#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/47/7114770.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_7114770
loop_
_publ_author_name
'Göbel, Angela'
'Imhof, Wolfgang'
_publ_section_title
;
 One-pot ruthenium catalyzed synthesis of spiro[pyrrolidin-2-one]
 derivatives by a [2 + 2 + 1] cycloaddition of ketimines, carbon monoxide
 and ethylene
;
_journal_issue                   7
_journal_name_full               'Chemical Communications'
_journal_page_first              593
_journal_paper_doi               10.1039/b008290m
_journal_year                    2001
_chemical_formula_sum            'C24 H27 N3 O2'
_chemical_formula_weight         389.49
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2350(4)
_cell_length_b                   11.1009(6)
_cell_length_c                   23.0091(15)
_cell_measurement_temperature    183(2)
_cell_volume                     2103.4(2)
_computing_cell_refinement       DENZO
_computing_data_collection       DENZO
_computing_data_reduction        DENZO
_computing_molecular_graphics    XP
_computing_publication_material  XP
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measurement_device       KAPPA-CCD
_diffrn_measurement_method       'phi-scan, omega-scan'
_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  0.1073
_diffrn_reflns_av_sigmaI/netI    0.1452
_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       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11462
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.88(247)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.987
_refine_ls_goodness_of_fit_obs   1.069
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_restrained_S_obs      1.069
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_obs          0.0830
_refine_ls_shift/esd_max         -0.152
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0779P)²+0.6955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1741
_refine_ls_wR_factor_obs         0.1507
_reflns_number_observed          3079
_reflns_number_total             4734
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b008290m.txt
_cod_data_source_block           kat
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorhmbic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.6955P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.6955P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7114770
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.8878(3) 0.5240(3) 0.22062(13) 0.0276(7) Uani 1 d .
C1 C 0.8451(4) 0.5468(4) 0.2822(2) 0.0394(10) Uani 1 d .
H1A H 0.8952(4) 0.6224(4) 0.2963(2) 0.042(3) Uiso 1 calc R
H1B H 0.8807(4) 0.4794(4) 0.3073(2) 0.042(3) Uiso 1 calc R
C2 C 0.6601(4) 0.5568(4) 0.2812(2) 0.0372(9) Uani 1 d .
H2A H 0.6088(4) 0.4769(4) 0.2866(2) 0.042(3) Uiso 1 calc R
H2B H 0.6211(4) 0.6118(4) 0.3121(2) 0.042(3) Uiso 1 calc R
C3 C 0.6232(4) 0.6074(4) 0.2213(2) 0.0361(9) Uani 1 d .
H3A H 0.6452(4) 0.6950(4) 0.2195(2) 0.042(3) Uiso 1 calc R
H3B H 0.5090(4) 0.5923(4) 0.2101(2) 0.042(3) Uiso 1 calc R
C4 C 0.7403(4) 0.5372(3) 0.1829(2) 0.0275(8) Uani 1 d .
H4 H 0.6938(4) 0.4555(3) 0.1753(2) 0.021(8) Uiso 1 calc R
C5 C 0.7931(4) 0.5918(3) 0.1263(2) 0.0325(8) Uani 1 d .
H5A H 0.6980(4) 0.6048(3) 0.1007(2) 0.042(3) Uiso 1 calc R
H5B H 0.8466(4) 0.6704(3) 0.1331(2) 0.042(3) Uiso 1 calc R
O1 O 0.9050(3) 0.5091(2) 0.09948(11) 0.0322(6) Uani 1 d .
C6 C 1.0477(4) 0.4863(3) 0.1321(2) 0.0274(8) Uani 1 d .
C7 C 1.0391(4) 0.5248(3) 0.1967(2) 0.0261(8) Uani 1 d .
C8 C 1.0872(4) 0.3509(3) 0.1287(2) 0.0332(9) Uani 1 d .
H8A H 1.0447(4) 0.3077(3) 0.1631(2) 0.042(3) Uiso 1 calc R
H8B H 1.0402(4) 0.3146(3) 0.0931(2) 0.042(3) Uiso 1 calc R
C9 C 1.2728(4) 0.3466(3) 0.1270(2) 0.0321(9) Uani 1 d .
H9A H 1.3178(4) 0.3352(3) 0.1665(2) 0.042(3) Uiso 1 calc R
H9B H 1.3110(4) 0.2802(3) 0.1018(2) 0.042(3) Uiso 1 calc R
C10 C 1.3224(4) 0.4670(3) 0.10255(14) 0.0260(7) Uani 1 d .
O2 O 1.4574(3) 0.4939(2) 0.08476(12) 0.0375(7) Uani 1 d .
N2 N 1.1888(3) 0.5409(2) 0.10221(12) 0.0245(6) Uani 1 d .
