# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1870445'
_audit_update_record             
;
2018-09-28 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   10.598(5)
_cell_length_b                   11.469(5)
_cell_length_c                   12.275(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1492.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4711
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      68.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.5770
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.727
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.868
_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      300(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            7294
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.278
_diffrn_reflns_theta_max         63.923
_diffrn_reflns_theta_full        63.923
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2310
_reflns_number_gt                1925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.976

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0628P)²+1.2578P] 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   0.6(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1978
_refine_ls_wR_factor_gt          0.1817
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.237
_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 0.6505(5) 0.3858(4) 0.5517(4) 0.0692(14) Uani 1 1 d . . . . .
C1 C 0.7248(6) 0.4259(5) 0.4868(6) 0.0525(16) Uani 1 1 d . . . . .
N1 N 0.7992(5) 0.3608(5) 0.4160(4) 0.0548(14) Uani 1 1 d . . . . .
O2 O 0.9437(5) 0.3976(5) 0.2796(5) 0.0813(16) Uani 1 1 d . . . . .
C2 C 0.7572(6) 0.5495(5) 0.4662(5) 0.0508(16) Uani 1 1 d . . . . .
C5 C 0.8484(10) 0.7588(8) 0.3972(9) 0.094(3) Uani 1 1 d . . . . .
H5 H 0.879247 0.830716 0.374587 0.112 Uiso 1 1 calc R U . . .
C4 C 0.7592(9) 0.7547(7) 0.4772(8) 0.083(3) Uani 1 1 d . . . . .
H4 H 0.729936 0.823987 0.507387 0.100 Uiso 1 1 calc R U . . .
O3 O 0.6556(4) 0.0431(4) 0.5003(4) 0.0650(13) Uani 1 1 d . . . . .
C3 C 0.7109(7) 0.6489(6) 0.5148(6) 0.0633(19) Uani 1 1 d . . . . .
H3 H 0.650616 0.645701 0.569796 0.076 Uiso 1 1 calc R U . . .
C6 C 0.8937(8) 0.6588(8) 0.3492(8) 0.082(2) Uani 1 1 d . . . . .
H6 H 0.953903 0.662147 0.294137 0.098 Uiso 1 1 calc R U . . .
C7 C 0.8472(6) 0.5541(6) 0.3850(5) 0.0584(18) Uani 1 1 d . . . . .
C8 C 0.8748(6) 0.4328(6) 0.3499(6) 0.0587(18) Uani 1 1 d . . . . .
C9 C 0.6100(6) 0.0972(5) 0.4088(5) 0.0483(15) Uani 1 1 d . . . . .
C10 C 0.5011(6) 0.0516(7) 0.3645(6) 0.064(2) Uani 1 1 d . . . . .
H10 H 0.464041 -0.014289 0.394982 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4476(7) 0.1040(9) 0.2749(7) 0.079(3) Uani 1 1 d . . . . .
H11 H 0.373866 0.073679 0.245143 0.095 Uiso 1 1 calc R U . . .
C12 C 0.5022(8) 0.2005(8) 0.2293(7) 0.080(2) Uani 1 1 d . . . . .
H12 H 0.464996 0.236900 0.169699 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6120(7) 0.2430(6) 0.2725(6) 0.0633(18) Uani 1 1 d . . . . .
H13 H 0.649784 0.307649 0.240443 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6685(6) 0.1921(5) 0.3627(5) 0.0480(15) Uani 1 1 d . . . . .
C15 C 0.7960(6) 0.2343(6) 0.4038(6) 0.0591(18) Uani 1 1 d . . . . .
H15 H 0.857264 0.215196 0.346637 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8366(7) 0.1648(6) 0.5058(7) 0.075(2) Uani 1 1 d . . . . .
H16A H 0.890520 0.100929 0.483050 0.090 Uiso 1 1 calc R U . . .
H16B H 0.886281 0.215448 0.552362 0.090 Uiso 1 1 calc R U . . .
C17 C 0.7300(7) 0.1166(6) 0.5704(6) 0.067(2) Uani 1 1 d . . . . .
H17 H 0.677546 0.180958 0.597081 0.080 Uiso 1 1 calc R U . . .
C18 C 0.7695(11) 0.0415(7) 0.6652(8) 0.101(3) Uani 1 1 d . . . . .
H18A H 0.696247 0.006128 0.697173 0.152 Uiso 1 1 calc R U . . .
H18B H 0.811408 0.088788 0.718613 0.152 Uiso 1 1 calc R U . . .
