 
data_C:\COMPAQ1\DUMI2016\FA50\fa50
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         6-ethyl-2-(3-phenylsydnon-4-yl)indolizine
_chemical_name_common             none
_chemical_melting_point           '400-402 K'
_chemical_formula_moiety          'C18 H15 N3 O2'
_chemical_formula_sum
 'C18 H15 N3 O2' 
_chemical_formula_weight          305.33

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       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    11.7917(5)
_cell_length_b                    7.5448(3)
_cell_length_c                    17.6610(8)
_cell_angle_alpha                 90
_cell_angle_beta                  101.754(2)
_cell_angle_gamma                 90
_cell_volume                      1538.28(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     6723
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             brown
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.318          
_exptl_crystal_F_000              640
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.250
_exptl_crystal_size_mid           0.160
_exptl_crystal_size_min           0.110
_exptl_absorpt_coefficient_mu     0.088
_shelx_estimated_absorpt_T_min    0.978
_shelx_estimated_absorpt_T_max    0.990
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_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   'Nonius Kappa CCD'
_diffrn_measurement_method        'phi- and omega-scans of 1.000 deg.'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6723
_diffrn_reflns_av_unetI/netI      0.0492
_diffrn_reflns_av_R_equivalents   0.0352
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          4.446
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  0.992
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   0.992
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.992
_reflns_number_total              3492
_reflns_number_gt                 2561
_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        'COLLECT,1998' 
_computing_cell_refinement        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction         'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXH (Sheldrick, 1997)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'  
_computing_publication_material   'PLATON (Spek, 1990)'
_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)+(0.0514P)²+0.2663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3492
_refine_ls_number_parameters      209
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0685
_refine_ls_R_factor_gt            0.0421
_refine_ls_wR_factor_ref          0.1120
_refine_ls_wR_factor_gt           0.0995
_refine_ls_goodness_of_fit_ref    1.016
_refine_ls_restrained_S_all       1.016
_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 -0.12348(8) 0.50491(13) 0.05957(5) 0.0402(3) Uani 1 1 d . . . . .
N2 N -0.07391(10) 0.60534(15) 0.12317(6) 0.0399(3) Uani 1 1 d . . . . .
N3 N 0.02729(9) 0.52783(14) 0.14826(6) 0.0333(3) Uani 1 1 d . . . . .
C4 C 0.04989(11) 0.38604(17) 0.10723(7) 0.0320(3) Uani 1 1 d . . . . .
C5 C -0.05036(11) 0.36492(17) 0.04847(7) 0.0343(3) Uani 1 1 d . . . . .
O6 O -0.07991(8) 0.25976(13) -0.00450(5) 0.0414(3) Uani 1 1 d . . . . .
C7 C 0.09988(11) 0.60438(17) 0.21658(7) 0.0346(3) Uani 1 1 d . . . . .
C8 C 0.14775(12) 0.76833(19) 0.21057(9) 0.0437(4) Uani 1 1 d . . . . .
H8 H 0.1329 0.8309 0.1629 0.052 Uiso 1 1 calc R U . . .
C9 C 0.21806(13) 0.8402(2) 0.27556(10) 0.0562(4) Uani 1 1 d . . . . .
H9 H 0.2527 0.9530 0.2727 0.067 Uiso 1 1 calc R U . . .
C10 C 0.23804(13) 0.7485(3) 0.34443(10) 0.0579(5) Uani 1 1 d . . . . .
H10 H 0.2869 0.7982 0.3888 0.070 Uiso 1 1 calc R U . . .
C11 C 0.18753(13) 0.5846(2) 0.34948(9) 0.0536(4) Uani 1 1 d . . . . .
H11 H 0.2008 0.5232 0.3974 0.064 Uiso 1 1 calc R U . . .
C12 C 0.11783(12) 0.5099(2) 0.28499(8) 0.0426(4) Uani 1 1 d . . . . .
H12 H 0.0833 0.3969 0.2876 0.051 Uiso 1 1 calc R U . . .
C13 C 0.15687(11) 0.28658(17) 0.11779(7) 0.0314(3) Uani 1 1 d . . . . .
C14 C 0.16464(11) 0.12293(17) 0.08312(7) 0.0337(3) Uani 1 1 d . . . . .
H14 H 0.1029 0.0612 0.0509 0.040 Uiso 1 1 calc R U . . .
