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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/58/1555882.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_1555882
loop_
_publ_author_name
'Cao, Yang'
'Zhang, Xiang'
'Lin, Guangyu'
'Zhang-Negrerie, Daisy'
'Du, Yunfei'
_publ_section_title
;
 Chiral Aryliodine-Mediated Enantioselective Organocatalytic
 Spirocyclization: Synthesis of Spirofurooxindoles via Cascade Oxidative
 C-O and C-C Bond Formation.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5580
_journal_page_last               5583
_journal_paper_doi               10.1021/acs.orglett.6b02816
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/8
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.56310(8)
_cell_length_b                   11.52249(11)
_cell_length_c                   13.97167(11)
_cell_measurement_reflns_used    10118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8250
_cell_measurement_theta_min      3.1180
_cell_volume                     1378.56(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/8 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11908
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.088
_diffrn_reflns_theta_min         4.975
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       0.0140(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0293
_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)+(0.0572P)²+0.0953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2868
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02816_si_003.cif
_cod_data_source_block           p20160406a
_cod_database_code               1555882
_shelx_shelxl_version_number     2014/8
_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   0.832
_shelx_estimated_absorpt_t_max   0.883
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.91621(18) 0.72976(14) 0.22006(10) 0.0639(4) Uani 1 1 d . .
O2 O 0.58509(15) 0.65849(9) 0.24215(8) 0.0461(3) Uani 1 1 d . .
O3 O 0.68752(14) 0.90477(10) 0.37881(9) 0.0506(3) Uani 1 1 d . .
O4 O 0.39988(15) 0.70678(11) 0.14208(9) 0.0511(3) Uani 1 1 d . .
N1 N 0.92536(15) 0.64700(12) 0.37008(10) 0.0440(3) Uani 1 1 d . .
C1 C 0.85432(18) 0.69718(14) 0.29312(11) 0.0431(3) Uani 1 1 d . .
C2 C 0.67880(17) 0.70755(13) 0.31769(11) 0.0393(3) Uani 1 1 d . .
C3 C 0.62956(17) 0.83612(13) 0.32273(11) 0.0387(3) Uani 1 1 d . .
C4 C 0.5100(2) 0.84869(13) 0.25284(12) 0.0433(3) Uani 1 1 d . .
H4 H 0.4547 0.9162 0.2391 0.052 Uiso 1 1 calc R U
C5 C 0.49155(18) 0.74405(14) 0.20988(11) 0.0401(3) Uani 1 1 d . .
C6 C 0.66574(17) 0.64372(13) 0.41036(11) 0.0385(3) Uani 1 1 d . .
C7 C 0.81507(17) 0.61158(13) 0.43924(11) 0.0396(3) Uani 1 1 d . .
C8 C 0.8399(2) 0.55318(15) 0.52397(13) 0.0489(4) Uani 1 1 d . .
H8 H 0.9397 0.5311 0.5429 0.059 Uiso 1 1 calc R U
C9 C 0.7099(2) 0.52859(17) 0.57987(13) 0.0557(4) Uani 1 1 d . .
H9 H 0.7235 0.4891 0.6373 0.067 Uiso 1 1 calc R U
C10 C 0.5611(2) 0.56100(17) 0.55274(13) 0.0536(4) Uani 1 1 d . .
H10 H 0.4763 0.5431 0.5916 0.064 Uiso 1 1 calc R U
C11 C 0.53787(19) 0.62050(15) 0.46711(13) 0.0470(4) Uani 1 1 d . .
H11 H 0.4384 0.6440 0.4487 0.056 Uiso 1 1 calc R U
C12 C 1.09398(19) 0.62726(17) 0.37532(14) 0.0524(4) Uani 1 1 d . .
H12A H 1.1266 0.6290 0.4418 0.063 Uiso 1 1 calc R U
H12B H 1.1476 0.6895 0.3421 0.063 Uiso 1 1 calc R U
C13 C 1.1397(3) 0.5146(3) 0.3325(3) 0.1034(11) Uani 1 1 d . .
H13A H 1.1096 0.5131 0.2663 0.155 Uiso 1 1 calc R U
H13B H 1.0884 0.4526 0.3659 0.155 Uiso 1 1 calc R U
H13C H 1.2508 0.5050 0.3374 0.155 Uiso 1 1 calc R U
C14 C 0.2857(2) 0.78910(19) 0.10481(14) 0.0589(5) Uani 1 1 d . .
H14A H 0.3380 0.8578 0.0807 0.071 Uiso 1 1 calc R U
H14B H 0.2142 0.8124 0.1551 0.071 Uiso 1 1 calc R U
C15 C 0.1989(3) 0.7307(3) 0.0263(2) 0.0841(8) Uani 1 1 d . .
