# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_170fin
_database_code_depnum_ccdc_archive 'CCDC 924149'
#TrackingRef '17660_web_deposit_cif_file_0_JavierAdrioSevilla_1360598383.rayos azlactona4c.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Br N2 O5'
_chemical_formula_weight         537.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   P6(5)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
_cell_length_a                   14.0226(2)
_cell_length_b                   14.0226(2)
_cell_length_c                   22.0805(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3760.07(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5784
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      65.83
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(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  '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            20231
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         67.18
_reflns_number_total             3617
_reflns_number_gt                3333
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0400P)^2^+0.6471P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_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   -0.008(15)
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Br1 Br 0.84835(3) 0.62052(3) 0.10354(2) 0.07547(15) Uani 1 1 d . . .
O1 O 0.3965(2) 0.7546(2) 0.15634(15) 0.0856(9) Uani 1 1 d . . .
O2 O 0.2143(3) 0.6843(2) 0.14784(17) 0.0862(9) Uani 1 1 d . . .
O3 O 0.33090(19) 0.57585(17) 0.05455(11) 0.0555(5) Uani 1 1 d . . .
O4 O 0.36362(19) 0.43828(17) 0.03480(9) 0.0510(5) Uani 1 1 d . . .
O5 O 0.10679(17) 0.29975(16) 0.04867(10) 0.0469(5) Uani 1 1 d . . .
N1 N 0.3642(2) 0.5601(2) 0.20958(14) 0.0574(7) Uani 1 1 d . . .
H1N H 0.4116 0.6006 0.2365 0.069 Uiso 1 1 calc R . .
N2 N 0.22717(17) 0.31335(16) 0.12087(10) 0.0351(5) Uani 1 1 d . . .
H2N H 0.2481 0.2783 0.1443 0.042 Uiso 1 1 calc R . .
C1 C 0.5249(2) 0.4355(2) 0.16030(15) 0.0460(7) Uani 1 1 d . . .
H1 H 0.4791 0.3650 0.1753 0.055 Uiso 1 1 calc R . .
C2 C 0.6324(2) 0.4669(3) 0.14411(16) 0.0530(7) Uani 1 1 d . . .
H2 H 0.6591 0.4185 0.1483 0.064 Uiso 1 1 calc R . .
C3 C 0.6988(2) 0.5723(2) 0.12162(15) 0.0517(7) Uani 1 1 d . . .
C4 C 0.6607(2) 0.6436(2) 0.11486(16) 0.0537(8) Uani 1 1 d . . .
H4 H 0.7066 0.7139 0.0996 0.064 Uiso 1 1 calc R . .
C5 C 0.5531(2) 0.6115(2) 0.13084(15) 0.0505(7) Uani 1 1 d . . .
H5 H 0.5267 0.6600 0.1257 0.061 Uiso 1 1 calc R . .
C6 C 0.4848(2) 0.5074(2) 0.15448(13) 0.0395(6) Uani 1 1 d . . .
C7 C 0.3696(2) 0.4727(2) 0.17676(13) 0.0420(6) Uani 1 1 d . . .
C8 C 0.2716(2) 0.5715(2) 0.19235(15) 0.0471(7) Uani 1 1 d . . .
C9 C 0.1955(2) 0.4694(2) 0.15359(14) 0.0416(6) Uani 1 1 d . . .
C10 C 0.2752(2) 0.4308(2) 0.12804(13) 0.0364(5) Uani 1 1 d . . .
C11 C 0.1010(2) 0.3867(2) 0.19184(15) 0.0477(7) Uani 1 1 d . . .
C12 C 0.1173(3) 0.3436(3) 0.24448(19) 0.0660(10) Uani 1 1 d . . .
H12 H 0.1880 0.3590 0.2543 0.079 Uiso 1 1 calc R . .
C13 C 0.0306(4) 0.2779(3) 0.2831(2) 0.0865(14) Uani 1 1 d . . .
