N2 C27 104.8(2) . . ?
C36 N2 O6 100.9(2) . . ?
C36 N2 C27 109.3(2) . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C26 120.7(4) . . ?
C26 C21 H21 119.6 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(4) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.2(4) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C27 119.2(3) . . ?
C25 C26 C21 118.0(3) . . ?
C25 C26 C27 122.8(3) . . ?
N2 C27 C26 107.7(2) . . ?
N2 C27 H27 107.3 . . ?
N2 C27 C28 112.5(2) . . ?
C26 C27 H27 107.3 . . ?
C26 C27 C28 114.4(2) . . ?
C28 C27 H27 107.3 . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C29 113.1(2) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C30 C29 C28 108.4(2) . . ?
C37 C29 C28 110.2(2) . . ?
C37 C29 C30 110.8(3) . . ?
C39 C29 C28 112.1(2) . . ?
C39 C29 C30 108.3(2) . . ?
C39 C29 C37 107.2(3) . . ?
O6 C30 C29 106.7(2) . . ?
O6 C30 H30 112.2 . . ?
O6 C30 C31 101.6(2) . . ?
C29 C30 H30 112.2 . . ?
C31 C30 C29 111.3(2) . . ?
C31 C30 H30 112.2 . . ?
C32 C31 C30 133.8(3) . . ?
C36 C31 C30 106.1(2) . . ?
C36 C31 C32 120.0(3) . . ?
C31 C32 H32 120.9 . . ?
C31 C32 C33 118.2(3) . . ?
C33 C32 H32 120.9 . . ?
C32 C33 H33 119.5 . . ?
C34 C33 C32 121.0(3) . . ?
C34 C33 H33 119.5 . . ?
C33 C34 H34 119.5 . . ?
C33 C34 C35 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 121.5 . . ?
C36 C35 C34 117.0(3) . . ?
C36 C35 H35 121.5 . . ?
C31 C36 N2 110.8(3) . . ?
C35 C36 N2 126.3(3) . . ?
C35 C36 C31 122.9(3) . . ?
O7 C37 O8 123.5(3) . . ?
O7 C37 C29 124.8(3) . . ?
O8 C37 C29 111.7(3) . . ?
O8 C38 H38A 109.5 . . ?
O8 C38 H38B 109.5 . . ?
O8 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O9 C39 O10 123.3(3) . . ?
O9 C39 C29 124.8(3) . . ?
O10 C39 C29 112.0(3) . . ?
O10 C40 H40A 109.5 . . ?
O10 C40 H40B 109.5 . . ?
O10 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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 N1 C7 C6 171.5(2) . . . . ?
O1 N1 C7 C8 -59.2(3) . . . . ?
O1 N1 C16 C11 23.6(3) . . . . ?
O1 N1 C16 C15 -154.7(3) . . . . ?
O1 C10 C11 C12 153.3(4) . . . . ?
O1 C10 C11 C16 -24.5(3) . . . . ?
N1 O1 C10 C9 -78.1(2) . . . . ?
N1 O1 C10 C11 39.3(3) . . . . ?
N1 C7 C8 C9 44.4(3) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C1 C6 C7 N1 -54.2(3) . . . . ?
C1 C6 C7 C8 178.1(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C7 -175.8(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 C7 175.8(3) . . . . ?
C5 C6 C7 N1 129.9(3) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 170.2(2) . . . . ?
C7 N1 C16 C11 -86.8(3) . . . . ?
C7 N1 C16 C15 95.0(4) . . . . ?
C7 C8 C9 C10 -42.3(3) . . . . ?
C7 C8 C9 C17 76.7(3) . . . . ?
C7 C8 C9 C19 -163.1(2) . . . . ?
C8 C9 C10 O1 59.5(3) . . . . ?
C8 C9 C10 C11 -51.1(3) . . . . ?
C8 C9 C17 O2 4.2(4) . . . . ?
C8 C9 C17 O3 -176.5(3) . . . . ?
C8 C9 C19 O4 137.2(3) . . . . ?