C11 C 1.1934(4) 0.6655(3) 0.08504(14) 0.0238(7) Uani 1 d .
C12 C 1.0894(4) 0.7070(3) 0.0419(2) 0.0308(8) Uani 1 d .
H12 H 1.0168(4) 0.6528(3) 0.0233(2) 0.037(4) Uiso 1 calc R
C13 C 1.0913(4) 0.8277(3) 0.0259(2) 0.0337(9) Uani 1 d .
H13 H 1.0181(4) 0.8556(3) -0.0030(2) 0.037(4) Uiso 1 calc R
C14 C 1.1995(5) 0.9088(3) 0.0519(2) 0.0296(8) Uani 1 d .
C15 C 1.3067(5) 0.8645(3) 0.0932(2) 0.0336(9) Uani 1 d .
H15 H 1.3837(5) 0.9176(3) 0.1102(2) 0.037(4) Uiso 1 calc R
C16 C 1.3043(4) 0.7436(3) 0.1106(2) 0.0317(8) Uani 1 d .
H16 H 1.3774(4) 0.7153(3) 0.1395(2) 0.037(4) Uiso 1 calc R
C17 C 1.1983(6) 1.0418(3) 0.0352(2) 0.0462(10) Uani 1 d .
H17A H 1.1050(34) 1.0815(10) 0.0535(17) 0.131(10) Uiso 1 calc R
H17B H 1.1901(58) 1.0494(3) -0.0071(2) 0.131(10) Uiso 1 calc R
H17C H 1.2989(27) 1.0799(10) 0.0486(18) 0.131(10) Uiso 1 calc R
N3 N 1.1783(3) 0.5406(3) 0.22065(13) 0.0307(7) Uani 1 d .
C18 C 1.2065(4) 0.5592(3) 0.2809(2) 0.0284(8) Uani 1 d .
C19 C 1.2077(4) 0.4644(3) 0.3201(2) 0.0372(9) Uani 1 d .
H19 H 1.1833(4) 0.3855(3) 0.3068(2) 0.037(4) Uiso 1 calc R
C20 C 1.2440(4) 0.4824(4) 0.3788(2) 0.0389(10) Uani 1 d .
H20 H 1.2410(4) 0.4162(4) 0.4049(2) 0.037(4) Uiso 1 calc R
C21 C 1.2846(4) 0.5968(4) 0.3995(2) 0.0348(9) Uani 1 d .
C22 C 1.2899(4) 0.6910(3) 0.3597(2) 0.0331(9) Uani 1 d .
H22 H 1.3193(4) 0.7693(3) 0.3726(2) 0.037(4) Uiso 1 calc R
C23 C 1.2529(4) 0.6729(3) 0.3012(2) 0.0301(8) Uani 1 d .
H23 H 1.2593(4) 0.7386(3) 0.2748(2) 0.037(4) Uiso 1 calc R
C24 C 1.3189(6) 0.6189(5) 0.4636(2) 0.0580(13) Uani 1 d .
H24A H 1.2166(9) 0.6174(38) 0.4853(3) 0.131(10) Uiso 1 calc R
H24B H 1.3709(47) 0.6976(17) 0.4683(3) 0.131(10) Uiso 1 calc R
H24C H 1.3912(42) 0.5558(22) 0.4783(5) 0.131(10) Uiso 1 calc R
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
C7 N1 C1 127.0(3)
C7 N1 C4 120.4(3)
C1 N1 C4 110.1(3)
N1 C1 C2 103.6(3)
N1 C1 H1A 111.0(2)
C2 C1 H1A 111.0(2)
N1 C1 H1B 111.0(2)
C2 C1 H1B 111.0(2)
H1A C1 H1B 109.0
C3 C2 C1 103.8(3)
C3 C2 H2A 111.0(2)
C1 C2 H2A 111.0(2)
C3 C2 H2B 111.0(2)
C1 C2 H2B 111.0(2)
H2A C2 H2B 109.0
C2 C3 C4 102.2(3)
C2 C3 H3A 111.3(2)
C4 C3 H3A 111.3(2)
C2 C3 H3B 111.3(2)
C4 C3 H3B 111.3(2)
H3A C3 H3B 109.2
N1 C4 C5 107.9(3)
N1 C4 C3 103.1(3)
C5 C4 C3 118.7(3)
N1 C4 H4 108.9(2)
C5 C4 H4 108.9(2)
C3 C4 H4 108.9(2)
O1 C5 C4 107.4(3)
O1 C5 H5A 110.2(2)
C4 C5 H5A 110.2(2)
O1 C5 H5B 110.2(2)
C4 C5 H5B 110.2(2)
H5A C5 H5B 108.5
C6 O1 C5 114.7(3)
O1 C6 N2 109.4(3)
O1 C6 C7 114.9(3)
N2 C6 C7 111.7(3)
O1 C6 C8 108.8(3)
