# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_yur109
_audit_block_doi                 10.5517/ccdc.csd.cc25bx9r
_database_code_depnum_ccdc_archive 'CCDC 2006484'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Chemistry Department of Moscow State University
Russia
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;


#
# Model has Chirality at C3  (Sohnke SpGr)  "S"
# Model has Chirality at C4  (Sohnke SpGr)  "S"
# Model has Chirality at C41 (Sohnke SpGr)  "R"  
#
_vrf_PLAT026_I                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        26% Check 
RESPONSE: The crystals were of very-very poor quality
;

_chemical_name_systematic        
'(3S,4S)-Tert-butyl 3-hydroxy-4-(((R)-1-phenylethyl)amino)-3-((E)-styryl)piperidine-1-carboxylate hydrobromide'
_chemical_name_common            ?
_chemical_melting_point_gt       503
_chemical_melting_point_lt       504
_chemical_formula_moiety         'C26 H35 N2 O3, Br'
_chemical_formula_sum            'C26 H35 Br N2 O3'
_chemical_formula_weight         503.46
_chemical_absolute_configuration ad
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_preparation       EtOH

_cell_length_a                   9.1272(13)
_cell_length_b                   11.6147(14)
_cell_length_c                   25.235(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'x+1/2, -y+1/2, -z+'
'-x+, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.2759
_refine_ls_R_factor_gt           0.0949
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1095

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
BR1 Br 0.8054(2) 0.63010(16) 0.01282(8) 0.0819(7) Uani 1 1 d . . . . .
N1 N 0.3920(15) 0.5671(11) 0.1554(5) 0.045(4) Uani 1 1 d . U . . .
C2 C 0.2425(18) 0.5448(14) 0.1512(7) 0.069(6) Uani 1 1 d . U . . .
H2A H 0.1962 0.5709 0.1837 0.082 Uiso 1 1 calc R U . . .
H2B H 0.2298 0.4619 0.1496 0.082 Uiso 1 1 calc R U . . .
C3 C 0.1572(13) 0.5983(10) 0.1040(5) 0.024(3) Uani 1 1 d . U . . .
C4 C 0.2438(19) 0.5519(15) 0.0546(7) 0.069(6) Uani 1 1 d . U . . .
H4 H 0.2311 0.4683 0.0518 0.083 Uiso 1 1 calc R U . . .
C5 C 0.399(2) 0.5798(14) 0.0557(7) 0.079(6) Uani 1 1 d . U . . .
H5A H 0.4103 0.6627 0.0537 0.095 Uiso 1 1 calc R U . . .
H5B H 0.4459 0.5464 0.0249 0.095 Uiso 1 1 calc R U . . .
C6 C 0.480(2) 0.5325(15) 0.1092(7) 0.076(6) Uani 1 1 d . U . . .
H6A H 0.4885 0.4493 0.1079 0.091 Uiso 1 1 calc R U . . .
H6B H 0.5777 0.5649 0.1118 0.091 Uiso 1 1 calc R U . . .
C11 C 0.478(3) 0.644(2) 0.1831(13) 0.120(11) Uani 1 1 d . . . . .
O11 O 0.5804(19) 0.6831(12) 0.1771(6) 0.085(5) Uani 1 1 d . . . . .
O12 O 0.3649(13) 0.6917(11) 0.2206(6) 0.081(4) Uani 1 1 d . . . . .
C13 C 0.4031(14) 0.7834(15) 0.2627(7) 0.104(8) Uani 1 1 d D . . . .
C14 C 0.4540(18) 0.8812(16) 0.2313(7) 0.128(4) Uani 1 1 d D . . . .
H14A H 0.5383 0.8588 0.2110 0.193 Uiso 1 1 calc R U . . .
H14B H 0.3774 0.9057 0.2078 0.193 Uiso 1 1 calc R U . . .
H14C H 0.4799 0.9435 0.2545 0.193 Uiso 1 1 calc R U . . .
C15 C 0.5203(17) 0.7381(16) 0.2961(7) 0.128(4) Uani 1 1 d D . . . .
H15A H 0.4840 0.6740 0.3163 0.193 Uiso 1 1 calc R U . . .
H15B H 0.6003 0.7131 0.2743 0.193 Uiso 1 1 calc R U . . .
H15C H 0.5536 0.7972 0.3198 0.193 Uiso 1 1 calc R U . . .
C16 C 0.2747(18) 0.8142(14) 0.2942(7) 0.128(4) Uani 1 1 d D . . . .
H16A H 0.2435 0.7486 0.3144 0.193 Uiso 1 1 calc R U . . .
H16B H 0.2993 0.8760 0.3179 0.193 Uiso 1 1 calc R U . . .
H16C H 0.1969 0.8382 0.2711 0.193 Uiso 1 1 calc R U . . .
O3 O 0.0266(13) 0.5367(8) 0.1086(4) 0.065(3) Uani 1 1 d . U . . .
H3 H -0.0305 0.5573 0.0854 0.097 Uiso 1 1 calc R U . . .
C31 C 0.157(2) 0.7284(13) 0.1137(6) 0.064(4) Uani 1 1 d . U . . .
H31 H 0.2378 0.7706 0.1024 0.077 Uiso 1 1 calc R U . . .
C32 C 0.053(2) 0.7826(13) 0.1364(7) 0.064(4) Uani 1 1 d . U . . .
H32 H -0.0299 0.7433 0.1479 0.077 Uiso 1 1 calc R U . . .
C33 C 0.0635(17) 0.8957(9) 0.1433(6) 0.111(3) Uani 1 1 d G U . . .
C34 C 0.1577(14) 0.9788(12) 0.1230(5) 0.111(3) Uani 1 1 d G U . . .
H34 H 0.2231 0.9597 0.0961 0.133 Uiso 1 1 calc R U . . .
C35 C 0.1541(14) 1.0904(11) 0.1429(5) 0.111(3) Uani 1 1 d G U . . .
H35 H 0.2171 1.1460 0.1293 0.133 Uiso 1 1 calc R U . . .
C36 C 0.0563(17) 1.1189(9) 0.1830(5) 0.111(3) Uani 1 1 d G U . . .
H36 H 0.0539 1.1936 0.1963 0.133 Uiso 1 1 calc R U . . .
C37 C -0.0379(14) 1.0358(14) 0.2033(4) 0.111(3) Uani 1 1 d G U . . .
H37 H -0.1033 1.0549 0.2301 0.133 Uiso 1 1 calc R U . . .
C38 C -0.0342(15) 0.9242(12) 0.1834(6) 0.111(3) Uani 1 1 d G U . . .
H38 H -0.0972 0.8686 0.1970 0.133 Uiso 1 1 calc R U . . .
N4 N 0.1862(15) 0.6101(9) 0.0042(5) 0.070(4) Uani 1 1 d . . . . .
H4A H 0.0888 0.6074 0.0052 0.084 Uiso 1 1 calc R U . . .
H4B H 0.2116 0.6840 0.0056 0.084 Uiso 1 1 calc R U . . .
C41 C 0.2341(18) 0.5641(15) -0.0488(8) 0.096(7) Uani 1 1 d D . . . .
H41 H 0.3360 0.5855 -0.0561 0.115 Uiso 1 1 calc R U . . .
C42 C 0.129(2) 0.620(2) -0.0904(8) 0.128(4) Uani 1 1 d . . . . .
H42A H 0.1542 0.5937 -0.1252 0.193 Uiso 1 1 calc R U . . .
H42B H 0.0296 0.5985 -0.0825 0.193 Uiso 1 1 calc R U . . .
H42C H 0.1379 0.7023 -0.0888 0.193 Uiso 1 1 calc R U . . .
C43 C 0.2152(11) 0.4282(7) -0.0496(4) 0.095(3) Uani 1 1 d G . . . .
C44 C 0.3344(10) 0.3582(9) -0.0613(4) 0.095(3) Uani 1 1 d DG . . . .
H44 H 0.4249 0.3909 -0.0691 0.114 Uiso 1 1 calc R U . . .
C45 C 0.3182(14) 0.2392(9) -0.0614(4) 0.095(3) Uani 1 1 d G . . . .
H45 H 0.3979 0.1923 -0.0693 0.114 Uiso 1 1 calc R U . . .
C46 C 0.1830(16) 0.1902(7) -0.0499(5) 0.095(3) Uani 1 1 d G . . . .
H46 H 0.1722 0.1106 -0.0500 0.114 Uiso 1 1 calc R U . . .
C47 C 0.0638(13) 0.2603(9) -0.0382(5) 0.095(3) Uani 1 1 d G . . . .
H47 H -0.0267 0.2276 -0.0305 0.114 Uiso 1 1 calc R U . . .
C48 C 0.0799(10) 0.3793(9) -0.0381(4) 0.095(3) Uani 1 1 d DG . . . .
H48 H 0.0002 0.4262 -0.0303 0.114 Uiso 1 1 calc R U . . .


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
N1 C11 1.38(3) . ?
N1 C2 1.394(17) . ?
N1 C6 1.471(19) . ?
C2 C3 1.554(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.395(14) . ?
C3 C31 1.531(17) . ?
C3 C4 1.573(18) . ?
C4 C5 1.45(2) . ?
C4 N4 1.533(17) . ?
C4 H4 0.9800 . ?
C5 C6 1.64(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 O11 1.05(2) . ?
C11 O12 1.51(3) . ?
O12 C13 1.54(2) . ?
C13 C14 1.461(12) . ?
C13 C16 1.461(12) . ?
C13 C15 1.461(12) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 H3 0.8200 . ?
C31 C32 1.27(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.329(17) . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 C37 1.3900 . ?
C36 H36 0.9300 . ?
C37 C38 1.3900 . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
N4 C41 1.506(17) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
C41 C42 1.56(2) . ?
C41 C43 1.587(17) . ?
C41 H41 0.9800 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.3900 . ?
C43 C48 1.3900 . ?
C44 C45 1.3900 . ?
C44 H44 0.9300 . ?
C45 C46 1.3900 . ?
C45 H45 0.9300 . ?
C46 C47 1.3900 . ?
C46 H46 0.9300 . ?
C47 C48 1.3900 . ?
C47 H47 0.9300 . ?
C48 H48 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
C11 N1 C2 135.8(19) . . ?
C11 N1 C6 105.5(19) . . ?
C2 N1 C6 115.1(15) . . ?
N1 C2 C3 118.3(14) . . ?
N1 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
N1 C2 H2B 107.7 . . ?
C3 C2 H2B 107.7 . . ?
H2A C2 H2B 107.1 . . ?
O3 C3 C31 119.5(12) . . ?
O3 C3 C2 99.1(10) . . ?
C31 C3 C2 105.8(12) . . ?
O3 C3 C4 108.6(10) . . ?
C31 C3 C4 117.8(12) . . ?
C2 C3 C4 102.7(11) . . ?
C5 C4 N4 104.6(15) . . ?
C5 C4 C3 113.4(15) . . ?
N4 C4 C3 109.5(13) . . ?
C5 C4 H4 109.7 . . ?
N4 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C4 C5 C6 112.6(16) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 C5 108.3(14) . . ?
N1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O11 C11 N1 136(4) . . ?
O11 C11 O12 123(3) . . ?
N1 C11 O12 99.6(19) . . ?
C11 O12 C13 122.1(14) . . ?
C14 C13 C16 111.1(9) . . ?
C14 C13 C15 111.1(9) . . ?
C16 C13 C15 111.1(9) . . ?
C14 C13 O12 103.6(14) . . ?
C16 C13 O12 111.3(14) . . ?
C15 C13 O12 108.3(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 O3 H3 109.5 . . ?
C32 C31 C3 124.0(16) . . ?
C32 C31 H31 118.0 . . ?
C3 C31 H31 118.0 . . ?
C31 C32 C33 119.5(18) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C32 C33 C34 133.1(15) . . ?
C32 C33 C38 106.5(15) . . ?
C34 C33 C38 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C33 120.0 . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
C41 N4 C4 118.7(13) . . ?
C41 N4 H4A 107.6 . . ?
C4 N4 H4A 107.6 . . ?
C41 N4 H4B 107.6 . . ?
C4 N4 H4B 107.6 . . ?
H4A N4 H4B 107.1 . . ?
N4 C41 C42 105.6(14) . . ?
N4 C41 C43 109.4(13) . . ?
C42 C41 C43 109.8(14) . . ?
N4 C41 H41 110.6 . . ?
C42 C41 H41 110.6 . . ?
C43 C41 H41 110.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C48 120.0 . . ?
C44 C43 C41 120.00(5) . . ?
C48 C43 C41 120.00(5) . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C47 C46 C45 120.0 . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C48 C47 C46 120.0 . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C47 C48 C43 120.0 . . ?
C47 C48 H48 120.0 . . ?
C43 C48 H48 120.0 . . ?

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
C11 N1 C2 C3 97(3) . . . . ?
C6 N1 C2 C3 -57.7(19) . . . . ?
N1 C2 C3 O3 168.2(14) . . . . ?
N1 C2 C3 C31 -67.5(18) . . . . ?
N1 C2 C3 C4 56.6(17) . . . . ?
O3 C3 C4 C5 -160.2(14) . . . . ?
C31 C3 C4 C5 60(2) . . . . ?
C2 C3 C4 C5 -55.9(18) . . . . ?
O3 C3 C4 N4 83.3(14) . . . . ?
C31 C3 C4 N4 -56.6(16) . . . . ?
C2 C3 C4 N4 -172.3(12) . . . . ?
N4 C4 C5 C6 176.0(12) . . . . ?
C3 C4 C5 C6 57(2) . . . . ?
C11 N1 C6 C5 -114.3(17) . . . . ?
C2 N1 C6 C5 47.8(19) . . . . ?
C4 C5 C6 N1 -49(2) . . . . ?
C2 N1 C11 O11 -152(3) . . . . ?
C6 N1 C11 O11 5(4) . . . . ?
C2 N1 C11 O12 11(3) . . . . ?
C6 N1 C11 O12 167.5(14) . . . . ?
O11 C11 O12 C13 -15(4) . . . . ?
N1 C11 O12 C13 179.2(12) . . . . ?
C11 O12 C13 C14 61.2(17) . . . . ?
C11 O12 C13 C16 -179.3(16) . . . . ?
C11 O12 C13 C15 -56.9(18) . . . . ?
O3 C3 C31 C32 15(2) . . . . ?
C2 C3 C31 C32 -95.4(19) . . . . ?
C4 C3 C31 C32 150.6(16) . . . . ?
C3 C31 C32 C33 179.5(15) . . . . ?
C31 C32 C33 C34 13(3) . . . . ?
C31 C32 C33 C38 -159.7(15) . . . . ?
C32 C33 C34 C35 -171.8(17) . . . . ?
C38 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C36 C37 C38 C33 0.0 . . . . ?
C32 C33 C38 C37 173.8(13) . . . . ?
C34 C33 C38 C37 0.0 . . . . ?
C5 C4 N4 C41 68.8(18) . . . . ?
C3 C4 N4 C41 -169.3(13) . . . . ?
C4 N4 C41 C42 166.3(14) . . . . ?
C4 N4 C41 C43 48.2(16) . . . . ?
N4 C41 C43 C44 -124.0(10) . . . . ?
C42 C41 C43 C44 120.5(12) . . . . ?
N4 C41 C43 C48 55.3(15) . . . . ?
C42 C41 C43 C48 -60.3(15) . . . . ?
C48 C43 C44 C45 0.0 . . . . ?
C41 C43 C44 C45 179.3(11) . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C44 C45 C46 C47 0.0 . . . . ?
C45 C46 C47 C48 0.0 . . . . ?
C46 C47 C48 C43 0.0 . . . . ?
C44 C43 C48 C47 0.0 . . . . ?
C41 C43 C48 C47 -179.3(11) . . . . ?

