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# This journal is © The Royal Society of Chemistry 2013


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data_20120058_0ma
_database_code_depnum_ccdc_archive 'CCDC 909191'
#TrackingRef '20120058_0ma.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N5 O2'
_chemical_formula_weight         335.37
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   16.640(8)
_cell_length_b                   7.053(4)
_cell_length_c                   14.173(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.753(8)
_cell_angle_gamma                90.00
_cell_volume                     1628.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4013
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.00
_exptl_crystal_description       clear
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9884
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2794
_reflns_number_gt                2495
_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 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^)+(0.1183P)^2^+3.5187P] 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     SHELXL
_refine_ls_extinction_coef       0.001(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2794
_refine_ls_number_parameters     239
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2193
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          2.385
_refine_ls_shift/su_mean         0.029
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 0.42222(14) 0.3740(3) 0.93265(19) 0.0326(6) Uani 1 1 d . . .
O2 O 0.81916(18) 0.1556(3) 0.82140(19) 0.0383(7) Uani 1 1 d . . .
H6 H 0.8285 0.1602 0.7668 0.057 Uiso 1 1 calc R . .
N1 N 0.52314(16) -0.0396(4) 0.86818(18) 0.0218(6) Uani 1 1 d . . .
N3 N 0.60356(15) -0.0103(4) 0.91261(19) 0.0212(6) Uani 1 1 d . . .
N2 N 0.55634(15) 0.2791(4) 0.96718(19) 0.0212(6) Uani 1 1 d . . .
H4 H 0.5703 0.3804 1.0002 0.025 Uiso 1 1 calc R . .
N4 N 0.80799(16) 0.3077(4) 1.11746(19) 0.0232(6) Uani 1 1 d . . .
N5 N 0.83402(16) 0.1704(4) 1.06295(19) 0.0213(6) Uani 1 1 d . . .
C3 C 0.3884(2) -0.0017(5) 0.8182(2) 0.0247(7) Uani 1 1 d . . .
H1 H 0.3354 0.0472 0.8074 0.030 Uiso 1 1 calc R . .
C4 C 0.45782(19) 0.0805(4) 0.8722(2) 0.0217(7) Uani 1 1 d . . .
C6 C 0.61690(18) 0.1480(4) 0.9597(2) 0.0187(7) Uani 1 1 d . . .
C7 C 0.70033(19) 0.1877(4) 1.0106(2) 0.0197(7) Uani 1 1 d . . .
C8 C 0.77172(18) 0.0945(4) 0.9977(2) 0.0190(7) Uani 1 1 d . . .
C9 C 0.78457(18) -0.0622(4) 0.9325(2) 0.0199(7) Uani 1 1 d . . .
C14 C 0.80600(18) -0.0262(4) 0.8441(2) 0.0206(7) Uani 1 1 d . . .
C13 C 0.8169(2) -0.1763(4) 0.7846(2) 0.0239(7) Uani 1 1 d . . .
H7 H 0.8318 -0.1526 0.7258 0.029 Uiso 1 1 calc R . .
C12 C 0.80584(19) -0.3613(4) 0.8123(2) 0.0248(7) Uani 1 1 d . . .
H8 H 0.8128 -0.4611 0.7718 0.030 Uiso 1 1 calc R . .
C2 C 0.4128(2) -0.1740(5) 0.7824(2) 0.0281(8) Uani 1 1 d . . .
H2 H 0.3784 -0.2592 0.7434 0.034 Uiso 1 1 calc R . .
C1 C 0.4958(2) -0.1948(5) 0.8148(2) 0.0270(8) Uani 1 1 d . . .
H3 H 0.5276 -0.2968 0.8025 0.032 Uiso 1 1 calc R . .
C5 C 0.47477(19) 0.2548(4) 0.9242(2) 0.0224(7) Uani 1 1 d . . .
C18 C 0.7276(2) 0.3177(4) 1.0853(2) 0.0229(7) Uani 1 1 d . . .
H5 H 0.6933 0.4009 1.1094 0.028 Uiso 1 1 calc R . .
C10 C 0.7734(2) -0.2443(5) 0.9588(3) 0.0267(8) Uani 1 1 d D . .
C11 C 0.7845(2) -0.3986(5) 0.8998(3) 0.0290(8) Uani 1 1 d . . .
H9 H 0.7776 -0.5226 0.9192 0.035 Uiso 1 1 calc R . .
C15 C 0.92223(19) 0.1289(4) 1.0742(2) 0.0245(7) Uani 1 1 d . . .
H11 H 0.9282 0.0336 1.0258 0.029 Uiso 1 1 calc R . .
C16 C 0.9677(2) 0.3050(5) 1.0536(3) 0.0395(10) Uani 1 1 d . . .
H15 H 0.9443 0.3508 0.9902 0.059 Uiso 1 1 calc R . .
H16 H 1.0246 0.2749 1.0574 0.059 Uiso 1 1 calc R . .
H17 H 0.9632 0.4011 1.1002 0.059 Uiso 1 1 calc R . .
C17 C 0.9567(2) 0.0454(6) 1.1721(3) 0.0437(10) Uani 1 1 d . . .
H13 H 0.9526 0.1367 1.2211 0.066 Uiso 1 1 calc R . .
H14 H 1.0133 0.0126 1.1761 0.066 Uiso 1 1 calc R . .
H12 H 0.9262 -0.0662 1.1814 0.066 Uiso 1 1 calc R . .