N15 N 0.27704(9) 0.06643(14) 0.10363(6) 0.0319(3) Uani 1 1 d . . . . .
C16 C 0.32511(11) -0.09237(18) 0.08637(8) 0.0374(3) Uani 1 1 d . . . . .
H16 H 0.2780 -0.1770 0.0548 0.045 Uiso 1 1 calc R U . . .
C17 C 0.43830(12) -0.12829(18) 0.11399(8) 0.0379(3) Uani 1 1 d . . . . .
C18 C 0.50799(12) 0.0023(2) 0.16052(8) 0.0398(3) Uani 1 1 d . . . . .
H18 H 0.5881 -0.0202 0.1792 0.048 Uiso 1 1 calc R U . . .
C19 C 0.46184(11) 0.15804(19) 0.17852(7) 0.0378(3) Uani 1 1 d . . . . .
H19 H 0.5097 0.2426 0.2097 0.045 Uiso 1 1 calc R U . . .
C20 C 0.34279(11) 0.19489(17) 0.15106(7) 0.0328(3) Uani 1 1 d . . . . .
C21 C 0.26894(11) 0.33163(18) 0.15966(7) 0.0349(3) Uani 1 1 d . . . . .
H21 H 0.2895 0.4372 0.1885 0.042 Uiso 1 1 calc R U . . .
C22 C 0.49129(13) -0.3017(2) 0.09600(9) 0.0495(4) Uani 1 1 d . . . . .
H22A H 0.4287 -0.3826 0.0709 0.059 Uiso 1 1 calc R U . . .
H22B H 0.5309 -0.3574 0.1450 0.059 Uiso 1 1 calc R U . . .
C23 C 0.57737(16) -0.2795(3) 0.04358(12) 0.0706(5) Uani 1 1 d . . . . .
H23A H 0.5380 -0.2287 -0.0059 0.106 Uiso 1 1 calc R U . . .
H23B H 0.6098 -0.3953 0.0346 0.106 Uiso 1 1 calc R U . . .
H23C H 0.6399 -0.2001 0.0682 0.106 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 1.3819(14) . ?
O1 C5 1.4023(16) . ?
N2 N3 1.3218(15) . ?
N3 C4 1.3487(16) . ?
N3 C7 1.4496(16) . ?
C4 C5 1.4142(18) . ?
C4 C13 1.4468(18) . ?
C5 O6 1.2220(15) . ?
C7 C8 1.3728(19) . ?
C7 C12 1.3815(19) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3895(18) . ?
C13 C21 1.4179(18) . ?
C14 N15 1.3689(16) . ?
C14 H14 0.9500 . ?
N15 C16 1.3856(16) . ?
N15 C20 1.4063(16) . ?
C16 C17 1.3519(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.431(2) . ?
C17 C22 1.5109(19) . ?
C18 C19 1.3594(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.4162(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3782(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.516(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
N2 O1 C5 110.88(9) . . ?
N3 N2 O1 103.50(10) . . ?
N2 N3 C4 115.75(11) . . ?
N2 N3 C7 116.26(10) . . ?
C4 N3 C7 127.98(11) . . ?
N3 C4 C5 104.87(11) . . ?
N3 C4 C13 127.20(11) . . ?
C5 C4 C13 127.78(12) . . ?
O6 C5 O1 120.56(11) . . ?
O6 C5 C4 134.46(12) . . ?
O1 C5 C4 104.97(11) . . ?
C8 C7 C12 122.72(13) . . ?
C8 C7 N3 118.49(12) . . ?
C12 C7 N3 118.79(12) . . ?
C7 C8 C9 118.40(15) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.15(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.49(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.21(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C7 C12 C11 118.02(15) . . ?
C7 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C14 C13 C21 107.74(11) . . ?
C14 C13 C4 122.56(11) . . ?
C21 C13 C4 129.67(12) . . ?
N15 C14 C13 107.90(11) . . ?
N15 C14 H14 126.1 . . ?
C13 C14 H14 126.1 . . ?
C14 N15 C16 128.93(11) . . ?
C14 N15 C20 109.24(10) . . ?
C16 N15 C20 121.76(10) . . ?
C17 C16 N15 120.80(12) . . ?
C17 C16 H16 119.6 . . ?
N15 C16 H16 119.6 . . ?
C16 C17 C18 118.59(13) . . ?
C16 C17 C22 121.19(13) . . ?
