# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1428773'
_audit_update_record             
;
2015-09-30 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(2R,3R,4R)-3'-Methyl-4-(nitromethyl)-1',2-diphenyl spiro[chroman-3,4'-pyrazol]-5'(1'H)-one"
_chemical_name_common            NO
_chemical_melting_point          427-428
_chemical_formula_moiety         'C29 H31 N3 O5'
_chemical_formula_sum            'C29 H31 N3 O5'
_chemical_formula_weight         501.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.007(4)
_cell_length_b                   13.691(4)
_cell_length_c                   11.577(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.6366(10)
_cell_angle_gamma                90
_cell_volume                     1317.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    914
_cell_measurement_theta_min      30.10
_cell_measurement_theta_max      77.60

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.708
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            22397
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.228
_diffrn_reflns_theta_max         77.702
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total             4797
_reflns_number_gt                4707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_max     0.704
_reflns_Friedel_fraction_full    0.728

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.1527P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0184(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     338
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61964(16) 0.47599(11) 1.08648(12) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.73126(16) 0.42653(11) 0.75420(12) 0.0391(3) Uani 1 1 d . . . . .
O3 O 1.12253(18) 0.15579(13) 1.05753(16) 0.0553(4) Uani 1 1 d . . . . .
O4 O 1.15365(17) 0.31140(12) 1.04905(15) 0.0509(4) Uani 1 1 d . . . . .
O5 O 0.87968(19) 0.16142(12) 0.73513(14) 0.0505(4) Uani 1 1 d . . . . .
N1 N 0.54251(18) 0.30362(12) 0.73084(14) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.48170(17) 0.25249(12) 0.80998(15) 0.0363(3) Uani 1 1 d . . . . .
N3 N 1.07072(18) 0.23927(13) 1.03917(14) 0.0376(4) Uani 1 1 d . . . . .
C1 C 0.6087(2) 0.47211(13) 0.95989(16) 0.0323(4) Uani 1 1 d . . . . .
H1 H 0.6826 0.5228 0.9494 0.039 Uiso 1 1 calc R U . . .
C2 C 0.66206(19) 0.37082(13) 0.92881(15) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.83954(19) 0.35271(13) 1.01996(15) 0.0294(3) Uani 1 1 d . . . . .
H3 H 0.9088 0.4006 0.9984 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8586(2) 0.37251(14) 1.15441(16) 0.0327(4) Uani 1 1 d . . . . .
C5 C 0.7501(2) 0.43444(15) 1.17847(17) 0.0366(4) Uani 1 1 d . . . . .
C6 C 0.7642(3) 0.45276(18) 1.3010(2) 0.0470(5) Uani 1 1 d . . . . .
H6 H 0.6892 0.4946 1.3157 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8861(3) 0.41048(19) 1.40056(19) 0.0493(5) Uani 1 1 d . . . . .
H7 H 0.8955 0.4235 1.4837 0.059 Uiso 1 1 calc R U . . .
C8 C 0.9956(3) 0.34883(18) 1.37931(18) 0.0469(5) Uani 1 1 d . . . . .
H8 H 1.0800 0.3196 1.4478 0.056 Uiso 1 1 calc R U . . .
C9 C 0.9809(2) 0.33017(16) 1.25750(17) 0.0388(4) Uani 1 1 d . . . . .
H9 H 1.0557 0.2876 1.2437 0.047 Uiso 1 1 calc R U . . .
C10 C 0.65320(19) 0.37328(13) 0.79423(16) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.54651(19) 0.28857(13) 0.92059(17) 0.0310(3) Uani 1 1 d . . . . .
C12 C 0.5076(2) 0.24847(16) 1.02511(19) 0.0412(4) Uani 1 1 d . . . . .
H12A H 0.4332 0.1934 0.9946 0.049 Uiso 1 1 calc R U . . .
H12B H 0.4572 0.2995 1.0572 0.049 Uiso 1 1 calc R U . . .
H12C H 0.6066 0.2262 1.0924 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4372(2) 0.49987(13) 0.87685(17) 0.0334(4) Uani 1 1 d . . . . .