C8 C9 C19 O5 -43.2(3) . . . . ?
C9 C10 C11 C12 -92.9(4) . . . . ?
C9 C10 C11 C16 89.3(3) . . . . ?
C10 O1 N1 C7 76.5(2) . . . . ?
C10 O1 N1 C16 -39.1(3) . . . . ?
C10 C9 C17 O2 123.2(4) . . . . ?
C10 C9 C17 O3 -57.5(3) . . . . ?
C10 C9 C19 O4 16.3(4) . . . . ?
C10 C9 C19 O5 -164.1(2) . . . . ?
C10 C11 C12 C13 -176.9(3) . . . . ?
C10 C11 C16 N1 0.1(3) . . . . ?
C10 C11 C16 C15 178.5(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C11 C16 N1 -178.1(3) . . . . ?
C12 C11 C16 C15 0.3(5) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C13 C14 C15 C16 1.6(6) . . . . ?
C14 C15 C16 N1 176.6(3) . . . . ?
C14 C15 C16 C11 -1.4(5) . . . . ?
C16 N1 C7 C6 -80.2(3) . . . . ?
C16 N1 C7 C8 49.1(3) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C17 C9 C10 O1 -59.9(3) . . . . ?
C17 C9 C10 C11 -170.6(2) . . . . ?
C17 C9 C19 O4 -101.5(4) . . . . ?
C17 C9 C19 O5 78.1(3) . . . . ?
C18 O3 C17 O2 -0.8(5) . . . . ?
C18 O3 C17 C9 179.9(3) . . . . ?
C19 C9 C10 O1 -177.1(2) . . . . ?
C19 C9 C10 C11 72.3(3) . . . . ?
C19 C9 C17 O2 -119.1(4) . . . . ?
C19 C9 C17 O3 60.2(3) . . . . ?
C20 O5 C19 O4 -0.9(5) . . . . ?
C20 O5 C19 C9 179.6(3) . . . . ?
O6 N2 C27 C26 174.8(2) . . . . ?
O6 N2 C27 C28 -58.2(3) . . . . ?
O6 N2 C36 C31 22.3(3) . . . . ?
O6 N2 C36 C35 -159.6(3) . . . . ?
O6 C30 C31 C32 160.4(3) . . . . ?
O6 C30 C31 C36 -24.3(3) . . . . ?
N2 O6 C30 C29 -78.3(3) . . . . ?
N2 O6 C30 C31 38.4(3) . . . . ?
N2 C27 C28 C29 44.0(3) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C21 C26 C27 N2 -49.9(3) . . . . ?
C21 C26 C27 C28 -175.8(3) . . . . ?
C22 C21 C26 C25 -1.4(5) . . . . ?
C22 C21 C26 C27 179.8(3) . . . . ?
C22 C23 C24 C25 -1.3(6) . . . . ?
C23 C24 C25 C26 0.6(5) . . . . ?
C24 C25 C26 C21 0.8(5) . . . . ?
C24 C25 C26 C27 179.6(3) . . . . ?
C25 C26 C27 N2 131.3(3) . . . . ?
C25 C26 C27 C28 5.4(4) . . . . ?
C26 C21 C22 C23 0.6(6) . . . . ?
C26 C27 C28 C29 167.3(2) . . . . ?
C27 N2 C36 C31 -87.7(3) . . . . ?
C27 N2 C36 C35 90.3(4) . . . . ?
C27 C28 C29 C30 -42.9(3) . . . . ?
C27 C28 C29 C37 78.5(3) . . . . ?
C27 C28 C29 C39 -162.3(2) . . . . ?
C28 C29 C30 O6 59.8(3) . . . . ?
C28 C29 C30 C31 -50.3(3) . . . . ?
C28 C29 C37 O7 8.3(5) . . . . ?
C28 C29 C37 O8 -173.4(3) . . . . ?
C28 C29 C39 O9 141.2(3) . . . . ?
C28 C29 C39 O10 -38.8(3) . . . . ?
