# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_kct81_a
_database_code_depnum_ccdc_archive 'CCDC 1911989'
loop_
_audit_author_name
_audit_author_address
'Toru Okawara'
;National Institute of Technology, Kitakyushu College
Japan
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C20 H25 N O8'
_chemical_formula_sum            'C20 H25 N O8'
_chemical_formula_weight         407.42
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   20.82(11)
_cell_length_b                   12.78(6)
_cell_length_c                   17.52(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.80(4)
_cell_angle_gamma                90
_cell_volume                     4605(41)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2004
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.36
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.4504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1462 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.6046. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.1751
_exptl_crystal_description       block
_exptl_crystal_F_000             1729.1292
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10080
_diffrn_reflns_theta_full        23.4720
_diffrn_reflns_theta_max         23.47
_diffrn_reflns_theta_min         1.88
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9877
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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              22
_reflns_limit_h_min              -23
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2124
_reflns_number_total             3367
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3233
_refine_diff_density_min         -0.3556
_refine_diff_density_rms         0.1117
_refine_ls_d_res_high            0.8922
_refine_ls_d_res_low             10.8536
_refine_ls_goodness_of_fit_ref   1.0483
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0767
_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)+(0.1437P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2312
_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:
 C19(H19a,H19b), C14(H14a,H14b), C15(H15a,H15b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C16(H16a,H16b,H16c), C20(H20a,H20b,
 H20c), C18(H18a,H18b,H18c)
;
_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 0.53255(12) 0.81282(19) 0.17027(16) 0.0841(8) Uani 1.000000 .
O2 O 0.69040(13) 1.0034(2) 0.34953(15) 0.0950(9) Uani 1.000000 .
O3 O 0.62715(12) 0.7429(2) 0.22629(16) 0.0904(9) Uani 1.000000 .
O4 O 0.70501(12) 0.8349(2) 0.31840(13) 0.0860(8) Uani 1.000000 .
O5 O 0.60827(17) 1.2676(2) 0.2121(2) 0.1157(11) Uani 1.000000 .
O6 O 0.52341(15) 1.3597(2) 0.14670(19) 0.1057(9) Uani 1.000000 .
O7 O 0.35546(12) 1.0465(2) -0.04106(15) 0.0909(9) Uani 1.000000 .
O8 O 0.39425(10) 0.8996(2) 0.02661(13) 0.0735(7) Uani 1.000000 .
N1 N 0.49040(11) 1.0023(2) 0.11679(14) 0.0578(7) Uani 1.000000 .
H1 H 0.48996(11) 0.9351(2) 0.12051(14) 0.0694(9) Uiso 1.000000 R
C1 C 0.53482(14) 1.0668(3) 0.16152(17) 0.0573(8) Uani 1.000000 .
C2 C 0.51730(15) 1.1736(3) 0.13719(19) 0.0619(9) Uani 1.000000 .
C3 C 0.46210(15) 1.1683(3) 0.07518(18) 0.0639(9) Uani 1.000000 .
C4 C 0.44683(14) 1.0597(3) 0.06535(18) 0.0583(8) Uani 1.000000 .
C5 C 0.58780(14) 1.0307(3) 0.22009(18) 0.0620(9) Uani 1.000000 .
H5 H 0.60898(14) 1.0851(3) 0.24898(18) 0.0744(11) Uiso 1.000000 R
C6 C 0.61363(14) 0.9322(3) 0.24222(18) 0.0629(9) Uani 1.000000 .
C7 C 0.58744(16) 0.8291(3) 0.2092(2) 0.0697(10) Uani 1.000000 .
C8 C 0.67182(17) 0.9296(3) 0.3065(2) 0.0716(10) Uani 1.000000 .
C9 C 0.5548(2) 1.2692(3) 0.1698(2) 0.0744(10) Uani 1.000000 .
C10 C 0.39397(15) 1.0048(3) 0.01080(19) 0.0655(9) Uani 1.000000 .
C11 C 0.69761(19) 0.7599(4) 0.2541(2) 0.0905(13) Uani 1.000000 .
C12 C 0.7239(2) 0.6540(4) 0.2877(3) 0.1221(17) Uani 1.000000 .
H12a H 0.6997(12) 0.6325(15) 0.3275(15) 0.183(3) Uiso 1.000000 GR
H12b H 0.7193(17) 0.6023(8) 0.2475(5) 0.183(3) Uiso 1.000000 GR
H12c H 0.7689(5) 0.6611(8) 0.309(2) 0.183(3) Uiso 1.000000 GR
C13 C 0.7322(2) 0.7993(4) 0.1887(2) 0.1188(17) Uani 1.000000 .
