# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20150925ngd1_0m
_database_code_depnum_ccdc_archive 'CCDC 1486451'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 F2 N2 O4'
_chemical_formula_weight         414.40

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3577(8)
_cell_length_b                   11.4090(9)
_cell_length_c                   11.7512(8)
_cell_angle_alpha                63.086(2)
_cell_angle_beta                 75.619(2)
_cell_angle_gamma                69.263(2)
_cell_volume                     1040.37(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3942
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7429
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3630
_reflns_number_gt                2870
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0505P)²+0.3672P] 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       0.081(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3630
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.5628(3) 0.8847(2) 0.3970(2) 0.0608(6) Uani 1 1 d . . .
H1 H 0.5095 0.8785 0.4768 0.073 Uiso 1 1 calc R . .
C2 C 0.6922(3) 0.9298(2) 0.3538(3) 0.0736(7) Uani 1 1 d . . .
C3 C 0.7760(3) 0.9392(3) 0.2383(3) 0.0846(9) Uani 1 1 d . . .
H3 H 0.8635 0.9697 0.2122 0.101 Uiso 1 1 calc R . .
C4 C 0.7268(3) 0.9024(3) 0.1628(3) 0.0809(8) Uani 1 1 d . . .
H4 H 0.7820 0.9070 0.0840 0.097 Uiso 1 1 calc R . .
C5 C 0.5965(3) 0.8583(2) 0.2014(2) 0.0630(6) Uani 1 1 d . . .
H5 H 0.5638 0.8348 0.1480 0.076 Uiso 1 1 calc R . .
C6 C 0.5143(2) 0.84900(19) 0.31866(19) 0.0480(5) Uani 1 1 d . . .
C7 C 0.3414(2) 0.7179(2) 0.47777(18) 0.0476(5) Uani 1 1 d . . .
C8 C 0.2152(4) 0.4798(3) 0.6483(4) 0.1130(12) Uani 1 1 d . . .
H8A H 0.2339 0.4578 0.5752 0.170 Uiso 1 1 calc R . .
H8B H 0.1570 0.4233 0.7169 0.170 Uiso 1 1 calc R . .
H8C H 0.3114 0.4637 0.6757 0.170 Uiso 1 1 calc R . .
C9 C 0.1267(3) 0.6270(2) 0.6128(2) 0.0625(6) Uani 1 1 d . . .
C10 C -0.0309(3) 0.6556(4) 0.5794(3) 0.1074(12) Uani 1 1 d . . .
H10A H -0.0838 0.7511 0.5557 0.161 Uiso 1 1 calc R . .
H10B H -0.0880 0.6021 0.6523 0.161 Uiso 1 1 calc R . .
H10C H -0.0216 0.6317 0.5087 0.161 Uiso 1 1 calc R . .
C11 C 0.1182(4) 0.6772(4) 0.7147(3) 0.1016(10) Uani 1 1 d . . .
H11A H 0.2200 0.6565 0.7350 0.152 Uiso 1 1 calc R . .
H11B H 0.0573 0.6324 0.7905 0.152 Uiso 1 1 calc R . .
H11C H 0.0720 0.7744 0.6830 0.152 Uiso 1 1 calc R . .
C12 C 0.2659(2) 0.87546(19) 0.26174(17) 0.0446(5) Uani 1 1 d . . .
C13 C 0.1904(3) 1.0067(2) 0.2282(2) 0.0593(6) Uani 1 1 d . . .
H13A H 0.2078 1.0570 0.2648 0.071 Uiso 1 1 calc R . .
H13B H 0.1200 1.0486 0.1680 0.071 Uiso 1 1 calc R . .
C14 C 0.2538(2) 0.78958(19) 0.20582(16) 0.0433(5) Uani 1 1 d . . .
C15 C 0.3203(2) 0.6591(2) 0.22475(17) 0.0460(5) Uani 1 1 d . . .
H15 H 0.3919 0.5970 0.2824 0.055 Uiso 1 1 calc R . .
C16 C 0.1620(2) 0.7509(2) 0.07133(19) 0.0490(5) Uani 1 1 d . . .
C17 C 0.3129(2) 0.50608(19) 0.12659(17) 0.0430(5) Uani 1 1 d . . .
