# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2006082'
loop_
_audit_author_name
_audit_author_address
liyan
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30

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

_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                   8.53180(10)
_cell_length_b                   9.34100(10)
_cell_length_c                   18.0021(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1434.69(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    3817
_cell_measurement_theta_min      4.8970
_cell_measurement_theta_max      71.1520

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_T_min  0.39040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            4843
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.913
_diffrn_reflns_theta_max         71.260
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2688
_reflns_number_gt                2622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.990

_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0505P)²+0.1206P] 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     SHELXL
_refine_ls_extinction_coef       0.0268(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O3 O -0.04151(19) 0.78901(16) 0.62237(10) 0.0691(5) Uani 1 1 d . . . . .
O1 O 0.1280(2) 0.6518(2) 0.71970(8) 0.0776(6) Uani 1 1 d . . . . .
N1 N 0.0431(2) 0.66848(18) 0.60173(9) 0.0516(4) Uani 1 1 d . . . . .
O2 O -0.0755(3) 0.6811(2) 0.48994(11) 0.0876(6) Uani 1 1 d . . . . .
C10 C 0.3734(2) 0.47203(19) 0.66561(10) 0.0431(4) Uani 1 1 d . . . . .
C5 C 0.1248(2) 0.6005(2) 0.65852(10) 0.0479(4) Uani 1 1 d . . . . .
C4 C 0.2021(2) 0.4568(2) 0.64045(10) 0.0434(4) Uani 1 1 d . . . . .
C2 C 0.1097(2) 0.4934(2) 0.50762(10) 0.0505(4) Uani 1 1 d . . . . .
C15 C 0.4696(3) 0.5644(2) 0.62700(12) 0.0569(5) Uani 1 1 d . . . . .
H15 H 0.4307 0.6138 0.5861 0.068 Uiso 1 1 calc R U . . .
C1 C 0.0175(3) 0.6199(2) 0.52972(12) 0.0563(5) Uani 1 1 d . . . . .
C3 C 0.1961(2) 0.4162(2) 0.55879(10) 0.0459(4) Uani 1 1 d . . . . .
C11 C 0.4330(3) 0.3990(3) 0.72612(12) 0.0601(5) Uani 1 1 d . . . . .
H11 H 0.3694 0.3369 0.7529 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1058(3) 0.4519(3) 0.43282(12) 0.0707(7) Uani 1 1 d . . . . .
H6 H 0.0493 0.5058 0.3986 0.085 Uiso 1 1 calc R U . . .
C12 C 0.5888(3) 0.4188(3) 0.74677(16) 0.0774(8) Uani 1 1 d . . . . .
H12 H 0.6291 0.3684 0.7870 0.093 Uiso 1 1 calc R U . . .
C16 C 0.1095(3) 0.3445(3) 0.68512(13) 0.0638(6) Uani 1 1 d . . . . .
H16A H 0.1561 0.2519 0.6782 0.096 Uiso 1 1 calc R U . . .
H16B H 0.0029 0.3426 0.6682 0.096 Uiso 1 1 calc R U . . .
H16C H 0.1119 0.3691 0.7369 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6828(3) 0.5110(3) 0.70879(16) 0.0783(8) Uani 1 1 d . . . . .
H13 H 0.7863 0.5244 0.7235 0.094 Uiso 1 1 calc R U . . .
C14 C 0.6250(3) 0.5840(3) 0.64885(17) 0.0740(7) Uani 1 1 d . . . . .
H14 H 0.6892 0.6467 0.6227 0.089 Uiso 1 1 calc R U . . .
C9 C 0.2740(3) 0.2938(3) 0.53425(15) 0.0680(6) Uani 1 1 d . . . . .
H9 H 0.3311 0.2389 0.5678 0.082 Uiso 1 1 calc R U . . .
C17 C 0.0434(4) 0.9164(3) 0.60392(18) 0.0792(8) Uani 1 1 d . . . . .
H17A H 0.0504 0.9252 0.5509 0.119 Uiso 1 1 calc R U . . .
H17B H 0.1469 0.9112 0.6246 0.119 Uiso 1 1 calc R U . . .
H17C H -0.0102 0.9982 0.6239 0.119 Uiso 1 1 calc R U . . .