H13a H 0.7294(16) 0.7472(13) 0.1489(10) 0.178(3) Uiso 1.000000 GR
H13b H 0.7119(12) 0.8627(16) 0.1678(14) 0.178(3) Uiso 1.000000 GR
H13c H 0.7771(5) 0.813(3) 0.2084(5) 0.178(3) Uiso 1.000000 GR
C14 C 0.42404(17) 1.2576(3) 0.0291(2) 0.0764(10) Uani 1.000000 .
H14a H 0.45336(17) 1.3158(3) 0.0255(2) 0.0917(12) Uiso 1.000000 R
H14b H 0.40864(17) 1.2333(3) -0.0229(2) 0.0917(12) Uiso 1.000000 R
C15 C 0.36467(19) 1.2975(3) 0.0659(3) 0.0962(13) Uani 1.000000 .
H15a H 0.33405(19) 1.2404(3) 0.0667(3) 0.1155(16) Uiso 1.000000 R
H15b H 0.37964(19) 1.3181(3) 0.1189(3) 0.1155(16) Uiso 1.000000 R
C16 C 0.3291(2) 1.3917(4) 0.0219(3) 0.1338(19) Uani 1.000000 .
H16a H 0.3184(18) 1.3747(13) -0.0319(5) 0.201(3) Uiso 1.000000 GR
H16b H 0.2899(11) 1.407(2) 0.0426(16) 0.201(3) Uiso 1.000000 GR
H16c H 0.3569(8) 1.4520(9) 0.028(2) 0.201(3) Uiso 1.000000 GR
C17 C 0.5577(3) 1.4596(3) 0.1697(3) 0.1267(18) Uani 1.000000 .
H17a H 0.5638(3) 1.4682(3) 0.2253(3) 0.152(2) Uiso 1.000000 R
H17b H 0.5999(3) 1.4609(3) 0.1527(3) 0.152(2) Uiso 1.000000 R
C18 C 0.5152(4) 1.5436(5) 0.1311(5) 0.195(3) Uani 1.000000 .
H18a H 0.511(3) 1.535(4) 0.0761(4) 0.292(5) Uiso 1.000000 GR
H18b H 0.4731(13) 1.539(4) 0.147(3) 0.292(5) Uiso 1.000000 GR
H18c H 0.534(2) 1.6106(5) 0.145(4) 0.292(5) Uiso 1.000000 GR
C19 C 0.34367(18) 0.8340(3) -0.0196(2) 0.0900(12) Uani 1.000000 .
H19a H 0.30097(18) 0.8537(3) -0.0088(2) 0.1080(15) Uiso 1.000000 R
H19b H 0.34461(18) 0.8443(3) -0.0743(2) 0.1080(15) Uiso 1.000000 R
C20 C 0.3573(2) 0.7202(4) 0.0017(3) 0.1119(16) Uani 1.000000 .
H20a H 0.3265(12) 0.6764(4) -0.0300(15) 0.168(2) Uiso 1.000000 GR
H20b H 0.4005(7) 0.7024(9) -0.007(2) 0.168(2) Uiso 1.000000 GR
H20c H 0.3534(18) 0.7096(7) 0.0550(7) 0.168(2) Uiso 1.000000 GR


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 C7 1.255(6) . ?
O2 C8 1.231(6) . ?
O3 C7 1.382(6) . ?
O3 C11 1.489(9) . ?
O4 C8 1.393(7) . ?
O4 C11 1.469(7) . ?
O5 C9 1.239(7) . ?
O6 C9 1.359(7) . ?
O6 C17 1.488(7) . ?
O7 C10 1.237(6) . ?
O8 C10 1.373(8) . ?
O8 C19 1.485(6) . ?
N1 C1 1.388(6) . ?
N1 C4 1.387(6) . ?
C1 C2 1.459(8) . ?
C1 C5 1.462(7) . ?
C2 C3 1.457(7) . ?
C2 C9 1.514(7) . ?
C3 C4 1.427(8) . ?
C3 C14 1.545(7) . ?
C4 C10 1.515(7) . ?
C5 C6 1.399(7) . ?
C6 C7 1.507(8) . ?
C6 C8 1.523(7) . ?
C11 C12 1.543(8) . ?
C11 C13 1.529(8) . ?
C14 C15 1.564(8) . ?
C15 C16 1.554(8) . ?
C17 C18 1.486(9) . ?
C19 C20 1.517(9) . ?

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
C11 O3 C7 118.8(3) . . ?
C11 O4 C8 117.4(3) . . ?
C17 O6 C9 117.4(4) . . ?
C19 O8 C10 117.5(3) . . ?
