# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ki_a
_database_code_depnum_ccdc_archive 'CCDC 2130060'
loop_
_audit_author_name
_audit_author_address
'Kento Iwai'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'1,3-Diethyl 2-(tert-butylcarboxyamino)-2-(1-methylindol-3-yl)propanedioate'
_chemical_name_common            ?
_chemical_melting_point          401.1-401.8
_chemical_formula_moiety         'C21 H28 N2 O6'
_chemical_formula_sum            'C21 H28 N2 O6'
_chemical_formula_weight         404.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   10.3357(3)
_cell_length_b                   7.9301(2)
_cell_length_c                   13.6175(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.526(3)
_cell_angle_gamma                90
_cell_volume                     1064.32(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(1)

_cell_measurement_reflns_used    10093

_cell_measurement_theta_min      2.1810

_cell_measurement_theta_max      29.3740


_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             430
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2

_exptl_crystal_size_mid          0.2

_exptl_crystal_size_min          0.05

_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.23533

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(1)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            13103
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3961
_reflns_number_gt                3615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(9)
_chemical_absolute_configuration ?

_refine_ls_number_reflns         3961
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.5956(3) 0.5848(4) 0.2968(2) 0.0268(6) Uani 1 1 d . . . . .
N1 N 0.4596(2) 0.6506(3) 0.25217(18) 0.0284(5) Uani 1 1 d . . . . .
H1 H 0.449515 0.755576 0.230235 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3478(3) 0.5560(4) 0.2431(2) 0.0279(6) Uani 1 1 d . . . . .
O1 O 0.3513(2) 0.4090(3) 0.26862(17) 0.0363(5) Uani 1 1 d . . . . .
O2 O 0.23647(19) 0.6504(3) 0.20276(16) 0.0347(5) Uani 1 1 d . . . . .
C3 C 0.1003(3) 0.5812(4) 0.1908(2) 0.0354(7) Uani 1 1 d . . . . .
C4 C 0.0734(4) 0.4346(7) 0.1190(4) 0.0716(14) Uani 1 1 d . . . . .
H2 H 0.091000 0.466964 0.054772 0.107 Uiso 1 1 calc R U . . .
H3 H -0.021500 0.399669 0.104194 0.107 Uiso 1 1 calc R U . . .
H4 H 0.133008 0.340788 0.150904 0.107 Uiso 1 1 calc R U . . .
C5 C 0.0880(4) 0.5375(6) 0.2946(3) 0.0599(11) Uani 1 1 d . . . . .
H5 H 0.145824 0.440194 0.322473 0.090 Uiso 1 1 calc R U . . .
H6 H -0.006570 0.509847 0.288112 0.090 Uiso 1 1 calc R U . . .
H7 H 0.116812 0.633987 0.341019 0.090 Uiso 1 1 calc R U . . .
C6 C 0.0091(3) 0.7286(6) 0.1459(3) 0.0629(12) Uani 1 1 d . . . . .
H8 H 0.034004 0.825312 0.192620 0.094 Uiso 1 1 calc R U . . .
H9 H -0.085479 0.697529 0.137112 0.094 Uiso 1 1 calc R U . . .
H10 H 0.019675 0.758496 0.078939 0.094 Uiso 1 1 calc R U . . .
C7 C 0.6041(3) 0.4869(4) 0.3973(2) 0.0275(6) Uani 1 1 d . . . . .
O3 O 0.6533(2) 0.3503(2) 0.42033(15) 0.0310(5) Uani 1 1 d . . . . .