H10 H 0.7553(13) -0.276(3) 1.0130(12) 0.66(2) Uani 1 1 d 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
O1 0.0221(12) 0.0189(11) 0.0514(16) -0.0040(11) -0.0053(11) 0.0047(10)
O2 0.0584(18) 0.0223(13) 0.0347(14) 0.0016(10) 0.0111(13) -0.0021(11)
N1 0.0216(14) 0.0230(14) 0.0212(13) -0.0034(10) 0.0050(10) -0.0027(11)
N3 0.0158(13) 0.0241(14) 0.0228(13) -0.0022(11) 0.0018(10) -0.0009(10)
N2 0.0184(13) 0.0172(12) 0.0264(13) -0.0031(11) 0.0004(10) -0.0003(10)
N4 0.0218(14) 0.0204(13) 0.0262(14) -0.0065(11) 0.0019(11) -0.0009(10)
N5 0.0163(13) 0.0193(13) 0.0274(14) -0.0028(11) 0.0026(10) -0.0017(10)
C3 0.0209(16) 0.0271(17) 0.0240(16) 0.0028(13) -0.0002(12) 0.0003(13)
C4 0.0224(16) 0.0210(15) 0.0216(15) 0.0018(12) 0.0043(12) 0.0006(12)
C6 0.0165(15) 0.0210(15) 0.0191(14) 0.0020(12) 0.0050(11) 0.0006(12)
C7 0.0169(15) 0.0190(15) 0.0235(15) 0.0022(12) 0.0048(12) 0.0002(11)
C8 0.0200(15) 0.0178(15) 0.0193(14) 0.0012(12) 0.0047(12) -0.0014(12)
C9 0.0157(14) 0.0212(15) 0.0224(15) -0.0009(12) 0.0029(11) 0.0020(12)
C14 0.0184(15) 0.0178(15) 0.0250(16) 0.0001(12) 0.0032(12) -0.0024(12)
C13 0.0236(16) 0.0217(16) 0.0250(16) -0.0027(13) 0.0019(13) -0.0002(12)
C12 0.0205(16) 0.0181(15) 0.0330(18) -0.0047(13) -0.0011(13) -0.0010(12)
C2 0.0274(18) 0.0287(17) 0.0270(17) -0.0074(14) 0.0030(14) -0.0076(14)
C1 0.0274(18) 0.0261(17) 0.0277(16) -0.0100(14) 0.0061(13) -0.0026(13)
C5 0.0191(15) 0.0198(15) 0.0257(16) 0.0033(13) -0.0017(12) -0.0002(13)
C18 0.0223(16) 0.0196(15) 0.0275(16) -0.0027(12) 0.0065(13) -0.0006(12)
C10 0.0275(17) 0.0204(19) 0.0329(18) 0.0045(15) 0.0079(14) -0.0062(15)
C11 0.0318(18) 0.0153(15) 0.0386(19) 0.0018(14) 0.0040(15) -0.0025(13)
C15 0.0186(16) 0.0200(15) 0.0346(18) -0.0011(13) 0.0046(13) -0.0007(12)
C16 0.0236(18) 0.0286(19) 0.064(3) 0.0094(18) 0.0025(17) -0.0041(14)
C17 0.0246(19) 0.040(2) 0.064(3) 0.019(2) 0.0015(17) 0.0040(16)
H10 0.106(14) -0.400(12) 2.00(6) 1.26(3) -0.40(2) -0.400(13)
_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 C5 1.236(4) . ?
O2 C14 1.351(4) . ?
O2 H6 0.8200 . ?
N1 C1 1.355(4) . ?
N1 N3 1.374(4) . ?
N1 C4 1.388(4) . ?
N3 C6 1.297(4) . ?
N2 C5 1.380(4) . ?
N2 C6 1.387(4) . ?
N2 H4 0.8600 . ?
N4 C18 1.324(4) . ?
N4 N5 1.363(4) . ?
N5 C8 1.351(4) . ?
N5 C15 1.473(4) . ?
C3 C4 1.378(5) . ?
C3 C2 1.408(5) . ?
C3 H1 0.9300 . ?
C4 C5 1.431(4) . ?
C6 C7 1.455(4) . ?
C7 C8 1.402(4) . ?
C7 C18 1.404(5) . ?
C8 C9 1.483(4) . ?
C9 C10 1.361(5) . ?
C9 C14 1.394(4) . ?
C14 C13 1.389(5) . ?
C13 C12 1.386(5) . ?
C13 H7 0.9300 . ?
C12 C11 1.383(5) . ?
C12 H8 0.9300 . ?
C2 C1 1.372(5) . ?
C2 H2 0.9300 . ?
C1 H3 0.9300 . ?
C18 H5 0.9300 . ?
C10 C11 1.408(5) . ?
C10 H10 0.907(10) . ?
C11 H9 0.9300 . ?
C15 C17 1.509(5) . ?
C15 C16 1.514(5) . ?
C15 H11 0.9800 . ?
C16 H15 0.9600 . ?
C16 H16 0.9600 . ?
C16 H17 0.9600 . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H12 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
C14 O2 H6 109.5 . . ?
C1 N1 N3 124.2(3) . . ?
C1 N1 C4 109.8(3) . . ?
N3 N1 C4 126.0(3) . . ?
C6 N3 N1 114.4(3) . . ?
C5 N2 C6 123.2(3) . . ?
C5 N2 H4 118.4 . . ?
C6 N2 H4 118.4 . . ?
C18 N4 N5 105.0(2) . . ?
C8 N5 N4 112.4(2) . . ?
C8 N5 C15 127.2(3) . . ?
N4 N5 C15 120.3(2) . . ?
C4 C3 C2 107.0(3) . . ?
C4 C3 H1 126.5 . . ?
C2 C3 H1 126.5 . . ?
C3 C4 N1 107.2(3) . . ?
C3 C4 C5 134.7(3) . . ?
N1 C4 C5 118.1(3) . . ?
N3 C6 N2 124.2(3) . . ?
N3 C6 C7 117.8(3) . . ?
N2 C6 C7 117.9(3) . . ?
C8 C7 C18 104.6(3) . . ?
C8 C7 C6 126.4(3) . . ?
C18 C7 C6 128.9(3) . . ?
N5 C8 C7 106.1(3) . . ?
N5 C8 C9 122.2(3) . . ?
C7 C8 C9 131.6(3) . . ?
C10 C9 C14 119.5(3) . . ?
C10 C9 C8 119.2(3) . . ?
C14 C9 C8 121.3(3) . . ?
O2 C14 C13 122.1(3) . . ?
O2 C14 C9 118.1(3) . . ?
C13 C14 C9 119.8(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H7 119.9 . . ?
C14 C13 H7 119.9 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H8 119.8 . . ?
C13 C12 H8 119.8 . . ?
C1 C2 C3 108.4(3) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
N1 C1 C2 107.5(3) . . ?
N1 C1 H3 126.2 . . ?
C2 C1 H3 126.2 . . ?
O1 C5 N2 121.6(3) . . ?
O1 C5 C4 124.4(3) . . ?
N2 C5 C4 114.0(3) . . ?
N4 C18 C7 111.9(3) . . ?
N4 C18 H5 124.1 . . ?
C7 C18 H5 124.1 . . ?
C9 C10 C11 121.7(3) . . ?
C9 C10 H10 123.4(12) . . ?
C11 C10 H10 114.8(12) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H9 120.8 . . ?
C10 C11 H9 120.8 . . ?
N5 C15 C17 111.2(3) . . ?
N5 C15 C16 110.1(3) . . ?
C17 C15 C16 112.7(3) . . ?
N5 C15 H11 107.5 . . ?
C17 C15 H11 107.5 . . ?
C16 C15 H11 107.5 . . ?
C15 C16 H15 109.5 . . ?
C15 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
C15 C16 H17 109.5 . . ?
H15 C16 H17 109.5 . . ?
H16 C16 H17 109.5 . . ?
C15 C17 H13 109.5 . . ?
C15 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
C15 C17 H12 109.5 . . ?
H13 C17 H12 109.5 . . ?
H14 C17 H12 109.5 . . ?
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
C1 N1 N3 C6 179.6(3) . . . . ?
