# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_exp_9334
_database_code_depnum_ccdc_archive 'CCDC 2519407'
loop_
_audit_author_name
_audit_author_address
'WuJie Guo'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-12-26 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
_space_group_name_Hall           '-P 2yn'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
_cell_length_a                   10.3059(5)
_cell_length_b                   7.5527(4)
_cell_length_c                   20.5225(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.542(5)
_cell_angle_gamma                90.00
_cell_volume                     1583.6
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C4 C 0.2804(2) 0.3445(3) 0.18321(11)
C3 C 0.3550(2) 0.4528(3) 0.14564(12)
H3 H 0.3112 0.5278 0.1126
C1 C 0.5579(2) 0.3416(3) 0.20367(12)
N1 N 0.14770(18) 0.3469(2) 0.17335(10)
O1 O 0.77139(16) 0.4275(2) 0.18389(10)
C2 C 0.4892(2) 0.4513(3) 0.15606(12)
H2 H 0.5365 0.5262 0.1304
C7 C 0.6996(2) 0.3386(3) 0.21370(13)
H7 H 0.7404 0.2603 0.2464
C9 C 0.0719(2) 0.2379(3) 0.21299(13)
H9A H 0.0894 0.1126 0.2053
H9B H -0.0216 0.2620 0.2007
H9C H 0.0968 0.2657 0.2596
C5 C 0.3506(2) 0.2349(3) 0.23188(12)
H5 H 0.3043 0.1610 0.2584
C6 C 0.4854(2) 0.2350(3) 0.24098(12)
H6 H 0.5303 0.1601 0.2737
C8 C 0.0780(2) 0.4500(3) 0.11969(12)
H8A H 0.1023 0.5751 0.1253
H8B H -0.0166 0.4372 0.1201
H8C H 0.1013 0.4071 0.0777
C12 C 0.4624(2) 0.7430(3) 0.00661(12)
H12 H 0.4160 0.6840 -0.0302
C10 C 0.6694(2) 0.8194(3) 0.07085(12)
C13 C 0.3929(2) 0.8370(3) 0.05050(12)
N2 N 0.25893(18) 0.8409(3) 0.04161(10)
C15 C 0.6002(2) 0.9115(3) 0.11386(12)
H15 H 0.6473 0.9687 0.1509
O2 O 0.88005(17) 0.7407(2) 0.04477(10)
C14 C 0.4664(2) 0.9223(3) 0.10457(12)
H14 H 0.4226 0.9877 0.1347
C16 C 0.8103(2) 0.8115(3) 0.08087(14)
H16 H 0.8532 0.8668 0.1194
C11 C 0.5968(2) 0.7365(3) 0.01690(12)
H11 H 0.6418 0.6739 -0.0135
C18 C 0.1888(2) 0.9505(3) 0.08353(13)
H18A H 0.2128 0.9154 0.1295
H18B H 0.0943 0.9350 0.0712
H18C H 0.2118 1.0751 0.0782
C17 C 0.1848(2) 0.7532(3) -0.01463(13)
H17A H 0.2049 0.8085 -0.0553
H17B H 0.0910 0.7645 -0.0119
H17C H 0.2087 0.6276 -0.0145
C4 C 1.2804(2) 0.3445(3) 0.18321(11)
C3 C 1.3550(2) 0.4528(3) 0.14564(12)
H3 H 1.3112 0.5278 0.1126
C1 C 1.5579(2) 0.3416(3) 0.20367(12)
N1 N 1.14770(18) 0.3469(2) 0.17335(10)
O1 O 1.77139(16) 0.4275(2) 0.18389(10)
C2 C 1.4892(2) 0.4513(3) 0.15606(12)
H2 H 1.5365 0.5262 0.1304
C7 C 1.6996(2) 0.3386(3) 0.21370(13)
H7 H 1.7404 0.2603 0.2464
C9 C 1.0719(2) 0.2379(3) 0.21299(13)
H9A H 1.0894 0.1126 0.2053
H9B H 0.9784 0.2620 0.2007
