# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014


data_1_RS-NPX-BPY_CCDC_No_931856

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O3, 0.5 (C10 H8 N2)'
_chemical_formula_sum            'C19 H18 N O3'
_chemical_formula_weight         308.34

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   P21/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                   7.624(6)
_cell_length_b                   5.800(4)
_cell_length_c                   36.02(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.017(8)
_cell_angle_gamma                90.00
_cell_volume                     1593(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2804
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9853
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   
;
(ABSCOR; Higashi, 1995)
;
_exptl_special_details           
; 
 Rigaku CrystalClear-SM Expert 2.0 r4 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_chemical_absolute_configuration rm
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13044
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3089
_reflns_number_gt                2359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
In RS-NPX--BPY, the anisotropic displacement parameters for bipyridine
was too large, which indicated the orientational disorder. The .lst file also
suggested possible splits over two positions for C15 and C16. A reasonable
model was obtained by splting the components into two (C15-C16 and C15'-C16'
with site occupancies as 0.64 and 0.36 respectively) using PART instructions
in SHELX.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+3.3446P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.1980
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_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 0.7980(4) 0.0488(5) 0.91176(8) 0.0438(8) Uani 1 1 d . . .
H1 H 0.8743 0.0616 0.9278 0.066 Uiso 1 1 d R . .
O2 O 0.7381(5) 0.3874(6) 0.93869(8) 0.0536(9) Uani 1 1 d . . .
O3 O 0.8134(3) 0.3550(4) 0.67324(6) 0.0236(6) Uani 1 1 d . . .
C1 C 0.7090(6) 0.2428(7) 0.91526(11) 0.0362(10) Uani 1 1 d . . .
C2 C 0.5628(5) 0.2593(8) 0.88651(11) 0.0359(10) Uani 1 1 d . . .
H2 H 0.5049 0.1086 0.8855 0.043 Uiso 1 1 calc R . .
C3 C 0.4251(6) 0.4352(9) 0.89588(12) 0.0476(12) Uani 1 1 d . . .
H3A H 0.3361 0.4349 0.8770 0.071 Uiso 1 1 calc R . .
H3B H 0.4780 0.5852 0.8972 0.071 Uiso 1 1 calc R . .
H3C H 0.3732 0.3980 0.9194 0.071 Uiso 1 1 calc R . .
C4 C 0.6442(5) 0.3050(6) 0.84800(10) 0.0253(8) Uani 1 1 d . . .
C5 C 0.7418(5) 0.5088(7) 0.84108(10) 0.0277(9) Uani 1 1 d . . .
H5 H 0.7637 0.6105 0.8605 0.033 Uiso 1 1 calc R . .
C6 C 0.8044(5) 0.5587(6) 0.80625(10) 0.0225(8) Uani 1 1 d . . .
H6 H 0.8684 0.6932 0.8025 0.027 Uiso 1 1 calc R . .
C7 C 0.7729(4) 0.4080(6) 0.77587(9) 0.0174(7) Uani 1 1 d . . .
C8 C 0.8241(4) 0.4640(6) 0.73874(9) 0.0193(8) Uani 1 1 d . . .
H8 H 0.8866 0.5983 0.7339 0.023 Uiso 1 1 calc R . .
C9 C 0.7801(4) 0.3177(6) 0.71036(9) 0.0197(8) Uani 1 1 d . . .
C10 C 0.6910(4) 0.1074(6) 0.71753(10) 0.0222(8) Uani 1 1 d . . .
H10 H 0.6635 0.0093 0.6979 0.027 Uiso 1 1 calc R . .
C11 C 0.6452(4) 0.0477(6) 0.75296(10) 0.0205(8) Uani 1 1 d . . .
H11 H 0.5910 -0.0933 0.7574 0.025 Uiso 1 1 calc R . .
C12 C 0.6797(4) 0.1994(6) 0.78304(9) 0.0194(8) Uani 1 1 d . . .
C13 C 0.6176(5) 0.1537(6) 0.81955(10) 0.0243(8) Uani 1 1 d . . .
H13 H 0.5574 0.0173 0.8241 0.029 Uiso 1 1 calc R . .
C14 C 0.9012(5) 0.5651(7) 0.66382(10) 0.0304(9) Uani 1 1 d . . .
H14A H 0.9153 0.5740 0.6374 0.046 Uiso 1 1 calc R . .
H14B H 1.0144 0.5684 0.6755 0.046 Uiso 1 1 calc R . .
H14C H 0.8329 0.6938 0.6723 0.046 Uiso 1 1 calc R . .
N1 N 1.0906(5) 0.0312(8) 0.95250(10) 0.0507(11) Uani 1 1 d . . .
C15 C 1.161(3) -0.179(4) 0.9544(6) 0.037(5) Uani 0.36(3) 1 d P A 1
H15 H 1.1070 -0.3065 0.9438 0.044 Uiso 0.36(3) 1 calc PR A 1
C16 C 1.318(3) -0.196(4) 0.9728(6) 0.037(5) Uani 0.36(3) 1 d P A 1
H16 H 1.3690 -0.3413 0.9748 0.044 Uiso 0.36(3) 1 calc PR A 1
C15' C 1.227(2) -0.116(3) 0.9434(4) 0.048(3) Uani 0.64(3) 1 d P A 2
H15' H 1.2084 -0.2124 0.9232 0.057 Uiso 0.64(3) 1 calc PR A 2
C16' C 1.389(2) -0.137(2) 0.9611(4) 0.047(4) Uani 0.64(3) 1 d P A 2
H16' H 1.4735 -0.2427 0.9535 0.057 Uiso 0.64(3) 1 calc PR A 2
C17 C 1.4135(6) 0.0071(8) 0.99032(10) 0.0435(12) Uani 1 1 d . . .
C18 C 1.2972(6) 0.1835(9) 0.99610(14) 0.0503(13) Uani 1 1 d . A .
H18 H 1.3233 0.2991 1.0131 0.060 Uiso 1 1 calc R . .
C19 C 1.1399(6) 0.1899(9) 0.97652(14) 0.0512(13) Uani 1 1 d . A .
H19 H 1.0650 0.3137 0.9806 0.061 Uiso 1 1 calc R . .


_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 1.320(5) . ?
O1 H1 0.8224 . ?
O2 C1 1.210(5) . ?
O3 C9 1.378(4) . ?
O3 C14 1.431(5) . ?
C1 C2 1.524(6) . ?
C2 C3 1.502(6) . ?
C2 C4 1.543(5) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C13 1.364(5) . ?
C4 C5 1.418(6) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.421(5) . ?
C6 H6 0.9300 . ?
C7 C12 1.427(5) . ?
C7 C8 1.431(5) . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(5) . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.420(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.423(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 C19 1.318(6) . ?
N1 C15 1.333(18) . ?
N1 C15' 1.385(13) . ?
C15 C16 1.37(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.52(2) . ?
C16 H16 0.9300 . ?
C15' C16' 1.394(14) . ?
C15' H15' 0.9300 . ?
C16' C17 1.358(11) . ?
C16' H16' 0.9300 . ?
C17 C18 1.370(6) . ?
C17 C17 1.494(9) 3_857 ?
C18 C19 1.391(7) . ?
C18 H18 0.9300 . ?
C19 H19 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
C1 O1 H1 102.7 . . ?
C9 O3 C14 116.7(3) . . ?
O2 C1 O1 124.3(4) . . ?
O2 C1 C2 124.3(4) . . ?
O1 C1 C2 111.4(4) . . ?
C3 C2 C1 113.6(4) . . ?
C3 C2 C4 111.5(3) . . ?
C1 C2 C4 109.1(3) . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C4 C2 H2 107.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C13 C4 C5 118.8(3) . . ?
C13 C4 C2 120.3(4) . . ?
C5 C4 C2 120.8(4) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C12 117.8(3) . . ?
C6 C7 C8 122.3(3) . . ?
C12 C7 C8 119.8(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 O3 125.6(3) . . ?
C8 C9 C10 120.9(3) . . ?
O3 C9 C10 113.5(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 C7 118.6(3) . . ?
C13 C12 C7 119.4(3) . . ?
C4 C13 C12 121.7(4) . . ?
C4 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 N1 C15 119.3(8) . . ?
C19 N1 C15' 111.8(7) . . ?
N1 C15 C16 116.4(15) . . ?
N1 C15 H15 121.8 . . ?
C16 C15 H15 121.8 . . ?
C15 C16 C17 124.1(14) . . ?
C15 C16 H16 118.0 . . ?
C17 C16 H16 118.0 . . ?
N1 C15' C16' 127.7(9) . . ?
N1 C15' H15' 116.2 . . ?
C16' C15' H15' 116.2 . . ?
C17 C16' C15' 115.0(10) . . ?
C17 C16' H16' 122.5 . . ?
C15' C16' H16' 122.5 . . ?
C16' C17 C18 119.3(6) . . ?
C16' C17 C17 116.7(7) . 3_857 ?
C18 C17 C17 122.8(5) . 3_857 ?
C18 C17 C16 109.4(8) . . ?
C17 C17 C16 125.0(8) 3_857 . ?
C17 C18 C19 120.0(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
N1 C19 C18 124.1(5) . . ?
N1 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?