_refine_ls_abs_structure_details 
;
 Flack x determined using 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)

######################################################################## 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'
O O 0.0492 0.0322 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_cell_measurement_reflns_used    10079
_cell_measurement_theta_min      4.190
_cell_measurement_theta_max      70.120

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.305
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.115
_exptl_absorpt_process_details   
;
 Walker, N. & Stuart, D. (1983). Acta. Cryst. A39, 158-166.
;
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.812


_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
'65 runs, 2929 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10079
_diffrn_reflns_av_unetI/netI     0.3324
_diffrn_reflns_av_R_equivalents  0.1161
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.190
_diffrn_reflns_theta_max         70.120
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5003
_reflns_number_gt                1293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.982

_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    ?
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_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)+(0.0010P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5003
_refine_ls_number_parameters     181
_refine_ls_number_restraints     97
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_restrained_S_all      0.841
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_yur101
_audit_block_doi                 10.5517/cc106c2n
_database_code_depnum_ccdc_archive 'CCDC 929630'
_audit_update_record             
;
2013-03-17 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
;
(3R,3aS,8aS)-3-phenyl-1-((R)-1-phenylethyl)hexahydro-1H-
oxepino[3,4-b]pyrrol-4(2H)-one
;
_chemical_melting_point_gt       393
_chemical_melting_point_lt       394
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H25 N O2'
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       'Ethanol--Methyl / tert--butyl ether'
_exptl_crystal_density_diffrn    1.211

_cell_length_a                   5.72800(10)
_cell_length_b                   16.4639(3)
_cell_length_c                   19.5056(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1839.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1258
_refine_ls_abs_structure_Flack   ?

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
C1 C 0.8021(4) 0.22239(13) 0.81020(10) 0.0643(5) Uani 1 1 d . . .
H1 H 0.6548 0.2521 0.8054 0.077 Uiso 1 1 calc R . .
C2 C 0.7482(4) 0.13439(13) 0.82841(10) 0.0667(5) Uani 1 1 d . . .
H2A H 0.7639 0.1255 0.8773 0.080 Uiso 1 1 calc R . .
H2B H 0.5908 0.1201 0.8146 0.080 Uiso 1 1 calc R . .
N3 N 0.9194(4) 0.08679(9) 0.79060(7) 0.0600(4) Uani 1 1 d . . .
C4 C 0.9248(4) 0.12377(11) 0.72253(8) 0.0594(4) Uani 1 1 d . . .
H4 H 0.7819 0.1089 0.6979 0.071 Uiso 1 1 calc R . .
C5 C 1.1345(5) 0.09709(14) 0.68043(10) 0.0717(6) Uani 1 1 d . . .
H5A H 1.2756 0.1189 0.7009 0.086 Uiso 1 1 calc R . .
H5B H 1.1453 0.0383 0.6813 0.086 Uiso 1 1 calc R . .
O6 O 1.1181(4) 0.12390(10) 0.61119(7) 0.0804(5) Uani 1 1 d . . .
C7 C 1.1336(6) 0.20968(14) 0.60212(11) 0.0800(7) Uani 1 1 d . . .
H7A H 1.1938 0.2207 0.5566 0.096 Uiso 1 1 calc R . .
H7B H 1.2449 0.2312 0.6349 0.096 Uiso 1 1 calc R . .
C8 C 0.9048(6) 0.25399(13) 0.61076(10) 0.0777(6) Uani 1 1 d . . .
H8A H 0.9251 0.3086 0.5930 0.093 Uiso 1 1 calc R . .
H8B H 0.7902 0.2273 0.5819 0.093 Uiso 1 1 calc R . .
C9 C 0.8036(5) 0.26087(13) 0.68103(11) 0.0740(6) Uani 1 1 d . . .
O9 O 0.6271(6) 0.29939(18) 0.69018(12) 0.1294(11) Uani 1 1 d . . .
C10 C 0.9173(2) 0.21479(6) 0.73923(4) 0.0609(4) Uani 1 1 d . . .
H10 H 1.0786 0.2340 0.7433 0.073 Uiso 1 1 calc R . .
C11 C 0.9595(2) 0.26815(6) 0.86055(4) 0.0653(5) Uani 1 1 d R . .
C12 C 0.9141(2) 0.34930(6) 0.87508(4) 0.0845(7) Uani 1 1 d R . .
H12 H 0.7866 0.3751 0.8551 0.101 Uiso 1 1 calc R . .
C13 C 1.0594(2) 0.39193(6) 0.91940(4) 0.0948(9) Uani 1 1 d R . .
H13 H 1.0291 0.4462 0.9291 0.114 Uiso 1 1 calc R . .
C14 C 1.2501(2) 0.35342(6) 0.94920(4) 0.0973(10) Uani 1 1 d R . .
H14 H 1.3473 0.3819 0.9788 0.117 Uiso 1 1 calc R . .
C15 C 1.2955(2) 0.27227(6) 0.93467(4) 0.0912(8) Uani 1 1 d R . .
H15 H 1.4230 0.2465 0.9546 0.109 Uiso 1 1 calc R . .
C16 C 1.1501(2) 0.22964(6) 0.89035(4) 0.0804(6) Uani 1 1 d R . .
H16 H 1.1805 0.1754 0.8806 0.097 Uiso 1 1 calc R . .
C31 C 0.8926(2) -0.00006(5) 0.79425(4) 0.0678(5) Uani 1 1 d . . .
H31 H 1.0305 -0.0234 0.7720 0.081 Uiso 1 1 calc R . .
C32 C 0.8951(2) -0.03039(5) 0.86783(4) 0.0638(5) Uani 1 1 d R . .
C33 C 0.7057(2) -0.06704(5) 0.89990(4) 0.0716(5) Uani 1 1 d R . .
H33 H 0.5711 -0.0785 0.8750 0.086 Uiso 1 1 calc R . .
C34 C 0.7174(2) -0.08662(5) 0.96916(4) 0.0811(7) Uani 1 1 d R . .
H34 H 0.5907 -0.1111 0.9906 0.097 Uiso 1 1 calc R . .
C35 C 0.9185(2) -0.06953(5) 1.00636(4) 0.0809(7) Uani 1 1 d R . .
H35 H 0.9263 -0.0826 1.0527 0.097 Uiso 1 1 calc R . .
C36 C 1.1079(2) -0.03287(5) 0.97430(4) 0.0798(6) Uani 1 1 d R . .
H36 H 1.2425 -0.0214 0.9992 0.096 Uiso 1 1 calc R . .
C37 C 1.0962(2) -0.01330(5) 0.90503(4) 0.0710(5) Uani 1 1 d R . .
H37 H 1.2230 0.0112 0.8836 0.085 Uiso 1 1 calc R . .
C38 C 0.6746(6) -0.03379(14) 0.75421(12) 0.0859(8) Uani 1 1 d . . .
H38A H 0.5345 -0.0114 0.7735 0.129 Uiso 1 1 calc R . .
H38B H 0.6706 -0.0919 0.7580 0.129 Uiso 1 1 calc R . .
H38C H 0.6859 -0.0187 0.7068 0.129 Uiso 1 1 calc 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
C1 C2 1.523(3) . ?
C1 C11 1.531(2) . ?
C1 C10 1.539(2) . ?
C1 H1 0.9800 . ?
C2 N3 1.456(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C31 1.4398(17) . ?
N3 C4 1.461(2) . ?
C4 C5 1.520(3) . ?
C4 C10 1.534(2) . ?
C4 H4 0.9800 . ?
C5 O6 1.424(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O6 C7 1.426(3) . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.493(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O9 1.207(4) . ?
C9 C10 1.513(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.3902 . ?
C11 C16 1.3903 . ?
C12 C13 1.3903 . ?
C12 H12 0.9300 . ?
C13 C14 1.3902 . ?
C13 H13 0.9300 . ?
C14 C15 1.3902 . ?
C14 H14 0.9300 . ?
C15 C16 1.3904 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C32 1.5197 . ?
C31 C38 1.574(3) . ?
C31 H31 0.9800 . ?
C32 C33 1.3902 . ?
C32 C37 1.3903 . ?
C33 C34 1.3906 . ?
C33 H33 0.9300 . ?
C34 C35 1.3903 . ?
C34 H34 0.9300 . ?
C35 C36 1.3902 . ?
C35 H35 0.9300 . ?
C36 C37 1.3906 . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C2 C1 C11 115.95(16) . . ?
C2 C1 C10 102.66(14) . . ?
C11 C1 C10 111.38(16) . . ?
C2 C1 H1 108.9 . . ?
C11 C1 H1 108.9 . . ?
C10 C1 H1 108.9 . . ?
N3 C2 C1 104.92(17) . . ?
N3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
N3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C31 N3 C2 115.96(16) . . ?
C31 N3 C4 117.44(12) . . ?
C2 N3 C4 104.50(15) . . ?
N3 C4 C5 112.81(18) . . ?
N3 C4 C10 102.32(12) . . ?
C5 C4 C10 114.80(16) . . ?
N3 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C10 C4 H4 108.9 . . ?
O6 C5 C4 111.8(2) . . ?
O6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
O6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C5 O6 C7 114.87(16) . . ?
O6 C7 C8 114.2(2) . . ?
O6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
O6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 118.5(2) . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
O9 C9 C8 120.1(2) . . ?
O9 C9 C10 120.9(2) . . ?
C8 C9 C10 118.9(2) . . ?
C9 C10 C4 110.04(12) . . ?
C9 C10 C1 116.73(15) . . ?
C4 C10 C1 106.42(12) . . ?
C9 C10 H10 107.8 . . ?
C4 C10 H10 107.8 . . ?
C1 C10 H10 107.8 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C1 119.57(9) . . ?
C16 C11 C1 120.42(9) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.0 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N3 C31 C32 111.83(7) . . ?
N3 C31 C38 114.25(13) . . ?
C32 C31 C38 111.11(10) . . ?
N3 C31 H31 106.4 . . ?
C32 C31 H31 106.4 . . ?
C38 C31 H31 106.4 . . ?
C33 C32 C37 120.0 . . ?
C33 C32 C31 124.1 . . ?
C37 C32 C31 115.7 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C32 C37 C36 120.0 . . ?
C32 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C31 C38 H38A 109.5 . . ?
C31 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C31 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
C11 C1 C2 N3 -95.31(19) . . . . ?
C10 C1 C2 N3 26.3(2) . . . . ?
C1 C2 N3 C31 -174.59(15) . . . . ?
C1 C2 N3 C4 -43.6(2) . . . . ?
C31 N3 C4 C5 -64.3(3) . . . . ?
C2 N3 C4 C5 165.62(18) . . . . ?
C31 N3 C4 C10 171.81(15) . . . . ?
C2 N3 C4 C10 41.7(2) . . . . ?
N3 C4 C5 O6 171.19(17) . . . . ?
C10 C4 C5 O6 -72.1(2) . . . . ?
C4 C5 O6 C7 67.2(3) . . . . ?
C5 O6 C7 C8 -85.0(3) . . . . ?
O6 C7 C8 C9 71.2(3) . . . . ?
C7 C8 C9 O9 176.3(3) . . . . ?
C7 C8 C9 C10 -7.4(3) . . . . ?
O9 C9 C10 C4 119.1(3) . . . . ?
C8 C9 C10 C4 -57.2(3) . . . . ?
O9 C9 C10 C1 -2.2(3) . . . . ?
C8 C9 C10 C1 -178.5(2) . . . . ?
N3 C4 C10 C9 -151.78(18) . . . . ?
C5 C4 C10 C9 85.7(2) . . . . ?
N3 C4 C10 C1 -24.4(2) . . . . ?
C5 C4 C10 C1 -146.98(16) . . . . ?
C2 C1 C10 C9 122.35(18) . . . . ?
C11 C1 C10 C9 -112.93(17) . . . . ?
C2 C1 C10 C4 -0.9(2) . . . . ?
C11 C1 C10 C4 123.81(14) . . . . ?
C2 C1 C11 C12 -141.58(14) . . . . ?
C10 C1 C11 C12 101.53(13) . . . . ?
C2 C1 C11 C16 40.03(19) . . . . ?
C10 C1 C11 C16 -76.86(14) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C1 C11 C12 C13 -178.40(10) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C1 C11 C16 C15 178.38(10) . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C2 N3 C31 C32 -56.73(17) . . . . ?
C4 N3 C31 C38 -53.9(2) . . . . ?
N3 C31 C32 C33 115.28(10) . . . . ?
C38 C31 C32 C33 -13.70(12) . . . . ?
N3 C31 C32 C37 -59.44(10) . . . . ?
C38 C31 C32 C37 171.59(12) . . . . ?
C37 C32 C33 C34 0.0 . . . . ?
C31 C32 C33 C34 -174.5 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C33 C32 C37 C36 0.0 . . . . ?
C31 C32 C37 C36 174.9 . . . . ?
C35 C36 C37 C32 0.0 . . . . ?


