# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_danxie
_database_code_depnum_ccdc_archive 'CCDC 1823823'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        3c
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.194(2)
_cell_length_b                   14.232(3)
_cell_length_c                   12.523(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.045(6)
_cell_angle_gamma                90
_cell_volume                     1746.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6140
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17222
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.216
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2547
_reflns_number_total             3992
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.067
_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)+(0.0995P)²+0.1672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H24C)=Sof(H24D)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C24(H24C,H24D), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C1AA(H1AA,H1AB,H1AC), C3(H3A,H3B,H3C)
3.d Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA)
;
_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 0.30972(13) 0.21902(9) 0.53354(10) 0.0520(4) Uani 1 1 d . . . . .
C2 C -0.00618(17) 0.19893(12) 0.44107(13) 0.0400(4) Uani 1 1 d . . . . .
N3 N 0.09173(18) 0.08244(11) 0.58808(13) 0.0557(5) Uani 1 1 d . . . . .
C4 C 0.2019(2) 0.07790(13) 0.55900(15) 0.0500(5) Uani 1 1 d . . . . .
C5 C 0.10898(17) 0.18474(13) 0.38727(13) 0.0419(4) Uani 1 1 d . . . . .
C7 C -0.11308(18) 0.26033(13) 0.39524(15) 0.0457(5) Uani 1 1 d . . . . .
H7 H -0.1107 0.2949 0.3328 0.055 Uiso 1 1 calc R . . . .
C8 C 0.17155(17) 0.27797(13) 0.37078(14) 0.0419(4) Uani 1 1 d . . . . .
C9 C 0.28369(18) 0.29393(14) 0.46091(15) 0.0466(5) Uani 1 1 d . . . . .
C10 C -0.0111(2) 0.14738(13) 0.53478(15) 0.0491(5) Uani 1 1 d . . . . .
O11 O 0.42065(19) 0.00565(13) 0.60195(16) 0.0894(6) Uani 1 1 d . . . . .
C12 C 0.23422(18) 0.13939(13) 0.47164(14) 0.0469(5) Uani 1 1 d . . . . .
C13 C -0.2223(2) 0.27197(15) 0.43871(18) 0.0573(5) Uani 1 1 d . . . . .
C14 C -0.1201(2) 0.15781(18) 0.57924(19) 0.0669(6) Uani 1 1 d . . . . .
H14 H -0.1234 0.1229 0.6412 0.080 Uiso 1 1 calc R . . . .
C15 C 0.0559(2) 0.12730(16) 0.28077(16) 0.0594(6) Uani 1 1 d . . . . .
H15A H 0.0278 0.0664 0.2989 0.089 Uiso 1 1 calc GR . . . .
H15B H 0.1271 0.1204 0.2447 0.089 Uiso 1 1 calc GR . . . .
H15C H -0.0204 0.1591 0.2319 0.089 Uiso 1 1 calc GR . . . .
C16 C 0.1360(2) 0.34475(15) 0.28775(16) 0.0521(5) Uani 1 1 d . . . . .
H16 H 0.0627 0.3346 0.2255 0.063 Uiso 1 1 calc R . . . .
O17 O 0.2776(2) -0.03511(13) 0.69988(15) 0.0944(6) Uani 1 1 d . . . . .
C18 C 0.3582(2) 0.37521(16) 0.47382(18) 0.0616(6) Uani 1 1 d . . . . .
H18 H 0.4318 0.3853 0.5359 0.074 Uiso 1 1 calc R . . . .
C19 C 0.3121(3) 0.01172(15) 0.62146(18) 0.0641(6) Uani 1 1 d . . . . .
C20 C 0.3193(2) 0.44137(18) 0.3908(2) 0.0694(6) Uani 1 1 d . . . . .
H20 H 0.3677 0.4975 0.3974 0.083 Uiso 1 1 calc R . . . .
C21 C 0.2110(2) 0.42686(17) 0.29847(19) 0.0638(6) Uani 1 1 d . . . . .
