#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/40/1504029.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_1504029
loop_
_publ_author_name
'Castaldi, M. Paola'
'Troast, Dawn M.'
'Porco, Jr, John A'
_publ_section_title
;
 Stereoselective synthesis of spirocyclic oxindoles via Prins
 cyclizations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3362
_journal_page_last               3365
_journal_paper_doi               10.1021/ol901201k
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H25 Br F N O3'
_chemical_formula_sum            'C29 H25 Br F N O3'
_chemical_formula_weight         534.41
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.302(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6456(5)
_cell_length_b                   8.2771(3)
_cell_length_c                   13.6743(6)
_cell_measurement_reflns_used    6011
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.31
_cell_volume                     1197.63(9)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18197
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  0.9173
_exptl_absorpt_correction_T_min  0.3339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0117P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0566
_reflns_number_gt                4826
_reflns_number_total             5728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901201k_si_003.cif
_cod_data_source_block           porco119
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
Br1 Br 0.216504(16) 0.59565(3) 0.700026(11) 0.02961(4) Uani 1 1 d
F1 F 0.45111(14) -0.00184(19) 0.06237(9) 0.0698(4) Uani 1 1 d
O1 O 0.27923(12) -0.06995(15) 0.56760(9) 0.0304(3) Uani 1 1 d
O2 O 0.19883(10) 0.19536(14) 0.70172(8) 0.0191(3) Uani 1 1 d
O3 O 0.04363(11) 0.02901(14) 0.83043(8) 0.0274(3) Uani 1 1 d
N1 N 0.19492(12) 0.12112(19) 0.45755(9) 0.0221(4) Uani 1 1 d
C1 C 0.24948(15) 0.0678(2) 0.54835(12) 0.0211(5) Uani 1 1 d
C2 C 0.26598(15) 0.2159(2) 0.61782(12) 0.0174(4) Uani 1 1 d
C3 C 0.40718(15) 0.2499(2) 0.64890(13) 0.0217(4) Uani 1 1 d
H3 H 0.4082(15) 0.359(2) 0.6792(12) 0.020(5) Uiso 1 1 d
C4 C 0.49627(17) 0.2383(3) 0.56837(15) 0.0323(5) Uani 1 1 d
H4B H 0.4570(19) 0.188(2) 0.5140(15) 0.048(7) Uiso 1 1 d
H4A H 0.5260(18) 0.349(3) 0.5503(13) 0.044(6) Uiso 1 1 d
C5 C 0.60462(17) 0.1266(3) 0.60877(14) 0.0328(6) Uani 1 1 d
H5B H 0.6871(19) 0.187(2) 0.6203(14) 0.046(6) Uiso 1 1 d
H5A H 0.6250(19) 0.044(3) 0.5661(14) 0.048(7) Uiso 1 1 d
C6 C 0.56292(17) 0.0617(2) 0.70161(14) 0.0316(6) Uani 1 1 d
H6 H 0.6072(16) -0.018(2) 0.7420(13) 0.028(5) Uiso 1 1 d
C7 C 0.45876(15) 0.1284(2) 0.72409(12) 0.0249(5) Uani 1 1 d
C8 C 0.38470(15) 0.1003(4) 0.80892(11) 0.0328(4) Uani 1 1 d
H8B H 0.3917(17) 0.213(2) 0.8468(14) 0.031(5) Uiso 1 1 d
H8A H 0.4135(18) 0.027(2) 0.8537(14) 0.033(6) Uiso 1 1 d
C9 C 0.24567(15) 0.0740(3) 0.77228(11) 0.0235(4) Uani 1 1 d
H9 H 0.2270(14) -0.029(2) 0.7415(12) 0.007(4) Uiso 1 1 d
C10 C 0.20089(14) 0.3468(2) 0.55484(11) 0.0158(4) Uani 1 1 d
C11 C 0.17361(15) 0.5045(2) 0.57375(12) 0.0188(4) Uani 1 1 d
C12 C 0.10840(13) 0.5997(3) 0.50147(11) 0.0221(3) Uani 1 1 d
H12 H 0.0949(16) 0.700(2) 0.5204(12) 0.020(5) Uiso 1 1 d
C13 C 0.07121(16) 0.5359(2) 0.41003(13) 0.0237(5) Uani 1 1 d
H13 H 0.0263(13) 0.586(3) 0.3618(10) 0.019(4) Uiso 1 1 d
C14 C 0.09754(16) 0.3765(2) 0.38836(12) 0.0240(4) Uani 1 1 d
H14 H 0.0730(17) 0.335(2) 0.3285(14) 0.031(5) Uiso 1 1 d
C15 C 0.16240(16) 0.2849(2) 0.46145(13) 0.0205(4) Uani 1 1 d
C16 C 0.16708(14) 0.0915(4) 0.85652(11) 0.0254(4) Uani 1 1 d
H16B H 0.1644(15) 0.213(2) 0.8746(12) 0.022(5) Uiso 1 1 d