H9C H 1.0968 0.2657 0.2596
C5 C 1.3506(2) 0.2349(3) 0.23188(12)
H5 H 1.3043 0.1610 0.2584
C6 C 1.4854(2) 0.2350(3) 0.24098(12)
H6 H 1.5303 0.1601 0.2737
C8 C 1.0780(2) 0.4500(3) 0.11969(12)
H8A H 1.1023 0.5751 0.1253
H8B H 0.9834 0.4372 0.1201
H8C H 1.1013 0.4071 0.0777
C12 C 1.4624(2) 0.7430(3) 0.00661(12)
H12 H 1.4160 0.6840 -0.0302
C10 C 1.6694(2) 0.8194(3) 0.07085(12)
C13 C 1.3929(2) 0.8370(3) 0.05050(12)
N2 N 1.25893(18) 0.8409(3) 0.04161(10)
C15 C 1.6002(2) 0.9115(3) 0.11386(12)
H15 H 1.6473 0.9687 0.1509
O2 O 1.88005(17) 0.7407(2) 0.04477(10)
C14 C 1.4664(2) 0.9223(3) 0.10457(12)
H14 H 1.4226 0.9877 0.1347
C16 C 1.8103(2) 0.8115(3) 0.08087(14)
H16 H 1.8532 0.8668 0.1194
C11 C 1.5968(2) 0.7365(3) 0.01690(12)
H11 H 1.6418 0.6739 -0.0135
C18 C 1.1888(2) 0.9505(3) 0.08353(13)
H18A H 1.2128 0.9154 0.1295
H18B H 1.0943 0.9350 0.0712
H18C H 1.2118 1.0751 0.0782
C17 C 1.1848(2) 0.7532(3) -0.01463(13)
H17A H 1.2049 0.8085 -0.0553
H17B H 1.0910 0.7645 -0.0119
H17C H 1.2087 0.6276 -0.0145
C4 C 0.2196(2) -0.1555(3) 0.31679(11)
C3 C 0.1450(2) -0.0472(3) 0.35436(12)
H3 H 0.1888 0.0278 0.3874
C1 C -0.0579(2) -0.1584(3) 0.29633(12)
N1 N 0.35230(18) -0.1531(2) 0.32665(10)
O1 O -0.27139(16) -0.0725(2) 0.31611(10)
C2 C 0.0108(2) -0.0487(3) 0.34394(12)
H2 H -0.0365 0.0262 0.3696
C7 C -0.1996(2) -0.1614(3) 0.28630(13)
H7 H -0.2404 -0.2397 0.2536
C9 C 0.4281(2) -0.2621(3) 0.28701(13)
H9A H 0.4106 -0.3874 0.2947
H9B H 0.5216 -0.2380 0.2993
H9C H 0.4032 -0.2343 0.2404
C5 C 0.1494(2) -0.2651(3) 0.26812(12)
H5 H 0.1957 -0.3390 0.2416
C6 C 0.0146(2) -0.2650(3) 0.25902(12)
H6 H -0.0303 -0.3399 0.2263
C8 C 0.4220(2) -0.0500(3) 0.38031(12)
H8A H 0.3977 0.0751 0.3747
H8B H 0.5166 -0.0628 0.3799
H8C H 0.3987 -0.0929 0.4223
C4 C 1.2196(2) -0.1555(3) 0.31679(11)
C3 C 1.1450(2) -0.0472(3) 0.35436(12)
H3 H 1.1888 0.0278 0.3874
C1 C 0.9421(2) -0.1584(3) 0.29633(12)
N1 N 1.35230(18) -0.1531(2) 0.32665(10)
O1 O 0.72861(16) -0.0725(2) 0.31611(10)
C2 C 1.0108(2) -0.0487(3) 0.34394(12)
H2 H 0.9635 0.0262 0.3696
C7 C 0.8004(2) -0.1614(3) 0.28630(13)
H7 H 0.7596 -0.2397 0.2536
C9 C 1.4281(2) -0.2621(3) 0.28701(13)
H9A H 1.4106 -0.3874 0.2947
H9B H 1.5216 -0.2380 0.2993
H9C H 1.4032 -0.2343 0.2404
C5 C 1.1494(2) -0.2651(3) 0.26812(12)
H5 H 1.1957 -0.3390 0.2416
C6 C 1.0146(2) -0.2650(3) 0.25902(12)
H6 H 0.9697 -0.3399 0.2263
C8 C 1.4220(2) -0.0500(3) 0.38031(12)
H8A H 1.3977 0.0751 0.3747
H8B H 1.5166 -0.0628 0.3799
H8C H 1.3987 -0.0929 0.4223
C12 C 0.0376(2) -0.7570(3) 0.49339(12)
H12 H 0.0840 -0.8160 0.5302
C10 C -0.1694(2) -0.6806(3) 0.42915(12)