H15A H 0.2685 0.7156 -0.0260 0.126 Uiso 1 1 calc R U
H15B H 0.1154 0.7800 0.0050 0.126 Uiso 1 1 calc R U
H15C H 0.1565 0.6588 0.0493 0.126 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O2 C2 106.79(11)
C5 O4 C14 116.69(14)
C1 N1 C7 111.33(13)
C1 N1 C12 123.05(15)
C7 N1 C12 125.52(14)
O1 C1 N1 126.96(16)
O1 C1 C2 126.10(15)
N1 C1 C2 106.93(13)
O2 C2 C6 113.58(12)
O2 C2 C3 104.95(11)
C6 C2 C3 114.40(12)
O2 C2 C1 110.38(12)
C6 C2 C1 103.14(12)
C3 C2 C1 110.50(12)
O3 C3 C4 131.94(15)
O3 C3 C2 122.78(14)
C4 C3 C2 105.27(12)
C5 C4 C3 107.29(13)
C5 C4 H4 126.4
C3 C4 H4 126.4
O4 C5 O2 111.11(13)
O4 C5 C4 133.23(15)
O2 C5 C4 115.66(14)
C11 C6 C7 120.79(14)
C11 C6 C2 130.84(14)
C7 C6 C2 108.28(13)
C8 C7 C6 121.40(15)
C8 C7 N1 128.74(14)
C6 C7 N1 109.85(13)
C7 C8 C9 117.31(15)
C7 C8 H8 121.3
C9 C8 H8 121.3
C10 C9 C8 122.01(16)
C10 C9 H9 119.0
C8 C9 H9 119.0
C9 C10 C11 120.01(16)
C9 C10 H10 120.0
C11 C10 H10 120.0
C6 C11 C10 118.45(15)
C6 C11 H11 120.8
C10 C11 H11 120.8
N1 C12 C13 112.12(18)
N1 C12 H12A 109.2
C13 C12 H12A 109.2
N1 C12 H12B 109.2
C13 C12 H12B 109.2
H12A C12 H12B 107.9
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O4 C14 C15 107.72(19)
O4 C14 H14A 110.2
C15 C14 H14A 110.2
O4 C14 H14B 110.2
C15 C14 H14B 110.2
H14A C14 H14B 108.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.210(2)
O2 C5 1.3479(18)
O2 C2 1.4413(18)
O3 C3 1.2190(19)
O4 C5 1.3030(19)
O4 C14 1.459(2)
N1 C1 1.364(2)
N1 C7 1.411(2)
N1 C12 1.464(2)
C1 C2 1.546(2)
C2 C6 1.493(2)
C2 C3 1.542(2)
C3 C4 1.422(2)
C4 C5 1.356(2)
C4 H4 0.9300
C6 C11 1.378(2)
C6 C7 1.391(2)
C7 C8 1.378(2)
C8 C9 1.389(3)
C8 H8 0.9300
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.393(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.483(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.486(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C7 N1 C1 O1 -175.19(17)
C12 N1 C1 O1 1.3(3)
C7 N1 C1 C2 6.14(17)
C12 N1 C1 C2 -177.33(15)
C5 O2 C2 C6 123.96(13)
C5 O2 C2 C3 -1.71(15)
C5 O2 C2 C1 -120.78(14)
O1 C1 C2 O2 52.9(2)
N1 C1 C2 O2 -128.47(13)
O1 C1 C2 C6 174.51(17)
N1 C1 C2 C6 -6.80(16)
O1 C1 C2 C3 -62.8(2)
N1 C1 C2 C3 115.89(14)
O2 C2 C3 O3 -179.09(14)
C6 C2 C3 O3 55.75(19)
C1 C2 C3 O3 -60.10(19)
O2 C2 C3 C4 1.83(16)
C6 C2 C3 C4 -123.33(14)
C1 C2 C3 C4 120.82(14)
O3 C3 C4 C5 179.78(16)
C2 C3 C4 C5 -1.26(18)
C14 O4 C5 O2 176.33(14)
C14 O4 C5 C4 -3.5(3)
C2 O2 C5 O4 -178.83(13)
C2 O2 C5 C4 1.03(19)
C3 C4 C5 O4 -179.97(16)
C3 C4 C5 O2 0.2(2)
O2 C2 C6 C11 -58.8(2)
C3 C2 C6 C11 61.6(2)
C1 C2 C6 C11 -178.31(17)
O2 C2 C6 C7 124.61(13)
C3 C2 C6 C7 -114.92(14)
C1 C2 C6 C7 5.13(15)
C11 C6 C7 C8 1.6(2)
C2 C6 C7 C8 178.60(14)
C11 C6 C7 N1 -178.77(15)
C2 C6 C7 N1 -1.80(17)
C1 N1 C7 C8 176.64(16)
C12 N1 C7 C8 0.2(3)
C1 N1 C7 C6 -2.92(18)
C12 N1 C7 C6 -179.35(15)
C6 C7 C8 C9 -0.6(2)
N1 C7 C8 C9 179.91(17)
C7 C8 C9 C10 -0.1(3)
C8 C9 C10 C11 -0.2(3)
C7 C6 C11 C10 -1.9(3)
C2 C6 C11 C10 -178.09(15)
C9 C10 C11 C6 1.2(3)
C1 N1 C12 C13 -87.4(3)
C7 N1 C12 C13 88.6(3)
C5 O4 C14 C15 177.74(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305509