H18C H 0.825929 -0.018175 0.640092 0.152 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 C1 1.210(8) . ?
C1 N1 1.391(8) . ?
C1 C2 1.481(8) . ?
N1 C8 1.408(8) . ?
N1 C15 1.460(8) . ?
O2 C8 1.200(9) . ?
C2 C3 1.377(9) . ?
C2 C7 1.380(9) . ?
C5 C4 1.364(13) . ?
C5 C6 1.376(13) . ?
C5 H5 0.9300 . ?
C4 C3 1.395(11) . ?
C4 H4 0.9300 . ?
O3 C9 1.371(8) . ?
O3 C17 1.440(8) . ?
C3 H3 0.9300 . ?
C6 C7 1.370(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.486(10) . ?
C9 C14 1.375(9) . ?
C9 C10 1.379(9) . ?
C10 C11 1.376(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.521(8) . ?
C15 C16 1.545(11) . ?
C15 H15 0.9800 . ?
C16 C17 1.487(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.507(10) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O1 C1 N1 125.2(6) . . ?
O1 C1 C2 128.8(6) . . ?
N1 C1 C2 106.0(6) . . ?
C1 N1 C8 111.6(5) . . ?
C1 N1 C15 125.8(5) . . ?
C8 N1 C15 122.5(6) . . ?
C3 C2 C7 121.8(6) . . ?
C3 C2 C1 129.5(6) . . ?
C7 C2 C1 108.7(6) . . ?
C4 C5 C6 121.5(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C4 C3 121.5(8) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C9 O3 C17 114.7(5) . . ?
C2 C3 C4 116.5(8) . . ?
C2 C3 H3 121.8 . . ?
C4 C3 H3 121.8 . . ?
C7 C6 C5 117.8(9) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 120.9(7) . . ?
C6 C7 C8 131.0(7) . . ?
C2 C7 C8 108.0(6) . . ?
O2 C8 N1 124.3(7) . . ?
O2 C8 C7 130.0(7) . . ?
N1 C8 C7 105.7(6) . . ?
O3 C9 C14 122.4(5) . . ?
O3 C9 C10 116.5(6) . . ?
C14 C9 C10 121.1(7) . . ?
C11 C10 C9 119.6(8) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.4(7) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.3(8) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.8(8) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C9 C14 C13 117.8(6) . . ?
C9 C14 C15 121.1(6) . . ?
C13 C14 C15 120.9(7) . . ?
N1 C15 C14 111.8(5) . . ?
N1 C15 C16 115.0(6) . . ?
C14 C15 C16 110.6(6) . . ?
N1 C15 H15 106.3 . . ?
C14 C15 H15 106.3 . . ?
C16 C15 H15 106.3 . . ?
C17 C16 C15 114.3(5) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O3 C17 C16 108.3(6) . . ?
O3 C17 C18 106.2(6) . . ?
C16 C17 C18 114.4(7) . . ?
O3 C17 H17 109.3 . . ?
C16 C17 H17 109.3 . . ?
C18 C17 H17 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C1 N1 C8 179.3(6) . . . . ?
C2 C1 N1 C8 -1.3(7) . . . . ?
O1 C1 N1 C15 3.3(11) . . . . ?
C2 C1 N1 C15 -177.3(6) . . . . ?
O1 C1 C2 C3 -0.4(11) . . . . ?
N1 C1 C2 C3 -179.7(6) . . . . ?
O1 C1 C2 C7 179.8(7) . . . . ?
N1 C1 C2 C7 0.4(7) . . . . ?
C6 C5 C4 C3 0.7(13) . . . . ?
C7 C2 C3 C4 0.4(9) . . . . ?
C1 C2 C3 C4 -179.4(7) . . . . ?
C5 C4 C3 C2 -0.6(11) . . . . ?
C4 C5 C6 C7 -0.6(13) . . . . ?
C5 C6 C7 C2 0.4(11) . . . . ?
C5 C6 C7 C8 179.1(8) . . . . ?
C3 C2 C7 C6 -0.3(10) . . . . ?
C1 C2 C7 C6 179.5(6) . . . . ?
C3 C2 C7 C8 -179.3(6) . . . . ?
C1 C2 C7 C8 0.6(7) . . . . ?
C1 N1 C8 O2 -177.2(7) . . . . ?
C15 N1 C8 O2 -1.0(10) . . . . ?
C1 N1 C8 C7 1.6(7) . . . . ?
C15 N1 C8 C7 177.8(6) . . . . ?
C6 C7 C8 O2 -1.4(13) . . . . ?
C2 C7 C8 O2 177.4(7) . . . . ?