C13 C 0.1071(2) -0.6630(3) 0.44950(12)
N2 N 0.24107(18) -0.6591(3) 0.45839(10)
C15 C -0.1002(2) -0.5885(3) 0.38614(12)
H15 H -0.1473 -0.5313 0.3491
O2 O -0.38005(17) -0.7593(2) 0.45523(10)
C14 C 0.0336(2) -0.5777(3) 0.39543(12)
H14 H 0.0774 -0.5123 0.3653
C16 C -0.3103(2) -0.6885(3) 0.41913(14)
H16 H -0.3532 -0.6332 0.3806
C11 C -0.0968(2) -0.7635(3) 0.48310(12)
H11 H -0.1418 -0.8261 0.5135
C18 C 0.3112(2) -0.5495(3) 0.41647(13)
H18A H 0.2872 -0.5846 0.3705
H18B H 0.4057 -0.5650 0.4288
H18C H 0.2882 -0.4249 0.4218
C17 C 0.3152(2) -0.7468(3) 0.51463(13)
H17A H 0.2951 -0.6915 0.5553
H17B H 0.4090 -0.7355 0.5119
H17C H 0.2913 -0.8724 0.5145
C12 C 1.0376(2) -0.7570(3) 0.49339(12)
H12 H 1.0840 -0.8160 0.5302
C10 C 0.8306(2) -0.6806(3) 0.42915(12)
C13 C 1.1071(2) -0.6630(3) 0.44950(12)
N2 N 1.24107(18) -0.6591(3) 0.45839(10)
C15 C 0.8998(2) -0.5885(3) 0.38614(12)
H15 H 0.8527 -0.5313 0.3491
O2 O 0.61995(17) -0.7593(2) 0.45523(10)
C14 C 1.0336(2) -0.5777(3) 0.39543(12)
H14 H 1.0774 -0.5123 0.3653
C16 C 0.6897(2) -0.6885(3) 0.41913(14)
H16 H 0.6468 -0.6332 0.3806
C11 C 0.9032(2) -0.7635(3) 0.48310(12)
H11 H 0.8582 -0.8261 0.5135
C18 C 1.3112(2) -0.5495(3) 0.41647(13)
H18A H 1.2872 -0.5846 0.3705
H18B H 1.4057 -0.5650 0.4288
H18C H 1.2882 -0.4249 0.4218
C17 C 1.3152(2) -0.7468(3) 0.51463(13)
H17A H 1.2951 -0.6915 0.5553
H17B H 1.4090 -0.7355 0.5119
H17C H 1.2913 -0.8724 0.5145

#END
####################################################################### 
# 
# 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_exp_9331
_database_code_depnum_ccdc_archive 'CCDC 2519406'
loop_
_audit_author_name
_audit_author_address
'WuJie Guo'
;
China
;
_audit_update_record             
;
2025-12-26 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19
_space_group_name_Hall           'P 2ac 2ab'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
_cell_length_a                   6.0983(5)
_cell_length_b                   7.3384(7)
_cell_length_c                   20.8985(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     935.245
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O2 O -0.7208(2) -0.5641(2) -0.07081(7)
O1 O -0.4228(2) -0.4391(2) -0.02496(7)
C2 C -0.4323(3) -0.5938(3) -0.24867(10)
H2 H -0.5063 -0.6555 -0.2823
C6 C -0.1264(3) -0.4181(3) -0.20949(10)
H6 H 0.0092 -0.3574 -0.2163
C4 C -0.4173(3) -0.5058(3) -0.13690(10)
C1 C -0.2328(3) -0.5041(3) -0.26127(9)
N1 N -0.1479(3) -0.5016(3) -0.32202(8)
C7 C -0.5141(3) -0.4988(3) -0.07225(10)
C5 C -0.2172(3) -0.4213(3) -0.14895(10)
H5 H -0.1411 -0.3644 -0.1147
C9 C 0.0608(3) -0.4141(3) -0.33600(11)
