#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/22/2242219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242219
loop_
_publ_author_name
'Rivera, Augusto'
'Rojas, Jicli José'
'Ríos-Motta, Jaime'
'Bolte, Michael'
_publ_section_title
;
 C---I···N short contacts as tools for the
 construction of the crystal packing in the crystal structure of
 3,3'-(ethane-1,2-diyl)bis(6-iodo-3,4-dihydro-2H-1,3-benzoxazine)
;
_journal_coeditor_code           HB7668
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              664
_journal_page_last               666
_journal_paper_doi               10.1107/S2056989017005047
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C18 H18 I2 N2 O2'
_chemical_formula_moiety         'C18 H18 I2 N2 O2'
_chemical_formula_sum            'C18 H18 I2 N2 O2'
_chemical_formula_weight         548.14
_chemical_name_systematic
;
3,3'-(Ethane-1,2-diyl)bis(6-iodo-3,4-dihydro-2H-1,3-benzoxazine)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 123.607(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4200(9)
_cell_length_b                   5.9477(2)
_cell_length_c                   17.8414(8)
_cell_measurement_reflns_used    39259
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      3.34
_cell_volume                     1804.69(14)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39259
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.678
_diffrn_reflns_theta_min         3.629
_exptl_absorpt_coefficient_mu    3.498
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.270
_refine_diff_density_max         1.458
_refine_diff_density_min         -1.347
_refine_ls_extinction_coef       0.0034(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+4.0804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                2456
_reflns_number_total             2531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7668sup1.cif
_cod_data_source_block           I
_cod_database_code               2242219
_cod_database_fobs_code          2242219
_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   0.430
_shelx_estimated_absorpt_t_max   0.452
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
I I1 0.60686(2) -0.05887(3) 0.93105(2) 0.02375(9) Uani d 1
O O1 0.68205(12) 0.6146(3) 0.71878(13) 0.0231(4) Uani d 1
N N1 0.60465(12) 0.4020(4) 0.58050(14) 0.0174(4) Uani d 1
C C1 0.53347(15) 0.5410(4) 0.54603(16) 0.0207(5) Uani d 1
H H1A 0.545662 0.699539 0.541455 0.025 Uiso calc 1
H H1B 0.516975 0.534394 0.588747 0.025 Uiso calc 1
C C2 0.67584(15) 0.5254(5) 0.63881(17) 0.0214(5) Uani d 1
H H2A 0.678708 0.651795 0.604633 0.026 Uiso calc 1
H H2B 0.721287 0.425521 0.657944 0.026 Uiso calc 1
C C3 0.66459(15) 0.4585(4) 0.76215(17) 0.0187(4) Uani d 1
C C4 0.62686(14) 0.2547(4) 0.72243(15) 0.0171(4) Uani d 1
C C5 0.60538(15) 0.1994(4) 0.62851(16) 0.0199(4) Uani d 1
H H5A 0.643793 0.090235 0.632478 0.024 Uiso calc 1
H H5B 0.552776 0.128136 0.594033 0.024 Uiso calc 1
C C6 0.61047(15) 0.1080(4) 0.77133(16) 0.0191(4) Uani d 1
H H6 0.585192 -0.031336 0.745502 0.023 Uiso calc 1
C C7 0.63083(15) 0.1641(5) 0.85739(16) 0.0208(5) Uani d 1
C C8 0.66757(17) 0.3687(5) 0.89574(17) 0.0250(5) Uani d 1
H H8 0.681043 0.407706 0.954297 0.030 Uiso calc 1
C C9 0.68424(17) 0.5143(5) 0.84831(17) 0.0236(5) Uani d 1
H H9 0.709313 0.653654 0.874439 0.028 Uiso calc 1
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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 O1 C2 . . 113.3(2)
C2 N1 C5 . . 108.45(19)
C2 N1 C1 . . 112.6(2)
C5 N1 C1 . . 113.0(2)
N1 C1 C1 . 5_666 111.0(3)
N1 C1 H1A . . 109.4
C1 C1 H1A 5_666 . 109.4
N1 C1 H1B . . 109.4
C1 C1 H1B 5_666 . 109.4
H1A C1 H1B . . 108.0
N1 C2 O1 . . 113.5(2)
N1 C2 H2A . . 108.9
O1 C2 H2A . . 108.9
N1 C2 H2B . . 108.9
O1 C2 H2B . . 108.9
H2A C2 H2B . . 107.7
O1 C3 C9 . . 116.9(2)
O1 C3 C4 . . 122.7(2)
C9 C3 C4 . . 120.3(2)
C6 C4 C3 . . 118.6(2)
C6 C4 C5 . . 122.1(2)
C3 C4 C5 . . 119.3(2)
N1 C5 C4 . . 111.6(2)
N1 C5 H5A . . 109.3
C4 C5 H5A . . 109.3
N1 C5 H5B . . 109.3
C4 C5 H5B . . 109.3
H5A C5 H5B . . 108.0
C7 C6 C4 . . 120.7(2)
C7 C6 H6 . . 119.7
C4 C6 H6 . . 119.7
C6 C7 C8 . . 120.1(2)
C6 C7 I1 . . 120.46(19)
C8 C7 I1 . . 119.41(18)
C9 C8 C7 . . 119.7(2)
C9 C8 H8 . . 120.2
C7 C8 H8 . . 120.2
C8 C9 C3 . . 120.5(3)
C8 C9 H9 . . 119.7
C3 C9 H9 . . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C7 . 2.107(3)
O1 C3 . 1.376(3)
O1 C2 . 1.460(3)
N1 C2 . 1.435(3)
N1 C5 . 1.474(3)
N1 C1 . 1.478(3)
C1 C1 5_666 1.523(5)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C9 . 1.397(4)
C3 C4 . 1.400(3)
C4 C6 . 1.399(3)
C4 C5 . 1.515(3)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 C7 . 1.391(3)
C6 H6 . 0.9500
C7 C8 . 1.394(4)
C8 C9 . 1.378(4)
C8 H8 . 0.9500
C9 H9 . 0.9500
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
I1 N1 3.378(2) 6_556 n
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_site_symmetry_4
_geom_torsion
C2 N1 C1 C1 5_666 150.8(3)
C5 N1 C1 C1 5_666 -85.9(3)
C5 N1 C2 O1 . -65.2(3)
C1 N1 C2 O1 . 60.5(3)
C3 O1 C2 N1 . 47.5(3)
C2 O1 C3 C9 . 167.3(2)
C2 O1 C3 C4 . -14.5(3)
O1 C3 C4 C6 . -179.0(2)
C9 C3 C4 C6 . -0.9(4)
O1 C3 C4 C5 . 1.2(4)
C9 C3 C4 C5 . 179.3(2)
C2 N1 C5 C4 . 48.3(3)
C1 N1 C5 C4 . -77.2(2)
C6 C4 C5 N1 . 161.7(2)
C3 C4 C5 N1 . -18.6(3)
C3 C4 C6 C7 . 0.4(4)
C5 C4 C6 C7 . -179.9(2)
C4 C6 C7 C8 . 0.3(4)
C4 C6 C7 I1 . -179.47(18)
C6 C7 C8 C9 . -0.6(4)
I1 C7 C8 C9 . 179.2(2)
C7 C8 C9 C3 . 0.1(4)
O1 C3 C9 C8 . 178.9(3)
C4 C3 C9 C8 . 0.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 85607566