##########################################################################
_audit_creation_method           SHELXL97

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 0.0000 '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'
O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_measurement_reflns_used    13080
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      71.19

_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '3493 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2085
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         71.88
_reflns_number_total             2085
_reflns_number_gt                1849
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X--AREA (STOE & CIE, 2012)'
_computing_cell_refinement       'X--AREA (STOE & CIE, 2012)'
_computing_data_reduction        'X--AREA (STOE & CIE, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep--3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0795P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         2085
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        71.88
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_yur102
_audit_block_doi                 10.5517/cc106c3p
_database_code_depnum_ccdc_archive 'CCDC 929631'
_audit_update_record             
;
2013-03-17 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
;
(3RS,3aSR,8aRS)-1-benzyl-3-phenylhexahydro-1H-oxepino[3,4-b]pyrrol-
4(2H)-one hydrobromide salt
;
_chemical_melting_point_gt       493
_chemical_melting_point_lt       498 # (decomp).
_chemical_formula_moiety         'C21 H24 N O2, Br'
_chemical_formula_sum            'C21 H24 Br N O2'
_chemical_formula_weight         402.31

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       EtOH--H2O
_exptl_crystal_density_diffrn    1.326

_cell_length_a                   12.3577(4)
_cell_length_b                   7.09170(10)
_cell_length_c                   23.2830(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.081(3)
_cell_angle_gamma                90.00
_cell_volume                     2014.88(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1000

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
Br1 Br 0.88864(4) 1.21867(6) 0.919264(19) 0.06991(17) Uani 1 1 d . . .
C1 C 0.7425(3) 0.7666(5) 0.95225(16) 0.0581(9) Uani 1 1 d . . .
H1 H 0.7291 0.9018 0.9460 0.070 Uiso 1 1 calc R . .
C2 C 0.8654(3) 0.7360(6) 0.96879(16) 0.0607(10) Uani 1 1 d . . .
H2A H 0.8967 0.8241 0.9987 0.073 Uiso 1 1 calc R . .
H2B H 0.8813 0.6084 0.9826 0.073 Uiso 1 1 calc R . .
N3 N 0.9081(2) 0.7707(4) 0.91368(13) 0.0501(7) Uani 1 1 d . . .
H3 H 0.908(3) 0.903(7) 0.9073(16) 0.075 Uiso 1 1 d . . .
C4 C 0.8234(3) 0.6967(5) 0.86462(15) 0.0510(8) Uani 1 1 d . . .
H4 H 0.8478 0.5747 0.8516 0.061 Uiso 1 1 calc R . .
C5 C 0.8122(3) 0.8367(5) 0.81402(15) 0.0588(9) Uani 1 1 d . . .
H5A H 0.7701 0.9451 0.8231 0.071 Uiso 1 1 calc R . .
H5B H 0.8843 0.8805 0.8087 0.071 Uiso 1 1 calc R . .
O6 O 0.7592(2) 0.7513(4) 0.76153(11) 0.0635(7) Uani 1 1 d . . .
C7 C 0.6437(3) 0.7724(6) 0.75269(18) 0.0662(10) Uani 1 1 d . . .
H7A H 0.6142 0.7375 0.7130 0.079 Uiso 1 1 calc R . .
H7B H 0.6256 0.9036 0.7580 0.079 Uiso 1 1 calc R . .
C8 C 0.5907(3) 0.6516(7) 0.79421(18) 0.0751(12) Uani 1 1 d . . .
H8A H 0.5121 0.6477 0.7817 0.090 Uiso 1 1 calc R . .
H8B H 0.6186 0.5238 0.7942 0.090 Uiso 1 1 calc R . .
C9 C 0.6153(3) 0.7326(6) 0.85481(17) 0.0607(10) Uani 1 1 d . . .
O9 O 0.5554(2) 0.8467(5) 0.87182(14) 0.0940(10) Uani 1 1 d . . .
C10 C 0.7187(3) 0.6670(5) 0.89325(15) 0.0509(8) Uani 1 1 d . . .
H10 H 0.7114 0.5317 0.9004 0.061 Uiso 1 1 calc R . .
C11 C 0.6795(3) 0.7011(6) 0.99925(18) 0.0631(10) Uani 1 1 d . . .
C12 C 0.6813(4) 0.5142(7) 1.0176(2) 0.0825(13) Uani 1 1 d . . .
H12 H 0.7171 0.4237 0.9986 0.099 Uiso 1 1 calc R . .
C13 C 0.6304(4) 0.4626(9) 1.0636(2) 0.1017(17) Uani 1 1 d . . .
H13 H 0.6319 0.3376 1.0758 0.122 Uiso 1 1 calc R . .
C14 C 0.5778(5) 0.5951(12) 1.0915(2) 0.112(2) Uani 1 1 d . . .
H14 H 0.5427 0.5595 1.1223 0.134 Uiso 1 1 calc R . .
C15 C 0.5762(5) 0.7780(10) 1.0747(3) 0.1086(19) Uani 1 1 d . . .
H15 H 0.5419 0.8674 1.0949 0.130 Uiso 1 1 calc R . .
C16 C 0.6251(4) 0.8337(7) 1.0278(2) 0.0840(14) Uani 1 1 d . . .
H16 H 0.6214 0.9588 1.0156 0.101 Uiso 1 1 calc R . .
C31 C 1.0222(3) 0.6903(5) 0.91708(16) 0.0584(9) Uani 1 1 d . . .
H31A H 1.0188 0.5541 0.9204 0.070 Uiso 1 1 calc R . .
H31B H 1.0679 0.7378 0.9518 0.070 Uiso 1 1 calc R . .
C32 C 1.0742(3) 0.7407(6) 0.8643(2) 0.0643(11) Uani 1 1 d . . .
C33 C 1.1198(4) 0.9182(7) 0.8604(2) 0.0871(14) Uani 1 1 d . . .
H33 H 1.1202 1.0049 0.8904 0.105 Uiso 1 1 calc R . .
C34 C 1.1653(4) 0.9653(9) 0.8110(3) 0.111(2) Uani 1 1 d . . .
H34 H 1.1984 1.0822 0.8087 0.133 Uiso 1 1 calc R . .
C35 C 1.1614(5) 0.8404(12) 0.7661(3) 0.119(2) Uani 1 1 d . . .
H35 H 1.1903 0.8740 0.7330 0.143 Uiso 1 1 calc R . .
C36 C 1.1148(4) 0.6644(12) 0.7694(3) 0.116(2) Uani 1 1 d . . .
H36 H 1.1125 0.5791 0.7389 0.139 Uiso 1 1 calc R . .
C37 C 1.0713(3) 0.6167(8) 0.8190(2) 0.0852(14) Uani 1 1 d . . .
H37 H 1.0398 0.4985 0.8214 0.102 Uiso 1 1 calc 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
C1 C11 1.512(5) . ?
C1 C2 1.522(5) . ?
C1 C10 1.531(5) . ?
C1 H1 0.9800 . ?
C2 N3 1.483(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C4 1.516(4) . ?
N3 C31 1.512(4) . ?
N3 H3 0.95(5) . ?
C4 C5 1.530(5) . ?
C4 C10 1.560(4) . ?
C4 H4 0.9800 . ?
C5 O6 1.427(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O6 C7 1.418(4) . ?
C7 C8 1.515(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O9 1.206(4) . ?
C9 C10 1.513(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.392(6) . ?
C11 C16 1.385(5) . ?
C12 C13 1.377(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C32 1.517(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.388(6) . ?
C32 C37 1.370(6) . ?
C33 C34 1.398(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.366(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(7) . ?
C36 H36 0.9300 . ?
C37 H37 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
C11 C1 C2 112.3(3) . . ?
C11 C1 C10 117.4(3) . . ?
C2 C1 C10 101.7(3) . . ?
C11 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C10 C1 H1 108.3 . . ?
N3 C2 C1 103.6(3) . . ?
N3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
N3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C2 N3 C4 107.3(3) . . ?
C2 N3 C31 110.4(3) . . ?
C4 N3 C31 115.9(3) . . ?
C2 N3 H3 108(2) . . ?
C4 N3 H3 104(2) . . ?
C31 N3 H3 111(2) . . ?
N3 C4 C5 108.9(3) . . ?
N3 C4 C10 104.2(3) . . ?
C5 C4 C10 115.9(3) . . ?
N3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C10 C4 H4 109.2 . . ?
O6 C5 C4 111.0(3) . . ?
O6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
O6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 O6 C5 113.3(3) . . ?
O6 C7 C8 112.0(3) . . ?
O6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
O6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 109.7(4) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O9 C9 C8 121.2(4) . . ?
O9 C9 C10 121.2(3) . . ?
C8 C9 C10 117.6(3) . . ?
C9 C10 C1 114.4(3) . . ?
C9 C10 C4 112.7(3) . . ?
C1 C10 C4 105.5(3) . . ?
C9 C10 H10 108.0 . . ?
C1 C10 H10 108.0 . . ?
C4 C10 H10 108.0 . . ?
C12 C11 C16 119.0(4) . . ?
C12 C11 C1 121.9(4) . . ?
C16 C11 C1 118.9(4) . . ?
C11 C12 C13 120.3(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 119.3(5) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
N3 C31 C32 112.3(3) . . ?
N3 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
N3 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C37 119.6(4) . . ?
C33 C32 C31 119.6(4) . . ?
C37 C32 C31 120.7(4) . . ?
C32 C33 C34 119.3(5) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 120.4(6) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 120.4(6) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.1(6) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C36 C37 C32 121.1(6) . . ?
C36 C37 H37 119.4 . . ?
C32 C37 H37 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 N3 168.7(3) . . . . ?
C10 C1 C2 N3 42.3(4) . . . . ?
C1 C2 N3 C4 -35.7(4) . . . . ?
C1 C2 N3 C31 -162.8(3) . . . . ?
C2 N3 C4 C5 138.5(3) . . . . ?
C31 N3 C4 C5 -97.7(3) . . . . ?
C2 N3 C4 C10 14.3(3) . . . . ?
C31 N3 C4 C10 138.1(3) . . . . ?
N3 C4 C5 O6 163.1(3) . . . . ?
C10 C4 C5 O6 -79.9(4) . . . . ?
C4 C5 O6 C7 90.4(4) . . . . ?
C5 O6 C7 C8 -71.6(4) . . . . ?
O6 C7 C8 C9 71.8(4) . . . . ?
C7 C8 C9 O9 90.3(4) . . . . ?
C7 C8 C9 C10 -89.0(4) . . . . ?
O9 C9 C10 C1 -3.8(5) . . . . ?
C8 C9 C10 C1 175.6(3) . . . . ?
O9 C9 C10 C4 -124.2(4) . . . . ?
C8 C9 C10 C4 55.1(4) . . . . ?
C11 C1 C10 C9 79.3(4) . . . . ?
C2 C1 C10 C9 -157.7(3) . . . . ?
C11 C1 C10 C4 -156.3(3) . . . . ?
C2 C1 C10 C4 -33.3(4) . . . . ?
N3 C4 C10 C9 137.8(3) . . . . ?
C5 C4 C10 C9 18.3(5) . . . . ?
N3 C4 C10 C1 12.4(4) . . . . ?
C5 C4 C10 C1 -107.2(3) . . . . ?
C2 C1 C11 C12 -61.0(5) . . . . ?
C10 C1 C11 C12 56.5(5) . . . . ?
C2 C1 C11 C16 114.2(4) . . . . ?
C10 C1 C11 C16 -128.4(4) . . . . ?
C16 C11 C12 C13 -0.5(7) . . . . ?
C1 C11 C12 C13 174.7(4) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C15 -0.8(9) . . . . ?
C13 C14 C15 C16 2.0(10) . . . . ?
C14 C15 C16 C11 -2.3(8) . . . . ?
C12 C11 C16 C15 1.6(7) . . . . ?
C1 C11 C16 C15 -173.7(4) . . . . ?
C2 N3 C31 C32 -173.8(3) . . . . ?
C4 N3 C31 C32 64.0(4) . . . . ?
N3 C31 C32 C33 79.4(5) . . . . ?
N3 C31 C32 C37 -97.1(5) . . . . ?
C37 C32 C33 C34 -2.0(7) . . . . ?
C31 C32 C33 C34 -178.5(4) . . . . ?
C32 C33 C34 C35 2.3(8) . . . . ?
C33 C34 C35 C36 -1.5(10) . . . . ?
C34 C35 C36 C37 0.4(9) . . . . ?
C35 C36 C37 C32 -0.1(8) . . . . ?
C33 C32 C37 C36 0.9(7) . . . . ?
C31 C32 C37 C36 177.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 Br1 0.95(5) 2.28(5) 3.190(3) 162(3) .

############################################################################

_audit_creation_method           SHELXL97

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'
O O 0.0492 0.0322 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_measurement_reflns_used    16692
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      71.38

_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '3493 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3925
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.1544
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         71.73
_reflns_number_total             3925
_reflns_number_gt                2156
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'STOE X--AREA (Stoe & Cie, 2012)'
_computing_cell_refinement       'STOE X--AREA (Stoe & Cie, 2012)'
_computing_data_reduction        'STOE X--RED (Stoe & Cie, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0182P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3925
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.740
_refine_ls_restrained_S_all      0.740
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        71.73
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_yur100
_audit_block_doi                 10.5517/cc106c1m
_database_code_depnum_ccdc_archive 'CCDC 929629'
_audit_update_record             
;
2013-03-17 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
;
(3R,3aS,8aR)-3-phenyl-1-((R)-1-phenylethyl)hexahydro-1H-
oxepino[3,4-b]pyrrol-4(2H)-one
;
_chemical_melting_point_gt       409
_chemical_melting_point_lt       410
_chemical_formula_moiety         'C22 H25 N O2'
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_chemical_absolute_configuration unk

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       'Ethanol--Methyl / tert--butyl ether'
_exptl_crystal_density_diffrn    1.194

_cell_length_a                   5.6234(2)
_cell_length_b                   15.5257(5)
_cell_length_c                   21.3791(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1866.55(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0859
_refine_ls_abs_structure_Flack   ?