C18 C 0.2296(3) 0.4801(2) 0.06263(19) 0.0538(5) Uani 1 1 d . . .
H18 H 0.1400 0.5440 0.0285 0.065 Uiso 1 1 calc R . .
C19 C 0.2837(3) 0.3567(2) 0.0513(2) 0.0616(6) Uani 1 1 d . . .
C20 C 0.4140(3) 0.2596(2) 0.0985(2) 0.0674(7) Uani 1 1 d . . .
H20 H 0.4470 0.1774 0.0884 0.081 Uiso 1 1 calc R . .
C21 C 0.4953(3) 0.2871(2) 0.1617(2) 0.0709(7) Uani 1 1 d . . .
H21 H 0.5851 0.2226 0.1950 0.085 Uiso 1 1 calc R . .
C22 C 0.4454(3) 0.4095(2) 0.1764(2) 0.0575(6) Uani 1 1 d . . .
H22 H 0.5011 0.4266 0.2198 0.069 Uiso 1 1 calc R . .
F1 F 0.7360(2) 0.9701(2) 0.4301(2) 0.1138(7) Uani 1 1 d . . .
F2 F 0.1992(2) 0.33091(17) -0.00957(17) 0.0997(6) Uani 1 1 d . . .
N1 N 0.37576(19) 0.80786(16) 0.35484(14) 0.0456(4) Uani 1 1 d . . .
N2 N 0.26347(18) 0.63146(16) 0.14267(14) 0.0442(4) Uani 1 1 d . . .
O1 O 0.43060(18) 0.65407(17) 0.55798(13) 0.0651(4) Uani 1 1 d . . .
O2 O 0.19780(17) 0.71319(15) 0.49103(12) 0.0560(4) Uani 1 1 d . . .
O3 O 0.0903(2) 0.77388(16) -0.01153(16) 0.0714(5) Uani 1 1 d . . .
O4 O 0.15533(16) 0.84845(13) 0.11149(12) 0.0508(4) 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 C2 1.374(3) . ?
C1 C6 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(4) . ?
C2 F1 1.368(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.435(3) . ?
C7 O1 1.206(2) . ?
C7 O2 1.332(2) . ?
C7 N1 1.380(2) . ?
C8 C9 1.494(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.474(2) . ?
C9 C10 1.506(4) . ?
C9 C11 1.520(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.323(3) . ?
C12 N1 1.443(2) . ?
C12 C14 1.450(3) . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C15 1.329(3) . ?
C14 O4 1.387(2) . ?
C15 N2 1.400(2) . ?
C15 H15 0.9300 . ?
C16 O3 1.199(2) . ?
C16 O4 1.370(2) . ?
C16 N2 1.381(2) . ?
C17 C22 1.380(3) . ?
C17 C18 1.385(3) . ?
C17 N2 1.424(2) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(4) . ?
C19 F2 1.363(3) . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
C2 C1 C6 118.0(2) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C3 C2 F1 119.0(3) . . ?
C3 C2 C1 123.4(3) . . ?
F1 C2 C1 117.6(3) . . ?
C4 C3 C2 117.6(2) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 N1 120.94(18) . . ?
C5 C6 N1 119.4(2) . . ?
O1 C7 O2 126.77(18) . . ?
O1 C7 N1 124.02(19) . . ?
O2 C7 N1 109.20(16) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C8 110.1(2) . . ?
O2 C9 C10 102.02(18) . . ?
C8 C9 C10 111.7(3) . . ?
O2 C9 C11 108.4(2) . . ?
C8 C9 C11 112.7(3) . . ?
C10 C9 C11 111.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 121.14(19) . . ?
C13 C12 C14 124.53(19) . . ?
N1 C12 C14 114.25(16) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 O4 108.78(16) . . ?
C15 C14 C12 133.34(18) . . ?
O4 C14 C12 117.88(16) . . ?
C14 C15 N2 107.99(17) . . ?
C14 C15 H15 126.0 . . ?
N2 C15 H15 126.0 . . ?
O3 C16 O4 123.02(18) . . ?
O3 C16 N2 130.17(19) . . ?
O4 C16 N2 106.81(16) . . ?
C22 C17 C18 119.96(19) . . ?