H21 H 0.1882 0.4724 0.2432 0.077 Uiso 1 1 calc R . . . .
C22 C -0.2238(2) 0.21953(18) 0.5323(2) 0.0713(7) Uani 1 1 d . . . . .
H22 H -0.2961 0.2264 0.5635 0.086 Uiso 1 1 calc R . . . .
C23 C -0.3358(3) 0.3392(2) 0.3857(2) 0.0874(8) Uani 1 1 d . . . . .
H23A H -0.3274 0.3581 0.3142 0.131 Uiso 1 1 calc GR . . . .
H23B H -0.3300 0.3936 0.4321 0.131 Uiso 1 1 calc GR . . . .
H23C H -0.4222 0.3089 0.3768 0.131 Uiso 1 1 calc GR . . . .
C24 C 0.3814(4) -0.0990(2) 0.7679(3) 0.1244(14) Uani 1 1 d . . . . .
H24C H 0.3420 -0.1606 0.7715 0.149 Uiso 0.718(13) 1 calc R . P A 2
H24D H 0.4568 -0.1058 0.7353 0.149 Uiso 0.718(13) 1 calc R . P A 2
H24A H 0.3830 -0.1552 0.7245 0.149 Uiso 0.282(13) 1 calc R . P A 1
H24B H 0.4697 -0.0689 0.7801 0.149 Uiso 0.282(13) 1 calc R . P A 1
C1AA C 0.4299(6) -0.0589(5) 0.8796(4) 0.097(2) Uani 0.718(13) 1 d . . P A 2
H1AA H 0.4841 -0.0042 0.8773 0.145 Uiso 0.718(13) 1 calc GR . P A 2
H1AB H 0.4843 -0.1045 0.9289 0.145 Uiso 0.718(13) 1 calc GR . P A 2
H1AC H 0.3531 -0.0417 0.9057 0.145 Uiso 0.718(13) 1 calc GR . P A 2
C3 C 0.3699(15) -0.1227(13) 0.8555(11) 0.096(6) Uani 0.282(13) 1 d . . P A 1
H3A H 0.3595 -0.0683 0.8976 0.144 Uiso 0.282(13) 1 calc GR . P A 1
H3B H 0.4498 -0.1569 0.8949 0.144 Uiso 0.282(13) 1 calc GR . P A 1
H3C H 0.2910 -0.1623 0.8449 0.144 Uiso 0.282(13) 1 calc GR . P A 1
O0AA O 0.31227(16) 0.09631(12) 0.41108(12) 0.0719(5) Uani 1 1 d . . . . .
H0AA H 0.3745 0.0669 0.4533 0.108 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 C9 1.379(2) . ?
O1 C12 1.465(2) . ?
C2 C5 1.520(2) . ?
C2 C7 1.391(2) . ?
C2 C10 1.396(3) . ?
N3 C4 1.275(3) . ?
N3 C10 1.418(2) . ?
C4 C12 1.507(3) . ?
C4 C19 1.508(3) . ?
C5 C8 1.511(3) . ?
C5 C12 1.555(2) . ?
C5 C15 1.530(2) . ?
C7 C13 1.378(3) . ?
C8 C9 1.385(2) . ?
C8 C16 1.381(3) . ?
C9 C18 1.369(3) . ?
C10 C14 1.382(3) . ?
O11 C19 1.200(3) . ?
C12 O0AA 1.385(2) . ?
C13 C22 1.392(3) . ?
C13 C23 1.507(3) . ?
C14 C22 1.375(3) . ?
C16 C21 1.383(3) . ?
O17 C19 1.313(3) . ?
O17 C24 1.475(3) . ?
C18 C20 1.377(3) . ?
C20 C21 1.376(3) . ?
C24 C1AA 1.464(6) . ?
C24 C3 1.184(11) . ?

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
C9 O1 C12 105.77(13) . . ?
C7 C2 C5 120.91(16) . . ?
C7 C2 C10 118.09(17) . . ?
C10 C2 C5 120.93(15) . . ?