C4 N1 N3 C6 -1.8(4) . . . . ?
C18 N4 N5 C8 -0.1(3) . . . . ?
C18 N4 N5 C15 175.8(3) . . . . ?
C2 C3 C4 N1 0.6(4) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C1 N1 C4 C3 -1.1(4) . . . . ?
N3 N1 C4 C3 -179.9(3) . . . . ?
C1 N1 C4 C5 -178.9(3) . . . . ?
N3 N1 C4 C5 2.3(4) . . . . ?
N1 N3 C6 N2 0.8(4) . . . . ?
N1 N3 C6 C7 178.7(2) . . . . ?
C5 N2 C6 N3 -0.4(5) . . . . ?
C5 N2 C6 C7 -178.3(3) . . . . ?
N3 C6 C7 C8 15.1(5) . . . . ?
N2 C6 C7 C8 -166.8(3) . . . . ?
N3 C6 C7 C18 -161.4(3) . . . . ?
N2 C6 C7 C18 16.6(5) . . . . ?
N4 N5 C8 C7 -0.2(3) . . . . ?
C15 N5 C8 C7 -175.7(3) . . . . ?
N4 N5 C8 C9 -177.8(3) . . . . ?
C15 N5 C8 C9 6.6(5) . . . . ?
C18 C7 C8 N5 0.4(3) . . . . ?
C6 C7 C8 N5 -176.8(3) . . . . ?
C18 C7 C8 C9 177.7(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
N5 C8 C9 C10 94.3(4) . . . . ?
C7 C8 C9 C10 -82.7(4) . . . . ?
N5 C8 C9 C14 -87.2(4) . . . . ?
C7 C8 C9 C14 95.8(4) . . . . ?
C10 C9 C14 O2 -178.0(3) . . . . ?
C8 C9 C14 O2 3.5(4) . . . . ?
C10 C9 C14 C13 -1.0(5) . . . . ?
C8 C9 C14 C13 -179.5(3) . . . . ?
O2 C14 C13 C12 177.5(3) . . . . ?
C9 C14 C13 C12 0.6(5) . . . . ?
C14 C13 C12 C11 -0.6(5) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
N3 N1 C1 C2 180.0(3) . . . . ?
C4 N1 C1 C2 1.2(4) . . . . ?
C3 C2 C1 N1 -0.8(4) . . . . ?
C6 N2 C5 O1 179.7(3) . . . . ?
C6 N2 C5 C4 0.8(4) . . . . ?
C3 C4 C5 O1 2.5(6) . . . . ?
N1 C4 C5 O1 179.5(3) . . . . ?
C3 C4 C5 N2 -178.7(3) . . . . ?
N1 C4 C5 N2 -1.7(4) . . . . ?
N5 N4 C18 C7 0.3(3) . . . . ?
C8 C7 C18 N4 -0.5(4) . . . . ?
C6 C7 C18 N4 176.7(3) . . . . ?
C14 C9 C10 C11 1.2(5) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C13 C12 C11 C10 0.8(5) . . . . ?
C9 C10 C11 C12 -1.2(5) . . . . ?
C8 N5 C15 C17 -118.2(4) . . . . ?
N4 N5 C15 C17 66.6(4) . . . . ?
C8 N5 C15 C16 116.2(4) . . . . ?
N4 N5 C15 C16 -59.1(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.094


data_20120061_0ma
_database_code_depnum_ccdc_archive 'CCDC 909192'
#TrackingRef '20120061_0ma.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            x2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Br N5 O2'
_chemical_formula_weight         448.28
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           Triclinic
_symmetry_space_group_name_H-M   p-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   7.0998(5)
_cell_length_b                   10.4533(7)
_cell_length_c                   14.2795(10)
_cell_angle_alpha                103.513(5)
_cell_angle_beta                 104.362(4)
_cell_angle_gamma                101.119(4)
_cell_volume                     962.19(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4540
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      25.00
_exptl_crystal_description       clear
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14062
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3394
_reflns_number_gt                2807
_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 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^)+(0.0219P)^2^+1.4376P] 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     SHELXL
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30449(5) 1.20028(3) 0.22432(4) 0.07282(17) Uani 1 1 d . . .
O1 O -0.1004(4) 0.2257(2) 0.43266(15) 0.0569(6) Uani 1 1 d . . .
O2 O 0.0459(3) 0.5850(2) 0.39939(15) 0.0484(5) Uani 1 1 d . . .
H5 H 0.067(6) 0.637(4) 0.453(3) 0.073 Uiso 1 1 d . . .
N1 N -0.2929(3) 0.0570(2) 0.16720(16) 0.0368(5) Uani 1 1 d . . .
N2 N -0.2686(3) 0.1629(2) 0.12552(16) 0.0387(5) Uani 1 1 d . . .
N3 N -0.0466(3) 0.6002(2) 0.13484(16) 0.0379(5) Uani 1 1 d . . .
N4 N -0.2300(4) 0.5442(2) 0.06122(18) 0.0483(6) Uani 1 1 d . . .
N5 N -0.1344(3) 0.3034(2) 0.29480(16) 0.0381(5) Uani 1 1 d . . .
H4 H -0.0846 0.3861 0.3336 0.046 Uiso 1 1 calc R . .
C1 C -0.3712(5) -0.1515(3) 0.1795(2) 0.0494(8) Uani 1 1 d . . .
H1 H -0.4175 -0.2459 0.1624 0.059 Uiso 1 1 calc R . .
C2 C -0.3733(4) -0.0763(3) 0.1125(2) 0.0442(7) Uani 1 1 d . . .
H3 H -0.4212 -0.1105 0.0423 0.053 Uiso 1 1 calc R . .
C3 C -0.1900(4) 0.2827(3) 0.19172(19) 0.0349(6) Uani 1 1 d . . .
C4 C -0.1625(4) 0.4020(3) 0.15559(19) 0.0363(6) Uani 1 1 d . . .
C5 C -0.0007(4) 0.5171(3) 0.19312(18) 0.0327(6) Uani 1 1 d . . .
C6 C 0.0518(4) 0.7404(3) 0.1523(2) 0.0390(6) Uani 1 1 d . . .
C7 C 0.0570(5) 0.7897(3) 0.0717(2) 0.0478(7) Uani 1 1 d . . .
H13 H 0.0079 0.7321 0.0056 0.057 Uiso 1 1 calc R . .
C8 C 0.1380(5) 0.9279(3) 0.0926(3) 0.0534(8) Uani 1 1 d . . .
H14 H 0.1452 0.9662 0.0406 0.064 Uiso 1 1 calc R . .
C9 C 0.2079(4) 1.0077(3) 0.1915(3) 0.0486(8) Uani 1 1 d . . .