C29 C30 C31 C32 -86.4(4) . . . . ?
C29 C30 C31 C36 88.9(3) . . . . ?
C30 O6 N2 C27 75.9(2) . . . . ?
C30 O6 N2 C36 -37.7(3) . . . . ?
C30 C29 C37 O7 128.2(4) . . . . ?
C30 C29 C37 O8 -53.5(4) . . . . ?
C30 C29 C39 O9 21.7(4) . . . . ?
C30 C29 C39 O10 -158.3(3) . . . . ?
C30 C31 C32 C33 175.9(3) . . . . ?
C30 C31 C36 N2 0.9(3) . . . . ?
C30 C31 C36 C35 -177.2(3) . . . . ?
C31 C32 C33 C34 -0.1(5) . . . . ?
C32 C31 C36 N2 177.0(3) . . . . ?
C32 C31 C36 C35 -1.1(5) . . . . ?
C32 C33 C34 C35 -0.9(5) . . . . ?
C33 C34 C35 C36 0.8(5) . . . . ?
C34 C35 C36 N2 -177.7(3) . . . . ?
C34 C35 C36 C31 0.2(5) . . . . ?
C36 N2 C27 C26 -77.7(3) . . . . ?
C36 N2 C27 C28 49.2(3) . . . . ?
C36 C31 C32 C33 1.0(5) . . . . ?
C37 C29 C30 O6 -61.2(3) . . . . ?
C37 C29 C30 C31 -171.2(2) . . . . ?
C37 C29 C39 O9 -97.9(4) . . . . ?
C37 C29 C39 O10 82.1(3) . . . . ?
C38 O8 C37 O7 0.3(6) . . . . ?
C38 O8 C37 C29 -178.0(3) . . . . ?
C39 C29 C30 O6 -178.4(2) . . . . ?
C39 C29 C30 C31 71.5(3) . . . . ?
C39 C29 C37 O7 -113.9(4) . . . . ?
C39 C29 C37 O8 64.4(3) . . . . ?
C40 O10 C39 O9 -1.0(5) . . . . ?
C40 O10 C39 C29 179.0(3) . . . . ?

_olex2_date_sample_data_collection 2016-06-29
_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_wangzhh_0228_2
_database_code_depnum_ccdc_archive 'CCDC 1539625'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Br N O5'
_chemical_formula_sum            'C20 H18 Br N O5'
_chemical_formula_weight         432.26
_chemical_absolute_configuration ad
_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'
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'

_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      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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.8280(3)
_cell_length_b                   11.7422(5)
_cell_length_c                   23.4879(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1883.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1580
_cell_measurement_theta_min      3.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73588
_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_absorpt_special_details   ?
_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    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.451
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   38.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000 -180.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0137857000
_diffrn_orient_matrix_UB_12      0.0336434000
_diffrn_orient_matrix_UB_13      -0.0247529000
_diffrn_orient_matrix_UB_21      0.0132838000
_diffrn_orient_matrix_UB_22      0.0501093000
_diffrn_orient_matrix_UB_23      0.0164175000
_diffrn_orient_matrix_UB_31      0.1021160000
_diffrn_orient_matrix_UB_32      -0.0019642000
_diffrn_orient_matrix_UB_33      -0.0054784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                2403
_reflns_number_total             3367
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 670 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.049
_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)+(0.0343P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1013
_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:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_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
Br1 Br 0.61853(14) 0.90707(7) 0.12210(4) 0.0885(4) Uani 1 1 d . . . . .
O1 O 1.2654(5) 1.2920(3) 0.10617(16) 0.0395(10) Uani 1 1 d . . . . .
O2 O 1.0966(7) 1.1586(4) 0.26316(19) 0.0603(13) Uani 1 1 d . . . . .
O3 O 0.9602(6) 1.3245(4) 0.28682(17) 0.0515(12) Uani 1 1 d . . . . .
O4 O 1.4729(6) 1.3294(4) 0.2233(2) 0.0567(13) Uani 1 1 d . . . . .
