# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_biisoindoline
_database_code_depnum_ccdc_archive 'CCDC 2065589'
loop_
_audit_author_name
_audit_author_address
haiyu
;Fujian Medical University
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_audit_creation_date             2021-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.006(6)
_cell_length_b                   6.157(2)
_cell_length_c                   27.288(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2521.3(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5896
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.4894
_cell_measurement_theta_min      2.0169
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14357
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.986
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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                1836
_reflns_number_total             2798
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.084
_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)+(0.0737P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1475
_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
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.81942(10) -0.0176(2) 0.34795(5) 0.0562(4) Uani 1 1 d . . . . .
N2 N 0.83806(10) -0.5661(2) 0.41749(6) 0.0487(4) Uani 1 1 d . . . . .
H2 H 0.7803 -0.5722 0.4120 0.058 Uiso 1 1 calc R U . . .
O3 O 0.84993(11) -0.8876(2) 0.46004(5) 0.0642(5) Uani 1 1 d . . . . .
N4 N 0.88973(10) -0.3527(2) 0.34852(6) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.85091(12) -0.1760(3) 0.32678(7) 0.0421(4) Uani 1 1 d . . . . .
C6 C 0.98379(12) -0.4544(3) 0.41912(6) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.97740(12) -0.6533(3) 0.44237(6) 0.0444(4) Uani 1 1 d . . . . .
C8 C 0.85614(11) -0.2152(3) 0.27338(7) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.89415(12) -0.4171(3) 0.26516(7) 0.0431(4) Uani 1 1 d . . . . .
C10 C 0.88245(13) -0.7237(3) 0.44172(7) 0.0453(5) Uani 1 1 d . . . . .
C11 C 0.82764(13) -0.0835(3) 0.23531(7) 0.0478(5) Uani 1 1 d . . . . .
H11 H 0.8016 0.0544 0.2415 0.057 Uiso 1 1 calc R U . . .
C12 C 0.83835(14) -0.1595(4) 0.18789(7) 0.0559(5) Uani 1 1 d . . . . .
H12 H 0.8189 -0.0735 0.1611 0.067 Uiso 1 1 calc R U . . .
C13 C 0.91521(14) -0.5220(3) 0.31336(7) 0.0493(5) Uani 1 1 d . . . . .
H13A H 0.8798 -0.6558 0.3182 0.059 Uiso 1 1 calc R U . . .
H13B H 0.9794 -0.5575 0.3160 0.059 Uiso 1 1 calc R U . . .
C14 C 0.89281(12) -0.3860(3) 0.40124(7) 0.0439(4) Uani 1 1 d . . . . .
H14 H 0.8740 -0.2501 0.4184 0.053 Uiso 1 1 calc R U . . .
C15 C 0.87713(15) -0.3599(4) 0.17932(8) 0.0585(6) Uani 1 1 d . . . . .
H15 H 0.8843 -0.4087 0.1465 0.070 Uiso 1 1 calc R U . . .
C16 C 0.90584(13) -0.4912(3) 0.21754(7) 0.0543(5) Uani 1 1 d . . . . .
H16 H 0.9328 -0.6281 0.2113 0.065 Uiso 1 1 calc R U . . .
C17 C 1.05179(15) -0.7490(4) 0.46362(7) 0.0593(6) Uani 1 1 d . . . . .
H17 H 1.0474 -0.8862 0.4794 0.071 Uiso 1 1 calc R U . . .
C18 C 1.06379(14) -0.3458(4) 0.41644(7) 0.0608(6) Uani 1 1 d . . . . .
H18 H 1.0683 -0.2095 0.4003 0.073 Uiso 1 1 calc R U . . .
C19 C 1.13204(15) -0.6408(5) 0.46141(8) 0.0716(7) Uani 1 1 d . . . . .
H19 H 1.1835 -0.7034 0.4760 0.086 Uiso 1 1 calc R U . . .
C20 C 1.13833(15) -0.4427(5) 0.43824(9) 0.0741(7) Uani 1 1 d . . . . .
H20 H 1.1942 -0.3704 0.4370 0.089 Uiso 1 1 calc R U . . .


_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 C5 1.228(2) . ?
N2 H2 0.8800 . ?
N2 C10 1.350(2) . ?
N2 C14 1.449(2) . ?
