# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_bwsx1094_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1911403'
loop_
_audit_author_name
_audit_author_address
' Xin Sun'
;Huanghuai University
China
;
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           32
_space_group_name_H-M_alt        'P b a 2'
_space_group_name_Hall           'P 2 -2ab'

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

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

_cell_length_a                   13.9466(16)
_cell_length_b                   23.367(3)
_cell_length_c                   8.8425(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2881.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9001
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.72

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.2902
_exptl_transmission_factor_max   0.3375
_exptl_crystal_size_max          1.800
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31450
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.700
_diffrn_reflns_theta_max         31.054
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8481
_reflns_number_gt                7029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.879
_reflns_Friedel_fraction_full    0.993

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0578P)²+0.1733P] 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 x determined using 2762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8481
_refine_ls_number_parameters     363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.44602(9) 0.66297(5) 0.33624(14) 0.0204(3) Uani 1 1 d . . . . .
O002 O 1.09379(9) 0.66211(5) -0.16176(14) 0.0221(3) Uani 1 1 d . . . . .
O003 O 0.30422(10) 0.62919(7) 0.26266(16) 0.0314(3) Uani 1 1 d . . . . .
O004 O 1.23144(10) 0.62325(7) -0.23601(17) 0.0353(4) Uani 1 1 d . . . . .
N005 N 0.88176(12) 0.53187(7) 0.7421(2) 0.0299(4) Uani 1 1 d . . . . .
N006 N 0.65141(13) 0.52827(7) 1.2368(2) 0.0306(4) Uani 1 1 d . . . . .
C007 C 0.46425(13) 0.58743(7) 0.8064(2) 0.0195(3) Uani 1 1 d . . . . .
H007 H 0.3995 0.5990 0.7933 0.023 Uiso 1 1 calc R U . . .
C008 C 0.94099(12) 0.56381(7) 0.4774(2) 0.0205(3) Uani 1 1 d . . . . .
C009 C 0.61198(12) 0.66447(7) 0.4098(2) 0.0187(3) Uani 1 1 d . . . . .
H009 H 0.6405 0.6335 0.3566 0.022 Uiso 1 1 calc R U . . .
C00A C 0.52374(12) 0.58200(7) 0.6798(2) 0.0174(3) Uani 1 1 d . . . . .
C00B C 0.59277(13) 0.55855(7) 0.9703(2) 0.0201(3) Uani 1 1 d . . . . .
C00C C 0.92765(12) 0.66745(8) -0.0889(2) 0.0194(3) Uani 1 1 d . . . . .
H00C H 0.8979 0.6366 -0.1408 0.023 Uiso 1 1 calc R U . . .
C00D C 0.66334(12) 0.71227(8) 0.4287(2) 0.0206(4) Uani 1 1 d . . . . .
C00E C 0.49812(13) 0.57615(7) 0.9504(2) 0.0202(3) Uani 1 1 d . . . . .
H00E H 0.4570 0.5804 1.0353 0.024 Uiso 1 1 calc R U . . .
C00F C 1.04550(12) 0.59679(7) 0.0280(2) 0.0181(3) Uani 1 1 d . . . . .
H00F H 1.0088 0.5704 -0.0397 0.022 Uiso 1 1 calc R U . . .
C00G C 1.06914(13) 0.59407(7) 0.3140(2) 0.0202(3) Uani 1 1 d . . . . .
H00G H 1.1332 0.6070 0.3013 0.024 Uiso 1 1 calc R U . . .
C00H C 1.01099(12) 0.58598(7) 0.1868(2) 0.0185(3) Uani 1 1 d . . . . .
C00I C 0.90730(13) 0.54715(8) 0.6251(2) 0.0235(4) Uani 1 1 d . . . . .
C00J C 1.15204(12) 0.58803(8) -0.0075(2) 0.0222(4) Uani 1 1 d . . . . .
H00A H 1.1929 0.6011 0.0773 0.027 Uiso 1 1 calc R U . . .
H00B H 1.1662 0.5473 -0.0292 0.027 Uiso 1 1 calc R U . . .
C00K C 0.49039(12) 0.59481(7) 0.52102(19) 0.0168(3) Uani 1 1 d . . . . .
H00K H 0.5257 0.5684 0.4517 0.020 Uiso 1 1 calc R U . . .
C00L C 0.38341(12) 0.58858(8) 0.4855(2) 0.0204(3) Uani 1 1 d . . . . .
H00D H 0.3670 0.5485 0.4602 0.024 Uiso 1 1 calc R U . . .
H00H H 0.3435 0.6012 0.5720 0.024 Uiso 1 1 calc R U . . .
C00M C 1.02712(11) 0.65885(7) -0.0302(2) 0.0175(3) Uani 1 1 d . . . . .
C00N C 1.03456(13) 0.58350(7) 0.4582(2) 0.0206(3) Uani 1 1 d . . . . .
H00N H 1.0745 0.5897 0.5437 0.025 Uiso 1 1 calc R U . . .
C00O C 0.51212(11) 0.65705(7) 0.46783(19) 0.0162(3) Uani 1 1 d . . . . .
C00P C 0.62616(14) 0.54232(8) 1.1184(2) 0.0230(4) Uani 1 1 d . . . . .
C00Q C 0.36995(12) 0.62740(8) 0.3508(2) 0.0215(4) Uani 1 1 d . . . . .
C00R C 1.05634(12) 0.70572(7) 0.08082(19) 0.0184(3) Uani 1 1 d . . . . .
H00J H 1.1265 0.7043 0.0973 0.022 Uiso 1 1 calc R U . . .
H00L H 1.0244 0.6992 0.1793 0.022 Uiso 1 1 calc R U . . .
C00S C 1.16657(13) 0.62465(8) -0.1456(2) 0.0236(4) Uani 1 1 d . . . . .
C00T C 0.88135(13) 0.55616(8) 0.3519(2) 0.0241(4) Uani 1 1 d . . . . .
H00T H 0.8172 0.5433 0.3647 0.029 Uiso 1 1 calc R U . . .
C00U C 0.87835(12) 0.71591(8) -0.0727(2) 0.0214(4) Uani 1 1 d . . . . .
C00V C 0.65377(12) 0.55329(8) 0.8458(2) 0.0235(4) Uani 1 1 d . . . . .
H00V H 0.7185 0.5418 0.8593 0.028 Uiso 1 1 calc R U . . .
