# 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_cu_yxy_hqf_0m
_database_code_depnum_ccdc_archive 'CCDC 2074968'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Yang'
;ShanghaiTech University
China
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O4'
_chemical_formula_sum            'C23 H24 N2 O4'
_chemical_formula_weight         392.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   10.8014(2)
_cell_length_b                   10.8014(2)
_cell_length_c                   31.6209(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3194.96(14)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.74
_cell_measurement_theta_min      4.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6312
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1761 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.8369.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            80320
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.281
_diffrn_reflns_theta_min         4.727
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4385
_reflns_number_total             4587
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 2055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4587
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.075
_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)+(0.0300P)²+0.3924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00K(H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00M(H00M), C00O(H00O), C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00Q(H00A,H00D,H00F), C00R(H00L,H00N,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,
 H00V,H00W)
;
_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
O001 O 0.31244(12) 0.90181(12) 0.45155(4) 0.0319(3) Uani 1 1 d . . . . .
O002 O 0.44152(14) 0.81077(14) 0.42168(4) 0.0393(3) Uani 1 1 d . . . . .
O003 O 0.79265(17) 1.16067(17) 0.40015(4) 0.0507(4) Uani 1 1 d . . . . .
O004 O 0.90682(14) 1.20583(16) 0.46250(5) 0.0463(3) Uani 1 1 d . . . . .
N005 N 0.54856(14) 1.03763(15) 0.44903(4) 0.0267(3) Uani 1 1 d . . . . .
N006 N 0.67420(14) 1.03460(15) 0.46062(4) 0.0281(3) Uani 1 1 d . . . . .
C007 C 0.55439(18) 0.81836(19) 0.52477(6) 0.0340(4) Uani 1 1 d . . . . .
H007 H 0.549428 0.793587 0.495742 0.041 Uiso 1 1 calc R . . . .
C008 C 0.63097(17) 0.96032(18) 0.53706(5) 0.0283(3) Uani 1 1 d . . . . .
C009 C 0.45033(16) 1.20073(16) 0.46457(5) 0.0251(3) Uani 1 1 d . . . . .
C00A C 0.54158(16) 1.14127(16) 0.47629(5) 0.0247(3) Uani 1 1 d . . . . .
C00B C 0.63578(17) 1.17559(17) 0.50774(5) 0.0276(3) Uani 1 1 d . . . . .
H00B H 0.657359 1.247657 0.528323 0.033 Uiso 1 1 calc R . . . .
C00C C 0.39866(19) 1.25532(18) 0.49542(5) 0.0306(3) Uani 1 1 d . . . . .
H00C H 0.419651 1.251040 0.524376 0.037 Uiso 1 1 calc R . . . .
C00D C 0.43083(18) 0.90382(18) 0.43936(5) 0.0284(3) Uani 1 1 d . . . . .
C00E C 0.41856(18) 1.20922(18) 0.42211(5) 0.0301(3) Uani 1 1 d . . . . .
H00E H 0.453135 1.172292 0.400781 0.036 Uiso 1 1 calc R . . . .
C00F C 0.70309(17) 1.08127(17) 0.50543(5) 0.0275(3) Uani 1 1 d . . . . .
C00G C 0.3163(2) 1.3161(2) 0.48393(6) 0.0380(4) Uani 1 1 d . . . . .
H00G H 0.281109 1.352872 0.505127 0.046 Uiso 1 1 calc R . . . .
C00H C 0.4846(2) 0.7118(2) 0.55512(7) 0.0439(5) Uani 1 1 d . . . . .
H00H H 0.431636 0.614457 0.546712 0.053 Uiso 1 1 calc R . . . .
C00I C 0.2855(2) 1.3234(2) 0.44197(7) 0.0411(4) Uani 1 1 d . . . . .
H00I H 0.228806 1.364544 0.434368 0.049 Uiso 1 1 calc R . . . .
C00J C 0.3376(2) 1.2705(2) 0.41078(6) 0.0376(4) Uani 1 1 d . . . . .
H00J H 0.317632 1.276554 0.381840 0.045 Uiso 1 1 calc R . . . .
C00K C 0.86874(18) 1.1575(2) 0.50624(6) 0.0377(4) Uani 1 1 d . . . . .
H00K H 0.907975 1.241450 0.525789 0.045 Uiso 1 1 calc R . . . .
C00L C 0.7931(2) 1.1383(2) 0.43713(6) 0.0381(4) Uani 1 1 d . . . . .
C00M C 0.4922(2) 0.7476(3) 0.59737(7) 0.0494(6) Uani 1 1 d . . . . .
H00M H 0.444409 0.674875 0.617989 0.059 Uiso 1 1 calc R . . . .
C00N C 0.16937(19) 0.78651(19) 0.43810(6) 0.0354(4) Uani 1 1 d . . . . .
C00O C 0.5694(2) 0.8892(3) 0.60960(6) 0.0460(5) Uani 1 1 d . . . . .
H00O H 0.575062 0.913567 0.638686 0.055 Uiso 1 1 calc R . . . .
C00P C 0.6382(2) 0.9956(2) 0.57983(6) 0.0365(4) Uani 1 1 d . . . . .
H00P H 0.690632 1.092779 0.588428 0.044 Uiso 1 1 calc R . . . .
C00Q C 0.1611(2) 0.7807(3) 0.39035(7) 0.0502(5) Uani 1 1 d . . . . .
H00A H 0.193468 0.876691 0.379178 0.075 Uiso 1 1 calc GR . . . .
