# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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#######################################################################

data_mo_20210309b_0ma
_database_code_depnum_ccdc_archive 'CCDC 2111609'
loop_
_audit_author_name
_audit_author_address
'qi Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
1-(4-(9H-carbazol-9-yl)phenyl)-3-(propylamino)pyrrolidine-2,5-dione
_chemical_formula_moiety         'C25 H23 N3 O2'
_chemical_formula_sum            'C25 H24 N3 O2'
_chemical_formula_weight         398.47
_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 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.3990(8)
_cell_length_b                   13.512(2)
_cell_length_c                   18.260(3)
_cell_angle_alpha                71.730(4)
_cell_angle_beta                 90
_cell_angle_gamma                80.63
_cell_volume                     1015.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7055
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6109
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1488 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.8193.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.674
_diffrn_reflns_Laue_measured_fraction_max 0.711
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13347
_diffrn_reflns_point_group_measured_fraction_full 0.674
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.802
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.674
_diffrn_measured_fraction_theta_max 0.711
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             3428
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.234
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      0.946
_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)+(0.1600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.2313
_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.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
  C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.8582(6) 0.10443(15) 0.54652(10) 0.0641(6) Uani 1 1 d . . . . .
O2 O 0.1057(6) 0.39627(14) 0.45338(11) 0.0661(6) Uani 1 1 d . . . . .
N1 N 0.6202(7) 0.34142(16) 0.79621(11) 0.0552(7) Uani 1 1 d . . . . .
N2 N 0.4810(6) 0.25364(14) 0.51806(11) 0.0460(5) Uani 1 1 d . . . . .
N3 N 0.7302(6) 0.12265(16) 0.38414(12) 0.0473(6) Uani 1 1 d . . . . .
H3 H 0.849(8) 0.064(2) 0.4157(15) 0.057 Uiso 1 1 d R . . . .
C1 C 0.5340(8) 0.4396(2) 0.80772(14) 0.0542(7) Uani 1 1 d . . . . .
C2 C 0.3351(10) 0.5290(2) 0.76194(16) 0.0623(8) Uani 1 1 d . . . . .
H2 H 0.2421 0.5310 0.7156 0.075 Uiso 1 1 calc R . . . .
C3 C 0.2842(11) 0.6144(2) 0.78935(17) 0.0754(11) Uani 1 1 d . . . . .
H3A H 0.1519 0.6755 0.7609 0.090 Uiso 1 1 calc R . . . .
C4 C 0.4260(12) 0.6115(2) 0.85869(18) 0.0842(13) Uani 1 1 d . . . . .
H4 H 0.3913 0.6713 0.8745 0.101 Uiso 1 1 calc R . . . .
C5 C 0.6147(12) 0.5224(3) 0.90374(17) 0.0777(12) Uani 1 1 d . . . . .
H5 H 0.7025 0.5209 0.9505 0.093 Uiso 1 1 calc R . . . .
C6 C 0.6744(9) 0.4336(2) 0.87894(14) 0.0573(8) Uani 1 1 d . . . . .
C7 C 0.8509(9) 0.3292(2) 0.91180(14) 0.0595(8) Uani 1 1 d . . . . .
C8 C 1.0395(12) 0.2769(3) 0.97951(17) 0.0817(11) Uani 1 1 d . . . . .
H8 H 1.0705 0.3119 1.0146 0.098 Uiso 1 1 calc R . . . .
C9 C 1.1771(13) 0.1737(3) 0.99321(19) 0.0924(13) Uani 1 1 d . . . . .
H9 H 1.3018 0.1391 1.0380 0.111 Uiso 1 1 calc R . . . .
C10 C 1.1341(11) 0.1199(3) 0.94170(17) 0.0784(10) Uani 1 1 d . . . . .
H10 H 1.2317 0.0501 0.9523 0.094 Uiso 1 1 calc R . . . .
C11 C 0.9478(9) 0.1686(2) 0.87461(16) 0.0649(9) Uani 1 1 d . . . . .
H11 H 0.9164 0.1322 0.8405 0.078 Uiso 1 1 calc R . . . .
C12 C 0.8095(8) 0.2734(2) 0.85998(13) 0.0540(7) Uani 1 1 d . . . . .
C13 C 0.5773(8) 0.32104(18) 0.72505(13) 0.0505(7) Uani 1 1 d . . . . .
C14 C 0.6619(8) 0.38789(18) 0.65745(13) 0.0518(7) Uani 1 1 d . . . . .
H14 H 0.7420 0.4473 0.6579 0.062 Uiso 1 1 calc R . . . .
C15 C 0.6282(8) 0.36696(18) 0.58881(13) 0.0502(7) Uani 1 1 d . . . . .
H15 H 0.6833 0.4126 0.5429 0.060 Uiso 1 1 calc R . . . .
C16 C 0.5127(7) 0.27828(17) 0.58870(12) 0.0462(6) Uani 1 1 d . . . . .
C17 C 0.4256(8) 0.2119(2) 0.65537(14) 0.0562(8) Uani 1 1 d . . . . .
H17 H 0.3450 0.1526 0.6548 0.067 Uiso 1 1 calc R . . . .
