Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Wenhao Hu'
_publ_contact_author_address     
;
Key Laboratory for Asymmetric Synthesis
Chengdu Institute of Organic Chemistry
Chengdu
CHINA
;

_publ_contact_author_email       HUWH@CIOC.AC.CN

_publ_section_title              
;
Novel C-C bond formation through addition of
ammonium ylides to arylaldehydes: an facile approach to
beta-aryl-beta-hydroxy alpha-amino acids framework
;
loop_
_publ_author_name
'Wenhao Hu'
'Chen Zhiyong'
'Mi Aiqiao'
'Wang Yuanhua'

data_y1419
_database_code_depnum_ccdc_archive 'CCDC 211232'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O6'
_chemical_formula_weight         422.43

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.919(2)
_cell_length_b                   16.766(4)
_cell_length_c                   25.021(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4161.9(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    27
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      12.42

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.099
_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      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.80
_diffrn_reflns_number            4870
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4088
_reflns_number_gt                1698
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens 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^)+(0.0340P)^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     SHELXL
_refine_ls_extinction_coef       0.00164(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4088
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.803
_refine_ls_restrained_S_all      0.803
_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 0.3241(2) 0.84198(11) 0.44856(8) 0.0604(6) Uani 1 1 d . . .
O2 O 0.48680(18) 0.81338(10) 0.29449(7) 0.0464(5) Uani 1 1 d . . .
O3 O 0.66633(19) 0.73399(11) 0.28927(8) 0.0543(6) Uani 1 1 d . . .
O4 O 0.38303(18) 0.64378(11) 0.25676(7) 0.0444(5) Uani 1 1 d . . .
H4O H 0.3335 0.6593 0.2327 0.053 Uiso 1 1 calc R . .
O5 O 0.1431(2) 0.77378(12) 0.36164(9) 0.0643(6) Uani 1 1 d . . .
O6 O -0.0588(2) 0.73285(14) 0.35050(10) 0.0879(8) Uani 1 1 d . . .
N1 N 0.4261(2) 0.73221(13) 0.38858(9) 0.0367(6) Uani 1 1 d . . .
N2 N 0.0616(3) 0.72023(16) 0.35469(10) 0.0508(7) Uani 1 1 d . . .
C1 C 0.4591(3) 0.83105(16) 0.45614(11) 0.0443(8) Uani 1 1 d . . .
C2 C 0.5382(4) 0.87102(18) 0.49283(12) 0.0627(10) Uani 1 1 d . . .
H2 H 0.5000 0.9090 0.5153 0.075 Uiso 1 1 calc R . .
C3 C 0.6740(4) 0.8544(2) 0.49600(13) 0.0691(10) Uani 1 1 d . . .
H3 H 0.7267 0.8795 0.5217 0.083 Uiso 1 1 calc R . .
C4 C 0.7316(3) 0.80099(18) 0.46139(12) 0.0605(9) Uani 1 1 d . . .
H4 H 0.8240 0.7918 0.4627 0.073 Uiso 1 1 calc R . .
C5 C 0.6523(3) 0.76037(15) 0.42424(11) 0.0444(7) Uani 1 1 d . . .
H5 H 0.6924 0.7241 0.4011 0.053 Uiso 1 1 calc R . .