O4 O 0.5555(2) 0.5850(3) 0.45823(15) 0.0319(5) Uani 1 1 d . . . . .
C8 C 0.5647(4) 0.5155(4) 0.5591(2) 0.0387(8) Uani 1 1 d . . . . .
H11 H 0.539662 0.394597 0.551973 0.046 Uiso 1 1 calc R U . . .
H12 H 0.499980 0.574735 0.587856 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7061(4) 0.5342(5) 0.6312(2) 0.0476(9) Uani 1 1 d . . . . .
H13 H 0.769571 0.471432 0.604175 0.071 Uiso 1 1 calc R U . . .
H14 H 0.709511 0.489763 0.699110 0.071 Uiso 1 1 calc R U . . .
H15 H 0.731273 0.653780 0.637451 0.071 Uiso 1 1 calc R U . . .
C10 C 0.6859(3) 0.7416(4) 0.3297(2) 0.0259(6) Uani 1 1 d . . . . .
O5 O 0.6508(2) 0.8822(2) 0.29897(15) 0.0325(5) Uani 1 1 d . . . . .
O6 O 0.80700(18) 0.7026(2) 0.39456(15) 0.0298(5) Uani 1 1 d . . . . .
C11 C 0.8942(3) 0.8466(4) 0.4357(2) 0.0351(7) Uani 1 1 d . . . . .
H16 H 0.843195 0.932451 0.461801 0.042 Uiso 1 1 calc R U . . .
H17 H 0.925758 0.898617 0.380936 0.042 Uiso 1 1 calc R U . . .
C12 C 1.0128(3) 0.7857(4) 0.5213(2) 0.0384(7) Uani 1 1 d . . . . .
H18 H 0.980500 0.732012 0.574377 0.058 Uiso 1 1 calc R U . . .
H19 H 1.071350 0.881395 0.551328 0.058 Uiso 1 1 calc R U . . .
H20 H 1.064420 0.703655 0.494314 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6436(3) 0.4846(4) 0.2201(2) 0.0254(6) Uani 1 1 d . . . . .
C14 C 0.6892(3) 0.3215(4) 0.2248(2) 0.0277(6) Uani 1 1 d . . . . .
H21 H 0.698521 0.247024 0.281122 0.033 Uiso 1 1 calc R U . . .
N2 N 0.7193(2) 0.2820(3) 0.13618(19) 0.0294(5) Uani 1 1 d . . . . .
C15 C 0.7039(3) 0.4361(4) -0.0278(2) 0.0297(6) Uani 1 1 d . . . . .
H22 H 0.737677 0.346795 -0.059660 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6656(3) 0.5871(4) -0.0774(2) 0.0330(7) Uani 1 1 d . . . . .
H23 H 0.671886 0.602125 -0.144994 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6172(3) 0.7199(4) -0.0296(2) 0.0313(6) Uani 1 1 d . . . . .
H24 H 0.591576 0.823172 -0.065518 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6062(3) 0.7032(4) 0.0684(2) 0.0276(6) Uani 1 1 d . . . . .
H25 H 0.573511 0.793930 0.099859 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6916(3) 0.4184(4) 0.0707(2) 0.0278(6) Uani 1 1 d . . . . .
C20 C 0.6441(3) 0.5504(3) 0.1209(2) 0.0248(6) Uani 1 1 d . . . . .
C21 C 0.7609(4) 0.1167(4) 0.1104(3) 0.0425(8) Uani 1 1 d . . . . .
H26 H 0.759778 0.036151 0.164767 0.064 Uiso 1 1 calc R U . . .
H27 H 0.852881 0.123726 0.104380 0.064 Uiso 1 1 calc R U . . .
H28 H 0.698162 0.078752 0.044821 0.064 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
C1 N1 1.451(3) . ?
C1 C13 1.511(4) . ?
C1 C10 1.538(4) . ?
C1 C7 1.552(4) . ?
N1 C2 1.352(4) . ?
C2 O1 1.214(3) . ?
C2 O2 1.343(3) . ?
O2 C3 1.473(3) . ?
C3 C4 1.490(5) . ?
C3 C5 1.496(5) . ?
C3 C6 1.510(5) . ?
C7 O3 1.197(4) . ?
C7 O4 1.341(3) . ?
O4 C8 1.456(4) . ?
C8 C9 1.502(5) . ?
C10 O5 1.208(3) . ?
C10 O6 1.333(3) . ?
O6 C11 1.458(3) . ?
C11 C12 1.495(5) . ?
C13 C14 1.371(4) . ?
C13 C20 1.449(4) . ?
C14 N2 1.370(4) . ?
N2 C19 1.376(4) . ?
N2 C21 1.456(4) . ?
C15 C16 1.373(4) . ?
C15 C19 1.393(4) . ?
C16 C17 1.407(4) . ?
C17 C18 1.379(4) . ?
C18 C20 1.402(4) . ?
C19 C20 1.416(4) . ?

