# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1571775'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.0342(9)
_cell_length_b                   14.3895(15)
_cell_length_c                   14.5074(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.707(3)
_cell_angle_gamma                90.00
_cell_volume                     1846.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4091
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      22.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3255
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3255
_reflns_number_gt                2244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.6447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3255
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1024(2) 0.66979(13) 0.15473(17) 0.0724(6) Uani 1 1 d . . .
O2 O -0.01335(18) 0.52730(11) 0.19023(13) 0.0539(5) Uani 1 1 d . . .
O3 O 0.39900(17) 0.72140(11) 0.06569(10) 0.0450(4) Uani 1 1 d . . .
H3B H 0.3287 0.7104 0.0246 0.054 Uiso 1 1 d R . .
N1 N 0.6653(2) 0.76927(15) 0.39677(14) 0.0528(6) Uani 1 1 d . . .
C1 C 0.4173(3) 0.80226(17) 0.30830(16) 0.0454(6) Uani 1 1 d . . .
H1A H 0.3218 0.8266 0.3077 0.054 Uiso 1 1 calc R . .
C2 C 0.5244(3) 0.80159(19) 0.39019(17) 0.0524(6) Uani 1 1 d . . .
H2A H 0.4977 0.8250 0.4443 0.063 Uiso 1 1 calc R . .
C3 C 0.6960(3) 0.73501(17) 0.31799(18) 0.0512(6) Uani 1 1 d . . .
H3A H 0.7926 0.7114 0.3205 0.061 Uiso 1 1 calc R . .
C4 C 0.5963(3) 0.73159(16) 0.23278(16) 0.0428(6) Uani 1 1 d . . .
H4A H 0.6253 0.7062 0.1802 0.051 Uiso 1 1 calc R . .
C5 C 0.4519(2) 0.76664(14) 0.22669(14) 0.0348(5) Uani 1 1 d . . .
C6 C 0.3365(2) 0.76937(15) 0.13384(15) 0.0374(5) Uani 1 1 d . . .
C7 C 0.1890(2) 0.72584(16) 0.14741(15) 0.0385(5) Uani 1 1 d . . .
H7A H 0.1138 0.7670 0.1562 0.046 Uiso 1 1 calc R . .
C8 C 0.1546(2) 0.63585(15) 0.14819(15) 0.0377(5) Uani 1 1 d . . .
C9 C 0.0000(3) 0.61466(17) 0.16419(16) 0.0427(6) Uani 1 1 d . . .
C10 C -0.1552(3) 0.5015(2) 0.2138(2) 0.0649(8) Uani 1 1 d . . .
H10A H -0.1521 0.4372 0.2316 0.097 Uiso 1 1 calc R . .
H10B H -0.2356 0.5112 0.1602 0.097 Uiso 1 1 calc R . .
H10C H -0.1726 0.5390 0.2653 0.097 Uiso 1 1 calc R . .
C11 C 0.2590(2) 0.55695(15) 0.14148(16) 0.0409(5) Uani 1 1 d . . .
C12 C 0.3666(3) 0.52873(18) 0.2169(2) 0.0543(7) Uani 1 1 d . . .
H12A H 0.3759 0.5594 0.2742 0.065 Uiso 1 1 calc R . .
C13 C 0.4623(3) 0.4544(2) 0.2087(2) 0.0700(8) Uani 1 1 d U . .
H13A H 0.5349 0.4356 0.2602 0.084 Uiso 1 1 calc R . .
C14 C 0.4487(3) 0.4094(2) 0.1241(3) 0.0742(8) Uani 1 1 d U . .
H14A H 0.5128 0.3602 0.1181 0.089 Uiso 1 1 calc R . .
C15 C 0.3422(4) 0.4365(2) 0.0495(2) 0.0748(9) Uani 1 1 d . . .
H15A H 0.3342 0.4059 -0.0078 0.090 Uiso 1 1 calc R . .
C16 C 0.2460(3) 0.50834(18) 0.05668(19) 0.0581(7) Uani 1 1 d . . .
H16A H 0.1717 0.5249 0.0050 0.070 Uiso 1 1 calc R . .
C17 C 0.3088(3) 0.87103(17) 0.10492(19) 0.0556(7) Uani 1 1 d . . .
H17A H 0.4017 0.8986 0.0960 0.083 Uiso 1 1 calc R . .
H17B H 0.2724 0.9040 0.1534 0.083 Uiso 1 1 calc R . .
H17C H 0.2350 0.8744 0.0472 0.083 Uiso 1 1 calc R . .


_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 C9 1.206(3) . ?
