# 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_191240lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1985032'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'methyl 1-benzyl-5-(3-methoxypropyl)-3-(2-nitrophenyl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N3 O7'
_chemical_formula_weight         481.49

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.5539(6)
_cell_length_b                   21.1479(12)
_cell_length_c                   10.7227(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.937(3)
_cell_angle_gamma                90
_cell_volume                     2263.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6258
_cell_measurement_theta_min      2.3528
_cell_measurement_theta_max      26.3500

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6931
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18444
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4640
_reflns_number_gt                3794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+1.0820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4640
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.29371(12) 0.06597(6) 0.60676(12) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.10895(11) 0.14865(6) 0.08863(11) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.53106(12) 0.18755(6) 0.36258(11) 0.0234(3) Uani 1 1 d . . . . .
O4 O 0.10426(12) 0.15628(6) -0.25065(12) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.01116(12) 0.07551(6) -0.36761(11) 0.0252(3) Uani 1 1 d . . . . .
O6 O 0.70634(11) 0.12232(5) 0.22857(11) 0.0177(3) Uani 1 1 d . . . . .
O7 O 0.75128(11) 0.22600(5) 0.23148(11) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.31183(13) 0.16365(6) 0.24886(13) 0.0147(3) Uani 1 1 d . . . . .
N2 N 0.48606(13) 0.12718(6) 0.02627(12) 0.0129(3) Uani 1 1 d . . . . .
N3 N 0.08474(13) 0.09942(7) -0.26487(13) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.76262(18) 0.15700(8) -0.28243(16) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.8066 0.1393 -0.3387 0.024 Uiso 1 1 calc R U . . .
C2 C 0.83634(17) 0.17569(8) -0.15550(16) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.9310 0.1712 -0.1252 0.021 Uiso 1 1 calc R U . . .
C3 C 0.77174(16) 0.20101(7) -0.07262(15) 0.0155(3) Uani 1 1 d . . . . .
H14 H 0.8228 0.2134 0.0143 0.019 Uiso 1 1 calc R U . . .
C4 C 0.63315(16) 0.20836(7) -0.11558(15) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.56051(16) 0.23587(7) -0.02736(15) 0.0140(3) Uani 1 1 d . . . . .
H18 H 0.4708 0.2504 -0.0829 0.017 Uiso 1 1 calc R U . . .
H13 H 0.6106 0.2733 0.0187 0.017 Uiso 1 1 calc R U . . .
C6 C 0.54367(15) 0.18863(7) 0.07682(15) 0.0119(3) Uani 1 1 d . . . . .
C7 C 0.43364(15) 0.21453(7) 0.12901(15) 0.0131(3) Uani 1 1 d . . . . .
H5 H 0.4349 0.2618 0.1311 0.016 Uiso 1 1 calc R U . . .
C8 C 0.43733(16) 0.18769(7) 0.26136(15) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.27205(17) 0.13987(8) 0.35896(16) 0.0174(3) Uani 1 1 d . . . . .
H23 H 0.1775 0.1515 0.3447 0.021 Uiso 1 1 calc R U . . .
H24 H 0.3279 0.1603 0.4415 0.021 Uiso 1 1 calc R U . . .
C10 C 0.28691(18) 0.06852(8) 0.37401(17) 0.0213(4) Uani 1 1 d . . . . .
H25 H 0.3831 0.0573 0.4004 0.026 Uiso 1 1 calc R U . . .
H4 H 0.2411 0.0482 0.2879 0.026 Uiso 1 1 calc R U . . .
C11 C 0.22816(19) 0.04308(9) 0.47627(17) 0.0258(4) Uani 1 1 d . . . . .
H27 H 0.1322 0.0548 0.4497 0.031 Uiso 1 1 calc R U . . .
H26 H 0.2336 -0.0037 0.4770 0.031 Uiso 1 1 calc R U . . .
C12 C 0.41024(18) 0.03116(9) 0.67368(19) 0.0292(4) Uani 1 1 d . . . . .
H28 H 0.3871 -0.0136 0.6760 0.044 Uiso 1 1 calc R U . . .
H2 H 0.4484 0.0471 0.7640 0.044 Uiso 1 1 calc R U . . .
H3 H 0.4760 0.0358 0.6275 0.044 Uiso 1 1 calc R U . . .
C13 C 0.22475(16) 0.16526(7) 0.12045(15) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.30061(15) 0.18980(7) 0.03169(15) 0.0125(3) Uani 1 1 d . . . . .
H22 H 0.2499 0.2242 -0.0276 0.015 Uiso 1 1 calc R U . . .
C15 C 0.34359(15) 0.13621(7) -0.04872(15) 0.0122(3) Uani 1 1 d . . . . .
H6 H 0.3334 0.1515 -0.1397 0.015 Uiso 1 1 calc R U . . .
C16 C 0.26838(15) 0.07397(7) -0.05540(15) 0.0128(3) Uani 1 1 d . . . . .
