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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b_a
_audit_block_doi                 10.5517/ccdc.csd.cc2396rd
_database_code_depnum_ccdc_archive 'CCDC 1945273'
loop_
_audit_author_name
_audit_author_address
'ling ling li'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O'
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_weight         227.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.93000(10)
_cell_length_b                   8.7765(2)
_cell_length_c                   24.7421(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1287.69(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7455
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      68.02

_exptl_crystal_description       block
_exptl_crystal_colour            coulorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.6789
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.571
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18841
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.573
_diffrn_reflns_theta_max         68.308
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2353
_reflns_number_gt                2161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0619P)²+0.0791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(12)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4570(3) 0.49838(18) 0.65247(6) 0.0677(4) Uani 1 1 d . . . . .
N1 N 0.9784(4) 0.6134(3) 0.52633(9) 0.0892(7) Uani 1 1 d . . . . .
C1 C 0.7005(4) 0.3344(2) 0.60148(8) 0.0610(5) Uani 1 1 d . . . . .
C2 C 0.7023(6) 0.2204(3) 0.56291(10) 0.0862(8) Uani 1 1 d . . . . .
H2 H 0.586364 0.215016 0.537662 0.103 Uiso 1 1 calc R U . . .
C3 C 0.8732(8) 0.1153(4) 0.56152(14) 0.1090(11) Uani 1 1 d . . . . .
H3 H 0.873559 0.040094 0.535038 0.131 Uiso 1 1 calc R U . . .
C4 C 1.0434(6) 0.1204(4) 0.59890(17) 0.1075(12) Uani 1 1 d . . . . .
H4 H 1.161052 0.050480 0.597303 0.129 Uiso 1 1 calc R U . . .
C5 C 1.0394(5) 0.2300(3) 0.63902(17) 0.0994(10) Uani 1 1 d . . . . .
H5 H 1.152624 0.232297 0.665028 0.119 Uiso 1 1 calc R U . . .
C7 C 0.5201(3) 0.4527(3) 0.59944(8) 0.0600(5) Uani 1 1 d . . . . .
H7 H 0.387608 0.407438 0.582041 0.072 Uiso 1 1 calc R U . . .
C6 C 0.8676(4) 0.3361(3) 0.64051(12) 0.0775(7) Uani 1 1 d . . . . .
H6 H 0.864080 0.408862 0.667816 0.093 Uiso 1 1 calc R U . . .
C8 C 0.5773(4) 0.6059(3) 0.56906(8) 0.0625(5) Uani 1 1 d . . . . .
H8 H 0.466989 0.619750 0.539976 0.075 Uiso 1 1 calc R U . . .
C9 C 0.5357(4) 0.7294(3) 0.61190(9) 0.0674(6) Uani 1 1 d . . . . .
H9 H 0.468118 0.820005 0.595333 0.081 Uiso 1 1 calc R U . . .
C10 C 0.3641(4) 0.6480(3) 0.64756(10) 0.0719(6) Uani 1 1 d . . . . .
H10 H 0.220128 0.641729 0.628251 0.086 Uiso 1 1 calc R U . . .
C11 C 0.3241(5) 0.7175(4) 0.70262(11) 0.0882(8) Uani 1 1 d . . . . .
H11A H 0.240345 0.645842 0.724697 0.106 Uiso 1 1 calc R U . . .
H11B H 0.232730 0.808452 0.698551 0.106 Uiso 1 1 calc R U . . .
C12 C 0.5411(5) 0.7589(4) 0.73136(12) 0.0982(10) Uani 1 1 d . . . . .
H12A H 0.622249 0.666725 0.740832 0.118 Uiso 1 1 calc R U . . .
H12B H 0.506496 0.813247 0.764478 0.118 Uiso 1 1 calc R U . . .
C13 C 0.6875(6) 0.8579(4) 0.69533(14) 0.1010(10) Uani 1 1 d . . . . .
H13A H 0.607679 0.951047 0.686411 0.121 Uiso 1 1 calc R U . . .
H13B H 0.824781 0.885213 0.714340 0.121 Uiso 1 1 calc R U . . .
