# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_d23190
_database_code_depnum_ccdc_archive 'CCDC 2077525'
loop_
_audit_author_name
_audit_author_address
'Maruti Yadav'
;Pukyong National University
South Korea
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 F N2 O3'
_chemical_formula_sum            'C26 H17 F N2 O3'
_chemical_formula_weight         424.42

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'
F F 0.0171 0.0103 '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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_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'
'-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                   6.8865(7)
_cell_length_b                   22.291(3)
_cell_length_c                   25.817(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3963.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8758
_cell_measurement_theta_min      2.414
_cell_measurement_theta_max      24.9

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20978
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3505
_reflns_number_gt                2929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_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)+(0.0571P)²+0.8835P] 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_number_reflns         3505
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.3293(2) 0.56808(6) 0.52801(5) 0.0233(3) Uani 1 1 d . . .
C2 C 0.4666(2) 0.61213(6) 0.50386(5) 0.0221(3) Uani 1 1 d . . .
C3 C 0.3938(2) 0.66717(7) 0.48656(6) 0.0262(3) Uani 1 1 d . . .
H3 H 0.2596 0.6760 0.4906 0.031 Uiso 1 1 calc R . .
C4 C 0.5151(2) 0.70892(7) 0.46362(6) 0.0303(4) Uani 1 1 d . . .
H4 H 0.4650 0.7466 0.4527 0.036 Uiso 1 1 calc R . .
C5 C 0.7106(2) 0.69562(7) 0.45654(6) 0.0323(4) Uani 1 1 d . . .
H5 H 0.7937 0.7239 0.4402 0.039 Uiso 1 1 calc R . .
C6 C 0.7842(2) 0.64109(7) 0.47324(6) 0.0305(4) Uani 1 1 d . . .
H6 H 0.9177 0.6320 0.4683 0.037 Uiso 1 1 calc R . .
C7 C 0.6633(2) 0.59964(7) 0.49727(5) 0.0256(3) Uani 1 1 d . . .
H7 H 0.7149 0.5626 0.5092 0.031 Uiso 1 1 calc R . .
C8 C 0.3766(2) 0.54189(6) 0.57702(5) 0.0225(3) Uani 1 1 d . . .
C9 C 0.2502(2) 0.50382(7) 0.60212(5) 0.0231(3) Uani 1 1 d . . .
C10 C 0.5090(2) 0.50653(7) 0.65733(5) 0.0228(3) Uani 1 1 d . . .
C11 C 0.6508(2) 0.45537(6) 0.66432(5) 0.0225(3) Uani 1 1 d . . .
C12 C 0.6399(2) 0.40442(7) 0.63339(6) 0.0308(4) Uani 1 1 d . . .
H12 H 0.5361 0.4002 0.6094 0.037 Uiso 1 1 calc R . .
C13 C 0.7799(3) 0.35956(7) 0.63723(6) 0.0357(4) Uani 1 1 d . . .
H13 H 0.7731 0.3247 0.6161 0.043 Uiso 1 1 calc R . .
C14 C 0.9278(2) 0.36691(7) 0.67223(6) 0.0316(4) Uani 1 1 d . . .
C15 C 0.9412(2) 0.41606(7) 0.70417(6) 0.0317(4) Uani 1 1 d . . .
H15 H 1.0438 0.4195 0.7286 0.038 Uiso 1 1 calc R . .
C16 C 0.8015(2) 0.46053(7) 0.69989(6) 0.0273(4) Uani 1 1 d . . .
H16 H 0.8089 0.4949 0.7215 0.033 Uiso 1 1 calc R . .
C17 C 0.5309(2) 0.60063(7) 0.69322(6) 0.0227(3) Uani 1 1 d . . .
C18 C 0.5348(2) 0.63957(7) 0.73899(6) 0.0243(3) Uani 1 1 d . . .
C19 C 0.5520(2) 0.61428(8) 0.78842(6) 0.0284(4) Uani 1 1 d . . .
H19 H 0.5583 0.5719 0.7923 0.034 Uiso 1 1 calc R . .
C20 C 0.5598(2) 0.65085(8) 0.83159(6) 0.0359(4) Uani 1 1 d . . .
H20 H 0.5719 0.6335 0.8650 0.043 Uiso 1 1 calc R . .
C21 C 0.5503(3) 0.71248(9) 0.82648(7) 0.0411(5) Uani 1 1 d . . .
H21 H 0.5564 0.7374 0.8563 0.049 Uiso 1 1 calc R . .