C10 C -0.2971(4) 0.4254(3) 0.0743(2) 0.0460(7) Uani 1 1 d . . .
H10 H -0.4197 0.3636 0.0343 0.055 Uiso 1 1 calc R . .
C11 C -0.2388(4) 0.0675(3) 0.2698(2) 0.0383(6) Uani 1 1 d . . .
C12 C -0.2878(5) -0.0621(3) 0.2777(2) 0.0471(7) Uani 1 1 d . . .
H2 H -0.2690 -0.0861 0.3374 0.057 Uiso 1 1 calc R . .
C13 C -0.1530(4) 0.2012(3) 0.3397(2) 0.0397(6) Uani 1 1 d . . .
C14 C 0.1983(4) 0.5514(2) 0.27014(19) 0.0323(6) Uani 1 1 d . . .
C15 C 0.3698(4) 0.5500(3) 0.2399(2) 0.0403(6) Uani 1 1 d . . .
H9 H 0.3573 0.5220 0.1714 0.048 Uiso 1 1 calc R . .
C16 C 0.5586(4) 0.5896(3) 0.3107(3) 0.0524(8) Uani 1 1 d . . .
H8 H 0.6727 0.5883 0.2900 0.063 Uiso 1 1 calc R . .
C17 C 0.5766(4) 0.6309(4) 0.4120(3) 0.0575(9) Uani 1 1 d . . .
H7 H 0.7039 0.6594 0.4597 0.069 Uiso 1 1 calc R . .
C18 C 0.4087(4) 0.6307(3) 0.4440(2) 0.0496(8) Uani 1 1 d . . .
H6 H 0.4223 0.6572 0.5128 0.060 Uiso 1 1 calc R . .
C19 C 0.2192(4) 0.5908(3) 0.3729(2) 0.0368(6) Uani 1 1 d . . .
C20 C 0.1252(4) 0.8151(2) 0.24762(18) 0.0313(6) Uani 1 1 d . . .
H11 H 0.1224 0.7761 0.2997 0.038 Uiso 1 1 calc R . .
C21 C 0.2031(5) 0.9477(3) 0.2670(2) 0.0527(8) Uani 1 1 d . . .
H12 H 0.2564 1.0020 0.3341 0.063 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0539(2) 0.0404(2) 0.1301(4) 0.0293(2) 0.0338(2) 0.01391(15)
O1 0.0761(16) 0.0509(13) 0.0323(11) 0.0021(9) 0.0113(11) 0.0106(11)
O2 0.0350(11) 0.0545(13) 0.0374(11) -0.0101(9) 0.0107(9) -0.0002(9)
N1 0.0361(12) 0.0321(12) 0.0348(12) 0.0017(10) 0.0085(10) 0.0051(10)
N2 0.0392(13) 0.0326(12) 0.0345(12) 0.0017(10) 0.0065(10) 0.0035(10)
N3 0.0364(12) 0.0356(12) 0.0345(12) 0.0063(10) 0.0028(10) 0.0084(10)
N4 0.0445(14) 0.0440(14) 0.0413(13) 0.0056(11) -0.0044(11) 0.0090(11)
N5 0.0382(13) 0.0301(12) 0.0342(12) -0.0025(9) 0.0075(10) 0.0020(10)
C1 0.0502(18) 0.0319(15) 0.0574(19) 0.0041(14) 0.0143(15) 0.0050(13)
C2 0.0455(17) 0.0334(15) 0.0406(16) -0.0017(13) 0.0086(13) 0.0026(12)
C3 0.0267(13) 0.0364(14) 0.0326(14) 0.0005(11) 0.0053(11) 0.0051(11)
C4 0.0347(14) 0.0331(14) 0.0333(14) 0.0003(11) 0.0068(12) 0.0076(11)
C5 0.0316(13) 0.0326(13) 0.0304(13) 0.0027(11) 0.0086(11) 0.0102(11)
C6 0.0324(14) 0.0375(15) 0.0499(17) 0.0150(13) 0.0119(13) 0.0144(12)
C7 0.0496(18) 0.0519(18) 0.0442(17) 0.0142(14) 0.0159(14) 0.0172(15)
C8 0.0529(19) 0.056(2) 0.068(2) 0.0327(17) 0.0269(17) 0.0225(16)
C9 0.0380(16) 0.0372(16) 0.076(2) 0.0186(16) 0.0223(16) 0.0150(13)
C10 0.0411(16) 0.0387(16) 0.0397(16) -0.0020(13) -0.0032(13) 0.0057(13)
C11 0.0366(15) 0.0391(15) 0.0347(14) 0.0042(12) 0.0099(12) 0.0098(12)
C12 0.0499(18) 0.0445(17) 0.0462(17) 0.0122(14) 0.0148(14) 0.0124(14)
C13 0.0370(15) 0.0413(15) 0.0355(16) 0.0025(12) 0.0114(12) 0.0088(12)
C14 0.0292(13) 0.0277(13) 0.0368(14) 0.0076(11) 0.0074(11) 0.0065(10)
C15 0.0378(15) 0.0407(15) 0.0451(16) 0.0142(13) 0.0146(13) 0.0121(12)
C16 0.0324(16) 0.064(2) 0.066(2) 0.0227(17) 0.0178(15) 0.0168(14)
C17 0.0284(15) 0.071(2) 0.062(2) 0.0171(18) -0.0007(15) 0.0098(15)
C18 0.0412(17) 0.0567(19) 0.0371(16) 0.0068(14) 0.0001(13) 0.0059(14)
C19 0.0302(14) 0.0341(14) 0.0380(15) 0.0049(12) 0.0059(12) 0.0033(11)
C20 0.0387(14) 0.0248(12) 0.0254(12) 0.0065(10) 0.0047(11) 0.0047(11)
C21 0.0523(19) 0.0452(17) 0.0536(19) 0.0077(15) 0.0111(15) 0.0118(15)
_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 C9 1.900(3) . ?
O1 C13 1.235(3) . ?
O2 C19 1.368(3) . ?
O2 H5 0.79(4) . ?
N1 C2 1.356(3) . ?
N1 N2 1.377(3) . ?
N1 C11 1.391(3) . ?
N2 C3 1.300(3) . ?
N3 C5 1.366(3) . ?
N3 N4 1.372(3) . ?
N3 C6 1.430(3) . ?
N4 C10 1.314(4) . ?
N5 C13 1.371(4) . ?
N5 C3 1.378(3) . ?
N5 H4 0.8600 . ?
C1 C2 1.371(4) . ?
C1 C12 1.397(4) . ?
C1 H1 0.9300 . ?
C2 H3 0.9300 . ?
C3 C4 1.454(4) . ?
C4 C5 1.384(4) . ?
C4 C10 1.412(4) . ?
C5 C14 1.478(3) . ?
C6 C20 1.314(4) . ?
C6 C7 1.373(4) . ?
