#------------------------------------------------------------------------------
#$Date: 2024-10-06 07:05:33 +0200 (Sun 06 de Oct de 2024) $
#$Revision: 295098 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133458.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7133458
loop_
_publ_author_name
'Maiti, Sandip'
'Parui, Nabin'
'Halder, Joydev'
'Dash, Jyotirmayee'
_publ_section_title
;
 Synthesis of triazole-fused tetracyclic spirooxindole derivatives
 via metal-free Huisgen cycloaddition.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10009
_journal_page_last               10012
_journal_paper_doi               10.1039/d4cc02534b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_chemical_name_systematic        Spirooxindole2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.630(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.422(4)
_cell_length_b                   20.895(10)
_cell_length_c                   7.919(4)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    229.07
_cell_measurement_theta_max      28.378
_cell_measurement_theta_min      2.272
_cell_volume                     1493.8(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      229.07
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16226
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_min         2.256
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1690 before and 0.1211 after correction.
The Ratio of minimum to maximum transmission is 0.3615.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0902P)²+0.4189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2752
_reflns_number_total             3717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02534b2.cif
_cod_data_source_block           mo_jd260923_0m
_cod_depositor_comments
'Adding full bibliography for 7133457--7133458.cif.'
_cod_original_cell_volume        1493.7(13)
_cod_database_code               7133458
_shelx_shelxl_version_number     2016/6
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C14(H14), C6(H6), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
O2 O 0.26577(17) 0.49743(7) 0.3631(2) 0.0439(4) Uani 1 1 d . . . . .
N1 N 0.08112(17) 0.42885(7) 0.3889(2) 0.0275(4) Uani 1 1 d . . . . .
N2 N 0.59876(17) 0.36238(8) 0.8807(2) 0.0287(4) Uani 1 1 d . . . . .
N3 N 0.6511(2) 0.33324(9) 1.0398(2) 0.0374(4) Uani 1 1 d . . . . .
N4 N 0.5819(2) 0.35891(9) 1.1467(2) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.2244(2) 0.45038(9) 0.4291(3) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.2117(2) 0.35875(8) 0.6028(2) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.0708(2) 0.37374(8) 0.4897(2) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.4120(2) 0.44521(9) 0.7261(3) 0.0277(4) Uani 1 1 d . . . . .
H11A H 0.482963 0.472086 0.689175 0.033 Uiso 1 1 calc R U . . .
H11B H 0.342841 0.473706 0.761318 0.033 Uiso 1 1 calc R U . . .
C7 C 0.32402(19) 0.40462(8) 0.5664(2) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.2261(2) 0.30679(9) 0.7164(3) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.318785 0.296430 0.794607 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0550(2) 0.33767(9) 0.4823(3) 0.0311(4) Uani 1 1 d . . . . .
H4 H -0.147869 0.348130 0.404636 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4944(2) 0.40655(9) 0.8831(3) 0.0275(4) Uani 1 1 d . . . . .
C5 C -0.0366(2) 0.28485(9) 0.5965(3) 0.0335(5) Uani 1 1 d . . . . .
H5 H -0.118717 0.258969 0.594303 0.040 Uiso 1 1 calc R U . . .
C9 C 0.4283(2) 0.37195(9) 0.4709(2) 0.0292(4) Uani 1 1 d . . . . .
H9A H 0.366231 0.352487 0.362131 0.035 Uiso 1 1 calc R U . . .
H9B H 0.487262 0.405484 0.436517 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4846(2) 0.40357(10) 1.0530(3) 0.0343(5) Uani 1 1 d . . . . .
H14 H 0.420678 0.428495 1.097998 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1009(2) 0.27012(9) 0.7128(3) 0.0338(5) Uani 1 1 d . . . . .
H6 H 0.109817 0.235143 0.789740 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5351(2) 0.32050(10) 0.5727(3) 0.0329(4) Uani 1 1 d . . . . .
H10A H 0.477299 0.287679 0.611922 0.039 Uiso 1 1 calc R U . . .