C6 C7 C8 N1 179.9(7) . . . . ?
C2 C7 C8 N1 -1.3(7) . . . . ?
C17 O3 C9 C14 26.1(8) . . . . ?
C17 O3 C9 C10 -153.8(6) . . . . ?
O3 C9 C10 C11 177.7(6) . . . . ?
C14 C9 C10 C11 -2.2(10) . . . . ?
C9 C10 C11 C12 0.4(11) . . . . ?
C10 C11 C12 C13 1.3(12) . . . . ?
C11 C12 C13 C14 -1.3(11) . . . . ?
O3 C9 C14 C13 -177.7(6) . . . . ?
C10 C9 C14 C13 2.2(9) . . . . ?
O3 C9 C14 C15 6.9(9) . . . . ?
C10 C9 C14 C15 -173.1(6) . . . . ?
C12 C13 C14 C9 -0.5(10) . . . . ?
C12 C13 C14 C15 174.9(6) . . . . ?
C1 N1 C15 C14 62.9(9) . . . . ?
C8 N1 C15 C14 -112.7(6) . . . . ?
C1 N1 C15 C16 -64.3(8) . . . . ?
C8 N1 C15 C16 120.2(7) . . . . ?
C9 C14 C15 N1 -135.2(6) . . . . ?
C13 C14 C15 N1 49.6(8) . . . . ?
C9 C14 C15 C16 -5.7(8) . . . . ?
C13 C14 C15 C16 179.1(6) . . . . ?
N1 C15 C16 C17 101.0(7) . . . . ?
C14 C15 C16 C17 -26.7(8) . . . . ?
C9 O3 C17 C16 -57.1(7) . . . . ?
C9 O3 C17 C18 179.6(6) . . . . ?
C15 C16 C17 O3 57.5(8) . . . . ?
C15 C16 C17 C18 175.7(7) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1870462'
_audit_update_record             
;
2018-09-28 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.506(10)
_cell_length_b                   4.840(8)
_cell_length_c                   16.85(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.13(7)
_cell_angle_gamma                90
_cell_volume                     914(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4416
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      68.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   0.5070
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.884
_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      300(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            6738
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         59.368
_diffrn_reflns_theta_full        59.368
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             2470
_reflns_number_gt                2021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.958

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0574P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_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         2470
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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 0.8080(3) 0.1256(9) 0.4831(2) 0.0869(11) Uani 1 1 d . . . . .
H1 H 0.471(6) -0.035(15) 0.277(4) 0.12(3) Uiso 1 1 d . . . . .
C1 C 0.8125(4) 0.2393(11) 0.4097(4) 0.0748(14) Uani 1 1 d . . . . .
O2 O 0.5166(4) 0.1111(9) 0.2881(3) 0.0987(13) Uani 1 1 d . . . . .
C2 C 0.9105(5) 0.4074(14) 0.4095(5) 0.099(2) Uani 1 1 d . . . . .
H2 H 0.969513 0.428280 0.456975 0.119 Uiso 1 1 calc R U . . .
C5 C 0.7373(6) 0.3355(13) 0.2705(4) 0.0942(19) Uani 1 1 d . . . . .
H5 H 0.679232 0.313916 0.222519 0.113 Uiso 1 1 calc R U . . .
O4 O 0.4039(3) 0.6132(8) 0.2540(2) 0.0845(11) Uani 1 1 d . . . . .
C4 C 0.8353(8) 0.5062(16) 0.2706(6) 0.117(2) Uani 1 1 d . . . . .
H4 H 0.842548 0.596302 0.223237 0.140 Uiso 1 1 calc R U . . .
O3 O 0.2079(3) 0.7837(7) 0.0233(2) 0.0808(11) Uani 1 1 d . . . . .
C3 C 0.9207(7) 0.5394(17) 0.3414(6) 0.120(3) Uani 1 1 d . . . . .
H3 H 0.985818 0.653988 0.342242 0.144 Uiso 1 1 calc R U . . .
C6 C 0.7248(4) 0.1972(9) 0.3403(3) 0.0702(14) Uani 1 1 d . . . . .
H6 H 0.449(6) 0.467(16) 0.264(4) 0.13(3) Uiso 1 1 d . . . . .
C7 C 0.6214(4) 0.0118(10) 0.3422(3) 0.0737(15) Uani 1 1 d . . . . .
H7 H 0.639240 -0.171730 0.323485 0.088 Uiso 1 1 calc R U . . .
C8 C 0.6061(4) -0.0148(12) 0.4270(3) 0.0792(15) Uani 1 1 d . . . . .