C7 C8 1.378(4) . ?
C7 H13 0.9300 . ?
C8 C9 1.371(5) . ?
C8 H14 0.9300 . ?
C9 C21 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C11 C13 1.428(4) . ?
C12 H2 0.9300 . ?
C14 C15 1.390(4) . ?
C14 C19 1.389(4) . ?
C15 C16 1.381(4) . ?
C15 H9 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H8 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H7 0.9300 . ?
C18 C19 1.387(4) . ?
C18 H6 0.9300 . ?
C20 C21 1.324(4) . ?
C20 H11 0.9300 . ?
C21 H12 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
C19 O2 H5 111(3) . . ?
C2 N1 N2 124.2(2) . . ?
C2 N1 C11 109.2(2) . . ?
N2 N1 C11 126.5(2) . . ?
C3 N2 N1 114.1(2) . . ?
C5 N3 N4 112.5(2) . . ?
C5 N3 C6 128.3(2) . . ?
N4 N3 C6 118.2(2) . . ?
C10 N4 N3 104.2(2) . . ?
C13 N5 C3 124.5(2) . . ?
C13 N5 H4 117.8 . . ?
C3 N5 H4 117.8 . . ?
C2 C1 C12 108.4(3) . . ?
C2 C1 H1 125.8 . . ?
C12 C1 H1 125.8 . . ?
N1 C2 C1 107.6(2) . . ?
N1 C2 H3 126.2 . . ?
C1 C2 H3 126.2 . . ?
N2 C3 N5 123.5(2) . . ?
N2 C3 C4 118.5(2) . . ?
N5 C3 C4 118.0(2) . . ?
C5 C4 C10 104.9(2) . . ?
C5 C4 C3 127.9(2) . . ?
C10 C4 C3 127.2(2) . . ?
N3 C5 C4 105.8(2) . . ?
N3 C5 C14 121.4(2) . . ?
C4 C5 C14 132.5(2) . . ?
C20 C6 C7 124.4(3) . . ?
C20 C6 N3 115.7(2) . . ?
C7 C6 N3 119.8(3) . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 H13 121.3 . . ?
C6 C7 H13 121.3 . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 H14 120.6 . . ?
C9 C8 H14 120.6 . . ?
C21 C9 C8 119.4(3) . . ?
C21 C9 Br1 120.0(2) . . ?
C8 C9 Br1 120.6(2) . . ?
N4 C10 C4 112.6(2) . . ?
N4 C10 H10 123.7 . . ?
C4 C10 H10 123.7 . . ?
C12 C11 N1 107.3(2) . . ?
C12 C11 C13 135.3(3) . . ?
N1 C11 C13 117.4(2) . . ?
C11 C12 C1 107.4(3) . . ?
C11 C12 H2 126.3 . . ?
C1 C12 H2 126.3 . . ?
O1 C13 N5 121.7(2) . . ?
O1 C13 C11 124.3(3) . . ?
N5 C13 C11 114.0(2) . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 C5 119.8(2) . . ?
C19 C14 C5 121.2(2) . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H9 119.7 . . ?
C14 C15 H9 119.7 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H8 120.2 . . ?
C15 C16 H8 120.2 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H7 119.5 . . ?
C18 C17 H7 119.5 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H6 120.3 . . ?
C19 C18 H6 120.3 . . ?
O2 C19 C14 117.1(2) . . ?
O2 C19 C18 122.5(3) . . ?
C14 C19 C18 120.4(3) . . ?
C6 C20 C21 117.8(3) . . ?
C6 C20 H11 121.1 . . ?
C21 C20 H11 121.1 . . ?
C20 C21 C9 122.2(3) . . ?
C20 C21 H12 118.9 . . ?
C9 C21 H12 118.9 . . ?
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
C2 N1 N2 C3 179.5(3) . . . . ?
C11 N1 N2 C3 -1.3(4) . . . . ?
C5 N3 N4 C10 -0.2(3) . . . . ?
C6 N3 N4 C10 -169.7(2) . . . . ?
N2 N1 C2 C1 179.4(2) . . . . ?
C11 N1 C2 C1 0.0(3) . . . . ?
C12 C1 C2 N1 0.1(3) . . . . ?
N1 N2 C3 N5 0.2(4) . . . . ?
N1 N2 C3 C4 -178.5(2) . . . . ?
C13 N5 C3 N2 0.7(4) . . . . ?
C13 N5 C3 C4 179.4(2) . . . . ?
N2 C3 C4 C5 -140.0(3) . . . . ?
N5 C3 C4 C5 41.3(4) . . . . ?
N2 C3 C4 C10 40.4(4) . . . . ?
N5 C3 C4 C10 -138.4(3) . . . . ?
N4 N3 C5 C4 -0.2(3) . . . . ?
C6 N3 C5 C4 168.0(2) . . . . ?
N4 N3 C5 C14 173.8(2) . . . . ?
C6 N3 C5 C14 -18.0(4) . . . . ?
C10 C4 C5 N3 0.4(3) . . . . ?
C3 C4 C5 N3 -179.3(2) . . . . ?
C10 C4 C5 C14 -172.6(3) . . . . ?
C3 C4 C5 C14 7.7(5) . . . . ?
C5 N3 C6 C20 -34.0(4) . . . . ?
N4 N3 C6 C20 133.6(3) . . . . ?
C5 N3 C6 C7 148.7(3) . . . . ?
N4 N3 C6 C7 -43.7(4) . . . . ?
C20 C6 C7 C8 -2.6(4) . . . . ?
N3 C6 C7 C8 174.4(3) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C21 2.7(5) . . . . ?
C7 C8 C9 Br1 -175.8(2) . . . . ?
N3 N4 C10 C4 0.5(3) . . . . ?
C5 C4 C10 N4 -0.6(3) . . . . ?
C3 C4 C10 N4 179.1(3) . . . . ?
C2 N1 C11 C12 -0.1(3) . . . . ?
N2 N1 C11 C12 -179.5(2) . . . . ?
C2 N1 C11 C13 -179.3(2) . . . . ?
N2 N1 C11 C13 1.3(4) . . . . ?
N1 C11 C12 C1 0.2(3) . . . . ?
C13 C11 C12 C1 179.1(3) . . . . ?
C2 C1 C12 C11 -0.2(4) . . . . ?
C3 N5 C13 O1 179.9(3) . . . . ?
C3 N5 C13 C11 -0.6(4) . . . . ?
C12 C11 C13 O1 0.3(5) . . . . ?
N1 C11 C13 O1 179.1(3) . . . . ?
C12 C11 C13 N5 -179.2(3) . . . . ?
N1 C11 C13 N5 -0.3(4) . . . . ?
N3 C5 C14 C15 -67.6(3) . . . . ?
C4 C5 C14 C15 104.5(3) . . . . ?