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
N1 C1 C13 112.2(2) . . ?
N1 C1 C10 104.9(2) . . ?
C13 C1 C10 109.2(2) . . ?
N1 C1 C7 109.9(2) . . ?
C13 C1 C7 113.8(2) . . ?
C10 C1 C7 106.2(2) . . ?
C2 N1 C1 122.2(2) . . ?
O1 C2 O2 126.9(3) . . ?
O1 C2 N1 123.8(3) . . ?
O2 C2 N1 109.4(2) . . ?
C2 O2 C3 120.6(2) . . ?
O2 C3 C4 110.3(3) . . ?
O2 C3 C5 109.4(3) . . ?
C4 C3 C5 112.7(4) . . ?
O2 C3 C6 102.4(3) . . ?
C4 C3 C6 111.6(3) . . ?
C5 C3 C6 109.9(3) . . ?
O3 C7 O4 124.9(3) . . ?
O3 C7 C1 126.2(2) . . ?
O4 C7 C1 108.8(2) . . ?
C7 O4 C8 115.7(2) . . ?
O4 C8 C9 110.7(3) . . ?
O5 C10 O6 124.6(3) . . ?
O5 C10 C1 123.5(2) . . ?
O6 C10 C1 111.8(2) . . ?
C10 O6 C11 114.9(2) . . ?
O6 C11 C12 108.3(3) . . ?
C14 C13 C20 106.6(2) . . ?
C14 C13 C1 130.0(3) . . ?
C20 C13 C1 123.3(3) . . ?
N2 C14 C13 109.9(3) . . ?
C14 N2 C19 109.4(2) . . ?
C14 N2 C21 125.5(3) . . ?
C19 N2 C21 124.8(3) . . ?
C16 C15 C19 117.7(3) . . ?
C15 C16 C17 121.0(3) . . ?
C18 C17 C16 121.3(3) . . ?
C17 C18 C20 119.0(3) . . ?
N2 C19 C15 130.0(3) . . ?
N2 C19 C20 107.6(2) . . ?
C15 C19 C20 122.4(3) . . ?
C18 C20 C19 118.5(3) . . ?
C18 C20 C13 135.0(3) . . ?
C19 C20 C13 106.4(3) . . ?

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
C13 C1 N1 C2 82.2(3) . . . . ?
C10 C1 N1 C2 -159.3(2) . . . . ?
C7 C1 N1 C2 -45.5(3) . . . . ?
C1 N1 C2 O1 -2.0(4) . . . . ?
C1 N1 C2 O2 177.8(2) . . . . ?
O1 C2 O2 C3 3.7(4) . . . . ?
N1 C2 O2 C3 -176.0(2) . . . . ?
C2 O2 C3 C4 -62.3(4) . . . . ?
C2 O2 C3 C5 62.2(4) . . . . ?
C2 O2 C3 C6 178.8(3) . . . . ?
N1 C1 C7 O3 132.8(3) . . . . ?
C13 C1 C7 O3 6.1(4) . . . . ?
C10 C1 C7 O3 -114.2(3) . . . . ?
N1 C1 C7 O4 -51.4(3) . . . . ?
C13 C1 C7 O4 -178.1(2) . . . . ?
C10 C1 C7 O4 61.6(3) . . . . ?
O3 C7 O4 C8 -0.2(4) . . . . ?
C1 C7 O4 C8 -176.1(2) . . . . ?
C7 O4 C8 C9 78.9(3) . . . . ?
N1 C1 C10 O5 -16.5(3) . . . . ?
C13 C1 C10 O5 104.0(3) . . . . ?
C7 C1 C10 O5 -132.8(3) . . . . ?
N1 C1 C10 O6 164.4(2) . . . . ?
C13 C1 C10 O6 -75.2(3) . . . . ?
C7 C1 C10 O6 48.0(3) . . . . ?
O5 C10 O6 C11 5.7(4) . . . . ?
C1 C10 O6 C11 -175.2(2) . . . . ?
C10 O6 C11 C12 169.1(2) . . . . ?
N1 C1 C13 C14 -123.5(3) . . . . ?
C10 C1 C13 C14 120.5(3) . . . . ?
C7 C1 C13 C14 2.0(4) . . . . ?
N1 C1 C13 C20 54.1(3) . . . . ?
C10 C1 C13 C20 -61.8(3) . . . . ?
C7 C1 C13 C20 179.7(2) . . . . ?
C20 C13 C14 N2 0.7(3) . . . . ?
C1 C13 C14 N2 178.6(3) . . . . ?
C13 C14 N2 C19 -1.0(3) . . . . ?
C13 C14 N2 C21 -175.3(3) . . . . ?
C19 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C20 -0.1(4) . . . . ?
C14 N2 C19 C15 -178.8(3) . . . . ?
C21 N2 C19 C15 -4.5(5) . . . . ?
C14 N2 C19 C20 1.0(3) . . . . ?
C21 N2 C19 C20 175.3(3) . . . . ?
C16 C15 C19 N2 178.5(3) . . . . ?
C16 C15 C19 C20 -1.3(4) . . . . ?
C17 C18 C20 C19 -0.4(4) . . . . ?
C17 C18 C20 C13 -177.9(3) . . . . ?
N2 C19 C20 C18 -178.8(2) . . . . ?
C15 C19 C20 C18 1.1(4) . . . . ?
N2 C19 C20 C13 -0.6(3) . . . . ?
C15 C19 C20 C13 179.3(2) . . . . ?
C14 C13 C20 C18 177.7(3) . . . . ?
C1 C13 C20 C18 -0.4(5) . . . . ?
C14 C13 C20 C19 -0.1(3) . . . . ?
C1 C13 C20 C19 -178.2(2) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045