C00W C 0.51494(12) 0.76211(7) 0.5248(2) 0.0200(3) Uani 1 1 d . . . . .
H00M H 0.4943 0.7918 0.5979 0.024 Uiso 1 1 calc R U . . .
H00O H 0.4833 0.7700 0.4268 0.024 Uiso 1 1 calc R U . . .
C00X C 1.02848(13) 0.76459(7) 0.0201(2) 0.0207(3) Uani 1 1 d . . . . .
H00Q H 1.0502 0.7946 0.0912 0.025 Uiso 1 1 calc R U . . .
H00R H 1.0602 0.7712 -0.0786 0.025 Uiso 1 1 calc R U . . .
C00Y C 0.61883(13) 0.56501(8) 0.7022(2) 0.0222(4) Uani 1 1 d . . . . .
H00Y H 0.6603 0.5614 0.6175 0.027 Uiso 1 1 calc R U . . .
C00Z C 0.48517(12) 0.70322(7) 0.58198(19) 0.0176(3) Uani 1 1 d . . . . .
H00S H 0.4150 0.7026 0.5991 0.021 Uiso 1 1 calc R U . . .
H00U H 0.5173 0.6953 0.6796 0.021 Uiso 1 1 calc R U . . .
C010 C 0.91678(13) 0.56747(8) 0.2088(2) 0.0235(4) Uani 1 1 d . . . . .
H010 H 0.8761 0.5625 0.1236 0.028 Uiso 1 1 calc R U . . .
C011 C 0.91991(13) 0.76800(8) 0.0010(2) 0.0228(4) Uani 1 1 d . . . . .
H01A H 0.8900 0.7731 0.1016 0.027 Uiso 1 1 calc R U . . .
H01B H 0.9040 0.8020 -0.0609 0.027 Uiso 1 1 calc R U . . .
C012 C 0.62349(13) 0.76438(7) 0.5055(2) 0.0226(4) Uani 1 1 d . . . . .
H01C H 0.6404 0.7987 0.4454 0.027 Uiso 1 1 calc R U . . .
H01D H 0.6537 0.7683 0.6062 0.027 Uiso 1 1 calc R U . . .
C013 C 0.76556(14) 0.71656(9) 0.3754(3) 0.0326(5) Uani 1 1 d . . . . .
H01E H 0.7837 0.6810 0.3240 0.049 Uiso 1 1 calc R U . . .
H01F H 0.8078 0.7227 0.4625 0.049 Uiso 1 1 calc R U . . .
H01G H 0.7718 0.7488 0.3051 0.049 Uiso 1 1 calc R U . . .
C014 C 0.77653(14) 0.72112(10) -0.1260(3) 0.0342(5) Uani 1 1 d . . . . .
H01H H 0.7574 0.6856 -0.1768 0.051 Uiso 1 1 calc R U . . .
H01I H 0.7713 0.7532 -0.1970 0.051 Uiso 1 1 calc R U . . .
H01J H 0.7345 0.7279 -0.0391 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00Q 1.354(2) . ?
O001 C00O 1.491(2) . ?
O002 C00S 1.348(2) . ?
O002 C00M 1.491(2) . ?
O003 C00Q 1.204(2) . ?
O004 C00S 1.208(2) . ?
N005 C00I 1.151(3) . ?
N006 C00P 1.152(3) . ?
C007 C00E 1.383(2) . ?
C007 C00A 1.399(2) . ?
C007 H007 0.9500 . ?
C008 C00N 1.394(3) . ?
C008 C00T 1.398(3) . ?
C008 C00I 1.442(3) . ?
C009 C00D 1.337(2) . ?
C009 C00O 1.494(2) . ?
C009 H009 0.9500 . ?
C00A C00Y 1.398(2) . ?
C00A C00K 1.509(2) . ?
C00B C00E 1.394(2) . ?
C00B C00V 1.397(3) . ?
C00B C00P 1.441(3) . ?
C00C C00U 1.333(2) . ?
C00C C00M 1.495(2) . ?
C00C H00C 0.9500 . ?
C00D C012 1.501(3) . ?
C00D C013 1.505(3) . ?
C00E H00E 0.9500 . ?
C00F C00H 1.506(2) . ?
C00F C00J 1.532(2) . ?
C00F C00M 1.560(2) . ?
C00F H00F 1.0000 . ?
C00G C00N 1.386(3) . ?
C00G C00H 1.399(2) . ?
C00G H00G 0.9500 . ?
C00H C010 1.397(3) . ?
C00J C00S 1.505(3) . ?
C00J H00A 0.9900 . ?
C00J H00B 0.9900 . ?
C00K C00L 1.532(2) . ?
C00K C00O 1.558(2) . ?
C00K H00K 1.0000 . ?
C00L C00Q 1.509(3) . ?
C00L H00D 0.9900 . ?
C00L H00H 0.9900 . ?
C00M C00R 1.526(2) . ?
C00N H00N 0.9500 . ?
C00O C00Z 1.524(2) . ?
C00R C00X 1.527(2) . ?
C00R H00J 0.9900 . ?
C00R H00L 0.9900 . ?
C00T C010 1.384(3) . ?
C00T H00T 0.9500 . ?
C00U C011 1.497(3) . ?
C00U C014 1.501(3) . ?
C00V C00Y 1.387(3) . ?
C00V H00V 0.9500 . ?
C00W C00Z 1.524(2) . ?
C00W C012 1.525(3) . ?
C00W H00M 0.9900 . ?
C00W H00O 0.9900 . ?
C00X C011 1.526(3) . ?
C00X H00Q 0.9900 . ?
C00X H00R 0.9900 . ?
C00Y H00Y 0.9500 . ?
C00Z H00S 0.9900 . ?
C00Z H00U 0.9900 . ?
C010 H010 0.9500 . ?
C011 H01A 0.9900 . ?
C011 H01B 0.9900 . ?
C012 H01C 0.9900 . ?
C012 H01D 0.9900 . ?
C013 H01E 0.9800 . ?
C013 H01F 0.9800 . ?
C013 H01G 0.9800 . ?
C014 H01H 0.9800 . ?
C014 H01I 0.9800 . ?
C014 H01J 0.9800 . ?

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
C00Q O001 C00O 110.70(13) . . ?
C00S O002 C00M 110.71(13) . . ?
C00E C007 C00A 121.10(16) . . ?
C00E C007 H007 119.5 . . ?
C00A C007 H007 119.5 . . ?
