#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/68/7226816.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_7226816
loop_
_publ_author_name
'Li, Jian'
'Jiang, Hui'
'Jie, Haohua'
_publ_section_title
;
 Scandium triflate-catalyzed selective ring opening and rearrangement
 reaction of spiro-epoxyoxindole and carbonyl compound
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA21264F
_journal_year                    2016
_chemical_formula_sum            'C13 H14 F N O3'
_chemical_formula_weight         251.25
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-20 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.209(7)
_cell_length_b                   8.898(7)
_cell_length_c                   15.070(12)
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.59
_cell_volume                     1234.9(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5873
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_coef       0.0151(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0285
_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)+(0.0356P)²+0.0607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0715
_reflns_number_gt                1874
_reflns_number_total             2065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra21264f2.cif
_cod_data_source_block           121229b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1234.8(17)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7226816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6426(3) 1.0606(2) 0.44610(14) 0.0734(6) Uani 1 1 d .
C2 C 0.6115(2) 0.9411(2) 0.39344(15) 0.0714(6) Uani 1 1 d .
H2 H 0.5608 0.9547 0.3407 0.086 Uiso 1 1 calc R
C3 C 0.6562(2) 0.7979(2) 0.41892(14) 0.0647(5) Uani 1 1 d .
H3 H 0.6364 0.7142 0.3840 0.078 Uiso 1 1 calc R
C4 C 0.73072(18) 0.78509(18) 0.49773(12) 0.0511(4) Uani 1 1 d .
C5 C 0.76245(19) 0.90880(19) 0.54974(13) 0.0510(4) Uani 1 1 d .
C6 C 0.7172(2) 1.0496(2) 0.52430(13) 0.0654(5) Uani 1 1 d .
H6 H 0.7365 1.1338 0.5588 0.079 Uiso 1 1 calc R
C7 C 0.85116(17) 0.6861(2) 0.61585(13) 0.0543(4) Uani 1 1 d .
C8 C 0.83942(16) 0.85704(18) 0.63136(12) 0.0494(4) Uani 1 1 d .
C9 C 0.76520(19) 0.8977(2) 0.71854(12) 0.0540(4) Uani 1 1 d .
H9A H 0.6611 0.9085 0.7109 0.065 Uiso 1 1 calc R
H9B H 0.7841 0.8228 0.7639 0.065 Uiso 1 1 calc R
C10 C 0.97975(19) 1.02123(18) 0.71721(13) 0.0560(4) Uani 1 1 d .
C11 C 1.0381(3) 1.1727(2) 0.69013(19) 0.0943(8) Uani 1 1 d .
H11A H 1.0296 1.2414 0.7390 0.141 Uiso 1 1 calc R
H11B H 0.9834 1.2100 0.6406 0.141 Uiso 1 1 calc R
H11C H 1.1383 1.1631 0.6737 0.141 Uiso 1 1 calc R
C12 C 1.0652(2) 0.9497(3) 0.79038(16) 0.0757(6) Uani 1 1 d .
H12A H 1.0262 0.8520 0.8029 0.114 Uiso 1 1 calc R
H12B H 1.0595 1.0111 0.8426 0.114 Uiso 1 1 calc R
H12C H 1.1649 0.9402 0.7725 0.114 Uiso 1 1 calc R
C13 C 0.7651(2) 0.5039(2) 0.50287(18) 0.0745(6) Uani 1 1 d .
H13A H 0.6634 0.4802 0.5030 0.112 Uiso 1 1 calc R
H13B H 0.8162 0.4331 0.5394 0.112 Uiso 1 1 calc R
H13C H 0.8017 0.4988 0.4433 0.112 Uiso 1 1 calc R
F1 F 0.5965(2) 1.19892(16) 0.41968(11) 0.1154(6) Uani 1 1 d .
N1 N 0.78629(15) 0.65478(15) 0.53763(10) 0.0549(4) Uani 1 1 d .
O1 O 0.90608(14) 0.59533(15) 0.66637(10) 0.0732(4) Uani 1 1 d .
O2 O 0.83135(12) 1.03738(12) 0.73998(8) 0.0571(3) Uani 1 1 d .
O3 O 0.98043(12) 0.92164(13) 0.64145(9) 0.0615(4) Uani 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'
F F 0.0171 0.0103 '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
C2 C1 F1 118.1(2)
C2 C1 C6 123.6(2)
F1 C1 C6 118.25(19)
C1 C2 C3 119.5(2)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 117.46(18)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 C5 121.90(17)
C3 C4 N1 128.34(16)
C5 C4 N1 109.76(16)
C6 C5 C4 120.21(19)
C6 C5 C8 130.93(17)
C4 C5 C8 108.78(15)
C1 C6 C5 117.26(19)
C1 C6 H6 121.4
C5 C6 H6 121.4
O1 C7 N1 126.27(17)
O1 C7 C8 125.97(18)
N1 C7 C8 107.74(16)
O3 C8 C5 113.29(14)
O3 C8 C9 102.73(13)
C5 C8 C9 115.09(14)
O3 C8 C7 110.44(13)
C5 C8 C7 102.28(14)
C9 C8 C7 113.33(14)
O2 C9 C8 102.20(13)
O2 C9 H9A 111.3
C8 C9 H9A 111.3
O2 C9 H9B 111.3
C8 C9 H9B 111.3
H9A C9 H9B 109.2
O2 C10 O3 104.94(13)
O2 C10 C12 111.84(16)
O3 C10 C12 108.61(15)
O2 C10 C11 108.58(16)
O3 C10 C11 109.45(17)
C12 C10 C11 113.09(19)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C7 N1 C4 111.40(14)
C7 N1 C13 124.35(16)
C4 N1 C13 124.04(17)
C10 O2 C9 105.65(12)
C8 O3 C10 109.09(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.357(3)
C1 F1 1.362(2)
C1 C6 1.368(3)
C2 C3 1.392(3)
C2 H2 0.9300
C3 C4 1.377(3)
C3 H3 0.9300
C4 C5 1.382(3)
C4 N1 1.403(2)
C5 C6 1.375(3)
C5 C8 1.492(3)
C6 H6 0.9300
C7 O1 1.220(2)
C7 N1 1.351(3)
C7 C8 1.543(3)
C8 O3 1.428(2)
C8 C9 1.525(3)
C9 O2 1.421(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O2 1.416(2)
C10 O3 1.445(2)
C10 C12 1.497(3)
C10 C11 1.507(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 N1 1.455(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202886
