#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036407.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_4036407
loop_
_publ_author_name
'Liu, Gong-Qing'
'Yang, Chun-Hua'
'Li, Yue-Ming'
_publ_section_title
;
 Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)2-Promoted
 Intramolecular Halooxygenation of N-Allylcarboxamides.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11339
_journal_page_last               11350
_journal_paper_doi               10.1021/acs.joc.5b01832
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C11 H12 I N O2'
_chemical_formula_weight         317.12
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.334(3)
_cell_length_b                   6.3606(13)
_cell_length_c                   23.307(5)
_cell_measurement_reflns_used    5092
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8824
_cell_measurement_theta_min      1.7475
_cell_volume                     2273.2(8)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16784
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_T_max  0.7301
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       0.0023(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   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0382
_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)+(0.0362P)²+2.0728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2336
_reflns_number_total             2721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01832_si_002.cif
_cod_data_source_block           r150414c1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4036407
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
I1 I 0.08415(19) 0.4408(6) 1.16266(14) 0.0239(4) Uani 0.467(7) 1 d PD A 1
O1 O 0.0777(5) 0.7807(17) 1.0017(3) 0.0264(13) Uani 0.467(7) 1 d PD A 1
N1 N 0.1717(19) 1.024(3) 1.0393(8) 0.026(4) Uani 0.467(7) 1 d PD A 1
C1 C 0.1055(6) 0.5015(12) 1.0691(3) 0.031(2) Uani 0.467(7) 1 d PD A 1
H1A H 0.1673 0.4798 1.0583 0.037 Uiso 0.467(7) 1 calc PR A 1
H1B H 0.0681 0.4097 1.0452 0.037 Uiso 0.467(7) 1 calc PR A 1
C2 C 0.0794(5) 0.7301(11) 1.0632(3) 0.0247(18) Uani 0.467(7) 1 d PD A 1
H2A H 0.0211 0.7558 1.0811 0.030 Uiso 0.467(7) 1 calc PR A 1
C3 C 0.1481(19) 0.883(3) 1.0874(10) 0.0381(11) Uani 0.467(7) 1 d PD A 1
H3A H 0.1236 0.9652 1.1197 0.046 Uiso 0.467(7) 1 calc PR A 1
H3B H 0.2000 0.8057 1.1011 0.046 Uiso 0.467(7) 1 calc PR A 1
C4 C 0.1293(9) 0.956(2) 0.9961(4) 0.0264(8) Uani 0.467(7) 1 d PD A 1
I1' I 0.1042(2) 0.4226(6) 1.15917(13) 0.0283(4) Uani 0.533(7) 1 d PD A 2
O1' O 0.1095(5) 0.7418(14) 0.9967(3) 0.0264(13) Uani 0.533(7) 1 d PD A 2
N1' N 0.1535(15) 1.044(3) 1.0420(7) 0.026(4) Uani 0.533(7) 1 d PD A 2
C1' C 0.0547(4) 0.5486(10) 1.0775(2) 0.0237(15) Uani 0.533(7) 1 d PD A 2
H1'A H 0.0379 0.4340 1.0509 0.028 Uiso 0.533(7) 1 calc PR A 2
H1'B H 0.0039 0.6419 1.0837 0.028 Uiso 0.533(7) 1 calc PR A 2
C2' C 0.1319(4) 0.6699(11) 1.0548(2) 0.0261(16) Uani 0.533(7) 1 d PD A 2
H2'A H 0.1852 0.5794 1.0540 0.031 Uiso 0.533(7) 1 calc PR A 2
C3' C 0.1503(17) 0.878(3) 1.0864(8) 0.0381(11) Uani 0.533(7) 1 d PD A 2
H3'A H 0.1035 0.9079 1.1145 0.046 Uiso 0.533(7) 1 calc PR A 2
H3'B H 0.2066 0.8698 1.1072 0.046 Uiso 0.533(7) 1 calc PR A 2
C4' C 0.1324(7) 0.9515(19) 0.9954(3) 0.0264(8) Uani 0.533(7) 1 d PD A 2
O2 O 0.12592(17) 1.3164(4) 0.77627(10) 0.0309(6) Uani 1 1 d . . .
