# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Jeffrey Johnston'
_publ_contact_author_email       JEFFREY.N.JOHNSTON@VANDERBILT.EDU

_publ_section_title              
;
Br\/onsted Acid Activation of ?-Diazo Imide:
A syn-Selective Glycolate Mannich Reaction
;
loop_
_publ_author_name
'Jeffrey Johnston'
'Hubert Muchalski'
'Timothy L. Troyer'

# Attachment '07022.cif'

data_07022
_database_code_depnum_ccdc_archive 'CCDC 734742'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O5'
_chemical_formula_sum            'C25 H22 N2 O5'
_chemical_formula_weight         430.45

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
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.0853(3)
_cell_length_b                   16.6495(6)
_cell_length_c                   13.6635(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0620(9)
_cell_angle_gamma                90.00
_cell_volume                     2168.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9197
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_details      
'0.30 degree frames measured for 15 seconds each'
_diffrn_measurement_method       \w-scans
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_detector_area_resol_mean 44.52
_diffrn_standards_number         353
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  853
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            33553
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4997
_reflns_number_gt                4204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_structure_solution    'SIR-2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003), XTEL (loc. libr.)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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^)+(0.0402P)^2^+0.8004P] 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         4997
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.57235(8) -0.14505(5) 0.60237(6) 0.02495(18) Uani 1 1 d . . .
O2 O 0.78961(9) -0.15107(5) 0.59096(6) 0.02805(19) Uani 1 1 d . . .
C2 C 0.71417(12) -0.13967(7) 0.64094(8) 0.0234(2) Uani 1 1 d . . .
N3 N 0.75284(10) -0.12020(6) 0.74610(7) 0.0235(2) Uani 1 1 d . . .
O4 O 0.63590(9) -0.09975(6) 0.86453(6) 0.0313(2) Uani 1 1 d . . .
C4 C 0.63677(12) -0.11442(7) 0.77855(8) 0.0245(2) Uani 1 1 d . . .
C5 C 0.51114(12) -0.12804(7) 0.68225(8) 0.0238(2) Uani 1 1 d . . .
H5 H 0.4523 -0.1739 0.6917 0.029(3) Uiso 1 1 calc R . .
C6 C 0.42659(11) -0.04984(7) 0.65782(8) 0.0225(2) Uani 1 1 d . . .
H6 H 0.3890 -0.0396 0.7160 0.024(3) Uiso 1 1 calc R . .
N7 N 0.52318(10) 0.01447(6) 0.65824(7) 0.02167(19) Uani 1 1 d . . .
H7N H 0.5572(14) 0.0066(8) 0.6072(11) 0.027(3) Uiso 1 1 d . . .
C8 C 0.47125(11) 0.09735(7) 0.65238(8) 0.0216(2) Uani 1 1 d . . .
H8 H 0.4030 0.1073 0.5817 0.022(3) Uiso 1 1 calc R . .
C9 C 0.40040(12) 0.11432(7) 0.73274(9) 0.0231(2) Uani 1 1 d . . .
C10 C 0.27746(12) 0.15909(7) 0.70468(10) 0.0275(2) Uani 1 1 d . . .
H10 H 0.2337 0.1740 0.6344 0.030(4) Uiso 1 1 calc R . .
C11 C 0.21790(14) 0.18221(8) 0.77912(11) 0.0345(3) Uani 1 1 d . . .
H11 H 0.1343 0.2132 0.7596 0.043(4) Uiso 1 1 calc R . .
C12 C 0.28084(15) 0.15990(8) 0.88157(11) 0.0367(3) Uani 1 1 d . . .
H12 H 0.2409 0.1762 0.9325 0.048(5) Uiso 1 1 calc R . .
C13 C 0.40127(14) 0.11409(8) 0.90970(10) 0.0342(3) Uani 1 1 d . . .
H13 H 0.4431 0.0980 0.9798 0.045(4) Uiso 1 1 calc R . .
