# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Chemical Science'

_journal_coden_Cambridge         1475
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Paolo Melchiorre'
_publ_contact_author_email       pmelchiorre@iciq.es

_publ_section_title              
;
Dioxindole in asymmetric catalytic synthesis:
direct access to 3-substituted 3-hydroxy-2-oxindoles via
1,4-additions to nitroalkenes

;
loop_
_publ_author_name
M.Retini
G.Bergonzini
P.Melchiorre

# Attachment '- CCDC 859399.cif'

data_mo_grb295b_0m
_database_code_depnum_ccdc_archive 'CCDC 859399'
#TrackingRef '- CCDC 859399.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Br N2 O4'
_chemical_formula_weight         467.31

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.1970(8)
_cell_length_b                   7.4443(5)
_cell_length_c                   12.4368(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.003(2)
_cell_angle_gamma                90.00
_cell_volume                     1026.56(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9111
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8224
_exptl_absorpt_correction_T_max  0.9051
_exptl_absorpt_process_details   
;
SADABS Version 2008/1 Bruker-Nonius
Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
;
It should be noted that the esd's of the cell dimensions are probably too low;
they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            17795
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         32.65
_reflns_number_total             6761
_reflns_number_gt                6291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-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^)+(0.1000P)^2^+0.1940P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.008(5)
_refine_ls_number_reflns         6761
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   0.696
_refine_ls_restrained_S_all      0.696
_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 0.809562(17) -0.10701(3) -0.172571(12) 0.03045(6) Uani 1 1 d . . .
N1 N 0.96759(12) -0.0203(2) 0.30761(12) 0.0206(3) Uani 1 1 d . . .
N2 N 0.6874(2) 0.5899(2) 0.31053(13) 0.0326(4) Uani 1 1 d . . .
O1 O 0.86819(13) 0.10774(19) 0.43845(10) 0.0262(3) Uani 1 1 d . . .
O2 O 0.66503(10) 0.03918(16) 0.26191(10) 0.0174(2) Uani 1 1 d . . .
H2A H 0.6713 -0.0725 0.2706 0.026 Uiso 1 1 calc R . .
O3 O 0.5875(2) 0.6576(2) 0.30534(16) 0.0507(5) Uani 1 1 d . . .
O4 O 0.7794(2) 0.6758(2) 0.30575(16) 0.0491(5) Uani 1 1 d . . .
C1 C 0.94405(14) -0.0527(2) 0.19552(14) 0.0186(3) Uani 1 1 d . . .
C2 C 1.01322(15) -0.1483(2) 0.13184(16) 0.0242(3) Uani 1 1 d . . .
H2 H 1.0878 -0.2004 0.1622 0.029 Uiso 1 1 calc R . .
C3 C 0.97034(16) -0.1662(2) 0.02164(16) 0.0248(3) Uani 1 1 d . . .
H3 H 1.0156 -0.2317 -0.0243 0.030 Uiso 1 1 calc R . .
C4 C 0.86095(14) -0.0879(2) -0.02103(13) 0.0204(3) Uani 1 1 d . . .
C5 C 0.78979(14) 0.0054(2) 0.04368(13) 0.0172(3) Uani 1 1 d . . .
H5 H 0.7143 0.0551 0.0137 0.021 Uiso 1 1 calc R . .
C6 C 0.83262(12) 0.0233(2) 0.15333(12) 0.0151(2) Uani 1 1 d . . .
C7 C 0.77798(13) 0.1112(2) 0.24453(12) 0.0151(2) Uani 1 1 d . . .
C8 C 0.87468(14) 0.0695(2) 0.34422(13) 0.0194(3) Uani 1 1 d . . .
C9 C 0.76045(13) 0.3166(2) 0.22998(12) 0.0162(2) Uani 1 1 d . . .
H9 H 0.8420 0.3735 0.2353 0.019 Uiso 1 1 calc R . .
C10 C 0.69145(13) 0.36200(18) 0.11960(12) 0.0152(3) Uani 1 1 d . . .
C11 C 0.57254(13) 0.3053(2) 0.08941(13) 0.0183(3) Uani 1 1 d . . .
H11 H 0.5290 0.2537 0.1421 0.022 Uiso 1 1 calc R . .