C18 C17 C22 120.22(12) . . ?
C19 C18 C17 121.28(12) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.38(12) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 N15 107.31(11) . . ?
C21 C20 C19 135.54(12) . . ?
N15 C20 C19 117.15(12) . . ?
C20 C21 C13 107.81(11) . . ?
C20 C21 H21 126.1 . . ?
C13 C21 H21 126.1 . . ?
C17 C22 C23 112.94(14) . . ?
C17 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C17 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5 O1 N2 N3 1.00(13) . . . . ?
O1 N2 N3 C4 0.28(14) . . . . ?
O1 N2 N3 C7 -179.28(10) . . . . ?
N2 N3 C4 C5 -1.40(14) . . . . ?
C7 N3 C4 C5 178.10(12) . . . . ?
N2 N3 C4 C13 174.35(12) . . . . ?
C7 N3 C4 C13 -6.2(2) . . . . ?
N2 O1 C5 O6 179.05(11) . . . . ?
N2 O1 C5 C4 -1.82(13) . . . . ?
N3 C4 C5 O6 -179.20(14) . . . . ?
C13 C4 C5 O6 5.1(2) . . . . ?
N3 C4 C5 O1 1.85(13) . . . . ?
C13 C4 C5 O1 -173.86(12) . . . . ?
N2 N3 C7 C8 -69.32(15) . . . . ?
C4 N3 C7 C8 111.18(15) . . . . ?
N2 N3 C7 C12 110.52(14) . . . . ?
C4 N3 C7 C12 -68.98(17) . . . . ?
C12 C7 C8 C9 0.9(2) . . . . ?
N3 C7 C8 C9 -179.24(13) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
N3 C7 C12 C11 179.80(12) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
N3 C4 C13 C14 167.02(12) . . . . ?
C5 C4 C13 C14 -18.2(2) . . . . ?
N3 C4 C13 C21 -15.4(2) . . . . ?
C5 C4 C13 C21 159.41(13) . . . . ?
C21 C13 C14 N15 0.96(14) . . . . ?
C4 C13 C14 N15 179.02(11) . . . . ?
C13 C14 N15 C16 176.43(12) . . . . ?
C13 C14 N15 C20 -0.69(14) . . . . ?
C14 N15 C16 C17 -177.73(13) . . . . ?
C20 N15 C16 C17 -0.93(19) . . . . ?
N15 C16 C17 C18 -0.9(2) . . . . ?
N15 C16 C17 C22 179.52(12) . . . . ?
C16 C17 C18 C19 1.5(2) . . . . ?
C22 C17 C18 C19 -178.91(12) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C14 N15 C20 C21 0.14(14) . . . . ?
C16 N15 C20 C21 -177.23(11) . . . . ?
C14 N15 C20 C19 179.52(11) . . . . ?
C16 N15 C20 C19 2.15(17) . . . . ?
C18 C19 C20 C21 177.63(14) . . . . ?
C18 C19 C20 N15 -1.53(19) . . . . ?
N15 C20 C21 C13 0.46(14) . . . . ?
C19 C20 C21 C13 -178.76(14) . . . . ?
C14 C13 C21 C20 -0.88(14) . . . . ?
C4 C13 C21 C20 -178.76(13) . . . . ?
C16 C17 C22 C23 111.62(17) . . . . ?
C18 C17 C22 C23 -67.91(18) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C14 H14 O6  0.95 2.55 3.2707(16) 132.5 3
C16 H16 O6  0.95 2.41 3.2159(16) 143.1 3
C14 H14 O6  0.95 2.64 3.1557(16) 114.3 .
C14 H14 O6  0.95 2.55 3.2707(16) 132.5 3
C16 H16 O6  0.95 2.41 3.2159(16) 143.1 3
C14 H14 O6  0.95 2.64 3.1557(16) 114.3 .
C14 H14 O6  0.95 2.55 3.2707(16) 132.5 3
C16 H16 O6  0.95 2.41 3.2159(16) 143.1 3
C14 H14 O6  0.95 2.64 3.1557(16) 114.3 .
C14 H14 O6  0.95 2.55 3.2707(16) 132.5 3
C16 H16 O6  0.95 2.41 3.2159(16) 143.1 3
 
_refine_diff_density_max    0.252
_refine_diff_density_min   -0.300
_refine_diff_density_rms    0.058