C22 C 0.5319(3) 0.73783(8) 0.77800(7) 0.0410(4) Uani 1 1 d . . .
H22 H 0.5246 0.7802 0.7746 0.049 Uiso 1 1 calc R . .
C23 C 0.5239(2) 0.70191(7) 0.73424(6) 0.0321(4) Uani 1 1 d . . .
H23 H 0.5110 0.7197 0.7010 0.039 Uiso 1 1 calc R . .
C24 C 0.5586(2) 0.61048(7) 0.64211(6) 0.0225(3) Uani 1 1 d . . .
C25 C 0.5961(2) 0.66695(7) 0.61838(6) 0.0265(3) Uani 1 1 d . . .
C26 C 0.5494(2) 0.55165(6) 0.61235(5) 0.0212(3) Uani 1 1 d . . .
H26 H 0.6748 0.5427 0.5944 0.025 Uiso 1 1 calc R . .
F1 F 1.06870(16) 0.32431(5) 0.67515(4) 0.0498(3) Uani 1 1 d . . .
N1 N 0.07367(18) 0.48584(6) 0.58848(5) 0.0289(3) Uani 1 1 d . . .
H1D H 0.0356 0.4939 0.5541 0.035 Uiso 1 1 d R . .
H1E H 0.0139 0.4539 0.6075 0.035 Uiso 1 1 d R . .
N2 N 0.6258(2) 0.71210(6) 0.59836(5) 0.0401(4) Uani 1 1 d . . .
O1 O 0.17421(15) 0.55596(5) 0.50509(4) 0.0338(3) Uani 1 1 d . . .
O2 O 0.31611(14) 0.48263(5) 0.64824(4) 0.0262(3) Uani 1 1 d . . .
O3 O 0.50019(16) 0.54072(4) 0.70402(4) 0.0264(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2507(18) . ?
C1 C8 1.431(2) . ?
C1 C2 1.499(2) . ?
C2 C7 1.393(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.377(2) . ?
C8 C26 1.515(2) . ?
C9 N1 1.3278(19) . ?
C9 O2 1.3590(17) . ?
C10 O3 1.4276(17) . ?
C10 O2 1.4500(17) . ?
C10 C11 1.512(2) . ?
C10 C26 1.5612(19) . ?
C11 C12 1.390(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(2) . ?
C13 H13 0.9500 . ?
C14 F1 1.3599(18) . ?
C14 C15 1.374(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C24 1.351(2) . ?
C17 O3 1.3805(17) . ?
C17 C18 1.466(2) . ?
C18 C23 1.397(2) . ?
C18 C19 1.400(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.424(2) . ?
C24 C26 1.521(2) . ?
C25 N2 1.1497(19) . ?
C26 H26 1.0000 . ?
N1 H1D 0.9424 . ?
N1 H1E 0.9583 . ?

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 C8 121.63(13) . . ?
O1 C1 C2 118.92(12) . . ?
C8 C1 C2 119.45(12) . . ?
C7 C2 C3 119.02(14) . . ?
C7 C2 C1 122.22(13) . . ?
C3 C2 C1 118.75(13) . . ?
C4 C3 C2 120.66(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.84(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.00(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.20(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.27(14) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C1 121.59(13) . . ?
C9 C8 C26 107.54(12) . . ?
C1 C8 C26 130.72(13) . . ?
N1 C9 O2 115.67(13) . . ?
N1 C9 C8 129.76(14) . . ?
O2 C9 C8 114.55(13) . . ?
O3 C10 O2 107.09(11) . . ?
O3 C10 C11 109.21(11) . . ?
O2 C10 C11 109.50(12) . . ?
O3 C10 C26 106.95(11) . . ?
O2 C10 C26 106.25(11) . . ?
C11 C10 C26 117.36(12) . . ?
C12 C11 C16 119.14(14) . . ?
C12 C11 C10 120.83(13) . . ?
C16 C11 C10 119.91(13) . . ?
C11 C12 C13 120.56(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.37(15) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
F1 C14 C13 118.88(15) . . ?
F1 C14 C15 118.39(14) . . ?
C13 C14 C15 122.72(15) . . ?
C14 C15 C16 118.42(15) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 120.77(14) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C24 C17 O3 112.10(13) . . ?
C24 C17 C18 133.48(14) . . ?
O3 C17 C18 114.36(12) . . ?
C23 C18 C19 119.01(14) . . ?
C23 C18 C17 121.14(14) . . ?
C19 C18 C17 119.85(14) . . ?
