#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224744.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224744
loop_
_publ_author_name
'Wang, Jing'
'Zhu, Song-Lei'
_publ_section_title
;
 Ethyl
 6'-amino-5'-cyano-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-3'-carboxylate
;
_journal_coeditor_code           PV2248
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o197
_journal_paper_doi               10.1107/S1600536809054075
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H15 N3 O4'
_chemical_formula_moiety         'C17 H15 N3 O4'
_chemical_formula_sum            'C17 H15 N3 O4'
_chemical_formula_weight         325.32
_chemical_melting_point_gt       511
_chemical_melting_point_lt       512
_chemical_name_systematic
;Ethyl
 6'-amino-5'-cyano-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-3'-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.435(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7812(16)
_cell_length_b                   19.998(4)
_cell_length_c                   10.044(2)
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     1520.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976)  and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14692
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.6420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                2550
_reflns_number_total             2779
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2248.cif
_cod_data_source_block           I
_cod_original_cell_volume        1520.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224744
_cod_database_fobs_code          2224744
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.02630(14) 0.40611(6) 0.47320(10) 0.0250(3) Uani d . 1 . .
O O2 -0.29838(16) 0.31533(6) 0.74767(13) 0.0361(3) Uani d . 1 . .
O O3 -0.15237(13) 0.38754(5) 0.90531(10) 0.0210(3) Uani d . 1 . .
O O4 0.02295(14) 0.52209(5) 0.82365(11) 0.0220(3) Uani d . 1 . .
N N1 0.21452(16) 0.45913(6) 0.98355(12) 0.0198(3) Uani d . 1 . .
H H1 0.2470 0.4898 1.0472 0.024 Uiso calc R 1 . .
N N2 0.52683(18) 0.47764(7) 0.73427(15) 0.0310(3) Uani d . 1 . .
N N3 0.2201(2) 0.44309(8) 0.42427(14) 0.0266(3) Uani d . 1 . .
H H3A 0.322(3) 0.4642(10) 0.446(2) 0.039(6) Uiso d . 1 . .
H H3B 0.144(3) 0.4529(10) 0.343(2) 0.039(5) Uiso d . 1 . .
C C1 -0.1291(2) 0.38438(8) 0.56013(15) 0.0213(3) Uani d . 1 . .
C C2 -0.07153(19) 0.38461(7) 0.69607(15) 0.0186(3) Uani d . 1 . .
C C3 0.11176(19) 0.40821(7) 0.76868(15) 0.0172(3) Uani d . 1 . .
C C4 0.21368(19) 0.42787(7) 0.66251(15) 0.0178(3) Uani d . 1 . .
C C5 0.1420(2) 0.42671(7) 0.52598(15) 0.0198(3) Uani d . 1 . .
C C6 -0.3046(2) 0.36409(10) 0.47479(18) 0.0324(4) Uani d . 1 . .
H H6A -0.2958 0.3193 0.4374 0.049 Uiso calc R 1 . .
H H6B -0.3417 0.3960 0.3995 0.049 Uiso calc R 1 . .
H H6C -0.3916 0.3637 0.5313 0.049 Uiso calc R 1 . .
C C7 -0.18809(19) 0.35822(8) 0.78223(16) 0.0212(3) Uani d . 1 . .
C C8 -0.2410(2) 0.35970(8) 1.00633(16) 0.0252(4) Uani d . 1 . .
H H8A -0.3478 0.3347 0.9593 0.030 Uiso calc R 1 . .
H H8B -0.2782 0.3963 1.0598 0.030 Uiso calc R 1 . .
C C9 -0.1167(3) 0.31383(10) 1.1002(2) 0.0395(5) Uani d . 1 . .
H H9A -0.0801 0.2778 1.0467 0.059 Uiso calc R 1 . .
H H9B -0.1762 0.2947 1.1673 0.059 Uiso calc R 1 . .
H H9C -0.0125 0.3390 1.1479 0.059 Uiso calc R 1 . .
C C10 0.10541(19) 0.47069(7) 0.86000(15) 0.0167(3) Uani d . 1 . .
C C11 0.26981(19) 0.39209(8) 0.99810(15) 0.0200(3) Uani d . 1 . .
C C12 0.3617(2) 0.35940(9) 1.11389(17) 0.0267(4) Uani d . 1 . .
H H12 0.4029 0.3825 1.1979 0.032 Uiso calc R 1 . .
