# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_181109_s2_hhz
_database_code_depnum_ccdc_archive 'CCDC 1968182'
loop_
_audit_author_name
_audit_author_address
'He Huizi'
;Sichuan University
China
;
_audit_update_record             
;
2019-11-26 deposited with the CCDC.	2020-05-12 downloaded from the CCDC.
;
_audit_creation_date             2018-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H28 N2 O5'
_chemical_formula_sum            'C27 H28 N2 O5'
_chemical_formula_weight         460.51
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   5.1905(5)
_cell_length_b                   9.3677(7)
_cell_length_c                   23.713(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.729(12)
_cell_angle_gamma                90
_cell_volume                     1149.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    805
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6480
_cell_measurement_theta_min      3.4580
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41090
_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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_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     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2976
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.379
_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 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00    0.00   0.6000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   19.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.20   56.00   0.6000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000  -60.0000 127

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   69.00   0.6000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000   90.0000 125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0046933000
_diffrn_orient_matrix_UB_12      0.0665987000
_diffrn_orient_matrix_UB_13      -0.0142678000
_diffrn_orient_matrix_UB_21      -0.0013818000
_diffrn_orient_matrix_UB_22      0.0358526000
_diffrn_orient_matrix_UB_23      0.0263083000
_diffrn_orient_matrix_UB_31      0.1371061000
_diffrn_orient_matrix_UB_32      0.0026628000
_diffrn_orient_matrix_UB_33      0.0022758000
_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                1855
_reflns_number_total             2976
_reflns_odcompleteness_completeness 96.63
_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         0.458
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_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     158
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.049
_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)+(0.0662P)²+0.5474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1644
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.491(2)
 0.509(2)
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. Others
 Fixed Sof: H10A(0.5) H10B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_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
O1 O 0.0119(4) 0.3410(2) 0.35226(10) 0.0450(7) Uani 1 1 d . . . . .
O2 O 0.1380(5) 0.1299(2) 0.32525(13) 0.0684(9) Uani 1 1 d . . . . .
O3 O 0.5000 0.5456(3) 0.2500 0.0389(9) Uani 1 2 d S T P . .
N1 N -0.3245(6) 0.7841(3) 0.41022(14) 0.0568(10) Uani 1 1 d . . . . .
C1 C 0.1622(7) 0.2573(4) 0.32020(17) 0.0437(9) Uani 1 1 d . . . . .
C2 C 0.3362(6) 0.3256(3) 0.28448(15) 0.0375(8) Uani 1 1 d . . . . .
C3 C 0.3417(6) 0.4690(3) 0.28296(15) 0.0337(8) Uani 1 1 d . . . . .
C4 C 0.1814(6) 0.5571(3) 0.31435(14) 0.0317(8) Uani 1 1 d . . . . .
C5 C 0.1678(7) 0.7061(3) 0.31287(14) 0.0380(9) Uani 1 1 d . . . . .
H5 H 0.2748 0.7560 0.2902 0.046 Uiso 1 1 calc R . . . .
C6 C 0.0032(6) 0.7801(3) 0.34352(15) 0.0413(10) Uani 1 1 d . . . . .
H6 H -0.0024 0.8791 0.3409 0.050 Uiso 1 1 calc R . . . .
C7 C -0.1606(7) 0.7087(4) 0.37948(16) 0.0405(9) Uani 1 1 d . . . . .
C8 C -0.1469(6) 0.5600(3) 0.38139(15) 0.0406(9) Uani 1 1 d . . . . .
H8 H -0.2503 0.5096 0.4047 0.049 Uiso 1 1 calc R . . . .
C9 C 0.0175(6) 0.4878(3) 0.34930(14) 0.0356(9) Uani 1 1 d . . . . .
C10 C 0.5000 0.2324(5) 0.2500 0.0462(14) Uani 1 2 d S T P . .
H10A H 0.6099 0.1717 0.2749 0.055 Uiso 0.5 1 calc R . . . .
H10B H 0.3901 0.1718 0.2251 0.055 Uiso 0.5 1 calc R . . . .
C11 C -0.3853(9) 0.9404(5) 0.3972(2) 0.0853(16) Uani 1 1 d . . . . .
H11A H -0.3569 0.9603 0.3581 0.102 Uiso 1 1 calc R . . . .
H11B H -0.5656 0.9591 0.4024 0.102 Uiso 1 1 calc R . . . .
C12 C -0.2293(11) 1.0298(6) 0.4326(2) 0.114(2) Uani 1 1 d . . . . .
H12A H -0.0508 1.0098 0.4281 0.170 Uiso 1 1 calc GR . . . .
H12B H -0.2640 1.0135 0.4712 0.170 Uiso 1 1 calc GR . . . .
H12C H -0.2660 1.1275 0.4228 0.170 Uiso 1 1 calc GR . . . .
C13 C -0.4731(7) 0.7162(4) 0.45204(17) 0.0534(11) Uani 1 1 d . . . . .