C14 C 0.7460(4) 0.7726(3) 0.64392(12) 0.0753(6) Uani 1 1 d . . . . .
H14A H 0.829018 0.680966 0.653071 0.090 Uiso 1 1 calc R U . . .
H14B H 0.842631 0.835905 0.621621 0.090 Uiso 1 1 calc R U . . .
C15 C 0.8040(4) 0.6099(3) 0.54516(9) 0.0670(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.422(3) . ?
O1 C10 1.429(3) . ?
N1 C15 1.135(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.383(3) . ?
C1 C7 1.491(3) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.578(3) . ?
C7 H7 0.9800 . ?
C6 H6 0.9300 . ?
C8 C15 1.469(3) . ?
C8 C9 1.536(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.524(3) . ?
C9 C14 1.526(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.511(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.516(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C7 O1 C10 106.39(17) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 C7 119.0(2) . . ?
C6 C1 C7 122.0(2) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O1 C7 C1 110.72(17) . . ?
O1 C7 C8 104.80(17) . . ?
C1 C7 C8 117.10(17) . . ?
O1 C7 H7 108.0 . . ?
C1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C15 C8 C9 114.1(2) . . ?
C15 C8 C7 114.11(18) . . ?
C9 C8 C7 103.80(16) . . ?
C15 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C10 C9 C14 111.19(19) . . ?
C10 C9 C8 100.13(18) . . ?
C14 C9 C8 113.73(19) . . ?
C10 C9 H9 110.5 . . ?
C14 C9 H9 110.5 . . ?
C8 C9 H9 110.5 . . ?
O1 C10 C11 110.8(2) . . ?
O1 C10 C9 102.87(17) . . ?
C11 C10 C9 115.9(2) . . ?
O1 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C10 C11 C12 112.8(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 110.3(3) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 109.9(2) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C9 111.8(2) . . ?
C13 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N1 C15 C8 179.5(3) . . ?

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 C1 C2 C3 -3.4(4) . . . . ?
C7 C1 C2 C3 176.0(2) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C10 O1 C7 C1 155.87(17) . . . . ?
C10 O1 C7 C8 28.7(2) . . . . ?
C2 C1 C7 O1 145.2(2) . . . . ?
C6 C1 C7 O1 -35.5(3) . . . . ?
C2 C1 C7 C8 -94.8(2) . . . . ?
C6 C1 C7 C8 84.5(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C2 C1 C6 C5 3.4(4) . . . . ?
C7 C1 C6 C5 -176.0(2) . . . . ?
O1 C7 C8 C15 124.6(2) . . . . ?
C1 C7 C8 C15 1.5(3) . . . . ?
O1 C7 C8 C9 -0.2(2) . . . . ?
C1 C7 C8 C9 -123.3(2) . . . . ?
C15 C8 C9 C10 -150.60(19) . . . . ?
C7 C8 C9 C10 -25.8(2) . . . . ?
C15 C8 C9 C14 -31.9(3) . . . . ?
C7 C8 C9 C14 92.9(2) . . . . ?
C7 O1 C10 C11 -171.3(2) . . . . ?
C7 O1 C10 C9 -46.8(2) . . . . ?
C14 C9 C10 O1 -76.6(2) . . . . ?
C8 C9 C10 O1 44.0(2) . . . . ?
C14 C9 C10 C11 44.5(3) . . . . ?
C8 C9 C10 C11 165.0(2) . . . . ?
O1 C10 C11 C12 70.8(3) . . . . ?
C9 C10 C11 C12 -45.9(3) . . . . ?
C10 C11 C12 C13 52.8(3) . . . . ?
C11 C12 C13 C14 -60.3(3) . . . . ?
C12 C13 C14 C9 60.3(3) . . . . ?
C10 C9 C14 C13 -51.3(3) . . . . ?
C8 C9 C14 C13 -163.4(2) . . . . ?