C14 C 0.46176(13) 0.09140(8) 0.83605(9) 0.0284(3) Uani 1 1 d . . .
H14 H 0.5452 0.0602 0.8560 0.032(4) Uiso 1 1 calc R . .
C15 C 0.59427(12) 0.15510(7) 0.67189(8) 0.0224(2) Uani 1 1 d . . .
C16 C 0.57213(13) 0.23089(7) 0.62642(10) 0.0291(3) Uani 1 1 d . . .
H16 H 0.4828 0.2442 0.5787 0.036(4) Uiso 1 1 calc R . .
C17 C 0.67936(15) 0.28704(8) 0.65015(11) 0.0361(3) Uani 1 1 d . . .
H17 H 0.6629 0.3386 0.6188 0.043(4) Uiso 1 1 calc R . .
C18 C 0.81032(14) 0.26852(8) 0.71927(11) 0.0362(3) Uani 1 1 d . . .
H18 H 0.8833 0.3074 0.7361 0.049(5) Uiso 1 1 calc R . .
C19 C 0.83403(13) 0.19284(8) 0.76371(10) 0.0332(3) Uani 1 1 d . . .
H19 H 0.9240 0.1795 0.8104 0.031(4) Uiso 1 1 calc R . .
C20 C 0.72680(12) 0.13633(7) 0.74027(9) 0.0272(2) Uani 1 1 d . . .
H20 H 0.7440 0.0846 0.7711 0.031(4) Uiso 1 1 calc R . .
O21 O 0.28964(9) -0.02691(5) 0.47765(6) 0.02786(19) Uani 1 1 d . . .
C21 C 0.30102(12) -0.05880(7) 0.55884(9) 0.0242(2) Uani 1 1 d . . .
O22 O 0.20534(10) -0.10686(7) 0.57592(7) 0.0424(3) Uani 1 1 d . . .
C22 C 0.08189(16) -0.12385(13) 0.48755(12) 0.0561(5) Uani 1 1 d . . .
H22A H 0.0162 -0.1566 0.5098 0.068(6) Uiso 1 1 calc R . .
H22B H 0.1096 -0.1532 0.4351 0.070(6) Uiso 1 1 calc R . .
H22C H 0.0365 -0.0733 0.4580 0.080(7) Uiso 1 1 calc R . .
C23 C 0.89196(12) -0.09677(7) 0.80673(9) 0.0247(2) Uani 1 1 d . . .
C24 C 0.95071(14) -0.12615(8) 0.90633(9) 0.0332(3) Uani 1 1 d . . .
H24 H 0.9016 -0.1641 0.9335 0.036(4) Uiso 1 1 calc R . .
C25 C 1.08274(15) -0.09909(10) 0.96584(10) 0.0407(3) Uani 1 1 d . . .
H25 H 1.1239 -0.1183 1.0346 0.054(5) Uiso 1 1 calc R . .
C26 C 1.15444(14) -0.04465(9) 0.92615(11) 0.0388(3) Uani 1 1 d . . .
H26 H 1.2440 -0.0258 0.9679 0.045(4) Uiso 1 1 calc R . .
C27 C 1.09639(14) -0.01720(8) 0.82540(11) 0.0357(3) Uani 1 1 d . . .
H27 H 1.1475 0.0190 0.7975 0.043(4) Uiso 1 1 calc R . .
C28 C 0.96364(13) -0.04253(7) 0.76526(10) 0.0294(3) Uani 1 1 d . . .