C8 C 0.2673(3) 0.2534(3) 0.46082(17) 0.0833(9) Uani 1 1 d . . . . .
H8 H 0.3195 0.1712 0.4454 0.100 Uiso 1 1 calc R U . . .
C7 C 0.1848(3) 0.3325(4) 0.40999(15) 0.0867(9) Uani 1 1 d . . . . .
H7 H 0.1826 0.3052 0.3603 0.104 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
O3 N1 1.388(2) . ?
O3 C17 1.432(3) . ?
O1 C5 1.201(2) . ?
N1 C5 1.391(3) . ?
N1 C1 1.391(3) . ?
O2 C1 1.212(3) . ?
C10 C15 1.379(3) . ?
C10 C11 1.382(3) . ?
C10 C4 1.537(2) . ?
C5 C4 1.530(3) . ?
C4 C3 1.519(3) . ?
C4 C16 1.540(3) . ?
C2 C3 1.383(3) . ?
C2 C6 1.402(3) . ?
C2 C1 1.474(3) . ?
C15 C14 1.394(3) . ?
C15 H15 0.9300 . ?
C3 C9 1.394(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C12 C13 1.361(5) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C9 C8 1.376(3) . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 C7 1.371(5) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O3 C17 110.40(18) . . ?
O3 N1 C5 115.75(16) . . ?
O3 N1 C1 115.61(17) . . ?
C5 N1 C1 127.94(17) . . ?
C15 C10 C11 119.14(19) . . ?
C15 C10 C4 118.40(17) . . ?
C11 C10 C4 122.45(18) . . ?
O1 C5 N1 120.22(19) . . ?
O1 C5 C4 122.31(18) . . ?
N1 C5 C4 117.41(16) . . ?
C3 C4 C5 114.22(15) . . ?
C3 C4 C10 109.89(14) . . ?
C5 C4 C10 105.44(15) . . ?
C3 C4 C16 108.54(17) . . ?
C5 C4 C16 105.37(15) . . ?
C10 C4 C16 113.40(16) . . ?
C3 C2 C6 120.6(2) . . ?
C3 C2 C1 121.54(17) . . ?
C6 C2 C1 117.9(2) . . ?
C10 C15 C14 120.4(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O2 C1 N1 120.0(2) . . ?
O2 C1 C2 124.6(2) . . ?
N1 C1 C2 115.40(17) . . ?
C2 C3 C9 118.09(19) . . ?
C2 C3 C4 122.14(18) . . ?
C9 C3 C4 119.71(18) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C6 C2 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C8 C9 C3 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C3 C9 H9 119.7 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?

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
C17 O3 N1 C5 99.9(2) . . . . ?
C17 O3 N1 C1 -88.9(2) . . . . ?
O3 N1 C5 O1 -5.0(3) . . . . ?
C1 N1 C5 O1 -174.9(2) . . . . ?
O3 N1 C5 C4 172.29(15) . . . . ?
C1 N1 C5 C4 2.4(3) . . . . ?
O1 C5 C4 C3 -175.4(2) . . . . ?
N1 C5 C4 C3 7.4(2) . . . . ?
O1 C5 C4 C10 -54.6(2) . . . . ?
N1 C5 C4 C10 128.12(17) . . . . ?
O1 C5 C4 C16 65.6(2) . . . . ?
N1 C5 C4 C16 -111.7(2) . . . . ?
C15 C10 C4 C3 55.1(2) . . . . ?
C11 C10 C4 C3 -126.2(2) . . . . ?
C15 C10 C4 C5 -68.5(2) . . . . ?
C11 C10 C4 C5 110.2(2) . . . . ?
C15 C10 C4 C16 176.76(19) . . . . ?
C11 C10 C4 C16 -4.6(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C4 C10 C15 C14 178.6(2) . . . . ?
O3 N1 C1 O2 -1.0(3) . . . . ?
C5 N1 C1 O2 169.0(2) . . . . ?
O3 N1 C1 C2 178.95(17) . . . . ?
C5 N1 C1 C2 -11.1(3) . . . . ?
C3 C2 C1 O2 -170.3(2) . . . . ?
C6 C2 C1 O2 8.8(3) . . . . ?
C3 C2 C1 N1 9.8(3) . . . . ?