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
C1 C 1.1167(6) 0.88089(18) 0.24403(10) 0.0403(7) Uani 1 1 d . . .
H1 H 1.2772 0.8971 0.2306 0.048 Uiso 1 1 calc R . .
C2 C 0.9372(6) 0.93282(17) 0.20630(10) 0.0449(8) Uani 1 1 d . . .
H2A H 0.7801 0.9291 0.2248 0.054 Uiso 1 1 calc R . .
H2B H 0.9838 0.9929 0.2041 0.054 Uiso 1 1 calc R . .
N3 N 0.9400(5) 0.89297(14) 0.14373(8) 0.0447(7) Uani 1 1 d . . .
C4 C 0.9723(7) 0.79959(17) 0.15344(11) 0.0477(8) Uani 1 1 d . . .
H4 H 0.8170 0.7713 0.1504 0.057 Uiso 1 1 calc R . .
C5 C 1.1363(8) 0.76164(19) 0.10456(12) 0.0638(10) Uani 1 1 d . . .
H5A H 1.1015 0.7874 0.0643 0.077 Uiso 1 1 calc R . .
H5B H 1.2997 0.7755 0.1152 0.077 Uiso 1 1 calc R . .
O6 O 1.1111(6) 0.67039(14) 0.10006(9) 0.0762(8) Uani 1 1 d . . .
C7 C 1.2695(10) 0.6248(2) 0.13856(16) 0.0949(16) Uani 1 1 d . . .
H7A H 1.4305 0.6422 0.1282 0.114 Uiso 1 1 calc R . .
H7B H 1.2552 0.5639 0.1292 0.114 Uiso 1 1 calc R . .
C8 C 1.2336(9) 0.6370(2) 0.20636(13) 0.0726(12) Uani 1 1 d . . .
H8A H 1.3418 0.5997 0.2291 0.087 Uiso 1 1 calc R . .
H8B H 1.0725 0.6204 0.2172 0.087 Uiso 1 1 calc R . .
C9 C 1.2754(8) 0.7297(2) 0.22606(12) 0.0530(9) Uani 1 1 d . . .
O9 O 1.4712(5) 0.75525(17) 0.24234(10) 0.0702(7) Uani 1 1 d . . .
C10 C 1.0618(3) 0.79082(7) 0.21905(5) 0.0456(8) Uani 1 1 d . . .
H10 H 0.9316 0.7673 0.2443 0.055 Uiso 1 1 calc R . .
C11 C 1.0965(3) 0.89589(7) 0.31478(5) 0.0399(7) Uani 1 1 d R . .
C12 C 0.9001(3) 0.86541(7) 0.34749(5) 0.0503(8) Uani 1 1 d R . .
H12 H 0.7802 0.8360 0.3265 0.060 Uiso 1 1 calc R . .
C13 C 0.8830(3) 0.87885(7) 0.41161(5) 0.0605(9) Uani 1 1 d R . .
H13 H 0.7516 0.8585 0.4335 0.073 Uiso 1 1 calc R . .
C14 C 1.0622(3) 0.92278(7) 0.44303(5) 0.0656(11) Uani 1 1 d R . .
H14 H 1.0508 0.9318 0.4859 0.079 Uiso 1 1 calc R . .
C15 C 1.2586(3) 0.95327(7) 0.41032(5) 0.0673(10) Uani 1 1 d R . .
H15 H 1.3785 0.9827 0.4313 0.081 Uiso 1 1 calc R . .
C16 C 1.2757(3) 0.93982(7) 0.34620(5) 0.0558(9) Uani 1 1 d R . .
H16 H 1.4071 0.9602 0.3243 0.067 Uiso 1 1 calc R . .
C31 C 0.7269(3) 0.91730(9) 0.10910(5) 0.0533(9) Uani 1 1 d . . .
H31 H 0.5894 0.8971 0.1331 0.064 Uiso 1 1 calc R . .
C32 C 0.7063(3) 1.01475(9) 0.10357(5) 0.0507(8) Uani 1 1 d R . .
C33 C 0.5082(3) 1.05727(9) 0.12724(5) 0.0622(9) Uani 1 1 d R . .
H33 H 0.3864 1.0261 0.1460 0.075 Uiso 1 1 calc R . .
C34 C 0.4923(3) 1.14641(9) 0.12285(5) 0.0761(11) Uani 1 1 d R . .
H34 H 0.3598 1.1749 0.1387 0.091 Uiso 1 1 calc R . .
C35 C 0.6744(3) 1.19303(9) 0.09481(5) 0.0778(12) Uani 1 1 d R . .
H35 H 0.6637 1.2527 0.0919 0.093 Uiso 1 1 calc R . .
C36 C 0.8724(3) 1.15052(9) 0.07114(5) 0.0768(12) Uani 1 1 d R . .
H36 H 0.9943 1.1817 0.0524 0.092 Uiso 1 1 calc R . .
C37 C 0.8884(3) 1.06138(9) 0.07553(5) 0.0597(10) Uani 1 1 d R . .
H37 H 1.0209 1.0329 0.0597 0.072 Uiso 1 1 calc R . .
C38 C 0.7095(8) 0.8777(2) 0.04409(12) 0.0726(12) Uani 1 1 d . . .
H38A H 0.8373 0.8987 0.0186 0.109 Uiso 1 1 calc R . .
H38B H 0.5602 0.8932 0.0255 0.109 Uiso 1 1 calc R . .
H38C H 0.7200 0.8161 0.0473 0.109 Uiso 1 1 calc 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
C1 C2 1.523(4) . ?
C1 C10 1.528(3) . ?
C1 C11 1.535(2) . ?
C1 H1 0.9800 . ?
C2 N3 1.474(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C31 1.459(3) . ?
N3 C4 1.476(3) . ?
C4 C10 1.497(3) . ?
C4 C5 1.513(4) . ?
C4 H4 0.9800 . ?
C5 O6 1.427(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O6 C7 1.404(5) . ?
C7 C8 1.476(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O9 1.221(4) . ?
C9 C10 1.538(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13 0.9300 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C32 1.5220 . ?
C31 C38 1.523(3) . ?
C31 H31 0.9800 . ?
C32 C33 1.3900 . ?
C32 C37 1.3900 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 C37 1.3900 . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C2 C1 C10 99.52(19) . . ?
C2 C1 C11 113.1(2) . . ?
C10 C1 C11 117.92(18) . . ?
C2 C1 H1 108.6 . . ?
C10 C1 H1 108.6 . . ?
C11 C1 H1 108.6 . . ?
N3 C2 C1 104.5(2) . . ?
N3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
N3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C31 N3 C4 115.3(2) . . ?
C31 N3 C2 110.1(2) . . ?
C4 N3 C2 106.62(18) . . ?
N3 C4 C10 105.23(18) . . ?
N3 C4 C5 111.1(2) . . ?
C10 C4 C5 114.0(3) . . ?
N3 C4 H4 108.8 . . ?
C10 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
O6 C5 C4 111.9(3) . . ?
O6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
O6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 O6 C5 113.4(3) . . ?
O6 C7 C8 115.1(4) . . ?
O6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
O6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 111.9(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O9 C9 C8 121.8(4) . . ?
O9 C9 C10 122.1(3) . . ?
C8 C9 C10 115.9(3) . . ?
C4 C10 C1 108.19(15) . . ?
C4 C10 C9 114.20(18) . . ?
C1 C10 C9 111.9(2) . . ?
C4 C10 H10 107.4 . . ?
C1 C10 H10 107.4 . . ?
C9 C10 H10 107.4 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C1 120.19(13) . . ?
C16 C11 C1 119.81(13) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N3 C31 C32 111.06(10) . . ?
N3 C31 C38 114.3(2) . . ?
C32 C31 C38 109.01(13) . . ?
N3 C31 H31 107.4 . . ?
C32 C31 H31 107.4 . . ?
C38 C31 H31 107.4 . . ?
C33 C32 C37 120.0 . . ?
C33 C32 C31 120.3 . . ?
C37 C32 C31 119.7 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C32 120.0 . . ?
C36 C37 H37 120.0 . . ?
C32 C37 H37 120.0 . . ?
C31 C38 H38A 109.5 . . ?
C31 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C31 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
C10 C1 C2 N3 -39.1(3) . . . . ?
C11 C1 C2 N3 -165.1(2) . . . . ?
C1 C2 N3 C31 161.9(2) . . . . ?
C1 C2 N3 C4 36.2(3) . . . . ?
C31 N3 C4 C10 -139.50(19) . . . . ?
C2 N3 C4 C10 -17.0(3) . . . . ?
C31 N3 C4 C5 96.6(3) . . . . ?
C2 N3 C4 C5 -140.9(3) . . . . ?
N3 C4 C5 O6 -161.2(3) . . . . ?
C10 C4 C5 O6 80.1(3) . . . . ?
C4 C5 O6 C7 -92.0(4) . . . . ?
C5 O6 C7 C8 65.2(5) . . . . ?
O6 C7 C8 C9 -63.5(6) . . . . ?
C7 C8 C9 O9 -90.1(5) . . . . ?
C7 C8 C9 C10 85.0(5) . . . . ?
N3 C4 C10 C1 -8.4(3) . . . . ?
C5 C4 C10 C1 113.6(2) . . . . ?
N3 C4 C10 C9 -133.7(3) . . . . ?
C5 C4 C10 C9 -11.7(3) . . . . ?
C2 C1 C10 C4 29.1(3) . . . . ?
C11 C1 C10 C4 151.7(2) . . . . ?
C2 C1 C10 C9 155.73(19) . . . . ?
C11 C1 C10 C9 -81.6(3) . . . . ?
O9 C9 C10 C4 114.7(3) . . . . ?
C8 C9 C10 C4 -60.4(3) . . . . ?
O9 C9 C10 C1 -8.6(3) . . . . ?
C8 C9 C10 C1 176.3(2) . . . . ?
C2 C1 C11 C12 69.6(2) . . . . ?
C10 C1 C11 C12 -45.9(3) . . . . ?
C2 C1 C11 C16 -110.7(2) . . . . ?
C10 C1 C11 C16 133.89(18) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C1 C11 C12 C13 179.75(13) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C1 C11 C16 C15 -179.75(13) . . . . ?
C4 N3 C31 C32 178.12(16) . . . . ?
C2 N3 C31 C32 57.5(2) . . . . ?
C4 N3 C31 C38 -58.1(3) . . . . ?
C2 N3 C31 C38 -178.7(2) . . . . ?
N3 C31 C32 C33 -121.03(11) . . . . ?
C38 C31 C32 C33 112.18(19) . . . . ?
N3 C31 C32 C37 58.02(11) . . . . ?
C38 C31 C32 C37 -68.77(19) . . . . ?
C37 C32 C33 C34 0.0 . . . . ?
C31 C32 C33 C34 179.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C32 0.0 . . . . ?
C33 C32 C37 C36 0.0 . . . . ?
C31 C32 C37 C36 -179.1 . . . . ?

##########################################################################

_audit_creation_method           SHELXL97

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 0.0000 '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'
O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_measurement_reflns_used    9725
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      70.08

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '3493 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2114
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.1423
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         71.23
_reflns_number_total             2114
_reflns_number_gt                1112
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X--AREA (STOE & CIE, 2012)'
_computing_cell_refinement       'X--AREA (STOE & CIE, 2012)'
_computing_data_reduction        'X--AREA (STOE & CIE, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep--3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         2114
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.549
_refine_ls_restrained_S_all      0.549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes
;

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        71.23
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_YUR107
_audit_block_doi                 10.5517/ccdc.csd.cc2344zd
_database_code_depnum_ccdc_archive 'CCDC 1940413'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Moscow State University, Chemistry Department
Russia
;
_audit_update_record             
;
2019-07-14 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
(3S,4R)-tert-butyl-4-hydroxy-3-((R)-phenylethylamino)-4-styrylpiperidine-1-carboxylate
_chemical_name_common            ?
_chemical_melting_point_gt       418
_chemical_melting_point_lt       420
_chemical_formula_moiety         'C26 H34 N2 O3'
_chemical_formula_sum            'C26 H34 N2 O3'
_chemical_formula_weight         422.55
_chemical_absolute_configuration unk

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_preparation       MTBE

_cell_length_a                   5.7669(2)
_cell_length_b                   13.5407(5)
_cell_length_c                   31.6039(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2467.88(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'x+1/2, -y+1/2, -z+'
'-x+, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1751

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
N1 N 0.5256(8) 0.8954(2) 0.76807(11) 0.0728(11) Uani 1 1 d . . . . .
C2 C 0.4065(9) 0.8565(3) 0.73128(13) 0.0724(12) Uani 1 1 d . . . . .
H2A H 0.2549 0.8870 0.7289 0.087 Uiso 1 1 calc R U . . .
H2B H 0.3845 0.7859 0.7346 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5439(9) 0.8763(3) 0.69150(14) 0.0712(12) Uani 1 1 d . . . . .
H3 H 0.4511 0.8550 0.6672 0.085 Uiso 1 1 calc R U . . .
C4 C 0.5936(9) 0.9887(2) 0.68679(14) 0.0735(12) Uani 1 1 d . . . . .
O41 O 0.3704(7) 1.0325(2) 0.68145(10) 0.0855(10) Uani 1 1 d . . . . .
H41 H 0.3765 1.0910 0.6880 0.128 Uiso 1 1 calc R U . . .
C5 C 0.7054(10) 1.0274(2) 0.72715(14) 0.0755(13) Uani 1 1 d . . . . .
H5A H 0.8604 1.0002 0.7296 0.091 Uiso 1 1 calc R U . . .
H5B H 0.7196 1.0987 0.7252 0.091 Uiso 1 1 calc R U . . .
C6 C 0.5703(11) 1.0018(3) 0.76592(14) 0.0805(14) Uani 1 1 d . . . . .
H6A H 0.6563 1.0222 0.7908 0.097 Uiso 1 1 calc R U . . .
H6B H 0.4241 1.0372 0.7657 0.097 Uiso 1 1 calc R U . . .
C11 C 0.6302(10) 0.8331(3) 0.79658(13) 0.0753(13) Uani 1 1 d . . . . .
O11 O 0.6094(7) 0.74416(18) 0.79510(9) 0.0856(10) Uani 1 1 d . . . . .
O12 O 0.7441(8) 0.8838(2) 0.82596(10) 0.0906(11) Uani 1 1 d . . . . .
C13 C 0.8780(12) 0.8343(3) 0.85935(16) 0.0881(15) Uani 1 1 d . . . . .
C14 C 0.988(2) 0.9186(5) 0.8820(2) 0.165(4) Uani 1 1 d . . . . .
H14A H 1.0816 0.8939 0.9049 0.247 Uiso 1 1 calc R U . . .
H14B H 1.0847 0.9549 0.8627 0.247 Uiso 1 1 calc R U . . .
H14C H 0.8703 0.9613 0.8931 0.247 Uiso 1 1 calc R U . . .
C15 C 0.7179(15) 0.7767(5) 0.88774(17) 0.116(2) Uani 1 1 d . . . . .
H15A H 0.8067 0.7446 0.9095 0.173 Uiso 1 1 calc R U . . .
H15B H 0.6079 0.8208 0.9005 0.173 Uiso 1 1 calc R U . . .
H15C H 0.6370 0.7279 0.8714 0.173 Uiso 1 1 calc R U . . .
C16 C 1.0541(14) 0.7667(5) 0.8395(2) 0.130(2) Uani 1 1 d . . . . .
H16A H 1.1416 0.7343 0.8613 0.195 Uiso 1 1 calc R U . . .
H16B H 0.9760 0.7180 0.8226 0.195 Uiso 1 1 calc R U . . .
H16C H 1.1569 0.8045 0.8219 0.195 Uiso 1 1 calc R U . . .
N31 N 0.7609(8) 0.82069(19) 0.69137(11) 0.0722(10) Uani 1 1 d . . . . .
H31 H 0.8575 0.8501 0.6771 0.108 Uiso 1 1 calc R U . . .
C32 C 0.7332(10) 0.7163(2) 0.67872(14) 0.0740(12) Uani 1 1 d . . . . .
H32 H 0.5931 0.6899 0.6921 0.089 Uiso 1 1 calc R U . . .
C33 C 0.9429(12) 0.6605(3) 0.6957(2) 0.1041(19) Uani 1 1 d . . . . .
H33A H 0.9309 0.5920 0.6880 0.156 Uiso 1 1 calc R U . . .
H33B H 1.0819 0.6878 0.6837 0.156 Uiso 1 1 calc R U . . .
H33C H 0.9480 0.6663 0.7259 0.156 Uiso 1 1 calc R U . . .
C34 C 0.7121(12) 0.7045(3) 0.63191(16) 0.0879(16) Uani 1 1 d . . . . .
C35 C 0.5486(16) 0.6425(5) 0.6147(2) 0.127(2) Uani 1 1 d . . . . .
H35 H 0.4433 0.6100 0.6321 0.153 Uiso 1 1 calc R U . . .
C36 C 0.541(3) 0.6287(8) 0.5712(3) 0.207(6) Uani 1 1 d . . . . .
H36 H 0.4378 0.5828 0.5601 0.249 Uiso 1 1 calc R U . . .
C37 C 0.672(4) 0.6766(8) 0.5459(3) 0.234(9) Uani 1 1 d . . . . .
H37 H 0.6521 0.6693 0.5169 0.281 Uiso 1 1 calc R U . . .
C38 C 0.848(4) 0.7415(8) 0.5616(3) 0.267(10) Uani 1 1 d . . . . .
H38 H 0.9461 0.7756 0.5433 0.320 Uiso 1 1 calc R U . . .
C39 C 0.867(2) 0.7513(6) 0.6052(2) 0.170(5) Uani 1 1 d . . . . .
H39 H 0.9856 0.7897 0.6166 0.204 Uiso 1 1 calc R U . . .
C42 C 0.7485(11) 1.0070(3) 0.64903(15) 0.0806(13) Uani 1 1 d . . . . .
H42 H 0.9042 0.9904 0.6518 0.097 Uiso 1 1 calc R U . . .
C43 C 0.6832(12) 1.0443(3) 0.61270(15) 0.0887(16) Uani 1 1 d . . . . .
H43 H 0.5275 1.0610 0.6100 0.106 Uiso 1 1 calc R U . . .
C44 C 0.8342(12) 1.0622(4) 0.57544(15) 0.0897(16) Uani 1 1 d . . . . .
C45 C 1.0422(15) 1.0137(4) 0.5694(2) 0.113(2) Uani 1 1 d . . . . .
H45 H 1.0931 0.9686 0.5895 0.135 Uiso 1 1 calc R U . . .
C46 C 1.1753(15) 1.0311(5) 0.5341(2) 0.121(2) Uani 1 1 d . . . . .
H46 H 1.3164 0.9987 0.5308 0.145 Uiso 1 1 calc R U . . .
C47 C 1.101(2) 1.0962(6) 0.5036(2) 0.136(3) Uani 1 1 d . . . . .
H47 H 1.1884 1.1074 0.4794 0.163 Uiso 1 1 calc R U . . .
C48 C 0.895(2) 1.1439(6) 0.5097(2) 0.136(3) Uani 1 1 d . . . . .
H48 H 0.8449 1.1892 0.4896 0.163 Uiso 1 1 calc R U . . .
C49 C 0.7595(16) 1.1266(4) 0.54504(16) 0.111(2) Uani 1 1 d . . . . .
H49 H 0.6179 1.1587 0.5481 0.133 Uiso 1 1 calc R U . . .