C00N C008 C00T 120.16(17) . . ?
C00N C008 C00I 120.29(17) . . ?
C00T C008 C00I 119.39(16) . . ?
C00D C009 C00O 123.59(16) . . ?
C00D C009 H009 118.2 . . ?
C00O C009 H009 118.2 . . ?
C00Y C00A C007 118.36(16) . . ?
C00Y C00A C00K 118.70(16) . . ?
C007 C00A C00K 122.93(15) . . ?
C00E C00B C00V 120.22(16) . . ?
C00E C00B C00P 119.90(17) . . ?
C00V C00B C00P 119.76(16) . . ?
C00U C00C C00M 123.75(16) . . ?
C00U C00C H00C 118.1 . . ?
C00M C00C H00C 118.1 . . ?
C009 C00D C012 122.39(16) . . ?
C009 C00D C013 121.60(17) . . ?
C012 C00D C013 116.01(16) . . ?
C007 C00E C00B 119.73(17) . . ?
C007 C00E H00E 120.1 . . ?
C00B C00E H00E 120.1 . . ?
C00H C00F C00J 118.59(15) . . ?
C00H C00F C00M 114.27(14) . . ?
C00J C00F C00M 102.47(14) . . ?
C00H C00F H00F 106.9 . . ?
C00J C00F H00F 106.9 . . ?
C00M C00F H00F 106.9 . . ?
C00N C00G C00H 120.91(16) . . ?
C00N C00G H00G 119.5 . . ?
C00H C00G H00G 119.5 . . ?
C010 C00H C00G 118.39(17) . . ?
C010 C00H C00F 118.83(16) . . ?
C00G C00H C00F 122.78(15) . . ?
N005 C00I C008 177.5(2) . . ?
C00S C00J C00F 102.75(14) . . ?
C00S C00J H00A 111.2 . . ?
C00F C00J H00A 111.2 . . ?
C00S C00J H00B 111.2 . . ?
C00F C00J H00B 111.2 . . ?
H00A C00J H00B 109.1 . . ?
C00A C00K C00L 118.16(14) . . ?
C00A C00K C00O 113.95(13) . . ?
C00L C00K C00O 102.49(13) . . ?
C00A C00K H00K 107.2 . . ?
C00L C00K H00K 107.2 . . ?
C00O C00K H00K 107.2 . . ?
C00Q C00L C00K 103.05(14) . . ?
C00Q C00L H00D 111.2 . . ?
C00K C00L H00D 111.2 . . ?
C00Q C00L H00H 111.2 . . ?
C00K C00L H00H 111.2 . . ?
H00D C00L H00H 109.1 . . ?
O002 C00M C00C 107.48(14) . . ?
O002 C00M C00R 107.38(13) . . ?
C00C C00M C00R 112.02(14) . . ?
O002 C00M C00F 101.68(12) . . ?
C00C C00M C00F 113.08(14) . . ?
C00R C00M C00F 114.28(14) . . ?
C00G C00N C008 119.78(17) . . ?
C00G C00N H00N 120.1 . . ?
C008 C00N H00N 120.1 . . ?
O001 C00O C009 107.31(14) . . ?
O001 C00O C00Z 107.37(13) . . ?
C009 C00O C00Z 112.03(13) . . ?
O001 C00O C00K 101.65(12) . . ?
C009 C00O C00K 113.15(14) . . ?
C00Z C00O C00K 114.37(14) . . ?
N006 C00P C00B 178.4(2) . . ?
O003 C00Q O001 120.93(17) . . ?
O003 C00Q C00L 128.80(16) . . ?
O001 C00Q C00L 110.27(14) . . ?
C00M C00R C00X 110.63(14) . . ?
C00M C00R H00J 109.5 . . ?
C00X C00R H00J 109.5 . . ?
C00M C00R H00L 109.5 . . ?
C00X C00R H00L 109.5 . . ?
H00J C00R H00L 108.1 . . ?
O004 C00S O002 120.78(18) . . ?
O004 C00S C00J 128.50(17) . . ?
O002 C00S C00J 110.72(15) . . ?
C010 C00T C008 119.27(16) . . ?
C010 C00T H00T 120.4 . . ?
C008 C00T H00T 120.4 . . ?
C00C C00U C011 122.54(16) . . ?
C00C C00U C014 121.55(18) . . ?
C011 C00U C014 115.91(16) . . ?
C00Y C00V C00B 119.34(16) . . ?
C00Y C00V H00V 120.3 . . ?
C00B C00V H00V 120.3 . . ?
C00Z C00W C012 109.84(14) . . ?
C00Z C00W H00M 109.7 . . ?
C012 C00W H00M 109.7 . . ?
C00Z C00W H00O 109.7 . . ?
C012 C00W H00O 109.7 . . ?
H00M C00W H00O 108.2 . . ?
C011 C00X C00R 109.78(14) . . ?
C011 C00X H00Q 109.7 . . ?
C00R C00X H00Q 109.7 . . ?
C011 C00X H00R 109.7 . . ?
C00R C00X H00R 109.7 . . ?
H00Q C00X H00R 108.2 . . ?
C00V C00Y C00A 121.24(17) . . ?
C00V C00Y H00Y 119.4 . . ?
C00A C00Y H00Y 119.4 . . ?
C00W C00Z C00O 110.63(14) . . ?
C00W C00Z H00S 109.5 . . ?
C00O C00Z H00S 109.5 . . ?
C00W C00Z H00U 109.5 . . ?
C00O C00Z H00U 109.5 . . ?
H00S C00Z H00U 108.1 . . ?
C00T C010 C00H 121.47(17) . . ?
C00T C010 H010 119.3 . . ?
C00H C010 H010 119.3 . . ?
C00U C011 C00X 112.96(15) . . ?
C00U C011 H01A 109.0 . . ?
C00X C011 H01A 109.0 . . ?
C00U C011 H01B 109.0 . . ?
C00X C011 H01B 109.0 . . ?
H01A C011 H01B 107.8 . . ?
C00D C012 C00W 112.97(15) . . ?
C00D C012 H01C 109.0 . . ?
C00W C012 H01C 109.0 . . ?
C00D C012 H01D 109.0 . . ?
C00W C012 H01D 109.0 . . ?
H01C C012 H01D 107.8 . . ?
C00D C013 H01E 109.5 . . ?
C00D C013 H01F 109.5 . . ?
H01E C013 H01F 109.5 . . ?