N2 C6 C8 102.1(3)
C7 C6 C8 109.2(3)
N3 C7 N1 130.1(3)
N3 C7 C6 114.1(3)
N1 C7 C6 115.3(3)
C9 C8 C6 104.1(3)
C9 C8 H8A 110.9(2)
C6 C8 H8A 110.9(2)
C9 C8 H8B 110.9(2)
C6 C8 H8B 110.9(2)
H8A C8 H8B 109.0
C10 C9 C8 104.6(3)
C10 C9 H9A 110.8(2)
C8 C9 H9A 110.8(2)
C10 C9 H9B 110.8(2)
C8 C9 H9B 110.8(2)
H9A C9 H9B 108.9
O2 C10 N2 125.6(3)
O2 C10 C9 126.1(3)
N2 C10 C9 108.3(3)
C10 N2 C11 123.7(3)
C10 N2 C6 112.5(3)
C11 N2 C6 122.8(3)
C12 C11 C16 120.0(3)
C12 C11 N2 119.9(3)
C16 C11 N2 120.0(3)
C13 C12 C11 120.1(3)
C13 C12 H12 120.0(2)
C11 C12 H12 120.0(2)
C12 C13 C14 121.0(3)
C12 C13 H13 119.5(2)
C14 C13 H13 119.5(2)
C15 C14 C13 117.9(3)
C15 C14 C17 121.3(4)
C13 C14 C17 120.8(4)
C14 C15 C16 121.7(3)
C14 C15 H15 119.1(2)
C16 C15 H15 119.1(2)
C15 C16 C11 119.1(3)
C15 C16 H16 120.4(2)
C11 C16 H16 120.5(2)
C14 C17 H17A 109.5(2)
C14 C17 H17B 109.5(2)
H17A C17 H17B 109.5
C14 C17 H17C 109.5(2)
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C7 N3 C18 125.8(3)
C23 C18 C19 117.7(3)
C23 C18 N3 120.2(3)
C19 C18 N3 121.7(3)
C18 C19 C20 121.5(4)
C18 C19 H19 119.3(2)
C20 C19 H19 119.3(2)
C21 C20 C19 120.7(4)
C21 C20 H20 119.7(2)
C19 C20 H20 119.7(2)
C20 C21 C22 117.8(3)
C20 C21 C24 121.4(4)
C22 C21 C24 120.8(4)
C23 C22 C21 121.4(3)
C23 C22 H22 119.3(2)
C21 C22 H22 119.3(2)
C18 C23 C22 120.8(3)
C18 C23 H23 119.6(2)
C22 C23 H23 119.6(2)
C21 C24 H24A 109.5(2)
C21 C24 H24B 109.5(3)
H24A C24 H24B 109.5
C21 C24 H24C 109.5(2)
H24A C24 H24C 109.5
H24B C24 H24C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.362(4)
N1 C1 1.482(5)
N1 C4 1.500(4)
C1 C2 1.527(5)
C1 H1A 0.99
C1 H1B 0.99
C2 C3 1.520(6)
C2 H2A 0.99
C2 H2B 0.99
C3 C4 1.523(5)
C3 H3A 0.99
C3 H3B 0.99
C4 C5 1.502(5)
C4 H4 1.00
C5 O1 1.439(4)
C5 H5A 0.99
C5 H5B 0.99
O1 C6 1.417(4)
C6 N2 1.480(4)
C6 C7 1.549(5)
C6 C8 1.540(5)
C7 N3 1.284(4)
C8 C9 1.530(5)
C8 H8A 0.99
C8 H8B 0.99
C9 C10 1.507(5)
C9 H9A 0.99
C9 H9B 0.99
C10 O2 1.221(4)
C10 N2 1.372(4)
N2 C11 1.440(4)
C11 C12 1.390(5)
C11 C16 1.389(5)
C12 C13 1.389(5)
C12 H12 0.95
C13 C14 1.400(5)
C13 H13 0.95
C14 C15 1.388(5)
C14 C17 1.525(5)
C15 C16 1.401(5)
C15 H15 0.95
C16 H16 0.95
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
N3 C18 1.420(5)
C18 C23 1.399(5)
C18 C19 1.386(5)
C19 C20 1.398(6)
C19 H19 0.95
C20 C21 1.396(6)
C20 H20 0.95
C21 C22 1.390(5)
C21 C24 1.521(6)
C22 C23 1.394(5)
C22 H22 0.95
C23 H23 0.95
C24 H24A 0.98
C24 H24B 0.98
C24 H24C 0.98
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139185097