H13 H 0.0433 0.2485 0.3179 0.104 Uiso 1 1 calc R . .
C14 C -0.0734(4) 0.2568(4) 0.2697(3) 0.1016(18) Uani 1 1 d . . .
H14 H -0.1314 0.2141 0.2957 0.122 Uiso 1 1 calc R . .
C15 C -0.0921(3) 0.2982(6) 0.2183(3) 0.115(2) Uani 1 1 d . . .
H15 H -0.1631 0.2829 0.2091 0.138 Uiso 1 1 calc R . .
C16 C -0.0047(3) 0.3641(4) 0.1788(2) 0.0838(14) Uani 1 1 d . . .
H16 H -0.0181 0.3925 0.1438 0.101 Uiso 1 1 calc R . .
C17 C 0.3042(3) 0.6805(3) 0.16225(17) 0.0612(9) Uani 1 1 d . . .
C18 C 0.2321(6) 0.7872(4) 0.1214(3) 0.131(2) Uani 1 1 d . . .
H18A H 0.2756 0.8028 0.0853 0.197 Uiso 1 1 calc R . .
H18B H 0.2701 0.8460 0.1499 0.197 Uiso 1 1 calc R . .
H18C H 0.1624 0.7806 0.1115 0.197 Uiso 1 1 calc R . .
C19 C 0.3236(2) 0.4897(2) 0.06807(13) 0.0400(6) Uani 1 1 d . . .
C20 C 0.4232(4) 0.4948(4) -0.0194(2) 0.0873(14) Uani 1 1 d . . .
H20A H 0.3719 0.4871 -0.0504 0.131 Uiso 1 1 calc R . .
H20B H 0.4665 0.4634 -0.0331 0.131 Uiso 1 1 calc R . .
H20C H 0.4708 0.5715 -0.0105 0.131 Uiso 1 1 calc R . .
C21 C 0.1499(2) 0.2572(2) 0.07812(12) 0.0368(6) Uani 1 1 d . . .
C22 C 0.1210(2) 0.1402(2) 0.06994(12) 0.0382(6) Uani 1 1 d . . .
C23 C 0.2011(3) 0.1094(2) 0.07559(15) 0.0497(7) Uani 1 1 d . . .
H23 H 0.2733 0.1619 0.0852 0.060 Uiso 1 1 calc R . .
C24 C 0.1732(4) 0.0014(3) 0.0670(2) 0.0700(10) Uani 1 1 d . . .
H24 H 0.2268 -0.0188 0.0705 0.084 Uiso 1 1 calc R . .
C25 C 0.0674(4) -0.0763(3) 0.05328(19) 0.0724(10) Uani 1 1 d . . .
H25 H 0.0492 -0.1491 0.0476 0.087 Uiso 1 1 calc R . .
C26 C -0.0116(3) -0.0477(3) 0.04792(19) 0.0692(10) Uani 1 1 d . . .
H26 H -0.0837 -0.1014 0.0390 0.083 Uiso 1 1 calc R . .
C27 C 0.0143(3) 0.0613(2) 0.05564(15) 0.0521(7) Uani 1 1 d . . .
H27 H -0.0398 0.0807 0.0512 0.062 Uiso 1 1 calc R . .
H7 H 0.350(2) 0.408(3) 0.2059(15) 0.041(8) Uiso 1 1 d . . .
H8 H 0.233(2) 0.572(2) 0.2321(15) 0.042(8) Uiso 1 1 d . . .
