#------------------------------------------------------------------------------
#$Date: 2021-06-26 08:53:12 +0300 (Sat, 26 Jun 2021) $
#$Revision: 266715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243855.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_2243855
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Grishina, Maria M.'
'Khrustalev, Victor N.'
'Akkurt, Mehmet'
'Huseynova, Afet T.'
'Akobirshoeva, Anzurat A.'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of ethyl
 6'-amino-2'-(chloromethyl)-5'-cyano-2-oxo-1,2-dihydrospiro[indoline-3,4'-pyran]-3'-carboxylate
;
_journal_coeditor_code           VM2250
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              739
_journal_page_last               743
_journal_paper_doi               10.1107/S2056989021006459
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C17 H14 Cl N3 O4'
_chemical_formula_moiety         'C17 H14 Cl N3 O4'
_chemical_formula_sum            'C17 H14 Cl N3 O4'
_chemical_formula_weight         359.76
_chemical_name_systematic
'Ethyl 6'-amino-2'-(chloromethyl)-5'-cyano-2-oxo-1,2-dihydrospiro[indoline-3,4'-pyran]-3'-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                98.8503(7)
_cell_angle_beta                 108.0048(7)
_cell_angle_gamma                96.3852(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0218(2)
_cell_length_b                   10.2278(3)
_cell_length_c                   10.6714(3)
_cell_measurement_reflns_used    6340
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.51
_cell_measurement_theta_min      2.59
_cell_volume                     810.92(4)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.589
_diffrn_reflns_theta_min         2.590
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.628
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0366P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                4685
_reflns_number_total             5899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2250sup1.cif
_cod_data_source_block           I
_cod_database_code               2243855
_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.
;
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.00786(5) 0.62296(4) 0.86942(4) 0.03426(11) Uani d 1 . .
O O1 0.20564(12) 0.57639(8) 0.66693(9) 0.01580(17) Uani d 1 . .
O O2 0.34827(14) 0.39501(10) 1.01602(9) 0.0221(2) Uani d 1 . .
O O3 0.24269(13) 0.20082(9) 0.86649(9) 0.01705(17) Uani d 1 . .
O O4 -0.01410(11) 0.18103(8) 0.54781(9) 0.01560(17) Uani d 1 . .
N N1 0.22730(14) 0.07160(10) 0.58525(11) 0.01426(19) Uani d 1 . .
H H1 0.171(2) -0.0075(17) 0.5472(17) 0.017 Uiso d 1 . .
N N2 0.20156(16) 0.58493(11) 0.45919(12) 0.0189(2) Uani d 1 . .
H H2A 0.198(2) 0.5484(18) 0.3819(19) 0.023 Uiso d 1 . .
H H2B 0.158(2) 0.6601(18) 0.4714(18) 0.023 Uiso d 1 . .
C C1 0.14677(15) 0.18025(11) 0.59191(11) 0.0124(2) Uani d 1 . .
C C2 0.23180(15) 0.51172(11) 0.55510(12) 0.0137(2) Uani d 1 . .
C C3 0.28549(15) 0.38996(11) 0.54920(12) 0.0131(2) Uani d 1 . .
C C4 0.29313(15) 0.30748(11) 0.65670(11) 0.01141(19) Uani d 1 . .
C C5 0.27019(15) 0.39250(11) 0.77759(11) 0.01218(19) Uani d 1 . .
C C6 0.23527(15) 0.51749(12) 0.77729(12) 0.0138(2) Uani d 1 . .
C C7 0.32238(18) 0.33266(13) 0.43295(13) 0.0182(2) Uani d 1 . .
N N7 0.3547(2) 0.28501(14) 0.33968(13) 0.0300(3) Uani d 1 . .
C C8 0.29278(15) 0.33459(12) 0.90096(12) 0.0139(2) Uani d 1 . .
C C9 0.2632(2) 0.12998(14) 0.97758(14) 0.0231(3) Uani d 1 . .
H H9A 0.1751 0.1491 1.0225 0.028 Uiso calc 1 . .
H H9B 0.3840 0.1588 1.0446 0.028 Uiso calc 1 . .
C C10 0.2340(3) -0.01675(15) 0.91875(16) 0.0317(3) Uani d 1 . .
H H10A 0.2419 -0.0684 0.9899 0.048 Uiso calc 1 . .
H H10B 0.3251 -0.0348 0.8779 0.048 Uiso calc 1 . .
H H10C 0.1160 -0.0431 0.8500 0.048 Uiso calc 1 . .
C C11 0.21988(17) 0.61386(13) 0.89102(13) 0.0187(2) Uani d 1 . .
H H11A 0.2843 0.7039 0.8960 0.022 Uiso calc 1 . .
H H11B 0.2752 0.5848 0.9765 0.022 Uiso calc 1 . .
