#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:49:23 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301117 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/03/7160346.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_7160346
loop_
_publ_author_name
'Lotfi Nosood, Yazdanbakhsh'
'Fattahi Ghahnavieh, Negin'
'Takallou, Ahmad'
'Rostami, Ali'
'Ebrahimi, Amirhossein'
'Anwar, Muhammad U.'
'Al-Harrasi, Ahmed'
_publ_section_title
;
 Microwave-assisted [3 + 2] cycloaddition reactions of dicyanoepoxides
 with benzylidene Meldrum's acids.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4084
_journal_page_last               4089
_journal_paper_doi               10.1039/d4ob01702a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C25 H20 N2 O5'
_chemical_formula_weight         428.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-13 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                115.4180(10)
_cell_angle_beta                 104.594(2)
_cell_angle_gamma                105.643(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7433(4)
_cell_length_b                   11.4423(5)
_cell_length_c                   11.6498(5)
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.1505
_cell_measurement_theta_min      2.315
_cell_volume                     1128.77(9)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-23 && APEX4 2022.10-0'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.185
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.15(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0605
_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)+(0.1071P)²+0.5351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.2278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3071
_reflns_number_total             4609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01702a2.cif
_cod_data_source_block           MD_34_B_R1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160345--7160346.cif.'
_cod_original_cell_volume        1128.76(8)
_cod_database_code               7160346
_shelx_shelxl_version_number     2019/1
_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.
;
_diffrn_measurement_ambient_temperature_device_make '296 K'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48390(19) 0.87300(19) 0.67333(18) 0.0528(5) Uani 1 1 d . . . . .
O2 O 0.55649(19) 0.6108(2) 0.6536(2) 0.0563(5) Uani 1 1 d . . . . .
O3 O 0.3902(2) 0.4609(2) 0.6634(2) 0.0651(6) Uani 1 1 d . . . . .
O4 O 0.1680(2) 0.4691(2) 0.6420(2) 0.0634(6) Uani 1 1 d . . . . .
O5 O 0.1227(2) 0.6396(2) 0.6301(2) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.1766(3) 0.8794(3) 0.5097(3) 0.0721(7) Uani 1 1 d . . . . .
N2 N 0.5124(3) 0.8387(3) 0.3828(3) 0.0781(8) Uani 1 1 d . . . . .
C8 C 0.2392(3) 0.3765(3) 0.6097(4) 0.0649(8) Uani 1 1 d . . . . .
C9 C 0.2005(3) 0.5823(3) 0.6283(3) 0.0477(6) Uani 1 1 d . . . . .
C10 C 0.1864(3) 0.5456(3) 0.3559(3) 0.0491(6) Uani 1 1 d . . . . .
H10 H 0.103155 0.546496 0.365265 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1799(3) 0.4642(3) 0.2311(3) 0.0549(7) Uani 1 1 d . . . . .
H11 H 0.264987 0.461669 0.228618 0.066 Uiso 1 1 calc R U . . .
C12 C 0.0547(3) 0.3773(3) 0.0957(3) 0.0559(7) Uani 1 1 d . . . . .
C13 C -0.0707(3) 0.3933(4) 0.0744(3) 0.0709(9) Uani 1 1 d . . . . .
H13 H -0.078676 0.462201 0.148682 0.085 Uiso 1 1 calc R U . . .
C14 C -0.1838(4) 0.3080(5) -0.0559(4) 0.0881(12) Uani 1 1 d . . . . .
H14 H -0.267690 0.319478 -0.069293 0.106 Uiso 1 1 calc R U . . .
C15 C -0.1732(4) 0.2053(5) -0.1673(4) 0.0895(12) Uani 1 1 d . . . . .
H15 H -0.250728 0.146082 -0.254610 0.107 Uiso 1 1 calc R U . . .
C16 C -0.0500(5) 0.1913(5) -0.1488(4) 0.0951(12) Uani 1 1 d . . . . .
H16 H -0.041971 0.123863 -0.224103 0.114 Uiso 1 1 calc R U . . .
C17 C 0.0633(4) 0.2765(4) -0.0191(3) 0.0807(10) Uani 1 1 d . . . . .
H17 H 0.147833 0.266332 -0.007976 0.097 Uiso 1 1 calc R U . . .
C18 C 0.5350(3) 0.8530(3) 0.8756(3) 0.0502(6) Uani 1 1 d . . . . .
C19 C 0.6771(3) 0.9340(3) 0.9188(3) 0.0671(8) Uani 1 1 d . . . . .
H19 H 0.706607 0.959762 0.861146 0.081 Uiso 1 1 calc R U . . .
C20 C 0.7767(4) 0.9775(4) 1.0489(4) 0.0810(10) Uani 1 1 d . . . . .
H20 H 0.872376 1.034009 1.078737 0.097 Uiso 1 1 calc R U . . .
C21 C 0.7350(4) 0.9379(4) 1.1329(3) 0.0799(10) Uani 1 1 d . . . . .
H21 H 0.802270 0.966081 1.219019 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5955(5) 0.8575(4) 1.0907(3) 0.0803(10) Uani 1 1 d . . . . .
H22 H 0.567419 0.830356 1.148138 0.096 Uiso 1 1 calc R U . . .
C23 C 0.4935(4) 0.8150(4) 0.9622(3) 0.0667(8) Uani 1 1 d . . . . .
H23 H 0.397624 0.761227 0.934897 0.080 Uiso 1 1 calc R U . . .
C24 C 0.2224(5) 0.3046(5) 0.6897(5) 0.0950(13) Uani 1 1 d . . . . .
H24A H 0.122795 0.250716 0.660634 0.142 Uiso 1 1 calc R U . . .
