# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_171102_s1_lmc
_database_code_depnum_ccdc_archive 'CCDC 1894501'
loop_
_audit_author_name
_audit_author_address
'Mengchen Liu'
;West China School of Pharmacy, West China Hospital, Sichuan University
China
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H25 N O6'
_chemical_formula_sum            'C21 H25 N O6'
_chemical_formula_weight         387.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5802(4)
_cell_length_b                   22.7364(9)
_cell_length_c                   9.9113(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.471(4)
_cell_angle_gamma                90
_cell_volume                     1887.90(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5020
_cell_measurement_theta_min      3.9620
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80636
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.989
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   46.00   0.8000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   55.40   0.8000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   21.60   0.8000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -66.00  -34.80   0.8000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  120.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0064185000
_diffrn_orient_matrix_UB_12      -0.0227845000
_diffrn_orient_matrix_UB_13      0.0474156000
_diffrn_orient_matrix_UB_21      -0.0465120000
_diffrn_orient_matrix_UB_22      0.0186830000
_diffrn_orient_matrix_UB_23      0.0329865000
_diffrn_orient_matrix_UB_31      -0.0704381000
_diffrn_orient_matrix_UB_32      -0.0102630000
_diffrn_orient_matrix_UB_33      -0.0451161000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2796
_reflns_number_total             3857
_reflns_odcompleteness_completeness 99.77
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.3867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1033
_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:
 C2(H2), C4(H4), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,
 H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24583(14) 0.60308(5) 0.18179(11) 0.0492(3) Uani 1 1 d . . . . .
O2 O 0.15824(14) 0.54830(5) -0.01564(12) 0.0558(3) Uani 1 1 d . . . . .
O3 O 0.50184(14) 0.59058(5) 0.29947(10) 0.0477(3) Uani 1 1 d . . . . .
O4 O 0.58223(19) 0.64600(6) 0.48881(13) 0.0779(5) Uani 1 1 d . . . . .
O5 O 1.09007(17) 0.41931(7) 0.75798(15) 0.0783(5) Uani 1 1 d . . . . .
O6 O 0.9630(2) 0.36188(7) 0.60036(16) 0.0854(5) Uani 1 1 d . . . . .
N1 N 0.98582(19) 0.40958(8) 0.65643(16) 0.0566(4) Uani 1 1 d . . . . .
C1 C 0.22389(19) 0.60220(7) 0.03314(15) 0.0407(4) Uani 1 1 d . . . . .
C2 C 0.1136(2) 0.65100(8) -0.03753(18) 0.0514(5) Uani 1 1 d . . . . .
H2 H 0.0013 0.6392 -0.0524 0.062 Uiso 1 1 calc R . . . .
C3 C 0.1660(2) 0.65784(9) -0.17526(18) 0.0597(5) Uani 1 1 d . . . . .
H3A H 0.1542 0.6984 -0.2064 0.072 Uiso 1 1 calc R . . . .
H3B H 0.1016 0.6331 -0.2455 0.072 Uiso 1 1 calc R . . . .
C4 C 0.3437(2) 0.63898(8) -0.14845(16) 0.0491(4) Uani 1 1 d . . . . .
H4 H 0.3480 0.6034 -0.2032 0.059 Uiso 1 1 calc R . . . .
C5 C 0.4568(2) 0.68360(10) -0.19256(19) 0.0655(6) Uani 1 1 d . . . . .
H5A H 0.4545 0.6778 -0.2899 0.079 Uiso 1 1 calc R . . . .
H5B H 0.4165 0.7228 -0.1822 0.079 Uiso 1 1 calc R . . . .
C6 C 0.6305(2) 0.68073(10) -0.1131(2) 0.0706(6) Uani 1 1 d . . . . .
H6A H 0.6604 0.6397 -0.0976 0.085 Uiso 1 1 calc R . . . .
H6B H 0.6976 0.6975 -0.1704 0.085 Uiso 1 1 calc R . . . .
C7 C 0.6653(2) 0.71245(9) 0.0259(2) 0.0658(6) Uani 1 1 d . . . . .
H7A H 0.7796 0.7186 0.0537 0.079 Uiso 1 1 calc R . . . .
H7B H 0.6152 0.7509 0.0131 0.079 Uiso 1 1 calc R . . . .
C8 C 0.6101(2) 0.68159(8) 0.14307(18) 0.0494(4) Uani 1 1 d . . . . .
H8A H 0.6362 0.7063 0.2246 0.059 Uiso 1 1 calc R . . . .
H8B H 0.6701 0.6454 0.1638 0.059 Uiso 1 1 calc R . . . .
C9 C 0.43286(18) 0.66686(7) 0.11638(15) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.3844(2) 0.63449(8) 0.23715(16) 0.0442(4) Uani 1 1 d . . . . .
H10 H 0.3653 0.6625 0.3069 0.053 Uiso 1 1 calc R . . . .
C11 C 0.38265(19) 0.62012(7) 0.00361(14) 0.0356(4) Uani 1 1 d . . . . .
H11 H 0.4587(17) 0.5891(6) 0.0195(13) 0.028(4) Uiso 1 1 d . . . . .
C12 C 0.1461(2) 0.70595(8) 0.0523(2) 0.0582(5) Uani 1 1 d . . . . .
H12A H 0.1104 0.6994 0.1376 0.070 Uiso 1 1 calc R . . . .
H12B H 0.0858 0.7387 0.0044 0.070 Uiso 1 1 calc R . . . .
C13 C 0.3242(2) 0.72155(7) 0.08634(18) 0.0493(4) Uani 1 1 d . . . . .
H13A H 0.3460 0.7473 0.1663 0.059 Uiso 1 1 calc R . . . .
H13B H 0.3497 0.7429 0.0092 0.059 Uiso 1 1 calc R . . . .
C14 C 0.5876(2) 0.60112(8) 0.42663(16) 0.0470(4) Uani 1 1 d . . . . .
C15 C 0.68996(19) 0.55001(7) 0.48349(14) 0.0404(4) Uani 1 1 d . . . . .
C16 C 0.8016(2) 0.55758(8) 0.60654(16) 0.0492(4) Uani 1 1 d . . . . .
H16 H 0.8108 0.5940 0.6504 0.059 Uiso 1 1 calc R . . . .
C17 C 0.8987(2) 0.51204(8) 0.66419(16) 0.0490(4) Uani 1 1 d . . . . .
H17 H 0.9743 0.5172 0.7460 0.059 Uiso 1 1 calc R . . . .
C18 C 0.88095(19) 0.45871(8) 0.59776(15) 0.0425(4) Uani 1 1 d . . . . .
C19 C 0.7701(2) 0.44930(8) 0.47778(16) 0.0503(4) Uani 1 1 d . . . . .