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
N1 C11 1.374(6) . ?
N1 C2 1.450(5) . ?
N1 C6 1.465(5) . ?
C2 C3 1.510(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N31 1.460(6) . ?
C3 C4 1.555(5) . ?
C3 H3 0.9800 . ?
C4 O41 1.427(6) . ?
C4 C42 1.512(7) . ?
C4 C5 1.523(6) . ?
O41 H41 0.8200 . ?
C5 C6 1.493(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 O11 1.212(5) . ?
C11 O12 1.328(5) . ?
O12 C13 1.469(6) . ?
C13 C14 1.491(8) . ?
C13 C15 1.506(9) . ?
C13 C16 1.505(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N31 C32 1.477(4) . ?
N31 H31 0.8200 . ?
C32 C34 1.493(6) . ?
C32 C33 1.523(8) . ?
C32 H32 0.9800 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.375(9) . ?
C34 C39 1.383(9) . ?
C35 C36 1.389(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.27(2) . ?
C36 H36 0.9300 . ?
C37 C38 1.43(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.391(11) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C42 C43 1.309(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.485(8) . ?
C43 H43 0.9300 . ?
C44 C49 1.367(8) . ?
C44 C45 1.381(9) . ?
C45 C46 1.374(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.375(11) . ?
C46 H46 0.9300 . ?
C47 C48 1.363(12) . ?
C47 H47 0.9300 . ?
C48 C49 1.384(11) . ?
C48 H48 0.9300 . ?
C49 H49 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
C11 N1 C2 120.7(3) . . ?
C11 N1 C6 123.8(4) . . ?
C2 N1 C6 113.8(3) . . ?
N1 C2 C3 110.8(4) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N31 C3 C2 111.1(3) . . ?
N31 C3 C4 110.3(4) . . ?
C2 C3 C4 110.5(3) . . ?
N31 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
O41 C4 C42 111.8(4) . . ?
O41 C4 C5 109.7(4) . . ?
C42 C4 C5 110.8(4) . . ?
O41 C4 C3 104.6(4) . . ?
C42 C4 C3 110.2(3) . . ?
C5 C4 C3 109.6(3) . . ?
C4 O41 H41 109.5 . . ?
C6 C5 C4 112.7(4) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 C5 111.0(3) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O11 C11 O12 126.1(4) . . ?
O11 C11 N1 122.8(4) . . ?
O12 C11 N1 111.0(3) . . ?
C11 O12 C13 121.8(3) . . ?
O12 C13 C14 102.8(4) . . ?
O12 C13 C15 110.0(5) . . ?
C14 C13 C15 111.8(6) . . ?
O12 C13 C16 109.4(5) . . ?
C14 C13 C16 112.2(7) . . ?
C15 C13 C16 110.3(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 N31 C32 113.7(4) . . ?
C3 N31 H31 109.5 . . ?
C32 N31 H31 112.9 . . ?
N31 C32 C34 112.3(3) . . ?
N31 C32 C33 107.1(4) . . ?
C34 C32 C33 111.1(4) . . ?
N31 C32 H32 108.7 . . ?
C34 C32 H32 108.7 . . ?
C33 C32 H32 108.7 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 118.8(6) . . ?
C35 C34 C32 120.9(5) . . ?
C39 C34 C32 120.1(6) . . ?
C34 C35 C36 119.7(10) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C37 C36 C35 122.2(13) . . ?
C37 C36 H36 118.9 . . ?
C35 C36 H36 118.9 . . ?
C36 C37 C38 121.1(9) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C39 C38 C37 117.1(11) . . ?
C39 C38 H38 121.4 . . ?
C37 C38 H38 121.4 . . ?
C34 C39 C38 120.7(10) . . ?
C34 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C43 C42 C4 125.8(6) . . ?
C43 C42 H42 117.1 . . ?
C4 C42 H42 117.1 . . ?
C42 C43 C44 126.1(6) . . ?
C42 C43 H43 116.9 . . ?
C44 C43 H43 116.9 . . ?
C49 C44 C45 118.6(6) . . ?
C49 C44 C43 118.5(6) . . ?
C45 C44 C43 122.8(5) . . ?
C46 C45 C44 121.1(6) . . ?
C46 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C45 C46 C47 120.2(8) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C48 C47 C46 118.5(8) . . ?
C48 C47 H47 120.8 . . ?
C46 C47 H47 120.8 . . ?
C47 C48 C49 121.7(8) . . ?
C47 C48 H48 119.2 . . ?
C49 C48 H48 119.2 . . ?
C44 C49 C48 119.8(8) . . ?
C44 C49 H49 120.1 . . ?
C48 C49 H49 120.1 . . ?

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
C11 N1 C2 C3 -107.6(5) . . . . ?
C6 N1 C2 C3 58.4(5) . . . . ?
N1 C2 C3 N31 66.8(4) . . . . ?
N1 C2 C3 C4 -56.0(5) . . . . ?
N31 C3 C4 O41 172.2(3) . . . . ?
C2 C3 C4 O41 -64.6(5) . . . . ?
N31 C3 C4 C42 51.9(5) . . . . ?
C2 C3 C4 C42 175.1(4) . . . . ?
N31 C3 C4 C5 -70.2(5) . . . . ?
C2 C3 C4 C5 53.0(6) . . . . ?
O41 C4 C5 C6 62.0(4) . . . . ?
C42 C4 C5 C6 -174.1(3) . . . . ?
C3 C4 C5 C6 -52.3(5) . . . . ?
C11 N1 C6 C5 109.0(5) . . . . ?
C2 N1 C6 C5 -56.5(6) . . . . ?
C4 C5 C6 N1 53.4(5) . . . . ?
C2 N1 C11 O11 -7.6(8) . . . . ?
C6 N1 C11 O11 -172.2(5) . . . . ?
C2 N1 C11 O12 175.2(4) . . . . ?
C6 N1 C11 O12 10.6(7) . . . . ?
O11 C11 O12 C13 5.1(8) . . . . ?
N1 C11 O12 C13 -177.8(5) . . . . ?
C11 O12 C13 C14 175.5(6) . . . . ?
C11 O12 C13 C15 -65.3(6) . . . . ?
C11 O12 C13 C16 56.0(7) . . . . ?
C2 C3 N31 C32 80.2(4) . . . . ?
C4 C3 N31 C32 -157.0(3) . . . . ?
C3 N31 C32 C34 78.8(6) . . . . ?
C3 N31 C32 C33 -158.9(4) . . . . ?
N31 C32 C34 C35 -135.9(6) . . . . ?
C33 C32 C34 C35 104.1(7) . . . . ?
N31 C32 C34 C39 48.2(8) . . . . ?
C33 C32 C34 C39 -71.7(7) . . . . ?
C39 C34 C35 C36 -0.5(13) . . . . ?
C32 C34 C35 C36 -176.3(8) . . . . ?
C34 C35 C36 C37 -5(2) . . . . ?
C35 C36 C37 C38 6(3) . . . . ?
C36 C37 C38 C39 -1(2) . . . . ?
C35 C34 C39 C38 4.5(14) . . . . ?
C32 C34 C39 C38 -179.5(10) . . . . ?
C37 C38 C39 C34 -3.7(19) . . . . ?
O41 C4 C42 C43 -10.2(6) . . . . ?
C5 C4 C42 C43 -132.9(4) . . . . ?
C3 C4 C42 C43 105.7(5) . . . . ?
C4 C42 C43 C44 -179.8(4) . . . . ?
C42 C43 C44 C49 -161.0(5) . . . . ?
C42 C43 C44 C45 21.6(8) . . . . ?
C49 C44 C45 C46 1.5(9) . . . . ?
C43 C44 C45 C46 178.9(5) . . . . ?
C44 C45 C46 C47 -1.3(10) . . . . ?
C45 C46 C47 C48 1.2(11) . . . . ?
C46 C47 C48 C49 -1.5(12) . . . . ?
C45 C44 C49 C48 -1.7(9) . . . . ?
C43 C44 C49 C48 -179.2(6) . . . . ?
C47 C48 C49 C44 1.8(11) . . . . ?

_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.8(6)

########################################################################### 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'
O O 0.0492 0.0322 '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'

_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.
;

_cell_measurement_reflns_used    8656
_cell_measurement_theta_min      3.551
_cell_measurement_theta_max      70.348

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.059
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D. (1983). Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9283
_exptl_absorpt_correction_T_max  0.9431

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_details      
'63 runs, 3113 frames, detector distance = 42 mm'
_diffrn_reflns_number            8656
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_av_R_equivalents  0.0713 # before absorption correction
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.551
_diffrn_reflns_theta_max         70.348
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4579
_reflns_number_gt                2491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.963

_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       'X--AREA       (STOE & CIE, 2012)'
_computing_cell_refinement       'X--AREA       (STOE & CIE, 2012)'
_computing_data_reduction        'X--AREA       (STOE & CIE, 2012)'
_computing_structure_solution    'SHELXS97      (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep--3      (Farrugia,   1997)'
_computing_publication_material  'WinGX         (Farrugia,   1999)'

_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)+(0.0932P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dixmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4579
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_restrained_S_all      0.848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_YUR104
_audit_block_doi                 10.5517/ccdc.csd.cc2344jy
_database_code_depnum_ccdc_archive 'CCDC 1940399'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Moscow State University, Chemistry Department
Russia
;
_audit_update_record             
;
2019-07-14 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
;
(3S,4R)-3-((R)-phenylethylamino)-4-styryltetrahydro-2H-pyran-4-ol hydrobromide 
;
_chemical_name_common            ?
_chemical_melting_point_gt       446
_chemical_melting_point_lt       448
_chemical_formula_moiety         'C21 H26 N O2, Br'
_chemical_formula_sum            'C21 H26 Br N O2'
_chemical_formula_weight         404.33
_chemical_absolute_configuration ad

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_preparation       'EtOH - MTBE'

_cell_length_a                   10.2800(4)
_cell_length_b                   10.8668(5)
_cell_length_c                   17.8313(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1991.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'x+1/2, -y+1/2, -z+'
'-x+, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.0798