C4 N3 C10 119.57(16) . . ?
N3 C4 C12 124.37(16) . . ?
N3 C4 C19 118.2(2) . . ?
C12 C4 C19 117.3(2) . . ?
C2 C5 C12 110.10(14) . . ?
C2 C5 C15 109.10(15) . . ?
C8 C5 C2 110.54(14) . . ?
C8 C5 C12 99.15(14) . . ?
C8 C5 C15 114.27(16) . . ?
C15 C5 C12 113.37(14) . . ?
C13 C7 C2 122.62(18) . . ?
C9 C8 C5 108.49(15) . . ?
C16 C8 C5 132.40(16) . . ?
C16 C8 C9 119.10(18) . . ?
O1 C9 C8 112.07(16) . . ?
C18 C9 O1 125.19(17) . . ?
C18 C9 C8 122.74(18) . . ?
C2 C10 N3 123.00(18) . . ?
C14 C10 C2 120.10(18) . . ?
C14 C10 N3 116.90(18) . . ?
O1 C12 C4 104.67(14) . . ?
O1 C12 C5 104.54(14) . . ?
C4 C12 C5 115.56(16) . . ?
O0AA C12 O1 109.56(16) . . ?
O0AA C12 C4 114.47(16) . . ?
O0AA C12 C5 107.45(14) . . ?
C7 C13 C22 117.75(19) . . ?
C7 C13 C23 120.5(2) . . ?
C22 C13 C23 121.7(2) . . ?
C22 C14 C10 120.3(2) . . ?
C8 C16 C21 119.04(19) . . ?
C19 O17 C24 116.6(3) . . ?
C9 C18 C20 117.0(2) . . ?
O11 C19 C4 122.4(2) . . ?
O11 C19 O17 124.7(2) . . ?
O17 C19 C4 112.9(2) . . ?
C21 C20 C18 121.9(2) . . ?
C20 C21 C16 120.2(2) . . ?
C14 C22 C13 121.1(2) . . ?
C1AA C24 O17 108.1(3) . . ?
C3 C24 O17 118.2(6) . . ?

_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_sanxie
_database_code_depnum_ccdc_archive 'CCDC 1823825'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O5'
_chemical_formula_sum            'C20 H20 N2 O5'
_chemical_formula_weight         368.38
_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'

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

_cell_length_a                   9.1376(8)
_cell_length_b                   9.5813(9)
_cell_length_c                   10.8392(10)
_cell_angle_alpha                105.957(3)
_cell_angle_beta                 95.789(3)
_cell_angle_gamma                98.506(3)
_cell_volume                     892.32(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7543
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1426 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.8905.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             388
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13547
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.976
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3249
_reflns_number_total             4036
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.040
_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)+(0.0723P)²+0.1906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C15(H15), N19(H19), C20(H20), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.08483(11) 0.16067(11) 0.13650(9) 0.0403(3) Uani 1 1 d . . . . .
N2 N -0.10878(12) 0.29890(13) 0.34178(11) 0.0347(3) Uani 1 1 d . . . . .
O3 O -0.24049(11) 0.18552(12) 0.50932(11) 0.0448(3) Uani 1 1 d . . . . .
O4 O 0.16467(12) 0.40996(14) 0.15462(12) 0.0512(3) Uani 1 1 d . . . . .
H4 H 0.0981 0.4310 0.1102 0.077 Uiso 1 1 calc GR . . . .
C5 C 0.21892(16) 0.24130(17) 0.53908(13) 0.0385(3) Uani 1 1 d . . . . .
H5 H 0.3222 0.2509 0.5435 0.046 Uiso 1 1 calc R . . . .
C6 C 0.21536(14) 0.32410(14) 0.33794(12) 0.0313(3) Uani 1 1 d . . . . .
O7 O -0.11160(14) 0.41586(19) 0.06327(14) 0.0742(5) Uani 1 1 d . . . . .
C8 C -0.01935(15) 0.25492(15) 0.43142(13) 0.0318(3) Uani 1 1 d . . . . .