C6 C2 C1 N1 -171.1(2) . . . . ?
C6 C2 C3 C9 -2.2(3) . . . . ?
C1 C2 C3 C9 176.88(19) . . . . ?
C6 C2 C3 C4 -179.39(19) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C5 C4 C3 C2 -8.3(3) . . . . ?
C10 C4 C3 C2 -126.53(19) . . . . ?
C16 C4 C3 C2 108.9(2) . . . . ?
C5 C4 C3 C9 174.59(19) . . . . ?
C10 C4 C3 C9 56.3(2) . . . . ?
C16 C4 C3 C9 -68.2(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C4 C10 C11 C12 -179.1(2) . . . . ?
C3 C2 C6 C7 1.4(3) . . . . ?
C1 C2 C6 C7 -177.7(2) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C10 C15 C14 C13 0.2(4) . . . . ?
C2 C3 C9 C8 1.4(3) . . . . ?
C4 C3 C9 C8 178.6(2) . . . . ?
C3 C9 C8 C7 0.3(4) . . . . ?
C2 C6 C7 C8 0.3(4) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_liyan-cxf-co-allyl
_database_code_depnum_ccdc_archive 'CCDC 2006083'
loop_
_audit_author_name
_audit_author_address
liyan
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.84850(10)
_cell_length_b                   12.7347(2)
_cell_length_c                   9.08320(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.4380(10)
_cell_angle_gamma                90
_cell_volume                     907.82(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2150
_cell_measurement_theta_min      5.9890
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8523
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.032
_diffrn_reflns_theta_min         5.637
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                3185
_reflns_number_total             3231
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.143
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.026
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C5(H5), C3(H3), C4(H4), C16(H16), C13(H13), C19(H19),
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_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
O21 O 0.31439(13) 0.56283(12) 0.47548(14) 0.0563(3) Uani 1 1 d . . . . .
O23 O 0.39365(19) 0.37256(12) 0.5835(2) 0.0696(4) Uani 1 1 d . . . . .
N9 N 0.47640(14) 0.53812(11) 0.53076(14) 0.0449(3) Uani 1 1 d . . . . .
C11 C 0.78583(16) 0.56941(13) 0.36333(15) 0.0413(3) Uani 1 1 d . . . . .
C12 C 0.7499(2) 0.64830(15) 0.26138(17) 0.0502(4) Uani 1 1 d . . . . .
H12 H 0.716912 0.714333 0.294305 0.060 Uiso 1 1 calc R . . . .
C10 C 0.50054(19) 0.44244(14) 0.58828(17) 0.0477(3) Uani 1 1 d . . . . .
C6 C 0.6766(2) 0.42616(13) 0.65058(16) 0.0452(3) Uani 1 1 d . . . . .
C1 C 0.80850(18) 0.49686(13) 0.62094(15) 0.0416(3) Uani 1 1 d . . . . .
C7 C 0.77201(16) 0.59416(11) 0.52874(15) 0.0390(3) Uani 1 1 d . . . . .
C8 C 0.58609(18) 0.62912(12) 0.56033(16) 0.0416(3) Uani 1 1 d . . . . .
H8 H 0.555649 0.684662 0.490229 0.050 Uiso 1 1 calc R . . . .
C2 C 0.9713(2) 0.47311(15) 0.67321(17) 0.0496(4) Uani 1 1 d . . . . .
H2 H 1.061355 0.518277 0.653502 0.059 Uiso 1 1 calc R . . . .
C18 C 0.5606(2) 0.67215(15) 0.71715(19) 0.0539(4) Uani 1 1 d . . . . .
H18A H 0.613958 0.624554 0.786963 0.065 Uiso 1 1 calc R . . . .
H18B H 0.617629 0.739482 0.725519 0.065 Uiso 1 1 calc R . . . .
C5 C 0.7063(3) 0.33595(15) 0.7330(2) 0.0572(4) Uani 1 1 d . . . . .
H5 H 0.617200 0.289947 0.752237 0.069 Uiso 1 1 calc R . . . .
C3 C 0.9999(2) 0.38208(17) 0.75487(19) 0.0597(4) Uani 1 1 d . . . . .
H3 H 1.109411 0.366862 0.788455 0.072 Uiso 1 1 calc R . . . .