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
BR1 Br 0.03524(10) 0.13032(9) 0.96486(7) 0.0542(3) Uani 1 1 d . . . . .
O1 O -0.5676(7) 0.0318(6) 0.8647(5) 0.063(2) Uani 1 1 d . . . . .
C2 C -0.5054(8) 0.0811(8) 0.9274(5) 0.049(3) Uani 1 1 d . . . . .
H2A H -0.5377 0.0416 0.9725 0.058 Uiso 1 1 calc R U . . .
H2B H -0.5238 0.1684 0.9309 0.058 Uiso 1 1 calc R U . . .
C3 C -0.3578(8) 0.0608(8) 0.9209(5) 0.037(2) Uani 1 1 d . . . . .
H3 H -0.3414 -0.0280 0.9214 0.045 Uiso 1 1 calc R U . . .
C4 C -0.2991(8) 0.1140(10) 0.8485(5) 0.041(2) Uani 1 1 d . . . . .
C5 C -0.3851(10) 0.0680(9) 0.7837(6) 0.051(3) Uani 1 1 d . . . . .
H5A H -0.3594 0.1092 0.7378 0.061 Uiso 1 1 calc R U . . .
H5B H -0.3711 -0.0196 0.7769 0.061 Uiso 1 1 calc R U . . .
C6 C -0.5278(12) 0.0909(9) 0.7977(6) 0.062(3) Uani 1 1 d . . . . .
H6A H -0.5435 0.1787 0.8017 0.075 Uiso 1 1 calc R U . . .
H6B H -0.5783 0.0597 0.7558 0.075 Uiso 1 1 calc R U . . .
N31 N -0.2922(6) 0.1169(7) 0.9893(4) 0.0391(17) Uani 1 1 d . . . . .
H31A H -0.3126 0.1965 0.9906 0.047 Uiso 1 1 calc R U . . .
H31B H -0.2066 0.1120 0.9825 0.047 Uiso 1 1 calc R U . . .
C32 C -0.3232(10) 0.0624(8) 1.0661(5) 0.043(2) Uani 1 1 d . . . . .
H32 H -0.4152 0.0783 1.0768 0.052 Uiso 1 1 calc R U . . .
C33 C -0.2421(11) 0.1316(12) 1.1238(5) 0.066(3) Uani 1 1 d . . . . .
H33A H -0.2600 0.2181 1.1202 0.099 Uiso 1 1 calc R U . . .
H33B H -0.2639 0.1031 1.1732 0.099 Uiso 1 1 calc R U . . .
H33C H -0.1515 0.1171 1.1144 0.099 Uiso 1 1 calc R U . . .
C34 C -0.3026(9) -0.0753(8) 1.0670(5) 0.042(2) Uani 1 1 d . . . . .
C35 C -0.4061(9) -0.1511(8) 1.0779(6) 0.058(3) Uani 1 1 d . . . . .
H35 H -0.4889 -0.1172 1.0818 0.069 Uiso 1 1 calc R U . . .
C36 C -0.3916(11) -0.2768(9) 1.0832(7) 0.061(3) Uani 1 1 d . . . . .
H36 H -0.4641 -0.3272 1.0887 0.074 Uiso 1 1 calc R U . . .
C37 C -0.2695(10) -0.3268(10) 1.0805(7) 0.061(3) Uani 1 1 d . . . . .
H37 H -0.2585 -0.4113 1.0859 0.074 Uiso 1 1 calc R U . . .
C38 C -0.1631(10) -0.2521(10) 1.0698(7) 0.062(3) Uani 1 1 d . . . . .
H38 H -0.0802 -0.2861 1.0678 0.075 Uiso 1 1 calc R U . . .
C39 C -0.1798(9) -0.1244(10) 1.0620(5) 0.053(3) Uani 1 1 d . . . . .
H39 H -0.1084 -0.0737 1.0535 0.064 Uiso 1 1 calc R U . . .
O41 O -0.1762(7) 0.0605(6) 0.8348(4) 0.0521(19) Uani 1 1 d . . . . .
H41 H -0.117(9) 0.090(9) 0.860(6) 0.063 Uiso 1 1 d . U . . .
C42 C -0.2949(9) 0.2539(8) 0.8508(5) 0.040(2) Uani 1 1 d . . . . .
H42 H -0.3625 0.2941 0.8754 0.048 Uiso 1 1 calc R U . . .
C43 C -0.2049(11) 0.3216(9) 0.8213(6) 0.055(3) Uani 1 1 d . . . . .
H43 H -0.1377 0.2804 0.7970 0.066 Uiso 1 1 calc R U . . .
C44 C -0.1977(9) 0.4583(9) 0.8220(6) 0.043(2) Uani 1 1 d . . . . .
C45 C -0.1278(11) 0.5194(10) 0.7667(7) 0.062(3) Uani 1 1 d . . . . .
H45 H -0.0810 0.4745 0.7315 0.075 Uiso 1 1 calc R U . . .
C46 C -0.1272(11) 0.6468(10) 0.7638(6) 0.062(3) Uani 1 1 d . . . . .
H46 H -0.0806 0.6862 0.7261 0.075 Uiso 1 1 calc R U . . .
C47 C -0.1940(11) 0.7161(10) 0.8154(7) 0.059(3) Uani 1 1 d . . . . .
H47 H -0.1932 0.8016 0.8130 0.071 Uiso 1 1 calc R U . . .
C48 C -0.2627(11) 0.6554(9) 0.8713(7) 0.057(3) Uani 1 1 d . . . . .
H48 H -0.3087 0.7008 0.9067 0.068 Uiso 1 1 calc R U . . .
C49 C -0.2637(10) 0.5294(9) 0.8748(7) 0.052(3) Uani 1 1 d . . . . .
H49 H -0.3091 0.4906 0.9132 0.062 Uiso 1 1 calc R U . . .


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 C2 1.394(10) . ?
O1 C6 1.418(12) . ?
C2 C3 1.537(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N31 1.522(10) . ?
C3 C4 1.538(12) . ?
C3 H3 0.9800 . ?
C4 O41 1.412(10) . ?
C4 C42 1.522(13) . ?
C4 C5 1.538(13) . ?
C5 C6 1.509(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N31 C32 1.526(11) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
C32 C34 1.511(12) . ?
C32 C33 1.523(13) . ?
C32 H32 0.9800 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.360(12) . ?
C34 C39 1.374(11) . ?
C35 C36 1.377(13) . ?
C35 H35 0.9300 . ?
C36 C37 1.369(13) . ?
C36 H36 0.9300 . ?
C37 C38 1.376(14) . ?
C37 H37 0.9300 . ?
C38 C39 1.405(14) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
O41 H41 0.82(10) . ?
C42 C43 1.293(13) . ?
C42 H42 0.9300 . ?
C43 C44 1.488(13) . ?
C43 H43 0.9300 . ?
C44 C45 1.388(14) . ?
C44 C49 1.395(14) . ?
C45 C46 1.385(14) . ?
C45 H45 0.9300 . ?
C46 C47 1.373(15) . ?
C46 H46 0.9300 . ?
C47 C48 1.388(15) . ?
C47 H47 0.9300 . ?
C48 C49 1.371(14) . ?
C48 H48 0.9300 . ?
C49 H49 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
C2 O1 C6 111.7(7) . . ?
O1 C2 C3 109.7(7) . . ?
O1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
O1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N31 C3 C2 108.7(7) . . ?
N31 C3 C4 110.4(7) . . ?
C2 C3 C4 113.4(7) . . ?
N31 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
O41 C4 C42 113.0(8) . . ?
O41 C4 C3 110.0(8) . . ?
C42 C4 C3 111.4(8) . . ?
O41 C4 C5 104.5(8) . . ?
C42 C4 C5 111.2(8) . . ?
C3 C4 C5 106.4(8) . . ?
C6 C5 C4 112.4(8) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 C5 110.2(9) . . ?
O1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C3 N31 C32 118.1(7) . . ?
C3 N31 H31A 107.8 . . ?
C32 N31 H31A 107.8 . . ?
C3 N31 H31B 107.8 . . ?
C32 N31 H31B 107.8 . . ?
H31A N31 H31B 107.1 . . ?
C34 C32 C33 113.9(9) . . ?
C34 C32 N31 111.4(8) . . ?
C33 C32 N31 107.5(8) . . ?
C34 C32 H32 108.0 . . ?
C33 C32 H32 108.0 . . ?
N31 C32 H32 108.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 119.5(8) . . ?
C35 C34 C32 119.4(8) . . ?
C39 C34 C32 120.9(9) . . ?
C34 C35 C36 121.7(9) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C37 C36 C35 119.4(10) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C38 120.0(10) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C39 120.0(10) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C34 C39 C38 119.3(9) . . ?
C34 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
C4 O41 H41 114(7) . . ?
C43 C42 C4 125.2(9) . . ?
C43 C42 H42 117.4 . . ?
C4 C42 H42 117.4 . . ?
C42 C43 C44 126.9(11) . . ?
C42 C43 H43 116.6 . . ?
C44 C43 H43 116.6 . . ?
C45 C44 C49 117.8(10) . . ?
C45 C44 C43 119.9(11) . . ?
C49 C44 C43 122.3(10) . . ?
C46 C45 C44 120.5(11) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C47 C46 C45 121.4(10) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C46 C47 C48 118.3(10) . . ?
C46 C47 H47 120.8 . . ?
C48 C47 H47 120.8 . . ?
C49 C48 C47 120.8(12) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C48 C49 C44 121.2(11) . . ?
C48 C49 H49 119.4 . . ?
C44 C49 H49 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C2 C3 -62.2(10) . . . . ?
O1 C2 C3 N31 179.2(7) . . . . ?
O1 C2 C3 C4 56.1(10) . . . . ?
N31 C3 C4 O41 76.1(9) . . . . ?
C2 C3 C4 O41 -161.7(7) . . . . ?
N31 C3 C4 C42 -50.0(9) . . . . ?
C2 C3 C4 C42 72.2(9) . . . . ?
N31 C3 C4 C5 -171.3(7) . . . . ?
C2 C3 C4 C5 -49.1(10) . . . . ?
O41 C4 C5 C6 166.7(8) . . . . ?
C42 C4 C5 C6 -71.1(11) . . . . ?
C3 C4 C5 C6 50.4(11) . . . . ?
C2 O1 C6 C5 64.3(10) . . . . ?
C4 C5 C6 O1 -58.6(11) . . . . ?
C2 C3 N31 C32 63.8(9) . . . . ?
C4 C3 N31 C32 -171.3(7) . . . . ?
C3 N31 C32 C34 52.7(11) . . . . ?
C3 N31 C32 C33 178.1(7) . . . . ?
C33 C32 C34 C35 122.9(11) . . . . ?
N31 C32 C34 C35 -115.4(10) . . . . ?
C33 C32 C34 C39 -52.8(13) . . . . ?
N31 C32 C34 C39 69.0(12) . . . . ?
C39 C34 C35 C36 -0.7(16) . . . . ?
C32 C34 C35 C36 -176.4(10) . . . . ?
C34 C35 C36 C37 2.6(18) . . . . ?
C35 C36 C37 C38 -2.3(19) . . . . ?
C36 C37 C38 C39 0.2(18) . . . . ?
C35 C34 C39 C38 -1.4(15) . . . . ?
C32 C34 C39 C38 174.3(9) . . . . ?
C37 C38 C39 C34 1.6(16) . . . . ?
O41 C4 C42 C43 21.0(15) . . . . ?
C3 C4 C42 C43 145.4(10) . . . . ?
C5 C4 C42 C43 -96.2(12) . . . . ?
C4 C42 C43 C44 179.7(10) . . . . ?
C42 C43 C44 C45 -155.6(11) . . . . ?
C42 C43 C44 C49 22(2) . . . . ?
C49 C44 C45 C46 -1.6(16) . . . . ?
C43 C44 C45 C46 175.7(11) . . . . ?
C44 C45 C46 C47 0.7(18) . . . . ?
C45 C46 C47 C48 0.1(17) . . . . ?
C46 C47 C48 C49 0.1(17) . . . . ?
C47 C48 C49 C44 -1.1(18) . . . . ?
C45 C44 C49 C48 1.8(16) . . . . ?
C43 C44 C49 C48 -175.5(11) . . . . ?

_refine_ls_abs_structure_details 
;
 Flack x determined using 490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(18)
############################################################################# 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_measurement_reflns_used    15216
_cell_measurement_theta_min      2.727
_cell_measurement_theta_max      31.012

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.077
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.681
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.208
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D. (1983). Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7948
_exptl_absorpt_correction_T_max  0.8125

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'LFF Sealed Tube'
_diffrn_detector                 'Hybride pixel array detector'
_diffrn_detector_type            'DECTRIS Pilatus--100K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source                   'SEIFERT Iso--Debyeflex 3003'
_diffrn_measurement_device       'Four cyrcle diffractometer'
_diffrn_measurement_device_type  STADI--VARY
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'Plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'Rotation method'
_diffrn_measurement_details      
'40 runs, 1726 frames, detector distance = 42 mm'
_diffrn_reflns_number            15216
_diffrn_reflns_av_unetI/netI     0.2603
_diffrn_reflns_av_R_equivalents  0.0536 # before absorption correction'
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         31.012
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6277
_reflns_number_gt                1856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    1.000

_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       'X--AREA       (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA       (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA       (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97      (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick,  2015)'
_computing_molecular_graphics    'Ortep--3      (Farrugia,   1997)'
_computing_publication_material  'WinGX         (Farrugia,   1999)'

_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)+(0.0020P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6277
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.659
_refine_ls_restrained_S_all      0.659
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_Yur111
_audit_block_doi                 10.5517/ccdc.csd.cc111p4x
_database_code_depnum_ccdc_archive 'CCDC 954928'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Chemistry Department of Moscow State University
Russia
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
'(3RS,3aSR,8aRS)--tert--butyl /1--benzyl--4--oxo--3--phenyloctahydropyrrolo[2,3--d]/azepine--6(2H)--carboxylate'

_chemical_melting_point_gt       420
_chemical_melting_point_lt       421
_chemical_formula_moiety         'C26 H32 N2 O3'
_chemical_formula_sum            'C26 H32 N2 O3'
_chemical_formula_weight         420.54
_chemical_compound_source        'synthesis as described'

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       CH₃OH
_exptl_crystal_density_diffrn    1.200

_cell_length_a                   11.490(2)
_cell_length_b                   17.453(3)
_cell_length_c                   23.207(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4653.8(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(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_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'x+1/2, -y+1/2, -z+'
'-x+, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x-1/2, y+, -z-1/2'
'-x-1/2, y-1/2, z+'
'x+, -y-1/2, z-1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0965

