# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_zyp-3-85
_database_code_depnum_ccdc_archive 'CCDC 1913835'
loop_
_audit_author_name
_audit_author_address
'Zhu yuping '
;Shanghai University
China
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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   'P 21/c'

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

_cell_length_a                   5.556(3)
_cell_length_b                   25.565(13)
_cell_length_c                   11.983(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.38(2)
_cell_angle_gamma                90.00
_cell_volume                     1648.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9100
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0.0
_diffrn_standards_interval_count 0.0
_diffrn_standards_interval_time  0.0
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            10338
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.65
_reflns_number_total             3845
_reflns_number_gt                2276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0830P)²+0.1501P] 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     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3845
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.3799(2) -0.08627(6) 0.11280(13) 0.0752(5) Uani 1 1 d . . .
O2 O -0.0408(4) -0.17813(7) 0.12862(19) 0.1227(9) Uani 1 1 d . . .
O3 O 0.2603(3) -0.05812(5) 0.40901(11) 0.0668(4) Uani 1 1 d . . .
N1 N -0.4441(3) -0.04828(8) 0.18659(17) 0.0725(6) Uani 1 1 d . . .
N2 N 0.1335(3) -0.12751(6) 0.28619(14) 0.0568(4) Uani 1 1 d . . .
C1 C -0.1124(3) -0.08424(9) 0.12359(17) 0.0608(6) Uani 1 1 d . . .
C2 C -0.0140(3) -0.04450(7) 0.21768(15) 0.0499(5) Uani 1 1 d . . .
H2 H 0.0812 -0.0166 0.1992 0.048(5) Uiso 1 1 d R . .
C3 C -0.2497(3) -0.02487(8) 0.24397(17) 0.0569(5) Uani 1 1 d . . .
C4 C -0.0078(4) -0.13609(9) 0.1750(2) 0.0723(6) Uani 1 1 d . . .
C5 C 0.1449(3) -0.07511(7) 0.31746(16) 0.0512(5) Uani 1 1 d . . .
C6 C -0.2604(4) 0.01668(8) 0.3300(2) 0.0695(6) Uani 1 1 d . . .
H6A H -0.1826 0.0037 0.4065 0.099(9) Uiso 1 1 d R . .
H6B H -0.4329 0.0242 0.3272 0.101(8) Uiso 1 1 d R . .
C7 C -0.1327(4) 0.06679(8) 0.30949(16) 0.0561(5) Uani 1 1 d . . .
C8 C 0.1069(4) 0.07705(9) 0.37207(19) 0.0650(6) Uani 1 1 d . . .
H8 H 0.1880 0.0523 0.4252 0.107(9) Uiso 1 1 d R . .
C9 C 0.2294(6) 0.12202(11) 0.3589(3) 0.0881(8) Uani 1 1 d . . .
H9 H 0.3909 0.1275 0.4025 0.176(17) Uiso 1 1 d R . .
C10 C 0.1144(7) 0.15767(12) 0.2828(3) 0.1043(9) Uani 1 1 d U . .
H10 H 0.1993 0.1883 0.2754 0.128(12) Uiso 1 1 d R . .
C11 C -0.1187(7) 0.15101(13) 0.2169(3) 0.1105(10) Uani 1 1 d U . .
H11 H -0.1929 0.1765 0.1642 0.180(16) Uiso 1 1 d R . .