O3 C10 1.227(2) . ?
N4 C5 1.369(2) . ?
N4 C13 1.467(2) . ?
N4 C14 1.454(2) . ?
C5 C8 1.479(2) . ?
C6 C7 1.383(3) . ?
C6 C14 1.510(3) . ?
C6 C18 1.376(3) . ?
C7 C10 1.489(3) . ?
C7 C17 1.389(3) . ?
C8 C9 1.386(2) . ?
C8 C11 1.385(3) . ?
C9 C13 1.499(3) . ?
C9 C16 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C15 1.384(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C18 C20 1.400(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9500 . ?

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
C10 N2 H2 122.6 . . ?
C10 N2 C14 114.84(16) . . ?
C14 N2 H2 122.6 . . ?
C5 N4 C13 113.07(15) . . ?
C5 N4 C14 123.69(15) . . ?
C14 N4 C13 122.56(14) . . ?
O1 C5 N4 126.21(18) . . ?
O1 C5 C8 127.82(17) . . ?
N4 C5 C8 105.96(15) . . ?
C7 C6 C14 109.42(15) . . ?
C18 C6 C7 121.01(18) . . ?
C18 C6 C14 129.53(17) . . ?
C6 C7 C10 108.59(15) . . ?
C6 C7 C17 120.75(19) . . ?
C17 C7 C10 130.58(19) . . ?
C9 C8 C5 109.12(15) . . ?
C11 C8 C5 128.83(17) . . ?
C11 C8 C9 122.04(17) . . ?
C8 C9 C13 109.34(16) . . ?
C8 C9 C16 119.89(17) . . ?
C16 C9 C13 130.76(17) . . ?
N2 C10 C7 105.58(16) . . ?
O3 C10 N2 126.46(18) . . ?
O3 C10 C7 127.94(17) . . ?
C8 C11 H11 121.1 . . ?
C8 C11 C12 117.83(19) . . ?
C12 C11 H11 121.1 . . ?
C11 C12 H12 119.7 . . ?
C15 C12 C11 120.52(19) . . ?
C15 C12 H12 119.7 . . ?
N4 C13 C9 102.28(14) . . ?
N4 C13 H13A 111.3 . . ?
N4 C13 H13B 111.3 . . ?
C9 C13 H13A 111.3 . . ?
C9 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
N2 C14 N4 113.13(14) . . ?
N2 C14 C6 101.57(14) . . ?
N2 C14 H14 109.7 . . ?
N4 C14 C6 112.82(15) . . ?
N4 C14 H14 109.7 . . ?
C6 C14 H14 109.7 . . ?
C12 C15 H15 119.2 . . ?
C12 C15 C16 121.51(19) . . ?
C16 C15 H15 119.2 . . ?
C9 C16 H16 120.9 . . ?
C15 C16 C9 118.19(19) . . ?
C15 C16 H16 120.9 . . ?
C7 C17 H17 120.7 . . ?
C19 C17 C7 118.7(2) . . ?
C19 C17 H17 120.7 . . ?
C6 C18 H18 121.1 . . ?
C6 C18 C20 117.9(2) . . ?
C20 C18 H18 121.1 . . ?
C17 C19 H19 119.7 . . ?
C17 C19 C20 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C20 H20 119.4 . . ?
C19 C20 C18 121.2(2) . . ?
C19 C20 H20 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C8 C9 -178.18(18) . . . . ?
O1 C5 C8 C11 0.4(3) . . . . ?
N4 C5 C8 C9 2.58(19) . . . . ?
N4 C5 C8 C11 -178.79(18) . . . . ?
C5 N4 C13 C9 5.0(2) . . . . ?
C5 N4 C14 N2 111.56(19) . . . . ?
C5 N4 C14 C6 -133.83(17) . . . . ?
C5 C8 C9 C13 0.5(2) . . . . ?
C5 C8 C9 C16 179.73(15) . . . . ?
C5 C8 C11 C12 -178.57(16) . . . . ?
C6 C7 C10 N2 1.1(2) . . . . ?
C6 C7 C10 O3 -177.49(19) . . . . ?
C6 C7 C17 C19 0.5(3) . . . . ?
C6 C18 C20 C19 0.4(3) . . . . ?
C7 C6 C14 N2 0.38(19) . . . . ?
