# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_210917_sakurai_0ma
_database_code_depnum_ccdc_archive 'CCDC 2129011'
loop_
_audit_author_name
_audit_author_address
'Takuya Suga'
;Kanazawa University
Japan
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.393
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 0.01920 0.00962 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 0.05239 0.03376 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 0.03256 0.01839 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      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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   9.8436(4)
_cell_length_b                   18.8060(7)
_cell_length_c                   18.8060(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3481.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      72.50
_cell_measurement_theta_min      4.70
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8305.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             1428.615
_exptl_crystal_size_max          1.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9930
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27009
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9930
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         4.70
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9930
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3203
_reflns_number_total             3421
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1820
_refine_diff_density_min         -0.2501
_refine_diff_density_rms         0.0423
_refine_ls_d_res_high            0.8083
_refine_ls_d_res_low             9.4030
_refine_ls_goodness_of_fit_ref   1.0380
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.0380
_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)+(0.0399P)²+1.4007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0871
_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 Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C13(H13a,H13b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C14(H14), C4(H4), C17(H17), C1a(H1a), C18(H18), C16(H16),
 C8(H8), C7(H7), N1(H1)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_atom_sites_solution_primary     iterative
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 1.27564(8) 0.71206(4) 0.46895(4) 0.02527(19) Uani 1.000000 .
O2 O 1.62486(8) 0.72915(4) 0.24248(4) 0.0259(2) Uani 1.000000 .
O3 O 1.47479(8) 0.68836(4) 0.41521(4) 0.02577(19) Uani 1.000000 .
N2 N 1.42682(9) 0.79571(5) 0.31764(5) 0.0184(2) Uani 1.000000 .
N1 N 1.40222(9) 0.74060(5) 0.26853(4) 0.0180(2) Uani 1.000000 .
C1 C 1.50551(10) 0.71210(6) 0.23176(5) 0.0178(2) Uani 1.000000 .
C2 C 1.34409(11) 0.79002(5) 0.37783(5) 0.0174(2) Uani 1.000000 .
C3 C 1.19839(11) 0.90440(5) 0.37244(5) 0.0181(2) Uani 1.000000 .
C4 C 1.10821(12) 0.94122(6) 0.41730(6) 0.0224(2) Uani 1.000000 .
C5 C 1.46603(11) 0.65864(6) 0.17656(5) 0.0189(2) Uani 1.000000 .
C6 C 1.37434(11) 0.72485(6) 0.42150(6) 0.0195(2) Uani 1.000000 .
C7 C 1.25404(11) 0.83839(6) 0.40201(5) 0.0185(2) Uani 1.000000 .
C8 C 1.33791(11) 0.65780(6) 0.14491(6) 0.0213(2) Uani 1.000000 .
C9 C 1.22240(11) 0.93262(6) 0.30398(6) 0.0190(2) Uani 1.000000 .
C10 C 1.07184(13) 1.03214(6) 0.33011(6) 0.0266(3) Uani 1.000000 .
C11 C 1.31189(11) 0.89561(6) 0.25106(6) 0.0212(2) Uani 1.000000 .
C12 C 1.15900(12) 0.99649(6) 0.28482(6) 0.0228(2) Uani 1.000000 .
C13 C 1.29911(13) 0.65346(6) 0.51753(6) 0.0284(3) Uani 1.000000 .
C14 C 1.04554(13) 1.00395(6) 0.39689(6) 0.0267(3) Uani 1.000000 .
C15 C 1.44193(11) 0.86498(6) 0.28340(6) 0.0212(2) Uani 1.000000 .
C16 C 1.30716(14) 0.60673(6) 0.09408(6) 0.0291(3) Uani 1.000000 .
C17 C 1.56261(13) 0.60828(6) 0.15638(6) 0.0279(3) Uani 1.000000 .
C18 C 1.40323(16) 0.55606(6) 0.07498(6) 0.0355(3) Uani 1.000000 .
