#------------------------------------------------------------------------------
#$Date: 2022-08-26 04:08:30 +0300 (Fri, 26 Aug 2022) $
#$Revision: 277408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245383.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_7245383
loop_
_publ_author_name
'Nivetha, Narayanasamy'
'Martiz, Reshma Mary'
'Patil, Shashank M.'
'Ramu, Ramith'
'Sreenivasa, Swamy'
'Velmathi, Sivan'
_publ_section_title
;
 Benzodioxole grafted spirooxindole pyrrolidinyl derivatives: synthesis,
 characterization, molecular docking and anti-diabetic activity
;
_journal_issue                   37
_journal_name_full               'RSC Advances'
_journal_page_first              24192
_journal_page_last               24207
_journal_paper_doi               10.1039/D2RA04452H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C28 H23 F N2 O4'
_chemical_formula_weight         470.48
_chemical_name_systematic
(1'R,2'S,3R)-2'-(benzo[d][1,3]dioxole-5-carbonyl)-1'-(3-fluorophenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one
_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   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2022-01-23 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                104.108(7)
_cell_angle_beta                 91.854(7)
_cell_angle_gamma                117.657(8)
_cell_formula_units_Z            2
_cell_length_a                   9.9780(11)
_cell_length_b                   10.7417(12)
_cell_length_c                   12.4901(14)
_cell_measurement_reflns_used    11034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1133.4(2)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11826
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       Block
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0520
_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)+(0.0737P)²+0.4722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4306
_reflns_number_total             5167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra04452h2.cif
_cod_data_source_block           shelx
_cod_database_code               7245383
_shelx_shelxl_version_number     2016/4
_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   0.981
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.32849(13) 0.53368(13) 0.00826(10) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.21198(14) 0.55766(14) 0.39529(10) 0.0294(3) Uani 1 1 d . . . . .
F1 F -0.18112(19) 0.79867(17) 0.22158(14) 0.0593(4) Uani 1 1 d . . . . .
N2 N 0.02887(14) 0.31052(14) 0.04191(11) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.73476(15) 1.03042(15) 0.52655(13) 0.0384(3) Uani 1 1 d . . . . .
O4 O 0.79187(16) 1.12702(15) 0.37727(14) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.41024(16) 0.41302(17) 0.09885(12) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.497370 0.437413 0.076792 0.029 Uiso 1 1 calc R U . . .
C18 C 0.21128(18) 0.30603(17) 0.19066(13) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.16873(17) 0.39105(17) 0.12734(13) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.14126(17) 0.51364(16) 0.20130(13) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.151681 0.582384 0.158846 0.020 Uiso 1 1 calc R U . . .
C23 C -0.10093(17) 0.51662(17) 0.26254(13) 0.0184(3) Uani 1 1 d . . . . .
C10 C -0.02875(17) 0.42570(16) 0.20979(13) 0.0170(3) Uani 1 1 d . . . . .
H10 H -0.039327 0.357904 0.253203 0.020 Uiso 1 1 calc R U . . .
C16 C 0.31090(17) 0.45615(17) 0.06960(13) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.24706(18) 0.60075(17) 0.31369(13) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.39056(18) 0.74034(17) 0.32306(14) 0.0203(3) Uani 1 1 d . . . . .
C28 C -0.16619(19) 0.49513(19) 0.35803(14) 0.0224(3) Uani 1 1 d . . . . .
H28 H -0.162723 0.426534 0.389668 0.027 Uiso 1 1 calc R U . . .
C11 C -0.09562(17) 0.33637(17) 0.08644(13) 0.0190(3) Uani 1 1 d . . . . .
H11 H -0.117989 0.394360 0.046481 0.023 Uiso 1 1 calc R U . . .
C17 C 0.35421(19) 0.32354(19) 0.16962(14) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.48898(19) 0.81270(18) 0.42760(15) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.465798 0.775162 0.488313 0.028 Uiso 1 1 calc R U . . .
C24 C -0.1054(2) 0.62087(19) 0.21645(15) 0.0252(4) Uani 1 1 d . . . . .
H24 H -0.062057 0.637736 0.153122 0.030 Uiso 1 1 calc R U . . .
C2 C 0.62022(19) 0.94080(18) 0.43544(16) 0.0256(4) Uani 1 1 d . . . . .