H19 H 0.7593 0.4124 0.4362 0.060 Uiso 1 1 calc R . . . .
C20 C 0.6747(2) 0.49557(8) 0.41987(16) 0.0477(4) Uani 1 1 d . . . . .
H20 H 0.5998 0.4901 0.3377 0.057 Uiso 1 1 calc R . . . .
C21 C 0.2568(2) 0.49808(8) 0.0229(2) 0.0633(5) Uani 1 1 d . . . . .
H21A H 0.3116 0.5016 0.1178 0.095 Uiso 1 1 calc GR . . . .
H21B H 0.3334 0.4955 -0.0345 0.095 Uiso 1 1 calc GR . . . .
H21C H 0.1918 0.4633 0.0115 0.095 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
O1 C1 1.4445(18) . ?
O1 C10 1.3939(19) . ?
O2 C1 1.3913(19) . ?
O2 C21 1.423(2) . ?
O3 C10 1.4576(19) . ?
O3 C14 1.3367(18) . ?
O4 C14 1.198(2) . ?
O5 N1 1.2138(19) . ?
O6 N1 1.215(2) . ?
N1 C18 1.473(2) . ?
C1 C2 1.527(2) . ?
C1 C11 1.510(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(3) . ?
C2 C12 1.525(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.551(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.532(3) . ?
C4 C11 1.533(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.529(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.518(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(2) . ?
C9 C10 1.537(2) . ?
C9 C11 1.535(2) . ?
C9 C13 1.544(2) . ?
C10 H10 0.9800 . ?
C11 H11 0.951(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.534(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.492(2) . ?
C15 C16 1.389(2) . ?
C15 C20 1.382(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(2) . ?
C18 C19 1.370(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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 C1 108.71(12) . . ?
C1 O2 C21 116.17(13) . . ?
C14 O3 C10 117.78(13) . . ?
O5 N1 O6 124.00(18) . . ?
O5 N1 C18 117.84(17) . . ?
O6 N1 C18 118.16(16) . . ?
O1 C1 C2 112.91(14) . . ?
O1 C1 C11 105.64(12) . . ?
O2 C1 O1 108.69(13) . . ?
O2 C1 C2 108.45(12) . . ?
O2 C1 C11 119.00(14) . . ?
C11 C1 C2 102.17(13) . . ?
C1 C2 H2 111.2 . . ?
C1 C2 C3 102.14(14) . . ?
C3 C2 H2 111.2 . . ?
C12 C2 C1 108.09(14) . . ?
C12 C2 H2 111.2 . . ?
C12 C2 C3 112.63(16) . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C2 C3 C4 106.60(13) . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
C3 C4 H4 106.7 . . ?
C5 C4 C3 115.36(15) . . ?
C5 C4 H4 106.7 . . ?
C5 C4 C11 116.67(14) . . ?
C11 C4 C3 104.09(14) . . ?
C11 C4 H4 106.7 . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 C4 115.60(16) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 115.05(18) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 116.10(16) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C7 C8 C9 115.70(14) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C8 C9 C10 113.44(13) . . ?
C8 C9 C11 113.04(13) . . ?
C8 C9 C13 113.25(14) . . ?
C10 C9 C13 106.41(13) . . ?
C11 C9 C10 98.91(12) . . ?
C11 C9 C13 110.76(12) . . ?
O1 C10 O3 105.59(13) . . ?
O1 C10 C9 106.86(12) . . ?
O1 C10 H10 110.6 . . ?
O3 C10 C9 112.31(13) . . ?
O3 C10 H10 110.6 . . ?
C9 C10 H10 110.6 . . ?
C1 C11 C4 104.58(13) . . ?
C1 C11 C9 99.71(12) . . ?
C1 C11 H11 112.6(8) . . ?
C4 C11 C9 119.31(13) . . ?
C4 C11 H11 111.5(8) . . ?
C9 C11 H11 108.6(8) . . ?
C2 C12 H12A 109.3 . . ?
C2 C12 H12B 109.3 . . ?
C2 C12 C13 111.44(15) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C9 C13 H13A 109.0 . . ?
C9 C13 H13B 109.0 . . ?
C12 C13 C9 112.80(14) . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O3 C14 C15 112.07(14) . . ?
O4 C14 O3 124.29(16) . . ?
O4 C14 C15 123.64(15) . . ?
C16 C15 C14 118.24(15) . . ?
C20 C15 C14 122.35(14) . . ?
C20 C15 C16 119.40(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.86(16) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.17(15) . . ?
C18 C17 H17 120.9 . . ?
C17 C18 N1 119.06(15) . . ?
C19 C18 N1 118.35(16) . . ?
C19 C18 C17 122.58(16) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.72(17) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.24(15) . . ?
C19 C20 H20 119.9 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 156.42(13) . . . . ?
O1 C1 C2 C12 37.46(19) . . . . ?
O1 C1 C11 C4 -161.51(13) . . . . ?
O1 C1 C11 C9 -37.61(14) . . . . ?
O2 C1 C2 C3 -83.07(16) . . . . ?
O2 C1 C2 C12 157.97(14) . . . . ?
O2 C1 C11 C4 76.10(17) . . . . ?
O2 C1 C11 C9 -160.00(13) . . . . ?
O3 C14 C15 C16 171.25(15) . . . . ?
O3 C14 C15 C20 -10.3(2) . . . . ?
O4 C14 C15 C16 -9.5(3) . . . . ?
O4 C14 C15 C20 168.99(19) . . . . ?
O5 N1 C18 C17 -3.9(2) . . . . ?
O5 N1 C18 C19 175.58(16) . . . . ?
O6 N1 C18 C17 176.21(17) . . . . ?
O6 N1 C18 C19 -4.3(2) . . . . ?
N1 C18 C19 C20 -178.05(15) . . . . ?
C1 O1 C10 O3 -106.72(13) . . . . ?
C1 O1 C10 C9 13.04(17) . . . . ?
C1 C2 C3 C4 -27.80(18) . . . . ?
C1 C2 C12 C13 52.7(2) . . . . ?
C2 C1 C11 C4 -43.22(16) . . . . ?
C2 C1 C11 C9 80.68(14) . . . . ?
C2 C3 C4 C5 -127.25(16) . . . . ?
C2 C3 C4 C11 1.87(19) . . . . ?
C2 C12 C13 C9 -39.5(2) . . . . ?
C3 C2 C12 C13 -59.3(2) . . . . ?
C3 C4 C5 C6 153.27(17) . . . . ?
C3 C4 C11 C1 25.33(17) . . . . ?
C3 C4 C11 C9 -84.91(18) . . . . ?
C4 C5 C6 C7 -81.9(2) . . . . ?
C5 C4 C11 C1 153.66(16) . . . . ?