H9 H 0.168(2) 0.487(2) 0.1194(16) 0.045(8) Uiso 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
Br1 0.04401(18) 0.0594(2) 0.1060(3) -0.0204(2) 0.01838(19) 0.01315(16)
O1 0.0808(18) 0.0419(13) 0.101(2) 0.0013(13) 0.0188(16) 0.0058(13)
O2 0.098(2) 0.0478(13) 0.123(2) 0.0079(14) -0.0051(18) 0.0449(14)
O3 0.0658(13) 0.0433(11) 0.0619(14) 0.0150(10) 0.0062(11) 0.0307(10)
O4 0.0664(13) 0.0485(11) 0.0416(11) 0.0107(9) 0.0144(10) 0.0313(10)
O5 0.0563(11) 0.0424(10) 0.0496(11) -0.0019(9) -0.0141(9) 0.0302(9)
N1 0.0517(14) 0.0565(15) 0.0614(17) -0.0245(13) -0.0113(12) 0.0250(13)
N2 0.0397(11) 0.0302(10) 0.0366(12) 0.0014(9) -0.0050(9) 0.0183(9)
C1 0.0388(14) 0.0361(14) 0.0566(19) 0.0050(13) 0.0013(12) 0.0138(12)
C2 0.0456(15) 0.0441(16) 0.070(2) -0.0021(14) 0.0009(14) 0.0233(13)
C3 0.0428(15) 0.0420(15) 0.0579(19) -0.0119(13) 0.0021(13) 0.0119(12)
C4 0.0505(16) 0.0340(13) 0.063(2) 0.0017(13) 0.0095(15) 0.0111(12)
C5 0.0472(15) 0.0347(14) 0.065(2) 0.0048(13) 0.0025(14) 0.0167(12)
C6 0.0380(13) 0.0318(13) 0.0437(15) -0.0012(11) -0.0029(11) 0.0137(11)
C7 0.0389(14) 0.0400(14) 0.0435(16) -0.0022(12) -0.0010(11) 0.0169(11)
C8 0.0474(15) 0.0369(14) 0.0553(19) -0.0056(13) 0.0067(14) 0.0197(12)
C9 0.0404(14) 0.0379(14) 0.0483(17) -0.0035(12) -0.0009(12) 0.0208(12)
C10 0.0366(12) 0.0316(12) 0.0406(14) 0.0005(10) -0.0007(11) 0.0169(10)
C11 0.0395(14) 0.0390(14) 0.0586(19) -0.0111(13) 0.0063(13) 0.0150(12)
C12 0.063(2) 0.058(2) 0.081(3) 0.0215(18) 0.0266(18) 0.0337(17)
C13 0.101(3) 0.060(2) 0.091(3) 0.022(2) 0.047(3) 0.035(2)
C14 0.065(3) 0.087(3) 0.104(4) -0.020(3) 0.037(3) 0.002(2)
C15 0.0362(19) 0.168(5) 0.089(4) -0.037(4) 0.008(2) 0.011(2)
C16 0.0395(18) 0.120(4) 0.071(3) -0.027(2) -0.0037(17) 0.024(2)
C17 0.072(2) 0.0361(15) 0.070(2) -0.0052(15) 0.0079(18) 0.0225(16)
C18 0.188(6) 0.065(3) 0.165(6) 0.010(3) -0.025(5) 0.082(4)
C19 0.0412(14) 0.0347(13) 0.0432(16) 0.0026(11) -0.0013(11) 0.0183(11)
C20 0.116(4) 0.082(3) 0.066(3) 0.032(2) 0.048(3) 0.052(3)
C21 0.0390(13) 0.0350(13) 0.0361(14) 0.0010(10) -0.0005(11) 0.0183(11)
C22 0.0465(14) 0.0328(12) 0.0322(14) 0.0022(10) -0.0004(11) 0.0174(11)
C23 0.0589(18) 0.0433(15) 0.0532(18) -0.0064(13) -0.0076(14) 0.0302(14)
C24 0.094(3) 0.056(2) 0.077(2) -0.0070(18) -0.010(2) 0.051(2)
C25 0.105(3) 0.0388(17) 0.072(2) -0.0060(16) -0.005(2) 0.0349(19)
C26 0.070(2) 0.0415(17) 0.068(2) -0.0073(16) -0.0104(18) 0.0067(16)
C27 0.0530(17) 0.0425(15) 0.0522(18) -0.0022(13) -0.0099(14) 0.0175(14)
_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
Br1 C3 1.897(3) . ?