C17 C 0.14911(16) 0.05737(7) -0.15360(15) 0.0141(3) Uani 1 1 d . . . . .
C18 C 0.08225(16) 0.00101(8) -0.15110(17) 0.0187(3) Uani 1 1 d . . . . .
H10 H 0.0013 -0.0084 -0.2197 0.022 Uiso 1 1 calc R U . . .
C19 C 0.13328(17) -0.04122(8) -0.04920(17) 0.0202(4) Uani 1 1 d . . . . .
H9 H 0.0871 -0.0794 -0.0459 0.024 Uiso 1 1 calc R U . . .
C20 C 0.25303(17) -0.02711(8) 0.04836(16) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.2899 -0.0561 0.1185 0.022 Uiso 1 1 calc R U . . .
C21 C 0.31940(16) 0.02920(7) 0.04411(16) 0.0157(3) Uani 1 1 d . . . . .
H7 H 0.4022 0.0375 0.1111 0.019 Uiso 1 1 calc R U . . .
C22 C 0.62489(18) 0.16426(9) -0.32670(16) 0.0226(4) Uani 1 1 d . . . . .
H15 H 0.5742 0.1519 -0.4138 0.027 Uiso 1 1 calc R U . . .
C23 C 0.56047(17) 0.18976(8) -0.24363(16) 0.0196(4) Uani 1 1 d . . . . .
H16 H 0.4658 0.1945 -0.2746 0.023 Uiso 1 1 calc R U . . .
C24 C 0.67827(15) 0.18202(7) 0.18746(15) 0.0133(3) Uani 1 1 d . . . . .
C25 C 0.82807(18) 0.11532(9) 0.33861(17) 0.0250(4) Uani 1 1 d . . . . .
H20 H 0.9036 0.1323 0.3149 0.037 Uiso 1 1 calc R U . . .
H21 H 0.8436 0.0704 0.3610 0.037 Uiso 1 1 calc R U . . .
H19 H 0.8198 0.1385 0.4147 0.037 Uiso 1 1 calc R U . . .
H11 H 0.5354 0.1057 -0.0208 0.080 Uiso 1 1 d . . . . .


_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 C12 1.413(2) . ?
O1 C11 1.429(2) . ?
O2 C13 1.2095(19) . ?
O3 C8 1.208(2) . ?
O4 N3 1.2211(18) . ?
O5 N3 1.2317(18) . ?
O6 C24 1.3384(19) . ?
O6 C25 1.4425(19) . ?
O7 C24 1.2023(19) . ?
N1 C8 1.384(2) . ?
N1 C13 1.386(2) . ?
N1 C9 1.4644(19) . ?
N2 C6 1.4623(19) . ?
N2 C15 1.4694(19) . ?
N2 H11 0.9502 . ?
N3 C17 1.466(2) . ?
C1 C22 1.383(3) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(2) . ?
C2 H17 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H14 0.9500 . ?
C4 C23 1.395(2) . ?
C4 C5 1.514(2) . ?
C5 C6 1.551(2) . ?
C5 H18 0.9900 . ?
C5 H13 0.9900 . ?
C6 C24 1.533(2) . ?
C6 C7 1.544(2) . ?
C7 C8 1.517(2) . ?
C7 C14 1.544(2) . ?
C7 H5 1.0000 . ?
C9 C10 1.520(2) . ?
C9 H23 0.9900 . ?
C9 H24 0.9900 . ?
C10 C11 1.522(2) . ?
C10 H25 0.9900 . ?
C10 H4 0.9900 . ?
C11 H27 0.9900 . ?
C11 H26 0.9900 . ?
C12 H28 0.9800 . ?
C12 H2 0.9800 . ?
C12 H3 0.9800 . ?
C13 C14 1.520(2) . ?
C14 C15 1.577(2) . ?
C14 H22 1.0000 . ?
C15 C16 1.527(2) . ?
C15 H6 1.0000 . ?
C16 C21 1.397(2) . ?
C16 C17 1.399(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.378(2) . ?
C18 H10 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H9 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H8 0.9500 . ?
C21 H7 0.9500 . ?
C22 C23 1.393(2) . ?
C22 H15 0.9500 . ?
C23 H16 0.9500 . ?
C25 H20 0.9800 . ?
C25 H21 0.9800 . ?
C25 H19 0.9800 . ?

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
C12 O1 C11 112.69(14) . . ?
C24 O6 C25 114.17(13) . . ?
C8 N1 C13 113.11(13) . . ?
C8 N1 C9 124.32(13) . . ?
C13 N1 C9 122.56(13) . . ?
C6 N2 C15 108.42(11) . . ?
C6 N2 H11 112.8 . . ?
C15 N2 H11 114.3 . . ?
O4 N3 O5 123.22(14) . . ?
O4 N3 C17 118.74(13) . . ?
O5 N3 C17 118.03(14) . . ?