C4 C 0.8685(3) 0.31439(18) 0.7865(2) 0.0636(5) Uani 1 1 d . . . . .
H4 H 0.888274 0.254765 0.843233 0.076 Uiso 1 1 calc R . . . .
C17 C 0.89470(19) 0.68515(15) 0.56628(18) 0.0499(4) Uani 1 1 d . . . . .
H17A H 1.005873 0.669530 0.528754 0.075 Uiso 1 1 calc GR . . . .
H17B H 0.901330 0.693680 0.671178 0.075 Uiso 1 1 calc GR . . . .
H17C H 0.853228 0.748834 0.522264 0.075 Uiso 1 1 calc GR . . . .
C16 C 0.8343(3) 0.47155(18) 0.3115(2) 0.0600(4) Uani 1 1 d . . . . .
H16 H 0.858787 0.417896 0.377779 0.072 Uiso 1 1 calc R . . . .
C13 C 0.7628(3) 0.6296(2) 0.11129(19) 0.0649(5) Uani 1 1 d . . . . .
H13 H 0.738802 0.683136 0.044694 0.078 Uiso 1 1 calc R . . . .
C19 C 0.3778(3) 0.6856(3) 0.7571(3) 0.0792(7) Uani 1 1 d . . . . .
H19 H 0.311363 0.729803 0.698851 0.095 Uiso 1 1 calc R . . . .
C14 C 0.8105(4) 0.5328(2) 0.0607(2) 0.0761(6) Uani 1 1 d . . . . .
H14 H 0.818765 0.520443 -0.039851 0.091 Uiso 1 1 calc R . . . .
C15 C 0.8464(4) 0.4530(2) 0.1609(2) 0.0784(7) Uani 1 1 d . . . . .
H15 H 0.878739 0.387086 0.127106 0.094 Uiso 1 1 calc R . . . .
C22 C 0.3019(3) 0.5322(3) 0.3250(2) 0.0757(6) Uani 1 1 d . . . . .
H22A H 0.391770 0.564694 0.270305 0.114 Uiso 1 1 calc GR . . . .
H22B H 0.193713 0.553948 0.285585 0.114 Uiso 1 1 calc GR . . . .
H22C H 0.311785 0.457219 0.317800 0.114 Uiso 1 1 calc GR . . . .
C20 C 0.3052(5) 0.6396(4) 0.8679(4) 0.1154(15) Uani 1 1 d . . . . .
H20A H 0.199(8) 0.659(5) 0.906(6) 0.17(2) Uiso 1 1 d . . . . .
H20B H 0.383(6) 0.574(5) 0.927(5) 0.139(16) Uiso 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
O21 N9 1.3993(16) . ?
O21 C22 1.424(3) . ?
O23 C10 1.224(2) . ?
N9 C10 1.339(2) . ?
N9 C8 1.467(2) . ?
C11 C12 1.394(2) . ?
C11 C7 1.5398(18) . ?
C11 C16 1.386(3) . ?
C12 C13 1.388(2) . ?
C10 C6 1.504(2) . ?
C6 C1 1.399(2) . ?
C6 C5 1.390(2) . ?
C1 C7 1.522(2) . ?
C1 C2 1.393(2) . ?
C7 C8 1.5544(18) . ?
C7 C17 1.543(2) . ?
C8 C18 1.541(2) . ?
C2 C3 1.394(3) . ?
C18 C19 1.493(3) . ?
C5 C4 1.387(3) . ?
C3 C4 1.376(3) . ?
C16 C15 1.392(3) . ?
C13 C14 1.368(4) . ?
C19 C20 1.299(5) . ?
C14 C15 1.391(4) . ?

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
N9 O21 C22 109.78(13) . . ?
O21 N9 C8 114.74(13) . . ?
C10 N9 O21 118.04(13) . . ?
C10 N9 C8 124.50(12) . . ?
C12 C11 C7 119.04(14) . . ?
C16 C11 C12 118.48(14) . . ?
C16 C11 C7 122.48(14) . . ?
C13 C12 C11 120.85(17) . . ?
O23 C10 N9 123.60(15) . . ?
O23 C10 C6 122.74(17) . . ?
N9 C10 C6 113.54(13) . . ?
C1 C6 C10 121.18(14) . . ?
C5 C6 C10 117.80(15) . . ?