C C12 0.41277(15) 0.10561(12) 0.64735(12) 0.0137(2) Uani d 1 . .
C C13 0.53735(17) 0.02074(13) 0.66518(13) 0.0181(2) Uani d 1 . .
H H13 0.5037 -0.0737 0.6349 0.022 Uiso calc 1 . .
C C14 0.71502(17) 0.08061(14) 0.72987(13) 0.0201(2) Uani d 1 . .
H H14 0.8044 0.0255 0.7431 0.024 Uiso calc 1 . .
C C15 0.76464(16) 0.21894(14) 0.77546(13) 0.0188(2) Uani d 1 . .
H H15 0.8866 0.2568 0.8189 0.023 Uiso calc 1 . .
C C16 0.63576(16) 0.30242(12) 0.75758(12) 0.0150(2) Uani d 1 . .
H H16 0.6684 0.3968 0.7893 0.018 Uiso calc 1 . .
C C17 0.45955(15) 0.24390(12) 0.69254(11) 0.0126(2) 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'
Cl Cl 0.1484 0.1585 '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
C2 O1 C6 . . 119.01(9) ?
C8 O3 C9 . . 115.95(10) ?
C1 N1 C12 . . 111.77(10) ?
C1 N1 H1 . . 123.4(11) ?
C12 N1 H1 . . 124.8(11) ?
C2 N2 H2A . . 118.0(12) ?
C2 N2 H2B . . 119.3(11) ?
H2A N2 H2B . . 120.6(16) ?
O4 C1 N1 . . 126.32(11) ?
O4 C1 C4 . . 125.13(10) ?
N1 C1 C4 . . 108.42(9) ?
N2 C2 O1 . . 110.94(10) ?
N2 C2 C3 . . 127.13(11) ?
O1 C2 C3 . . 121.91(10) ?
C2 C3 C7 . . 118.87(11) ?
C2 C3 C4 . . 122.67(10) ?
C7 C3 C4 . . 118.26(10) ?
C5 C4 C3 . . 109.52(9) ?
C5 C4 C17 . . 112.86(9) ?
C3 C4 C17 . . 112.55(9) ?
C5 C4 C1 . . 113.49(9) ?
C3 C4 C1 . . 107.25(9) ?
C17 C4 C1 . . 100.85(9) ?
C6 C5 C8 . . 120.03(10) ?
C6 C5 C4 . . 121.88(10) ?
C8 C5 C4 . . 118.07(9) ?
C5 C6 O1 . . 123.81(11) ?
C5 C6 C11 . . 127.27(11) ?
O1 C6 C11 . . 108.91(10) ?
N7 C7 C3 . . 178.80(14) ?
O2 C8 O3 . . 123.11(11) ?
O2 C8 C5 . . 127.00(11) ?
O3 C8 C5 . . 109.89(10) ?
O3 C9 C10 . . 106.89(11) ?
O3 C9 H9A . . 110.3 ?
C10 C9 H9A . . 110.3 ?
O3 C9 H9B . . 110.3 ?
C10 C9 H9B . . 110.3 ?
H9A C9 H9B . . 108.6 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C6 C11 Cl1 . . 110.59(9) ?
C6 C11 H11A . . 109.5 ?
Cl1 C11 H11A . . 109.5 ?
C6 C11 H11B . . 109.5 ?
Cl1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C13 C12 C17 . . 122.36(11) ?
C13 C12 N1 . . 128.15(11) ?
C17 C12 N1 . . 109.49(10) ?
C12 C13 C14 . . 116.79(12) ?
C12 C13 H13 . . 121.6 ?
C14 C13 H13 . . 121.6 ?
C15 C14 C13 . . 121.72(11) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 120.36(12) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C17 C16 C15 . . 118.24(11) ?
C17 C16 H16 . . 120.9 ?
C15 C16 H16 . . 120.9 ?
C16 C17 C12 . . 120.53(11) ?
C16 C17 C4 . . 130.24(11) ?
C12 C17 C4 . . 109.23(10) ?
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
Cl1 C11 . 1.7842(13) ?
O1 C2 . 1.3595(15) ?
O1 C6 . 1.3725(14) ?
O2 C8 . 1.2063(15) ?
O3 C8 . 1.3417(14) ?
O3 C9 . 1.4586(15) ?
O4 C1 . 1.2308(14) ?
N1 C1 . 1.3495(14) ?
N1 C12 . 1.4064(15) ?
N1 H1 . 0.853(17) ?
N2 C2 . 1.3379(15) ?
N2 H2A . 0.843(19) ?
N2 H2B . 0.889(18) ?
C1 C4 . 1.5592(16) ?
C2 C3 . 1.3610(15) ?
C3 C7 . 1.4183(17) ?
C3 C4 . 1.5156(16) ?
C4 C5 . 1.5138(16) ?
C4 C17 . 1.5183(16) ?