C12 C 0.51783(15) 0.3239(2) -0.01723(15) 0.0229(3) Uani 1 1 d . . .
H12 H 0.4373 0.2836 -0.0374 0.027 Uiso 1 1 calc R . .
C13 C 0.58000(14) 0.4011(3) -0.09458(12) 0.0239(3) Uani 1 1 d . . .
H13 H 0.5437 0.4078 -0.1682 0.029 Uiso 1 1 calc R . .
C14 C 0.69547(15) 0.4685(2) -0.06394(14) 0.0223(3) Uani 1 1 d . . .
H14 H 0.7368 0.5277 -0.1156 0.027 Uiso 1 1 calc R . .
C15 C 0.75037(14) 0.4485(2) 0.04346(13) 0.0186(3) Uani 1 1 d . . .
H15 H 0.8292 0.4950 0.0645 0.022 Uiso 1 1 calc R . .
C16 C 0.69766(15) 0.3897(3) 0.32253(11) 0.0215(2) Uani 1 1 d . . .
H16A H 0.6165 0.3356 0.3195 0.026 Uiso 1 1 calc R . .
H16B H 0.7450 0.3589 0.3934 0.026 Uiso 1 1 calc R . .
C17 C 1.06640(14) -0.1018(4) 0.38041(14) 0.0289(3) Uani 1 1 d . . .
H17A H 1.0823 -0.2232 0.3532 0.035 Uiso 1 1 calc R . .
H17B H 1.0415 -0.1156 0.4533 0.035 Uiso 1 1 calc R . .
C18 C 1.18193(15) 0.0071(3) 0.39063(14) 0.0259(3) Uani 1 1 d . . .
C19 C 1.18357(15) 0.1837(3) 0.42609(15) 0.0276(4) Uani 1 1 d . . .
H19 H 1.1106 0.2383 0.4402 0.033 Uiso 1 1 calc R . .
C20 C 1.28990(19) 0.2825(4) 0.44145(17) 0.0401(5) Uani 1 1 d . . .
H20 H 1.2897 0.4039 0.4650 0.048 Uiso 1 1 calc R . .
C21 C 1.39690(18) 0.2009(5) 0.42173(18) 0.0508(8) Uani 1 1 d . . .
H21 H 1.4704 0.2665 0.4327 0.061 Uiso 1 1 calc R . .
C22 C 1.39621(18) 0.0266(5) 0.38658(18) 0.0519(8) Uani 1 1 d . . .
H22 H 1.4695 -0.0276 0.3731 0.062 Uiso 1 1 calc R . .
C23 C 1.28939(17) -0.0728(4) 0.37032(16) 0.0395(6) Uani 1 1 d . . .
H23 H 1.2899 -0.1935 0.3457 0.047 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 0.05052(11) 0.02233(8) 0.02006(8) -0.00560(7) 0.01046(6) -0.00745(8)
N1 0.0189(6) 0.0189(6) 0.0224(6) 0.0054(5) -0.0028(5) 0.0010(5)
N2 0.0673(12) 0.0148(7) 0.0162(6) -0.0014(5) 0.0076(7) 0.0047(7)
O1 0.0357(6) 0.0235(6) 0.0178(5) 0.0010(5) -0.0020(5) -0.0003(5)
O2 0.0187(5) 0.0109(5) 0.0232(5) 0.0014(4) 0.0050(4) -0.0006(4)
O3 0.0780(13) 0.0290(8) 0.0407(9) -0.0050(7) -0.0075(9) 0.0273(9)
O4 0.0954(14) 0.0158(7) 0.0434(9) -0.0053(6) 0.0352(10) -0.0151(8)
C1 0.0173(6) 0.0146(6) 0.0238(7) 0.0041(5) 0.0018(5) -0.0001(5)
C2 0.0202(6) 0.0162(8) 0.0371(9) 0.0021(6) 0.0071(6) 0.0038(5)
C3 0.0262(7) 0.0189(7) 0.0324(8) -0.0017(6) 0.0144(6) 0.0013(6)
C4 0.0275(7) 0.0125(7) 0.0228(6) -0.0034(6) 0.0094(5) -0.0039(6)
C5 0.0201(6) 0.0138(6) 0.0180(6) -0.0018(5) 0.0032(5) -0.0004(5)
C6 0.0154(5) 0.0115(6) 0.0183(6) 0.0003(5) 0.0018(4) 0.0008(5)
C7 0.0156(5) 0.0125(6) 0.0167(6) -0.0003(5) 0.0001(4) -0.0006(5)
C8 0.0217(6) 0.0155(7) 0.0191(6) 0.0025(5) -0.0034(5) -0.0016(5)
C9 0.0214(6) 0.0109(6) 0.0160(6) 0.0005(5) 0.0022(5) -0.0016(5)
C10 0.0181(5) 0.0110(7) 0.0162(5) 0.0011(4) 0.0018(4) 0.0008(4)
C11 0.0171(6) 0.0154(7) 0.0224(7) 0.0016(5) 0.0024(5) 0.0023(5)
C12 0.0200(6) 0.0192(7) 0.0275(8) 0.0007(6) -0.0033(5) 0.0043(6)
C13 0.0284(7) 0.0224(7) 0.0192(6) 0.0009(8) -0.0022(5) 0.0065(8)
C14 0.0260(7) 0.0205(7) 0.0207(7) 0.0041(6) 0.0042(5) 0.0019(6)
C15 0.0206(6) 0.0148(6) 0.0207(6) 0.0033(5) 0.0041(5) -0.0012(5)
C16 0.0352(7) 0.0110(5) 0.0193(5) -0.0008(7) 0.0074(5) 0.0019(7)
C17 0.0253(7) 0.0276(8) 0.0312(7) 0.0109(9) -0.0053(5) 0.0037(8)
C18 0.0184(7) 0.0401(10) 0.0181(7) 0.0056(7) -0.0012(5) 0.0059(6)
C19 0.0209(7) 0.0406(11) 0.0213(7) 0.0036(7) 0.0025(6) -0.0009(7)
C20 0.0325(9) 0.0644(16) 0.0232(8) -0.0016(9) 0.0031(7) -0.0168(10)
C21 0.0208(8) 0.108(3) 0.0240(9) -0.0036(12) 0.0038(7) -0.0160(11)
C22 0.0181(7) 0.114(3) 0.0242(9) -0.0066(12) 0.0043(6) 0.0095(11)
C23 0.0267(8) 0.0675(19) 0.0226(7) -0.0015(9) -0.0025(6) 0.0169(9)