C20 C19 C18 120.06(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.51(16) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.90(16) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.44(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.07(16) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C17 C24 C25 126.13(14) . . ?
C17 C24 C26 110.32(13) . . ?
C25 C24 C26 123.53(12) . . ?
N2 C25 C24 178.77(16) . . ?
C8 C26 C24 117.41(12) . . ?
C8 C26 C10 102.42(11) . . ?
C24 C26 C10 100.79(11) . . ?
C8 C26 H26 111.7 . . ?
C24 C26 H26 111.7 . . ?
C10 C26 H26 111.7 . . ?
C9 N1 H1D 116.6 . . ?
C9 N1 H1E 118.8 . . ?
H1D N1 H1E 120.3 . . ?
C9 O2 C10 108.65(11) . . ?
C17 O3 C10 109.83(11) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_d23287
_database_code_depnum_ccdc_archive 'CCDC 2083114'
loop_
_audit_author_name
_audit_author_address
'Maruti Yadav'
;Pukyong National University
South Korea
;
_audit_update_record             
;
2021-05-12 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H26 N2 O4'
_chemical_formula_sum            'C33 H26 N2 O4'
_chemical_formula_weight         514.56

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/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                   17.799(3)
_cell_length_b                   9.2371(19)
_cell_length_c                   18.139(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.941(4)
_cell_angle_gamma                90.00
_cell_volume                     2704.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1344
_cell_measurement_theta_min      2.523
_cell_measurement_theta_max      20.189

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27646
_diffrn_reflns_av_R_equivalents  0.1844
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.13
_reflns_number_total             4808
_reflns_number_gt                1952
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_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)+(0.0778P)²+0.0000P] 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_number_reflns         4808
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.2023
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 0.2523(3) 0.6197(5) 0.4080(3) 0.0440(12) Uani 1 1 d . . .
C2 C 0.2449(3) 0.5333(5) 0.4701(2) 0.0365(11) Uani 1 1 d . . .
C3 C 0.2653(3) 0.3907(5) 0.4857(2) 0.0345(11) Uani 1 1 d . . .
C4 C 0.2998(3) 0.2795(5) 0.4522(2) 0.0361(11) Uani 1 1 d . . .
C5 C 0.3205(3) 0.3102(5) 0.3885(3) 0.0463(12) Uani 1 1 d . . .
H5 H 0.3115 0.4045 0.3654 0.056 Uiso 1 1 calc R . .
C6 C 0.3546(3) 0.2029(5) 0.3582(3) 0.0541(14) Uani 1 1 d . . .
H6 H 0.3687 0.2258 0.3145 0.065 Uiso 1 1 calc R . .
C7 C 0.3687(3) 0.0648(5) 0.3894(3) 0.0536(14) Uani 1 1 d . . .
C8 C 0.4055(3) -0.0508(5) 0.3556(3) 0.0740(17) Uani 1 1 d . . .
H8A H 0.3611 -0.0994 0.3100 0.111 Uiso 1 1 calc R . .
H8B H 0.4351 -0.1217 0.3982 0.111 Uiso 1 1 calc R . .
H8C H 0.4442 -0.0061 0.3367 0.111 Uiso 1 1 calc R . .
C9 C 0.3466(3) 0.0359(5) 0.4523(3) 0.0584(14) Uani 1 1 d . . .
H9 H 0.3552 -0.0588 0.4749 0.070 Uiso 1 1 calc R . .
C10 C 0.3125(3) 0.1397(5) 0.4836(3) 0.0495(13) Uani 1 1 d . . .
H10 H 0.2977 0.1158 0.5267 0.059 Uiso 1 1 calc R . .
C11 C 0.2154(2) 0.4693(4) 0.5729(2) 0.0331(10) Uani 1 1 d . . .
C12 C 0.1893(2) 0.4379(5) 0.6385(2) 0.0345(11) Uani 1 1 d . . .
C13 C 0.1732(2) 0.2975(5) 0.6519(2) 0.0353(11) Uani 1 1 d . . .
H13 H 0.1826 0.2218 0.6213 0.042 Uiso 1 1 calc R . .
C14 C 0.1431(3) 0.2633(5) 0.7104(2) 0.0342(11) Uani 1 1 d . . .
C15 C 0.1303(2) 0.3764(4) 0.7570(2) 0.0331(10) Uani 1 1 d . . .
C16 C 0.1490(3) 0.5193(5) 0.7432(3) 0.0434(12) Uani 1 1 d . . .
H16 H 0.1416 0.5960 0.7744 0.052 Uiso 1 1 calc R . .