H16A H 0.2041(17) 0.039(2) 0.9151(13) 0.031(6) Uiso 1 1 d
C17 C -0.03819(17) 0.0348(2) 0.90090(13) 0.0251(5) Uani 1 1 d
C18 C -0.01352(17) 0.1139(3) 0.99018(12) 0.0341(5) Uani 1 1 d
H18 H 0.0660(19) 0.161(2) 1.0060(13) 0.042(6) Uiso 1 1 d
C19 C -0.10284(18) 0.1120(4) 1.05602(13) 0.0429(6) Uani 1 1 d
H19 H -0.081(2) 0.162(3) 1.1156(16) 0.067(8) Uiso 1 1 d
C20 C -0.21645(19) 0.0342(3) 1.03422(15) 0.0377(6) Uani 1 1 d
H20 H -0.2720(17) 0.0326(19) 1.0715(12) 0.023(5) Uiso 1 1 d
C21 C -0.24089(19) -0.0432(3) 0.94487(15) 0.0365(6) Uani 1 1 d
H21 H -0.3193(19) -0.084(3) 0.9270(15) 0.044(6) Uiso 1 1 d
C22 C -0.15245(18) -0.0425(3) 0.87902(14) 0.0320(5) Uani 1 1 d
H22 H -0.1730(18) -0.093(3) 0.8145(14) 0.037(5) Uiso 1 1 d
C23 C 0.15567(19) 0.0127(2) 0.37688(13) 0.0283(5) Uani 1 1 d
H23B H 0.0635(17) 0.0351(19) 0.3532(12) 0.026(5) Uiso 1 1 d
H23 H 0.1552(19) -0.108(3) 0.4083(15) 0.049(6) Uiso 1 1 d
C24 C 0.23577(17) 0.0185(2) 0.29263(12) 0.0226(4) Uani 1 1 d
C25 C 0.2037(2) -0.0844(3) 0.21402(14) 0.0361(5) Uani 1 1 d
H25 H 0.130(2) -0.154(3) 0.2110(16) 0.047(6) Uiso 1 1 d
C26 C 0.2762(2) -0.0926(3) 0.13641(15) 0.0463(6) Uani 1 1 d
H26 H 0.252(2) -0.162(3) 0.0815(16) 0.050(7) Uiso 1 1 d
C27 C 0.3786(2) 0.0060(3) 0.13845(14) 0.0410(6) Uani 1 1 d
C28 C 0.41268(17) 0.1106(4) 0.21358(13) 0.0369(5) Uani 1 1 d
H28 H 0.484(2) 0.173(2) 0.2133(16) 0.054(7) Uiso 1 1 d
C29 C 0.34028(17) 0.1150(3) 0.29112(12) 0.0309(5) Uani 1 1 d
H29 H 0.3664(17) 0.187(2) 0.3388(13) 0.027(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 O2 C9 116.97(12)
C17 O3 C16 116.93(13)
C1 N1 C15 110.82(14)
C1 N1 C23 122.93(16)
C15 N1 C23 125.21(14)
O1 C1 N1 124.91(16)
O1 C1 C2 127.27(15)
N1 C1 C2 107.82(15)
O2 C2 C10 107.81(13)
O2 C2 C3 111.06(13)
C10 C2 C3 113.57(14)
O2 C2 C1 111.46(14)
C10 C2 C1 101.81(13)
C3 C2 C1 110.79(13)
C7 C3 C4 103.99(14)
C7 C3 C2 109.82(14)
C4 C3 C2 116.85(14)
C5 C4 C3 106.21(15)
C6 C5 C4 104.00(15)
C7 C6 C5 112.84(17)
C6 C7 C8 130.76(18)
C6 C7 C3 112.27(16)
C8 C7 C3 116.95(16)
C7 C8 C9 110.10(13)
O2 C9 C16 105.35(16)
O2 C9 C8 111.84(16)
C16 C9 C8 109.64(13)
C11 C10 C15 118.44(15)
C11 C10 C2 132.28(15)
C15 C10 C2 109.27(15)
C10 C11 C12 120.46(16)
C10 C11 Br1 121.17(12)
C12 C11 Br1 118.31(14)
C13 C12 C11 120.0(2)
C12 C13 C14 120.99(17)
C15 C14 C13 117.73(16)
C14 C15 C10 122.36(16)
C14 C15 N1 127.65(16)
C10 C15 N1 109.94(14)
O3 C16 C9 110.48(14)
O3 C17 C22 116.45(16)
O3 C17 C18 124.30(16)
C22 C17 C18 119.24(18)
C19 C18 C17 119.49(19)
C20 C19 C18 121.2(2)
C19 C20 C21 119.07(19)
C22 C21 C20 120.23(19)
C21 C22 C17 120.80(18)
N1 C23 C24 115.00(15)
C29 C24 C25 118.55(18)
C29 C24 C23 123.91(16)
C25 C24 C23 117.50(17)
C26 C25 C24 121.0(2)
C27 C26 C25 118.0(2)
C28 C27 F1 118.7(2)
C28 C27 C26 122.9(2)
F1 C27 C26 118.40(19)
C27 C28 C29 118.2(2)
C24 C29 C28 121.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.8937(16)
F1 C27 1.363(2)
O1 C1 1.205(2)
O2 C2 1.4269(19)
O2 C9 1.443(2)
O3 C17 1.369(2)
O3 C16 1.421(2)
N1 C1 1.384(2)
N1 C15 1.402(2)
N1 C23 1.447(2)
C1 C2 1.549(2)
C2 C10 1.505(2)
C2 C3 1.542(2)
C3 C7 1.499(2)
C3 C4 1.533(3)
C4 C5 1.533(3)
C5 C6 1.490(3)
C6 C7 1.305(2)
C7 C8 1.491(2)
C8 C9 1.525(2)
C9 C16 1.503(2)
C10 C11 1.368(2)
C10 C15 1.395(2)
C11 C12 1.389(2)
C12 C13 1.375(2)
C13 C14 1.387(3)
C14 C15 1.378(2)
C17 C22 1.378(3)
C17 C18 1.385(3)
C18 C19 1.379(2)
C19 C20 1.374(3)
C20 C21 1.379(3)
C21 C22 1.372(3)
C23 C24 1.508(3)
C24 C29 1.371(3)
C24 C25 1.384(3)
C25 C26 1.381(3)
C26 C27 1.359(3)
C27 C28 1.362(3)
C28 C29 1.378(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038353