H8A H 0.547340 -0.156527 0.429190 0.095 Uiso 1 1 calc R U . . .
H8B H 0.577099 0.158512 0.444038 0.095 Uiso 1 1 calc R U . . .
C9 C 0.7217(4) -0.0886(13) 0.4837(3) 0.0794(15) Uani 1 1 d . . . . .
H9 H 0.751233 -0.259912 0.464314 0.095 Uiso 1 1 calc R U . . .
C10 C 0.7149(6) -0.129(2) 0.5701(4) 0.129(3) Uani 1 1 d . . . . .
H10A H 0.668874 -0.291106 0.574466 0.193 Uiso 1 1 calc R U . . .
H10B H 0.677482 0.029312 0.588199 0.193 Uiso 1 1 calc R U . . .
H10C H 0.793948 -0.149897 0.603495 0.193 Uiso 1 1 calc R U . . .
C11 C 0.1685(4) 0.8541(10) 0.0909(3) 0.0644(13) Uani 1 1 d . . . . .
C12 C 0.0736(4) 1.0381(11) 0.0794(4) 0.0792(15) Uani 1 1 d . . . . .
H12 H 0.039058 1.100755 0.027187 0.095 Uiso 1 1 calc R U . . .
C13 C 0.0300(5) 1.1287(14) 0.1443(4) 0.0895(17) Uani 1 1 d . . . . .
H13 H -0.033565 1.252122 0.136014 0.107 Uiso 1 1 calc R U . . .
C14 C 0.0800(5) 1.0377(12) 0.2200(4) 0.0900(17) Uani 1 1 d . . . . .
H14 H 0.051349 1.099314 0.264280 0.108 Uiso 1 1 calc R U . . .
C15 C 0.1742(5) 0.8519(11) 0.2318(3) 0.0782(15) Uani 1 1 d . . . . .
H15 H 0.207376 0.789956 0.284281 0.094 Uiso 1 1 calc R U . . .
C16 C 0.2207(4) 0.7555(9) 0.1679(3) 0.0628(12) Uani 1 1 d . . . . .
C17 C 0.3208(4) 0.5519(10) 0.1796(3) 0.0651(13) Uani 1 1 d . . . . .
H17 H 0.288653 0.366178 0.183427 0.078 Uiso 1 1 calc R U . . .
C18 C 0.3788(4) 0.5604(13) 0.1089(3) 0.0823(16) Uani 1 1 d . . . . .
H18A H 0.433378 0.405813 0.112139 0.099 Uiso 1 1 calc R U . . .
H18B H 0.424538 0.729646 0.110758 0.099 Uiso 1 1 calc R U . . .
C19 C 0.2862(5) 0.5468(12) 0.0295(3) 0.0777(15) Uani 1 1 d . . . . .
H19 H 0.238658 0.378666 0.029346 0.093 Uiso 1 1 calc R U . . .
C20 C 0.3349(6) 0.5491(19) -0.0454(4) 0.120(3) Uani 1 1 d . . . . .
H20A H 0.270105 0.549583 -0.092774 0.180 Uiso 1 1 calc R U . . .
H20B H 0.383091 0.387675 -0.046133 0.180 Uiso 1 1 calc R U . . .
H20C H 0.382685 0.711592 -0.045554 0.180 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 C1 1.365(7) . ?
O1 C9 1.437(7) . ?
C1 C6 1.375(7) . ?
C1 C2 1.391(8) . ?
O2 C7 1.420(6) . ?
O2 H1 0.87(7) . ?
C2 C3 1.341(9) . ?
C2 H2 0.9300 . ?
C5 C6 1.389(8) . ?
C5 C4 1.397(10) . ?
C5 H5 0.9300 . ?
O4 C17 1.424(6) . ?
O4 H6 0.87(8) . ?
C4 C3 1.372(11) . ?
C4 H4 0.9300 . ?
O3 C11 1.360(6) . ?
O3 C19 1.447(6) . ?
C3 H3 0.9300 . ?
C6 C7 1.496(7) . ?
C7 C8 1.484(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.494(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.489(8) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.386(7) . ?
C11 C12 1.389(7) . ?
C12 C13 1.374(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.350(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.495(6) . ?
C17 C18 1.493(7) . ?
C17 H17 0.9800 . ?
C18 C19 1.510(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.493(7) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C1 O1 C9 117.7(4) . . ?
O1 C1 C6 122.6(5) . . ?
O1 C1 C2 115.8(5) . . ?
C6 C1 C2 121.6(6) . . ?