O2 C9 1.325(3) . ?
O2 C10 1.441(3) . ?
O3 C6 1.414(3) . ?
O3 H3B 0.7938 . ?
N1 C3 1.325(3) . ?
N1 C2 1.340(3) . ?
C1 C2 1.372(3) . ?
C1 C5 1.383(3) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.528(3) . ?
C6 C7 1.520(3) . ?
C6 C17 1.528(3) . ?
C7 C8 1.332(3) . ?
C7 H7A 0.9300 . ?
C8 C11 1.492(3) . ?
C8 C9 1.493(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.370(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.395(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.353(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C9 O2 C10 116.67(19) . . ?
C6 O3 H3B 104.5 . . ?
C3 N1 C2 115.5(2) . . ?
C2 C1 C5 119.8(2) . . ?
C2 C1 H1A 120.1 . . ?
C5 C1 H1A 120.1 . . ?
N1 C2 C1 123.9(2) . . ?
N1 C2 H2A 118.1 . . ?
C1 C2 H2A 118.1 . . ?
N1 C3 C4 125.1(2) . . ?
N1 C3 H3A 117.4 . . ?
C4 C3 H3A 117.4 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C1 C5 C4 117.0(2) . . ?
C1 C5 C6 120.88(19) . . ?
C4 C5 C6 122.09(19) . . ?
O3 C6 C7 111.98(17) . . ?
O3 C6 C5 107.82(17) . . ?
C7 C6 C5 109.54(17) . . ?
O3 C6 C17 109.96(18) . . ?
C7 C6 C17 109.34(19) . . ?
C5 C6 C17 108.12(18) . . ?
C8 C7 C6 127.8(2) . . ?
C8 C7 H7A 116.1 . . ?
C6 C7 H7A 116.1 . . ?
C7 C8 C11 126.0(2) . . ?
C7 C8 C9 115.3(2) . . ?
C11 C8 C9 118.58(19) . . ?
O1 C9 O2 123.0(2) . . ?
O1 C9 C8 124.7(2) . . ?
O2 C9 C8 112.36(19) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 C8 121.9(2) . . ?
C16 C11 C8 119.8(2) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C3 N1 C2 C1 -1.4(4) . . . . ?
C5 C1 C2 N1 1.1(4) . . . . ?
C2 N1 C3 C4 0.7(4) . . . . ?
N1 C3 C4 C5 0.3(4) . . . . ?
C2 C1 C5 C4 0.0(3) . . . . ?
C2 C1 C5 C6 -178.0(2) . . . . ?
C3 C4 C5 C1 -0.6(3) . . . . ?
C3 C4 C5 C6 177.3(2) . . . . ?
C1 C5 C6 O3 -175.18(19) . . . . ?
C4 C5 C6 O3 7.0(3) . . . . ?
C1 C5 C6 C7 -53.1(3) . . . . ?
C4 C5 C6 C7 129.0(2) . . . . ?
C1 C5 C6 C17 66.0(3) . . . . ?
C4 C5 C6 C17 -111.9(2) . . . . ?
O3 C6 C7 C8 38.8(3) . . . . ?
C5 C6 C7 C8 -80.8(3) . . . . ?
C17 C6 C7 C8 160.9(2) . . . . ?
C6 C7 C8 C11 4.0(4) . . . . ?
C6 C7 C8 C9 179.4(2) . . . . ?
C10 O2 C9 O1 -4.3(4) . . . . ?
C10 O2 C9 C8 175.8(2) . . . . ?
C7 C8 C9 O1 17.7(3) . . . . ?
C11 C8 C9 O1 -166.5(2) . . . . ?
C7 C8 C9 O2 -162.4(2) . . . . ?
C11 C8 C9 O2 13.4(3) . . . . ?
C7 C8 C11 C12 77.8(3) . . . . ?
C9 C8 C11 C12 -97.4(3) . . . . ?
C7 C8 C11 C16 -103.6(3) . . . . ?
C9 C8 C11 C16 81.2(3) . . . . ?
C16 C11 C12 C13 1.1(4) . . . . ?
C8 C11 C12 C13 179.7(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C11 1.7(5) . . . . ?
C12 C11 C16 C15 -2.1(4) . . . . ?
