# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_exp_1362-5
_database_code_depnum_ccdc_archive 'CCDC 2057122'
loop_
_audit_author_name
_audit_author_address
'Yumin Kim' 'Seoul National University'
_audit_update_record             
;
2021-01-19 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        DTTP4
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H20 N2 O2'
_chemical_oxdiff_usercomment     'ethylmaleimide based FP'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.6320(8)
_cell_length_b                   9.0024(9)
_cell_length_c                   29.319(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3070.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    292.6(3)
_cell_measurement_theta_max      24.5700
_cell_measurement_theta_min      3.2700
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.073
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_min         2.235
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  58.00   1.00    8.74    --  -11.04  41.00-114.00   67
  2  ω    -46.00   9.00   1.00    8.74    --  -11.04 -41.00  92.00   55
  3  ω    -19.00  30.00   1.00    8.74    --  -11.04 -99.00 -90.00   49
  4  ω    -12.00  17.00   1.00    8.74    --  -11.04 -99.00   0.00   29
  5  ω    -17.00  45.00   1.00    8.74    --   11.51 -99.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405091000
_diffrn_orient_matrix_UB_12      0.0434096000
_diffrn_orient_matrix_UB_13      -0.0122350000
_diffrn_orient_matrix_UB_21      0.0412594000
_diffrn_orient_matrix_UB_22      -0.0574803000
_diffrn_orient_matrix_UB_23      0.0022942000
_diffrn_orient_matrix_UB_31      -0.0193200000
_diffrn_orient_matrix_UB_32      -0.0319564000
_diffrn_orient_matrix_UB_33      -0.0207467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2106
_reflns_number_total             3770
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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         0.148
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.035
_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)+(0.0484P)²+0.9336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1553
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C1(H1), C5(H5), C4(H4), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_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
O14 O 0.33134(13) 0.2691(2) 0.49954(5) 0.0605(5) Uani 1 1 d . . . . .
O10 O 0.16421(14) 0.65856(19) 0.37538(5) 0.0587(5) Uani 1 1 d . . . . .
N15 N 0.47986(14) 0.3653(2) 0.45744(5) 0.0403(4) Uani 1 1 d . . . . .
N8 N 0.35143(17) 0.7064(2) 0.35357(6) 0.0506(5) Uani 1 1 d . . . . .
C18 C 0.52329(17) 0.4568(2) 0.42377(6) 0.0412(5) Uani 1 1 d . . . . .
C11 C 0.33027(17) 0.5385(2) 0.41049(6) 0.0392(5) Uani 1 1 d . . . . .
C20 C 0.44791(17) 0.5449(2) 0.40085(6) 0.0399(5) Uani 1 1 d . . . . .
C9 C 0.2682(2) 0.6400(3) 0.37904(7) 0.0463(6) Uani 1 1 d . . . . .
C12 C 0.28679(18) 0.4493(3) 0.44330(6) 0.0441(5) Uani 1 1 d . . . . .
H12 H 0.208217 0.448841 0.449171 0.053 Uiso 1 1 calc R . . . .
C13 C 0.36228(17) 0.3555(3) 0.46899(7) 0.0435(5) Uani 1 1 d . . . . .
C16 C 0.55587(18) 0.2598(3) 0.48180(7) 0.0486(6) Uani 1 1 d . . . . .
H16A H 0.526230 0.242577 0.512264 0.058 Uiso 1 1 calc R . . . .
H16B H 0.632191 0.302243 0.484590 0.058 Uiso 1 1 calc R . . . .
C6 C 0.3511(2) 0.7658(3) 0.27120(7) 0.0496(6) Uani 1 1 d . . . . .
C21 C 0.46955(19) 0.6594(3) 0.36424(7) 0.0490(6) Uani 1 1 d . . . . .
H21 H 0.503796 0.611413 0.337486 0.059 Uiso 1 1 calc R . . . .
C17 C 0.5629(2) 0.1144(3) 0.45649(8) 0.0561(6) Uani 1 1 d . . . . .
H17A H 0.600513 0.129668 0.427719 0.084 Uiso 1 1 calc GR . . . .
H17B H 0.486764 0.076816 0.451362 0.084 Uiso 1 1 calc GR . . . .
H17C H 0.605916 0.044169 0.474250 0.084 Uiso 1 1 calc GR . . . .
C19 C 0.64979(18) 0.4544(3) 0.41427(8) 0.0605(7) Uani 1 1 d . . . . .
H19A H 0.689887 0.504539 0.438390 0.091 Uiso 1 1 calc GR . . . .
H19B H 0.664817 0.503705 0.385855 0.091 Uiso 1 1 calc GR . . . .