C00D C013 H01G 109.5 . . ?
H01E C013 H01G 109.5 . . ?
H01F C013 H01G 109.5 . . ?
C00U C014 H01H 109.5 . . ?
C00U C014 H01I 109.5 . . ?
H01H C014 H01I 109.5 . . ?
C00U C014 H01J 109.5 . . ?
H01H C014 H01J 109.5 . . ?
H01I C014 H01J 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
C00E C007 C00A C00Y -0.2(3) . . . . ?
C00E C007 C00A C00K -178.93(16) . . . . ?
C00O C009 C00D C012 -2.5(3) . . . . ?
C00O C009 C00D C013 176.67(18) . . . . ?
C00A C007 C00E C00B -0.6(3) . . . . ?
C00V C00B C00E C007 1.2(3) . . . . ?
C00P C00B C00E C007 -175.00(16) . . . . ?
C00N C00G C00H C010 0.6(2) . . . . ?
C00N C00G C00H C00F -179.87(16) . . . . ?
C00J C00F C00H C010 -150.34(17) . . . . ?
C00M C00F C00H C010 88.64(19) . . . . ?
C00J C00F C00H C00G 30.1(2) . . . . ?
C00M C00F C00H C00G -90.90(19) . . . . ?
C00H C00F C00J C00S -157.22(14) . . . . ?
C00M C00F C00J C00S -30.36(17) . . . . ?
C00Y C00A C00K C00L 154.72(16) . . . . ?
C007 C00A C00K C00L -26.6(2) . . . . ?
C00Y C00A C00K C00O -84.87(19) . . . . ?
C007 C00A C00K C00O 93.85(19) . . . . ?
C00A C00K C00L C00Q 156.16(14) . . . . ?
C00O C00K C00L C00Q 29.99(16) . . . . ?
C00S O002 C00M C00C -143.44(15) . . . . ?
C00S O002 C00M C00R 95.87(16) . . . . ?
C00S O002 C00M C00F -24.44(17) . . . . ?
C00U C00C C00M O002 -104.3(2) . . . . ?
C00U C00C C00M C00R 13.4(3) . . . . ?
C00U C00C C00M C00F 144.33(18) . . . . ?
C00H C00F C00M O002 162.68(13) . . . . ?
C00J C00F C00M O002 33.09(15) . . . . ?
C00H C00F C00M C00C -82.39(18) . . . . ?
C00J C00F C00M C00C 148.02(15) . . . . ?
C00H C00F C00M C00R 47.35(19) . . . . ?
C00J C00F C00M C00R -82.24(16) . . . . ?
C00H C00G C00N C008 0.8(3) . . . . ?
C00T C008 C00N C00G -1.7(3) . . . . ?
C00I C008 C00N C00G 173.71(16) . . . . ?
C00Q O001 C00O C009 144.71(14) . . . . ?
C00Q O001 C00O C00Z -94.68(15) . . . . ?
C00Q O001 C00O C00K 25.72(16) . . . . ?
C00D C009 C00O O001 103.56(19) . . . . ?
C00D C009 C00O C00Z -14.1(2) . . . . ?
C00D C009 C00O C00K -145.15(17) . . . . ?
C00A C00K C00O O001 -162.39(13) . . . . ?
C00L C00K C00O O001 -33.54(15) . . . . ?
C00A C00K C00O C009 82.87(18) . . . . ?
C00L C00K C00O C009 -148.28(15) . . . . ?
C00A C00K C00O C00Z -47.05(19) . . . . ?
C00L C00K C00O C00Z 81.81(16) . . . . ?
C00O O001 C00Q O003 173.65(16) . . . . ?
C00O O001 C00Q C00L -6.81(19) . . . . ?
C00K C00L C00Q O003 163.95(19) . . . . ?
C00K C00L C00Q O001 -15.54(18) . . . . ?
O002 C00M C00R C00X 72.60(16) . . . . ?
C00C C00M C00R C00X -45.2(2) . . . . ?
C00F C00M C00R C00X -175.45(14) . . . . ?
C00M O002 C00S O004 -175.40(17) . . . . ?
C00M O002 C00S C00J 5.20(19) . . . . ?
C00F C00J C00S O004 -162.55(19) . . . . ?
C00F C00J C00S O002 16.80(19) . . . . ?
C00N C008 C00T C010 1.0(3) . . . . ?
C00I C008 C00T C010 -174.39(17) . . . . ?
C00M C00C C00U C011 2.8(3) . . . . ?
C00M C00C C00U C014 -176.40(18) . . . . ?
C00E C00B C00V C00Y -0.9(3) . . . . ?
C00P C00B C00V C00Y 175.30(17) . . . . ?
C00M C00R C00X C011 61.65(18) . . . . ?
C00B C00V C00Y C00A 0.0(3) . . . . ?
C007 C00A C00Y C00V 0.5(3) . . . . ?
C00K C00A C00Y C00V 179.28(16) . . . . ?
C012 C00W C00Z C00O -61.94(18) . . . . ?
O001 C00O C00Z C00W -71.78(16) . . . . ?
C009 C00O C00Z C00W 45.80(19) . . . . ?
C00K C00O C00Z C00W 176.26(14) . . . . ?
C008 C00T C010 C00H 0.4(3) . . . . ?
C00G C00H C010 C00T -1.2(3) . . . . ?
C00F C00H C010 C00T 179.20(16) . . . . ?
C00C C00U C011 C00X 13.6(3) . . . . ?
C014 C00U C011 C00X -167.11(17) . . . . ?
C00R C00X C011 C00U -45.0(2) . . . . ?
C009 C00D C012 C00W -13.5(3) . . . . ?
C013 C00D C012 C00W 167.29(17) . . . . ?
C00Z C00W C012 C00D 44.8(2) . . . . ?

