# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_190801a
_database_code_depnum_ccdc_archive 'CCDC 2016806'
loop_
_audit_author_name
_audit_author_address
lishunian
;CCDC
China
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2021-02-07 downloaded from the CCDC.
;
_audit_creation_date             2019-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C17 H18 N4 O3)'
_chemical_formula_sum            'C34 H36 N8 O6'
_chemical_formula_weight         652.71
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0735(2)
_cell_length_b                   14.3919(3)
_cell_length_c                   13.0757(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.248(2)
_cell_angle_gamma                90
_cell_volume                     1674.69(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10960
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.9390
_cell_measurement_theta_min      4.5700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15734
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.446
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  17.00   1.00    0.10    --  -48.45  62.00 155.00   81
  2  ω   -117.00 -32.00   1.00    0.10    --  -48.45 -62.00  17.00   85
  3  ω    -16.00  21.00   1.00    0.10    --   48.45 -62.00  17.00   37
  4  ω   -113.00 -87.00   1.00    0.60    --  -86.25 -62.00  17.00   26
  5  ω    -51.00 -25.00   1.00    0.60    --  -86.25  62.00 155.00   26
  6  ω    150.00 177.00   1.00    0.60    --  106.49  62.00 155.00   27
  7  ω     91.00 133.00   1.00    0.60    --  106.49  62.00 155.00   42
  8  ω     38.00 123.00   1.00    0.60    --  106.49 -62.00  17.00   85
  9  ω   -120.00 -70.00   1.00    0.10    --  -48.45-125.00-180.00   50
 10  ω   -120.00 -73.00   1.00    0.10    --  -48.45-125.00  60.00   47
 11  ω    -59.00  27.00   1.00    0.10    --  -48.45  19.00 150.00   86
 12  ω     52.00  77.00   1.00    0.10    --   48.45  62.00 155.00   25
 13  ω   -157.00-116.00   1.00    0.60    --  -86.25 -38.00 -90.00   41
 14  ω   -100.00 -71.00   1.00    0.60    --  -86.25 -57.00-120.00   29
 15  ω   -157.00-104.00   1.00    0.60    --  -86.25 -57.00-120.00   53
 16  ω   -147.00 -73.00   1.00    0.60    --  -86.25 -38.00-120.00   74
 17  ω   -104.00 -73.00   1.00    0.60    --  -86.25 -38.00 -90.00   31
 18  ω     34.00 120.00   1.00    0.60    --  106.49 -38.00   0.00   86
 19  ω     94.00 178.00   1.00    0.60    --  106.49  19.00  90.00   84
 20  ω     39.00 117.00   1.00    0.60    --  106.49 -57.00 -90.00   78
 21  ω     93.00 177.00   1.00    0.60    --  106.49  57.00 -30.00   84
 22  ω     92.00 173.00   1.00    0.60    --  106.49  57.00 -60.00   81
 23  ω     34.00 109.00   1.00    0.60    --  106.49 -99.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356973000
_diffrn_orient_matrix_UB_12      0.0053254000
_diffrn_orient_matrix_UB_13      0.1199354000
_diffrn_orient_matrix_UB_21      -0.1179338000
_diffrn_orient_matrix_UB_22      0.0776504000
_diffrn_orient_matrix_UB_23      -0.0033734000
_diffrn_orient_matrix_UB_31      -0.1215445000
_diffrn_orient_matrix_UB_32      -0.0735437000
_diffrn_orient_matrix_UB_33      0.0052115000
_diffrn_oxdiff_ac3_digest_frames 
;
01d8997e60fe2c4ba03ab87e89cd286e3101333e00d
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                5480
_reflns_number_total             5886
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5886
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.169
_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)+(0.0329P)²+0.3447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N5 \\sim N7 \\sim N8: within 2A with sigma of 0.004 and sigma for terminal
atoms of 0.008
3.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C24(H24A,H24B), C27(H27A,H27B), C29(H29A,H29B), C32(H32A,
 H32B), C11(H11A,H11B), C25(H25A,H25B), C28(H28A,H28B), C30(H30A,H30B),
 C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C17(H17), C19(H19), C22(H22), N1(H1), C12(H12), C23(H23), C26(H26)
3.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.0842(2) 0.70351(14) 0.11642(15) 0.0315(4) Uani 1 1 d . . . . .
