#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/02/1520223.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_1520223
loop_
_publ_author_name
'Skvorcova, Marija'
'Grigorjeva, Liene'
'Jirgensons, Aigars'
_publ_section_title
;
 Tetrahydro-1,3-oxazepines via Intramolecular Amination of
 Cyclopropylmethyl Cation.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2902
_journal_page_last               2904
_journal_paper_doi               10.1021/acs.orglett.5b01014
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C14 H16 Cl3 N O3'
_chemical_formula_weight         352.63
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   16.1172(12)
_cell_length_b                   16.1172(12)
_cell_length_c                   5.6393(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1268.63(16)
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1382
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3642
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2304
_refine_ls_R_factor_gt           0.0888
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0920P)²+0.9116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2421
_reflns_number_gt                1527
_reflns_number_total             3642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01014_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1520223.cif.'
_cod_original_cell_volume        1268.6(2)
_cod_database_code               1520223
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
Cl1 Cl 0.40633(18) 0.9495(2) 0.7827(6) 0.1203(11) Uani 1 1 d .
Cl2 Cl 0.4392(2) 0.7926(2) 0.7749(8) 0.1369(13) Uani 1 1 d .
C2 C 0.5667(5) 0.9653(5) 0.9793(14) 0.0588(18) Uani 1 1 d .
C3 C 0.7221(5) 1.0496(6) 0.7847(12) 0.0593(19) Uani 1 1 d .
H3 H 0.7459 1.0409 0.9373 0.071 Uiso 1 1 calc R
N1 N 0.6173(4) 0.9876(4) 0.7865(11) 0.0671(17) Uani 1 1 d .
H1 H 0.5883 0.9650 0.6539 0.080 Uiso 1 1 calc R
C10 C 0.7653(5) 1.0156(5) 0.5908(12) 0.061(2) Uani 1 1 d .
H10 H 0.7408 1.0233 0.4383 0.073 Uiso 1 1 calc R
C5 C 0.7231(6) 1.1893(7) 0.5799(16) 0.074(2) Uani 1 1 d .
H5 H 0.6842 1.1470 0.4632 0.088 Uiso 1 1 calc R
C11 C 0.7360(6) 0.9121(7) 0.6142(15) 0.076(2) Uani 1 1 d .
O1 O 0.5957(4) 0.9936(5) 1.1783(10) 0.0882(17) Uani 1 1 d .
C4 C 0.7521(5) 1.1541(6) 0.7648(13) 0.057(2) Uani 1 1 d .
O3 O 0.9157(5) 1.0416(5) 0.4302(14) 0.113(2) Uani 1 1 d .
H3A H 0.9482 1.0823 0.3314 0.170 Uiso 1 1 calc R
C14 C 0.8737(6) 1.0784(6) 0.5840(16) 0.078(2) Uani 1 1 d .
H14A H 0.8903 1.1424 0.5328 0.094 Uiso 1 1 calc R
H14B H 0.8992 1.0833 0.7425 0.094 Uiso 1 1 calc R
O2 O 0.8673(5) 0.8943(6) 0.7344(11) 0.111(2) Uani 1 1 d .
H2 H 0.8720 0.9050 0.5914 0.166 Uiso 1 1 calc R
C13 C 0.7795(8) 0.8815(8) 0.8156(19) 0.102(3) Uani 1 1 d .
H13A H 0.7893 0.9204 0.9555 0.122 Uiso 1 1 calc R
H13B H 0.7369 0.8149 0.8566 0.122 Uiso 1 1 calc R
C8 C 0.8351(8) 1.3156(8) 0.912(2) 0.098(3) Uani 1 1 d .
H8 H 0.8716 1.3583 1.0310 0.117 Uiso 1 1 calc R
C9 C 0.8089(7) 1.2193(7) 0.9292(15) 0.079(2) Uani 1 1 d .
H9 H 0.8310 1.1992 1.0568 0.095 Uiso 1 1 calc R
C7 C 0.8079(8) 1.3465(7) 0.725(2) 0.101(3) Uani 1 1 d .
H7 H 0.8290 1.4114 0.7072 0.122 Uiso 1 1 calc R
C1 C 0.4574(6) 0.8937(7) 0.9465(14) 0.080(3) Uani 1 1 d .