O1 C17 1.194(4) . ?
O2 C17 1.327(5) . ?
O2 C18 1.458(5) . ?
O3 C19 1.198(3) . ?
O4 C19 1.334(4) . ?
O4 C20 1.447(4) . ?
O5 C21 1.227(3) . ?
N1 C8 1.436(4) . ?
N1 C7 1.458(4) . ?
N1 H1N 0.8600 . ?
N2 C21 1.353(3) . ?
N2 C10 1.442(3) . ?
N2 H2N 0.8600 . ?
C1 C6 1.384(4) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(4) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(4) . ?
C7 C10 1.574(4) . ?
C7 H7 1.03(3) . ?
C8 C17 1.513(4) . ?
C8 C9 1.547(4) . ?
C8 H8 1.03(3) . ?
C9 C11 1.510(4) . ?
C9 C10 1.570(4) . ?
C9 H9 0.94(3) . ?
C10 C19 1.528(4) . ?
C11 C12 1.381(5) . ?
C11 C16 1.381(5) . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.491(4) . ?
C22 C27 1.381(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.393(5) . ?
C26 H26 0.9300 . ?
C27 H27 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
C17 O2 C18 116.1(4) . . ?
C19 O4 C20 116.3(3) . . ?
C8 N1 C7 113.0(2) . . ?
C8 N1 H1N 123.5 . . ?
C7 N1 H1N 123.5 . . ?
C21 N2 C10 121.5(2) . . ?
C21 N2 H2N 119.3 . . ?
C10 N2 H2N 119.3 . . ?
C6 C1 C2 121.1(3) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 Br1 119.1(2) . . ?
C2 C3 Br1 119.3(2) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 119.4(2) . . ?
C5 C6 C7 121.7(2) . . ?
N1 C7 C6 112.7(2) . . ?
N1 C7 C10 105.4(2) . . ?
C6 C7 C10 117.4(2) . . ?
N1 C7 H7 108.8(17) . . ?
C6 C7 H7 105.1(17) . . ?
C10 C7 H7 107.1(17) . . ?
N1 C8 C17 113.3(3) . . ?
N1 C8 C9 106.7(2) . . ?
C17 C8 C9 114.3(3) . . ?
N1 C8 H8 106.1(17) . . ?
C17 C8 H8 105.3(16) . . ?
C9 C8 H8 110.9(16) . . ?
C11 C9 C8 109.6(2) . . ?
C11 C9 C10 116.1(2) . . ?
C8 C9 C10 103.7(2) . . ?
C11 C9 H9 109.3(18) . . ?
C8 C9 H9 112.5(18) . . ?
C10 C9 H9 105.6(19) . . ?
N2 C10 C19 110.5(2) . . ?
N2 C10 C9 115.3(2) . . ?
C19 C10 C9 109.0(2) . . ?
N2 C10 C7 109.1(2) . . ?
C19 C10 C7 109.1(2) . . ?
C9 C10 C7 103.7(2) . . ?
C12 C11 C16 117.9(3) . . ?
C12 C11 C9 122.2(3) . . ?
C16 C11 C9 119.3(3) . . ?
C11 C12 C13 121.7(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.2(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O1 C17 O2 125.2(3) . . ?
O1 C17 C8 125.1(3) . . ?
O2 C17 C8 109.4(3) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 124.1(3) . . ?
O3 C19 C10 123.5(3) . . ?
O4 C19 C10 112.2(2) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 N2 122.2(2) . . ?
O5 C21 C22 122.8(2) . . ?
N2 C21 C22 115.0(2) . . ?
C27 C22 C23 119.3(3) . . ?
C27 C22 C21 119.9(3) . . ?
