# Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Green Chemistry'

_journal_coden_Cambridge         1048

_publ_contact_author_name        'Ji-Chang Xiao'
_publ_contact_author_email       JCHXIAO@MAIL.SIOC.AC.CN

_publ_section_title              
;
Enantioselective Aldol Reaction of Cyclic
Ketones with Aryl Aldehydes Catalyzed by Cyclohexanediamine
Derived Salt in the Presence of Water
;
loop_
_publ_author_name
'Ji-Chang Xiao'
'Jin-Hong Lin'
'Cheng-Pan Zhang'

data_cd28552
_database_code_depnum_ccdc_archive 'CCDC 737246'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H31 F3 N2 O3 S'
_chemical_formula_weight         376.48

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   7.6593(7)
_cell_length_b                   12.5747(11)
_cell_length_c                   20.4376(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1968.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4186
_cell_measurement_theta_min      5.137
_cell_measurement_theta_max      47.384

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7596
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11642
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4266
_reflns_number_gt                3621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4266
_refine_ls_number_parameters     231
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.985
_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
S1 S 0.35597(7) 0.92002(4) -0.01882(2) 0.03985(14) Uani 1 1 d . . .
F1 F 0.4889(2) 1.02108(14) -0.11860(7) 0.0764(5) Uani 1 1 d . . .
F2 F 0.3325(3) 0.88692(14) -0.14433(7) 0.0819(5) Uani 1 1 d . . .
F3 F 0.2119(2) 1.03074(15) -0.11248(9) 0.0875(5) Uani 1 1 d . . .
O1 O 0.50994(19) 0.85500(13) -0.01829(8) 0.0544(4) Uani 1 1 d . . .
O2 O 0.3630(3) 1.01447(13) 0.01920(8) 0.0672(4) Uani 1 1 d . . .
O3 O 0.19693(18) 0.85916(13) -0.01290(8) 0.0559(4) Uani 1 1 d . . .
N1 N 0.8560(3) 0.86246(15) 0.04921(9) 0.0426(4) Uani 1 1 d D . .
N2 N 0.9511(2) 0.92773(15) 0.17347(7) 0.0415(4) Uani 1 1 d . . .
C1 C 0.8228(3) 0.97517(16) 0.06711(9) 0.0384(5) Uani 1 1 d . . .
H1 H 0.7041 0.9811 0.0846 0.046 Uiso 1 1 calc R . .
C2 C 0.8384(3) 1.04635(18) 0.00753(10) 0.0521(5) Uani 1 1 d . . .
H2A H 0.7520 1.0259 -0.0248 0.062 Uiso 1 1 calc R . .
H2B H 0.9532 1.0382 -0.0119 0.062 Uiso 1 1 calc R . .
C3 C 0.8104(4) 1.1621(2) 0.02729(15) 0.0716(8) Uani 1 1 d . . .
H3A H 0.8279 1.2076 -0.0105 0.086 Uiso 1 1 calc R . .
H3B H 0.6912 1.1715 0.0423 0.086 Uiso 1 1 calc R . .
C4 C 0.9340(5) 1.1943(2) 0.08061(15) 0.0822(9) Uani 1 1 d . . .
H4A H 0.9100 1.2671 0.0933 0.099 Uiso 1 1 calc R . .
H4B H 1.0527 1.1912 0.0642 0.099 Uiso 1 1 calc R . .
C5 C 0.9180(4) 1.12269(18) 0.14011(13) 0.0631(7) Uani 1 1 d . . .
H5A H 0.8019 1.1293 0.1587 0.076 Uiso 1 1 calc R . .
H5B H 1.0019 1.1443 0.1731 0.076 Uiso 1 1 calc R . .
C6 C 0.9516(3) 1.00631(16) 0.12048(9) 0.0399(5) Uani 1 1 d . . .
H6 H 1.0681 1.0040 0.1007 0.048 Uiso 1 1 calc R . .
C7 C 1.1208(3) 0.9267(2) 0.20792(10) 0.0544(6) Uani 1 1 d . . .
H7A H 1.1044 0.8959 0.2510 0.065 Uiso 1 1 calc R . .
H7B H 1.1599 0.9994 0.2138 0.065 Uiso 1 1 calc R . .
C8 C 1.2627(3) 0.8648(2) 0.17248(12) 0.0608(7) Uani 1 1 d . . .
H8A H 1.2701 0.8900 0.1277 0.073 Uiso 1 1 calc R . .
H8B H 1.3739 0.8789 0.1934 0.073 Uiso 1 1 calc R . .
C9 C 1.2318(4) 0.7471(3) 0.17179(18) 0.0862(9) Uani 1 1 d . . .
H9A H 1.1232 0.7335 0.1488 0.103 Uiso 1 1 calc R . .
H9B H 1.2165 0.7233 0.2166 0.103 Uiso 1 1 calc R . .
C10 C 1.3723(5) 0.6810(3) 0.14083(16) 0.0921(10) Uani 1 1 d . . .
H10A H 1.4069 0.7127 0.1001 0.138 Uiso 1 1 calc R . .
H10B H 1.3288 0.6105 0.1329 0.138 Uiso 1 1 calc R . .
H10C H 1.4711 0.6774 0.1696 0.138 Uiso 1 1 calc R . .
C11 C 0.8062(3) 0.9395(2) 0.22058(10) 0.0504(6) Uani 1 1 d . . .
H11A H 0.7032 0.9646 0.1977 0.060 Uiso 1 1 calc R . .
H11B H 0.8375 0.9924 0.2531 0.060 Uiso 1 1 calc R . .
C12 C 0.7641(3) 0.8357(2) 0.25459(12) 0.0612(6) Uani 1 1 d . . .
H12A H 0.8708 0.8062 0.2725 0.073 Uiso 1 1 calc R . .
H12B H 0.7192 0.7857 0.2226 0.073 Uiso 1 1 calc R . .
C13 C 0.6319(4) 0.8481(3) 0.30906(12) 0.0732(8) Uani 1 1 d . . .
H13A H 0.6821 0.8917 0.3434 0.088 Uiso 1 1 calc R . .
H13B H 0.5302 0.8849 0.2922 0.088 Uiso 1 1 calc R . .
C14 C 0.5753(4) 0.7434(3) 0.33785(16) 0.1074(13) Uani 1 1 d . . .
H14A H 0.5284 0.6991 0.3039 0.161 Uiso 1 1 calc R . .