C5 C4 C11 C9 43.4(2) . . . . ?
C5 C6 C7 C8 75.5(2) . . . . ?
C6 C7 C8 C9 -56.7(2) . . . . ?
C7 C8 C9 C10 178.74(15) . . . . ?
C7 C8 C9 C11 67.2(2) . . . . ?
C7 C8 C9 C13 -59.8(2) . . . . ?
C8 C9 C10 O1 -155.70(13) . . . . ?
C8 C9 C10 O3 -40.37(18) . . . . ?
C8 C9 C11 C1 163.17(13) . . . . ?
C8 C9 C11 C4 -83.94(18) . . . . ?
C8 C9 C13 C12 177.07(14) . . . . ?
C10 O1 C1 O2 144.70(13) . . . . ?
C10 O1 C1 C2 -94.93(15) . . . . ?
C10 O1 C1 C11 15.93(16) . . . . ?
C10 O3 C14 O4 -5.4(3) . . . . ?
C10 O3 C14 C15 173.83(13) . . . . ?
C10 C9 C11 C1 42.89(14) . . . . ?
C10 C9 C11 C4 155.79(14) . . . . ?
C10 C9 C13 C12 -57.64(18) . . . . ?
C11 C1 C2 C3 43.43(16) . . . . ?
C11 C1 C2 C12 -75.54(16) . . . . ?
C11 C4 C5 C6 30.6(3) . . . . ?
C11 C9 C10 O1 -35.72(15) . . . . ?
C11 C9 C10 O3 79.61(14) . . . . ?
C11 C9 C13 C12 48.87(19) . . . . ?
C12 C2 C3 C4 87.91(18) . . . . ?
C13 C9 C10 O1 79.12(15) . . . . ?
C13 C9 C10 O3 -165.55(12) . . . . ?
C13 C9 C11 C1 -68.52(15) . . . . ?
C13 C9 C11 C4 44.37(19) . . . . ?
C14 O3 C10 O1 -133.52(14) . . . . ?
C14 O3 C10 C9 110.39(16) . . . . ?
C14 C15 C16 C17 179.69(16) . . . . ?
C14 C15 C20 C19 -178.77(16) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C15 C20 C19 -0.3(3) . . . . ?
C16 C17 C18 N1 178.88(15) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C18 C19 C20 C15 -0.9(3) . . . . ?
C20 C15 C16 C17 1.2(3) . . . . ?
C21 O2 C1 O1 -66.19(18) . . . . ?
C21 O2 C1 C2 170.72(15) . . . . ?
C21 O2 C1 C11 54.7(2) . . . . ?


_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_161117_s5_lmc
_database_code_depnum_ccdc_archive 'CCDC 1894504'
loop_
_audit_author_name
_audit_author_address
'Mengchen Liu'
;West China School of Pharmacy, West China Hospital, Sichuan University
China
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;
_audit_creation_date             2016-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H23 N O7'
_chemical_formula_sum            'C21 H23 N O7'
_chemical_formula_weight         401.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   25.935(2)
_cell_length_b                   6.1347(4)
_cell_length_c                   12.1361(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1930.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1421
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8760
_cell_measurement_theta_min      3.2900
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81104
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5825
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.142
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   12.40   0.7000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -28.00   28.00   0.7000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -38.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   67.30   0.7000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000 -150.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0272736000
_diffrn_orient_matrix_UB_12      -0.0037635000
_diffrn_orient_matrix_UB_13      0.0034050000
_diffrn_orient_matrix_UB_21      0.0016027000
_diffrn_orient_matrix_UB_22      0.0068655000
_diffrn_orient_matrix_UB_23      0.0582493000
_diffrn_orient_matrix_UB_31      -0.0009817000
_diffrn_orient_matrix_UB_32      0.1154054000
_diffrn_orient_matrix_UB_33      -0.0033373000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.446
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.493
_reflns_number_gt                2306
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.70
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.017
_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)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1031
_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:
 C1(H1), C2(H2), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69600(11) 0.4411(4) 0.5705(2) 0.0619(8) Uani 1 1 d . . . . .
O2 O 0.61394(14) 0.9700(4) 0.1527(3) 0.0837(10) Uani 1 1 d . . . . .
O3 O 0.64871(13) 0.6546(4) 0.1922(2) 0.0774(10) Uani 1 1 d . . . . .
O4 O 0.59623(11) 0.5064(4) 0.6193(2) 0.0556(7) Uani 1 1 d . . . . .
O5 O 0.63056(12) 0.5653(4) 0.7861(2) 0.0635(8) Uani 1 1 d . . . . .
O6 O 0.47540(14) -0.4129(5) 0.7882(3) 0.0862(10) Uani 1 1 d . . . . .
O7 O 0.50778(13) -0.3823(5) 0.9493(3) 0.0830(10) Uani 1 1 d . . . . .
N1 N 0.50103(14) -0.3171(5) 0.8568(3) 0.0576(9) Uani 1 1 d . . . . .
C1 C 0.70723(13) 0.8003(5) 0.4986(3) 0.0416(8) Uani 1 1 d . . . . .
H1 H 0.7009 0.9466 0.5281 0.050 Uiso 1 1 calc R . . . .
C2 C 0.74926(14) 0.7834(5) 0.4141(3) 0.0485(9) Uani 1 1 d . . . . .
H2 H 0.7678 0.6442 0.4143 0.058 Uiso 1 1 calc R . . . .
C3 C 0.78251(17) 0.9804(7) 0.3869(4) 0.0691(12) Uani 1 1 d . . . . .
H3A H 0.7729 1.1009 0.4344 0.083 Uiso 1 1 calc R . . . .
H3B H 0.8184 0.9456 0.4009 0.083 Uiso 1 1 calc R . . . .
C4 C 0.77621(18) 1.0474(9) 0.2685(5) 0.0884(15) Uani 1 1 d . . . . .
H4A H 0.7759 0.9165 0.2237 0.106 Uiso 1 1 calc R . . . .
H4B H 0.8064 1.1312 0.2474 0.106 Uiso 1 1 calc R . . . .
C5 C 0.72907(16) 1.1792(6) 0.2400(4) 0.0627(12) Uani 1 1 d . . . . .
H5A H 0.7187 1.1396 0.1658 0.075 Uiso 1 1 calc R . . . .
H5B H 0.7392 1.3314 0.2381 0.075 Uiso 1 1 calc R . . . .
C6 C 0.68159(15) 1.1607(5) 0.3138(3) 0.0484(9) Uani 1 1 d . . . . .
H6A H 0.6552 1.2568 0.2848 0.058 Uiso 1 1 calc R . . . .
H6B H 0.6907 1.2139 0.3865 0.058 Uiso 1 1 calc R . . . .