C23 C22 C21 120.8(2) . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C22 C27 C26 119.4(3) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        67.18
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.035


data_datos_0m
_database_code_depnum_ccdc_archive 'CCDC 924150'
#TrackingRef '17661_web_deposit_cif_file_1_JavierAdrioSevilla_1360598383.datos_6c.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Br N2 O5'
_chemical_formula_weight         537.40
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?
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                   9.7611(2)
_cell_length_b                   9.9993(2)
_cell_length_c                   25.5619(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0310(10)
_cell_angle_gamma                90.00
_cell_volume                     2491.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_T_max  0.7074
_exptl_absorpt_process_details   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41585
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.97
_reflns_number_total             5421
_reflns_number_gt                3231
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         5421
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.008
_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
Br1 Br 0.29747(3) 0.82840(4) 0.447779(15) 0.09022(18) Uani 1 1 d . . .
C1 C 0.4667(3) 0.7791(3) 0.48327(11) 0.0560(7) Uani 1 1 d . . .
C2 C 0.5838(3) 0.8487(3) 0.47537(11) 0.0626(8) Uani 1 1 d . . .
H2A H 0.5815 0.9222 0.4530 0.075 Uiso 1 1 calc R . .
C3 C 0.7067(3) 0.8097(2) 0.50074(10) 0.0502(6) Uani 1 1 d . . .
H3 H 0.7863 0.8579 0.4955 0.060 Uiso 1 1 calc R . .
C4 C 0.7124(2) 0.7004(2) 0.53360(9) 0.0395(5) Uani 1 1 d . . .
C5 C 0.5909(3) 0.6330(3) 0.54130(11) 0.0617(7) Uani 1 1 d . . .
H5 H 0.5919 0.5598 0.5637 0.074 Uiso 1 1 calc R . .
C6 C 0.4684(3) 0.6723(3) 0.51640(12) 0.0683(8) Uani 1 1 d . . .
H6 H 0.3878 0.6262 0.5222 0.082 Uiso 1 1 calc R . .
C7 C 0.8444(2) 0.65412(19) 0.56179(8) 0.0355(5) Uani 1 1 d . . .
H7 H 0.8465 0.5562 0.5607 0.043 Uiso 1 1 calc R . .
C8 C 0.8652(2) 0.69953(19) 0.62101(8) 0.0319(5) Uani 1 1 d . . .
C9 C 1.0161(2) 0.75548(19) 0.62630(8) 0.0323(5) Uani 1 1 d . . .
H9 H 1.0637 0.7139 0.6569 0.039 Uiso 1 1 calc R . .
C10 C 1.0792(2) 0.7024(2) 0.57652(8) 0.0367(5) Uani 1 1 d . . .
H10 H 1.1491 0.7657 0.5659 0.044 Uiso 1 1 calc R . .
C11 C 1.1450(2) 0.5646(2) 0.58354(9) 0.0408(6) Uani 1 1 d . . .
C12 C 1.3248(3) 0.4430(3) 0.62649(13) 0.0724(9) Uani 1 1 d . . .
H12A H 1.2674 0.3813 0.6441 0.109 Uiso 1 1 calc R . .
H12B H 1.4071 0.4589 0.6478 0.109 Uiso 1 1 calc R . .
H12C H 1.3479 0.4058 0.5935 0.109 Uiso 1 1 calc R . .
C13 C 1.0245(2) 0.90655(19) 0.63241(8) 0.0337(5) Uani 1 1 d . . .
C14 C 1.0339(2) 0.9598(2) 0.68260(10) 0.0438(6) Uani 1 1 d . . .
H14 H 1.0379 0.9026 0.7113 0.053 Uiso 1 1 calc R . .
C15 C 1.0375(3) 1.0968(2) 0.69058(12) 0.0568(7) Uani 1 1 d . . .
H15 H 1.0414 1.1311 0.7245 0.068 Uiso 1 1 calc R . .
C16 C 1.0352(3) 1.1812(2) 0.64876(14) 0.0607(8) Uani 1 1 d . . .