C19 C 1.17438(13) 0.64713(6) 0.56305(6) 0.0281(3) Uani 1.000000 .
C1a C 1.53077(15) 0.55689(7) 0.10626(7) 0.0357(3) Uani 1.000000 .
H12 H 1.17612(12) 1.01557(6) 0.24008(6) 0.0274(3) Uiso 1.000000 R
H10 H 1.03131(13) 1.07452(6) 0.31598(6) 0.0319(3) Uiso 1.000000 R
H14 H 0.98627(13) 1.02701(6) 0.42773(6) 0.0320(3) Uiso 1.000000 R
H4 H 1.09003(12) 0.92281(6) 0.46220(6) 0.0269(3) Uiso 1.000000 R
H17 H 1.64877(13) 0.60919(6) 0.17665(6) 0.0335(3) Uiso 1.000000 R
H1a H 1.59502(15) 0.52292(7) 0.09359(7) 0.0429(4) Uiso 1.000000 R
H18 H 1.38201(16) 0.52164(6) 0.04125(6) 0.0426(4) Uiso 1.000000 R
H16 H 1.22194(14) 0.60643(6) 0.07274(6) 0.0349(3) Uiso 1.000000 R
H8 H 1.27316(11) 0.69141(6) 0.15784(6) 0.0256(3) Uiso 1.000000 R
H7 H 1.22011(11) 0.82759(6) 0.44688(5) 0.0222(3) Uiso 1.000000 R
H11a H 1.26088(11) 0.85731(6) 0.22913(6) 0.0254(3) Uiso 1.000000 R
H11b H 1.33635(11) 0.92905(6) 0.21393(6) 0.0254(3) Uiso 1.000000 R
H13a H 1.31419(13) 0.60975(6) 0.49129(6) 0.0341(3) Uiso 1.000000 R
H13b H 1.37829(13) 0.66279(6) 0.54678(6) 0.0341(3) Uiso 1.000000 R
H15a H 1.47641(11) 0.89846(6) 0.31823(6) 0.0254(3) Uiso 1.000000 R
H15b H 1.50952(11) 0.86082(6) 0.24610(6) 0.0254(3) Uiso 1.000000 R
H19a H 1.09657(19) 0.6390(5) 0.53336(7) 0.0421(4) Uiso 1.000000 GR
H19b H 1.1850(4) 0.6080(3) 0.5954(3) 0.0421(4) Uiso 1.000000 GR
H19c H 1.1619(5) 0.6903(2) 0.5895(4) 0.0421(4) Uiso 1.000000 GR
H1 H 1.32086(9) 0.72521(5) 0.26213(4) 0.0216(2) 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 C6 1.3408(13) . ?
O1 C13 1.4500(13) . ?
O2 C1 1.2344(13) . ?
O3 C6 1.2093(13) . ?
N2 N1 1.4091(12) . ?
N2 C2 1.3984(13) . ?
N2 C15 1.4608(14) . ?
N1 C1 1.3414(13) . ?
N1 H1 0.8600 . ?
C1 C5 1.4965(15) . ?
C2 C6 1.5052(14) . ?
C2 C7 1.3490(15) . ?
C3 C4 1.4069(15) . ?
C3 C7 1.4664(14) . ?
C3 C9 1.4125(15) . ?
C4 C14 1.3856(16) . ?
C4 H4 0.9300 . ?
C5 C8 1.3946(15) . ?
C5 C17 1.3945(15) . ?
C7 H7 0.9300 . ?
C8 C16 1.3885(16) . ?
C8 H8 0.9300 . ?
C9 C11 1.5002(15) . ?
C9 C12 1.4008(15) . ?
C10 C12 1.3824(17) . ?
C10 C14 1.3874(17) . ?
C10 H10 0.9300 . ?
C11 C15 1.5298(15) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C12 H12 0.9300 . ?
C13 C19 1.5016(16) . ?