C7 C 0.65825(13) 0.9335(4) 0.3265(3) 0.0361(8) Uani 1 1 d . . . . .
C8 C 0.61088(14) 0.9500(5) 0.4047(3) 0.0476(9) Uani 1 1 d . . . . .
H8A H 0.6180 1.0629 0.4586 0.057 Uiso 1 1 calc R . . . .
H8B H 0.5816 0.9983 0.3614 0.057 Uiso 1 1 calc R . . . .
C9 C 0.59476(14) 0.7430(5) 0.4674(3) 0.0498(9) Uani 1 1 d . . . . .
H9A H 0.5585 0.7562 0.4855 0.060 Uiso 1 1 calc R . . . .
H9B H 0.5982 0.6203 0.4175 0.060 Uiso 1 1 calc R . . . .
C10 C 0.62383(14) 0.6870(5) 0.5736(3) 0.0465(9) Uani 1 1 d . . . . .
H10 H 0.6223 0.8109 0.6244 0.056 Uiso 1 1 calc R . . . .
C11 C 0.68019(15) 0.6225(6) 0.5543(3) 0.0435(8) Uani 1 1 d . . . . .
C12 C 0.69438(12) 0.7686(5) 0.3770(3) 0.0372(8) Uani 1 1 d . . . . .
H12 H 0.6841 0.6184 0.3604 0.045 Uiso 1 1 calc R . . . .
C13 C 0.63822(14) 0.8584(5) 0.2146(3) 0.0451(9) Uani 1 1 d . . . . .
C14 C 0.6286(3) 0.5656(7) 0.0900(4) 0.106(2) Uani 1 1 d . . . . .
H14A H 0.6408 0.6512 0.0292 0.158 Uiso 1 1 calc GR . . . .
H14B H 0.5916 0.5689 0.0917 0.158 Uiso 1 1 calc GR . . . .
H14C H 0.6402 0.4178 0.0817 0.158 Uiso 1 1 calc GR . . . .
C15 C 0.60465(15) 0.4597(6) 0.7254(3) 0.0472(9) Uani 1 1 d . . . . .
C16 C 0.57595(13) 0.2587(5) 0.7576(3) 0.0432(8) Uani 1 1 d . . . . .
C17 C 0.54249(14) 0.1534(6) 0.6863(3) 0.0509(9) Uani 1 1 d . . . . .
H17 H 0.5369 0.2092 0.6161 0.061 Uiso 1 1 calc R . . . .
C18 C 0.51729(15) -0.0346(6) 0.7193(3) 0.0520(10) Uani 1 1 d . . . . .
H18 H 0.4948 -0.1065 0.6720 0.062 Uiso 1 1 calc R . . . .
C19 C 0.52631(14) -0.1119(5) 0.8230(3) 0.0460(9) Uani 1 1 d . . . . .
C20 C 0.55850(15) -0.0106(5) 0.8955(3) 0.0530(10) Uani 1 1 d . . . . .
H20 H 0.5637 -0.0680 0.9655 0.064 Uiso 1 1 calc R . . . .
C21 C 0.58328(14) 0.1780(5) 0.8636(3) 0.0469(9) Uani 1 1 d . . . . .
H21 H 0.6048 0.2509 0.9126 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.202(4) . ?
O2 C13 1.196(4) . ?
O3 C13 1.308(4) . ?
O3 C14 1.451(5) . ?
O4 C10 1.431(4) . ?
O4 C15 1.337(4) . ?
O5 C15 1.189(4) . ?
O6 N1 1.216(5) . ?
O7 N1 1.205(5) . ?
N1 C19 1.478(5) . ?
C1 H1 0.9800 . ?
C1 C2 1.500(5) . ?
C1 C11 1.463(5) . ?
C1 C12 1.525(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.520(5) . ?
C2 C12 1.496(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.504(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.506(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.527(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.527(4) . ?
C7 C8 1.555(5) . ?
C7 C12 1.509(4) . ?
C7 C13 1.526(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.539(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.532(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.532(5) . ?
C12 H12 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.492(5) . ?
C16 C17 1.385(5) . ?
C16 C21 1.391(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(5) . ?
C19 C20 1.362(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(5) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O3 C14 117.5(3) . . ?
C15 O4 C10 117.2(3) . . ?
O6 N1 C19 117.7(4) . . ?
O7 N1 O6 123.9(4) . . ?
O7 N1 C19 118.5(4) . . ?
C2 C1 H1 115.7 . . ?
C2 C1 C12 59.3(2) . . ?
C11 C1 H1 115.7 . . ?
C11 C1 C2 127.8(3) . . ?
C11 C1 C12 104.3(3) . . ?
C12 C1 H1 115.7 . . ?
C1 C2 H2 114.5 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 114.5 . . ?
C12 C2 C1 61.2(2) . . ?
C12 C2 H2 114.5 . . ?
C12 C2 C3 121.5(3) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
C3 C4 C5 117.0(4) . . ?
H4A C4 H4B 107.3 . . ?
C5 C4 H4A 108.0 . . ?
C5 C4 H4B 108.0 . . ?
C4 C5 H5A 107.6 . . ?
C4 C5 H5B 107.6 . . ?
C4 C5 C6 118.7(3) . . ?
H5A C5 H5B 107.1 . . ?
C6 C5 H5A 107.6 . . ?
C6 C5 H5B 107.6 . . ?
C5 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C5 C6 C7 116.5(3) . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C6 C7 C8 108.4(2) . . ?
C12 C7 C6 114.0(3) . . ?
C12 C7 C8 106.7(3) . . ?
C12 C7 C13 111.7(3) . . ?
C13 C7 C6 108.7(3) . . ?
C13 C7 C8 107.1(3) . . ?
C7 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
C8 C9 H9A 107.8 . . ?
C8 C9 H9B 107.8 . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9A 107.8 . . ?
C10 C9 H9B 107.8 . . ?
O4 C10 C9 104.7(3) . . ?
O4 C10 H10 109.6 . . ?
O4 C10 C11 109.6(3) . . ?
C9 C10 H10 109.6 . . ?
C9 C10 C11 113.5(3) . . ?
C11 C10 H10 109.6 . . ?
O1 C11 C1 127.0(3) . . ?
O1 C11 C10 122.7(3) . . ?
C1 C11 C10 109.6(3) . . ?
C1 C12 H12 112.2 . . ?
C2 C12 C1 59.5(2) . . ?
C2 C12 C7 132.2(3) . . ?
C2 C12 H12 112.2 . . ?
C7 C12 C1 116.3(3) . . ?
C7 C12 H12 112.2 . . ?
O2 C13 O3 121.8(3) . . ?
O2 C13 C7 124.4(3) . . ?
O3 C13 C7 113.8(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C16 110.3(3) . . ?
O5 C15 O4 124.9(3) . . ?