N3 C5 C14 C19 109.7(3) . . . . ?
C4 C5 C14 C19 -78.2(4) . . . . ?
C19 C14 C15 C16 -1.3(4) . . . . ?
C5 C14 C15 C16 176.1(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C15 C14 C19 O2 -177.2(2) . . . . ?
C5 C14 C19 O2 5.5(4) . . . . ?
C15 C14 C19 C18 1.4(4) . . . . ?
C5 C14 C19 C18 -176.0(3) . . . . ?
C17 C18 C19 O2 178.4(3) . . . . ?
C17 C18 C19 C14 -0.1(5) . . . . ?
C7 C6 C20 C21 2.4(4) . . . . ?
N3 C6 C20 C21 -174.7(3) . . . . ?
C6 C20 C21 C9 0.4(5) . . . . ?
C8 C9 C21 C20 -2.9(5) . . . . ?
Br1 C9 C21 C20 175.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.049


data_H:\Report\20120067\20120067.CIF
_database_code_depnum_ccdc_archive 'CCDC 909193'
#TrackingRef '20120067.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            X3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N5 O4'
_chemical_formula_weight         391.39
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                   7.1731(2)
_cell_length_b                   9.0580(3)
_cell_length_c                   15.2735(5)
_cell_angle_alpha                96.9650(10)
_cell_angle_beta                 93.3370(10)
_cell_angle_gamma                112.6080(10)
_cell_volume                     903.39(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87
_exptl_crystal_description       Columnar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11939
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.57
_reflns_number_total             4057
_reflns_number_gt                3810
_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 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^)+(0.0427P)^2^+0.4451P] 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     SHELXL
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     273
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_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 0.26413(12) 0.43421(9) 0.35576(5) 0.01877(18) Uani 1 1 d . . .
O2 O 0.35410(13) 0.60481(11) 0.48521(5) 0.0251(2) Uani 1 1 d . . .
O3 O 0.90234(15) 0.80404(11) -0.04276(6) 0.0280(2) Uani 1 1 d . . .
O4 O 0.99470(12) 1.06590(10) 0.18660(5) 0.01709(17) Uani 1 1 d . . .
H8 H 1.030(2) 1.1252(19) 0.1471(11) 0.026 Uiso 1 1 d . . .
N1 N 0.72418(14) 0.48104(11) 0.13262(6) 0.0163(2) Uani 1 1 d . . .
N2 N 0.72137(14) 0.43055(11) 0.04360(6) 0.0168(2) Uani 1 1 d . . .
C10 C 0.73699(16) 0.79338(13) 0.42305(7) 0.0142(2) Uani 1 1 d . . .
N4 N 0.83937(14) 0.74396(11) 0.09491(6) 0.0164(2) Uani 1 1 d . . .
H4 H 0.8725 0.8448 0.1146 0.020 Uiso 1 1 calc R . .
N5 N 0.72753(15) 0.85218(12) 0.50642(6) 0.0188(2) Uani 1 1 d D . .
H14 H 0.6234(18) 0.8050(17) 0.5322(10) 0.028 Uiso 1 1 d D . .
H13 H 0.8304(18) 0.9329(15) 0.5345(9) 0.028 Uiso 1 1 d D . .
C1 C -0.06644(18) 0.44730(15) 0.35575(8) 0.0218(2) Uani 1 1 d . . .
H17 H -0.0099 0.5548 0.3889 0.033 Uiso 1 1 calc R . .
H18 H -0.2032 0.3922 0.3688 0.033 Uiso 1 1 calc R . .
H1 H -0.0668 0.4531 0.2934 0.033 Uiso 1 1 calc R . .
C2 C 0.05977(17) 0.35618(13) 0.38113(8) 0.0186(2) Uani 1 1 d . . .
H16 H 0.0670 0.3553 0.4447 0.022 Uiso 1 1 calc R . .
H15 H -0.0025 0.2450 0.3512 0.022 Uiso 1 1 calc R . .
C3 C 0.39128(17) 0.56451(13) 0.41180(7) 0.0166(2) Uani 1 1 d . . .
C4 C 0.57831(16) 0.65413(13) 0.37302(7) 0.0142(2) Uani 1 1 d . . .
C5 C 0.60156(16) 0.60970(13) 0.28608(7) 0.0144(2) Uani 1 1 d . . .
H7 H 0.5001 0.5188 0.2524 0.017 Uiso 1 1 calc R . .
C6 C 0.77323(16) 0.69751(13) 0.24739(7) 0.0138(2) Uani 1 1 d . . .
C7 C 0.78223(16) 0.63631(13) 0.15404(7) 0.0140(2) Uani 1 1 d . . .
C8 C 0.78187(17) 0.52983(14) -0.02079(7) 0.0175(2) Uani 1 1 d . . .
C9 C 0.76061(18) 0.43068(16) -0.10040(8) 0.0219(2) Uani 1 1 d . . .
H2 H 0.7897 0.4638 -0.1551 0.026 Uiso 1 1 calc R . .
N3 N 0.90862(14) 0.87410(11) 0.38678(6) 0.01397(19) Uani 1 1 d . . .
C11 C 0.92666(16) 0.82955(12) 0.30195(7) 0.0130(2) Uani 1 1 d . . .
C12 C 0.66454(19) 0.27378(14) 0.00634(8) 0.0229(2) Uani 1 1 d . . .
H6 H 0.6187 0.1843 0.0356 0.028 Uiso 1 1 calc R . .
C13 C 0.68719(19) 0.27122(16) -0.08305(8) 0.0251(3) Uani 1 1 d . . .
H5 H 0.6585 0.1792 -0.1246 0.030 Uiso 1 1 calc R . .
C14 C 0.84696(17) 0.70036(14) 0.00587(7) 0.0182(2) Uani 1 1 d . . .
C15 C 1.13117(16) 0.92582(12) 0.27547(7) 0.0135(2) Uani 1 1 d . . .
C16 C 1.16211(16) 1.04459(12) 0.22097(7) 0.0144(2) Uani 1 1 d . . .
C17 C 1.35742(17) 1.13789(13) 0.20303(7) 0.0175(2) Uani 1 1 d . . .
H9 H 1.3767 1.2165 0.1666 0.021 Uiso 1 1 calc R . .
C18 C 1.52287(17) 1.11363(14) 0.23946(7) 0.0194(2) Uani 1 1 d . . .
H10 H 1.6528 1.1751 0.2268 0.023 Uiso 1 1 calc R . .
C19 C 1.49552(17) 0.99783(14) 0.29489(8) 0.0194(2) Uani 1 1 d . . .
H12 H 1.6067 0.9821 0.3196 0.023 Uiso 1 1 calc R . .
C20 C 1.30107(17) 0.90596(13) 0.31304(7) 0.0165(2) Uani 1 1 d . . .