C4 N1 C1 111.4(3) . . ?
C2 C1 N1 106.0(3) . . ?
C5 C1 N1 125.1(3) . . ?
C5 C1 C2 128.9(3) . . ?
C3 C2 C1 107.9(3) . . ?
C9 C2 C1 123.5(3) . . ?
C9 C2 C3 128.5(3) . . ?
C4 C3 C2 105.7(3) . . ?
C14 C3 C2 129.6(3) . . ?
C14 C3 C4 124.6(3) . . ?
C3 C4 N1 108.9(3) . . ?
C10 C4 N1 120.3(3) . . ?
C10 C4 C3 130.8(3) . . ?
C6 C5 C1 134.0(3) . . ?
C7 C6 C5 125.3(3) . . ?
C8 C6 C5 116.9(3) . . ?
C8 C6 C7 117.7(3) . . ?
O3 C7 O1 116.8(3) . . ?
C6 C7 O1 126.8(3) . . ?
C6 C7 O3 116.3(3) . . ?
O4 C8 O2 118.1(3) . . ?
C6 C8 O2 125.1(4) . . ?
C6 C8 O4 116.7(3) . . ?
O6 C9 O5 122.6(4) . . ?
C2 C9 O5 125.2(4) . . ?
C2 C9 O6 112.1(3) . . ?
O8 C10 O7 123.5(3) . . ?
C4 C10 O7 126.2(3) . . ?
C4 C10 O8 110.2(3) . . ?
O4 C11 O3 109.2(3) . . ?
C12 C11 O3 105.7(4) . . ?
C12 C11 O4 106.8(3) . . ?
C13 C11 O3 110.9(3) . . ?
C13 C11 O4 110.7(4) . . ?
C13 C11 C12 113.3(3) . . ?
C15 C14 C3 113.6(3) . . ?
C16 C15 C14 113.2(3) . . ?
C18 C17 O6 105.6(4) . . ?
C20 C19 O8 108.4(3) . . ?

_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_yano070
_database_code_depnum_ccdc_archive 'CCDC 1911990'
loop_
_audit_author_name
_audit_author_address
'Toru Okawara'
;National Institute of Technology, Kitakyushu College
Japan
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C20 H25 N3 O7'
_chemical_formula_sum            'C20 H25 N3 O7'
_chemical_formula_weight         419.44
_chemical_oxdiff_formula         C
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   17.799(2)
_cell_length_b                   5.2201(7)
_cell_length_c                   21.974(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.833(13)
_cell_angle_gamma                90
_cell_volume                     1998.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.2350
_cell_measurement_theta_min      3.2960
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3941
_exptl_crystal_description       plate
_exptl_crystal_F_000             888.5297
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12866
_diffrn_reflns_theta_full        26.3696
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.69
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00-180.00  193
  2  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00  60.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0007436000
_diffrn_orient_matrix_UB_12      -0.0105357000
_diffrn_orient_matrix_UB_13      0.0320643000
_diffrn_orient_matrix_UB_21      -0.0169279000
_diffrn_orient_matrix_UB_22      0.1232493000
_diffrn_orient_matrix_UB_23      -0.0007292000
_diffrn_orient_matrix_UB_31      -0.0370130000
_diffrn_orient_matrix_UB_32      -0.0561452000
_diffrn_orient_matrix_UB_33      -0.0077396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -22
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2400
_reflns_number_total             4094
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_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)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.6459
_refine_diff_density_min         -0.5536
_refine_diff_density_rms         0.1388
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             7.5702
_refine_ls_goodness_of_fit_ref   1.1119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.1119
_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)+(0.1061P)²+2.3620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2756
_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:
 C12(H12a,H12b), C19(H19a,H19b), C13(H13a,H13b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C20(H20a,H20b,H20c), C16(H16a,H16b,H16c), C18(H18a,H18b,
 H18c), C14(H14a,H14b,H14c)
;
_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 0.38421(17) 0.7240(6) 0.23384(15) 0.0363(8) Uani 1.000000 .
O7 O 0.08303(17) 1.5452(6) 0.15964(15) 0.0385(8) Uani 1.000000 .
O2 O 0.18212(19) 0.6982(7) 0.34497(17) 0.0449(9) Uani 1.000000 .
O6 O 0.35272(17) 1.5187(6) 0.05901(15) 0.0370(8) Uani 1.000000 .
O4 O 0.42244(18) 1.2111(7) 0.11478(16) 0.0450(9) Uani 1.000000 .
O5 O 0.10412(19) 1.2814(7) 0.24110(17) 0.0477(10) Uani 1.000000 .