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
C00L H00H O004 0.99 2.36 3.348(2) 172.1 1_456
C00L H00D N006 0.99 2.68 3.540(2) 145.3 2_664
C00J H00A O003 0.99 2.35 3.337(2) 173.8 1_655
C00C H00C N005 0.95 2.67 3.561(2) 157.0 1_554
C009 H009 N006 0.95 2.68 3.574(3) 156.5 1_554
C00L H00H O004 0.99 2.36 3.348(2) 172.1 1_456
C00L H00D N006 0.99 2.68 3.540(2) 145.3 2_664
C00J H00A O003 0.99 2.35 3.337(2) 173.8 1_655
C00C H00C N005 0.95 2.67 3.561(2) 157.0 1_554
C009 H009 N006 0.95 2.68 3.574(3) 156.5 1_554
C009 H009 N006 0.95 2.68 3.574(3) 156.5 1_554
C00C H00C N005 0.95 2.67 3.561(2) 157.0 1_554
C00J H00A O003 0.99 2.35 3.337(2) 173.8 1_655
C00L H00D N006 0.99 2.68 3.540(2) 145.3 2_664
C00L H00H O004 0.99 2.36 3.348(2) 172.1 1_456

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_mo_bwsx1271_0m
_database_code_depnum_ccdc_archive 'CCDC 1911404'
loop_
_audit_author_name
_audit_author_address
' Xin Sun'
;Huanghuai University
China
;
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 F3 O2'
_chemical_formula_sum            'C16 H15 F3 O2'
_chemical_formula_weight         296.28

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.5914(10)
_cell_length_b                   16.4477(16)
_cell_length_c                   7.9363(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.959(2)
_cell_angle_gamma                90
_cell_volume                     1372.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3782
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      29.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.5189
_exptl_transmission_factor_max   0.5647
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15271
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.937
_diffrn_reflns_theta_max         30.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4091
_reflns_number_gt                3096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0723P)²+0.2364P] 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         4091
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.80204(9) 1.20412(5) 0.54348(12) 0.0336(2) Uani 1 1 d . . . . .
F2 F 0.80523(10) 1.07027(6) 0.34889(11) 0.0378(3) Uani 1 1 d . . . . .
F3 F 0.85572(8) 1.04176(5) 1.03348(10) 0.0253(2) Uani 1 1 d . . . . .
O1 O 0.76554(9) 0.76743(6) 0.91307(12) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.91230(10) 0.68264(6) 0.83656(13) 0.0246(2) Uani 1 1 d . . . . .
C1 C 0.81548(13) 1.13048(8) 0.61880(19) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.82912(13) 1.12442(8) 0.79242(18) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.8298 1.1714 0.8623 0.027 Uiso 1 1 calc R U . . .
C3 C 0.84185(12) 1.04728(8) 0.86176(16) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.84229(12) 0.97626(8) 0.76719(15) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.85446(12) 0.89465(7) 0.85546(16) 0.0159(2) Uani 1 1 d . . . . .
H3 H 0.9037 0.9035 0.9696 0.019 Uiso 1 1 calc R U . . .
C6 C 0.72587(12) 0.85391(8) 0.88478(16) 0.0173(3) Uani 1 1 d . . . . .
C7 C 0.67711(13) 0.88225(8) 1.04402(17) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.7373 0.8973 1.1374 0.024 Uiso 1 1 calc R U . . .
C8 C 0.55321(13) 0.88751(8) 1.06218(18) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.45063(13) 0.86430(9) 0.9228(2) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.4080 0.9143 0.8752 0.031 Uiso 1 1 calc R U . . .
H10 H 0.3862 0.8309 0.9714 0.031 Uiso 1 1 calc R U . . .
C10 C 0.81650(14) 1.06175(9) 0.51908(17) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.83033(14) 0.98513(8) 0.59075(16) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.8317 0.9386 0.5202 0.026 Uiso 1 1 calc R U . . .
C12 C 0.87077(13) 0.75083(8) 0.83829(16) 0.0187(3) Uani 1 1 d . . . . .
C13 C 0.92173(13) 0.82766(8) 0.76791(17) 0.0193(3) Uani 1 1 d . . . . .
H5 H 0.9004 0.8304 0.6431 0.023 Uiso 1 1 calc R U . . .
H4 H 1.0152 0.8314 0.7964 0.023 Uiso 1 1 calc R U . . .
C14 C 0.62354(13) 0.85476(8) 0.73219(17) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.6534 0.8239 0.6375 0.025 Uiso 1 1 calc R U . . .
H13 H 0.6068 0.9114 0.6938 0.025 Uiso 1 1 calc R U . . .
C15 C 0.50111(14) 0.81673(9) 0.7797(2) 0.0268(3) Uani 1 1 d . . . . .
H11 H 0.4361 0.8162 0.6790 0.032 Uiso 1 1 calc R U . . .
H12 H 0.5178 0.7598 0.8162 0.032 Uiso 1 1 calc R U . . .
C16 C 0.51036(15) 0.91859(9) 1.2241(2) 0.0289(3) Uani 1 1 d . . . . .
H7 H 0.5846 0.9355 1.3020 0.043 Uiso 1 1 calc R U . . .
H8 H 0.4650 0.8754 1.2769 0.043 Uiso 1 1 calc R U . . .
H9 H 0.4535 0.9652 1.1989 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3506(15) . ?
F2 C10 1.3487(16) . ?
F3 C3 1.3560(15) . ?
O1 C12 1.3525(16) . ?
O1 C6 1.4923(15) . ?
O2 C12 1.2054(16) . ?
C1 C2 1.372(2) . ?
C1 C10 1.381(2) . ?
C2 C3 1.3829(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3887(17) . ?
C4 C11 1.3983(17) . ?
C4 C5 1.5124(17) . ?
C5 C13 1.5246(17) . ?
C5 C6 1.5604(18) . ?
C5 H3 1.0000 . ?
C6 C7 1.4964(18) . ?
C6 C14 1.5243(19) . ?
C7 C8 1.3402(19) . ?
C7 H6 0.9500 . ?
C8 C9 1.503(2) . ?
C8 C16 1.503(2) . ?
C9 C15 1.528(2) . ?
C9 H1 0.9900 . ?
C9 H10 0.9900 . ?
C10 C11 1.3832(19) . ?
C11 H15 0.9500 . ?
C12 C13 1.5077(19) . ?
C13 H5 0.9900 . ?
C13 H4 0.9900 . ?
C14 C15 1.528(2) . ?
C14 H14 0.9900 . ?
C14 H13 0.9900 . ?
C15 H11 0.9900 . ?
C15 H12 0.9900 . ?
C16 H7 0.9800 . ?
C16 H8 0.9800 . ?
C16 H9 0.9800 . ?

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
C12 O1 C6 111.00(10) . . ?
F1 C1 C2 120.16(13) . . ?
F1 C1 C10 119.23(13) . . ?
C2 C1 C10 120.61(12) . . ?
C1 C2 C3 117.37(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
F3 C3 C2 117.06(11) . . ?
F3 C3 C4 118.67(11) . . ?