O5 C15 C16 124.8(4) . . ?
C17 C16 C15 122.3(3) . . ?
C17 C16 C21 119.8(3) . . ?
C21 C16 C15 117.9(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.3(4) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 N1 118.4(3) . . ?
C20 C19 N1 118.8(3) . . ?
C20 C19 C18 122.8(3) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C16 C21 H21 120.2 . . ?
C20 C21 C16 119.6(3) . . ?
C20 C21 H21 120.2 . . ?

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
O4 C10 C11 O1 4.1(5) . . . . ?
O4 C10 C11 C1 175.0(3) . . . . ?
O4 C15 C16 C17 -5.0(5) . . . . ?
O4 C15 C16 C21 175.6(3) . . . . ?
O5 C15 C16 C17 173.8(4) . . . . ?
O5 C15 C16 C21 -5.7(5) . . . . ?
O6 N1 C19 C18 3.6(5) . . . . ?
O6 N1 C19 C20 -174.8(4) . . . . ?
O7 N1 C19 C18 -177.9(4) . . . . ?
O7 N1 C19 C20 3.6(5) . . . . ?
N1 C19 C20 C21 178.3(3) . . . . ?
C1 C2 C3 C4 -117.6(4) . . . . ?
C1 C2 C12 C7 99.2(4) . . . . ?
C2 C1 C11 O1 25.4(6) . . . . ?
C2 C1 C11 C10 -145.0(3) . . . . ?
C2 C1 C12 C7 -125.4(3) . . . . ?
C2 C3 C4 C5 79.6(5) . . . . ?
C3 C2 C12 C1 -109.9(4) . . . . ?
C3 C2 C12 C7 -10.7(6) . . . . ?
C3 C4 C5 C6 -24.4(6) . . . . ?
C4 C5 C6 C7 -58.8(5) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C5 C6 C7 C12 61.1(4) . . . . ?
C5 C6 C7 C13 -64.2(4) . . . . ?
C6 C7 C8 C9 -155.4(3) . . . . ?
C6 C7 C12 C1 69.6(4) . . . . ?
C6 C7 C12 C2 -2.0(5) . . . . ?
C6 C7 C13 O2 -44.3(5) . . . . ?
C6 C7 C13 O3 137.6(3) . . . . ?
C7 C8 C9 C10 82.2(4) . . . . ?
C8 C7 C12 C1 -49.9(3) . . . . ?
C8 C7 C12 C2 -121.6(4) . . . . ?
C8 C7 C13 O2 72.5(4) . . . . ?
C8 C7 C13 O3 -105.6(3) . . . . ?
C8 C9 C10 O4 172.8(3) . . . . ?
C8 C9 C10 C11 -67.7(4) . . . . ?
C9 C10 C11 O1 -112.6(3) . . . . ?
C9 C10 C11 C1 58.3(4) . . . . ?
C10 O4 C15 O5 5.3(6) . . . . ?
C10 O4 C15 C16 -175.9(3) . . . . ?
C11 C1 C2 C3 -163.9(4) . . . . ?
C11 C1 C2 C12 84.4(4) . . . . ?
C11 C1 C12 C2 -125.8(3) . . . . ?
C11 C1 C12 C7 108.8(3) . . . . ?
C12 C1 C2 C3 111.7(4) . . . . ?
C12 C1 C11 O1 87.4(4) . . . . ?
C12 C1 C11 C10 -83.0(3) . . . . ?
C12 C2 C3 C4 -44.7(6) . . . . ?
C12 C7 C8 C9 -32.3(4) . . . . ?
C12 C7 C13 O2 -171.0(4) . . . . ?
C12 C7 C13 O3 10.9(4) . . . . ?
C13 C7 C8 C9 87.5(4) . . . . ?
C13 C7 C12 C1 -166.7(3) . . . . ?
C13 C7 C12 C2 121.7(4) . . . . ?
C14 O3 C13 O2 -1.5(6) . . . . ?
C14 O3 C13 C7 176.6(4) . . . . ?
C15 O4 C10 C9 -163.0(3) . . . . ?
C15 O4 C10 C11 74.9(4) . . . . ?
C15 C16 C17 C18 179.0(3) . . . . ?
C15 C16 C21 C20 -178.3(3) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C17 C16 C21 C20 2.3(5) . . . . ?
C17 C18 C19 N1 -177.6(3) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C16 -1.5(5) . . . . ?
C21 C16 C17 C18 -1.5(6) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_171031_s3_lmc
_database_code_depnum_ccdc_archive 'CCDC 1894502'
loop_
_audit_author_name
_audit_author_address
'Mengchen Liu'
;West China School of Pharmacy, West China Hospital, Sichuan University
China
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H19 Br O4'
_chemical_formula_sum            'C15 H19 Br O4'
_chemical_formula_weight         343.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br1
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5237(4)
_cell_length_b                   12.453(2)
_cell_length_c                   17.0481(11)
_cell_angle_alpha                110.953(12)
_cell_angle_beta                 90.094(5)
_cell_angle_gamma                95.229(9)
_cell_volume                     1484.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2960
_cell_measurement_theta_min      3.5210
_shelx_estimated_absorpt_T_max   0.543
_shelx_estimated_absorpt_T_min   0.443
_exptl_absorpt_coefficient_mu    2.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85980
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10585
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.964
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00   12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00  -62.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -42.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -57.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   -2.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0042085000
_diffrn_orient_matrix_UB_12      0.0606528000
_diffrn_orient_matrix_UB_13      0.0158298000
_diffrn_orient_matrix_UB_21      0.0147047000
_diffrn_orient_matrix_UB_22      0.0013680000
_diffrn_orient_matrix_UB_23      0.0414679000
_diffrn_orient_matrix_UB_31      0.0934900000
_diffrn_orient_matrix_UB_32      0.0086096000
_diffrn_orient_matrix_UB_33      -0.0041490000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5929
_reflns_number_total             10585
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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 1.171.37.35 (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         0.596
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         10585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4528(10)
 0.5472(10)
2. 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
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C10(H10), C11(H11), C16(H16), C17(H17), C25(H25), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,
 H14B), C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B), C29(H29A,H29B)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.19150(9) 0.16604(7) 1.08357(4) 0.0674(3) Uani 1 1 d . . . . .
O1 O 0.6975(6) 0.1250(4) 0.7394(3) 0.0632(13) Uani 1 1 d . . . . .
O2 O 0.8621(5) 0.4389(3) 1.0739(2) 0.0616(12) Uani 1 1 d . . . . .
O3 O 0.4981(6) 0.3369(4) 0.9251(3) 0.0775(15) Uani 1 1 d . . . . .
O4 O 0.7011(6) 0.4082(4) 0.8576(3) 0.0776(14) Uani 1 1 d . . . . .