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 C1 C2 C3 -16.4(6) . . . . ?
O1 C1 C2 C3 162.5(4) . . . . ?
O2 C1 C2 C4 108.7(5) . . . . ?
O1 C1 C2 C4 -72.4(4) . . . . ?
C3 C2 C4 C13 -113.2(4) . . . . ?
C1 C2 C4 C13 120.4(4) . . . . ?
C3 C2 C4 C5 64.2(5) . . . . ?
C1 C2 C4 C5 -62.1(5) . . . . ?
C13 C4 C5 C6 2.0(5) . . . . ?
C2 C4 C5 C6 -175.4(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C12 -2.3(5) . . . . ?
C5 C6 C7 C8 174.9(3) . . . . ?
C6 C7 C8 C9 -176.0(3) . . . . ?
C12 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 O3 176.8(3) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C14 O3 C9 C8 -0.1(5) . . . . ?
C14 O3 C9 C10 179.3(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
O3 C9 C10 C11 -178.6(3) . . . . ?
C9 C10 C11 C12 2.6(5) . . . . ?
C10 C11 C12 C13 173.3(3) . . . . ?
C10 C11 C12 C7 -3.9(5) . . . . ?
C6 C7 C12 C11 179.3(3) . . . . ?
C8 C7 C12 C11 2.1(5) . . . . ?
C6 C7 C12 C13 2.0(5) . . . . ?
C8 C7 C12 C13 -175.2(3) . . . . ?
C5 C4 C13 C12 -2.3(5) . . . . ?
C2 C4 C13 C12 175.2(3) . . . . ?
C11 C12 C13 C4 -177.0(3) . . . . ?
C7 C12 C13 C4 0.3(5) . . . . ?
C19 N1 C15 C16 -20(2) . . . . ?
C15' N1 C15 C16 63.7(19) . . . . ?
N1 C15 C16 C17 -1(2) . . . . ?
C19 N1 C15' C16' 12.3(15) . . . . ?
C15 N1 C15' C16' -99(2) . . . . ?
N1 C15' C16' C17 -0.9(15) . . . . ?
C15' C16' C17 C18 -11.1(15) . . . . ?
C15' C16' C17 C17 -179.0(7) . . . 3_857 ?
C15' C16' C17 C16 66.8(18) . . . . ?
C15 C16 C17 C16' -95(2) . . . . ?
C15 C16 C17 C18 20.5(19) . . . . ?
C15 C16 C17 C17 -178.4(11) . . . 3_857 ?
C16' C17 C18 C19 11.3(13) . . . . ?
C17 C17 C18 C19 178.4(5) 3_857 . . . ?
C16 C17 C18 C19 -20.0(13) . . . . ?
C15 N1 C19 C18 21.6(18) . . . . ?
C15' N1 C19 C18 -12.2(11) . . . . ?
C17 C18 C19 N1 1.5(8) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 931856'

#===END

data_3_RS-NPX-PIZ__CCDC_No_931857

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            RS-Naproxen-Piperidine
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 O3, 0.5 (C4 H10 N2)'
_chemical_formula_sum            'C16 H18 N O3'
_chemical_formula_weight         272.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   7.966(4)
_cell_length_b                   6.012(3)
_cell_length_c                   28.985(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.739(7)
_cell_angle_gamma                90.00
_cell_volume                     1387.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2834
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   
;
(ABSCOR; Higashi, 1995)
;
_exptl_special_details           
; 
 Rigaku CrystalClear-SM Expert 2.0 r4 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_chemical_absolute_configuration rm
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6743
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0852
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3120
_reflns_number_gt                1755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
In RS-NPX--PIZ, the anisotropic displacement parameters for  propionic
acid side chain of naproxen was too large, which indicated the orientational
disorder of the alkyl group. The .lst file also suggested possible splits over
two positions for C2 and C3. A reasonable model was obtained by splting the
components into two (C2-C3 and C2'-C3' with site occupancies as 0.61 and 0.39
respectively) using PART instructions in SHELX.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0511P)²+1.1632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.2913(4) 1.0277(4) 0.04324(10) 0.0597(9) Uani 1 1 d . A .
O2 O 0.1507(4) 1.3312(5) 0.05905(10) 0.0670(9) Uani 1 1 d . A .
O3 O 0.3608(3) 0.8424(4) 0.34881(8) 0.0441(7) Uani 1 1 d . . .
C1 C 0.1723(6) 1.1279(7) 0.06165(13) 0.0523(12) Uani 1 1 d . . .
C2 C 0.0296(10) 1.0335(14) 0.0931(3) 0.0326(19) Uani 0.606(11) 1 d P A 1
H2 H -0.0483 1.1514 0.1018 0.039 Uiso 0.606(11) 1 calc PR A 1
C3 C -0.0636(9) 0.8445(14) 0.0675(2) 0.046(3) Uani 0.606(11) 1 d P A 1
H3C H 0.0154 0.7324 0.0589 0.069 Uiso 0.606(11) 1 calc PR A 1
H3B H -0.1193 0.9027 0.0402 0.069 Uiso 0.606(11) 1 calc PR A 1
H3A H -0.1451 0.7805 0.0872 0.069 Uiso 0.606(11) 1 calc PR A 1
C2' C 0.0734(16) 0.9342(19) 0.0831(4) 0.032(3) Uani 0.394(11) 1 d P A 2
H2' H 0.0907 0.7905 0.0680 0.039 Uiso 0.394(11) 1 calc PR A 2
C3' C -0.1046(14) 1.014(2) 0.0805(4) 0.047(4) Uani 0.394(11) 1 d P A 2
H3'A H -0.1120 1.1564 0.0951 0.070 Uiso 0.394(11) 1 calc PR A 2
H3'B H -0.1750 0.9095 0.0959 0.070 Uiso 0.394(11) 1 calc PR A 2
H3'C H -0.1411 1.0261 0.0487 0.070 Uiso 0.394(11) 1 calc PR A 2
C4 C 0.1222(5) 0.9346(8) 0.13628(14) 0.0552(12) Uani 1 1 d . . .
C5 C 0.2084(5) 0.7319(7) 0.14271(12) 0.0500(11) Uani 1 1 d . A .
H5 H 0.2168 0.6350 0.1179 0.060 Uiso 1 1 calc R . .
C6 C 0.2803(5) 0.6734(6) 0.18456(11) 0.0400(9) Uani 1 1 d . . .
H6 H 0.3391 0.5402 0.1875 0.048 Uiso 1 1 calc R A .
C7 C 0.2657(4) 0.8129(5) 0.22308(11) 0.0293(7) Uani 1 1 d . A .
C8 C 0.3319(4) 0.7500(5) 0.26741(10) 0.0296(8) Uani 1 1 d . . .
H8 H 0.3911 0.6176 0.2712 0.035 Uiso 1 1 calc R A .
C9 C 0.3074(4) 0.8868(5) 0.30440(11) 0.0328(8) Uani 1 1 d . A .
C10 C 0.2204(5) 1.0891(6) 0.29869(13) 0.0416(9) Uani 1 1 d . . .
H10 H 0.2045 1.1801 0.3241 0.050 Uiso 1 1 calc R A .
C11 C 0.1595(5) 1.1530(6) 0.25663(14) 0.0428(9) Uani 1 1 d . A .
H11 H 0.1043 1.2887 0.2535 0.051 Uiso 1 1 calc R . .
C12 C 0.1788(4) 1.0165(5) 0.21748(12) 0.0335(8) Uani 1 1 d . . .
C13 C 0.1092(5) 1.0703(7) 0.17321(15) 0.0496(11) Uani 1 1 d . A .
H13 H 0.0523 1.2045 0.1694 0.060 Uiso 1 1 calc R . .
C14 C 0.4488(5) 0.6365(7) 0.35581(13) 0.0551(11) Uani 1 1 d . . .
H14A H 0.4812 0.6217 0.3878 0.083 Uiso 1 1 calc R . .
H14B H 0.5472 0.6351 0.3375 0.083 Uiso 1 1 calc R . .
H14C H 0.3769 0.5150 0.3468 0.083 Uiso 1 1 calc R . .
N1 N 0.3699(4) 0.6126(5) 0.02359(10) 0.0464(8) Uani 1 1 d . . .
H1 H 0.2810 0.6224 0.0396 0.056 Uiso 1 1 calc R . .
C15 C 0.3698(5) 0.6039(6) -0.02730(13) 0.0506(11) Uani 1 1 d . . .
H15A H 0.4263 0.7342 -0.0390 0.061 Uiso 1 1 calc R . .
H15B H 0.2549 0.6051 -0.0394 0.061 Uiso 1 1 calc R . .
C16 C 0.5430(5) 0.6022(6) 0.04342(13) 0.0511(11) Uani 1 1 d . . .
H16A H 0.5397 0.6017 0.0768 0.061 Uiso 1 1 calc R . .
H16B H 0.6052 0.7326 0.0341 0.061 Uiso 1 1 calc R . .