C2 C3 C4 124.27(12) . . ?
C3 C4 C11 116.60(11) . . ?
C3 C4 C5 120.13(11) . . ?
C11 C4 C5 123.27(11) . . ?
C4 C5 C13 116.66(11) . . ?
C4 C5 C6 115.05(10) . . ?
C13 C5 C6 102.83(10) . . ?
C4 C5 H3 107.2 . . ?
C13 C5 H3 107.2 . . ?
C6 C5 H3 107.2 . . ?
O1 C6 C7 106.83(10) . . ?
O1 C6 C14 106.76(10) . . ?
C7 C6 C14 112.53(11) . . ?
O1 C6 C5 101.35(9) . . ?
C7 C6 C5 112.89(11) . . ?
C14 C6 C5 115.28(11) . . ?
C8 C7 C6 123.61(13) . . ?
C8 C7 H6 118.2 . . ?
C6 C7 H6 118.2 . . ?
C7 C8 C9 122.31(13) . . ?
C7 C8 C16 120.99(14) . . ?
C9 C8 C16 116.69(13) . . ?
C8 C9 C15 112.97(12) . . ?
C8 C9 H1 109.0 . . ?
C15 C9 H1 109.0 . . ?
C8 C9 H10 109.0 . . ?
C15 C9 H10 109.0 . . ?
H1 C9 H10 107.8 . . ?
F2 C10 C1 118.89(12) . . ?
F2 C10 C11 119.90(13) . . ?
C1 C10 C11 121.20(12) . . ?
C10 C11 C4 119.94(12) . . ?
C10 C11 H15 120.0 . . ?
C4 C11 H15 120.0 . . ?
O2 C12 O1 120.94(12) . . ?
O2 C12 C13 128.91(13) . . ?
O1 C12 C13 110.14(11) . . ?
C12 C13 C5 103.23(10) . . ?
C12 C13 H5 111.1 . . ?
C5 C13 H5 111.1 . . ?
C12 C13 H4 111.1 . . ?
C5 C13 H4 111.1 . . ?
H5 C13 H4 109.1 . . ?
C6 C14 C15 110.08(11) . . ?
C6 C14 H14 109.6 . . ?
C15 C14 H14 109.6 . . ?
C6 C14 H13 109.6 . . ?
C15 C14 H13 109.6 . . ?
H14 C14 H13 108.2 . . ?
C9 C15 C14 110.96(11) . . ?
C9 C15 H11 109.4 . . ?
C14 C15 H11 109.4 . . ?
C9 C15 H12 109.4 . . ?
C14 C15 H12 109.4 . . ?
H11 C15 H12 108.0 . . ?
C8 C16 H7 109.5 . . ?
C8 C16 H8 109.5 . . ?
H7 C16 H8 109.5 . . ?
C8 C16 H9 109.5 . . ?
H7 C16 H9 109.5 . . ?
H8 C16 H9 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
F1 C1 C2 C3 179.69(12) . . . . ?
C10 C1 C2 C3 -0.9(2) . . . . ?
C1 C2 C3 F3 179.79(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
F3 C3 C4 C11 -178.73(11) . . . . ?
C2 C3 C4 C11 0.7(2) . . . . ?
F3 C3 C4 C5 1.64(19) . . . . ?
C2 C3 C4 C5 -178.90(13) . . . . ?
C3 C4 C5 C13 -148.82(13) . . . . ?
C11 C4 C5 C13 31.57(18) . . . . ?
C3 C4 C5 C6 90.58(15) . . . . ?
C11 C4 C5 C6 -89.02(15) . . . . ?
C12 O1 C6 C7 -143.33(11) . . . . ?
C12 O1 C6 C14 96.06(12) . . . . ?
C12 O1 C6 C5 -24.96(13) . . . . ?
C4 C5 C6 O1 160.81(10) . . . . ?
C13 C5 C6 O1 32.90(12) . . . . ?
C4 C5 C6 C7 -85.27(13) . . . . ?
C13 C5 C6 C7 146.82(11) . . . . ?
C4 C5 C6 C14 45.97(15) . . . . ?
C13 C5 C6 C14 -81.94(13) . . . . ?
O1 C6 C7 C8 -100.60(14) . . . . ?
C14 C6 C7 C8 16.26(18) . . . . ?
C5 C6 C7 C8 148.86(13) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C6 C7 C8 C16 -178.36(12) . . . . ?
C7 C8 C9 C15 13.43(19) . . . . ?
C16 C8 C9 C15 -167.54(12) . . . . ?
F1 C1 C10 F2 0.6(2) . . . . ?
C2 C1 C10 F2 -178.76(13) . . . . ?
F1 C1 C10 C11 179.85(13) . . . . ?
C2 C1 C10 C11 0.5(2) . . . . ?
F2 C10 C11 C4 179.87(13) . . . . ?
C1 C10 C11 C4 0.6(2) . . . . ?
C3 C4 C11 C10 -1.2(2) . . . . ?
C5 C4 C11 C10 178.42(13) . . . . ?
C6 O1 C12 O2 -174.67(12) . . . . ?
C6 O1 C12 C13 6.38(14) . . . . ?
O2 C12 C13 C5 -163.22(14) . . . . ?
O1 C12 C13 C5 15.63(14) . . . . ?
C4 C5 C13 C12 -156.63(11) . . . . ?
C6 C5 C13 C12 -29.74(13) . . . . ?
O1 C6 C14 C15 70.89(13) . . . . ?
C7 C6 C14 C15 -46.00(14) . . . . ?
C5 C6 C14 C15 -177.42(11) . . . . ?
C8 C9 C15 C14 -43.69(17) . . . . ?
C6 C14 C15 C9 60.68(15) . . . . ?