C6 C 0.5150(3) 0.77347(15) 0.42149(10) 0.0351(7) Uani 1 1 d . . .
C7 C 0.4669(2) 0.69050(14) 0.34046(10) 0.0324(6) Uani 1 1 d . . .
C8 C 0.5398(2) 0.61221(15) 0.35297(11) 0.0346(7) Uani 1 1 d . . .
C9 C 0.6087(3) 0.57019(16) 0.31384(12) 0.0454(8) Uani 1 1 d . . .
H9 H 0.6160 0.5914 0.2796 0.054 Uiso 1 1 calc R . .
C10 C 0.6667(3) 0.49712(17) 0.32506(14) 0.0615(9) Uani 1 1 d . . .
H10 H 0.7143 0.4703 0.2986 0.074 Uiso 1 1 calc R . .
C11 C 0.6546(3) 0.46378(18) 0.37491(16) 0.0701(11) Uani 1 1 d . . .
H11 H 0.6921 0.4141 0.3820 0.084 Uiso 1 1 calc R . .
C12 C 0.5871(3) 0.50425(17) 0.41408(13) 0.0603(9) Uani 1 1 d . . .
H12 H 0.5800 0.4824 0.4481 0.072 Uiso 1 1 calc R . .
C13 C 0.5286(3) 0.57830(16) 0.40324(11) 0.0454(8) Uani 1 1 d . . .
H13 H 0.4818 0.6050 0.4300 0.054 Uiso 1 1 calc R . .
C14 C 0.3376(2) 0.67517(15) 0.30624(10) 0.0346(6) Uani 1 1 d . . .
H14 H 0.2922 0.7262 0.2997 0.042 Uiso 1 1 calc R . .
C15 C 0.2364(3) 0.61677(15) 0.33102(10) 0.0377(7) Uani 1 1 d . . .
C16 C 0.2648(3) 0.53526(16) 0.32884(11) 0.0489(8) Uani 1 1 d . . .
H16 H 0.3466 0.5185 0.3145 0.059 Uiso 1 1 calc R . .
C17 C 0.1746(3) 0.47866(18) 0.34735(13) 0.0599(9) Uani 1 1 d . . .
H17 H 0.1982 0.4250 0.3465 0.072 Uiso 1 1 calc R . .
C18 C 0.0514(4) 0.5004(2) 0.36689(13) 0.0667(10) Uani 1 1 d . . .
H18 H -0.0079 0.4618 0.3796 0.080 Uiso 1 1 calc R . .
C19 C 0.0153(3) 0.5799(2) 0.36776(11) 0.0543(9) Uani 1 1 d . . .
H19 H -0.0700 0.5954 0.3793 0.065 Uiso 1 1 calc R . .
C20 C 0.1090(3) 0.63640(17) 0.35106(10) 0.0411(7) Uani 1 1 d . . .
C21 C 0.2568(3) 0.89896(18) 0.48105(13) 0.0872(13) Uani 1 1 d . . .
H21A H 0.2728 0.8870 0.5180 0.105 Uiso 1 1 calc R . .
H21B H 0.1617 0.8970 0.4740 0.105 Uiso 1 1 calc R . .
H21C H 0.2904 0.9513 0.4731 0.105 Uiso 1 1 calc R . .
C22 C 0.5537(3) 0.74592(15) 0.30504(11) 0.0376(7) Uani 1 1 d . . .
C23 C 0.5521(3) 0.86863(15) 0.25846(12) 0.0652(10) Uani 1 1 d . . .
H23A H 0.6474 0.8686 0.2650 0.078 Uiso 1 1 calc R . .
H23B H 0.5169 0.9213 0.2642 0.078 Uiso 1 1 calc R . .
H23C H 0.5352 0.8528 0.2222 0.078 Uiso 1 1 calc R . .
H1N H 0.349(2) 0.7584(12) 0.3872(9) 0.023(7) 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
O1 0.0710(16) 0.0533(13) 0.0569(14) -0.0137(11) 0.0141(13) 0.0195(12)
O2 0.0466(12) 0.0317(10) 0.0608(13) 0.0115(10) 0.0119(11) 0.0054(10)
O3 0.0407(12) 0.0557(13) 0.0665(14) 0.0067(11) 0.0206(11) 0.0065(11)
O4 0.0444(12) 0.0607(12) 0.0279(10) -0.0032(10) -0.0035(10) 0.0076(10)
O5 0.0446(13) 0.0549(13) 0.0934(18) -0.0168(13) -0.0025(13) 0.0082(12)
O6 0.0359(13) 0.1026(19) 0.125(2) -0.0282(17) 0.0018(15) 0.0180(13)
N1 0.0336(14) 0.0407(14) 0.0359(13) -0.0069(12) 0.0014(12) 0.0041(13)
N2 0.0312(15) 0.0661(18) 0.0550(17) -0.0119(15) 0.0014(14) 0.0067(15)
C1 0.059(2) 0.0399(18) 0.0340(17) 0.0034(15) 0.0037(17) 0.0000(17)
C2 0.101(3) 0.050(2) 0.0379(19) -0.0096(16) 0.003(2) 0.002(2)