_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 1.256(5) . ?
O2 C1 1.237(5) . ?
O3 C9 1.370(4) . ?
O3 C14 1.434(4) . ?
C1 C2' 1.547(11) . ?
C1 C2 1.584(8) . ?
C2 C3 1.536(12) . ?
C2 C4 1.552(8) . ?
C2 H2 0.9800 . ?
C3 H3C 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3A 0.9600 . ?
C2' C3' 1.497(19) . ?
C2' C4 1.577(11) . ?
C2' H2' 0.9800 . ?
C3' H3'A 0.9600 . ?
C3' H3'B 0.9600 . ?
C3' H3'C 0.9600 . ?
C4 C13 1.353(6) . ?
C4 C5 1.408(6) . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.413(4) . ?
C7 C8 1.425(4) . ?
C8 C9 1.370(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(5) . ?
C10 C11 1.354(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.413(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.420(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 C15 1.476(5) . ?
N1 C16 1.479(5) . ?
N1 H1 0.8600 . ?
C15 C16 1.502(5) 3_665 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C15 1.502(5) 3_665 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C9 O3 C14 116.0(3) . . ?
O2 C1 O1 123.6(4) . . ?
O2 C1 C2' 134.2(7) . . ?
O1 C1 C2' 102.1(6) . . ?
O2 C1 C2 106.7(5) . . ?
O1 C1 C2 129.6(5) . . ?
C3 C2 C4 108.5(6) . . ?
C3 C2 C1 109.3(6) . . ?
C4 C2 C1 105.6(5) . . ?
C3 C2 H2 111.1 . . ?
C4 C2 H2 111.1 . . ?
C1 C2 H2 111.1 . . ?
C3' C2' C1 103.4(9) . . ?
C3' C2' C4 104.8(9) . . ?
C1 C2' C4 106.2(7) . . ?
C3' C2' H2' 113.8 . . ?
C1 C2' H2' 113.8 . . ?
C4 C2' H2' 113.8 . . ?
C2' C3' H3'A 109.5 . . ?
C2' C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C2' C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C13 C4 C5 117.8(3) . . ?
C13 C4 C2 111.2(5) . . ?
C5 C4 C2 131.0(5) . . ?
C13 C4 C2' 138.7(6) . . ?
C5 C4 C2' 103.5(6) . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C12 118.6(3) . . ?
C6 C7 C8 121.4(3) . . ?
C12 C7 C8 120.0(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O3 C9 C8 124.8(3) . . ?
O3 C9 C10 114.6(3) . . ?
C8 C9 C10 120.6(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 118.4(3) . . ?
C11 C12 C13 123.0(3) . . ?
C7 C12 C13 118.5(3) . . ?
C4 C13 C12 122.7(4) . . ?
C4 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 N1 C16 111.0(3) . . ?
C15 N1 H1 124.5 . . ?
C16 N1 H1 124.5 . . ?
N1 C15 C16 110.7(3) . 3_665 ?
N1 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 3_665 . ?
N1 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 3_665 . ?
H15A C15 H15B 108.1 . . ?
N1 C16 C15 110.4(3) . 3_665 ?
N1 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 3_665 . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 3_665 . ?
H16A C16 H16B 108.1 . . ?

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 C1 C2 C3 126.8(6) . . . . ?
O1 C1 C2 C3 -55.5(8) . . . . ?
C2' C1 C2 C3 -44.7(12) . . . . ?
O2 C1 C2 C4 -116.6(5) . . . . ?
O1 C1 C2 C4 61.1(7) . . . . ?
C2' C1 C2 C4 72.0(12) . . . . ?
O2 C1 C2' C3' 28.9(12) . . . . ?
O1 C1 C2' C3' -148.3(8) . . . . ?
C2 C1 C2' C3' 40.3(11) . . . . ?
O2 C1 C2' C4 -81.2(9) . . . . ?
O1 C1 C2' C4 101.7(7) . . . . ?
C2 C1 C2' C4 -69.7(12) . . . . ?
C3 C2 C4 C13 -138.9(6) . . . . ?
C1 C2 C4 C13 103.9(6) . . . . ?
C3 C2 C4 C5 38.7(9) . . . . ?
C1 C2 C4 C5 -78.4(7) . . . . ?
C3 C2 C4 C2' 48.5(11) . . . . ?
C1 C2 C4 C2' -68.7(11) . . . . ?
C3' C2' C4 C13 -46.5(11) . . . . ?
C1 C2' C4 C13 62.5(12) . . . . ?
C3' C2' C4 C5 136.4(8) . . . . ?
C1 C2' C4 C5 -114.5(7) . . . . ?
C3' C2' C4 C2 -36.0(11) . . . . ?
C1 C2' C4 C2 73.0(10) . . . . ?
C13 C4 C5 C6 -1.2(6) . . . . ?
C2 C4 C5 C6 -178.8(5) . . . . ?
C2' C4 C5 C6 176.5(5) . . . . ?
C4 C5 C6 C7 1.9(6) . . . . ?
C5 C6 C7 C12 -1.4(5) . . . . ?
C5 C6 C7 C8 176.7(3) . . . . ?
C6 C7 C8 C9 -176.8(3) . . . . ?
C12 C7 C8 C9 1.2(5) . . . . ?
C14 O3 C9 C8 0.2(5) . . . . ?
C14 O3 C9 C10 179.6(3) . . . . ?
C7 C8 C9 O3 178.2(3) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
O3 C9 C10 C11 -179.5(3) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C7 -1.1(5) . . . . ?
C10 C11 C12 C13 176.4(3) . . . . ?
C6 C7 C12 C11 177.9(3) . . . . ?
C8 C7 C12 C11 -0.2(5) . . . . ?
C6 C7 C12 C13 0.3(5) . . . . ?
C8 C7 C12 C13 -177.8(3) . . . . ?
C5 C4 C13 C12 0.2(6) . . . . ?
C2 C4 C13 C12 178.2(4) . . . . ?
C2' C4 C13 C12 -176.5(7) . . . . ?
C11 C12 C13 C4 -177.2(4) . . . . ?
C7 C12 C13 C4 0.2(6) . . . . ?
C16 N1 C15 C16 57.0(4) . . . 3_665 ?
C15 N1 C16 C15 -56.8(4) . . . 3_665 ?
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 931857'