O3 O 0.3776(2) 0.1314(7) 0.38180(17) 0.0451(9) Uani 1.000000 .
N2 N 0.2769(2) 0.4040(7) 0.36014(19) 0.0361(9) Uani 1.000000 .
N3 N 0.3801(2) 0.4249(7) 0.30669(17) 0.0322(9) Uani 1.000000 .
C9 C 0.3479(2) 0.3074(9) 0.3519(2) 0.0321(10) Uani 1.000000 .
C6 C 0.2755(2) 0.7331(8) 0.2822(2) 0.0281(10) Uani 1.000000 .
N1 N 0.3065(2) 1.1062(7) 0.17505(17) 0.0310(9) Uani 1.000000 .
C11 C 0.1228(2) 1.3691(9) 0.1956(2) 0.0303(10) Uani 1.000000 .
C4 C 0.2983(2) 1.2921(8) 0.1315(2) 0.0284(9) Uani 1.000000 .
C7 C 0.3489(2) 0.6346(9) 0.2714(2) 0.0303(10) Uani 1.000000 .
C2 C 0.1945(2) 1.2965(8) 0.1745(2) 0.0302(10) Uani 1.000000 .
C12 C 0.1949(2) 1.6270(9) 0.0846(2) 0.0332(10) Uani 1.000000 .
C19 C 0.0154(3) 1.6443(10) 0.1802(2) 0.0416(12) Uani 1.000000 .
C8 C 0.2408(2) 0.6136(9) 0.3304(2) 0.0342(10) Uani 1.000000 .
C1 C 0.2446(2) 1.1000(8) 0.2029(2) 0.0294(9) Uani 1.000000 .
C3 C 0.2275(2) 1.4176(8) 0.1286(2) 0.0289(10) Uani 1.000000 .
C15 C 0.4526(2) 0.3198(10) 0.2960(2) 0.0377(11) Uani 1.000000 .
C10 C 0.3634(3) 1.3326(9) 0.1010(2) 0.0344(10) Uani 1.000000 .
C5 C 0.2343(2) 0.9301(8) 0.2507(2) 0.0319(10) Uani 1.000000 .
C20 C -0.0165(3) 1.8538(10) 0.1355(2) 0.0418(12) Uani 1.000000 .
C16 C 0.2419(3) 0.2766(9) 0.4073(2) 0.0411(12) Uani 1.000000 .
C13 C 0.1367(3) 1.5224(9) 0.0293(2) 0.0382(11) Uani 1.000000 .
C18 C 0.3954(3) 1.7945(9) -0.0131(2) 0.0427(12) Uani 1.000000 .
C17 C 0.4184(3) 1.5725(10) 0.0297(2) 0.0419(12) Uani 1.000000 .
C14 C 0.0988(3) 1.7309(11) -0.0130(2) 0.0489(14) Uani 1.000000 .
H1 H 0.3463(2) 1.0030(7) 0.18425(17) 0.0372(10) Uiso 1.000000 R
H12a H 0.1697(2) 1.7556(9) 0.1068(2) 0.0398(12) Uiso 1.000000 R
H12b H 0.2371(2) 1.7133(9) 0.0694(2) 0.0398(12) Uiso 1.000000 R
H19a H -0.0231(3) 1.5069(10) 0.1795(2) 0.0499(14) Uiso 1.000000 R
H19b H 0.0299(3) 1.7125(10) 0.2230(2) 0.0499(14) Uiso 1.000000 R
H15a H 0.4949(3) 0.434(3) 0.3146(13) 0.0565(17) Uiso 1.000000 GR
H15b H 0.4610(9) 0.150(3) 0.3152(13) 0.0565(17) Uiso 1.000000 GR
H15c H 0.4503(7) 0.306(6) 0.2512(2) 0.0565(17) Uiso 1.000000 GR
H5 H 0.1876(2) 0.9601(8) 0.2640(2) 0.0383(12) Uiso 1.000000 R
H20a H -0.0319(19) 1.7824(15) 0.0935(4) 0.0627(18) Uiso 1.000000 GR
H20b H -0.0612(12) 1.931(5) 0.1480(10) 0.0627(18) Uiso 1.000000 GR
H20c H 0.0229(7) 1.985(3) 0.1357(12) 0.0627(18) Uiso 1.000000 GR
H16a H 0.2745(10) 0.133(4) 0.4255(11) 0.0616(18) Uiso 1.000000 GR
H16b H 0.2371(18) 0.3996(19) 0.4399(8) 0.0616(18) Uiso 1.000000 GR
H16c H 0.1910(8) 0.212(6) 0.3877(4) 0.0616(18) Uiso 1.000000 GR
H13a H 0.1630(3) 1.4036(9) 0.0054(2) 0.0458(13) Uiso 1.000000 R
H13b H 0.0969(3) 1.4241(9) 0.0448(2) 0.0458(13) Uiso 1.000000 R
H18a H 0.3455(10) 1.759(3) -0.0402(11) 0.0640(18) Uiso 1.000000 GR
H18b H 0.392(2) 1.9490(16) 0.0115(2) 0.0640(18) Uiso 1.000000 GR
H18c H 0.4339(11) 1.821(4) -0.0385(12) 0.0640(18) Uiso 1.000000 GR
H17a H 0.4645(3) 1.6157(10) 0.0616(2) 0.0502(15) Uiso 1.000000 R
H17b H 0.4302(3) 1.4213(10) 0.0061(2) 0.0502(15) Uiso 1.000000 R
H14a H 0.0596(15) 1.6563(13) -0.0462(10) 0.073(2) Uiso 1.000000 GR
H14b H 0.0747(19) 1.853(4) 0.0108(4) 0.073(2) Uiso 1.000000 GR
H14c H 0.1374(5) 1.819(5) -0.0314(14) 0.073(2) Uiso 1.000000 GR


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 C7 1.228(5) . ?