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
N1 N 0.75526(10) 0.38753(7) 0.50371(4) 0.0509(3) Uani 1 1 d . . . . .
C2 C 0.84908(13) 0.43129(9) 0.47642(6) 0.0554(4) Uani 1 1 d . . . . .
H2A H 0.9197 0.4285 0.4993 0.067 Uiso 1 1 calc R U . . .
H2B H 0.8271 0.4846 0.4721 0.067 Uiso 1 1 calc R U . . .
C3 C 0.86726(11) 0.39371(8) 0.41736(6) 0.0486(3) Uani 1 1 d . . . . .
H3 H 0.9509 0.3871 0.4106 0.058 Uiso 1 1 calc R U . . .
C4 C 0.81032(11) 0.31425(7) 0.42406(5) 0.0436(3) Uani 1 1 d . . . . .
H4 H 0.7384 0.3145 0.4013 0.052 Uiso 1 1 calc R U . . .
C5 C 0.88396(11) 0.24810(8) 0.40282(6) 0.0489(3) Uani 1 1 d . . . . .
C6 C 0.83133(12) 0.16915(8) 0.40481(7) 0.0576(4) Uani 1 1 d . . . . .
H6A H 0.8429 0.1449 0.3676 0.069 Uiso 1 1 calc R U . . .
H6B H 0.8731 0.1391 0.4332 0.069 Uiso 1 1 calc R U . . .
N7 N 0.70851(11) 0.16692(7) 0.41857(5) 0.0572(3) Uani 1 1 d . . . . .
C8 C 0.67580(16) 0.17562(10) 0.47892(7) 0.0688(4) Uani 1 1 d . . . . .
H8A H 0.7328 0.1495 0.5027 0.083 Uiso 1 1 calc R U . . .
H8B H 0.6012 0.1509 0.4851 0.083 Uiso 1 1 calc R U . . .
C9 C 0.66715(13) 0.25864(10) 0.49841(7) 0.0616(4) Uani 1 1 d . . . . .
H9A H 0.6495 0.2593 0.5393 0.074 Uiso 1 1 calc R U . . .
H9B H 0.6023 0.2824 0.4785 0.074 Uiso 1 1 calc R U . . .
C10 C 0.77537(12) 0.30719(8) 0.48824(5) 0.0492(3) Uani 1 1 d . . . . .
H10 H 0.8407 0.2867 0.5106 0.059 Uiso 1 1 calc R U . . .
C11 C 0.75039(16) 0.40050(10) 0.56634(6) 0.0650(4) Uani 1 1 d . . . . .
H11A H 0.8248 0.3870 0.5833 0.078 Uiso 1 1 calc R U . . .
H11B H 0.6915 0.3675 0.5831 0.078 Uiso 1 1 calc R U . . .
C12 C 0.72261(13) 0.48245(10) 0.58047(6) 0.0586(4) Uani 1 1 d . . . . .
C13 C 0.61487(15) 0.51283(11) 0.56725(9) 0.0800(5) Uani 1 1 d . . . . .
H13 H 0.5590 0.4827 0.5492 0.096 Uiso 1 1 calc R U . . .
C14 C 0.59010(18) 0.58939(13) 0.58119(10) 0.0967(7) Uani 1 1 d . . . . .
H14 H 0.5181 0.6103 0.5719 0.116 Uiso 1 1 calc R U . . .
C15 C 0.6727(2) 0.63337(12) 0.60859(9) 0.0895(6) Uani 1 1 d . . . . .
H15 H 0.6556 0.6837 0.6185 0.107 Uiso 1 1 calc R U . . .
C16 C 0.7793(2) 0.60367(13) 0.62127(8) 0.0858(6) Uani 1 1 d . . . . .
H16 H 0.8354 0.6340 0.6390 0.103 Uiso 1 1 calc R U . . .
C17 C 0.80338(16) 0.52906(11) 0.60778(6) 0.0708(5) Uani 1 1 d . . . . .
H17 H 0.8759 0.5090 0.6172 0.085 Uiso 1 1 calc R U . . .
C31 C 0.81408(12) 0.43426(7) 0.36617(6) 0.0490(3) Uani 1 1 d . . . . .
C32 C 0.70453(14) 0.46733(8) 0.36940(7) 0.0594(4) Uani 1 1 d . . . . .
H32 H 0.6672 0.4706 0.4049 0.071 Uiso 1 1 calc R U . . .
C33 C 0.64990(17) 0.49551(9) 0.32083(7) 0.0725(5) Uani 1 1 d . . . . .
H33 H 0.5764 0.5175 0.3238 0.087 Uiso 1 1 calc R U . . .
C34 C 0.7038(2) 0.49109(10) 0.26807(8) 0.0779(5) Uani 1 1 d . . . . .
H34 H 0.6664 0.5092 0.2353 0.093 Uiso 1 1 calc R U . . .
C35 C 0.8133(2) 0.45979(11) 0.26391(7) 0.0809(5) Uani 1 1 d . . . . .
H35 H 0.8504 0.4576 0.2283 0.097 Uiso 1 1 calc R U . . .
C36 C 0.86877(15) 0.43130(9) 0.31281(6) 0.0647(4) Uani 1 1 d . . . . .
H36 H 0.9428 0.4102 0.3097 0.078 Uiso 1 1 calc R U . . .
O5 O 0.98193(9) 0.25597(7) 0.38506(5) 0.0719(3) Uani 1 1 d . . . . .
C71 C 0.62617(13) 0.18225(9) 0.37780(7) 0.0565(4) Uani 1 1 d . . . . .
O71 O 0.52337(10) 0.18994(8) 0.38880(5) 0.0798(4) Uani 1 1 d . . . . .
O72 O 0.67526(8) 0.18789(6) 0.32562(4) 0.0575(3) Uani 1 1 d . . . . .
C73 C 0.60505(13) 0.20706(9) 0.27436(6) 0.0562(4) Uani 1 1 d . . . . .
C74 C 0.69476(16) 0.20560(13) 0.22697(8) 0.0841(6) Uani 1 1 d . . . . .
H74A H 0.6582 0.2175 0.1909 0.126 Uiso 1 1 calc R U . . .
H74B H 0.7541 0.2428 0.2350 0.126 Uiso 1 1 calc R U . . .
H74C H 0.7291 0.1555 0.2249 0.126 Uiso 1 1 calc R U . . .
C75 C 0.55332(18) 0.28573(10) 0.28100(9) 0.0840(5) Uani 1 1 d . . . . .
H75A H 0.5078 0.2978 0.2475 0.126 Uiso 1 1 calc R U . . .
H75B H 0.5045 0.2869 0.3146 0.126 Uiso 1 1 calc R U . . .
H75C H 0.6147 0.3227 0.2851 0.126 Uiso 1 1 calc R U . . .
C76 C 0.51419(16) 0.14643(11) 0.26443(9) 0.0843(6) Uani 1 1 d . . . . .
H76A H 0.4690 0.1594 0.2310 0.126 Uiso 1 1 calc R U . . .
H76B H 0.5515 0.0979 0.2585 0.126 Uiso 1 1 calc R U . . .
H76C H 0.4641 0.1433 0.2975 0.126 Uiso 1 1 calc R U . . .


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
N1 C2 1.4651(18) . ?
N1 C10 1.4657(18) . ?
N1 C11 1.4721(16) . ?
C2 C3 1.5338(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C31 1.5118(19) . ?
C3 C4 1.5412(19) . ?
C3 H3 0.9800 . ?
C4 C5 1.5140(18) . ?
C4 C10 1.5474(17) . ?
C4 H4 0.9800 . ?
C5 O5 1.2066(16) . ?
C5 C6 1.505(2) . ?
C6 N7 1.4474(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N7 C71 1.3645(18) . ?
N7 C8 1.458(2) . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.523(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C11 C12 1.502(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.381(2) . ?
C12 C17 1.387(2) . ?
C13 C14 1.404(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C31 C32 1.387(2) . ?
C31 C36 1.3897(19) . ?
C32 C33 1.381(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.393(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C71 O71 1.2160(18) . ?
C71 O72 1.3395(17) . ?
O72 C73 1.4758(16) . ?
C73 C75 1.504(2) . ?
C73 C76 1.504(2) . ?
C73 C74 1.508(2) . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?

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
C2 N1 C10 106.07(11) . . ?
C2 N1 C11 112.00(12) . . ?
C10 N1 C11 113.26(11) . . ?
N1 C2 C3 105.28(11) . . ?
N1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
N1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C31 C3 C2 116.55(12) . . ?
C31 C3 C4 109.21(10) . . ?
C2 C3 C4 103.70(10) . . ?
C31 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C5 C4 C3 114.58(11) . . ?
C5 C4 C10 113.44(11) . . ?
C3 C4 C10 106.20(10) . . ?
C5 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
C10 C4 H4 107.4 . . ?
O5 C5 C6 119.31(13) . . ?
O5 C5 C4 123.08(14) . . ?
C6 C5 C4 117.61(12) . . ?
N7 C6 C5 115.03(12) . . ?
N7 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
N7 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C71 N7 C6 121.19(13) . . ?
C71 N7 C8 117.84(13) . . ?
C6 N7 C8 117.41(12) . . ?
N7 C8 C9 113.68(12) . . ?
N7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 115.50(13) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
N1 C10 C9 111.44(12) . . ?
N1 C10 C4 101.56(10) . . ?
C9 C10 C4 113.91(11) . . ?
N1 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
C4 C10 H10 109.9 . . ?
N1 C11 C12 111.72(12) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 118.42(16) . . ?
C13 C12 C11 120.50(16) . . ?
C17 C12 C11 121.07(15) . . ?
C12 C13 C14 119.73(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 121.82(18) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C32 C31 C36 118.30(14) . . ?
C32 C31 C3 121.29(12) . . ?
C36 C31 C3 120.00(14) . . ?
C33 C32 C31 121.12(15) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C32 120.15(18) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.82(17) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C36 120.21(16) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 120.37(17) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
O71 C71 O72 126.21(14) . . ?
O71 C71 N7 123.34(15) . . ?
O72 C71 N7 110.44(13) . . ?
C71 O72 C73 121.01(11) . . ?
O72 C73 C75 109.90(12) . . ?
O72 C73 C76 110.08(13) . . ?
C75 C73 C76 112.56(14) . . ?
O72 C73 C74 102.14(12) . . ?
C75 C73 C74 111.13(15) . . ?
C76 C73 C74 110.54(15) . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C73 C75 H75A 109.5 . . ?
C73 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C73 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C73 C76 H76A 109.5 . . ?
C73 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C73 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?

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
C10 N1 C2 C3 38.80(14) . . . . ?
C11 N1 C2 C3 162.83(11) . . . . ?
N1 C2 C3 C31 101.26(14) . . . . ?
N1 C2 C3 C4 -18.76(14) . . . . ?
C31 C3 C4 C5 102.79(13) . . . . ?
C2 C3 C4 C5 -132.31(11) . . . . ?
C31 C3 C4 C10 -131.16(11) . . . . ?
C2 C3 C4 C10 -6.27(13) . . . . ?
C3 C4 C5 O5 4.03(18) . . . . ?
C10 C4 C5 O5 -118.16(15) . . . . ?
C3 C4 C5 C6 -176.56(11) . . . . ?
C10 C4 C5 C6 61.26(15) . . . . ?
O5 C5 C6 N7 -171.25(13) . . . . ?
C4 C5 C6 N7 9.31(18) . . . . ?
C5 C6 N7 C71 79.50(17) . . . . ?
C5 C6 N7 C8 -78.74(16) . . . . ?
C71 N7 C8 C9 -74.72(18) . . . . ?
C6 N7 C8 C9 84.27(17) . . . . ?
N7 C8 C9 C10 -54.99(19) . . . . ?
C2 N1 C10 C9 -163.26(11) . . . . ?
C11 N1 C10 C9 73.50(15) . . . . ?
C2 N1 C10 C4 -41.61(13) . . . . ?
C11 N1 C10 C4 -164.84(12) . . . . ?
C8 C9 C10 N1 175.05(12) . . . . ?
C8 C9 C10 C4 60.87(16) . . . . ?
C5 C4 C10 N1 155.46(11) . . . . ?
C3 C4 C10 N1 28.72(13) . . . . ?
C5 C4 C10 C9 -84.62(15) . . . . ?
C3 C4 C10 C9 148.65(12) . . . . ?
C2 N1 C11 C12 63.50(17) . . . . ?
C10 N1 C11 C12 -176.59(13) . . . . ?
N1 C11 C12 C13 66.9(2) . . . . ?
N1 C11 C12 C17 -114.08(16) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 C14 179.50(16) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -0.6(2) . . . . ?
C11 C12 C17 C16 -179.60(15) . . . . ?
C2 C3 C31 C32 -40.44(18) . . . . ?
C4 C3 C31 C32 76.59(15) . . . . ?
C2 C3 C31 C36 147.09(13) . . . . ?
C4 C3 C31 C36 -95.89(15) . . . . ?
C36 C31 C32 C33 1.1(2) . . . . ?
C3 C31 C32 C33 -171.52(14) . . . . ?
C31 C32 C33 C34 0.0(2) . . . . ?
C32 C33 C34 C35 -1.2(3) . . . . ?
C33 C34 C35 C36 1.2(3) . . . . ?
C32 C31 C36 C35 -1.1(2) . . . . ?
C3 C31 C36 C35 171.61(14) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C6 N7 C71 O71 -171.01(15) . . . . ?
C8 N7 C71 O71 -12.9(2) . . . . ?
C6 N7 C71 O72 8.50(19) . . . . ?
C8 N7 C71 O72 166.65(12) . . . . ?
O71 C71 O72 C73 1.8(2) . . . . ?
N7 C71 O72 C73 -177.74(11) . . . . ?
C71 O72 C73 C75 62.88(18) . . . . ?
C71 O72 C73 C76 -61.65(17) . . . . ?
C71 O72 C73 C74 -179.09(14) . . . . ?
################################################################## 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'

_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.
;

_cell_measurement_reflns_used    25
_cell_measurement_theta_min      39.93
_cell_measurement_theta_max      44.92

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.062
_exptl_absorpt_process_details   
;
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Cubic fit to sin(theta)/lambda - 24 parameters
;
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_correction_T_ave  0.8419
_exptl_absorpt_Rmerge_before     0.0639
_exptl_absorpt_Rmerge_after      0.0629

_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD--4'
_diffrn_measurement_method       'non--profiled ω--scans'
_diffrn_standards_number         1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 -20
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        2
_diffrn_standards_decay_corr_max 1.022
_diffrn_standards_decay_corr_min 0.983
_diffrn_reflns_number            4997
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             4488
_reflns_number_gt                3469
_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_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_data_collection       'CAD4 Express  (Enraf--Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express  (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4       (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS97      (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep--3      (Farrugia,  1997)'
_computing_publication_material  'WinGX         (Farrugia,  1999)'

_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)+(0.0481P)²+0.7275P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4488
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.026

####################################################################### 
# 
# 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_Yur108
_audit_block_doi                 10.5517/ccdc.csd.cc235tfk
_database_code_depnum_ccdc_archive 'CCDC 1942008'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Moscow State University, Chemistry Department
Russia
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_chemical_name_systematic        
'(3R,3aS,8aS)-tert-butyl 4-oxo-3-phenyl-1-((R)-1-phenylethyl)octahydropyrrolo[2,3-c]azepine-7(1H)-carboxylate'
_chemical_name_common            ?
_chemical_melting_point_gt       404
_chemical_melting_point_lt       407
_chemical_formula_moiety         'C27 H34 N2 O3'
_chemical_formula_sum            'C27 H34 N2 O3'
_chemical_formula_weight         434.56
_chemical_absolute_configuration unk

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_preparation       'MTBE - Hexane'

_cell_length_a                   5.8222(2)
_cell_length_b                   18.1399(5)
_cell_length_c                   23.3280(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2463.77(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'x+1/2, -y+1/2, -z+'
'-x+, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1079