O9 O 0.24214(13) 0.17894(16) 0.73178(10) 0.0574(3) Uani 1 1 d . . . . .
C10 C 0.13652(15) 0.26930(14) 0.43795(12) 0.0313(3) Uani 1 1 d . . . . .
C11 C -0.05395(15) 0.33179(15) 0.24711(13) 0.0345(3) Uani 1 1 d . . . . .
C12 C 0.30646(14) 0.21162(14) 0.27422(12) 0.0310(3) Uani 1 1 d . . . . .
C13 C -0.08911(15) 0.20518(15) 0.52578(13) 0.0343(3) Uani 1 1 d . . . . .
C14 C 0.44762(15) 0.18804(16) 0.31052(14) 0.0366(3) Uani 1 1 d . . . . .
H14 H 0.5088 0.2522 0.3840 0.044 Uiso 1 1 calc R . . . .
C15 C -0.00521(17) 0.17793(16) 0.62738(14) 0.0396(3) Uani 1 1 d . . . . .
H15 H -0.0516 0.1461 0.6899 0.048 Uiso 1 1 calc R . . . .
C16 C 0.14942(17) 0.19892(17) 0.63437(13) 0.0402(3) Uani 1 1 d . . . . .
C17 C 0.21871(15) 0.11750(16) 0.16258(13) 0.0350(3) Uani 1 1 d . . . . .
C18 C 0.10196(15) 0.31441(16) 0.21838(13) 0.0347(3) Uani 1 1 d . . . . .
N19 N -0.29092(15) 0.38967(18) 0.18568(15) 0.0539(4) Uani 1 1 d . . . . .
H19 H -0.3139 0.3638 0.2522 0.065 Uiso 1 1 calc R . . . .
C20 C 0.49668(17) 0.06609(18) 0.23479(16) 0.0448(4) Uani 1 1 d . . . . .
H20 H 0.5918 0.0488 0.2573 0.054 Uiso 1 1 calc R . . . .
C21 C -0.15501(16) 0.38399(17) 0.15704(15) 0.0411(3) Uani 1 1 d . . . . .
C22 C -0.3140(2) 0.1467(2) 0.6085(2) 0.0611(5) Uani 1 1 d . . . . .
H22A H -0.4201 0.1389 0.5871 0.092 Uiso 1 1 calc GR . . . .
H22B H -0.2786 0.2213 0.6899 0.092 Uiso 1 1 calc GR . . . .
H22C H -0.2929 0.0536 0.6152 0.092 Uiso 1 1 calc GR . . . .
C23 C 0.26336(19) -0.00536(18) 0.08813(15) 0.0464(4) Uani 1 1 d . . . . .
H23 H 0.2015 -0.0698 0.0151 0.056 Uiso 1 1 calc R . . . .
C24 C 0.4046(2) -0.02895(19) 0.12662(16) 0.0503(4) Uani 1 1 d . . . . .
H24 H 0.4381 -0.1110 0.0782 0.060 Uiso 1 1 calc R . . . .
C25 C 0.30416(18) 0.47965(17) 0.40320(17) 0.0476(4) Uani 1 1 d . . . . .
H25A H 0.2367 0.5452 0.4330 0.071 Uiso 1 1 calc GR . . . .
H25B H 0.3583 0.5128 0.3420 0.071 Uiso 1 1 calc GR . . . .
H25C H 0.3733 0.4788 0.4757 0.071 Uiso 1 1 calc GR . . . .
C26 C 0.1787(3) 0.1535(3) 0.84004(18) 0.0740(6) Uani 1 1 d . . . . .
H26A H 0.1109 0.0604 0.8128 0.111 Uiso 1 1 calc GR . . . .
H26B H 0.1254 0.2311 0.8748 0.111 Uiso 1 1 calc GR . . . .
H26C H 0.2569 0.1519 0.9055 0.111 Uiso 1 1 calc GR . . . .