H28 H 0.9224 -0.0230 0.6967 0.035(4) 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 0.0271(4) 0.0273(4) 0.0205(4) -0.0024(3) 0.0080(3) -0.0006(3)
O2 0.0333(4) 0.0288(4) 0.0248(4) 0.0001(3) 0.0133(3) 0.0024(3)
C2 0.0293(6) 0.0193(5) 0.0210(5) 0.0017(4) 0.0075(4) 0.0007(4)
N3 0.0254(5) 0.0255(5) 0.0194(4) 0.0006(4) 0.0072(4) 0.0008(4)
O4 0.0336(5) 0.0418(5) 0.0199(4) 0.0017(3) 0.0108(3) -0.0004(4)
C4 0.0284(6) 0.0243(5) 0.0213(5) 0.0031(4) 0.0090(4) -0.0002(4)
C5 0.0271(6) 0.0255(6) 0.0203(5) 0.0010(4) 0.0097(4) -0.0035(4)
C6 0.0227(5) 0.0265(6) 0.0197(5) -0.0005(4) 0.0088(4) -0.0028(4)
N7 0.0227(5) 0.0227(5) 0.0220(4) -0.0015(4) 0.0107(4) -0.0023(4)
C8 0.0222(5) 0.0250(5) 0.0175(5) -0.0001(4) 0.0061(4) 0.0006(4)
C9 0.0231(5) 0.0241(5) 0.0236(5) -0.0049(4) 0.0096(4) -0.0046(4)
C10 0.0249(6) 0.0244(6) 0.0343(6) -0.0008(5) 0.0114(5) -0.0033(4)
C11 0.0314(6) 0.0248(6) 0.0552(8) -0.0065(6) 0.0248(6) -0.0033(5)
C12 0.0455(8) 0.0322(7) 0.0447(8) -0.0147(6) 0.0316(6) -0.0130(6)
C13 0.0389(7) 0.0407(7) 0.0267(6) -0.0102(5) 0.0160(5) -0.0140(6)
C14 0.0269(6) 0.0360(7) 0.0226(5) -0.0040(5) 0.0084(5) -0.0044(5)
C15 0.0254(5) 0.0254(5) 0.0192(5) -0.0027(4) 0.0109(4) -0.0014(4)
C16 0.0309(6) 0.0282(6) 0.0302(6) 0.0017(5) 0.0126(5) 0.0019(5)
C17 0.0406(7) 0.0265(6) 0.0459(8) 0.0028(5) 0.0208(6) -0.0022(5)
C18 0.0350(7) 0.0340(7) 0.0450(8) -0.0049(6) 0.0204(6) -0.0113(5)
C19 0.0259(6) 0.0413(7) 0.0328(6) -0.0008(5) 0.0101(5) -0.0060(5)
C20 0.0268(6) 0.0294(6) 0.0257(6) 0.0022(5) 0.0090(5) -0.0024(5)
O21 0.0283(4) 0.0332(5) 0.0220(4) 0.0013(3) 0.0080(3) -0.0026(3)
C21 0.0230(5) 0.0279(6) 0.0239(5) -0.0023(4) 0.0105(4) -0.0025(4)
O22 0.0316(5) 0.0633(7) 0.0287(5) 0.0058(4) 0.0050(4) -0.0227(5)
C22 0.0357(8) 0.0863(13) 0.0389(8) 0.0025(8) 0.0021(6) -0.0312(8)
C23 0.0250(5) 0.0251(5) 0.0232(5) -0.0025(4) 0.0067(4) 0.0028(4)
C24 0.0330(6) 0.0413(7) 0.0252(6) 0.0033(5) 0.0094(5) 0.0015(5)
C25 0.0360(7) 0.0555(9) 0.0251(6) 0.0001(6) 0.0022(5) 0.0031(6)
C26 0.0291(6) 0.0421(8) 0.0388(7) -0.0093(6) 0.0022(5) -0.0016(6)
C27 0.0334(7) 0.0282(6) 0.0431(7) -0.0015(5) 0.0093(6) -0.0040(5)
C28 0.0314(6) 0.0239(6) 0.0303(6) 0.0024(5) 0.0066(5) 0.0011(5)

_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 C2 1.3561(14) . ?
O1 C5 1.4466(13) . ?