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
N1 N 0.0577(9) 0.0609(2) 0.04835(17) 0.0548(12) Uani 1 1 d . . . . .
C2 C 0.2309(12) 0.0102(3) 0.0705(2) 0.0686(17) Uani 1 1 d . . . . .
H2A H 0.1955 -0.0044 0.1096 0.082 Uiso 1 1 calc R U . . .
H2B H 0.3823 0.0325 0.0697 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2185(10) -0.0572(3) 0.0292(2) 0.0552(14) Uani 1 1 d . . . . .
H3 H 0.3746 -0.0700 0.0171 0.066 Uiso 1 1 calc R U . . .
C4 C 0.0862(10) -0.0274(2) -0.02275(19) 0.0479(13) Uani 1 1 d . . . . .
H4 H -0.0718 -0.0458 -0.0208 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1848(12) -0.0485(3) -0.0795(3) 0.0596(15) Uani 1 1 d . . . . .
C6 C 0.0364(13) -0.0443(3) -0.1320(2) 0.0739(19) Uani 1 1 d . . . . .
H6A H -0.0341 -0.0922 -0.1380 0.089 Uiso 1 1 calc R U . . .
H6B H 0.1339 -0.0344 -0.1648 0.089 Uiso 1 1 calc R U . . .
C7 C -0.1516(11) 0.0134(3) -0.1301(2) 0.0676(17) Uani 1 1 d . . . . .
H7A H -0.2105 0.0206 -0.1686 0.081 Uiso 1 1 calc R U . . .
H7B H -0.2766 -0.0049 -0.1066 0.081 Uiso 1 1 calc R U . . .
N8 N -0.0777(8) 0.0841(2) -0.10759(18) 0.0561(12) Uani 1 1 d . . . . .
C9 C -0.1034(11) 0.0966(3) -0.0469(2) 0.0622(16) Uani 1 1 d . . . . .
H9A H -0.2532 0.0794 -0.0346 0.075 Uiso 1 1 calc R U . . .
H9B H -0.0939 0.1491 -0.0391 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0812(10) 0.0567(2) -0.01385(18) 0.0487(13) Uani 1 1 d . . . . .
H10 H 0.2310 0.0770 -0.0247 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0542(13) 0.1354(3) 0.0744(2) 0.0683(17) Uani 1 1 d . . . . .
H11 H -0.0850 0.1598 0.0605 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2566(15) 0.1846(4) 0.0576(3) 0.110(3) Uani 1 1 d . . . . .
H12A H 0.2419 0.2316 0.0761 0.164 Uiso 1 1 calc R U . . .
H12B H 0.3977 0.1617 0.0692 0.164 Uiso 1 1 calc R U . . .
H12C H 0.2572 0.1914 0.0168 0.164 Uiso 1 1 calc R U . . .
C13 C 0.0251(12) 0.1258(3) 0.1389(2) 0.0612(17) Uani 1 1 d . . . . .
C14 C 0.1860(12) 0.1507(3) 0.1780(2) 0.0654(16) Uani 1 1 d . . . . .
H14 H 0.3153 0.1758 0.1652 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1555(12) 0.1384(3) 0.2359(3) 0.0706(17) Uani 1 1 d . . . . .
H15 H 0.2665 0.1547 0.2616 0.085 Uiso 1 1 calc R U . . .
C16 C -0.0336(12) 0.1028(3) 0.2561(3) 0.0682(17) Uani 1 1 d . . . . .
H16 H -0.0527 0.0947 0.2952 0.082 Uiso 1 1 calc R U . . .
C17 C -0.1969(12) 0.0790(3) 0.2171(2) 0.0715(18) Uani 1 1 d . . . . .
H17 H -0.3283 0.0552 0.2302 0.086 Uiso 1 1 calc R U . . .
C18 C -0.1672(12) 0.0902(3) 0.1594(2) 0.0665(17) Uani 1 1 d . . . . .
H18 H -0.2782 0.0737 0.1338 0.080 Uiso 1 1 calc R U . . .
C31 C 0.1095(12) -0.1238(3) 0.0555(2) 0.0589(15) Uani 1 1 d . . . . .
C32 C -0.0989(14) -0.1198(3) 0.0842(2) 0.0771(19) Uani 1 1 d . . . . .
H32 H -0.1745 -0.0748 0.0869 0.092 Uiso 1 1 calc R U . . .
C33 C -0.1952(15) -0.1815(4) 0.1086(3) 0.096(2) Uani 1 1 d . . . . .
H33 H -0.3344 -0.1774 0.1278 0.116 Uiso 1 1 calc R U . . .
C34 C -0.092(2) -0.2478(5) 0.1052(3) 0.108(3) Uani 1 1 d . . . . .
H34 H -0.1590 -0.2889 0.1222 0.129 Uiso 1 1 calc R U . . .
C35 C 0.108(2) -0.2539(4) 0.0770(3) 0.105(3) Uani 1 1 d . . . . .
H35 H 0.1774 -0.2999 0.0741 0.126 Uiso 1 1 calc R U . . .
C36 C 0.2144(14) -0.1926(3) 0.0518(2) 0.082(2) Uani 1 1 d . . . . .
H36 H 0.3539 -0.1978 0.0328 0.099 Uiso 1 1 calc R U . . .
O5 O 0.3839(9) -0.0679(2) -0.08502(19) 0.0862(13) Uani 1 1 d . . . . .
C81 C 0.0512(11) 0.1310(3) -0.1396(2) 0.0557(15) Uani 1 1 d . . . . .
O81 O 0.1340(9) 0.1876(2) -0.12057(16) 0.0867(16) Uani 1 1 d . . . . .
O82 O 0.0731(7) 0.10583(18) -0.19286(15) 0.0647(10) Uani 1 1 d . . . . .
C83 C 0.2159(11) 0.1431(3) -0.2351(2) 0.0604(15) Uani 1 1 d . . . . .
C84 C 0.1230(12) 0.2195(3) -0.2473(3) 0.083(2) Uani 1 1 d . . . . .
H84A H 0.2187 0.2434 -0.2752 0.124 Uiso 1 1 calc R U . . .
H84B H -0.0307 0.2157 -0.2619 0.124 Uiso 1 1 calc R U . . .
H84C H 0.1220 0.2479 -0.2125 0.124 Uiso 1 1 calc R U . . .
C85 C 0.1900(15) 0.0940(3) -0.2872(3) 0.098(2) Uani 1 1 d . . . . .
H85A H 0.2788 0.1137 -0.3183 0.147 Uiso 1 1 calc R U . . .
H85B H 0.2437 0.0453 -0.2781 0.147 Uiso 1 1 calc R U . . .
H85C H 0.0312 0.0917 -0.2981 0.147 Uiso 1 1 calc R U . . .
C86 C 0.4601(13) 0.1455(4) -0.2148(3) 0.111(3) Uani 1 1 d . . . . .
H86A H 0.5532 0.1701 -0.2428 0.167 Uiso 1 1 calc R U . . .
H86B H 0.4680 0.1717 -0.1791 0.167 Uiso 1 1 calc R U . . .
H86C H 0.5156 0.0961 -0.2094 0.167 Uiso 1 1 calc R U . . .

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
N1 C10 1.460(6) . ?
N1 C2 1.460(7) . ?
N1 C11 1.481(6) . ?
C2 C3 1.558(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C31 1.495(7) . ?
C3 C4 1.534(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.494(7) . ?
C4 C10 1.539(6) . ?
C4 H4 0.9800 . ?
C5 O5 1.218(7) . ?
C5 C6 1.500(8) . ?
C6 C7 1.516(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N8 1.451(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 C81 1.359(6) . ?
N8 C9 1.441(6) . ?
C9 C10 1.509(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C11 C13 1.524(7) . ?
C11 C12 1.530(9) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.377(8) . ?
C13 C14 1.382(8) . ?
C14 C15 1.382(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C31 C32 1.387(9) . ?
C31 C36 1.392(8) . ?
C32 C33 1.376(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.345(10) . ?
C33 H33 0.9300 . ?
C34 C35 1.343(11) . ?
C34 H34 0.9300 . ?
C35 C36 1.403(10) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C81 O81 1.217(6) . ?
C81 O82 1.330(6) . ?
O82 C83 1.456(6) . ?
C83 C86 1.500(9) . ?
C83 C85 1.514(8) . ?
C83 C84 1.515(7) . ?
C84 H84A 0.9600 . ?
C84 H84B 0.9600 . ?
C84 H84C 0.9600 . ?
C85 H85A 0.9600 . ?
C85 H85B 0.9600 . ?
C85 H85C 0.9600 . ?
C86 H86A 0.9600 . ?
C86 H86B 0.9600 . ?
C86 H86C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 104.7(4) . . ?
C10 N1 C11 117.3(4) . . ?
C2 N1 C11 116.0(5) . . ?
N1 C2 C3 104.1(4) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
C31 C3 C4 113.3(4) . . ?
C31 C3 C2 113.5(5) . . ?
C4 C3 C2 103.6(4) . . ?
C31 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C5 C4 C3 114.6(5) . . ?
C5 C4 C10 112.4(4) . . ?
C3 C4 C10 104.6(4) . . ?
C5 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C10 C4 H4 108.3 . . ?
O5 C5 C4 122.2(6) . . ?
O5 C5 C6 118.5(6) . . ?
C4 C5 C6 119.3(6) . . ?
C5 C6 C7 115.3(5) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N8 C7 C6 114.0(5) . . ?
N8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C81 N8 C9 119.9(5) . . ?
C81 N8 C7 121.2(4) . . ?
C9 N8 C7 117.7(4) . . ?
N8 C9 C10 110.7(4) . . ?
N8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C9 114.6(4) . . ?
N1 C10 C4 100.8(3) . . ?
C9 C10 C4 114.9(5) . . ?
N1 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C4 C10 H10 108.7 . . ?
N1 C11 C13 107.7(4) . . ?
N1 C11 C12 114.6(6) . . ?
C13 C11 C12 114.0(5) . . ?
N1 C11 H11 106.7 . . ?
C13 C11 H11 106.7 . . ?
C12 C11 H11 106.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.4(5) . . ?
C18 C13 C11 119.0(6) . . ?
C14 C13 C11 122.5(6) . . ?
C15 C14 C13 120.3(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 121.2(6) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.5(6) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 120.8(6) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 120.7(6) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C32 C31 C36 117.4(6) . . ?
C32 C31 C3 121.8(5) . . ?
C36 C31 C3 120.8(6) . . ?
C33 C32 C31 120.9(7) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 121.5(8) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C33 119.2(8) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 121.6(8) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C31 C36 C35 119.4(7) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
O81 C81 O82 126.3(5) . . ?
O81 C81 N8 123.1(5) . . ?
O82 C81 N8 110.5(5) . . ?
C81 O82 C83 121.8(4) . . ?
O82 C83 C86 110.0(5) . . ?
O82 C83 C85 102.3(5) . . ?
C86 C83 C85 111.4(6) . . ?
O82 C83 C84 110.4(4) . . ?
C86 C83 C84 111.8(5) . . ?
C85 C83 C84 110.6(5) . . ?
C83 C84 H84A 109.5 . . ?
C83 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C83 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
C83 C85 H85A 109.5 . . ?
C83 C85 H85B 109.5 . . ?
H85A C85 H85B 109.5 . . ?
C83 C85 H85C 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?
C83 C86 H86A 109.5 . . ?
C83 C86 H86B 109.5 . . ?
H86A C86 H86B 109.5 . . ?
C83 C86 H86C 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 109.5 . . ?

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
C10 N1 C2 C3 -40.4(5) . . . . ?
C11 N1 C2 C3 -171.4(5) . . . . ?
N1 C2 C3 C31 -107.3(5) . . . . ?
N1 C2 C3 C4 16.0(6) . . . . ?
C31 C3 C4 C5 -100.7(5) . . . . ?
C2 C3 C4 C5 135.9(5) . . . . ?
C31 C3 C4 C10 135.8(5) . . . . ?
C2 C3 C4 C10 12.3(6) . . . . ?
C3 C4 C5 O5 -20.9(7) . . . . ?
C10 C4 C5 O5 98.4(6) . . . . ?
C3 C4 C5 C6 160.5(4) . . . . ?
C10 C4 C5 C6 -80.2(6) . . . . ?
O5 C5 C6 C7 -149.7(5) . . . . ?
C4 C5 C6 C7 29.0(7) . . . . ?
C5 C6 C7 N8 43.9(7) . . . . ?
C6 C7 N8 C81 75.7(6) . . . . ?
C6 C7 N8 C9 -91.7(6) . . . . ?
C81 N8 C9 C10 -90.9(5) . . . . ?
C7 N8 C9 C10 76.6(6) . . . . ?
C2 N1 C10 C9 171.8(4) . . . . ?
C11 N1 C10 C9 -58.0(7) . . . . ?
C2 N1 C10 C4 47.8(5) . . . . ?
C11 N1 C10 C4 178.0(5) . . . . ?
N8 C9 C10 N1 -175.0(4) . . . . ?
N8 C9 C10 C4 -58.9(6) . . . . ?
C5 C4 C10 N1 -161.2(5) . . . . ?
C3 C4 C10 N1 -36.2(5) . . . . ?
C5 C4 C10 C9 75.0(6) . . . . ?
C3 C4 C10 C9 -160.0(4) . . . . ?
C10 N1 C11 C13 179.2(5) . . . . ?
C2 N1 C11 C13 -56.1(7) . . . . ?
C10 N1 C11 C12 -52.9(7) . . . . ?
C2 N1 C11 C12 71.8(6) . . . . ?
N1 C11 C13 C18 -59.7(7) . . . . ?
C12 C11 C13 C18 172.1(5) . . . . ?
N1 C11 C13 C14 119.6(6) . . . . ?
C12 C11 C13 C14 -8.7(8) . . . . ?
C18 C13 C14 C15 1.5(8) . . . . ?
C11 C13 C14 C15 -177.7(5) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 C17 -0.1(9) . . . . ?
C15 C16 C17 C18 0.8(9) . . . . ?
C16 C17 C18 C13 -0.4(9) . . . . ?
C14 C13 C18 C17 -0.8(8) . . . . ?
C11 C13 C18 C17 178.5(5) . . . . ?
C4 C3 C31 C32 -68.6(7) . . . . ?
C2 C3 C31 C32 49.2(7) . . . . ?
C4 C3 C31 C36 111.2(6) . . . . ?
C2 C3 C31 C36 -130.9(6) . . . . ?
C36 C31 C32 C33 0.9(9) . . . . ?
C3 C31 C32 C33 -179.3(5) . . . . ?
C31 C32 C33 C34 -0.5(10) . . . . ?
C32 C33 C34 C35 -0.6(12) . . . . ?
C33 C34 C35 C36 1.2(13) . . . . ?
C32 C31 C36 C35 -0.3(9) . . . . ?
C3 C31 C36 C35 179.9(6) . . . . ?
C34 C35 C36 C31 -0.8(11) . . . . ?
C9 N8 C81 O81 -5.9(9) . . . . ?
C7 N8 C81 O81 -173.0(6) . . . . ?
C9 N8 C81 O82 173.5(5) . . . . ?
C7 N8 C81 O82 6.4(7) . . . . ?
O81 C81 O82 C83 3.6(9) . . . . ?
N8 C81 O82 C83 -175.8(4) . . . . ?
C81 O82 C83 C86 60.5(7) . . . . ?
C81 O82 C83 C85 178.9(5) . . . . ?
C81 O82 C83 C84 -63.4(7) . . . . ?

_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.9(6)

########################################################################## 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'
O O 0.0492 0.0322 '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'

_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.
;

_cell_measurement_reflns_used    11555
_cell_measurement_theta_min      3.790
_cell_measurement_theta_max      70.147

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.060
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D. (1983). Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_T_max  0.9443


_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE'
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
'99 runs, 3720 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11555
_diffrn_reflns_av_unetI/netI     0.2659
_diffrn_reflns_av_R_equivalents  0.0817 # before absorption correction
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.790
_diffrn_reflns_theta_max         70.147
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4629
_reflns_number_gt                1574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.988

_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       'X--AREA       (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA       (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA       (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97      (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick,  2015)'
_computing_molecular_graphics    'Ortep--3      (Farrugia,   1997)'
_computing_publication_material  'WinGX         (Farrugia,   1999)'

_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)+(0.0018P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4629
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.527
_refine_ls_restrained_S_all      0.527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030