C27 C -0.4038(2) 0.4371(2) 0.1112(2) 0.0653(5) Uani 1 1 d . . . . .
H27A H -0.3804 0.4252 0.0250 0.098 Uiso 1 1 calc GR . . . .
H27B H -0.4060 0.5391 0.1522 0.098 Uiso 1 1 calc GR . . . .
H27C H -0.4998 0.3783 0.1072 0.098 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 C17 1.3754(17) . ?
O1 C18 1.4721(17) . ?
N2 C8 1.3986(17) . ?
N2 C11 1.2799(17) . ?
O3 C13 1.3547(16) . ?
O3 C22 1.4276(18) . ?
O4 C18 1.3844(16) . ?
C5 C10 1.3767(19) . ?
C5 C16 1.386(2) . ?
C6 C10 1.5259(18) . ?
C6 C12 1.5178(18) . ?
C6 C18 1.5480(18) . ?
C6 C25 1.525(2) . ?
O7 C21 1.2246(18) . ?
C8 C10 1.4032(18) . ?
C8 C13 1.4104(18) . ?
O9 C16 1.3595(17) . ?
O9 C26 1.423(2) . ?
C11 C18 1.5117(19) . ?
C11 C21 1.5098(19) . ?
C12 C14 1.3793(19) . ?
C12 C17 1.3823(19) . ?
C13 C15 1.384(2) . ?
C14 C20 1.393(2) . ?
C15 C16 1.389(2) . ?
C17 C23 1.375(2) . ?
N19 C21 1.315(2) . ?
N19 C27 1.447(2) . ?
C20 C24 1.378(2) . ?
C23 C24 1.386(2) . ?

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
C17 O1 C18 105.80(10) . . ?
C11 N2 C8 119.99(12) . . ?
C13 O3 C22 117.35(12) . . ?
C10 C5 C16 120.66(13) . . ?
C10 C6 C18 110.84(10) . . ?
C12 C6 C10 108.96(10) . . ?
C12 C6 C18 99.46(10) . . ?
C12 C6 C25 115.15(11) . . ?
C25 C6 C10 109.00(11) . . ?
C25 C6 C18 113.12(12) . . ?
N2 C8 C10 123.14(12) . . ?
N2 C8 C13 117.65(11) . . ?
C10 C8 C13 119.00(12) . . ?
C16 O9 C26 117.80(14) . . ?
C5 C10 C6 120.05(12) . . ?
C5 C10 C8 119.64(12) . . ?
C8 C10 C6 120.22(11) . . ?
N2 C11 C18 123.57(12) . . ?
N2 C11 C21 117.17(12) . . ?
C21 C11 C18 119.20(12) . . ?
C14 C12 C6 132.32(12) . . ?
C14 C12 C17 119.88(12) . . ?
C17 C12 C6 107.74(11) . . ?
O3 C13 C8 115.90(12) . . ?
O3 C13 C15 123.25(12) . . ?
C15 C13 C8 120.85(12) . . ?
C12 C14 C20 118.65(14) . . ?
C13 C15 C16 118.85(13) . . ?
C5 C16 C15 120.88(13) . . ?
O9 C16 C5 115.61(13) . . ?
O9 C16 C15 123.50(13) . . ?
O1 C17 C12 112.62(12) . . ?
C23 C17 O1 124.97(13) . . ?
C23 C17 C12 122.42(13) . . ?
O1 C18 C6 104.24(10) . . ?
O1 C18 C11 104.61(11) . . ?
O4 C18 O1 109.94(11) . . ?
O4 C18 C6 108.39(11) . . ?
O4 C18 C11 114.40(11) . . ?
C11 C18 C6 114.67(11) . . ?
C21 N19 C27 123.53(15) . . ?
C24 C20 C14 120.18(14) . . ?
O7 C21 C11 121.18(13) . . ?
O7 C21 N19 123.51(14) . . ?
N19 C21 C11 115.30(13) . . ?
C17 C23 C24 117.08(15) . . ?
C20 C24 C23 121.71(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