H19C H 0.675760 0.353331 0.412468 0.091 Uiso 1 1 calc GR . . . .
C7 C 0.3258(2) 0.8181(3) 0.31913(7) 0.0606(7) Uani 1 1 d . . . . .
H7A H 0.370741 0.906497 0.325375 0.073 Uiso 1 1 calc R . . . .
H7B H 0.245162 0.844834 0.321247 0.073 Uiso 1 1 calc R . . . .
C1 C 0.2846(3) 0.6557(3) 0.25190(9) 0.0702(8) Uani 1 1 d . . . . .
H1 H 0.224027 0.615116 0.268425 0.084 Uiso 1 1 calc R . . . .
C5 C 0.4399(2) 0.8246(3) 0.24615(9) 0.0707(8) Uani 1 1 d . . . . .
H5 H 0.485852 0.898804 0.258592 0.085 Uiso 1 1 calc R . . . .
C22 C 0.5440(3) 0.7899(3) 0.37898(10) 0.0778(9) Uani 1 1 d . . . . .
H22A H 0.554924 0.855959 0.353635 0.117 Uiso 1 1 calc GR . . . .
H22B H 0.617300 0.753949 0.389208 0.117 Uiso 1 1 calc GR . . . .
H22C H 0.506764 0.842216 0.403395 0.117 Uiso 1 1 calc GR . . . .
C4 C 0.4611(3) 0.7734(5) 0.20211(11) 0.0938(11) Uani 1 1 d . . . . .
H4 H 0.520963 0.813622 0.185092 0.113 Uiso 1 1 calc R . . . .
C3 C 0.3941(4) 0.6642(5) 0.18403(10) 0.1045(14) Uani 1 1 d . . . . .
H3 H 0.408300 0.629828 0.154658 0.125 Uiso 1 1 calc R . . . .
C2 C 0.3067(4) 0.6055(4) 0.20870(10) 0.0976(12) Uani 1 1 d . . . . .
H2 H 0.261433 0.530644 0.196219 0.117 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
O14 C13 1.240(3) . ?
O10 C9 1.226(3) . ?
N15 C18 1.382(3) . ?
N15 C13 1.412(3) . ?
N15 C16 1.481(3) . ?
N8 C9 1.361(3) . ?
N8 C21 1.471(3) . ?
N8 C7 1.456(3) . ?
C18 C20 1.360(3) . ?
C18 C19 1.498(3) . ?
C11 C20 1.399(3) . ?
C11 C9 1.486(3) . ?
C11 C12 1.351(3) . ?
C20 C21 1.509(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.433(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.507(3) . ?
C6 C7 1.511(3) . ?
C6 C1 1.379(4) . ?
C6 C5 1.373(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.523(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1 0.9300 . ?
C1 C2 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.393(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.362(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.355(5) . ?
C2 H2 0.9300 . ?

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
C18 N15 C13 124.27(18) . . ?
C18 N15 C16 120.58(17) . . ?
C13 N15 C16 114.98(17) . . ?
C9 N8 C21 114.94(18) . . ?
C9 N8 C7 122.5(2) . . ?
C7 N8 C21 122.51(19) . . ?
N15 C18 C19 118.9(2) . . ?
C20 C18 N15 117.72(18) . . ?
C20 C18 C19 123.4(2) . . ?
C20 C11 C9 108.93(19) . . ?
C12 C11 C20 122.3(2) . . ?
C12 C11 C9 128.7(2) . . ?
C18 C20 C11 120.5(2) . . ?
C18 C20 C21 129.95(19) . . ?
C11 C20 C21 109.59(18) . . ?
O10 C9 N8 126.5(2) . . ?
O10 C9 C11 128.1(2) . . ?
N8 C9 C11 105.36(19) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.68(19) . . ?
C13 C12 H12 120.2 . . ?
O14 C13 N15 119.60(19) . . ?
O14 C13 C12 124.89(19) . . ?
N15 C13 C12 115.51(19) . . ?
N15 C16 H16A 109.5 . . ?
N15 C16 H16B 109.5 . . ?
N15 C16 C17 110.61(17) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 C1 118.7(2) . . ?
N8 C21 C20 101.05(17) . . ?
N8 C21 H21 109.6 . . ?
N8 C21 C22 111.7(2) . . ?
C20 C21 H21 109.6 . . ?
C20 C21 C22 114.84(19) . . ?
C22 C21 H21 109.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N8 C7 C6 112.95(19) . . ?
N8 C7 H7A 109.0 . . ?
N8 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.1 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?


_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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.539