C19 C 0.1372(2) 0.22043(19) 0.25921(15) 0.0253(4) Uani 1 1 d . . . . .
H19 H 0.042324 0.208159 0.275541 0.030 Uiso 1 1 calc R U . . .
C15 C -0.0333(2) 0.15162(18) -0.00868(15) 0.0261(4) Uani 1 1 d . . . . .
H15A H 0.042290 0.122630 0.006829 0.031 Uiso 1 1 calc R U . . .
H15B H -0.062144 0.125130 -0.089191 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6555(2) 0.99888(19) 0.34644(17) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.4272(2) 0.79968(19) 0.23438(15) 0.0288(4) Uani 1 1 d . . . . .
H5 H 0.360676 0.750449 0.166106 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4258(2) 0.2592(2) 0.21355(16) 0.0295(4) Uani 1 1 d . . . . .
H22 H 0.521904 0.273559 0.198785 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2064(2) 0.1528(2) 0.30348(15) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.156560 0.094190 0.348769 0.035 Uiso 1 1 calc R U . . .
C13 C -0.23690(19) 0.18358(19) 0.06364(16) 0.0278(4) Uani 1 1 d . . . . .
H13A H -0.290430 0.177567 0.127236 0.033 Uiso 1 1 calc R U . . .
H13B H -0.307375 0.162181 -0.002041 0.033 Uiso 1 1 calc R U . . .
C27 C -0.2363(2) 0.5753(2) 0.40624(16) 0.0302(4) Uani 1 1 d . . . . .
H27 H -0.279316 0.559956 0.469943 0.036 Uiso 1 1 calc R U . . .
C26 C -0.2427(2) 0.6776(2) 0.36042(18) 0.0353(5) Uani 1 1 d . . . . .
H26 H -0.290592 0.730824 0.391575 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3485(2) 0.1723(2) 0.28062(16) 0.0321(4) Uani 1 1 d . . . . .
H21 H 0.392805 0.126221 0.310746 0.038 Uiso 1 1 calc R U . . .
C25 C -0.1756(2) 0.6979(2) 0.26711(18) 0.0332(4) Uani 1 1 d . . . . .
C6 C 0.5611(2) 0.9313(2) 0.24478(18) 0.0377(5) Uani 1 1 d . . . . .
H6 H 0.584973 0.971201 0.185250 0.045 Uiso 1 1 calc R U . . .
C1 C 0.8510(2) 1.1404(2) 0.4876(2) 0.0432(5) Uani 1 1 d . . . . .
H1A H 0.941151 1.127871 0.486512 0.052 Uiso 1 1 calc R U . . .
H1B H 0.880145 1.237169 0.537148 0.052 Uiso 1 1 calc R U . . .
C14 C -0.1733(2) 0.0773(2) 0.0445(2) 0.0395(5) Uani 1 1 d . . . . .
H14A H -0.144528 0.065190 0.114610 0.047 Uiso 1 1 calc R U . . .
H14B H -0.247469 -0.018038 -0.005440 0.047 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
C15 N2 C12 118.53(13) . . ?
C15 N2 C11 108.62(12) . . ?
C12 N2 C11 110.07(12) . . ?
C2 O3 C1 105.63(16) . . ?
C7 O4 C1 105.46(16) . . ?
C16 N1 C17 111.74(13) . . ?
C16 N1 H1 124.1 . . ?
C17 N1 H1 124.1 . . ?
C19 C18 C17 118.60(15) . . ?
C19 C18 C12 133.14(14) . . ?
C17 C18 C12 108.25(13) . . ?
N2 C12 C18 118.95(13) . . ?
N2 C12 C16 109.05(12) . . ?
C18 C12 C16 101.31(12) . . ?
N2 C12 C9 100.81(11) . . ?
C18 C12 C9 115.38(13) . . ?
C16 C12 C9 111.54(12) . . ?
C8 C9 C10 114.16(12) . . ?
C8 C9 C12 115.92(12) . . ?
C10 C9 C12 101.25(12) . . ?
C8 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C12 C9 H9 108.4 . . ?
C28 C23 C24 119.25(14) . . ?
C28 C23 C10 119.69(14) . . ?
C24 C23 C10 121.05(14) . . ?
C23 C10 C9 115.24(13) . . ?
C23 C10 C11 115.32(13) . . ?
C9 C10 C11 100.14(12) . . ?
