# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_fro5799
_database_code_depnum_ccdc_archive 'CCDC 1050885'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-05-19 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 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   7.4874(6)
_cell_length_b                   7.3181(4)
_cell_length_c                   15.1101(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.139(5)
_cell_angle_gamma                90.00
_cell_volume                     806.26(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1263
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7457
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4431
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.01
_diffrn_reflns_theta_max         66.54
_reflns_number_total             2009
_reflns_number_gt                1805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0598P)²+0.2392P] 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   -0.2(4)
_refine_ls_number_reflns         2009
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8091(3) -0.0427(3) 0.25228(16) 0.0501(6) Uani 1 1 d . . .
C1 C 0.7654(4) 0.1046(4) 0.27921(19) 0.0387(7) Uani 1 1 d . . .
N2 N 0.5870(3) 0.1616(3) 0.26281(15) 0.0354(6) Uani 1 1 d . . .
C3 C 0.5327(4) 0.3369(5) 0.29511(19) 0.0406(7) Uani 1 1 d . . .
H3 H 0.3970 0.3360 0.2821 0.049 Uiso 1 1 calc R . .
C4 C 0.5864(5) 0.5048(5) 0.2454(2) 0.0521(9) Uani 1 1 d . . .
H4A H 0.4960 0.5210 0.1878 0.063 Uiso 1 1 calc R . .
H4B H 0.5826 0.6138 0.2825 0.063 Uiso 1 1 calc R . .
C5 C 0.7753(5) 0.4885(5) 0.2259(2) 0.0536(9) Uani 1 1 d . . .
H5A H 0.7690 0.4072 0.1737 0.064 Uiso 1 1 calc R . .
H5B H 0.8149 0.6091 0.2096 0.064 Uiso 1 1 calc R . .
C5A C 0.9151(5) 0.4154(4) 0.3058(2) 0.0441(8) Uani 1 1 d . . .
C6 C 1.0510(5) 0.5264(5) 0.3568(3) 0.0541(9) Uani 1 1 d . . .
H6 H 1.0596 0.6491 0.3398 0.065 Uiso 1 1 calc R . .
C7 C 1.1727(5) 0.4591(6) 0.4314(3) 0.0548(9) Uani 1 1 d . . .
H7 H 1.2628 0.5366 0.4655 0.066 Uiso 1 1 calc R . .
C8 C 1.1645(4) 0.2779(5) 0.4572(2) 0.0494(9) Uani 1 1 d . . .
H8 H 1.2480 0.2326 0.5087 0.059 Uiso 1 1 calc R . .
C9 C 1.0325(4) 0.1651(5) 0.4066(2) 0.0418(7) Uani 1 1 d . . .
H9 H 1.0279 0.0415 0.4228 0.050 Uiso 1 1 calc R . .
C9A C 0.9060(4) 0.2327(4) 0.33174(19) 0.0350(7) Uani 1 1 d . . .
C10 C 0.4393(4) 0.0407(4) 0.21386(18) 0.0366(7) Uani 1 1 d . . .
H10 H 0.4997 -0.0656 0.1925 0.044 Uiso 1 1 calc R . .
C11 C 0.3255(4) -0.0334(6) 0.2777(2) 0.0475(8) Uani 1 1 d . . .
H11A H 0.2650 0.0673 0.3021 0.057 Uiso 1 1 calc R . .
H11B H 0.2308 -0.1166 0.2447 0.057 Uiso 1 1 calc R . .
O12 O 0.4439(4) -0.1270(4) 0.34888(15) 0.0673(8) Uani 1 1 d . . .
H12 H 0.3994 -0.1273 0.3944 0.101 Uiso 1 1 calc R . .
C13 C 0.5961(4) 0.3525(5) 0.3953(2) 0.0392(7) Uani 1 1 d . . .
N14 N 0.6378(3) 0.3687(4) 0.47210(18) 0.0466(7) Uani 1 1 d . . .
C15 C 0.3295(4) 0.1363(4) 0.12966(19) 0.0395(7) Uani 1 1 d . . .
C16 C 0.1571(4) 0.2078(6) 0.1223(2) 0.0553(10) Uani 1 1 d . . .