C22 C17 N2 119.11(17) . . ?
C18 C17 N2 120.93(18) . . ?
C19 C18 C17 117.8(2) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C20 C19 F2 118.8(2) . . ?
C20 C19 C18 123.8(2) . . ?
F2 C19 C18 117.3(2) . . ?
C19 C20 C21 117.6(2) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 119.9(2) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C7 N1 C6 121.45(16) . . ?
C7 N1 C12 120.99(16) . . ?
C6 N1 C12 117.23(15) . . ?
C16 N2 C15 107.94(16) . . ?
C16 N2 C17 125.86(16) . . ?
C15 N2 C17 125.93(16) . . ?
C7 O2 C9 122.09(15) . . ?
C16 O4 C14 108.47(14) . . ?

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
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C1 C2 F1 177.5(2) . . . . ?
F1 C2 C3 C4 -178.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 N1 -176.7(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 N1 177.7(2) . . . . ?
C13 C12 C14 C15 178.9(2) . . . . ?
N1 C12 C14 C15 2.2(3) . . . . ?
C13 C12 C14 O4 -0.7(3) . . . . ?
N1 C12 C14 O4 -177.39(15) . . . . ?
O4 C14 C15 N2 -0.6(2) . . . . ?
C12 C14 C15 N2 179.82(19) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
N2 C17 C18 C19 -179.67(17) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C17 C18 C19 F2 178.74(18) . . . . ?
F2 C19 C20 C21 -178.7(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
N2 C17 C22 C21 -179.97(19) . . . . ?
C20 C21 C22 C17 -0.4(4) . . . . ?
O1 C7 N1 C6 -10.0(3) . . . . ?
O2 C7 N1 C6 170.67(16) . . . . ?
O1 C7 N1 C12 176.74(19) . . . . ?
O2 C7 N1 C12 -2.5(2) . . . . ?
C1 C6 N1 C7 -44.4(3) . . . . ?
C5 C6 N1 C7 138.3(2) . . . . ?
C1 C6 N1 C12 129.0(2) . . . . ?
C5 C6 N1 C12 -48.2(2) . . . . ?
C13 C12 N1 C7 105.9(2) . . . . ?
C14 C12 N1 C7 -77.3(2) . . . . ?
C13 C12 N1 C6 -67.6(2) . . . . ?
C14 C12 N1 C6 109.22(19) . . . . ?
O3 C16 N2 C15 178.3(2) . . . . ?
O4 C16 N2 C15 -1.2(2) . . . . ?
O3 C16 N2 C17 4.0(4) . . . . ?
O4 C16 N2 C17 -175.52(16) . . . . ?
C14 C15 N2 C16 1.1(2) . . . . ?
C14 C15 N2 C17 175.46(17) . . . . ?
C22 C17 N2 C16 161.0(2) . . . . ?
C18 C17 N2 C16 -19.4(3) . . . . ?
C22 C17 N2 C15 -12.4(3) . . . . ?
C18 C17 N2 C15 167.24(18) . . . . ?
O1 C7 O2 C9 1.5(3) . . . . ?
N1 C7 O2 C9 -179.24(17) . . . . ?
C8 C9 O2 C7 -60.8(3) . . . . ?
C10 C9 O2 C7 -179.5(2) . . . . ?
C11 C9 O2 C7 62.9(3) . . . . ?
O3 C16 O4 C14 -178.7(2) . . . . ?
N2 C16 O4 C14 0.8(2) . . . . ?
C15 C14 O4 C16 -0.1(2) . . . . ?
C12 C14 O4 C16 179.53(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_20150107ngd21_0m
_database_code_depnum_ccdc_archive 'CCDC 1486452'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N2 O4'
_chemical_formula_weight         434.52

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.797(13)
_cell_length_b                   11.711(15)
_cell_length_c                   12.514(15)
_cell_angle_alpha                113.344(17)
_cell_angle_beta                 96.823(19)
_cell_angle_gamma                113.413(19)
_cell_volume                     1259(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3173
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6603
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4351
_reflns_number_gt                3229
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.2767
_refine_ls_wR_factor_gt          0.2702
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.7604(4) 0.5982(5) 1.2561(4) 0.0757(16) Uani 1 1 d . . .