_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 C4 1.8978(16) . ?
N1 C8 1.367(2) . ?
N1 C1 1.403(2) . ?
N1 C17 1.460(2) . ?
N2 O4 1.222(3) . ?
N2 O3 1.220(3) . ?
N2 C16 1.501(3) . ?
O1 C8 1.218(2) . ?
O2 C7 1.4178(18) . ?
C1 C2 1.380(2) . ?
C1 C6 1.404(2) . ?
C2 C3 1.394(3) . ?
C3 C4 1.393(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.511(2) . ?
C7 C9 1.549(2) . ?
C7 C8 1.559(2) . ?
C9 C10 1.517(2) . ?
C9 C16 1.530(2) . ?
C10 C15 1.386(2) . ?
C10 C11 1.397(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.390(2) . ?
C14 C15 1.398(2) . ?
C17 C18 1.517(3) . ?
C18 C19 1.386(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.390(3) . ?
C20 C21 1.395(4) . ?
C21 C22 1.369(5) . ?
C22 C23 1.397(4) . ?

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
C8 N1 C1 111.63(13) . . ?
C8 N1 C17 122.87(15) . . ?
C1 N1 C17 124.46(16) . . ?
O4 N2 O3 123.7(2) . . ?
O4 N2 C16 118.1(2) . . ?
O3 N2 C16 118.2(2) . . ?
C2 C1 C6 122.28(15) . . ?
C2 C1 N1 128.02(15) . . ?
C6 C1 N1 109.66(14) . . ?
C1 C2 C3 118.00(15) . . ?
C4 C3 C2 119.91(15) . . ?
C3 C4 C5 122.11(15) . . ?
C3 C4 Br1 118.41(12) . . ?
C5 C4 Br1 119.47(12) . . ?
C6 C5 C4 117.90(14) . . ?
C5 C6 C1 119.76(14) . . ?
C5 C6 C7 131.20(13) . . ?
C1 C6 C7 109.01(13) . . ?
O2 C7 C6 114.43(12) . . ?
O2 C7 C9 106.86(12) . . ?
C6 C7 C9 113.45(13) . . ?
O2 C7 C8 109.81(12) . . ?
C6 C7 C8 101.64(12) . . ?
C9 C7 C8 110.62(12) . . ?
O1 C8 N1 125.79(15) . . ?
O1 C8 C7 126.20(15) . . ?
N1 C8 C7 108.00(13) . . ?
C10 C9 C16 111.86(12) . . ?
C10 C9 C7 111.46(12) . . ?
C16 C9 C7 109.09(13) . . ?
C15 C10 C11 118.90(13) . . ?
C15 C10 C9 119.41(13) . . ?
C11 C10 C9 121.47(13) . . ?
C12 C11 C10 120.24(15) . . ?
C11 C12 C13 120.42(15) . . ?
C12 C13 C14 119.78(14) . . ?
C13 C14 C15 119.47(15) . . ?
C10 C15 C14 120.95(15) . . ?
N2 C16 C9 108.36(14) . . ?
N1 C17 C18 113.17(18) . . ?
C19 C18 C23 119.20(19) . . ?
C19 C18 C17 120.47(17) . . ?
C23 C18 C17 120.2(2) . . ?
C18 C19 C20 121.3(2) . . ?
C19 C20 C21 119.1(3) . . ?
C22 C21 C20 120.1(2) . . ?
C21 C22 C23 121.0(2) . . ?
C18 C23 C22 119.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -175.83(16) . . . . ?