C13 H13a 0.9700 . ?
C13 H13b 0.9700 . ?
C14 H14 0.9300 . ?
C15 H15a 0.9700 . ?
C15 H15b 0.9700 . ?
C16 C18 1.3898(19) . ?
C16 H16 0.9300 . ?
C17 C1a 1.3859(18) . ?
C17 H17 0.9300 . ?
C18 C1a 1.386(2) . ?
C18 H18 0.9300 . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
C1a H1a 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
C13 O1 C6 116.11(9) . . ?
C2 N2 N1 111.97(8) . . ?
C15 N2 N1 112.61(8) . . ?
C15 N2 C2 118.96(9) . . ?
C1 N1 N2 120.10(8) . . ?
H1 N1 N2 119.95(5) . . ?
H1 N1 C1 119.95(6) . . ?
N1 C1 O2 122.24(10) . . ?
C5 C1 O2 122.34(9) . . ?
C5 C1 N1 115.42(9) . . ?
C6 C2 N2 112.88(9) . . ?
C7 C2 N2 127.15(10) . . ?
C7 C2 C6 119.67(9) . . ?
C7 C3 C4 115.15(9) . . ?
C9 C3 C4 117.86(10) . . ?
C9 C3 C7 126.96(10) . . ?
C14 C4 C3 122.27(10) . . ?
H4 C4 C3 118.87(6) . . ?
H4 C4 C14 118.87(7) . . ?
C8 C5 C1 122.57(9) . . ?
C17 C5 C1 117.90(10) . . ?
C17 C5 C8 119.52(10) . . ?
O3 C6 O1 123.76(10) . . ?
C2 C6 O1 111.46(9) . . ?
C2 C6 O3 124.77(10) . . ?
C3 C7 C2 133.50(10) . . ?
H7 C7 C2 113.25(6) . . ?
H7 C7 C3 113.25(6) . . ?
C16 C8 C5 119.92(11) . . ?
H8 C8 C5 120.04(6) . . ?
H8 C8 C16 120.04(7) . . ?
C11 C9 C3 121.91(10) . . ?
C12 C9 C3 118.82(10) . . ?
C12 C9 C11 119.26(10) . . ?
C14 C10 C12 119.22(11) . . ?
H10 C10 C12 120.39(7) . . ?
H10 C10 C14 120.39(7) . . ?
C15 C11 C9 113.72(9) . . ?
H11a C11 C9 108.82(6) . . ?
H11a C11 C15 108.82(6) . . ?
H11b C11 C9 108.82(6) . . ?
H11b C11 C15 108.82(6) . . ?
H11b C11 H11a 107.7 . . ?
C10 C12 C9 122.27(10) . . ?
H12 C12 C9 118.86(7) . . ?
H12 C12 C10 118.86(7) . . ?
C19 C13 O1 106.81(9) . . ?
H13a C13 O1 110.36(6) . . ?
H13a C13 C19 110.36(7) . . ?
H13b C13 O1 110.36(6) . . ?
H13b C13 C19 110.36(7) . . ?
H13b C13 H13a 108.6 . . ?
C10 C14 C4 119.53(11) . . ?
H14 C14 C4 120.23(7) . . ?
H14 C14 C10 120.23(7) . . ?
C11 C15 N2 115.21(9) . . ?
H15a C15 N2 108.47(5) . . ?
H15a C15 C11 108.47(6) . . ?
H15b C15 N2 108.47(6) . . ?
H15b C15 C11 108.47(6) . . ?
H15b C15 H15a 107.5 . . ?
C18 C16 C8 120.26(12) . . ?
H16 C16 C8 119.87(7) . . ?
H16 C16 C18 119.87(8) . . ?
C1a C17 C5 120.30(12) . . ?
H17 C17 C5 119.85(7) . . ?
H17 C17 C1a 119.85(8) . . ?
C1a C18 C16 119.92(11) . . ?
H18 C18 C16 120.04(8) . . ?