H24B H 0.265864 0.375886 0.788265 0.142 Uiso 1 1 calc R U . . .
H24C H 0.267727 0.241035 0.671660 0.142 Uiso 1 1 calc R U . . .
C25 C 0.1772(4) 0.2760(4) 0.4544(4) 0.0831(10) Uani 1 1 d . . . . .
H25A H 0.076320 0.222417 0.419418 0.125 Uiso 1 1 calc R U . . .
H25B H 0.220938 0.211127 0.432979 0.125 Uiso 1 1 calc R U . . .
H25C H 0.194641 0.329838 0.411106 0.125 Uiso 1 1 calc R U . . .
C1 C 0.4227(3) 0.8068(3) 0.7380(3) 0.0463(6) Uani 1 1 d . . . . .
H1 H 0.351071 0.840105 0.757326 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3419(2) 0.6401(3) 0.6222(3) 0.0439(6) Uani 1 1 d . . . . .
C3 C 0.3255(2) 0.6361(3) 0.4822(2) 0.0450(6) Uani 1 1 d . . . . .
H3 H 0.394599 0.603988 0.454142 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3834(3) 0.7987(3) 0.5335(3) 0.0483(6) Uani 1 1 d . . . . .
C5 C 0.4576(3) 0.8259(3) 0.4509(3) 0.0562(7) Uani 1 1 d . . . . .
C6 C 0.2671(3) 0.8459(3) 0.5206(3) 0.0533(6) Uani 1 1 d . . . . .
C7 C 0.4380(3) 0.5688(3) 0.6446(3) 0.0464(6) Uani 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
_geom_angle_publ_flag
C4 O1 C1 106.30(18) . . ?
C7 O3 C8 120.7(2) . . ?
C9 O4 C8 121.6(2) . . ?
O3 C8 O4 110.2(2) . . ?
O3 C8 C25 110.1(3) . . ?
O4 C8 C25 109.3(3) . . ?
O3 C8 C24 106.5(3) . . ?
O4 C8 C24 106.0(3) . . ?
C25 C8 C24 114.5(3) . . ?
O5 C9 O4 119.4(2) . . ?
O5 C9 C2 122.3(2) . . ?
O4 C9 C2 118.2(2) . . ?
C11 C10 C3 120.8(2) . . ?
C10 C11 C12 127.9(3) . . ?
C13 C12 C17 117.8(3) . . ?
C13 C12 C11 123.7(3) . . ?
C17 C12 C11 118.5(3) . . ?
C14 C13 C12 120.4(3) . . ?
C13 C14 C15 120.3(4) . . ?
C16 C15 C14 119.8(3) . . ?
C15 C16 C17 120.1(4) . . ?
C16 C17 C12 121.5(4) . . ?
C19 C18 C23 119.2(3) . . ?
C19 C18 C1 122.1(2) . . ?
C23 C18 C1 118.8(3) . . ?
C18 C19 C20 119.9(3) . . ?
C21 C20 C19 120.5(3) . . ?
C22 C21 C20 119.9(3) . . ?
C21 C22 C23 120.7(3) . . ?
C18 C23 C22 119.8(3) . . ?
O1 C1 C18 110.2(2) . . ?
O1 C1 C2 105.43(18) . . ?
C18 C1 C2 117.3(2) . . ?
C9 C2 C7 115.2(2) . . ?
C9 C2 C3 113.4(2) . . ?
C7 C2 C3 107.71(18) . . ?
C9 C2 C1 107.48(19) . . ?
C7 C2 C1 109.34(19) . . ?
C3 C2 C1 102.94(19) . . ?
C10 C3 C4 113.2(2) . . ?
C10 C3 C2 121.0(2) . . ?
C4 C3 C2 102.28(19) . . ?
O1 C4 C5 108.2(2) . . ?
O1 C4 C6 111.8(2) . . ?
C5 C4 C6 109.3(2) . . ?
O1 C4 C3 106.05(19) . . ?
C5 C4 C3 109.5(2) . . ?
C6 C4 C3 111.9(2) . . ?
N2 C5 C4 176.1(3) . . ?
N1 C6 C4 178.8(3) . . ?
O2 C7 O3 119.3(2) . . ?
O2 C7 C2 122.4(2) . . ?
O3 C7 C2 118.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.404(3) . ?
O1 C1 1.430(3) . ?
O2 C7 1.192(3) . ?
O3 C7 1.335(3) . ?
O3 C8 1.443(4) . ?
O4 C9 1.337(3) . ?
O4 C8 1.445(3) . ?
O5 C9 1.193(3) . ?
N1 C6 1.135(4) . ?
N2 C5 1.134(4) . ?
C8 C25 1.494(5) . ?
C8 C24 1.498(5) . ?
C9 C2 1.517(3) . ?
C10 C11 1.318(4) . ?
C10 C3 1.490(3) . ?
C11 C12 1.466(4) . ?
C12 C13 1.384(4) . ?
C12 C17 1.387(4) . ?
C13 C14 1.376(5) . ?
C14 C15 1.383(6) . ?
C15 C16 1.351(6) . ?
C16 C17 1.373(5) . ?
C18 C19 1.376(4) . ?
C18 C23 1.380(4) . ?
C18 C1 1.503(3) . ?
C19 C20 1.392(4) . ?
C20 C21 1.361(5) . ?
C21 C22 1.354(6) . ?
C22 C23 1.392(5) . ?
C1 C2 1.587(3) . ?
C2 C7 1.517(3) . ?
C2 C3 1.575(3) . ?
C3 C4 1.562(4) . ?
C4 C5 1.473(4) . ?
C4 C6 1.488(4) . ?