C8 C11 C16 C15 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.011 0.000 0.000 238 89 ' '
2 -0.065 0.500 0.500 238 89 ' '
_platon_squeeze_details          
;
;

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

data_exp_206
_database_code_depnum_ccdc_archive 'CCDC 1845002'
loop_
_audit_author_name
_audit_author_address
'Chaofan Huang'
;Fudan University
China
;
_audit_update_record             
;
2018-05-24 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;
_audit_creation_date             2018-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.95790(10)
_cell_length_b                   12.9023(2)
_cell_length_c                   14.8437(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1524.08(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9310
_cell_measurement_theta_min      4.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15571
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.541
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -43.00   1.00    1.00    --    0.00 -19.00  60.00   41
  2  ω    -51.00  -6.00   1.00    1.00    --    0.00 -82.00-180.00   45
  3  ω    -89.00 -20.00   1.00    1.00    --    0.00 -38.00-120.00   69
  4  ω     -4.00  22.00   1.00    1.00    --    0.00 -82.00-180.00   26
  5  ω    -22.00  20.00   1.00    1.00    --    0.00 -19.00  60.00   42
  6  ω     15.00  88.00   1.00    1.00    --    0.00  19.00   0.00   73
  7  ω      7.00 116.00   1.00    1.00    --   95.80 -82.00 -30.00  109
  8  ω     47.00 120.00   1.00    1.00    --   95.80 -61.00  90.00   73
  9  ω     75.00 112.00   1.00    1.00    --   95.80  45.00-180.00   37
 10  ω     84.00 112.00   1.00    1.00    --   95.80 -82.00  60.00   28
 11  ω     68.00 126.00   1.00    1.00    --   95.80  15.00 -30.00   58
 12  ω    160.00 185.00   1.00    1.00    --   95.80  15.00 -30.00   25
 13  ω     28.00  84.00   1.00    1.00    --   95.80 -82.00  90.00   56
 14  ω    100.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   27
 15  ω     52.00 113.00   1.00    1.00    --   95.80 -45.00   0.00   61
 16  ω     19.00  44.00   1.00    1.00    --   95.80 -61.00  90.00   25
 17  ω      7.00 101.00   1.00    1.00    --   95.80 -61.00 -30.00   94
 18  ω      7.00 127.00   1.00    1.00    --   95.80 -82.00-180.00  120
 19  ω     62.00 106.00   1.00    1.00    --   95.80 -82.00-120.00   44
 20  ω    100.00 184.00   1.00    1.00    --   95.80  30.00-150.00   84
 21  ω     68.00 185.00   1.00    1.00    --   95.80  15.00 -90.00  117
 22  ω     55.00  83.00   1.00    1.00    --   95.80 -61.00-180.00   28
 23  ω     28.00 101.00   1.00    1.00    --   95.80 -82.00 -90.00   73
 24  ω    123.00 177.00   1.00    1.00    --   95.80  45.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343244000
_diffrn_orient_matrix_UB_12      0.1163248000
_diffrn_orient_matrix_UB_13      -0.0143711000
_diffrn_orient_matrix_UB_21      0.1872937000
_diffrn_orient_matrix_UB_22      0.0175561000
_diffrn_orient_matrix_UB_23      -0.0213308000
_diffrn_orient_matrix_UB_31      -0.0348627000
_diffrn_orient_matrix_UB_32      -0.0203794000
_diffrn_orient_matrix_UB_33      -0.1005616000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2617
_reflns_number_total             2710
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.083
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(7)
_refine_ls_extinction_coef       0.0040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.11841(17) 0.54839(15) 0.49972(11) 0.0717(5) Uani 1 1 d . . . . .
H1 H 1.213770 0.550603 0.520565 0.108 Uiso 1 1 calc GR . . . .
O2 O 0.48618(16) 0.58375(13) 0.51646(9) 0.0599(4) Uani 1 1 d . . . . .
O3 O 0.53904(15) 0.63173(12) 0.37523(9) 0.0564(4) Uani 1 1 d . . . . .
C1 C 0.9173(3) 0.34898(16) 0.64669(12) 0.0499(5) Uani 1 1 d . . . . .
H1A H 0.852764 0.389088 0.685587 0.060 Uiso 1 1 calc R . . . .
C2 C 0.9193(3) 0.24307(17) 0.65707(15) 0.0632(6) Uani 1 1 d . . . . .
H2 H 0.855798 0.212356 0.702376 0.076 Uiso 1 1 calc R . . . .
C3 C 1.0144(4) 0.18272(19) 0.60102(18) 0.0767(7) Uani 1 1 d . . . . .
H3 H 1.016448 0.111142 0.608334 0.092 Uiso 1 1 calc R . . . .
C4 C 1.1063(4) 0.2284(2) 0.53423(19) 0.0861(8) Uani 1 1 d . . . . .
H4 H 1.171874 0.187767 0.496297 0.103 Uiso 1 1 calc R . . . .