O2 C2 1.1919(14) . ?
C2 N3 1.3984(14) . ?
N3 C4 1.3839(15) . ?
N3 C23 1.4310(15) . ?
O4 C4 1.2028(14) . ?
C4 C5 1.5163(16) . ?
C5 C6 1.5322(16) . ?
C5 H5 1.0000 . ?
C6 N7 1.4462(14) . ?
C6 C21 1.5285(15) . ?
C6 H6 1.0000 . ?
N7 C8 1.4689(14) . ?
N7 H7N 0.881(14) . ?
C8 C9 1.5193(15) . ?
C8 C15 1.5227(15) . ?
C8 H8 1.0000 . ?
C9 C10 1.3890(16) . ?
C9 C14 1.3967(16) . ?
C10 C11 1.3937(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3887(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3919(17) . ?
C15 C20 1.3934(16) . ?
C16 C17 1.3855(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3851(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3896(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O21 C21 1.2010(14) . ?
C21 O22 1.3315(14) . ?
O22 C22 1.4513(16) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.3840(17) . ?
C23 C28 1.3880(17) . ?
C24 C25 1.3893(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3881(18) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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 O1 C5 110.47(8) . . ?
O2 C2 O1 123.80(10) . . ?
O2 C2 N3 127.56(11) . . ?
O1 C2 N3 108.63(9) . . ?
C4 N3 C2 111.35(9) . . ?
C4 N3 C23 124.58(9) . . ?
C2 N3 C23 123.35(9) . . ?
O4 C4 N3 127.14(11) . . ?
O4 C4 C5 127.40(11) . . ?
N3 C4 C5 105.43(9) . . ?
O1 C5 C4 104.03(9) . . ?
O1 C5 C6 110.26(9) . . ?
C4 C5 C6 108.05(9) . . ?
O1 C5 H5 111.4 . . ?
C4 C5 H5 111.4 . . ?
C6 C5 H5 111.4 . . ?
N7 C6 C21 115.98(9) . . ?
N7 C6 C5 107.58(9) . . ?
C21 C6 C5 110.56(9) . . ?
N7 C6 H6 107.5 . . ?
C21 C6 H6 107.5 . . ?
C5 C6 H6 107.5 . . ?
C6 N7 C8 117.88(9) . . ?
C6 N7 H7N 108.8(9) . . ?
C8 N7 H7N 108.7(9) . . ?
N7 C8 C9 112.26(9) . . ?
N7 C8 C15 109.15(9) . . ?
C9 C8 C15 107.74(9) . . ?
N7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C15 C8 H8 109.2 . . ?
C10 C9 C14 119.11(11) . . ?
C10 C9 C8 119.24(10) . . ?
C14 C9 C8 121.46(10) . . ?
C9 C10 C11 120.36(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.92(12) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.08(11) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.28(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.23(12) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 C20 118.78(11) . . ?
C16 C15 C8 119.44(10) . . ?
C20 C15 C8 121.61(10) . . ?
C17 C16 C15 120.54(12) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.48(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.42(12) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.33(12) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.44(11) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O21 C21 O22 124.85(11) . . ?
O21 C21 C6 125.15(10) . . ?
O22 C21 C6 110.00(9) . . ?
C21 O22 C22 116.44(10) . . ?
O22 C22 H22A 109.5 . . ?
O22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 121.23(11) . . ?
C24 C23 N3 119.79(11) . . ?
C28 C23 N3 118.94(10) . . ?
C23 C24 C25 118.79(13) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 120.62(13) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.18(12) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 120.05(13) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 119.10(12) . . ?
C23 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?

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
C5 O1 C2 O2 179.86(11) . . . . ?
C5 O1 C2 N3 0.67(12) . . . . ?
O2 C2 N3 C4 -177.73(11) . . . . ?
O1 C2 N3 C4 1.43(12) . . . . ?