H16 H 0.0982 0.1942 0.1706 0.066 Uiso 1 1 calc R . .
C17 C 0.0690(6) 0.3002(7) 0.0442(3) 0.0771(14) Uani 1 1 d . . .
H17 H -0.0487 0.3490 0.0404 0.093 Uiso 1 1 calc R . .
C18 C 0.1520(6) 0.3208(6) -0.0271(2) 0.0692(12) Uani 1 1 d . . .
H18 H 0.0915 0.3832 -0.0798 0.083 Uiso 1 1 calc R . .
C19 C 0.3235(6) 0.2502(6) -0.0213(2) 0.0591(10) Uani 1 1 d . . .
H19 H 0.3805 0.2630 -0.0703 0.071 Uiso 1 1 calc R . .
C20 C 0.4131(5) 0.1599(5) 0.0567(2) 0.0461(8) Uani 1 1 d . . .
H20 H 0.5319 0.1140 0.0606 0.055 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 C1 1.223(4) . ?
C1 N2 1.367(4) . ?
C1 C9A 1.496(4) . ?
N2 C3 1.463(4) . ?
N2 C10 1.477(4) . ?
C3 C13 1.485(4) . ?
C3 C4 1.541(5) . ?
C3 H3 0.9900 . ?
C4 C5 1.514(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C5A 1.505(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5A C6 1.390(5) . ?
C5A C9A 1.399(4) . ?
C6 C7 1.371(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9400 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9400 . ?
C9 C9A 1.390(4) . ?
C9 H9 0.9400 . ?
C10 C15 1.519(4) . ?
C10 C11 1.524(4) . ?
C10 H10 0.9900 . ?
C11 O12 1.407(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
O12 H12 0.8300 . ?
C13 N14 1.137(4) . ?
C15 C16 1.374(4) . ?
C15 C20 1.397(4) . ?
C16 C17 1.389(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.370(6) . ?
C17 H17 0.9400 . ?
C18 C19 1.368(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.384(5) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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 N2 122.2(3) . . ?
O1 C1 C9A 121.3(3) . . ?
N2 C1 C9A 116.5(3) . . ?
C1 N2 C3 122.8(2) . . ?
C1 N2 C10 119.8(2) . . ?
C3 N2 C10 117.3(2) . . ?
N2 C3 C13 111.0(3) . . ?
N2 C3 C4 114.4(2) . . ?
C13 C3 C4 112.2(3) . . ?
N2 C3 H3 106.2 . . ?
C13 C3 H3 106.2 . . ?
C4 C3 H3 106.2 . . ?
C5 C4 C3 113.0(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5A C5 C4 112.5(3) . . ?
C5A C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C5A C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5A C9A 118.7(3) . . ?
C6 C5A C5 121.6(3) . . ?
C9A C5A C5 119.7(3) . . ?
C7 C6 C5A 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5A C6 H6 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C9A 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C9A C9 H9 119.7 . . ?
C9 C9A C5A 120.0(3) . . ?
C9 C9A C1 118.4(3) . . ?
C5A C9A C1 121.6(3) . . ?
N2 C10 C15 110.2(3) . . ?
N2 C10 C11 111.0(2) . . ?
C15 C10 C11 114.8(2) . . ?
N2 C10 H10 106.8 . . ?
C15 C10 H10 106.8 . . ?
C11 C10 H10 106.8 . . ?
O12 C11 C10 108.1(2) . . ?
O12 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
O12 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 O12 H12 109.5 . . ?
N14 C13 C3 177.0(3) . . ?
C16 C15 C20 118.1(3) . . ?
C16 C15 C10 124.2(3) . . ?
C20 C15 C10 117.6(3) . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 C3 179.6(3) . . . . ?
C9A C1 N2 C3 -0.7(4) . . . . ?
O1 C1 N2 C10 2.2(4) . . . . ?
C9A C1 N2 C10 -178.1(2) . . . . ?
C1 N2 C3 C13 -56.9(4) . . . . ?
C10 N2 C3 C13 120.5(3) . . . . ?
C1 N2 C3 C4 71.4(3) . . . . ?
C10 N2 C3 C4 -111.2(3) . . . . ?
