 
data_C:\COMPAQ1\DUMI2016\FA119\FA119
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         
'Ethyl 8-ethyl-5-methyl-3-[(3-phenylsydnon-4-yl)-oxomethyl]-indolizine-1-carboxylate'
_chemical_name_common             none
_chemical_melting_point           '480-482 K'
_chemical_formula_moiety          'C23 H21 N3 O5' 
_chemical_formula_sum
 'C23 H21 N3 O5' 
_chemical_formula_weight          419.43

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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, -z'
 
_cell_length_a                    8.9685(5)
_cell_length_b                    10.6487(7)
_cell_length_c                    11.0785(7)
_cell_angle_alpha                 93.4800(10)
_cell_angle_beta                  95.8860(10)
_cell_angle_gamma                 109.3060(10)
_cell_volume                      988.21(11)
_cell_formula_units_Z             2
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     5162
_cell_measurement_theta_min       2.59
_cell_measurement_theta_max       27.08
 
_exptl_crystal_description        block
_exptl_crystal_colour             orange
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.410          
_exptl_crystal_F_000              440
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.230
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.101
_shelx_estimated_absorpt_T_min    0.970
_shelx_estimated_absorpt_T_max    0.980
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.90
_exptl_absorpt_correction_T_max   0.98
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker Apex II diffractometer'
_diffrn_measurement_method        'phi- and omega-scans of 0.5 deg.'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             16785
_diffrn_reflns_av_unetI/netI      0.0358
_diffrn_reflns_av_R_equivalents   0.0407
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.857
_diffrn_reflns_theta_max          27.150
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4376
_reflns_number_gt                 3586
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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        'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_cell_refinement        'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_data_reduction         'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_structure_solution     'SHELXS (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'POV-Ray for Windows, 2003'
_computing_publication_material   'PLATON (A.L. Spek, 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0452P)²+0.2322P] 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          4376
_refine_ls_number_parameters      283
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0499
_refine_ls_R_factor_gt            0.0390
_refine_ls_wR_factor_ref          0.1014
_refine_ls_wR_factor_gt           0.0948
_refine_ls_goodness_of_fit_ref    1.045
_refine_ls_restrained_S_all       1.045
_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 0.42171(12) -0.09983(9) 0.30995(9) 0.0330(2) Uani 1 1 d . . . . .
N2 N 0.32326(15) -0.09304(12) 0.20937(11) 0.0311(3) Uani 1 1 d . . . . .
N3 N 0.38141(13) 0.02995(10) 0.18205(10) 0.0223(2) Uani 1 1 d . . . . .
C4 C 0.51103(15) 0.10975(13) 0.25874(11) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.54400(16) 0.02589(13) 0.34584(13) 0.0245(3) Uani 1 1 d . . . . .
O6 O 0.64483(12) 0.03760(10) 0.43016(9) 0.0317(2) Uani 1 1 d . . . . .
C7 C 0.29761(15) 0.06203(13) 0.07554(12) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.27610(16) -0.01781(14) -0.03265(13) 0.0277(3) Uani 1 1 d . . . . .
H8 H 0.3175 -0.0891 -0.0372 0.033 Uiso 1 1 calc R U . . .