O5 O 1.2991(5) 1.4900(3) 0.2198(2) 0.0497(12) Uani 1 1 d . . . . .
N1 N 1.0888(6) 1.3340(4) 0.07674(19) 0.0353(11) Uani 1 1 d . . . . .
C1 C 0.9621(8) 1.2362(5) 0.0824(2) 0.0371(14) Uani 1 1 d . . . . .
C2 C 0.8037(9) 1.2088(5) 0.0486(2) 0.0452(16) Uani 1 1 d . . . . .
H2 H 0.7674 1.2545 0.0181 0.054 Uiso 1 1 calc R . . . .
C3 C 0.7010(9) 1.1110(6) 0.0617(3) 0.0508(17) Uani 1 1 d . . . . .
H3 H 0.5942 1.0896 0.0396 0.061 Uiso 1 1 calc R . . . .
C4 C 0.7563(10) 1.0454(5) 0.1072(3) 0.0499(16) Uani 1 1 d . . . . .
C5 C 0.9150(9) 1.0721(5) 0.1420(2) 0.0446(16) Uani 1 1 d . . . . .
H5 H 0.9499 1.0269 0.1729 0.054 Uiso 1 1 calc R . . . .
C6 C 1.0164(8) 1.1685(4) 0.1283(2) 0.0346(13) Uani 1 1 d . . . . .
C7 C 1.1897(8) 1.2281(5) 0.1544(2) 0.0337(13) Uani 1 1 d . . . . .
H7 H 1.2863 1.1740 0.1692 0.040 Uiso 1 1 calc R . . . .
C8 C 1.1291(8) 1.3163(4) 0.1995(2) 0.0304(12) Uani 1 1 d . . . . .
C9 C 0.9702(7) 1.3946(4) 0.1745(2) 0.0304(12) Uani 1 1 d . . . . .
H9A H 0.9571 1.4616 0.1983 0.036 Uiso 1 1 calc R . . . .
H9B H 0.8457 1.3548 0.1746 0.036 Uiso 1 1 calc R . . . .
C10 C 1.0196(7) 1.4316(4) 0.1132(2) 0.0324(12) Uani 1 1 d . . . . .
H10 H 1.1290 1.4853 0.1160 0.039 Uiso 1 1 calc R . . . .
C11 C 0.8583(8) 1.4917(5) 0.0810(2) 0.0310(13) Uani 1 1 d . . . . .
C12 C 0.9078(9) 1.5770(5) 0.0426(2) 0.0419(15) Uani 1 1 d . . . . .
H12 H 1.0373 1.6011 0.0404 0.050 Uiso 1 1 calc R . . . .
C13 C 0.7705(10) 1.6267(5) 0.0078(3) 0.0526(18) Uani 1 1 d . . . . .
H13 H 0.8076 1.6835 -0.0176 0.063 Uiso 1 1 calc R . . . .
C14 C 0.5785(10) 1.5925(6) 0.0106(3) 0.0568(18) Uani 1 1 d . . . . .
H14 H 0.4849 1.6253 -0.0130 0.068 Uiso 1 1 calc R . . . .
C15 C 0.5267(9) 1.5093(6) 0.0487(3) 0.0547(19) Uani 1 1 d . . . . .
H15 H 0.3968 1.4859 0.0507 0.066 Uiso 1 1 calc R . . . .
C16 C 0.6622(8) 1.4601(5) 0.0840(3) 0.0444(16) Uani 1 1 d . . . . .
H16 H 0.6228 1.4052 0.1101 0.053 Uiso 1 1 calc R . . . .
C17 C 1.0622(8) 1.2562(5) 0.2528(2) 0.0362(14) Uani 1 1 d . . . . .
C18 C 0.8902(11) 1.2742(6) 0.3393(3) 0.070(2) Uani 1 1 d . . . . .
H18A H 0.8107 1.2090 0.3307 0.105 Uiso 1 1 calc GR . . . .
H18B H 0.8137 1.3292 0.3598 0.105 Uiso 1 1 calc GR . . . .