H18 C18 C1a 120.04(7) . . ?
H19a C19 C13 109.5 . . ?
H19b C19 C13 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C13 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C18 C1a C17 120.08(12) . . ?
H1a C1a C17 119.96(8) . . ?
H1a C1a C18 119.96(7) . . ?

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 C6 C2 N2 -166.00(8) . . . . ?
O1 C6 C2 C7 19.84(11) . . . . ?
O2 C1 N1 N2 4.85(13) . . . . ?
O2 C1 C5 C8 -155.01(10) . . . . ?
O2 C1 C5 C17 24.69(12) . . . . ?
O3 C6 C2 N2 14.21(12) . . . . ?
O3 C6 C2 C7 -159.95(11) . . . . ?
N2 N1 C1 C5 -174.75(9) . . . . ?
N2 C2 C7 C3 9.70(14) . . . . ?
N2 C15 C11 C9 82.38(10) . . . . ?
N1 C1 C5 C8 24.59(11) . . . . ?
N1 C1 C5 C17 -155.70(9) . . . . ?
C1 C5 C8 C16 -179.86(10) . . . . ?
C1 C5 C17 C1a 179.04(10) . . . . ?
C2 C7 C3 C4 -177.75(13) . . . . ?
C2 C7 C3 C9 4.55(15) . . . . ?
C3 C4 C14 C10 -0.12(13) . . . . ?
C3 C9 C11 C15 -42.12(11) . . . . ?
C3 C9 C12 C10 -1.21(12) . . . . ?
C4 C14 C10 C12 0.80(13) . . . . ?
C5 C8 C16 C18 0.50(13) . . . . ?
C5 C17 C1a C18 1.12(13) . . . . ?
C8 C16 C18 C1a -0.63(14) . . . . ?
C9 C12 C10 C14 -0.13(13) . . . . ?
C16 C18 C1a C17 -0.17(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'Ukaji 6'
####################################################################### 
# 
# 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_191207_rtakahashi4_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2129155'
loop_
_audit_author_name
_audit_author_address
'Takuya Suga'
;Kanazawa University
Japan
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        'Ukaji 4a'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4 O3'
_chemical_formula_weight         364.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.9174(3)
_cell_length_b                   16.0704(9)
_cell_length_c                   11.6190(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.199(3)
_cell_angle_gamma                90
_cell_volume                     918.18(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    7892
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      72.36

_exptl_crystal_description       rectangular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.744
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6994
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.804
_diffrn_reflns_theta_max         72.649
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3403
_reflns_number_gt                3300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_fraction_full    0.929

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0876P)²+0.6314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_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 0.5588(6) 0.35430(18) 0.3003(3) 0.0291(7) Uani 1 1 d . . . . .
O2 O 0.8276(7) 0.45324(19) 0.3786(3) 0.0340(7) Uani 1 1 d . . . . .
O3 O 0.6369(7) 0.62643(19) 0.5018(3) 0.0324(7) Uani 1 1 d . . . . .
N1 N 0.2595(8) 0.5707(2) 0.4172(3) 0.0264(7) Uani 1 1 d . . . . .
H24 H 0.118(14) 0.525(4) 0.430(5) 0.047(16) Uiso 1 1 d . . . . .
N2 N 0.2791(7) 0.6109(2) 0.3093(3) 0.0263(7) Uani 1 1 d . . . . .
N3 N 0.3258(8) 0.4578(2) 0.1670(3) 0.0294(8) Uani 1 1 d . . . . .
N4 N 0.1651(10) 0.4313(3) 0.1064(4) 0.0428(11) Uani 1 1 d . . . . .
C1 C 0.6527(8) 0.4325(3) 0.3107(4) 0.0247(8) Uani 1 1 d . . . . .
C2 C 0.4407(9) 0.5794(3) 0.5046(4) 0.0256(8) Uani 1 1 d . . . . .