N2 C3 C4 C5 -40.4(4) . . . . ?
C13 C3 C4 C5 87.3(3) . . . . ?
C3 C4 C5 C5A -43.8(4) . . . . ?
C4 C5 C5A C6 -108.2(4) . . . . ?
C4 C5 C5A C9A 69.9(4) . . . . ?
C9A C5A C6 C7 -0.7(5) . . . . ?
C5 C5A C6 C7 177.4(3) . . . . ?
C5A C6 C7 C8 0.8(5) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C9A -1.5(5) . . . . ?
C8 C9 C9A C5A 1.7(4) . . . . ?
C8 C9 C9A C1 -179.9(3) . . . . ?
C6 C5A C9A C9 -0.6(4) . . . . ?
C5 C5A C9A C9 -178.7(3) . . . . ?
C6 C5A C9A C1 -179.0(3) . . . . ?
C5 C5A C9A C1 2.9(4) . . . . ?
O1 C1 C9A C9 -50.9(4) . . . . ?
N2 C1 C9A C9 129.5(3) . . . . ?
O1 C1 C9A C5A 127.5(3) . . . . ?
N2 C1 C9A C5A -52.1(4) . . . . ?
C1 N2 C10 C15 -122.8(3) . . . . ?
C3 N2 C10 C15 59.7(3) . . . . ?
C1 N2 C10 C11 108.9(3) . . . . ?
C3 N2 C10 C11 -68.6(3) . . . . ?
N2 C10 C11 O12 -57.8(4) . . . . ?
C15 C10 C11 O12 176.4(3) . . . . ?
N2 C3 C13 N14 -145(7) . . . . ?
C4 C3 C13 N14 85(7) . . . . ?
N2 C10 C15 C16 -105.0(4) . . . . ?
C11 C10 C15 C16 21.2(5) . . . . ?
N2 C10 C15 C20 71.9(3) . . . . ?
C11 C10 C15 C20 -161.8(3) . . . . ?
C20 C15 C16 C17 0.3(5) . . . . ?
C10 C15 C16 C17 177.2(4) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 -0.2(7) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C18 C19 C20 C15 1.3(6) . . . . ?
C16 C15 C20 C19 -1.1(5) . . . . ?
C10 C15 C20 C19 -178.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 N14 0.83 2.10 2.906(3) 164.4 2_646

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        66.54
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_fro5803
_database_code_depnum_ccdc_archive 'CCDC 1050886'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-05-19 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 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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'

_cell_length_a                   7.9192(2)
_cell_length_b                   14.3040(9)
_cell_length_c                   14.6004(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1653.88(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2108
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7958
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor,2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6802
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.06
_diffrn_reflns_theta_max         66.73
_reflns_number_total             2771
_reflns_number_gt                2607
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0566P)²+0.2974P] 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   -0.0(3)
_refine_ls_number_reflns         2771
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.02747(17) 0.13559(9) 0.19504(13) 0.0627(5) Uani 1 1 d . . .
C1 C 0.9016(2) 0.09234(12) 0.16933(12) 0.0385(4) Uani 1 1 d . . .
N2 N 0.90422(17) -0.00168(9) 0.16000(9) 0.0344(3) Uani 1 1 d . . .
C3 C 0.7651(2) -0.05344(13) 0.11647(12) 0.0409(4) Uani 1 1 d . . .
H3 H 0.8065 -0.1180 0.1068 0.049 Uiso 1 1 calc R . .
C4 C 0.6045(2) -0.06144(15) 0.17502(15) 0.0548(5) Uani 1 1 d . . .
H4A H 0.5071 -0.0696 0.1344 0.066 Uiso 1 1 calc R . .
H4B H 0.6129 -0.1173 0.2136 0.066 Uiso 1 1 calc R . .
C5A C 0.5865(2) 0.11366(15) 0.18428(12) 0.0459(4) Uani 1 1 d . . .
C5 C 0.5740(2) 0.02317(16) 0.23582(14) 0.0560(6) Uani 1 1 d . . .
H5A H 0.4615 0.0183 0.2634 0.067 Uiso 1 1 calc R . .