H1A H 0.7315 0.6557 1.2340 0.114 Uiso 1 1 calc R . .
H1B H 0.7228 0.5857 1.3188 0.114 Uiso 1 1 calc R . .
H1C H 0.7246 0.5069 1.1849 0.114 Uiso 1 1 calc R . .
C2 C 0.9675(5) 0.5794(4) 1.3401(4) 0.0681(13) Uani 1 1 d . . .
H2A H 0.9255 0.4857 1.2704 0.102 Uiso 1 1 calc R . .
H2B H 0.9352 0.5730 1.4068 0.102 Uiso 1 1 calc R . .
H2C H 1.0696 0.6215 1.3653 0.102 Uiso 1 1 calc R . .
C3 C 0.9846(5) 0.8234(5) 1.4072(4) 0.0777(16) Uani 1 1 d . . .
H3A H 1.0849 0.8621 1.4452 0.117 Uiso 1 1 calc R . .
H3B H 0.9374 0.8241 1.4676 0.117 Uiso 1 1 calc R . .
H3C H 0.9705 0.8800 1.3738 0.117 Uiso 1 1 calc R . .
C4 C 0.9229(4) 0.6717(4) 1.3047(3) 0.0537(11) Uani 1 1 d . . .
C5 C 1.0956(4) 0.7222(4) 1.1974(3) 0.0494(10) Uani 1 1 d . . .
C6 C 1.2535(5) 0.7915(4) 0.9697(4) 0.0634(13) Uani 1 1 d . . .
H6 H 1.1830 0.8043 0.9341 0.076 Uiso 1 1 calc R . .
C7 C 1.3799(5) 0.8229(5) 0.9400(4) 0.0778(16) Uani 1 1 d . . .
H7 H 1.3919 0.8557 0.8833 0.093 Uiso 1 1 calc R . .
C8 C 1.4856(5) 0.8065(5) 0.9919(5) 0.0845(18) Uani 1 1 d . . .
H8 H 1.5690 0.8283 0.9716 0.101 Uiso 1 1 calc R . .
C9 C 1.4659(5) 0.7567(5) 1.0757(5) 0.0737(15) Uani 1 1 d . . .
H9 H 1.5379 0.7457 1.1114 0.088 Uiso 1 1 calc R . .
C10 C 1.3429(4) 0.7227(4) 1.1083(4) 0.0621(13) Uani 1 1 d . . .
H10 H 1.3319 0.6892 1.1645 0.075 Uiso 1 1 calc R . .
C11 C 1.2353(4) 0.7405(4) 1.0536(3) 0.0493(10) Uani 1 1 d . . .
C12 C 0.9826(4) 0.6560(3) 0.9909(3) 0.0439(9) Uani 1 1 d . . .
C13 C 0.8816(4) 0.6241(3) 0.9152(3) 0.0434(9) Uani 1 1 d . . .
C14 C 0.7603(3) 0.5930(3) 0.8266(3) 0.0425(9) Uani 1 1 d . . .
C15 C 0.6338(4) 0.5635(4) 0.8439(4) 0.0674(14) Uani 1 1 d . . .
H15A H 0.6222 0.5627 0.9162 0.081 Uiso 1 1 calc R . .
H15B H 0.5573 0.5438 0.7838 0.081 Uiso 1 1 calc R . .
C16 C 0.8951(5) 0.8636(4) 0.8223(4) 0.0603(12) Uani 1 1 d . . .
H16 H 0.8213 0.8552 0.8554 0.072 Uiso 1 1 calc R . .
C17 C 1.0002(5) 0.9974(5) 0.8502(5) 0.0800(17) Uani 1 1 d . . .
H17 H 0.9968 1.0787 0.9010 0.096 Uiso 1 1 calc R . .
C18 C 1.1084(6) 1.0080(5) 0.8022(5) 0.0881(18) Uani 1 1 d . . .
H18 H 1.1796 1.0975 0.8211 0.106 Uiso 1 1 calc R . .
C19 C 1.1144(5) 0.8893(5) 0.7263(4) 0.0795(16) Uani 1 1 d . . .
H19 H 1.1892 0.8990 0.6943 0.095 Uiso 1 1 calc R . .