C17 C 0.1777(3) 0.5498(5) 0.6856(2) 0.0414(12) Uani 1 1 d . . .
H17 H 0.1899 0.6470 0.6773 0.050 Uiso 1 1 calc R . .
C18 C 0.0993(3) 0.3423(5) 0.8151(2) 0.0401(11) Uani 1 1 d . . .
H18 H 0.0911 0.4168 0.8470 0.048 Uiso 1 1 calc R . .
C19 C 0.0813(3) 0.2026(5) 0.8249(2) 0.0377(11) Uani 1 1 d . . .
C20 C 0.0336(3) 0.2616(5) 0.9267(3) 0.0649(16) Uani 1 1 d . . .
H20A H 0.0842 0.3139 0.9612 0.097 Uiso 1 1 calc R . .
H20B H 0.0105 0.2144 0.9610 0.097 Uiso 1 1 calc R . .
H20C H -0.0071 0.3298 0.8898 0.097 Uiso 1 1 calc R . .
C21 C 0.0923(3) 0.0895(5) 0.7775(3) 0.0416(12) Uani 1 1 d . . .
H21 H 0.0783 -0.0072 0.7845 0.050 Uiso 1 1 calc R . .
C22 C 0.1227(3) 0.1196(5) 0.7224(3) 0.0433(12) Uani 1 1 d . . .
H22 H 0.1305 0.0433 0.6913 0.052 Uiso 1 1 calc R . .
C23 C 0.2130(3) 0.5860(5) 0.5266(2) 0.0348(11) Uani 1 1 d . . .
C24 C 0.1790(3) 0.7326(4) 0.5247(2) 0.0329(11) Uani 1 1 d . . .
C25 C 0.0953(3) 0.7601(5) 0.4661(3) 0.0419(12) Uani 1 1 d . . .
C26 C 0.2214(3) 0.8417(5) 0.5756(3) 0.0391(11) Uani 1 1 d . . .
C27 C 0.3078(3) 0.8379(5) 0.6398(3) 0.0396(11) Uani 1 1 d . . .
C28 C 0.3702(3) 0.7607(5) 0.6305(3) 0.0537(13) Uani 1 1 d . . .
H28 H 0.3581 0.7074 0.5820 0.064 Uiso 1 1 calc R . .
C29 C 0.4497(3) 0.7610(5) 0.6913(3) 0.0580(14) Uani 1 1 d . . .
H29 H 0.4916 0.7072 0.6840 0.070 Uiso 1 1 calc R . .
C30 C 0.4699(3) 0.8376(5) 0.7624(3) 0.0527(13) Uani 1 1 d . . .
C31 C 0.5570(3) 0.8347(6) 0.8288(3) 0.0772(17) Uani 1 1 d . . .
H31A H 0.5828 0.7414 0.8280 0.116 Uiso 1 1 calc R . .
H31B H 0.5552 0.8479 0.8817 0.116 Uiso 1 1 calc R . .
H31C H 0.5894 0.9130 0.8199 0.116 Uiso 1 1 calc R . .
C32 C 0.4076(3) 0.9144(5) 0.7711(3) 0.0580(14) Uani 1 1 d . . .
H32 H 0.4198 0.9668 0.8198 0.070 Uiso 1 1 calc R . .
C33 C 0.3278(3) 0.9167(5) 0.7103(3) 0.0518(13) Uani 1 1 d . . .
H33 H 0.2865 0.9729 0.7171 0.062 Uiso 1 1 calc R . .
N1 N 0.2559(3) 0.6916(4) 0.3578(3) 0.0688(14) Uani 1 1 d . . .
N2 N 0.0513(2) 0.6525(4) 0.4179(2) 0.0555(11) Uani 1 1 d . . .
H2A H -0.0001 0.6678 0.3825 0.067 Uiso 1 1 calc R . .
H2B H 0.0738 0.5664 0.4216 0.067 Uiso 1 1 calc R . .
O1 O 0.24691(16) 0.3505(3) 0.54891(16) 0.0365(7) Uani 1 1 d . . .
O2 O 0.05259(18) 0.1552(3) 0.88066(18) 0.0490(9) Uani 1 1 d . . .
O3 O 0.06171(19) 0.8833(3) 0.45973(18) 0.0547(9) Uani 1 1 d . . .
O4 O 0.18558(18) 0.9705(3) 0.57354(17) 0.0490(9) Uani 1 1 d . . .
H4' H 0.1293 0.9580 0.5408 0.059 Uiso 1 1 d 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
C1 N1 1.151(5) . ?