C23 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
O1 C16 N1 126.29(14) . . ?
O1 C16 C12 125.19(14) . . ?
N1 C16 C12 108.51(13) . . ?
O2 C8 C4 120.86(15) . . ?
O2 C8 C9 119.66(14) . . ?
C4 C8 C9 119.46(13) . . ?
C5 C4 C3 120.37(15) . . ?
C5 C4 C8 122.42(15) . . ?
C3 C4 C8 117.21(14) . . ?
C27 C28 C23 120.54(16) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
N2 C11 C10 104.62(12) . . ?
N2 C11 C13 105.93(12) . . ?
C10 C11 C13 116.67(13) . . ?
N2 C11 H11 109.8 . . ?
C10 C11 H11 109.8 . . ?
C13 C11 H11 109.8 . . ?
C22 C17 C18 123.15(16) . . ?
C22 C17 N1 126.67(15) . . ?
C18 C17 N1 110.18(14) . . ?
C2 C3 C4 116.78(16) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C25 C24 C23 118.23(16) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C3 C2 O3 128.15(17) . . ?
C3 C2 C7 122.34(17) . . ?
O3 C2 C7 109.51(15) . . ?
C18 C19 C20 119.31(16) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
N2 C15 C14 105.84(14) . . ?
N2 C15 H15A 110.6 . . ?
C14 C15 H15A 110.6 . . ?
N2 C15 H15B 110.6 . . ?
C14 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
O4 C7 C6 127.99(18) . . ?
O4 C7 C2 110.17(17) . . ?
C6 C7 C2 121.84(16) . . ?
C4 C5 C6 121.78(17) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C17 C22 C21 117.21(16) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C21 C20 C19 120.59(17) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C14 C13 C11 104.96(14) . . ?
C14 C13 H13A 110.8 . . ?
C11 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C11 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C26 C27 C28 120.58(16) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C25 C26 C27 117.68(16) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C20 C21 C22 121.12(16) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
F1 C25 C24 118.22(17) . . ?
F1 C25 C26 118.06(16) . . ?
C24 C25 C26 123.72(17) . . ?
C7 C6 C5 116.89(18) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O3 C1 O4 108.34(15) . . ?
O3 C1 H1A 110.0 . . ?
O4 C1 H1A 110.0 . . ?
O3 C1 H1B 110.0 . . ?
O4 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C15 C14 C13 103.16(15) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
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 C16 1.2229(19) . ?
O2 C8 1.2159(19) . ?
F1 C25 1.360(2) . ?
N2 C15 1.471(2) . ?
N2 C12 1.472(2) . ?
N2 C11 1.4896(19) . ?
O3 C2 1.374(2) . ?
O3 C1 1.422(3) . ?
O4 C7 1.365(2) . ?
O4 C1 1.428(3) . ?
N1 C16 1.348(2) . ?
N1 C17 1.402(2) . ?
N1 H1 0.8600 . ?
C18 C19 1.385(2) . ?
C18 C17 1.392(2) . ?
C18 C12 1.527(2) . ?
C12 C16 1.553(2) . ?
C12 C9 1.556(2) . ?
C9 C8 1.519(2) . ?
C9 C10 1.534(2) . ?
C9 H9 0.9800 . ?
C23 C28 1.395(2) . ?
C23 C24 1.395(2) . ?
C23 C10 1.509(2) . ?
C10 C11 1.535(2) . ?
C10 H10 0.9800 . ?
C8 C4 1.491(2) . ?
C4 C5 1.386(2) . ?
C4 C3 1.410(2) . ?
C28 C27 1.388(2) . ?
C28 H28 0.9300 . ?
C11 C13 1.536(2) . ?
C11 H11 0.9800 . ?
C17 C22 1.381(2) . ?
C3 C2 1.368(2) . ?
C3 H3 0.9300 . ?
C24 C25 1.374(2) . ?
C24 H24 0.9300 . ?
C2 C7 1.381(3) . ?
C19 C20 1.395(2) . ?
C19 H19 0.9300 . ?
C15 C14 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C7 C6 1.366(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C22 C21 1.387(3) . ?
C22 H22 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C27 C26 1.382(3) . ?
C27 H27 0.9300 . ?
C26 C25 1.376(3) . ?
C26 H26 0.9300 . ?
C21 H21 0.9300 . ?
C6 H6 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