C5 C 0.1299(2) 1.0507(5) 0.93808(13) 0.0217(6) Uani 1 1 d D . .
C6 C 0.0903(2) 0.9500(6) 0.89192(16) 0.0271(8) Uani 1 1 d . A .
H6A H 0.0644 0.8156 0.8970 0.032 Uiso 1 1 calc R . .
C7 C 0.0889(2) 1.0460(6) 0.83859(13) 0.0246(8) Uani 1 1 d . . .
H7A H 0.0601 0.9795 0.8074 0.030 Uiso 1 1 calc R A .
C8 C 0.1293(2) 1.2388(5) 0.83054(13) 0.0239(7) Uani 1 1 d . A .
C9 C 0.1702(2) 1.3399(5) 0.87645(14) 0.0262(7) Uani 1 1 d . . .
H9A H 0.1980 1.4718 0.8711 0.031 Uiso 1 1 calc R A .
C10 C 0.1695(2) 1.2448(5) 0.92988(14) 0.0253(7) Uani 1 1 d . A .
H10A H 0.1966 1.3133 0.9614 0.030 Uiso 1 1 calc R . .
C11 C 0.1664(3) 1.5152(6) 0.76520(16) 0.0439(11) Uani 1 1 d . . .
H11A H 0.1589 1.5518 0.7247 0.066 Uiso 1 1 calc R . .
H11B H 0.2287 1.5063 0.7742 0.066 Uiso 1 1 calc R . .
H11C H 0.1392 1.6234 0.7892 0.066 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'
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
C4 O1 C2 105.1(6)
C4 N1 C3 105.7(13)
C2 C1 I1 102.4(5)
C2 C1 H1A 111.3
I1 C1 H1A 111.3
C2 C1 H1B 111.3
I1 C1 H1B 111.3
H1A C1 H1B 109.2
O1 C2 C1 107.7(6)
O1 C2 C3 103.3(11)
C1 C2 C3 113.2(13)
O1 C2 H2A 110.8
C1 C2 H2A 110.8
C3 C2 H2A 110.8
N1 C3 C2 105.8(13)
N1 C3 H3A 110.6
C2 C3 H3A 110.6
N1 C3 H3B 110.6
C2 C3 H3B 110.6
H3A C3 H3B 108.7
N1 C4 O1 119.5(9)
N1 C4 C5 125.7(14)
O1 C4 C5 114.8(9)
C4' O1' C2' 105.2(6)
C4' N1' C3' 105.1(12)
C2' C1' I1' 102.7(4)
C2' C1' H1'A 111.2
I1' C1' H1'A 111.2
C2' C1' H1'B 111.2
I1' C1' H1'B 111.2
H1'A C1' H1'B 109.1
O1' C2' C1' 107.4(5)
O1' C2' C3' 102.5(10)
C1' C2' C3' 114.5(10)
O1' C2' H2'A 110.7
C1' C2' H2'A 110.7
C3' C2' H2'A 110.7
N1' C3' C2' 106.4(12)
N1' C3' H3'A 110.4
C2' C3' H3'A 110.4
N1' C3' H3'B 110.4
C2' C3' H3'B 110.4
H3'A C3' H3'B 108.6
N1' C4' O1' 119.4(8)
N1' C4' C5 125.5(13)
O1' C4' C5 115.2(8)
C8 O2 C11 118.2(3)
C10 C5 C6 119.6(3)
C10 C5 C4 119.2(6)
C6 C5 C4 121.2(6)
C10 C5 C4' 119.5(6)
C6 C5 C4' 120.9(6)
C4 C5 C4' 2.3(9)
C7 C6 C5 119.9(3)
C7 C6 H6A 120.1
C5 C6 H6A 120.1
C6 C7 C8 120.3(3)
C6 C7 H7A 119.9