C9 C 0.19233(18) 0.00936(16) -0.13425(14) 0.0343(3) Uani 1 1 d . . . . .
H9 H 0.1764 -0.0434 -0.2098 0.041 Uiso 1 1 calc R U . . .
C10 C 0.13197(18) 0.11272(16) -0.12611(15) 0.0363(4) Uani 1 1 d . . . . .
H10 H 0.0744 0.1306 -0.1960 0.044 Uiso 1 1 calc R U . . .
C11 C 0.15499(18) 0.19064(16) -0.01627(15) 0.0364(4) Uani 1 1 d . . . . .
H11 H 0.1128 0.2615 -0.0114 0.044 Uiso 1 1 calc R U . . .
C12 C 0.23886(17) 0.16612(14) 0.08641(13) 0.0299(3) Uani 1 1 d . . . . .
H12 H 0.2554 0.2192 0.1619 0.036 Uiso 1 1 calc R U . . .
C13 C 0.60749(14) 0.24511(12) 0.23361(11) 0.0197(3) Uani 1 1 d . . . . .
O14 O 0.60173(11) 0.27636(9) 0.12835(8) 0.0264(2) Uani 1 1 d . . . . .
C15 C 0.69711(14) 0.33435(12) 0.33979(11) 0.0196(3) Uani 1 1 d . . . . .
N16 N 0.81732(12) 0.45907(10) 0.33806(9) 0.0188(2) Uani 1 1 d . . . . .
C17 C 0.92554(15) 0.49685(13) 0.25481(12) 0.0221(3) Uani 1 1 d . . . . .
C18 C 1.03300(16) 0.62401(14) 0.27356(13) 0.0274(3) Uani 1 1 d . . . . .
H18 H 1.1059 0.6541 0.2164 0.033 Uiso 1 1 calc R U . . .
C19 C 1.03800(16) 0.71089(13) 0.37510(13) 0.0266(3) Uani 1 1 d . . . . .
H19 H 1.1125 0.7993 0.3837 0.032 Uiso 1 1 calc R U . . .
C20 C 0.93882(15) 0.67250(13) 0.46255(12) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.82586(15) 0.54098(12) 0.44594(11) 0.0193(3) Uani 1 1 d . . . . .
C22 C 0.70946(15) 0.46217(12) 0.51512(11) 0.0205(3) Uani 1 1 d . . . . .
C23 C 0.63676(15) 0.33715(13) 0.44976(12) 0.0210(3) Uani 1 1 d . . . . .
H23 H 0.5574 0.2644 0.4766 0.025 Uiso 1 1 calc R U . . .
C24 C 0.93165(17) 0.39920(14) 0.15428(13) 0.0286(3) Uani 1 1 d . . . . .
H24A H 0.8460 0.3890 0.0880 0.043 Uiso 1 1 calc R U . . .
H24B H 0.9182 0.3125 0.1854 0.043 Uiso 1 1 calc R U . . .
H24C H 1.0348 0.4321 0.1235 0.043 Uiso 1 1 calc R U . . .
C25 C 0.95374(16) 0.77360(13) 0.56890(13) 0.0264(3) Uani 1 1 d . . . . .
H25A H 1.0636 0.8389 0.5823 0.032 Uiso 1 1 calc R U . . .
H25B H 0.9344 0.7272 0.6435 0.032 Uiso 1 1 calc R U . . .
C26 C 0.8360(2) 0.84785(16) 0.54699(17) 0.0409(4) Uani 1 1 d . . . . .
H26A H 0.8558 0.8950 0.4739 0.061 Uiso 1 1 calc R U . . .
H26B H 0.8494 0.9126 0.6175 0.061 Uiso 1 1 calc R U . . .
H26C H 0.7270 0.7837 0.5355 0.061 Uiso 1 1 calc R U . . .
C27 C 0.65712(16) 0.49591(13) 0.63082(12) 0.0238(3) Uani 1 1 d . . . . .
O28 O 0.70898(15) 0.59963(11) 0.69559(11) 0.0509(3) Uani 1 1 d . . . . .
O29 O 0.53576(12) 0.39214(10) 0.65686(9) 0.0314(2) Uani 1 1 d . . . . .
C30 C 0.46739(18) 0.41012(16) 0.76730(13) 0.0315(3) Uani 1 1 d . . . . .
H30A H 0.3558 0.3484 0.7588 0.038 Uiso 1 1 calc R U . . .
H30B H 0.4660 0.5027 0.7777 0.038 Uiso 1 1 calc R U . . .
C31 C 0.5582(2) 0.38450(19) 0.87764(15) 0.0445(4) Uani 1 1 d . . . . .
H31A H 0.5680 0.2958 0.8648 0.067 Uiso 1 1 calc R U . . .
H31B H 0.5018 0.3881 0.9483 0.067 Uiso 1 1 calc R U . . .
H31C H 0.6646 0.4527 0.8925 0.067 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 N2 1.3699(15) . ?
O1 C5 1.4242(16) . ?
N2 N3 1.3068(16) . ?
N3 C4 1.3608(16) . ?
N3 C7 1.4528(17) . ?
C4 C5 1.4271(19) . ?
C4 C13 1.4755(17) . ?
C5 O6 1.2017(16) . ?
C7 C12 1.3797(19) . ?
C7 C8 1.3847(18) . ?
C8 C9 1.387(2) . ?
C9 C10 1.380(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.385(2) . ?
C13 O14 1.2326(15) . ?
C13 C15 1.4486(17) . ?
C15 C23 1.3854(18) . ?
C15 N16 1.4097(15) . ?
N16 C17 1.3874(16) . ?
N16 C21 1.4162(16) . ?
C17 C18 1.3666(19) . ?
C17 C24 1.4948(18) . ?
C18 C19 1.400(2) . ?
C19 C20 1.3716(19) . ?
C20 C21 1.4192(17) . ?
C20 C25 1.5111(18) . ?
C21 C22 1.4298(17) . ?
C22 C23 1.3907(18) . ?
C22 C27 1.4735(18) . ?
C25 C26 1.524(2) . ?
C27 O28 1.2028(17) . ?
C27 O29 1.3405(16) . ?
O29 C30 1.4534(16) . ?
C30 C31 1.488(2) . ?
 