C20 C 1.0100(4) 0.7552(4) 0.6972(4) 0.0606(12) Uani 1 1 d . . .
H20 H 1.0140 0.6747 0.6456 0.073 Uiso 1 1 calc R . .
C21 C 0.8993(4) 0.7420(3) 0.7454(3) 0.0442(9) Uani 1 1 d . . .
C22 C 0.7168(4) 0.4964(4) 0.6017(3) 0.0497(10) Uani 1 1 d . . .
C23 C 0.5250(5) 0.2443(4) 0.4851(4) 0.0634(13) Uani 1 1 d . . .
C24 C 0.6143(6) 0.1877(5) 0.4197(5) 0.093(2) Uani 1 1 d . . .
H24A H 0.6645 0.2474 0.3874 0.140 Uiso 1 1 calc R . .
H24B H 0.5531 0.0923 0.3535 0.140 Uiso 1 1 calc R . .
H24C H 0.6819 0.1877 0.4770 0.140 Uiso 1 1 calc R . .
C25 C 0.4366(6) 0.2755(6) 0.4096(6) 0.123(2) Uani 1 1 d . . .
H25A H 0.4028 0.3334 0.4618 0.185 Uiso 1 1 calc R . .
H25B H 0.3566 0.1877 0.3457 0.185 Uiso 1 1 calc R . .
H25C H 0.4942 0.3253 0.3733 0.185 Uiso 1 1 calc R . .
C26 C 0.4396(6) 0.1517(5) 0.5343(5) 0.099(2) Uani 1 1 d . . .
H26A H 0.5026 0.1416 0.5864 0.149 Uiso 1 1 calc R . .
H26B H 0.3707 0.0596 0.4668 0.149 Uiso 1 1 calc R . .
H26C H 0.3911 0.1951 0.5809 0.149 Uiso 1 1 calc R . .
N1 N 1.1027(3) 0.7005(3) 1.0792(2) 0.0463(8) Uani 1 1 d . . .
N2 N 0.7868(3) 0.6055(3) 0.7207(2) 0.0454(8) Uani 1 1 d . . .
O1 O 1.2004(3) 0.7801(3) 1.2839(2) 0.0703(10) Uani 1 1 d . . .
O2 O 0.9618(3) 0.6714(3) 1.1943(2) 0.0555(8) Uani 1 1 d . . .
O3 O 0.7386(3) 0.5084(3) 0.5134(2) 0.0711(10) Uani 1 1 d . . .
O4 O 0.6225(3) 0.3786(3) 0.6010(2) 0.0623(9) 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 C4 1.523(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.529(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.515(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O2 1.490(5) . ?
C5 O1 1.195(4) . ?
C5 O2 1.315(5) . ?
C5 N1 1.415(5) . ?
C6 C11 1.395(7) . ?
C6 C7 1.402(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.406(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.438(5) . ?
C12 C13 1.173(5) . ?
C12 N1 1.357(5) . ?
C13 C14 1.425(5) . ?
C14 C15 1.336(6) . ?
C14 N2 1.440(5) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 C21 1.389(6) . ?
C16 C17 1.387(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 N2 1.449(5) . ?
C22 O3 1.207(5) . ?
C22 O4 1.346(5) . ?
C22 N2 1.370(4) . ?
C23 O4 1.483(4) . ?
C23 C26 1.507(8) . ?
C23 C25 1.508(8) . ?
C23 C24 1.517(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C1 102.2(3) . . ?
O2 C4 C3 110.1(4) . . ?
C1 C4 C3 111.1(4) . . ?
O2 C4 C2 109.5(4) . . ?
C1 C4 C2 108.9(4) . . ?
C3 C4 C2 114.4(4) . . ?
O1 C5 O2 128.0(4) . . ?
O1 C5 N1 122.0(4) . . ?
O2 C5 N1 110.0(3) . . ?
C11 C6 C7 118.9(5) . . ?
C11 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.7(5) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 118.5(5) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C10 122.6(5) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C9 C10 C11 117.9(5) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C6 C11 C10 120.4(4) . . ?
C6 C11 N1 119.2(4) . . ?
C10 C11 N1 120.3(4) . . ?