H5B H 0.6571 0.0232 0.2856 0.067 Uiso 1 1 calc R . .
C6 C 0.4454(3) 0.17008(19) 0.17037(16) 0.0636(6) Uani 1 1 d . . .
H6 H 0.3407 0.1520 0.1950 0.076 Uiso 1 1 calc R . .
C7 C 0.4568(3) 0.25158(19) 0.12134(18) 0.0695(7) Uani 1 1 d . . .
H7 H 0.3602 0.2887 0.1128 0.083 Uiso 1 1 calc R . .
C8 C 0.6082(3) 0.27936(16) 0.08461(16) 0.0632(6) Uani 1 1 d . . .
H8 H 0.6145 0.3342 0.0493 0.076 Uiso 1 1 calc R . .
C9A C 0.7418(2) 0.14367(12) 0.14922(12) 0.0391(4) Uani 1 1 d . . .
C9 C 0.7521(3) 0.22612(13) 0.09982(14) 0.0486(5) Uani 1 1 d . . .
H9 H 0.8568 0.2461 0.0765 0.058 Uiso 1 1 calc R . .
C10 C 1.0569(2) -0.05422(12) 0.18793(12) 0.0386(4) Uani 1 1 d . . .
H10 H 1.1374 -0.0068 0.2109 0.046 Uiso 1 1 calc R . .
C11 C 1.0193(3) -0.11731(14) 0.26857(14) 0.0519(5) Uani 1 1 d . . .
H11A H 1.1248 -0.1450 0.2910 0.062 Uiso 1 1 calc R . .
H11B H 0.9701 -0.0803 0.3183 0.062 Uiso 1 1 calc R . .
O12 O 0.90529(19) -0.18976(10) 0.24341(12) 0.0641(4) Uani 1 1 d . . .
H12 H 0.9400 -0.2404 0.2638 0.096 Uiso 1 1 calc R . .
C13 C 0.7308(3) -0.01430(15) 0.02455(13) 0.0499(5) Uani 1 1 d . . .
N14 N 0.7067(3) 0.01257(18) -0.04764(13) 0.0783(6) Uani 1 1 d . . .
C15 C 1.1432(2) -0.10025(13) 0.10683(14) 0.0418(4) Uani 1 1 d . . .
C16 C 1.1619(3) -0.05220(18) 0.02569(16) 0.0636(6) Uani 1 1 d . . .
H16 H 1.1122 0.0071 0.0194 0.076 Uiso 1 1 calc R . .
C17 C 1.2523(3) -0.0894(3) -0.04669(18) 0.0851(8) Uani 1 1 d . . .
H17 H 1.2628 -0.0554 -0.1015 0.102 Uiso 1 1 calc R . .
C18 C 1.3266(3) -0.1756(2) -0.0390(2) 0.0837(9) Uani 1 1 d . . .
H18 H 1.3883 -0.2009 -0.0881 0.100 Uiso 1 1 calc R . .
C19 C 1.3100(3) -0.22377(19) 0.0401(2) 0.0773(8) Uani 1 1 d . . .
H19 H 1.3613 -0.2827 0.0458 0.093 Uiso 1 1 calc R . .
C20 C 1.2187(3) -0.18776(14) 0.11292(17) 0.0551(5) Uani 1 1 d . . .
H20 H 1.2077 -0.2229 0.1670 0.066 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 C1 1.232(2) . ?
C1 N2 1.352(2) . ?
C1 C9A 1.492(2) . ?
N2 C3 1.471(2) . ?
N2 C10 1.481(2) . ?
C3 C13 1.479(3) . ?
C3 C4 1.537(3) . ?
C3 H3 0.9900 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5A C6 1.393(3) . ?
C5A C9A 1.400(3) . ?
C5A C5 1.501(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9400 . ?
C9A C9 1.385(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.513(3) . ?
C10 C15 1.517(3) . ?
C10 H10 0.9900 . ?
C11 O12 1.423(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
O12 H12 0.8300 . ?
C13 N14 1.138(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.351(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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 N2 121.17(16) . . ?
O1 C1 C9A 119.94(15) . . ?
N2 C1 C9A 118.88(15) . . ?
C1 N2 C3 122.16(14) . . ?