#===END

data_2_S-NPX-BPY__CCDC_No_931858

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H14 O3), C10 H8 N2'
_chemical_formula_sum            'C38 H36 N2 O6'
_chemical_formula_weight         616.69

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   15.206(6)
_cell_length_b                   5.766(2)
_cell_length_c                   19.370(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.189(5)
_cell_angle_gamma                90.00
_cell_volume                     1583.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3567
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9853
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   
;
(ABSCOR; Higashi, 1995)
;
_exptl_special_details           
; 
 Rigaku CrystalClear-SM Expert 2.0 r4 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_chemical_absolute_configuration rm
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14102
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.1164
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.46
_reflns_number_total             7113
_reflns_number_gt                4073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   ?
_refine_ls_number_reflns         7113
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 1.0165(2) 0.4074(5) 0.82060(15) 0.0400(7) Uani 1 1 d . . .
H1 H 0.9898 0.4333 0.8509 0.060 Uiso 1 1 calc R . .
O2 O 1.0083(3) 0.0440(6) 0.85438(16) 0.0757(11) Uani 1 1 d . . .
O3 O 0.77426(15) 0.0152(4) 0.34267(12) 0.0308(6) Uani 1 1 d . . .
C1 C 1.0327(3) 0.1819(7) 0.8188(2) 0.0339(10) Uani 1 1 d . . .
C2 C 1.0841(2) 0.1204(6) 0.76795(17) 0.0282(9) Uani 1 1 d . . .
H2 H 1.1231 0.2568 0.7647 0.034 Uiso 1 1 calc R . .
C3 C 1.1500(3) -0.0878(6) 0.7969(2) 0.0420(11) Uani 1 1 d . . .
H3A H 1.1827 -0.1218 0.7627 0.063 Uiso 1 1 calc R . .
H3C H 1.1130 -0.2232 0.8005 0.063 Uiso 1 1 calc R . .
H3B H 1.1965 -0.0513 0.8459 0.063 Uiso 1 1 calc R . .
C4 C 1.0113(2) 0.0738(6) 0.69108(17) 0.0222(8) Uani 1 1 d . . .
C5 C 0.9560(2) -0.1316(6) 0.67716(19) 0.0250(8) Uani 1 1 d . . .
H5 H 0.9622 -0.2359 0.7166 0.030 Uiso 1 1 calc R . .
C6 C 0.8941(2) -0.1803(7) 0.60770(17) 0.0245(8) Uani 1 1 d . . .
H6 H 0.8570 -0.3172 0.5998 0.029 Uiso 1 1 calc R . .
C7 C 0.8838(2) -0.0312(5) 0.54708(18) 0.0190(8) Uani 1 1 d . . .
C8 C 0.8255(2) -0.0908(6) 0.47314(17) 0.0223(8) Uani 1 1 d . . .
H8 H 0.7889 -0.2288 0.4635 0.027 Uiso 1 1 calc R . .
C9 C 0.8230(2) 0.0532(6) 0.41649(17) 0.0229(8) Uani 1 1 d . . .
C10 C 0.8732(2) 0.2664(6) 0.43074(18) 0.0259(8) Uani 1 1 d . . .
H10 H 0.8692 0.3669 0.3909 0.031 Uiso 1 1 calc R . .
C11 C 0.9269(2) 0.3273(6) 0.50129(17) 0.0243(8) Uani 1 1 d . . .
H11 H 0.9584 0.4727 0.5103 0.029 Uiso 1 1 calc R . .
C12 C 0.9365(2) 0.1785(6) 0.56125(17) 0.0197(8) Uani 1 1 d . . .
C13 C 0.9995(2) 0.2255(6) 0.63395(17) 0.0220(8) Uani 1 1 d . . .
H13 H 1.0346 0.3658 0.6434 0.026 Uiso 1 1 calc R . .
C14 C 0.7227(2) -0.1985(7) 0.32329(18) 0.0369(10) Uani 1 1 d . . .
H14A H 0.6911 -0.2072 0.2694 0.055 Uiso 1 1 calc R . .
H14B H 0.6755 -0.2050 0.3468 0.055 Uiso 1 1 calc R . .
H14C H 0.7663 -0.3294 0.3404 0.055 Uiso 1 1 calc R . .
O1' O 0.49544(19) 0.3080(6) 0.81531(13) 0.0432(7) Uani 1 1 d . . .
H1' H 0.4772 0.3298 0.8509 0.065 Uiso 1 1 calc R . .
O2' O 0.5795(2) 0.0355(6) 0.88870(14) 0.0629(9) Uani 1 1 d . . .
O3' O 0.27455(15) 0.0211(4) 0.34817(11) 0.0296(6) Uani 1 1 d . . .
C1' C 0.5562(2) 0.1376(8) 0.83126(19) 0.0342(10) Uani 1 1 d . . .
C2' C 0.5968(2) 0.0922(7) 0.77160(17) 0.0290(9) Uani 1 1 d . . .
H2' H 0.6326 0.2344 0.7681 0.035 Uiso 1 1 calc R . .
C3' C 0.6671(3) -0.1072(6) 0.79266(19) 0.0400(11) Uani 1 1 d . . .
H3D H 0.6925 -0.1311 0.7533 0.060 Uiso 1 1 calc R . .
H3F H 0.6354 -0.2489 0.7992 0.060 Uiso 1 1 calc R . .
H3E H 0.7188 -0.0701 0.8391 0.060 Uiso 1 1 calc R . .
C4' C 0.5204(2) 0.0570(6) 0.69622(17) 0.0225(8) Uani 1 1 d . . .
C5' C 0.4633(2) -0.1462(6) 0.68101(19) 0.0258(8) Uani 1 1 d . . .
H5' H 0.4703 -0.2536 0.7198 0.031 Uiso 1 1 calc R . .
C6' C 0.3992(2) -0.1904(7) 0.61228(16) 0.0235(8) Uani 1 1 d . . .
H6' H 0.3611 -0.3257 0.6043 0.028 Uiso 1 1 calc R . .
C7' C 0.3882(2) -0.0380(6) 0.55254(18) 0.0217(8) Uani 1 1 d . . .
C8' C 0.3290(2) -0.0908(6) 0.47883(17) 0.0221(8) Uani 1 1 d . . .
H8' H 0.2923 -0.2287 0.4686 0.027 Uiso 1 1 calc R . .
C9' C 0.3249(2) 0.0577(6) 0.42235(16) 0.0230(8) Uani 1 1 d . . .
C10' C 0.3757(2) 0.2672(6) 0.43732(18) 0.0248(8) Uani 1 1 d . . .
H10' H 0.3713 0.3698 0.3978 0.030 Uiso 1 1 calc R . .
C11' C 0.4311(2) 0.3245(6) 0.50783(17) 0.0211(7) Uani 1 1 d . . .
H11' H 0.4634 0.4690 0.5172 0.025 Uiso 1 1 calc R . .
C12' C 0.4413(2) 0.1706(6) 0.56753(17) 0.0205(8) Uani 1 1 d . . .
C13' C 0.5071(2) 0.2116(6) 0.63999(17) 0.0227(8) Uani 1 1 d . . .
H13' H 0.5429 0.3508 0.6497 0.027 Uiso 1 1 calc R . .
C14' C 0.2227(2) -0.1893(7) 0.32782(17) 0.0312(9) Uani 1 1 d . . .
H14D H 0.1905 -0.1943 0.2739 0.047 Uiso 1 1 calc R . .
H14E H 0.1759 -0.1972 0.3517 0.047 Uiso 1 1 calc R . .
H14F H 0.2659 -0.3213 0.3438 0.047 Uiso 1 1 calc R . .
N1 N 0.9128(2) 0.5168(6) 0.90392(16) 0.0359(8) Uani 1 1 d . . .
N2 N 0.6033(2) 0.8015(7) 1.09294(15) 0.0370(8) Uani 1 1 d . . .
C15 C 0.9202(3) 0.7170(7) 0.94023(19) 0.0363(10) Uani 1 1 d . . .
H15 H 0.9676 0.8237 0.9399 0.044 Uiso 1 1 calc R . .
C16 C 0.8622(2) 0.7766(7) 0.97829(18) 0.0337(9) Uani 1 1 d . . .
H16 H 0.8712 0.9201 1.0040 0.040 Uiso 1 1 calc R . .
C17 C 0.7909(2) 0.6281(7) 0.97907(17) 0.0285(9) Uani 1 1 d . . .
C18 C 0.7845(3) 0.4202(6) 0.9424(2) 0.0364(10) Uani 1 1 d . . .
H18 H 0.7377 0.3103 0.9418 0.044 Uiso 1 1 calc R . .
C19 C 0.8462(3) 0.3712(7) 0.9064(2) 0.0403(10) Uani 1 1 d . . .
H19 H 0.8407 0.2257 0.8822 0.048 Uiso 1 1 calc R . .
C20 C 0.7257(2) 0.6913(7) 1.01762(17) 0.0280(9) Uani 1 1 d . . .
C21 C 0.7421(3) 0.8782(6) 1.06598(19) 0.0327(9) Uani 1 1 d . . .
H21 H 0.7960 0.9735 1.0744 0.039 Uiso 1 1 calc R . .
C22 C 0.6808(3) 0.9255(7) 1.1015(2) 0.0358(10) Uani 1 1 d . . .
H22 H 0.6943 1.0543 1.1343 0.043 Uiso 1 1 calc R . .
C23 C 0.5867(3) 0.6214(8) 1.04613(19) 0.0397(10) Uani 1 1 d . . .
H23 H 0.5324 0.5292 1.0390 0.048 Uiso 1 1 calc R . .
C24 C 0.6443(2) 0.5628(7) 1.00777(18) 0.0384(10) Uani 1 1 d . . .
H24 H 0.6285 0.4349 0.9746 0.046 Uiso 1 1 calc R . .