C1 C2 1.431(6) . ?
C2 C3 1.364(5) . ?
C2 C23 1.451(5) . ?
C3 O1 1.369(4) . ?
C3 C4 1.457(5) . ?
C4 C5 1.382(5) . ?
C4 C10 1.391(6) . ?
C5 C6 1.390(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.381(6) . ?
C7 C8 1.511(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C23 1.355(5) . ?
C11 O1 1.384(4) . ?
C11 C12 1.478(5) . ?
C12 C13 1.372(5) . ?
C12 C17 1.410(5) . ?
C13 C14 1.411(5) . ?
C13 H13 0.9500 . ?
C14 C22 1.417(6) . ?
C14 C15 1.423(5) . ?
C15 C16 1.409(5) . ?
C15 C18 1.415(5) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.359(5) . ?
C18 H18 0.9500 . ?
C19 O2 1.382(4) . ?
C19 C21 1.418(6) . ?
C20 O2 1.420(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.351(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.478(5) . ?
C24 C26 1.361(5) . ?
C24 C25 1.442(6) . ?
C25 O3 1.268(5) . ?
C25 N2 1.337(5) . ?
C26 O4 1.343(5) . ?
C26 C27 1.487(6) . ?
C27 C33 1.381(6) . ?
C27 C28 1.389(6) . ?
C28 C29 1.380(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(6) . ?
C29 H29 0.9500 . ?
C30 C32 1.379(6) . ?
C30 C31 1.509(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.383(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
O4 H4' 0.9317 . ?

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 C1 C2 177.7(5) . . ?
C3 C2 C1 126.8(4) . . ?
C3 C2 C23 109.0(4) . . ?
C1 C2 C23 124.3(4) . . ?
C2 C3 O1 107.5(3) . . ?
C2 C3 C4 135.7(4) . . ?
O1 C3 C4 116.8(4) . . ?
C5 C4 C10 118.7(4) . . ?
C5 C4 C3 120.9(4) . . ?
C10 C4 C3 120.5(4) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 122.2(5) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C9 117.0(4) . . ?
C6 C7 C8 121.6(4) . . ?
C9 C7 C8 121.5(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 122.3(5) . . ?
C10 C9 H9 118.9 . . ?
C7 C9 H9 118.9 . . ?
C9 C10 C4 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C4 C10 H10 120.0 . . ?
C23 C11 O1 110.3(3) . . ?
C23 C11 C12 135.7(4) . . ?
O1 C11 C12 113.8(3) . . ?
C13 C12 C17 119.4(4) . . ?
C13 C12 C11 119.2(4) . . ?
C17 C12 C11 121.3(4) . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C22 121.9(4) . . ?
C13 C14 C15 119.3(4) . . ?
C22 C14 C15 118.7(4) . . ?
C16 C15 C18 122.4(4) . . ?
C16 C15 C14 118.2(4) . . ?
C18 C15 C14 119.3(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C15 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C15 C18 H18 120.1 . . ?
C18 C19 O2 125.2(4) . . ?
C18 C19 C21 121.3(4) . . ?
O2 C19 C21 113.5(4) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C19 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C19 C21 H21 120.1 . . ?
C21 C22 C14 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C14 C22 H22 119.5 . . ?
C11 C23 C2 104.6(4) . . ?
C11 C23 C24 130.5(4) . . ?
C2 C23 C24 124.7(4) . . ?
C26 C24 C25 118.4(4) . . ?
C26 C24 C23 123.9(4) . . ?
C25 C24 C23 117.7(4) . . ?
O3 C25 N2 119.0(4) . . ?
O3 C25 C24 121.7(4) . . ?
N2 C25 C24 119.3(4) . . ?
O4 C26 C24 121.0(4) . . ?
O4 C26 C27 111.4(4) . . ?
C24 C26 C27 127.5(4) . . ?
C33 C27 C28 118.4(4) . . ?
C33 C27 C26 119.3(4) . . ?
C28 C27 C26 122.2(4) . . ?
C29 C28 C27 120.3(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 121.6(5) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C32 C30 C29 117.7(5) . . ?
C32 C30 C31 121.5(5) . . ?
C29 C30 C31 120.8(5) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 121.5(5) . . ?
C30 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C27 C33 C32 120.5(5) . . ?
C27 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C25 N2 H2A 120.0 . . ?
C25 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 O1 C11 108.6(3) . . ?
C19 O2 C20 117.7(3) . . ?
C26 O4 H4' 106.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.064