O3 O 0.2052(2) 0.51608(14) 0.05984(14) 0.0345(4) Uani 1 1 d . . . . .
O6 O 0.4784(3) 0.98927(15) 0.0986(2) 0.0603(8) Uani 1 1 d . . . . .
N1 N 0.3594(3) 0.62055(16) 0.00115(18) 0.0328(5) Uani 1 1 d . . . . .
H1 H 0.3933 0.5846 -0.0414 0.039 Uiso 1 1 calc R . . . .
N3 N 0.3788(3) 0.56741(18) 0.43165(19) 0.0365(6) Uani 1 1 d . . . . .
N4 N 0.2453(3) 0.55330(19) 0.39133(19) 0.0376(6) Uani 1 1 d . . . . .
N6 N 0.4975(4) 0.5738(2) 0.4778(2) 0.0517(7) Uani 1 1 d . . . . .
C1 C 0.2626(3) 0.59319(19) 0.0621(2) 0.0286(6) Uani 1 1 d . . . . .
C5 C 0.3978(3) 0.71522(19) 0.0160(2) 0.0306(6) Uani 1 1 d . . . . .
C6 C 0.1911(3) 0.59761(19) 0.2930(2) 0.0292(6) Uani 1 1 d . . . . .
C7 C 0.3262(3) 0.75260(19) 0.0908(2) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.2992(3) 0.65550(19) 0.24722(19) 0.0271(5) Uani 1 1 d . . . . .
H11A H 0.3940 0.6227 0.2539 0.032 Uiso 1 1 calc R . . . .
H11B H 0.3179 0.7133 0.2857 0.032 Uiso 1 1 calc R . . . .
C12 C 0.3462(3) 0.84458(19) 0.1201(2) 0.0330(6) Uani 1 1 d . . . . .
H12 H 0.2971 0.8700 0.1696 0.040 Uiso 1 1 calc R . . . .
C16 C 0.2379(3) 0.67682(18) 0.1321(2) 0.0279(6) Uani 1 1 d . . . . .
C18 C 0.0481(3) 0.5862(2) 0.2468(2) 0.0341(6) Uani 1 1 d . . . . .
C20 C -0.0155(3) 0.6350(2) 0.1468(2) 0.0354(6) Uani 1 1 d . . . . .
H20 H -0.0402 0.5887 0.0911 0.042 Uiso 1 1 calc R . . . .
C21 C 0.4422(4) 0.8979(2) 0.0732(2) 0.0395(7) Uani 1 1 d . . . . .
C23 C 0.4896(4) 0.7686(2) -0.0333(3) 0.0413(7) Uani 1 1 d . . . . .
H23 H 0.5353 0.7435 -0.0848 0.050 Uiso 1 1 calc R . . . .
C25 C -0.1578(3) 0.6882(3) 0.1558(3) 0.0508(9) Uani 1 1 d . . . . .
H25A H -0.2013 0.7152 0.0888 0.061 Uiso 1 1 calc R . . . .
H25B H -0.1324 0.7384 0.2057 0.061 Uiso 1 1 calc R . . . .
C26 C 0.5116(4) 0.8605(2) -0.0034(3) 0.0452(7) Uani 1 1 d . . . . .
H26 H 0.5735 0.8978 -0.0350 0.054 Uiso 1 1 calc R . . . .
C28 C -0.2060(4) 0.5782(3) 0.2948(4) 0.0594(10) Uani 1 1 d . . . . .
H28A H -0.2788 0.5358 0.3143 0.071 Uiso 1 1 calc R . . . .
H28B H -0.1836 0.6255 0.3484 0.071 Uiso 1 1 calc R . . . .
C30 C -0.0625(4) 0.5250(3) 0.2882(3) 0.0492(8) Uani 1 1 d . . . . .
