#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/51/7115168.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_7115168
loop_
_publ_author_name
'Jones, Raymond C. F.'
'Martin, Jason N.'
'Smith, Paul'
'Gelbrich, Tomas'
'Light, Mark E.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Synthesis of ene-1,1-diamines and pyrrolo[1,2-a]imidazolediones by
 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              1949
_journal_paper_doi               10.1039/b005530l
_journal_year                    2000
_chemical_formula_sum            'C25 H30 N2 O3'
_chemical_formula_weight         406.51
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.211(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.9087(10)
_cell_length_b                   6.8778(4)
_cell_length_c                   24.9780(10)
_cell_measurement_temperature    150(2)
_cell_volume                     4438.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1029
_diffrn_reflns_av_sigmaI/netI    0.1849
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8729
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9905
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00099(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1882
_refine_ls_R_factor_gt           0.0662
_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)+(0.0025P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                1505
_reflns_number_total             3468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005530l.txt
_cod_data_source_block           s92
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7115168
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'
'-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
O1 O 0.22411(9) 0.6826(4) 0.04372(8) 0.0412(7) Uani 1 1 d .
O2 O 0.11678(10) 0.2784(4) 0.08141(11) 0.0700(10) Uani 1 1 d .
O3 O 0.07957(10) 0.3151(4) -0.01062(11) 0.0494(8) Uani 1 1 d .
N1 N 0.16624(10) 0.2058(5) -0.05682(11) 0.0327(8) Uani 1 1 d .
N2 N 0.20930(10) 0.4790(4) -0.04721(11) 0.0371(9) Uani 1 1 d .
H2 H 0.2205 0.5943 -0.0339 0.050 Uiso 1 1 calc .
C1 C 0.17879(13) 0.3691(6) -0.02591(14) 0.0321(10) Uani 1 1 d .
C2 C 0.19145(15) 0.1992(6) -0.10153(15) 0.0416(11) Uani 1 1 d .
H2A H 0.1656 0.1932 -0.1385 0.055(12) Uiso 1 1 calc R
H2B H 0.2148 0.0854 -0.0973 0.055(13) Uiso 1 1 calc R
C3 C 0.22232(14) 0.3910(5) -0.09444(14) 0.0339(10) Uani 1 1 d .
H3 H 0.2602 0.3617 -0.0842 0.024(9) Uiso 1 1 calc R
C4 C 0.14698(14) 0.0251(5) -0.04039(14) 0.0377(10) Uani 1 1 d .
H4A H 0.1417 0.0426 -0.0030 0.034(9) Uiso 1 1 calc R
H4B H 0.1737 -0.0766 -0.0372 0.072(14) Uiso 1 1 calc R
C5 C 0.09698(14) -0.0450(6) -0.08003(15) 0.0344(10) Uani 1 1 d .
C6 C 0.07970(16) -0.2293(6) -0.07254(17) 0.0407(11) Uani 1 1 d .
H6 H 0.0987 -0.3077 -0.0424 0.059(13) Uiso 1 1 calc R
C7 C 0.03496(18) -0.2992(7) -0.10871(19) 0.0575(13) Uani 1 1 d .
H7 H 0.0234 -0.4262 -0.1031 0.047(12) Uiso 1 1 calc R
C8 C 0.00659(18) -0.1905(8) -0.1525(2) 0.0705(15) Uani 1 1 d .
H8 H -0.0242 -0.2406 -0.1774 0.068(14) Uiso 1 1 calc R
C9 C 0.02393(17) -0.0061(8) -0.15962(19) 0.0640(14) Uani 1 1 d .
H9 H 0.0049 0.0717 -0.1898 0.066(13) Uiso 1 1 calc R
C10 C 0.06838(16) 0.0666(6) -0.12354(17) 0.0479(12) Uani 1 1 d .
H10 H 0.0794 0.1947 -0.1287 0.033(10) Uiso 1 1 calc R
C11 C 0.20766(14) 0.5141(5) -0.14686(14) 0.0317(9) Uani 1 1 d .
C12 C 0.16921(14) 0.6523(6) -0.15682(15) 0.0405(11) Uani 1 1 d .
H12 H 0.1520 0.6782 -0.1292 0.029(9) Uiso 1 1 calc R
C13 C 0.15527(15) 0.7542(6) -0.20645(16) 0.0507(12) Uani 1 1 d .
H13 H 0.1291 0.8511 -0.2126 0.024(10) Uiso 1 1 calc R
C14 C 0.17979(16) 0.7139(6) -0.24722(16) 0.0494(12) Uani 1 1 d .
H14 H 0.1699 0.7813 -0.2818 0.061(13) Uiso 1 1 calc R
C15 C 0.21814(15) 0.5771(6) -0.23762(15) 0.0445(11) Uani 1 1 d .
H15 H 0.2351 0.5497 -0.2654 0.041(11) Uiso 1 1 calc R
C16 C 0.23212(14) 0.4790(6) -0.18745(15) 0.0400(11) Uani 1 1 d .
H16 H 0.2591 0.3855 -0.1808 0.034(11) Uiso 1 1 calc R
C17 C 0.16498(13) 0.4211(5) 0.02329(13) 0.0320(10) Uani 1 1 d .