C3 C 0.3770(9) 0.5266(3) 0.6085(4) 0.0290(9) Uani 1 1 d . . . . .
C4 C 0.5244(8) 0.5830(3) 0.2464(4) 0.0238(8) Uani 1 1 d . . . . .
H25 H 0.684090 0.597109 0.293189 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4011(8) 0.7030(2) 0.1128(4) 0.0241(8) Uani 1 1 d . . . . .
C6 C 0.5473(8) 0.6294(3) 0.1319(4) 0.0256(8) Uani 1 1 d . . . . .
C7 C 0.5159(8) 0.4899(3) 0.2334(4) 0.0243(8) Uani 1 1 d . . . . .
C8 C 0.2071(9) 0.7368(3) 0.2007(4) 0.0295(9) Uani 1 1 d . . . . .
H1 H 0.022478 0.722905 0.178153 0.035 Uiso 1 1 calc R U . . .
H2 H 0.222067 0.796997 0.202761 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7662(10) 0.6433(3) -0.0529(4) 0.0357(10) Uani 1 1 d . . . . .
H3 H 0.889739 0.623606 -0.106797 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6203(10) 0.7164(3) -0.0733(4) 0.0342(10) Uani 1 1 d . . . . .
H4 H 0.644173 0.745403 -0.141738 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4427(9) 0.7452(3) 0.0074(4) 0.0301(9) Uani 1 1 d . . . . .
H5 H 0.346376 0.793868 -0.007316 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2633(10) 0.7023(3) 0.3195(4) 0.0324(10) Uani 1 1 d . . . . .
H6 H 0.433378 0.724248 0.349167 0.039 Uiso 1 1 calc R U . . .
H7 H 0.118612 0.717809 0.371814 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7236(9) 0.6005(3) 0.0494(4) 0.0328(9) Uani 1 1 d . . . . .
H8 H 0.816802 0.551032 0.062371 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6750(9) 0.2922(3) 0.3793(4) 0.0312(9) Uani 1 1 d . . . . .
H9 H 0.542479 0.248716 0.393568 0.037 Uiso 1 1 calc R U . . .
H10 H 0.718891 0.318385 0.452273 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9253(11) 0.2551(3) 0.3290(5) 0.0407(11) Uani 1 1 d . . . . .
H11 H 0.881094 0.228630 0.257283 0.061 Uiso 1 1 calc R U . . .
H12 H 0.998848 0.214588 0.381325 0.061 Uiso 1 1 calc R U . . .
H13 H 1.057230 0.298053 0.316089 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2805(12) 0.4283(5) 0.8007(5) 0.0537(16) Uani 1 1 d . . . . .
H23 H 0.247158 0.397318 0.866841 0.08(3) Uiso 1 1 calc R . . A 2
C17 C 0.4000(17) 0.5516(6) 0.7150(8) 0.0301(18) Uani 0.5 1 d . . P B 2
H18 H 0.451817 0.606376 0.728710 0.036 Uiso 0.5 1 calc R U P B 2
C18 C 0.3507(18) 0.5003(6) 0.8088(8) 0.0319(19) Uani 0.5 1 d . . P B 2
H19 H 0.372743 0.522589 0.882086 0.038 Uiso 0.5 1 calc R U P B 2
C19 C 0.2879(17) 0.4387(5) 0.5861(7) 0.0264(16) Uani 0.5 1 d . . P B 2
H20 H 0.261588 0.419418 0.511368 0.032 Uiso 0.5 1 calc R U P B 2
C20 C 0.123(2) 0.5099(6) 0.6418(9) 0.036(2) Uani 0.5 1 d . . P B 1
H14 H -0.022839 0.529435 0.598114 0.043 Uiso 0.5 1 calc R U P B 1
C21 C 0.2461(17) 0.3872(5) 0.6798(8) 0.0270(17) Uani 0.5 1 d . . P B 2
H21 H 0.200160 0.331348 0.671216 0.032 Uiso 0.5 1 calc R U P B 2
C22 C 0.601(2) 0.5091(6) 0.6866(8) 0.034(2) Uani 0.5 1 d . . P B 1
H15 H 0.776320 0.527658 0.671239 0.040 Uiso 0.5 1 calc R U P B 1
C23 C 0.073(2) 0.4643(7) 0.7395(10) 0.042(2) Uani 0.5 1 d . . P B 1
H16 H -0.104835 0.457827 0.764672 0.050 Uiso 0.5 1 calc R U P B 1
C24 C 0.544(2) 0.4642(7) 0.7838(9) 0.039(2) Uani 0.5 1 d . . P B 1
H17 H 0.678531 0.456985 0.839558 0.047 Uiso 0.5 1 calc R U P B 1


_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 C1 1.344(5) . ?