C C13 0.3917(2) 0.29121(9) 1.10268(18) 0.0312(4) Uani d . 1 . .
H H13 0.4564 0.2675 1.1802 0.037 Uiso calc R 1 . .
C C14 0.3292(2) 0.25720(9) 0.98083(19) 0.0311(4) Uani d . 1 . .
H H14 0.3489 0.2105 0.9765 0.037 Uiso calc R 1 . .
C C15 0.2374(2) 0.29119(8) 0.86432(17) 0.0249(4) Uani d . 1 . .
H H15 0.1948 0.2681 0.7805 0.030 Uiso calc R 1 . .
C C16 0.21024(19) 0.35887(7) 0.87391(15) 0.0185(3) Uani d . 1 . .
C C17 0.3870(2) 0.45422(8) 0.70497(15) 0.0203(3) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C1 . . 119.69(11) ?
C7 O3 C8 . . 116.35(12) ?
C10 N1 C11 . . 111.76(12) ?
C10 N1 H1 . . 124.1 ?
C11 N1 H1 . . 124.1 ?
C5 N3 H3A . . 118.2(13) ?
C5 N3 H3B . . 114.7(13) ?
H3A N3 H3B . . 118.5(19) ?
C2 C1 O1 . . 122.60(13) ?
C2 C1 C6 . . 129.37(14) ?
O1 C1 C6 . . 108.01(13) ?
C1 C2 C7 . . 119.26(14) ?
C1 C2 C3 . . 123.16(13) ?
C7 C2 C3 . . 117.53(13) ?
C16 C3 C2 . . 113.49(12) ?
C16 C3 C4 . . 113.29(12) ?
C2 C3 C4 . . 109.16(12) ?
C16 C3 C10 . . 101.03(12) ?
C2 C3 C10 . . 112.18(12) ?
C4 C3 C10 . . 107.37(11) ?
C5 C4 C17 . . 116.72(13) ?
C5 C4 C3 . . 123.09(13) ?
C17 C4 C3 . . 119.97(13) ?
N3 C5 C4 . . 127.76(14) ?
N3 C5 O1 . . 110.01(13) ?
C4 C5 O1 . . 122.21(13) ?
C1 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O2 C7 O3 . . 123.98(14) ?
O2 C7 C2 . . 125.02(14) ?
O3 C7 C2 . . 110.98(12) ?
O3 C8 C9 . . 109.26(13) ?
O3 C8 H8A . . 109.8 ?
C9 C8 H8A . . 109.8 ?
O3 C8 H8B . . 109.8 ?
C9 C8 H8B . . 109.8 ?
H8A C8 H8B . . 108.3 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O4 C10 N1 . . 126.37(14) ?
O4 C10 C3 . . 125.82(13) ?
N1 C10 C3 . . 107.73(12) ?
C12 C11 C16 . . 121.85(15) ?
C12 C11 N1 . . 128.74(15) ?
C16 C11 N1 . . 109.36(13) ?
C11 C12 C13 . . 117.36(16) ?
C11 C12 H12 . . 121.3 ?
C13 C12 H12 . . 121.3 ?
C14 C13 C12 . . 121.40(15) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 120.47(16) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C16 C15 C14 . . 118.46(16) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
C15 C16 C11 . . 120.43(14) ?
C15 C16 C3 . . 130.66(14) ?
C11 C16 C3 . . 108.82(13) ?
N2 C17 C4 . . 176.79(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.3577(19) ?
O1 C1 . 1.3840(19) ?
O2 C7 . 1.2058(19) ?
O3 C7 . 1.3378(19) ?
O3 C8 . 1.4631(18) ?
O4 C10 . 1.2218(18) ?
N1 C10 . 1.3508(19) ?
N1 C11 . 1.405(2) ?
N1 H1 . 0.8800 ?
N2 C17 . 1.158(2) ?
N3 C5 . 1.345(2) ?
N3 H3A . 0.88(2) ?
N3 H3B . 0.91(2) ?
C1 C2 . 1.334(2) ?
C1 C6 . 1.490(2) ?
C2 C7 . 1.488(2) ?
C2 C3 . 1.518(2) ?
C3 C16 . 1.517(2) ?
C3 C4 . 1.521(2) ?
C3 C10 . 1.558(2) ?
C4 C5 . 1.355(2) ?