C12 C -0.2477(6) 0.10348(12) 0.2306(2) 0.0922(8) Uani 1 1 d . . .
H12 H -0.4082 0.0979 0.1859 0.119(11) Uiso 1 1 d R . .
C13 C 0.2559(4) -0.16896(8) 0.3613(2) 0.0622(6) Uani 1 1 d . . .
C14 C 0.1701(4) -0.18234(9) 0.4552(2) 0.0731(6) Uani 1 1 d . . .
H14 H 0.0381 -0.1641 0.4715 0.082(7) Uiso 1 1 d R . .
C15 C 0.2802(5) -0.22316(10) 0.5260(3) 0.0903(8) Uani 1 1 d . . .
H15 H 0.2211 -0.2325 0.5893 0.135(13) Uiso 1 1 d R . .
C16 C 0.4740(6) -0.24927(11) 0.5024(3) 0.0980(9) Uani 1 1 d . . .
H16 H 0.5472 -0.2767 0.5499 0.107(10) Uiso 1 1 d R . .
C17 C 0.5636(5) -0.23600(11) 0.4102(4) 0.1004(10) Uani 1 1 d . . .
H17 H 0.6978 -0.2541 0.3956 0.135(12) Uiso 1 1 d R . .
C18 C 0.4531(4) -0.19503(10) 0.3371(3) 0.0825(7) Uani 1 1 d . . .
H18 H 0.5122 -0.1858 0.2737 0.068(6) Uiso 1 1 d R . .
C19 C -0.0698(5) -0.07428(15) 0.0057(2) 0.0958(9) Uani 1 1 d . . .
H19A H -0.1403 -0.0412 -0.0230 0.21(2) Uiso 1 1 d R . .
H19B H -0.1471 -0.1016 -0.0459 0.095(8) Uiso 1 1 d R . .
H19C H 0.1055 -0.0740 0.0110 0.118(10) Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0434(8) 0.1001(12) 0.0794(10) -0.0357(9) 0.0099(7) -0.0120(7)
O2 0.1222(16) 0.0895(13) 0.1277(17) -0.0627(12) -0.0232(13) 0.0087(11)
O3 0.0794(10) 0.0614(9) 0.0524(8) -0.0131(6) 0.0026(7) -0.0041(7)
N1 0.0448(9) 0.0907(14) 0.0850(13) -0.0269(10) 0.0217(9) -0.0084(9)
N2 0.0518(9) 0.0550(10) 0.0635(10) -0.0165(8) 0.0140(7) -0.0069(7)
C1 0.0416(10) 0.0824(14) 0.0575(11) -0.0237(10) 0.0107(8) -0.0090(9)
C2 0.0411(9) 0.0625(11) 0.0479(10) -0.0101(8) 0.0148(8) -0.0085(8)
C3 0.0448(10) 0.0693(13) 0.0598(11) -0.0116(9) 0.0191(9) -0.0081(9)
C4 0.0579(12) 0.0757(15) 0.0786(15) -0.0352(12) 0.0085(11) -0.0076(11)
C5 0.0467(10) 0.0569(11) 0.0523(11) -0.0127(9) 0.0169(8) -0.0087(8)
C6 0.0616(13) 0.0777(14) 0.0796(16) -0.0216(12) 0.0372(12) -0.0106(10)
C7 0.0532(11) 0.0633(12) 0.0555(11) -0.0067(9) 0.0205(9) 0.0083(9)
C8 0.0631(13) 0.0673(13) 0.0678(13) -0.0046(11) 0.0222(11) -0.0027(10)
C9 0.099(2) 0.0829(18) 0.0926(18) -0.0154(15) 0.0422(16) -0.0184(15)
C10 0.152(2) 0.0731(18) 0.106(2) 0.0044(17) 0.0661(18) 0.004(2)
C11 0.154(2) 0.091(2) 0.094(2) 0.0336(17) 0.0459(17) 0.055(2)
C12 0.0844(19) 0.115(2) 0.0764(16) 0.0050(16) 0.0184(15) 0.0360(16)
C13 0.0512(11) 0.0528(11) 0.0834(15) -0.0180(10) 0.0180(10) -0.0069(9)
C14 0.0685(14) 0.0641(14) 0.0895(17) -0.0015(12) 0.0250(12) 0.0027(11)
C15 0.0952(19) 0.0706(16) 0.100(2) 0.0050(14) 0.0156(16) 0.0001(14)
C16 0.090(2) 0.0647(16) 0.127(3) -0.0099(17) 0.0051(19) 0.0041(14)
C17 0.0673(16) 0.0704(17) 0.156(3) -0.0322(18) 0.0141(18) 0.0131(13)
C18 0.0670(14) 0.0760(16) 0.111(2) -0.0256(14) 0.0350(14) -0.0035(12)
C19 0.0821(18) 0.153(3) 0.0534(13) -0.0337(16) 0.0193(12) -0.0249(18)