O1 C14 1.470(5) . ?
O2 C1 1.212(5) . ?
O3 C2 1.226(5) . ?
N1 C2 1.356(6) . ?
N1 N2 1.413(5) . ?
N1 H24 1.02(7) . ?
N2 C12 1.475(5) . ?
N2 C4 1.482(5) . ?
N3 N4 1.139(6) . ?
N3 C7 1.315(6) . ?
C1 C7 1.451(5) . ?
C2 C3 1.510(6) . ?
C3 C17 1.306(10) . ?
C3 C20 1.337(11) . ?
C3 C22 1.453(11) . ?
C3 C19 1.501(9) . ?
C4 C7 1.504(5) . ?
C4 C6 1.529(6) . ?
C4 H25 0.9800 . ?
C5 C6 1.402(6) . ?
C5 C11 1.416(6) . ?
C5 C8 1.501(6) . ?
C6 C13 1.376(6) . ?
C8 C12 1.513(6) . ?
C8 H1 0.9700 . ?
C8 H2 0.9700 . ?
C9 C13 1.389(7) . ?
C9 C10 1.396(7) . ?
C9 H3 0.9300 . ?
C10 C11 1.364(7) . ?
C10 H4 0.9300 . ?
C11 H5 0.9300 . ?
C12 H6 0.9700 . ?
C12 H7 0.9700 . ?
C13 H8 0.9300 . ?
C14 C15 1.489(7) . ?
C14 H9 0.9700 . ?
C14 H10 0.9700 . ?
C15 H11 0.9600 . ?
C15 H12 0.9600 . ?
C15 H13 0.9600 . ?
C16 C18 1.212(12) . ?
C16 C23 1.370(12) . ?
C16 C24 1.434(13) . ?
C16 C21 1.562(11) . ?
C16 H23 0.9300 . ?
C17 C18 1.388(13) . ?
C17 H18 0.9300 . ?
C18 H19 0.9300 . ?
C19 C21 1.384(12) . ?
C19 H20 0.9300 . ?
C20 C23 1.374(15) . ?
C20 H14 0.9300 . ?
C21 H21 0.9300 . ?
C22 C24 1.369(14) . ?
C22 H15 0.9300 . ?
C23 H16 0.9300 . ?
C24 H17 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
C1 O1 C14 116.5(3) . . ?
C2 N1 N2 124.8(3) . . ?
C2 N1 H24 114(4) . . ?
N2 N1 H24 120(4) . . ?
N1 N2 C12 112.3(3) . . ?
N1 N2 C4 110.9(3) . . ?
C12 N2 C4 112.6(3) . . ?
N4 N3 C7 177.7(5) . . ?
O2 C1 O1 123.9(4) . . ?
O2 C1 C7 123.7(4) . . ?
O1 C1 C7 112.4(3) . . ?
O3 C2 N1 123.9(4) . . ?
O3 C2 C3 122.3(4) . . ?
N1 C2 C3 113.8(4) . . ?
C20 C3 C22 119.3(7) . . ?
C17 C3 C19 118.6(6) . . ?
C17 C3 C2 124.5(6) . . ?