H10B H 0.582584 0.299966 0.491671 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6565(2) 0.34446(10) 0.7335(3) 0.0342(5) Uani 1 1 d . . . . .
H12A H 0.731144 0.310825 0.772769 0.041 Uiso 1 1 calc R U . . .
H12B H 0.705192 0.381674 0.699272 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0420(2) 0.45800(10) 0.2553(3) 0.0352(5) Uani 1 1 d . . . . .
H15A H -0.027309 0.504454 0.257573 0.042 Uiso 1 1 calc R U . . .
H15B H -0.133942 0.449596 0.285890 0.042 Uiso 1 1 calc R U . . .
C16 C -0.0596(3) 0.43423(10) 0.0710(3) 0.0404(5) Uani 1 1 d . . . . .
H16 H -0.139836 0.450610 -0.018393 0.048 Uiso 1 1 calc R U . . .
C17 C 0.0259(3) 0.39305(12) 0.0235(4) 0.0472(6) Uani 1 1 d . . . . .
H17A H 0.004(4) 0.3803(15) -0.101(5) 0.077(10) Uiso 1 1 d . . . . .
H17B H 0.111(3) 0.3727(12) 0.112(3) 0.044(7) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C3 110.91(15) . . ?
C8 N1 C15 123.78(16) . . ?
C3 N1 C15 125.28(16) . . ?
N3 N2 C12 120.20(16) . . ?
C13 N2 N3 111.44(16) . . ?
C13 N2 C12 128.36(17) . . ?
N4 N3 N2 107.29(17) . . ?
N3 N4 C14 107.84(17) . . ?
O2 C8 N1 125.15(18) . . ?
O2 C8 C7 126.22(17) . . ?
N1 C8 C7 108.61(15) . . ?
C3 C2 C7 108.72(15) . . ?
C1 C2 C3 118.97(17) . . ?
C1 C2 C7 132.26(17) . . ?
C2 C3 N1 109.53(15) . . ?
C4 C3 N1 127.57(17) . . ?
C4 C3 C2 122.90(17) . . ?
H11A C11 H11B 107.6 . . ?
C7 C11 H11A 108.7 . . ?
C7 C11 H11B 108.7 . . ?
C13 C11 H11A 108.7 . . ?
C13 C11 H11B 108.7 . . ?
C13 C11 C7 114.24(16) . . ?
C8 C7 C11 108.08(15) . . ?
C8 C7 C9 105.65(15) . . ?
C2 C7 C8 102.03(14) . . ?
C2 C7 C11 115.44(15) . . ?
C2 C7 C9 112.76(15) . . ?
C11 C7 C9 111.81(15) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.22(18) . . ?
C6 C1 H1 120.4 . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.83(18) . . ?
C5 C4 H4 121.6 . . ?
N2 C13 C11 124.22(17) . . ?
N2 C13 C14 103.59(17) . . ?
C14 C13 C11 132.15(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.26(18) . . ?
C6 C5 H5 119.4 . . ?
C7 C9 H9A 107.9 . . ?
C7 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 C7 117.50(16) . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
N4 C14 C13 109.83(18) . . ?
N4 C14 H14 125.1 . . ?
C13 C14 H14 125.1 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.78(18) . . ?
C5 C6 H6 119.6 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C10 C9 115.43(17) . . ?
C12 C10 H10A 108.4 . . ?
C12 C10 H10B 108.4 . . ?
N2 C12 C10 112.67(16) . . ?
N2 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C10 C12 H12A 109.1 . . ?
C10 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
N1 C15 C16 114.17(18) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16 116.9 . . ?
C17 C16 C15 126.2(2) . . ?
C17 C16 H16 116.9 . . ?
C16 C17 H17A 119.8(19) . . ?
C16 C17 H17B 121.4(15) . . ?
H17A C17 H17B 119(2) . . ?
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
O2 C8 1.228(2) . ?
N1 C8 1.371(2) . ?
N1 C3 1.420(2) . ?
N1 C15 1.461(2) . ?
N2 N3 1.358(2) . ?
N2 C13 1.352(2) . ?
N2 C12 1.469(2) . ?