H9A H 0.1678 -0.4466 -0.3029
H9B H 0.0410 -0.2816 -0.3367
H9C H 0.1140 -0.4551 -0.3778
C8 C -0.2746(4) -0.5678(3) -0.37576(10)
H8A H -0.4163 -0.5048 -0.3770
H8B H -0.2989 -0.6992 -0.3711
H8C H -0.1945 -0.5443 -0.4156
C3 C -0.5215(4) -0.5931(3) -0.18801(10)
H3 H -0.6571 -0.6534 -0.1808
C10 C -0.8336(4) -0.5507(4) -0.01007(10)
H10A H -0.7667 -0.6351 0.0206
H10B H -0.9885 -0.5822 -0.0159
H10C H -0.8219 -0.4259 0.0062
O2 O 0.2208(2) -0.4359(2) 0.42919(7)
O1 O -0.0772(2) -0.5609(2) 0.47504(7)
C2 C -0.0677(3) -0.4062(3) 0.25133(10)
H2 H 0.0063 -0.3445 0.2177
C6 C -0.3736(3) -0.5819(3) 0.29051(10)
H6 H -0.5092 -0.6426 0.2837
C4 C -0.0827(3) -0.4942(3) 0.36310(10)
C1 C -0.2672(3) -0.4959(3) 0.23873(9)
N1 N -0.3521(3) -0.4984(3) 0.17798(8)
C7 C 0.0141(3) -0.5012(3) 0.42775(10)
C5 C -0.2828(3) -0.5787(3) 0.35105(10)
H5 H -0.3589 -0.6356 0.3853
C9 C -0.5608(3) -0.5859(3) 0.16400(11)
H9A H -0.6678 -0.5534 0.1971
H9B H -0.5410 -0.7184 0.1633
H9C H -0.6140 -0.5449 0.1222
C8 C -0.2254(4) -0.4322(3) 0.12424(10)
H8A H -0.0837 -0.4952 0.1230
H8B H -0.2011 -0.3008 0.1289
H8C H -0.3055 -0.4557 0.0844
C3 C 0.0215(4) -0.4069(3) 0.31199(10)
H3 H 0.1571 -0.3466 0.3192
C10 C 0.3336(4) -0.4493(4) 0.48993(10)
H10A H 0.2667 -0.3649 0.5206
H10B H 0.4885 -0.4178 0.4841
H10C H 0.3219 -0.5741 0.5062
O2 O -1.2208(2) 0.0641(2) 0.07081(7)
O1 O -0.9228(2) -0.0609(2) 0.02496(7)
C2 C -0.9323(3) 0.0938(3) 0.24867(10)
H2 H -1.0063 0.1555 0.2823
C6 C -0.6264(3) -0.0819(3) 0.20949(10)
H6 H -0.4908 -0.1426 0.2163
C4 C -0.9173(3) 0.0058(3) 0.13690(10)
C1 C -0.7328(3) 0.0041(3) 0.26127(9)
N1 N -0.6479(3) 0.0016(3) 0.32202(8)
C7 C -1.0141(3) -0.0012(3) 0.07225(10)
C5 C -0.7172(3) -0.0787(3) 0.14895(10)
H5 H -0.6411 -0.1356 0.1147
C9 C -0.4392(3) -0.0859(3) 0.33600(11)
H9A H -0.3322 -0.0534 0.3029
H9B H -0.4590 -0.2184 0.3367
H9C H -0.3860 -0.0449 0.3778
C8 C -0.7746(4) 0.0678(3) 0.37576(10)
H8A H -0.9163 0.0048 0.3770
H8B H -0.7989 0.1992 0.3711
H8C H -0.6945 0.0443 0.4156
C3 C -1.0215(4) 0.0931(3) 0.18801(10)
H3 H -1.1571 0.1534 0.1808
C10 C -1.3336(4) 0.0507(4) 0.01007(10)
H10A H -1.2667 0.1351 -0.0206
H10B H -1.4885 0.0822 0.0159
H10C H -1.3219 -0.0741 -0.0062
O2 O -0.2792(2) -0.0641(2) -0.42919(7)
O1 O -0.5772(2) 0.0609(2) -0.47504(7)
C2 C -0.5677(3) -0.0938(3) -0.25133(10)
H2 H -0.4937 -0.1555 -0.2177
C6 C -0.8736(3) 0.0819(3) -0.29051(10)
H6 H -1.0092 0.1426 -0.2837
C4 C -0.5827(3) -0.0058(3) -0.36310(10)
C1 C -0.7672(3) -0.0041(3) -0.23873(9)
N1 N -0.8521(3) -0.0016(3) -0.17798(8)
C7 C -0.4859(3) 0.0012(3) -0.42775(10)