C22 C1 C2 119.80(15) . . ?
C22 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 120.07(16) . . ?
C1 C2 H17 120.0 . . ?
C3 C2 H17 120.0 . . ?
C2 C3 C4 120.78(15) . . ?
C2 C3 H14 119.6 . . ?
C4 C3 H14 119.6 . . ?
C3 C4 C23 118.51(15) . . ?
C3 C4 C5 121.79(14) . . ?
C23 C4 C5 119.69(14) . . ?
C4 C5 C6 113.71(12) . . ?
C4 C5 H18 108.8 . . ?
C6 C5 H18 108.8 . . ?
C4 C5 H13 108.8 . . ?
C6 C5 H13 108.8 . . ?
H18 C5 H13 107.7 . . ?
N2 C6 C24 112.03(12) . . ?
N2 C6 C7 100.28(12) . . ?
C24 C6 C7 111.64(12) . . ?
N2 C6 C5 115.87(12) . . ?
C24 C6 C5 108.79(12) . . ?
C7 C6 C5 107.94(12) . . ?
C8 C7 C14 104.31(12) . . ?
C8 C7 C6 114.35(13) . . ?
C14 C7 C6 105.12(12) . . ?
C8 C7 H5 110.9 . . ?
C14 C7 H5 110.9 . . ?
C6 C7 H5 110.9 . . ?
O3 C8 N1 124.40(14) . . ?
O3 C8 C7 127.31(15) . . ?
N1 C8 C7 108.27(13) . . ?
N1 C9 C10 112.33(13) . . ?
N1 C9 H23 109.1 . . ?
C10 C9 H23 109.1 . . ?
N1 C9 H24 109.1 . . ?
C10 C9 H24 109.1 . . ?
H23 C9 H24 107.9 . . ?
C9 C10 C11 112.04(14) . . ?
C9 C10 H25 109.2 . . ?
C11 C10 H25 109.2 . . ?
C9 C10 H4 109.2 . . ?
C11 C10 H4 109.2 . . ?
H25 C10 H4 107.9 . . ?
O1 C11 C10 113.86(14) . . ?
O1 C11 H27 108.8 . . ?
C10 C11 H27 108.8 . . ?
O1 C11 H26 108.8 . . ?
C10 C11 H26 108.8 . . ?
H27 C11 H26 107.7 . . ?
O1 C12 H28 109.5 . . ?
O1 C12 H2 109.5 . . ?
H28 C12 H2 109.5 . . ?
O1 C12 H3 109.5 . . ?
H28 C12 H3 109.5 . . ?
H2 C12 H3 109.5 . . ?
O2 C13 N1 123.84(14) . . ?
O2 C13 C14 127.72(14) . . ?
N1 C13 C14 108.44(13) . . ?
C13 C14 C7 103.93(12) . . ?
C13 C14 C15 113.60(12) . . ?
C7 C14 C15 104.67(12) . . ?
C13 C14 H22 111.4 . . ?
C7 C14 H22 111.4 . . ?
C15 C14 H22 111.4 . . ?
N2 C15 C16 109.75(12) . . ?
N2 C15 C14 102.65(11) . . ?
C16 C15 C14 114.07(12) . . ?
N2 C15 H6 110.0 . . ?
C16 C15 H6 110.0 . . ?
C14 C15 H6 110.0 . . ?
C21 C16 C17 115.76(14) . . ?
C21 C16 C15 118.86(14) . . ?
C17 C16 C15 125.37(14) . . ?
C18 C17 C16 122.63(15) . . ?
C18 C17 N3 115.58(14) . . ?
C16 C17 N3 121.77(14) . . ?
C19 C18 C17 120.05(15) . . ?
C19 C18 H10 120.0 . . ?
C17 C18 H10 120.0 . . ?
C18 C19 C20 118.99(15) . . ?
C18 C19 H9 120.5 . . ?
C20 C19 H9 120.5 . . ?
C19 C20 C21 120.35(15) . . ?
C19 C20 H8 119.8 . . ?
C21 C20 H8 119.8 . . ?
C20 C21 C16 122.15(15) . . ?
C20 C21 H7 118.9 . . ?
C16 C21 H7 118.9 . . ?
C1 C22 C23 120.02(16) . . ?
C1 C22 H15 120.0 . . ?
C23 C22 H15 120.0 . . ?
C22 C23 C4 120.81(16) . . ?
C22 C23 H16 119.6 . . ?
C4 C23 H16 119.6 . . ?
O7 C24 O6 123.73(14) . . ?
O7 C24 C6 123.23(14) . . ?
O6 C24 C6 113.04(13) . . ?
O6 C25 H20 109.5 . . ?
O6 C25 H21 109.5 . . ?
H20 C25 H21 109.5 . . ?
O6 C25 H19 109.5 . . ?
H20 C25 H19 109.5 . . ?
H21 C25 H19 109.5 . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6