C18 C 0.4583(9) 0.23356(19) 0.72410(14) 0.0588(8) Uani 1 1 d . . . . .
H18 H 0.3994 0.1886 0.7698 0.071 Uiso 1 1 calc R . . . .
C19 C 0.2718(7) 0.31504(18) 0.45556(13) 0.0480(7) Uani 1 1 d . . . . .
C20 C 0.3026(7) 0.26185(18) 0.39440(13) 0.0482(6) Uani 1 1 d . . . . .
H20A H 0.4018 0.3024 0.3503 0.058 Uiso 1 1 calc R . . . .
H20B H 0.1017 0.2542 0.3772 0.058 Uiso 1 1 calc R . . . .
C21 C 0.4995(7) 0.15434(18) 0.43270(13) 0.0444(6) Uani 1 1 d . . . . .
H21 H 0.3644 0.1012 0.4479 0.053 Uiso 1 1 calc R . . . .
C22 C 0.6425(7) 0.16441(17) 0.50515(13) 0.0453(6) Uani 1 1 d . . . . .
C23 C 0.5815(7) 0.1032(2) 0.31888(14) 0.0515(7) Uani 1 1 d . . . . .
H23A H 0.4370 0.1661 0.2907 0.062 Uiso 1 1 calc R . . . .
H23B H 0.4657 0.0460 0.3387 0.062 Uiso 1 1 calc R . . . .
C24 C 0.8103(8) 0.0751(2) 0.26467(15) 0.0543(7) Uani 1 1 d . . . . .
H24A H 0.9411 0.0081 0.2913 0.065 Uiso 1 1 calc R . . . .
H24B H 0.9407 0.1287 0.2489 0.065 Uiso 1 1 calc R . . . .
C25 C 0.6513(10) 0.0666(3) 0.19342(16) 0.0710(10) Uani 1 1 d . . . . .
H25A H 0.8031 0.0559 0.1576 0.107 Uiso 1 1 calc GR . . . .
H25B H 0.5083 0.1306 0.1694 0.107 Uiso 1 1 calc GR . . . .
H25C H 0.5424 0.0079 0.2083 0.107 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 C22 1.222(4) . ?
O2 C19 1.205(3) . ?
N1 C1 1.400(3) . ?
N1 C12 1.405(4) . ?
N1 C13 1.429(3) . ?
N2 C16 1.442(3) . ?
N2 C19 1.412(3) . ?
N2 C22 1.383(3) . ?
N3 H3 0.90(3) . ?
N3 C21 1.448(3) . ?
N3 C23 1.473(3) . ?
C1 C2 1.395(5) . ?
C1 C6 1.413(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.398(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(4) . ?
C6 C7 1.437(5) . ?
C7 C8 1.406(5) . ?
C7 C12 1.411(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C13 C14 1.374(3) . ?
C13 C18 1.373(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(3) . ?
C16 C17 1.364(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.501(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.518(4) . ?
C21 H21 0.9800 . ?
C21 C22 1.518(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.499(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.522(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C1 N1 C12 108.7(2) . . ?
C1 N1 C13 125.1(2) . . ?
C12 N1 C13 125.0(2) . . ?
C19 N2 C16 124.0(2) . . ?
C22 N2 C16 123.7(2) . . ?
C22 N2 C19 112.21(19) . . ?
C21 N3 H3 104.9(19) . . ?
C21 N3 C23 110.3(2) . . ?
C23 N3 H3 112.5(17) . . ?
N1 C1 C6 107.8(3) . . ?
C2 C1 N1 128.9(3) . . ?
C2 C1 C6 123.2(2) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 C1 116.2(3) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 108.1(2) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 133.7(3) . . ?
C8 C7 C6 134.8(3) . . ?
C8 C7 C12 118.6(3) . . ?
C12 C7 C6 106.6(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
N1 C12 C7 108.7(2) . . ?
C11 C12 N1 129.6(2) . . ?
C11 C12 C7 121.7(3) . . ?
C14 C13 N1 119.9(2) . . ?
C18 C13 N1 120.3(2) . . ?
C18 C13 C14 119.8(2) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 N2 120.67(19) . . ?
C17 C16 N2 118.59(19) . . ?
C17 C16 C15 120.7(2) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
O2 C19 N2 124.4(2) . . ?
O2 C19 C20 127.8(2) . . ?
N2 C19 C20 107.8(2) . . ?
C19 C20 H20A 110.7 . . ?
C19 C20 H20B 110.7 . . ?
C19 C20 C21 105.21(19) . . ?
H20A C20 H20B 108.8 . . ?
C21 C20 H20A 110.7 . . ?
C21 C20 H20B 110.7 . . ?
N3 C21 C20 113.91(19) . . ?
N3 C21 H21 108.7 . . ?
N3 C21 C22 112.2(2) . . ?
C20 C21 H21 108.7 . . ?
C20 C21 C22 104.33(17) . . ?
C22 C21 H21 108.7 . . ?
O1 C22 N2 124.9(2) . . ?
O1 C22 C21 127.1(2) . . ?
N2 C22 C21 107.9(2) . . ?
N3 C23 H23A 109.1 . . ?
N3 C23 H23B 109.1 . . ?
N3 C23 C24 112.4(2) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C23 C24 C25 111.7(3) . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