C12 C 0.6739(9) 0.8472(8) 0.468(2) 0.116(4) Uani 1 1 d .
H12A H 0.6473 0.8653 0.3460 0.139 Uiso 1 1 calc R
H12B H 0.6568 0.7832 0.4854 0.139 Uiso 1 1 calc R
C6 C 0.7484(7) 1.2817(8) 0.5606(19) 0.091(3) Uani 1 1 d .
H6 H 0.7256 1.3019 0.4348 0.110 Uiso 1 1 calc R
Cl3 Cl 0.4017(2) 0.8578(5) 1.2109(6) 0.232(3) 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'
Cl Cl 0.1484 0.1585 '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
O1 C2 N1 126.9(7)
O1 C2 C1 117.9(7)
N1 C2 C1 115.2(7)
N1 C3 C4 112.2(6)
N1 C3 C10 109.5(6)
C4 C3 C10 113.4(6)
C2 N1 C3 122.9(6)
C11 C10 C14 111.2(7)
C11 C10 C3 112.9(6)
C14 C10 C3 110.8(6)
C6 C5 C4 122.9(9)
C12 C11 C10 121.5(9)
C12 C11 C13 119.7(10)
C10 C11 C13 118.8(8)
C9 C4 C5 115.9(8)
C9 C4 C3 122.0(8)
C5 C4 C3 122.1(7)
O3 C14 C10 111.8(7)
O2 C13 C11 107.4(8)
C7 C8 C9 120.0(9)
C4 C9 C8 121.7(9)
C8 C7 C6 119.2(10)
C2 C1 Cl3 111.1(6)
C2 C1 Cl1 109.2(6)
Cl3 C1 Cl1 109.6(6)
C2 C1 Cl2 110.4(6)
Cl3 C1 Cl2 110.4(6)
Cl1 C1 Cl2 106.1(5)
C5 C6 C7 120.1(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.755(10)
Cl2 C1 1.789(10)
C2 O1 1.214(9)
C2 N1 1.298(9)
C2 C1 1.560(11)
C3 N1 1.472(9)
C3 C4 1.507(11)
C3 C10 1.536(10)
C10 C11 1.496(12)
C10 C14 1.520(11)
C5 C6 1.336(12)
C5 C4 1.375(11)
C11 C12 1.316(12)
C11 C13 1.540(14)
C4 C9 1.356(11)
O3 C14 1.401(10)
O2 C13 1.400(12)
C8 C7 1.328(15)
C8 C9 1.394(13)
C7 C6 1.369(14)
C1 Cl3 1.687(8)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C2 N1 C3 2.9(12)
C1 C2 N1 C3 -176.4(7)
C4 C3 N1 C2 -87.9(8)
C10 C3 N1 C2 145.3(7)
N1 C3 C10 C11 -54.6(8)
C4 C3 C10 C11 179.3(7)
N1 C3 C10 C14 179.9(6)
C4 C3 C10 C14 53.8(8)
C14 C10 C11 C12 -127.9(10)
C3 C10 C11 C12 106.9(10)
C14 C10 C11 C13 52.4(10)
C3 C10 C11 C13 -72.9(9)
C6 C5 C4 C9 -0.1(12)
C6 C5 C4 C3 179.5(8)
N1 C3 C4 C9 122.5(7)
C10 C3 C4 C9 -112.8(8)
N1 C3 C4 C5 -57.0(9)
C10 C3 C4 C5 67.6(9)
C11 C10 C14 O3 45.9(9)
C3 C10 C14 O3 172.3(7)
C12 C11 C13 O2 95.0(12)
C10 C11 C13 O2 -85.2(10)
C5 C4 C9 C8 0.7(12)
C3 C4 C9 C8 -178.9(8)
C7 C8 C9 C4 -3.1(15)
C9 C8 C7 C6 4.7(16)
O1 C2 C1 Cl3 -7.5(10)
N1 C2 C1 Cl3 171.9(7)
O1 C2 C1 Cl1 113.4(7)
N1 C2 C1 Cl1 -67.2(8)
O1 C2 C1 Cl2 -130.3(7)
N1 C2 C1 Cl2 49.1(8)
C4 C5 C6 C7 1.8(14)
C8 C7 C6 C5 -4.2(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045443
