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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/31/1513161.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_1513161
loop_
_publ_author_name
'Mercalli, Valentina'
'Meneghetti, Fiorella'
'Tron, Gian Cesare'
_publ_section_title
;
 Isocyanide-Mediated Multicomponent Synthesis of C-Oximinoamidines
;
_journal_issue                   22
_journal_name_full               'Organic Letters'
_journal_page_first              5902
_journal_paper_doi               10.1021/ol403062m
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C17 H25 N3 O2'
_chemical_formula_weight         303.4
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-26T11:27:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.620(8)
_cell_length_b                   8.989(8)
_cell_length_c                   15.810(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      9
_cell_volume                     1640(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.249
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3670
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2178
_reflns_number_gt                1735
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403062m_si_002.cif
_cod_data_source_block           mv222
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               1513161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21884(18) 0.2662(2) 0.24195(12) 0.0539(5) Uani 1 1 d . . .
N1 N 0.22159(18) 0.4202(2) 0.24606(12) 0.0479(6) Uani 1 1 d . A .
N2 N 0.49851(17) 0.3351(2) 0.25738(12) 0.0454(6) Uani 1 1 d . . .
N3 N 0.40679(18) 0.3404(2) 0.11961(13) 0.0488(6) Uani 1 1 d . . .
C4 C 0.3357(2) 0.6355(3) 0.23166(15) 0.0440(6) Uani 1 1 d . A .
C7 C 0.31755(19) 0.4728(3) 0.22834(13) 0.0415(6) Uani 1 1 d . . .
C8 C 0.4133(2) 0.3754(3) 0.20432(14) 0.0413(6) Uani 1 1 d . A .
O2 O 0.3865(2) 0.2253(4) -0.04737(16) 0.0977(10) Uani 1 1 d . . .
C9 C 0.5004(2) 0.3756(3) 0.34726(16) 0.0537(7) Uani 1 1 d . . .
H9A H 0.4447 0.4544 0.3524 0.064 Uiso 1 1 calc R . .
H9B H 0.5766 0.4132 0.3684 0.064 Uiso 1 1 calc R . .
C2 C 0.4491(3) 0.8502(3) 0.20734(18) 0.0612(8) Uani 1 1 d . A .
H2 H 0.5155 0.8906 0.1888 0.073 Uiso 1 1 calc R . .
C3 C 0.4312(2) 0.6988(3) 0.20509(17) 0.0531(7) Uani 1 1 d . . .
H3 H 0.4864 0.6378 0.1847 0.064 Uiso 1 1 calc R A .
C15 C 0.4913(4) 0.2406(6) 0.0928(2) 0.0817(12) Uani 1 1 d . A .
C5 C 0.2544(3) 0.7291(3) 0.26175(19) 0.0615(8) Uani 1 1 d . . .
H5 H 0.1882 0.6892 0.2807 0.074 Uiso 1 1 calc R A .
C1 C 0.3676(3) 0.9413(3) 0.23743(19) 0.0657(8) Uani 1 1 d . . .
H1 H 0.3784 1.0438 0.2398 0.079 Uiso 1 1 calc R A .
C10 C 0.4726(5) 0.2480(5) 0.3998(2) 0.0947(14) Uani 1 1 d . . .
H10A H 0.5315 0.172 0.3978 0.114 Uiso 1 1 calc R . .
H10B H 0.399 0.2058 0.3761 0.114 Uiso 1 1 calc R . .
C6 C 0.2715(3) 0.8792(4) 0.2635(2) 0.0720(9) Uani 1 1 d . A .
H6 H 0.2159 0.9405 0.2831 0.086 Uiso 1 1 calc R . .