C7 C6 C14 N4 -121.03(16) . . . . ?
C7 C6 C18 C20 -0.3(3) . . . . ?
C7 C17 C19 C20 -0.5(3) . . . . ?
C8 C9 C13 N4 -3.1(2) . . . . ?
C8 C9 C16 C15 -1.1(3) . . . . ?
C8 C11 C12 C15 -0.6(3) . . . . ?
C9 C8 C11 C12 -0.1(3) . . . . ?
C10 N2 C14 N4 121.57(18) . . . . ?
C10 N2 C14 C6 0.4(2) . . . . ?
C10 C7 C17 C19 -175.71(19) . . . . ?
C11 C8 C9 C13 -178.26(17) . . . . ?
C11 C8 C9 C16 1.0(3) . . . . ?
C11 C12 C15 C16 0.4(3) . . . . ?
C12 C15 C16 C9 0.4(3) . . . . ?
C13 N4 C5 O1 175.95(18) . . . . ?
C13 N4 C5 C8 -4.8(2) . . . . ?
C13 N4 C14 N2 -58.3(2) . . . . ?
C13 N4 C14 C6 56.3(2) . . . . ?
C13 C9 C16 C15 177.93(19) . . . . ?
C14 N2 C10 O3 177.73(18) . . . . ?
C14 N2 C10 C7 -0.9(2) . . . . ?
C14 N4 C5 O1 5.2(3) . . . . ?
C14 N4 C5 C8 -175.53(14) . . . . ?
C14 N4 C13 C9 175.82(14) . . . . ?
C14 C6 C7 C10 -0.9(2) . . . . ?
C14 C6 C7 C17 -177.90(16) . . . . ?
C14 C6 C18 C20 176.98(19) . . . . ?
C16 C9 C13 N4 177.76(18) . . . . ?
C17 C7 C10 N2 177.70(19) . . . . ?
C17 C7 C10 O3 -0.9(3) . . . . ?
C17 C19 C20 C18 0.1(3) . . . . ?
C18 C6 C7 C10 176.89(16) . . . . ?
C18 C6 C7 C17 -0.1(3) . . . . ?
C18 C6 C14 N2 -177.19(18) . . . . ?
C18 C6 C14 N4 61.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2-lactam-isoindolinone
_database_code_depnum_ccdc_archive 'CCDC 2065590'
loop_
_audit_author_name
_audit_author_address
haiyu
;Fujian Medical University
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.806(3)
_cell_length_b                   11.637(3)
_cell_length_c                   9.954(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.446(4)
_cell_angle_gamma                90
_cell_volume                     1094.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.1500
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.1547
_cell_measurement_theta_max      27.4855
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.3119
_exptl_crystal_F_000             456.2227
_exptl_crystal_description       Prism
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8554
_diffrn_reflns_theta_full        27.4844
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.59
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -7
_reflns_number_gt                1717
_reflns_number_total             2504
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.1982
_refine_diff_density_min         -0.2286
_refine_diff_density_rms         0.0412
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             7.8608
_refine_ls_goodness_of_fit_ref   1.0483
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.0483
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1413
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C11(H11), C13(H13), C14(H14)
;
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_refinement_flags_posn
O1 O 0.01512(12) 0.55720(9) 0.83470(10) 0.0631(3) Uani 1.000000 .
N2 N 0.14306(12) 0.80198(10) 1.20182(11) 0.0507(3) Uani 1.000000 .
N3 N 0.10373(14) 0.63236(10) 1.05488(12) 0.0544(3) Uani 1.000000 .
H3 H 0.05671(14) 0.58772(10) 1.09822(12) 0.0652(4) Uiso 1.000000 R
C4 C 0.08968(16) 0.62574(11) 0.91634(14) 0.0494(4) Uani 1.000000 .
C5 C 0.18279(15) 0.71555(12) 0.88389(14) 0.0484(4) Uani 1.000000 .
C6 C 0.20353(15) 0.71982(12) 1.12659(14) 0.0502(4) Uani 1.000000 .
H6 H 0.28607(15) 0.68153(12) 1.19237(14) 0.0602(4) Uiso 1.000000 R
O7 O 0.24425(16) 0.72920(13) 1.41750(12) 0.0949(5) Uani 1.000000 .