_symmetry_cell_setting           monoclinic
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/Dichloromethane'
####################################################################### 
# 
# 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_ki_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2130061'
loop_
_audit_author_name
_audit_author_address
'Kento Iwai'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-(1-Methylindol-3-yl)-2-(pivaloylamino)acetic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O3'
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_weight         288.34

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                   11.4946(8)
_cell_length_b                   11.5682(6)
_cell_length_c                   11.8250(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.642(7)
_cell_angle_gamma                90
_cell_volume                     1521.33(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(1)

_cell_measurement_reflns_used    4634

_cell_measurement_theta_min      2.2110

_cell_measurement_theta_max      27.1280


_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1

_exptl_crystal_size_mid          0.07

_exptl_crystal_size_min          0.05

_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.29923

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(1)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            11412
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2829
_reflns_number_gt                2041
_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       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0510P)²+0.1457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O001 O 0.45940(13) 0.37172(11) 0.46740(11) 0.0383(4) Uani 1 1 d . . . . .
O002 O 0.54074(14) 0.23186(11) 0.38143(12) 0.0406(4) Uani 1 1 d . . . . .
H20 H 0.459(3) 0.2182(19) 0.341(2) 0.068(8) Uiso 1 1 d . . . . .
O003 O 0.83312(14) 0.32049(11) 0.74370(11) 0.0419(4) Uani 1 1 d . . . . .
N004 N 0.66463(15) 0.40096(12) 0.63541(12) 0.0338(4) Uani 1 1 d . . . . .
H19 H 0.605192 0.450025 0.631227 0.041 Uiso 1 1 calc R U . . .
N005 N 0.86180(16) 0.53812(13) 0.40749(14) 0.0364(4) Uani 1 1 d . . . . .
C006 C 0.54540(19) 0.31722(15) 0.45690(15) 0.0317(5) Uani 1 1 d . . . . .
C007 C 0.74910(18) 0.40054(16) 0.46283(16) 0.0340(5) Uani 1 1 d . . . . .
C008 C 0.74509(19) 0.38535(15) 0.73769(16) 0.0334(5) Uani 1 1 d . . . . .
C009 C 0.80306(19) 0.35244(16) 0.37682(16) 0.0357(5) Uani 1 1 d . . . . .
C00A C 0.87173(19) 0.44066(16) 0.34316(17) 0.0370(5) Uani 1 1 d . . . . .
C00B C 0.67296(19) 0.33858(15) 0.53045(16) 0.0343(5) Uani 1 1 d . . . . .
H1 H 0.710911 0.261799 0.555148 0.041 Uiso 1 1 calc R U . . .
C00C C 0.78808(19) 0.51287(16) 0.47839(17) 0.0363(5) Uani 1 1 d . . . . .
H2 H 0.766743 0.565801 0.531200 0.044 Uiso 1 1 calc R U . . .
C00D C 0.72431(19) 0.44468(15) 0.84673(16) 0.0361(5) Uani 1 1 d . . . . .
C00E C 0.8042(2) 0.24148(17) 0.32725(18) 0.0418(5) Uani 1 1 d . . . . .
H3 H 0.760277 0.179496 0.349123 0.050 Uiso 1 1 calc R U . . .