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
C13 H5 O2 0.99 2.46 3.4169(17) 162.2 4_575
C7 H6 O2 0.95 2.64 3.3665(18) 133.9 4_576
C2 H2 F1 0.95 2.54 3.4848(16) 173.0 4_586
C13 H5 O2 0.99 2.46 3.4169(17) 162.2 4_575
C7 H6 O2 0.95 2.64 3.3665(18) 133.9 4_576
C2 H2 F1 0.95 2.54 3.4848(16) 173.0 4_586
C2 H2 F1 0.95 2.54 3.4848(16) 173.0 4_586
C7 H6 O2 0.95 2.64 3.3665(18) 133.9 4_576
C13 H5 O2 0.99 2.46 3.4169(17) 162.2 4_575
C2 H2 F1 0.95 2.54 3.4848(16) 173.0 4_586
C7 H6 O2 0.95 2.64 3.3665(18) 133.9 4_576
C13 H5 O2 0.99 2.46 3.4169(17) 162.2 4_575
C2 H2 F1 0.95 2.54 3.4848(16) 173.0 4_586
C7 H6 O2 0.95 2.64 3.3665(18) 133.9 4_576
C13 H5 O2 0.99 2.46 3.4169(17) 162.2 4_575

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_mo_bwsx01093_0m
_database_code_depnum_ccdc_archive 'CCDC 2111150'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-09-22 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5290(10)
_cell_length_b                   17.7336(19)
_cell_length_c                   8.6854(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.621(2)
_cell_angle_gamma                90
_cell_volume                     1390.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6517
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   0.3936
_exptl_transmission_factor_max   0.4334
_exptl_crystal_size_max          0.870
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15426
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.255
_diffrn_reflns_theta_max         30.942
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4108
_reflns_number_gt                3473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0562P)²+0.3579P] 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         4108
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04908(7) 0.07947(4) 0.76205(8) 0.01814(15) Uani 1 1 d . . . . .
O2 O 1.22236(8) 0.06558(4) 1.00309(9) 0.02336(17) Uani 1 1 d . . . . .
N1 N 0.17759(10) 0.25088(5) 0.84857(13) 0.0286(2) Uani 1 1 d . . . . .
C1 C 0.73394(13) 0.03933(7) 0.36865(12) 0.0264(2) Uani 1 1 d . . . . .
H1 H 0.6407 0.0675 0.3191 0.032 Uiso 1 1 calc R U . . .
H8 H 0.7405 -0.0004 0.2913 0.032 Uiso 1 1 calc R U . . .
C2 C 0.72969(11) 0.00295(6) 0.52408(12) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.79995(10) 0.03283(5) 0.66973(11) 0.01678(18) Uani 1 1 d . . . . .
H16 H 0.7916 0.0078 0.7631 0.020 Uiso 1 1 calc R U . . .
C4 C 0.89100(10) 0.10334(5) 0.69481(11) 0.01543(18) Uani 1 1 d . . . . .
C5 C 0.87401(10) 0.15553(5) 0.83215(11) 0.01460(17) Uani 1 1 d . . . . .
H17 H 0.9162 0.2057 0.8178 0.018 Uiso 1 1 calc R U . . .
C6 C 0.71677(10) 0.16950(5) 0.82948(11) 0.01409(17) Uani 1 1 d . . . . .
C7 C 0.64153(10) 0.12215(5) 0.90625(11) 0.01606(18) Uani 1 1 d . . . . .
H3 H 0.6880 0.0773 0.9579 0.019 Uiso 1 1 calc R U . . .
C8 C 0.49977(10) 0.13994(5) 0.90769(11) 0.01722(18) Uani 1 1 d . . . . .
H2 H 0.4494 0.1072 0.9590 0.021 Uiso 1 1 calc R U . . .
C9 C 0.43195(10) 0.20633(5) 0.83295(11) 0.01631(18) Uani 1 1 d . . . . .
C10 C 0.28915(11) 0.22948(5) 0.84114(13) 0.0203(2) Uani 1 1 d . . . . .
C11 C 0.64391(10) 0.23389(5) 0.74980(11) 0.01649(18) Uani 1 1 d . . . . .
H5 H 0.6918 0.2652 0.6931 0.020 Uiso 1 1 calc R U . . .
C12 C 0.50324(11) 0.25296(5) 0.75174(11) 0.01714(18) Uani 1 1 d . . . . .
H4 H 0.4559 0.2973 0.6984 0.021 Uiso 1 1 calc R U . . .
C13 C 1.09917(10) 0.08618(5) 0.92439(12) 0.01737(18) Uani 1 1 d . . . . .
C14 C 0.98142(10) 0.12020(6) 0.98567(11) 0.01738(18) Uani 1 1 d . . . . .
H7 H 1.0239 0.1589 1.0699 0.021 Uiso 1 1 calc R U . . .
H6 H 0.9318 0.0810 1.0309 0.021 Uiso 1 1 calc R U . . .
C15 C 0.86455(13) 0.09288(6) 0.39693(12) 0.0251(2) Uani 1 1 d . . . . .
H9 H 0.8530 0.1227 0.2972 0.030 Uiso 1 1 calc R U . . .
H10 H 0.9574 0.0635 0.4214 0.030 Uiso 1 1 calc R U . . .
C16 C 0.87356(12) 0.14604(6) 0.53812(12) 0.0207(2) Uani 1 1 d . . . . .
H11 H 0.9588 0.1805 0.5545 0.025 Uiso 1 1 calc R U . . .
H12 H 0.7825 0.1771 0.5107 0.025 Uiso 1 1 calc R U . . .
C17 C 0.64375(13) -0.06909(6) 0.50893(15) 0.0295(2) Uani 1 1 d . . . . .
H13 H 0.6400 -0.0842 0.6161 0.044 Uiso 1 1 calc R U . . .
H15 H 0.6923 -0.1087 0.4657 0.044 Uiso 1 1 calc R U . . .
H14 H 0.5428 -0.0614 0.4351 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3417(12) . ?
O1 C4 1.4926(11) . ?
O2 C13 1.2110(12) . ?
N1 C10 1.1498(14) . ?
C1 C2 1.5084(15) . ?
C1 C15 1.5219(17) . ?
C1 H1 0.9900 . ?
C1 H8 0.9900 . ?
C2 C3 1.3373(13) . ?
C2 C17 1.5005(15) . ?
C3 C4 1.4977(13) . ?
C3 H16 0.9500 . ?
C4 C16 1.5194(13) . ?
C4 C5 1.5584(12) . ?
C5 C6 1.5116(12) . ?
C5 C14 1.5318(13) . ?
C5 H17 1.0000 . ?
C6 C11 1.3993(13) . ?
C6 C7 1.4032(13) . ?
C7 C8 1.3911(13) . ?
C7 H3 0.9500 . ?
C8 C9 1.3991(13) . ?
C8 H2 0.9500 . ?
C9 C12 1.3960(13) . ?
C9 C10 1.4446(13) . ?
C11 C12 1.3878(13) . ?
C11 H5 0.9500 . ?
C12 H4 0.9500 . ?
C13 C14 1.5125(13) . ?