_refine_diff_density_max         0.103
_refine_diff_density_min         -0.142
_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_ta_a
_audit_block_doi                 10.5517/ccdc.csd.cc234pjh
_database_code_depnum_ccdc_archive 'CCDC 1940926'
loop_
_audit_author_name
_audit_author_address
'ling ling li'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-11 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 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.6461(6)
_cell_length_b                   11.4107(16)
_cell_length_c                   24.622(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1305.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4571
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.5193
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8758
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.590
_diffrn_reflns_theta_max         63.758
_diffrn_reflns_theta_full        63.758
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2155
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_max     0.999
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2155
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.8469(6) 1.0117(3) 0.36128(11) 0.0378(7) Uani 1 1 d . . . . .
O2 O -1.5729(7) 0.7558(3) 0.17914(11) 0.0440(8) Uani 1 1 d . . . . .
N1 N -0.5868(10) 0.6117(4) 0.38846(16) 0.0562(11) Uani 1 1 d . . . . .
C1 C -0.6075(8) 1.0340(4) 0.39971(16) 0.0361(9) Uani 1 1 d . . . . .
H1 H -0.4398 1.0604 0.3789 0.043 Uiso 1 1 calc R U . . .
C2 C -0.6887(10) 1.1280(4) 0.43817(16) 0.0423(11) Uani 1 1 d . . . . .
H2 H -0.7617 1.1977 0.4243 0.051 Uiso 1 1 calc R U . . .
C3 C -0.6623(10) 1.1174(4) 0.49103(17) 0.0453(11) Uani 1 1 d . . . . .
H3 H -0.7019 1.1822 0.5127 0.054 Uiso 1 1 calc R U . . .
C4 C -0.5711(11) 1.0055(4) 0.51798(16) 0.0465(11) Uani 1 1 d . . . . .
H4A H -0.6641 0.9988 0.5531 0.056 Uiso 1 1 calc R U . . .
H4B H -0.3646 1.0063 0.5237 0.056 Uiso 1 1 calc R U . . .
C5 C -0.6524(10) 0.9010(4) 0.48276(15) 0.0433(11) Uani 1 1 d . . . . .
H5A H -0.8603 0.8936 0.4816 0.052 Uiso 1 1 calc R U . . .
H5B H -0.5747 0.8300 0.4987 0.052 Uiso 1 1 calc R U . . .
C6 C -0.5367(9) 0.9150(4) 0.42503(16) 0.0374(10) Uani 1 1 d . . . . .
H6 H -0.3278 0.9031 0.4250 0.045 Uiso 1 1 calc R U . . .
C7 C -0.6752(9) 0.8336(4) 0.38427(16) 0.0359(9) Uani 1 1 d . . . . .
C8 C -0.8506(9) 0.8950(4) 0.35093(15) 0.0336(9) Uani 1 1 d . . . . .
C9 C -1.0435(8) 0.8594(4) 0.30642(15) 0.0331(9) Uani 1 1 d . . . . .
C10 C -1.0804(9) 0.7423(4) 0.29209(16) 0.0394(10) Uani 1 1 d . . . . .
H10 H -0.9826 0.6845 0.3113 0.047 Uiso 1 1 calc R U . . .
C11 C -1.2594(9) 0.7105(4) 0.24992(19) 0.0407(10) Uani 1 1 d . . . . .
H11 H -1.2838 0.6318 0.2411 0.049 Uiso 1 1 calc R U . . .
C12 C -1.4042(8) 0.7971(4) 0.22041(16) 0.0358(10) Uani 1 1 d . . . . .
C13 C -1.3698(9) 0.9140(4) 0.23376(15) 0.0371(10) Uani 1 1 d . . . . .
H13 H -1.4656 0.9716 0.2141 0.045 Uiso 1 1 calc R U . . .
C14 C -1.1916(9) 0.9447(4) 0.27669(15) 0.0351(9) Uani 1 1 d . . . . .
H14 H -1.1703 1.0233 0.2858 0.042 Uiso 1 1 calc R U . . .
C15 C -0.6306(10) 0.7104(4) 0.38570(16) 0.0418(10) Uani 1 1 d . . . . .
C16 C -1.7233(11) 0.8406(4) 0.14712(18) 0.0484(12) Uani 1 1 d . . . . .
H16A H -1.5876 0.8940 0.1312 0.073 Uiso 1 1 calc R U . . .
H16B H -1.8547 0.8833 0.1698 0.073 Uiso 1 1 calc R U . . .