C5 C -0.7828(3) 0.0787(3) -0.35105(10)
H5 H -0.8589 0.1356 -0.3853
C9 C -1.0608(3) 0.0859(3) -0.16400(11)
H9A H -1.1678 0.0534 -0.1971
H9B H -1.0410 0.2184 -0.1633
H9C H -1.1140 0.0449 -0.1222
C8 C -0.7254(4) -0.0678(3) -0.12424(10)
H8A H -0.5837 -0.0048 -0.1230
H8B H -0.7011 -0.1992 -0.1289
H8C H -0.8055 -0.0443 -0.0844
C3 C -0.4785(4) -0.0931(3) -0.31199(10)
H3 H -0.3429 -0.1534 -0.3192
C10 C -0.1664(4) -0.0507(4) -0.48993(10)
H10A H -0.2333 -0.1351 -0.5206
H10B H -0.0115 -0.0822 -0.4841
H10C H -0.1781 0.0741 -0.5062

#END
####################################################################### 
# 
# 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_exp_9402
_database_code_depnum_ccdc_archive 'CCDC 2518935'
loop_
_audit_author_name
_audit_author_address
'WuJie Guo'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-12-26 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2024-09-27
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_chemical_absolute_configuration unk
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.6298(10)
_cell_length_b                   7.9243(18)
_cell_length_c                   19.897(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     887.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    524
_cell_measurement_temperature    120.20(10)
_cell_measurement_theta_max      26.6570
_cell_measurement_theta_min      4.0830
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3542
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.8073
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00    8.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   44.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -99.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289    0.0000    0.0000 118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0023356000
_diffrn_orient_matrix_UB_12      -0.0632362000
_diffrn_orient_matrix_UB_13      0.0252109000
_diffrn_orient_matrix_UB_21      -0.0777617000
_diffrn_orient_matrix_UB_22      0.0492230000
_diffrn_orient_matrix_UB_23      0.0201017000
_diffrn_orient_matrix_UB_31      -0.0992253000
_diffrn_orient_matrix_UB_32      -0.0399936000
_diffrn_orient_matrix_UB_33      -0.0151778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1071
_reflns_number_total             1698
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2869(4) 0.4631(3) 0.06696(10) 0.0507(7) Uani 1 1 d . . .
C2 C 0.0559(5) 0.4586(4) 0.26655(13) 0.0308(7) Uani 1 1 d . . .
H2 H -0.0799 0.5219 0.2794 0.037 Uiso 1 1 calc R . .
C4 C 0.3804(5) 0.2724(4) 0.29328(13) 0.0322(7) Uani 1 1 d . . .