C3 0.097(3) 0.059(2) 0.052(2) -0.0009(19) -0.021(2) -0.024(2)
C4 0.063(2) 0.058(2) 0.061(2) 0.0059(19) -0.011(2) -0.0181(19)
C5 0.0498(19) 0.0398(17) 0.0435(18) -0.0038(15) -0.0039(16) -0.0027(16)
C6 0.0439(18) 0.0326(15) 0.0288(15) 0.0006(13) 0.0017(14) -0.0032(15)
C7 0.0323(15) 0.0336(15) 0.0313(16) -0.0025(13) 0.0001(13) 0.0041(13)
C8 0.0329(16) 0.0341(15) 0.0369(16) -0.0023(14) -0.0045(14) -0.0003(13)
C9 0.0434(18) 0.0447(17) 0.0482(19) -0.0021(16) -0.0040(16) 0.0072(16)
C10 0.060(2) 0.049(2) 0.076(2) -0.0064(19) -0.001(2) 0.0195(18)
C11 0.074(3) 0.0378(19) 0.099(3) 0.001(2) -0.021(2) 0.016(2)
C12 0.077(2) 0.0437(19) 0.060(2) 0.0134(18) -0.026(2) -0.0036(19)
C13 0.0507(19) 0.0393(17) 0.0460(18) 0.0001(15) -0.0100(16) -0.0057(16)
C14 0.0325(15) 0.0384(15) 0.0330(15) -0.0042(13) 0.0024(14) 0.0061(14)
C15 0.0407(17) 0.0418(17) 0.0307(16) -0.0006(14) -0.0059(15) 0.0003(15)
C16 0.0491(19) 0.0422(17) 0.055(2) -0.0025(17) -0.0124(17) -0.0011(17)
C17 0.065(2) 0.045(2) 0.070(2) 0.0023(18) -0.019(2) -0.0107(19)
C18 0.073(3) 0.069(3) 0.059(2) 0.016(2) -0.008(2) -0.034(2)
C19 0.0440(19) 0.077(2) 0.0420(19) 0.0029(18) -0.0014(16) -0.019(2)
C20 0.0385(16) 0.0508(19) 0.0340(17) -0.0065(15) -0.0065(15) -0.0018(16)
C21 0.106(3) 0.070(2) 0.086(3) -0.019(2) 0.039(3) 0.026(2)
C22 0.0362(17) 0.0373(16) 0.0392(16) -0.0056(14) -0.0020(15) 0.0003(15)
C23 0.082(3) 0.0438(17) 0.070(2) 0.0112(18) 0.015(2) -0.0058(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.364(3) . ?
O1 C21 1.421(3) . ?
O2 C22 1.338(3) . ?
O2 C23 1.446(3) . ?
O3 C22 1.202(3) . ?
O4 C14 1.419(3) . ?
O4 H4O 0.8200 . ?
O5 N2 1.221(3) . ?
O6 N2 1.217(2) . ?
N1 C6 1.391(3) . ?
N1 C7 1.450(3) . ?
N1 H1N 0.89(2) . ?
N2 C20 1.485(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.411(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.531(3) . ?
C7 C22 1.546(3) . ?
C7 C14 1.563(3) . ?
C8 C13 1.385(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.533(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.396(3) . ?
C15 C20 1.399(4) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 C21 118.1(3) . . ?
C22 O2 C23 116.3(2) . . ?
C14 O4 H4O 109.5 . . ?
C6 N1 C7 123.7(2) . . ?
C6 N1 H1N 109.1(14) . . ?
C7 N1 H1N 116.7(15) . . ?
O6 N2 O5 122.3(3) . . ?
O6 N2 C20 118.1(3) . . ?
O5 N2 C20 119.6(2) . . ?
O1 C1 C2 125.8(3) . . ?
O1 C1 C6 113.1(3) . . ?
C2 C1 C6 121.1(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 N1 125.2(3) . . ?
C5 C6 C1 117.8(3) . . ?
N1 C6 C1 117.0(3) . . ?
N1 C7 C8 112.1(2) . . ?
N1 C7 C22 110.0(2) . . ?
C8 C7 C22 111.7(2) . . ?
N1 C7 C14 107.8(2) . . ?
C8 C7 C14 111.0(2) . . ?
C22 C7 C14 103.98(19) . . ?
C13 C8 C9 118.2(2) . . ?
C13 C8 C7 120.0(2) . . ?
C9 C8 C7 121.6(2) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 120.5(3) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O4 C14 C15 108.9(2) . . ?
O4 C14 C7 106.17(19) . . ?
C15 C14 C7 114.9(2) . . ?