C5 C6 C1 120.95(15) . . ?
C6 C1 C7 119.57(13) . . ?
C2 C1 C6 118.19(15) . . ?
C2 C1 C7 122.20(14) . . ?
C11 C7 C8 108.18(11) . . ?
C11 C7 C17 108.71(11) . . ?
C1 C7 C11 110.86(12) . . ?
C1 C7 C8 107.74(11) . . ?
C1 C7 C17 112.04(13) . . ?
C17 C7 C8 109.22(12) . . ?
N9 C8 C7 106.87(12) . . ?
N9 C8 C18 111.71(12) . . ?
C18 C8 C7 113.66(12) . . ?
C1 C2 C3 120.41(16) . . ?
C19 C18 C8 113.43(15) . . ?
C4 C5 C6 120.14(17) . . ?
C4 C3 C2 120.92(16) . . ?
C3 C4 C5 119.36(18) . . ?
C11 C16 C15 120.48(19) . . ?
C14 C13 C12 120.42(19) . . ?
C20 C19 C18 124.4(3) . . ?
C13 C14 C15 119.54(17) . . ?
C14 C15 C16 120.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_liyan-cxf-co-meoh
_database_code_depnum_ccdc_archive 'CCDC 2006084'
loop_
_audit_author_name
_audit_author_address
liyan
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.87176(11)
_cell_length_b                   12.32287(17)
_cell_length_c                   16.6389(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6914
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4480
_cell_measurement_theta_min      4.4470
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.867
_diffrn_reflns_theta_min         4.465
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2995
_reflns_number_total             3210
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1331
_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
2. Rigid bond restraints
 C3, C4, C5, C6, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of
0.001
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C6(H6), C12(H12), C4(H4), C13(H13), C3(H3), C14(H14),
 C5(H5)
4.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.42719(19) 0.01027(13) 0.14039(10) 0.0567(4) Uani 1 1 d . . . . .
N1 N 0.5171(2) -0.12919(14) 0.22947(11) 0.0504(4) Uani 1 1 d . . . . .
C8 C 0.4076(2) -0.03579(15) 0.21733(12) 0.0445(4) Uani 1 1 d . . . . .
H8 H 0.433590 0.019165 0.258090 0.053 Uiso 1 1 calc R . . . .
C10 C 0.1990(2) -0.10795(17) 0.31561(13) 0.0486(5) Uani 1 1 d . . . . .
C7 C 0.2217(2) -0.07260(16) 0.22726(12) 0.0462(4) Uani 1 1 d . . . . .
C2 C 0.3267(3) -0.23686(19) 0.15165(13) 0.0579(5) Uani 1 1 d . U . . .
O2 O 0.67916(19) -0.10444(15) 0.25887(10) 0.0628(4) Uani 1 1 d . . . . .
C9 C 0.4980(3) -0.22240(17) 0.18775(15) 0.0577(5) Uani 1 1 d . . . . .
C1 C 0.1920(3) -0.16697(18) 0.16999(13) 0.0520(5) Uani 1 1 d . . . . .
O3 O 0.6112(3) -0.29047(16) 0.18362(17) 0.0873(6) Uani 1 1 d . . . . .
C16 C 0.1047(3) 0.02491(18) 0.20965(17) 0.0620(6) Uani 1 1 d . . . . .
H16A H 0.145830 0.087653 0.237764 0.093 Uiso 1 1 calc GR . . . .
H16B H -0.008587 0.008571 0.227287 0.093 Uiso 1 1 calc GR . . . .
H16C H 0.103930 0.039204 0.152933 0.093 Uiso 1 1 calc GR . . . .
C15 C 0.2331(4) -0.0347(2) 0.37647(16) 0.0648(6) Uani 1 1 d . . . . .
H15 H 0.265313 0.035695 0.363401 0.078 Uiso 1 1 calc R . . . .
C11 C 0.1449(3) -0.21154(19) 0.33653(15) 0.0604(6) Uani 1 1 d . . . . .
H11 H 0.118446 -0.261516 0.296568 0.072 Uiso 1 1 calc R . . . .
C17 C 0.5877(3) 0.0597(3) 0.12906(19) 0.0757(8) Uani 1 1 d . . . . .