C7 O2 H1 104(5) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C6 C5 C4 121.5(7) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C17 O4 H6 105(5) . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C11 O3 C19 117.3(4) . . ?
C2 C3 C4 120.2(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C1 C6 C5 116.8(5) . . ?
C1 C6 C7 120.3(5) . . ?
C5 C6 C7 122.9(5) . . ?
O2 C7 C8 112.2(4) . . ?
O2 C7 C6 110.3(4) . . ?
C8 C7 C6 110.0(4) . . ?
O2 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C7 C8 C9 110.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 C10 106.9(5) . . ?
O1 C9 C8 109.8(5) . . ?
C10 C9 C8 114.8(5) . . ?
O1 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C16 122.8(4) . . ?
O3 C11 C12 116.4(5) . . ?
C16 C11 C12 120.7(5) . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.8(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 122.3(5) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C11 C16 C15 116.7(5) . . ?
C11 C16 C17 120.5(5) . . ?
C15 C16 C17 122.8(4) . . ?
O4 C17 C18 111.4(4) . . ?
O4 C17 C16 108.8(4) . . ?
C18 C17 C16 110.4(4) . . ?
O4 C17 H17 108.8 . . ?
C18 C17 H17 108.8 . . ?
C16 C17 H17 108.8 . . ?
C17 C18 C19 110.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
O3 C19 C20 106.3(5) . . ?
O3 C19 C18 109.4(5) . . ?
C20 C19 C18 115.0(5) . . ?
O3 C19 H19 108.7 . . ?
C20 C19 H19 108.7 . . ?
C18 C19 H19 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C9 O1 C1 C6 12.9(7) . . . . ?
C9 O1 C1 C2 -168.6(5) . . . . ?
O1 C1 C2 C3 -176.9(6) . . . . ?
C6 C1 C2 C3 1.7(9) . . . . ?
C6 C5 C4 C3 -0.4(10) . . . . ?
C1 C2 C3 C4 -1.2(11) . . . . ?
C5 C4 C3 C2 0.6(11) . . . . ?
O1 C1 C6 C5 177.0(5) . . . . ?
C2 C1 C6 C5 -1.4(7) . . . . ?
O1 C1 C6 C7 -2.5(7) . . . . ?
C2 C1 C6 C7 179.1(5) . . . . ?
C4 C5 C6 C1 0.8(8) . . . . ?
C4 C5 C6 C7 -179.7(5) . . . . ?
C1 C6 C7 O2 146.2(5) . . . . ?
C5 C6 C7 O2 -33.3(7) . . . . ?
C1 C6 C7 C8 21.9(6) . . . . ?
C5 C6 C7 C8 -157.6(5) . . . . ?
O2 C7 C8 C9 -173.6(4) . . . . ?
C6 C7 C8 C9 -50.4(6) . . . . ?
C1 O1 C9 C10 -166.8(5) . . . . ?
C1 O1 C9 C8 -41.6(6) . . . . ?
C7 C8 C9 O1 61.3(6) . . . . ?
C7 C8 C9 C10 -178.2(6) . . . . ?
C19 O3 C11 C16 15.8(6) . . . . ?
C19 O3 C11 C12 -165.7(4) . . . . ?
O3 C11 C12 C13 -177.9(5) . . . . ?
C16 C11 C12 C13 0.7(7) . . . . ?
C11 C12 C13 C14 -0.1(9) . . . . ?
C12 C13 C14 C15 -0.5(9) . . . . ?
C13 C14 C15 C16 0.5(8) . . . . ?
O3 C11 C16 C15 177.8(4) . . . . ?
C12 C11 C16 C15 -0.7(6) . . . . ?
O3 C11 C16 C17 -3.1(7) . . . . ?
C12 C11 C16 C17 178.4(4) . . . . ?
C14 C15 C16 C11 0.1(7) . . . . ?
C14 C15 C16 C17 -179.0(5) . . . . ?
C11 C16 C17 O4 142.9(4) . . . . ?
C15 C16 C17 O4 -38.0(6) . . . . ?
C11 C16 C17 C18 20.5(6) . . . . ?
C15 C16 C17 C18 -160.5(5) . . . . ?
O4 C17 C18 C19 -169.7(4) . . . . ?
C16 C17 C18 C19 -48.8(6) . . . . ?
C11 O3 C19 C20 -168.9(4) . . . . ?
C11 O3 C19 C18 -44.2(6) . . . . ?
C17 C18 C19 O3 61.5(6) . . . . ?
C17 C18 C19 C20 -179.0(5) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049