H4 H 0.4686 0.2074 0.3247 0.039 Uiso 1 1 calc R . .
C3 C 0.1832(5) 0.3650(4) 0.31570(14) 0.0276(7) Uani 1 1 d . . .
C6 C 0.3262(5) 0.3664(4) 0.17844(13) 0.0277(7) Uani 1 1 d . . .
C1 C 0.1278(5) 0.4581(4) 0.20060(13) 0.0301(7) Uani 1 1 d . . .
H1 H 0.0400 0.5221 0.1688 0.036 Uiso 1 1 calc R . .
C5 C 0.4491(5) 0.2733(4) 0.22676(13) 0.0321(8) Uani 1 1 d . . .
H5 H 0.5835 0.2090 0.2135 0.039 Uiso 1 1 calc R . .
C10 C 0.2333(4) 0.2668(4) 0.43220(13) 0.0412(8) Uani 1 1 d . . .
H10A H 0.1730 0.1510 0.4295 0.062 Uiso 1 1 calc R . .
H10B H 0.2007 0.3127 0.4770 0.062 Uiso 1 1 calc R . .
H10C H 0.4051 0.2668 0.4242 0.062 Uiso 1 1 calc R . .
C8 C 0.6015(5) 0.2696(4) 0.08299(14) 0.0455(9) Uani 1 1 d . . .
H8A H 0.6069 0.2721 0.0338 0.068 Uiso 1 1 calc R . .
H8B H 0.5833 0.1528 0.0983 0.068 Uiso 1 1 calc R . .
H8C H 0.7493 0.3166 0.1011 0.068 Uiso 1 1 calc R . .
C7 C 0.3947(5) 0.3728(4) 0.10721(14) 0.0347(8) Uani 1 1 d . . .
C9 C -0.0943(5) 0.4611(4) 0.40317(15) 0.0444(9) Uani 1 1 d . . .
H9A H -0.0799 0.5800 0.3903 0.067 Uiso 1 1 calc R . .
H9B H -0.1109 0.4526 0.4521 0.067 Uiso 1 1 calc R . .
H9C H -0.2345 0.4120 0.3815 0.067 Uiso 1 1 calc R . .
N1 N 0.1168(4) 0.3701(3) 0.38186(12) 0.0369(7) Uani 1 1 d . . .


_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 C7 1.234(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.421(4) . ?
C2 C1 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.403(4) . ?
C4 C5 1.379(4) . ?
C3 N1 1.369(3) . ?
C6 C1 1.403(4) . ?
C6 C5 1.395(4) . ?
C6 C7 1.470(4) . ?
C1 H1 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 N1 1.450(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C7 1.502(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 N1 1.453(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
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C5 C4 C3 121.6(3) . . ?
C4 C3 C2 116.9(3) . . ?
N1 C3 C2 120.6(3) . . ?
N1 C3 C4 122.5(3) . . ?
C1 C6 C7 119.6(3) . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C7 123.5(3) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 H1 118.8 . . ?
C6 C1 H1 118.8 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
O1 C7 C6 121.1(3) . . ?
O1 C7 C8 119.3(3) . . ?
C6 C7 C8 119.6(3) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
C3 N1 C10 121.6(2) . . ?
C3 N1 C9 121.2(3) . . ?
C10 N1 C9 116.7(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
C2 C3 N1 C10 175.7(3) . . . . ?
C2 C3 N1 C9 4.4(4) . . . . ?
C4 C3 N1 C10 -5.9(4) . . . . ?
C4 C3 N1 C9 -177.3(3) . . . . ?
C3 C2 C1 C6 0.3(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 N1 177.7(3) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C1 C6 C7 O1 3.2(4) . . . . ?
C1 C6 C7 C8 -177.7(3) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C5 C4 C3 N1 -177.8(3) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C5 C6 C7 O1 -176.6(3) . . . . ?
C5 C6 C7 C8 2.5(4) . . . . ?
C7 C6 C1 C2 -179.4(3) . . . . ?
C7 C6 C5 C4 179.2(3) . . . . ?