C14 H7 0.9900 . ?
C14 H6 0.9900 . ?
C15 C16 1.5272(14) . ?
C15 H9 0.9900 . ?
C15 H10 0.9900 . ?
C16 H11 0.9900 . ?
C16 H12 0.9900 . ?
C17 H13 0.9800 . ?
C17 H15 0.9800 . ?
C17 H14 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C4 111.22(7) . . ?
C2 C1 C15 112.13(9) . . ?
C2 C1 H1 109.2 . . ?
C15 C1 H1 109.2 . . ?
C2 C1 H8 109.2 . . ?
C15 C1 H8 109.2 . . ?
H1 C1 H8 107.9 . . ?
C3 C2 C17 120.98(10) . . ?
C3 C2 C1 121.93(10) . . ?
C17 C2 C1 117.09(9) . . ?
C2 C3 C4 124.07(9) . . ?
C2 C3 H16 118.0 . . ?
C4 C3 H16 118.0 . . ?
O1 C4 C3 106.59(7) . . ?
O1 C4 C16 107.45(7) . . ?
C3 C4 C16 113.15(8) . . ?
O1 C4 C5 101.97(7) . . ?
C3 C4 C5 114.22(7) . . ?
C16 C4 C5 112.41(7) . . ?
C6 C5 C14 117.64(8) . . ?
C6 C5 C4 115.48(7) . . ?
C14 C5 C4 102.68(7) . . ?
C6 C5 H17 106.8 . . ?
C14 C5 H17 106.8 . . ?
C4 C5 H17 106.8 . . ?
C11 C6 C7 118.38(8) . . ?
C11 C6 C5 118.30(8) . . ?
C7 C6 C5 123.30(8) . . ?
C8 C7 C6 120.89(8) . . ?
C8 C7 H3 119.6 . . ?
C6 C7 H3 119.6 . . ?
C7 C8 C9 119.52(9) . . ?
C7 C8 H2 120.2 . . ?
C9 C8 H2 120.2 . . ?
C12 C9 C8 120.38(8) . . ?
C12 C9 C10 118.33(9) . . ?
C8 C9 C10 121.27(9) . . ?
N1 C10 C9 177.20(11) . . ?
C12 C11 C6 121.43(9) . . ?
C12 C11 H5 119.3 . . ?
C6 C11 H5 119.3 . . ?
C11 C12 C9 119.31(9) . . ?
C11 C12 H4 120.3 . . ?
C9 C12 H4 120.3 . . ?
O2 C13 O1 121.46(9) . . ?
O2 C13 C14 128.03(9) . . ?
O1 C13 C14 110.50(8) . . ?
C13 C14 C5 102.79(7) . . ?
C13 C14 H7 111.2 . . ?
C5 C14 H7 111.2 . . ?
C13 C14 H6 111.2 . . ?
C5 C14 H6 111.2 . . ?
H7 C14 H6 109.1 . . ?
C1 C15 C16 110.38(8) . . ?
C1 C15 H9 109.6 . . ?
C16 C15 H9 109.6 . . ?
C1 C15 H10 109.6 . . ?
C16 C15 H10 109.6 . . ?
H9 C15 H10 108.1 . . ?
C4 C16 C15 111.94(8) . . ?
C4 C16 H11 109.2 . . ?
C15 C16 H11 109.2 . . ?
C4 C16 H12 109.2 . . ?
C15 C16 H12 109.2 . . ?
H11 C16 H12 107.9 . . ?
C2 C17 H13 109.5 . . ?
C2 C17 H15 109.5 . . ?
H13 C17 H15 109.5 . . ?
C2 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
H15 C17 H14 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
C15 C1 C2 C3 20.64(13) . . . . ?
C15 C1 C2 C17 -158.88(9) . . . . ?
C17 C2 C3 C4 178.36(9) . . . . ?
C1 C2 C3 C4 -1.14(15) . . . . ?
C13 O1 C4 C3 -97.64(8) . . . . ?
C13 O1 C4 C16 140.78(8) . . . . ?
C13 O1 C4 C5 22.41(9) . . . . ?
C2 C3 C4 O1 -107.28(10) . . . . ?
C2 C3 C4 C16 10.61(13) . . . . ?
C2 C3 C4 C5 140.93(9) . . . . ?
O1 C4 C5 C6 -160.99(7) . . . . ?
C3 C4 C5 C6 -46.44(11) . . . . ?
C16 C4 C5 C6 84.24(10) . . . . ?
O1 C4 C5 C14 -31.64(8) . . . . ?
C3 C4 C5 C14 82.90(9) . . . . ?
C16 C4 C5 C14 -146.42(8) . . . . ?
C14 C5 C6 C11 144.18(9) . . . . ?
C4 C5 C6 C11 -94.22(10) . . . . ?
C14 C5 C6 C7 -34.21(12) . . . . ?
C4 C5 C6 C7 87.40(11) . . . . ?
C11 C6 C7 C8 -2.02(13) . . . . ?
C5 C6 C7 C8 176.37(8) . . . . ?
C6 C7 C8 C9 -0.64(14) . . . . ?
C7 C8 C9 C12 2.59(14) . . . . ?
C7 C8 C9 C10 -175.76(9) . . . . ?
C7 C6 C11 C12 2.82(13) . . . . ?
C5 C6 C11 C12 -175.64(8) . . . . ?
C6 C11 C12 C9 -0.94(14) . . . . ?
C8 C9 C12 C11 -1.81(14) . . . . ?
C10 C9 C12 C11 176.59(9) . . . . ?
C4 O1 C13 O2 175.70(8) . . . . ?
C4 O1 C13 C14 -3.34(10) . . . . ?
O2 C13 C14 C5 163.43(10) . . . . ?
O1 C13 C14 C5 -17.61(10) . . . . ?
C6 C5 C14 C13 157.89(8) . . . . ?
C4 C5 C14 C13 29.90(9) . . . . ?
C2 C1 C15 C16 -48.52(11) . . . . ?
O1 C4 C16 C15 78.13(10) . . . . ?
C3 C4 C16 C15 -39.24(11) . . . . ?
C5 C4 C16 C15 -170.47(8) . . . . ?
C1 C15 C16 C4 59.09(11) . . . . ?

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
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655
C3 H16 O2 0.95 2.45 3.3987(12) 175.6 3_757
C5 H17 N1 1.00 2.55 3.3143(13) 133.3 1_655

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054