H13A H -0.5506 0.6297 0.4358 0.064 Uiso 1 1 calc R . . . .
H13B H -0.6123 0.7797 0.4606 0.064 Uiso 1 1 calc R . . . .
C14 C -0.3172(9) 0.6789(4) 0.50628(18) 0.0733(14) Uani 1 1 d . . . . .
H14A H -0.1838 0.6124 0.4985 0.110 Uiso 1 1 calc GR . . . .
H14B H -0.4280 0.6365 0.5321 0.110 Uiso 1 1 calc GR . . . .
H14C H -0.2401 0.7639 0.5228 0.110 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 1.378(4) . ?
O1 C9 1.378(3) . ?
O2 C1 1.206(4) . ?
O3 C3 1.381(3) . ?
O3 C3 1.381(3) 2_655 ?
N1 C7 1.362(4) . ?
N1 C11 1.523(5) . ?
N1 C13 1.452(4) . ?
C1 C2 1.439(5) . ?
C2 C3 1.344(4) . ?
C2 C10 1.506(4) . ?
C3 C4 1.424(4) . ?
C4 C5 1.398(4) . ?
C4 C9 1.395(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.356(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.420(4) . ?
C7 C8 1.395(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(4) . ?
C10 C2 1.506(4) 2_655 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.396(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.503(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 121.7(3) . . ?
C3 O3 C3 117.4(3) 2_655 . ?
C7 N1 C11 121.2(3) . . ?
C7 N1 C13 121.9(3) . . ?
C13 N1 C11 116.5(3) . . ?
O1 C1 C2 118.9(3) . . ?
O2 C1 O1 116.1(3) . . ?
O2 C1 C2 125.0(3) . . ?
C1 C2 C10 118.1(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 C10 123.4(3) . . ?
O3 C3 C4 113.3(3) . . ?
C2 C3 O3 123.3(3) . . ?
C2 C3 C4 123.4(3) . . ?
C5 C4 C3 126.5(3) . . ?
C9 C4 C3 116.9(3) . . ?
C9 C4 C5 116.6(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
N1 C7 C6 120.6(3) . . ?
N1 C7 C8 122.2(3) . . ?
C8 C7 C6 117.2(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
O1 C9 C4 120.7(3) . . ?
C8 C9 O1 116.7(3) . . ?
C8 C9 C4 122.6(3) . . ?
C2 C10 C2 109.1(4) 2_655 . ?
C2 C10 H10A 109.9 . . ?
C2 C10 H10A 109.9 2_655 . ?
C2 C10 H10B 109.9 2_655 . ?
C2 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 N1 110.8(5) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
N1 C13 C14 114.0(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -1.3(5) . . . . ?
O1 C1 C2 C10 179.7(3) . . . . ?
O2 C1 C2 C3 179.8(4) . . . . ?
O2 C1 C2 C10 0.7(6) . . . . ?
O3 C3 C4 C5 2.1(5) . . . . ?
O3 C3 C4 C9 -179.3(3) . . . . ?
N1 C7 C8 C9 179.1(4) . . . . ?
C1 O1 C9 C4 -1.4(5) . . . . ?
C1 O1 C9 C8 177.6(3) . . . . ?
C1 C2 C3 O3 -179.7(3) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C1 C2 C10 C2 179.3(4) . . . 2_655 ?
C2 C3 C4 C5 -176.8(4) . . . . ?
C2 C3 C4 C9 1.8(5) . . . . ?
C3 O3 C3 C2 0.3(3) 2_655 . . . ?
C3 O3 C3 C4 -178.6(3) 2_655 . . . ?
C3 C2 C10 C2 0.3(3) . . . 2_655 ?
C3 C4 C5 C6 178.3(4) . . . . ?
C3 C4 C9 O1 -0.7(5) . . . . ?
C3 C4 C9 C8 -179.6(3) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C5 C4 C9 O1 178.1(3) . . . . ?
C5 C4 C9 C8 -0.8(5) . . . . ?
C5 C6 C7 N1 179.8(4) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C7 N1 C11 C12 -96.6(5) . . . . ?
C7 N1 C13 C14 75.5(5) . . . . ?
C7 C8 C9 O1 -177.8(3) . . . . ?
C7 C8 C9 C4 1.2(5) . . . . ?
C9 O1 C1 O2 -178.5(3) . . . . ?
C9 O1 C1 C2 2.5(5) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C10 C2 C3 O3 -0.6(5) . . . . ?
C10 C2 C3 C4 178.1(3) . . . . ?
C11 N1 C7 C6 14.6(6) . . . . ?
C11 N1 C7 C8 -164.9(4) . . . . ?
C11 N1 C13 C14 -111.8(4) . . . . ?
C13 N1 C7 C6 -173.0(4) . . . . ?
C13 N1 C7 C8 7.5(6) . . . . ?
C13 N1 C11 C12 90.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.491(2)
2 0.509(2)