_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 1.326(4) . ?
O1 H1 0.8400 . ?
O2 C1 1.195(4) . ?
O3 C9 1.370(3) . ?
O3 C14 1.436(4) . ?
C1 C2 1.505(5) . ?
C2 C4 1.524(4) . ?
C2 C3 1.534(5) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C13 1.370(4) . ?
C4 C5 1.421(5) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(5) . ?
C6 H6 0.9500 . ?
C7 C12 1.421(4) . ?
C7 C8 1.428(4) . ?
C8 C9 1.366(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(5) . ?
C10 C11 1.360(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.414(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1' C1' 1.307(4) . ?
O1' H1' 0.8400 . ?
O2' C1' 1.194(4) . ?
O3' C9' 1.378(3) . ?
O3' C14' 1.423(4) . ?
C1' C2' 1.517(5) . ?
C2' C4' 1.515(4) . ?
C2' C3' 1.522(5) . ?
C2' H2' 1.0000 . ?
C3' H3D 0.9800 . ?
C3' H3F 0.9800 . ?
C3' H3E 0.9800 . ?
C4' C13' 1.365(4) . ?
C4' C5' 1.424(5) . ?
C5' C6' 1.360(4) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.414(5) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.418(4) . ?
C7' C12' 1.419(4) . ?
C8' C9' 1.373(4) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.407(5) . ?
C10' C11' 1.361(4) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.421(4) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.418(4) . ?
C13' H13' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
N1 C19 1.329(5) . ?
N1 C15 1.335(5) . ?
N2 C22 1.337(5) . ?
N2 C23 1.341(5) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(5) . ?
C17 C20 1.486(5) . ?
C18 C19 1.385(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.390(5) . ?
C20 C24 1.396(5) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9500 . ?
C24 H24 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
C1 O1 H1 109.5 . . ?
C9 O3 C14 116.6(3) . . ?
O2 C1 O1 122.6(4) . . ?
O2 C1 C2 124.3(4) . . ?
O1 C1 C2 113.1(4) . . ?
C1 C2 C4 108.4(3) . . ?
C1 C2 C3 111.7(3) . . ?
C4 C2 C3 111.5(3) . . ?
C1 C2 H2 108.4 . . ?
C4 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3C C3 H3B 109.5 . . ?
C13 C4 C5 118.9(3) . . ?
C13 C4 C2 120.9(3) . . ?
C5 C4 C2 120.2(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C12 118.0(3) . . ?
C6 C7 C8 121.8(3) . . ?
C12 C7 C8 120.1(3) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 O3 126.1(3) . . ?
C8 C9 C10 120.9(3) . . ?
O3 C9 C10 113.0(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 122.4(3) . . ?
C11 C12 C7 118.4(3) . . ?
C13 C12 C7 119.2(3) . . ?
C4 C13 C12 121.7(3) . . ?
C4 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1' O1' H1' 109.5 . . ?
C9' O3' C14' 117.6(3) . . ?
O2' C1' O1' 122.5(4) . . ?
O2' C1' C2' 124.0(4) . . ?
O1' C1' C2' 113.4(3) . . ?
C4' C2' C1' 112.1(3) . . ?
C4' C2' C3' 112.1(3) . . ?
C1' C2' C3' 111.5(3) . . ?
C4' C2' H2' 106.9 . . ?
C1' C2' H2' 106.9 . . ?
C3' C2' H2' 106.9 . . ?
C2' C3' H3D 109.5 . . ?
C2' C3' H3F 109.5 . . ?
H3D C3' H3F 109.5 . . ?
C2' C3' H3E 109.5 . . ?
H3D C3' H3E 109.5 . . ?
H3F C3' H3E 109.5 . . ?
C13' C4' C5' 117.9(3) . . ?
C13' C4' C2' 121.5(3) . . ?
C5' C4' C2' 120.5(3) . . ?
C6' C5' C4' 121.6(3) . . ?
C6' C5' H5' 119.2 . . ?
C4' C5' H5' 119.2 . . ?
C5' C6' C7' 121.0(3) . . ?
C5' C6' H6' 119.5 . . ?
C7' C6' H6' 119.5 . . ?
C6' C7' C8' 122.3(3) . . ?
C6' C7' C12' 118.0(3) . . ?
C8' C7' C12' 119.7(3) . . ?
C9' C8' C7' 119.9(3) . . ?
C9' C8' H8' 120.1 . . ?
C7' C8' H8' 120.1 . . ?
C8' C9' O3' 125.7(3) . . ?
C8' C9' C10' 120.5(3) . . ?
O3' C9' C10' 113.8(3) . . ?
C11' C10' C9' 120.7(3) . . ?
C11' C10' H10' 119.7 . . ?
C9' C10' H10' 119.7 . . ?
C10' C11' C12' 120.7(3) . . ?
C10' C11' H11' 119.6 . . ?
C12' C11' H11' 119.6 . . ?
C13' C12' C7' 119.3(3) . . ?
C13' C12' C11' 122.1(3) . . ?
C7' C12' C11' 118.4(3) . . ?
C4' C13' C12' 122.0(3) . . ?
C4' C13' H13' 119.0 . . ?
C12' C13' H13' 119.0 . . ?
O3' C14' H14D 109.5 . . ?
O3' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
O3' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C19 N1 C15 116.6(3) . . ?
C22 N2 C23 116.1(3) . . ?
N1 C15 C16 123.2(4) . . ?
N1 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 116.2(4) . . ?
C18 C17 C20 122.4(3) . . ?
C16 C17 C20 121.4(3) . . ?
C17 C18 C19 120.1(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
N1 C19 C18 123.6(4) . . ?
N1 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
C21 C20 C24 116.0(3) . . ?
C21 C20 C17 122.6(3) . . ?
C24 C20 C17 121.4(3) . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
N2 C22 C21 124.1(4) . . ?
N2 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
N2 C23 C24 123.6(4) . . ?
N2 C23 H23 118.2 . . ?
C24 C23 H23 118.2 . . ?
C23 C24 C20 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C20 C24 H24 120.0 . . ?