C5 C 1.1024(3) 0.3351(2) 0.52259(15) 0.0691(6) Uani 1 1 d . . . . .
H5 H 1.163137 0.365137 0.475867 0.083 Uiso 1 1 calc R . . . .
C6 C 1.0095(2) 0.39713(14) 0.57946(11) 0.0428(4) Uani 1 1 d . . . . .
C7 C 1.0044(2) 0.51510(15) 0.56761(12) 0.0477(4) Uani 1 1 d . . . . .
C8 C 0.8281(2) 0.54383(14) 0.53878(12) 0.0423(4) Uani 1 1 d . . . . .
H8 H 0.747411 0.538381 0.583843 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7697(2) 0.57561(13) 0.45947(11) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.8658(2) 0.58660(14) 0.37335(11) 0.0392(4) Uani 1 1 d . . . . .
C11 C 0.9028(2) 0.49956(16) 0.32250(13) 0.0511(5) Uani 1 1 d . . . . .
H11 H 0.872778 0.434423 0.343965 0.061 Uiso 1 1 calc R . . . .
C12 C 0.9836(3) 0.5079(2) 0.24028(14) 0.0626(6) Uani 1 1 d . . . . .
H12 H 1.007515 0.448571 0.207104 0.075 Uiso 1 1 calc R . . . .
C13 C 1.0282(3) 0.6027(2) 0.20777(14) 0.0667(6) Uani 1 1 d . . . . .
H13 H 1.081698 0.608383 0.152290 0.080 Uiso 1 1 calc R . . . .
C14 C 0.9934(3) 0.68991(19) 0.25775(15) 0.0635(6) Uani 1 1 d . . . . .
H14 H 1.024458 0.754683 0.235901 0.076 Uiso 1 1 calc R . . . .
C15 C 0.9129(2) 0.68251(16) 0.33991(13) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.890243 0.742157 0.372920 0.060 Uiso 1 1 calc R . . . .
C16 C 0.5841(2) 0.59711(14) 0.45582(11) 0.0398(4) Uani 1 1 d . . . . .
C17 C 0.3620(2) 0.6540(2) 0.36216(16) 0.0697(7) Uani 1 1 d . . . . .
H17A H 0.346071 0.686309 0.304534 0.105 Uiso 1 1 calc GR . . . .
H17B H 0.323735 0.699803 0.408808 0.105 Uiso 1 1 calc GR . . . .
H17C H 0.299035 0.590576 0.364482 0.105 Uiso 1 1 calc GR . . . .
C18 C 1.0440(3) 0.56980(17) 0.65656(15) 0.0664(6) Uani 1 1 d . . . . .
H18A H 1.151723 0.547368 0.678191 0.100 Uiso 1 1 calc GR . . . .
H18B H 0.959264 0.552971 0.700193 0.100 Uiso 1 1 calc GR . . . .
H18C H 1.045886 0.643400 0.647098 0.100 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 C7 1.422(2) . ?
O2 C16 1.203(2) . ?
O3 C16 1.326(2) . ?
O3 C17 1.451(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.375(3) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C6 C7 1.533(3) . ?
C7 C8 1.513(2) . ?
C7 C18 1.530(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.330(2) . ?
C9 C10 1.496(2) . ?
C9 C16 1.504(2) . ?
C10 C11 1.385(3) . ?
C10 C15 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C7 O1 H1 109.5 . . ?
C16 O3 C17 116.73(15) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C6 121.33(19) . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 120.94(16) . . ?
C5 C6 C1 117.70(19) . . ?
C5 C6 C7 121.34(18) . . ?
O1 C7 C6 111.39(16) . . ?
O1 C7 C8 108.48(14) . . ?
O1 C7 C18 109.93(17) . . ?
C8 C7 C6 107.45(15) . . ?
C8 C7 C18 108.78(17) . . ?
C18 C7 C6 110.72(15) . . ?
C7 C8 H8 114.7 . . ?
C9 C8 C7 130.51(16) . . ?
C9 C8 H8 114.7 . . ?
C8 C9 C10 127.35(15) . . ?
C8 C9 C16 115.58(15) . . ?
C10 C9 C16 116.98(13) . . ?
C11 C10 C9 119.82(16) . . ?
C11 C10 C15 118.16(16) . . ?
C15 C10 C9 121.94(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.40(19) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
O2 C16 O3 123.24(15) . . ?
O2 C16 C9 125.64(15) . . ?
O3 C16 C9 111.11(13) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.053
_oxdiff_exptl_absorpt_empirical_full_min 0.570