H17A H 0.590049 0.095543 0.077848 0.114 Uiso 1 1 calc GR . . . .
H17B H 0.674855 0.005233 0.130703 0.114 Uiso 1 1 calc GR . . . .
H17C H 0.607127 0.111818 0.170940 0.114 Uiso 1 1 calc GR . . . .
C6 C 0.0328(3) -0.1888(2) 0.13731(17) 0.0691(6) Uani 1 1 d . U . . .
H6 H -0.058593 -0.144057 0.149670 0.083 Uiso 1 1 calc R . . . .
C12 C 0.1303(4) -0.2408(2) 0.41694(18) 0.0759(8) Uani 1 1 d . . . . .
H12 H 0.093074 -0.310009 0.430511 0.091 Uiso 1 1 calc R . . . .
C4 C 0.1421(5) -0.3433(3) 0.0683(2) 0.0895(7) Uani 1 1 d . U . . .
H4 H 0.125594 -0.401691 0.033731 0.107 Uiso 1 1 calc R . . . .
C13 C 0.1705(5) -0.1678(3) 0.47655(16) 0.0857(10) Uani 1 1 d . . . . .
H13 H 0.164203 -0.188325 0.530246 0.103 Uiso 1 1 calc R . . . .
C3 C 0.3026(4) -0.3248(3) 0.10103(18) 0.0789(7) Uani 1 1 d . U . . .
H3 H 0.392472 -0.371012 0.089003 0.095 Uiso 1 1 calc R . . . .
C14 C 0.2201(5) -0.0642(3) 0.45635(17) 0.0825(9) Uani 1 1 d . . . . .
H14 H 0.244956 -0.014130 0.496455 0.099 Uiso 1 1 calc R . . . .
C18 C 0.6960(4) -0.1439(3) 0.33874(17) 0.0869(9) Uani 1 1 d . . . . .
H18A H 0.688499 -0.221630 0.338606 0.130 Uiso 1 1 calc GR . . . .
H18B H 0.606817 -0.114439 0.371491 0.130 Uiso 1 1 calc GR . . . .
H18C H 0.804127 -0.122190 0.360071 0.130 Uiso 1 1 calc GR . . . .
C5 C 0.0093(4) -0.2769(3) 0.0864(2) 0.0822(7) Uani 1 1 d . U . . .
H5 H -0.097405 -0.290528 0.064681 0.099 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 C8 1.409(2) . ?
O1 C17 1.415(3) . ?
N1 C8 1.452(2) . ?
N1 O2 1.400(2) . ?
N1 C9 1.350(3) . ?
C8 C7 1.541(3) . ?
C10 C7 1.544(3) . ?
C10 C15 1.383(4) . ?
C10 C11 1.390(3) . ?
C7 C1 1.522(3) . ?
C7 C16 1.542(3) . ?
C2 C9 1.487(3) . ?
C2 C1 1.400(3) . ?
C2 C3 1.386(4) . ?
O2 C18 1.421(3) . ?
C9 O3 1.226(3) . ?
C1 C6 1.392(3) . ?
C15 C14 1.382(4) . ?
C11 C12 1.390(3) . ?
C6 C5 1.389(4) . ?
C12 C13 1.376(5) . ?
C4 C3 1.394(5) . ?
C4 C5 1.362(5) . ?
C13 C14 1.376(5) . ?

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 C17 113.09(17) . . ?
O2 N1 C8 114.63(17) . . ?
C9 N1 C8 122.46(18) . . ?
C9 N1 O2 117.79(18) . . ?
O1 C8 N1 112.38(16) . . ?
O1 C8 C7 108.66(16) . . ?
N1 C8 C7 108.38(15) . . ?
C15 C10 C7 119.40(19) . . ?
C15 C10 C11 118.4(2) . . ?
C11 C10 C7 122.2(2) . . ?
C8 C7 C10 107.17(16) . . ?
C8 C7 C16 108.51(16) . . ?
C1 C7 C8 107.70(17) . . ?
C1 C7 C10 111.28(16) . . ?
C1 C7 C16 112.62(18) . . ?
C16 C7 C10 109.36(17) . . ?
C1 C2 C9 121.7(2) . . ?
C3 C2 C9 117.6(2) . . ?
C3 C2 C1 120.7(2) . . ?