H16 H 1.0383 1.2732 0.6541 0.073 Uiso 1 1 calc R . .
C17 C 1.0284(3) 1.1309(2) 0.59868(12) 0.0549(7) Uani 1 1 d . . .
H17 H 1.0281 1.1889 0.5702 0.066 Uiso 1 1 calc R . .
C18 C 1.0218(2) 0.9936(2) 0.59036(10) 0.0451(6) Uani 1 1 d . . .
H18 H 1.0155 0.9602 0.5564 0.054 Uiso 1 1 calc R . .
C19 C 0.7392(2) 0.82994(18) 0.68413(9) 0.0327(5) Uani 1 1 d . . .
C20 C 0.6314(2) 0.9336(2) 0.69125(9) 0.0404(6) Uani 1 1 d . . .
C21 C 0.5110(3) 0.9370(3) 0.65999(11) 0.0587(7) Uani 1 1 d . . .
H21 H 0.4966 0.8760 0.6328 0.070 Uiso 1 1 calc R . .
C22 C 0.4111(3) 1.0331(3) 0.66973(14) 0.0815(10) Uani 1 1 d . . .
H22 H 0.3296 1.0350 0.6492 0.098 Uiso 1 1 calc R . .
C23 C 0.4325(4) 1.1237(3) 0.70905(16) 0.0820(11) Uani 1 1 d . . .
H23 H 0.3656 1.1871 0.7153 0.098 Uiso 1 1 calc R . .
C24 C 0.5507(4) 1.1215(3) 0.73910(13) 0.0767(10) Uani 1 1 d . . .
H24 H 0.5652 1.1849 0.7654 0.092 Uiso 1 1 calc R . .
C25 C 0.6521(3) 1.0250(2) 0.73114(11) 0.0569(7) Uani 1 1 d . . .
H25 H 0.7321 1.0229 0.7525 0.068 Uiso 1 1 calc R . .
C4EA C 0.7088(3) 0.4091(2) 0.68718(11) 0.0615(8) Uani 1 1 d . . .
H4E1 H 0.7526 0.3369 0.6697 0.092 Uiso 1 1 calc R . .
H4E2 H 0.6128 0.3901 0.6890 0.092 Uiso 1 1 calc R . .
H4E3 H 0.7495 0.4187 0.7220 0.092 Uiso 1 1 calc R . .
C8NG C 0.8553(2) 0.5732(2) 0.65472(9) 0.0364(5) Uani 1 1 d . . .
N1 N 0.96596(19) 0.70374(17) 0.53767(7) 0.0380(4) Uani 1 1 d . . .
H1 H 0.9699 0.7296 0.5057 0.046 Uiso 1 1 calc R . .
N2 N 0.76111(18) 0.79626(15) 0.63421(7) 0.0333(4) Uani 1 1 d . . .
H2 H 0.7119 0.8332 0.6093 0.040 Uiso 1 1 calc R . .
O1 O 1.10836(19) 0.46681(16) 0.55963(7) 0.0615(5) Uani 1 1 d . . .
O2 O 1.25203(16) 0.56796(15) 0.61770(7) 0.0531(4) Uani 1 1 d . . .
O3 O 0.95381(17) 0.51272(14) 0.67206(7) 0.0507(4) Uani 1 1 d . . .
O4 O 0.72641(17) 0.53253(13) 0.65818(6) 0.0479(4) Uani 1 1 d . . .