H18C H 0.9999 1.2512 0.3621 0.105 Uiso 1 1 calc GR . . . .
C19 C 1.3221(8) 1.3791(5) 0.2158(2) 0.0349(14) Uani 1 1 d . . . . .
C20 C 1.4754(10) 1.5554(6) 0.2341(4) 0.071(2) Uani 1 1 d . . . . .
H20A H 1.5583 1.5608 0.2012 0.106 Uiso 1 1 calc GR . . . .
H20B H 1.5449 1.5177 0.2642 0.106 Uiso 1 1 calc GR . . . .
H20C H 1.4385 1.6304 0.2462 0.106 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
Br1 C4 1.909(6) . ?
O1 N1 1.475(5) . ?
O1 C7 1.453(6) . ?
O2 C17 1.195(7) . ?
O3 C17 1.328(7) . ?
O3 C18 1.447(7) . ?
O4 C19 1.197(6) . ?
O5 C19 1.314(6) . ?
O5 C20 1.467(7) . ?
N1 C1 1.443(7) . ?
N1 C10 1.507(7) . ?
C1 C2 1.380(8) . ?
C1 C6 1.390(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 C5 1.394(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(7) . ?
C6 C7 1.505(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.538(7) . ?
C8 C9 1.538(7) . ?
C8 C17 1.509(8) . ?
C8 C19 1.558(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.540(7) . ?
C10 H10 0.9800 . ?
C10 C11 1.511(7) . ?
C11 C12 1.390(7) . ?
C11 C16 1.391(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(8) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C7 O1 N1 104.3(3) . . ?
C17 O3 C18 116.1(5) . . ?
C19 O5 C20 115.9(5) . . ?
O1 N1 C10 104.1(4) . . ?
C1 N1 O1 100.4(4) . . ?
C1 N1 C10 111.4(4) . . ?
C2 C1 N1 127.1(5) . . ?
C2 C1 C6 121.4(5) . . ?
C6 C1 N1 111.5(5) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.7(6) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(6) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 Br1 119.0(5) . . ?
C3 C4 C5 123.0(6) . . ?
C5 C4 Br1 117.9(5) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 C4 116.3(6) . . ?
C6 C5 H5 121.9 . . ?
C1 C6 C7 105.0(5) . . ?
C5 C6 C1 121.5(5) . . ?
C5 C6 C7 133.5(5) . . ?
O1 C7 C6 101.7(4) . . ?
O1 C7 H7 111.9 . . ?
O1 C7 C8 106.5(4) . . ?
C6 C7 H7 111.9 . . ?
C6 C7 C8 112.5(4) . . ?
C8 C7 H7 111.9 . . ?
C7 C8 C9 109.2(4) . . ?
C7 C8 C19 105.1(4) . . ?
C9 C8 C19 114.1(4) . . ?
C17 C8 C7 109.8(4) . . ?
C17 C8 C9 112.5(5) . . ?
C17 C8 C19 105.8(4) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C8 C9 C10 111.7(4) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N1 C10 C9 112.7(4) . . ?
N1 C10 H10 106.7 . . ?
N1 C10 C11 107.4(4) . . ?
C9 C10 H10 106.7 . . ?
C11 C10 C9 116.1(4) . . ?
C11 C10 H10 106.7 . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 C16 117.3(5) . . ?
C16 C11 C10 123.5(5) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(6) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(6) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(6) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(6) . . ?
C15 C16 H16 119.7 . . ?
O2 C17 O3 124.0(6) . . ?
O2 C17 C8 123.9(6) . . ?
O3 C17 C8 112.1(5) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O5 125.1(5) . . ?
O4 C19 C8 122.2(5) . . ?
O5 C19 C8 112.7(5) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C5 C6 176.6(4) . . . . ?
O1 N1 C1 C2 -157.2(5) . . . . ?
O1 N1 C1 C6 23.5(5) . . . . ?
O1 N1 C10 C9 -60.0(5) . . . . ?
O1 N1 C10 C11 170.9(4) . . . . ?