C1 C 1.0016(6) 0.1632(4) 1.0030(3) 0.0425(14) Uani 1 1 d . . . . .
H1 H 0.9535 0.0830 0.9726 0.051 Uiso 1 1 calc R . . . .
C2 C 0.8499(7) 0.2329(5) 1.0480(3) 0.0447(15) Uani 1 1 d . . . . .
H2 H 0.8520 0.2476 1.1084 0.054 Uiso 1 1 calc R . . . .
C3 C 0.6700(7) 0.1752(5) 1.0044(4) 0.0592(19) Uani 1 1 d . . . . .
H3A H 0.5783 0.2268 1.0269 0.071 Uiso 1 1 calc R . . . .
H3B H 0.6392 0.1052 1.0162 0.071 Uiso 1 1 calc R . . . .
C4 C 0.6740(7) 0.1449(5) 0.9092(3) 0.0454(17) Uani 1 1 d . . . . .
H4A H 0.5522 0.1266 0.8863 0.055 Uiso 1 1 calc R . . . .
H4B H 0.7355 0.0760 0.8850 0.055 Uiso 1 1 calc R . . . .
C5 C 0.7648(6) 0.2400(4) 0.8814(3) 0.0310(13) Uani 1 1 d . . . . .
C6 C 0.8098(8) 0.1912(5) 0.7878(4) 0.0433(15) Uani 1 1 d . . . . .
C7 C 0.9854(8) 0.2270(5) 0.7608(3) 0.0624(17) Uani 1 1 d . . . . .
H7A H 1.0091 0.3103 0.7865 0.075 Uiso 1 1 calc R . . . .
H7B H 0.9796 0.2072 0.7003 0.075 Uiso 1 1 calc R . . . .
C8 C 1.1389(8) 0.1714(6) 0.7836(4) 0.069(2) Uani 1 1 d . . . . .
H8A H 1.1676 0.1081 0.7339 0.082 Uiso 1 1 calc R . . . .
H8B H 1.2427 0.2279 0.7994 0.082 Uiso 1 1 calc R . . . .
C9 C 1.1061(7) 0.1255(5) 0.8540(4) 0.0535(19) Uani 1 1 d . . . . .
H9A H 1.2093 0.0878 0.8607 0.064 Uiso 1 1 calc R . . . .
H9B H 1.0044 0.0674 0.8377 0.064 Uiso 1 1 calc R . . . .
C10 C 1.0709(6) 0.2175(4) 0.9392(3) 0.0321(13) Uani 1 1 d . . . . .
H10 H 1.1843 0.2638 0.9620 0.039 Uiso 1 1 calc R . . . .
C11 C 0.9336(6) 0.3004(4) 0.9375(3) 0.0313(13) Uani 1 1 d . . . . .
H11 H 0.9882 0.3648 0.9226 0.038 Uiso 1 1 calc R . . . .
C12 C 0.8804(6) 0.3411(5) 1.0290(4) 0.0390(15) Uani 1 1 d . . . . .
C13 C 0.6362(8) 0.3329(5) 0.8908(4) 0.0496(16) Uani 1 1 d . . . . .
C14 C 0.6068(11) 0.5093(6) 0.8693(5) 0.117(3) Uani 1 1 d . . . . .
H14A H 0.5197 0.5152 0.9122 0.141 Uiso 1 1 calc R . . . .
H14B H 0.6918 0.5776 0.8901 0.141 Uiso 1 1 calc R . . . .
C15 C 0.5224(10) 0.5094(6) 0.7999(5) 0.106(3) Uani 1 1 d . . . . .
H15A H 0.6080 0.5079 0.7579 0.158 Uiso 1 1 calc GR . . . .
H15B H 0.4616 0.5779 0.8134 0.158 Uiso 1 1 calc GR . . . .
H15C H 0.4373 0.4425 0.7788 0.158 Uiso 1 1 calc GR . . . .
Br2 Br 0.66443(10) 0.15937(7) 0.23252(4) 0.0738(3) Uani 1 1 d . . . . .
O5 O 0.3563(5) 0.4346(4) 0.3903(2) 0.0612(12) Uani 1 1 d . . . . .
O6 O 0.2097(6) 0.1347(4) 0.5746(3) 0.0724(14) Uani 1 1 d . . . . .
O7 O 0.0093(6) 0.3426(4) 0.4955(3) 0.0710(14) Uani 1 1 d . . . . .
O8 O 0.2238(5) 0.4149(4) 0.5962(3) 0.0685(13) Uani 1 1 d . . . . .
C16 C 0.4858(6) 0.1573(5) 0.3149(3) 0.0434(14) Uani 1 1 d . . . . .
H16 H 0.4381 0.0770 0.3035 0.052 Uiso 1 1 calc R . . . .
C17 C 0.3320(7) 0.2268(5) 0.3113(3) 0.0475(15) Uani 1 1 d . . . . .
H17 H 0.3251 0.2406 0.2583 0.057 Uiso 1 1 calc R . . . .
C18 C 0.1567(7) 0.1731(6) 0.3308(4) 0.062(2) Uani 1 1 d . . . . .
H18A H 0.1196 0.1023 0.2841 0.074 Uiso 1 1 calc R . . . .
H18B H 0.0658 0.2258 0.3368 0.074 Uiso 1 1 calc R . . . .
C19 C 0.1715(7) 0.1462(5) 0.4113(4) 0.0546(19) Uani 1 1 d . . . . .
H19A H 0.2316 0.0767 0.3990 0.066 Uiso 1 1 calc R . . . .
H19B H 0.0520 0.1303 0.4283 0.066 Uiso 1 1 calc R . . . .
C20 C 0.2720(6) 0.2428(4) 0.4852(3) 0.0371(14) Uani 1 1 d . . . . .
C21 C 0.3205(8) 0.1953(5) 0.5546(4) 0.0486(16) Uani 1 1 d . . . . .
C22 C 0.5074(8) 0.2303(5) 0.5947(4) 0.0660(18) Uani 1 1 d . . . . .
H22A H 0.5101 0.2128 0.6457 0.079 Uiso 1 1 calc R . . . .
H22B H 0.5329 0.3133 0.6106 0.079 Uiso 1 1 calc R . . . .
C23 C 0.6557(7) 0.1708(6) 0.5380(4) 0.0570(19) Uani 1 1 d . . . . .
H23A H 0.7600 0.2263 0.5475 0.068 Uiso 1 1 calc R . . . .
H23B H 0.6885 0.1086 0.5551 0.068 Uiso 1 1 calc R . . . .
C24 C 0.6077(7) 0.1213(5) 0.4442(4) 0.0435(17) Uani 1 1 d . . . . .