C17 N1 C1 C2 -7.3(3) . . . . ?
C8 N1 C1 C6 2.09(19) . . . . ?
C17 N1 C1 C6 170.66(16) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
N1 C1 C2 C3 178.70(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 Br1 177.33(13) . . . . ?
C3 C4 C5 C6 1.8(2) . . . . ?
Br1 C4 C5 C6 -177.28(12) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -178.60(15) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
N1 C1 C6 C5 -179.02(14) . . . . ?
C2 C1 C6 C7 177.58(15) . . . . ?
N1 C1 C6 C7 -0.48(18) . . . . ?
C5 C6 C7 O2 59.0(2) . . . . ?
C1 C6 C7 O2 -119.29(14) . . . . ?
C5 C6 C7 C9 -64.0(2) . . . . ?
C1 C6 C7 C9 117.73(14) . . . . ?
C5 C6 C7 C8 177.28(16) . . . . ?
C1 C6 C7 C8 -1.03(16) . . . . ?
C1 N1 C8 O1 176.34(17) . . . . ?
C17 N1 C8 O1 7.6(3) . . . . ?
C1 N1 C8 C7 -2.72(18) . . . . ?
C17 N1 C8 C7 -171.51(16) . . . . ?
O2 C7 C8 O1 -55.3(2) . . . . ?
C6 C7 C8 O1 -176.82(16) . . . . ?
C9 C7 C8 O1 62.4(2) . . . . ?
O2 C7 C8 N1 123.77(14) . . . . ?
C6 C7 C8 N1 2.24(16) . . . . ?
C9 C7 C8 N1 -118.53(14) . . . . ?
O2 C7 C9 C10 -74.58(15) . . . . ?
C6 C7 C9 C10 52.46(16) . . . . ?
C8 C7 C9 C10 165.92(12) . . . . ?
O2 C7 C9 C16 49.43(15) . . . . ?
C6 C7 C9 C16 176.48(12) . . . . ?
C8 C7 C9 C16 -70.06(16) . . . . ?
C16 C9 C10 C15 126.28(16) . . . . ?
C7 C9 C10 C15 -111.29(15) . . . . ?
C16 C9 C10 C11 -59.20(19) . . . . ?
C7 C9 C10 C11 63.23(18) . . . . ?
C15 C10 C11 C12 4.6(2) . . . . ?
C9 C10 C11 C12 -169.94(14) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -3.3(3) . . . . ?
C12 C13 C14 C15 3.6(3) . . . . ?
C11 C10 C15 C14 -4.3(2) . . . . ?
C9 C10 C15 C14 170.35(15) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
O4 N2 C16 C9 -55.2(2) . . . . ?
O3 N2 C16 C9 124.36(17) . . . . ?
C10 C9 C16 N2 -59.21(17) . . . . ?
C7 C9 C16 N2 177.01(13) . . . . ?
C8 N1 C17 C18 -103.23(19) . . . . ?
C1 N1 C17 C18 89.4(2) . . . . ?
N1 C17 C18 C19 57.9(2) . . . . ?
N1 C17 C18 C23 -125.8(2) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 C20 176.55(17) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C19 C18 C23 C22 0.3(3) . . . . ?
C17 C18 C23 C22 -176.11(18) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.061