C14 C 0.4055(3) 0.53886(18) 0.7591(2) 0.0490(5) Uani 1 1 d . . . . .
H14 H 0.4902 0.5457 0.7299 0.059 Uiso 1 1 calc R U . . .
C15 C 0.2511(4) 0.5678(2) 0.6838(2) 0.0667(8) Uani 1 1 d . . . . .
H15 H 0.2307 0.5946 0.6035 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1267(3) 0.5583(2) 0.7243(3) 0.0659(7) Uani 1 1 d . . . . .
H16 H 0.0213 0.5788 0.6724 0.079 Uiso 1 1 calc R U . . .
C17 C 0.1562(3) 0.51871(18) 0.8407(3) 0.0528(6) Uani 1 1 d . . . . .
H17 H 0.0704 0.5115 0.8686 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3114(2) 0.48923(15) 0.9177(2) 0.0411(4) Uani 1 1 d . . . . .
H18 H 0.3311 0.4620 0.9978 0.049 Uiso 1 1 calc R U . . .
C19 C 0.4902(2) 0.27377(16) 0.60348(18) 0.0415(4) Uani 1 1 d . . . . .
C20 C 0.3888(3) 0.1937(2) 0.5633(2) 0.0564(6) Uani 1 1 d . . . . .
H20 H 0.3525 0.1601 0.6194 0.068 Uiso 1 1 calc R U . . .
C21 C 0.3406(3) 0.1632(3) 0.4381(3) 0.0758(10) Uani 1 1 d . . . . .
H21 H 0.2725 0.1078 0.4099 0.091 Uiso 1 1 calc R U . . .
C22 C 0.3907(3) 0.2124(3) 0.3558(2) 0.0743(10) Uani 1 1 d . . . . .
H22 H 0.3565 0.1917 0.2712 0.089 Uiso 1 1 calc R U . . .
C23 C 0.4897(4) 0.2908(3) 0.3967(2) 0.0741(9) Uani 1 1 d . . . . .
H23 H 0.5251 0.3242 0.3401 0.089 Uiso 1 1 calc R U . . .
C24 C 0.5404(3) 0.3232(2) 0.5204(2) 0.0601(6) Uani 1 1 d . . . . .
H24 H 0.6086 0.3786 0.5473 0.072 Uiso 1 1 calc R U . . .
C25 C 0.89081(19) 0.25042(15) 0.99792(16) 0.0338(4) Uani 1 1 d . . . . .
H25A H 0.8517 0.2026 1.0438 0.041 Uiso 1 1 calc R U . . .
H25B H 0.8391 0.2349 0.9076 0.041 Uiso 1 1 calc R U . . .
C26 C 0.7346(4) 0.0323(2) 0.7786(3) 0.0647(7) Uani 1 1 d . . . . .
H26A H 0.6598 0.0780 0.7929 0.078 Uiso 1 1 calc R U . . .
H26B H 0.8257 0.0202 0.8576 0.078 Uiso 1 1 calc R U . . .
H26C H 0.6791 -0.0294 0.7460 0.078 Uiso 1 1 calc R U . . .
C27 C 0.7947(3) 0.07526(19) 0.6856(2) 0.0559(6) Uani 1 1 d . . . . .
H27A H 0.8661 0.0280 0.6674 0.067 Uiso 1 1 calc R U . . .
H27B H 0.7029 0.0898 0.6064 0.067 Uiso 1 1 calc R U . . .
C28 C 0.9583(3) 0.2007(2) 0.6591(2) 0.0571(6) Uani 1 1 d . . . . .
H28A H 0.8770 0.2213 0.5772 0.068 Uiso 1 1 calc R U . . .
H28B H 1.0272 0.1501 0.6440 0.068 Uiso 1 1 calc R U . . .
C29 C 1.0578(3) 0.2856(2) 0.7231(2) 0.0608(7) Uani 1 1 d . . . . .
H29A H 1.1114 0.3125 0.6708 0.073 Uiso 1 1 calc R U . . .
H29B H 1.1390 0.2648 0.8037 0.073 Uiso 1 1 calc R U . . .