_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 N1 1.418(2) . ?
O1 C1 1.461(2) . ?
O2 C4 1.203(2) . ?
O3 C5 1.206(2) . ?
N1 C3 1.276(2) . ?
N2 C4 1.386(3) . ?
N2 C5 1.388(2) . ?
N2 C13 1.446(3) . ?
C1 C19 1.511(3) . ?
C1 C2 1.515(3) . ?
C1 C4 1.515(3) . ?
C2 C3 1.507(3) . ?
C2 C5 1.516(3) . ?
C2 H2 0.9461 . ?
C3 C6 1.492(3) . ?
C6 C7 1.514(3) . ?
C6 H6A 0.9701 . ?
C6 H6B 0.9699 . ?
C7 C12 1.372(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.334(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.350(5) . ?
C10 H10 0.9299 . ?
C11 C12 1.441(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9298 . ?
C13 C14 1.370(3) . ?
C13 C18 1.374(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.355(4) . ?
C15 H15 0.9301 . ?
C16 C17 1.362(5) . ?
C16 H16 0.9301 . ?
C17 C18 1.405(4) . ?
C17 H17 0.9299 . ?
C18 H18 0.9301 . ?
C19 H19A 0.9599 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9599 . ?

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 O1 C1 109.19(13) . . ?
C3 N1 O1 110.30(16) . . ?
C4 N2 C5 112.92(17) . . ?
C4 N2 C13 123.29(16) . . ?
C5 N2 C13 123.79(16) . . ?
O1 C1 C19 108.39(17) . . ?
O1 C1 C2 105.11(14) . . ?
C19 C1 C2 118.1(2) . . ?
O1 C1 C4 106.49(17) . . ?
C19 C1 C4 113.2(2) . . ?
C2 C1 C4 104.65(16) . . ?
C3 C2 C1 101.97(14) . . ?
C3 C2 C5 111.92(16) . . ?
C1 C2 C5 105.82(16) . . ?
C3 C2 H2 111.3 . . ?
C1 C2 H2 116.8 . . ?
C5 C2 H2 108.9 . . ?
N1 C3 C6 122.19(18) . . ?
N1 C3 C2 113.22(17) . . ?
C6 C3 C2 124.57(16) . . ?
O2 C4 N2 124.8(2) . . ?
O2 C4 C1 126.5(2) . . ?
N2 C4 C1 108.72(16) . . ?
O3 C5 N2 124.86(18) . . ?
O3 C5 C2 127.28(17) . . ?
N2 C5 C2 107.85(15) . . ?
C3 C6 C7 112.94(17) . . ?
C3 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C3 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 117.8(2) . . ?
C12 C7 C6 122.2(2) . . ?
C8 C7 C6 120.0(2) . . ?
C9 C8 C7 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 122.7(3) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 121.3 . . ?
C7 C12 C11 119.7(3) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C18 120.7(2) . . ?
C14 C13 N2 119.23(18) . . ?
C18 C13 N2 120.1(2) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 118.6(3) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C1 C19 H19A 109.8 . . ?
C1 C19 H19B 109.3 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.3 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_zyp-2-101
_database_code_depnum_ccdc_archive 'CCDC 1985053'
loop_
_audit_author_name
_audit_author_address
'Zhu yuping '
;Shanghai University
China
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 N O3'
_chemical_formula_weight         213.19

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   'P 21'