N1 O2 C18 109.72(19) . . ?
N1 C9 C2 114.23(18) . . ?
O3 C9 N1 122.0(2) . . ?
O3 C9 C2 123.7(2) . . ?
C2 C1 C7 119.4(2) . . ?
C6 C1 C7 122.1(2) . . ?
C6 C1 C2 118.5(2) . . ?
C14 C15 C10 121.2(3) . . ?
C10 C11 C12 120.3(3) . . ?
C5 C6 C1 120.6(3) . . ?
C13 C12 C11 120.4(3) . . ?
C5 C4 C3 120.7(3) . . ?
C12 C13 C14 119.7(3) . . ?
C2 C3 C4 119.3(3) . . ?
C13 C14 C15 120.0(3) . . ?
C4 C5 C6 120.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_47
_database_code_depnum_ccdc_archive 'CCDC 2006085'
loop_
_audit_author_name
_audit_author_address
'Yan Li'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-06-01 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.37420(10)
_cell_length_b                   8.59040(10)
_cell_length_c                   12.08780(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.0020(10)
_cell_angle_gamma                90
_cell_volume                     751.656(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8710
_cell_measurement_theta_min      5.1160
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9272
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         3.725
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                2783
_reflns_number_total             2808
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.420
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.193
_refine_ls_abs_structure_details 
;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.247
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1331
_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 Ternary CH refined with riding coordinates:
 C8(H006)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H007), C12(H00D), C14(H00E), C13(H00F), C15(H00G), C2(H00H), C5(H00I),
 C3(H00J), C4(H00K)
2.c Idealised Me refined as rotating group:
 C17(H00A,H00B,H00C), C20(H00L,H00M,H00N)
2.d Idealised tetrahedral OH refined as rotating group:
 O18(H001)
;
_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
O18 O 0.7307(2) 0.4902(2) 0.52811(12) 0.0510(4) Uani 1 1 d . . . . .
H001 H 0.698793 0.440296 0.469819 0.077 Uiso 1 1 calc GR . . . .
O19 O 0.3424(2) 0.6034(2) 0.52581(13) 0.0548(5) Uani 1 1 d . . . . .
O21 O 0.4642(3) 0.8418(2) 0.66021(16) 0.0649(5) Uani 1 1 d . . . . .
N9 N 0.4930(2) 0.5873(2) 0.61502(15) 0.0430(4) Uani 1 1 d . . . . .
C11 C 0.5842(2) 0.3503(2) 0.79085(15) 0.0353(4) Uani 1 1 d . . . . .
C8 C 0.6129(2) 0.4559(3) 0.60289(15) 0.0382(4) Uani 1 1 d . . . . .
H006 H 0.535537 0.366834 0.573367 0.046 Uiso 1 1 calc R . . . .
C16 C 0.5546(3) 0.4210(3) 0.88873(17) 0.0455(5) Uani 1 1 d . . . . .
H007 H 0.620249 0.510547 0.914294 0.055 Uiso 1 1 calc R . . . .
C7 C 0.7224(2) 0.4137(2) 0.72155(15) 0.0352(4) Uani 1 1 d . . . . .
C17 C 0.8616(3) 0.2844(3) 0.7099(2) 0.0478(5) Uani 1 1 d . . . . .
H00A H 0.918291 0.247725 0.783442 0.072 Uiso 1 1 calc GR . . . .
H00B H 0.954934 0.324901 0.672253 0.072 Uiso 1 1 calc GR . . . .
H00C H 0.798591 0.199921 0.666904 0.072 Uiso 1 1 calc GR . . . .
C1 C 0.8186(3) 0.5609(2) 0.77397(16) 0.0378(4) Uani 1 1 d . . . . .
C12 C 0.4847(3) 0.2154(3) 0.75483(18) 0.0464(5) Uani 1 1 d . . . . .
H00D H 0.503626 0.164742 0.689991 0.056 Uiso 1 1 calc R . . . .
C14 C 0.3281(3) 0.2287(3) 0.9118(2) 0.0537(6) Uani 1 1 d . . . . .
H00E H 0.241557 0.189361 0.951184 0.064 Uiso 1 1 calc R . . . .
C13 C 0.3570(3) 0.1561(3) 0.8155(2) 0.0557(6) Uani 1 1 d . . . . .