H29C H 0.9890 0.3358 0.7373 0.073 Uiso 1 1 calc R U . . .


_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 C5 1.370(2) . ?
O1 C1 1.432(2) . ?
O2 C10 1.221(2) . ?
O3 N3 1.222(2) . ?
O4 N3 1.217(2) . ?
O5 C27 1.403(3) . ?
O5 C28 1.430(3) . ?
N1 C10 1.371(2) . ?
N1 N2 1.420(2) . ?
N1 C19 1.424(2) . ?
N2 C11 1.284(3) . ?
N3 C25 1.510(2) . ?
C1 C13 1.521(2) . ?
C1 C2 1.554(2) . ?
C1 H1 1.0000 . ?
C2 C11 1.511(2) . ?
C2 C10 1.529(2) . ?
C2 C3 1.559(2) . ?
C3 C4 1.523(2) . ?
C3 C25 1.526(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.400(3) . ?
C4 C9 1.401(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.488(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.388(3) . ?
C13 C18 1.393(3) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.387(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.408(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.358(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.499(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.481(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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
C5 O1 C1 118.74(13) . . ?
C27 O5 C28 112.70(17) . . ?
C10 N1 N2 112.30(14) . . ?
C10 N1 C19 129.55(16) . . ?
N2 N1 C19 118.05(16) . . ?
C11 N2 N1 108.27(15) . . ?
O4 N3 O3 124.28(16) . . ?
O4 N3 C25 119.53(16) . . ?
O3 N3 C25 116.16(17) . . ?
O1 C1 C13 106.88(13) . . ?
O1 C1 C2 111.38(14) . . ?
C13 C1 C2 113.95(14) . . ?
O1 C1 H1 108.2 . . ?
C13 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C11 C2 C10 100.81(14) . . ?
C11 C2 C1 114.38(13) . . ?
C10 C2 C1 108.45(14) . . ?
C11 C2 C3 115.20(14) . . ?
C10 C2 C3 109.32(12) . . ?
C1 C2 C3 108.23(14) . . ?
C4 C3 C25 114.32(15) . . ?
C4 C3 C2 110.24(13) . . ?
C25 C3 C2 109.27(13) . . ?
C4 C3 H3 107.6 . . ?
C25 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C5 C4 C9 117.47(16) . . ?
C5 C4 C3 119.90(16) . . ?
C9 C4 C3 122.63(15) . . ?
O1 C5 C6 115.48(17) . . ?
O1 C5 C4 123.54(16) . . ?
C6 C5 C4 120.87(18) . . ?
C7 C6 C5 120.37(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.94(18) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.65(19) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 121.71(18) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O2 C10 N1 128.21(16) . . ?
O2 C10 C2 126.00(16) . . ?
N1 C10 C2 105.79(14) . . ?
N2 C11 C12 120.65(17) . . ?
N2 C11 C2 112.78(15) . . ?
C12 C11 C2 126.56(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.17(18) . . ?
C14 C13 C1 119.45(16) . . ?
C18 C13 C1 121.36(17) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.9(2) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C24 C19 C20 120.1(2) . . ?
C24 C19 N1 120.8(2) . . ?
C20 C19 N1 119.1(2) . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C24 C23 119.4(3) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
N3 C25 C3 113.36(15) . . ?
N3 C25 H25A 108.9 . . ?
C3 C25 H25A 108.9 . . ?
N3 C25 H25B 108.9 . . ?
C3 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 C26 109.1(2) . . ?
O5 C27 H27A 109.9 . . ?
C26 C27 H27A 109.9 . . ?
O5 C27 H27B 109.9 . . ?
C26 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
O5 C28 C29 109.59(19) . . ?
O5 C28 H28A 109.8 . . ?
C29 C28 H28A 109.8 . . ?
O5 C28 H28B 109.8 . . ?
C29 C28 H28B 109.8 . . ?
H28A C28 H28B 108.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 N2 C11 1.6(2) . . . . ?
C19 N1 N2 C11 178.23(15) . . . . ?
C5 O1 C1 C13 166.18(16) . . . . ?