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

_cell_length_a                   5.611(5)
_cell_length_b                   6.369(5)
_cell_length_c                   13.868(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.958(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     491.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2850
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0.0
_diffrn_standards_interval_count 0.0
_diffrn_standards_interval_time  0.0
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            2938
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.61
_reflns_number_total             1972
_reflns_number_gt                1792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0569P)²+0.0126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.7(12)
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.2019(3) 0.4895(3) 0.68104(11) 0.0474(4) Uani 1 1 d . . .
C2 C 0.3509(3) 0.6781(3) 0.66367(10) 0.0424(3) Uani 1 1 d . . .
C3 C 0.5752(3) 0.7159(3) 0.71994(10) 0.0433(4) Uani 1 1 d . . .
C4 C 0.6747(3) 0.5719(3) 0.80153(10) 0.0468(4) Uani 1 1 d . . .
C5 C 0.5221(3) 0.3919(3) 0.81898(11) 0.0441(4) Uani 1 1 d . . .
C6 C 0.3080(3) 0.3593(3) 0.76354(12) 0.0471(4) Uani 1 1 d . . .
C7 C 0.2661(3) 0.8165(3) 0.58902(11) 0.0507(4) Uani 1 1 d . . .
H7 H 0.1187 0.7920 0.5524 0.061 Uiso 1 1 calc R . .
C8 C 0.4019(3) 0.9906(3) 0.56942(13) 0.0574(4) Uani 1 1 d . . .
H8 H 0.3459 1.0821 0.5195 0.069 Uiso 1 1 calc R . .
C9 C 0.6220(3) 1.0274(3) 0.62473(13) 0.0596(5) Uani 1 1 d . . .
H9 H 0.7125 1.1440 0.6116 0.072 Uiso 1 1 calc R . .
C10 C 0.7080(3) 0.8910(3) 0.69955(12) 0.0523(4) Uani 1 1 d . . .
H10 H 0.8551 0.9174 0.7361 0.063 Uiso 1 1 calc R . .
C11 C 0.5456(3) 0.2180(3) 0.88543(11) 0.0527(4) Uani 1 1 d . . .
C12 C 0.7460(4) 0.1670(4) 0.96363(13) 0.0676(5) Uani 1 1 d . . .
H12A H 0.7096 0.0392 0.9955 0.101 Uiso 1 1 calc R . .
H12B H 0.7641 0.2793 1.0101 0.101 Uiso 1 1 calc R . .
H12C H 0.8927 0.1500 0.9353 0.101 Uiso 1 1 calc R . .
N1 N 0.3582(3) 0.0935(3) 0.87004(12) 0.0642(4) Uani 1 1 d . . .
O1 O 0.0138(2) 0.4462(2) 0.63140(10) 0.0681(4) Uani 1 1 d . . .
O2 O 0.8710(2) 0.6022(3) 0.84887(10) 0.0742(4) Uani 1 1 d . . .
O3 O 0.2020(2) 0.1833(2) 0.79065(9) 0.0632(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0388(8) 0.0557(10) 0.0464(8) -0.0082(7) 0.0003(6) -0.0099(7)
C2 0.0380(7) 0.0466(9) 0.0424(7) -0.0070(7) 0.0041(5) -0.0067(7)
C3 0.0384(7) 0.0475(9) 0.0436(7) -0.0093(7) 0.0035(6) -0.0067(7)
C4 0.0414(8) 0.0534(10) 0.0436(8) -0.0077(7) -0.0025(6) -0.0101(7)
C5 0.0427(7) 0.0483(9) 0.0413(7) -0.0042(6) 0.0045(6) -0.0024(7)
C6 0.0421(8) 0.0472(10) 0.0521(8) -0.0028(7) 0.0055(6) -0.0131(7)
C7 0.0433(8) 0.0612(11) 0.0467(8) -0.0033(7) 0.0016(6) 0.0002(8)
C8 0.0604(10) 0.0548(11) 0.0574(9) 0.0063(8) 0.0091(8) 0.0000(9)
C9 0.0625(11) 0.0522(11) 0.0660(11) -0.0016(8) 0.0153(9) -0.0136(8)
C10 0.0453(8) 0.0538(10) 0.0573(9) -0.0047(8) 0.0043(7) -0.0154(8)
C11 0.0544(9) 0.0565(11) 0.0485(8) -0.0029(7) 0.0119(7) -0.0014(8)
C12 0.0720(11) 0.0736(14) 0.0561(10) 0.0121(10) 0.0034(8) 0.0080(11)
N1 0.0636(9) 0.0623(10) 0.0669(9) 0.0103(8) 0.0088(7) -0.0081(8)
O1 0.0509(7) 0.0776(9) 0.0704(8) 0.0002(7) -0.0152(6) -0.0241(7)
O2 0.0561(7) 0.0884(11) 0.0703(8) 0.0103(8) -0.0237(6) -0.0249(8)
O3 0.0574(7) 0.0614(8) 0.0698(7) 0.0049(7) 0.0031(6) -0.0216(7)

_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
C1 O1 1.220(2) . ?
C1 C6 1.479(2) . ?
C1 C2 1.499(2) . ?
C2 C7 1.398(2) . ?
C2 C3 1.419(2) . ?
C3 C10 1.389(2) . ?
C3 C4 1.510(2) . ?
C4 O2 1.227(2) . ?
C4 C5 1.469(2) . ?
C5 C6 1.361(2) . ?
C5 C11 1.437(3) . ?
C6 O3 1.343(2) . ?
C7 C8 1.391(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.394(3) . ?
C11 N1 1.313(3) . ?
C11 C12 1.500(3) . ?
N1 O3 1.440(2) . ?

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 C6 123.35(16) . . ?
O1 C1 C2 123.49(17) . . ?
C6 C1 C2 113.16(13) . . ?
C7 C2 C3 119.98(14) . . ?
C7 C2 C1 118.52(14) . . ?
C3 C2 C1 121.49(14) . . ?
C10 C3 C2 119.08(15) . . ?
C10 C3 C4 118.77(14) . . ?
C2 C3 C4 122.15(13) . . ?
O2 C4 C5 122.55(16) . . ?
O2 C4 C3 122.14(16) . . ?
C5 C4 C3 115.30(13) . . ?
C6 C5 C11 104.54(15) . . ?
C6 C5 C4 121.22(15) . . ?
C11 C5 C4 134.21(15) . . ?
O3 C6 C5 111.07(15) . . ?
O3 C6 C1 122.27(14) . . ?
C5 C6 C1 126.62(14) . . ?
C8 C7 C2 120.13(16) . . ?
C7 C8 C9 119.79(17) . . ?
C8 C9 C10 120.61(17) . . ?
C3 C10 C9 120.41(16) . . ?
N1 C11 C5 110.57(16) . . ?
N1 C11 C12 120.15(19) . . ?
C5 C11 C12 129.28(18) . . ?
C11 N1 O3 106.60(16) . . ?
C6 O3 N1 107.23(13) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