O5 O 0.80280(17) 0.77835(15) 0.72103(6) 0.0449(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
Br1 0.0528(2) 0.1232(3) 0.0917(3) -0.0060(2) -0.02467(18) 0.02596(18)
C1 0.0401(16) 0.0763(18) 0.0506(17) -0.0090(15) -0.0076(13) 0.0159(14)
C2 0.0551(19) 0.0708(18) 0.0614(19) 0.0132(14) -0.0019(15) 0.0188(14)
C3 0.0404(15) 0.0568(15) 0.0533(16) 0.0048(12) 0.0005(12) 0.0062(11)
C4 0.0395(14) 0.0435(12) 0.0353(13) -0.0096(10) -0.0012(11) 0.0044(10)
C5 0.0483(18) 0.0701(17) 0.0652(19) 0.0134(14) -0.0121(14) -0.0116(14)
C6 0.0397(17) 0.090(2) 0.075(2) 0.0042(17) -0.0053(15) -0.0081(14)
C7 0.0396(13) 0.0295(11) 0.0374(13) -0.0043(9) 0.0007(11) 0.0029(9)
C8 0.0330(12) 0.0284(10) 0.0345(13) -0.0016(9) 0.0026(10) 0.0037(9)
C9 0.0325(12) 0.0303(10) 0.0339(13) -0.0004(9) -0.0013(10) 0.0035(9)
C10 0.0343(13) 0.0372(11) 0.0388(14) -0.0029(10) 0.0035(11) 0.0038(9)
C11 0.0355(14) 0.0456(13) 0.0417(14) -0.0052(11) 0.0051(11) 0.0082(10)
C12 0.0578(19) 0.0689(18) 0.089(2) 0.0001(16) -0.0139(16) 0.0287(15)
C13 0.0294(12) 0.0313(11) 0.0404(14) -0.0039(10) 0.0018(10) 0.0005(9)
C14 0.0429(15) 0.0441(13) 0.0439(15) -0.0045(11) -0.0012(11) -0.0084(10)
C15 0.0506(17) 0.0501(15) 0.0699(19) -0.0257(14) 0.0061(14) -0.0097(12)
C16 0.0485(17) 0.0330(13) 0.101(3) -0.0129(15) 0.0098(16) -0.0033(11)
C17 0.0450(16) 0.0366(13) 0.083(2) 0.0145(14) 0.0039(14) 0.0020(11)
C18 0.0457(15) 0.0409(13) 0.0488(15) 0.0037(11) 0.0026(12) 0.0030(11)
C19 0.0330(12) 0.0320(11) 0.0338(14) 0.0046(10) 0.0072(10) 0.0013(9)
C20 0.0456(15) 0.0389(12) 0.0381(14) 0.0070(10) 0.0164(12) 0.0090(10)
C21 0.0473(17) 0.0722(17) 0.0576(17) 0.0049(13) 0.0122(14) 0.0177(13)
C22 0.061(2) 0.108(2) 0.078(2) 0.028(2) 0.0256(18) 0.0413(19)
C23 0.093(3) 0.072(2) 0.086(3) 0.022(2) 0.047(2) 0.046(2)
C24 0.108(3) 0.0530(16) 0.073(2) -0.0051(15) 0.044(2) 0.0163(18)
C25 0.0680(19) 0.0509(14) 0.0538(17) -0.0040(13) 0.0217(14) 0.0075(13)
C4EA 0.0615(19) 0.0456(14) 0.078(2) 0.0209(13) 0.0069(15) -0.0101(13)
C8NG 0.0414(14) 0.0312(11) 0.0370(13) -0.0028(9) 0.0044(11) 0.0020(10)
N1 0.0377(11) 0.0479(10) 0.0288(10) 0.0042(8) 0.0035(9) 0.0058(8)
N2 0.0331(10) 0.0341(9) 0.0328(11) 0.0013(8) 0.0016(8) 0.0090(8)
O1 0.0674(13) 0.0472(10) 0.0679(12) -0.0215(9) -0.0153(10) 0.0192(9)
O2 0.0401(10) 0.0531(9) 0.0648(12) -0.0076(8) -0.0105(9) 0.0133(8)
O3 0.0482(11) 0.0362(8) 0.0676(12) 0.0118(8) 0.0012(9) 0.0110(8)
O4 0.0432(10) 0.0378(8) 0.0627(11) 0.0135(7) 0.0017(8) -0.0042(7)
O5 0.0504(10) 0.0476(9) 0.0368(9) 0.0059(7) 0.0039(8) 0.0083(8)
_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
Br1 C1 1.907(3) . ?
