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#$Date: 2021-08-26 01:10:28 +0300 (Thu, 26 Aug 2021) $
#$Revision: 268203 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564396.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_1564396
loop_
_publ_author_name
'Fominova, Kateryna'
'Diachuk, Taras'
'Granat, Dmitry'
'Savchuk, Taras'
'Vilchynskyi, Vladyslav'
'Svitlychnyi, Oleksiy'
'Meliantsev, Vladyslav'
'Kovalchuk, Igor'
'Litskan, Eduard'
'Levterov, Vadym V.'
'Badlo, Valentyn R.'
'Vaskevych, Ruslan I.'
'Vaskevych, Alla I.'
'Bolbut, Andrii V.'
'Semeno, Volodymyr V.'
'Iminov, Rustam'
'Shvydenko, Kostiantyn'
'Kuznetsova, Anastasiia S.'
'Dmytriv, Yurii V.'
'Vysochyn, Daniil'
'Ripenko, Vasyl'
'Tolmachev, Andrei A.'
'Pavlova, Olexandra'
'Kuznietsova, Halyna'
'Pishel, Iryna'
'Borysko, Petro'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Oxa-spirocycles: synthesis, properties and applications
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03615G
_journal_year                    2021
_chemical_formula_moiety         'C11 H19 I2 N O3'
_chemical_formula_sum            'C11 H19 I2 N O3'
_chemical_formula_weight         467.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.683(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8354(10)
_cell_length_b                   5.8785(4)
_cell_length_c                   18.7559(12)
_cell_measurement_reflns_used    3543
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.20
_cell_volume                     1616.95(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.781
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.888
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0301P)²+1.0543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2443
_reflns_number_total             3085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03615g2.cif
_cod_data_source_block           xr341
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1564396
_shelx_shelxl_version_number     2016/4
_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_min   0.257
_shelx_estimated_absorpt_t_max   0.860
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
I1 I -0.08445(3) 0.02738(6) 0.59219(2) 0.03405(13) Uani 1 1 d . . . . .
I2 I 0.27812(3) 0.38760(9) 0.48087(2) 0.05604(17) Uani 1 1 d . . . . .
N1 N 0.0902(3) 0.5674(7) 0.6985(2) 0.0273(10) Uani 1 1 d . . . . .
O1 O -0.0259(2) 0.5863(6) 0.76086(19) 0.0322(9) Uani 1 1 d . . . . .
O2 O 0.1059(2) 0.7768(7) 0.80115(19) 0.0351(9) Uani 1 1 d . . . . .
O3 O 0.2163(3) 0.2508(7) 0.6373(2) 0.0299(9) Uani 1 1 d . . . . .
C1 C 0.1808(3) 0.6246(9) 0.6818(3) 0.0285(12) Uani 1 1 d . . . . .
H1A H 0.228825 0.587354 0.722755 0.034 Uiso 1 1 calc R U . . .
H1B H 0.184860 0.788172 0.670105 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1895(3) 0.4753(9) 0.6158(3) 0.0264(12) Uani 1 1 d . . . . .
C3 C 0.0904(3) 0.4594(9) 0.5790(3) 0.0263(12) Uani 1 1 d . . . . .
H3A H 0.081466 0.324025 0.547339 0.032 Uiso 1 1 calc R U . . .
H3B H 0.073040 0.596806 0.549654 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0333(3) 0.4399(8) 0.6406(3) 0.0230(11) Uani 1 1 d . . . . .
H4 H -0.026953 0.516868 0.626963 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0602(3) 0.6521(9) 0.7568(3) 0.0278(12) Uani 1 1 d . . . . .
C6 C -0.0737(4) 0.6640(9) 0.8196(3) 0.0310(13) Uani 1 1 d . . . . .
C7 C -0.0257(5) 0.5728(11) 0.8908(3) 0.0510(17) Uani 1 1 d . . . . .
H7A H -0.057633 0.624678 0.929880 0.077 Uiso 1 1 calc R U . . .
H7B H -0.025607 0.406163 0.889402 0.077 Uiso 1 1 calc R U . . .
H7C H 0.037280 0.628531 0.899128 0.077 Uiso 1 1 calc R U . . .
C8 C -0.1670(4) 0.5508(11) 0.7994(3) 0.0440(16) Uani 1 1 d . . . . .
H8A H -0.206089 0.590396 0.835229 0.066 Uiso 1 1 calc R U . . .
H8B H -0.195260 0.604208 0.751729 0.066 Uiso 1 1 calc R U . . .
H8C H -0.159301 0.385335 0.798258 0.066 Uiso 1 1 calc R U . . .
C9 C -0.0833(4) 0.9184(9) 0.8183(3) 0.0430(15) Uani 1 1 d . . . . .
H9A H -0.115244 0.966959 0.857790 0.064 Uiso 1 1 calc R U . . .
H9B H -0.022617 0.988283 0.824240 0.064 Uiso 1 1 calc R U . . .
H9C H -0.118113 0.965811 0.772153 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2551(4) 0.5872(9) 0.5722(3) 0.0318(13) Uani 1 1 d . . . . .
H10A H 0.314088 0.612689 0.603674 0.038 Uiso 1 1 calc R U . . .
H10B H 0.230563 0.737492 0.555213 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0199(3) 0.1990(9) 0.6649(3) 0.0270(12) Uani 1 1 d . . . . .
H11A H 0.002674 0.201315 0.713861 0.032 Uiso 1 1 calc R U . . .
H11B H 0.078029 0.114440 0.667351 0.032 Uiso 1 1 calc R U . . .
H3O H 0.261(4) 0.239(11) 0.657(3) 0.04(2) 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'
I I -0.4742 1.8119 '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
C5 N1 C1 121.3(4) . . ?
C5 N1 C4 124.5(4) . . ?
C1 N1 C4 113.6(4) . . ?
C5 O1 C6 121.4(4) . . ?
N1 C1 C2 103.5(4) . . ?
O3 C2 C10 112.5(4) . . ?
O3 C2 C3 106.2(4) . . ?
C10 C2 C3 115.9(4) . . ?
O3 C2 C1 110.8(4) . . ?
C10 C2 C1 109.0(4) . . ?
C3 C2 C1 101.8(4) . . ?
C2 C3 C4 105.6(4) . . ?
N1 C4 C11 109.9(4) . . ?
N1 C4 C3 101.3(4) . . ?
C11 C4 C3 114.2(4) . . ?
O2 C5 N1 123.7(5) . . ?
O2 C5 O1 124.2(5) . . ?
N1 C5 O1 112.0(4) . . ?
O1 C6 C9 110.6(4) . . ?
O1 C6 C7 109.5(5) . . ?
C9 C6 C7 113.4(5) . . ?
O1 C6 C8 101.5(4) . . ?
C9 C6 C8 110.5(5) . . ?
C7 C6 C8 110.6(5) . . ?
C2 C10 I2 112.7(4) . . ?
C4 C11 I1 111.3(3) . . ?
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
I1 C11 2.154(5) . ?
I2 C10 2.146(5) . ?
N1 C5 1.338(6) . ?
N1 C1 1.464(6) . ?
N1 C4 1.476(6) . ?
O1 C5 1.347(6) . ?
O1 C6 1.471(6) . ?
O2 C5 1.232(6) . ?
O3 C2 1.419(6) . ?
C1 C2 1.540(7) . ?
C2 C10 1.512(7) . ?
C2 C3 1.530(7) . ?
C3 C4 1.535(7) . ?
C4 C11 1.510(7) . ?
C6 C9 1.502(7) . ?
C6 C7 1.513(8) . ?
C6 C8 1.530(7) . ?