C20 C3 C2 122.7(6) . . ?
C22 C3 C2 116.7(5) . . ?
C19 C3 C2 116.8(5) . . ?
N2 C4 C7 109.2(3) . . ?
N2 C4 C6 110.1(3) . . ?
C7 C4 C6 113.6(4) . . ?
N2 C4 H25 107.9 . . ?
C7 C4 H25 107.9 . . ?
C6 C4 H25 107.9 . . ?
C6 C5 C11 117.7(4) . . ?
C6 C5 C8 121.7(4) . . ?
C11 C5 C8 120.6(4) . . ?
C13 C6 C5 119.9(4) . . ?
C13 C6 C4 119.4(4) . . ?
C5 C6 C4 120.7(4) . . ?
N3 C7 C1 116.1(4) . . ?
N3 C7 C4 117.9(4) . . ?
C1 C7 C4 123.9(4) . . ?
C5 C8 C12 111.9(4) . . ?
C5 C8 H1 109.2 . . ?
C12 C8 H1 109.2 . . ?
C5 C8 H2 109.2 . . ?
C12 C8 H2 109.2 . . ?
H1 C8 H2 107.9 . . ?
C13 C9 C10 118.9(4) . . ?
C13 C9 H3 120.6 . . ?
C10 C9 H3 120.6 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H4 120.0 . . ?
C9 C10 H4 120.0 . . ?
C10 C11 C5 121.8(4) . . ?
C10 C11 H5 119.1 . . ?
C5 C11 H5 119.1 . . ?
N2 C12 C8 107.6(4) . . ?
N2 C12 H6 110.2 . . ?
C8 C12 H6 110.2 . . ?
N2 C12 H7 110.2 . . ?
C8 C12 H7 110.2 . . ?
H6 C12 H7 108.5 . . ?
C6 C13 C9 121.8(4) . . ?
C6 C13 H8 119.1 . . ?
C9 C13 H8 119.1 . . ?
O1 C14 C15 110.3(4) . . ?
O1 C14 H9 109.6 . . ?
C15 C14 H9 109.6 . . ?
O1 C14 H10 109.6 . . ?
C15 C14 H10 109.6 . . ?
H9 C14 H10 108.1 . . ?
C14 C15 H11 109.5 . . ?
C14 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
C14 C15 H13 109.5 . . ?
H11 C15 H13 109.5 . . ?
H12 C15 H13 109.5 . . ?
C23 C16 C24 115.5(7) . . ?
C18 C16 C21 120.2(6) . . ?
C18 C16 H23 119.9 . . ?
C21 C16 H23 119.9 . . ?
C3 C17 C18 123.1(8) . . ?
C3 C17 H18 118.4 . . ?
C18 C17 H18 118.4 . . ?
C16 C18 C17 123.9(8) . . ?
C16 C18 H19 118.1 . . ?
C17 C18 H19 118.1 . . ?
C21 C19 C3 118.1(7) . . ?
C21 C19 H20 121.0 . . ?
C3 C19 H20 121.0 . . ?
C3 C20 C23 120.9(9) . . ?
C3 C20 H14 119.5 . . ?
C23 C20 H14 119.5 . . ?
C19 C21 C16 116.0(7) . . ?
C19 C21 H21 122.0 . . ?
C16 C21 H21 122.0 . . ?
C24 C22 C3 117.5(8) . . ?
C24 C22 H15 121.3 . . ?
C3 C22 H15 121.3 . . ?
C16 C23 C20 121.4(9) . . ?
C16 C23 H16 119.3 . . ?
C20 C23 H16 119.3 . . ?
C22 C24 C16 120.8(9) . . ?
C22 C24 H17 119.6 . . ?
C16 C24 H17 119.6 . . ?

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
C2 N1 N2 C12 -63.0(5) . . . . ?
C2 N1 N2 C4 64.0(5) . . . . ?