H14B H 0.4875 0.7556 0.3705 0.161 Uiso 1 1 calc R . .
H14C H 0.6740 0.7088 0.3575 0.161 Uiso 1 1 calc R . .
C15 C 0.3472(3) 0.96721(19) -0.10329(11) 0.0523(5) Uani 1 1 d . . .
H1A H 0.761(2) 0.837(2) 0.0344(12) 0.058(8) Uiso 1 1 d D . .
H1B H 0.864(3) 0.8316(17) 0.0873(8) 0.052(6) Uiso 1 1 d D . .
H1C H 0.949(2) 0.8567(18) 0.0261(10) 0.048(6) Uiso 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
S1 0.0374(2) 0.0390(2) 0.0431(2) 0.0021(2) 0.0025(2) -0.0014(2)
F1 0.0713(10) 0.0887(12) 0.0693(9) 0.0248(9) 0.0115(8) -0.0198(9)
F2 0.1030(12) 0.0919(12) 0.0508(7) -0.0154(8) -0.0053(9) -0.0069(10)
F3 0.0787(11) 0.0902(12) 0.0936(12) 0.0323(10) -0.0122(9) 0.0281(9)
O1 0.0430(8) 0.0537(9) 0.0666(10) 0.0081(9) -0.0063(8) 0.0049(7)
O2 0.0808(11) 0.0581(9) 0.0628(9) -0.0173(9) 0.0102(10) -0.0063(10)
O3 0.0413(8) 0.0564(9) 0.0701(10) 0.0088(9) 0.0088(7) -0.0056(7)
N1 0.0411(10) 0.0488(10) 0.0380(9) -0.0068(8) 0.0009(10) -0.0027(10)
N2 0.0379(9) 0.0514(10) 0.0351(8) -0.0047(8) 0.0017(7) 0.0013(9)
C1 0.0332(11) 0.0432(11) 0.0388(10) -0.0035(8) 0.0026(8) 0.0035(9)
C2 0.0493(13) 0.0620(13) 0.0449(11) 0.0080(10) -0.0002(10) 0.0070(11)
C3 0.0826(19) 0.0578(15) 0.0745(17) 0.0215(14) 0.0101(15) 0.0197(14)
C4 0.113(2) 0.0393(14) 0.094(2) 0.0010(14) 0.0040(19) -0.0024(16)
C5 0.0783(18) 0.0455(13) 0.0655(15) -0.0135(12) 0.0011(13) -0.0010(12)
C6 0.0376(10) 0.0414(11) 0.0407(10) -0.0059(9) 0.0026(9) -0.0002(9)
C7 0.0485(13) 0.0703(15) 0.0445(11) -0.0086(12) -0.0098(9) -0.0009(13)
C8 0.0441(13) 0.088(2) 0.0502(13) 0.0041(14) -0.0073(11) 0.0012(13)
C9 0.0695(18) 0.080(2) 0.109(2) -0.009(2) 0.0011(18) 0.0085(17)
C10 0.084(2) 0.103(2) 0.089(2) -0.0115(19) -0.0016(18) 0.025(2)
C11 0.0478(13) 0.0633(15) 0.0401(10) -0.0059(10) 0.0043(9) 0.0034(11)
C12 0.0573(15) 0.0755(18) 0.0507(13) 0.0030(13) 0.0077(11) -0.0033(13)
C13 0.0586(15) 0.113(2) 0.0480(13) 0.0037(14) 0.0078(12) -0.0107(18)
C14 0.086(2) 0.160(4) 0.077(2) 0.033(2) 0.0084(17) -0.041(2)
C15 0.0499(13) 0.0555(13) 0.0514(12) 0.0065(11) -0.0009(12) 0.0014(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
S1 O2 1.4204(16) . ?
S1 O1 1.4350(15) . ?
S1 O3 1.4436(15) . ?
S1 C15 1.827(2) . ?
F1 C15 1.317(3) . ?
F2 C15 1.317(3) . ?
F3 C15 1.322(3) . ?
N1 C1 1.486(3) . ?
N1 H1A 0.846(16) . ?
N1 H1B 0.873(15) . ?
N1 H1C 0.860(16) . ?
N2 C6 1.466(3) . ?
N2 C11 1.476(3) . ?
N2 C7 1.479(3) . ?
C1 C2 1.516(3) . ?
C1 C6 1.522(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.499(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.518(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.539(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9800 . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.499(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.500(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.513(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 S1 O1 116.17(11) . . ?
O2 S1 O3 115.44(11) . . ?
O1 S1 O3 113.01(8) . . ?
O2 S1 C15 104.29(11) . . ?
O1 S1 C15 102.85(11) . . ?
O3 S1 C15 102.73(11) . . ?
S1 O1 H1A 140.8(6) . . ?
C1 N1 H1A 107.4(17) . . ?
C1 N1 H1B 102.5(15) . . ?
H1A N1 H1B 102(2) . . ?
C1 N1 H1C 110.9(16) . . ?
H1A N1 H1C 119(2) . . ?
H1B N1 H1C 113(2) . . ?
C6 N2 C11 114.61(17) . . ?
C6 N2 C7 110.82(17) . . ?
C11 N2 C7 110.56(16) . . ?
N1 C1 C2 110.61(16) . . ?
N1 C1 C6 108.14(17) . . ?
C2 C1 C6 111.89(18) . . ?
N1 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
C6 C1 H1 108.7 . . ?
C1 C2 C3 109.86(19) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 111.1(2) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.8(2) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 110.0(2) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N2 C6 C1 110.75(17) . . ?
N2 C6 C5 116.60(17) . . ?
C1 C6 C5 108.84(19) . . ?
N2 C6 H6 106.7 . . ?
C1 C6 H6 106.7 . . ?
C5 C6 H6 106.7 . . ?
N2 C7 C8 113.96(18) . . ?
N2 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.4(2) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 116.0(3) . . ?
C8 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 111.9(2) . . ?
N2 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.0(3) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F2 108.2(2) . . ?
F1 C15 F3 107.53(19) . . ?
F2 C15 F3 107.8(2) . . ?
F1 C15 S1 111.19(17) . . ?
F2 C15 S1 110.85(16) . . ?
F3 C15 S1 111.06(17) . . ?