C4 C17 . 1.418(2) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C8 C9 . 1.497(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C11 C12 . 1.380(2) ?
C11 C16 . 1.394(2) ?
C12 C13 . 1.392(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.397(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.377(2) ?
C15 H15 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 N2 3_667 0.88 2.56 3.321(2) 146
N1 H1 O3 3_567 0.88 2.64 3.337(2) 137
N3 H3A N2 3_666 0.88(2) 2.64(2) 3.223(2) 124(2)
N3 H3B O4 3_566 0.91(2) 1.93(2) 2.841(2) 177(2)
C13 H13 O2 4_666 0.95 2.50 3.293(2) 141
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C1 C2 . . . . 2.1(2) ?
C5 O1 C1 C6 . . . . -179.13(13) ?
O1 C1 C2 C7 . . . . -177.92(13) ?
C6 C1 C2 C7 . . . . 3.6(3) ?
O1 C1 C2 C3 . . . . -0.4(2) ?
C6 C1 C2 C3 . . . . -178.80(15) ?
C1 C2 C3 C16 . . . . -129.44(15) ?
C7 C2 C3 C16 . . . . 48.16(17) ?
C1 C2 C3 C4 . . . . -2.1(2) ?
C7 C2 C3 C4 . . . . 175.55(12) ?
C1 C2 C3 C10 . . . . 116.82(16) ?
C7 C2 C3 C10 . . . . -65.58(16) ?
C16 C3 C4 C5 . . . . 130.57(15) ?
C2 C3 C4 C5 . . . . 3.1(2) ?
C10 C3 C4 C5 . . . . -118.77(15) ?
C16 C3 C4 C17 . . . . -54.99(18) ?
C2 C3 C4 C17 . . . . 177.50(13) ?
C10 C3 C4 C17 . . . . 55.67(17) ?
C17 C4 C5 N3 . . . . 5.3(2) ?
C3 C4 C5 N3 . . . . 179.89(15) ?
C17 C4 C5 O1 . . . . -176.31(13) ?
C3 C4 C5 O1 . . . . -1.7(2) ?
C1 O1 C5 N3 . . . . 177.58(13) ?
C1 O1 C5 C4 . . . . -1.1(2) ?
C8 O3 C7 O2 . . . . 6.8(2) ?
C8 O3 C7 C2 . . . . -172.00(12) ?
C1 C2 C7 O2 . . . . 29.0(2) ?
C3 C2 C7 O2 . . . . -148.67(16) ?
C1 C2 C7 O3 . . . . -152.16(14) ?
C3 C2 C7 O3 . . . . 30.15(18) ?
C7 O3 C8 C9 . . . . 98.97(16) ?
C11 N1 C10 O4 . . . . 172.10(14) ?
C11 N1 C10 C3 . . . . -11.17(16) ?
C16 C3 C10 O4 . . . . -172.22(14) ?
C2 C3 C10 O4 . . . . -51.02(19) ?
C4 C3 C10 O4 . . . . 68.90(18) ?
C16 C3 C10 N1 . . . . 11.03(14) ?
C2 C3 C10 N1 . . . . 132.23(13) ?
C4 C3 C10 N1 . . . . -107.85(13) ?
C10 N1 C11 C12 . . . . -170.85(15) ?
C10 N1 C11 C16 . . . . 6.45(17) ?
C16 C11 C12 C13 . . . . -0.6(2) ?
N1 C11 C12 C13 . . . . 176.36(14) ?
C11 C12 C13 C14 . . . . -1.1(2) ?
C12 C13 C14 C15 . . . . 1.6(2) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
C14 C15 C16 C11 . . . . -1.4(2) ?
C14 C15 C16 C3 . . . . -177.64(14) ?
C12 C11 C16 C15 . . . . 1.9(2) ?
N1 C11 C16 C15 . . . . -175.60(13) ?
C12 C11 C16 C3 . . . . 178.90(13) ?
N1 C11 C16 C3 . . . . 1.38(16) ?
C2 C3 C16 C15 . . . . 49.0(2) ?
C4 C3 C16 C15 . . . . -76.2(2) ?
C10 C3 C16 C15 . . . . 169.28(15) ?
C2 C3 C16 C11 . . . . -127.57(13) ?
C4 C3 C16 C11 . . . . 107.22(14) ?
C10 C3 C16 C11 . . . . -7.30(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2014854