C00F C 0.9276(2) 0.64554(16) 0.40585(18) 0.0416(5) Uani 1 1 d . . . . .
H4 H 0.883326 0.694471 0.341651 0.062 Uiso 1 1 calc R U . . .
H5 H 1.007338 0.628159 0.394573 0.062 Uiso 1 1 calc R U . . .
H6 H 0.936336 0.686211 0.480234 0.062 Uiso 1 1 calc R U . . .
C00G C 0.6183(2) 0.52863(17) 0.82063(17) 0.0424(5) Uani 1 1 d . . . . .
H7 H 0.631813 0.588761 0.766967 0.064 Uiso 1 1 calc R U . . .
H8 H 0.610884 0.564426 0.893587 0.064 Uiso 1 1 calc R U . . .
H9 H 0.544217 0.486555 0.784573 0.064 Uiso 1 1 calc R U . . .
C00H C 0.9387(2) 0.42453(18) 0.26166(17) 0.0422(5) Uani 1 1 d . . . . .
H10 H 0.984035 0.485584 0.240127 0.051 Uiso 1 1 calc R U . . .
C00I C 0.8708(2) 0.22514(18) 0.24627(19) 0.0461(6) Uani 1 1 d . . . . .
H11 H 0.872085 0.150932 0.212206 0.055 Uiso 1 1 calc R U . . .
C00J C 0.8394(2) 0.50972(17) 0.90752(17) 0.0425(5) Uani 1 1 d . . . . .
H12 H 0.907854 0.456391 0.922336 0.064 Uiso 1 1 calc R U . . .
H13 H 0.830839 0.541400 0.981854 0.064 Uiso 1 1 calc R U . . .
H14 H 0.853112 0.572924 0.857228 0.064 Uiso 1 1 calc R U . . .
C00K C 0.9362(2) 0.31517(19) 0.21330(19) 0.0465(6) Uani 1 1 d . . . . .
H15 H 0.979901 0.301127 0.156430 0.056 Uiso 1 1 calc R U . . .
C00L C 0.7014(2) 0.34726(18) 0.92686(18) 0.0480(6) Uani 1 1 d . . . . .
H16 H 0.628503 0.304977 0.887639 0.072 Uiso 1 1 calc R U . . .
H17 H 0.691081 0.380520 0.999918 0.072 Uiso 1 1 calc R U . . .
H18 H 0.770097 0.294178 0.944113 0.072 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
O001 C006 1.205(2) . ?
O002 C006 1.323(2) . ?
O003 C008 1.247(2) . ?
N004 C008 1.336(2) . ?
N004 C00B 1.460(2) . ?
N005 C00C 1.366(3) . ?
N005 C00A 1.381(2) . ?
N005 C00F 1.457(2) . ?
C006 C00B 1.524(3) . ?
C007 C00C 1.372(3) . ?
C007 C009 1.431(3) . ?
C007 C00B 1.508(3) . ?
C008 C00D 1.532(3) . ?
C009 C00A 1.408(3) . ?
C009 C00E 1.413(3) . ?
C00A C00H 1.390(3) . ?
C00D C00G 1.527(3) . ?
C00D C00J 1.534(3) . ?
C00D C00L 1.537(3) . ?
C00E C00I 1.381(3) . ?
C00H C00K 1.386(3) . ?
C00I C00K 1.396(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
C008 N004 C00B 121.58(17) . . ?
C00C N005 C00A 108.30(16) . . ?
C00C N005 C00F 126.52(16) . . ?
C00A N005 C00F 124.99(18) . . ?
O001 C006 O002 124.45(18) . . ?
O001 C006 C00B 123.52(16) . . ?
O002 C006 C00B 112.03(17) . . ?
C00C C007 C009 106.14(18) . . ?
C00C C007 C00B 126.37(18) . . ?
C009 C007 C00B 127.31(17) . . ?
O003 C008 N004 119.93(17) . . ?
O003 C008 C00D 121.23(16) . . ?
N004 C008 C00D 118.80(18) . . ?
C00A C009 C00E 118.5(2) . . ?
C00A C009 C007 107.08(17) . . ?
C00E C009 C007 134.4(2) . . ?
N005 C00A C00H 128.99(19) . . ?
N005 C00A C009 107.81(19) . . ?
C00H C00A C009 123.17(18) . . ?
N004 C00B C007 112.81(15) . . ?
N004 C00B C006 107.76(17) . . ?
C007 C00B C006 112.22(15) . . ?
N005 C00C C007 110.65(17) . . ?
C00G C00D C008 113.64(16) . . ?
C00G C00D C00J 109.42(16) . . ?
C008 C00D C00J 108.34(18) . . ?
C00G C00D C00L 109.79(19) . . ?
C008 C00D C00L 106.13(15) . . ?
C00J C00D C00L 109.42(17) . . ?
C00I C00E C009 118.5(2) . . ?
C00K C00H C00A 116.8(2) . . ?
C00E C00I C00K 121.53(19) . . ?
C00H C00K C00I 121.5(2) . . ?