H30A H -0.0166 0.5025 0.3569 0.059 Uiso 1 1 calc R . . . .
H30B H -0.0873 0.4717 0.2427 0.059 Uiso 1 1 calc R . . . .
C31 C 0.3909(6) 1.0364(2) 0.1626(3) 0.0655(12) Uani 1 1 d . . . . .
H31A H 0.2885 1.0408 0.1262 0.098 Uiso 1 1 calc GR . . . .
H31B H 0.4306 1.0977 0.1784 0.098 Uiso 1 1 calc GR . . . .
H31C H 0.3949 1.0024 0.2263 0.098 Uiso 1 1 calc GR . . . .
C34 C -0.2731(4) 0.6238(3) 0.1912(4) 0.0615(10) Uani 1 1 d . . . . .
H34A H -0.3612 0.6594 0.1985 0.074 Uiso 1 1 calc R . . . .
H34B H -0.3042 0.5763 0.1389 0.074 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
O2 C16 1.422(3) . ?
O2 C20 1.445(3) . ?
O3 C1 1.224(3) . ?
O6 C21 1.380(4) . ?
O6 C31 1.432(4) . ?
N1 C1 1.354(3) . ?
N1 C5 1.410(4) . ?
N3 N4 1.240(4) . ?
N3 N6 1.131(4) . ?
N4 C6 1.433(4) . ?
C1 C16 1.555(4) . ?
C5 C7 1.384(4) . ?
C5 C23 1.381(4) . ?
C6 C11 1.498(4) . ?
C6 C18 1.331(4) . ?
C7 C12 1.380(4) . ?
C7 C16 1.514(4) . ?
C11 C16 1.531(4) . ?
C12 C21 1.390(4) . ?
C18 C20 1.496(4) . ?
C18 C30 1.512(4) . ?
C20 C25 1.525(4) . ?
C21 C26 1.392(4) . ?
C23 C26 1.382(5) . ?
C25 C34 1.535(5) . ?
C28 C30 1.528(5) . ?
C28 C34 1.521(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C20 115.1(2) . . ?
C21 O6 C31 117.4(3) . . ?
C1 N1 C5 111.8(2) . . ?
N6 N3 N4 171.9(3) . . ?
N3 N4 C6 116.4(2) . . ?
O3 C1 N1 124.8(3) . . ?
O3 C1 C16 127.3(2) . . ?
N1 C1 C16 107.8(2) . . ?
C7 C5 N1 109.6(2) . . ?
C23 C5 N1 129.0(2) . . ?
C23 C5 C7 121.5(3) . . ?
N4 C6 C11 118.0(2) . . ?
C18 C6 N4 119.1(2) . . ?
C18 C6 C11 122.9(2) . . ?
C5 C7 C16 109.0(2) . . ?
C12 C7 C5 120.9(2) . . ?
C12 C7 C16 129.9(2) . . ?
C6 C11 C16 111.3(2) . . ?
C7 C12 C21 117.9(2) . . ?
O2 C16 C1 112.0(2) . . ?
O2 C16 C7 109.1(2) . . ?
O2 C16 C11 110.7(2) . . ?
C7 C16 C1 101.6(2) . . ?
C7 C16 C11 112.3(2) . . ?
C11 C16 C1 110.9(2) . . ?
C6 C18 C20 121.0(2) . . ?
C6 C18 C30 124.4(3) . . ?
C20 C18 C30 114.6(3) . . ?
O2 C20 C18 113.9(2) . . ?
O2 C20 C25 105.3(2) . . ?
C18 C20 C25 110.8(3) . . ?
O6 C21 C12 124.1(3) . . ?
O6 C21 C26 115.0(3) . . ?
C12 C21 C26 120.9(3) . . ?
C5 C23 C26 117.9(3) . . ?
C20 C25 C34 111.0(3) . . ?
C23 C26 C21 120.9(3) . . ?
C34 C28 C30 111.3(3) . . ?
C18 C30 C28 111.1(3) . . ?
C28 C34 C25 110.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.904
_oxdiff_exptl_absorpt_empirical_full_min 0.574