C8 C 0.20918(16) 0.74443(13) 0.75733(15) 0.0559(4) Uani 1.000000 .
H8 H 0.16331(16) 0.70532(13) 0.67373(15) 0.0670(5) Uiso 1.000000 R
C9 C 0.16948(18) 0.79983(15) 1.34190(17) 0.0636(5) Uani 1.000000 .
C10 C 0.25050(15) 0.77109(12) 1.00599(15) 0.0514(4) Uani 1.000000 .
C11 C 0.30430(17) 0.83185(15) 0.75774(17) 0.0651(5) Uani 1.000000 .
H11 H 0.32469(17) 0.85367(15) 0.67318(17) 0.0781(5) Uiso 1.000000 R
C12 C 0.0463(2) 0.89135(15) 1.13440(19) 0.0773(6) Uani 1.000000 .
H12a H 0.0918(2) 0.94346(15) 1.08067(19) 0.0927(7) Uiso 1.000000 R
H12b H -0.0397(2) 0.85792(15) 1.07066(19) 0.0927(7) Uiso 1.000000 R
C13 C 0.37031(19) 0.88808(16) 0.88047(19) 0.0740(5) Uani 1.000000 .
H13 H 0.43465(19) 0.94858(16) 0.87803(19) 0.0888(6) Uiso 1.000000 R
C14 C 0.34536(18) 0.85878(15) 1.00643(18) 0.0689(5) Uani 1.000000 .
H14 H 0.39176(18) 0.89754(15) 1.09012(18) 0.0827(6) Uiso 1.000000 R
C15 C 0.0103(2) 0.95474(18) 1.2533(2) 0.0897(6) Uani 1.000000 .
H15a H 0.0377(2) 1.03661(18) 1.2532(2) 0.1076(8) Uiso 1.000000 R
H15b H -0.0926(2) 0.95046(18) 1.2442(2) 0.1076(8) Uiso 1.000000 R
C16 C 0.0912(2) 0.89763(18) 1.3848(2) 0.0910(6) Uani 1.000000 .
H16a H 0.0259(2) 0.86896(18) 1.4379(2) 0.1093(8) Uiso 1.000000 R
H16b H 0.1582(2) 0.95238(18) 1.4442(2) 0.1093(8) Uiso 1.000000 R


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 C4 1.2306(16) . ?
N2 C6 1.4363(18) . ?
N2 C9 1.3488(19) . ?
N2 C12 1.4468(19) . ?
N3 C4 1.3510(18) . ?
N3 C6 1.4598(18) . ?
C4 C5 1.4790(19) . ?
C5 C8 1.3930(19) . ?
C5 C10 1.380(2) . ?
C6 C10 1.518(2) . ?
O7 C9 1.219(2) . ?
C8 C11 1.379(2) . ?
C9 C16 1.497(3) . ?
C10 C14 1.380(2) . ?
C11 C13 1.385(2) . ?
C12 C15 1.514(3) . ?
C13 C14 1.383(2) . ?
C15 C16 1.494(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
C9 N2 C6 122.29(12) . . ?
C12 N2 C6 123.20(12) . . ?
C12 N2 C9 114.49(13) . . ?
C6 N3 C4 114.31(11) . . ?
N3 C4 O1 126.31(13) . . ?
C5 C4 O1 127.33(13) . . ?
C5 C4 N3 106.35(12) . . ?
C8 C5 C4 129.95(13) . . ?
C10 C5 C4 108.58(12) . . ?
C10 C5 C8 121.44(13) . . ?
N3 C6 N2 113.76(11) . . ?
C10 C6 N2 113.90(12) . . ?
C10 C6 N3 101.10(11) . . ?
C11 C8 C5 117.61(14) . . ?
O7 C9 N2 124.69(16) . . ?
C16 C9 N2 108.00(15) . . ?
C16 C9 O7 127.31(16) . . ?
C6 C10 C5 109.65(12) . . ?
C14 C10 C5 120.98(13) . . ?
C14 C10 C6 129.38(14) . . ?
C13 C11 C8 120.52(14) . . ?
C15 C12 N2 104.38(15) . . ?
C14 C13 C11 121.96(15) . . ?
C13 C14 C10 117.48(15) . . ?
C16 C15 C12 106.77(16) . . ?
C15 C16 C9 106.30(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