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 C1 C2 C4 90.1(5) . . . . ?
O1 C1 C2 C4 -89.9(4) . . . . ?
O2 C1 C2 C3 -33.2(5) . . . . ?
O1 C1 C2 C3 146.8(3) . . . . ?
C1 C2 C4 C13 109.3(4) . . . . ?
C3 C2 C4 C13 -127.3(4) . . . . ?
C1 C2 C4 C5 -72.2(4) . . . . ?
C3 C2 C4 C5 51.2(4) . . . . ?
C13 C4 C5 C6 1.8(5) . . . . ?
C2 C4 C5 C6 -176.7(3) . . . . ?
C4 C5 C6 C7 1.0(5) . . . . ?
C5 C6 C7 C12 -3.2(5) . . . . ?
C5 C6 C7 C8 174.3(3) . . . . ?
C6 C7 C8 C9 -175.9(3) . . . . ?
C12 C7 C8 C9 1.6(5) . . . . ?
C7 C8 C9 O3 176.9(3) . . . . ?
C7 C8 C9 C10 -3.7(5) . . . . ?
C14 O3 C9 C8 -1.5(4) . . . . ?
C14 O3 C9 C10 179.1(3) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
O3 C9 C10 C11 -178.6(3) . . . . ?
C9 C10 C11 C12 2.0(5) . . . . ?
C10 C11 C12 C13 173.1(3) . . . . ?
C10 C11 C12 C7 -4.0(5) . . . . ?
C6 C7 C12 C11 179.8(3) . . . . ?
C8 C7 C12 C11 2.2(5) . . . . ?
C6 C7 C12 C13 2.6(5) . . . . ?
C8 C7 C12 C13 -175.0(3) . . . . ?
C5 C4 C13 C12 -2.4(5) . . . . ?
C2 C4 C13 C12 176.1(3) . . . . ?
C11 C12 C13 C4 -176.9(3) . . . . ?
C7 C12 C13 C4 0.2(5) . . . . ?
O2' C1' C2' C4' 129.4(4) . . . . ?
O1' C1' C2' C4' -53.4(4) . . . . ?
O2' C1' C2' C3' 2.8(5) . . . . ?
O1' C1' C2' C3' 180.0(3) . . . . ?
C1' C2' C4' C13' 113.5(4) . . . . ?
C3' C2' C4' C13' -120.3(4) . . . . ?
C1' C2' C4' C5' -69.8(4) . . . . ?
C3' C2' C4' C5' 56.5(4) . . . . ?
C13' C4' C5' C6' 1.9(5) . . . . ?
C2' C4' C5' C6' -175.0(3) . . . . ?
C4' C5' C6' C7' 1.5(5) . . . . ?
C5' C6' C7' C8' 173.4(3) . . . . ?
C5' C6' C7' C12' -4.3(5) . . . . ?
C6' C7' C8' C9' -176.5(3) . . . . ?
C12' C7' C8' C9' 1.2(5) . . . . ?
C7' C8' C9' O3' 176.2(3) . . . . ?
C7' C8' C9' C10' -2.8(5) . . . . ?
C14' O3' C9' C8' -0.5(4) . . . . ?
C14' O3' C9' C10' 178.6(3) . . . . ?
C8' C9' C10' C11' 1.2(5) . . . . ?
O3' C9' C10' C11' -178.0(3) . . . . ?
C9' C10' C11' C12' 2.1(5) . . . . ?
C6' C7' C12' C13' 3.8(5) . . . . ?
C8' C7' C12' C13' -174.0(3) . . . . ?
C6' C7' C12' C11' 179.7(3) . . . . ?
C8' C7' C12' C11' 1.9(5) . . . . ?
C10' C11' C12' C13' 172.2(3) . . . . ?
C10' C11' C12' C7' -3.6(5) . . . . ?
C5' C4' C13' C12' -2.4(5) . . . . ?
C2' C4' C13' C12' 174.5(3) . . . . ?
C7' C12' C13' C4' -0.5(5) . . . . ?
C11' C12' C13' C4' -176.3(3) . . . . ?
C19 N1 C15 C16 -0.7(5) . . . . ?
N1 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 C18 2.1(5) . . . . ?
C15 C16 C17 C20 -178.1(3) . . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C20 C17 C18 C19 179.1(3) . . . . ?
C15 N1 C19 C18 1.8(6) . . . . ?
C17 C18 C19 N1 -0.9(6) . . . . ?
C18 C17 C20 C21 167.5(3) . . . . ?
C16 C17 C20 C21 -12.3(5) . . . . ?
C18 C17 C20 C24 -11.6(5) . . . . ?
C16 C17 C20 C24 168.5(3) . . . . ?
C24 C20 C21 C22 0.9(5) . . . . ?
C17 C20 C21 C22 -178.4(3) . . . . ?
C23 N2 C22 C21 -0.1(5) . . . . ?
C20 C21 C22 N2 -0.2(6) . . . . ?
C22 N2 C23 C24 -0.4(5) . . . . ?
N2 C23 C24 C20 1.1(6) . . . . ?
C21 C20 C24 C23 -1.3(5) . . . . ?
C17 C20 C24 C23 178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 931858'


#===END

data_4_S-NPX-PIZ__CCDC_No_931859

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            S-Naproxen-Piperidine
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H13 O3), C4 H10 N2'
_chemical_formula_sum            'C32 H36 N2 O6'
_chemical_formula_weight         544.63