H24A H 0.7059 0.0805 0.4149 0.052 Uiso 1 1 calc R . . . .
H24B H 0.5040 0.0652 0.4345 0.052 Uiso 1 1 calc R . . . .
C25 C 0.5681(6) 0.2093(4) 0.4067(3) 0.0369(14) Uani 1 1 d . . . . .
H25 H 0.6819 0.2532 0.4048 0.044 Uiso 1 1 calc R . . . .
C26 C 0.4371(6) 0.2987(4) 0.4545(3) 0.0306(14) Uani 1 1 d . . . . .
H26 H 0.4987 0.3633 0.5008 0.037 Uiso 1 1 calc R . . . .
C27 C 0.3735(6) 0.3372(6) 0.3860(4) 0.0420(15) Uani 1 1 d . . . . .
C28 C 0.1498(8) 0.3377(5) 0.5253(4) 0.0462(16) Uani 1 1 d . . . . .
C29 C 0.1312(10) 0.5180(6) 0.6380(4) 0.091(2) Uani 1 1 d . . . . .
H29A H 0.2187 0.5844 0.6614 0.109 Uiso 1 1 calc R . . . .
H29B H 0.0568 0.5320 0.5968 0.109 Uiso 1 1 calc R . . . .
C30 C 0.0236(9) 0.5062(6) 0.7028(5) 0.096(3) Uani 1 1 d . . . . .
H30A H -0.0668 0.4428 0.6795 0.144 Uiso 1 1 calc GR . . . .
H30B H -0.0319 0.5760 0.7295 0.144 Uiso 1 1 calc GR . . . .
H30C H 0.0965 0.4917 0.7436 0.144 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 C1 1.970(4) . ?
O1 C6 1.208(6) . ?
O2 C12 1.205(6) . ?
O3 C13 1.189(6) . ?
O4 C13 1.318(6) . ?
O4 C14 1.454(6) . ?
C1 C2 1.533(6) . ?
C1 C10 1.541(6) . ?
C2 C3 1.529(7) . ?
C2 C12 1.492(7) . ?
C3 C4 1.531(7) . ?
C4 C5 1.532(7) . ?
C5 C6 1.542(7) . ?
C5 C11 1.549(6) . ?
C5 C13 1.540(7) . ?
C6 C7 1.483(7) . ?
C7 C8 1.517(7) . ?
C8 C9 1.514(7) . ?
C9 C10 1.536(7) . ?
C10 C11 1.533(6) . ?
C11 C12 1.525(7) . ?
C14 C15 1.342(8) . ?
Br2 C16 1.950(5) . ?
O5 C27 1.208(6) . ?
O6 C21 1.204(6) . ?
O7 C28 1.188(6) . ?
O8 C28 1.328(6) . ?
O8 C29 1.467(6) . ?
C16 C17 1.520(6) . ?
C16 C25 1.566(6) . ?
C17 C18 1.515(7) . ?
C17 C27 1.510(7) . ?
C18 C19 1.531(7) . ?
C19 C20 1.534(7) . ?
C20 C21 1.557(7) . ?
C20 C26 1.551(6) . ?
C20 C28 1.527(7) . ?
C21 C22 1.519(8) . ?
C22 C23 1.540(7) . ?
C23 C24 1.524(7) . ?
C24 C25 1.503(7) . ?
C25 C26 1.559(6) . ?
C26 C27 1.504(7) . ?
C29 C30 1.413(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 C14 118.5(5) . . ?
C2 C1 Br1 111.2(4) . . ?
C2 C1 C10 106.3(4) . . ?
C10 C1 Br1 111.9(3) . . ?
C3 C2 C1 110.2(4) . . ?
C12 C2 C1 102.9(4) . . ?
C12 C2 C3 104.8(4) . . ?
C2 C3 C4 111.8(4) . . ?
C3 C4 C5 114.9(5) . . ?
C4 C5 C6 110.9(4) . . ?
C4 C5 C11 110.9(4) . . ?
C4 C5 C13 109.6(4) . . ?
C6 C5 C11 111.2(4) . . ?
C13 C5 C6 106.7(4) . . ?
C13 C5 C11 107.3(4) . . ?
O1 C6 C5 117.5(5) . . ?
O1 C6 C7 122.9(5) . . ?
C7 C6 C5 119.6(5) . . ?
C6 C7 C8 113.5(5) . . ?
C9 C8 C7 115.7(5) . . ?
C8 C9 C10 114.7(5) . . ?
C9 C10 C1 112.0(4) . . ?
C11 C10 C1 105.1(4) . . ?
C11 C10 C9 115.8(4) . . ?
C10 C11 C5 113.7(4) . . ?
C12 C11 C5 108.2(4) . . ?
C12 C11 C10 100.0(4) . . ?
O2 C12 C2 128.8(5) . . ?
O2 C12 C11 126.7(5) . . ?
C2 C12 C11 104.5(5) . . ?
O3 C13 O4 124.7(5) . . ?
O3 C13 C5 124.1(6) . . ?
O4 C13 C5 111.1(5) . . ?
C15 C14 O4 114.9(7) . . ?
C28 O8 C29 117.6(5) . . ?
C17 C16 Br2 112.1(4) . . ?
C17 C16 C25 107.1(4) . . ?
C25 C16 Br2 111.5(3) . . ?
C18 C17 C16 111.5(5) . . ?
C27 C17 C16 102.8(4) . . ?
C27 C17 C18 104.6(4) . . ?
C17 C18 C19 112.0(5) . . ?
C18 C19 C20 114.6(5) . . ?
C19 C20 C21 109.8(5) . . ?
C19 C20 C26 110.8(4) . . ?
C26 C20 C21 112.9(4) . . ?
C28 C20 C19 109.5(4) . . ?
C28 C20 C21 106.3(4) . . ?
C28 C20 C26 107.3(4) . . ?
O6 C21 C20 119.3(6) . . ?
O6 C21 C22 123.4(6) . . ?
C22 C21 C20 117.2(5) . . ?
C21 C22 C23 114.5(5) . . ?
C24 C23 C22 115.3(5) . . ?
C25 C24 C23 114.7(5) . . ?
C24 C25 C16 114.7(4) . . ?
C24 C25 C26 116.8(4) . . ?
C26 C25 C16 103.6(4) . . ?
C20 C26 C25 112.8(4) . . ?
C27 C26 C20 107.6(4) . . ?
C27 C26 C25 101.5(4) . . ?
O5 C27 C17 127.6(5) . . ?
O5 C27 C26 127.7(6) . . ?
C26 C27 C17 104.7(5) . . ?
O7 C28 O8 125.0(5) . . ?
O7 C28 C20 124.0(6) . . ?
O8 C28 C20 111.0(5) . . ?
C30 C29 O8 112.1(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 C1 C2 C3 -144.2(4) . . . . ?