C5 C6 . 1.3390(16) ?
C5 C8 . 1.4944(16) ?
C6 C11 . 1.4871(17) ?
C7 N7 . 1.1550(18) ?
C9 C10 . 1.497(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.3837(16) ?
C12 C17 . 1.3907(16) ?
C13 C14 . 1.3966(19) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.393(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3995(17) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3840(16) ?
C16 H16 . 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
_geom_hbond_publ_flag
N1 H1 O4 2_556 0.853(17) 1.981(17) 2.8292(14) 173.0(17) yes
N2 H2B O4 2_566 0.887(18) 2.095(18) 2.9636(15) 166.0(17) yes
C11 H11B O2 . 0.99 2.15 2.9039(17) 131 yes
C13 H13 N7 2_656 0.95 2.56 3.333(2) 138 yes
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
C12 N1 C1 O4 . . . . -179.07(12) ?
C12 N1 C1 C4 . . . . 4.71(13) ?
C6 O1 C2 N2 . . . . -178.30(10) ?
C6 O1 C2 C3 . . . . 0.39(17) ?
N2 C2 C3 C7 . . . . 2.90(19) ?
O1 C2 C3 C7 . . . . -175.56(11) ?
N2 C2 C3 C4 . . . . -171.94(12) ?
O1 C2 C3 C4 . . . . 9.61(18) ?
C2 C3 C4 C5 . . . . -11.44(15) ?
C7 C3 C4 C5 . . . . 173.69(10) ?
C2 C3 C4 C17 . . . . -137.85(12) ?
C7 C3 C4 C17 . . . . 47.28(14) ?
C2 C3 C4 C1 . . . . 112.13(12) ?
C7 C3 C4 C1 . . . . -62.74(13) ?
O4 C1 C4 C5 . . . . 58.07(15) ?
N1 C1 C4 C5 . . . . -125.66(10) ?
O4 C1 C4 C3 . . . . -63.02(15) ?
N1 C1 C4 C3 . . . . 113.24(10) ?
O4 C1 C4 C17 . . . . 179.05(11) ?
N1 C1 C4 C17 . . . . -4.69(12) ?
C3 C4 C5 C6 . . . . 4.62(15) ?
C17 C4 C5 C6 . . . . 130.85(11) ?
C1 C4 C5 C6 . . . . -115.19(12) ?
C3 C4 C5 C8 . . . . -173.65(9) ?
C17 C4 C5 C8 . . . . -47.42(13) ?
C1 C4 C5 C8 . . . . 66.54(13) ?
C8 C5 C6 O1 . . . . -177.31(10) ?
C4 C5 C6 O1 . . . . 4.46(18) ?
C8 C5 C6 C11 . . . . 1.96(18) ?
C4 C5 C6 C11 . . . . -176.28(11) ?
C2 O1 C6 C5 . . . . -7.59(17) ?
C2 O1 C6 C11 . . . . 173.03(10) ?
C9 O3 C8 O2 . . . . -1.51(17) ?
C9 O3 C8 C5 . . . . 178.03(10) ?
C6 C5 C8 O2 . . . . -29.78(18) ?
C4 C5 C8 O2 . . . . 148.52(12) ?
C6 C5 C8 O3 . . . . 150.69(11) ?
C4 C5 C8 O3 . . . . -31.00(14) ?
C8 O3 C9 C10 . . . . -169.29(12) ?
C5 C6 C11 Cl1 . . . . -103.28(13) ?
O1 C6 C11 Cl1 . . . . 76.07(11) ?
C1 N1 C12 C13 . . . . 176.98(12) ?
C1 N1 C12 C17 . . . . -2.67(14) ?
C17 C12 C13 C14 . . . . -0.81(18) ?
N1 C12 C13 C14 . . . . 179.59(12) ?
C12 C13 C14 C15 . . . . 0.58(19) ?
C13 C14 C15 C16 . . . . 0.2(2) ?
C14 C15 C16 C17 . . . . -0.69(18) ?
C15 C16 C17 C12 . . . . 0.48(17) ?
C15 C16 C17 C4 . . . . -178.77(11) ?
C13 C12 C17 C16 . . . . 0.29(18) ?
N1 C12 C17 C16 . . . . 179.96(10) ?
C13 C12 C17 C4 . . . . 179.68(11) ?
N1 C12 C17 C4 . . . . -0.65(13) ?
C5 C4 C17 C16 . . . . -56.14(16) ?
C3 C4 C17 C16 . . . . 68.46(15) ?
C1 C4 C17 C16 . . . . -177.56(12) ?
C5 C4 C17 C12 . . . . 124.55(10) ?
C3 C4 C17 C12 . . . . -110.86(11) ?
C1 C4 C17 C12 . . . . 3.13(12) ?

_cod_database_fobs_code 2243855