H16C H -1.8284 0.8015 0.1189 0.073 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 C8 1.356(5) . ?
O1 C1 1.482(5) . ?
O2 C12 1.367(5) . ?
O2 C16 1.431(6) . ?
N1 C15 1.147(6) . ?
C1 C2 1.480(6) . ?
C1 C6 1.530(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.313(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.500(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.522(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.528(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.512(6) . ?
C6 H6 0.9800 . ?
C7 C8 1.353(6) . ?
C7 C15 1.421(6) . ?
C8 C9 1.473(5) . ?
C9 C10 1.393(6) . ?
C9 C14 1.399(6) . ?
C10 C11 1.379(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(6) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C8 O1 C1 107.4(3) . . ?
C12 O2 C16 117.2(4) . . ?
C2 C1 O1 110.0(3) . . ?
C2 C1 C6 115.9(3) . . ?
O1 C1 C6 105.6(3) . . ?
C2 C1 H1 108.4 . . ?
O1 C1 H1 108.4 . . ?
C6 C1 H1 108.4 . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 122.9(4) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C5 110.2(4) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 111.2(4) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 113.8(4) . . ?
C7 C6 C1 100.6(3) . . ?
C5 C6 C1 113.3(3) . . ?
C7 C6 H6 109.6 . . ?
C5 C6 H6 109.6 . . ?
C1 C6 H6 109.6 . . ?
C8 C7 C15 128.0(4) . . ?
C8 C7 C6 109.9(4) . . ?
C15 C7 C6 122.0(4) . . ?
C7 C8 O1 112.8(3) . . ?
C7 C8 C9 132.5(4) . . ?
O1 C8 C9 114.7(3) . . ?
C10 C9 C14 118.3(4) . . ?
C10 C9 C8 121.9(4) . . ?
C14 C9 C8 119.8(4) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O2 C12 C13 125.1(4) . . ?
O2 C12 C11 114.7(4) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N1 C15 C7 177.3(5) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C8 O1 C1 C2 -144.1(3) . . . . ?
C8 O1 C1 C6 -18.4(4) . . . . ?
O1 C1 C2 C3 129.4(5) . . . . ?
C6 C1 C2 C3 9.8(6) . . . . ?
C1 C2 C3 C4 -5.4(8) . . . . ?
C2 C3 C4 C5 -26.8(6) . . . . ?
C3 C4 C5 C6 53.1(5) . . . . ?
C4 C5 C6 C7 -163.9(4) . . . . ?
C4 C5 C6 C1 -49.8(5) . . . . ?
C2 C1 C6 C7 140.5(4) . . . . ?
O1 C1 C6 C7 18.4(4) . . . . ?
C2 C1 C6 C5 18.6(5) . . . . ?
O1 C1 C6 C5 -103.4(4) . . . . ?
C5 C6 C7 C8 108.3(4) . . . . ?
C1 C6 C7 C8 -13.3(4) . . . . ?
C5 C6 C7 C15 -68.2(5) . . . . ?
C1 C6 C7 C15 170.3(4) . . . . ?
C15 C7 C8 O1 178.6(4) . . . . ?
C6 C7 C8 O1 2.4(5) . . . . ?
C15 C7 C8 C9 -0.9(8) . . . . ?
C6 C7 C8 C9 -177.0(4) . . . . ?
C1 O1 C8 C7 10.3(4) . . . . ?
C1 O1 C8 C9 -170.2(3) . . . . ?
C7 C8 C9 C10 2.0(7) . . . . ?
O1 C8 C9 C10 -177.5(3) . . . . ?
C7 C8 C9 C14 -176.9(4) . . . . ?
O1 C8 C9 C14 3.6(5) . . . . ?
C14 C9 C10 C11 -0.4(6) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C16 O2 C12 C13 0.5(6) . . . . ?
C16 O2 C12 C11 -179.2(3) . . . . ?
C10 C11 C12 O2 179.2(4) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
O2 C12 C13 C14 -179.9(3) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C9 0.6(6) . . . . ?
C10 C9 C14 C13 -0.4(6) . . . . ?
C8 C9 C14 C13 178.6(4) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052