Br1 C1 C2 C12 104.4(4) . . . . ?
Br1 C1 C10 C9 101.1(4) . . . . ?
Br1 C1 C10 C11 -132.4(3) . . . . ?
O1 C6 C7 C8 -105.8(6) . . . . ?
C1 C2 C3 C4 -48.8(6) . . . . ?
C1 C2 C12 O2 -142.2(5) . . . . ?
C1 C2 C12 C11 40.1(5) . . . . ?
C1 C10 C11 C5 -81.0(5) . . . . ?
C1 C10 C11 C12 34.1(5) . . . . ?
C2 C1 C10 C9 -137.4(4) . . . . ?
C2 C1 C10 C11 -10.8(5) . . . . ?
C2 C3 C4 C5 -44.4(7) . . . . ?
C3 C2 C12 O2 102.4(6) . . . . ?
C3 C2 C12 C11 -75.3(5) . . . . ?
C3 C4 C5 C6 164.0(4) . . . . ?
C3 C4 C5 C11 39.9(6) . . . . ?
C3 C4 C5 C13 -78.4(5) . . . . ?
C4 C5 C6 O1 43.4(6) . . . . ?
C4 C5 C6 C7 -137.0(5) . . . . ?
C4 C5 C11 C10 56.7(5) . . . . ?
C4 C5 C11 C12 -53.4(5) . . . . ?
C4 C5 C13 O3 9.4(7) . . . . ?
C4 C5 C13 O4 -172.0(4) . . . . ?
C5 C6 C7 C8 74.7(6) . . . . ?
C5 C11 C12 O2 -105.1(6) . . . . ?
C5 C11 C12 C2 72.7(5) . . . . ?
C6 C5 C11 C10 -67.2(5) . . . . ?
C6 C5 C11 C12 -177.3(4) . . . . ?
C6 C5 C13 O3 129.5(6) . . . . ?
C6 C5 C13 O4 -51.8(6) . . . . ?
C6 C7 C8 C9 -21.0(8) . . . . ?
C7 C8 C9 C10 -61.9(7) . . . . ?
C8 C9 C10 C1 168.4(4) . . . . ?
C8 C9 C10 C11 48.0(6) . . . . ?
C9 C10 C11 C5 43.2(6) . . . . ?
C9 C10 C11 C12 158.3(5) . . . . ?
C10 C1 C2 C3 93.8(5) . . . . ?
C10 C1 C2 C12 -17.6(5) . . . . ?
C10 C11 C12 O2 135.8(5) . . . . ?
C10 C11 C12 C2 -46.5(5) . . . . ?
C11 C5 C6 O1 167.3(5) . . . . ?
C11 C5 C6 C7 -13.1(6) . . . . ?
C11 C5 C13 O3 -111.1(6) . . . . ?
C11 C5 C13 O4 67.5(5) . . . . ?
C12 C2 C3 C4 61.3(6) . . . . ?
C13 O4 C14 C15 -108.9(8) . . . . ?
C13 C5 C6 O1 -75.9(6) . . . . ?
C13 C5 C6 C7 103.6(5) . . . . ?
C13 C5 C11 C10 176.4(4) . . . . ?
C13 C5 C11 C12 66.3(5) . . . . ?
C14 O4 C13 O3 5.5(9) . . . . ?
C14 O4 C13 C5 -173.1(5) . . . . ?
Br2 C16 C17 C18 145.8(4) . . . . ?
Br2 C16 C17 C27 -102.6(4) . . . . ?
Br2 C16 C25 C24 -101.6(4) . . . . ?
Br2 C16 C25 C26 130.0(3) . . . . ?
O6 C21 C22 C23 107.7(6) . . . . ?
C16 C17 C18 C19 49.8(7) . . . . ?
C16 C17 C27 O5 140.1(5) . . . . ?
C16 C17 C27 C26 -41.1(5) . . . . ?
C16 C25 C26 C20 83.7(5) . . . . ?
C16 C25 C26 C27 -31.2(5) . . . . ?
C17 C16 C25 C24 135.4(4) . . . . ?
C17 C16 C25 C26 6.9(5) . . . . ?
C17 C18 C19 C20 44.6(7) . . . . ?
C18 C17 C27 O5 -103.2(6) . . . . ?
C18 C17 C27 C26 75.5(5) . . . . ?
C18 C19 C20 C21 -165.7(5) . . . . ?
C18 C19 C20 C26 -40.3(6) . . . . ?
C18 C19 C20 C28 77.9(6) . . . . ?
C19 C20 C21 O6 -44.6(6) . . . . ?
C19 C20 C21 C22 136.3(5) . . . . ?
C19 C20 C26 C25 -56.8(5) . . . . ?
C19 C20 C26 C27 54.4(5) . . . . ?
C19 C20 C28 O7 -10.2(7) . . . . ?
C19 C20 C28 O8 171.5(5) . . . . ?
C20 C21 C22 C23 -73.3(6) . . . . ?
C20 C26 C27 O5 105.5(6) . . . . ?
C20 C26 C27 C17 -73.3(5) . . . . ?
C21 C20 C26 C25 66.9(6) . . . . ?
C21 C20 C26 C27 178.1(4) . . . . ?
C21 C20 C28 O7 -128.9(6) . . . . ?
C21 C20 C28 O8 52.9(6) . . . . ?
C21 C22 C23 C24 20.6(8) . . . . ?
C22 C23 C24 C25 63.0(6) . . . . ?
C23 C24 C25 C16 -169.5(4) . . . . ?
C23 C24 C25 C26 -48.1(6) . . . . ?
C24 C25 C26 C20 -43.4(6) . . . . ?
C24 C25 C26 C27 -158.3(5) . . . . ?
C25 C16 C17 C18 -91.6(5) . . . . ?
C25 C16 C17 C27 20.0(5) . . . . ?
C25 C26 C27 O5 -135.8(5) . . . . ?
C25 C26 C27 C17 45.4(5) . . . . ?
C26 C20 C21 O6 -168.8(5) . . . . ?
C26 C20 C21 C22 12.1(6) . . . . ?
C26 C20 C28 O7 110.1(6) . . . . ?
C26 C20 C28 O8 -68.2(5) . . . . ?
C27 C17 C18 C19 -60.7(6) . . . . ?
C28 O8 C29 C30 96.7(7) . . . . ?
C28 C20 C21 O6 73.8(7) . . . . ?
C28 C20 C21 C22 -105.3(5) . . . . ?
C28 C20 C26 C25 -176.3(4) . . . . ?
C28 C20 C26 C27 -65.1(6) . . . . ?
C29 O8 C28 O7 -4.3(8) . . . . ?
C29 O8 C28 C20 173.9(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4528(10)
2 0.5472(10)