C5 O1 C1 C2 41.1(2) . . . . ?
O1 C1 C2 C11 70.43(19) . . . . ?
C13 C1 C2 C11 -50.57(19) . . . . ?
O1 C1 C2 C10 -177.96(13) . . . . ?
C13 C1 C2 C10 61.04(18) . . . . ?
O1 C1 C2 C3 -59.47(17) . . . . ?
C13 C1 C2 C3 179.53(13) . . . . ?
C11 C2 C3 C4 -80.07(18) . . . . ?
C10 C2 C3 C4 167.31(15) . . . . ?
C1 C2 C3 C4 49.37(18) . . . . ?
C11 C2 C3 C25 46.37(18) . . . . ?
C10 C2 C3 C25 -66.25(17) . . . . ?
C1 C2 C3 C25 175.80(13) . . . . ?
C25 C3 C4 C5 -147.02(17) . . . . ?
C2 C3 C4 C5 -23.5(2) . . . . ?
C25 C3 C4 C9 32.3(2) . . . . ?
C2 C3 C4 C9 155.85(17) . . . . ?
C1 O1 C5 C6 171.42(18) . . . . ?
C1 O1 C5 C4 -12.5(3) . . . . ?
C9 C4 C5 O1 -176.01(18) . . . . ?
C3 C4 C5 O1 3.3(3) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 179.26(18) . . . . ?
O1 C5 C6 C7 176.7(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C5 C4 C9 C8 -0.3(3) . . . . ?
C3 C4 C9 C8 -179.67(19) . . . . ?
N2 N1 C10 O2 177.00(17) . . . . ?
C19 N1 C10 O2 0.8(3) . . . . ?
N2 N1 C10 C2 -2.37(18) . . . . ?
C19 N1 C10 C2 -178.56(17) . . . . ?
C11 C2 C10 O2 -177.24(17) . . . . ?
C1 C2 C10 O2 62.3(2) . . . . ?
C3 C2 C10 O2 -55.5(2) . . . . ?
C11 C2 C10 N1 2.15(17) . . . . ?
C1 C2 C10 N1 -118.29(15) . . . . ?
C3 C2 C10 N1 123.90(15) . . . . ?
N1 N2 C11 C12 -179.09(15) . . . . ?
N1 N2 C11 C2 0.02(19) . . . . ?
C10 C2 C11 N2 -1.36(18) . . . . ?
C1 C2 C11 N2 114.77(16) . . . . ?
C3 C2 C11 N2 -118.87(16) . . . . ?
C10 C2 C11 C12 177.70(16) . . . . ?
C1 C2 C11 C12 -66.2(2) . . . . ?
C3 C2 C11 C12 60.2(2) . . . . ?
O1 C1 C13 C14 155.11(18) . . . . ?
C2 C1 C13 C14 -81.4(2) . . . . ?
O1 C1 C13 C18 -23.3(2) . . . . ?
C2 C1 C13 C18 100.19(19) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C1 C13 C14 C15 -177.7(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
C1 C13 C18 C17 177.72(19) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C10 N1 C19 C24 -6.5(3) . . . . ?
N2 N1 C19 C24 177.50(19) . . . . ?
C10 N1 C19 C20 172.98(18) . . . . ?
N2 N1 C19 C20 -3.0(2) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
N1 C19 C20 C21 -178.5(2) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C20 C19 C24 C23 -0.9(4) . . . . ?
N1 C19 C24 C23 178.6(2) . . . . ?
C22 C23 C24 C19 0.7(4) . . . . ?
O4 N3 C25 C3 -21.8(2) . . . . ?
O3 N3 C25 C3 159.97(15) . . . . ?
C4 C3 C25 N3 -79.43(17) . . . . ?
C2 C3 C25 N3 156.50(14) . . . . ?
C28 O5 C27 C26 172.7(2) . . . . ?
C27 O5 C28 C29 -174.5(2) . . . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.032


_exptl_crystal_recrystallization_method 'Vapour Deposition'
_chemical_compound_source        'Fidalrestat,Sorbinil,Catechln and so on'