C18 C 0.12032(17) 0.3301(5) 0.03603(18) 0.0451(11) Uani 1 1 d .
C19 C 0.03410(18) 0.2185(8) -0.0035(2) 0.0730(15) Uani 1 1 d .
H19A H 0.0071 0.2158 -0.0392 0.14(2) Uiso 1 1 calc R
H19B H 0.0213 0.2892 0.0241 0.127(19) Uiso 1 1 calc R
H19C H 0.0430 0.0852 0.0095 0.12(2) Uiso 1 1 calc R
C20 C 0.19200(14) 0.5759(6) 0.05787(13) 0.0327(10) Uani 1 1 d .
C21 C 0.18106(14) 0.6223(5) 0.11244(13) 0.0394(10) Uani 1 1 d .
H21A H 0.2133 0.6681 0.1395 0.025(9) Uiso 1 1 calc R
H21B H 0.1697 0.5026 0.1276 0.044(11) Uiso 1 1 calc R
C22 C 0.13950(16) 0.7773(6) 0.10559(14) 0.0464(11) Uani 1 1 d .
H22A H 0.1079 0.7338 0.0771 0.041(11) Uiso 1 1 calc R
H22B H 0.1516 0.8984 0.0919 0.064(13) Uiso 1 1 calc R
C23 C 0.12583(16) 0.8208(6) 0.15984(15) 0.0474(11) Uani 1 1 d .
H23A H 0.1583 0.8315 0.1904 0.048(12) Uiso 1 1 calc R
H23B H 0.1082 0.9485 0.1562 0.073(14) Uiso 1 1 calc R
C24 C 0.09160(16) 0.6706(6) 0.17577(14) 0.0483(11) Uani 1 1 d .
H24A H 0.1056 0.5395 0.1723 0.038(11) Uiso 1 1 calc R
H24B H 0.0566 0.6783 0.1493 0.063(13) Uiso 1 1 calc R
C25 C 0.08733(16) 0.6967(7) 0.23509(14) 0.0560(12) Uani 1 1 d .
H25A H 0.0652 0.5945 0.2433 0.018(9) Uiso 1 1 calc R
H25B H 0.0722 0.8242 0.2384 0.077(16) Uiso 1 1 calc R
H25C H 0.1219 0.6882 0.2616 0.073(14) Uiso 1 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
C18 O3 C19 115.8(4)
C1 N1 C4 127.1(3)
C1 N1 C2 111.6(3)
C4 N1 C2 118.0(3)
C1 N2 C3 113.8(3)
N2 C1 N1 109.1(3)
N2 C1 C17 122.7(3)
N1 C1 C17 128.1(3)
N1 C2 C3 103.6(3)
N2 C3 C11 113.9(3)
N2 C3 C2 101.8(3)
C11 C3 C2 112.1(3)
N1 C4 C5 114.3(3)
C10 C5 C6 118.9(4)
C10 C5 C4 122.6(4)
C6 C5 C4 118.5(4)
C7 C6 C5 119.9(4)
C8 C7 C6 121.7(5)
C7 C8 C9 118.1(5)
C10 C9 C8 120.9(5)
C9 C10 C5 120.4(4)
C16 C11 C12 118.6(4)
C16 C11 C3 118.4(4)
C12 C11 C3 122.9(3)
C11 C12 C13 121.0(3)
C12 C13 C14 119.4(4)
C15 C14 C13 119.9(4)
C14 C15 C16 119.8(4)
C11 C16 C15 121.2(4)
C1 C17 C20 119.7(3)
C1 C17 C18 120.5(3)
C20 C17 C18 119.6(3)
O2 C18 O3 121.4(4)
O2 C18 C17 127.5(4)
O3 C18 C17 111.0(3)
O1 C20 C17 122.5(3)
O1 C20 C21 117.0(3)
C17 C20 C21 120.5(3)
C20 C21 C22 111.7(3)
C21 C22 C23 112.9(3)
C24 C23 C22 114.5(3)
C23 C24 C25 113.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C20 1.257(3)
O2 C18 1.217(4)
O3 C18 1.363(4)
O3 C19 1.446(4)
N1 C1 1.351(4)
N1 C4 1.449(4)
N1 C2 1.460(3)
N2 C1 1.331(3)
N2 C3 1.453(4)
C1 C17 1.425(4)
C2 C3 1.543(4)
C3 C11 1.516(4)
C4 C5 1.510(4)
C5 C10 1.377(4)
C5 C6 1.381(4)
C6 C7 1.375(5)
C7 C8 1.369(5)
C8 C9 1.379(5)
C9 C10 1.375(5)
C11 C16 1.376(4)
C11 C12 1.376(4)
C12 C13 1.382(4)
C13 C14 1.387(4)
C14 C15 1.367(4)
C15 C16 1.380(4)
C17 C20 1.435(4)
C17 C18 1.467(4)
C20 C21 1.507(4)
C21 C22 1.520(4)
C22 C23 1.529(4)
C23 C24 1.510(4)
C24 C25 1.528(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139185212