O4 C14 H14 108.9 . . ?
C15 C14 H14 108.9 . . ?
C7 C14 H14 108.9 . . ?
C16 C15 C20 115.2(3) . . ?
C16 C15 C14 118.5(2) . . ?
C20 C15 C14 125.9(2) . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 118.6(3) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C15 123.5(3) . . ?
C19 C20 N2 114.5(3) . . ?
C15 C20 N2 122.1(3) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 O2 122.5(3) . . ?
O3 C22 C7 127.3(3) . . ?
O2 C22 C7 110.2(2) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C21 O1 C1 C2 -0.3(4) . . . . ?
C21 O1 C1 C6 -179.7(2) . . . . ?
O1 C1 C2 C3 -179.6(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C1 C2 C3 C4 2.8(5) . . . . ?
C2 C3 C4 C5 -2.9(5) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 N1 -175.3(2) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
C7 N1 C6 C5 -22.3(4) . . . . ?
C7 N1 C6 C1 160.3(2) . . . . ?
O1 C1 C6 C5 177.2(2) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?
O1 C1 C6 N1 -5.2(3) . . . . ?
C2 C1 C6 N1 175.5(2) . . . . ?
C6 N1 C7 C8 74.8(3) . . . . ?
C6 N1 C7 C22 -50.1(3) . . . . ?
C6 N1 C7 C14 -162.8(2) . . . . ?
N1 C7 C8 C13 17.3(3) . . . . ?
C22 C7 C8 C13 141.2(2) . . . . ?
C14 C7 C8 C13 -103.2(3) . . . . ?
N1 C7 C8 C9 -168.1(2) . . . . ?
C22 C7 C8 C9 -44.2(3) . . . . ?
C14 C7 C8 C9 71.3(3) . . . . ?
C13 C8 C9 C10 -1.2(4) . . . . ?
C7 C8 C9 C10 -175.8(2) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C10 C11 C12 -1.4(5) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C9 C8 C13 C12 0.9(4) . . . . ?
C7 C8 C13 C12 175.6(2) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?
N1 C7 C14 O4 172.68(19) . . . . ?
C8 C7 C14 O4 -64.2(3) . . . . ?
C22 C7 C14 O4 56.0(2) . . . . ?
N1 C7 C14 C15 -66.9(3) . . . . ?
C8 C7 C14 C15 56.2(3) . . . . ?
C22 C7 C14 C15 176.4(2) . . . . ?
O4 C14 C15 C16 42.2(3) . . . . ?
C7 C14 C15 C16 -76.7(3) . . . . ?
O4 C14 C15 C20 -130.4(3) . . . . ?
C7 C14 C15 C20 110.7(3) . . . . ?
C20 C15 C16 C17 -2.5(4) . . . . ?
C14 C15 C16 C17 -175.9(3) . . . . ?
C15 C16 C17 C18 2.4(5) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -3.3(5) . . . . ?
C18 C19 C20 C15 3.0(4) . . . . ?
C18 C19 C20 N2 -178.7(3) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C14 C15 C20 C19 172.7(2) . . . . ?
C16 C15 C20 N2 -178.3(2) . . . . ?
C14 C15 C20 N2 -5.5(4) . . . . ?
O6 N2 C20 C19 -28.5(4) . . . . ?
O5 N2 C20 C19 151.6(3) . . . . ?
O6 N2 C20 C15 149.8(3) . . . . ?
O5 N2 C20 C15 -30.1(4) . . . . ?
C23 O2 C22 O3 5.9(4) . . . . ?
C23 O2 C22 C7 -175.7(2) . . . . ?
N1 C7 C22 O3 122.8(3) . . . . ?
C8 C7 C22 O3 -2.2(4) . . . . ?
C14 C7 C22 O3 -122.0(3) . . . . ?
N1 C7 C22 O2 -55.5(3) . . . . ?
C8 C7 C22 O2 179.5(2) . . . . ?
C14 C7 C22 O2 59.7(2) . . . . ?

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
N1 H1N O5 0.89(2) 2.15(2) 2.970(3) 153.2(19) .
O4 H4O O3 0.82 2.15 2.870(3) 146.6 6_556

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045