H00F H 0.290819 0.066541 0.790459 0.067 Uiso 1 1 calc R . . . .
C10 C 0.5524(3) 0.7201(3) 0.67091(16) 0.0440(5) Uani 1 1 d . . . . .
C6 C 0.7334(3) 0.7048(3) 0.74963(15) 0.0413(4) Uani 1 1 d . . . . .
C15 C 0.4282(3) 0.3604(3) 0.94984(19) 0.0543(6) Uani 1 1 d . . . . .
H00G H 0.411438 0.408592 1.016041 0.065 Uiso 1 1 calc R . . . .
C2 C 0.9883(3) 0.5572(3) 0.8475(2) 0.0517(5) Uani 1 1 d . . . . .
H00H H 1.047891 0.462373 0.864582 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8161(4) 0.8407(3) 0.7986(2) 0.0557(6) Uani 1 1 d . . . . .
H00I H 0.757851 0.936192 0.782192 0.067 Uiso 1 1 calc R . . . .
C3 C 1.0706(3) 0.6926(4) 0.8960(2) 0.0635(7) Uani 1 1 d . . . . .
H00J H 1.184056 0.687671 0.945196 0.076 Uiso 1 1 calc R . . . .
C4 C 0.9853(4) 0.8331(4) 0.8717(2) 0.0649(7) Uani 1 1 d . . . . .
H00K H 1.040681 0.923635 0.904270 0.078 Uiso 1 1 calc R . . . .
C20 C 0.1787(4) 0.5519(8) 0.5608(4) 0.1080(18) Uani 1 1 d . . . . .
H00L H 0.078025 0.551730 0.497315 0.162 Uiso 1 1 calc GR . . . .
H00M H 0.150430 0.620707 0.617712 0.162 Uiso 1 1 calc GR . . . .
H00N H 0.197094 0.448404 0.590824 0.162 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
O18 C8 1.399(2) . ?
O19 N9 1.400(2) . ?
O19 C20 1.424(3) . ?
O21 C10 1.225(3) . ?
N9 C8 1.458(3) . ?
N9 C10 1.355(3) . ?
C11 C16 1.384(3) . ?
C11 C7 1.537(2) . ?
C11 C12 1.396(3) . ?
C8 C7 1.549(2) . ?
C16 C15 1.396(3) . ?
C7 C17 1.537(3) . ?
C7 C1 1.527(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.391(3) . ?
C12 C13 1.396(3) . ?
C14 C13 1.372(4) . ?
C14 C15 1.381(4) . ?
C10 C6 1.490(3) . ?
C6 C5 1.395(3) . ?
C2 C3 1.389(4) . ?
C5 C4 1.386(4) . ?
C3 C4 1.367(5) . ?

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
N9 O19 C20 109.50(19) . . ?
O19 N9 C8 113.98(17) . . ?
C10 N9 O19 115.72(17) . . ?
C10 N9 C8 123.87(16) . . ?
C16 C11 C7 122.65(18) . . ?
C16 C11 C12 118.14(18) . . ?
C12 C11 C7 119.21(17) . . ?
O18 C8 N9 111.39(18) . . ?
O18 C8 C7 111.67(14) . . ?
N9 C8 C7 107.87(15) . . ?
C11 C16 C15 121.3(2) . . ?
C11 C7 C8 107.74(14) . . ?
C17 C7 C11 108.50(16) . . ?
C17 C7 C8 108.90(16) . . ?
C1 C7 C11 111.78(15) . . ?
C1 C7 C8 108.03(16) . . ?
C1 C7 C17 111.77(15) . . ?
C6 C1 C7 119.51(16) . . ?
C2 C1 C7 122.5(2) . . ?
C2 C1 C6 118.0(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C14 C15 119.7(2) . . ?
C14 C13 C12 120.6(2) . . ?
O21 C10 N9 123.4(2) . . ?
O21 C10 C6 122.4(2) . . ?
N9 C10 C6 114.15(18) . . ?
C1 C6 C10 121.73(19) . . ?
C1 C6 C5 120.65(19) . . ?
C5 C6 C10 117.6(2) . . ?
C14 C15 C16 119.8(2) . . ?
C3 C2 C1 121.2(2) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C5 120.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