C8 C7 H7A 119.9
O2 C8 C7 115.5(3)
O2 C8 C9 124.3(3)
C7 C8 C9 120.3(3)
C10 C9 C8 119.0(3)
C10 C9 H9A 120.5
C8 C9 H9A 120.5
C9 C10 C5 121.0(3)
C9 C10 H10A 119.5
C5 C10 H10A 119.5
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.239(6)
O1 C4 1.376(11)
O1 C2 1.470(7)
N1 C4 1.275(8)
N1 C3 1.479(9)
C1 C2 1.514(8)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.542(10)
C2 H2A 1.0000
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.478(7)
I1' C1' 2.201(5)
O1' C4' 1.380(10)
O1' C2' 1.469(6)
N1' C4' 1.275(7)
N1' C3' 1.479(8)
C1' C2' 1.509(7)
C1' H1'A 0.9900
C1' H1'B 0.9900
C2' C3' 1.541(10)
C2' H2'A 1.0000
C3' H3'A 0.9900
C3' H3'B 0.9900
C4' C5 1.478(7)
O2 C8 1.359(4)
O2 C11 1.431(5)
C5 C10 1.389(5)
C5 C6 1.391(5)
C6 C7 1.385(5)
C6 H6A 0.9500
C7 C8 1.387(5)
C7 H7A 0.9500
C8 C9 1.397(5)
C9 C10 1.385(5)
C9 H9A 0.9500
C10 H10A 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
C4 O1 C2 C1 -127.3(9)
C4 O1 C2 C3 -7.3(15)
I1 C1 C2 O1 -171.4(5)
I1 C1 C2 C3 75.0(13)
C4 N1 C3 C2 -3(3)
O1 C2 C3 N1 7(2)
C1 C2 C3 N1 123(2)
C3 N1 C4 O1 -2(2)
C3 N1 C4 C5 178(2)
C2 O1 C4 N1 6.3(8)
C2 O1 C4 C5 -173.8(8)
C4' O1' C2' C1' 132.6(7)
C4' O1' C2' C3' 11.6(12)
I1' C1' C2' O1' 173.6(5)
I1' C1' C2' C3' -73.2(11)
C4' N1' C3' C2' 5(2)
O1' C2' C3' N1' -11(2)
C1' C2' C3' N1' -126.5(16)
C3' N1' C4' O1' 2.7(17)
C3' N1' C4' C5 -177.3(17)
C2' O1' C4' N1' -9.9(7)
C2' O1' C4' C5 170.1(6)
N1 C4 C5 C10 -9.3(7)
O1 C4 C5 C10 170.8(6)
N1 C4 C5 C6 171.7(11)
O1 C4 C5 C6 -8.3(11)
N1 C4 C5 C4' 87(26)
O1 C4 C5 C4' -93(26)
N1' C4' C5 C10 14.1(6)
O1' C4' C5 C10 -165.9(6)
N1' C4' C5 C6 -167.6(9)
O1' C4' C5 C6 12.4(9)
N1' C4' C5 C4 -71(26)
O1' C4' C5 C4 109(26)
C10 C5 C6 C7 -1.6(5)
C4 C5 C6 C7 177.4(6)
C4' C5 C6 C7 -179.9(5)
C5 C6 C7 C8 2.3(5)
C11 O2 C8 C7 179.9(3)
C11 O2 C8 C9 -0.4(5)
C6 C7 C8 O2 178.3(3)
C6 C7 C8 C9 -1.4(5)
O2 C8 C9 C10 -179.8(3)
C7 C8 C9 C10 -0.1(5)
C8 C9 C10 C5 0.7(5)
C6 C5 C10 C9 0.1(5)
C4 C5 C10 C9 -178.9(6)
C4' C5 C10 C9 178.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329931