H00D H 0.062081 0.716364 0.381569 0.075 Uiso 1 1 calc GR . . . .
H00F H 0.222362 0.745108 0.379353 0.075 Uiso 1 1 calc GR . . . .
C00R C 0.9287(2) 1.0620(2) 0.51731(8) 0.0500(5) Uani 1 1 d . . . . .
H00L H 0.881946 0.975135 0.499995 0.075 Uiso 1 1 calc GR . . . .
H00N H 0.911208 1.035994 0.547292 0.075 Uiso 1 1 calc GR . . . .
H00Q H 1.031767 1.112638 0.511822 0.075 Uiso 1 1 calc GR . . . .
C00S C 0.0737(2) 0.8383(2) 0.45641(8) 0.0521(5) Uani 1 1 d . . . . .
H00R H 0.081503 0.841659 0.487312 0.078 Uiso 1 1 calc GR . . . .
H00S H -0.025571 0.772629 0.448196 0.078 Uiso 1 1 calc GR . . . .
H00T H 0.103409 0.934149 0.445555 0.078 Uiso 1 1 calc GR . . . .
C00T C 0.1403(2) 0.6465(2) 0.45765(8) 0.0517(5) Uani 1 1 d . . . . .
H00U H 0.207145 0.618937 0.445987 0.078 Uiso 1 1 calc GR . . . .
H00V H 0.042058 0.572081 0.451251 0.078 Uiso 1 1 calc GR . . . .
H00W H 0.152963 0.657838 0.488369 0.078 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
O001 C00D 1.325(2) . ?
O001 C00N 1.482(2) . ?
O002 C00D 1.205(2) . ?
O003 C00L 1.195(2) . ?
O004 C00K 1.463(2) . ?
O004 C00L 1.337(3) . ?
N005 N006 1.4217(19) . ?
N005 C00A 1.444(2) . ?
N005 C00D 1.401(2) . ?
N006 C00F 1.484(2) . ?
N006 C00L 1.420(2) . ?
C007 C008 1.385(2) . ?
C007 C00H 1.395(3) . ?
C008 C00F 1.515(2) . ?
C008 C00P 1.396(2) . ?
C009 C00A 1.468(2) . ?
C009 C00C 1.393(2) . ?
C009 C00E 1.400(2) . ?
C00A C00B 1.336(2) . ?
C00B C00F 1.521(2) . ?
C00C C00G 1.392(3) . ?
C00E C00J 1.382(3) . ?
C00F C00K 1.551(2) . ?
C00G C00I 1.380(3) . ?
C00H C00M 1.382(3) . ?
C00I C00J 1.392(3) . ?
C00K C00R 1.508(3) . ?
C00M C00O 1.382(4) . ?
C00N C00Q 1.512(3) . ?
C00N C00S 1.514(3) . ?
C00N C00T 1.514(3) . ?
C00O C00P 1.380(3) . ?

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
C00D O001 C00N 121.51(13) . . ?
C00L O004 C00K 110.77(14) . . ?
N006 N005 C00A 106.52(12) . . ?
C00D N005 N006 114.66(13) . . ?
C00D N005 C00A 123.90(13) . . ?
N005 N006 C00F 106.22(12) . . ?
C00L N006 N005 110.15(13) . . ?
C00L N006 C00F 106.13(14) . . ?
C008 C007 C00H 119.83(19) . . ?
C007 C008 C00F 122.29(16) . . ?
C007 C008 C00P 119.65(17) . . ?
C00P C008 C00F 118.00(16) . . ?
C00C C009 C00A 120.47(14) . . ?
C00C C009 C00E 118.73(15) . . ?
C00E C009 C00A 120.74(14) . . ?
N005 C00A C009 119.67(13) . . ?
C00B C00A N005 109.37(14) . . ?
C00B C00A C009 130.66(14) . . ?
C00A C00B C00F 109.35(14) . . ?
C00G C00C C009 120.17(16) . . ?
O001 C00D N005 108.92(13) . . ?
O002 C00D O001 127.97(16) . . ?
O002 C00D N005 123.08(15) . . ?
C00J C00E C009 120.96(16) . . ?
N006 C00F C008 114.03(13) . . ?
N006 C00F C00B 100.58(12) . . ?
N006 C00F C00K 100.77(13) . . ?
C008 C00F C00B 109.51(13) . . ?
C008 C00F C00K 113.96(14) . . ?
C00B C00F C00K 117.03(14) . . ?
C00I C00G C00C 120.46(17) . . ?
C00M C00H C007 120.2(2) . . ?
C00G C00I C00J 119.97(18) . . ?
C00E C00J C00I 119.70(17) . . ?
O004 C00K C00F 102.58(14) . . ?
O004 C00K C00R 108.87(17) . . ?
C00R C00K C00F 114.61(15) . . ?
O003 C00L O004 124.92(18) . . ?
O003 C00L N006 125.29(19) . . ?
O004 C00L N006 109.78(15) . . ?
C00H C00M C00O 119.90(18) . . ?
O001 C00N C00Q 109.68(15) . . ?
O001 C00N C00S 101.38(14) . . ?
O001 C00N C00T 109.30(15) . . ?
C00Q C00N C00S 111.11(19) . . ?
C00Q C00N C00T 112.80(18) . . ?
C00T C00N C00S 111.96(18) . . ?
C00P C00O C00M 120.4(2) . . ?
C00O C00P C008 120.02(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