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
C00B N004 C008 O003 3.6(3) . . . . ?
C00B N004 C008 C00D -174.20(17) . . . . ?
C00C C007 C009 C00A -0.9(2) . . . . ?
C00B C007 C009 C00A -176.31(18) . . . . ?
C00C C007 C009 C00E 176.2(2) . . . . ?
C00B C007 C009 C00E 0.8(4) . . . . ?
C00C N005 C00A C00H -178.62(19) . . . . ?
C00F N005 C00A C00H -3.3(3) . . . . ?
C00C N005 C00A C009 -0.7(2) . . . . ?
C00F N005 C00A C009 174.54(17) . . . . ?
C00E C009 C00A N005 -176.64(17) . . . . ?
C007 C009 C00A N005 1.0(2) . . . . ?
C00E C009 C00A C00H 1.4(3) . . . . ?
C007 C009 C00A C00H 179.01(18) . . . . ?
C008 N004 C00B C007 -88.5(2) . . . . ?
C008 N004 C00B C006 147.06(17) . . . . ?
C00C C007 C00B N004 -13.1(3) . . . . ?
C009 C007 C00B N004 161.44(18) . . . . ?
C00C C007 C00B C006 108.8(2) . . . . ?
C009 C007 C00B C006 -76.6(2) . . . . ?
O001 C006 C00B N004 19.9(2) . . . . ?
O002 C006 C00B N004 -159.71(15) . . . . ?
O001 C006 C00B C007 -104.9(2) . . . . ?
O002 C006 C00B C007 75.51(19) . . . . ?
C00A N005 C00C C007 0.2(2) . . . . ?
C00F N005 C00C C007 -174.99(18) . . . . ?
C009 C007 C00C N005 0.4(2) . . . . ?
C00B C007 C00C N005 175.92(18) . . . . ?
O003 C008 C00D C00G 175.04(18) . . . . ?
N004 C008 C00D C00G -7.2(3) . . . . ?
O003 C008 C00D C00J 53.2(2) . . . . ?
N004 C008 C00D C00J -129.06(18) . . . . ?
O003 C008 C00D C00L -64.2(2) . . . . ?
N004 C008 C00D C00L 113.53(19) . . . . ?
C00A C009 C00E C00I -1.3(3) . . . . ?
C007 C009 C00E C00I -178.1(2) . . . . ?
N005 C00A C00H C00K 177.3(2) . . . . ?
C009 C00A C00H C00K -0.3(3) . . . . ?
C009 C00E C00I C00K 0.2(3) . . . . ?
C00A C00H C00K C00I -0.9(3) . . . . ?
C00E C00I C00K C00H 1.0(3) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045


_symmetry_cell_setting           monoclinic
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