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
N2 O1 C5 111.02(10) . . ?
N3 N2 O1 105.00(10) . . ?
N2 N3 C4 114.97(11) . . ?
N2 N3 C7 115.56(10) . . ?
C4 N3 C7 129.47(11) . . ?
N3 C4 C5 105.54(11) . . ?
N3 C4 C13 123.04(12) . . ?
C5 C4 C13 130.31(12) . . ?
O6 C5 O1 120.31(12) . . ?
O6 C5 C4 136.20(13) . . ?
O1 C5 C4 103.43(11) . . ?
C12 C7 C8 122.91(13) . . ?
C12 C7 N3 119.60(12) . . ?
C8 C7 N3 117.46(12) . . ?
C7 C8 C9 118.06(13) . . ?
C10 C9 C8 120.33(14) . . ?
C9 C10 C11 120.25(15) . . ?
C12 C11 C10 120.61(14) . . ?
C7 C12 C11 117.84(13) . . ?
O14 C13 C15 124.97(11) . . ?
O14 C13 C4 119.61(11) . . ?
C15 C13 C4 115.33(11) . . ?
C23 C15 N16 107.10(11) . . ?
C23 C15 C13 122.59(11) . . ?
N16 C15 C13 125.72(11) . . ?
C17 N16 C15 128.13(11) . . ?
C17 N16 C21 122.62(10) . . ?
C15 N16 C21 108.89(10) . . ?
C18 C17 N16 117.22(12) . . ?
C18 C17 C24 121.47(12) . . ?
N16 C17 C24 121.17(11) . . ?
C17 C18 C19 121.47(12) . . ?
C20 C19 C18 122.15(12) . . ?
C19 C20 C21 117.82(12) . . ?
C19 C20 C25 118.13(12) . . ?
C21 C20 C25 124.04(12) . . ?
N16 C21 C20 118.35(11) . . ?
N16 C21 C22 106.31(10) . . ?
C20 C21 C22 135.34(12) . . ?
C23 C22 C21 107.60(11) . . ?
C23 C22 C27 121.13(12) . . ?
C21 C22 C27 131.18(11) . . ?
C15 C23 C22 110.02(11) . . ?
C20 C25 C26 111.80(12) . . ?
O28 C27 O29 122.11(12) . . ?
O28 C27 C22 127.80(13) . . ?
O29 C27 C22 110.08(11) . . ?
C27 O29 C30 117.09(11) . . ?
O29 C30 C31 112.22(12) . . ?
 
_refine_diff_density_max    0.229
_refine_diff_density_min   -0.209
_refine_diff_density_rms    0.041