C1 C2 1.363(4) . ?
C1 C6 1.363(4) . ?
C2 C3 1.389(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 C7 1.515(3) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.453(3) . ?
C7 C8 1.583(3) . ?
C7 H7 0.9800 . ?
C8 N2 1.455(2) . ?
C8 C8NG 1.535(3) . ?
C8 C9 1.575(3) . ?
C9 C13 1.520(3) . ?
C9 C10 1.538(3) . ?
C9 H9 0.9800 . ?
C10 N1 1.447(3) . ?
C10 C11 1.526(3) . ?
C10 H10 0.9800 . ?
C11 O1 1.198(3) . ?
C11 O2 1.326(3) . ?
C12 O2 1.449(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.382(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O5 1.216(3) . ?
C19 N2 1.348(3) . ?
C19 C20 1.495(3) . ?
C20 C25 1.377(3) . ?
C20 C21 1.386(4) . ?
C21 C22 1.400(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.352(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.405(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C4EA O4 1.455(3) . ?
C4EA H4E1 0.9600 . ?
C4EA H4E2 0.9600 . ?
C4EA H4E3 0.9600 . ?
C8NG O3 1.200(3) . ?
C8NG O4 1.330(3) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
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 120.6(3) . . ?
C2 C1 Br1 120.7(2) . . ?
C6 C1 Br1 118.7(2) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C7 122.6(2) . . ?
C5 C4 C7 119.7(2) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C4 112.75(18) . . ?
N1 C7 C8 103.97(17) . . ?
C4 C7 C8 115.46(17) . . ?
N1 C7 H7 108.1 . . ?
C4 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
N2 C8 C8NG 110.58(17) . . ?
N2 C8 C9 113.91(16) . . ?
C8NG C8 C9 109.28(17) . . ?
N2 C8 C7 110.90(17) . . ?
C8NG C8 C7 106.98(16) . . ?
C9 C8 C7 104.84(16) . . ?
C13 C9 C10 113.97(17) . . ?
C13 C9 C8 114.00(16) . . ?
C10 C9 C8 102.72(16) . . ?
C13 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
N1 C10 C11 113.02(18) . . ?
N1 C10 C9 103.85(17) . . ?
C11 C10 C9 113.52(18) . . ?
N1 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
O1 C11 O2 124.1(2) . . ?
O1 C11 C10 124.3(2) . . ?
O2 C11 C10 111.52(19) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.36(19) . . ?
C18 C13 C9 123.17(19) . . ?
C14 C13 C9 118.46(19) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O5 C19 N2 121.90(19) . . ?
O5 C19 C20 122.2(2) . . ?
N2 C19 C20 115.87(19) . . ?
C25 C20 C21 119.8(2) . . ?
C25 C20 C19 118.3(2) . . ?
C21 C20 C19 121.9(2) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C24 119.1(3) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
O4 C4EA H4E1 109.5 . . ?
O4 C4EA H4E2 109.5 . . ?
H4E1 C4EA H4E2 109.5 . . ?
O4 C4EA H4E3 109.5 . . ?
H4E1 C4EA H4E3 109.5 . . ?
H4E2 C4EA H4E3 109.5 . . ?
O3 C8NG O4 124.32(19) . . ?
O3 C8NG C8 123.3(2) . . ?
O4 C8NG C8 112.12(19) . . ?
C10 N1 C7 108.50(17) . . ?
C10 N1 H1 125.8 . . ?
C7 N1 H1 125.8 . . ?
C19 N2 C8 122.23(18) . . ?
C19 N2 H2 118.9 . . ?
C8 N2 H2 118.9 . . ?
C11 O2 C12 116.29(19) . . ?
C8NG O4 C4EA 115.51(18) . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.074