O1 C7 C8 C9 60.3(5) . . . . ?
O1 C7 C8 C17 -175.9(4) . . . . ?
O1 C7 C8 C19 -62.5(5) . . . . ?
N1 O1 C7 C6 39.9(4) . . . . ?
N1 O1 C7 C8 -78.0(4) . . . . ?
N1 C1 C2 C3 -179.7(5) . . . . ?
N1 C1 C6 C5 179.1(5) . . . . ?
N1 C1 C6 C7 0.6(6) . . . . ?
N1 C10 C11 C12 -87.1(5) . . . . ?
N1 C10 C11 C16 87.3(6) . . . . ?
C1 N1 C10 C9 47.4(5) . . . . ?
C1 N1 C10 C11 -81.7(5) . . . . ?
C1 C2 C3 C4 0.6(9) . . . . ?
C1 C6 C7 O1 -25.0(5) . . . . ?
C1 C6 C7 C8 88.6(5) . . . . ?
C2 C1 C6 C5 -0.2(9) . . . . ?
C2 C1 C6 C7 -178.8(5) . . . . ?
C2 C3 C4 Br1 -177.2(5) . . . . ?
C2 C3 C4 C5 -0.2(10) . . . . ?
C3 C4 C5 C6 -0.4(9) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
C4 C5 C6 C7 178.6(6) . . . . ?
C5 C6 C7 O1 156.7(6) . . . . ?
C5 C6 C7 C8 -89.7(7) . . . . ?
C6 C1 C2 C3 -0.4(8) . . . . ?
C6 C7 C8 C9 -50.3(6) . . . . ?
C6 C7 C8 C17 73.5(6) . . . . ?
C6 C7 C8 C19 -173.1(5) . . . . ?
C7 O1 N1 C1 -39.1(4) . . . . ?
C7 O1 N1 C10 76.3(4) . . . . ?
C7 C8 C9 C10 -43.7(5) . . . . ?
C7 C8 C17 O2 16.8(8) . . . . ?
C7 C8 C17 O3 -163.0(4) . . . . ?
C7 C8 C19 O4 -42.9(7) . . . . ?
C7 C8 C19 O5 136.6(5) . . . . ?
C8 C9 C10 N1 45.5(5) . . . . ?
C8 C9 C10 C11 169.9(4) . . . . ?
C9 C8 C17 O2 138.7(6) . . . . ?
C9 C8 C17 O3 -41.2(6) . . . . ?
C9 C8 C19 O4 -162.6(6) . . . . ?
C9 C8 C19 O5 17.0(7) . . . . ?
C9 C10 C11 C12 145.8(5) . . . . ?
C9 C10 C11 C16 -39.7(7) . . . . ?
C10 N1 C1 C2 93.0(6) . . . . ?
C10 N1 C1 C6 -86.3(5) . . . . ?
C10 C11 C12 C13 173.3(5) . . . . ?
C10 C11 C16 C15 -172.4(6) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
C12 C11 C16 C15 2.2(9) . . . . ?
C12 C13 C14 C15 0.5(10) . . . . ?
C13 C14 C15 C16 0.1(10) . . . . ?
C14 C15 C16 C11 -1.5(10) . . . . ?
C16 C11 C12 C13 -1.6(8) . . . . ?
C17 C8 C9 C10 -165.9(4) . . . . ?
C17 C8 C19 O4 73.2(7) . . . . ?
C17 C8 C19 O5 -107.2(6) . . . . ?
C18 O3 C17 O2 0.4(9) . . . . ?
C18 O3 C17 C8 -179.8(5) . . . . ?
C19 C8 C9 C10 73.6(5) . . . . ?
C19 C8 C17 O2 -96.2(6) . . . . ?
C19 C8 C17 O3 84.0(6) . . . . ?
C20 O5 C19 O4 0.6(10) . . . . ?
C20 O5 C19 C8 -179.0(5) . . . . ?


_olex2_date_sample_data_collection 2017-02-28
_olex2_submission_special_instructions 'No special instructions were received'