H11 H 1.2832 0.8297 0.3509 0.020 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0140(4) 0.0181(4) 0.0198(4) 0.0006(3) 0.0045(3) 0.0018(3)
O2 0.0200(4) 0.0300(5) 0.0164(4) 0.0001(3) 0.0064(3) 0.0006(4)
O3 0.0410(6) 0.0297(5) 0.0171(4) 0.0107(3) 0.0074(4) 0.0155(4)
O4 0.0185(4) 0.0186(4) 0.0162(4) 0.0072(3) 0.0031(3) 0.0080(3)
N1 0.0164(5) 0.0178(4) 0.0123(4) 0.0003(3) 0.0028(3) 0.0047(4)
N2 0.0160(5) 0.0185(4) 0.0134(4) -0.0003(3) 0.0020(3) 0.0048(4)
C10 0.0147(5) 0.0156(5) 0.0129(5) 0.0034(4) 0.0017(4) 0.0062(4)
N4 0.0195(5) 0.0160(4) 0.0130(4) 0.0025(3) 0.0016(3) 0.0062(4)
N5 0.0163(5) 0.0208(5) 0.0133(4) -0.0002(4) 0.0035(4) 0.0013(4)
C1 0.0175(6) 0.0233(6) 0.0225(6) 0.0033(4) 0.0034(4) 0.0058(5)
C2 0.0142(5) 0.0178(5) 0.0201(5) 0.0041(4) 0.0047(4) 0.0014(4)
C3 0.0155(5) 0.0178(5) 0.0152(5) 0.0036(4) 0.0016(4) 0.0048(4)
C4 0.0133(5) 0.0155(5) 0.0137(5) 0.0032(4) 0.0017(4) 0.0050(4)
C5 0.0134(5) 0.0145(5) 0.0143(5) 0.0018(4) 0.0000(4) 0.0046(4)
C6 0.0149(5) 0.0152(5) 0.0115(5) 0.0024(4) 0.0016(4) 0.0062(4)
C7 0.0114(5) 0.0173(5) 0.0123(5) 0.0021(4) 0.0009(4) 0.0046(4)
C8 0.0153(5) 0.0247(6) 0.0125(5) 0.0023(4) 0.0010(4) 0.0081(4)
C9 0.0188(6) 0.0328(6) 0.0138(5) -0.0016(4) -0.0002(4) 0.0115(5)
N3 0.0144(4) 0.0145(4) 0.0125(4) 0.0028(3) 0.0017(3) 0.0049(3)
C11 0.0139(5) 0.0135(5) 0.0129(5) 0.0040(4) 0.0015(4) 0.0062(4)
C12 0.0220(6) 0.0188(5) 0.0229(6) -0.0036(4) 0.0040(5) 0.0043(5)
C13 0.0212(6) 0.0281(6) 0.0209(6) -0.0079(5) 0.0007(5) 0.0080(5)
C14 0.0184(6) 0.0246(6) 0.0134(5) 0.0046(4) 0.0014(4) 0.0100(5)
C15 0.0145(5) 0.0129(5) 0.0113(4) -0.0001(4) 0.0024(4) 0.0037(4)
C16 0.0157(5) 0.0140(5) 0.0125(5) 0.0005(4) 0.0019(4) 0.0052(4)
C17 0.0196(6) 0.0140(5) 0.0158(5) 0.0028(4) 0.0040(4) 0.0030(4)
C18 0.0148(5) 0.0185(5) 0.0194(5) 0.0001(4) 0.0038(4) 0.0012(4)
C19 0.0147(5) 0.0221(5) 0.0198(5) 0.0012(4) -0.0001(4) 0.0064(4)
C20 0.0180(5) 0.0165(5) 0.0146(5) 0.0030(4) 0.0015(4) 0.0064(4)
_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 C3 1.3394(13) . ?
O1 C2 1.4610(13) . ?
O2 C3 1.2132(14) . ?
O3 C14 1.2280(14) . ?
O4 C16 1.3726(13) . ?
O4 H8 0.842(17) . ?
N1 C7 1.2964(14) . ?
N1 N2 1.3775(12) . ?
N2 C12 1.3558(15) . ?
N2 C8 1.3886(14) . ?
C10 N5 1.3353(14) . ?
C10 N3 1.3575(14) . ?
C10 C4 1.4253(15) . ?
N4 C7 1.3725(13) . ?
N4 C14 1.3797(14) . ?
N4 H4 0.8600 . ?
N5 H14 0.851(9) . ?
N5 H13 0.858(9) . ?
C1 C2 1.5041(16) . ?
C1 H17 0.9600 . ?
C1 H18 0.9600 . ?
C1 H1 0.9600 . ?
C2 H16 0.9700 . ?
C2 H15 0.9700 . ?
C3 C4 1.4770(15) . ?
C4 C5 1.3787(14) . ?
C5 C6 1.3942(15) . ?
C5 H7 0.9300 . ?
C6 C11 1.4056(15) . ?
C6 C7 1.4802(14) . ?
C8 C9 1.3844(15) . ?
C8 C14 1.4285(16) . ?
C9 C13 1.3993(19) . ?
C9 H2 0.9300 . ?
N3 C11 1.3382(13) . ?
C11 C15 1.4990(14) . ?
C12 C13 1.3828(17) . ?
C12 H6 0.9300 . ?
C13 H5 0.9300 . ?
C15 C16 1.3982(14) . ?
C15 C20 1.3996(15) . ?
C16 C17 1.3938(15) . ?
C17 C18 1.3856(16) . ?
C17 H9 0.9300 . ?
C18 C19 1.3900(16) . ?
C18 H10 0.9300 . ?
C19 C20 1.3869(16) . ?
C19 H12 0.9300 . ?
C20 H11 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
C3 O1 C2 115.95(8) . . ?
C16 O4 H8 108.3(11) . . ?
C7 N1 N2 114.09(9) . . ?
C12 N2 N1 124.22(10) . . ?
C12 N2 C8 109.64(9) . . ?
N1 N2 C8 126.11(9) . . ?
N5 C10 N3 116.30(10) . . ?
N5 C10 C4 123.19(10) . . ?
N3 C10 C4 120.51(9) . . ?
C7 N4 C14 124.04(9) . . ?
C7 N4 H4 118.0 . . ?
C14 N4 H4 118.0 . . ?
C10 N5 H14 119.7(11) . . ?
C10 N5 H13 119.2(10) . . ?
H14 N5 H13 120.9(14) . . ?
C2 C1 H17 109.5 . . ?
C2 C1 H18 109.5 . . ?
H17 C1 H18 109.5 . . ?
C2 C1 H1 109.5 . . ?
H17 C1 H1 109.5 . . ?
H18 C1 H1 109.5 . . ?
O1 C2 C1 109.35(9) . . ?
