#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034805.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_4034805
loop_
_publ_author_name
'Espinoza-Hicks, Carlos'
'Montoya, Pablo'
'Bautista, Rafael'
'Jiménez-Vázquez, Hugo A'
'Rodríguez-Valdez, Luz M'
'Camacho-Dávila, Alejandro A'
'Cossío, Fernando P'
'Delgado, Francisco'
'Tamariz, Joaquín'
_publ_section_title
;
 Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and
 Selectivity in Diels-Alder Cycloadditions.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5347
_journal_page_last               5364
_journal_paper_doi               10.1021/acs.joc.7b02344
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7477(13)
_cell_length_b                   7.4516(3)
_cell_length_c                   7.8082(4)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    292
_cell_measurement_theta_max      31.4060
_cell_measurement_theta_min      3.1340
_cell_volume                     1381.73(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  XcalSMo
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7092
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.581
_diffrn_reflns_theta_min         2.865
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0577
_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)+(0.0430P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1664
_reflns_number_total             2303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02344_si_002.cif
_cod_data_source_block           0073-jt
_cod_original_cell_volume        1381.71(12)
_cod_database_code               4034805
_shelx_shelxl_version_number     2014/7
_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_max   0.958
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C2'(H2'), C5'(H5'), C3'(H3'), C4'(H4')
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.04384(5) 0.13833(13) 0.79921(15) 0.0430(3) Uani 1 1 d . . .
O2 O 0.0000 0.41163(16) 0.7500 0.0580(4) Uani 1 2 d S T P
C5 C 0.02786(6) -0.04407(14) 0.79093(16) 0.0434(3) Uani 1 1 d . . .
C2 C 0.0000 0.2489(2) 0.7500 0.0424(4) Uani 1 2 d S T P
C1' C 0.09710(6) 0.20407(17) 0.85374(18) 0.0449(3) Uani 1 1 d . . .
C6' C 0.10018(7) 0.34156(19) 0.9725(2) 0.0547(4) Uani 1 1 d . . .
H6' H 0.0675 0.3916 1.0175 0.066 Uiso 1 1 calc R . .
C2' C 0.14580(7) 0.1297(2) 0.7869(2) 0.0625(4) Uani 1 1 d . . .
H2' H 0.1438 0.0381 0.7062 0.075 Uiso 1 1 calc R . .
C7 C 0.05626(8) -0.18339(19) 0.8518(2) 0.0564(4) Uani 1 1 d . . .
C5' C 0.15236(9) 0.4036(3) 1.0236(3) 0.0788(6) Uani 1 1 d . . .
H5' H 0.1547 0.4968 1.1026 0.095 Uiso 1 1 calc R . .
C3' C 0.19761(8) 0.1933(3) 0.8417(3) 0.0838(6) Uani 1 1 d . . .
H3' H 0.2305 0.1432 0.7984 0.101 Uiso 1 1 calc R . .
C4' C 0.20061(9) 0.3299(3) 0.9596(3) 0.0908(7) Uani 1 1 d . . .
H4' H 0.2355 0.3720 0.9959 0.109 Uiso 1 1 calc R . .
H7A H 0.0945(7) -0.169(2) 0.900(2) 0.060(5) Uiso 1 1 d . . .
H7B H 0.0398(7) -0.306(2) 0.841(2) 0.065(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'
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
C5 N1 C1' 125.75(11) . .
C2 N1 C5 111.01(11) . .
C2 N1 C1' 123.23(10) . .
N1 C5 C5 105.17(7) . 4_556
C7 C5 N1 126.89(14) . .
C7 C5 C5 127.86(10) . 4_556
N1 C2 N1 106.82(14) 4_556 .
O2 C2 N1 126.59(7) . 4_556
O2 C2 N1 126.59(7) . .
C6' C1' N1 120.19(13) . .
C6' C1' C2' 120.31(15) . .
C2' C1' N1 119.49(14) . .
C1' C6' H6' 120.4 . .
C5' C6' C1' 119.25(17) . .
C5' C6' H6' 120.4 . .
C1' C2' H2' 120.4 . .
C1' C2' C3' 119.22(19) . .
C3' C2' H2' 120.4 . .
C5 C7 H7A 121.1(10) . .
C5 C7 H7B 119.0(10) . .
H7A C7 H7B 119.8(14) . .
C6' C5' H5' 119.6 . .
C4' C5' C6' 120.8(2) . .
C4' C5' H5' 119.6 . .
C2' C3' H3' 119.8 . .
C4' C3' C2' 120.4(2) . .
C4' C3' H3' 119.8 . .
C5' C4' C3' 119.98(19) . .
C5' C4' H4' 120.0 . .
C3' C4' H4' 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.4126(15) .
N1 C2 1.3821(14) .
N1 C1' 1.4216(17) .
O2 C2 1.213(2) .
C5 C5 1.470(3) 4_556
C5 C7 1.3259(19) .
C2 N1 1.3821(14) 4_556
C1' C6' 1.384(2) .
C1' C2' 1.385(2) .
C6' H6' 0.9300 .
C6' C5' 1.382(2) .
C2' H2' 0.9300 .
C2' C3' 1.386(3) .
C7 H7A 0.990(17) .
C7 H7B 0.996(17) .
C5' H5' 0.9300 .
C5' C4' 1.365(3) .
C3' H3' 0.9300 .
C3' C4' 1.374(3) .
C4' H4' 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 54752227