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   P21

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

_cell_length_a                   8.029(4)
_cell_length_b                   6.118(3)
_cell_length_c                   28.045(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.990(7)
_cell_angle_gamma                90.00
_cell_volume                     1374.3(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3184
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   
;
(ABSCOR; Higashi, 1995)
;
_exptl_special_details           
; 
 Rigaku CrystalClear-SM Expert 2.0 r4 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_chemical_absolute_configuration rm
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             5112
_reflns_number_gt                2996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0520P)²+0.0796P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   ?
_refine_ls_number_reflns         5112
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.3596(5) 0.6081(6) 0.32356(14) 0.0426(11) Uani 1 1 d . . .
O2 O 0.2402(4) 0.3097(6) 0.29138(14) 0.0306(9) Uani 1 1 d . . .
O3 O 0.9043(4) 0.5572(6) 0.60196(12) 0.0292(9) Uani 1 1 d . . .
C1 C 0.3499(6) 0.4045(8) 0.31962(18) 0.0233(12) Uani 1 1 d . . .
C2 C 0.4723(6) 0.2558(8) 0.34845(17) 0.0207(11) Uani 1 1 d . . .
H2 H 0.4064 0.1302 0.3600 0.025 Uiso 1 1 calc R . .
C3 C 0.5961(6) 0.1621(9) 0.31459(18) 0.0293(13) Uani 1 1 d . . .
H3A H 0.6703 0.0577 0.3320 0.044 Uiso 1 1 calc R . .
H3B H 0.6625 0.2811 0.3022 0.044 Uiso 1 1 calc R . .
H3C H 0.5346 0.0875 0.2879 0.044 Uiso 1 1 calc R . .
C4 C 0.5647(6) 0.3582(8) 0.39211(18) 0.0219(12) Uani 1 1 d . . .
C5 C 0.6462(6) 0.5618(8) 0.39153(18) 0.0240(12) Uani 1 1 d . . .
H5 H 0.6386 0.6454 0.3629 0.029 Uiso 1 1 calc R . .
C6 C 0.7364(6) 0.6436(9) 0.43109(18) 0.0245(12) Uani 1 1 d . . .
H6 H 0.7916 0.7803 0.4291 0.029 Uiso 1 1 calc R . .
C7 C 0.7482(6) 0.5255(8) 0.47514(17) 0.0191(11) Uani 1 1 d . . .
C8 C 0.8350(5) 0.6070(9) 0.51658(18) 0.0225(12) Uani 1 1 d . . .
H8 H 0.8941 0.7413 0.5158 0.027 Uiso 1 1 calc R . .
C9 C 0.8331(6) 0.4900(9) 0.55822(18) 0.0231(12) Uani 1 1 d . . .
C10 C 0.7516(6) 0.2895(9) 0.56052(19) 0.0257(12) Uani 1 1 d . . .
H10 H 0.7508 0.2138 0.5901 0.031 Uiso 1 1 calc R . .
C11 C 0.6722(6) 0.2017(8) 0.51984(18) 0.0237(12) Uani 1 1 d . . .
H11 H 0.6211 0.0620 0.5210 0.028 Uiso 1 1 calc R . .
C12 C 0.6665(6) 0.3198(8) 0.47590(18) 0.0212(11) Uani 1 1 d . . .
C13 C 0.5762(5) 0.2390(8) 0.43395(17) 0.0193(11) Uani 1 1 d . . .
H13 H 0.5230 0.1006 0.4349 0.023 Uiso 1 1 calc R . .
C14 C 0.9818(7) 0.7664(9) 0.6040(2) 0.0353(14) Uani 1 1 d . . .
H14A H 1.0258 0.7963 0.6368 0.053 Uiso 1 1 calc R . .
H14B H 0.8996 0.8784 0.5938 0.053 Uiso 1 1 calc R . .
H14C H 1.0736 0.7685 0.5827 0.053 Uiso 1 1 calc R . .
O1' O 0.8111(4) 0.2405(6) 0.20435(13) 0.0270(9) Uani 1 1 d . . .
O2' O 0.6772(4) -0.0742(6) 0.18973(14) 0.0360(10) Uani 1 1 d . . .
O3' O 0.8655(4) 0.4650(6) -0.10352(12) 0.0312(9) Uani 1 1 d . . .
C1' C 0.6904(6) 0.1302(9) 0.18529(17) 0.0221(12) Uani 1 1 d . . .
C2' C 0.5523(6) 0.2460(8) 0.15390(18) 0.0237(12) Uani 1 1 d . . .
H2' H 0.4642 0.1350 0.1449 0.028 Uiso 1 1 calc R . .
C3' C 0.4719(6) 0.4241(9) 0.18319(19) 0.0314(14) Uani 1 1 d . . .
H3D H 0.3813 0.4941 0.1635 0.047 Uiso 1 1 calc R . .
H3E H 0.5561 0.5338 0.1933 0.047 Uiso 1 1 calc R . .
H3F H 0.4270 0.3582 0.2114 0.047 Uiso 1 1 calc R . .
C4' C 0.6211(6) 0.3267(8) 0.10825(18) 0.0224(12) Uani 1 1 d . . .
C5' C 0.7001(6) 0.5309(8) 0.10585(17) 0.0239(12) Uani 1 1 d . . .
H5' H 0.7056 0.6227 0.1332 0.029 Uiso 1 1 calc R . .
C6' C 0.7703(6) 0.6032(8) 0.06478(17) 0.0225(12) Uani 1 1 d . . .
H6' H 0.8237 0.7416 0.0644 0.027 Uiso 1 1 calc R . .
C7' C 0.7617(6) 0.4689(8) 0.02354(18) 0.0226(12) Uani 1 1 d . . .
C8' C 0.8289(5) 0.5418(9) -0.01959(18) 0.0242(12) Uani 1 1 d . . .
H8' H 0.8852 0.6781 -0.0205 0.029 Uiso 1 1 calc R . .
C9' C 0.8114(6) 0.4141(9) -0.05916(19) 0.0248(12) Uani 1 1 d . . .
C10' C 0.7317(6) 0.2082(9) -0.0580(2) 0.0313(13) Uani 1 1 d . . .
H10' H 0.7208 0.1210 -0.0861 0.038 Uiso 1 1 calc R . .
C11' C 0.6704(6) 0.1338(8) -0.01670(18) 0.0250(12) Uani 1 1 d . . .
H11' H 0.6194 -0.0063 -0.0161 0.030 Uiso 1 1 calc R . .
C12' C 0.6821(6) 0.2633(9) 0.02505(18) 0.0231(12) Uani 1 1 d . . .
C13' C 0.6147(6) 0.1980(8) 0.06814(18) 0.0221(11) Uani 1 1 d . . .
H13' H 0.5627 0.0588 0.0693 0.026 Uiso 1 1 calc R . .
C14' C 0.9406(7) 0.6739(9) -0.10778(19) 0.0346(14) Uani 1 1 d . . .
H14D H 0.9751 0.6927 -0.1404 0.052 Uiso 1 1 calc R . .
H14E H 1.0385 0.6850 -0.0850 0.052 Uiso 1 1 calc R . .
H14F H 0.8600 0.7879 -0.1009 0.052 Uiso 1 1 calc R . .
N1 N 1.1618(5) 0.8920(8) 0.27636(15) 0.0278(11) Uani 1 1 d . . .
H1 H 1.2525 0.9092 0.2954 0.033 Uiso 1 1 calc R . .
N2 N 0.9061(4) 0.6481(7) 0.22302(14) 0.0251(10) Uani 1 1 d . . .
H1' H 0.8150 0.6310 0.2041 0.030 Uiso 1 1 calc R . .
C15 C 0.9891(6) 0.8731(9) 0.2929(2) 0.0321(14) Uani 1 1 d . . .
H15A H 0.9205 0.9975 0.2804 0.038 Uiso 1 1 calc R . .
H15B H 0.9940 0.8790 0.3283 0.038 Uiso 1 1 calc R . .
C16 C 0.9092(6) 0.6605(9) 0.27585(18) 0.0288(13) Uani 1 1 d . . .
H16A H 0.9734 0.5358 0.2902 0.035 Uiso 1 1 calc R . .
H16B H 0.7939 0.6520 0.2861 0.035 Uiso 1 1 calc R . .
C17 C 1.0763(6) 0.6679(9) 0.20620(19) 0.0289(13) Uani 1 1 d . . .
H17A H 1.0698 0.6650 0.1708 0.035 Uiso 1 1 calc R . .
H17B H 1.1446 0.5417 0.2180 0.035 Uiso 1 1 calc R . .
C18 C 1.1596(6) 0.8780(9) 0.22373(18) 0.0274(13) Uani 1 1 d . . .
H18A H 1.2754 0.8828 0.2137 0.033 Uiso 1 1 calc R . .
H18B H 1.0982 1.0046 0.2092 0.033 Uiso 1 1 calc R . .