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
O2 S1 O1 H1A 11.5(10) . . . . ?
O3 S1 O1 H1A -125.3(10) . . . . ?
C15 S1 O1 H1A 124.7(10) . . . . ?
N1 C1 C2 C3 -178.0(2) . . . . ?
C6 C1 C2 C3 -57.4(3) . . . . ?
C1 C2 C3 C4 55.5(3) . . . . ?
C2 C3 C4 C5 -56.6(3) . . . . ?
C3 C4 C5 C6 57.7(3) . . . . ?
C11 N2 C6 C1 -80.4(2) . . . . ?
C7 N2 C6 C1 153.61(17) . . . . ?
C11 N2 C6 C5 44.8(3) . . . . ?
C7 N2 C6 C5 -81.2(2) . . . . ?
N1 C1 C6 N2 -50.0(2) . . . . ?
C2 C1 C6 N2 -172.10(16) . . . . ?
N1 C1 C6 C5 -179.47(18) . . . . ?
C2 C1 C6 C5 58.5(2) . . . . ?
C4 C5 C6 N2 176.5(2) . . . . ?
C4 C5 C6 C1 -57.4(3) . . . . ?
C6 N2 C7 C8 -79.7(2) . . . . ?
C11 N2 C7 C8 152.1(2) . . . . ?
N2 C7 C8 C9 -69.3(3) . . . . ?
C7 C8 C9 C10 -176.7(2) . . . . ?
C6 N2 C11 C12 155.21(18) . . . . ?
C7 N2 C11 C12 -78.7(2) . . . . ?
N2 C11 C12 C13 172.82(19) . . . . ?
C11 C12 C13 C14 173.6(2) . . . . ?
O2 S1 C15 F1 62.25(19) . . . . ?
O1 S1 C15 F1 -59.41(18) . . . . ?
O3 S1 C15 F1 -176.96(17) . . . . ?
O2 S1 C15 F2 -177.28(19) . . . . ?
O1 S1 C15 F2 61.1(2) . . . . ?
O3 S1 C15 F2 -56.5(2) . . . . ?
O2 S1 C15 F3 -57.45(19) . . . . ?
O1 S1 C15 F3 -179.11(16) . . . . ?
O3 S1 C15 F3 63.34(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
N1 H1C O3 0.860(16) 2.058(17) 2.904(3) 168(2) 1_655
N1 H1B N2 0.873(15) 2.24(2) 2.767(2) 118.9(18) .
N1 H1A O3 0.846(16) 2.56(2) 3.131(2) 126(2) 4_565
N1 H1A O1 0.846(16) 2.218(19) 2.989(3) 152(2) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051