C14 O1 C1 O2 1.5(6) . . . . ?
C14 O1 C1 C7 -177.0(4) . . . . ?
N2 N1 C2 O3 3.5(6) . . . . ?
N2 N1 C2 C3 -177.6(4) . . . . ?
O3 C2 C3 C17 40.1(8) . . . . ?
N1 C2 C3 C17 -138.8(6) . . . . ?
O3 C2 C3 C20 144.5(7) . . . . ?
N1 C2 C3 C20 -34.4(8) . . . . ?
O3 C2 C3 C22 -22.3(7) . . . . ?
N1 C2 C3 C22 158.8(5) . . . . ?
O3 C2 C3 C19 -138.3(5) . . . . ?
N1 C2 C3 C19 42.8(6) . . . . ?
N1 N2 C4 C7 56.7(4) . . . . ?
C12 N2 C4 C7 -176.5(4) . . . . ?
N1 N2 C4 C6 -178.0(3) . . . . ?
C12 N2 C4 C6 -51.2(4) . . . . ?
C11 C5 C6 C13 -0.1(6) . . . . ?
C8 C5 C6 C13 -179.9(4) . . . . ?
C11 C5 C6 C4 176.7(4) . . . . ?
C8 C5 C6 C4 -3.1(6) . . . . ?
N2 C4 C6 C13 -165.8(4) . . . . ?
C7 C4 C6 C13 -43.0(5) . . . . ?
N2 C4 C6 C5 17.5(5) . . . . ?
C7 C4 C6 C5 140.2(4) . . . . ?
O2 C1 C7 N3 -178.3(4) . . . . ?
O1 C1 C7 N3 0.1(5) . . . . ?
O2 C1 C7 C4 -14.9(7) . . . . ?
O1 C1 C7 C4 163.5(4) . . . . ?
N2 C4 C7 N3 67.2(5) . . . . ?
C6 C4 C7 N3 -56.1(5) . . . . ?
N2 C4 C7 C1 -95.9(5) . . . . ?
C6 C4 C7 C1 140.8(4) . . . . ?
C6 C5 C8 C12 20.0(6) . . . . ?
C11 C5 C8 C12 -159.8(4) . . . . ?
C13 C9 C10 C11 1.0(7) . . . . ?
C9 C10 C11 C5 0.2(7) . . . . ?
C6 C5 C11 C10 -0.6(6) . . . . ?
C8 C5 C11 C10 179.2(4) . . . . ?
N1 N2 C12 C8 -164.4(3) . . . . ?
C4 N2 C12 C8 69.5(4) . . . . ?
C5 C8 C12 N2 -50.6(5) . . . . ?
C5 C6 C13 C9 1.2(7) . . . . ?
C4 C6 C13 C9 -175.6(4) . . . . ?
C10 C9 C13 C6 -1.7(7) . . . . ?
C1 O1 C14 C15 -88.0(5) . . . . ?
C19 C3 C17 C18 1.2(11) . . . . ?
C2 C3 C17 C18 -177.2(7) . . . . ?
C21 C16 C18 C17 1.2(13) . . . . ?
C3 C17 C18 C16 -0.5(14) . . . . ?
C17 C3 C19 C21 -2.8(10) . . . . ?
C2 C3 C19 C21 175.7(6) . . . . ?
C22 C3 C20 C23 -10.9(13) . . . . ?
C2 C3 C20 C23 -177.4(8) . . . . ?
C3 C19 C21 C16 3.4(10) . . . . ?
C18 C16 C21 C19 -2.8(11) . . . . ?
C20 C3 C22 C24 10.0(12) . . . . ?
C2 C3 C22 C24 177.3(7) . . . . ?
C24 C16 C23 C20 21.8(15) . . . . ?
C3 C20 C23 C16 -5.8(16) . . . . ?
C3 C22 C24 C16 6.8(14) . . . . ?
C23 C16 C24 C22 -22.2(14) . . . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.065