_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 1.252(6) . ?
O2 C1 1.281(6) . ?
O3 C9 1.380(6) . ?
O3 C14 1.422(6) . ?
C1 C2 1.529(7) . ?
C2 C4 1.522(7) . ?
C2 C3 1.533(6) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C13 1.379(6) . ?
C4 C5 1.408(7) . ?
C5 C6 1.376(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.429(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(7) . ?
C7 C12 1.420(6) . ?
C8 C9 1.371(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(7) . ?
C10 C11 1.377(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.427(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.427(7) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1' C1' 1.268(6) . ?
O2' C1' 1.262(6) . ?
O3' C9' 1.382(6) . ?
O3' C14' 1.422(6) . ?
C1' C2' 1.540(6) . ?
C2' C4' 1.512(7) . ?
C2' C3' 1.534(7) . ?
C2' H2' 1.0000 . ?
C3' H3D 0.9800 . ?
C3' H3E 0.9800 . ?
C3' H3F 0.9800 . ?
C4' C13' 1.371(7) . ?
C4' C5' 1.405(7) . ?
C5' C6' 1.389(6) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.416(6) . ?
C6' H6' 0.9500 . ?
C7' C12' 1.413(7) . ?
C7' C8' 1.429(7) . ?
C8' C9' 1.356(7) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.414(7) . ?
C10' C11' 1.368(7) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.412(7) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.416(6) . ?
C13' H13' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
N1 C18 1.477(6) . ?
N1 C15 1.497(6) . ?
N1 H1 0.8800 . ?
N2 C17 1.481(6) . ?
N2 C16 1.482(6) . ?
N2 H1' 0.8800 . ?
C15 C16 1.513(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.515(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C9 O3 C14 117.2(4) . . ?
O1 C1 O2 122.7(5) . . ?
O1 C1 C2 120.8(5) . . ?
O2 C1 C2 116.5(4) . . ?
C4 C2 C1 116.1(4) . . ?
C4 C2 C3 110.6(4) . . ?
C1 C2 C3 108.4(4) . . ?
C4 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C13 C4 C5 118.3(5) . . ?
C13 C4 C2 117.9(5) . . ?
C5 C4 C2 123.8(5) . . ?
C6 C5 C4 122.1(5) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C12 120.4(4) . . ?
C8 C7 C6 122.4(5) . . ?
C12 C7 C6 117.3(5) . . ?
C9 C8 C7 119.0(5) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 O3 125.0(5) . . ?
C8 C9 C10 122.1(5) . . ?
O3 C9 C10 112.8(5) . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 118.3(5) . . ?
C7 C12 C13 120.2(5) . . ?
C11 C12 C13 121.4(5) . . ?
C4 C13 C12 121.2(5) . . ?
C4 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9' O3' C14' 116.1(4) . . ?
O2' C1' O1' 123.6(5) . . ?
O2' C1' C2' 116.8(5) . . ?
O1' C1' C2' 119.7(5) . . ?
C4' C2' C3' 114.4(4) . . ?
C4' C2' C1' 110.1(4) . . ?
C3' C2' C1' 109.5(4) . . ?
C4' C2' H2' 107.5 . . ?
C3' C2' H2' 107.5 . . ?
C1' C2' H2' 107.5 . . ?
C2' C3' H3D 109.5 . . ?
C2' C3' H3E 109.5 . . ?
H3D C3' H3E 109.5 . . ?
C2' C3' H3F 109.5 . . ?
H3D C3' H3F 109.5 . . ?
H3E C3' H3F 109.5 . . ?
C13' C4' C5' 117.6(5) . . ?
C13' C4' C2' 120.8(5) . . ?
C5' C4' C2' 121.6(5) . . ?
C6' C5' C4' 122.2(5) . . ?
C6' C5' H5' 118.9 . . ?
C4' C5' H5' 118.9 . . ?
C5' C6' C7' 119.5(5) . . ?
C5' C6' H6' 120.2 . . ?
C7' C6' H6' 120.2 . . ?
C12' C7' C6' 119.2(5) . . ?
C12' C7' C8' 120.1(4) . . ?
C6' C7' C8' 120.7(5) . . ?
C9' C8' C7' 119.3(5) . . ?
C9' C8' H8' 120.4 . . ?
C7' C8' H8' 120.4 . . ?
C8' C9' O3' 125.9(5) . . ?
C8' C9' C10' 121.0(5) . . ?
O3' C9' C10' 113.1(5) . . ?
C11' C10' C9' 120.4(5) . . ?
C11' C10' H10' 119.8 . . ?
C9' C10' H10' 119.8 . . ?
C10' C11' C12' 120.6(5) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' C7' 118.6(5) . . ?
C11' C12' C13' 122.8(5) . . ?
C7' C12' C13' 118.5(5) . . ?
C4' C13' C12' 122.9(5) . . ?
C4' C13' H13' 118.5 . . ?
C12' C13' H13' 118.5 . . ?
O3' C14' H14D 109.5 . . ?
O3' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
O3' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C18 N1 C15 111.0(4) . . ?
C18 N1 H1 124.5 . . ?
C15 N1 H1 124.5 . . ?
C17 N2 C16 111.2(4) . . ?
C17 N2 H1' 124.4 . . ?
C16 N2 H1' 124.4 . . ?
N1 C15 C16 110.5(4) . . ?
N1 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N1 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C15 109.8(4) . . ?
N2 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N2 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N2 C17 C18 111.2(4) . . ?
N2 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N1 C18 C17 110.3(4) . . ?
N1 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N1 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?

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
O1 C1 C2 C4 19.0(7) . . . . ?
O2 C1 C2 C4 -161.7(4) . . . . ?
O1 C1 C2 C3 -106.1(6) . . . . ?
O2 C1 C2 C3 73.2(5) . . . . ?
C1 C2 C4 C13 135.0(5) . . . . ?
C3 C2 C4 C13 -101.0(5) . . . . ?
C1 C2 C4 C5 -48.4(6) . . . . ?
C3 C2 C4 C5 75.6(6) . . . . ?
C13 C4 C5 C6 0.3(7) . . . . ?
C2 C4 C5 C6 -176.3(4) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C5 C6 C7 C8 -178.1(4) . . . . ?
C5 C6 C7 C12 1.4(7) . . . . ?
C12 C7 C8 C9 -3.0(7) . . . . ?
C6 C7 C8 C9 176.4(4) . . . . ?
C7 C8 C9 O3 -175.9(4) . . . . ?
C7 C8 C9 C10 1.8(7) . . . . ?
C14 O3 C9 C8 1.6(7) . . . . ?
C14 O3 C9 C10 -176.3(4) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
O3 C9 C10 C11 179.1(4) . . . . ?
C9 C10 C11 C12 -2.9(7) . . . . ?
C8 C7 C12 C11 1.3(6) . . . . ?
C6 C7 C12 C11 -178.2(4) . . . . ?
C8 C7 C12 C13 179.0(4) . . . . ?
C6 C7 C12 C13 -0.5(6) . . . . ?
C10 C11 C12 C7 1.7(7) . . . . ?
C10 C11 C12 C13 -176.0(4) . . . . ?
C5 C4 C13 C12 0.7(7) . . . . ?
C2 C4 C13 C12 177.4(4) . . . . ?
C7 C12 C13 C4 -0.6(7) . . . . ?
C11 C12 C13 C4 177.1(4) . . . . ?
O2' C1' C2' C4' -110.3(5) . . . . ?
O1' C1' C2' C4' 68.4(6) . . . . ?
O2' C1' C2' C3' 123.1(5) . . . . ?
O1' C1' C2' C3' -58.2(5) . . . . ?
C3' C2' C4' C13' -145.2(5) . . . . ?
C1' C2' C4' C13' 90.9(5) . . . . ?
C3' C2' C4' C5' 37.6(6) . . . . ?
C1' C2' C4' C5' -86.2(5) . . . . ?
C13' C4' C5' C6' -0.1(7) . . . . ?
C2' C4' C5' C6' 177.1(4) . . . . ?
C4' C5' C6' C7' 0.5(7) . . . . ?
C5' C6' C7' C12' -0.2(7) . . . . ?
C5' C6' C7' C8' 178.3(4) . . . . ?
C12' C7' C8' C9' 1.7(7) . . . . ?
C6' C7' C8' C9' -176.7(5) . . . . ?
C7' C8' C9' O3' 178.2(5) . . . . ?
C7' C8' C9' C10' -1.7(7) . . . . ?
C14' O3' C9' C8' -2.3(7) . . . . ?
C14' O3' C9' C10' 177.5(4) . . . . ?
C8' C9' C10' C11' 0.1(8) . . . . ?
O3' C9' C10' C11' -179.8(5) . . . . ?
C9' C10' C11' C12' 1.5(8) . . . . ?
C10' C11' C12' C7' -1.4(7) . . . . ?
C10' C11' C12' C13' 177.4(5) . . . . ?
C6' C7' C12' C11' 178.3(5) . . . . ?
C8' C7' C12' C11' -0.2(7) . . . . ?
C6' C7' C12' C13' -0.5(7) . . . . ?
C8' C7' C12' C13' -179.0(4) . . . . ?
C5' C4' C13' C12' -0.6(7) . . . . ?
C2' C4' C13' C12' -177.9(4) . . . . ?
C11' C12' C13' C4' -177.8(5) . . . . ?
C7' C12' C13' C4' 1.0(7) . . . . ?
C18 N1 C15 C16 57.7(6) . . . . ?
C17 N2 C16 C15 57.4(5) . . . . ?
N1 C15 C16 N2 -57.6(6) . . . . ?
C16 N2 C17 C18 -56.8(6) . . . . ?
C15 N1 C18 C17 -56.2(5) . . . . ?
N2 C17 C18 N1 55.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.063

#===END







_database_code_depnum_ccdc_archive 'CCDC 931859'