C13 C12 N1 176.7(4) . . ?
C12 C13 C14 176.9(4) . . ?
C15 C14 C13 122.8(4) . . ?
C15 C14 N2 122.2(4) . . ?
C13 C14 N2 114.8(3) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C21 C16 C17 120.6(5) . . ?
C21 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.0(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 120.3(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 N2 122.7(3) . . ?
C16 C21 N2 117.8(4) . . ?
O3 C22 O4 126.9(3) . . ?
O3 C22 N2 123.6(3) . . ?
O4 C22 N2 109.5(3) . . ?
O4 C23 C26 101.1(4) . . ?
O4 C23 C25 108.1(4) . . ?
C26 C23 C25 113.4(5) . . ?
O4 C23 C24 108.5(4) . . ?
C26 C23 C24 111.9(5) . . ?
C25 C23 C24 113.0(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C12 N1 C5 118.5(3) . . ?
C12 N1 C11 118.5(3) . . ?
C5 N1 C11 122.5(3) . . ?
C22 N2 C14 124.1(3) . . ?
C22 N2 C21 119.7(3) . . ?
C14 N2 C21 116.2(2) . . ?
C5 O2 C4 121.2(3) . . ?
C22 O4 C23 122.3(3) . . ?

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
C11 C6 C7 C8 -0.8(6) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C7 C6 C11 C10 0.7(5) . . . . ?
C7 C6 C11 N1 -176.5(3) . . . . ?
C9 C10 C11 C6 -0.3(5) . . . . ?
C9 C10 C11 N1 177.0(3) . . . . ?
N1 C12 C13 C14 -32(14) . . . . ?
C12 C13 C14 C15 -82(8) . . . . ?
C12 C13 C14 N2 94(8) . . . . ?
C21 C16 C17 C18 -0.7(8) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C17 C18 C19 C20 -0.2(8) . . . . ?
C18 C19 C20 C21 -0.1(7) . . . . ?
C19 C20 C21 C16 -0.1(6) . . . . ?
C19 C20 C21 N2 -179.1(4) . . . . ?
C17 C16 C21 C20 0.4(6) . . . . ?
C17 C16 C21 N2 179.6(4) . . . . ?
C13 C12 N1 C5 107(7) . . . . ?
C13 C12 N1 C11 -65(8) . . . . ?
O1 C5 N1 C12 -169.1(4) . . . . ?
O2 C5 N1 C12 10.3(5) . . . . ?
O1 C5 N1 C11 2.9(6) . . . . ?
O2 C5 N1 C11 -177.7(3) . . . . ?
C6 C11 N1 C12 27.3(5) . . . . ?
C10 C11 N1 C12 -150.0(3) . . . . ?
C6 C11 N1 C5 -144.8(4) . . . . ?
C10 C11 N1 C5 38.0(5) . . . . ?
O3 C22 N2 C14 179.1(4) . . . . ?
O4 C22 N2 C14 -0.5(5) . . . . ?
O3 C22 N2 C21 -3.5(6) . . . . ?
O4 C22 N2 C21 176.9(3) . . . . ?
C15 C14 N2 C22 -62.8(6) . . . . ?
C13 C14 N2 C22 121.3(4) . . . . ?
C15 C14 N2 C21 119.7(4) . . . . ?
C13 C14 N2 C21 -56.1(5) . . . . ?
C20 C21 N2 C22 -49.5(5) . . . . ?
C16 C21 N2 C22 131.4(4) . . . . ?
C20 C21 N2 C14 128.1(4) . . . . ?
C16 C21 N2 C14 -51.0(5) . . . . ?
O1 C5 O2 C4 -4.6(7) . . . . ?
N1 C5 O2 C4 176.0(3) . . . . ?
C1 C4 O2 C5 -177.5(4) . . . . ?
C3 C4 O2 C5 64.4(5) . . . . ?
C2 C4 O2 C5 -62.1(4) . . . . ?
O3 C22 O4 C23 -2.7(7) . . . . ?
N2 C22 O4 C23 176.8(4) . . . . ?
C26 C23 O4 C22 -177.2(4) . . . . ?
C25 C23 O4 C22 -57.9(6) . . . . ?
C24 C23 O4 C22 65.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.074