C14 C 0.2985(5) 0.3418(8) 0.0642(3) 0.0710(14) Uani 0.75 1 d P A 1
H14A H 0.2565 0.4318 0.075 0.085 Uiso 0.75 1 calc PR A 1
H14B H 0.252 0.2578 0.0784 0.085 Uiso 0.75 1 calc PR A 1
C14A C 0.3318(18) 0.426(2) 0.0591(11) 0.078(5) Uani 0.25 1 d P A 2
H14C H 0.3673 0.5212 0.0492 0.093 Uiso 0.25 1 calc PR A 2
H14D H 0.2584 0.4443 0.0808 0.093 Uiso 0.25 1 calc PR A 2
C16 C 0.4911(5) 0.2328(8) -0.0001(3) 0.0794(15) Uani 0.75 1 d P A 1
H16A H 0.5313 0.3197 -0.0181 0.095 Uiso 0.75 1 calc PR A 1
H16B H 0.5356 0.1462 -0.013 0.095 Uiso 0.75 1 calc PR A 1
C16A C 0.448(2) 0.164(2) 0.0174(13) 0.098(8) Uani 0.25 1 d P A 2
H16C H 0.515 0.1198 -0.0045 0.118 Uiso 0.25 1 calc PR A 2
H16D H 0.4025 0.0814 0.0351 0.118 Uiso 0.25 1 calc PR A 2
C17 C 0.3119(4) 0.3351(6) -0.0260(2) 0.0947(13) Uani 1 1 d . A .
H17A H 0.2364 0.3187 -0.0578 0.114 Uiso 1 1 calc R B 1
H17B H 0.3401 0.4306 -0.0434 0.114 Uiso 1 1 calc R B 1
C11 C 0.4656(5) 0.2912(5) 0.4926(2) 0.1084(17) Uani 1 1 d . . .
H11A H 0.5422 0.3235 0.5165 0.13 Uiso 1 1 calc R . .
H11B H 0.4149 0.3769 0.4925 0.13 Uiso 1 1 calc R . .
C13 C 0.3135(5) 0.1191(8) 0.5245(4) 0.154(3) Uani 1 1 d . . .
H13A H 0.2985 0.0505 0.5684 0.231 Uiso 1 1 calc R . .
H13B H 0.3124 0.067 0.4714 0.231 Uiso 1 1 calc R . .
H13C H 0.2549 0.195 0.5191 0.231 Uiso 1 1 calc R . .
C12 C 0.4284(6) 0.1884(8) 0.5469(3) 0.147(2) Uani 1 1 d . . .
H12A H 0.4284 0.2355 0.602 0.176 Uiso 1 1 calc R . .
H12B H 0.4854 0.1092 0.5536 0.176 Uiso 1 1 calc R . .
H1A H 0.147(4) 0.246(4) 0.245(2) 0.073(10) Uiso 1 1 d . . .
H15A H 0.453(6) 0.147(7) 0.115(4) 0.16(2) Uiso 1 1 d . . .
H15B H 0.578(5) 0.268(5) 0.117(3) 0.118(15) 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 0 '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 0.006 '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 O1 112.2(2)
C8 N2 C9 119.4(2)
C8 N3 C15 118.2(2)
C8 N3 C14 122.4(3)
C15 N3 C14 113.9(3)
C3 C4 C5 117.7(3)
C3 C4 C7 121.5(2)
C5 C4 C7 120.8(2)
N1 C7 C4 119.0(2)
N1 C7 C8 122.3(2)
C4 C7 C8 118.7(2)
N2 C8 N3 121.9(2)
N2 C8 C7 122.8(2)
N3 C8 C7 115.11(19)
C16 O2 C17 112.2(3)
N2 C9 C10 112.0(2)
C3 C2 C1 119.2(3)
C4 C3 C2 122.2(3)
N3 C15 C16 113.9(3)
C6 C5 C4 120.2(3)
C6 C1 C2 119.0(3)
C9 C10 C11 112.5(3)
C1 C6 C5 121.6(3)
N3 C14 C17 114.1(4)
O2 C16 C15 116.8(5)
O2 C17 C14 114.3(4)
C12 C11 C10 119.2(4)
C11 C12 C13 118.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.386(3)
N1 C7 1.272(3)
N2 C8 1.273(3)
N2 C9 1.464(3)
N3 C8 1.369(3)
N3 C15 1.430(4)
N3 C14A 1.440(18)
N3 C14 1.447(5)
C4 C3 1.357(4)
C4 C5 1.390(4)
C4 C7 1.477(4)
C7 C8 1.500(3)
O2 C16A 1.30(2)
O2 C16 1.352(6)
O2 C17 1.382(5)
C9 C10 1.474(5)
C2 C3 1.377(4)
C2 C1 1.378(4)
C15 C16A 1.42(2)
C15 C16 1.470(6)
C5 C6 1.364(5)
C1 C6 1.355(5)
C10 C11 1.528(5)
C14 C17 1.453(6)
C14A C17 1.568(19)
C11 C12 1.365(7)
C13 C12 1.479(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136715195