O1 C2 H16 109.8 . . ?
C1 C2 H16 109.8 . . ?
O1 C2 H15 109.8 . . ?
C1 C2 H15 109.8 . . ?
H16 C2 H15 108.3 . . ?
O2 C3 O1 123.45(10) . . ?
O2 C3 C4 124.37(10) . . ?
O1 C3 C4 112.16(9) . . ?
C5 C4 C10 117.79(10) . . ?
C5 C4 C3 121.06(10) . . ?
C10 C4 C3 121.10(9) . . ?
C4 C5 C6 121.69(10) . . ?
C4 C5 H7 119.2 . . ?
C6 C5 H7 119.2 . . ?
C5 C6 C11 117.17(9) . . ?
C5 C6 C7 116.66(9) . . ?
C11 C6 C7 126.05(9) . . ?
N1 C7 N4 124.14(10) . . ?
N1 C7 C6 116.85(9) . . ?
N4 C7 C6 118.90(9) . . ?
C9 C8 N2 107.31(10) . . ?
C9 C8 C14 134.78(11) . . ?
N2 C8 C14 117.91(9) . . ?
C8 C9 C13 107.11(10) . . ?
C8 C9 H2 126.4 . . ?
C13 C9 H2 126.4 . . ?
C11 N3 C10 120.47(9) . . ?
N3 C11 C6 122.24(9) . . ?
N3 C11 C15 112.79(9) . . ?
C6 C11 C15 124.79(9) . . ?
N2 C12 C13 107.54(11) . . ?
N2 C12 H6 126.2 . . ?
C13 C12 H6 126.2 . . ?
C12 C13 C9 108.41(10) . . ?
C12 C13 H5 125.8 . . ?
C9 C13 H5 125.8 . . ?
O3 C14 N4 120.29(11) . . ?
O3 C14 C8 126.07(10) . . ?
N4 C14 C8 113.63(10) . . ?
C16 C15 C20 118.40(10) . . ?
C16 C15 C11 122.83(9) . . ?
C20 C15 C11 118.53(9) . . ?
O4 C16 C17 121.70(9) . . ?
O4 C16 C15 117.79(9) . . ?
C17 C16 C15 120.50(10) . . ?
C18 C17 C16 120.03(10) . . ?
C18 C17 H9 120.0 . . ?
C16 C17 H9 120.0 . . ?
C17 C18 C19 120.31(10) . . ?
C17 C18 H10 119.8 . . ?
C19 C18 H10 119.8 . . ?
C20 C19 C18 119.48(10) . . ?
C20 C19 H12 120.3 . . ?
C18 C19 H12 120.3 . . ?
C19 C20 C15 121.25(10) . . ?
C19 C20 H11 119.4 . . ?
C15 C20 H11 119.4 . . ?
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
C7 N1 N2 C12 -179.53(11) . . . . ?
C7 N1 N2 C8 2.92(15) . . . . ?
C3 O1 C2 C1 81.06(12) . . . . ?
C2 O1 C3 O2 10.21(16) . . . . ?
C2 O1 C3 C4 -168.58(9) . . . . ?
N5 C10 C4 C5 176.93(10) . . . . ?
N3 C10 C4 C5 -2.95(15) . . . . ?
N5 C10 C4 C3 -0.51(16) . . . . ?
N3 C10 C4 C3 179.62(9) . . . . ?
O2 C3 C4 C5 -173.78(11) . . . . ?
O1 C3 C4 C5 5.00(14) . . . . ?
O2 C3 C4 C10 3.58(17) . . . . ?
O1 C3 C4 C10 -177.64(9) . . . . ?
C10 C4 C5 C6 -0.38(15) . . . . ?
C3 C4 C5 C6 177.06(9) . . . . ?
C4 C5 C6 C11 2.80(15) . . . . ?
C4 C5 C6 C7 179.05(9) . . . . ?
N2 N1 C7 N4 -0.86(15) . . . . ?
N2 N1 C7 C6 175.32(9) . . . . ?
C14 N4 C7 N1 -1.74(17) . . . . ?
C14 N4 C7 C6 -177.85(10) . . . . ?
C5 C6 C7 N1 -41.97(14) . . . . ?
C11 C6 C7 N1 133.90(11) . . . . ?
C5 C6 C7 N4 134.42(10) . . . . ?
C11 C6 C7 N4 -49.72(15) . . . . ?
C12 N2 C8 C9 0.28(13) . . . . ?
N1 N2 C8 C9 178.13(10) . . . . ?
C12 N2 C8 C14 179.81(10) . . . . ?
N1 N2 C8 C14 -2.34(16) . . . . ?
N2 C8 C9 C13 -0.10(13) . . . . ?
C14 C8 C9 C13 -179.52(13) . . . . ?
N5 C10 N3 C11 -176.16(9) . . . . ?
C4 C10 N3 C11 3.72(15) . . . . ?
C10 N3 C11 C6 -1.14(15) . . . . ?
C10 N3 C11 C15 -176.38(9) . . . . ?
C5 C6 C11 N3 -2.11(15) . . . . ?
C7 C6 C11 N3 -177.95(9) . . . . ?
C5 C6 C11 C15 172.55(9) . . . . ?
C7 C6 C11 C15 -3.30(16) . . . . ?
N1 N2 C12 C13 -178.25(10) . . . . ?
C8 N2 C12 C13 -0.35(14) . . . . ?
N2 C12 C13 C9 0.28(14) . . . . ?
C8 C9 C13 C12 -0.11(14) . . . . ?
C7 N4 C14 O3 -179.01(11) . . . . ?
C7 N4 C14 C8 2.24(15) . . . . ?
C9 C8 C14 O3 0.4(2) . . . . ?
N2 C8 C14 O3 -178.97(11) . . . . ?
C9 C8 C14 N4 179.06(12) . . . . ?
N2 C8 C14 N4 -0.32(15) . . . . ?
N3 C11 C15 C16 -106.53(11) . . . . ?
C6 C11 C15 C16 78.37(14) . . . . ?
N3 C11 C15 C20 67.76(12) . . . . ?
C6 C11 C15 C20 -107.34(12) . . . . ?
C20 C15 C16 O4 -178.19(9) . . . . ?
C11 C15 C16 O4 -3.89(15) . . . . ?
C20 C15 C16 C17 1.52(15) . . . . ?
C11 C15 C16 C17 175.82(9) . . . . ?
O4 C16 C17 C18 179.53(10) . . . . ?
C15 C16 C17 C18 -0.16(16) . . . . ?
C16 C17 C18 C19 -0.82(16) . . . . ?
C17 C18 C19 C20 0.40(17) . . . . ?
C18 C19 C20 C15 1.01(16) . . . . ?
C16 C15 C20 C19 -1.95(16) . . . . ?
C11 C15 C20 C19 -176.50(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045