C1 N2 C10 119.33(14) . . ?
C3 N2 C10 118.34(14) . . ?
N2 C3 C13 109.81(15) . . ?
N2 C3 C4 114.63(15) . . ?
C13 C3 C4 112.38(16) . . ?
N2 C3 H3 106.5 . . ?
C13 C3 H3 106.5 . . ?
C4 C3 H3 106.5 . . ?
C5 C4 C3 113.37(16) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5A C9A 118.3(2) . . ?
C6 C5A C5 121.32(19) . . ?
C9A C5A C5 120.38(16) . . ?
C5A C5 C4 112.56(16) . . ?
C5A C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C5A C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5A 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5A C6 H6 119.5 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C9A C5A 120.23(17) . . ?
C9 C9A C1 118.14(17) . . ?
C5A C9A C1 121.49(16) . . ?
C9A C9 C8 120.1(2) . . ?
C9A C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C10 C11 110.89(14) . . ?
N2 C10 C15 111.90(14) . . ?
C11 C10 C15 115.91(15) . . ?
N2 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
C15 C10 H10 105.8 . . ?
O12 C11 C10 110.99(16) . . ?
O12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 O12 H12 109.5 . . ?
N14 C13 C3 177.3(2) . . ?
C16 C15 C20 117.3(2) . . ?
C16 C15 C10 120.20(17) . . ?
C20 C15 C10 122.32(19) . . ?
C15 C16 C17 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 120.7(2) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 C3 -170.56(18) . . . . ?
C9A C1 N2 C3 10.3(2) . . . . ?
O1 C1 N2 C10 4.7(3) . . . . ?
C9A C1 N2 C10 -174.38(15) . . . . ?
C1 N2 C3 C13 54.0(2) . . . . ?
C10 N2 C3 C13 -121.35(17) . . . . ?
C1 N2 C3 C4 -73.6(2) . . . . ?
C10 N2 C3 C4 111.02(18) . . . . ?
N2 C3 C4 C5 33.0(2) . . . . ?
C13 C3 C4 C5 -93.3(2) . . . . ?
C6 C5A C5 C4 112.6(2) . . . . ?
C9A C5A C5 C4 -67.7(2) . . . . ?
C3 C4 C5 C5A 49.6(2) . . . . ?
C9A C5A C6 C7 1.9(3) . . . . ?
C5 C5A C6 C7 -178.4(2) . . . . ?
C5A C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C9 -2.2(4) . . . . ?
C6 C5A C9A C9 -1.8(3) . . . . ?
C5 C5A C9A C9 178.46(17) . . . . ?
C6 C5A C9A C1 173.66(18) . . . . ?
C5 C5A C9A C1 -6.0(3) . . . . ?
O1 C1 C9A C9 43.7(3) . . . . ?
N2 C1 C9A C9 -137.15(18) . . . . ?
O1 C1 C9A C5A -131.9(2) . . . . ?
N2 C1 C9A C5A 47.3(2) . . . . ?
C5A C9A C9 C8 -0.2(3) . . . . ?
C1 C9A C9 C8 -175.81(17) . . . . ?
C7 C8 C9 C9A 2.2(3) . . . . ?
C1 N2 C10 C11 114.46(18) . . . . ?
C3 N2 C10 C11 -70.07(19) . . . . ?
C1 N2 C10 C15 -114.43(17) . . . . ?
C3 N2 C10 C15 61.04(19) . . . . ?
N2 C10 C11 O12 66.5(2) . . . . ?
C15 C10 C11 O12 -62.5(2) . . . . ?
N2 C3 C13 N14 113(5) . . . . ?
C4 C3 C13 N14 -118(5) . . . . ?
N2 C10 C15 C16 42.7(2) . . . . ?
C11 C10 C15 C16 171.17(19) . . . . ?
N2 C10 C15 C20 -143.03(17) . . . . ?
C11 C10 C15 C20 -14.5(2) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C10 C15 C16 C17 174.5(2) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C16 C15 C20 C19 0.6(3) . . . . ?
C10 C15 C20 C19 -173.85(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.73
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
#=============================================================================
#  end of cif data for "fro5803" (compound 3S-11)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