N3 N4 1.322(3) . ?
N4 C14 1.368(3) . ?
C8 C7 1.547(3) . ?
C2 C3 1.408(3) . ?
C2 C7 1.515(2) . ?
C2 C1 1.392(3) . ?
C3 C4 1.392(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C7 1.551(3) . ?
C11 C13 1.499(3) . ?
C7 C9 1.558(3) . ?
C1 H1 0.9400 . ?
C1 C6 1.400(3) . ?
C4 H4 0.9400 . ?
C4 C5 1.406(3) . ?
C13 C14 1.376(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.392(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.535(3) . ?
C14 H14 0.9400 . ?
C6 H6 0.9400 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C12 1.531(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 C16 1.504(3) . ?
C16 H16 0.9400 . ?
C16 C17 1.305(4) . ?
C17 H17A 0.98(4) . ?
C17 H17B 1.00(3) . ?
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
O2 C8 C7 C2 177.58(19) . . . . ?
O2 C8 C7 C11 55.5(3) . . . . ?
O2 C8 C7 C9 -64.4(2) . . . . ?
N1 C8 C7 C2 -3.93(19) . . . . ?
N1 C8 C7 C11 -126.04(16) . . . . ?
N1 C8 C7 C9 114.14(17) . . . . ?
N1 C3 C4 C5 -179.96(17) . . . . ?
N1 C15 C16 C17 -2.3(3) . . . . ?
N2 N3 N4 C14 0.8(2) . . . . ?
N2 C13 C14 N4 0.3(2) . . . . ?
N3 N2 C13 C11 -177.88(17) . . . . ?
N3 N2 C13 C14 0.2(2) . . . . ?
N3 N2 C12 C10 121.5(2) . . . . ?
N3 N4 C14 C13 -0.7(2) . . . . ?
C8 N1 C3 C2 1.0(2) . . . . ?
C8 N1 C3 C4 -178.23(18) . . . . ?
C8 N1 C15 C16 85.0(2) . . . . ?
C8 C7 C9 C10 -176.61(16) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C7 C9 C10 -66.0(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C3 N1 C8 O2 -179.46(19) . . . . ?
C3 N1 C8 C7 2.0(2) . . . . ?
C3 N1 C15 C16 -92.7(2) . . . . ?
C3 C2 C7 C8 4.48(19) . . . . ?
C3 C2 C7 C11 121.40(17) . . . . ?
C3 C2 C7 C9 -108.38(17) . . . . ?
C3 C2 C1 C6 1.3(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C11 C7 C9 C10 66.1(2) . . . . ?
C11 C13 C14 N4 178.16(19) . . . . ?
C7 C2 C3 N1 -3.6(2) . . . . ?
C7 C2 C3 C4 175.65(16) . . . . ?
C7 C2 C1 C6 -175.72(19) . . . . ?
C7 C11 C13 N2 58.5(2) . . . . ?
C7 C11 C13 C14 -119.0(2) . . . . ?
C7 C9 C10 C12 -66.4(2) . . . . ?
C1 C2 C3 N1 178.76(16) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C7 C8 -178.31(19) . . . . ?
C1 C2 C7 C11 -61.4(3) . . . . ?
C1 C2 C7 C9 68.8(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C13 N2 N3 N4 -0.6(2) . . . . ?
C13 N2 C12 C10 -58.6(3) . . . . ?
C13 C11 C7 C8 170.26(15) . . . . ?
C13 C11 C7 C2 56.8(2) . . . . ?
C13 C11 C7 C9 -73.9(2) . . . . ?
C9 C10 C12 N2 71.6(2) . . . . ?
C12 N2 N3 N4 179.28(17) . . . . ?
C12 N2 C13 C11 2.2(3) . . . . ?
C12 N2 C13 C14 -179.73(19) . . . . ?
C15 N1 C8 O2 2.6(3) . . . . ?
C15 N1 C8 C7 -175.92(17) . . . . ?
C15 N1 C3 C2 178.87(17) . . . . ?
C15 N1 C3 C4 -0.3(3) . . . . ?