O2 C2 N3 C23 11.64(18) . . . . ?
O1 C2 N3 C23 -169.21(10) . . . . ?
C2 N3 C4 O4 178.84(12) . . . . ?
C23 N3 C4 O4 -10.66(19) . . . . ?
C2 N3 C4 C5 -2.77(12) . . . . ?
C23 N3 C4 C5 167.73(10) . . . . ?
C2 O1 C5 C4 -2.26(11) . . . . ?
C2 O1 C5 C6 113.38(10) . . . . ?
O4 C4 C5 O1 -178.64(11) . . . . ?
N3 C4 C5 O1 2.98(11) . . . . ?
O4 C4 C5 C6 64.19(15) . . . . ?
N3 C4 C5 C6 -114.20(10) . . . . ?
O1 C5 C6 N7 -62.75(11) . . . . ?
C4 C5 C6 N7 50.33(11) . . . . ?
O1 C5 C6 C21 64.82(11) . . . . ?
C4 C5 C6 C21 177.90(9) . . . . ?
C21 C6 N7 C8 64.74(13) . . . . ?
C5 C6 N7 C8 -170.91(9) . . . . ?
C6 N7 C8 C9 51.28(12) . . . . ?
C6 N7 C8 C15 170.66(9) . . . . ?
N7 C8 C9 C10 -138.45(10) . . . . ?
C15 C8 C9 C10 101.35(12) . . . . ?
N7 C8 C9 C14 46.66(14) . . . . ?
C15 C8 C9 C14 -73.54(13) . . . . ?
C14 C9 C10 C11 1.34(17) . . . . ?
C8 C9 C10 C11 -173.67(11) . . . . ?
C9 C10 C11 C12 -0.56(18) . . . . ?
C10 C11 C12 C13 -0.77(19) . . . . ?
C11 C12 C13 C14 1.29(19) . . . . ?
C12 C13 C14 C9 -0.49(19) . . . . ?
C10 C9 C14 C13 -0.83(17) . . . . ?
C8 C9 C14 C13 174.07(11) . . . . ?
N7 C8 C15 C16 150.66(10) . . . . ?
C9 C8 C15 C16 -87.20(12) . . . . ?
N7 C8 C15 C20 -34.12(13) . . . . ?
C9 C8 C15 C20 88.02(12) . . . . ?
C20 C15 C16 C17 -1.08(17) . . . . ?
C8 C15 C16 C17 174.28(11) . . . . ?
C15 C16 C17 C18 0.17(19) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C15 -0.03(19) . . . . ?
C16 C15 C20 C19 1.01(17) . . . . ?
C8 C15 C20 C19 -174.24(11) . . . . ?
N7 C6 C21 O21 13.49(17) . . . . ?
C5 C6 C21 O21 -109.30(13) . . . . ?
N7 C6 C21 O22 -166.13(10) . . . . ?
C5 C6 C21 O22 71.07(12) . . . . ?
O21 C21 O22 C22 2.8(2) . . . . ?
C6 C21 O22 C22 -177.55(13) . . . . ?
C4 N3 C23 C24 52.30(16) . . . . ?
C2 N3 C23 C24 -138.31(12) . . . . ?
C4 N3 C23 C28 -125.53(12) . . . . ?
C2 N3 C23 C28 43.86(16) . . . . ?
C28 C23 C24 C25 1.36(19) . . . . ?
N3 C23 C24 C25 -176.41(12) . . . . ?
C23 C24 C25 C26 -0.6(2) . . . . ?
C24 C25 C26 C27 -1.1(2) . . . . ?
C25 C26 C27 C28 2.1(2) . . . . ?
C24 C23 C28 C27 -0.35(18) . . . . ?
N3 C23 C28 C27 177.44(11) . . . . ?
C26 C27 C28 C23 -1.40(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7N O21 0.881(14) 2.240(15) 3.0568(12) 154.1(12) 3_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037