O7 C11 1.320(5) . ?
O7 C19 1.463(5) . ?
O2 C8 1.235(5) . ?
O6 C10 1.327(6) . ?
O6 C17 1.474(5) . ?
O4 C10 1.211(5) . ?
O5 C11 1.206(5) . ?
O3 C9 1.189(6) . ?
N2 C9 1.407(6) . ?
N2 C8 1.366(6) . ?
N2 C16 1.471(6) . ?
N3 C9 1.387(6) . ?
N3 C7 1.389(6) . ?
N3 C15 1.465(5) . ?
C6 C7 1.468(6) . ?
C6 C8 1.470(6) . ?
C6 C5 1.366(6) . ?
N1 C4 1.350(6) . ?
N1 C1 1.366(5) . ?
C11 C2 1.494(6) . ?
C4 C3 1.411(6) . ?
C4 C10 1.467(6) . ?
C2 C1 1.417(6) . ?
C2 C3 1.415(6) . ?
C12 C3 1.495(6) . ?
C12 C13 1.528(7) . ?
C19 C20 1.502(7) . ?
C1 C5 1.414(6) . ?
C13 C14 1.498(7) . ?
C18 C17 1.495(7) . ?

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
C19 O7 C11 115.8(3) . . ?
C17 O6 C10 115.5(3) . . ?
C8 N2 C9 124.9(4) . . ?
C16 N2 C9 116.7(4) . . ?
C16 N2 C8 118.3(4) . . ?
C7 N3 C9 124.9(4) . . ?
C15 N3 C9 117.1(4) . . ?
C15 N3 C7 118.0(4) . . ?
N2 C9 O3 121.0(4) . . ?
N3 C9 O3 122.4(4) . . ?
N3 C9 N2 116.6(4) . . ?
C8 C6 C7 119.1(4) . . ?
C5 C6 C7 125.8(4) . . ?
C5 C6 C8 115.1(4) . . ?
C1 N1 C4 110.8(4) . . ?
O5 C11 O7 123.8(4) . . ?
C2 C11 O7 112.2(4) . . ?
C2 C11 O5 124.0(4) . . ?
C3 C4 N1 109.3(4) . . ?
C10 C4 N1 116.5(4) . . ?
C10 C4 C3 134.1(4) . . ?
N3 C7 O1 118.3(4) . . ?
C6 C7 O1 124.8(4) . . ?
C6 C7 N3 116.9(4) . . ?
C1 C2 C11 123.2(4) . . ?
C3 C2 C11 127.8(4) . . ?
C3 C2 C1 108.8(4) . . ?
C13 C12 C3 111.3(4) . . ?
C20 C19 O7 106.3(4) . . ?
N2 C8 O2 120.1(4) . . ?
C6 C8 O2 122.5(4) . . ?
C6 C8 N2 117.4(4) . . ?
C2 C1 N1 106.1(4) . . ?
C5 C1 N1 125.9(4) . . ?
C5 C1 C2 128.0(4) . . ?
C2 C3 C4 105.0(4) . . ?
C12 C3 C4 126.3(4) . . ?
C12 C3 C2 128.7(4) . . ?
O4 C10 O6 123.4(4) . . ?
C4 C10 O6 114.1(4) . . ?
C4 C10 O4 122.5(4) . . ?
C1 C5 C6 135.3(4) . . ?
C14 C13 C12 112.3(4) . . ?
C18 C17 O6 106.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.812
